# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_Substance_2b
_database_code_depnum_ccdc_archive 'CCDC 1873711'
_audit_update_record             
;
2018-10-17 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 H19 N2), 2(C7 H7 O3 S), H2 O'
_chemical_formula_sum            'C62 H54 N4 O7 S2 '
_chemical_formula_weight         1031.21

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           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_formula_units_Z            2
_cell_length_a                   16.19500(59)
_cell_length_b                   9.75520(29)
_cell_length_c                   16.75330(80)
_cell_angle_alpha                90.0000
_cell_angle_beta                 101.7706(15)
_cell_angle_gamma                90.0000

_cell_volume                     2591.122(176)
_cell_measurement_reflns_used    7550
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.878
_cell_measurement_temperature    173(2)




_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1084
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11181
_diffrn_reflns_av_R_equivalents  0.1123
_diffrn_reflns_av_sigmaI/netI    0.1710
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         27.89
_reflns_number_total             6155
_reflns_number_gt                2745
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0605P)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         6155
_refine_ls_number_parameters     350
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1966
_refine_ls_R_factor_gt           0.0734
_refine_ls_wR_factor_ref         0.1700
_refine_ls_wR_factor_gt          0.1328
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0.001
_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
S26 S 0.30364(6) -0.42278(8) -0.14484(5) 0.0369(3) Uani 1 1 d . . .
N1 N 0.17851(16) 0.0095(2) 0.15451(16) 0.0309(6) Uani 1 1 d . . .
O29 O 0.30299(17) -0.5211(2) -0.20928(17) 0.0589(7) Uani 1 1 d . . .
C16 C 0.27430(19) 0.1176(3) -0.0524(2) 0.0314(8) Uani 1 1 d . . .
C12 C 0.0996(2) -0.0514(3) 0.1524(2) 0.0312(8) Uani 1 1 d . . .
C6 C 0.1568(2) 0.0044(3) 0.2846(2) 0.0341(8) Uani 1 1 d . . .
C15 C 0.27337(19) 0.2125(3) 0.0090(2) 0.0304(8) Uani 1 1 d . . .
H15 H 0.2939 0.3005 0.0043 0.036 Uiso 1 1 calc R . .
N20 N 0.39273(17) 0.1182(2) -0.12521(16) 0.0319(6) Uani 1 1 d . . .
C14 C 0.24232(19) 0.1780(3) 0.07714(19) 0.0301(8) Uani 1 1 d . . .
H14 H 0.2413 0.2429 0.1176 0.036 Uiso 1 1 calc R . .
C18 C 0.2158(2) -0.0509(3) 0.0254(2) 0.0360(8) Uani 1 1 d . . .
H18 H 0.1982 -0.1403 0.0315 0.043 Uiso 1 1 calc R . .
C31 C 0.1567(2) -0.2735(3) -0.1775(2) 0.0356(8) Uani 1 1 d . . .
H31 H 0.1870 -0.2090 -0.2007 0.043 Uiso 1 1 calc R . .
C13 C 0.21257(19) 0.0462(3) 0.08525(19) 0.0289(7) Uani 1 1 d . . .
C7 C 0.0845(2) -0.0566(3) 0.2317(2) 0.0331(8) Uani 1 1 d . . .
O27 O 0.33940(16) -0.4831(3) -0.06631(16) 0.0621(8) Uani 1 1 d . . .
C2 C 0.2902(2) 0.1051(3) 0.2686(2) 0.0421(9) Uani 1 1 d . . .
H2 H 0.3277 0.1305 0.2360 0.051 Uiso 1 1 calc R . .
O28 O 0.33836(16) -0.2934(2) -0.16036(18) 0.0586(8) Uani 1 1 d . . .
C1 C 0.2130(2) 0.0446(3) 0.2353(2) 0.0324(8) Uani 1 1 d . . .
C30 C 0.1958(2) -0.3926(3) -0.14387(19) 0.0315(8) Uani 1 1 d . . .
C17 C 0.2450(2) -0.0142(3) -0.0430(2) 0.0400(9) Uani 1 1 d . . .
H17 H 0.2453 -0.0788 -0.0837 0.048 Uiso 1 1 calc R . .
C32 C 0.0729(2) -0.2510(3) -0.1765(2) 0.0429(9) Uani 1 1 d . . .
H32 H 0.0473 -0.1707 -0.1991 0.051 Uiso 1 1 calc R . .
C8 C 0.0090(2) -0.1098(3) 0.2454(2) 0.0408(9) Uani 1 1 d . . .
H8 H -0.0015 -0.1136 0.2979 0.049 Uiso 1 1 calc R . .
C11 C 0.0404(2) -0.0982(3) 0.0858(2) 0.0393(9) Uani 1 1 d . . .
H11 H 0.0504 -0.0946 0.0331 0.047 Uiso 1 1 calc R . .
C19 C 0.3030(2) 0.1566(3) -0.1296(2) 0.0376(8) Uani 1 1 d . . .
H19A H 0.2679 0.1107 -0.1757 0.045 Uiso 1 1 calc R . .
H19B H 0.2965 0.2547 -0.1382 0.045 Uiso 1 1 calc R . .
C25 C 0.4114(3) -0.0018(3) -0.1547(2) 0.0506(10) Uani 1 1 d . . .
H25 H 0.3682 -0.0602 -0.1793 0.061 Uiso 1 1 calc R . .
C9 C -0.0496(2) -0.1563(3) 0.1806(3) 0.0478(10) Uani 1 1 d . . .
H9 H -0.1002 -0.1923 0.1891 0.057 Uiso 1 1 calc R . .
C3 C 0.3092(3) 0.1259(3) 0.3520(2) 0.0519(10) Uani 1 1 d . . .
H3 H 0.3602 0.1666 0.3756 0.062 Uiso 1 1 calc R . .
C10 C -0.0343(2) -0.1505(3) 0.1018(2) 0.0437(9) Uani 1 1 d . . .
H10 H -0.0753 -0.1826 0.0587 0.052 Uiso 1 1 calc R . .
C5 C 0.1780(3) 0.0279(3) 0.3690(2) 0.0466(10) Uani 1 1 d . . .
H5 H 0.1410 0.0034 0.4023 0.056 Uiso 1 1 calc R . .
C4 C 0.2539(3) 0.0875(4) 0.4013(2) 0.0526(10) Uani 1 1 d . . .
H4 H 0.2687 0.1026 0.4572 0.063 Uiso 1 1 calc R . .
C34 C 0.0657(2) -0.4642(3) -0.1111(2) 0.0498(10) Uani 1 1 d . . .
H34 H 0.0352 -0.5296 -0.0888 0.060 Uiso 1 1 calc R . .
C35 C 0.1488(2) -0.4888(3) -0.1114(2) 0.0424(9) Uani 1 1 d . . .
H35 H 0.1739 -0.5701 -0.0899 0.051 Uiso 1 1 calc R . .
C33 C 0.0257(2) -0.3453(3) -0.1426(2) 0.0469(10) Uani 1 1 d . . .
C21 C 0.4535(3) 0.2038(4) -0.0904(3) 0.0629(13) Uani 1 1 d . . .
H21 H 0.4393 0.2879 -0.0707 0.076 Uiso 1 1 calc R . .
C36 C -0.0655(2) -0.3164(4) -0.1392(3) 0.0737(14) Uani 1 1 d . . .
H36A H -0.0866 -0.3888 -0.1100 0.111 Uiso 1 1 calc R . .
H36B H -0.0986 -0.3113 -0.1936 0.111 Uiso 1 1 calc R . .
H36C H -0.0690 -0.2309 -0.1117 0.111 Uiso 1 1 calc R . .
C23 C 0.5560(3) 0.0457(5) -0.1123(3) 0.0729(13) Uani 1 1 d . . .
H23 H 0.6122 0.0201 -0.1069 0.088 Uiso 1 1 calc R . .
C24 C 0.4935(3) -0.0400(4) -0.1492(3) 0.0682(13) Uani 1 1 d . . .
H24 H 0.5065 -0.1235 -0.1704 0.082 Uiso 1 1 calc R . .
C22 C 0.5358(3) 0.1695(5) -0.0833(3) 0.0789(15) Uani 1 1 d . . .
H22 H 0.5781 0.2297 -0.0589 0.095 Uiso 1 1 calc R . .
O37 O 0.4834(4) 0.4450(7) 0.0384(4) 0.0705(17) Uani 0.50 1 d PD . .
H37A H 0.454(5) 0.478(9) -0.013(3) 0.085 Uiso 0.50 1 d PD . .
H37B H 0.5432(14) 0.448(8) 0.046(6) 0.085 Uiso 0.50 1 d PD . .


_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
S26 O28 1.427(2) . ?
S26 O29 1.443(2) . ?
S26 O27 1.450(3) . ?
S26 C30 1.774(3) . ?
N1 C1 1.398(4) . ?
N1 C12 1.403(4) . ?
N1 C13 1.428(4) . ?
C16 C15 1.387(4) . ?
C16 C17 1.391(4) . ?
C16 C19 1.510(4) . ?
C12 C11 1.392(5) . ?
C12 C7 1.401(4) . ?
C6 C5 1.403(5) . ?
C6 C1 1.404(4) . ?
C6 C7 1.445(5) . ?
C15 C14 1.379(4) . ?
C15 H15 0.9300 . ?
N20 C25 1.329(4) . ?
N20 C21 1.331(4) . ?
N20 C19 1.487(4) . ?
C14 C13 1.390(4) . ?
C14 H14 0.9300 . ?
C18 C17 1.373(4) . ?
C18 C13 1.388(4) . ?
C18 H18 0.9300 . ?
C31 C32 1.379(5) . ?
C31 C30 1.386(4) . ?
C31 H31 0.9300 . ?
C7 C8 1.389(5) . ?
C2 C3 1.382(5) . ?
C2 C1 1.391(5) . ?
C2 H2 0.9300 . ?
C30 C35 1.387(4) . ?
C17 H17 0.9300 . ?
C32 C33 1.389(5) . ?
C32 H32 0.9300 . ?
C8 C9 1.366(5) . ?
C8 H8 0.9300 . ?
C11 C10 1.389(4) . ?
C11 H11 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C25 C24 1.366(5) . ?
C25 H25 0.9300 . ?
C9 C10 1.392(5) . ?
C9 H9 0.9300 . ?
C3 C4 1.388(5) . ?
C3 H3 0.9300 . ?
C10 H10 0.9300 . ?
C5 C4 1.368(5) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C34 C35 1.369(5) . ?
C34 C33 1.379(5) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C33 C36 1.516(5) . ?
C21 C22 1.356(6) . ?
C21 H21 0.9300 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C23 C24 1.360(6) . ?
C23 C22 1.367(6) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C22 H22 0.9300 . ?
O37 H37A 0.95(2) . ?
O37 H37B 0.95(2) . ?

