# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences.
# This journal is © The Royal Society of Chemistry and Owner Societies 2017

####################################################################### 
# 
# 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_C23H20N2O3S_scd0687
_database_code_depnum_ccdc_archive 'CCDC 1520537'
#Added by publCIF



_audit_update_record             
;
2016-12-02 deposited with the CCDC.
2017-04-25 downloaded from the CCDC.
;
_publcif_datablock.id            {ba3733f1-61e9-444e-b5c0-acd77cd1d62e}

_diffrn_radiation_monochromator  'HELIOS optics'
#Added by publCIF




_cell_special_details            ?
#Added by publCIF




_symmetry_space_group_name_hall  '-P 2yn'
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H20 N2 O3 S'
_chemical_formula_sum            'C23 H20 N2 O3 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.020(2)
_cell_length_b                   11.238(3)
_cell_length_c                   17.984(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.851(11)
_cell_angle_gamma                90
_cell_volume                     1981.9(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    9872
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      30.54

_exptl_crystal_description       fragment
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.191
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6962
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS microfocus tube'
_diffrn_measurement_device_type  
;
Bruker Kappa D8 Quest CMOS diffractometer (with an Oxford Cryosystems cryostream
cooler)
;

_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40647
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.150
_diffrn_reflns_theta_max         30.568
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6036
_reflns_number_gt                4727
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXTL Intrinsic Phasing (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (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)+(0.0553P)²+1.4457P] 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         6036
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1250
_refine_ls_wR_factor_gt          0.1155
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_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 0.09433(4) 0.68704(4) 1.09423(2) 0.02240(11) Uani 1 1 d . . . . .
O1 O 0.23573(12) 0.62998(9) 0.64027(6) 0.0161(2) Uani 1 1 d . . . . .
O2 O 0.26045(15) 0.70686(12) 0.29997(7) 0.0293(3) Uani 1 1 d . . . . .
O3 O 0.30310(13) 0.88550(10) 0.34421(7) 0.0230(3) Uani 1 1 d . . . . .
N1 N 0.37356(13) 0.49005(11) 0.71927(7) 0.0152(3) Uani 1 1 d . . . . .
N2 N 0.27667(14) 0.77976(12) 0.35197(7) 0.0166(3) Uani 1 1 d . . . . .
C1 C 0.24436(15) 0.66190(12) 0.56935(8) 0.0115(3) Uani 1 1 d . . . . .
C2 C 0.24697(14) 0.78363(12) 0.55468(8) 0.0113(3) Uani 1 1 d . . . . .
H2 H 0.2418 0.8395 0.5936 0.014 Uiso 1 1 calc R U . . .
C3 C 0.25712(14) 0.82269(13) 0.48303(8) 0.0120(3) Uani 1 1 d . . . . .
H3A H 0.2597 0.9053 0.4723 0.014 Uiso 1 1 calc R U . . .
C4 C 0.26346(14) 0.73890(13) 0.42699(8) 0.0121(3) Uani 1 1 d . . . . .
C5 C 0.25773(15) 0.61751(13) 0.44012(8) 0.0141(3) Uani 1 1 d . . . . .
H5 H 0.2605 0.5622 0.4005 0.017 Uiso 1 1 calc R U . . .
