#------------------------------------------------------------------------------
#$Date: 2020-07-31 02:44:12 +0300 (Fri, 31 Jul 2020) $
#$Revision: 254687 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/86/1558695.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_1558695
loop_
_publ_author_name
'Chen, Xi'
'Spiering, Glenn A.'
'Slebodnick, Carla'
'Long, Timothy E.'
'Moore, Robert B.'
_publ_section_title
;
 Deciphering the 3D Microstructures of a Doubly Charged Homopolymer
 through a Complementary Correlation of Monomer Crystallography and
 Polymer Powder X-ray Diffraction
;
_journal_name_full               Macromolecules
_journal_paper_doi               10.1021/acs.macromol.0c01270
_journal_year                    2020
_chemical_formula_moiety         '1.24(Br), 0.76(Cl), H2 O, C33 H58 N2'
_chemical_formula_sum            'C33 H60 Br1.24 Cl0.76 N2 O'
_chemical_formula_weight         626.86
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.864(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.70540(10)
_cell_length_b                   40.6996(9)
_cell_length_c                   12.4989(3)
_cell_measurement_reflns_used    14588
_cell_measurement_temperature    100.00(12)
_cell_measurement_theta_max      74.9640
_cell_measurement_theta_min      3.6800
_cell_volume                     3403.28(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53a (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      100.00(12)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -25.00  37.00   0.50    1.00    --  -42.55  19.00  60.00  124
  2  ω     -4.00  31.00   0.50    1.00    --  -42.55  38.00 -90.00   70
  3  ω    -43.00  -6.00   0.50    1.00    --  -42.55  38.00 -90.00   74
  4  ω    -54.00  31.00   0.50    1.00    --  -42.55  92.00 -26.00  170
  5  ω    -47.00 -16.00   0.50    4.00    --  -90.25  45.00   0.00   62
  6  ω    -74.00 -49.00   0.50    4.00    --  -90.25  92.00 -26.00   50
  7  ω    -51.00 -19.00   0.50    4.00    --  -90.25  45.00-180.00   64
  8  ω   -113.00 -86.00   0.50    1.00    --  -42.55 -77.00-180.00   54
  9  ω   -146.00-119.00   0.50    4.00    --  -90.25 -92.00-138.00   54
 10  ω   -116.00 -78.00   0.50    1.00    --  -42.55-125.00 -30.00   76
 11  ω   -116.00 -82.00   0.50    1.00    --  -42.55-125.00   0.00   68
 12  ω   -115.00 -89.00   0.50    1.00    --  -42.55 -77.00  90.00   52
 13  ω    -14.00  78.00   0.50    1.00    --   42.55 -92.00-138.00  184
 14  ω     85.00 115.00   0.50    1.00    --   42.55  77.00-120.00   60
 15  ω     99.00 138.00   0.50    4.00    --  111.75  92.00 -26.00   78
 16  ω    107.00 177.00   0.50    4.00    --  111.75  30.00  30.00  140
 17  ω    139.00 177.00   0.50    4.00    --  111.75  45.00   0.00   76
 18  ω    127.00 178.00   0.50    4.00    --  111.75  15.00 -30.00  102
 19  ω    130.00 178.00   0.50    4.00    --  111.75  15.00-120.00   96
 20  ω     84.00  94.00   0.50    4.00    --  111.75 -94.00-120.00   20
 21  ω     78.00  93.50   0.50    4.00    --  111.75 -92.00-138.00   31
 22  ω     40.00  71.00   0.50    4.00    --  111.75 -92.00-138.00   62
 23  ω     46.00 117.00   0.50    4.00    --  111.75-125.00-150.00  142
 24  ω     39.00  99.00   0.50    4.00    --  111.75 -77.00 -90.00  120
 25  ω     43.00 108.00   0.50    4.00    --  111.75-125.00-120.00  130
 26  ω     43.00 106.00   0.50    4.00    --  111.75-125.00 -60.00  126
 27  ω     38.00 109.00   0.50    4.00    --  111.75 -94.00 -30.00  142
 28  ω     41.00 116.00   0.50    4.00    --  111.75-125.00  90.00  150
 29  ω     58.00 116.00   0.50    4.00    --  111.75-125.00 150.00  116
 30  ω     39.00  66.00   0.50    4.00    --  111.75 -61.00   0.00   54
