#------------------------------------------------------------------------------
#$Date: 2020-06-04 02:26:04 +0300 (Thu, 04 Jun 2020) $
#$Revision: 252584 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/84/4038457.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4038457
loop_
_publ_author_name
'Ruppel, Michael'
'Gazetas, Lampros-Pascal'
'Lungerich, Dominik'
'Hampel, Frank'
'Jux, Norbert'
_publ_section_title
;
 Investigations of low-symmetrical tetraaryltetrabenzoporphyrins produced
 by mixed condensation reactions.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00293
_journal_year                    2020
_chemical_formula_moiety         'C H2 Cl2, C80 H74 N4 O4, 0.8[CH2Cl2]'
_chemical_formula_sum            'C81 H76 Cl2 N4 O4'
_chemical_formula_weight         1240.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-07
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.1090(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.81190(10)
_cell_length_b                   27.3640(4)
_cell_length_c                   23.5338(3)
_cell_measurement_reflns_used    10535
_cell_measurement_temperature    153.00(10)
_cell_measurement_theta_max      63.6660
_cell_measurement_theta_min      4.0830
_cell_volume                     6952.39(15)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      153.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6144
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -107.00 -65.00   1.00    1.00    --  -42.31-137.00  82.00   42
  2  ω    -70.00  31.00   1.00    1.00    --  -42.31  57.00 120.00  101
  3  ω     59.00 156.00   1.00    2.54    --   87.05  30.00-180.00   97
  4  ω      4.00 103.00   1.00    2.54    --   87.05 -94.00 120.00   99
  5  ω     32.00  90.00   1.00    2.54    --   87.05-125.00 -90.00   58
  6  ω     33.00 110.00   1.00    2.54    --   87.05-125.00  90.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0661803000
_diffrn_orient_matrix_UB_12      0.0224620000
_diffrn_orient_matrix_UB_13      0.0534500000
_diffrn_orient_matrix_UB_21      0.0264432000
_diffrn_orient_matrix_UB_22      -0.0516192000
_diffrn_orient_matrix_UB_23      0.0237780000
_diffrn_orient_matrix_UB_31      0.1236044000
_diffrn_orient_matrix_UB_32      -0.0009440000
_diffrn_orient_matrix_UB_33      -0.0295998000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21182
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        63.824
_diffrn_reflns_theta_max         63.824
_diffrn_reflns_theta_min         3.738
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.250
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.575
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic dark violet'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_description       block
_exptl_crystal_F_000             2624
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of DCM/TFA and methanol  by solvent layering'
_exptl_crystal_size_max          0.301
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.147
_refine_diff_density_max         0.731
_refine_diff_density_min         -1.302
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.00046(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     836
_refine_ls_number_reflns         11068
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0697
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1211P)²+6.2034P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1942
_refine_ls_wR_factor_ref         0.2086
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9079
_reflns_number_total             11068
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00293_si_002.cif
_cod_data_source_block           19jux_mr04
_cod_database_code               4038457
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C80 H74 N4 O4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.838
_shelx_estimated_absorpt_t_min   0.705
_diffrn_oxdiff_digest_frames
;
011a8c6ed5c004d10c03808b4aeed97cf800496373a
;
_diffrn_oxdiff_digest_hkl
;
0158324e1e9654ecd79f82b38f406ce62ff72e
;
_reflns_odcompleteness_completeness 98.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl2-C200 \\sim Cl2A-C200 \\sim Cl1-C200 \\sim Cl1A-C200
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Cl2) = Uanis(Cl2A) = Uanis(Cl1) = Uanis(Cl1A)
4. Others
 Sof(Cl1A)=Sof(Cl2A)=Sof(H20C)=Sof(H20D)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(H20B)=Sof(H20A)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C200(H20B,H20A), C200(H20C,H20D)
5.b Aromatic/amide H refined with riding coordinates:
 N11(H11), N61(H61), C14(H14), C15(H15), C16(H16), C17(H17), C22(H22),
 C23(H23), C25(H25), C26(H26), C34(H34), C35(H35), C36(H36), C37(H37), C42(H42),
  C44(H44), C46(H46), C64(H64), C65(H65), C66(H66), C67(H67), C72(H72),
 C73(H73), C75(H75), C76(H76), C84(H84), C85(H85), C86(H86), C87(H87), C92(H92),
  C94(H94), C96(H96)
5.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C), C50(H50A,H50B,
 H50C), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C), C54(H54A,H54B,H54C), C80(H80A,
 H80B,H80C), C98(H98A,H98B,H98C), C99(H99A,H99B,H99C), C100(H10A,H10B,H10C),
 C102(H10D,H10E,H10F), C103(H10G,H10H,H10I), C104(H10J,H10K,H10L)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_date_sample_data_collection 2019-08-21
_olex2_diffrn_ambient_temperature_device 'Cryojet - Oxford Instruments'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop in perfluoroether oil'
_olex2_submission_original_sample_id MR244-trans
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.126
_oxdiff_exptl_absorpt_empirical_full_min 0.922
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.25019(18) 0.55693(7) 1.03720(8) 0.1011(4) Uani 0.822(2) 1 d D . P A 1
Cl1A Cl 0.1414(8) 0.5351(3) 1.0615(3) 0.1011(4) Uani 0.178(2) 1 d D . P A 2
Cl2 Cl 0.12097(19) 0.58127(8) 0.93049(8) 0.1011(4) Uani 0.822(2) 1 d D . P A 1
Cl2A Cl 0.1660(9) 0.5603(4) 0.9474(4) 0.1011(4) Uani 0.178(2) 1 d D . P A 2
C200 C 0.1105(6) 0.5682(3) 1.0043(2) 0.110(2) Uani 1 1 d D . . . .
H20B H 0.071743 0.596261 1.022989 0.131 Uiso 0.822(2) 1 calc R . P A 1
H20A H 0.056399 0.539362 1.008543 0.131 Uiso 0.822(2) 1 calc R . P A 1
H20C H 0.019577 0.566627 0.996909 0.131 Uiso 0.178(2) 1 calc R . P A 2
H20D H 0.129953 0.602363 1.015243 0.131 Uiso 0.178(2) 1 calc R . P A 2
O28 O -0.0237(3) 0.49888(11) 0.24475(10) 0.0727(9) Uani 1 1 d . . . . .
O29 O 0.0706(2) 0.42721(9) 0.23054(9) 0.0523(6) Uani 1 1 d . . . . .
O78 O 0.8384(3) 0.57808(17) 0.98346(11) 0.1005(14) Uani 1 1 d . . . . .
O79 O 0.6659(2) 0.56002(8) 1.02528(8) 0.0408(5) Uani 1 1 d . . . . .
N11 N 0.25585(19) 0.45649(8) 0.58592(9) 0.0246(5) Uani 1 1 d . . . . .
H11 H 0.315203 0.475169 0.601011 0.030 Uiso 1 1 calc R . . . .
N31 N 0.37761(19) 0.54800(8) 0.54917(9) 0.0253(5) Uani 1 1 d . . . . .
N61 N 0.4481(2) 0.57432(8) 0.66668(9) 0.0293(5) Uani 1 1 d . . . . .
H61 H 0.433606 0.546934 0.647898 0.035 Uiso 1 1 calc R . . . .
N81 N 0.35277(19) 0.47820(8) 0.70313(9) 0.0257(5) Uani 1 1 d . . . . .