C6 C 0.24793(15) 0.57780(13) 0.51207(8) 0.0135(3) Uani 1 1 d . . . . .
C7 C 0.23910(18) 0.45277(13) 0.53099(9) 0.0192(3) Uani 1 1 d . . . . .
H7 H 0.2366 0.3941 0.4927 0.023 Uiso 1 1 calc R U . . .
C8 C 0.23447(19) 0.41950(13) 0.60134(9) 0.0200(3) Uani 1 1 d . . . . .
H8 H 0.2235 0.3373 0.6109 0.024 Uiso 1 1 calc R U . . .
C9 C 0.24556(16) 0.50474(12) 0.66631(8) 0.0150(3) Uani 1 1 d . . . . .
C10 C 0.35743(15) 0.52799(12) 0.79070(8) 0.0121(3) Uani 1 1 d . . . . .
C11 C 0.45668(15) 0.55621(13) 0.85382(8) 0.0135(3) Uani 1 1 d . . . . .
H11 H 0.5508 0.5519 0.8524 0.016 Uiso 1 1 calc R U . . .
C12 C 0.41399(15) 0.59115(13) 0.91965(8) 0.0127(3) Uani 1 1 d . . . . .
H12 H 0.4810 0.6099 0.9636 0.015 Uiso 1 1 calc R U . . .
C13 C 0.27659(14) 0.59952(12) 0.92332(8) 0.0103(3) Uani 1 1 d . . . . .
C14 C 0.17768(14) 0.57023(12) 0.85795(8) 0.0109(3) Uani 1 1 d . . . . .
H14 H 0.0834 0.5751 0.8588 0.013 Uiso 1 1 calc R U . . .
C15 C 0.21890(15) 0.53451(12) 0.79295(8) 0.0113(3) Uani 1 1 d . . . . .
C16 C 0.13640(16) 0.49264(13) 0.71720(8) 0.0140(3) Uani 1 1 d . . . . .
C17 C 0.50119(18) 0.51365(16) 0.69497(10) 0.0241(4) Uani 1 1 d . . . . .
H17A H 0.5767 0.4762 0.7306 0.036 Uiso 1 1 calc R U . . .
H17B H 0.5163 0.5997 0.6940 0.036 Uiso 1 1 calc R U . . .
H17C H 0.4963 0.4809 0.6440 0.036 Uiso 1 1 calc R U . . .
C18 C 0.00830(16) 0.56633(15) 0.68811(9) 0.0201(3) Uani 1 1 d . . . . .
H18A H 0.0311 0.6512 0.6928 0.030 Uiso 1 1 calc R U . . .
H18B H -0.0603 0.5482 0.7182 0.030 Uiso 1 1 calc R U . . .
H18C H -0.0282 0.5469 0.6347 0.030 Uiso 1 1 calc R U . . .
C19 C 0.09789(18) 0.36105(14) 0.72449(9) 0.0199(3) Uani 1 1 d . . . . .
H19A H 0.0409 0.3536 0.7625 0.030 Uiso 1 1 calc R U . . .
H19B H 0.1810 0.3137 0.7403 0.030 Uiso 1 1 calc R U . . .
H19C H 0.0472 0.3322 0.6753 0.030 Uiso 1 1 calc R U . . .
C20 C 0.23623(14) 0.63732(12) 0.99428(8) 0.0108(3) Uani 1 1 d . . . . .
C21 C 0.32987(15) 0.67267(13) 1.06213(8) 0.0139(3) Uani 1 1 d . . . . .
H21 H 0.4258 0.6757 1.0661 0.017 Uiso 1 1 calc R U . . .
C22 C 0.26679(15) 0.70190(13) 1.12103(8) 0.0135(3) Uani 1 1 d . . . . .
H22 H 0.3133 0.7270 1.1700 0.016 Uiso 1 1 calc R U . . .
C23 C 0.10466(16) 0.64166(15) 1.00472(9) 0.0172(3) Uani 1 1 d . . . . .
H23 H 0.0276 0.6217 0.9664 0.021 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 C22 1.7042(16) . ?
S1 C23 1.7119(16) . ?
O1 C1 1.3446(17) . ?
O1 C9 1.4802(17) . ?
O2 N2 1.2287(18) . ?
O3 N2 1.2317(18) . ?
N1 C10 1.3941(19) . ?
N1 C9 1.441(2) . ?
N1 C17 1.458(2) . ?
N2 C4 1.4567(19) . ?
C1 C2 1.3945(19) . ?
C1 C6 1.4039(19) . ?
C2 C3 1.385(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.388(2) . ?
C5 C6 1.391(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.453(2) . ?
C7 C8 1.329(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.497(2) . ?
C8 H8 0.9500 . ?
C9 C16 1.570(2) . ?
C10 C11 1.384(2) . ?
C10 C15 1.399(2) . ?
C11 C12 1.395(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.395(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.412(2) . ?
C13 C20 1.478(2) . ?
C14 C15 1.377(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.516(2) . ?
C16 C18 1.527(2) . ?
C16 C19 1.541(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C23 1.370(2) . ?
C20 C21 1.434(2) . ?
C21 C22 1.380(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

