#------------------------------------------------------------------------------
#$Date: 2022-04-15 03:40:53 +0300 (Fri, 15 Apr 2022) $
#$Revision: 274544 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/86/7158639.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_7158639
loop_
_publ_author_name
'Glavaš, Mladena'
'Gredičak, Matija'
'Stefanic, Zoran'
'Jerić, Ivanka'
_publ_section_title
;
 Synthesis of 14-membered enediyne-embedded macrocycles
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00090C
_journal_year                    2022
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C39 H42 N2 O4'
_chemical_formula_sum            'C39 H42 N2 O4'
_chemical_formula_weight         602.74
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-25 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                91.779(2)
_cell_angle_beta                 96.053(3)
_cell_angle_gamma                91.867(3)
_cell_formula_units_Z            2
_cell_length_a                   11.4922(4)
_cell_length_b                   11.9793(4)
_cell_length_c                   12.3100(4)
_cell_measurement_reflns_used    12663
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.8530
_cell_measurement_theta_min      3.8800
_cell_volume                     1683.34(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     10.00  36.00   1.00    1.50    --   42.00  71.00  -5.19   26
  2  ω     58.00 118.00   1.00    1.50    --   42.00  71.00  -5.19   60
  3  ω     94.00 147.00   1.00    1.50    --   74.00  73.00  26.04   53
  4  ω    109.00 145.00   1.00    1.50    --   66.00  77.00  90.42   36
  5  ω    130.00 171.00   1.00    7.50    --  111.00  77.00  30.00   41
  6  ω    146.00 173.00   1.00    7.50    --  111.00 112.00  30.00   27
  7  ω    120.00 177.00   1.00    7.50    --  111.00  77.00   0.00   57
  8  ω    147.00 175.00   1.00    7.50    --  111.00  77.00-120.00   28
  9  ω    122.00 178.00   1.00    7.50    --  111.00  77.00 -90.00   56
 10  ω    106.00 133.00   1.00    7.50    --  111.00 112.00  30.00   27
 11  ω    115.00 173.00   1.00    7.50    --  111.00  77.00  90.00   58
 12  ω    132.00 178.00   1.00    7.50    --  111.00  61.00 150.00   46
 13  ω    126.00 151.00   1.00    7.50    --  111.00  77.00 150.00   25
 14  ω    115.00 141.00   1.00    7.50    --  111.00  61.00  90.00   26
 15  ω     88.00 146.00   1.00    1.50    --   70.00  75.00  71.40   58
 16  ω     86.00 141.00   1.00    7.50    --  111.00  61.00  30.00   55
 17  ω     83.00 133.00   1.00    7.50    --  111.00  61.00   0.00   50
 18  ω     82.00 144.00   1.00    7.50    --  111.00  61.00 -60.00   62
 19  ω     77.00 103.00   1.00    7.50    --  111.00  77.00  30.00   26
 20  ω     81.00 107.00   1.00    7.50    --  111.00  61.00  60.00   26
 21  ω     81.00 107.00   1.00    7.50    --  111.00  61.00  90.00   26
 22  ω     81.00 136.00   1.00    7.50    --  111.00  61.00 120.00   55
 23  ω     82.00 107.00   1.00    7.50    --  111.00  61.00 150.00   25
 24  ω     78.00 106.00   1.00    7.50    --  111.00  77.00  90.00   28
 25  ω     78.00 178.00   1.00    7.50    --  111.00  77.00 120.00  100
 26  ω     77.00 174.00   1.00    7.50    --  111.00  77.00  60.00   97
 27  ω     83.00 154.00   1.00    7.50    --  111.00  61.00-120.00   71
 28  ω     82.00 169.00   1.00    7.50    --  111.00  61.00-180.00   87
 29  ω     77.00 113.00   1.00    7.50    --  111.00  77.00-180.00   36
 30  ω     81.00 144.00   1.00    7.50    --  111.00  61.00-150.00   63
 31  ω     77.00 103.00   1.00    7.50    --  111.00  77.00-120.00   26
 32  ω     81.00 152.00   1.00    7.50    --  111.00  61.00 -90.00   71
 33  ω     77.00 103.00   1.00    7.50    --  111.00  77.00   0.00   26
 34  ω     78.00 174.00   1.00    7.50    --  111.00  77.00 -30.00   96
 35  ω     77.00 116.00   1.00    7.50    --  111.00  77.00 150.00   39
 36  ω     37.00  71.00   1.00    1.50    --   70.00  75.00  71.40   34
 37  ω     41.00  68.00   1.00    1.50    --   74.00  73.00  26.04   27
 38  ω     45.00  70.00   1.00    7.50    --   78.00  75.00  -7.25   25
 39  ω     38.00  79.00   1.00    1.50    --   70.00  77.00 -55.78   41
 40  ω     77.00 102.00   1.00    7.50    --  111.00  77.00 -90.00   25
 41  ω     77.00 159.00   1.00    7.50    --  111.00  77.00 -60.00   82
 42  ω     77.00 157.00   1.00    7.50    --  111.00  77.00-150.00   80
 43  ω    120.00 145.00   1.00    7.50    --  111.00 -77.00-150.00   25
 44  ω     81.00 109.00   1.00    7.50    --  111.00-112.00 -90.00   28
 45  ω     52.00  78.00   1.00    7.50    --  111.00-112.00 -90.00   26