C12 C 0.2142(2) 0.45891(9) 0.52988(11) 0.0246(5) Uani 1 1 d . . . . .
C13 C 0.1097(2) 0.42545(10) 0.52382(11) 0.0269(6) Uani 1 1 d . . . . .
C14 C 0.0200(2) 0.41747(11) 0.47915(12) 0.0311(6) Uani 1 1 d . . . . .
H14 H 0.027026 0.432782 0.443244 0.037 Uiso 1 1 calc R . . . .
C15 C -0.0787(3) 0.38675(11) 0.48874(12) 0.0333(6) Uani 1 1 d . . . . .
H15 H -0.140546 0.381482 0.459165 0.040 Uiso 1 1 calc R . . . .
C16 C -0.0887(3) 0.36363(11) 0.54056(13) 0.0345(6) Uani 1 1 d . . . . .
H16 H -0.156893 0.342482 0.545708 0.041 Uiso 1 1 calc R . . . .
C17 C -0.0021(2) 0.37061(10) 0.58477(12) 0.0298(6) Uani 1 1 d . . . . .
H17 H -0.009973 0.354450 0.620116 0.036 Uiso 1 1 calc R . . . .
C18 C 0.0986(2) 0.40214(9) 0.57678(11) 0.0257(5) Uani 1 1 d . . . . .
C19 C 0.1950(2) 0.42187(9) 0.61584(11) 0.0253(5) Uani 1 1 d . . . . .
C20 C 0.2649(2) 0.48817(10) 0.48821(10) 0.0245(5) Uani 1 1 d . . . . .
C21 C 0.2142(2) 0.48052(10) 0.42858(11) 0.0259(6) Uani 1 1 d . . . . .
C22 C 0.1292(3) 0.51432(10) 0.40563(11) 0.0299(6) Uani 1 1 d . . . . .
H22 H 0.106051 0.541433 0.427919 0.036 Uiso 1 1 calc R . . . .
C23 C 0.0782(3) 0.50902(11) 0.35102(12) 0.0336(6) Uani 1 1 d . . . . .
H23 H 0.019928 0.532290 0.336026 0.040 Uiso 1 1 calc R . . . .
C24 C 0.1118(3) 0.46968(11) 0.31789(12) 0.0340(6) Uani 1 1 d . . . . .
C25 C 0.1982(3) 0.43591(11) 0.34036(12) 0.0326(6) Uani 1 1 d . . . . .
H25 H 0.222341 0.409130 0.317786 0.039 Uiso 1 1 calc R . . . .
C26 C 0.2489(2) 0.44123(10) 0.39536(11) 0.0285(6) Uani 1 1 d . . . . .
H26 H 0.307409 0.418075 0.410418 0.034 Uiso 1 1 calc R . . . .
C27 C 0.0540(3) 0.46200(13) 0.26016(13) 0.0426(7) Uani 1 1 d . . . . .
C30 C -0.0970(5) 0.4920(2) 0.19219(18) 0.0875(17) Uani 1 1 d . . . . .
H30A H -0.042460 0.491324 0.160275 0.131 Uiso 1 1 calc GR . . . .
H30B H -0.156133 0.518979 0.186954 0.131 Uiso 1 1 calc GR . . . .
H30C H -0.142196 0.461015 0.193690 0.131 Uiso 1 1 calc GR . . . .
C32 C 0.4342(2) 0.59182(10) 0.54010(11) 0.0254(5) Uani 1 1 d . . . . .
C33 C 0.4513(2) 0.59848(10) 0.47901(11) 0.0268(6) Uani 1 1 d . . . . .
C34 C 0.5085(3) 0.63472(11) 0.44694(12) 0.0327(6) Uani 1 1 d . . . . .
H34 H 0.549371 0.661645 0.465230 0.039 Uiso 1 1 calc R . . . .
C35 C 0.5041(3) 0.63032(11) 0.38853(12) 0.0341(6) Uani 1 1 d . . . . .
H35 H 0.538826 0.655275 0.366311 0.041 Uiso 1 1 calc R . . . .
C36 C 0.4495(2) 0.58993(11) 0.36169(12) 0.0325(6) Uani 1 1 d . . . . .
H36 H 0.447393 0.587766 0.321360 0.039 Uiso 1 1 calc R . . . .
C37 C 0.3983(2) 0.55301(11) 0.39240(11) 0.0301(6) Uani 1 1 d . . . . .
H37 H 0.364941 0.524766 0.373780 0.036 Uiso 1 1 calc R . . . .
C38 C 0.3963(2) 0.55782(10) 0.45183(11) 0.0264(6) Uani 1 1 d . . . . .
C39 C 0.3471(2) 0.52764(10) 0.49722(10) 0.0253(5) Uani 1 1 d . . . . .
C40 C 0.4614(2) 0.62683(10) 0.58258(11) 0.0274(6) Uani 1 1 d . . . . .
C41 C 0.4995(3) 0.67679(10) 0.56454(11) 0.0284(6) Uani 1 1 d . . . . .
C42 C 0.6219(3) 0.69148(10) 0.57377(11) 0.0318(6) Uani 1 1 d . . . . .
H42 H 0.679634 0.669977 0.592621 0.038 Uiso 1 1 calc R . . . .
C43 C 0.6617(3) 0.73705(11) 0.55596(12) 0.0327(6) Uani 1 1 d . . . . .
C44 C 0.5753(3) 0.76740(10) 0.52821(12) 0.0335(6) Uani 1 1 d . . . . .
H44 H 0.601230 0.798514 0.515497 0.040 Uiso 1 1 calc R . . . .
C45 C 0.4513(3) 0.75388(10) 0.51825(11) 0.0326(6) Uani 1 1 d . . . . .
C46 C 0.4143(3) 0.70832(10) 0.53728(11) 0.0302(6) Uani 1 1 d . . . . .
H46 H 0.330179 0.698625 0.531634 0.036 Uiso 1 1 calc R . . . .
C47 C 0.7978(3) 0.75161(12) 0.56815(14) 0.0423(7) Uani 1 1 d . . . . .
C48 C 0.8809(3) 0.71526(15) 0.53916(19) 0.0606(10) Uani 1 1 d . . . . .
H48A H 0.869382 0.682585 0.555077 0.091 Uiso 1 1 calc GR . . . .
H48B H 0.967695 0.725136 0.545602 0.091 Uiso 1 1 calc GR . . . .
H48C H 0.859142 0.714722 0.498202 0.091 Uiso 1 1 calc GR . . . .
C49 C 0.8244(4) 0.75163(18) 0.63224(17) 0.0657(11) Uani 1 1 d . . . . .
H49A H 0.770371 0.775396 0.649788 0.099 Uiso 1 1 calc GR . . . .
H49B H 0.911151 0.760518 0.640880 0.099 Uiso 1 1 calc GR . . . .
H49C H 0.808699 0.718975 0.647380 0.099 Uiso 1 1 calc GR . . . .
C50 C 0.8252(4) 0.80243(14) 0.5449(2) 0.0636(11) Uani 1 1 d . . . . .
H50A H 0.805128 0.803097 0.503797 0.095 Uiso 1 1 calc GR . . . .
H50B H 0.913174 0.809995 0.552349 0.095 Uiso 1 1 calc GR . . . .
H50C H 0.774850 0.826756 0.563661 0.095 Uiso 1 1 calc GR . . . .
C51 C 0.3568(3) 0.78657(11) 0.48504(14) 0.0423(7) Uani 1 1 d . . . . .
