 
data_ia186
 
_audit_creation_method            SHELXL-2014/6
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety
 'C39 H36 Br N7 O3 S, 3(C2 H3 N)'
_chemical_formula_sum
 'C45 H45 Br N10 O3 S' 
_chemical_formula_weight          885.88

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'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_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.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    10.2603(5)
_cell_length_b                    11.4150(6)
_cell_length_c                    36.6392(19)
_cell_angle_alpha                 90
_cell_angle_beta                  94.6830(10)
_cell_angle_gamma                 90
_cell_volume                      4276.9(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     999
_cell_measurement_theta_min       3
_cell_measurement_theta_max       25
 
_exptl_crystal_description        plate    
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.376          
_exptl_crystal_F_000              1840
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.310
_exptl_crystal_size_mid           0.290
_exptl_crystal_size_min           0.250
_exptl_absorpt_coefficient_mu     1.063
_shelx_estimated_absorpt_T_min    0.734
_shelx_estimated_absorpt_T_max    0.777
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6509  
_exptl_absorpt_correction_T_max   0.7461
_exptl_absorpt_process_details    'Bruker SADABS'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker SMART APEX II diffractometer'
_diffrn_detector_type             'Bruker APEX II CCD area detector'
_diffrn_measurement_method        'omega scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             59467
_diffrn_reflns_av_unetI/netI      0.0279
_diffrn_reflns_av_R_equivalents   0.0434
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -46
_diffrn_reflns_limit_l_max        46
_diffrn_reflns_theta_min          1.869
_diffrn_reflns_theta_max          27.000
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.999
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.999
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.999
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              9330
_reflns_number_gt                 8271
_reflns_threshold_expression      'I>2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX2'             
_computing_cell_refinement        'Bruker SAINT'             
_computing_data_reduction         'Bruker SAINT'             
_computing_structure_solution     'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement   'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material   'SHELXTL (Sheldrick, 2008)'
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0244P)²+11.4527P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          9330
_refine_ls_number_parameters      552
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0641
_refine_ls_R_factor_gt            0.0564
_refine_ls_wR_factor_ref          0.1261
_refine_ls_wR_factor_gt           0.1232
_refine_ls_goodness_of_fit_ref    1.161
_refine_ls_restrained_S_all       1.161
_refine_ls_shift/su_max           0.005
_refine_ls_shift/su_mean          0.000
 
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 0.89484(4) 0.84279(3) 0.56198(2) 0.04058(12) Uani 1 1 d . . . . .
S1 S 0.42344(7) 0.50195(6) 0.61362(2) 0.01586(14) Uani 1 1 d . . . . .
O1 O 0.41611(19) 0.79049(17) 0.73018(5) 0.0176(4) Uani 1 1 d . . . . .
O2 O 0.59016(19) 0.27718(17) 0.68050(5) 0.0169(4) Uani 1 1 d . . . . .
O3 O 0.4272(2) 0.36372(18) 0.53963(5) 0.0218(4) Uani 1 1 d . . . . .
N1 N 0.4280(2) 0.58864(19) 0.73242(6) 0.0128(4) Uani 1 1 d . . . . .
N2 N 0.2374(2) 0.67116(19) 0.71423(6) 0.0141(5) Uani 1 1 d . . . . .
N3 N 0.3844(2) 0.38575(19) 0.71279(6) 0.0118(4) Uani 1 1 d . . . . .
H3N H 0.451(3) 0.355(3) 0.7255(9) 0.014(8) Uiso 1 1 d . . . . .
N4 N 0.4270(2) 0.4111(2) 0.67794(6) 0.0132(4) Uani 1 1 d . . . . .
N5 N 0.2552(2) 0.5461(2) 0.66408(6) 0.0136(5) Uani 1 1 d . . . . .
N6 N 0.5729(2) 0.1907(2) 0.59403(7) 0.0198(5) Uani 1 1 d . . . . .
N7 N 0.2517(2) 0.2849(2) 0.56622(7) 0.0203(5) Uani 1 1 d . . . . .
C1 C 0.3661(3) 0.6930(2) 0.72586(7) 0.0134(5) Uani 1 1 d . . . . .
C2 C 0.3357(2) 0.4908(2) 0.72952(7) 0.0118(5) Uani 1 1 d . . . . .
C3 C 0.2254(3) 0.5481(2) 0.70267(7) 0.0126(5) Uani 1 1 d . . . . .
C4 C 0.3533(3) 0.4887(2) 0.65570(7) 0.0130(5) Uani 1 1 d . . . . .
C5 C 0.5203(3) 0.3463(2) 0.66304(7) 0.0140(5) Uani 1 1 d . . . . .