 46  ω     40.00  78.00   1.00    7.50    --  111.00 -77.00-150.00   38
 47  ω     35.00 111.00   1.00    7.50    --  111.00-112.00-150.00   76
 48  ω     40.00 115.00   1.00    7.50    --  111.00-112.00 -30.00   75
 49  ω     38.00  63.00   1.00    7.50    --  111.00-112.00 120.00   25
 50  ω     82.00 115.00   1.00    7.50    --  111.00-112.00 120.00   33
 51  ω     38.00  85.00   1.00    7.50    --  111.00 -95.00 150.00   47
 52  ω     37.00 130.00   1.00    7.50    --  111.00 -61.00   0.00   93
 53  ω     35.00  72.00   1.00    1.50    --   66.00  77.00  90.42   37
 54  ω     32.00  76.00   1.00    1.50    --   66.00  77.00 137.41   44
 55  ω     19.00  44.00   1.00    1.50    --   54.00  81.00  90.32   25
 56  ω      9.00  42.00   1.00    1.50    --   42.00  79.00 130.61   33
 57  ω     10.00  35.00   1.00    1.50    --   46.00  84.00  39.32   25
 58  ω     19.00  44.00   1.00    1.50    --   54.00  82.00   3.06   25
 59  ω     29.00  54.00   1.00    1.50    --   62.00  75.00 -67.86   25
 60  ω     27.00  55.00   1.00    1.50    --   58.00  76.00-107.11   28
 61  ω     29.00  71.00   1.00    1.50    --   62.00  76.00-145.21   42
 62  ω     33.00  65.00   1.00    1.50    --   66.00  75.00-170.54   32
 63  ω      3.00  28.00   1.00    1.50    --   42.00  91.00-155.60   25
 64  ω    -71.00 -33.00   1.00    1.50    --  -40.62 -38.00   0.00   38
 65  ω    -65.00  34.00   1.00    1.50    --  -40.62  38.00 150.00   99
 66  ω      4.00  81.00   1.00    1.50    --   40.62-126.00  60.00   77
 67  ω     33.00 109.00   1.00    7.50    --  111.00 -95.00   0.00   76
 68  ω      6.00  99.00   1.00    1.50    --   40.62-126.00-120.00   93
 69  ω   -116.00 -91.00   1.00    1.50    --  -40.62 -38.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0488169000
_diffrn_orient_matrix_UB_12      0.0811690000
_diffrn_orient_matrix_UB_13      0.0946248000
_diffrn_orient_matrix_UB_21      0.0291430000
_diffrn_orient_matrix_UB_22      0.0875807000
_diffrn_orient_matrix_UB_23      -0.0830245000
_diffrn_orient_matrix_UB_31      -0.1223252000
_diffrn_orient_matrix_UB_32      0.0481366000
_diffrn_orient_matrix_UB_33      0.0031845000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            33048
_diffrn_reflns_point_group_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.986
_diffrn_reflns_theta_min         3.694
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_description       prism
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details
;
 Flack x determined using 4264 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     821
_refine_ls_number_reflns         12807
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0749
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1557P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2022
_refine_ls_wR_factor_ref         0.2190
_reflns_Friedel_coverage         0.843
_reflns_Friedel_fraction_full    0.863
_reflns_Friedel_fraction_max     0.833
_reflns_number_gt                11452
_reflns_number_total             12807
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00090c2.cif
_cod_data_source_block           m-332g
_cod_database_code               7158639
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C39H42N2O4
_chemical_oxdiff_usercomment
'odrediti apsolutnu konfiguraciju, 1 kiralni centar poznat'
_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 99.64
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C16(H16), C1A(H1AA), C16A(H16A)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C14(H14A,H14B), C28(H28A,H28B), C33(H33A,H33B),
 C2A(H2AA,H2AB), C3A(H3AA,H3AB), C14A(H14C,H14D), C28A(H28C,H28D), C33A(H33C,
 H33D)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C19(H19), C20(H20), C21(H21), C22(H22),
 C23(H23), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39), N1(H1A), C7A(H7A),
 C8A(H8A), C9A(H9A), C10A(H10A), C19A(H19A), C20A(H20A), C21A(H21A), C22A(H22A),
  C23A(H23A), C35A(H35A), C36A(H36A), C37A(H37A), C38A(H38A), C39A(H39A),
 N1A(H1AB)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C30(H30A,H30B,H30C), C31(H31A,H31B,
 H31C), C32(H32A,H32B,H32C), C26A(H26D,H26E,H26F), C27A(H27D,H27E,H27F),
 C30A(H30D,H30E,H30F), C31A(H31D,H31E,H31F), C32A(H32D,H32E,H32F)
;
_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 1.766
_oxdiff_exptl_absorpt_empirical_full_min 0.483
loop_
_space_group_symop_operation_xyz
'x, y, z'
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
C1 C 0.2350(3) 0.7480(3) 0.4241(3) 0.0475(7) Uani 1 1 d . . . . .
