#------------------------------------------------------------------------------
#$Date: 2020-09-06 12:31:59 +0300 (Sun, 06 Sep 2020) $
#$Revision: 256060 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/49/7704912.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_7704912
loop_
_publ_author_name
'Sathiya Kamatchi, Thangavel'
'Mohamed Subarkhan, Mohamed Kasim'
'Ramesh, Rengan'
'Wang, Hangxiang'
'Małecki, Jan Grzegorz'
_publ_section_title
;
 Investigation into antiproliferative activity and apoptosis mechanism of
 new arene Ru(ii) carbazole-based hydrazone complexes.
;
_journal_issue                   32
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11385
_journal_page_last               11395
_journal_paper_doi               10.1039/d0dt01476a
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C19 H16 Br N3 O'
_chemical_formula_sum            'C19 H16 Br N3 O'
_chemical_formula_weight         382.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-08-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-09 deposited with the CCDC.	2020-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.856(4)
_cell_length_b                   8.3192(18)
_cell_length_c                   17.006(3)
_cell_measurement_reflns_used    2462
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.6120
_cell_measurement_theta_min      3.5320
_cell_volume                     3375.1(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4015
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  62.00   1.00   14.63    --  -11.93  38.00-150.00   64
  2  ω    -45.00  34.00   1.00   14.63    --  -11.93  77.00 -60.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0222073000
_diffrn_orient_matrix_UB_12      0.0077251000
_diffrn_orient_matrix_UB_13      -0.0275730000
_diffrn_orient_matrix_UB_21      0.0003375000
_diffrn_orient_matrix_UB_22      -0.0843599000
_diffrn_orient_matrix_UB_23      -0.0063723000
_diffrn_orient_matrix_UB_31      -0.0198762000
_diffrn_orient_matrix_UB_32      -0.0100889000
_diffrn_orient_matrix_UB_33      0.0305517000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.848
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12148
_diffrn_reflns_point_group_measured_fraction_full 0.839
_diffrn_reflns_point_group_measured_fraction_max 0.689
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.464
_diffrn_reflns_theta_min         3.416
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.446
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42149
_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            'pale yellow'
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 1357 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         6459
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0564
_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)+(0.0646P)²+1.9659P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1554
_reflns_Friedel_coverage         0.575
_reflns_Friedel_fraction_full    0.671
_reflns_Friedel_fraction_max     0.519
_reflns_number_gt                4033
_reflns_number_total             6459
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt01476a2.cif
_cod_data_source_block           c1brbh
_cod_depositor_comments
'Adding full bibliography for 7704909--7704913.cif.'
_cod_database_code               7704912
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'Br1 C19 H16 N3 O1'
_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 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
2. Others
 Sof(H9AA)=Sof(H9AB)=Sof(H11A)=Sof(H11B)=Sof(C10)=Sof(H10A)=Sof(H10B)=1-FVAR(1)
 Sof(H9BC)=Sof(H9BD)=Sof(H11C)=Sof(H11D)=Sof(C10A)=Sof(H10C)=Sof(H10D)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C9(H9BC,H9BD), C9(H9AA,H9AB), C11(H11C,H11D), C11(H11A,H11B), C10(H10A,H10B),
 C10A(H10C,H10D), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B)
3.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C3(H3A), C4(H4), C6(H6), C7(H7), C14(H14), C15(H15), C16(H16),
 C17(H17), N4(H4A), N6(H6A), C22(H22), C23(H23), C25(H25), C26(H26), C33(H33),
 C34(H34), C35(H35), C36(H36)
;
_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 1.892
_oxdiff_exptl_absorpt_empirical_full_min 0.745
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, 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 0.32328(4) 0.15185(11) 0.27933(8) 0.0826(4) Uani 1 1 d . . . . .
O1 O 0.1719(3) 0.8524(7) 0.3269(4) 0.0627(16) Uani 1 1 d . . . . .
N1 N 0.2097(3) 0.8991(8) 0.2067(4) 0.0462(16) Uani 1 1 d . . . . .
