#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/19/2221957.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2221957
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Quah, Ching Kheng'
'Sujith, K. V.'
'Kalluraya, B.'
_publ_section_title
N'-[(E)-4-Bromobenzylidene]-2-(4-isobutylphenyl)propanohydrazide
_journal_coeditor_code           CI2787
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1184
_journal_page_last               o1185
_journal_paper_doi               10.1107/S1600536809015542
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H23 Br N2 O'
_chemical_formula_moiety         'C20 H23 Br N2 O'
_chemical_formula_sum            'C20 H23 Br N2 O'
_chemical_formula_weight         387.31
_chemical_name_systematic
;
N'-[(E)-4-Bromobenzylidene]-2-(4-isobutylphenyl)propanohydrazide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.14400(10)
_cell_length_b                   12.01100(10)
_cell_length_c                   33.5670(4)
_cell_measurement_reflns_used    9400
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      31.65
_cell_measurement_theta_min      2.54
_cell_volume                     3686.62(7)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0588
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_limit_l_min       -58
_diffrn_reflns_number            120355
_diffrn_reflns_theta_full        38.57
_diffrn_reflns_theta_max         38.57
_diffrn_reflns_theta_min         1.21
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.239
_exptl_absorpt_correction_T_max  0.6822
_exptl_absorpt_correction_T_min  0.4067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.376
_exptl_crystal_size_min          0.185
_refine_diff_density_max         0.715
_refine_diff_density_min         -0.615
_refine_ls_abs_structure_details 'Flack (1983), 9205 Friedel pairs'
_refine_ls_abs_structure_Flack   0.595(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     448
_refine_ls_number_reflns         20557
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0416
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0498P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.1026
_reflns_number_gt                13317
_reflns_number_total             20557
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2787.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2221957
_cod_database_fobs_code          2221957
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1A 0.849271(19) 0.479672(14) 0.078235(6) 0.02563(4) Uani d . 1 . .
O O1A 0.88325(12) 1.00346(11) 0.27706(3) 0.0213(2) Uani d . 1 . .
N N1A 0.73139(15) 0.87330(12) 0.22421(4) 0.0173(3) Uani d . 1 . .
N N2A 0.66653(15) 0.94990(12) 0.24939(4) 0.0164(3) Uani d . 1 . .
C C1A 0.81210(19) 0.67440(14) 0.17959(5) 0.0184(3) Uani d . 1 . .
H H1AA 0.8601 0.6813 0.2039 0.022 Uiso calc R 1 . .
C C2A 0.85669(18) 0.59430(13) 0.15259(5) 0.0187(3) Uani d . 1 . .
H H2AA 0.9328 0.5460 0.1589 0.022 Uiso calc R 1 . .
C C3A 0.78674(19) 0.58675(14) 0.11603(5) 0.0189(3) Uani d . 1 . .
C C4A 0.6703(2) 0.65496(14) 0.10623(5) 0.0211(3) Uani d . 1 . .
H H4AA 0.6243 0.6487 0.0816 0.025 Uiso calc R 1 . .
C C5A 0.62366(19) 0.73315(14) 0.13401(5) 0.0192(3) Uani d . 1 . .
H H5AA 0.5437 0.7781 0.1281 0.023 Uiso calc R 1 . .
C C6A 0.6946(2) 0.74535(13) 0.17050(5) 0.0165(3) Uani d . 1 . .
C C7A 0.64467(19) 0.83222(13) 0.19787(5) 0.0176(3) Uani d . 1 . .
H H7AA 0.5490 0.8581 0.1962 0.021 Uiso calc R 1 . .
C C8A 0.74894(16) 1.00775(15) 0.27548(5) 0.0170(3) Uani d . 1 . .
C C9A 0.65950(18) 1.07453(13) 0.30584(5) 0.0172(3) Uani d . 1 . .
H H9AA 0.5624 1.0888 0.2946 0.021 Uiso calc R 1 . .
C C10A 0.64245(16) 0.99942(13) 0.34220(4) 0.0155(3) Uani d . 1 . .
C C11A 0.51587(18) 0.93583(14) 0.34705(5) 0.0185(3) Uani d . 1 . .
H H11A 0.4397 0.9428 0.3289 0.022 Uiso calc R 1 . .