C52 C 0.2480(4) 0.79737(15) 0.5210(2) 0.0665(11) Uani 1 1 d . . . . .
H52A H 0.206320 0.766742 0.529898 0.100 Uiso 1 1 calc GR . . . .
H52B H 0.189643 0.818967 0.499849 0.100 Uiso 1 1 calc GR . . . .
H52C H 0.277731 0.813392 0.556351 0.100 Uiso 1 1 calc GR . . . .
C53 C 0.3134(4) 0.75936(15) 0.43067(16) 0.0634(11) Uani 1 1 d . . . . .
H53A H 0.385499 0.749531 0.409923 0.095 Uiso 1 1 calc GR . . . .
H53B H 0.260371 0.780886 0.406615 0.095 Uiso 1 1 calc GR . . . .
H53C H 0.266414 0.730252 0.440680 0.095 Uiso 1 1 calc GR . . . .
C54 C 0.4147(4) 0.83510(13) 0.46707(18) 0.0599(10) Uani 1 1 d . . . . .
H54A H 0.449589 0.852185 0.500866 0.090 Uiso 1 1 calc GR . . . .
H54B H 0.350974 0.855545 0.447789 0.090 Uiso 1 1 calc GR . . . .
H54C H 0.480628 0.828506 0.441113 0.090 Uiso 1 1 calc GR . . . .
C62 C 0.4580(2) 0.61915(10) 0.64123(11) 0.0279(6) Uani 1 1 d . . . . .
C63 C 0.4707(2) 0.65493(10) 0.68681(11) 0.0284(6) Uani 1 1 d . . . . .
C64 C 0.4692(3) 0.70611(11) 0.68742(12) 0.0339(6) Uani 1 1 d . . . . .
H64 H 0.468507 0.723965 0.652781 0.041 Uiso 1 1 calc R . . . .
C65 C 0.4686(3) 0.73022(11) 0.73855(13) 0.0396(7) Uani 1 1 d . . . . .
H65 H 0.468004 0.764929 0.739263 0.048 Uiso 1 1 calc R . . . .
C66 C 0.4690(3) 0.70403(12) 0.78967(13) 0.0421(7) Uani 1 1 d . . . . .
H66 H 0.467166 0.721390 0.824572 0.051 Uiso 1 1 calc R . . . .
C67 C 0.4720(3) 0.65386(11) 0.79059(12) 0.0382(7) Uani 1 1 d . . . . .
H67 H 0.472883 0.636572 0.825621 0.046 Uiso 1 1 calc R . . . .
C68 C 0.4736(3) 0.62865(10) 0.73864(11) 0.0312(6) Uani 1 1 d . . . . .
C69 C 0.4636(3) 0.57718(10) 0.72501(11) 0.0299(6) Uani 1 1 d . . . . .
C70 C 0.4714(2) 0.53718(10) 0.76223(11) 0.0289(6) Uani 1 1 d . . . . .
C71 C 0.5332(3) 0.54704(10) 0.81948(11) 0.0301(6) Uani 1 1 d . . . . .
C72 C 0.4707(3) 0.54318(10) 0.86950(11) 0.0312(6) Uani 1 1 d . . . . .
H72 H 0.385053 0.535254 0.867581 0.037 Uiso 1 1 calc R . . . .
C73 C 0.5318(3) 0.55073(10) 0.92191(11) 0.0309(6) Uani 1 1 d . . . . .
H73 H 0.488043 0.548097 0.955704 0.037 Uiso 1 1 calc R . . . .
C74 C 0.6575(3) 0.56219(11) 0.92516(12) 0.0344(6) Uani 1 1 d . . . . .
C75 C 0.7202(3) 0.56755(12) 0.87508(12) 0.0377(7) Uani 1 1 d . . . . .
H75 H 0.805236 0.576513 0.876848 0.045 Uiso 1 1 calc R . . . .
C76 C 0.6581(3) 0.55977(11) 0.82313(12) 0.0347(6) Uani 1 1 d . . . . .
H76 H 0.701269 0.563153 0.789244 0.042 Uiso 1 1 calc R . . . .
C77 C 0.7304(3) 0.56793(13) 0.97978(13) 0.0429(7) Uani 1 1 d . . . . .
C80 C 0.7372(3) 0.55991(13) 1.07887(12) 0.0445(8) Uani 1 1 d . . . . .
H80A H 0.793457 0.531804 1.080315 0.067 Uiso 1 1 calc GR . . . .
H80B H 0.681101 0.557680 1.110108 0.067 Uiso 1 1 calc GR . . . .
H80C H 0.785451 0.590162 1.082605 0.067 Uiso 1 1 calc GR . . . .
C82 C 0.4294(2) 0.48974(10) 0.74950(10) 0.0262(6) Uani 1 1 d . . . . .
C83 C 0.4494(2) 0.44629(10) 0.78571(10) 0.0263(6) Uani 1 1 d . . . . .
C84 C 0.5312(3) 0.43519(11) 0.83212(11) 0.0314(6) Uani 1 1 d . . . . .
H84 H 0.587467 0.459094 0.847364 0.038 Uiso 1 1 calc R . . . .
C85 C 0.5286(3) 0.38887(11) 0.85529(12) 0.0353(7) Uani 1 1 d . . . . .
H85 H 0.584025 0.380846 0.886613 0.042 Uiso 1 1 calc R . . . .
C86 C 0.4462(3) 0.35384(11) 0.83345(12) 0.0354(7) Uani 1 1 d . . . . .
H86 H 0.443673 0.322680 0.851152 0.042 Uiso 1 1 calc R . . . .
C87 C 0.3675(3) 0.36342(10) 0.78642(11) 0.0319(6) Uani 1 1 d . . . . .
H87 H 0.313356 0.338899 0.770962 0.038 Uiso 1 1 calc R . . . .
C88 C 0.3698(2) 0.41022(10) 0.76209(10) 0.0256(5) Uani 1 1 d . . . . .
C89 C 0.3114(2) 0.43189(10) 0.71015(10) 0.0249(5) Uani 1 1 d . . . . .
C90 C 0.2255(2) 0.40805(10) 0.67206(11) 0.0256(5) Uani 1 1 d . . . . .
C91 C 0.1584(2) 0.36456(10) 0.69310(11) 0.0280(6) Uani 1 1 d . . . . .
C92 C 0.1831(3) 0.31767(10) 0.67335(12) 0.0324(6) Uani 1 1 d . . . . .
H92 H 0.248237 0.312990 0.648397 0.039 Uiso 1 1 calc R . . . .
C93 C 0.1142(3) 0.27786(11) 0.68947(13) 0.0384(7) Uani 1 1 d . . . . .
C94 C 0.0175(3) 0.28630(12) 0.72559(15) 0.0456(8) Uani 1 1 d . . . . .
H94 H -0.030727 0.259317 0.736899 0.055 Uiso 1 1 calc R . . . .
C95 C -0.0106(3) 0.33248(12) 0.74544(13) 0.0404(7) Uani 1 1 d . . . . .
C96 C 0.0636(2) 0.37150(11) 0.72963(12) 0.0324(6) Uani 1 1 d . . . . .
H96 H 0.048820 0.403248 0.744135 0.039 Uiso 1 1 calc R . . . .
C97 C 0.1390(4) 0.22574(12) 0.66809(17) 0.0563(10) Uani 1 1 d . . . . .