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
C22 S1 C23 92.38(7) . . ?
C1 O1 C9 122.73(11) . . ?
C10 N1 C9 108.54(12) . . ?
C10 N1 C17 119.69(13) . . ?
C9 N1 C17 119.82(13) . . ?
O2 N2 O3 123.71(13) . . ?
O2 N2 C4 118.15(13) . . ?
O3 N2 C4 118.14(13) . . ?
O1 C1 C2 116.65(12) . . ?
O1 C1 C6 122.19(13) . . ?
C2 C1 C6 121.14(13) . . ?
C3 C2 C1 119.67(13) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 118.87(13) . . ?
C2 C3 H3A 120.6 . . ?
C4 C3 H3A 120.6 . . ?
C5 C4 C3 122.21(13) . . ?
C5 C4 N2 118.83(13) . . ?
C3 C4 N2 118.96(13) . . ?
C4 C5 C6 119.14(13) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 118.94(13) . . ?
C5 C6 C7 123.20(13) . . ?
C1 C6 C7 117.86(13) . . ?
C8 C7 C6 120.72(14) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 123.46(14) . . ?
C7 C8 H8 118.3 . . ?
C9 C8 H8 118.3 . . ?
N1 C9 O1 108.08(12) . . ?
N1 C9 C8 110.84(13) . . ?
O1 C9 C8 111.84(12) . . ?
N1 C9 C16 103.70(11) . . ?
O1 C9 C16 104.94(11) . . ?
C8 C9 C16 116.79(13) . . ?
C11 C10 N1 128.78(14) . . ?
C11 C10 C15 120.97(13) . . ?
N1 C10 C15 110.25(13) . . ?
C10 C11 C12 117.82(13) . . ?
C10 C11 H11 121.1 . . ?
C12 C11 H11 121.1 . . ?
C13 C12 C11 122.46(13) . . ?
C13 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C12 C13 C14 118.40(13) . . ?
C12 C13 C20 120.53(13) . . ?
C14 C13 C20 121.07(13) . . ?
C15 C14 C13 119.54(13) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C10 120.81(13) . . ?
C14 C15 C16 130.54(13) . . ?
C10 C15 C16 108.60(12) . . ?
C15 C16 C18 113.86(12) . . ?
C15 C16 C19 108.75(12) . . ?
C18 C16 C19 110.01(13) . . ?
C15 C16 C9 100.39(12) . . ?
C18 C16 C9 112.99(12) . . ?
C19 C16 C9 110.46(12) . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C23 C20 C21 110.69(13) . . ?
C23 C20 C13 124.76(13) . . ?
C21 C20 C13 124.55(13) . . ?
C22 C21 C20 113.35(13) . . ?
C22 C21 H21 123.3 . . ?
C20 C21 H21 123.3 . . ?
C21 C22 S1 110.93(11) . . ?
C21 C22 H22 124.5 . . ?
S1 C22 H22 124.5 . . ?
C20 C23 S1 112.65(11) . . ?
C20 C23 H23 123.7 . . ?
S1 C23 H23 123.7 . . ?

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
C9 O1 C1 C2 -173.85(13) . . . . ?
C9 O1 C1 C6 7.4(2) . . . . ?
O1 C1 C2 C3 179.36(13) . . . . ?
C6 C1 C2 C3 -1.8(2) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C2 C3 C4 C5 1.1(2) . . . . ?
C2 C3 C4 N2 -178.88(13) . . . . ?
O2 N2 C4 C5 11.4(2) . . . . ?
O3 N2 C4 C5 -168.79(14) . . . . ?
O2 N2 C4 C3 -168.64(14) . . . . ?
O3 N2 C4 C3 11.2(2) . . . . ?
C3 C4 C5 C6 -1.3(2) . . . . ?
N2 C4 C5 C6 178.69(13) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
C4 C5 C6 C7 178.96(15) . . . . ?
O1 C1 C6 C5 -179.63(14) . . . . ?
C2 C1 C6 C5 1.6(2) . . . . ?
O1 C1 C6 C7 1.3(2) . . . . ?
C2 C1 C6 C7 -177.47(14) . . . . ?
C5 C6 C7 C8 177.75(16) . . . . ?
C1 C6 C7 C8 -3.2(2) . . . . ?
C6 C7 C8 C9 -3.5(3) . . . . ?
C10 N1 C9 O1 82.94(14) . . . . ?
C17 N1 C9 O1 -59.66(17) . . . . ?
C10 N1 C9 C8 -154.17(12) . . . . ?
C17 N1 C9 C8 63.23(17) . . . . ?
C10 N1 C9 C16 -28.08(14) . . . . ?
C17 N1 C9 C16 -170.68(13) . . . . ?
C1 O1 C9 N1 109.56(14) . . . . ?
C1 O1 C9 C8 -12.7(2) . . . . ?
C1 O1 C9 C16 -140.27(13) . . . . ?
C7 C8 C9 N1 -109.85(19) . . . . ?
C7 C8 C9 O1 10.8(2) . . . . ?
C7 C8 C9 C16 131.72(18) . . . . ?
C9 N1 C10 C11 -163.52(14) . . . . ?
C17 N1 C10 C11 -20.9(2) . . . . ?
C9 N1 C10 C15 17.00(16) . . . . ?
C17 N1 C10 C15 159.66(13) . . . . ?
N1 C10 C11 C12 -179.34(14) . . . . ?
C15 C10 C11 C12 0.1(2) . . . . ?
C10 C11 C12 C13 -0.7(2) . . . . ?
C11 C12 C13 C14 0.7(2) . . . . ?
C11 C12 C13 C20 -179.80(13) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C20 C13 C14 C15 -179.53(12) . . . . ?
C13 C14 C15 C10 -0.6(2) . . . . ?
C13 C14 C15 C16 176.59(13) . . . . ?
C11 C10 C15 C14 0.6(2) . . . . ?
N1 C10 C15 C14 -179.92(12) . . . . ?
C11 C10 C15 C16 -177.19(13) . . . . ?
N1 C10 C15 C16 2.34(16) . . . . ?
C14 C15 C16 C18 43.1(2) . . . . ?
C10 C15 C16 C18 -139.47(13) . . . . ?
C14 C15 C16 C19 -79.96(19) . . . . ?
C10 C15 C16 C19 97.49(14) . . . . ?
C14 C15 C16 C9 164.10(14) . . . . ?
C10 C15 C16 C9 -18.45(14) . . . . ?
N1 C9 C16 C15 27.46(13) . . . . ?
O1 C9 C16 C15 -85.84(13) . . . . ?
C8 C9 C16 C15 149.68(13) . . . . ?
N1 C9 C16 C18 149.10(12) . . . . ?
O1 C9 C16 C18 35.79(16) . . . . ?
C8 C9 C16 C18 -88.68(16) . . . . ?
N1 C9 C16 C19 -87.20(14) . . . . ?
O1 C9 C16 C19 159.50(12) . . . . ?
C8 C9 C16 C19 35.02(18) . . . . ?
C12 C13 C20 C23 -176.08(14) . . . . ?
C14 C13 C20 C23 3.4(2) . . . . ?
C12 C13 C20 C21 2.8(2) . . . . ?
C14 C13 C20 C21 -177.63(13) . . . . ?
C23 C20 C21 C22 0.17(18) . . . . ?
C13 C20 C21 C22 -178.88(13) . . . . ?
C20 C21 C22 S1 -0.17(16) . . . . ?
C23 S1 C22 C21 0.10(12) . . . . ?
C21 C20 C23 S1 -0.09(17) . . . . ?
C13 C20 C23 S1 178.96(11) . . . . ?
C22 S1 C23 C20 0.00(13) . . . . ?