C C12A 0.50265(19) 0.86228(13) 0.37874(5) 0.0182(3) Uani d . 1 . .
H H12A 0.4167 0.8217 0.3817 0.022 Uiso calc R 1 . .
C C13A 0.61539(18) 0.84797(13) 0.40622(4) 0.0172(3) Uani d . 1 . .
C C14A 0.74046(17) 0.91272(14) 0.40148(5) 0.0204(3) Uani d . 1 . .
H H14A 0.8167 0.9056 0.4196 0.025 Uiso calc R 1 . .
C C15A 0.75390(17) 0.98781(15) 0.37016(5) 0.0200(3) Uani d . 1 . .
H H15A 0.8382 1.0307 0.3679 0.024 Uiso calc R 1 . .
C C16A 0.60190(19) 0.76581(13) 0.43996(5) 0.0194(3) Uani d . 1 . .
H H16A 0.6991 0.7508 0.4502 0.023 Uiso calc R 1 . .
H H16B 0.5640 0.6965 0.4293 0.023 Uiso calc R 1 . .
C C17A 0.50438(19) 0.80147(14) 0.47485(5) 0.0219(3) Uani d . 1 . .
H H17A 0.4035 0.8064 0.4652 0.026 Uiso calc R 1 . .
C C18A 0.5468(3) 0.91335(16) 0.49144(6) 0.0442(6) Uani d . 1 . .
H H18A 0.5341 0.9693 0.4713 0.066 Uiso calc R 1 . .
H H18B 0.6473 0.9116 0.4997 0.066 Uiso calc R 1 . .
H H18C 0.4859 0.9305 0.5139 0.066 Uiso calc R 1 . .
C C19A 0.5104(2) 0.71186(15) 0.50728(5) 0.0274(4) Uani d . 1 . .
H H19A 0.4477 0.7328 0.5290 0.041 Uiso calc R 1 . .
H H19B 0.6090 0.7046 0.5168 0.041 Uiso calc R 1 . .
H H19C 0.4784 0.6420 0.4964 0.041 Uiso calc R 1 . .
C C20A 0.73368(19) 1.18646(15) 0.31432(6) 0.0229(4) Uani d . 1 . .
H H20A 0.6876 1.2212 0.3368 0.034 Uiso calc R 1 . .
H H20B 0.7246 1.2339 0.2914 0.034 Uiso calc R 1 . .
H H20C 0.8353 1.1744 0.3200 0.034 Uiso calc R 1 . .
Br Br1B 0.63994(2) -0.015149(14) 0.077318(5) 0.02449(4) Uani d . 1 . .
O O1B 0.61864(12) 0.49983(11) 0.27805(3) 0.0206(2) Uani d . 1 . .
N N1B 0.77028(15) 0.36554(11) 0.22662(4) 0.0161(3) Uani d . 1 . .
N N2B 0.83490(16) 0.44565(12) 0.25061(4) 0.0165(3) Uani d . 1 . .
C C1B 0.68109(19) 0.17270(13) 0.18046(5) 0.0175(3) Uani d . 1 . .
H H1BA 0.6314 0.1809 0.2045 0.021 Uiso calc R 1 . .
C C2B 0.63144(18) 0.09615(13) 0.15256(5) 0.0183(3) Uani d . 1 . .
H H2BA 0.5492 0.0529 0.1577 0.022 Uiso calc R 1 . .
C C3B 0.7075(2) 0.08541(13) 0.11670(5) 0.0190(3) Uani d . 1 . .
C C4B 0.83235(19) 0.14694(13) 0.10867(5) 0.0190(3) Uani d . 1 . .
H H4BA 0.8824 0.1379 0.0848 0.023 Uiso calc R 1 . .
C C5B 0.88101(19) 0.22226(13) 0.13705(5) 0.0180(3) Uani d . 1 . .
H H5BA 0.9654 0.2633 0.1323 0.022 Uiso calc R 1 . .
C C6B 0.8045(2) 0.23731(13) 0.17286(5) 0.0164(3) Uani d . 1 . .
C C7B 0.85619(19) 0.32373(13) 0.20041(5) 0.0175(3) Uani d . 1 . .
H H7BA 0.9524 0.3484 0.1988 0.021 Uiso calc R 1 . .
