# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_704
_database_code_depnum_ccdc_archive 'CCDC 1999651'
loop_
_audit_author_name
_audit_author_address
'Pavel A. Slepukhin'
;Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-03-23 deposited with the CCDC.	2021-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C45 H28 F6 N2 O2'
_chemical_formula_sum            'C45 H28 F6 N2 O2'
_chemical_formula_weight         742.69

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.8731(13)
_cell_length_b                   12.7566(16)
_cell_length_c                   14.5064(19)
_cell_angle_alpha                66.069(12)
_cell_angle_beta                 86.317(10)
_cell_angle_gamma                85.015(10)
_cell_volume                     1831.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1295
_cell_measurement_theta_min      3.5650
_cell_measurement_theta_max      22.8820

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             764
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_min  0.73521
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12914
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_av_sigmaI/netI    0.1393
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         26.37
_reflns_number_total             7267
_reflns_number_gt                2594
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7267
_refine_ls_number_parameters     508
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1986
_refine_ls_R_factor_gt           0.0718
_refine_ls_wR_factor_ref         0.1826
_refine_ls_wR_factor_gt          0.1256
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.4452(4) 0.4389(4) 0.3969(2) 0.1548(18) Uani 1 1 d . . .
F2 F 0.6138(4) 0.5036(4) 0.4078(2) 0.1529(18) Uani 1 1 d . . .
F3 F 0.6148(4) 0.3541(4) 0.3776(2) 0.1470(17) Uani 1 1 d . . .
F4 F 0.5203(4) 0.3828(4) 0.1999(3) 0.1537(17) Uani 1 1 d . . .
F5 F 0.5016(4) 0.5513(3) 0.0902(2) 0.1504(17) Uani 1 1 d . . .
F6 F 0.3678(4) 0.4899(4) 0.2095(3) 0.1655(18) Uani 1 1 d . . .
N1 N 0.8512(3) 0.8564(3) 0.0664(2) 0.0482(8) Uani 1 1 d . . .
N2 N 0.8671(3) 0.8138(3) 0.2374(2) 0.0531(9) Uani 1 1 d . . .
O1 O 0.6466(3) 0.7300(3) 0.1299(2) 0.0741(9) Uani 1 1 d . . .
O2 O 0.6823(3) 0.5404(3) 0.21378(19) 0.0712(9) Uani 1 1 d . . .
C1 C 0.8502(6) 0.6483(5) 0.4572(4) 0.119(2) Uani 1 1 d . . .
H1A H 0.7910 0.6273 0.4255 0.143 Uiso 1 1 calc R . .
C2 C 0.8980(8) 0.5686(6) 0.5486(5) 0.149(3) Uani 1 1 d . . .
H2A H 0.8694 0.4952 0.5781 0.179 Uiso 1 1 calc R . .
C3 C 0.8245(4) 0.8860(3) 0.1499(3) 0.0469(10) Uani 1 1 d . . .
C4 C 0.7242(4) 1.0167(4) 0.2190(3) 0.0510(11) Uani 1 1 d . . .
C5 C 0.7537(4) 0.9894(3) 0.1337(2) 0.0447(10) Uani 1 1 d . . .
C6 C 0.8380(4) 0.8412(4) 0.3191(2) 0.0494(10) Uani 1 1 d . . .
C7 C 0.7682(4) 0.9371(4) 0.3141(3) 0.0512(11) Uani 1 1 d . . .
C8 C 0.5578(7) 0.4552(6) 0.3596(4) 0.0946(19) Uani 1 1 d . . .
C9 C 0.7420(4) 1.0273(3) -0.0468(2) 0.0480(10) Uani 1 1 d . . .
C10 C 0.7100(4) 1.0624(4) 0.0363(3) 0.0490(10) Uani 1 1 d . . .
C11 C 0.9126(4) 0.7461(4) 0.0850(2) 0.0497(10) Uani 1 1 d . . .
C12 C 0.4886(7) 0.4886(6) 0.1862(5) 0.0991(19) Uani 1 1 d . . .
C13 C 0.6976(4) 1.1014(3) -0.1494(2) 0.0518(11) Uani 1 1 d . . .
C14 C 0.8064(4) 0.9274(4) -0.0286(2) 0.0478(10) Uani 1 1 d . . .
C15 C 0.8294(4) 0.8790(3) -0.1077(2) 0.0510(11) Uani 1 1 d . . .
C16 C 0.7272(4) 0.9548(4) 0.4088(3) 0.0554(11) Uani 1 1 d . . .
C17 C 0.6388(4) 1.1623(4) 0.0246(3) 0.0584(12) Uani 1 1 d . . .
C18 C 0.8508(4) 0.6451(4) 0.1253(2) 0.0503(10) Uani 1 1 d . . .
C19 C 0.8903(4) 0.7552(4) 0.4153(3) 0.0580(12) Uani 1 1 d . . .
C20 C 0.6498(5) 1.1183(4) 0.2019(3) 0.0636(13) Uani 1 1 d . . .
C21 C 0.6095(5) 1.1883(4) 0.1086(3) 0.0654(13) Uani 1 1 d . . .
C22 C 1.0356(5) 0.7421(5) 0.0571(3) 0.0700(13) Uani 1 1 d . . .
H22A H 1.0769 0.8095 0.0307 0.084 Uiso 1 1 calc R . .
C23 C 0.5790(4) 1.0997(4) -0.1747(3) 0.0651(13) Uani 1 1 d . . .
H23A H 0.5261 1.0503 -0.1271 0.078 Uiso 1 1 calc R . .
C24 C 0.7173(5) 0.6486(4) 0.1545(3) 0.0569(12) Uani 1 1 d . . .
C25 C 0.7479(4) 0.8084(4) -0.1162(3) 0.0615(13) Uani 1 1 d . . .
H25A H 0.6791 0.7895 -0.0725 0.074 Uiso 1 1 calc R . .
C27 C 0.7737(4) 1.1762(4) -0.2228(3) 0.0739(15) Uani 1 1 d . . .
H27A H 0.8549 1.1798 -0.2082 0.089 Uiso 1 1 calc R . .
C28 C 0.6522(4) 0.8773(4) 0.4807(3) 0.0689(14) Uani 1 1 d . . .
H28A H 0.6270 0.8153 0.4702 0.083 Uiso 1 1 calc R . .
C29 C 0.9449(6) 0.8595(6) -0.2454(4) 0.122(2) Uani 1 1 d . . .
H29A H 1.0123 0.8789 -0.2905 0.147 Uiso 1 1 calc R . .
C30 C 0.9160(5) 0.5427(4) 0.1347(3) 0.0667(13) Uani 1 1 d . . .
H30A H 0.8760 0.4747 0.1612 0.080 Uiso 1 1 calc R . .
C31 C 0.5579(4) 0.5313(4) 0.2483(3) 0.0665(13) Uani 1 1 d . . .
H31A H 0.5221 0.6079 0.2395 0.080 Uiso 1 1 calc R . .
C32 C 0.5360(5) 1.1688(4) -0.2683(3) 0.0750(14) Uani 1 1 d . . .
H32A H 0.4549 1.1653 -0.2832 0.090 Uiso 1 1 calc R . .
C33 C 1.0984(5) 0.6398(6) 0.0678(4) 0.0887(17) Uani 1 1 d . . .
H33A H 1.1818 0.6382 0.0491 0.106 Uiso 1 1 calc R . .
C34 C 0.6146(5) 0.8921(5) 0.5682(3) 0.0851(17) Uani 1 1 d . . .
H34A H 0.5639 0.8396 0.6155 0.102 Uiso 1 1 calc R . .
C35 C 0.7306(6) 1.2451(4) -0.3169(3) 0.0883(18) Uani 1 1 d . . .
H35A H 0.7829 1.2939 -0.3657 0.106 Uiso 1 1 calc R . .
C36 C 0.9295(5) 0.9046(5) -0.1731(3) 0.0907(18) Uani 1 1 d . . .
H36A H 0.9871 0.9523 -0.1689 0.109 Uiso 1 1 calc R . .
C37 C 1.0384(5) 0.5405(5) 0.1057(3) 0.0835(15) Uani 1 1 d . . .
H37A H 1.0805 0.4714 0.1118 0.100 Uiso 1 1 calc R . .
C38 C 0.7233(5) 1.0587(5) 0.5158(4) 0.0939(18) Uani 1 1 d . . .
H38A H 0.7474 1.1205 0.5271 0.113 Uiso 1 1 calc R . .
C39 C 0.7618(5) 1.0453(4) 0.4276(3) 0.0827(17) Uani 1 1 d . . .
H39A H 0.8118 1.0985 0.3804 0.099 Uiso 1 1 calc R . .
C40 C 0.9866(7) 0.5986(6) 0.5947(4) 0.114(2) Uani 1 1 d . . .
H40A H 1.0186 0.5462 0.6554 0.137 Uiso 1 1 calc R . .
C41 C 0.6102(6) 1.2420(4) -0.3390(3) 0.0795(16) Uani 1 1 d . . .
H41A H 0.5803 1.2897 -0.4021 0.095 Uiso 1 1 calc R . .
C42 C 0.6497(5) 0.9802(5) 0.5861(3) 0.0829(16) Uani 1 1 d . . .
H42A H 0.6244 0.9882 0.6456 0.099 Uiso 1 1 calc R . .
C43 C 0.7665(5) 0.7649(4) -0.1889(3) 0.0826(16) Uani 1 1 d . . .
H43A H 0.7093 0.7177 -0.1944 0.099 Uiso 1 1 calc R . .
C44 C 0.8660(6) 0.7892(5) -0.2523(4) 0.0966(19) Uani 1 1 d . . .
H44A H 0.8793 0.7575 -0.3000 0.116 Uiso 1 1 calc R . .
C45 C 0.9783(5) 0.7834(5) 0.4627(3) 0.0856(17) Uani 1 1 d . . .
H45A H 1.0061 0.8572 0.4349 0.103 Uiso 1 1 calc R . .
C26 C 1.0260(6) 0.7037(7) 0.5510(4) 0.107(2) Uani 1 1 d . . .
H26A H 1.0875 0.7240 0.5811 0.129 Uiso 1 1 calc R . .
H20 H 0.621(3) 1.134(3) 0.261(2) 0.065(11) Uiso 1 1 d . . .
H17 H 0.602(3) 1.217(3) -0.043(2) 0.047(10) Uiso 1 1 d . . .
H21 H 0.549(5) 1.261(5) 0.090(3) 0.13(2) Uiso 1 1 d . . .


_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
F1 C8 1.305(7) . ?
F2 C8 1.308(6) . ?
F3 C8 1.313(8) . ?
F4 C12 1.299(7) . ?
F5 C12 1.300(6) . ?
F6 C12 1.335(7) . ?
N1 C14 1.397(4) . ?
N1 C3 1.414(4) . ?
N1 C11 1.433(5) . ?
