#------------------------------------------------------------------------------
#$Date: 2022-09-20 11:29:04 +0300 (Tue, 20 Sep 2022) $
#$Revision: 277993 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/57/8105793.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_8105793
loop_
_publ_author_name
'Xing, Ai-Ping'
'Zeng, Dai'
_publ_section_title
;
 Crystal structure of
 (E)-2-(((6-bromopyridin-2-yl)methylene)amino)-3′,6′-bis(ethylamino)-2′,7′-dimethylspiro[isoindoline-1,9′-xanthen]-3-one---methanol
 (1:1), C32H30N5O2Br ⋅ CH4O
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              599
_journal_page_last               601
_journal_paper_doi               10.1515/ncrs-2018-0500
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C32 H30 Br N5 O2, C H4 O'
_chemical_formula_sum            'C33 H34 Br N5 O3'
_chemical_formula_weight         628.56
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                91.187(3)
_cell_angle_beta                 95.764(2)
_cell_angle_gamma                102.256(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1179(2)
_cell_length_b                   9.3291(3)
_cell_length_c                   18.4706(6)
_cell_measurement_reflns_used    7889
_cell_measurement_temperature    105.7(5)
_cell_measurement_theta_max      71.3020
_cell_measurement_theta_min      4.7920
_cell_volume                     1526.14(8)
_computing_cell_refinement       'CrysAlisPro [1] 2018)'
_computing_data_collection       'CrysAlisPro [1] 2018)'
_computing_data_reduction        'CrysAlisPro [1]2018)'
_computing_molecular_graphics    'Olex2 [2]'
_computing_publication_material  'Olex2 [2]'
_computing_structure_refinement  'ShelXL-2015 [3]'
_computing_structure_solution    'ShelXT-2015 [4]'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      105.7(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -62.00  24.00   1.00    2.00    --  -40.81  38.00  30.00   86
  2  ω    -65.00  32.00   1.00    2.00    --  -40.81  38.00 -90.00   97
  3  ω   -104.00 -19.00   1.00    2.00    --  -40.81 -38.00  90.00   85
  4  ω     14.00  78.00   1.00    2.00    --   40.81 -99.00  30.00   64
  5  ω     78.00 166.00   1.00    3.00    --  100.91  30.00 -90.00   88
  6  ω     63.00  89.00   1.00    3.00    --  100.91 -30.00-150.00   26
  7  ω     50.00 126.00   1.00    3.00    --  100.91 -30.00  30.00   76
  8  ω     35.00  90.00   1.00    3.00    --  100.91 -95.00-180.00   55
  9  ω     85.00 138.00   1.00    3.00    --  100.91  30.00-150.00   53
 10  ω     95.00 166.00   1.00    3.00    --  100.91 125.00  90.00   71
 11  ω    146.00 172.00   1.00    3.00    --  100.91 125.00-120.00   26
 12  ω     32.00  82.00   1.00    3.00    --  100.91 -95.00  90.00   50
 13  ω     29.00 127.00   1.00    3.00    --  100.91 -30.00 -60.00   98
 14  ω     87.00 112.00   1.00    3.00    --  100.91-125.00 -60.00   25
 15  ω     36.00 119.00   1.00    3.00    --  100.91 -61.00-180.00   83
 16  ω     60.00 118.00   1.00    3.00    --  100.91-125.00  60.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0427825000
_diffrn_orient_matrix_UB_12      -0.1270178000
_diffrn_orient_matrix_UB_13      0.0511570000
_diffrn_orient_matrix_UB_21      -0.0147377000
_diffrn_orient_matrix_UB_22      -0.1116099000
_diffrn_orient_matrix_UB_23      -0.0643774000
_diffrn_orient_matrix_UB_31      0.1679133000
_diffrn_orient_matrix_UB_32      -0.0044100000
_diffrn_orient_matrix_UB_33      0.0167078000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10106
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.434
_diffrn_reflns_theta_min         4.817
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.171
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       plate
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.921
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         5746
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0357
_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)+(0.0513P)²+1.0386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.0954
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5452
_reflns_number_total             5746
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0500_suppl.cif
_cod_data_source_block           1
_cod_original_cell_volume        1526.15(8)
_cod_database_code               8105793
_chemical_oxdiff_formula         'C H N O Br'
_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 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C31(H31A,H31B)
2.b Aromatic/amide H refined with riding coordinates:
 N5(H5), C6(H6), C22(H22), C16(H16), C12(H12), C25(H25), C11(H11), C19(H19),
 C4(H4A), C9(H9), C10(H10), C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C27(H27A,H27B,H27C), C30(H30A,H30B,H30C), C33(H33A,H33B,
 H33C), C32(H32A,H32B,H32C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3A)
;
_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 1.460
_oxdiff_exptl_absorpt_empirical_full_min 0.636
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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
Br1 Br 0.78841(3) 0.30993(3) 0.45262(2) 0.03812(9) Uani 1 1 d . . . . .