C C8B 0.75320(16) 0.50621(14) 0.27594(4) 0.0153(3) Uani d . 1 . .
C C9B 0.84083(18) 0.58372(12) 0.30309(4) 0.0144(3) Uani d . 1 . .
H H9BA 0.9371 0.5957 0.2910 0.017 Uiso calc R 1 . .
C C10B 0.86268(16) 0.52286(12) 0.34255(4) 0.0146(3) Uani d . 1 . .
C C11B 0.96862(18) 0.43906(13) 0.34546(5) 0.0165(3) Uani d . 1 . .
H H11B 1.0261 0.4219 0.3234 0.020 Uiso calc R 1 . .
C C12B 0.98872(19) 0.38154(13) 0.38080(5) 0.0188(3) Uani d . 1 . .
H H12B 1.0601 0.3265 0.3821 0.023 Uiso calc R 1 . .
C C13B 0.90454(18) 0.40422(13) 0.41439(5) 0.0182(3) Uani d . 1 . .
C C14B 0.80027(18) 0.48834(14) 0.41132(5) 0.0205(3) Uani d . 1 . .
H H14B 0.7433 0.5056 0.4334 0.025 Uiso calc R 1 . .
C C15B 0.77918(18) 0.54699(13) 0.37620(5) 0.0182(3) Uani d . 1 . .
H H15B 0.7088 0.6028 0.3751 0.022 Uiso calc R 1 . .
C C16B 0.9216(2) 0.33528(14) 0.45152(5) 0.0215(3) Uani d . 1 . .
H H16C 0.8740 0.3733 0.4735 0.026 Uiso calc R 1 . .
H H16D 1.0248 0.3293 0.4579 0.026 Uiso calc R 1 . .
C C17B 0.85697(19) 0.21766(13) 0.44763(5) 0.0195(3) Uani d . 1 . .
H H17B 0.9058 0.1806 0.4253 0.023 Uiso calc R 1 . .
C C18B 0.8867(2) 0.14987(15) 0.48509(5) 0.0313(4) Uani d . 1 . .
H H18D 0.8488 0.0759 0.4817 0.047 Uiso calc R 1 . .
H H18E 0.8399 0.1847 0.5075 0.047 Uiso calc R 1 . .
H H18F 0.9902 0.1463 0.4897 0.047 Uiso calc R 1 . .
C C19B 0.6939(2) 0.22087(16) 0.43873(6) 0.0285(4) Uani d . 1 . .
H H19D 0.6584 0.1464 0.4350 0.043 Uiso calc R 1 . .
H H19E 0.6771 0.2634 0.4149 0.043 Uiso calc R 1 . .
H H19F 0.6432 0.2549 0.4606 0.043 Uiso calc R 1 . .
C C20B 0.76379(18) 0.69647(14) 0.30640(5) 0.0190(3) Uani d . 1 . .
H H20D 0.8130 0.7416 0.3258 0.029 Uiso calc R 1 . .
H H20E 0.6641 0.6853 0.3144 0.029 Uiso calc R 1 . .
H H20F 0.7659 0.7332 0.2810 0.029 Uiso calc R 1 . .
H H1NA 0.568(2) 0.9602(19) 0.2475(6) 0.034(6) Uiso d . 1 . .
H H1NB 0.918(2) 0.4564(18) 0.2501(6) 0.022(6) Uiso d . 1 . .
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 0.0000 '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 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7A N1A N2A . . 114.27(13) ?
C8A N2A N1A . . 120.01(13) ?
C8A N2A H1NA . . 121.9(14) ?
N1A N2A H1NA . . 118.1(14) ?
C2A C1A C6A . . 120.33(16) ?
C2A C1A H1AA . . 119.8 ?
C6A C1A H1AA . . 119.8 ?
C1A C2A C3A . . 119.30(15) ?
C1A C2A H2AA . . 120.3 ?
C3A C2A H2AA . . 120.3 ?
C4A C3A C2A . . 121.77(15) ?
C4A C3A Br1A . . 118.38(13) ?
C2A C3A Br1A . . 119.85(13) ?
C3A C4A C5A . . 118.49(16) ?
C3A C4A H4AA . . 120.8 ?
C5A C4A H4AA . . 120.8 ?