N2 C3 1.314(4) . ?
N2 C6 1.379(4) . ?
O1 C24 1.180(5) . ?
O2 C24 1.369(4) . ?
O2 C31 1.410(5) . ?
C1 C19 1.348(6) . ?
C1 C2 1.402(7) . ?
C1 H1A 0.9300 . ?
C2 C40 1.369(8) . ?
C2 H2A 0.9300 . ?
C3 C5 1.409(5) . ?
C4 C20 1.407(6) . ?
C4 C7 1.424(5) . ?
C4 C5 1.425(5) . ?
C5 C10 1.425(5) . ?
C6 C7 1.360(6) . ?
C6 C19 1.491(5) . ?
C7 C16 1.514(5) . ?
C8 C31 1.509(6) . ?
C9 C14 1.334(5) . ?
C9 C10 1.460(5) . ?
C9 C13 1.488(5) . ?
C10 C17 1.386(6) . ?
C11 C22 1.375(6) . ?
C11 C18 1.394(5) . ?
C12 C31 1.495(6) . ?
C13 C23 1.367(5) . ?
C13 C27 1.389(5) . ?
C14 C15 1.507(5) . ?
C15 C25 1.362(5) . ?
C15 C36 1.367(5) . ?
C16 C39 1.375(5) . ?
C16 C28 1.387(5) . ?
C17 C21 1.398(5) . ?
C17 H17 1.03(3) . ?
C18 C30 1.390(6) . ?
C18 C24 1.487(6) . ?
C19 C45 1.365(5) . ?
C20 C21 1.360(6) . ?
C20 H20 0.98(4) . ?
C21 H21 1.04(6) . ?
C22 C33 1.373(7) . ?
C22 H22A 0.9300 . ?
C23 C32 1.370(5) . ?
C23 H23A 0.9300 . ?
C25 C43 1.375(6) . ?
C25 H25A 0.9300 . ?
C27 C35 1.376(6) . ?
C27 H27A 0.9300 . ?
C28 C34 1.388(5) . ?
C28 H28A 0.9300 . ?
C29 C44 1.330(7) . ?
C29 C36 1.382(6) . ?
C29 H29A 0.9300 . ?
C30 C37 1.371(6) . ?
C30 H30A 0.9300 . ?
C31 H31A 0.9800 . ?
C32 C41 1.350(6) . ?
C32 H32A 0.9300 . ?
C33 C37 1.366(6) . ?
C33 H33A 0.9300 . ?
C34 C42 1.343(6) . ?
C34 H34A 0.9300 . ?
C35 C41 1.375(6) . ?
C35 H35A 0.9300 . ?
C36 H36A 0.9300 . ?
C37 H37A 0.9300 . ?
C38 C42 1.374(6) . ?
C38 C39 1.392(5) . ?
C38 H38A 0.9300 . ?
C39 H39A 0.9300 . ?
C40 C26 1.326(7) . ?
C40 H40A 0.9300 . ?
C41 H41A 0.9300 . ?
C42 H42A 0.9300 . ?
C43 C44 1.346(7) . ?
C43 H43A 0.9300 . ?
C44 H44A 0.9300 . ?
C45 C26 1.372(7) . ?
C45 H45A 0.9300 . ?
C26 H26A 0.9300 . ?

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
C14 N1 C3 120.5(3) . . ?
C14 N1 C11 121.3(3) . . ?
C3 N1 C11 117.8(3) . . ?
C3 N2 C6 117.0(4) . . ?
C24 O2 C31 116.6(4) . . ?
C19 C1 C2 119.8(5) . . ?
C19 C1 H1A 120.1 . . ?
C2 C1 H1A 120.1 . . ?
C40 C2 C1 120.2(6) . . ?
C40 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
N2 C3 C5 124.9(3) . . ?
N2 C3 N1 117.1(4) . . ?
C5 C3 N1 118.0(3) . . ?
C20 C4 C7 125.8(3) . . ?
C20 C4 C5 116.7(4) . . ?
C7 C4 C5 117.5(4) . . ?
C3 C5 C4 117.5(3) . . ?
C3 C5 C10 121.2(3) . . ?
C4 C5 C10 121.2(4) . . ?
C7 C6 N2 123.9(3) . . ?
C7 C6 C19 122.5(3) . . ?
N2 C6 C19 113.6(4) . . ?
C6 C7 C4 119.1(3) . . ?
C6 C7 C16 121.0(3) . . ?
C4 C7 C16 119.6(4) . . ?
F1 C8 F2 108.1(6) . . ?
F1 C8 F3 107.9(5) . . ?
F2 C8 F3 108.1(6) . . ?
F1 C8 C31 111.0(6) . . ?
F2 C8 C31 109.8(5) . . ?
F3 C8 C31 111.9(5) . . ?
C14 C9 C10 119.5(3) . . ?
C14 C9 C13 121.2(3) . . ?
C10 C9 C13 119.3(4) . . ?
C17 C10 C5 119.1(3) . . ?
C17 C10 C9 123.0(4) . . ?
C5 C10 C9 117.9(4) . . ?
C22 C11 C18 119.7(4) . . ?
C22 C11 N1 117.9(4) . . ?
C18 C11 N1 122.3(4) . . ?
F4 C12 F5 107.3(6) . . ?
F4 C12 F6 104.9(5) . . ?
F5 C12 F6 107.2(6) . . ?
F4 C12 C31 113.9(6) . . ?
F5 C12 C31 112.0(5) . . ?
F6 C12 C31 111.0(5) . . ?
C23 C13 C27 117.3(4) . . ?
C23 C13 C9 121.0(3) . . ?
C27 C13 C9 121.7(4) . . ?
C9 C14 N1 122.8(3) . . ?
C9 C14 C15 122.3(3) . . ?
N1 C14 C15 114.8(4) . . ?
C25 C15 C36 118.1(4) . . ?
C25 C15 C14 119.7(3) . . ?
C36 C15 C14 122.2(4) . . ?
C39 C16 C28 117.7(3) . . ?
C39 C16 C7 122.7(3) . . ?
C28 C16 C7 119.6(3) . . ?
C10 C17 C21 119.5(4) . . ?
C10 C17 H17 123(2) . . ?
C21 C17 H17 118(2) . . ?
C30 C18 C11 118.4(4) . . ?
C30 C18 C24 121.4(4) . . ?
C11 C18 C24 120.2(4) . . ?
C1 C19 C45 119.0(4) . . ?
C1 C19 C6 120.2(4) . . ?
C45 C19 C6 120.8(4) . . ?
C21 C20 C4 121.9(4) . . ?
C21 C20 H20 120(2) . . ?
C4 C20 H20 118(2) . . ?
C20 C21 C17 121.7(5) . . ?
C20 C21 H21 127(3) . . ?
C17 C21 H21 111(3) . . ?
C33 C22 C11 120.9(5) . . ?
C33 C22 H22A 119.6 . . ?
C11 C22 H22A 119.6 . . ?
C13 C23 C32 121.9(4) . . ?
C13 C23 H23A 119.1 . . ?
C32 C23 H23A 119.1 . . ?
O1 C24 O2 122.2(5) . . ?
O1 C24 C18 127.2(4) . . ?
O2 C24 C18 110.6(4) . . ?
C15 C25 C43 120.4(4) . . ?
C15 C25 H25A 119.8 . . ?
C43 C25 H25A 119.8 . . ?
C35 C27 C13 120.8(4) . . ?
C35 C27 H27A 119.6 . . ?
C13 C27 H27A 119.6 . . ?
C16 C28 C34 120.2(4) . . ?
C16 C28 H28A 119.9 . . ?
C34 C28 H28A 119.9 . . ?
C44 C29 C36 121.8(5) . . ?
C44 C29 H29A 119.1 . . ?
C36 C29 H29A 119.1 . . ?
C37 C30 C18 121.2(5) . . ?
C37 C30 H30A 119.4 . . ?
C18 C30 H30A 119.4 . . ?
O2 C31 C12 109.1(4) . . ?
O2 C31 C8 107.0(4) . . ?
C12 C31 C8 114.7(5) . . ?
O2 C31 H31A 108.6 . . ?
C12 C31 H31A 108.6 . . ?
C8 C31 H31A 108.6 . . ?
C41 C32 C23 120.6(5) . . ?
C41 C32 H32A 119.7 . . ?
C23 C32 H32A 119.7 . . ?
C37 C33 C22 120.0(5) . . ?
C37 C33 H33A 120.0 . . ?
C22 C33 H33A 120.0 . . ?
C42 C34 C28 121.6(4) . . ?
C42 C34 H34A 119.2 . . ?
C28 C34 H34A 119.2 . . ?
C41 C35 C27 120.2(4) . . ?
C41 C35 H35A 119.9 . . ?
C27 C35 H35A 119.9 . . ?
C15 C36 C29 119.8(4) . . ?
C15 C36 H36A 120.1 . . ?
C29 C36 H36A 120.1 . . ?
C33 C37 C30 119.9(5) . . ?
C33 C37 H37A 120.1 . . ?
C30 C37 H37A 120.1 . . ?
C42 C38 C39 119.9(4) . . ?
C42 C38 H38A 120.1 . . ?
C39 C38 H38A 120.1 . . ?
C16 C39 C38 121.3(4) . . ?
C16 C39 H39A 119.4 . . ?
C38 C39 H39A 119.4 . . ?
C26 C40 C2 118.7(6) . . ?
C26 C40 H40A 120.6 . . ?
C2 C40 H40A 120.6 . . ?
C32 C41 C35 119.3(4) . . ?
C32 C41 H41A 120.4 . . ?
C35 C41 H41A 120.4 . . ?
C34 C42 C38 119.3(4) . . ?
C34 C42 H42A 120.3 . . ?
C38 C42 H42A 120.3 . . ?
C44 C43 C25 121.2(5) . . ?
C44 C43 H43A 119.4 . . ?
C25 C43 H43A 119.4 . . ?
C29 C44 C43 118.6(5) . . ?
C29 C44 H44A 120.7 . . ?
C43 C44 H44A 120.7 . . ?
C19 C45 C26 120.4(5) . . ?
C19 C45 H45A 119.8 . . ?
C26 C45 H45A 119.8 . . ?
C40 C26 C45 121.8(6) . . ?
C40 C26 H26A 119.1 . . ?