C98 C 0.2428(5) 0.22442(14) 0.62673(16) 0.0663(12) Uani 1 1 d . . . . .
H98A H 0.222215 0.246322 0.594648 0.099 Uiso 1 1 calc GR . . . .
H98B H 0.252370 0.191011 0.612622 0.099 Uiso 1 1 calc GR . . . .
H98C H 0.320406 0.235076 0.646331 0.099 Uiso 1 1 calc GR . . . .
C99 C 0.0215(5) 0.20582(18) 0.6370(3) 0.105(2) Uani 1 1 d . . . . .
H99A H -0.045492 0.204486 0.663446 0.158 Uiso 1 1 calc GR . . . .
H99B H 0.037478 0.172898 0.622776 0.158 Uiso 1 1 calc GR . . . .
H99C H -0.002765 0.227316 0.605052 0.158 Uiso 1 1 calc GR . . . .
C100 C 0.1764(4) 0.19339(13) 0.71956(19) 0.0636(11) Uani 1 1 d . . . . .
H10A H 0.251213 0.206683 0.739213 0.095 Uiso 1 1 calc GR . . . .
H10B H 0.192805 0.160114 0.706545 0.095 Uiso 1 1 calc GR . . . .
H10C H 0.108934 0.192744 0.745739 0.095 Uiso 1 1 calc GR . . . .
C101 C -0.1245(3) 0.34288(17) 0.77998(16) 0.0586(10) Uani 1 1 d . . . . .
C102 C -0.2181(5) 0.3679(4) 0.7416(3) 0.156(4) Uani 1 1 d . . . . .
H10D H -0.186326 0.399903 0.730715 0.234 Uiso 1 1 calc GR . . . .
H10E H -0.294841 0.372214 0.761320 0.234 Uiso 1 1 calc GR . . . .
H10F H -0.234818 0.348022 0.707366 0.234 Uiso 1 1 calc GR . . . .
C103 C -0.1784(4) 0.2954(2) 0.8038(2) 0.0981(19) Uani 1 1 d . . . . .
H10G H -0.203146 0.273462 0.772225 0.147 Uiso 1 1 calc GR . . . .
H10H H -0.250755 0.303138 0.825413 0.147 Uiso 1 1 calc GR . . . .
H10I H -0.115434 0.279264 0.828813 0.147 Uiso 1 1 calc GR . . . .
C104 C -0.0876(5) 0.3735(2) 0.8321(2) 0.0959(17) Uani 1 1 d . . . . .
H10J H -0.018372 0.357781 0.853534 0.144 Uiso 1 1 calc GR . . . .
H10K H -0.158300 0.376335 0.856231 0.144 Uiso 1 1 calc GR . . . .
H10L H -0.062510 0.406136 0.819985 0.144 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
7 4 -4 0.1184
-7 -4 4 0.1184
0 -11 -12 0.0810
0 11 12 0.0810
0 12 -11 0.0737
0 -12 11 0.0737
7 -3 -5 0.1316
-7 3 5 0.1316
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 C200 Cl2 112.4(4) . . ?
Cl1 C200 H20B 109.1 . . ?
Cl1 C200 H20A 109.1 . . ?
Cl1A C200 H20C 106.1 . . ?
Cl1A C200 H20D 106.1 . . ?
Cl2 C200 H20B 109.1 . . ?
Cl2 C200 H20A 109.1 . . ?
Cl2A C200 Cl1A 125.0(7) . . ?
Cl2A C200 H20C 106.1 . . ?
Cl2A C200 H20D 106.1 . . ?
H20B C200 H20A 107.9 . . ?
H20C C200 H20D 106.3 . . ?
C27 O28 C30 115.9(3) . . ?
C77 O79 C80 115.3(2) . . ?
C12 N11 H11 123.6 . . ?
C19 N11 H11 123.6 . . ?
C19 N11 C12 112.7(2) . . ?
C39 N31 C32 107.8(2) . . ?
C62 N61 H61 123.9 . . ?
C62 N61 C69 112.1(2) . . ?
C69 N61 H61 123.9 . . ?
C89 N81 C82 107.9(2) . . ?
N11 C12 C13 106.0(2) . . ?
N11 C12 C20 125.5(2) . . ?
C20 C12 C13 128.5(2) . . ?
C14 C13 C12 132.1(3) . . ?
C14 C13 C18 120.1(2) . . ?
C18 C13 C12 107.5(2) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 C13 118.5(3) . . ?
C15 C14 H14 120.7 . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.2(3) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.4(3) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 118.9(3) . . ?
C18 C17 H17 120.5 . . ?
C13 C18 C19 107.3(2) . . ?
C17 C18 C13 119.8(2) . . ?
C17 C18 C19 132.4(2) . . ?
N11 C19 C18 106.2(2) . . ?
N11 C19 C90 125.4(2) . . ?
C90 C19 C18 128.4(2) . . ?
C12 C20 C21 116.1(2) . . ?
C12 C20 C39 126.9(2) . . ?
C39 C20 C21 116.5(2) . . ?
C22 C21 C20 118.2(2) . . ?
C22 C21 C26 119.2(2) . . ?
C26 C21 C20 122.6(2) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 C21 120.9(3) . . ?
C23 C22 H22 119.5 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.1(3) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C25 119.3(3) . . ?
C23 C24 C27 121.0(3) . . ?
C25 C24 C27 119.6(3) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.4(3) . . ?
C26 C25 H25 119.8 . . ?
C21 C26 H26 120.0 . . ?
C25 C26 C21 120.0(2) . . ?
C25 C26 H26 120.0 . . ?
O28 C27 C24 111.5(3) . . ?
O29 C27 O28 123.2(3) . . ?
O29 C27 C24 125.3(3) . . ?
O28 C30 H30A 109.5 . . ?
O28 C30 H30B 109.5 . . ?
O28 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N31 C32 C33 110.0(2) . . ?
N31 C32 C40 124.4(2) . . ?
C40 C32 C33 125.4(2) . . ?
C34 C33 C32 133.9(3) . . ?
C38 C33 C32 106.0(2) . . ?
C38 C33 C34 120.2(2) . . ?
C33 C34 H34 120.7 . . ?
C35 C34 C33 118.7(3) . . ?
C35 C34 H34 120.7 . . ?
C34 C35 H35 119.5 . . ?
C34 C35 C36 121.0(3) . . ?
C36 C35 H35 119.5 . . ?
C35 C36 H36 119.4 . . ?
C37 C36 C35 121.2(3) . . ?
C37 C36 H36 119.4 . . ?
C36 C37 H37 120.6 . . ?
C36 C37 C38 118.8(3) . . ?
C38 C37 H37 120.6 . . ?
C33 C38 C37 120.0(2) . . ?
C33 C38 C39 106.0(2) . . ?
C37 C38 C39 134.0(3) . . ?
N31 C39 C20 124.5(2) . . ?
N31 C39 C38 109.9(2) . . ?
C20 C39 C38 124.8(2) . . ?
C32 C40 C41 118.1(2) . . ?
C62 C40 C32 125.8(2) . . ?
C62 C40 C41 116.1(2) . . ?
C42 C41 C40 119.7(2) . . ?
C42 C41 C46 119.5(3) . . ?
C46 C41 C40 120.8(2) . . ?
C41 C42 H42 119.3 . . ?
C41 C42 C43 121.3(3) . . ?
C43 C42 H42 119.3 . . ?
C42 C43 C47 119.0(3) . . ?