 31  ω     39.00 107.00   0.50    4.00    --  111.75 -94.00   0.00  136
 32  ω     38.00  72.00   0.50    4.00    --  111.75 -94.00-120.00   68
 33  ω     40.00 116.00   0.50    4.00    --  111.75-125.00-180.00  152
 34  ω     61.00 115.00   0.50    4.00    --  111.75  15.00 -30.00  108
 35  ω     91.00 126.00   0.50    4.00    --  111.75  45.00   0.00   70
 36  ω    100.00 178.00   0.50    4.00    --  111.75  45.00  90.00  156
 37  ω    143.00 169.00   0.50    4.00    --  111.75  30.00 120.00   52
 38  ω    107.00 135.00   0.50    4.00    --  111.75  30.00 120.00   56
 39  ω     38.00  71.00   0.50    4.00    --  111.75 -61.00  60.00   66
 40  ω     32.00  96.00   0.50    1.00    --   42.55-125.00  60.00  128
 41  ω     61.00 107.00   0.50    4.00    --  111.75  15.00-120.00   92
 42  ω     92.00 176.00   0.50    4.00    --  111.75 125.00-180.00  168
 43  ω     96.00 178.00   0.50    4.00    --  111.75 125.00-120.00  164
 44  ω    148.00 174.00   0.50    4.00    --  111.75  92.00 -26.00   52
 45  ω   -113.00 -85.00   0.50    1.00    --  -42.55-125.00-180.00   56
 46  ω   -116.00 -85.00   0.50    1.00    --  -42.55 -77.00 150.00   62
 47  ω     85.00 116.00   0.50    1.00    --   42.55  77.00  30.00   62
 48  ω    152.00 177.00   0.50    4.00    --  111.75  61.00  60.00   50
 49  ω    130.00 178.00   0.50    4.00    --  111.75  61.00  30.00   96
 50  ω    115.00 141.00   0.50    4.00    --  111.75 125.00  30.00   52
 51  ω     47.00  79.00   0.50    4.00    --  111.75-135.00  31.95   64
 52  ω    152.00 178.00   0.50    4.00    --  111.75 125.00  30.00   52
 53  ω     98.00 124.00   0.50    4.00    --  111.75-135.00  31.95   52
 54  ω     88.00 134.00   0.50    4.00    --  111.75  61.00  60.00   92
 55  ω     88.00 115.00   0.50    4.00    --  111.75  61.00  30.00   54
 56  ω    114.00 155.00   0.50    4.00    --  111.75  45.00  60.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1728522000
_diffrn_orient_matrix_UB_12      0.0046165000
_diffrn_orient_matrix_UB_13      0.0737897000
_diffrn_orient_matrix_UB_21      -0.0784441000
_diffrn_orient_matrix_UB_22      -0.0345962000
_diffrn_orient_matrix_UB_23      -0.0301192000
_diffrn_orient_matrix_UB_31      0.1302540000
_diffrn_orient_matrix_UB_32      -0.0146640000
_diffrn_orient_matrix_UB_33      0.0944012000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       51
_diffrn_reflns_limit_k_min       -51
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            49748
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.460
_diffrn_reflns_theta_min         3.707
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.707
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.512
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53a (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       plate
_exptl_crystal_F_000             1345
_exptl_crystal_recrystallization_method 'grown from CH3OH'
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.784
_refine_diff_density_min         -1.014
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         7161
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0511
_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)+(0.0595P)²+3.9605P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1354
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6189
_reflns_number_total             7161
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ma0c01270_si_002.cif
_cod_data_source_block           cs2557
_cod_database_code               1558695
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C33 H57 Br2 N2 H2 O'
_chemical_oxdiff_usercomment     'Xi Chen / TE Long (VBDC18BrCl)'
_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.