_refine_diff_density_max         0.579
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.067


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate / hexanes'
####################################################################### 
# 
# 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_C23H19BrN2O3S_scd0686
_database_code_depnum_ccdc_archive 'CCDC 1520538'
#Added by publCIF



_audit_update_record             
;
2016-12-02 deposited with the CCDC.
2017-04-25 downloaded from the CCDC.
;
_publcif_datablock.id            {b2fc8cfe-dd04-428d-821b-7dcadae91040}

_diffrn_radiation_monochromator  'HELIOS optics'
#Added by publCIF




_symmetry_space_group_name_hall  '-P 2ybc'
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H19 Br N2 O3 S'
_chemical_formula_sum            'C23 H19 Br N2 O3 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   19.967(7)
_cell_length_b                   11.759(3)
_cell_length_c                   8.670(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.660(18)
_cell_angle_gamma                90
_cell_volume                     2028.8(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    9908
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      30.04

_exptl_crystal_description       fragment
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    2.158
_shelx_estimated_absorpt_T_min   0.625
_shelx_estimated_absorpt_T_max   0.919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5999
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS microfocus tube'
_diffrn_measurement_device_type  
;
Bruker Kappa D8 Quest CMOS diffractometer (with an Oxford Cryosystems cryostream
cooler)
;