C45 C26 H26A 119.1 . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.053
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_663
_database_code_depnum_ccdc_archive 'CCDC 2004850'
loop_
_audit_author_name
_audit_author_address
'Pavel A. Slepukhin'
;Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-03-23 deposited with the CCDC.	2021-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H16 N2 O S'
_chemical_formula_sum            'C26 H16 N2 O S'
_chemical_formula_weight         404.47

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9557(7)
_cell_length_b                   9.9486(8)
_cell_length_c                   22.5422(17)
_cell_angle_alpha                98.812(6)
_cell_angle_beta                 91.216(6)
_cell_angle_gamma                97.590(6)
_cell_volume                     1965.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2090
_cell_measurement_theta_min      3.5600
_cell_measurement_theta_max      26.4370

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_min  0.84717
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur 3 CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17949
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_sigmaI/netI    0.1413
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         31.01
_reflns_number_total             10435
_reflns_number_gt                4298
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0650P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         10435
_refine_ls_number_parameters     565
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1891
_refine_ls_R_factor_gt           0.0740
_refine_ls_wR_factor_ref         0.2254
_refine_ls_wR_factor_gt          0.1492
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.86220(11) 0.79210(11) 0.04787(4) 0.0496(3) Uani 1 1 d . . .
N1 N 0.8609(3) 1.0809(3) 0.11464(13) 0.0434(7) Uani 1 1 d . . .
O1 O 0.8247(3) 1.4112(3) 0.03180(12) 0.0577(7) Uani 1 1 d . . .
C1 C 0.8647(4) 1.2083(4) 0.14908(16) 0.0441(9) Uani 1 1 d . . .
N2 N 0.7898(3) 1.1747(3) 0.02676(12) 0.0385(7) Uani 1 1 d . . .
C2 C 0.8920(4) 1.2230(4) 0.21121(17) 0.0499(10) Uani 1 1 d . . .
H2A H 0.9075 1.1471 0.2289 0.060 Uiso 1 1 calc R . .
C3 C 0.8958(5) 1.3491(5) 0.24608(19) 0.0616(12) Uani 1 1 d . . .
H3A H 0.9134 1.3580 0.2874 0.074 Uiso 1 1 calc R . .
C4 C 0.8736(5) 1.4643(5) 0.22031(19) 0.0643(12) Uani 1 1 d . . .
H4A H 0.8737 1.5488 0.2446 0.077 Uiso 1 1 calc R . .
C5 C 0.8517(5) 1.4529(5) 0.15941(19) 0.0559(11) Uani 1 1 d . . .
C6 C 0.8458(4) 1.3249(4) 0.12332(16) 0.0429(9) Uani 1 1 d . . .
C7 C 0.8209(4) 1.3140(4) 0.05847(16) 0.0424(8) Uani 1 1 d . . .
C9 C 0.7410(4) 1.1474(4) -0.03544(15) 0.0384(8) Uani 1 1 d . . .
C10 C 0.7367(4) 1.0205(4) -0.06771(15) 0.0396(8) Uani 1 1 d . . .
C11 C 0.7806(4) 0.9108(4) -0.03884(16) 0.0403(8) Uani 1 1 d . . .
C12 C 0.7845(4) 0.7704(4) -0.06352(19) 0.0466(9) Uani 1 1 d . . .
C13 C 0.8256(4) 0.6965(4) -0.02219(18) 0.0492(10) Uani 1 1 d . . .
C14 C 0.8204(4) 0.9362(4) 0.02091(15) 0.0392(8) Uani 1 1 d . . .
C15 C 0.8249(4) 1.0675(4) 0.05751(16) 0.0395(8) Uani 1 1 d . . .
C16 C 0.6816(4) 0.9835(4) -0.13161(16) 0.0419(8) Uani 1 1 d . . .
C17 C 0.5294(4) 0.9725(5) -0.14800(19) 0.0589(11) Uani 1 1 d . . .
H17A H 0.4603 0.9927 -0.1189 0.071 Uiso 1 1 calc R . .
C18 C 0.4809(5) 0.9320(5) -0.2069(2) 0.0697(13) Uani 1 1 d . . .
H18A H 0.3789 0.9242 -0.2176 0.084 Uiso 1 1 calc R . .
C19 C 0.5834(6) 0.9029(5) -0.2505(2) 0.0698(13) Uani 1 1 d . . .
H19A H 0.5503 0.8760 -0.2904 0.084 Uiso 1 1 calc R . .
C20 C 0.7325(5) 0.9136(5) -0.23500(19) 0.0642(12) Uani 1 1 d . . .
H20A H 0.8013 0.8936 -0.2643 0.077 Uiso 1 1 calc R . .
C21 C 0.7815(4) 0.9540(4) -0.17594(18) 0.0533(10) Uani 1 1 d . . .
H21A H 0.8838 0.9616 -0.1657 0.064 Uiso 1 1 calc R . .
C22 C 0.6853(4) 1.2590(4) -0.06373(15) 0.0398(8) Uani 1 1 d . . .
C23 C 0.5527(4) 1.3090(4) -0.04733(18) 0.0507(10) Uani 1 1 d . . .
H23A H 0.5014 1.2795 -0.0152 0.061 Uiso 1 1 calc R . .
C24 C 0.4954(5) 1.4025(4) -0.0781(2) 0.0598(11) Uani 1 1 d . . .
H24A H 0.4073 1.4368 -0.0662 0.072 Uiso 1 1 calc R . .
C25 C 0.5686(5) 1.4442(5) -0.1261(2) 0.0642(12) Uani 1 1 d . . .
H25A H 0.5286 1.5050 -0.1474 0.077 Uiso 1 1 calc R . .
C26 C 0.7017(6) 1.3965(5) -0.14300(19) 0.0677(13) Uani 1 1 d . . .
H26A H 0.7520 1.4257 -0.1754 0.081 Uiso 1 1 calc R . .
C27 C 0.7595(5) 1.3054(4) -0.11161(17) 0.0548(11) Uani 1 1 d . . .
H27A H 0.8500 1.2744 -0.1227 0.066 Uiso 1 1 calc R . .
S1A S 0.63925(12) 0.92148(12) 0.58615(4) 0.0580(3) Uani 1 1 d . . .
N1A N 0.8625(3) 1.1191(3) 0.52900(13) 0.0463(8) Uani 1 1 d . . .
O1A O 0.8280(3) 1.1360(3) 0.35149(12) 0.0665(8) Uani 1 1 d . . .
C1A C 0.9608(4) 1.2137(4) 0.50536(17) 0.0456(9) Uani 1 1 d . . .
N2A N 0.7899(3) 1.0068(3) 0.42789(12) 0.0428(7) Uani 1 1 d . . .
C2A C 1.0562(5) 1.3137(5) 0.54423(19) 0.0583(11) Uani 1 1 d . . .
H2AA H 1.0512 1.3166 0.5856 0.070 Uiso 1 1 calc R . .
C3A C 1.1570(5) 1.4074(5) 0.5217(2) 0.0728(13) Uani 1 1 d . . .
H3AA H 1.2220 1.4713 0.5479 0.087 Uiso 1 1 calc R . .
C4A C 1.1629(5) 1.4077(5) 0.4599(2) 0.0734(13) Uani 1 1 d . . .
H4AA H 1.2322 1.4712 0.4452 0.088 Uiso 1 1 calc R . .
C5A C 1.0672(5) 1.3150(5) 0.4212(2) 0.0617(12) Uani 1 1 d . . .
C6A C 0.9647(4) 1.2180(4) 0.44357(17) 0.0478(9) Uani 1 1 d . . .
C7A C 0.8594(4) 1.1222(4) 0.40270(17) 0.0482(9) Uani 1 1 d . . .
C9A C 0.7138(4) 0.8904(4) 0.38931(15) 0.0436(9) Uani 1 1 d . . .
C10A C 0.6064(4) 0.8032(4) 0.41045(16) 0.0461(9) Uani 1 1 d . . .
C11A C 0.5808(4) 0.8226(4) 0.47421(17) 0.0477(9) Uani 1 1 d . . .
C12A C 0.4795(5) 0.7434(5) 0.5074(2) 0.0582(11) Uani 1 1 d . . .
C13A C 0.4986(5) 0.7856(5) 0.5668(2) 0.0637(12) Uani 1 1 d . . .
C14A C 0.6722(4) 0.9230(4) 0.51169(16) 0.0473(9) Uani 1 1 d . . .
C15A C 0.7827(4) 1.0212(4) 0.49110(16) 0.0440(9) Uani 1 1 d . . .
C16A C 0.5170(4) 0.6828(4) 0.37100(16) 0.0485(9) Uani 1 1 d . . .
C17A C 0.3628(5) 0.6799(5) 0.36282(19) 0.0632(12) Uani 1 1 d . . .
H17B H 0.3160 0.7510 0.3827 0.076 Uiso 1 1 calc R . .
C18A C 0.2776(5) 0.5730(5) 0.3256(2) 0.0702(13) Uani 1 1 d . . .
H18B H 0.1742 0.5725 0.3205 0.084 Uiso 1 1 calc R . .
C19A C 0.3453(6) 0.4667(5) 0.2960(2) 0.0739(13) Uani 1 1 d . . .
H19B H 0.2883 0.3947 0.2707 0.089 Uiso 1 1 calc R . .
C20A C 0.4987(6) 0.4686(5) 0.3043(2) 0.0681(12) Uani 1 1 d . . .
H20B H 0.5448 0.3971 0.2844 0.082 Uiso 1 1 calc R . .
C21A C 0.5849(5) 0.5743(5) 0.34161(18) 0.0582(11) Uani 1 1 d . . .
H21B H 0.6879 0.5733 0.3472 0.070 Uiso 1 1 calc R . .
C22A C 0.7746(4) 0.8637(4) 0.32803(16) 0.0466(9) Uani 1 1 d . . .
C23A C 0.6814(5) 0.8382(4) 0.27612(17) 0.0551(10) Uani 1 1 d . . .
H23B H 0.5778 0.8374 0.2789 0.066 Uiso 1 1 calc R . .
C24A C 0.7436(6) 0.8142(5) 0.22045(18) 0.0646(12) Uani 1 1 d . . .
H24B H 0.6813 0.7977 0.1858 0.078 Uiso 1 1 calc R . .
C25A C 0.8957(6) 0.8145(5) 0.2157(2) 0.0674(13) Uani 1 1 d . . .
H25B H 0.9362 0.7999 0.1780 0.081 Uiso 1 1 calc R . .
C26A C 0.9885(5) 0.8362(5) 0.2664(2) 0.0622(12) Uani 1 1 d . . .
H26B H 1.0916 0.8341 0.2633 0.075 Uiso 1 1 calc R . .
C27A C 0.9273(4) 0.8612(4) 0.32222(17) 0.0508(10) Uani 1 1 d . . .
H27B H 0.9904 0.8766 0.3566 0.061 Uiso 1 1 calc R . .
H12 H 0.760(3) 0.730(4) -0.1063(15) 0.042(10) Uiso 1 1 d . . .
H13A H 0.452(4) 0.748(5) 0.6000(19) 0.072(13) Uiso 1 1 d . . .
H5 H 0.825(4) 1.541(4) 0.1414(17) 0.068(12) Uiso 1 1 d . . .
H5A H 1.069(4) 1.311(4) 0.3789(17) 0.055(12) Uiso 1 1 d . . .