H1 H 0.191781 0.692419 0.373833 0.057 Uiso 1 1 calc R . . . .
C2 C 0.2309(4) 0.8585(4) 0.3628(4) 0.0591(9) Uani 1 1 d . . . . .
H2A H 0.271856 0.917267 0.409311 0.071 Uiso 1 1 calc R . . . .
H2B H 0.271288 0.850126 0.297835 0.071 Uiso 1 1 calc R . . . .
C3 C 0.1047(5) 0.8932(4) 0.3293(4) 0.0672(11) Uani 1 1 d . . . . .
H3A H 0.061390 0.889482 0.392733 0.081 Uiso 1 1 calc R . . . .
H3B H 0.106952 0.970431 0.307990 0.081 Uiso 1 1 calc R . . . .
C4 C 0.0409(5) 0.8258(4) 0.2403(4) 0.0669(11) Uani 1 1 d . . . . .
C5 C -0.0099(5) 0.7738(4) 0.1645(4) 0.0690(11) Uani 1 1 d . . . . .
C6 C -0.0676(5) 0.7108(4) 0.0716(4) 0.0673(11) Uani 1 1 d . . . . .
C7 C -0.1851(6) 0.7271(5) 0.0343(6) 0.0839(16) Uani 1 1 d . . . . .
H7 H -0.227858 0.777722 0.071168 0.101 Uiso 1 1 calc R . . . .
C8 C -0.2379(6) 0.6677(6) -0.0576(6) 0.0888(17) Uani 1 1 d . . . . .
H8 H -0.315140 0.680202 -0.083490 0.107 Uiso 1 1 calc R . . . .
C9 C -0.1752(7) 0.5901(5) -0.1104(5) 0.0846(16) Uani 1 1 d . . . . .
H9 H -0.211095 0.550272 -0.171569 0.101 Uiso 1 1 calc R . . . .
C10 C -0.0611(6) 0.5709(5) -0.0739(4) 0.0772(13) Uani 1 1 d . . . . .
H10 H -0.020675 0.517172 -0.109364 0.093 Uiso 1 1 calc R . . . .
C11 C -0.0054(5) 0.6321(4) 0.0166(3) 0.0652(10) Uani 1 1 d . . . . .
C12 C 0.1148(5) 0.6184(5) 0.0522(3) 0.0712(12) Uani 1 1 d . . . . .
C13 C 0.2166(5) 0.6122(5) 0.0817(4) 0.0735(12) Uani 1 1 d . . . . .
C14 C 0.3392(6) 0.6082(6) 0.1192(4) 0.0815(15) Uani 1 1 d . . . . .
H14A H 0.383003 0.659491 0.078003 0.098 Uiso 1 1 calc R . . . .
H14B H 0.365769 0.533500 0.105899 0.098 Uiso 1 1 calc R . . . .
C15 C 0.3394(4) 0.5533(4) 0.2999(3) 0.0595(9) Uani 1 1 d . . . . .
C16 C 0.3681(3) 0.5867(3) 0.4213(3) 0.0468(7) Uani 1 1 d . . . . .
H16 H 0.450741 0.571217 0.441011 0.056 Uiso 1 1 calc R . . . .
C17 C 0.4460(3) 0.7739(3) 0.4907(3) 0.0480(7) Uani 1 1 d . . . . .
C18 C 0.5673(3) 0.7333(3) 0.4901(4) 0.0537(8) Uani 1 1 d . . . . .
C19 C 0.6156(4) 0.7154(4) 0.3920(5) 0.0681(11) Uani 1 1 d . . . . .
H19 H 0.569968 0.720371 0.325430 0.082 Uiso 1 1 calc R . . . .
C20 C 0.7329(6) 0.6900(5) 0.3955(8) 0.093(2) Uani 1 1 d . . . . .
H20 H 0.766628 0.678885 0.330751 0.112 Uiso 1 1 calc R . . . .
C21 C 0.8003(5) 0.6811(5) 0.4954(10) 0.104(3) Uani 1 1 d . . . . .
H21 H 0.878531 0.662896 0.496971 0.125 Uiso 1 1 calc R . . . .
C22 C 0.7528(5) 0.6989(5) 0.5909(8) 0.093(2) Uani 1 1 d . . . . .
H22 H 0.798362 0.692334 0.657316 0.111 Uiso 1 1 calc R . . . .
C23 C 0.6366(4) 0.7267(4) 0.5894(5) 0.0694(11) Uani 1 1 d . . . . .
H23 H 0.604939 0.741075 0.654652 0.083 Uiso 1 1 calc R . . . .
C24 C 0.1659(3) 0.7548(3) 0.5248(3) 0.0503(7) Uani 1 1 d . . . . .
C25 C 0.1415(4) 0.8696(4) 0.6951(3) 0.0578(9) Uani 1 1 d . . . . .
C26 C 0.0947(5) 0.7746(5) 0.7592(5) 0.0749(12) Uani 1 1 d . . . . .
H26A H 0.036197 0.731260 0.713129 0.112 Uiso 1 1 calc GR . . . .
H26B H 0.060674 0.804814 0.821203 0.112 Uiso 1 1 calc GR . . . .