O1 O 0.5079(2) 0.92439(15) 0.75648(9) 0.0403(4) Uani 1 1 d . . . . .
O2 O 0.48305(14) 0.23414(13) 0.78652(7) 0.0214(3) Uani 1 1 d . . . . .
O3 O 0.65957(15) 1.03774(16) 0.64014(9) 0.0317(3) Uani 1 1 d . . . . .
H3A H 0.6267 0.9873 0.6732 0.047 Uiso 1 1 calc GR . . . .
N1 N 0.67401(16) 0.46551(17) 0.55366(8) 0.0192(3) Uani 1 1 d . . . . .
N2 N 0.55231(16) 0.68183(16) 0.68502(8) 0.0165(3) Uani 1 1 d . . . . .
N3 N 0.49759(15) 0.67403(15) 0.75108(8) 0.0146(3) Uani 1 1 d . . . . .
N4 N 0.99018(18) 0.32581(18) 0.89547(8) 0.0205(3) Uani 1 1 d . . . . .
H4 H 1.066(3) 0.378(3) 0.8949(14) 0.030(7) Uiso 1 1 d . . . . .
N5 N -0.01397(18) 0.08987(18) 0.66897(10) 0.0279(4) Uani 1 1 d . . . . .
H5 H -0.0963 0.1137 0.6518 0.034 Uiso 1 1 calc R . . . .
C1 C 0.7342(2) 0.4802(2) 0.49153(10) 0.0236(4) Uani 1 1 d . . . . .
C2 C 0.7627(2) 0.6074(2) 0.45338(10) 0.0282(4) Uani 1 1 d . . . . .
H2 H 0.8061 0.6104 0.4098 0.034 Uiso 1 1 calc R . . . .
C3 C 0.7239(2) 0.7297(2) 0.48292(10) 0.0269(4) Uani 1 1 d . . . . .
H3 H 0.7403 0.8177 0.4591 0.032 Uiso 1 1 calc R . . . .
C4 C 0.6602(2) 0.7205(2) 0.54830(10) 0.0220(4) Uani 1 1 d . . . . .
H4A H 0.6333 0.8015 0.5691 0.026 Uiso 1 1 calc R . . . .
C5 C 0.63772(18) 0.58638(19) 0.58200(9) 0.0171(3) Uani 1 1 d . . . . .
C6 C 0.57475(18) 0.56734(18) 0.65250(9) 0.0160(3) Uani 1 1 d . . . . .
H6 H 0.5522 0.4756 0.6725 0.019 Uiso 1 1 calc R . . . .
C7 C 0.4831(2) 0.80476(19) 0.78312(11) 0.0223(4) Uani 1 1 d . . . . .
C8 C 0.43612(19) 0.76900(19) 0.85567(10) 0.0190(3) Uani 1 1 d . . . . .
C9 C 0.4092(2) 0.8627(2) 0.91038(11) 0.0245(4) Uani 1 1 d . . . . .
H9 H 0.4148 0.9619 0.9030 0.029 Uiso 1 1 calc R . . . .
C10 C 0.3740(2) 0.8026(2) 0.97593(10) 0.0249(4) Uani 1 1 d . . . . .
H10 H 0.3563 0.8623 1.0136 0.030 Uiso 1 1 calc R . . . .
C11 C 0.36478(19) 0.6531(2) 0.98620(10) 0.0215(4) Uani 1 1 d . . . . .
H11 H 0.3409 0.6147 1.0306 0.026 Uiso 1 1 calc R . . . .
C12 C 0.39081(18) 0.56050(19) 0.93086(9) 0.0169(3) Uani 1 1 d . . . . .
H12 H 0.3842 0.4609 0.9377 0.020 Uiso 1 1 calc R . . . .
C13 C 0.42680(17) 0.62134(18) 0.86546(9) 0.0141(3) Uani 1 1 d . . . . .
C14 C 0.46751(18) 0.54505(17) 0.79891(8) 0.0127(3) Uani 1 1 d . . . . .