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
O28 S26 O29 113.25(16) . . ?
O28 S26 O27 115.15(18) . . ?
O29 S26 O27 110.47(17) . . ?
O28 S26 C30 106.25(14) . . ?
O29 S26 C30 105.09(15) . . ?
O27 S26 C30 105.72(15) . . ?
C1 N1 C12 108.1(2) . . ?
C1 N1 C13 125.5(3) . . ?
C12 N1 C13 125.9(3) . . ?
C15 C16 C17 118.5(3) . . ?
C15 C16 C19 121.3(3) . . ?
C17 C16 C19 120.1(3) . . ?
C11 C12 C7 121.6(3) . . ?
C11 C12 N1 129.4(3) . . ?
C7 C12 N1 109.0(3) . . ?
C5 C6 C1 119.4(3) . . ?
C5 C6 C7 133.3(3) . . ?
C1 C6 C7 107.2(3) . . ?
C14 C15 C16 120.8(3) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C25 N20 C21 120.8(3) . . ?
C25 N20 C19 119.8(3) . . ?
C21 N20 C19 119.4(3) . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C17 C18 C13 119.7(3) . . ?
C17 C18 H18 120.2 . . ?
C13 C18 H18 120.2 . . ?
C32 C31 C30 119.9(3) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C18 C13 C14 119.7(3) . . ?
C18 C13 N1 119.6(3) . . ?
C14 C13 N1 120.7(3) . . ?
C8 C7 C12 120.0(3) . . ?
C8 C7 C6 133.1(3) . . ?
C12 C7 C6 106.9(3) . . ?
C3 C2 C1 117.6(3) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C1 N1 129.8(3) . . ?
C2 C1 C6 121.4(3) . . ?
N1 C1 C6 108.8(3) . . ?
C31 C30 C35 119.0(3) . . ?
C31 C30 S26 120.3(2) . . ?
C35 C30 S26 120.7(2) . . ?
C18 C17 C16 121.3(3) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C31 C32 C33 121.6(3) . . ?
C31 C32 H32 119.2 . . ?
C33 C32 H32 119.2 . . ?
C9 C8 C7 119.0(3) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C10 C11 C12 116.7(3) . . ?
C10 C11 H11 121.6 . . ?
C12 C11 H11 121.6 . . ?
N20 C19 C16 111.2(3) . . ?
N20 C19 H19A 109.4 . . ?
C16 C19 H19A 109.4 . . ?
N20 C19 H19B 109.4 . . ?
C16 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
N20 C25 C24 120.5(4) . . ?
N20 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C8 C9 C10 120.7(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C2 C3 C4 121.7(4) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C11 C10 C9 121.9(4) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C4 C5 C6 118.9(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C4 C3 121.0(4) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C35 C34 C33 122.0(3) . . ?
C35 C34 H34 119.0 . . ?
C33 C34 H34 119.0 . . ?
C34 C35 C30 120.2(3) . . ?
C34 C35 H35 119.9 . . ?
C30 C35 H35 119.9 . . ?
C34 C33 C32 117.4(3) . . ?
C34 C33 C36 121.8(3) . . ?
C32 C33 C36 120.9(3) . . ?
N20 C21 C22 120.6(4) . . ?
N20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C24 C23 C22 119.7(4) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C23 C24 C25 119.1(4) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 H24 120.4 . . ?
C21 C22 C23 119.3(4) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
H37A O37 H37B 115(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
C1 N1 C12 C11 177.3(3) . . . . ?
C13 N1 C12 C11 5.0(5) . . . . ?
C1 N1 C12 C7 -0.7(3) . . . . ?
C13 N1 C12 C7 -173.0(3) . . . . ?
C17 C16 C15 C14 -1.5(5) . . . . ?
C19 C16 C15 C14 176.1(3) . . . . ?
C16 C15 C14 C13 0.9(5) . . . . ?
C17 C18 C13 C14 -2.7(5) . . . . ?
C17 C18 C13 N1 177.1(3) . . . . ?
C15 C14 C13 C18 1.2(5) . . . . ?
C15 C14 C13 N1 -178.6(3) . . . . ?
C1 N1 C13 C18 136.5(3) . . . . ?
C12 N1 C13 C18 -52.5(4) . . . . ?
C1 N1 C13 C14 -43.6(4) . . . . ?
C12 N1 C13 C14 127.3(3) . . . . ?
C11 C12 C7 C8 0.2(4) . . . . ?
N1 C12 C7 C8 178.4(2) . . . . ?
C11 C12 C7 C6 -177.8(3) . . . . ?
N1 C12 C7 C6 0.4(3) . . . . ?
C5 C6 C7 C8 2.4(6) . . . . ?
C1 C6 C7 C8 -177.5(3) . . . . ?
C5 C6 C7 C12 -180.0(3) . . . . ?
C1 C6 C7 C12 0.1(3) . . . . ?
C3 C2 C1 N1 -178.7(3) . . . . ?
C3 C2 C1 C6 -0.9(5) . . . . ?
C12 N1 C1 C2 178.8(3) . . . . ?
C13 N1 C1 C2 -8.9(5) . . . . ?
C12 N1 C1 C6 0.8(3) . . . . ?
C13 N1 C1 C6 173.1(3) . . . . ?
C5 C6 C1 C2 1.3(4) . . . . ?
C7 C6 C1 C2 -178.8(3) . . . . ?
C5 C6 C1 N1 179.5(3) . . . . ?
C7 C6 C1 N1 -0.6(3) . . . . ?
C32 C31 C30 C35 1.5(5) . . . . ?
C32 C31 C30 S26 179.9(3) . . . . ?
O28 S26 C30 C31 17.2(3) . . . . ?
O29 S26 C30 C31 -103.1(3) . . . . ?
O27 S26 C30 C31 140.0(3) . . . . ?
O28 S26 C30 C35 -164.4(3) . . . . ?
O29 S26 C30 C35 75.3(3) . . . . ?
O27 S26 C30 C35 -41.6(3) . . . . ?
C13 C18 C17 C16 2.1(5) . . . . ?
C15 C16 C17 C18 0.0(5) . . . . ?
C19 C16 C17 C18 -177.7(3) . . . . ?
C30 C31 C32 C33 -0.1(5) . . . . ?
C12 C7 C8 C9 0.0(4) . . . . ?
C6 C7 C8 C9 177.4(3) . . . . ?
C7 C12 C11 C10 -0.1(4) . . . . ?
N1 C12 C11 C10 -177.9(3) . . . . ?
C25 N20 C19 C16 93.6(4) . . . . ?
C21 N20 C19 C16 -85.3(4) . . . . ?
C15 C16 C19 N20 97.3(3) . . . . ?
C17 C16 C19 N20 -85.1(4) . . . . ?
C21 N20 C25 C24 0.5(6) . . . . ?
C19 N20 C25 C24 -178.3(3) . . . . ?
C7 C8 C9 C10 -0.2(5) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C12 C11 C10 C9 -0.1(5) . . . . ?
C8 C9 C10 C11 0.2(5) . . . . ?
C1 C6 C5 C4 -1.2(5) . . . . ?
C7 C6 C5 C4 178.9(3) . . . . ?
C6 C5 C4 C3 0.7(5) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C33 C34 C35 C30 0.3(6) . . . . ?
C31 C30 C35 C34 -1.6(5) . . . . ?
S26 C30 C35 C34 180.0(3) . . . . ?
C35 C34 C33 C32 1.1(6) . . . . ?
C35 C34 C33 C36 -177.7(4) . . . . ?
C31 C32 C33 C34 -1.1(6) . . . . ?
C31 C32 C33 C36 177.7(4) . . . . ?
C25 N20 C21 C22 -0.9(6) . . . . ?
C19 N20 C21 C22 178.0(4) . . . . ?
C22 C23 C24 C25 -1.6(7) . . . . ?
N20 C25 C24 C23 0.7(6) . . . . ?
N20 C21 C22 C23 0.0(7) . . . . ?
C24 C23 C22 C21 1.3(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.89
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.059
####################################################################### 
# 
# 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_Substance_4
_database_code_depnum_ccdc_archive 'CCDC 1873712'
_audit_update_record             
;
2018-10-17 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H21 N2 1+, C7 H7 O3 S 1-'
_chemical_formula_sum            'C32 H28 N2 O3 S'
_chemical_formula_weight         520.62

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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, z+1/2'