H26C H 0.157701 0.727729 0.783757 0.112 Uiso 1 1 calc GR . . . .
C27 C 0.0384(5) 0.9345(5) 0.6434(5) 0.0762(13) Uani 1 1 d . . . . .
H27A H 0.067523 1.000260 0.611024 0.114 Uiso 1 1 calc GR . . . .
H27B H -0.010350 0.955849 0.698715 0.114 Uiso 1 1 calc GR . . . .
H27C H -0.006538 0.888190 0.588154 0.114 Uiso 1 1 calc GR . . . .
C28 C 0.2243(5) 0.9542(4) 0.7660(4) 0.0637(10) Uani 1 1 d . . . . .
H28A H 0.255681 1.004910 0.715498 0.076 Uiso 1 1 calc R . . . .
H28B H 0.174670 0.998036 0.808543 0.076 Uiso 1 1 calc R . . . .
C29 C 0.3294(5) 0.9223(4) 0.8464(4) 0.0694(11) Uani 1 1 d . . . . .
C30 C 0.4131(6) 0.8460(6) 0.7950(5) 0.0844(15) Uani 1 1 d . . . . .
H30A H 0.372987 0.776475 0.771580 0.127 Uiso 1 1 calc GR . . . .
H30B H 0.478171 0.832187 0.847867 0.127 Uiso 1 1 calc GR . . . .
H30C H 0.441051 0.881153 0.733248 0.127 Uiso 1 1 calc GR . . . .
C31 C 0.2929(8) 0.8705(7) 0.9497(5) 0.0912(18) Uani 1 1 d . . . . .
H31A H 0.270185 0.793294 0.934605 0.137 Uiso 1 1 calc GR . . . .
H31B H 0.228053 0.909586 0.973648 0.137 Uiso 1 1 calc GR . . . .
H31C H 0.357495 0.876017 1.006068 0.137 Uiso 1 1 calc GR . . . .
C32 C 0.3954(8) 1.0333(6) 0.8811(6) 0.0940(19) Uani 1 1 d . . . . .
H32A H 0.461184 1.019612 0.933155 0.141 Uiso 1 1 calc GR . . . .
H32B H 0.343822 1.082735 0.913781 0.141 Uiso 1 1 calc GR . . . .
H32C H 0.422382 1.066967 0.818165 0.141 Uiso 1 1 calc GR . . . .
C33 C 0.2967(4) 0.5110(3) 0.4889(3) 0.0515(8) Uani 1 1 d . . . . .
H33A H 0.215204 0.530809 0.477487 0.062 Uiso 1 1 calc R . . . .
H33B H 0.301497 0.434365 0.462531 0.062 Uiso 1 1 calc R . . . .
C34 C 0.3360(4) 0.5179(3) 0.6101(3) 0.0504(7) Uani 1 1 d . . . . .
C35 C 0.2522(5) 0.5275(4) 0.6832(4) 0.0707(12) Uani 1 1 d . . . . .
H35 H 0.173842 0.534363 0.657500 0.085 Uiso 1 1 calc R . . . .
C36 C 0.2865(8) 0.5267(7) 0.7963(5) 0.100(2) Uani 1 1 d . . . . .
H36 H 0.230733 0.534232 0.845250 0.119 Uiso 1 1 calc R . . . .
C37 C 0.4008(9) 0.5149(7) 0.8346(4) 0.099(2) Uani 1 1 d . . . . .
H37 H 0.422982 0.513631 0.909397 0.119 Uiso 1 1 calc R . . . .
C38 C 0.4832(6) 0.5049(5) 0.7621(5) 0.0811(14) Uani 1 1 d . . . . .
H38 H 0.561159 0.496424 0.788479 0.097 Uiso 1 1 calc R . . . .
C39 C 0.4523(4) 0.5072(4) 0.6507(4) 0.0600(9) Uani 1 1 d . . . . .
H39 H 0.509404 0.501585 0.602840 0.072 Uiso 1 1 calc R . . . .
N1 N 0.2079(3) 0.8274(3) 0.6056(3) 0.0517(7) Uani 1 1 d . . . . .
H1A H 0.279217 0.851665 0.605841 0.062 Uiso 1 1 calc R . . . .
N2 N 0.3551(3) 0.7065(2) 0.4441(2) 0.0456(6) Uani 1 1 d . . . . .
O1 O 0.0746(3) 0.6986(3) 0.5231(3) 0.0708(8) Uani 1 1 d . . . . .
O2 O 0.3621(3) 0.6379(3) 0.2352(2) 0.0671(8) Uani 1 1 d . . . . .
O3 O 0.3083(6) 0.4633(3) 0.2670(3) 0.0930(14) Uani 1 1 d . . . . .
O4 O 0.4318(3) 0.8673(2) 0.5297(2) 0.0551(6) Uani 1 1 d . . . . .
C1A C 0.7961(3) 1.2518(3) 0.5535(3) 0.0485(7) Uani 1 1 d . . . . .
H1AA H 0.836685 1.198166 0.601140 0.058 Uiso 1 1 calc R . . . .
C2A C 0.8086(4) 1.3642(3) 0.6186(3) 0.0574(9) Uani 1 1 d . . . . .