C4A C5A C6A . . 121.17(16) ?
C4A C5A H5AA . . 119.4 ?
C6A C5A H5AA . . 119.4 ?
C5A C6A C1A . . 118.87(15) ?
C5A C6A C7A . . 118.81(16) ?
C1A C6A C7A . . 122.32(15) ?
N1A C7A C6A . . 120.87(16) ?
N1A C7A H7AA . . 119.6 ?
C6A C7A H7AA . . 119.6 ?
O1A C8A N2A . . 124.37(16) ?
O1A C8A C9A . . 121.71(15) ?
N2A C8A C9A . . 113.78(13) ?
C10A C9A C20A . . 114.55(13) ?
C10A C9A C8A . . 106.07(12) ?
C20A C9A C8A . . 110.26(14) ?
C10A C9A H9AA . . 108.6 ?
C20A C9A H9AA . . 108.6 ?
C8A C9A H9AA . . 108.6 ?
C15A C10A C11A . . 118.25(14) ?
C15A C10A C9A . . 121.57(14) ?
C11A C10A C9A . . 120.10(14) ?
C12A C11A C10A . . 120.65(15) ?
C12A C11A H11A . . 119.7 ?
C10A C11A H11A . . 119.7 ?
C11A C12A C13A . . 121.41(15) ?
C11A C12A H12A . . 119.3 ?
C13A C12A H12A . . 119.3 ?
C14A C13A C12A . . 117.58(14) ?
C14A C13A C16A . . 121.26(15) ?
C12A C13A C16A . . 121.16(15) ?
C15A C14A C13A . . 121.43(15) ?
C15A C14A H14A . . 119.3 ?
C13A C14A H14A . . 119.3 ?
C14A C15A C10A . . 120.65(15) ?
C14A C15A H15A . . 119.7 ?
C10A C15A H15A . . 119.7 ?
C13A C16A C17A . . 116.02(13) ?
C13A C16A H16A . . 108.3 ?
C17A C16A H16A . . 108.3 ?
C13A C16A H16B . . 108.3 ?
C17A C16A H16B . . 108.3 ?
H16A C16A H16B . . 107.4 ?
C18A C17A C19A . . 110.80(15) ?
C18A C17A C16A . . 112.47(16) ?
C19A C17A C16A . . 109.00(14) ?
C18A C17A H17A . . 108.1 ?
C19A C17A H17A . . 108.1 ?
C16A C17A H17A . . 108.1 ?
C17A C18A H18A . . 109.5 ?
C17A C18A H18B . . 109.5 ?
H18A C18A H18B . . 109.5 ?
C17A C18A H18C . . 109.5 ?
H18A C18A H18C . . 109.5 ?
H18B C18A H18C . . 109.5 ?
C17A C19A H19A . . 109.5 ?
C17A C19A H19B . . 109.5 ?
H19A C19A H19B . . 109.5 ?
C17A C19A H19C . . 109.5 ?
H19A C19A H19C . . 109.5 ?
H19B C19A H19C . . 109.5 ?
C9A C20A H20A . . 109.5 ?
C9A C20A H20B . . 109.5 ?
H20A C20A H20B . . 109.5 ?
C9A C20A H20C . . 109.5 ?
H20A C20A H20C . . 109.5 ?
H20B C20A H20C . . 109.5 ?
C7B N1B N2B . . 114.15(13) ?
C8B N2B N1B . . 120.36(13) ?
C8B N2B H1NB . . 118.0(16) ?
N1B N2B H1NB . . 121.7(16) ?
C2B C1B C6B . . 120.66(15) ?
C2B C1B H1BA . . 119.7 ?
C6B C1B H1BA . . 119.7 ?
C1B C2B C3B . . 118.66(16) ?
C1B C2B H2BA . . 120.7 ?
C3B C2B H2BA . . 120.7 ?
C4B C3B C2B . . 121.92(15) ?
C4B C3B Br1B . . 118.22(12) ?
C2B C3B Br1B . . 119.86(13) ?
C3B C4B C5B . . 118.57(15) ?
C3B C4B H4BA . . 120.7 ?
C5B C4B H4BA . . 120.7 ?
C4B C5B C6B . . 120.84(16) ?
C4B C5B H5BA . . 119.6 ?