C15 C 0.33898(18) 0.42390(17) 0.76589(8) 0.0132(3) Uani 1 1 d . . . . .
C16 C 0.19806(18) 0.45211(18) 0.73991(9) 0.0147(3) Uani 1 1 d . . . . .
H16 H 0.1847 0.5480 0.7433 0.018 Uiso 1 1 calc R . . . .
C17 C 0.07825(18) 0.34380(19) 0.70950(9) 0.0156(3) Uani 1 1 d . . . . .
C18 C 0.0989(2) 0.19716(19) 0.70335(9) 0.0189(3) Uani 1 1 d . . . . .
C19 C 0.2375(2) 0.16709(19) 0.73041(10) 0.0196(4) Uani 1 1 d . . . . .
H19 H 0.2519 0.0715 0.7279 0.024 Uiso 1 1 calc R . . . .
C20 C 0.35380(19) 0.27985(18) 0.76104(9) 0.0160(3) Uani 1 1 d . . . . .
C21 C 0.60718(18) 0.33800(18) 0.81394(9) 0.0149(3) Uani 1 1 d . . . . .
C22 C 0.73331(19) 0.28247(19) 0.83740(9) 0.0164(3) Uani 1 1 d . . . . .
H22 H 0.7289 0.1821 0.8335 0.020 Uiso 1 1 calc R . . . .
C23 C 0.86612(19) 0.37787(19) 0.86671(9) 0.0166(3) Uani 1 1 d . . . . .
C24 C 0.87216(19) 0.53128(19) 0.87018(9) 0.0172(3) Uani 1 1 d . . . . .
C25 C 0.74419(18) 0.58040(18) 0.84643(9) 0.0156(3) Uani 1 1 d . . . . .
H25 H 0.7482 0.6808 0.8491 0.019 Uiso 1 1 calc R . . . .
C26 C 0.60813(18) 0.48628(18) 0.81841(8) 0.0132(3) Uani 1 1 d . . . . .
C27 C 1.01381(19) 0.6371(2) 0.90126(11) 0.0235(4) Uani 1 1 d . . . . .
H27A H 0.9978 0.7355 0.8996 0.035 Uiso 1 1 calc GR . . . .
H27B H 1.0948 0.6286 0.8732 0.035 Uiso 1 1 calc GR . . . .
H27C H 1.0393 0.6149 0.9508 0.035 Uiso 1 1 calc GR . . . .
C28 C -0.06798(19) 0.3804(2) 0.67836(10) 0.0212(4) Uani 1 1 d . . . . .
H28A H -0.0640 0.4828 0.6877 0.032 Uiso 1 1 calc GR . . . .
H28B H -0.1501 0.3228 0.7008 0.032 Uiso 1 1 calc GR . . . .
H28C H -0.0829 0.3587 0.6268 0.032 Uiso 1 1 calc GR . . . .
C29 C 0.9925(2) 0.1710(2) 0.89142(11) 0.0259(4) Uani 1 1 d . . . . .
H29A H 0.9780 0.1361 0.8408 0.031 Uiso 1 1 calc R . . . .
H29B H 0.9103 0.1160 0.9158 0.031 Uiso 1 1 calc R . . . .
C30 C 1.1420(2) 0.1454(3) 0.92711(13) 0.0354(5) Uani 1 1 d . . . . .
H30A H 1.2224 0.1928 0.9003 0.053 Uiso 1 1 calc GR . . . .
H30B H 1.1390 0.0419 0.9272 0.053 Uiso 1 1 calc GR . . . .
H30C H 1.1591 0.1853 0.9763 0.053 Uiso 1 1 calc GR . . . .
C31 C -0.0024(3) -0.0619(2) 0.65998(14) 0.0384(5) Uani 1 1 d . . . . .
H31A H 0.0972 -0.0645 0.6466 0.046 Uiso 1 1 calc R . . . .
H31B H -0.0757 -0.1089 0.6203 0.046 Uiso 1 1 calc R . . . .
C32 C -0.0286(3) -0.1485(3) 0.72768(19) 0.0579(8) Uani 1 1 d . . . . .
H32A H -0.0159 -0.2466 0.7189 0.087 Uiso 1 1 calc GR . . . .
H32B H -0.1292 -0.1515 0.7396 0.087 Uiso 1 1 calc GR . . . .
H32C H 0.0428 -0.1021 0.7675 0.087 Uiso 1 1 calc GR . . . .