_cell_length_a                   9.6828(2)
_cell_length_b                   11.6284(3)
_cell_length_c                   11.7511(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.0377(8)
_cell_angle_gamma                90
_cell_volume                     1302.87(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    8498
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             548
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.162
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5423
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_av_R_equivalents  0.0133
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.483
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5422
_reflns_number_gt                4773
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.995
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0405P)²+0.3529P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.38(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5422
_refine_ls_number_parameters     346
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.0903
_refine_ls_wR_factor_gt          0.0840
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_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
S1 S 0.30581(7) 0.41964(7) 0.08643(6) 0.02417(17) Uani 1 1 d . . . . .
O2 O 0.4106(2) 0.50915(19) 0.11996(18) 0.0295(5) Uani 1 1 d . . . . .
N1 N 0.7658(2) 0.4271(2) 0.9918(2) 0.0211(5) Uani 1 1 d . . . . .
N2 N 0.8716(2) 0.1753(2) 1.4842(2) 0.0237(5) Uani 1 1 d . . . . .
O1 O 0.1629(2) 0.4633(2) 0.0734(2) 0.0357(6) Uani 1 1 d . . . . .
C5 C 0.6274(3) 0.4200(3) 0.9491(3) 0.0242(6) Uani 1 1 d . . . . .
H5 H 0.562986 0.455147 0.988082 0.029 Uiso 1 1 calc R U . . .
C6 C 0.8547(3) 0.2544(3) 1.3911(2) 0.0211(6) Uani 1 1 d . . . . .
C7 C 0.3320(3) 0.1719(3) 0.3929(3) 0.0262(7) Uani 1 1 d . . . . .
C8 C 0.8259(3) 0.4071(3) 1.2058(3) 0.0218(6) Uani 1 1 d . . . . .
C9 C 0.7096(3) 0.3744(3) 1.2527(2) 0.0218(6) Uani 1 1 d . . . . .
H9 H 0.621504 0.403102 1.221255 0.026 Uiso 1 1 calc R U . . .
C10 C 0.9571(3) 0.3634(3) 1.2532(3) 0.0275(7) Uani 1 1 d . . . . .
H10 H 1.035703 0.385776 1.223224 0.033 Uiso 1 1 calc R U . . .
C11 C 0.6809(3) 0.0310(3) 1.4107(3) 0.0262(7) Uani 1 1 d . . . . .
H11 H 0.649614 0.067704 1.340657 0.031 Uiso 1 1 calc R U . . .
C12 C 0.3327(3) 0.3657(3) 0.3173(3) 0.0245(6) Uani 1 1 d . . . . .
H12 H 0.335448 0.444706 0.329964 0.029 Uiso 1 1 calc R U . . .
C13 C 0.3258(3) 0.1303(3) 0.2810(3) 0.0318(7) Uani 1 1 d . . . . .
H13 H 0.324139 0.051301 0.268269 0.038 Uiso 1 1 calc R U . . .
C14 C 0.3242(3) 0.3231(3) 0.2055(2) 0.0222(6) Uani 1 1 d . . . . .
O3 O 0.3321(2) 0.3525(2) -0.01178(19) 0.0360(6) Uani 1 1 d . . . . .
C16 C 0.3371(3) 0.2907(3) 0.4100(3) 0.0250(6) Uani 1 1 d . . . . .
H16 H 0.343467 0.320093 0.484337 0.030 Uiso 1 1 calc R U . . .
C17 C 0.7234(3) 0.2997(3) 1.3456(2) 0.0222(6) Uani 1 1 d . . . . .
H17 H 0.645371 0.279823 1.377544 0.027 Uiso 1 1 calc R U . . .
C18 C 0.3222(3) 0.2050(3) 0.1879(3) 0.0298(7) Uani 1 1 d . . . . .
H18 H 0.318347 0.175746 0.113756 0.036 Uiso 1 1 calc R U . . .
C19 C 0.8124(3) 0.4879(3) 1.1040(3) 0.0283(7) Uani 1 1 d . . . . .
H19A H 0.745319 0.547710 1.112862 0.034 Uiso 1 1 calc R U . . .
H19B H 0.902302 0.524300 1.102955 0.034 Uiso 1 1 calc R U . . .
C20 C 0.9573(3) 0.0875(3) 1.6557(3) 0.0285(7) Uani 1 1 d . . . . .
C21 C 1.0685(3) 0.2703(3) 1.6211(3) 0.0294(7) Uani 1 1 d . . . . .
H21 H 1.077463 0.333123 1.573980 0.035 Uiso 1 1 calc R U . . .
C22 C 0.9716(3) 0.1825(3) 1.5853(2) 0.0246(6) Uani 1 1 d . . . . .
C23 C 0.7930(3) 0.0749(3) 1.4902(3) 0.0235(6) Uani 1 1 d . . . . .
C24 C 0.7798(4) -0.0838(3) 1.6212(3) 0.0334(7) Uani 1 1 d . . . . .
H24 H 0.813053 -0.122735 1.689605 0.040 Uiso 1 1 calc R U . . .
C25 C 0.5813(3) 0.3614(3) 0.8488(3) 0.0253(6) Uani 1 1 d . . . . .
H25 H 0.485718 0.356742 0.819949 0.030 Uiso 1 1 calc R U . . .
C26 C 0.6768(3) 0.3088(3) 0.7897(3) 0.0261(7) Uani 1 1 d . . . . .
C27 C 0.6186(3) -0.0690(3) 1.4401(3) 0.0323(7) Uani 1 1 d . . . . .
H27 H 0.542893 -0.099337 1.389274 0.039 Uiso 1 1 calc R U . . .
C28 C 0.8182(3) 0.3179(3) 0.8363(3) 0.0293(7) Uani 1 1 d . . . . .
H28 H 0.884444 0.282991 0.799187 0.035 Uiso 1 1 calc R U . . .
C29 C 0.8434(3) 0.0177(3) 1.5943(3) 0.0275(7) Uani 1 1 d . . . . .
C30 C 0.3278(4) 0.0909(3) 0.4928(3) 0.0367(8) Uani 1 1 d . . . . .
H30A H 0.421824 0.072610 0.529283 0.055 Uiso 1 1 calc R U . . .
H30B H 0.279756 0.021548 0.464642 0.055 Uiso 1 1 calc R U . . .
H30C H 0.279208 0.126895 0.547809 0.055 Uiso 1 1 calc R U . . .
C31 C 0.9713(3) 0.2869(3) 1.3442(3) 0.0264(7) Uani 1 1 d . . . . .
H31 H 1.059105 0.257032 1.374446 0.032 Uiso 1 1 calc R U . . .
C32 C 0.6272(4) 0.2430(3) 0.6803(3) 0.0373(8) Uani 1 1 d . . . . .
H32A H 0.538647 0.273339 0.642764 0.056 Uiso 1 1 calc R U . . .
H32B H 0.616396 0.163366 0.698371 0.056 Uiso 1 1 calc R U . . .
H32C H 0.694684 0.250291 0.629843 0.056 Uiso 1 1 calc R U . . .
C33 C 1.0424(4) 0.0791(3) 1.7649(3) 0.0377(8) Uani 1 1 d . . . . .
H33 H 1.034850 0.016130 1.812236 0.045 Uiso 1 1 calc R U . . .
C34 C 0.6665(4) -0.1258(3) 1.5444(3) 0.0342(7) Uani 1 1 d . . . . .
H34 H 0.621610 -0.192365 1.562345 0.041 Uiso 1 1 calc R U . . .
C35 C 1.1504(3) 0.2594(3) 1.7298(3) 0.0355(8) Uani 1 1 d . . . . .
H35 H 1.215885 0.316189 1.755952 0.043 Uiso 1 1 calc R U . . .
C36 C 0.8612(3) 0.3782(3) 0.9372(3) 0.0277(7) Uani 1 1 d . . . . .
H36 H 0.956299 0.384902 0.967264 0.033 Uiso 1 1 calc R U . . .
C37 C 1.1371(4) 0.1653(3) 1.8008(3) 0.0413(9) Uani 1 1 d . . . . .
H37 H 1.193056 0.160904 1.873549 0.050 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
S1 O3 1.452(2) . ?
S1 O1 1.457(2) . ?
S1 O2 1.459(2) . ?
S1 C14 1.778(3) . ?
N1 C36 1.341(4) . ?
N1 C5 1.350(4) . ?
N1 C19 1.494(4) . ?
N2 C22 1.399(4) . ?
N2 C23 1.402(4) . ?
N2 C6 1.416(4) . ?
C5 C25 1.367(4) . ?
C5 H5 0.9300 . ?
C6 C31 1.392(4) . ?
C6 C17 1.394(4) . ?
C7 C13 1.393(4) . ?
C7 C16 1.395(4) . ?
C7 C30 1.511(5) . ?
C8 C9 1.390(4) . ?
C8 C10 1.392(4) . ?
C8 C19 1.508(4) . ?
C9 C17 1.383(4) . ?
C9 H9 0.9300 . ?
C10 C31 1.379(4) . ?
C10 H10 0.9300 . ?
C11 C27 1.382(5) . ?
C11 C23 1.399(4) . ?
C11 H11 0.9300 . ?
C12 C16 1.391(4) . ?
C12 C14 1.393(4) . ?
C12 H12 0.9300 . ?
C13 C18 1.393(5) . ?
C13 H13 0.9300 . ?
C14 C18 1.389(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C22 1.401(4) . ?
C20 C33 1.403(4) . ?
C20 C29 1.455(4) . ?
C21 C35 1.387(4) . ?
C21 C22 1.400(5) . ?
C21 H21 0.9300 . ?
C23 C29 1.403(4) . ?
C24 C34 1.382(5) . ?
C24 C29 1.393(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.391(4) . ?
C25 H25 0.9300 . ?
C26 C28 1.387(4) . ?
C26 C32 1.501(5) . ?
C27 C34 1.398(5) . ?
C27 H27 0.9300 . ?
C28 C36 1.377(5) . ?
C28 H28 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C37 1.375(5) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 C37 1.396(5) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C37 H37 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
O3 S1 O1 113.50(14) . . ?
O3 S1 O2 112.84(13) . . ?
O1 S1 O2 112.49(14) . . ?
O3 S1 C14 106.18(14) . . ?
O1 S1 C14 105.42(13) . . ?
O2 S1 C14 105.55(13) . . ?
C36 N1 C5 121.2(3) . . ?
C36 N1 C19 119.7(3) . . ?
C5 N1 C19 119.0(3) . . ?
C22 N2 C23 108.0(2) . . ?
C22 N2 C6 125.9(3) . . ?
C23 N2 C6 126.1(2) . . ?
N1 C5 C25 120.3(3) . . ?
N1 C5 H5 119.8 . . ?
C25 C5 H5 119.8 . . ?
C31 C6 C17 119.5(3) . . ?
C31 C6 N2 119.3(3) . . ?
C17 C6 N2 121.1(3) . . ?
C13 C7 C16 118.3(3) . . ?
C13 C7 C30 120.9(3) . . ?
C16 C7 C30 120.7(3) . . ?
C9 C8 C10 119.2(3) . . ?
C9 C8 C19 121.4(3) . . ?
C10 C8 C19 119.5(3) . . ?
C17 C9 C8 120.7(3) . . ?
C17 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C31 C10 C8 120.5(3) . . ?
C31 C10 H10 119.8 . . ?
C8 C10 H10 119.8 . . ?
C27 C11 C23 117.5(3) . . ?
C27 C11 H11 121.2 . . ?
C23 C11 H11 121.2 . . ?
C16 C12 C14 120.3(3) . . ?
C16 C12 H12 119.8 . . ?
C14 C12 H12 119.8 . . ?
C7 C13 C18 121.0(3) . . ?
C7 C13 H13 119.5 . . ?
C18 C13 H13 119.5 . . ?
C18 C14 C12 119.3(3) . . ?
C18 C14 S1 120.7(2) . . ?
C12 C14 S1 119.9(2) . . ?
C12 C16 C7 120.8(3) . . ?
C12 C16 H16 119.6 . . ?
C7 C16 H16 119.6 . . ?
C9 C17 C6 119.8(3) . . ?
C9 C17 H17 120.1 . . ?
C6 C17 H17 120.1 . . ?
C14 C18 C13 120.2(3) . . ?
C14 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
N1 C19 C8 112.1(2) . . ?
N1 C19 H19A 109.2 . . ?
C8 C19 H19A 109.2 . . ?
N1 C19 H19B 109.2 . . ?
C8 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C22 C20 C33 119.5(3) . . ?
C22 C20 C29 107.0(2) . . ?
C33 C20 C29 133.4(3) . . ?
C35 C21 C22 117.1(3) . . ?
C35 C21 H21 121.4 . . ?
C22 C21 H21 121.4 . . ?
N2 C22 C21 128.9(3) . . ?
N2 C22 C20 109.2(3) . . ?
C21 C22 C20 121.8(3) . . ?
C11 C23 N2 129.4(3) . . ?
C11 C23 C29 121.4(3) . . ?
N2 C23 C29 109.2(3) . . ?
C34 C24 C29 118.9(3) . . ?
C34 C24 H24 120.5 . . ?
C29 C24 H24 120.5 . . ?
C5 C25 C26 120.3(3) . . ?
C5 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C28 C26 C25 117.7(3) . . ?
C28 C26 C32 121.6(3) . . ?
C25 C26 C32 120.7(3) . . ?
C11 C27 C34 121.6(3) . . ?
C11 C27 H27 119.2 . . ?
C34 C27 H27 119.2 . . ?
C36 C28 C26 120.6(3) . . ?
C36 C28 H28 119.7 . . ?
C26 C28 H28 119.7 . . ?
C24 C29 C23 119.9(3) . . ?
C24 C29 C20 133.4(3) . . ?
C23 C29 C20 106.6(3) . . ?
C7 C30 H30A 109.5 . . ?
C7 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C7 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C10 C31 C6 120.3(3) . . ?
C10 C31 H31 119.9 . . ?
C6 C31 H31 119.9 . . ?
C26 C32 H32A 109.5 . . ?
C26 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C26 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C37 C33 C20 119.0(3) . . ?
C37 C33 H33 120.5 . . ?
C20 C33 H33 120.5 . . ?
C24 C34 C27 120.7(3) . . ?
C24 C34 H34 119.7 . . ?
C27 C34 H34 119.7 . . ?
C21 C35 C37 121.6(3) . . ?
C21 C35 H35 119.2 . . ?
C37 C35 H35 119.2 . . ?
N1 C36 C28 119.8(3) . . ?
N1 C36 H36 120.1 . . ?
C28 C36 H36 120.1 . . ?
C33 C37 C35 120.9(3) . . ?
C33 C37 H37 119.5 . . ?
C35 C37 H37 119.5 . . ?

