#------------------------------------------------------------------------------
#$Date: 2022-01-22 00:49:13 +0200 (Sat, 22 Jan 2022) $
#$Revision: 272192 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/96/7129601.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_7129601
loop_
_publ_author_name
'Oyamada, Yusuke'
'Inaba, Kazuto'
'Sasamori, Takahiro'
'Nakamura, Shuichi'
_publ_section_title
;
 Enantioselective reaction of N-cyano imines: decarboxylative Mannich-type
 reaction with malonic acid half thioesters
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC07191B
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H13 Br N2 O S'
_chemical_formula_sum            'C16 H13 Br N2 O S'
_chemical_formula_weight         361.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2021-01-08 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.943(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1214(2)
_cell_length_b                   7.30260(10)
_cell_length_c                   19.6104(4)
_cell_measurement_reflns_used    24339
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      30.7980
_cell_measurement_theta_min      2.1690
_cell_volume                     1531.40(5)
_computing_cell_refinement       CrysAlisPro
_computing_data_collection       CrystalClear
_computing_data_reduction        CrysAlisPro
_computing_molecular_graphics
'Yadokari-XG 2011 (Wakita Nemoto et al., 2011)'
_computing_publication_material
'Yadokari-XG 2011 (Wakita,Nemoto et al., 2011)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/1 (Sheldrick, 2018)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Rigaku VariMax Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            35795
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.621
_diffrn_reflns_theta_min         2.434
_diffrn_source                   'rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    2.820
_exptl_absorpt_correction_T_max  0.827
_exptl_absorpt_correction_T_min  0.766
_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            colorless
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.880
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
;
 Flack x determined using 3216 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.010(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         8896
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0422
_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)+(0.0485P)²+0.3389P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0871
_reflns_Friedel_coverage         0.821
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.915
_reflns_number_gt                7979
_reflns_number_total             8896
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc07191b2.cif
_cod_data_source_block           DCM1b
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7129601
_shelx_shelxl_version_number     2018/1
_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.
;
_shelx_estimated_absorpt_t_min   0.766
_shelx_estimated_absorpt_t_max   0.827
_oxdiff_exptl_absorpt_empirical_full_min 0.748
_oxdiff_exptl_absorpt_empirical_full_max 1.282
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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
C1 C 0.3221(3) 0.8210(5) 0.79308(19) 0.0312(7) Uani 1 1 d . . . . .
H1 H 0.243(3) 0.773(5) 0.7725(17) 0.016(8) Uiso 1 1 d . . . . .
C2 C 0.3405(3) 0.8131(5) 0.87242(17) 0.0271(6) Uani 1 1 d . . . . .
C3 C 0.2528(3) 0.7225(5) 0.89921(19) 0.0300(7) Uani 1 1 d . . . . .
H2 H 0.181(4) 0.671(7) 0.867(2) 0.033(10) Uiso 1 1 d . . . . .
C4 C 0.2681(3) 0.7127(5) 0.97199(19) 0.0298(7) Uani 1 1 d . . . . .
H3 H 0.213(4) 0.631(7) 0.989(2) 0.037(11) Uiso 1 1 d . . . . .
C5 C 0.3702(3) 0.7948(6) 1.01888(18) 0.0286(6) Uani 1 1 d . . . . .
H4 H 0.380(3) 0.773(7) 1.070(2) 0.034(11) Uiso 1 1 d . . . . .
C6 C 0.4584(3) 0.8851(5) 0.9924(2) 0.0287(7) Uani 1 1 d . . . . .
H5 H 0.529(3) 0.929(5) 1.0210(18) 0.018(9) Uiso 1 1 d . . . . .
C7 C 0.4434(3) 0.8933(5) 0.91996(19) 0.0293(7) Uani 1 1 d . . . . .
H6 H 0.502(4) 0.953(7) 0.903(2) 0.039(12) Uiso 1 1 d . . . . .
N1 N 0.4297(3) 0.7344(4) 0.77483(16) 0.0334(6) Uani 1 1 d . . . . .
H7 H 0.473834 0.793717 0.750944 0.040 Uiso 1 1 calc R U . . .
C8 C 0.4565(4) 0.5618(5) 0.7964(2) 0.0378(8) Uani 1 1 d . . . . .
N2 N 0.4824(4) 0.4160(5) 0.8166(2) 0.0531(9) Uani 1 1 d . . . . .
C9 C 0.3113(5) 1.0192(5) 0.7669(2) 0.0374(8) Uani 1 1 d . . . . .
H8 H 0.254(4) 1.088(7) 0.783(2) 0.041(12) Uiso 1 1 d . . . . .