;
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{Br1, Cl1}
{Br2, Cl2}
3. Uiso/Uaniso restraints and constraints
Uanis(C9A) = Uanis(C9B)
Uanis(C13A) = Uanis(C13B)
Uanis(Br1) = Uanis(Cl1)
Uanis(Br2) = Uanis(Cl2)
4. Rigid body (RIGU) restrains
 C9A, C9B, C10A, C10B, C11A, C11B, C12A, C12B, C13A, C13B, C14A, C14B, C15A,
 C15B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=Sof(C11B)=Sof(C12B)=Sof(H12B)=Sof(C13B)=
 Sof(H13B)=Sof(C14B)=Sof(H14B)=Sof(C15B)=Sof(H15C)=Sof(H15D)=1-FVAR(1)
 Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=
 Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=Sof(H15B)=FVAR(1)
 Sof(Cl1)=1-FVAR(2)
 Sof(Br1)=FVAR(2)
 Sof(Cl2)=1-FVAR(3)
 Sof(Br2)=FVAR(3)
6.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B),
 C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B),
  C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,
 H29B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B)
6.b Aromatic/amide H refined with riding coordinates:
 C9A(H9A), C9B(H9B), C10A(H10A), C10B(H10B), C12A(H12A), C12B(H12B),
 C13A(H13A), C13B(H13B), C14A(H14A), C14B(H14B)
6.c X=CH2 refined with riding coordinates:
 C15A(H15A,H15B), C15B(H15C,H15D)
6.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C)
;
_olex2_date_sample_data_collection 2019-10-11
_olex2_date_sample_submission    2019-09-26
_olex2_exptl_crystal_mounting_method 'Nylon loop with Paratone Oil'
_olex2_submission_original_sample_id VBDC18BrCl
_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 1.874
_oxdiff_exptl_absorpt_empirical_full_min 0.488
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
Br1 Br 0.39232(6) 0.17261(2) 0.65956(3) 0.04459(16) Uani 0.594(4) 1 d . . P A 1
Br2 Br 0.41972(6) 0.29745(2) 0.72779(3) 0.04425(15) Uani 0.647(4) 1 d . . P B 1
Cl1 Cl 0.39232(6) 0.17261(2) 0.65956(3) 0.04459(16) Uani 0.406(4) 1 d . . P A 2
Cl2 Cl 0.41972(6) 0.29745(2) 0.72779(3) 0.04425(15) Uani 0.353(4) 1 d . . P B 2
O2 O 0.3361(4) 0.22879(8) 0.8438(2) 0.0613(7) Uani 1 1 d . . . . .
H2C H 0.377(7) 0.2136(11) 0.787(4) 0.074 Uiso 1 1 d R . . . .
H2D H 0.373(7) 0.2480(11) 0.798(4) 0.074 Uiso 1 1 d R . . . .
N1 N -0.1023(3) 0.23400(6) 1.07903(17) 0.0321(5) Uani 1 1 d . . . . .
N2 N -0.1288(3) 0.29519(5) 1.03043(17) 0.0300(5) Uani 1 1 d . . . . .
C1 C 0.0828(4) 0.24559(7) 1.0289(2) 0.0377(6) Uani 1 1 d . . . . .
H1A H 0.115551 0.230320 0.970995 0.045 Uiso 1 1 calc R . . . .
H1B H 0.196815 0.245912 1.083481 0.045 Uiso 1 1 calc R . . . .
C2 C 0.0482(4) 0.27986(7) 0.9833(2) 0.0338(6) Uani 1 1 d . . . . .
H2A H 0.168246 0.293563 1.000031 0.041 Uiso 1 1 calc R . . . .
H2B H 0.024751 0.278602 0.904344 0.041 Uiso 1 1 calc R . . . .
C3 C -0.1253(4) 0.25444(7) 1.1776(2) 0.0369(6) Uani 1 1 d . . . . .
H3A H -0.020941 0.248341 1.233879 0.044 Uiso 1 1 calc R . . . .
H3B H -0.257532 0.250198 1.205571 0.044 Uiso 1 1 calc R . . . .
C4 C -0.1066(4) 0.29075(7) 1.1504(2) 0.0343(6) Uani 1 1 d . . . . .
H4A H -0.211481 0.303419 1.184301 0.041 Uiso 1 1 calc R . . . .
H4B H 0.025339 0.299089 1.178522 0.041 Uiso 1 1 calc R . . . .
C5 C -0.2805(4) 0.24010(7) 1.0017(2) 0.0345(6) Uani 1 1 d . . . . .
H5A H -0.400399 0.229530 1.028428 0.041 Uiso 1 1 calc R . . . .