C33 C 0.5438(2) 1.0981(2) 0.60476(12) 0.0307(4) Uani 1 1 d . . . . .
H33A H 0.5853 1.1677 0.5707 0.046 Uiso 1 1 calc GR . . . .
H33B H 0.4988 1.1466 0.6402 0.046 Uiso 1 1 calc GR . . . .
H33C H 0.4683 1.0211 0.5793 0.046 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'
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
C21 O2 C20 118.48(13) . .
N2 N3 C14 128.76(13) . .
N2 N3 C7 116.60(14) . .
C7 N3 C14 114.20(13) . .
C33 O3 H3A 109.5 . .
C1 N1 C5 116.37(16) . .
C6 N2 N3 120.99(14) . .
C23 N4 C29 121.74(16) . .
C23 N4 H4 115.4(19) . .
C29 N4 H4 115.7(19) . .
C18 N5 H5 118.2 . .
C18 N5 C31 123.54(16) . .
C31 N5 H5 118.2 . .
C16 C15 C14 121.63(14) . .
C20 C15 C14 121.52(14) . .
C20 C15 C16 116.84(15) . .
C16 C17 C18 118.61(15) . .
C16 C17 C28 121.24(15) . .
C18 C17 C28 120.00(15) . .
N2 C6 H6 121.3 . .
N2 C6 C5 117.39(15) . .
C5 C6 H6 121.3 . .
C25 C26 C14 120.88(14) . .
C21 C26 C14 122.18(14) . .
C21 C26 C25 116.83(15) . .
N1 C5 C6 114.99(15) . .
N1 C5 C4 122.99(16) . .
C4 C5 C6 122.01(16) . .
C12 C13 C14 127.66(15) . .
C8 C13 C14 111.58(15) . .
C8 C13 C12 120.70(16) . .
C21 C22 H22 120.1 . .
C21 C22 C23 119.79(15) . .
C23 C22 H22 120.1 . .
N3 C14 C15 112.52(13) . .
N3 C14 C26 111.62(13) . .
N3 C14 C13 99.11(12) . .
C15 C14 C13 112.21(13) . .
C26 C14 C15 110.70(13) . .
C26 C14 C13 110.21(13) . .
C15 C16 H16 118.5 . .
C17 C16 C15 123.05(15) . .
C17 C16 H16 118.5 . .
C13 C12 H12 121.0 . .
C13 C12 C11 117.99(17) . .
C11 C12 H12 121.0 . .
C26 C25 H25 118.4 . .
C24 C25 C26 123.18(16) . .
C24 C25 H25 118.4 . .
C13 C8 C7 109.16(15) . .
C13 C8 C9 121.91(17) . .
C9 C8 C7 128.88(17) . .
O2 C21 C26 123.03(15) . .
O2 C21 C22 114.66(14) . .
C26 C21 C22 122.30(15) . .
N4 C23 C22 121.38(16) . .
N4 C23 C24 119.26(16) . .
C22 C23 C24 119.30(15) . .
N5 C18 C17 119.84(16) . .
N5 C18 C19 121.23(17) . .
C19 C18 C17 118.89(15) . .
O2 C20 C15 123.64(15) . .
O2 C20 C19 113.93(15) . .
C15 C20 C19 122.43(16) . .
C12 C11 H11 119.5 . .
C12 C11 C10 121.08(17) . .
C10 C11 H11 119.5 . .
C25 C24 C23 118.56(15) . .
C25 C24 C27 120.81(16) . .
C23 C24 C27 120.61(15) . .
C18 C19 H19 119.9 . .
C20 C19 C18 120.14(16) . .
C20 C19 H19 119.9 . .
C5 C4 H4A 120.9 . .
C3 C4 C5 118.22(18) . .
C3 C4 H4A 120.9 . .
C17 C28 H28A 109.5 . .
C17 C28 H28B 109.5 . .
C17 C28 H28C 109.5 . .
H28A C28 H28B 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
N3 C7 C8 105.93(15) . .
O1 C7 N3 126.20(18) . .
O1 C7 C8 127.86(17) . .
C8 C9 H9 121.2 . .
C10 C9 C8 117.61(17) . .
C10 C9 H9 121.2 . .
C11 C10 H10 119.6 . .
C9 C10 C11 120.71(17) . .
C9 C10 H10 119.6 . .
N1 C1 Br1 116.16(14) . .
N1 C1 C2 125.85(18) . .
C2 C1 Br1 117.98(14) . .