C6B C5B H5BA . . 119.6 ?
C1B C6B C5B . . 119.29(15) ?
C1B C6B C7B . . 122.62(15) ?
C5B C6B C7B . . 118.06(16) ?
N1B C7B C6B . . 120.80(16) ?
N1B C7B H7BA . . 119.6 ?
C6B C7B H7BA . . 119.6 ?
O1B C8B N2B . . 123.79(15) ?
O1B C8B C9B . . 121.70(15) ?
N2B C8B C9B . . 114.50(13) ?
C10B C9B C8B . . 107.11(12) ?
C10B C9B C20B . . 114.91(13) ?
C8B C9B C20B . . 109.92(13) ?
C10B C9B H9BA . . 108.2 ?
C8B C9B H9BA . . 108.2 ?
C20B C9B H9BA . . 108.2 ?
C15B C10B C11B . . 118.15(14) ?
C15B C10B C9B . . 122.14(13) ?
C11B C10B C9B . . 119.70(13) ?
C12B C11B C10B . . 120.68(15) ?
C12B C11B H11B . . 119.7 ?
C10B C11B H11B . . 119.7 ?
C11B C12B C13B . . 121.51(15) ?
C11B C12B H12B . . 119.2 ?
C13B C12B H12B . . 119.2 ?
C12B C13B C14B . . 117.42(14) ?
C12B C13B C16B . . 120.39(15) ?
C14B C13B C16B . . 122.10(15) ?
C15B C14B C13B . . 121.77(15) ?
C15B C14B H14B . . 119.1 ?
C13B C14B H14B . . 119.1 ?
C14B C15B C10B . . 120.47(15) ?
C14B C15B H15B . . 119.8 ?
C10B C15B H15B . . 119.8 ?
C13B C16B C17B . . 113.29(13) ?
C13B C16B H16C . . 108.9 ?
C17B C16B H16C . . 108.9 ?
C13B C16B H16D . . 108.9 ?
C17B C16B H16D . . 108.9 ?
H16C C16B H16D . . 107.7 ?
C19B C17B C18B . . 110.54(15) ?
C19B C17B C16B . . 111.74(15) ?
C18B C17B C16B . . 110.65(13) ?
C19B C17B H17B . . 107.9 ?
C18B C17B H17B . . 107.9 ?
C16B C17B H17B . . 107.9 ?
C17B C18B H18D . . 109.5 ?
C17B C18B H18E . . 109.5 ?
H18D C18B H18E . . 109.5 ?
C17B C18B H18F . . 109.5 ?
H18D C18B H18F . . 109.5 ?
H18E C18B H18F . . 109.5 ?
C17B C19B H19D . . 109.5 ?
C17B C19B H19E . . 109.5 ?
H19D C19B H19E . . 109.5 ?
C17B C19B H19F . . 109.5 ?
H19D C19B H19F . . 109.5 ?
H19E C19B H19F . . 109.5 ?
C9B C20B H20D . . 109.5 ?
C9B C20B H20E . . 109.5 ?
H20D C20B H20E . . 109.5 ?
C9B C20B H20F . . 109.5 ?
H20D C20B H20F . . 109.5 ?
H20E C20B H20F . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1A C3A . 1.8948(17) ?
O1A C8A . 1.2304(19) ?
N1A C7A . 1.286(2) ?
N1A N2A . 1.3830(18) ?
N2A C8A . 1.348(2) ?
N2A H1NA . 0.91(2) ?
C1A C2A . 1.383(2) ?
C1A C6A . 1.405(3) ?
C1A H1AA . 0.93 ?
C2A C3A . 1.387(2) ?
C2A H2AA . 0.93 ?
C3A C4A . 1.383(2) ?
C4A C5A . 1.390(2) ?
C4A H4AA . 0.93 ?
C5A C6A . 1.394(2) ?
C5A H5AA . 0.93 ?
C6A C7A . 1.463(2) ?
C7A H7AA . 0.93 ?
C8A C9A . 1.533(2) ?
C9A C10A . 1.526(2) ?
C9A C20A . 1.532(2) ?
C9A H9AA . 0.98 ?
C10A C15A . 1.393(2) ?
C10A C11A . 1.396(2) ?
C11A C12A . 1.388(2) ?