H1 H 0.226(3) 0.852(9) 0.163(5) 0.04(2) Uiso 1 1 d . . . . .
N2 N 0.1838(2) 1.0468(8) 0.1979(4) 0.0443(16) Uani 1 1 d . . . . .
N3 N 0.1356(3) 1.3577(7) 0.1736(4) 0.0426(15) Uani 1 1 d . . . . .
H3 H 0.1228 1.3173 0.2166 0.051 Uiso 1 1 calc R . . . .
C1 C 0.2012(3) 0.8078(9) 0.2725(5) 0.0431(18) Uani 1 1 d . . . . .
C2 C 0.2319(3) 0.6509(9) 0.2724(5) 0.0401(17) Uani 1 1 d . . . . .
C3 C 0.2096(4) 0.5235(11) 0.3138(5) 0.054(2) Uani 1 1 d . . . . .
H3A H 0.1761 0.5373 0.3408 0.064 Uiso 1 1 calc R . . . .
C4 C 0.2362(4) 0.3753(11) 0.3161(5) 0.061(2) Uani 1 1 d . . . . .
H4 H 0.2204 0.2899 0.3437 0.073 Uiso 1 1 calc R . . . .
C5 C 0.2868(3) 0.3566(10) 0.2765(6) 0.0529(19) Uani 1 1 d . . . . .
C6 C 0.3089(4) 0.4795(12) 0.2341(7) 0.073(3) Uani 1 1 d . . . . .
H6 H 0.3419 0.4647 0.2059 0.088 Uiso 1 1 calc R . . . .
C7 C 0.2819(4) 0.6273(12) 0.2331(6) 0.066(3) Uani 1 1 d . . . . .
H7 H 0.2978 0.7122 0.2054 0.079 Uiso 1 1 calc R . . . .
C8 C 0.1957(3) 1.1244(10) 0.1338(5) 0.0452(19) Uani 1 1 d . . . . .
C9 C 0.2361(4) 1.0725(12) 0.0708(5) 0.061(2) Uani 1 1 d . . . . .
H9BC H 0.2160 1.0079 0.0326 0.073 Uiso 0.52(3) 1 calc R . P A 2
H9BD H 0.2645 1.0047 0.0945 0.073 Uiso 0.52(3) 1 calc R . P A 2
H9AA H 0.2341 0.9567 0.0646 0.073 Uiso 0.48(3) 1 calc R . P A 1
H9AB H 0.2740 1.0998 0.0867 0.073 Uiso 0.48(3) 1 calc R . P A 1
C11 C 0.2208(4) 1.3295(12) -0.0061(6) 0.070(3) Uani 1 1 d . . . . .
H11C H 0.2398 1.4226 -0.0279 0.084 Uiso 0.52(3) 1 calc R . P A 2
H11D H 0.1996 1.2782 -0.0478 0.084 Uiso 0.52(3) 1 calc R . P A 2
H11A H 0.2073 1.3714 -0.0559 0.084 Uiso 0.48(3) 1 calc R . P A 1
H11B H 0.2581 1.3718 0.0031 0.084 Uiso 0.48(3) 1 calc R . P A 1
C12 C 0.1820(3) 1.3806(10) 0.0596(5) 0.049(2) Uani 1 1 d . . . . .
C13 C 0.1516(3) 1.5273(10) 0.0724(5) 0.049(2) Uani 1 1 d . . . . .
C14 C 0.1448(4) 1.6716(11) 0.0310(6) 0.062(3) Uani 1 1 d . . . . .
H14 H 0.1623 1.6875 -0.0172 0.075 Uiso 1 1 calc R . . . .
C15 C 0.1116(5) 1.7885(12) 0.0634(6) 0.071(3) Uani 1 1 d . . . . .
H15 H 0.1065 1.8842 0.0361 0.085 Uiso 1 1 calc R . . . .
C16 C 0.0856(4) 1.7696(12) 0.1344(6) 0.061(3) Uani 1 1 d . . . . .
H16 H 0.0638 1.8530 0.1542 0.073 Uiso 1 1 calc R . . . .