H9 H 0.380(4) 1.072(7) 0.783(2) 0.039(12) Uiso 1 1 d . . . . .
C10 C 0.2692(4) 1.0340(5) 0.6867(2) 0.0350(8) Uani 1 1 d . . . . .
O1 O 0.2936(3) 0.9242(5) 0.64729(15) 0.0531(9) Uani 1 1 d . . . . .
S1 S 0.17921(13) 1.23359(15) 0.65774(6) 0.0491(3) Uani 1 1 d . . . . .
C11 C 0.1449(3) 1.2130(6) 0.56449(19) 0.0333(7) Uani 1 1 d . . . . .
C12 C 0.0260(4) 1.1519(5) 0.5263(2) 0.0356(8) Uani 1 1 d . . . . .
H10 H -0.030(4) 1.115(7) 0.551(2) 0.041(12) Uiso 1 1 d . . . . .
C13 C -0.0074(3) 1.1498(5) 0.4532(2) 0.0326(8) Uani 1 1 d . . . . .
H11 H -0.084(4) 1.119(6) 0.4285(19) 0.026(10) Uiso 1 1 d . . . . .
C14 C 0.0795(3) 1.2057(6) 0.41821(18) 0.0289(7) Uani 1 1 d . . . . .
C15 C 0.1986(3) 1.2630(5) 0.4549(2) 0.0324(8) Uani 1 1 d . . . . .
H12 H 0.256(4) 1.292(7) 0.427(2) 0.034(10) Uiso 1 1 d . . . . .
C16 C 0.2306(3) 1.2684(6) 0.52837(19) 0.0330(8) Uani 1 1 d . . . . .
H13 H 0.316(4) 1.308(8) 0.553(2) 0.045(12) Uiso 1 1 d . . . . .
Br1 Br 0.03418(3) 1.19659(5) 0.31754(2) 0.03968(11) Uani 1 1 d . . . . .
C17 C 0.6567(3) 0.1735(5) 0.70110(18) 0.0300(7) Uani 1 1 d . . . . .
H14 H 0.576(4) 0.150(6) 0.711(2) 0.038(11) Uiso 1 1 d . . . . .
C18 C 0.6467(3) 0.1846(5) 0.62227(16) 0.0258(6) Uani 1 1 d . . . . .
C19 C 0.7362(3) 0.2767(5) 0.59753(18) 0.0285(7) Uani 1 1 d . . . . .
H15 H 0.797(4) 0.334(7) 0.624(2) 0.040(12) Uiso 1 1 d . . . . .
C20 C 0.7256(3) 0.2829(6) 0.52538(17) 0.0282(6) Uani 1 1 d . . . . .
H16 H 0.780(4) 0.343(6) 0.506(2) 0.031(10) Uiso 1 1 d . . . . .
C21 C 0.6270(3) 0.1934(6) 0.47793(18) 0.0273(6) Uani 1 1 d . . . . .
H17 H 0.619(3) 0.190(6) 0.433(2) 0.026(9) Uiso 1 1 d . . . . .
C22 C 0.5392(3) 0.0991(5) 0.50244(19) 0.0275(7) Uani 1 1 d . . . . .
H18 H 0.468(3) 0.021(5) 0.4702(17) 0.015(8) Uiso 1 1 d . . . . .
C23 C 0.5491(3) 0.0950(5) 0.57482(18) 0.0268(7) Uani 1 1 d . . . . .
H19 H 0.486(4) 0.026(6) 0.5955(19) 0.030(10) Uiso 1 1 d . . . . .
N3 N 0.6956(3) 0.3520(4) 0.73568(16) 0.0377(7) Uani 1 1 d . . . . .
H20 H 0.755785 0.359485 0.775527 0.045 Uiso 1 1 calc R U . . .
C24 C 0.6363(4) 0.5012(5) 0.70440(19) 0.0347(7) Uani 1 1 d . . . . .
N4 N 0.5899(3) 0.6333(4) 0.67707(16) 0.0385(7) Uani 1 1 d . . . . .
C25 C 0.7491(4) 0.0263(5) 0.73559(19) 0.0335(7) Uani 1 1 d . . . . .
H21 H 0.829(4) 0.043(7) 0.726(2) 0.045(12) Uiso 1 1 d . . . . .
H22 H 0.720(4) -0.082(7) 0.709(2) 0.040(12) Uiso 1 1 d . . . . .
C26 C 0.7648(3) -0.0023(5) 0.81412(18) 0.0312(7) Uani 1 1 d . . . . .
O2 O 0.7420(3) 0.1095(4) 0.85361(14) 0.0450(7) Uani 1 1 d . . . . .