H13 H 0.836(4) 0.592(5) -0.0282(17) 0.070(12) Uiso 1 1 d . . .
H12A H 0.402(4) 0.662(5) 0.4835(18) 0.076(14) Uiso 1 1 d . . .


_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
S1 C13 1.715(4) . ?
S1 C14 1.722(4) . ?
N1 C15 1.303(4) . ?
N1 C1 1.377(5) . ?
O1 C7 1.211(4) . ?
C1 C2 1.398(5) . ?
C1 C6 1.402(5) . ?
N2 C15 1.422(4) . ?
N2 C9 1.434(4) . ?
N2 C7 1.448(5) . ?
C2 C3 1.370(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.396(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.368(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.396(5) . ?
C5 H5 1.07(4) . ?
C6 C7 1.459(5) . ?
C9 C10 1.352(5) . ?
C9 C22 1.496(5) . ?
C10 C11 1.446(5) . ?
C10 C16 1.487(5) . ?
C11 C14 1.363(5) . ?
C11 C12 1.428(5) . ?
C12 C13 1.346(5) . ?
C12 H12 0.99(3) . ?
C13 H13 1.05(4) . ?
C14 C15 1.429(5) . ?
C16 C21 1.379(5) . ?
C16 C17 1.390(5) . ?
C17 C18 1.371(6) . ?
C17 H17A 0.9300 . ?
C18 C19 1.382(6) . ?
C18 H18A 0.9300 . ?
C19 C20 1.359(6) . ?
C19 H19A 0.9300 . ?
C20 C21 1.375(5) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
C22 C23 1.383(5) . ?
C22 C27 1.386(5) . ?
C23 C24 1.385(5) . ?
C23 H23A 0.9300 . ?
C24 C25 1.366(6) . ?
C24 H24A 0.9300 . ?
C25 C26 1.380(6) . ?
C25 H25A 0.9300 . ?
C26 C27 1.377(5) . ?
C26 H26A 0.9300 . ?
C27 H27A 0.9300 . ?
S1A C14A 1.712(4) . ?
S1A C13A 1.718(5) . ?
N1A C15A 1.313(5) . ?
N1A C1A 1.379(5) . ?
O1A C7A 1.215(4) . ?
C1A C6A 1.401(5) . ?
C1A C2A 1.401(5) . ?
N2A C15A 1.414(4) . ?
N2A C9A 1.421(5) . ?
N2A C7A 1.433(5) . ?
C2A C3A 1.372(6) . ?
C2A H2AA 0.9300 . ?
C3A C4A 1.396(6) . ?
C3A H3AA 0.9300 . ?
C4A C5A 1.364(6) . ?
C4A H4AA 0.9300 . ?
C5A C6A 1.401(6) . ?
C5A H5A 0.95(4) . ?
C6A C7A 1.450(5) . ?
C9A C10A 1.353(5) . ?
C9A C22A 1.494(5) . ?
C10A C11A 1.448(5) . ?
C10A C16A 1.502(5) . ?
C11A C14A 1.370(5) . ?
C11A C12A 1.423(5) . ?
C12A C13A 1.340(6) . ?
C12A H12A 1.06(4) . ?
C13A H13A 0.97(4) . ?
C14A C15A 1.433(5) . ?
C16A C17A 1.386(5) . ?
C16A C21A 1.395(5) . ?
C17A C18A 1.379(6) . ?
C17A H17B 0.9300 . ?
C18A C19A 1.378(6) . ?
C18A H18B 0.9300 . ?
C19A C20A 1.380(6) . ?
C19A H19B 0.9300 . ?
C20A C21A 1.376(6) . ?
C20A H20B 0.9300 . ?
C21A H21B 0.9300 . ?
C22A C27A 1.379(5) . ?
C22A C23A 1.394(5) . ?
C23A C24A 1.384(5) . ?
C23A H23B 0.9300 . ?
C24A C25A 1.368(6) . ?
C24A H24B 0.9300 . ?
C25A C26A 1.371(6) . ?
C25A H25B 0.9300 . ?
C26A C27A 1.384(5) . ?
C26A H26B 0.9300 . ?
C27A H27B 0.9300 . ?

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
C13 S1 C14 90.48(19) . . ?
C15 N1 C1 118.4(3) . . ?
N1 C1 C2 119.4(3) . . ?
N1 C1 C6 121.7(3) . . ?
C2 C1 C6 118.9(4) . . ?
C15 N2 C9 121.1(3) . . ?
C15 N2 C7 117.6(3) . . ?
C9 N2 C7 121.0(3) . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C2 C3 C4 120.8(4) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C4 C5 C6 119.9(4) . . ?
C4 C5 H5 118(2) . . ?
C6 C5 H5 122(2) . . ?
C5 C6 C1 120.3(4) . . ?
C5 C6 C7 119.3(3) . . ?
C1 C6 C7 120.4(3) . . ?
O1 C7 N2 121.0(3) . . ?
O1 C7 C6 124.5(4) . . ?
N2 C7 C6 114.6(3) . . ?
C10 C9 N2 120.9(3) . . ?
C10 C9 C22 119.7(3) . . ?
N2 C9 C22 119.3(3) . . ?
C9 C10 C11 119.4(3) . . ?
C9 C10 C16 123.8(3) . . ?
C11 C10 C16 116.7(3) . . ?
C14 C11 C12 111.5(3) . . ?
C14 C11 C10 119.3(3) . . ?
C12 C11 C10 129.2(3) . . ?
C13 C12 C11 112.4(4) . . ?
C13 C12 H12 123(2) . . ?
C11 C12 H12 125(2) . . ?
C12 C13 S1 113.0(3) . . ?
C12 C13 H13 128(2) . . ?
S1 C13 H13 119(2) . . ?
C11 C14 C15 123.8(3) . . ?
C11 C14 S1 112.6(3) . . ?
C15 C14 S1 123.6(3) . . ?
N1 C15 N2 125.4(3) . . ?
N1 C15 C14 119.3(3) . . ?
N2 C15 C14 115.2(3) . . ?
C21 C16 C17 118.4(4) . . ?
C21 C16 C10 120.0(3) . . ?
C17 C16 C10 121.5(3) . . ?
C18 C17 C16 120.3(4) . . ?
C18 C17 H17A 119.9 . . ?
C16 C17 H17A 119.9 . . ?
C17 C18 C19 120.1(4) . . ?
C17 C18 H18A 119.9 . . ?
C19 C18 H18A 119.9 . . ?
C20 C19 C18 120.2(4) . . ?
C20 C19 H19A 119.9 . . ?
C18 C19 H19A 119.9 . . ?
C19 C20 C21 119.9(4) . . ?
C19 C20 H20A 120.1 . . ?
C21 C20 H20A 120.1 . . ?
C20 C21 C16 121.1(4) . . ?
C20 C21 H21A 119.4 . . ?
C16 C21 H21A 119.4 . . ?
C23 C22 C27 118.2(3) . . ?
C23 C22 C9 121.8(3) . . ?
C27 C22 C9 119.8(3) . . ?
C22 C23 C24 120.8(4) . . ?
C22 C23 H23A 119.6 . . ?
C24 C23 H23A 119.6 . . ?
C25 C24 C23 119.9(4) . . ?
C25 C24 H24A 120.0 . . ?
C23 C24 H24A 120.0 . . ?
C24 C25 C26 120.3(4) . . ?
C24 C25 H25A 119.9 . . ?
C26 C25 H25A 119.9 . . ?
C27 C26 C25 119.5(4) . . ?
C27 C26 H26A 120.2 . . ?
C25 C26 H26A 120.2 . . ?
C26 C27 C22 121.2(4) . . ?
C26 C27 H27A 119.4 . . ?
C22 C27 H27A 119.4 . . ?
C14A S1A C13A 89.8(2) . . ?
C15A N1A C1A 117.5(3) . . ?
N1A C1A C6A 122.4(4) . . ?
N1A C1A C2A 119.4(4) . . ?
C6A C1A C2A 118.2(4) . . ?
C15A N2A C9A 122.1(3) . . ?
C15A N2A C7A 117.7(3) . . ?
C9A N2A C7A 119.6(3) . . ?
C3A C2A C1A 120.5(4) . . ?
C3A C2A H2AA 119.8 . . ?
C1A C2A H2AA 119.8 . . ?
C2A C3A C4A 120.7(4) . . ?
C2A C3A H3AA 119.7 . . ?
C4A C3A H3AA 119.7 . . ?
C5A C4A C3A 120.0(5) . . ?
C5A C4A H4AA 120.0 . . ?
C3A C4A H4AA 120.0 . . ?
C4A C5A C6A 119.8(4) . . ?
C4A C5A H5A 122(2) . . ?
C6A C5A H5A 118(2) . . ?
C5A C6A C1A 120.7(4) . . ?
C5A C6A C7A 120.0(4) . . ?
C1A C6A C7A 119.3(4) . . ?
O1A C7A N2A 121.0(4) . . ?
O1A C7A C6A 124.7(4) . . ?
N2A C7A C6A 114.4(3) . . ?
C10A C9A N2A 120.6(3) . . ?
C10A C9A C22A 123.7(4) . . ?
N2A C9A C22A 115.3(3) . . ?
C9A C10A C11A 118.8(4) . . ?
C9A C10A C16A 122.8(3) . . ?
C11A C10A C16A 118.3(3) . . ?
C14A C11A C12A 111.1(4) . . ?
C14A C11A C10A 119.0(4) . . ?
C12A C11A C10A 129.6(4) . . ?
C13A C12A C11A 112.2(4) . . ?
C13A C12A H12A 129(2) . . ?
C11A C12A H12A 119(2) . . ?
C12A C13A S1A 113.7(3) . . ?
C12A C13A H13A 131(3) . . ?
S1A C13A H13A 116(3) . . ?
C11A C14A C15A 123.8(4) . . ?
C11A C14A S1A 113.2(3) . . ?
C15A C14A S1A 123.0(3) . . ?
N1A C15A N2A 124.6(4) . . ?
N1A C15A C14A 121.1(3) . . ?
N2A C15A C14A 114.1(3) . . ?
C17A C16A C21A 118.8(4) . . ?
C17A C16A C10A 119.2(3) . . ?
C21A C16A C10A 122.0(4) . . ?
C18A C17A C16A 120.9(4) . . ?
C18A C17A H17B 119.6 . . ?
C16A C17A H17B 119.6 . . ?
C19A C18A C17A 120.2(5) . . ?
C19A C18A H18B 119.9 . . ?
C17A C18A H18B 119.9 . . ?
C18A C19A C20A 119.2(5) . . ?
C18A C19A H19B 120.4 . . ?
C20A C19A H19B 120.4 . . ?
C21A C20A C19A 121.2(4) . . ?
C21A C20A H20B 119.4 . . ?
C19A C20A H20B 119.4 . . ?
C20A C21A C16A 119.7(4) . . ?