C44 C43 C42 117.8(3) . . ?
C44 C43 C47 123.2(3) . . ?
C43 C44 H44 118.8 . . ?
C43 C44 C45 122.4(3) . . ?
C45 C44 H44 118.8 . . ?
C44 C45 C51 122.4(3) . . ?
C46 C45 C44 118.3(3) . . ?
C46 C45 C51 119.3(3) . . ?
C41 C46 H46 119.7 . . ?
C45 C46 C41 120.6(3) . . ?
C45 C46 H46 119.7 . . ?
C48 C47 C43 109.2(3) . . ?
C48 C47 C50 107.6(3) . . ?
C49 C47 C43 108.2(3) . . ?
C49 C47 C48 111.1(3) . . ?
C49 C47 C50 109.0(3) . . ?
C50 C47 C43 111.8(3) . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C47 C49 H49A 109.5 . . ?
C47 C49 H49B 109.5 . . ?
C47 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C47 C50 H50A 109.5 . . ?
C47 C50 H50B 109.5 . . ?
C47 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C52 C51 C45 110.2(3) . . ?
C52 C51 C53 110.4(3) . . ?
C52 C51 C54 109.0(3) . . ?
C53 C51 C45 107.9(3) . . ?
C53 C51 C54 107.5(3) . . ?
C54 C51 C45 111.8(3) . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C51 C53 H53A 109.5 . . ?
C51 C53 H53B 109.5 . . ?
C51 C53 H53C 109.5 . . ?
H53A C53 H53B 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C51 C54 H54A 109.5 . . ?
C51 C54 H54B 109.5 . . ?
C51 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
N61 C62 C40 124.9(2) . . ?
N61 C62 C63 106.7(2) . . ?
C40 C62 C63 128.4(2) . . ?
C64 C63 C62 132.9(3) . . ?
C64 C63 C68 119.9(3) . . ?
C68 C63 C62 106.9(2) . . ?
C63 C64 H64 120.3 . . ?
C65 C64 C63 119.3(3) . . ?
C65 C64 H64 120.3 . . ?
C64 C65 H65 119.8 . . ?
C64 C65 C66 120.5(3) . . ?
C66 C65 H65 119.8 . . ?
C65 C66 H66 119.2 . . ?
C67 C66 C65 121.6(3) . . ?
C67 C66 H66 119.2 . . ?
C66 C67 H67 120.7 . . ?
C66 C67 C68 118.6(3) . . ?
C68 C67 H67 120.7 . . ?
C63 C68 C69 107.8(2) . . ?
C67 C68 C63 120.0(3) . . ?
C67 C68 C69 131.8(3) . . ?
N61 C69 C68 106.3(2) . . ?
N61 C69 C70 125.4(2) . . ?
C70 C69 C68 128.3(2) . . ?
C69 C70 C71 115.5(2) . . ?
C69 C70 C82 125.6(2) . . ?
C82 C70 C71 118.9(2) . . ?
C72 C71 C70 122.3(3) . . ?
C72 C71 C76 118.7(3) . . ?
C76 C71 C70 119.0(2) . . ?
C71 C72 H72 119.6 . . ?
C73 C72 C71 120.8(3) . . ?
C73 C72 H72 119.6 . . ?
C72 C73 H73 120.0 . . ?
C72 C73 C74 120.0(3) . . ?
C74 C73 H73 120.0 . . ?
C73 C74 C75 119.6(3) . . ?
C73 C74 C77 123.0(3) . . ?
C75 C74 C77 117.5(3) . . ?
C74 C75 H75 120.1 . . ?
C76 C75 C74 119.7(3) . . ?
C76 C75 H75 120.1 . . ?
C71 C76 H76 119.4 . . ?
C75 C76 C71 121.1(3) . . ?
C75 C76 H76 119.4 . . ?
O78 C77 O79 122.1(3) . . ?
O78 C77 C74 124.0(3) . . ?
O79 C77 C74 113.9(3) . . ?
O79 C80 H80A 109.5 . . ?
O79 C80 H80B 109.5 . . ?
O79 C80 H80C 109.5 . . ?
H80A C80 H80B 109.5 . . ?
H80A C80 H80C 109.5 . . ?
H80B C80 H80C 109.5 . . ?
N81 C82 C70 123.9(2) . . ?
N81 C82 C83 109.8(2) . . ?
C70 C82 C83 126.0(2) . . ?
C84 C83 C82 133.9(3) . . ?
C84 C83 C88 120.3(2) . . ?
C88 C83 C82 105.7(2) . . ?
C83 C84 H84 120.6 . . ?
C85 C84 C83 118.8(3) . . ?
C85 C84 H84 120.6 . . ?
C84 C85 H85 119.5 . . ?
C84 C85 C86 120.9(3) . . ?
C86 C85 H85 119.5 . . ?
C85 C86 H86 119.3 . . ?
C87 C86 C85 121.3(3) . . ?
C87 C86 H86 119.3 . . ?
C86 C87 H87 120.8 . . ?
C86 C87 C88 118.4(3) . . ?
C88 C87 H87 120.8 . . ?
C83 C88 C89 105.8(2) . . ?
C87 C88 C83 120.2(2) . . ?
C87 C88 C89 133.7(3) . . ?
N81 C89 C88 110.4(2) . . ?
N81 C89 C90 124.2(2) . . ?
C90 C89 C88 125.3(2) . . ?
C19 C90 C89 126.0(2) . . ?
C19 C90 C91 115.9(2) . . ?
C89 C90 C91 118.1(2) . . ?
C92 C91 C90 121.2(2) . . ?
C96 C91 C90 119.0(2) . . ?
C96 C91 C92 119.6(3) . . ?
C91 C92 H92 119.4 . . ?
C93 C92 C91 121.1(3) . . ?
C93 C92 H92 119.4 . . ?
C92 C93 C94 117.8(3) . . ?
C92 C93 C97 122.2(3) . . ?
C94 C93 C97 119.9(3) . . ?
C93 C94 H94 118.7 . . ?
C95 C94 C93 122.6(3) . . ?
C95 C94 H94 118.7 . . ?
C94 C95 C96 117.9(3) . . ?
C94 C95 C101 122.9(3) . . ?
C96 C95 C101 119.1(3) . . ?
C91 C96 C95 121.0(3) . . ?
C91 C96 H96 119.5 . . ?
C95 C96 H96 119.5 . . ?
C98 C97 C93 112.2(3) . . ?
C98 C97 C99 107.9(4) . . ?
C98 C97 C100 108.6(3) . . ?
C99 C97 C93 109.3(3) . . ?
C99 C97 C100 110.3(4) . . ?
C100 C97 C93 108.6(3) . . ?
C97 C98 H98A 109.5 . . ?
C97 C98 H98B 109.5 . . ?
C97 C98 H98C 109.5 . . ?
H98A C98 H98B 109.5 . . ?
H98A C98 H98C 109.5 . . ?
H98B C98 H98C 109.5 . . ?
C97 C99 H99A 109.5 . . ?
C97 C99 H99B 109.5 . . ?
C97 C99 H99C 109.5 . . ?
H99A C99 H99B 109.5 . . ?
H99A C99 H99C 109.5 . . ?
H99B C99 H99C 109.5 . . ?
C97 C100 H10A 109.5 . . ?
C97 C100 H10B 109.5 . . ?
C97 C100 H10C 109.5 . . ?
H10A C100 H10B 109.5 . . ?