S2 S 0.82959(11) -0.22215(15) 0.84224(5) 0.0406(2) Uani 1 1 d . . . . .
C27 C 0.8580(3) -0.2065(6) 0.93581(17) 0.0292(6) Uani 1 1 d . . . . .
C28 C 0.7699(3) -0.2739(5) 0.96789(19) 0.0312(8) Uani 1 1 d . . . . .
H23 H 0.701(4) -0.316(8) 0.941(2) 0.041(11) Uiso 1 1 d . . . . .
C29 C 0.7957(3) -0.2747(5) 1.04136(19) 0.0293(7) Uani 1 1 d . . . . .
H24 H 0.737(4) -0.326(7) 1.067(2) 0.032(10) Uiso 1 1 d . . . . .
C30 C 0.9105(3) -0.2071(6) 1.08105(16) 0.0280(6) Uani 1 1 d . . . . .
C31 C 0.9991(3) -0.1419(5) 1.0501(2) 0.0306(7) Uani 1 1 d . . . . .
H25 H 1.079(4) -0.105(7) 1.076(2) 0.036(11) Uiso 1 1 d . . . . .
C32 C 0.9721(3) -0.1406(5) 0.9763(2) 0.0318(7) Uani 1 1 d . . . . .
H26 H 1.029(4) -0.103(6) 0.955(2) 0.030(10) Uiso 1 1 d . . . . .
Br2 Br 0.94832(4) -0.20521(5) 1.18160(2) 0.03959(11) 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'
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'
S S 0.1246 0.1234 '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'
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
N1 C1 C2 110.0(3) . . ?
N1 C1 C9 108.5(3) . . ?
C2 C1 C9 110.9(3) . . ?
N1 C1 H1 118(2) . . ?
C2 C1 H1 106(2) . . ?
C9 C1 H1 103(2) . . ?
C7 C2 C3 118.6(3) . . ?
C7 C2 C1 121.8(3) . . ?
C3 C2 C1 119.6(3) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H2 120(2) . . ?
C2 C3 H2 119(2) . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H3 121(2) . . ?
C3 C4 H3 118(2) . . ?
C4 C5 C6 119.3(3) . . ?
C4 C5 H4 117(3) . . ?
C6 C5 H4 124(2) . . ?
C7 C6 C5 120.2(3) . . ?
C7 C6 H5 118(2) . . ?
C5 C6 H5 122(2) . . ?
C6 C7 C2 120.9(3) . . ?
C6 C7 H6 120(3) . . ?
C2 C7 H6 119(3) . . ?
C8 N1 C1 116.8(3) . . ?
C8 N1 H7 121.6 . . ?
C1 N1 H7 121.6 . . ?
N2 C8 N1 177.8(5) . . ?
C10 C9 C1 112.9(3) . . ?
C10 C9 H8 106(3) . . ?
C1 C9 H8 113(3) . . ?
C10 C9 H9 110(3) . . ?
C1 C9 H9 109(3) . . ?
H8 C9 H9 105(4) . . ?
O1 C10 C9 124.2(3) . . ?
O1 C10 S1 123.6(3) . . ?
C9 C10 S1 112.1(3) . . ?
C11 S1 C10 101.74(18) . . ?
C16 C11 C12 119.8(3) . . ?
C16 C11 S1 121.1(3) . . ?
C12 C11 S1 118.9(3) . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H10 120(3) . . ?
C11 C12 H10 119(3) . . ?
C12 C13 C14 118.9(3) . . ?
C12 C13 H11 121(2) . . ?
C14 C13 H11 120(2) . . ?
C15 C14 C13 121.7(3) . . ?
C15 C14 Br1 119.5(3) . . ?
C13 C14 Br1 118.7(3) . . ?
C16 C15 C14 119.0(3) . . ?
C16 C15 H12 124(2) . . ?
C14 C15 H12 117(2) . . ?
C15 C16 C11 120.2(3) . . ?
C15 C16 H13 117(3) . . ?
C11 C16 H13 123(3) . . ?
N3 C17 C25 110.2(3) . . ?
N3 C17 C18 110.5(3) . . ?
C25 C17 C18 110.1(3) . . ?
N3 C17 H14 104(3) . . ?
C25 C17 H14 110(3) . . ?
C18 C17 H14 113(2) . . ?
C23 C18 C19 119.8(3) . . ?
C23 C18 C17 118.9(3) . . ?
C19 C18 C17 121.3(3) . . ?
C20 C19 C18 120.1(3) . . ?
C20 C19 H15 116(3) . . ?
C18 C19 H15 123(3) . . ?
C19 C20 C21 119.8(3) . . ?