C20A C21A H21B 120.1 . . ?
C16A C21A H21B 120.1 . . ?
C27A C22A C23A 118.5(3) . . ?
C27A C22A C9A 119.4(3) . . ?
C23A C22A C9A 122.1(4) . . ?
C24A C23A C22A 119.7(4) . . ?
C24A C23A H23B 120.1 . . ?
C22A C23A H23B 120.1 . . ?
C25A C24A C23A 120.8(4) . . ?
C25A C24A H24B 119.6 . . ?
C23A C24A H24B 119.6 . . ?
C24A C25A C26A 120.3(4) . . ?
C24A C25A H25B 119.9 . . ?
C26A C25A H25B 119.9 . . ?
C25A C26A C27A 119.3(4) . . ?
C25A C26A H26B 120.4 . . ?
C27A C26A H26B 120.4 . . ?
C22A C27A C26A 121.5(4) . . ?
C22A C27A H27B 119.3 . . ?
C26A C27A H27B 119.3 . . ?

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
C15 N1 C1 C2 175.2(3) . . . . ?
C15 N1 C1 C6 -6.5(5) . . . . ?
N1 C1 C2 C3 -179.9(4) . . . . ?
C6 C1 C2 C3 1.7(6) . . . . ?
C1 C2 C3 C4 -0.4(6) . . . . ?
C2 C3 C4 C5 -1.8(7) . . . . ?
C3 C4 C5 C6 2.4(7) . . . . ?
C4 C5 C6 C1 -1.0(6) . . . . ?
C4 C5 C6 C7 179.4(4) . . . . ?
N1 C1 C6 C5 -179.4(3) . . . . ?
C2 C1 C6 C5 -1.1(6) . . . . ?
N1 C1 C6 C7 0.2(5) . . . . ?
C2 C1 C6 C7 178.5(3) . . . . ?
C15 N2 C7 O1 164.2(3) . . . . ?
C9 N2 C7 O1 -9.2(5) . . . . ?
C15 N2 C7 C6 -16.0(4) . . . . ?
C9 N2 C7 C6 170.6(3) . . . . ?
C5 C6 C7 O1 10.4(6) . . . . ?
C1 C6 C7 O1 -169.2(4) . . . . ?
C5 C6 C7 N2 -169.4(3) . . . . ?
C1 C6 C7 N2 11.1(5) . . . . ?
C15 N2 C9 C10 -4.5(5) . . . . ?
C7 N2 C9 C10 168.6(3) . . . . ?
C15 N2 C9 C22 171.7(3) . . . . ?
C7 N2 C9 C22 -15.1(4) . . . . ?
N2 C9 C10 C11 0.6(5) . . . . ?
C22 C9 C10 C11 -175.7(3) . . . . ?
N2 C9 C10 C16 177.5(3) . . . . ?
C22 C9 C10 C16 1.3(5) . . . . ?
C9 C10 C11 C14 2.4(5) . . . . ?
C16 C10 C11 C14 -174.8(3) . . . . ?
C9 C10 C11 C12 179.7(4) . . . . ?
C16 C10 C11 C12 2.6(5) . . . . ?
C14 C11 C12 C13 0.2(5) . . . . ?
C10 C11 C12 C13 -177.3(3) . . . . ?
C11 C12 C13 S1 -0.2(4) . . . . ?
C14 S1 C13 C12 0.1(3) . . . . ?
C12 C11 C14 C15 -179.2(3) . . . . ?
C10 C11 C14 C15 -1.5(5) . . . . ?
C12 C11 C14 S1 -0.1(4) . . . . ?
C10 C11 C14 S1 177.7(3) . . . . ?
C13 S1 C14 C11 0.0(3) . . . . ?
C13 S1 C14 C15 179.1(3) . . . . ?
C1 N1 C15 N2 0.7(5) . . . . ?
C1 N1 C15 C14 179.9(3) . . . . ?
C9 N2 C15 N1 -175.5(3) . . . . ?
C7 N2 C15 N1 11.1(5) . . . . ?
C9 N2 C15 C14 5.2(4) . . . . ?
C7 N2 C15 C14 -168.2(3) . . . . ?
C11 C14 C15 N1 178.4(3) . . . . ?
S1 C14 C15 N1 -0.7(5) . . . . ?
C11 C14 C15 N2 -2.3(5) . . . . ?
S1 C14 C15 N2 178.7(2) . . . . ?
C9 C10 C16 C21 110.8(4) . . . . ?
C11 C10 C16 C21 -72.2(5) . . . . ?
C9 C10 C16 C17 -71.6(5) . . . . ?
C11 C10 C16 C17 105.4(4) . . . . ?
C21 C16 C17 C18 0.6(6) . . . . ?
C10 C16 C17 C18 -177.0(4) . . . . ?
C16 C17 C18 C19 -0.5(7) . . . . ?
C17 C18 C19 C20 0.3(7) . . . . ?
C18 C19 C20 C21 -0.3(7) . . . . ?
C19 C20 C21 C16 0.4(7) . . . . ?
C17 C16 C21 C20 -0.5(6) . . . . ?
C10 C16 C21 C20 177.1(4) . . . . ?
C10 C9 C22 C23 109.0(4) . . . . ?
N2 C9 C22 C23 -67.3(5) . . . . ?
C10 C9 C22 C27 -64.7(5) . . . . ?
N2 C9 C22 C27 119.0(4) . . . . ?
C27 C22 C23 C24 0.3(6) . . . . ?
C9 C22 C23 C24 -173.5(4) . . . . ?
C22 C23 C24 C25 1.3(7) . . . . ?
C23 C24 C25 C26 -1.8(7) . . . . ?
C24 C25 C26 C27 0.7(7) . . . . ?
C25 C26 C27 C22 0.9(7) . . . . ?
C23 C22 C27 C26 -1.4(7) . . . . ?
C9 C22 C27 C26 172.6(4) . . . . ?
C15A N1A C1A C6A 7.7(5) . . . . ?
C15A N1A C1A C2A -175.3(3) . . . . ?
N1A C1A C2A C3A 178.8(4) . . . . ?
C6A C1A C2A C3A -4.0(6) . . . . ?
C1A C2A C3A C4A 2.1(7) . . . . ?
C2A C3A C4A C5A 0.5(7) . . . . ?
C3A C4A C5A C6A -1.1(7) . . . . ?
C4A C5A C6A C1A -0.9(6) . . . . ?
C4A C5A C6A C7A 178.0(4) . . . . ?
N1A C1A C6A C5A -179.5(3) . . . . ?
C2A C1A C6A C5A 3.4(6) . . . . ?
N1A C1A C6A C7A 1.6(5) . . . . ?
C2A C1A C6A C7A -175.5(3) . . . . ?
C15A N2A C7A O1A -155.6(3) . . . . ?
C9A N2A C7A O1A 16.1(5) . . . . ?
C15A N2A C7A C6A 23.3(4) . . . . ?
C9A N2A C7A C6A -165.0(3) . . . . ?
C5A C6A C7A O1A -17.0(6) . . . . ?
C1A C6A C7A O1A 161.9(4) . . . . ?
C5A C6A C7A N2A 164.1(3) . . . . ?
C1A C6A C7A N2A -17.0(5) . . . . ?
C15A N2A C9A C10A 14.1(5) . . . . ?
C7A N2A C9A C10A -157.2(3) . . . . ?
C15A N2A C9A C22A -158.4(3) . . . . ?
C7A N2A C9A C22A 30.3(4) . . . . ?
N2A C9A C10A C11A -6.0(5) . . . . ?
C22A C9A C10A C11A 165.8(3) . . . . ?
N2A C9A C10A C16A 176.8(3) . . . . ?
C22A C9A C10A C16A -11.4(6) . . . . ?
C9A C10A C11A C14A -4.1(6) . . . . ?
C16A C10A C11A C14A 173.2(3) . . . . ?
C9A C10A C11A C12A -177.7(4) . . . . ?
C16A C10A C11A C12A -0.4(6) . . . . ?
C14A C11A C12A C13A -0.2(5) . . . . ?
C10A C11A C12A C13A 173.8(4) . . . . ?
C11A C12A C13A S1A -0.5(5) . . . . ?
C14A S1A C13A C12A 0.8(4) . . . . ?
C12A C11A C14A C15A -178.2(4) . . . . ?
C10A C11A C14A C15A 7.1(6) . . . . ?
C12A C11A C14A S1A 0.8(4) . . . . ?
C10A C11A C14A S1A -173.9(3) . . . . ?
C13A S1A C14A C11A -0.9(3) . . . . ?
C13A S1A C14A C15A 178.1(3) . . . . ?
C1A N1A C15A N2A -0.5(5) . . . . ?
C1A N1A C15A C14A -176.7(3) . . . . ?
C9A N2A C15A N1A 172.8(3) . . . . ?
C7A N2A C15A N1A -15.8(5) . . . . ?
C9A N2A C15A C14A -10.8(5) . . . . ?
C7A N2A C15A C14A 160.7(3) . . . . ?
C11A C14A C15A N1A 176.9(3) . . . . ?
S1A C14A C15A N1A -2.0(5) . . . . ?
C11A C14A C15A N2A 0.3(5) . . . . ?
S1A C14A C15A N2A -178.6(2) . . . . ?
C9A C10A C16A C17A -115.7(4) . . . . ?
C11A C10A C16A C17A 67.1(5) . . . . ?
C9A C10A C16A C21A 63.5(5) . . . . ?
C11A C10A C16A C21A -113.7(4) . . . . ?
C21A C16A C17A C18A -1.0(6) . . . . ?
C10A C16A C17A C18A 178.2(4) . . . . ?
C16A C17A C18A C19A 0.2(7) . . . . ?
C17A C18A C19A C20A 0.3(7) . . . . ?
C18A C19A C20A C21A 0.1(7) . . . . ?
C19A C20A C21A C16A -0.9(7) . . . . ?
C17A C16A C21A C20A 1.4(6) . . . . ?
C10A C16A C21A C20A -177.8(4) . . . . ?
C10A C9A C22A C27A -122.4(4) . . . . ?
N2A C9A C22A C27A 49.8(5) . . . . ?
C10A C9A C22A C23A 56.2(6) . . . . ?
N2A C9A C22A C23A -131.6(4) . . . . ?
C27A C22A C23A C24A -1.4(6) . . . . ?
C9A C22A C23A C24A 179.9(4) . . . . ?
C22A C23A C24A C25A 0.3(7) . . . . ?
C23A C24A C25A C26A 1.2(7) . . . . ?
C24A C25A C26A C27A -1.6(7) . . . . ?
C23A C22A C27A C26A 1.0(6) . . . . ?
C9A C22A C27A C26A 179.7(4) . . . . ?