H2AA H 0.778045 1.422863 0.572255 0.069 Uiso 1 1 calc R . . . .
H2AB H 0.762724 1.360280 0.680243 0.069 Uiso 1 1 calc R . . . .
C3A C 0.9372(5) 1.3933(4) 0.6603(4) 0.0669(11) Uani 1 1 d . . . . .
H3AA H 0.984415 1.383029 0.600190 0.080 Uiso 1 1 calc R . . . .
H3AB H 0.944023 1.471677 0.683062 0.080 Uiso 1 1 calc R . . . .
C4A C 0.9853(5) 1.3276(4) 0.7511(4) 0.0667(11) Uani 1 1 d . . . . .
C5A C 1.0261(5) 1.2792(5) 0.8302(4) 0.0714(11) Uani 1 1 d . . . . .
C6A C 1.0814(5) 1.2307(5) 0.9261(4) 0.0729(12) Uani 1 1 d . . . . .
C7A C 1.1809(7) 1.2841(7) 0.9832(7) 0.098(2) Uani 1 1 d . . . . .
H7A H 1.209536 1.350746 0.957673 0.117 Uiso 1 1 calc R . . . .
C8A C 1.2377(7) 1.2408(8) 1.0763(7) 0.103(2) Uani 1 1 d . . . . .
H8A H 1.301817 1.279297 1.114169 0.124 Uiso 1 1 calc R . . . .
C9A C 1.1987(7) 1.1409(7) 1.1121(5) 0.0926(19) Uani 1 1 d . . . . .
H9A H 1.239039 1.109473 1.172503 0.111 Uiso 1 1 calc R . . . .
C10A C 1.0998(6) 1.0861(6) 1.0594(4) 0.0765(13) Uani 1 1 d . . . . .
H10A H 1.073072 1.018960 1.085547 0.092 Uiso 1 1 calc R . . . .
C11A C 1.0399(5) 1.1310(4) 0.9671(3) 0.0660(10) Uani 1 1 d . . . . .
C12A C 0.9349(5) 1.0744(4) 0.9174(3) 0.0648(10) Uani 1 1 d . . . . .
C13A C 0.8465(5) 1.0270(5) 0.8796(4) 0.0696(11) Uani 1 1 d . . . . .
C14A C 0.7365(7) 0.9717(6) 0.8351(4) 0.0867(18) Uani 1 1 d . . . . .
H14C H 0.673238 1.002464 0.871500 0.104 Uiso 1 1 calc R . . . .
H14D H 0.739221 0.892740 0.849956 0.104 Uiso 1 1 calc R . . . .
C15A C 0.6799(4) 1.0859(4) 0.6888(3) 0.0559(8) Uani 1 1 d . . . . .
C16A C 0.6539(3) 1.0928(3) 0.5638(3) 0.0487(7) Uani 1 1 d . . . . .
H16A H 0.570463 1.073649 0.545341 0.058 Uiso 1 1 calc R . . . .
C17A C 0.5847(3) 1.2739(3) 0.4955(3) 0.0463(7) Uani 1 1 d . . . . .
C18A C 0.4610(3) 1.2368(3) 0.5062(3) 0.0518(8) Uani 1 1 d . . . . .
C19A C 0.4218(4) 1.2319(4) 0.6092(4) 0.0618(9) Uani 1 1 d . . . . .
H19A H 0.474854 1.241431 0.671571 0.074 Uiso 1 1 calc R . . . .
C20A C 0.3034(5) 1.2126(5) 0.6189(6) 0.0790(15) Uani 1 1 d . . . . .
H20A H 0.277112 1.210066 0.687704 0.095 Uiso 1 1 calc R . . . .
C21A C 0.2256(5) 1.1975(5) 0.5269(7) 0.0857(18) Uani 1 1 d . . . . .
H21A H 0.146652 1.184137 0.533924 0.103 Uiso 1 1 calc R . . . .
C22A C 0.2621(5) 1.2017(4) 0.4260(6) 0.0815(16) Uani 1 1 d . . . . .
H22A H 0.208192 1.190580 0.364405 0.098 Uiso 1 1 calc R . . . .
C23A C 0.3801(4) 1.2226(4) 0.4141(4) 0.0644(10) Uani 1 1 d . . . . .
H23A H 0.404681 1.227088 0.344658 0.077 Uiso 1 1 calc R . . . .
C24A C 0.8632(3) 1.2555(3) 0.4514(3) 0.0516(7) Uani 1 1 d . . . . .
C25A C 0.8795(4) 1.3541(4) 0.2752(4) 0.0624(9) Uani 1 1 d . . . . .
C26A C 0.9295(6) 1.2548(6) 0.2175(5) 0.0815(15) Uani 1 1 d . . . . .
H26D H 0.996424 1.229315 0.262061 0.122 Uiso 1 1 calc GR . . . .
H26E H 0.952639 1.277156 0.148454 0.122 Uiso 1 1 calc GR . . . .
H26F H 0.871027 1.195364 0.205648 0.122 Uiso 1 1 calc GR . . . .
C27A C 0.9779(7) 1.4368(8) 0.3180(6) 0.099(2) Uani 1 1 d . . . . .