C17 C 0.0909(3) 1.6293(10) 0.1773(6) 0.053(2) Uani 1 1 d . . . . .
H17 H 0.0733 1.6168 0.2258 0.064 Uiso 1 1 calc R . . . .
C18 C 0.1237(3) 1.5070(9) 0.1450(4) 0.0391(17) Uani 1 1 d . . . . .
C19 C 0.1719(3) 1.2818(10) 0.1215(5) 0.0421(19) Uani 1 1 d . . . . .
C10 C 0.2226(15) 1.155(3) -0.0089(14) 0.079(11) Uani 0.48(3) 1 d . . P A 1
H10A H 0.2506 1.1225 -0.0470 0.094 Uiso 0.48(3) 1 calc R . P A 1
H10B H 0.1866 1.1158 -0.0273 0.094 Uiso 0.48(3) 1 calc R . P A 1
C10A C 0.2646(11) 1.209(3) 0.0285(15) 0.075(9) Uani 0.52(3) 1 d . . P A 2
H10C H 0.2876 1.1665 -0.0137 0.090 Uiso 0.52(3) 1 calc R . P A 2
H10D H 0.2891 1.2655 0.0648 0.090 Uiso 0.52(3) 1 calc R . P A 2
Br2 Br 0.42052(5) 0.82466(13) 0.34271(8) 0.0922(4) Uani 1 1 d . . . . .
O2 O 0.5848(2) 0.1424(7) 0.3223(3) 0.0587(16) Uani 1 1 d . . . . .
N4 N 0.5346(3) 0.0889(8) 0.4304(4) 0.0433(16) Uani 1 1 d . . . . .
H4A H 0.5092 0.1213 0.4628 0.052 Uiso 1 1 calc R . . . .
N5 N 0.5612(3) -0.0569(8) 0.4436(4) 0.0423(15) Uani 1 1 d . . . . .
N6 N 0.6124(3) -0.3613(8) 0.4732(4) 0.0439(16) Uani 1 1 d . . . . .
H6A H 0.6280 -0.3198 0.4324 0.053 Uiso 1 1 calc R . . . .
C20 C 0.5477(3) 0.1798(9) 0.3685(4) 0.0396(18) Uani 1 1 d . . . . .
C21 C 0.5153(3) 0.3338(9) 0.3606(4) 0.0407(18) Uani 1 1 d . . . . .
C22 C 0.5422(3) 0.4709(9) 0.3331(5) 0.0450(18) Uani 1 1 d . . . . .
H22 H 0.5795 0.4655 0.3171 0.054 Uiso 1 1 calc R . . . .
C23 C 0.5137(4) 0.6156(10) 0.3293(5) 0.052(2) Uani 1 1 d . . . . .
H23 H 0.5327 0.7081 0.3139 0.063 Uiso 1 1 calc R . . . .
C24 C 0.4575(4) 0.6246(10) 0.3481(6) 0.059(2) Uani 1 1 d . . . . .
C25 C 0.4300(4) 0.4893(13) 0.3718(6) 0.065(3) Uani 1 1 d . . . . .
H25 H 0.3920 0.4945 0.3839 0.078 Uiso 1 1 calc R . . . .
C26 C 0.4586(4) 0.3416(11) 0.3781(6) 0.057(2) Uani 1 1 d . . . . .
H26 H 0.4395 0.2497 0.3939 0.068 Uiso 1 1 calc R . . . .
C27 C 0.5482(3) -0.1320(10) 0.5068(5) 0.0416(19) Uani 1 1 d . . . . .
C28 C 0.5063(3) -0.0801(10) 0.5700(5) 0.054(2) Uani 1 1 d . . . . .
H28A H 0.5079 0.0358 0.5760 0.065 Uiso 1 1 calc R . . . .
H28B H 0.4687 -0.1080 0.5531 0.065 Uiso 1 1 calc R . . . .
C29 C 0.5178(4) -0.1584(10) 0.6490(5) 0.054(2) Uani 1 1 d . . . . .
H29A H 0.4889 -0.1266 0.6859 0.065 Uiso 1 1 calc R . . . .