C6 C 0.5216(3) 0.3692(2) 0.62182(7) 0.0141(5) Uani 1 1 d . . . . .
C7 C 0.6681(3) 0.3724(2) 0.61163(8) 0.0168(6) Uani 1 1 d . . . . .
H7A H 0.7235 0.3491 0.6342 0.020 Uiso 1 1 calc R U . . .
C8 C 0.6749(3) 0.2714(3) 0.58422(8) 0.0212(6) Uani 1 1 d . . . . .
H8A H 0.6574 0.2996 0.5587 0.025 Uiso 1 1 calc R U . . .
H8B H 0.7619 0.2332 0.5868 0.025 Uiso 1 1 calc R U . . .
C9 C 0.4586(3) 0.2614(2) 0.59986(8) 0.0162(5) Uani 1 1 d . . . . .
C10 C 0.3811(3) 0.3101(2) 0.56446(8) 0.0178(6) Uani 1 1 d . . . . .
C11 C 0.2317(3) 0.2165(3) 0.59727(8) 0.0207(6) Uani 1 1 d . . . . .
C12 C 0.1172(3) 0.1666(3) 0.60686(9) 0.0287(7) Uani 1 1 d . . . . .
H12A H 0.0365 0.1805 0.5929 0.034 Uiso 1 1 calc R U . . .
C13 C 0.1239(3) 0.0952(3) 0.63767(10) 0.0324(8) Uani 1 1 d . . . . .
H13A H 0.0462 0.0602 0.6450 0.039 Uiso 1 1 calc R U . . .
C14 C 0.2416(4) 0.0738(3) 0.65788(9) 0.0306(8) Uani 1 1 d . . . . .
H14A H 0.2436 0.0245 0.6788 0.037 Uiso 1 1 calc R U . . .
C15 C 0.3573(3) 0.1243(3) 0.64772(8) 0.0234(6) Uani 1 1 d . . . . .
H15A H 0.4384 0.1085 0.6612 0.028 Uiso 1 1 calc R U . . .
C16 C 0.3514(3) 0.1976(3) 0.61759(8) 0.0189(6) Uani 1 1 d . . . . .
C17 C 0.7211(3) 0.4872(3) 0.59913(8) 0.0181(6) Uani 1 1 d . . . . .
C18 C 0.6728(3) 0.5414(3) 0.56648(8) 0.0225(6) Uani 1 1 d . . . . .
H18A H 0.6036 0.5054 0.5517 0.027 Uiso 1 1 calc R U . . .
C19 C 0.7244(3) 0.6466(3) 0.55532(9) 0.0255(7) Uani 1 1 d . . . . .
H19A H 0.6898 0.6833 0.5334 0.031 Uiso 1 1 calc R U . . .
C20 C 0.8268(3) 0.6972(3) 0.57661(9) 0.0253(7) Uani 1 1 d . . . . .
C21 C 0.8782(3) 0.6456(3) 0.60867(9) 0.0253(7) Uani 1 1 d . . . . .
H21A H 0.9492 0.6808 0.6229 0.030 Uiso 1 1 calc R U . . .
C22 C 0.8238(3) 0.5407(3) 0.61986(8) 0.0211(6) Uani 1 1 d . . . . .
H22A H 0.8578 0.5053 0.6421 0.025 Uiso 1 1 calc R U . . .
C23 C 0.5591(3) 0.5796(3) 0.75043(8) 0.0190(6) Uani 1 1 d . . . . .
H23A H 0.5728 0.6420 0.7687 0.029 Uiso 1 1 calc R U . . .
H23B H 0.6234 0.5873 0.7322 0.029 Uiso 1 1 calc R U . . .
H23C H 0.5697 0.5032 0.7626 0.029 Uiso 1 1 calc R U . . .
C24 C 0.1609(3) 0.7604(2) 0.69341(8) 0.0182(6) Uani 1 1 d . . . . .
H24A H 0.1978 0.8380 0.6993 0.027 Uiso 1 1 calc R U . . .
H24B H 0.0701 0.7578 0.6998 0.027 Uiso 1 1 calc R U . . .
H24C H 0.1634 0.7453 0.6671 0.027 Uiso 1 1 calc R U . . .
C25 C 0.2895(2) 0.4556(2) 0.76647(7) 0.0129(5) Uani 1 1 d . . . . .
C26 C 0.2926(3) 0.5371(3) 0.79488(8) 0.0176(6) Uani 1 1 d . . . . .
H26A H 0.3268 0.6132 0.7914 0.021 Uiso 1 1 calc R U . . .
C27 C 0.2464(3) 0.5081(3) 0.82813(8) 0.0230(6) Uani 1 1 d . . . . .