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
C36 N1 C5 C25 0.5(4) . . . . ?
C19 N1 C5 C25 -177.6(3) . . . . ?
C22 N2 C6 C31 49.8(4) . . . . ?
C23 N2 C6 C31 -128.9(3) . . . . ?
C22 N2 C6 C17 -130.5(3) . . . . ?
C23 N2 C6 C17 50.8(4) . . . . ?
C10 C8 C9 C17 0.3(4) . . . . ?
C19 C8 C9 C17 179.6(3) . . . . ?
C9 C8 C10 C31 1.1(5) . . . . ?
C19 C8 C10 C31 -178.2(3) . . . . ?
C16 C7 C13 C18 -1.2(4) . . . . ?
C30 C7 C13 C18 176.6(3) . . . . ?
C16 C12 C14 C18 -0.9(4) . . . . ?
C16 C12 C14 S1 175.4(2) . . . . ?
O3 S1 C14 C18 -16.4(3) . . . . ?
O1 S1 C14 C18 104.3(3) . . . . ?
O2 S1 C14 C18 -136.4(2) . . . . ?
O3 S1 C14 C12 167.3(2) . . . . ?
O1 S1 C14 C12 -72.0(2) . . . . ?
O2 S1 C14 C12 47.3(2) . . . . ?
C14 C12 C16 C7 -0.5(4) . . . . ?
C13 C7 C16 C12 1.5(4) . . . . ?
C30 C7 C16 C12 -176.2(3) . . . . ?
C8 C9 C17 C6 -1.6(4) . . . . ?
C31 C6 C17 C9 1.5(4) . . . . ?
N2 C6 C17 C9 -178.3(3) . . . . ?
C12 C14 C18 C13 1.2(4) . . . . ?
S1 C14 C18 C13 -175.1(2) . . . . ?
C7 C13 C18 C14 -0.2(5) . . . . ?
C36 N1 C19 C8 -87.0(3) . . . . ?
C5 N1 C19 C8 91.2(3) . . . . ?
C9 C8 C19 N1 -81.5(4) . . . . ?
C10 C8 C19 N1 97.8(3) . . . . ?
C23 N2 C22 C21 -176.3(3) . . . . ?
C6 N2 C22 C21 4.8(5) . . . . ?
C23 N2 C22 C20 0.0(3) . . . . ?
C6 N2 C22 C20 -178.9(3) . . . . ?
C35 C21 C22 N2 175.9(3) . . . . ?
C35 C21 C22 C20 0.0(4) . . . . ?
C33 C20 C22 N2 -176.9(3) . . . . ?
C29 C20 C22 N2 0.5(3) . . . . ?
C33 C20 C22 C21 -0.3(4) . . . . ?
C29 C20 C22 C21 177.1(3) . . . . ?
C27 C11 C23 N2 -177.9(3) . . . . ?
C27 C11 C23 C29 2.1(4) . . . . ?
C22 N2 C23 C11 179.5(3) . . . . ?
C6 N2 C23 C11 -1.6(5) . . . . ?
C22 N2 C23 C29 -0.5(3) . . . . ?
C6 N2 C23 C29 178.4(3) . . . . ?
N1 C5 C25 C26 -0.1(5) . . . . ?
C5 C25 C26 C28 0.2(5) . . . . ?
C5 C25 C26 C32 179.2(3) . . . . ?
C23 C11 C27 C34 -1.0(5) . . . . ?
C25 C26 C28 C36 -0.6(5) . . . . ?
C32 C26 C28 C36 -179.6(3) . . . . ?
C34 C24 C29 C23 -0.6(5) . . . . ?
C34 C24 C29 C20 176.6(3) . . . . ?
C11 C23 C29 C24 -1.3(4) . . . . ?
N2 C23 C29 C24 178.7(3) . . . . ?
C11 C23 C29 C20 -179.2(3) . . . . ?
N2 C23 C29 C20 0.8(3) . . . . ?
C22 C20 C29 C24 -178.3(3) . . . . ?
C33 C20 C29 C24 -1.4(6) . . . . ?
C22 C20 C29 C23 -0.8(3) . . . . ?
C33 C20 C29 C23 176.1(3) . . . . ?
C8 C10 C31 C6 -1.2(5) . . . . ?
C17 C6 C31 C10 -0.1(5) . . . . ?
N2 C6 C31 C10 179.6(3) . . . . ?
C22 C20 C33 C37 0.7(5) . . . . ?
C29 C20 C33 C37 -175.9(3) . . . . ?
C29 C24 C34 C27 1.7(5) . . . . ?
C11 C27 C34 C24 -0.8(5) . . . . ?
C22 C21 C35 C37 -0.1(5) . . . . ?
C5 N1 C36 C28 -0.9(5) . . . . ?
C19 N1 C36 C28 177.2(3) . . . . ?
C26 C28 C36 N1 1.0(5) . . . . ?
C20 C33 C37 C35 -0.8(5) . . . . ?
C21 C35 C37 C33 0.6(5) . . . . ?

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_Substance_3
_database_code_depnum_ccdc_archive 'CCDC 1873713'
_audit_update_record             
;
2018-10-17 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H27 N2, C7 H7 O3 S'
_chemical_formula_sum            'C35 H34 N2 O3 S'
_chemical_formula_weight         562.70