H29B H 0.5534 -0.1201 0.6690 0.065 Uiso 1 1 calc R . . . .
C30 C 0.5193(4) -0.3417(10) 0.6437(6) 0.056(2) Uani 1 1 d . . . . .
H30A H 0.5313 -0.3865 0.6936 0.067 Uiso 1 1 calc R . . . .
H30B H 0.4822 -0.3826 0.6321 0.067 Uiso 1 1 calc R . . . .
C31 C 0.5586(3) -0.3902(10) 0.5813(4) 0.0427(18) Uani 1 1 d . . . . .
C32 C 0.5891(3) -0.5365(10) 0.5700(4) 0.0431(18) Uani 1 1 d . . . . .
C33 C 0.5927(4) -0.6856(10) 0.6082(5) 0.052(2) Uani 1 1 d . . . . .
H33 H 0.5714 -0.7041 0.6531 0.062 Uiso 1 1 calc R . . . .
C34 C 0.6273(4) -0.8041(11) 0.5804(6) 0.058(2) Uani 1 1 d . . . . .
H34 H 0.6300 -0.9015 0.6069 0.070 Uiso 1 1 calc R . . . .
C35 C 0.6584(4) -0.7779(11) 0.5117(6) 0.058(2) Uani 1 1 d . . . . .
H35 H 0.6810 -0.8606 0.4929 0.070 Uiso 1 1 calc R . . . .
C36 C 0.6570(4) -0.6352(11) 0.4710(5) 0.052(2) Uani 1 1 d . . . . .
H36 H 0.6779 -0.6197 0.4255 0.063 Uiso 1 1 calc R . . . .
C37 C 0.6221(3) -0.5134(9) 0.5018(4) 0.0409(18) Uani 1 1 d . . . . .
C38 C 0.5734(3) -0.2864(10) 0.5203(5) 0.0408(19) 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 0.0033 0.0016 '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 -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
N2 N1 H1 119(5) . . ?
C1 N1 H1 119(5) . . ?
C1 N1 N2 121.0(7) . . ?
C8 N2 N1 115.7(6) . . ?
C18 N3 H3 125.8 . . ?
C18 N3 C19 108.4(6) . . ?
C19 N3 H3 125.8 . . ?
O1 C1 N1 122.5(8) . . ?
O1 C1 C2 123.3(8) . . ?
N1 C1 C2 114.2(7) . . ?
C3 C2 C1 118.8(7) . . ?
C3 C2 C7 118.1(8) . . ?
C7 C2 C1 123.2(7) . . ?
C2 C3 H3A 119.3 . . ?
C2 C3 C4 121.5(8) . . ?
C4 C3 H3A 119.3 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.8(8) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 Br1 118.9(7) . . ?
C6 C5 Br1 120.4(7) . . ?
C6 C5 C4 120.7(8) . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.5(8) . . ?
C7 C6 H6 120.2 . . ?
C2 C7 C6 121.4(8) . . ?
C2 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
N2 C8 C9 126.5(7) . . ?
N2 C8 C19 119.1(7) . . ?
C19 C8 C9 114.2(7) . . ?
C8 C9 H9BC 108.7 . . ?
C8 C9 H9BD 108.7 . . ?
C8 C9 H9AA 109.4 . . ?
C8 C9 H9AB 109.4 . . ?
C8 C9 C10 111.2(11) . . ?
C8 C9 C10A 114.4(10) . . ?
H9BC C9 H9BD 107.6 . . ?
H9AA C9 H9AB 108.0 . . ?
C10 C9 H9AA 109.4 . . ?
C10 C9 H9AB 109.4 . . ?
C10A C9 H9BC 108.7 . . ?
C10A C9 H9BD 108.7 . . ?
H11C C11 H11D 108.4 . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 H11C 110.1 . . ?
C12 C11 H11D 110.1 . . ?
C12 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
C12 C11 C10A 108.1(10) . . ?
C10 C11 H11A 109.9 . . ?
C10 C11 H11B 109.9 . . ?
C10 C11 C12 108.8(11) . . ?