H27A H 0.2481 0.5646 0.8472 0.028 Uiso 1 1 calc R U . . .
C28 C 0.1974(3) 0.3966(3) 0.83373(8) 0.0242(6) Uani 1 1 d . . . . .
H28A H 0.1655 0.3767 0.8565 0.029 Uiso 1 1 calc R U . . .
C29 C 0.1956(3) 0.3148(3) 0.80575(8) 0.0208(6) Uani 1 1 d . . . . .
H29A H 0.1635 0.2381 0.8096 0.025 Uiso 1 1 calc R U . . .
C30 C 0.2399(3) 0.3435(2) 0.77225(8) 0.0157(5) Uani 1 1 d . . . . .
H30A H 0.2367 0.2871 0.7531 0.019 Uiso 1 1 calc R U . . .
C31 C 0.0926(3) 0.4951(2) 0.70711(7) 0.0147(5) Uani 1 1 d . . . . .
C32 C 0.0100(3) 0.5425(3) 0.73152(8) 0.0194(6) Uani 1 1 d . . . . .
H32A H 0.0332 0.6132 0.7441 0.023 Uiso 1 1 calc R U . . .
C33 C -0.1060(3) 0.4867(3) 0.73756(9) 0.0257(7) Uani 1 1 d . . . . .
H33A H -0.1623 0.5198 0.7541 0.031 Uiso 1 1 calc R U . . .
C34 C -0.1409(3) 0.3830(3) 0.71968(9) 0.0287(7) Uani 1 1 d . . . . .
H34A H -0.2206 0.3451 0.7240 0.034 Uiso 1 1 calc R U . . .
C35 C -0.0588(3) 0.3350(3) 0.69548(9) 0.0264(7) Uani 1 1 d . . . . .
H35A H -0.0817 0.2634 0.6834 0.032 Uiso 1 1 calc R U . . .
C36 C 0.0571(3) 0.3914(3) 0.68884(8) 0.0189(6) Uani 1 1 d . . . . .
H36A H 0.1121 0.3592 0.6718 0.023 Uiso 1 1 calc R U . . .
C37 C 0.5500(3) 0.0915(3) 0.56906(9) 0.0267(7) Uani 1 1 d . . . . .
H37A H 0.4780 0.0437 0.5769 0.040 Uiso 1 1 calc R U . . .
H37B H 0.6294 0.0437 0.5693 0.040 Uiso 1 1 calc R U . . .
H37C H 0.5272 0.1206 0.5442 0.040 Uiso 1 1 calc R U . . .
C38 C 0.1464(3) 0.3322(3) 0.54113(9) 0.0290(7) Uani 1 1 d . . . . .
H38A H 0.0862 0.2680 0.5328 0.035 Uiso 1 1 calc R U . . .
H38B H 0.1841 0.3651 0.5193 0.035 Uiso 1 1 calc R U . . .
C39 C 0.0698(4) 0.4272(4) 0.55907(12) 0.0459(10) Uani 1 1 d . . . . .
H39A H 0.0041 0.4601 0.5410 0.069 Uiso 1 1 calc R U . . .
H39B H 0.1297 0.4892 0.5683 0.069 Uiso 1 1 calc R U . . .
H39C H 0.0262 0.3934 0.5794 0.069 Uiso 1 1 calc R U . . .
N1S N 0.8860(3) 0.1342(3) 0.52658(9) 0.0373(7) Uani 1 1 d . . . . .
C1S C 0.8423(3) 0.0766(3) 0.50368(10) 0.0298(7) Uani 1 1 d . . . . .
C2S C 0.7878(5) 0.0007(4) 0.47439(13) 0.0551(12) Uani 1 1 d . . . . .
H2SA H 0.7794 0.0445 0.4513 0.083 Uiso 1 1 calc R U . . .
H2SB H 0.7014 -0.0270 0.4801 0.083 Uiso 1 1 calc R U . . .
H2SC H 0.8458 -0.0666 0.4720 0.083 Uiso 1 1 calc R U . . .
N2S N 0.5214(4) 0.1723(4) 0.47181(11) 0.0593(11) Uani 1 1 d . . . . .
C3S C 0.5916(5) 0.2498(4) 0.47440(11) 0.0494(11) Uani 1 1 d . . . . .
C4S C 0.6826(6) 0.3485(4) 0.47744(12) 0.0603(13) Uani 1 1 d . . . . .
H4SA H 0.7348 0.3493 0.4562 0.090 Uiso 1 1 calc R U . . .
H4SB H 0.7408 0.3405 0.4999 0.090 Uiso 1 1 calc R U . . .
H4SC H 0.6334 0.4219 0.4783 0.090 Uiso 1 1 calc R U . . .