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_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+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   29.4101(10)
_cell_length_b                   8.4373(2)
_cell_length_c                   30.7626(11)
_cell_angle_alpha                90
_cell_angle_beta                 115.777(2)
_cell_angle_gamma                90
_cell_volume                     6873.9(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    16500
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       paralelepiped
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.087
_exptl_crystal_F_000             2384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11412
_diffrn_reflns_av_unetI/netI     0.1362
_diffrn_reflns_av_R_equivalents  0.0798
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.523
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measured_fraction_theta_full 0.944
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_Laue_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_point_group_measured_fraction_full 0.944
_reflns_number_total             7378
_reflns_number_gt                3359
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
PLATON SQUEEZE procedure was used for modeling 
differction of the disordered ethyl acetate solvent                                         
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0910P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7378
_refine_ls_number_parameters     374
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1680
_refine_ls_R_factor_gt           0.0738
_refine_ls_wR_factor_ref         0.2083
_refine_ls_wR_factor_gt          0.1717
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0.003
_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
S1 S 0.67557(3) 0.24815(9) 0.39985(3) 0.0369(2) Uani 1 1 d . . . . .
N1 N 0.55268(10) 0.2156(3) 0.59796(10) 0.0357(7) Uani 1 1 d . . . . .
C14 C 0.47355(13) 0.3602(4) 0.57015(13) 0.0420(9) Uani 1 1 d . . . . .
H14 H 0.489311 0.448706 0.564853 0.050 Uiso 1 1 calc R U . . .
C1 C 0.59316(13) 0.1992(4) 0.64361(12) 0.0374(9) Uani 1 1 d . . . . .
C29 C 0.46344(17) 0.1381(6) 0.24057(18) 0.0880(17) Uani 1 1 d . . . . .
H29A H 0.462666 0.038394 0.225232 0.132 Uiso 1 1 calc R U . . .
H29B H 0.454412 0.221579 0.217092 0.132 Uiso 1 1 calc R U . . .
H29C H 0.439874 0.135732 0.254475 0.132 Uiso 1 1 calc R U . . .
C28 C 0.24796(15) 0.4136(4) 0.33021(13) 0.0519(10) Uani 1 1 d . . . . .
H28A H 0.233416 0.409287 0.295607 0.078 Uiso 1 1 calc R U . . .
H28B H 0.284112 0.412958 0.342973 0.078 Uiso 1 1 calc R U . . .
H28C H 0.237219 0.508798 0.340098 0.078 Uiso 1 1 calc R U . . .
O1 O 0.71036(9) 0.2496(3) 0.37801(9) 0.0499(7) Uani 1 1 d . . . . .
C19 C 0.34360(11) 0.2429(4) 0.55688(11) 0.0291(7) Uani 1 1 d . . . . .
H19A H 0.334728 0.150967 0.570535 0.035 Uiso 1 1 calc R U . . .
H19B H 0.337573 0.336713 0.571828 0.035 Uiso 1 1 calc R U . . .
O2 O 0.68277(9) 0.1128(3) 0.43109(9) 0.0487(7) Uani 1 1 d . . . . .
N2 N 0.31075(9) 0.2481(3) 0.50362(9) 0.0262(6) Uani 1 1 d . . . . .
C2 C 0.59201(14) 0.1751(5) 0.68753(14) 0.0502(10) Uani 1 1 d . . . . .
H2 H 0.561714 0.168013 0.690095 0.060 Uiso 1 1 calc R U . . .
C4 C 0.68338(15) 0.1766(5) 0.72356(16) 0.0591(12) Uani 1 1 d . . . . .
H4 H 0.713826 0.169191 0.751142 0.071 Uiso 1 1 calc R U . . .
C3 C 0.63866(17) 0.1618(5) 0.72797(14) 0.0600(12) Uani 1 1 d . . . . .
H3 H 0.639645 0.142926 0.758149 0.072 Uiso 1 1 calc R U . . .
O3 O 0.67401(10) 0.3973(3) 0.42298(9) 0.0532(7) Uani 1 1 d . . . . .
C22 C 0.25811(11) 0.2596(4) 0.40398(11) 0.0296(7) Uani 1 1 d . . . . .
C5 C 0.68424(14) 0.2015(4) 0.68034(14) 0.0475(10) Uani 1 1 d . . . . .
H5 H 0.714736 0.211370 0.678276 0.057 Uiso 1 1 calc R U . . .
C6 C 0.63826(13) 0.2120(4) 0.63891(13) 0.0389(9) Uani 1 1 d . . . . .
C7 C 0.62508(12) 0.2345(4) 0.58844(13) 0.0360(8) Uani 1 1 d . . . . .
C8 C 0.65292(14) 0.2459(4) 0.56142(14) 0.0416(9) Uani 1 1 d . . . . .
H8 H 0.688028 0.247247 0.576671 0.050 Uiso 1 1 calc R U . . .
C9 C 0.62764(15) 0.2550(4) 0.51235(15) 0.0462(10) Uani 1 1 d . . . . .
H9 H 0.645781 0.261328 0.494067 0.055 Uiso 1 1 calc R U . . .
C23 C 0.27063(12) 0.3965(4) 0.43208(11) 0.0303(8) Uani 1 1 d . . . . .
H23 H 0.261250 0.494804 0.417141 0.036 Uiso 1 1 calc R U . . .
C11 C 0.54668(13) 0.2461(4) 0.51486(13) 0.0393(8) Uani 1 1 d . . . . .
H11 H 0.511586 0.246074 0.499184 0.047 Uiso 1 1 calc R U . . .
C10 C 0.57531(15) 0.2551(4) 0.48934(14) 0.0440(9) Uani 1 1 d . . . . .
H10 H 0.559075 0.261262 0.455841 0.053 Uiso 1 1 calc R U . . .
C12 C 0.57200(12) 0.2372(4) 0.56426(12) 0.0346(8) Uani 1 1 d . . . . .
C13 C 0.50038(12) 0.2225(4) 0.58806(11) 0.0324(8) Uani 1 1 d . . . . .
C33 C 0.61408(13) 0.2226(4) 0.35216(12) 0.0350(8) Uani 1 1 d . . . . .
C15 C 0.42298(13) 0.3654(4) 0.56012(13) 0.0401(9) Uani 1 1 d . . . . .
H15 H 0.404839 0.458194 0.547852 0.048 Uiso 1 1 calc R U . . .
C16 C 0.39862(11) 0.2346(4) 0.56800(10) 0.0271(7) Uani 1 1 d . . . . .
C17 C 0.42629(13) 0.0984(4) 0.58563(13) 0.0426(9) Uani 1 1 d . . . . .
H17 H 0.410699 0.009546 0.590969 0.051 Uiso 1 1 calc R U . . .
C35 C 0.52430(16) 0.2533(5) 0.32067(15) 0.0566(11) Uani 1 1 d . . . . .
H35 H 0.496689 0.293380 0.324284 0.068 Uiso 1 1 calc R U . . .
C21 C 0.27140(12) 0.1162(4) 0.42895(12) 0.0357(8) Uani 1 1 d . . . . .
H21 H 0.262460 0.021295 0.411923 0.043 Uiso 1 1 calc R U . . .
C20 C 0.29766(12) 0.1134(4) 0.47864(12) 0.0333(8) Uani 1 1 d . . . . .
H20 H 0.306258 0.016785 0.494758 0.040 Uiso 1 1 calc R U . . .
C18 C 0.47703(13) 0.0911(4) 0.59558(13) 0.0429(9) Uani 1 1 d . . . . .
H18 H 0.495135 -0.002152 0.607273 0.051 Uiso 1 1 calc R U . . .
C34 C 0.57239(15) 0.2813(4) 0.35632(14) 0.0481(10) Uani 1 1 d . . . . .
H34 H 0.576672 0.340338 0.383371 0.058 Uiso 1 1 calc R U . . .
C25 C 0.23049(12) 0.2683(4) 0.34944(11) 0.0347(8) Uani 1 1 d . . . . .
C24 C 0.29638(12) 0.3889(4) 0.48107(12) 0.0316(8) Uani 1 1 d . . . . .
H24 H 0.304121 0.481832 0.499121 0.038 Uiso 1 1 calc R U . . .
C26 C 0.24101(16) 0.1180(5) 0.32679(13) 0.0536(11) Uani 1 1 d . . . . .
H26A H 0.226210 0.027867 0.334781 0.080 Uiso 1 1 calc R U . . .
H26B H 0.276809 0.102684 0.339134 0.080 Uiso 1 1 calc R U . . .
H26C H 0.226572 0.129947 0.292352 0.080 Uiso 1 1 calc R U . . .
C27 C 0.17384(14) 0.2830(5) 0.33471(13) 0.0581(12) Uani 1 1 d . . . . .
H27A H 0.162539 0.192543 0.346236 0.087 Uiso 1 1 calc R U . . .
H27B H 0.155968 0.288068 0.300162 0.087 Uiso 1 1 calc R U . . .
H27C H 0.167474 0.377697 0.348472 0.087 Uiso 1 1 calc R U . . .
C32 C 0.60676(15) 0.1368(5) 0.31194(14) 0.0551(11) Uani 1 1 d . . . . .
H32 H 0.634477 0.095648 0.308739 0.066 Uiso 1 1 calc R U . . .
C31 C 0.55863(17) 0.1105(5) 0.27591(16) 0.0671(13) Uani 1 1 d . . . . .
H31 H 0.554533 0.053830 0.248517 0.080 Uiso 1 1 calc R U . . .
C30 C 0.51633(16) 0.1676(5) 0.28007(16) 0.0574(11) Uani 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 O2 1.448(2) . ?
S1 O1 1.448(3) . ?
S1 O3 1.456(2) . ?
S1 C33 1.778(4) . ?
N1 C12 1.394(4) . ?
N1 C1 1.398(4) . ?
N1 C13 1.433(4) . ?
C14 C13 1.377(4) . ?
C14 C15 1.382(5) . ?
C14 H14 0.9300 . ?
C1 C2 1.381(5) . ?
C1 C6 1.400(5) . ?
C29 C30 1.521(6) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C28 C25 1.543(5) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C19 N2 1.498(4) . ?
C19 C16 1.503(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
N2 C20 1.332(4) . ?
N2 C24 1.348(4) . ?
C2 C3 1.399(5) . ?
C2 H2 0.9300 . ?
C4 C5 1.357(6) . ?
C4 C3 1.385(6) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C22 C23 1.393(4) . ?
C22 C21 1.395(4) . ?
C22 C25 1.515(4) . ?
C5 C6 1.401(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.440(5) . ?
C7 C8 1.401(5) . ?
C7 C12 1.408(5) . ?
C8 C9 1.364(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.386(5) . ?
C9 H9 0.9300 . ?
C23 C24 1.362(4) . ?
C23 H23 0.9300 . ?
C11 C12 1.373(5) . ?
C11 C10 1.380(5) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C13 C18 1.376(5) . ?
C33 C32 1.367(5) . ?
C33 C34 1.379(5) . ?
C15 C16 1.393(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(4) . ?
C17 C18 1.388(5) . ?
C17 H17 0.9300 . ?
C35 C30 1.372(6) . ?
C35 C34 1.382(5) . ?
C35 H35 0.9300 . ?
C21 C20 1.381(4) . ?
C21 H21 0.9300 . ?
C20 H20 0.9300 . ?
C18 H18 0.9300 . ?
C34 H34 0.9300 . ?
C25 C27 1.530(5) . ?
C25 C26 1.541(5) . ?
C24 H24 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C32 C31 1.384(5) . ?
C32 H32 0.9300 . ?
C31 C30 1.391(6) . ?
C31 H31 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
O2 S1 O1 112.69(15) . . ?
O2 S1 O3 112.59(16) . . ?
O1 S1 O3 113.49(15) . . ?
O2 S1 C33 104.75(15) . . ?
O1 S1 C33 106.76(16) . . ?
O3 S1 C33 105.73(15) . . ?
C12 N1 C1 108.4(3) . . ?
C12 N1 C13 125.7(3) . . ?
C1 N1 C13 125.7(3) . . ?
C13 C14 C15 119.3(3) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C2 C1 N1 128.7(3) . . ?
C2 C1 C6 122.7(3) . . ?
N1 C1 C6 108.7(3) . . ?
C30 C29 H29A 109.5 . . ?
C30 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C30 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N2 C19 C16 111.6(2) . . ?
N2 C19 H19A 109.3 . . ?
C16 C19 H19A 109.3 . . ?
N2 C19 H19B 109.3 . . ?
C16 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
C20 N2 C24 120.5(3) . . ?
C20 N2 C19 119.5(2) . . ?
C24 N2 C19 119.9(2) . . ?
C1 C2 C3 116.7(4) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 H2 121.6 . . ?
C5 C4 C3 122.2(4) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C4 C3 C2 120.8(4) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C23 C22 C21 116.3(3) . . ?
C23 C22 C25 121.1(3) . . ?
C21 C22 C25 122.6(3) . . ?
C4 C5 C6 118.6(4) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 119.0(4) . . ?
C1 C6 C7 107.4(3) . . ?
C5 C6 C7 133.7(4) . . ?
C8 C7 C12 119.0(3) . . ?
C8 C7 C6 134.1(3) . . ?
C12 C7 C6 106.8(3) . . ?
C9 C8 C7 118.8(3) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 121.0(4) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C24 C23 C22 121.1(3) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C12 C11 C10 117.5(3) . . ?
C12 C11 H11 121.3 . . ?
C10 C11 H11 121.3 . . ?
C11 C10 C9 121.7(4) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C11 C12 N1 129.1(3) . . ?
C11 C12 C7 121.9(3) . . ?
N1 C12 C7 108.8(3) . . ?
C18 C13 C14 120.4(3) . . ?
C18 C13 N1 120.0(3) . . ?
C14 C13 N1 119.6(3) . . ?
C32 C33 C34 118.5(3) . . ?
C32 C33 S1 121.0(3) . . ?
C34 C33 S1 120.4(3) . . ?
C14 C15 C16 121.4(3) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C17 C16 C15 118.0(3) . . ?
C17 C16 C19 121.5(3) . . ?
C15 C16 C19 120.6(3) . . ?
C16 C17 C18 121.3(3) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C30 C35 C34 121.6(4) . . ?
C30 C35 H35 119.2 . . ?
C34 C35 H35 119.2 . . ?
C20 C21 C22 120.8(3) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
N2 C20 C21 120.4(3) . . ?
N2 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C13 C18 C17 119.6(3) . . ?
C13 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C33 C34 C35 120.6(4) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 H34 119.7 . . ?
C22 C25 C27 108.8(3) . . ?
C22 C25 C26 110.2(3) . . ?
C27 C25 C26 109.9(3) . . ?
C22 C25 C28 110.8(3) . . ?
C27 C25 C28 108.8(3) . . ?
C26 C25 C28 108.3(3) . . ?
N2 C24 C23 120.7(3) . . ?
N2 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C33 C32 C31 120.9(4) . . ?
C33 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C32 C31 C30 121.0(4) . . ?
C32 C31 H31 119.5 . . ?
C30 C31 H31 119.5 . . ?
C35 C30 C31 117.4(4) . . ?
C35 C30 C29 121.6(4) . . ?
C31 C30 C29 121.0(4) . . ?