C25A C26A C27A C22A 0.5(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.834
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.063
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_744
_database_code_depnum_ccdc_archive 'CCDC 2004711'
loop_
_audit_author_name
_audit_author_address
'Pavel A. Slepukhin'
;Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-03-23 deposited with the CCDC.	2021-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H15 Br N2 O S'
_chemical_formula_weight         483.37

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.3877(11)
_cell_length_b                   13.2907(12)
_cell_length_c                   14.7438(13)
_cell_angle_alpha                105.626(8)
_cell_angle_beta                 107.407(8)
_cell_angle_gamma                103.726(8)
_cell_volume                     2092.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2409
_cell_measurement_theta_min      3.6580
_cell_measurement_theta_max      24.4640

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    2.085
_exptl_absorpt_correction_T_min  0.55454
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       omega
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.5253
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21802
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_av_sigmaI/netI    0.1419
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.64
_diffrn_reflns_theta_max         28.28
_reflns_number_total             10261
_reflns_number_gt                4046
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0446P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0007(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         10261
_refine_ls_number_parameters     560
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1786
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.1862
_refine_ls_wR_factor_gt          0.1255
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.02253(6) 0.51993(5) 0.14654(5) 0.0688(2) Uani 1 1 d . . .
Br1A Br 0.23403(7) 0.76215(6) 0.71546(6) 0.0804(3) Uani 1 1 d . . .
S1 S 0.18164(13) 0.44468(11) 0.10413(11) 0.0516(4) Uani 1 1 d . . .
S1A S 0.43292(13) 0.67952(12) 0.66855(11) 0.0556(4) Uani 1 1 d . . .
O1 O 0.3368(4) 0.0273(3) 0.0328(3) 0.0659(11) Uani 1 1 d . . .
C2 C 0.0612(5) 0.4192(5) 0.1402(4) 0.0503(14) Uani 1 1 d . . .
N2 N 0.2874(3) 0.1808(3) 0.0982(3) 0.0373(9) Uani 1 1 d . . .
N1 N 0.3703(4) 0.3485(3) 0.0713(3) 0.0486(11) Uani 1 1 d . . .
O1A O 0.6291(3) 0.2894(4) 0.6803(4) 0.0798(13) Uani 1 1 d . . .
N1A N 0.6099(4) 0.5690(4) 0.6247(3) 0.0485(11) Uani 1 1 d . . .
C15 C 0.2007(4) 0.3236(4) 0.1161(3) 0.0407(12) Uani 1 1 d . . .
N2A N 0.5198(4) 0.4035(4) 0.6531(3) 0.0458(11) Uani 1 1 d . . .
C16 C 0.0545(5) 0.1187(4) 0.2129(4) 0.0452(13) Uani 1 1 d . . .
C14 C 0.2913(4) 0.2858(4) 0.0942(3) 0.0397(11) Uani 1 1 d . . .
C6 C 0.2074(4) 0.1239(4) 0.1366(4) 0.0433(12) Uani 1 1 d . . .
C15A C 0.4409(4) 0.5530(4) 0.6714(4) 0.0437(12) Uani 1 1 d . . .
C13 C 0.4538(4) 0.3069(5) 0.0469(4) 0.0451(13) Uani 1 1 d . . .
C22 C 0.2165(5) 0.0194(4) 0.1522(4) 0.0422(12) Uani 1 1 d . . .
C4 C 0.1194(4) 0.2695(4) 0.1482(4) 0.0431(12) Uani 1 1 d . . .
C2A C 0.3082(5) 0.6549(5) 0.7020(4) 0.0622(16) Uani 1 1 d . . .
C27 C 0.1180(4) -0.0781(4) 0.0960(4) 0.0430(12) Uani 1 1 d . . .
H27 H 0.0498 -0.0773 0.0480 0.052 Uiso 1 1 calc R . .
C26 C 0.1197(5) -0.1766(4) 0.1103(4) 0.0507(14) Uani 1 1 d . . .
H26 H 0.0539 -0.2420 0.0713 0.061 Uiso 1 1 calc R . .
C3 C 0.0376(5) 0.3264(4) 0.1630(3) 0.0469(13) Uani 1 1 d . . .
H3 H -0.0234 0.3028 0.1852 0.056 Uiso 1 1 calc R . .
C24 C 0.3158(5) -0.0816(5) 0.2398(4) 0.0530(14) Uani 1 1 d . . .
H24 H 0.3819 -0.0825 0.2899 0.064 Uiso 1 1 calc R . .
C23 C 0.3166(5) 0.0160(5) 0.2242(4) 0.0530(14) Uani 1 1 d . . .
H23 H 0.3845 0.0800 0.2619 0.064 Uiso 1 1 calc R . .
C6A C 0.4217(4) 0.3381(5) 0.6679(4) 0.0452(13) Uani 1 1 d . . .
C5 C 0.1273(4) 0.1672(4) 0.1629(4) 0.0440(12) Uani 1 1 d . . .
C14A C 0.5294(5) 0.5085(4) 0.6471(4) 0.0460(13) Uani 1 1 d . . .
C20A C 0.0176(6) 0.2128(5) 0.6171(5) 0.0679(17) Uani 1 1 d . . .
H20A H -0.0531 0.1791 0.5585 0.081 Uiso 1 1 calc R . .
C16A C 0.2291(5) 0.3173(4) 0.6966(4) 0.0485(13) Uani 1 1 d . . .
C8 C 0.4515(5) 0.1990(5) 0.0375(4) 0.0510(14) Uani 1 1 d . . .
C17 C 0.1081(5) 0.1150(4) 0.3079(4) 0.0520(14) Uani 1 1 d . . .
H17 H 0.1916 0.1443 0.3408 0.062 Uiso 1 1 calc R . .
C21A C 0.1233(5) 0.2664(5) 0.6116(4) 0.0593(15) Uani 1 1 d . . .
H21A H 0.1233 0.2683 0.5490 0.071 Uiso 1 1 calc R . .
C5A C 0.3415(5) 0.3848(4) 0.6902(3) 0.0464(13) Uani 1 1 d . . .
C13A C 0.6927(5) 0.5243(5) 0.6056(4) 0.0511(14) Uani 1 1 d . . .
C4A C 0.3527(4) 0.4976(4) 0.6952(4) 0.0455(13) Uani 1 1 d . . .
C21 C -0.0728(5) 0.0736(4) 0.1666(4) 0.0511(14) Uani 1 1 d . . .
H21 H -0.1122 0.0754 0.1028 0.061 Uiso 1 1 calc R . .
C12 C 0.5444(5) 0.3757(5) 0.0286(4) 0.0652(17) Uani 1 1 d . . .
H12 H 0.5474 0.4479 0.0345 0.078 Uiso 1 1 calc R . .
C7 C 0.3567(5) 0.1261(5) 0.0548(4) 0.0495(14) Uani 1 1 d . . .
C7A C 0.6188(5) 0.3656(5) 0.6527(4) 0.0535(14) Uani 1 1 d . . .
C11A C 0.8666(6) 0.5431(6) 0.5597(4) 0.0717(19) Uani 1 1 d . . .
H11A H 0.9228 0.5830 0.5408 0.086 Uiso 1 1 calc R . .
C8A C 0.7030(5) 0.4266(5) 0.6192(4) 0.0507(14) Uani 1 1 d . . .
C9 C 0.5379(5) 0.1620(5) 0.0105(4) 0.0666(17) Uani 1 1 d . . .
H9 H 0.5361 0.0900 0.0036 0.080 Uiso 1 1 calc R . .
C18 C 0.0389(6) 0.0677(5) 0.3561(4) 0.0620(16) Uani 1 1 d . . .
H18 H 0.0765 0.0653 0.4200 0.074 Uiso 1 1 calc R . .
C12A C 0.7776(5) 0.5832(5) 0.5737(4) 0.0584(15) Uani 1 1 d . . .
H12A H 0.7728 0.6479 0.5626 0.070 Uiso 1 1 calc R . .
C19A C 0.0156(6) 0.2086(5) 0.7081(6) 0.0721(19) Uani 1 1 d . . .
H19A H -0.0562 0.1721 0.7117 0.087 Uiso 1 1 calc R . .
C25 C 0.2195(5) -0.1764(5) 0.1826(4) 0.0576(15) Uani 1 1 d . . .
H25 H 0.2212 -0.2422 0.1926 0.069 Uiso 1 1 calc R . .
C22A C 0.4004(5) 0.2175(5) 0.6416(4) 0.0506(14) Uani 1 1 d . . .
C10A C 0.8752(6) 0.4446(6) 0.5731(4) 0.0690(18) Uani 1 1 d . . .
H10A H 0.9354 0.4185 0.5621 0.083 Uiso 1 1 calc R . .
C20 C -0.1393(6) 0.0273(5) 0.2139(5) 0.0638(16) Uani 1 1 d . . .
H20 H -0.2229 -0.0030 0.1815 0.077 Uiso 1 1 calc R . .
C3A C 0.2755(5) 0.5581(4) 0.7128(4) 0.0515(14) Uani 1 1 d . . .
H3A H 0.2103 0.5327 0.7297 0.062 Uiso 1 1 calc R . .
C23A C 0.4016(5) 0.1685(5) 0.7146(5) 0.0590(15) Uani 1 1 d . . .
H23A H 0.4183 0.2126 0.7814 0.071 Uiso 1 1 calc R . .
C10 C 0.6244(6) 0.2303(6) -0.0056(5) 0.0719(18) Uani 1 1 d . . .
H10 H 0.6823 0.2048 -0.0223 0.086 Uiso 1 1 calc R . .
C18A C 0.1200(6) 0.2585(5) 0.7944(5) 0.0691(18) Uani 1 1 d . . .
H18A H 0.1193 0.2547 0.8563 0.083 Uiso 1 1 calc R . .
C11 C 0.6281(6) 0.3365(6) 0.0022(5) 0.0722(18) Uani 1 1 d . . .
H11 H 0.6872 0.3818 -0.0104 0.087 Uiso 1 1 calc R . .
C24A C 0.3782(5) 0.0559(6) 0.6888(6) 0.0720(19) Uani 1 1 d . . .
H24A H 0.3829 0.0248 0.7387 0.086 Uiso 1 1 calc R . .
C9A C 0.7924(5) 0.3868(5) 0.6028(4) 0.0650(17) Uani 1 1 d . . .
H9A H 0.7966 0.3211 0.6120 0.078 Uiso 1 1 calc R . .
C17A C 0.2271(5) 0.3150(5) 0.7894(4) 0.0595(16) Uani 1 1 d . . .
H17A H 0.2971 0.3510 0.8483 0.071 Uiso 1 1 calc R . .
C19 C -0.0837(6) 0.0253(5) 0.3084(5) 0.0666(17) Uani 1 1 d . . .
H19 H -0.1298 -0.0051 0.3403 0.080 Uiso 1 1 calc R . .
C27A C 0.3706(5) 0.1493(5) 0.5430(4) 0.0675(17) Uani 1 1 d . . .
H27A H 0.3664 0.1798 0.4927 0.081 Uiso 1 1 calc R . .