C10A C11 H11C 110.1 . . ?
C10A C11 H11D 110.1 . . ?
C13 C12 C11 131.4(8) . . ?
C19 C12 C11 120.8(8) . . ?
C19 C12 C13 107.8(7) . . ?
C14 C13 C12 135.1(8) . . ?
C14 C13 C18 119.2(8) . . ?
C18 C13 C12 105.6(7) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 C13 118.1(9) . . ?
C15 C14 H14 120.9 . . ?
C14 C15 H15 118.8 . . ?
C16 C15 C14 122.5(9) . . ?
C16 C15 H15 118.8 . . ?
C15 C16 H16 119.3 . . ?
C15 C16 C17 121.5(10) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 H17 121.4 . . ?
C16 C17 C18 117.3(9) . . ?
C18 C17 H17 121.4 . . ?
N3 C18 C13 108.8(7) . . ?
N3 C18 C17 129.8(7) . . ?
C17 C18 C13 121.4(8) . . ?
N3 C19 C8 124.4(7) . . ?
C12 C19 N3 109.3(7) . . ?
C12 C19 C8 126.3(7) . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
C11 C10 C9 115(2) . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C9 C10A C11 111.2(17) . . ?
C9 C10A H10C 109.4 . . ?
C9 C10A H10D 109.4 . . ?
C11 C10A H10C 109.4 . . ?
C11 C10A H10D 109.4 . . ?
H10C C10A H10D 108.0 . . ?
N5 N4 H4A 119.5 . . ?
C20 N4 H4A 119.5 . . ?
C20 N4 N5 121.0(6) . . ?
C27 N5 N4 116.7(6) . . ?
C37 N6 H6A 125.5 . . ?
C38 N6 H6A 125.5 . . ?
C38 N6 C37 109.0(7) . . ?
O2 C20 N4 122.1(7) . . ?
O2 C20 C21 122.1(7) . . ?
N4 C20 C21 115.7(7) . . ?
C22 C21 C20 119.6(7) . . ?
C26 C21 C20 121.5(7) . . ?
C26 C21 C22 118.9(7) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.1(7) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 119.5 . . ?
C24 C23 C22 121.0(8) . . ?
C24 C23 H23 119.5 . . ?
C23 C24 Br2 119.4(7) . . ?
C25 C24 Br2 121.2(7) . . ?
C25 C24 C23 119.4(8) . . ?
C24 C25 H25 119.7 . . ?
C24 C25 C26 120.6(8) . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 119.8(8) . . ?
C21 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
N5 C27 C28 127.6(7) . . ?
N5 C27 C38 117.9(7) . . ?
C38 C27 C28 114.5(7) . . ?
C27 C28 H28A 109.1 . . ?
C27 C28 H28B 109.1 . . ?
H28A C28 H28B 107.8 . . ?
C29 C28 C27 112.5(6) . . ?
C29 C28 H28A 109.1 . . ?
C29 C28 H28B 109.1 . . ?
C28 C29 H29A 109.1 . . ?
C28 C29 H29B 109.1 . . ?
C28 C29 C30 112.4(7) . . ?
H29A C29 H29B 107.9 . . ?
C30 C29 H29A 109.1 . . ?
C30 C29 H29B 109.1 . . ?
C29 C30 H30A 109.8 . . ?
C29 C30 H30B 109.8 . . ?
H30A C30 H30B 108.3 . . ?
C31 C30 C29 109.3(7) . . ?
C31 C30 H30A 109.8 . . ?
C31 C30 H30B 109.8 . . ?
C32 C31 C30 130.8(7) . . ?
C38 C31 C30 121.9(7) . . ?
C38 C31 C32 107.3(7) . . ?
C33 C32 C31 136.2(8) . . ?
C33 C32 C37 117.7(7) . . ?
C37 C32 C31 106.1(7) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 C32 120.9(8) . . ?
C34 C33 H33 119.6 . . ?
C33 C34 H34 120.1 . . ?
C33 C34 C35 119.7(9) . . ?
C35 C34 H34 120.1 . . ?
C34 C35 H35 118.6 . . ?