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
C12 N1 C1 C2 -179.7(4) . . . . ?
C13 N1 C1 C2 5.1(6) . . . . ?
C12 N1 C1 C6 0.6(4) . . . . ?
C13 N1 C1 C6 -174.6(3) . . . . ?
C16 C19 N2 C20 84.5(3) . . . . ?
C16 C19 N2 C24 -92.8(3) . . . . ?
N1 C1 C2 C3 179.6(3) . . . . ?
C6 C1 C2 C3 -0.7(5) . . . . ?
C5 C4 C3 C2 -1.2(7) . . . . ?
C1 C2 C3 C4 1.6(6) . . . . ?
C3 C4 C5 C6 -0.2(6) . . . . ?
C2 C1 C6 C5 -0.6(5) . . . . ?
N1 C1 C6 C5 179.1(3) . . . . ?
C2 C1 C6 C7 179.3(3) . . . . ?
N1 C1 C6 C7 -0.9(4) . . . . ?
C4 C5 C6 C1 1.1(5) . . . . ?
C4 C5 C6 C7 -178.8(4) . . . . ?
C1 C6 C7 C8 -175.8(4) . . . . ?
C5 C6 C7 C8 4.1(7) . . . . ?
C1 C6 C7 C12 1.0(4) . . . . ?
C5 C6 C7 C12 -179.1(4) . . . . ?
C12 C7 C8 C9 -1.7(5) . . . . ?
C6 C7 C8 C9 174.8(3) . . . . ?
C7 C8 C9 C10 0.8(5) . . . . ?
C21 C22 C23 C24 2.8(5) . . . . ?
C25 C22 C23 C24 -178.6(3) . . . . ?
C12 C11 C10 C9 0.1(5) . . . . ?
C8 C9 C10 C11 0.1(6) . . . . ?
C10 C11 C12 N1 -174.8(3) . . . . ?
C10 C11 C12 C7 -1.1(5) . . . . ?
C1 N1 C12 C11 174.4(3) . . . . ?
C13 N1 C12 C11 -10.4(5) . . . . ?
C1 N1 C12 C7 0.1(4) . . . . ?
C13 N1 C12 C7 175.2(3) . . . . ?
C8 C7 C12 C11 1.9(5) . . . . ?
C6 C7 C12 C11 -175.5(3) . . . . ?
C8 C7 C12 N1 176.7(3) . . . . ?
C6 C7 C12 N1 -0.6(4) . . . . ?
C15 C14 C13 C18 0.5(5) . . . . ?
C15 C14 C13 N1 179.2(3) . . . . ?
C12 N1 C13 C18 118.3(4) . . . . ?
C1 N1 C13 C18 -67.3(4) . . . . ?
C12 N1 C13 C14 -60.4(5) . . . . ?
C1 N1 C13 C14 113.9(4) . . . . ?
O2 S1 C33 C32 -88.1(3) . . . . ?
O1 S1 C33 C32 31.6(3) . . . . ?
O3 S1 C33 C32 152.8(3) . . . . ?
O2 S1 C33 C34 88.1(3) . . . . ?
O1 S1 C33 C34 -152.2(3) . . . . ?
O3 S1 C33 C34 -31.0(3) . . . . ?
C13 C14 C15 C16 0.4(5) . . . . ?
C14 C15 C16 C17 -0.8(5) . . . . ?
C14 C15 C16 C19 180.0(3) . . . . ?
N2 C19 C16 C17 -108.6(3) . . . . ?
N2 C19 C16 C15 70.6(4) . . . . ?
C15 C16 C17 C18 0.4(5) . . . . ?
C19 C16 C17 C18 179.6(3) . . . . ?
C23 C22 C21 C20 -3.0(5) . . . . ?
C25 C22 C21 C20 178.4(3) . . . . ?
C24 N2 C20 C21 3.4(5) . . . . ?
C19 N2 C20 C21 -173.9(3) . . . . ?
C22 C21 C20 N2 0.0(5) . . . . ?
C14 C13 C18 C17 -0.9(5) . . . . ?
N1 C13 C18 C17 -179.6(3) . . . . ?
C16 C17 C18 C13 0.4(6) . . . . ?
C32 C33 C34 C35 0.3(6) . . . . ?
S1 C33 C34 C35 -176.0(3) . . . . ?
C30 C35 C34 C33 -0.4(6) . . . . ?
C23 C22 C25 C27 -83.6(4) . . . . ?
C21 C22 C25 C27 94.9(4) . . . . ?
C23 C22 C25 C26 155.9(3) . . . . ?
C21 C22 C25 C26 -25.6(4) . . . . ?
C23 C22 C25 C28 36.0(4) . . . . ?
C21 C22 C25 C28 -145.4(3) . . . . ?
C20 N2 C24 C23 -3.6(5) . . . . ?
C19 N2 C24 C23 173.6(3) . . . . ?
C22 C23 C24 N2 0.5(5) . . . . ?
C34 C33 C32 C31 0.6(6) . . . . ?
S1 C33 C32 C31 176.8(3) . . . . ?
C33 C32 C31 C30 -1.4(7) . . . . ?
C34 C35 C30 C31 -0.4(7) . . . . ?
C34 C35 C30 C29 -179.4(4) . . . . ?
C32 C31 C30 C35 1.3(7) . . . . ?
C32 C31 C30 C29 -179.8(4) . . . . ?

_refine_diff_density_max         0.397
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.054



# start Validation Reply Form
_vrf_PLAT029_734new_i2a_ns_sq    
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low . 0.944 Why?
RESPONSE: The reason may be twofold. Data collection was carried out 
by rotation around the spindle axis only. Crystal remounting was not 
feasible. The data was collected in the space group C2/c and then 
transformed to the standard I2/a. 
;
# end Validation Reply Form
####################################################################### 
# 
# 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_Substance_2a
_database_code_depnum_ccdc_archive 'CCDC 1873714'
_audit_update_record             
;
2018-10-17 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H19 N2, Cl'
_chemical_formula_sum            'C24 H19 Cl N2'
_chemical_formula_weight         370.86

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           ?
_space_group_name_H-M_alt        'P c a b'
_space_group_name_Hall           '-P 2bc 2ac'

_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+1/2, -y, -z+1/2'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x-1/2, y, z-1/2'
'x-1/2, -y-1/2, z'