H5B H -0.256584 0.230439 0.930956 0.041 Uiso 1 1 calc R . . . .
C6 C -0.3150(4) 0.27701(7) 0.9900(2) 0.0323(5) Uani 1 1 d . . . . .
H6A H -0.348162 0.282529 0.913737 0.039 Uiso 1 1 calc R . . . .
H6B H -0.428722 0.283702 1.031649 0.039 Uiso 1 1 calc R . . . .
C7 C -0.0887(4) 0.19767(7) 1.1105(2) 0.0377(6) Uani 1 1 d . . . . .
H7A H 0.032642 0.194291 1.158822 0.045 Uiso 1 1 calc R . . . .
H7B H -0.205908 0.191934 1.150829 0.045 Uiso 1 1 calc R . . . .
C8 C -0.0812(5) 0.17480(7) 1.0160(2) 0.0394(6) Uani 1 1 d . . . . .
C9A C 0.1164(11) 0.1656(3) 0.9785(9) 0.0369(14) Uani 0.677(11) 1 d . U P C 1
H9A H 0.234985 0.173671 1.015123 0.044 Uiso 0.677(11) 1 calc R . P C 1
C9B C 0.062(3) 0.1678(7) 0.973(2) 0.0369(14) Uani 0.323(11) 1 d . U P C 2
H9B H 0.188775 0.176100 0.998830 0.044 Uiso 0.323(11) 1 calc R . P C 2
C10A C 0.1290(10) 0.14566(14) 0.8924(5) 0.0350(12) Uani 0.677(11) 1 d . U P C 1
H10A H 0.257103 0.140194 0.869513 0.042 Uiso 0.677(11) 1 calc R . P C 1
C10B C 0.043(3) 0.1454(3) 0.8766(12) 0.041(3) Uani 0.323(11) 1 d . U P C 2
H10B H 0.157412 0.139702 0.839633 0.049 Uiso 0.323(11) 1 calc R . P C 2
C11A C -0.0415(12) 0.13288(14) 0.8360(4) 0.0341(12) Uani 0.677(11) 1 d . U P C
1
C11B C -0.141(3) 0.1334(3) 0.8434(10) 0.039(3) Uani 0.323(11) 1 d . U P C 2
C12A C -0.2282(11) 0.14089(15) 0.8724(5) 0.0379(14) Uani 0.677(11) 1 d . U P C
1
H12A H -0.346449 0.132406 0.836404 0.046 Uiso 0.677(11) 1 calc R . P C 1
C12B C -0.305(2) 0.1416(3) 0.8977(12) 0.041(3) Uani 0.323(11) 1 d . U P C 2
H12B H -0.430993 0.132532 0.874952 0.050 Uiso 0.323(11) 1 calc R . P C 2
C13A C -0.2412(10) 0.16109(17) 0.9604(6) 0.0380(12) Uani 0.677(11) 1 d . U P C
1
H13A H -0.370341 0.165693 0.983550 0.046 Uiso 0.677(11) 1 calc R . P C 1
C13B C -0.291(2) 0.1629(4) 0.9858(14) 0.0380(12) Uani 0.323(11) 1 d . U P C 2
H13B H -0.403228 0.169240 1.023293 0.046 Uiso 0.323(11) 1 calc R . P C 2
C14A C -0.0182(9) 0.11156(13) 0.7435(4) 0.0419(14) Uani 0.677(11) 1 d . U P C 1
H14A H 0.114278 0.107015 0.725173 0.050 Uiso 0.677(11) 1 calc R . P C 1
C14B C -0.169(3) 0.1108(3) 0.7499(9) 0.059(4) Uani 0.323(11) 1 d . U P C 2
H14B H -0.302860 0.104280 0.731158 0.070 Uiso 0.323(11) 1 calc R . P C 2
C15A C -0.1677(12) 0.09790(15) 0.6823(5) 0.0521(16) Uani 0.677(11) 1 d . U P C
1
H15A H -0.302435 0.101798 0.697704 0.063 Uiso 0.677(11) 1 calc R . P C 1
H15B H -0.138893 0.084316 0.623443 0.063 Uiso 0.677(11) 1 calc R . P C 1
C15B C -0.038(4) 0.0993(4) 0.6925(14) 0.069(4) Uani 0.323(11) 1 d . U P C 2
H15C H 0.098207 0.104843 0.707032 0.083 Uiso 0.323(11) 1 calc R . P C 2
H15D H -0.076790 0.084972 0.634594 0.083 Uiso 0.323(11) 1 calc R . P C 2
C16 C -0.1443(4) 0.33158(7) 1.0054(2) 0.0346(6) Uani 1 1 d . . . . .