H10A C100 H10C 109.5 . . ?
H10B C100 H10C 109.5 . . ?
C95 C101 C103 111.4(4) . . ?
C102 C101 C95 107.6(3) . . ?
C102 C101 C103 110.5(5) . . ?
C102 C101 C104 112.1(6) . . ?
C104 C101 C95 110.2(3) . . ?
C104 C101 C103 105.1(4) . . ?
C101 C102 H10D 109.5 . . ?
C101 C102 H10E 109.5 . . ?
C101 C102 H10F 109.5 . . ?
H10D C102 H10E 109.5 . . ?
H10D C102 H10F 109.5 . . ?
H10E C102 H10F 109.5 . . ?
C101 C103 H10G 109.5 . . ?
C101 C103 H10H 109.5 . . ?
C101 C103 H10I 109.5 . . ?
H10G C103 H10H 109.5 . . ?
H10G C103 H10I 109.5 . . ?
H10H C103 H10I 109.5 . . ?
C101 C104 H10J 109.5 . . ?
C101 C104 H10K 109.5 . . ?
C101 C104 H10L 109.5 . . ?
H10J C104 H10K 109.5 . . ?
H10J C104 H10L 109.5 . . ?
H10K C104 H10L 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C200 1.688(6) . ?
Cl1A C200 1.641(9) . ?
Cl2 C200 1.783(6) . ?
Cl2A C200 1.512(9) . ?
C200 H20B 0.9900 . ?
C200 H20A 0.9900 . ?
C200 H20C 0.9900 . ?
C200 H20D 0.9900 . ?
O28 C27 1.350(4) . ?
O28 C30 1.445(4) . ?
O29 C27 1.199(4) . ?
O78 C77 1.198(4) . ?
O79 C77 1.327(4) . ?
O79 C80 1.442(3) . ?
N11 H11 0.8800 . ?
N11 C12 1.372(3) . ?
N11 C19 1.370(3) . ?
N31 C32 1.368(3) . ?
N31 C39 1.367(3) . ?
N61 H61 0.8800 . ?
N61 C62 1.372(3) . ?
N61 C69 1.376(3) . ?
N81 C82 1.371(3) . ?
N81 C89 1.357(3) . ?
C12 C13 1.456(4) . ?
C12 C20 1.400(4) . ?
C13 C14 1.408(4) . ?
C13 C18 1.411(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.375(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.410(4) . ?
C18 C19 1.456(4) . ?
C19 C90 1.398(4) . ?
C20 C21 1.494(3) . ?
C20 C39 1.407(4) . ?
C21 C22 1.392(4) . ?
C21 C26 1.393(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.379(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.389(4) . ?
C24 C25 1.397(4) . ?
C24 C27 1.479(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.386(4) . ?
C26 H26 0.9500 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C32 C33 1.471(4) . ?
C32 C40 1.404(4) . ?
C33 C34 1.409(4) . ?
C33 C38 1.400(4) . ?
C34 H34 0.9500 . ?
C34 C35 1.378(4) . ?
C35 H35 0.9500 . ?
C35 C36 1.389(4) . ?
C36 H36 0.9500 . ?
C36 C37 1.375(4) . ?
C37 H37 0.9500 . ?
C37 C38 1.406(4) . ?
C38 C39 1.473(4) . ?
C40 C41 1.496(4) . ?
C40 C62 1.399(4) . ?
C41 C42 1.390(4) . ?
C41 C46 1.393(4) . ?
C42 H42 0.9500 . ?
C42 C43 1.391(4) . ?
C43 C44 1.387(4) . ?
C43 C47 1.536(4) . ?
C44 H44 0.9500 . ?
C44 C45 1.397(4) . ?
C45 C46 1.391(4) . ?
C45 C51 1.539(4) . ?
C46 H46 0.9500 . ?
C47 C48 1.526(5) . ?
C47 C49 1.520(5) . ?
C47 C50 1.529(5) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C51 C52 1.514(5) . ?
C51 C53 1.532(5) . ?
C51 C54 1.538(4) . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C62 C63 1.453(4) . ?
C63 C64 1.401(4) . ?
C63 C68 1.415(4) . ?
C64 H64 0.9500 . ?
C64 C65 1.373(4) . ?
C65 H65 0.9500 . ?
C65 C66 1.400(4) . ?
C66 H66 0.9500 . ?
C66 C67 1.373(4) . ?
C67 H67 0.9500 . ?
C67 C68 1.405(4) . ?
C68 C69 1.447(4) . ?
C69 C70 1.402(4) . ?
C70 C71 1.496(4) . ?
C70 C82 1.403(4) . ?
C71 C72 1.393(4) . ?
C71 C76 1.393(4) . ?
C72 H72 0.9500 . ?
C72 C73 1.383(4) . ?
C73 H73 0.9500 . ?
C73 C74 1.393(4) . ?
C74 C75 1.399(4) . ?
C74 C77 1.480(4) . ?
C75 H75 0.9500 . ?
C75 C76 1.379(4) . ?
C76 H76 0.9500 . ?
C80 H80A 0.9800 . ?
C80 H80B 0.9800 . ?
C80 H80C 0.9800 . ?
C82 C83 1.472(4) . ?
C83 C84 1.401(4) . ?
C83 C88 1.405(4) . ?
C84 H84 0.9500 . ?
C84 C85 1.381(4) . ?
C85 H85 0.9500 . ?
C85 C86 1.389(4) . ?
C86 H86 0.9500 . ?
C86 C87 1.383(4) . ?
C87 H87 0.9500 . ?
C87 C88 1.404(4) . ?
C88 C89 1.470(4) . ?
C89 C90 1.415(4) . ?
C90 C91 1.492(4) . ?
C91 C92 1.395(4) . ?
C91 C96 1.386(4) . ?
C92 H92 0.9500 . ?
C92 C93 1.384(4) . ?
C93 C94 1.402(5) . ?
C93 C97 1.541(5) . ?
C94 H94 0.9500 . ?
C94 C95 1.387(5) . ?
C95 C96 1.398(4) . ?
C95 C101 1.539(5) . ?
C96 H96 0.9500 . ?
C97 C98 1.525(6) . ?
C97 C99 1.531(6) . ?
C97 C100 1.536(5) . ?
C98 H98A 0.9800 . ?
C98 H98B 0.9800 . ?
C98 H98C 0.9800 . ?
C99 H99A 0.9800 . ?
C99 H99B 0.9800 . ?
C99 H99C 0.9800 . ?
C100 H10A 0.9800 . ?
C100 H10B 0.9800 . ?
C100 H10C 0.9800 . ?
C101 C102 1.487(6) . ?
C101 C103 1.543(6) . ?
C101 C104 1.520(7) . ?
C102 H10D 0.9800 . ?
C102 H10E 0.9800 . ?
C102 H10F 0.9800 . ?
C103 H10G 0.9800 . ?
C103 H10H 0.9800 . ?
C103 H10I 0.9800 . ?
C104 H10J 0.9800 . ?
C104 H10K 0.9800 . ?
C104 H10L 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N11 C12 C13 C14 169.8(3) . . . . ?
N11 C12 C13 C18 -3.5(3) . . . . ?
N11 C12 C20 C21 173.0(2) . . . . ?
N11 C12 C20 C39 -15.1(4) . . . . ?
N11 C19 C90 C89 9.8(4) . . . . ?
N11 C19 C90 C91 -171.3(2) . . . . ?