N3S N 0.2645(4) 0.7956(4) 0.60119(10) 0.0573(10) Uani 1 1 d . . . . .
C5S C 0.3643(5) 0.8048(4) 0.61586(11) 0.0407(9) Uani 1 1 d . . . . .
C6S C 0.4939(4) 0.8147(4) 0.63496(13) 0.0514(11) Uani 1 1 d . . . . .
H6SA H 0.5510 0.7541 0.6260 0.077 Uiso 1 1 calc R U . . .
H6SB H 0.4876 0.8043 0.6613 0.077 Uiso 1 1 calc R U . . .
H6SC H 0.5303 0.8922 0.6304 0.077 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
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 C20 1.897(3) . ?
S1 C4 1.761(3) . ?
S1 C6 1.831(3) . ?
O1 C1 1.230(3) . ?
O2 C5 1.212(3) . ?
O3 C10 1.223(4) . ?
N1 C1 1.362(3) . ?
N1 C23 1.453(3) . ?
N1 C2 1.462(3) . ?
N2 C1 1.377(4) . ?
N2 C24 1.463(3) . ?
N2 C3 1.469(3) . ?
N3 N4 1.413(3) . ?
N3 C2 1.454(3) . ?
N3 H3N 0.87(3) . ?
N4 C5 1.359(3) . ?
N4 C4 1.386(3) . ?
N5 C4 1.260(4) . ?
N5 C3 1.471(3) . ?
N6 C9 1.454(4) . ?
N6 C8 1.461(4) . ?
N6 C37 1.463(4) . ?
N7 C10 1.365(4) . ?
N7 C11 1.409(4) . ?
N7 C38 1.464(4) . ?
C2 C25 1.524(4) . ?
C2 C3 1.580(4) . ?
C3 C31 1.511(4) . ?
C5 C6 1.534(4) . ?
C6 C7 1.578(4) . ?
C6 C9 1.580(4) . ?
C7 C17 1.506(4) . ?
C7 C8 1.534(4) . ?
C7 H7A 1.0000 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C16 1.509(4) . ?
C9 C10 1.567(4) . ?
C11 C12 1.377(4) . ?
C11 C16 1.400(4) . ?
C12 C13 1.389(5) . ?
C12 H12A 0.9500 . ?
C13 C14 1.385(5) . ?
C13 H13A 0.9500 . ?
C14 C15 1.397(5) . ?
C14 H14A 0.9500 . ?
C15 C16 1.383(4) . ?
C15 H15A 0.9500 . ?
C17 C22 1.389(4) . ?
C17 C18 1.400(4) . ?
C18 C19 1.387(4) . ?
C18 H18A 0.9500 . ?
C19 C20 1.383(5) . ?
C19 H19A 0.9500 . ?
C20 C21 1.379(5) . ?
C21 C22 1.396(4) . ?
C21 H21A 0.9500 . ?
C22 H22A 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.394(4) . ?
C25 C30 1.399(4) . ?
C26 C27 1.383(4) . ?
C26 H26A 0.9500 . ?
C27 C28 1.389(4) . ?
C27 H27A 0.9500 . ?
C28 C29 1.386(4) . ?
C28 H28A 0.9500 . ?
C29 C30 1.383(4) . ?
C29 H29A 0.9500 . ?
C30 H30A 0.9500 . ?
C31 C32 1.391(4) . ?
C31 C36 1.394(4) . ?
C32 C33 1.383(4) . ?
C32 H32A 0.9500 . ?
C33 C34 1.385(5) . ?
C33 H33A 0.9500 . ?
C34 C35 1.385(5) . ?
C34 H34A 0.9500 . ?
C35 C36 1.391(4) . ?
C35 H35A 0.9500 . ?
C36 H36A 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 C39 1.519(5) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
N1S C1S 1.130(5) . ?
C1S C2S 1.455(5) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?
N2S C3S 1.141(6) . ?
C3S C4S 1.461(7) . ?
C4S H4SA 0.9800 . ?
C4S H4SB 0.9800 . ?
C4S H4SC 0.9800 . ?
N3S C5S 1.122(6) . ?
C5S C6S 1.456(6) . ?
C6S H6SA 0.9800 . ?
C6S H6SB 0.9800 . ?
C6S H6SC 0.9800 . ?
 
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
C4 S1 C6 92.53(12) . . ?
C1 N1 C23 122.9(2) . . ?
C1 N1 C2 111.4(2) . . ?
C23 N1 C2 123.3(2) . . ?
C1 N2 C24 119.7(2) . . ?
C1 N2 C3 108.5(2) . . ?
C24 N2 C3 119.1(2) . . ?