C11A H11A . 0.93 ?
C12A C13A . 1.394(2) ?
C12A H12A . 0.93 ?
C13A C14A . 1.392(2) ?
C13A C16A . 1.507(2) ?
C14A C15A . 1.390(2) ?
C14A H14A . 0.93 ?
C15A H15A . 0.93 ?
C16A C17A . 1.533(2) ?
C16A H16A . 0.97 ?
C16A H16B . 0.97 ?
C17A C18A . 1.505(3) ?
C17A C19A . 1.532(2) ?
C17A H17A . 0.98 ?
C18A H18A . 0.96 ?
C18A H18B . 0.96 ?
C18A H18C . 0.96 ?
C19A H19A . 0.96 ?
C19A H19B . 0.96 ?
C19A H19C . 0.96 ?
C20A H20A . 0.96 ?
C20A H20B . 0.96 ?
C20A H20C . 0.96 ?
Br1B C3B . 1.8944(16) ?
O1B C8B . 1.2349(18) ?
N1B C7B . 1.282(2) ?
N1B N2B . 1.3868(18) ?
N2B C8B . 1.345(2) ?
N2B H1NB . 0.770(19) ?
C1B C2B . 1.389(2) ?
C1B C6B . 1.393(3) ?
C1B H1BA . 0.93 ?
C2B C3B . 1.396(2) ?
C2B H2BA . 0.93 ?
C3B C4B . 1.386(2) ?
C4B C5B . 1.387(2) ?
C4B H4BA . 0.93 ?
C5B C6B . 1.403(2) ?
C5B H5BA . 0.93 ?
C6B C7B . 1.468(2) ?
C7B H7BA . 0.93 ?
C8B C9B . 1.530(2) ?
C9B C10B . 1.526(2) ?
C9B C20B . 1.531(2) ?
C9B H9BA . 0.98 ?
C10B C15B . 1.394(2) ?
C10B C11B . 1.400(2) ?
C11B C12B . 1.385(2) ?
C11B H11B . 0.93 ?
C12B C13B . 1.392(2) ?
C12B H12B . 0.93 ?
C13B C14B . 1.393(2) ?
C13B C16B . 1.505(2) ?
C14B C15B . 1.387(2) ?
C14B H14B . 0.93 ?
C15B H15B . 0.93 ?
C16B C17B . 1.537(2) ?
C16B H16C . 0.97 ?
C16B H16D . 0.97 ?
C17B C19B . 1.522(3) ?
C17B C18B . 1.523(2) ?
C17B H17B . 0.98 ?
C18B H18D . 0.96 ?
C18B H18E . 0.96 ?
C18B H18F . 0.96 ?
C19B H19D . 0.96 ?
C19B H19E . 0.96 ?
C19B H19F . 0.96 ?
C20B H20D . 0.96 ?
C20B H20E . 0.96 ?
C20B H20F . 0.96 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2A H1NA O1B 3_655 0.91(2) 1.97(2) 2.830(2) 157(2) yes
N2B H1NB O1A 3_745 0.77(2) 2.11(2) 2.826(2) 155(2) yes
C7A H7AA O1B 3_655 0.93 2.45 3.241(2) 143 yes
C7B H7BA O1A 3_745 0.93 2.53 3.307(3) 141 yes
C20B H20F N1A . 0.96 2.56 3.494(2) 164 yes
C12A H12A Cg2 3_655 0.93 2.66 3.482(2) 148 yes
C12B H12B Cg1 3_745 0.93 2.79 3.680(2) 160 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7A N1A N2A C8A . . . . -172.90(15) ?
C6A C1A C2A C3A . . . . 1.7(3) ?
C1A C2A C3A C4A . . . . -2.0(3) ?
C1A C2A C3A Br1A . . . . 178.62(12) ?
C2A C3A C4A C5A . . . . 0.3(3) ?
Br1A C3A C4A C5A . . . . 179.62(13) ?
C3A C4A C5A C6A . . . . 1.8(3) ?
C4A C5A C6A C1A . . . . -2.1(3) ?
C4A C5A C6A C7A . . . . 177.39(16) ?
C2A C1A C6A C5A . . . . 0.3(3) ?
C2A C1A C6A C7A . . . . -179.19(15) ?