N31 C32 C33 C34 -176.2(3) . . . . ?
N31 C32 C33 C38 3.1(3) . . . . ?
N31 C32 C40 C41 -167.8(2) . . . . ?
N31 C32 C40 C62 13.3(4) . . . . ?
N61 C62 C63 C64 -171.0(3) . . . . ?
N61 C62 C63 C68 2.7(3) . . . . ?
N61 C69 C70 C71 158.3(3) . . . . ?
N61 C69 C70 C82 -20.1(5) . . . . ?
N81 C82 C83 C84 168.6(3) . . . . ?
N81 C82 C83 C88 -6.7(3) . . . . ?
N81 C89 C90 C19 17.9(4) . . . . ?
N81 C89 C90 C91 -161.0(2) . . . . ?
C12 N11 C19 C18 -4.3(3) . . . . ?
C12 N11 C19 C90 173.6(2) . . . . ?
C12 C13 C14 C15 -172.1(3) . . . . ?
C12 C13 C18 C17 174.6(2) . . . . ?
C12 C13 C18 C19 1.0(3) . . . . ?
C12 C20 C21 C22 102.3(3) . . . . ?
C12 C20 C21 C26 -77.9(3) . . . . ?
C12 C20 C39 N31 -9.4(4) . . . . ?
C12 C20 C39 C38 -179.0(2) . . . . ?
C13 C12 C20 C21 -7.0(4) . . . . ?
C13 C12 C20 C39 164.9(3) . . . . ?
C13 C14 C15 C16 -1.1(4) . . . . ?
C13 C18 C19 N11 1.9(3) . . . . ?
C13 C18 C19 C90 -175.9(3) . . . . ?
C14 C13 C18 C17 0.4(4) . . . . ?
C14 C13 C18 C19 -173.2(2) . . . . ?
C14 C15 C16 C17 0.7(4) . . . . ?
C15 C16 C17 C18 0.1(4) . . . . ?
C16 C17 C18 C13 -0.7(4) . . . . ?
C16 C17 C18 C19 171.0(3) . . . . ?
C17 C18 C19 N11 -170.6(3) . . . . ?
C17 C18 C19 C90 11.6(5) . . . . ?
C18 C13 C14 C15 0.5(4) . . . . ?
C18 C19 C90 C89 -172.8(2) . . . . ?
C18 C19 C90 C91 6.1(4) . . . . ?
C19 N11 C12 C13 4.9(3) . . . . ?
C19 N11 C12 C20 -175.0(2) . . . . ?
C19 C90 C91 C92 70.8(3) . . . . ?
C19 C90 C91 C96 -104.3(3) . . . . ?
C20 C12 C13 C14 -10.3(5) . . . . ?
C20 C12 C13 C18 176.4(3) . . . . ?
C20 C21 C22 C23 -179.4(3) . . . . ?
C20 C21 C26 C25 179.7(2) . . . . ?
C21 C20 C39 N31 162.4(2) . . . . ?
C21 C20 C39 C38 -7.1(4) . . . . ?
C21 C22 C23 C24 -0.4(4) . . . . ?
C22 C21 C26 C25 -0.5(4) . . . . ?
C22 C23 C24 C25 -0.4(4) . . . . ?
C22 C23 C24 C27 177.2(3) . . . . ?
C23 C24 C25 C26 0.7(4) . . . . ?
C23 C24 C27 O28 4.4(4) . . . . ?
C23 C24 C27 O29 -174.0(3) . . . . ?
C24 C25 C26 C21 -0.2(4) . . . . ?
C25 C24 C27 O28 -178.0(3) . . . . ?
C25 C24 C27 O29 3.6(5) . . . . ?
C26 C21 C22 C23 0.8(4) . . . . ?
C27 C24 C25 C26 -176.9(3) . . . . ?
C30 O28 C27 O29 6.1(6) . . . . ?
C30 O28 C27 C24 -172.4(4) . . . . ?
C32 N31 C39 C20 -165.6(2) . . . . ?
C32 N31 C39 C38 5.3(3) . . . . ?
C32 C33 C34 C35 -177.8(3) . . . . ?
C32 C33 C38 C37 -179.3(2) . . . . ?
C32 C33 C38 C39 0.1(3) . . . . ?
C32 C40 C41 C42 -108.0(3) . . . . ?
C32 C40 C41 C46 70.4(3) . . . . ?
C32 C40 C62 N61 11.6(4) . . . . ?
C32 C40 C62 C63 -172.1(3) . . . . ?
C33 C32 C40 C41 6.2(4) . . . . ?
C33 C32 C40 C62 -172.7(3) . . . . ?
C33 C34 C35 C36 -3.0(4) . . . . ?
C33 C38 C39 N31 -3.3(3) . . . . ?
C33 C38 C39 C20 167.6(2) . . . . ?
C34 C33 C38 C37 0.1(4) . . . . ?
C34 C33 C38 C39 179.6(2) . . . . ?
C34 C35 C36 C37 -0.1(4) . . . . ?
C35 C36 C37 C38 3.2(4) . . . . ?
C36 C37 C38 C33 -3.2(4) . . . . ?
C36 C37 C38 C39 177.6(3) . . . . ?
C37 C38 C39 N31 176.0(3) . . . . ?
C37 C38 C39 C20 -13.1(5) . . . . ?
C38 C33 C34 C35 2.9(4) . . . . ?
C39 N31 C32 C33 -5.2(3) . . . . ?
C39 N31 C32 C40 169.6(2) . . . . ?
C39 C20 C21 C22 -70.5(3) . . . . ?
C39 C20 C21 C26 109.3(3) . . . . ?
C40 C32 C33 C34 9.0(5) . . . . ?
C40 C32 C33 C38 -171.6(2) . . . . ?
C40 C41 C42 C43 177.9(2) . . . . ?
C40 C41 C46 C45 -177.0(2) . . . . ?
C40 C62 C63 C64 12.2(5) . . . . ?
C40 C62 C63 C68 -174.1(3) . . . . ?
C41 C40 C62 N61 -167.3(2) . . . . ?
C41 C40 C62 C63 9.0(4) . . . . ?
C41 C42 C43 C44 -0.5(4) . . . . ?
C41 C42 C43 C47 179.1(3) . . . . ?
C42 C41 C46 C45 1.3(4) . . . . ?
C42 C43 C44 C45 0.5(4) . . . . ?
C42 C43 C47 C48 60.3(4) . . . . ?
C42 C43 C47 C49 -60.8(4) . . . . ?
C42 C43 C47 C50 179.2(3) . . . . ?
C43 C44 C45 C46 0.3(4) . . . . ?
C43 C44 C45 C51 -177.1(3) . . . . ?
C44 C43 C47 C48 -120.2(3) . . . . ?
C44 C43 C47 C49 118.7(3) . . . . ?
C44 C43 C47 C50 -1.3(4) . . . . ?
C44 C45 C46 C41 -1.2(4) . . . . ?
C44 C45 C51 C52 -123.4(3) . . . . ?
C44 C45 C51 C53 116.0(3) . . . . ?
C44 C45 C51 C54 -2.0(4) . . . . ?
C46 C41 C42 C43 -0.4(4) . . . . ?
C46 C45 C51 C52 59.2(4) . . . . ?
C46 C45 C51 C53 -61.4(4) . . . . ?
C46 C45 C51 C54 -179.4(3) . . . . ?
C47 C43 C44 C45 -179.0(3) . . . . ?