N4 N3 C2 110.8(2) . . ?
N4 N3 H3N 106(2) . . ?
C2 N3 H3N 113(2) . . ?
C5 N4 C4 118.7(2) . . ?
C5 N4 N3 122.1(2) . . ?
C4 N4 N3 117.9(2) . . ?
C4 N5 C3 118.4(2) . . ?
C9 N6 C8 106.8(2) . . ?
C9 N6 C37 115.5(2) . . ?
C8 N6 C37 114.6(2) . . ?
C10 N7 C11 111.2(2) . . ?
C10 N7 C38 124.3(3) . . ?
C11 N7 C38 124.3(3) . . ?
O1 C1 N1 125.8(2) . . ?
O1 C1 N2 125.7(2) . . ?
N1 C1 N2 108.5(2) . . ?
N3 C2 N1 114.7(2) . . ?
N3 C2 C25 107.4(2) . . ?
N1 C2 C25 112.6(2) . . ?
N3 C2 C3 109.4(2) . . ?
N1 C2 C3 99.0(2) . . ?
C25 C2 C3 113.8(2) . . ?
N2 C3 N5 105.9(2) . . ?
N2 C3 C31 114.0(2) . . ?
N5 C3 C31 110.9(2) . . ?
N2 C3 C2 100.2(2) . . ?
N5 C3 C2 113.4(2) . . ?
C31 C3 C2 111.9(2) . . ?
N5 C4 N4 126.7(2) . . ?
N5 C4 S1 124.1(2) . . ?
N4 C4 S1 109.09(19) . . ?
O2 C5 N4 123.2(2) . . ?
O2 C5 C6 125.3(2) . . ?
N4 C5 C6 111.4(2) . . ?
C5 C6 C7 108.8(2) . . ?
C5 C6 C9 109.4(2) . . ?
C7 C6 C9 104.8(2) . . ?
C5 C6 S1 104.71(18) . . ?
C7 C6 S1 117.66(19) . . ?
C9 C6 S1 111.36(18) . . ?
C17 C7 C8 114.7(2) . . ?
C17 C7 C6 117.8(2) . . ?
C8 C7 C6 103.5(2) . . ?
C17 C7 H7A 106.7 . . ?
C8 C7 H7A 106.7 . . ?
C6 C7 H7A 106.7 . . ?
N6 C8 C7 103.9(2) . . ?
N6 C8 H8A 111.0 . . ?
C7 C8 H8A 111.0 . . ?
N6 C8 H8B 111.0 . . ?
C7 C8 H8B 111.0 . . ?
H8A C8 H8B 109.0 . . ?
N6 C9 C16 114.8(2) . . ?
N6 C9 C10 115.9(2) . . ?
C16 C9 C10 100.9(2) . . ?
N6 C9 C6 101.9(2) . . ?
C16 C9 C6 116.0(2) . . ?
C10 C9 C6 107.7(2) . . ?
O3 C10 N7 125.2(3) . . ?
O3 C10 C9 126.3(3) . . ?
N7 C10 C9 108.4(2) . . ?
C12 C11 C16 122.1(3) . . ?
C12 C11 N7 128.2(3) . . ?
C16 C11 N7 109.6(3) . . ?
C11 C12 C13 117.6(3) . . ?
C11 C12 H12A 121.2 . . ?
C13 C12 H12A 121.2 . . ?
C14 C13 C12 121.4(3) . . ?
C14 C13 H13A 119.3 . . ?
C12 C13 H13A 119.3 . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 H14A 119.7 . . ?
C15 C14 H14A 119.7 . . ?
C16 C15 C14 118.7(3) . . ?
C16 C15 H15A 120.7 . . ?
C14 C15 H15A 120.7 . . ?
C15 C16 C11 119.8(3) . . ?
C15 C16 C9 130.5(3) . . ?
C11 C16 C9 109.6(3) . . ?
C22 C17 C18 118.2(3) . . ?
C22 C17 C7 119.6(3) . . ?
C18 C17 C7 122.2(3) . . ?
C19 C18 C17 121.1(3) . . ?
C19 C18 H18A 119.4 . . ?
C17 C18 H18A 119.4 . . ?
C20 C19 C18 119.0(3) . . ?
C20 C19 H19A 120.5 . . ?
C18 C19 H19A 120.5 . . ?
C21 C20 C19 121.5(3) . . ?
C21 C20 Br1 119.4(2) . . ?
C19 C20 Br1 119.1(2) . . ?
C20 C21 C22 118.8(3) . . ?
C20 C21 H21A 120.6 . . ?
C22 C21 H21A 120.6 . . ?
C17 C22 C21 121.3(3) . . ?