H27D H 0.945406 1.503571 0.345237 0.148 Uiso 1 1 calc GR . . . .
H27E H 1.024085 1.454841 0.259934 0.148 Uiso 1 1 calc GR . . . .
H27F H 1.026565 1.404156 0.376010 0.148 Uiso 1 1 calc GR . . . .
C28A C 0.7881(5) 1.4154(4) 0.1989(4) 0.0717(12) Uani 1 1 d . . . . .
H28C H 0.753900 1.470045 0.244719 0.086 Uiso 1 1 calc R . . . .
H28D H 0.831882 1.457342 0.149628 0.086 Uiso 1 1 calc R . . . .
C29A C 0.6859(6) 1.3555(6) 0.1281(4) 0.0792(14) Uani 1 1 d . . . . .
C30A C 0.6154(6) 1.2741(6) 0.1895(5) 0.0845(15) Uani 1 1 d . . . . .
H30D H 0.665835 1.218429 0.220705 0.127 Uiso 1 1 calc GR . . . .
H30E H 0.554223 1.238568 0.139960 0.127 Uiso 1 1 calc GR . . . .
H30F H 0.581599 1.313726 0.246719 0.127 Uiso 1 1 calc GR . . . .
C31A C 0.7249(10) 1.2977(11) 0.0264(6) 0.122(3) Uani 1 1 d . . . . .
H31D H 0.767098 1.350587 -0.013020 0.184 Uiso 1 1 calc GR . . . .
H31E H 0.657329 1.268505 -0.019530 0.184 Uiso 1 1 calc GR . . . .
H31F H 0.774636 1.237581 0.047803 0.184 Uiso 1 1 calc GR . . . .
C32A C 0.6018(10) 1.4461(11) 0.0890(9) 0.137(4) Uani 1 1 d . . . . .
H32D H 0.577144 1.485677 0.151081 0.206 Uiso 1 1 calc GR . . . .
H32E H 0.534719 1.412040 0.045988 0.206 Uiso 1 1 calc GR . . . .
H32F H 0.640955 1.497408 0.045346 0.206 Uiso 1 1 calc GR . . . .
C33A C 0.7220(4) 1.0097(3) 0.5004(3) 0.0539(8) Uani 1 1 d . . . . .
H33C H 0.804749 1.030330 0.513413 0.065 Uiso 1 1 calc R . . . .
H33D H 0.711157 0.936014 0.529122 0.065 Uiso 1 1 calc R . . . .
C34A C 0.6871(4) 1.0029(3) 0.3783(3) 0.0541(8) Uani 1 1 d . . . . .
C35A C 0.7730(5) 0.9962(4) 0.3071(4) 0.0687(11) Uani 1 1 d . . . . .
H35A H 0.851567 1.003464 0.334554 0.082 Uiso 1 1 calc R . . . .
C36A C 0.7430(7) 0.9788(6) 0.1956(5) 0.0862(16) Uani 1 1 d . . . . .
H36A H 0.801495 0.974236 0.148992 0.103 Uiso 1 1 calc R . . . .
C37A C 0.6275(7) 0.9681(6) 0.1535(4) 0.0888(17) Uani 1 1 d . . . . .
H37A H 0.607707 0.955784 0.078753 0.107 Uiso 1 1 calc R . . . .
C38A C 0.5415(6) 0.9758(5) 0.2225(5) 0.0803(15) Uani 1 1 d . . . . .
H38A H 0.463253 0.969209 0.194004 0.096 Uiso 1 1 calc R . . . .
C39A C 0.5701(5) 0.9934(4) 0.3346(4) 0.0621(9) Uani 1 1 d . . . . .
H39A H 0.511025 0.998890 0.380493 0.074 Uiso 1 1 calc R . . . .
N1A N 0.8195(3) 1.3184(3) 0.3703(3) 0.0544(7) Uani 1 1 d . . . . .
H1AB H 0.749488 1.340486 0.373373 0.065 Uiso 1 1 calc R . . . .
N16A N 0.6727(3) 1.2086(2) 0.5341(2) 0.0461(6) Uani 1 1 d . . . . .
O1A O 0.9543(3) 1.2045(4) 0.4527(3) 0.0748(9) Uani 1 1 d . . . . .
O2A O 0.7121(4) 0.9847(3) 0.7177(3) 0.0718(9) Uani 1 1 d . . . . .
O3A O 0.6697(4) 1.1621(4) 0.7512(3) 0.0761(9) Uani 1 1 d . . . . .
O4A O 0.6033(3) 1.3651(2) 0.4559(3) 0.0567(6) Uani 1 1 d . . . . .
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'
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_
_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
C24 C1 C2 111.2(3) . . ?
N2 C1 C2 112.6(3) . . ?
N2 C1 C24 115.7(3) . . ?
C3 C2 C1 112.3(4) . . ?
C4 C3 C2 115.2(4) . . ?
C5 C4 C3 177.3(6) . . ?
C4 C5 C6 178.2(7) . . ?
C7 C6 C5 121.2(5) . . ?
C11 C6 C5 119.7(5) . . ?
C11 C6 C7 119.1(5) . . ?
C8 C7 C6 120.2(6) . . ?