_cell_length_a                   8.2062(2)
_cell_length_b                   18.5089(6)
_cell_length_c                   24.6576(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3745.19(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    13732
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             1552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.215
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7963
_diffrn_reflns_av_unetI/netI     0.1285
_diffrn_reflns_av_R_equivalents  0.1037
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.201
_diffrn_reflns_theta_max         27.518
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4274
_reflns_number_gt                2118
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0514P)²+0.6306P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4274
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1556
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.1384
_refine_ls_wR_factor_gt          0.1111
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_restrained_S_all      0.953
_refine_ls_shift/su_max          0.001
_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
Cl1 Cl 0.91668(8) 0.13194(4) 0.99020(3) 0.0393(2) Uani 1 1 d . . . . .
N1 N 0.4858(3) 0.13515(13) 0.76289(9) 0.0317(6) Uani 1 1 d . . . . .
C1 C 0.2960(3) 0.13196(15) 0.83870(10) 0.0307(7) Uani 1 1 d . . . . .
H1 H 0.216413 0.113435 0.815717 0.037 Uiso 1 1 calc R U . . .
N2 N 0.3933(3) 0.12193(12) 1.02122(8) 0.0276(5) Uani 1 1 d . . . . .
C2 C 0.3401(3) 0.18411(16) 0.98677(11) 0.0333(7) Uani 1 1 d . . . . .
H2A H 0.394444 0.227745 0.998911 0.040 Uiso 1 1 calc R U . . .
H2B H 0.223619 0.191154 0.990957 0.040 Uiso 1 1 calc R U . . .
C3 C 0.5040(3) 0.08237(17) 0.67942(11) 0.0327(7) Uani 1 1 d . . . . .
C4 C 0.5498(3) 0.18674(17) 0.72711(11) 0.0313(7) Uani 1 1 d . . . . .
C5 C 0.4505(3) 0.14756(15) 0.81877(10) 0.0282(7) Uani 1 1 d . . . . .
C6 C 0.2985(3) 0.06232(16) 1.02294(10) 0.0300(7) Uani 1 1 d . . . . .
H6 H 0.203829 0.060269 1.002249 0.036 Uiso 1 1 calc R U . . .
C7 C 0.5342(3) 0.18632(16) 0.90732(11) 0.0328(7) Uani 1 1 d . . . . .
H7 H 0.614443 0.204184 0.930336 0.039 Uiso 1 1 calc R U . . .
C8 C 0.4563(3) 0.07131(17) 0.73402(11) 0.0328(7) Uani 1 1 d . . . . .
C9 C 0.3788(3) 0.17141(15) 0.92764(11) 0.0288(7) Uani 1 1 d . . . . .
C10 C 0.5692(3) 0.17465(16) 0.85323(11) 0.0319(7) Uani 1 1 d . . . . .
H10 H 0.672631 0.184979 0.839905 0.038 Uiso 1 1 calc R U . . .
C11 C 0.5876(3) 0.25855(18) 0.73668(11) 0.0387(8) Uani 1 1 d . . . . .
H11 H 0.573563 0.279064 0.770797 0.046 Uiso 1 1 calc R U . . .
C12 C 0.5311(3) 0.12551(17) 1.04992(12) 0.0364(7) Uani 1 1 d . . . . .
H12 H 0.596777 0.166333 1.047466 0.044 Uiso 1 1 calc R U . . .
C13 C 0.3787(3) -0.04930(18) 0.71481(13) 0.0438(8) Uani 1 1 d . . . . .
H13 H 0.337914 -0.093749 0.725983 0.053 Uiso 1 1 calc R U . . .
C14 C 0.5764(3) 0.06942(18) 1.08298(12) 0.0426(8) Uani 1 1 d . . . . .
H14 H 0.671757 0.072270 1.103260 0.051 Uiso 1 1 calc R U . . .
C15 C 0.5633(3) 0.15573(17) 0.67537(11) 0.0334(7) Uani 1 1 d . . . . .
C16 C 0.2607(3) 0.14410(15) 0.89292(11) 0.0299(7) Uani 1 1 d . . . . .
H16 H 0.157146 0.133851 0.906142 0.036 Uiso 1 1 calc R U . . .
C17 C 0.3957(3) 0.00547(17) 0.75236(12) 0.0378(7) Uani 1 1 d . . . . .
H17 H 0.367779 -0.001365 0.788550 0.045 Uiso 1 1 calc R U . . .
C18 C 0.4799(3) 0.00918(17) 1.08584(11) 0.0383(8) Uani 1 1 d . . . . .
H18 H 0.508464 -0.028799 1.108639 0.046 Uiso 1 1 calc R U . . .
C19 C 0.6212(3) 0.1977(2) 0.63237(11) 0.0400(8) Uani 1 1 d . . . . .
H19 H 0.629986 0.178422 0.597672 0.048 Uiso 1 1 calc R U . . .
C20 C 0.4210(3) -0.03967(19) 0.66065(13) 0.0434(8) Uani 1 1 d . . . . .
H20 H 0.406800 -0.077397 0.636191 0.052 Uiso 1 1 calc R U . . .
C21 C 0.3409(3) 0.00499(16) 1.05496(11) 0.0345(7) Uani 1 1 d . . . . .
H21 H 0.276410 -0.036324 1.055813 0.041 Uiso 1 1 calc R U . . .
C22 C 0.6650(3) 0.2681(2) 0.64245(13) 0.0453(9) Uani 1 1 d . . . . .
H22 H 0.707579 0.296103 0.614513 0.054 Uiso 1 1 calc R U . . .
C23 C 0.4840(3) 0.02554(19) 0.64279(12) 0.0410(8) Uani 1 1 d . . . . .
H23 H 0.512952 0.031434 0.606589 0.049 Uiso 1 1 calc R U . . .
C24 C 0.6464(3) 0.29834(19) 0.69399(12) 0.0449(8) Uani 1 1 d . . . . .
H24 H 0.674607 0.346449 0.699502 0.054 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
N1 C8 1.401(4) . ?
N1 C4 1.402(3) . ?
N1 C5 1.427(3) . ?
C1 C16 1.386(4) . ?
C1 C5 1.391(3) . ?
C1 H1 0.9300 . ?
N2 C12 1.335(3) . ?
N2 C6 1.351(3) . ?
N2 C2 1.496(3) . ?
C2 C9 1.510(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C23 1.396(4) . ?
C3 C8 1.417(4) . ?
C3 C15 1.446(4) . ?
C4 C11 1.385(4) . ?
C4 C15 1.403(4) . ?
C5 C10 1.386(4) . ?
C6 C21 1.368(4) . ?
C6 H6 0.9300 . ?
C7 C10 1.381(4) . ?
C7 C9 1.398(4) . ?
C7 H7 0.9300 . ?
C8 C17 1.392(4) . ?
C9 C16 1.388(4) . ?
C10 H10 0.9300 . ?
C11 C24 1.373(4) . ?
C11 H11 0.9300 . ?
C12 C14 1.371(4) . ?
C12 H12 0.9300 . ?
C13 C17 1.380(4) . ?
C13 C20 1.391(4) . ?
C13 H13 0.9300 . ?
C14 C18 1.369(4) . ?
C14 H14 0.9300 . ?
C15 C19 1.398(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C21 1.374(4) . ?
C18 H18 0.9300 . ?
C19 C22 1.374(4) . ?
C19 H19 0.9300 . ?
C20 C23 1.385(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C24 1.397(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24 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
C8 N1 C4 108.6(2) . . ?
C8 N1 C5 126.3(2) . . ?
C4 N1 C5 125.0(2) . . ?
C16 C1 C5 119.8(2) . . ?
C16 C1 H1 120.1 . . ?
C5 C1 H1 120.1 . . ?
C12 N2 C6 120.8(2) . . ?
C12 N2 C2 120.7(2) . . ?
C6 N2 C2 118.5(2) . . ?
N2 C2 C9 111.5(2) . . ?
N2 C2 H2A 109.3 . . ?
C9 C2 H2A 109.3 . . ?
N2 C2 H2B 109.3 . . ?
C9 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C23 C3 C8 118.3(3) . . ?
C23 C3 C15 134.6(3) . . ?
C8 C3 C15 107.1(3) . . ?
C11 C4 N1 129.1(3) . . ?
C11 C4 C15 122.0(3) . . ?
N1 C4 C15 108.8(3) . . ?
C10 C5 C1 119.9(2) . . ?
C10 C5 N1 120.5(2) . . ?
C1 C5 N1 119.6(2) . . ?
N2 C6 C21 120.3(2) . . ?
N2 C6 H6 119.8 . . ?
C21 C6 H6 119.8 . . ?
C10 C7 C9 120.3(3) . . ?
C10 C7 H7 119.8 . . ?
C9 C7 H7 119.8 . . ?
C17 C8 N1 129.4(3) . . ?
C17 C8 C3 122.3(3) . . ?
N1 C8 C3 108.3(3) . . ?
C16 C9 C7 119.2(2) . . ?
C16 C9 C2 120.4(2) . . ?
C7 C9 C2 120.5(2) . . ?
C7 C10 C5 120.2(2) . . ?
C7 C10 H10 119.9 . . ?
C5 C10 H10 119.9 . . ?
C24 C11 C4 117.6(3) . . ?
C24 C11 H11 121.2 . . ?
C4 C11 H11 121.2 . . ?
N2 C12 C14 120.5(3) . . ?
N2 C12 H12 119.8 . . ?
C14 C12 H12 119.8 . . ?
C17 C13 C20 121.6(3) . . ?
C17 C13 H13 119.2 . . ?
C20 C13 H13 119.2 . . ?
C18 C14 C12 119.4(3) . . ?
C18 C14 H14 120.3 . . ?
C12 C14 H14 120.3 . . ?
C19 C15 C4 119.3(3) . . ?
C19 C15 C3 133.6(3) . . ?
C4 C15 C3 107.1(2) . . ?
C1 C16 C9 120.6(2) . . ?
C1 C16 H16 119.7 . . ?
C9 C16 H16 119.7 . . ?
C13 C17 C8 117.5(3) . . ?
C13 C17 H17 121.3 . . ?
C8 C17 H17 121.3 . . ?
C14 C18 C21 119.8(3) . . ?
C14 C18 H18 120.1 . . ?
C21 C18 H18 120.1 . . ?
C22 C19 C15 118.6(3) . . ?
C22 C19 H19 120.7 . . ?
C15 C19 H19 120.7 . . ?
C23 C20 C13 120.7(3) . . ?
C23 C20 H20 119.7 . . ?
C13 C20 H20 119.7 . . ?
C6 C21 C18 119.2(3) . . ?
C6 C21 H21 120.4 . . ?
C18 C21 H21 120.4 . . ?
C19 C22 C24 121.0(3) . . ?
C19 C22 H22 119.5 . . ?
C24 C22 H22 119.5 . . ?
C20 C23 C3 119.6(3) . . ?
C20 C23 H23 120.2 . . ?
C3 C23 H23 120.2 . . ?
C11 C24 C22 121.4(3) . . ?
C11 C24 H24 119.3 . . ?
C22 C24 H24 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
C12 N2 C2 C9 101.1(3) . . . . ?
C6 N2 C2 C9 -79.4(3) . . . . ?
C8 N1 C4 C11 175.6(3) . . . . ?
C5 N1 C4 C11 -1.9(4) . . . . ?
C8 N1 C4 C15 -0.7(3) . . . . ?
C5 N1 C4 C15 -178.1(2) . . . . ?
C16 C1 C5 C10 0.5(4) . . . . ?
C16 C1 C5 N1 -179.8(3) . . . . ?
C8 N1 C5 C10 129.1(3) . . . . ?
C4 N1 C5 C10 -54.0(4) . . . . ?
C8 N1 C5 C1 -50.6(4) . . . . ?
C4 N1 C5 C1 126.3(3) . . . . ?
C12 N2 C6 C21 1.1(4) . . . . ?
C2 N2 C6 C21 -178.4(2) . . . . ?
C4 N1 C8 C17 179.0(3) . . . . ?
C5 N1 C8 C17 -3.6(4) . . . . ?
C4 N1 C8 C3 0.7(3) . . . . ?
C5 N1 C8 C3 178.0(2) . . . . ?
C23 C3 C8 C17 2.1(4) . . . . ?
C15 C3 C8 C17 -178.8(2) . . . . ?
C23 C3 C8 N1 -179.5(2) . . . . ?
C15 C3 C8 N1 -0.4(3) . . . . ?
C10 C7 C9 C16 0.6(4) . . . . ?
C10 C7 C9 C2 180.0(3) . . . . ?
N2 C2 C9 C16 96.3(3) . . . . ?
N2 C2 C9 C7 -83.0(3) . . . . ?
C9 C7 C10 C5 -0.4(4) . . . . ?
C1 C5 C10 C7 -0.1(4) . . . . ?
N1 C5 C10 C7 -179.8(3) . . . . ?
N1 C4 C11 C24 -178.7(3) . . . . ?
C15 C4 C11 C24 -2.9(4) . . . . ?
C6 N2 C12 C14 -1.9(4) . . . . ?
C2 N2 C12 C14 177.6(3) . . . . ?
N2 C12 C14 C18 0.8(4) . . . . ?
C11 C4 C15 C19 2.0(4) . . . . ?
N1 C4 C15 C19 178.6(2) . . . . ?
C11 C4 C15 C3 -176.1(2) . . . . ?
N1 C4 C15 C3 0.5(3) . . . . ?
C23 C3 C15 C19 1.2(5) . . . . ?
C8 C3 C15 C19 -177.8(3) . . . . ?
C23 C3 C15 C4 178.8(3) . . . . ?
C8 C3 C15 C4 -0.1(3) . . . . ?
C5 C1 C16 C9 -0.3(4) . . . . ?
C7 C9 C16 C1 -0.3(4) . . . . ?
C2 C9 C16 C1 -179.6(3) . . . . ?
C20 C13 C17 C8 0.3(4) . . . . ?
N1 C8 C17 C13 -179.9(3) . . . . ?
C3 C8 C17 C13 -1.8(4) . . . . ?
C12 C14 C18 C21 1.2(4) . . . . ?
C4 C15 C19 C22 0.7(4) . . . . ?
C3 C15 C19 C22 178.2(3) . . . . ?
C17 C13 C20 C23 0.8(4) . . . . ?
N2 C6 C21 C18 0.8(4) . . . . ?
C14 C18 C21 C6 -2.0(4) . . . . ?
C15 C19 C22 C24 -2.4(4) . . . . ?
C13 C20 C23 C3 -0.6(4) . . . . ?
C8 C3 C23 C20 -0.8(4) . . . . ?
C15 C3 C23 C20 -179.7(3) . . . . ?
C4 C11 C24 C22 1.2(4) . . . . ?
C19 C22 C24 C11 1.5(4) . . . . ?

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_Substance_5
_database_code_depnum_ccdc_archive 'CCDC 1873715'
_audit_update_record             
;
2018-10-17 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 N2 1+, Br 1-, O'
_chemical_formula_sum            'C21 H21 Br N2 O'
_chemical_formula_weight         397.31