C17 C22 H22A 119.4 . . ?
C21 C22 H22A 119.3 . . ?
N1 C23 H23A 109.5 . . ?
N1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C24 H24A 109.5 . . ?
N2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C30 118.9(3) . . ?
C26 C25 C2 119.8(2) . . ?
C30 C25 C2 121.2(2) . . ?
C27 C26 C25 120.6(3) . . ?
C27 C26 H26A 119.7 . . ?
C25 C26 H26A 119.7 . . ?
C26 C27 C28 120.2(3) . . ?
C26 C27 H27A 119.9 . . ?
C28 C27 H27A 119.9 . . ?
C29 C28 C27 119.4(3) . . ?
C29 C28 H28A 120.3 . . ?
C27 C28 H28A 120.3 . . ?
C30 C29 C28 120.8(3) . . ?
C30 C29 H29A 119.6 . . ?
C28 C29 H29A 119.6 . . ?
C29 C30 C25 120.1(3) . . ?
C29 C30 H30A 120.0 . . ?
C25 C30 H30A 120.0 . . ?
C32 C31 C36 119.3(3) . . ?
C32 C31 C3 121.1(3) . . ?
C36 C31 C3 119.4(2) . . ?
C33 C32 C31 120.1(3) . . ?
C33 C32 H32A 119.9 . . ?
C31 C32 H32A 119.9 . . ?
C32 C33 C34 120.7(3) . . ?
C32 C33 H33A 119.7 . . ?
C34 C33 H33A 119.7 . . ?
C35 C34 C33 119.6(3) . . ?
C35 C34 H34A 120.2 . . ?
C33 C34 H34A 120.2 . . ?
C34 C35 C36 120.1(3) . . ?
C34 C35 H35A 119.9 . . ?
C36 C35 H35A 119.9 . . ?
C35 C36 C31 120.2(3) . . ?
C35 C36 H36A 119.9 . . ?
C31 C36 H36A 119.9 . . ?
N6 C37 H37A 109.5 . . ?
N6 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
N6 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N7 C38 C39 111.9(3) . . ?
N7 C38 H38A 109.2 . . ?
C39 C38 H38A 109.2 . . ?
N7 C38 H38B 109.2 . . ?
C39 C38 H38B 109.2 . . ?
H38A C38 H38B 107.9 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
N1S C1S C2S 178.9(4) . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
N2S C3S C4S 179.3(5) . . ?
C3S C4S H4SA 109.5 . . ?
C3S C4S H4SB 109.5 . . ?
H4SA C4S H4SB 109.5 . . ?
C3S C4S H4SC 109.5 . . ?
H4SA C4S H4SC 109.5 . . ?
H4SB C4S H4SC 109.5 . . ?
N3S C5S C6S 179.0(5) . . ?
C5S C6S H6SA 109.5 . . ?
C5S C6S H6SB 109.5 . . ?
H6SA C6S H6SB 109.5 . . ?
C5S C6S H6SC 109.5 . . ?
H6SA C6S H6SC 109.5 . . ?
H6SB C6S H6SC 109.5 . . ?
 
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
C2 N3 N4 C5 153.3(2) . . . . ?
C2 N3 N4 C4 -39.8(3) . . . . ?
C23 N1 C1 O1 8.8(4) . . . . ?
C2 N1 C1 O1 171.7(3) . . . . ?
C23 N1 C1 N2 -170.1(2) . . . . ?
C2 N1 C1 N2 -7.1(3) . . . . ?
C24 N2 C1 O1 22.6(4) . . . . ?
C3 N2 C1 O1 164.1(3) . . . . ?
C24 N2 C1 N1 -158.6(2) . . . . ?
C3 N2 C1 N1 -17.1(3) . . . . ?
N4 N3 C2 N1 -55.2(3) . . . . ?
N4 N3 C2 C25 178.9(2) . . . . ?
N4 N3 C2 C3 54.9(3) . . . . ?
C1 N1 C2 N3 141.9(2) . . . . ?
C23 N1 C2 N3 -55.2(3) . . . . ?
C1 N1 C2 C25 -94.9(3) . . . . ?
C23 N1 C2 C25 68.1(3) . . . . ?
C1 N1 C2 C3 25.6(3) . . . . ?
C23 N1 C2 C3 -171.5(2) . . . . ?
C1 N2 C3 N5 -86.5(2) . . . . ?
C24 N2 C3 N5 55.3(3) . . . . ?
C1 N2 C3 C31 151.3(2) . . . . ?
C24 N2 C3 C31 -66.9(3) . . . . ?
C1 N2 C3 C2 31.6(3) . . . . ?
C24 N2 C3 C2 173.4(2) . . . . ?