C36 C35 C34 122.7(9) . . ?
C36 C35 H35 118.6 . . ?
C35 C36 H36 121.7 . . ?
C35 C36 C37 116.6(8) . . ?
C37 C36 H36 121.7 . . ?
N6 C37 C32 108.7(7) . . ?
N6 C37 C36 128.9(8) . . ?
C36 C37 C32 122.4(7) . . ?
N6 C38 C27 126.5(8) . . ?
N6 C38 C31 108.9(7) . . ?
C31 C38 C27 124.5(7) . . ?
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
Br1 C5 1.914(8) . ?
O1 C1 1.216(9) . ?
N1 H1 0.94(8) . ?
N1 N2 1.384(9) . ?
N1 C1 1.368(11) . ?
N2 C8 1.299(10) . ?
N3 H3 0.8600 . ?
N3 C18 1.364(9) . ?
N3 C19 1.390(10) . ?
C1 C2 1.497(10) . ?
C2 C3 1.379(11) . ?
C2 C7 1.382(11) . ?
C3 H3A 0.9300 . ?
C3 C4 1.386(12) . ?
C4 H4 0.9300 . ?
C4 C5 1.391(12) . ?
C5 C6 1.358(13) . ?
C6 H6 0.9300 . ?
C6 C7 1.389(13) . ?
C7 H7 0.9300 . ?
C8 C9 1.504(11) . ?
C8 C19 1.442(11) . ?
C9 H9BC 0.9700 . ?
C9 H9BD 0.9700 . ?
C9 H9AA 0.9700 . ?
C9 H9AB 0.9700 . ?
C9 C10 1.55(3) . ?
C9 C10A 1.51(2) . ?
C11 H11C 0.9700 . ?
C11 H11D 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.512(13) . ?
C11 C10 1.45(3) . ?
C11 C10A 1.56(3) . ?
C12 C13 1.437(11) . ?
C12 C19 1.358(11) . ?
C13 C14 1.402(12) . ?
C13 C18 1.412(11) . ?
C14 H14 0.9300 . ?
C14 C15 1.371(14) . ?
C15 H15 0.9300 . ?
C15 C16 1.365(15) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(13) . ?
C17 H17 0.9300 . ?
C17 C18 1.397(11) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10A H10C 0.9700 . ?
C10A H10D 0.9700 . ?
Br2 C24 1.885(9) . ?
O2 C20 1.223(9) . ?
N4 H4A 0.8600 . ?
N4 N5 1.387(8) . ?
N4 C20 1.334(9) . ?
N5 C27 1.282(9) . ?
N6 H6A 0.8600 . ?
N6 C37 1.376(9) . ?
N6 C38 1.376(10) . ?
C20 C21 1.501(10) . ?
C21 C22 1.390(10) . ?
C21 C26 1.388(11) . ?
C22 H22 0.9300 . ?
C22 C23 1.384(11) . ?
C23 H23 0.9300 . ?
C23 C24 1.381(12) . ?
C24 C25 1.364(13) . ?
C25 H25 0.9300 . ?
C25 C26 1.409(12) . ?
C26 H26 0.9300 . ?
C27 C28 1.531(11) . ?
C27 C38 1.437(11) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.517(12) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.528(11) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C31 1.472(11) . ?
C31 C32 1.431(11) . ?
C31 C38 1.395(12) . ?
C32 C33 1.403(11) . ?
C32 C37 1.415(10) . ?
C33 H33 0.9300 . ?
C33 C34 1.369(12) . ?
C34 H34 0.9300 . ?
C34 C35 1.401(14) . ?
C35 H35 0.9300 . ?
C35 C36 1.375(13) . ?
C36 H36 0.9300 . ?
C36 C37 1.412(11) . ?
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
N3 H3 O2 0.86 2.04 2.805(8) 147.3 4_465
C3 H3A O2 0.93 2.66 3.285(10) 125.3 4_455
C17 H17 O2 0.93 2.72 3.348(11) 125.2 4_465
N6 H6A O1 0.86 2.10 2.866(8) 148.8 4