C51 C45 C46 C41 176.3(3) . . . . ?
C62 N61 C69 C68 5.3(3) . . . . ?
C62 N61 C69 C70 -173.0(3) . . . . ?
C62 C40 C41 C42 71.1(3) . . . . ?
C62 C40 C41 C46 -110.6(3) . . . . ?
C62 C63 C64 C65 172.1(3) . . . . ?
C62 C63 C68 C67 -173.2(3) . . . . ?
C62 C63 C68 C69 0.4(3) . . . . ?
C63 C64 C65 C66 -0.3(5) . . . . ?
C63 C68 C69 N61 -3.3(3) . . . . ?
C63 C68 C69 C70 174.9(3) . . . . ?
C64 C63 C68 C67 1.5(4) . . . . ?
C64 C63 C68 C69 175.1(3) . . . . ?
C64 C65 C66 C67 1.1(5) . . . . ?
C65 C66 C67 C68 -0.5(5) . . . . ?
C66 C67 C68 C63 -0.7(4) . . . . ?
C66 C67 C68 C69 -172.5(3) . . . . ?
C67 C68 C69 N61 169.2(3) . . . . ?
C67 C68 C69 C70 -12.6(5) . . . . ?
C68 C63 C64 C65 -1.0(4) . . . . ?
C68 C69 C70 C71 -19.6(4) . . . . ?
C68 C69 C70 C82 162.0(3) . . . . ?
C69 N61 C62 C40 171.9(3) . . . . ?
C69 N61 C62 C63 -5.1(3) . . . . ?
C69 C70 C71 C72 116.6(3) . . . . ?
C69 C70 C71 C76 -64.5(4) . . . . ?
C69 C70 C82 N81 -13.8(4) . . . . ?
C69 C70 C82 C83 172.7(3) . . . . ?
C70 C71 C72 C73 177.5(3) . . . . ?
C70 C71 C76 C75 -177.7(3) . . . . ?
C70 C82 C83 C84 -17.1(5) . . . . ?
C70 C82 C83 C88 167.6(2) . . . . ?
C71 C70 C82 N81 167.9(2) . . . . ?
C71 C70 C82 C83 -5.7(4) . . . . ?
C71 C72 C73 C74 -0.2(4) . . . . ?
C72 C71 C76 C75 1.2(4) . . . . ?
C72 C73 C74 C75 2.1(4) . . . . ?
C72 C73 C74 C77 -176.4(3) . . . . ?
C73 C74 C75 C76 -2.3(5) . . . . ?
C73 C74 C77 O78 -179.5(4) . . . . ?
C73 C74 C77 O79 1.5(5) . . . . ?
C74 C75 C76 C71 0.6(5) . . . . ?
C75 C74 C77 O78 2.0(6) . . . . ?
C75 C74 C77 O79 -176.9(3) . . . . ?
C76 C71 C72 C73 -1.4(4) . . . . ?
C77 C74 C75 C76 176.3(3) . . . . ?
C80 O79 C77 O78 -5.7(5) . . . . ?
C80 O79 C77 C74 173.3(3) . . . . ?
C82 N81 C89 C88 -3.8(3) . . . . ?
C82 N81 C89 C90 176.9(2) . . . . ?
C82 C70 C71 C72 -64.9(4) . . . . ?
C82 C70 C71 C76 114.1(3) . . . . ?
C82 C83 C84 C85 -177.2(3) . . . . ?
C82 C83 C88 C87 179.0(2) . . . . ?
C82 C83 C88 C89 4.1(3) . . . . ?
C83 C84 C85 C86 -0.4(4) . . . . ?
C83 C88 C89 N81 -0.4(3) . . . . ?
C83 C88 C89 C90 178.9(2) . . . . ?
C84 C83 C88 C87 2.9(4) . . . . ?
C84 C83 C88 C89 -172.0(2) . . . . ?
C84 C85 C86 C87 2.7(4) . . . . ?
C85 C86 C87 C88 -2.1(4) . . . . ?
C86 C87 C88 C83 -0.6(4) . . . . ?
C86 C87 C88 C89 172.6(3) . . . . ?
C87 C88 C89 N81 -174.3(3) . . . . ?
C87 C88 C89 C90 4.9(5) . . . . ?
C88 C83 C84 C85 -2.4(4) . . . . ?
C88 C89 C90 C19 -161.2(2) . . . . ?
C88 C89 C90 C91 19.9(4) . . . . ?
C89 N81 C82 C70 -167.9(2) . . . . ?
C89 N81 C82 C83 6.5(3) . . . . ?
C89 C90 C91 C92 -110.2(3) . . . . ?
C89 C90 C91 C96 74.8(3) . . . . ?
C90 C91 C92 C93 -174.9(2) . . . . ?
C90 C91 C96 C95 172.9(2) . . . . ?
C91 C92 C93 C94 1.0(4) . . . . ?
C91 C92 C93 C97 179.7(3) . . . . ?
C92 C91 C96 C95 -2.2(4) . . . . ?
C92 C93 C94 C95 -0.2(5) . . . . ?
C92 C93 C97 C98 -1.9(4) . . . . ?
C92 C93 C97 C99 -121.6(4) . . . . ?
C92 C93 C97 C100 118.1(4) . . . . ?
C93 C94 C95 C96 -1.8(5) . . . . ?
C93 C94 C95 C101 173.6(3) . . . . ?
C94 C93 C97 C98 176.7(3) . . . . ?
C94 C93 C97 C99 57.1(5) . . . . ?
C94 C93 C97 C100 -63.3(4) . . . . ?
C94 C95 C96 C91 3.0(4) . . . . ?
C94 C95 C101 C102 -104.8(6) . . . . ?
C94 C95 C101 C103 16.4(5) . . . . ?
C94 C95 C101 C104 132.7(4) . . . . ?
C96 C91 C92 C93 0.2(4) . . . . ?
C96 C95 C101 C102 70.4(6) . . . . ?
C96 C95 C101 C103 -168.3(3) . . . . ?
C96 C95 C101 C104 -52.1(5) . . . . ?
C97 C93 C94 C95 -178.9(3) . . . . ?
C101 C95 C96 C91 -172.5(3) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
6.6988 4.1570 -3.6105 0.3437 -0.1233 0.9309
-6.6988 -4.1570 3.6105 -0.3437 0.1233 -0.9309
-0.0077 -11.4070 -11.6872 -0.8814 0.3107 0.3557
0.0077 11.4070 11.6872 0.8814 -0.3107 -0.3557
0.2233 12.0899 -11.1924 -0.3119 -0.8843 0.3475
-0.2233 -12.0899 11.1924 0.3119 0.8843 -0.3475
6.5755 -3.2406 -5.3340 0.0773 0.2143 0.9737
-6.5755 3.2406 5.3340 -0.0773 -0.2143 -0.9737
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.143 0.140 0.807 123.6 34.9 '0.8 CH2Cl2'
2 -0.143 0.360 0.307 123.6 34.9 '0.8 CH2Cl2'
3 0.143 0.640 0.693 123.6 34.6 '0.8 CH2Cl2'
4 0.143 0.860 0.193 123.6 34.6 '0.8 CH2Cl2'
5 0.261 0.529 0.233 17.3 1.3 ?
6 0.261 0.971 0.733 17.3 1.3 ?
7 0.739 0.029 0.267 17.3 1.3 ?
8 0.739 0.471 0.767 17.3 1.3 ?