H16A H -0.035033 0.343207 1.046976 0.041 Uiso 1 1 calc R . . . .
H16B H -0.272470 0.339913 1.029585 0.041 Uiso 1 1 calc R . . . .
C17 C -0.1333(4) 0.33990(7) 0.8873(2) 0.0348(6) Uani 1 1 d . . . . .
H17A H -0.223683 0.325319 0.843118 0.042 Uiso 1 1 calc R . . . .
H17B H 0.004695 0.336540 0.865845 0.042 Uiso 1 1 calc R . . . .
C18 C -0.1948(5) 0.37565(7) 0.8694(2) 0.0392(6) Uani 1 1 d . . . . .
H18A H -0.115373 0.389563 0.921372 0.047 Uiso 1 1 calc R . . . .
H18B H -0.337182 0.378041 0.884316 0.047 Uiso 1 1 calc R . . . .
C19 C -0.1671(4) 0.38831(7) 0.7564(2) 0.0368(6) Uani 1 1 d . . . . .
H19A H -0.229811 0.410260 0.748246 0.044 Uiso 1 1 calc R . . . .
H19B H -0.237695 0.373396 0.703999 0.044 Uiso 1 1 calc R . . . .
C20 C 0.0514(4) 0.39090(7) 0.7300(2) 0.0350(6) Uani 1 1 d . . . . .
H20A H 0.129052 0.401119 0.791481 0.042 Uiso 1 1 calc R . . . .
H20B H 0.104962 0.368502 0.720467 0.042 Uiso 1 1 calc R . . . .
C21 C 0.0815(4) 0.41096(7) 0.6293(2) 0.0343(6) Uani 1 1 d . . . . .
H21A H 0.010472 0.400091 0.566896 0.041 Uiso 1 1 calc R . . . .
H21B H 0.021971 0.433016 0.637031 0.041 Uiso 1 1 calc R . . . .
C22 C 0.3013(4) 0.41472(7) 0.6080(2) 0.0354(6) Uani 1 1 d . . . . .
H22A H 0.358797 0.392661 0.597177 0.042 Uiso 1 1 calc R . . . .
H22B H 0.373073 0.424554 0.671983 0.042 Uiso 1 1 calc R . . . .
C23 C 0.3366(4) 0.43606(7) 0.5102(2) 0.0350(6) Uani 1 1 d . . . . .
H23A H 0.275651 0.425181 0.445095 0.042 Uiso 1 1 calc R . . . .
H23B H 0.268702 0.457446 0.517818 0.042 Uiso 1 1 calc R . . . .
C24 C 0.5570(4) 0.44213(7) 0.4957(2) 0.0336(5) Uani 1 1 d . . . . .
H24A H 0.625468 0.420687 0.490884 0.040 Uiso 1 1 calc R . . . .
H24B H 0.616492 0.453663 0.559875 0.040 Uiso 1 1 calc R . . . .
C25 C 0.5953(4) 0.46238(7) 0.3964(2) 0.0351(6) Uani 1 1 d . . . . .
H25A H 0.538807 0.450600 0.331963 0.042 Uiso 1 1 calc R . . . .
H25B H 0.524364 0.483633 0.400282 0.042 Uiso 1 1 calc R . . . .
C26 C 0.8157(4) 0.46898(7) 0.3840(2) 0.0336(5) Uani 1 1 d . . . . .
H26A H 0.887470 0.447735 0.382873 0.040 Uiso 1 1 calc R . . . .
H26B H 0.870961 0.481484 0.447168 0.040 Uiso 1 1 calc R . . . .
C27 C 0.8549(4) 0.48810(7) 0.2828(2) 0.0349(6) Uani 1 1 d . . . . .
H27A H 0.787432 0.509700 0.285283 0.042 Uiso 1 1 calc R . . . .