C19 C20 H16 125(3) . . ?
C21 C20 H16 116(3) . . ?
C22 C21 C20 120.2(3) . . ?
C22 C21 H17 117(3) . . ?
C20 C21 H17 122(3) . . ?
C21 C22 C23 119.9(3) . . ?
C21 C22 H18 123.8(19) . . ?
C23 C22 H18 116.1(19) . . ?
C18 C23 C22 120.2(3) . . ?
C18 C23 H19 117(2) . . ?
C22 C23 H19 123(2) . . ?
C24 N3 C17 117.7(3) . . ?
C24 N3 H20 121.2 . . ?
C17 N3 H20 121.2 . . ?
N4 C24 N3 177.0(5) . . ?
C17 C25 C26 115.3(3) . . ?
C17 C25 H21 112(3) . . ?
C26 C25 H21 111(3) . . ?
C17 C25 H22 105(3) . . ?
C26 C25 H22 111(3) . . ?
H21 C25 H22 101(4) . . ?
O2 C26 C25 125.2(3) . . ?
O2 C26 S2 123.5(3) . . ?
C25 C26 S2 111.2(2) . . ?
C27 S2 C26 101.73(18) . . ?
C32 C27 C28 120.7(3) . . ?
C32 C27 S2 119.3(3) . . ?
C28 C27 S2 119.8(3) . . ?
C29 C28 C27 120.0(3) . . ?
C29 C28 H23 123(3) . . ?
C27 C28 H23 117(3) . . ?
C28 C29 C30 118.4(3) . . ?
C28 C29 H24 123(2) . . ?
C30 C29 H24 119(2) . . ?
C31 C30 C29 122.3(3) . . ?
C31 C30 Br2 118.3(3) . . ?
C29 C30 Br2 119.4(3) . . ?
C30 C31 C32 118.9(3) . . ?
C30 C31 H25 123(3) . . ?
C32 C31 H25 118(3) . . ?
C27 C32 C31 119.7(3) . . ?
C27 C32 H26 119(3) . . ?
C31 C32 H26 121(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.481(5) . ?
C1 C2 1.514(5) . ?
C1 C9 1.530(5) . ?
C1 H1 0.93(3) . ?
C2 C7 1.391(5) . ?
C2 C3 1.395(5) . ?
C3 C4 1.392(5) . ?
C3 H2 0.95(4) . ?
C4 C5 1.386(5) . ?
C4 H3 0.97(5) . ?
C5 C6 1.396(5) . ?
C5 H4 1.00(4) . ?
C6 C7 1.384(5) . ?
C6 H5 0.89(4) . ?
C7 H6 0.92(5) . ?
N1 C8 1.336(5) . ?
N1 H7 0.8800 . ?
C8 N2 1.145(5) . ?
C9 C10 1.517(5) . ?
C9 H8 0.93(5) . ?
C9 H9 0.84(5) . ?
C10 O1 1.195(5) . ?
C10 S1 1.771(4) . ?
S1 C11 1.769(4) . ?
C11 C16 1.395(5) . ?
C11 C12 1.401(6) . ?
C12 C13 1.379(5) . ?
C12 H10 0.92(4) . ?
C13 C14 1.391(5) . ?
C13 H11 0.89(4) . ?
C14 C15 1.387(5) . ?
C14 Br1 1.900(3) . ?
C15 C16 1.386(5) . ?
C15 H12 0.97(4) . ?
C16 H13 0.98(5) . ?
C17 N3 1.478(5) . ?
C17 C25 1.512(5) . ?
C17 C18 1.521(5) . ?
C17 H14 0.98(4) . ?
C18 C23 1.385(5) . ?
C18 C19 1.394(5) . ?
C19 C20 1.388(5) . ?
C19 H15 0.84(5) . ?
C20 C21 1.391(5) . ?
C20 H16 0.91(4) . ?
C21 C22 1.384(5) . ?
C21 H17 0.87(4) . ?
C22 C23 1.394(5) . ?
C22 H18 1.04(3) . ?
C23 H19 1.03(4) . ?
N3 C24 1.332(5) . ?
N3 H20 0.8800 . ?
C24 N4 1.154(5) . ?
C25 C26 1.516(5) . ?
C25 H21 0.96(5) . ?
C25 H22 0.95(5) . ?
C26 O2 1.200(4) . ?
C26 S2 1.784(4) . ?
S2 C27 1.778(3) . ?
C27 C32 1.386(5) . ?
C27 C28 1.391(5) . ?
C28 C29 1.390(5) . ?
C28 H23 0.86(4) . ?
C29 C30 1.390(5) . ?
C29 H24 0.99(4) . ?