C26A C 0.3466(6) 0.0353(6) 0.5168(6) 0.089(2) Uani 1 1 d . . .
H26A H 0.3297 -0.0096 0.4502 0.107 Uiso 1 1 calc R . .
C25A C 0.3482(6) -0.0104(6) 0.5903(7) 0.085(2) Uani 1 1 d . . .
H25A H 0.3286 -0.0869 0.5726 0.101 Uiso 1 1 calc R . .


_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 C2 1.878(5) . ?
Br1A C2A 1.869(6) . ?
S1 C2 1.720(6) . ?
S1 C15 1.728(5) . ?
S1A C15A 1.718(5) . ?
S1A C2A 1.744(6) . ?
O1 C7 1.209(6) . ?
C2 C3 1.352(7) . ?
N2 C14 1.402(6) . ?
N2 C7 1.432(6) . ?
N2 C6 1.444(6) . ?
N1 C14 1.316(6) . ?
N1 C13 1.376(6) . ?
O1A C7A 1.208(7) . ?
N1A C14A 1.307(6) . ?
N1A C13A 1.361(6) . ?
C15 C4 1.372(7) . ?
C15 C14 1.419(6) . ?
N2A C14A 1.402(6) . ?
N2A C6A 1.427(6) . ?
N2A C7A 1.433(6) . ?
C16 C17 1.378(7) . ?
C16 C21 1.414(7) . ?
C16 C5 1.466(7) . ?
C6 C5 1.359(6) . ?
C6 C22 1.492(7) . ?
C15A C4A 1.358(7) . ?
C15A C14A 1.453(7) . ?
C13 C8 1.396(7) . ?
C13 C12 1.412(7) . ?
C22 C27 1.386(6) . ?
C22 C23 1.389(7) . ?
C4 C3 1.433(6) . ?
C4 C5 1.454(7) . ?
C2A C3A 1.321(8) . ?
C27 C26 1.385(7) . ?
C27 H27 0.9300 . ?
C26 C25 1.368(7) . ?
C26 H26 0.9300 . ?
C3 H3 0.9300 . ?
C24 C25 1.354(7) . ?
C24 C23 1.376(7) . ?
C24 H24 0.9300 . ?
C23 H23 0.9300 . ?
C6A C5A 1.363(7) . ?
C6A C22A 1.480(7) . ?
C20A C19A 1.366(8) . ?
C20A C21A 1.372(7) . ?
C20A H20A 0.9300 . ?
C16A C21A 1.374(7) . ?
C16A C17A 1.384(7) . ?
C16A C5A 1.511(7) . ?
C8 C9 1.395(7) . ?
C8 C7 1.468(7) . ?
C17 C18 1.409(7) . ?
C17 H17 0.9300 . ?
C21A H21A 0.9300 . ?
C5A C4A 1.452(7) . ?
C13A C8A 1.396(7) . ?
C13A C12A 1.429(7) . ?
C4A C3A 1.425(7) . ?
C21 C20 1.371(7) . ?
C21 H21 0.9300 . ?
C12 C11 1.374(8) . ?
C12 H12 0.9300 . ?
C7A C8A 1.454(8) . ?
C11A C12A 1.377(8) . ?
C11A C10A 1.399(9) . ?
C11A H11A 0.9300 . ?
C8A C9A 1.390(7) . ?
C9 C10 1.355(8) . ?
C9 H9 0.9300 . ?
C18 C19 1.364(8) . ?
C18 H18 0.9300 . ?
C12A H12A 0.9300 . ?
C19A C18A 1.373(8) . ?
C19A H19A 0.9300 . ?
C25 H25 0.9300 . ?
C22A C27A 1.372(7) . ?
C22A C23A 1.398(8) . ?
C10A C9A 1.383(8) . ?
C10A H10A 0.9300 . ?
C20 C19 1.367(8) . ?
C20 H20 0.9300 . ?
C3A H3A 0.9300 . ?
C23A C24A 1.375(8) . ?
C23A H23A 0.9300 . ?
C10 C11 1.373(9) . ?
C10 H10 0.9300 . ?
C18A C17A 1.395(8) . ?
C18A H18A 0.9300 . ?
C11 H11 0.9300 . ?
C24A C25A 1.363(8) . ?
C24A H24A 0.9300 . ?
C9A H9A 0.9300 . ?
C17A H17A 0.9300 . ?
C19 H19 0.9300 . ?
C27A C26A 1.392(9) . ?
C27A H27A 0.9300 . ?
C26A C25A 1.375(9) . ?
C26A H26A 0.9300 . ?
C25A H25A 0.9300 . ?

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
C2 S1 C15 89.5(3) . . ?
C15A S1A C2A 89.2(3) . . ?
C3 C2 S1 114.9(4) . . ?
C3 C2 Br1 126.3(4) . . ?
S1 C2 Br1 118.8(3) . . ?
C14 N2 C7 118.5(4) . . ?
C14 N2 C6 121.2(4) . . ?
C7 N2 C6 120.0(4) . . ?
C14 N1 C13 117.5(4) . . ?
C14A N1A C13A 115.9(5) . . ?
C4 C15 C14 124.6(5) . . ?
C4 C15 S1 112.8(4) . . ?
C14 C15 S1 122.6(4) . . ?
C14A N2A C6A 123.2(4) . . ?
C14A N2A C7A 117.4(5) . . ?
C6A N2A C7A 119.2(5) . . ?
C17 C16 C21 117.0(5) . . ?
C17 C16 C5 121.0(5) . . ?
C21 C16 C5 122.0(5) . . ?
N1 C14 N2 125.1(4) . . ?
N1 C14 C15 119.4(5) . . ?
N2 C14 C15 115.5(4) . . ?
C5 C6 N2 120.6(5) . . ?
C5 C6 C22 119.6(5) . . ?
N2 C6 C22 119.8(4) . . ?
C4A C15A C14A 123.7(5) . . ?
C4A C15A S1A 112.6(4) . . ?
C14A C15A S1A 123.6(4) . . ?
N1 C13 C8 122.9(5) . . ?
N1 C13 C12 118.5(5) . . ?
C8 C13 C12 118.6(5) . . ?
C27 C22 C23 118.2(5) . . ?
C27 C22 C6 118.5(4) . . ?
C23 C22 C6 123.2(5) . . ?
C15 C4 C3 112.2(5) . . ?
C15 C4 C5 118.1(5) . . ?
C3 C4 C5 129.6(5) . . ?
C3A C2A S1A 114.1(5) . . ?
C3A C2A Br1A 127.3(5) . . ?
S1A C2A Br1A 118.6(4) . . ?
C26 C27 C22 120.9(5) . . ?
C26 C27 H27 119.5 . . ?
C22 C27 H27 119.5 . . ?
C25 C26 C27 119.1(5) . . ?
C25 C26 H26 120.4 . . ?
C27 C26 H26 120.4 . . ?
C2 C3 C4 110.6(5) . . ?
C2 C3 H3 124.7 . . ?
C4 C3 H3 124.7 . . ?
C25 C24 C23 120.5(5) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C23 C22 120.3(5) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C5A C6A N2A 118.8(5) . . ?
C5A C6A C22A 122.4(5) . . ?
N2A C6A C22A 118.0(4) . . ?
C6 C5 C4 119.3(5) . . ?
C6 C5 C16 122.0(5) . . ?
C4 C5 C16 118.5(5) . . ?
N1A C14A N2A 126.9(5) . . ?
N1A C14A C15A 118.5(5) . . ?
N2A C14A C15A 114.6(5) . . ?
C19A C20A C21A 120.3(6) . . ?
C19A C20A H20A 119.9 . . ?
C21A C20A H20A 119.9 . . ?
C21A C16A C17A 118.6(5) . . ?
C21A C16A C5A 120.1(5) . . ?
C17A C16A C5A 121.0(5) . . ?
C9 C8 C13 119.5(5) . . ?
C9 C8 C7 121.3(5) . . ?
C13 C8 C7 119.1(5) . . ?
C16 C17 C18 121.4(5) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C20A C21A C16A 121.3(6) . . ?
C20A C21A H21A 119.3 . . ?
C16A C21A H21A 119.3 . . ?
C6A C5A C4A 120.8(5) . . ?
C6A C5A C16A 121.6(5) . . ?
C4A C5A C16A 117.1(5) . . ?
N1A C13A C8A 124.0(5) . . ?
N1A C13A C12A 118.3(6) . . ?
C8A C13A C12A 117.7(5) . . ?
C15A C4A C3A 112.6(5) . . ?
C15A C4A C5A 118.3(5) . . ?
C3A C4A C5A 128.8(5) . . ?
C20 C21 C16 121.2(6) . . ?
C20 C21 H21 119.4 . . ?
C16 C21 H21 119.4 . . ?
C11 C12 C13 120.3(6) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
O1 C7 N2 122.2(5) . . ?
O1 C7 C8 123.0(5) . . ?
N2 C7 C8 114.7(5) . . ?
O1A C7A N2A 120.5(6) . . ?
O1A C7A C8A 124.5(5) . . ?
N2A C7A C8A 115.0(5) . . ?
C12A C11A C10A 122.2(6) . . ?
C12A C11A H11A 118.9 . . ?
C10A C11A H11A 118.9 . . ?
C9A C8A C13A 121.9(6) . . ?
C9A C8A C7A 119.2(6) . . ?
C13A C8A C7A 118.9(5) . . ?
C10 C9 C8 120.5(6) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C19 C18 C17 119.5(6) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C11A C12A C13A 119.4(6) . . ?
C11A C12A H12A 120.3 . . ?
C13A C12A H12A 120.3 . . ?
C20A C19A C18A 119.7(6) . . ?
C20A C19A H19A 120.1 . . ?
C18A C19A H19A 120.1 . . ?
C24 C25 C26 120.9(5) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C27A C22A C23A 118.0(6) . . ?
C27A C22A C6A 120.7(6) . . ?
C23A C22A C6A 121.1(5) . . ?
C9A C10A C11A 118.5(6) . . ?
C9A C10A H10A 120.7 . . ?
C11A C10A H10A 120.7 . . ?
C19 C20 C21 120.5(6) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C2A C3A C4A 111.5(5) . . ?
C2A C3A H3A 124.3 . . ?
C4A C3A H3A 124.3 . . ?
C24A C23A C22A 120.8(6) . . ?
C24A C23A H23A 119.6 . . ?
C22A C23A H23A 119.6 . . ?
C9 C10 C11 121.2(6) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C19A C18A C17A 120.1(6) . . ?
C19A C18A H18A 120.0 . . ?
C17A C18A H18A 120.0 . . ?
C10 C11 C12 119.9(6) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C25A C24A C23A 120.1(7) . . ?
C25A C24A H24A 119.9 . . ?
C23A C24A H24A 119.9 . . ?
C10A C9A C8A 120.3(6) . . ?