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.3118(3)
_cell_length_b                   9.8222(2)
_cell_length_c                   26.0811(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3922.48(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    23037
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             1632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    2.106
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8360
_diffrn_reflns_av_unetI/netI     0.0965
_diffrn_reflns_av_R_equivalents  0.0830
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.660
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4484
_reflns_number_gt                2269
_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       'COLLECT (Bruker, 2001)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL Denzo (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1475P)²+3.9535P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4484
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1688
_refine_ls_R_factor_gt           0.0834
_refine_ls_wR_factor_ref         0.2786
_refine_ls_wR_factor_gt          0.2285
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_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 0.15503(6) 0.58680(7) -0.42199(3) 0.0647(4) Uani 1 1 d . . . . .
N1 N 0.1690(3) 0.3994(5) -0.2461(2) 0.0380(12) Uani 1 1 d . . . . .
N2 N 0.4546(3) 0.5233(5) -0.40937(17) 0.0360(11) Uani 1 1 d . . . . .
C15 C 0.3536(4) 0.5065(6) -0.3346(2) 0.0374(13) Uani 1 1 d . . . . .
H15A H 0.394403 0.548602 -0.310957 0.045 Uiso 1 1 calc R U . . .
H15B H 0.318762 0.578120 -0.350034 0.045 Uiso 1 1 calc R U . . .
C14 C 0.2949(4) 0.4110(5) -0.3056(2) 0.0366(13) Uani 1 1 d . . . . .
H14A H 0.330132 0.350139 -0.284921 0.044 Uiso 1 1 calc R U . . .
H14B H 0.261952 0.356142 -0.329797 0.044 Uiso 1 1 calc R U . . .
C5 C -0.0212(4) 0.1844(6) -0.2471(2) 0.0400(14) Uani 1 1 d . . . . .
H5 H -0.048242 0.125176 -0.224238 0.048 Uiso 1 1 calc R U . . .
C1 C 0.0958(3) 0.3419(5) -0.2686(2) 0.0311(12) Uani 1 1 d . . . . .
C6 C 0.0561(3) 0.2516(6) -0.2339(2) 0.0321(12) Uani 1 1 d . . . . .
C3 C -0.0161(4) 0.2974(6) -0.3293(2) 0.0430(15) Uani 1 1 d . . . . .
H3 H -0.041609 0.312401 -0.361143 0.052 Uiso 1 1 calc R U . . .
C12 C 0.1779(4) 0.3453(6) -0.1969(2) 0.0372(13) Uani 1 1 d . . . . .
C2 C 0.0614(4) 0.3649(6) -0.3171(2) 0.0376(13) Uani 1 1 d . . . . .
H2 H 0.088669 0.422653 -0.340349 0.045 Uiso 1 1 calc R U . . .
C13 C 0.2319(4) 0.4884(6) -0.2712(2) 0.0408(14) Uani 1 1 d . . . . .
H13A H 0.264935 0.536979 -0.245267 0.049 Uiso 1 1 calc R U . . .
H13B H 0.200688 0.555219 -0.291564 0.049 Uiso 1 1 calc R U . . .
C16 C 0.4034(4) 0.4325(6) -0.3757(2) 0.0450(15) Uani 1 1 d . . . . .
H16A H 0.442640 0.367796 -0.359661 0.054 Uiso 1 1 calc R U . . .
H16B H 0.362411 0.381350 -0.396575 0.054 Uiso 1 1 calc R U . . .
C17 C 0.5425(4) 0.5144(6) -0.4100(2) 0.0418(14) Uani 1 1 d . . . . .
H17 H 0.571128 0.454788 -0.387988 0.050 Uiso 1 1 calc R U . . .
C8 C 0.1055(4) 0.1860(7) -0.1406(2) 0.0457(16) Uani 1 1 d . . . . .
H8 H 0.061030 0.124001 -0.133974 0.055 Uiso 1 1 calc R U . . .
C18 C 0.5888(4) 0.5930(7) -0.4429(3) 0.0480(16) Uani 1 1 d . . . . .
H18 H 0.649150 0.583288 -0.444710 0.058 Uiso 1 1 calc R U . . .
C7 C 0.1103(4) 0.2535(6) -0.1874(2) 0.0352(13) Uani 1 1 d . . . . .
C4 C -0.0562(4) 0.2085(6) -0.2952(2) 0.0434(15) Uani 1 1 d . . . . .
H4 H -0.107379 0.164456 -0.304819 0.052 Uiso 1 1 calc R U . . .
C21 C 0.4121(4) 0.6110(8) -0.4389(3) 0.0525(18) Uani 1 1 d . . . . .
H21 H 0.351485 0.615942 -0.437557 0.063 Uiso 1 1 calc R U . . .
C19 C 0.5481(4) 0.6858(7) -0.4733(2) 0.0537(18) Uani 1 1 d . . . . .
H19 H 0.580433 0.742152 -0.494808 0.064 Uiso 1 1 calc R U . . .
C9 C 0.1677(5) 0.2131(8) -0.1045(3) 0.060(2) Uani 1 1 d . . . . .
H9 H 0.166515 0.166992 -0.073401 0.071 Uiso 1 1 calc R U . . .
C10 C 0.2332(4) 0.3094(8) -0.1138(3) 0.0575(19) Uani 1 1 d . . . . .
H10 H 0.273234 0.328345 -0.087905 0.069 Uiso 1 1 calc R U . . .
C11 C 0.2405(4) 0.3769(7) -0.1596(2) 0.0487(16) Uani 1 1 d . . . . .
H11 H 0.284530 0.440172 -0.165644 0.058 Uiso 1 1 calc R U . . .
C20 C 0.4580(5) 0.6951(9) -0.4719(3) 0.066(2) Uani 1 1 d . . . . .
H20 H 0.428786 0.756995 -0.492676 0.079 Uiso 1 1 calc R U . . .
O1W O 0.7543(3) 0.6639(6) -0.51365(19) 0.0786(17) Uani 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
N1 C1 1.385(7) . ?
N1 C12 1.396(8) . ?
N1 C13 1.456(7) . ?
N2 C21 1.327(8) . ?
N2 C17 1.349(8) . ?
N2 C16 1.477(8) . ?
C15 C14 1.503(8) . ?
C15 C16 1.504(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C14 C13 1.522(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C5 C4 1.384(9) . ?
C5 C6 1.398(8) . ?
C5 H5 0.9300 . ?
C1 C2 1.389(8) . ?
C1 C6 1.405(8) . ?
C6 C7 1.469(8) . ?
C3 C4 1.390(9) . ?
C3 C2 1.395(9) . ?
C3 H3 0.9300 . ?
C12 C7 1.395(8) . ?
C12 C11 1.399(9) . ?
C2 H2 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.354(9) . ?
C17 H17 0.9300 . ?
C8 C9 1.364(10) . ?
C8 C7 1.393(8) . ?
C8 H8 0.9300 . ?
C18 C19 1.359(10) . ?
C18 H18 0.9300 . ?
C4 H4 0.9300 . ?
C21 C20 1.384(10) . ?
C21 H21 0.9300 . ?
C19 C20 1.383(10) . ?
C19 H19 0.9300 . ?
C9 C10 1.400(11) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(10) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C20 H20 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
C1 N1 C12 108.3(4) . . ?
C1 N1 C13 126.1(5) . . ?
C12 N1 C13 125.3(5) . . ?
C21 N2 C17 121.6(5) . . ?
C21 N2 C16 118.5(5) . . ?
C17 N2 C16 119.9(5) . . ?
C14 C15 C16 111.1(5) . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C15 C14 C13 111.3(5) . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C4 C5 C6 118.0(5) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
N1 C1 C2 128.8(5) . . ?
N1 C1 C6 109.6(5) . . ?
C2 C1 C6 121.6(5) . . ?
C5 C6 C1 120.4(5) . . ?
C5 C6 C7 133.4(5) . . ?
C1 C6 C7 106.2(5) . . ?
C4 C3 C2 121.9(6) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C7 C12 N1 109.6(5) . . ?
C7 C12 C11 122.0(6) . . ?
N1 C12 C11 128.4(6) . . ?
C1 C2 C3 116.9(5) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 H2 121.5 . . ?
N1 C13 C14 112.6(5) . . ?
N1 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
N1 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
N2 C16 C15 113.6(5) . . ?
N2 C16 H16A 108.8 . . ?
C15 C16 H16A 108.8 . . ?
N2 C16 H16B 108.8 . . ?
C15 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
N2 C17 C18 119.6(6) . . ?
N2 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C9 C8 C7 118.4(6) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C17 C18 C19 120.8(6) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C8 C7 C12 120.1(5) . . ?
C8 C7 C6 133.6(5) . . ?
C12 C7 C6 106.4(5) . . ?
C5 C4 C3 121.1(6) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
N2 C21 C20 119.9(6) . . ?
N2 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C18 C19 C20 119.0(6) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C8 C9 C10 120.9(6) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 122.3(6) . . ?
C11 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
C10 C11 C12 116.2(6) . . ?
C10 C11 H11 121.9 . . ?
C12 C11 H11 121.9 . . ?
C19 C20 C21 119.0(6) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?

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
C16 C15 C14 C13 -169.1(5) . . . . ?
C12 N1 C1 C2 180.0(5) . . . . ?
C13 N1 C1 C2 -6.7(9) . . . . ?
C12 N1 C1 C6 0.8(6) . . . . ?
C13 N1 C1 C6 174.1(5) . . . . ?
C4 C5 C6 C1 0.7(8) . . . . ?
C4 C5 C6 C7 178.8(6) . . . . ?
N1 C1 C6 C5 177.7(5) . . . . ?
C2 C1 C6 C5 -1.6(8) . . . . ?
N1 C1 C6 C7 -0.9(6) . . . . ?
C2 C1 C6 C7 179.9(5) . . . . ?
C1 N1 C12 C7 -0.4(6) . . . . ?
C13 N1 C12 C7 -173.8(5) . . . . ?
C1 N1 C12 C11 -177.6(6) . . . . ?
C13 N1 C12 C11 9.0(9) . . . . ?
N1 C1 C2 C3 -177.1(5) . . . . ?
C6 C1 C2 C3 2.0(8) . . . . ?
C4 C3 C2 C1 -1.6(8) . . . . ?
C1 N1 C13 C14 -77.0(7) . . . . ?
C12 N1 C13 C14 95.2(6) . . . . ?
C15 C14 C13 N1 174.9(5) . . . . ?
C21 N2 C16 C15 -65.1(7) . . . . ?
C17 N2 C16 C15 115.8(6) . . . . ?
C14 C15 C16 N2 173.4(5) . . . . ?
C21 N2 C17 C18 -2.6(9) . . . . ?
C16 N2 C17 C18 176.5(6) . . . . ?
N2 C17 C18 C19 3.6(10) . . . . ?
C9 C8 C7 C12 0.6(9) . . . . ?
C9 C8 C7 C6 -179.3(6) . . . . ?
N1 C12 C7 C8 179.9(5) . . . . ?
C11 C12 C7 C8 -2.7(9) . . . . ?
N1 C12 C7 C6 -0.2(6) . . . . ?
C11 C12 C7 C6 177.3(5) . . . . ?
C5 C6 C7 C8 2.3(11) . . . . ?
C1 C6 C7 C8 -179.4(6) . . . . ?
C5 C6 C7 C12 -177.6(6) . . . . ?
C1 C6 C7 C12 0.6(6) . . . . ?
C6 C5 C4 C3 -0.3(8) . . . . ?
C2 C3 C4 C5 0.8(9) . . . . ?
C17 N2 C21 C20 0.7(10) . . . . ?
C16 N2 C21 C20 -178.4(6) . . . . ?
C17 C18 C19 C20 -2.7(11) . . . . ?
C7 C8 C9 C10 1.9(10) . . . . ?
C8 C9 C10 C11 -2.6(10) . . . . ?
C9 C10 C11 C12 0.6(10) . . . . ?
C7 C12 C11 C10 2.0(9) . . . . ?
N1 C12 C11 C10 178.9(6) . . . . ?
C18 C19 C20 C21 0.9(11) . . . . ?
N2 C21 C20 C19 0.1(11) . . . . ?

_refine_diff_density_max         1.816
_refine_diff_density_min         -1.122
_refine_diff_density_rms         0.133


# start Validation Reply Form
_vrf_PLAT306_new                 
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) ....... O1W Check  
RESPONSE: Water molecule was found in the structure. However
difference Fourier synthesis didn't locate positions of hydrogen atoms.  
;
# end Validation Reply Form