C30 C31 1.377(5) . ?
C30 Br2 1.900(3) . ?
C31 C32 1.394(5) . ?
C31 H25 0.93(4) . ?
C32 H26 0.89(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H7 N4 0.88 2.48 3.045(4) 122.2 . yes
C9 H8 Br2 0.93(5) 2.94(5) 3.874(4) 173(3) 2_667 yes
N3 H20 O2 0.88 2.41 2.845(4) 110.5 . yes
C25 H22 N4 0.95(5) 2.51(5) 3.401(5) 156(3) 1_545 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C7 59.2(5) . . . . ?
C9 C1 C2 C7 -60.8(4) . . . . ?
N1 C1 C2 C3 -120.5(4) . . . . ?
C9 C1 C2 C3 119.5(4) . . . . ?
C7 C2 C3 C4 0.0(5) . . . . ?
C1 C2 C3 C4 179.7(3) . . . . ?
C2 C3 C4 C5 0.7(6) . . . . ?
C3 C4 C5 C6 -0.8(6) . . . . ?
C4 C5 C6 C7 0.3(6) . . . . ?
C5 C6 C7 C2 0.4(6) . . . . ?
C3 C2 C7 C6 -0.5(5) . . . . ?
C1 C2 C7 C6 179.8(3) . . . . ?
C2 C1 N1 C8 55.9(4) . . . . ?
C9 C1 N1 C8 177.4(3) . . . . ?
N1 C1 C9 C10 69.6(4) . . . . ?
C2 C1 C9 C10 -169.4(3) . . . . ?
C1 C9 C10 O1 -31.7(6) . . . . ?
C1 C9 C10 S1 148.2(3) . . . . ?
O1 C10 S1 C11 -0.1(5) . . . . ?
C9 C10 S1 C11 180.0(3) . . . . ?
C10 S1 C11 C16 -82.5(4) . . . . ?
C10 S1 C11 C12 102.0(3) . . . . ?
C16 C11 C12 C13 -1.3(6) . . . . ?
S1 C11 C12 C13 174.2(3) . . . . ?
C11 C12 C13 C14 1.3(5) . . . . ?
C12 C13 C14 C15 0.0(6) . . . . ?
C12 C13 C14 Br1 178.4(3) . . . . ?
C13 C14 C15 C16 -1.4(6) . . . . ?
Br1 C14 C15 C16 -179.7(3) . . . . ?
C14 C15 C16 C11 1.4(6) . . . . ?
C12 C11 C16 C15 0.0(6) . . . . ?
S1 C11 C16 C15 -175.5(3) . . . . ?
N3 C17 C18 C23 -140.5(3) . . . . ?
C25 C17 C18 C23 97.6(4) . . . . ?
N3 C17 C18 C19 42.1(5) . . . . ?
C25 C17 C18 C19 -79.8(4) . . . . ?
C23 C18 C19 C20 1.8(5) . . . . ?
C17 C18 C19 C20 179.2(3) . . . . ?
C18 C19 C20 C21 -1.5(6) . . . . ?
C19 C20 C21 C22 0.3(6) . . . . ?
C20 C21 C22 C23 0.5(6) . . . . ?
C19 C18 C23 C22 -1.0(5) . . . . ?
C17 C18 C23 C22 -178.4(3) . . . . ?
C21 C22 C23 C18 -0.1(5) . . . . ?
C25 C17 N3 C24 169.2(3) . . . . ?
C18 C17 N3 C24 47.3(4) . . . . ?
N3 C17 C25 C26 59.6(4) . . . . ?
C18 C17 C25 C26 -178.3(3) . . . . ?
C17 C25 C26 O2 -23.1(6) . . . . ?
C17 C25 C26 S2 159.7(3) . . . . ?
O2 C26 S2 C27 -5.0(4) . . . . ?
C25 C26 S2 C27 172.2(3) . . . . ?
C26 S2 C27 C32 -89.6(3) . . . . ?
C26 S2 C27 C28 95.6(3) . . . . ?
C32 C27 C28 C29 0.4(6) . . . . ?
S2 C27 C28 C29 175.1(3) . . . . ?
C27 C28 C29 C30 0.0(5) . . . . ?
C28 C29 C30 C31 -0.7(6) . . . . ?
C28 C29 C30 Br2 179.7(3) . . . . ?
C29 C30 C31 C32 1.1(6) . . . . ?
Br2 C30 C31 C32 -179.3(3) . . . . ?
C28 C27 C32 C31 0.0(6) . . . . ?
S2 C27 C32 C31 -174.8(3) . . . . ?
C30 C31 C32 C27 -0.7(5) . . . . ?