C10A C9A H9A 119.8 . . ?
C8A C9A H9A 119.8 . . ?
C16A C17A C18A 120.0(6) . . ?
C16A C17A H17A 120.0 . . ?
C18A C17A H17A 120.0 . . ?
C18 C19 C20 120.4(6) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C22A C27A C26A 121.2(7) . . ?
C22A C27A H27A 119.4 . . ?
C26A C27A H27A 119.4 . . ?
C25A C26A C27A 119.3(7) . . ?
C25A C26A H26A 120.3 . . ?
C27A C26A H26A 120.3 . . ?
C24A C25A C26A 120.4(7) . . ?
C24A C25A H25A 119.8 . . ?
C26A C25A H25A 119.8 . . ?

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
C15 S1 C2 C3 1.6(4) . . . . ?
C15 S1 C2 Br1 -179.2(3) . . . . ?
C2 S1 C15 C4 -1.2(4) . . . . ?
C2 S1 C15 C14 178.6(4) . . . . ?
C13 N1 C14 N2 1.7(7) . . . . ?
C13 N1 C14 C15 -177.7(4) . . . . ?
C7 N2 C14 N1 -13.6(7) . . . . ?
C6 N2 C14 N1 172.0(4) . . . . ?
C7 N2 C14 C15 165.8(4) . . . . ?
C6 N2 C14 C15 -8.6(6) . . . . ?
C4 C15 C14 N1 -174.9(5) . . . . ?
S1 C15 C14 N1 5.3(6) . . . . ?
C4 C15 C14 N2 5.7(7) . . . . ?
S1 C15 C14 N2 -174.1(3) . . . . ?
C14 N2 C6 C5 4.8(7) . . . . ?
C7 N2 C6 C5 -169.5(4) . . . . ?
C14 N2 C6 C22 -172.3(4) . . . . ?
C7 N2 C6 C22 13.4(6) . . . . ?
C2A S1A C15A C4A 0.6(4) . . . . ?
C2A S1A C15A C14A 178.4(4) . . . . ?
C14 N1 C13 C8 5.4(7) . . . . ?
C14 N1 C13 C12 -175.9(5) . . . . ?
C5 C6 C22 C27 65.1(6) . . . . ?
N2 C6 C22 C27 -117.8(5) . . . . ?
C5 C6 C22 C23 -111.5(6) . . . . ?
N2 C6 C22 C23 65.6(7) . . . . ?
C14 C15 C4 C3 -179.2(4) . . . . ?
S1 C15 C4 C3 0.6(5) . . . . ?
C14 C15 C4 C5 1.2(7) . . . . ?
S1 C15 C4 C5 -179.0(3) . . . . ?
C15A S1A C2A C3A -0.8(5) . . . . ?
C15A S1A C2A Br1A -179.4(3) . . . . ?
C23 C22 C27 C26 -0.6(7) . . . . ?
C6 C22 C27 C26 -177.4(4) . . . . ?
C22 C27 C26 C25 1.3(8) . . . . ?
S1 C2 C3 C4 -1.6(6) . . . . ?
Br1 C2 C3 C4 179.4(3) . . . . ?
C15 C4 C3 C2 0.6(6) . . . . ?
C5 C4 C3 C2 -179.9(5) . . . . ?
C25 C24 C23 C22 2.6(8) . . . . ?
C27 C22 C23 C24 -1.3(8) . . . . ?
C6 C22 C23 C24 175.3(5) . . . . ?
C14A N2A C6A C5A -8.6(7) . . . . ?
C7A N2A C6A C5A 166.0(4) . . . . ?
C14A N2A C6A C22A 161.4(5) . . . . ?
C7A N2A C6A C22A -23.9(7) . . . . ?
N2 C6 C5 C4 2.5(7) . . . . ?
C22 C6 C5 C4 179.5(4) . . . . ?
N2 C6 C5 C16 -172.9(4) . . . . ?
C22 C6 C5 C16 4.2(7) . . . . ?
C15 C4 C5 C6 -5.4(7) . . . . ?
C3 C4 C5 C6 175.1(5) . . . . ?
C15 C4 C5 C16 170.2(4) . . . . ?
C3 C4 C5 C16 -9.4(8) . . . . ?
C17 C16 C5 C6 62.4(7) . . . . ?
C21 C16 C5 C6 -117.5(6) . . . . ?
C17 C16 C5 C4 -113.0(6) . . . . ?
C21 C16 C5 C4 67.1(6) . . . . ?
C13A N1A C14A N2A -0.2(7) . . . . ?
C13A N1A C14A C15A 178.1(4) . . . . ?
C6A N2A C14A N1A -173.4(5) . . . . ?
C7A N2A C14A N1A 11.9(7) . . . . ?
C6A N2A C14A C15A 8.3(6) . . . . ?
C7A N2A C14A C15A -166.4(4) . . . . ?
C4A C15A C14A N1A 179.6(5) . . . . ?
S1A C15A C14A N1A 2.1(7) . . . . ?
C4A C15A C14A N2A -1.9(7) . . . . ?
S1A C15A C14A N2A -179.5(3) . . . . ?
N1 C13 C8 C9 178.7(5) . . . . ?
C12 C13 C8 C9 0.0(8) . . . . ?
N1 C13 C8 C7 -0.4(8) . . . . ?
C12 C13 C8 C7 -179.1(5) . . . . ?
C21 C16 C17 C18 0.4(8) . . . . ?
C5 C16 C17 C18 -179.5(5) . . . . ?
C19A C20A C21A C16A -0.2(10) . . . . ?
C17A C16A C21A C20A -0.9(9) . . . . ?
C5A C16A C21A C20A -174.3(6) . . . . ?
N2A C6A C5A C4A 2.2(7) . . . . ?
C22A C6A C5A C4A -167.4(5) . . . . ?
N2A C6A C5A C16A 173.9(4) . . . . ?
C22A C6A C5A C16A 4.3(8) . . . . ?
C21A C16A C5A C6A -91.6(6) . . . . ?
C17A C16A C5A C6A 95.2(6) . . . . ?
C21A C16A C5A C4A 80.4(6) . . . . ?
C17A C16A C5A C4A -92.8(6) . . . . ?
C14A N1A C13A C8A -7.0(7) . . . . ?
C14A N1A C13A C12A 175.7(4) . . . . ?
C14A C15A C4A C3A -178.2(4) . . . . ?
S1A C15A C4A C3A -0.4(6) . . . . ?
C14A C15A C4A C5A -3.9(7) . . . . ?
S1A C15A C4A C5A 173.9(4) . . . . ?
C6A C5A C4A C15A 3.7(7) . . . . ?
C16A C5A C4A C15A -168.3(4) . . . . ?
C6A C5A C4A C3A 177.0(5) . . . . ?
C16A C5A C4A C3A 4.9(8) . . . . ?
C17 C16 C21 C20 -0.7(8) . . . . ?
C5 C16 C21 C20 179.2(5) . . . . ?
N1 C13 C12 C11 -178.7(5) . . . . ?
C8 C13 C12 C11 0.0(8) . . . . ?
C14 N2 C7 O1 -161.7(5) . . . . ?
C6 N2 C7 O1 12.7(8) . . . . ?
C14 N2 C7 C8 17.2(6) . . . . ?
C6 N2 C7 C8 -168.4(4) . . . . ?
C9 C8 C7 O1 -11.0(9) . . . . ?
C13 C8 C7 O1 168.0(5) . . . . ?
C9 C8 C7 N2 170.1(5) . . . . ?
C13 C8 C7 N2 -10.9(7) . . . . ?
C14A N2A C7A O1A 163.3(5) . . . . ?
C6A N2A C7A O1A -11.6(8) . . . . ?
C14A N2A C7A C8A -15.6(7) . . . . ?
C6A N2A C7A C8A 169.5(4) . . . . ?
N1A C13A C8A C9A -177.2(5) . . . . ?
C12A C13A C8A C9A 0.2(8) . . . . ?
N1A C13A C8A C7A 1.9(8) . . . . ?
C12A C13A C8A C7A 179.3(5) . . . . ?
O1A C7A C8A C9A 9.8(9) . . . . ?
N2A C7A C8A C9A -171.3(4) . . . . ?
O1A C7A C8A C13A -169.3(6) . . . . ?
N2A C7A C8A C13A 9.6(7) . . . . ?
C13 C8 C9 C10 0.6(9) . . . . ?
C7 C8 C9 C10 179.6(5) . . . . ?
C16 C17 C18 C19 -0.5(9) . . . . ?
C10A C11A C12A C13A 1.7(9) . . . . ?
N1A C13A C12A C11A 176.2(5) . . . . ?
C8A C13A C12A C11A -1.3(8) . . . . ?
C21A C20A C19A C18A 0.1(10) . . . . ?
C23 C24 C25 C26 -1.9(8) . . . . ?
C27 C26 C25 C24 0.0(8) . . . . ?
C5A C6A C22A C27A 106.9(6) . . . . ?
N2A C6A C22A C27A -62.8(7) . . . . ?
C5A C6A C22A C23A -68.5(7) . . . . ?
N2A C6A C22A C23A 121.8(5) . . . . ?
C12A C11A C10A C9A -1.0(9) . . . . ?
C16 C21 C20 C19 1.1(9) . . . . ?
S1A C2A C3A C4A 0.7(6) . . . . ?
Br1A C2A C3A C4A 179.1(4) . . . . ?
C15A C4A C3A C2A -0.2(7) . . . . ?
C5A C4A C3A C2A -173.8(5) . . . . ?
C27A C22A C23A C24A 2.6(8) . . . . ?
C6A C22A C23A C24A 178.1(5) . . . . ?
C8 C9 C10 C11 -1.2(10) . . . . ?
C20A C19A C18A C17A 1.1(9) . . . . ?
C9 C10 C11 C12 1.2(10) . . . . ?
C13 C12 C11 C10 -0.6(9) . . . . ?
C22A C23A C24A C25A -3.0(9) . . . . ?
C11A C10A C9A C8A -0.1(9) . . . . ?
C13A C8A C9A C10A 0.5(8) . . . . ?
C7A C8A C9A C10A -178.6(5) . . . . ?
C21A C16A C17A C18A 2.1(8) . . . . ?
C5A C16A C17A C18A 175.5(5) . . . . ?
C19A C18A C17A C16A -2.3(9) . . . . ?
C17 C18 C19 C20 0.8(9) . . . . ?
C21 C20 C19 C18 -1.1(9) . . . . ?
C23A C22A C27A C26A -2.4(9) . . . . ?
C6A C22A C27A C26A -177.9(6) . . . . ?
C22A C27A C26A C25A 2.6(11) . . . . ?
C23A C24A C25A C26A 3.1(10) . . . . ?
C27A C26A C25A C24A -2.9(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.644
_refine_diff_density_min         -0.648
_refine_diff_density_rms         0.082