N2A N1A C7A C6A . . . . -176.44(13) ?
C5A C6A C7A N1A . . . . -155.46(16) ?
C1A C6A C7A N1A . . . . 24.0(2) ?
N1A N2A C8A O1A . . . . 5.2(3) ?
N1A N2A C8A C9A . . . . -170.40(13) ?
O1A C8A C9A C10A . . . . -82.77(19) ?
N2A C8A C9A C10A . . . . 93.00(16) ?
O1A C8A C9A C20A . . . . 41.8(2) ?
N2A C8A C9A C20A . . . . -142.45(15) ?
C8A C9A C10A C11A . . . . -96.54(17) y
C8A C9A C10A C15A . . . . 80.18(18) y
C20A C9A C10A C11A . . . . 141.61(15) y
C20A C9A C10A C15A . . . . -41.7(2) y
C15A C10A C11A C12A . . . . -0.6(2) ?
C9A C10A C11A C12A . . . . 176.19(15) ?
C10A C11A C12A C13A . . . . -1.1(2) ?
C11A C12A C13A C14A . . . . 1.9(2) ?
C11A C12A C13A C16A . . . . -178.41(14) ?
C12A C13A C14A C15A . . . . -1.0(2) ?
C16A C13A C14A C15A . . . . 179.36(15) ?
C13A C14A C15A C10A . . . . -0.8(3) ?
C11A C10A C15A C14A . . . . 1.6(2) ?
C9A C10A C15A C14A . . . . -175.20(15) ?
C14A C13A C16A C17A . . . . 103.66(19) ?
C12A C13A C16A C17A . . . . -76.0(2) ?
C13A C16A C17A C18A . . . . -53.4(2) ?
C13A C16A C17A C19A . . . . -176.68(15) ?
C7B N1B N2B C8B . . . . 171.64(15) ?
C6B C1B C2B C3B . . . . -0.1(2) ?
C1B C2B C3B C4B . . . . 1.5(2) ?
C1B C2B C3B Br1B . . . . -178.25(12) ?
C2B C3B C4B C5B . . . . -0.9(2) ?
Br1B C3B C4B C5B . . . . 178.82(12) ?
C3B C4B C5B C6B . . . . -1.0(2) ?
C2B C1B C6B C5B . . . . -1.7(2) ?
C2B C1B C6B C7B . . . . 176.39(15) ?
C4B C5B C6B C1B . . . . 2.3(2) ?
C4B C5B C6B C7B . . . . -175.90(14) ?
N2B N1B C7B C6B . . . . 179.61(13) ?
C1B C6B C7B N1B . . . . -20.0(2) ?
C5B C6B C7B N1B . . . . 158.13(15) ?
N1B N2B C8B O1B . . . . -4.2(3) ?
N1B N2B C8B C9B . . . . 174.74(13) ?
O1B C8B C9B C10B . . . . 82.66(19) ?
N2B C8B C9B C10B . . . . -96.26(16) ?
O1B C8B C9B C20B . . . . -42.8(2) ?
N2B C8B C9B C20B . . . . 138.28(14) ?
C8B C9B C10B C11B . . . . 77.53(17) y
C8B C9B C10B C15B . . . . -101.83(16) y
C20B C9B C10B C11B . . . . -160.06(14) y
C20B C9B C10B C15B . . . . 20.6(2) y
C15B C10B C11B C12B . . . . 0.4(2) ?
C9B C10B C11B C12B . . . . -178.97(15) ?
C10B C11B C12B C13B . . . . 0.4(2) ?
C11B C12B C13B C14B . . . . -0.9(2) ?
C11B C12B C13B C16B . . . . 175.84(15) ?
C12B C13B C14B C15B . . . . 0.6(2) ?
C16B C13B C14B C15B . . . . -176.03(15) ?
C13B C14B C15B C10B . . . . 0.1(3) ?
C11B C10B C15B C14B . . . . -0.7(2) ?
C9B C10B C15B C14B . . . . 178.71(15) ?
C12B C13B C16B C17B . . . . -72.7(2) ?
C14B C13B C16B C17B . . . . 103.90(18) ?
C13B C16B C17B C19B . . . . -60.1(2) ?
C13B C16B C17B C18B . . . . 176.24(16) ?