C9 C8 C7 119.8(6) . . ?
C10 C9 C8 121.0(5) . . ?
C9 C10 C11 120.0(6) . . ?
C6 C11 C12 119.0(4) . . ?
C10 C11 C6 119.9(5) . . ?
C10 C11 C12 121.1(5) . . ?
C13 C12 C11 176.9(6) . . ?
C12 C13 C14 178.1(7) . . ?
C13 C14 O2 111.6(4) . . ?
O2 C15 C16 111.7(4) . . ?
O3 C15 C16 124.3(4) . . ?
O3 C15 O2 123.8(4) . . ?
C33 C16 C15 109.0(3) . . ?
N2 C16 C15 112.8(3) . . ?
N2 C16 C33 113.7(3) . . ?
N2 C17 C18 118.2(3) . . ?
O4 C17 C18 119.2(3) . . ?
O4 C17 N2 122.6(4) . . ?
C19 C18 C17 120.8(4) . . ?
C23 C18 C17 118.6(4) . . ?
C23 C18 C19 120.1(5) . . ?
C20 C19 C18 118.9(6) . . ?
C19 C20 C21 120.3(7) . . ?
C22 C21 C20 120.5(6) . . ?
C21 C22 C23 120.1(7) . . ?
C22 C23 C18 120.0(6) . . ?
N1 C24 C1 116.6(3) . . ?
O1 C24 C1 118.4(4) . . ?
O1 C24 N1 124.9(4) . . ?
C26 C25 C27 109.1(4) . . ?
C26 C25 C28 113.7(4) . . ?
C27 C25 C28 107.3(4) . . ?
N1 C25 C26 111.7(4) . . ?
N1 C25 C27 108.0(4) . . ?
N1 C25 C28 106.8(3) . . ?
C29 C28 C25 124.8(4) . . ?
C30 C29 C28 113.5(4) . . ?
C30 C29 C31 109.3(5) . . ?
C30 C29 C32 108.2(6) . . ?
C31 C29 C28 113.2(5) . . ?
C31 C29 C32 107.2(5) . . ?
C32 C29 C28 105.1(5) . . ?
C34 C33 C16 114.1(3) . . ?
C35 C34 C33 119.0(4) . . ?
C39 C34 C33 121.9(4) . . ?
C39 C34 C35 118.9(4) . . ?
C34 C35 C36 119.7(6) . . ?
C37 C36 C35 120.5(6) . . ?
C36 C37 C38 119.6(5) . . ?
C37 C38 C39 121.1(6) . . ?
C38 C39 C34 120.1(5) . . ?
C24 N1 C25 125.5(3) . . ?
C16 N2 C1 116.2(3) . . ?
C17 N2 C1 121.4(3) . . ?
C17 N2 C16 122.0(3) . . ?
C15 O2 C14 113.3(4) . . ?
C2A C1A C24A 111.3(3) . . ?
N16A C1A C2A 112.6(3) . . ?
N16A C1A C24A 115.6(3) . . ?
C3A C2A C1A 111.4(4) . . ?
C4A C3A C2A 114.9(4) . . ?
C5A C4A C3A 176.0(5) . . ?
C4A C5A C6A 174.7(6) . . ?
C7A C6A C5A 119.8(6) . . ?
C11A C6A C5A 122.6(5) . . ?
C11A C6A C7A 117.6(5) . . ?
C8A C7A C6A 122.1(8) . . ?
C9A C8A C7A 119.3(7) . . ?
C8A C9A C10A 120.6(6) . . ?
C9A C10A C11A 120.3(6) . . ?
C6A C11A C12A 121.2(4) . . ?
C10A C11A C6A 120.0(5) . . ?
C10A C11A C12A 118.8(5) . . ?
C13A C12A C11A 177.7(5) . . ?
C12A C13A C14A 178.2(7) . . ?
C13A C14A O2A 112.4(4) . . ?
O2A C15A C16A 111.8(4) . . ?
O3A C15A C16A 123.5(4) . . ?
O3A C15A O2A 124.7(4) . . ?
C33A C16A C15A 113.2(3) . . ?
N16A C16A C15A 108.6(3) . . ?
N16A C16A C33A 113.3(3) . . ?
N16A C17A C18A 119.0(3) . . ?
O4A C17A C18A 118.8(3) . . ?
O4A C17A N16A 122.1(4) . . ?
C19A C18A C17A 119.9(4) . . ?
C23A C18A C17A 120.4(4) . . ?
C23A C18A C19A 119.1(4) . . ?
C20A C19A C18A 120.0(5) . . ?
C21A C20A C19A 119.9(6) . . ?
C22A C21A C20A 121.0(5) . . ?
C21A C22A C23A 120.2(5) . . ?
C18A C23A C22A 119.8(5) . . ?
N1A C24A C1A 116.8(3) . . ?
O1A C24A C1A 117.9(4) . . ?
O1A C24A N1A 125.3(4) . . ?
C26A C25A C28A 112.5(4) . . ?
C27A C25A C26A 109.7(5) . . ?
C27A C25A C28A 108.9(5) . . ?
N1A C25A C26A 111.3(4) . . ?
N1A C25A C27A 107.5(4) . . ?