C4 N5 C3 N2 117.2(3) . . . . ?
C4 N5 C3 C31 -118.6(3) . . . . ?
C4 N5 C3 C2 8.3(3) . . . . ?
N3 C2 C3 N2 -153.1(2) . . . . ?
N1 C2 C3 N2 -32.8(2) . . . . ?
C25 C2 C3 N2 86.8(2) . . . . ?
N3 C2 C3 N5 -40.7(3) . . . . ?
N1 C2 C3 N5 79.6(2) . . . . ?
C25 C2 C3 N5 -160.8(2) . . . . ?
N3 C2 C3 C31 85.7(3) . . . . ?
N1 C2 C3 C31 -154.0(2) . . . . ?
C25 C2 C3 C31 -34.4(3) . . . . ?
C3 N5 C4 N4 10.7(4) . . . . ?
C3 N5 C4 S1 -165.68(19) . . . . ?
C5 N4 C4 N5 172.3(3) . . . . ?
N3 N4 C4 N5 4.9(4) . . . . ?
C5 N4 C4 S1 -10.9(3) . . . . ?
N3 N4 C4 S1 -178.20(18) . . . . ?
C6 S1 C4 N5 -166.9(2) . . . . ?
C6 S1 C4 N4 16.2(2) . . . . ?
C4 N4 C5 O2 179.3(2) . . . . ?
N3 N4 C5 O2 -14.0(4) . . . . ?
C4 N4 C5 C6 -2.6(3) . . . . ?
N3 N4 C5 C6 164.2(2) . . . . ?
O2 C5 C6 C7 -41.4(4) . . . . ?
N4 C5 C6 C7 140.5(2) . . . . ?
O2 C5 C6 C9 72.6(3) . . . . ?
N4 C5 C6 C9 -105.5(2) . . . . ?
O2 C5 C6 S1 -168.0(2) . . . . ?
N4 C5 C6 S1 13.9(3) . . . . ?
C4 S1 C6 C5 -16.76(19) . . . . ?
C4 S1 C6 C7 -137.6(2) . . . . ?
C4 S1 C6 C9 101.38(19) . . . . ?
C5 C6 C7 C17 -113.3(3) . . . . ?
C9 C6 C7 C17 129.8(3) . . . . ?
S1 C6 C7 C17 5.5(3) . . . . ?
C5 C6 C7 C8 118.9(2) . . . . ?
C9 C6 C7 C8 2.0(3) . . . . ?
S1 C6 C7 C8 -122.3(2) . . . . ?
C9 N6 C8 C7 44.4(3) . . . . ?
C37 N6 C8 C7 173.7(2) . . . . ?
C17 C7 C8 N6 -156.3(2) . . . . ?
C6 C7 C8 N6 -26.6(3) . . . . ?
C8 N6 C9 C16 -168.2(2) . . . . ?
C37 N6 C9 C16 63.1(3) . . . . ?
C8 N6 C9 C10 74.7(3) . . . . ?
C37 N6 C9 C10 -54.1(3) . . . . ?
C8 N6 C9 C6 -41.9(3) . . . . ?
C37 N6 C9 C6 -170.7(2) . . . . ?
C5 C6 C9 N6 -93.3(2) . . . . ?
C7 C6 C9 N6 23.2(3) . . . . ?
S1 C6 C9 N6 151.42(18) . . . . ?
C5 C6 C9 C16 32.2(3) . . . . ?
C7 C6 C9 C16 148.6(2) . . . . ?
S1 C6 C9 C16 -83.1(3) . . . . ?
C5 C6 C9 C10 144.3(2) . . . . ?
C7 C6 C9 C10 -99.2(2) . . . . ?
S1 C6 C9 C10 29.0(3) . . . . ?
C11 N7 C10 O3 176.7(3) . . . . ?
C38 N7 C10 O3 -8.8(5) . . . . ?
C11 N7 C10 C9 -4.6(3) . . . . ?
C38 N7 C10 C9 169.9(3) . . . . ?
N6 C9 C10 O3 -51.1(4) . . . . ?
C16 C9 C10 O3 -175.8(3) . . . . ?
C6 C9 C10 O3 62.2(3) . . . . ?
N6 C9 C10 N7 130.2(3) . . . . ?
C16 C9 C10 N7 5.6(3) . . . . ?
C6 C9 C10 N7 -116.5(2) . . . . ?
C10 N7 C11 C12 -174.6(3) . . . . ?
C38 N7 C11 C12 10.9(5) . . . . ?
C10 N7 C11 C16 1.6(3) . . . . ?
C38 N7 C11 C16 -172.9(3) . . . . ?
C16 C11 C12 C13 -0.4(5) . . . . ?