C24 C27 H27A 109.5 . .
C24 C27 H27B 109.5 . .
C24 C27 H27C 109.5 . .
H27A C27 H27B 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C4 C3 H3 120.2 . .
C2 C3 C4 119.57(18) . .
C2 C3 H3 120.2 . .
N4 C29 H29A 109.6 . .
N4 C29 H29B 109.6 . .
N4 C29 C30 110.48(17) . .
H29A C29 H29B 108.1 . .
C30 C29 H29A 109.6 . .
C30 C29 H29B 109.6 . .
C1 C2 H2 121.5 . .
C3 C2 C1 117.00(17) . .
C3 C2 H2 121.5 . .
C29 C30 H30A 109.5 . .
C29 C30 H30B 109.5 . .
C29 C30 H30C 109.5 . .
H30A C30 H30B 109.5 . .
H30A C30 H30C 109.5 . .
H30B C30 H30C 109.5 . .
O3 C33 H33A 109.5 . .
O3 C33 H33B 109.5 . .
O3 C33 H33C 109.5 . .
H33A C33 H33B 109.5 . .
H33A C33 H33C 109.5 . .
H33B C33 H33C 109.5 . .
N5 C31 H31A 108.9 . .
N5 C31 H31B 108.9 . .
N5 C31 C32 113.5(2) . .
H31A C31 H31B 107.7 . .
C32 C31 H31A 108.9 . .
C32 C31 H31B 108.9 . .
C31 C32 H32A 109.5 . .
C31 C32 H32B 109.5 . .
C31 C32 H32C 109.5 . .
H32A C32 H32B 109.5 . .
H32A C32 H32C 109.5 . .
H32B C32 H32C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.908(2) .
O2 C21 1.369(2) .
O2 C20 1.379(2) .
N3 N2 1.361(2) .
N3 C14 1.502(2) .
N3 C7 1.382(2) .
O3 H3A 0.8200 .
O3 C33 1.410(2) .
O1 C7 1.215(2) .
N1 C5 1.350(2) .
N1 C1 1.318(2) .
N2 C6 1.278(2) .
N4 C23 1.386(2) .
N4 C29 1.449(2) .
N4 H4 0.76(3) .
N5 H5 0.8600 .
N5 C18 1.367(2) .
N5 C31 1.449(3) .
C15 C14 1.513(2) .
C15 C16 1.405(2) .
C15 C20 1.381(2) .
C17 C16 1.384(2) .
C17 C18 1.424(2) .
C17 C28 1.507(2) .
C6 H6 0.9300 .
C6 C5 1.474(2) .
C26 C14 1.513(2) .
C26 C25 1.403(2) .
C26 C21 1.382(2) .
C5 C4 1.394(2) .
C13 C14 1.524(2) .
C13 C12 1.385(2) .
C13 C8 1.379(2) .
C22 H22 0.9300 .
C22 C21 1.393(2) .
C22 C23 1.394(2) .
C16 H16 0.9300 .
C12 H12 0.9300 .
C12 C11 1.395(2) .
C25 H25 0.9300 .
C25 C24 1.377(2) .
C8 C7 1.471(3) .
C8 C9 1.396(3) .
C23 C24 1.420(2) .
C18 C19 1.398(3) .
C20 C19 1.390(2) .
C11 H11 0.9300 .
C11 C10 1.397(3) .
C24 C27 1.503(2) .
C19 H19 0.9300 .
C4 H4A 0.9300 .
C4 C3 1.388(3) .
C28 H28A 0.9600 .
C28 H28B 0.9600 .
C28 H28C 0.9600 .
C9 H9 0.9300 .
C9 C10 1.383(3) .
C10 H10 0.9300 .
C1 C2 1.383(3) .
C27 H27A 0.9600 .
C27 H27B 0.9600 .
C27 H27C 0.9600 .
C3 H3 0.9300 .
C3 C2 1.382(3) .
C29 H29A 0.9700 .
C29 H29B 0.9700 .
C29 C30 1.522(3) .
C2 H2 0.9300 .
C30 H30A 0.9600 .
C30 H30B 0.9600 .
C30 H30C 0.9600 .
C33 H33A 0.9600 .
C33 H33B 0.9600 .
C33 H33C 0.9600 .
C31 H31A 0.9700 .
C31 H31B 0.9700 .
C31 C32 1.514(4) .
C32 H32A 0.9600 .
C32 H32B 0.9600 .
C32 H32C 0.9600 .