H27B H 0.795018 0.476021 0.219829 0.042 Uiso 1 1 calc R . . . .
C28 C 1.0766(4) 0.49365(7) 0.2680(2) 0.0349(6) Uani 1 1 d . . . . .
H28A H 1.136325 0.505734 0.331035 0.042 Uiso 1 1 calc R . . . .
H28B H 1.143970 0.472042 0.265712 0.042 Uiso 1 1 calc R . . . .
C29 C 1.1167(4) 0.51269(7) 0.1671(2) 0.0366(6) Uani 1 1 d . . . . .
H29A H 1.042285 0.533705 0.167024 0.044 Uiso 1 1 calc R . . . .
H29B H 1.065194 0.499906 0.103755 0.044 Uiso 1 1 calc R . . . .
C30 C 1.3377(4) 0.51997(7) 0.1570(2) 0.0346(6) Uani 1 1 d . . . . .
H30A H 1.410828 0.498895 0.154155 0.041 Uiso 1 1 calc R . . . .
H30B H 1.390251 0.531848 0.222065 0.041 Uiso 1 1 calc R . . . .
C31 C 1.3804(4) 0.54033(7) 0.0586(2) 0.0382(6) Uani 1 1 d . . . . .
H31A H 1.340073 0.527583 -0.006739 0.046 Uiso 1 1 calc R . . . .
H31B H 1.298098 0.560533 0.057772 0.046 Uiso 1 1 calc R . . . .
C32 C 1.5993(5) 0.54990(8) 0.0558(2) 0.0473(7) Uani 1 1 d . . . . .
H32A H 1.641084 0.561476 0.123263 0.057 Uiso 1 1 calc R . . . .
H32B H 1.680319 0.529619 0.053007 0.057 Uiso 1 1 calc R . . . .
C33 C 1.6453(6) 0.57167(9) -0.0379(3) 0.0580(9) Uani 1 1 d . . . . .
H33A H 1.606401 0.560346 -0.105343 0.087 Uiso 1 1 calc GR . . . .
H33B H 1.788780 0.576452 -0.034611 0.087 Uiso 1 1 calc GR . . . .
H33C H 1.570285 0.592262 -0.034403 0.087 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'
Br Br -0.6763 1.2805 '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
0 1 0 0.0145
0 -1 0 0.0165
0 1 1 0.0322
-4 -3 -2 0.0864
4 3 2 0.0964
1 -5 -4 0.0292
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
C1 N1 C5 108.8(2) . . ?
C1 N1 C7 111.9(2) . . ?
C3 N1 C1 107.5(2) . . ?
C3 N1 C5 108.3(2) . . ?
C3 N1 C7 109.4(2) . . ?
C5 N1 C7 110.8(2) . . ?
C2 N2 C4 108.3(2) . . ?
C2 N2 C6 108.9(2) . . ?
C2 N2 C16 111.8(2) . . ?
C4 N2 C6 107.35(19) . . ?
C4 N2 C16 108.9(2) . . ?
C6 N2 C16 111.5(2) . . ?
N1 C1 C2 109.6(2) . . ?
N2 C2 C1 109.9(2) . . ?
N1 C3 C4 109.8(2) . . ?
N2 C4 C3 109.5(2) . . ?
N1 C5 C6 109.4(2) . . ?
N2 C6 C5 109.5(2) . . ?
C8 C7 N1 113.6(2) . . ?
C7 C8 C13B 108.3(6) . . ?
C9A C8 C7 118.8(5) . . ?
C9B C8 C7 125.6(14) . . ?
C9B C8 C13B 126.1(14) . . ?
C13A C8 C7 126.0(4) . . ?
C13A C8 C9A 115.2(5) . . ?
C10A C9A C8 120.5(7) . . ?
C8 C9B C10B 119.1(18) . . ?
C9A C10A C11A 121.9(5) . . ?
C11B C10B C9B 119.0(13) . . ?
C10A C11A C14A 119.4(5) . . ?
C12A C11A C10A 117.9(5) . . ?
C12A C11A C14A 122.8(6) . . ?
C10B C11B C12B 120.0(12) . . ?
C10B C11B C14B 121.7(16) . . ?
C12B C11B C14B 118.4(15) . . ?
C13A C12A C11A 120.2(5) . . ?