N7 C11 C12 C13 175.3(3) . . . . ?
C11 C12 C13 C14 -0.6(5) . . . . ?
C12 C13 C14 C15 0.1(5) . . . . ?
C13 C14 C15 C16 1.3(5) . . . . ?
C14 C15 C16 C11 -2.2(4) . . . . ?
C14 C15 C16 C9 -178.4(3) . . . . ?
C12 C11 C16 C15 1.8(5) . . . . ?
N7 C11 C16 C15 -174.6(3) . . . . ?
C12 C11 C16 C9 178.8(3) . . . . ?
N7 C11 C16 C9 2.3(3) . . . . ?
N6 C9 C16 C15 46.5(4) . . . . ?
C10 C9 C16 C15 171.9(3) . . . . ?
C6 C9 C16 C15 -72.1(4) . . . . ?
N6 C9 C16 C11 -130.0(3) . . . . ?
C10 C9 C16 C11 -4.7(3) . . . . ?
C6 C9 C16 C11 111.4(3) . . . . ?
C8 C7 C17 C22 -121.1(3) . . . . ?
C6 C7 C17 C22 116.6(3) . . . . ?
C8 C7 C17 C18 57.0(4) . . . . ?
C6 C7 C17 C18 -65.2(4) . . . . ?
C22 C17 C18 C19 -1.1(4) . . . . ?
C7 C17 C18 C19 -179.2(3) . . . . ?
C17 C18 C19 C20 1.2(5) . . . . ?
C18 C19 C20 C21 -0.3(5) . . . . ?
C18 C19 C20 Br1 -178.6(2) . . . . ?
C19 C20 C21 C22 -0.8(5) . . . . ?
Br1 C20 C21 C22 177.5(2) . . . . ?
C18 C17 C22 C21 0.0(4) . . . . ?
C7 C17 C22 C21 178.2(3) . . . . ?
C20 C21 C22 C17 0.9(5) . . . . ?
N3 C2 C25 C26 151.6(2) . . . . ?
N1 C2 C25 C26 24.4(3) . . . . ?
C3 C2 C25 C26 -87.1(3) . . . . ?
N3 C2 C25 C30 -30.3(3) . . . . ?
N1 C2 C25 C30 -157.5(2) . . . . ?
C3 C2 C25 C30 90.9(3) . . . . ?
C30 C25 C26 C27 -0.6(4) . . . . ?
C2 C25 C26 C27 177.5(3) . . . . ?
C25 C26 C27 C28 0.7(5) . . . . ?
C26 C27 C28 C29 0.1(5) . . . . ?
C27 C28 C29 C30 -1.0(5) . . . . ?
C28 C29 C30 C25 1.1(4) . . . . ?
C26 C25 C30 C29 -0.3(4) . . . . ?
C2 C25 C30 C29 -178.4(2) . . . . ?
N2 C3 C31 C32 -22.0(4) . . . . ?
N5 C3 C31 C32 -141.4(3) . . . . ?
C2 C3 C31 C32 90.8(3) . . . . ?
N2 C3 C31 C36 163.5(2) . . . . ?
N5 C3 C31 C36 44.1(3) . . . . ?
C2 C3 C31 C36 -83.6(3) . . . . ?
C36 C31 C32 C33 0.2(4) . . . . ?
C3 C31 C32 C33 -174.3(3) . . . . ?
C31 C32 C33 C34 0.4(5) . . . . ?
C32 C33 C34 C35 -0.1(5) . . . . ?
C33 C34 C35 C36 -0.8(5) . . . . ?
C34 C35 C36 C31 1.4(4) . . . . ?
C32 C31 C36 C35 -1.1(4) . . . . ?
C3 C31 C36 C35 173.4(3) . . . . ?
C10 N7 C38 C39 -105.1(4) . . . . ?
C11 N7 C38 C39 68.7(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 
N3 H3N O1  0.87(3) 2.16(3) 3.006(3) 163(3) 2_646
 
_refine_diff_density_max    0.787
_refine_diff_density_min   -0.833
_refine_diff_density_rms    0.075

_publ_section_references
;
Bruker (2014). APEX2 (version 2014.11-0); SAINT (version 8.34A);
Bruker AXS Inc., Madison, WI, USA.

Bruker (2008). SADABS version 2008/1, SHELXTL version 2008/4,
Bruker AXS, Madison, Wisconsin, USA.

Sheldrick, G.M. (2015a). SHELXT version 2014/5, Acta Cryst. A71, 3-8

Sheldrick G.M. (2015b). SHELXL version 2014/6, Acta Cryst. C71, 3-8
;

_shelxl_version_number 2014/6