N1A C25A C28A 106.7(4) . . ?
C29A C28A C25A 123.6(5) . . ?
C28A C29A C32A 106.4(8) . . ?
C30A C29A C28A 114.0(4) . . ?
C30A C29A C31A 110.2(7) . . ?
C30A C29A C32A 106.1(7) . . ?
C31A C29A C28A 112.3(6) . . ?
C31A C29A C32A 107.2(7) . . ?
C34A C33A C16A 114.8(3) . . ?
C35A C34A C33A 119.7(4) . . ?
C35A C34A C39A 118.4(4) . . ?
C39A C34A C33A 121.7(4) . . ?
C36A C35A C34A 120.8(6) . . ?
C37A C36A C35A 120.4(6) . . ?
C38A C37A C36A 119.5(5) . . ?
C37A C38A C39A 120.8(6) . . ?
C38A C39A C34A 120.1(5) . . ?
C24A N1A C25A 126.7(4) . . ?
C16A N16A C1A 114.9(3) . . ?
C17A N16A C1A 121.9(3) . . ?
C17A N16A C16A 123.1(3) . . ?
C15A O2A C14A 114.8(4) . . ?
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
C1 C2 1.544(5) . ?
C1 C24 1.543(5) . ?
C1 N2 1.481(5) . ?
C2 C3 1.540(7) . ?
C3 C4 1.458(7) . ?
C4 C5 1.194(7) . ?
C5 C6 1.438(7) . ?
C6 C7 1.402(8) . ?
C6 C11 1.401(8) . ?
C7 C8 1.389(9) . ?
C8 C9 1.382(11) . ?
C9 C10 1.369(10) . ?
C10 C11 1.400(7) . ?
C11 C12 1.421(8) . ?
C12 C13 1.194(9) . ?
C13 C14 1.438(9) . ?
C14 O2 1.456(6) . ?
C15 C16 1.535(5) . ?
C15 O2 1.344(6) . ?
C15 O3 1.171(6) . ?
C16 C33 1.527(5) . ?
C16 N2 1.469(5) . ?
C17 C18 1.493(6) . ?
C17 N2 1.365(4) . ?
C17 O4 1.226(5) . ?
C18 C19 1.394(7) . ?
C18 C23 1.393(7) . ?
C19 C20 1.389(8) . ?
C20 C21 1.392(14) . ?
C21 C22 1.362(13) . ?
C22 C23 1.384(9) . ?
C24 N1 1.340(5) . ?
C24 O1 1.227(5) . ?
C25 C26 1.521(6) . ?
C25 C27 1.531(7) . ?
C25 C28 1.551(6) . ?
C25 N1 1.490(5) . ?
C28 C29 1.544(8) . ?
C29 C30 1.520(9) . ?
C29 C31 1.525(8) . ?
C29 C32 1.535(8) . ?
C33 C34 1.511(5) . ?
C34 C35 1.391(6) . ?
C34 C39 1.388(6) . ?
C35 C36 1.406(9) . ?
C36 C37 1.361(13) . ?
C37 C38 1.373(11) . ?
C38 C39 1.382(7) . ?
C1A C2A 1.540(5) . ?
C1A C24A 1.543(5) . ?
C1A N16A 1.486(5) . ?
C2A C3A 1.538(6) . ?
C3A C4A 1.458(7) . ?
C4A C5A 1.208(8) . ?
C5A C6A 1.430(7) . ?
C6A C7A 1.402(9) . ?
C6A C11A 1.400(9) . ?
C7A C8A 1.382(10) . ?
C8A C9A 1.367(13) . ?
C9A C10A 1.383(10) . ?
C10A C11A 1.397(7) . ?
C11A C12A 1.434(7) . ?
C12A C13A 1.191(8) . ?
C13A C14A 1.454(8) . ?
C14A O2A 1.457(6) . ?
C15A C16A 1.541(5) . ?
C15A O2A 1.327(6) . ?
C15A O3A 1.192(6) . ?
C16A C33A 1.532(6) . ?
C16A N16A 1.461(4) . ?
C17A C18A 1.496(5) . ?
C17A N16A 1.354(5) . ?
C17A O4A 1.231(5) . ?
C18A C19A 1.392(6) . ?
C18A C23A 1.391(6) . ?
C19A C20A 1.391(7) . ?
C20A C21A 1.370(11) . ?
C21A C22A 1.354(11) . ?
C22A C23A 1.396(8) . ?
C24A N1A 1.334(5) . ?
C24A O1A 1.228(6) . ?
C25A C26A 1.526(7) . ?
C25A C27A 1.519(8) . ?
C25A C28A 1.552(8) . ?
C25A N1A 1.487(5) . ?
C28A C29A 1.531(9) . ?
C29A C30A 1.517(9) . ?
C29A C31A 1.527(10) . ?
C29A C32A 1.532(10) . ?
C33A C34A 1.513(5) . ?
C34A C35A 1.390(7) . ?
C34A C39A 1.395(7) . ?
C35A C36A 1.388(8) . ?
C36A C37A 1.373(11) . ?
C37A C38A 1.373(11) . ?
C38A C39A 1.393(7) . ?