C11B C12B C13B 121.9(13) . . ?
C8 C13A C12A 124.2(5) . . ?
C12B C13B C8 114.0(10) . . ?
C15A C14A C11A 125.6(6) . . ?
C15B C14B C11B 128.4(19) . . ?
N2 C16 C17 114.3(2) . . ?
C16 C17 C18 109.0(2) . . ?
C17 C18 C19 114.2(2) . . ?
C18 C19 C20 113.7(2) . . ?
C21 C20 C19 113.4(2) . . ?
C22 C21 C20 112.4(2) . . ?
C21 C22 C23 113.6(2) . . ?
C24 C23 C22 113.0(2) . . ?
C23 C24 C25 113.8(2) . . ?
C26 C25 C24 113.3(2) . . ?
C25 C26 C27 113.5(2) . . ?
C26 C27 C28 113.6(2) . . ?
C29 C28 C27 113.8(2) . . ?
C28 C29 C30 113.3(2) . . ?
C29 C30 C31 114.1(2) . . ?
C32 C31 C30 113.1(2) . . ?
C33 C32 C31 114.5(3) . . ?
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
N1 C1 1.503(3) . ?
N1 C3 1.503(3) . ?
N1 C5 1.506(3) . ?
N1 C7 1.531(3) . ?
N2 C2 1.497(3) . ?
N2 C4 1.507(3) . ?
N2 C6 1.509(3) . ?
N2 C16 1.516(3) . ?
C1 C2 1.518(4) . ?
C3 C4 1.523(4) . ?
C5 C6 1.525(4) . ?
C7 C8 1.507(4) . ?
C8 C9A 1.483(8) . ?
C8 C9B 1.16(2) . ?
C8 C13A 1.358(8) . ?
C8 C13B 1.511(17) . ?
C9A C10A 1.354(13) . ?
C9B C10B 1.51(3) . ?
C10A C11A 1.402(7) . ?
C10B C11B 1.364(19) . ?
C11A C12A 1.399(8) . ?
C11A C14A 1.463(8) . ?
C11B C12B 1.371(19) . ?
C11B C14B 1.487(18) . ?
C12A C13A 1.381(9) . ?
C12B C13B 1.40(2) . ?
C14A C15A 1.340(10) . ?
C14B C15B 1.26(3) . ?
C16 C17 1.520(4) . ?
C17 C18 1.525(4) . ?
C18 C19 1.526(4) . ?
C19 C20 1.527(4) . ?
C20 C21 1.526(4) . ?
C21 C22 1.523(4) . ?
C22 C23 1.530(4) . ?
C23 C24 1.521(4) . ?
C24 C25 1.526(4) . ?
C25 C26 1.521(4) . ?
C26 C27 1.523(4) . ?
C27 C28 1.527(4) . ?
C28 C29 1.520(4) . ?
C29 C30 1.525(4) . ?
C30 C31 1.526(4) . ?
C31 C32 1.522(4) . ?
C32 C33 1.516(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2C Br1 0.99(5) 2.32(5) 3.285(3) 165(4) . yes
O2 H2C Cl1 0.99(5) 2.32(5) 3.285(3) 165(4) . yes
O2 H2D Br2 1.01(5) 2.23(5) 3.215(3) 166(4) . yes
O2 H2D Cl2 1.01(5) 2.23(5) 3.215(3) 166(4) . yes
C1 H1A O2 0.99 2.24 3.039(4) 136.5 . yes
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
N1 C1 C2 N2 17.2(3) . . . . ?
N1 C3 C4 N2 15.7(3) . . . . ?
N1 C5 C6 N2 17.5(3) . . . . ?
N1 C7 C8 C9A 90.7(6) . . . . ?
N1 C7 C8 C9B 84.0(17) . . . . ?
N1 C7 C8 C13A -90.0(5) . . . . ?
N1 C7 C8 C13B -95.5(8) . . . . ?
N2 C16 C17 C18 168.0(2) . . . . ?
C1 N1 C3 C4 49.5(3) . . . . ?
C1 N1 C5 C6 -68.2(3) . . . . ?
C1 N1 C7 C8 -65.4(3) . . . . ?
C2 N2 C4 C3 -67.5(3) . . . . ?
C2 N2 C6 C5 47.7(3) . . . . ?
C2 N2 C16 C17 50.9(3) . . . . ?
C3 N1 C1 C2 -68.9(3) . . . . ?
C3 N1 C5 C6 48.4(3) . . . . ?
C3 N1 C7 C8 175.6(2) . . . . ?
C4 N2 C2 C1 48.4(3) . . . . ?
C4 N2 C6 C5 -69.4(3) . . . . ?
C4 N2 C16 C17 170.5(2) . . . . ?
C5 N1 C1 C2 48.2(3) . . . . ?
C5 N1 C3 C4 -67.9(3) . . . . ?
C5 N1 C7 C8 56.2(3) . . . . ?
C6 N2 C2 C1 -68.0(3) . . . . ?
C6 N2 C4 C3 49.9(3) . . . . ?
C6 N2 C16 C17 -71.2(3) . . . . ?
C7 N1 C1 C2 170.9(2) . . . . ?
C7 N1 C3 C4 171.3(2) . . . . ?
C7 N1 C5 C6 168.4(2) . . . . ?
C7 C8 C9A C10A -178.5(7) . . . . ?
C7 C8 C9B C10B -177.9(12) . . . . ?
C7 C8 C13A C12A 178.3(5) . . . . ?
C7 C8 C13B C12B 179.3(11) . . . . ?
C8 C9A C10A C11A -0.4(13) . . . . ?
C8 C9B C10B C11B -1(3) . . . . ?
C9A C8 C13A C12A -2.4(9) . . . . ?
C9A C10A C11A C12A -1.0(10) . . . . ?
C9A C10A C11A C14A 179.9(7) . . . . ?
C9B C8 C13B C12B 0(2) . . . . ?
C9B C10B C11B C12B 0(2) . . . . ?
C9B C10B C11B C14B -179.1(15) . . . . ?
C10A C11A C12A C13A 0.7(8) . . . . ?
C10A C11A C14A C15A -179.6(5) . . . . ?
C10B C11B C12B C13B 2(2) . . . . ?
C10B C11B C14B C15B 2.0(19) . . . . ?
C11A C12A C13A C8 1.1(10) . . . . ?
C11B C12B C13B C8 -2(2) . . . . ?
C12A C11A C14A C15A 1.3(8) . . . . ?
C12B C11B C14B C15B -176.8(13) . . . . ?
C13A C8 C9A C10A 2.1(12) . . . . ?
C13B C8 C9B C10B 2(3) . . . . ?
C14A C11A C12A C13A 179.9(5) . . . . ?
C14B C11B C12B C13B -179.4(12) . . . . ?
C16 N2 C2 C1 168.4(2) . . . . ?
C16 N2 C4 C3 170.7(2) . . . . ?
C16 N2 C6 C5 171.5(2) . . . . ?
C16 C17 C18 C19 173.3(2) . . . . ?
C17 C18 C19 C20 -67.4(3) . . . . ?
C18 C19 C20 C21 -166.1(2) . . . . ?
C19 C20 C21 C22 176.9(2) . . . . ?
C20 C21 C22 C23 -177.4(2) . . . . ?
C21 C22 C23 C24 174.8(2) . . . . ?
C22 C23 C24 C25 178.0(2) . . . . ?
C23 C24 C25 C26 178.7(2) . . . . ?
C24 C25 C26 C27 177.9(2) . . . . ?
C25 C26 C27 C28 -177.8(2) . . . . ?
C26 C27 C28 C29 179.9(2) . . . . ?
C27 C28 C29 C30 176.3(2) . . . . ?
C28 C29 C30 C31 -177.6(2) . . . . ?
C29 C30 C31 C32 174.7(3) . . . . ?
C30 C31 C32 C33 -176.9(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
0.0000 1.0002 0.0003 0.0046 -0.0346 -0.0146
-0.0000 -1.0002 -0.0003 -0.0046 0.0346 0.0146
0.0002 0.9983 1.0001 0.0784 -0.0647 0.0798
-4.0006 -2.9908 -1.9969 0.5304 0.4774 -0.6657
4.0006 2.9908 1.9969 -0.5304 -0.4774 0.6657
0.9994 -4.9950 -4.0018 -0.4911 0.2149 -0.1744