_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41789
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.682
_diffrn_reflns_theta_max         30.627
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6241
_reflns_number_gt                4775
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXTL Intrinsic Phasing (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (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)+(0.0768P)²+9.5297P] 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         6241
_refine_ls_number_parameters     275
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.1058
_refine_ls_R_factor_gt           0.0803
_refine_ls_wR_factor_ref         0.2001
_refine_ls_wR_factor_gt          0.1859
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
O1 O 0.71188(11) 0.46073(18) 0.5082(3) 0.0124(4) Uani 1 1 d . . . . .
O2 O 0.48375(13) 0.3348(2) 0.0039(3) 0.0198(5) Uani 1 1 d . . . . .
O3 O 0.51069(13) 0.1688(2) 0.0976(3) 0.0207(5) Uani 1 1 d . . . . .
N1 N 0.67755(13) 0.5909(2) 0.6952(3) 0.0096(5) Uani 1 1 d . . . . .
N2 N 0.51708(13) 0.2726(2) 0.0951(3) 0.0134(5) Uani 1 1 d . . . . .
C1 C 0.66301(15) 0.4189(3) 0.4090(4) 0.0104(5) Uani 1 1 d . . . . .
C2 C 0.65643(17) 0.3011(3) 0.4023(4) 0.0137(6) Uani 1 1 d . . . . .
H2 H 0.6850 0.2540 0.4680 0.016 Uiso 1 1 calc R U . . .
C3 C 0.60807(16) 0.2533(3) 0.2994(4) 0.0136(6) Uani 1 1 d . . . . .
H3 H 0.6029 0.1731 0.2933 0.016 Uiso 1 1 calc R U . . .
C4 C 0.56707(15) 0.3243(3) 0.2049(4) 0.0120(6) Uani 1 1 d . . . . .
C5 C 0.57366(15) 0.4419(3) 0.2081(4) 0.0111(5) Uani 1 1 d . . . . .
H5 H 0.5452 0.4882 0.1412 0.013 Uiso 1 1 calc R U . . .
C6 C 0.62235(15) 0.4906(3) 0.3104(4) 0.0107(5) Uani 1 1 d . . . . .
C7 C 0.63707(16) 0.6120(3) 0.3167(4) 0.0121(6) Uani 1 1 d . . . . .
H7 H 0.6157 0.6614 0.2413 0.014 Uiso 1 1 calc R U . . .
C8 C 0.68028(16) 0.6543(3) 0.4275(4) 0.0118(6) Uani 1 1 d . . . . .
H8 H 0.6913 0.7328 0.4252 0.014 Uiso 1 1 calc R U . . .
C9 C 0.71184(15) 0.5817(2) 0.5550(3) 0.0097(5) Uani 1 1 d . . . . .
C10 C 0.72110(15) 0.5500(3) 0.8158(3) 0.0102(5) Uani 1 1 d . . . . .
C11 C 0.70673(17) 0.5088(3) 0.9595(4) 0.0143(6) Uani 1 1 d . . . . .
H11 H 0.6618 0.5035 0.9871 0.017 Uiso 1 1 calc R U . . .
C12 C 0.76072(19) 0.4752(3) 1.0622(4) 0.0203(7) Uani 1 1 d . . . . .
H12 H 0.7521 0.4467 1.1612 0.024 Uiso 1 1 calc R U . . .
C13 C 0.82675(19) 0.4828(4) 1.0228(4) 0.0249(8) Uani 1 1 d . . . . .
C14 C 0.84002(17) 0.5242(3) 0.8774(4) 0.0204(7) Uani 1 1 d . . . . .
H14 H 0.8850 0.5305 0.8499 0.025 Uiso 1 1 calc R U . . .
C15 C 0.78719(16) 0.5557(3) 0.7745(4) 0.0130(6) Uani 1 1 d . . . . .
C16 C 0.78645(15) 0.6051(3) 0.6125(4) 0.0129(6) Uani 1 1 d . . . . .
C17 C 0.60535(16) 0.5729(3) 0.6923(4) 0.0139(6) Uani 1 1 d . . . . .
H17A H 0.5898 0.5941 0.7928 0.021 Uiso 1 1 calc R U . . .
H17B H 0.5952 0.4926 0.6714 0.021 Uiso 1 1 calc R U . . .
H17C H 0.5825 0.6200 0.6110 0.021 Uiso 1 1 calc R U . . .
C18 C 0.83636(17) 0.5514(3) 0.5103(4) 0.0191(7) Uani 1 1 d . . . . .
H18A H 0.8320 0.4684 0.5133 0.029 Uiso 1 1 calc R U . . .
H18B H 0.8822 0.5730 0.5483 0.029 Uiso 1 1 calc R U . . .
H18C H 0.8271 0.5781 0.4036 0.029 Uiso 1 1 calc R U . . .
C19 C 0.79958(18) 0.7337(3) 0.6256(4) 0.0188(7) Uani 1 1 d . . . . .
H19A H 0.8438 0.7469 0.6803 0.028 Uiso 1 1 calc R U . . .
H19B H 0.7648 0.7692 0.6831 0.028 Uiso 1 1 calc R U . . .
H19C H 0.7985 0.7670 0.5218 0.028 Uiso 1 1 calc R U . . .
C20A C 0.8880(3) 0.4663(4) 1.1327(6) 0.0185(4) Uani 0.6904(10) 1 d D . P A 1
C21A C 0.9422(3) 0.5402(5) 1.1630(6) 0.0185(4) Uani 0.6904(10) 1 d D . P A 1
H21A H 0.9451 0.6095 1.1075 0.022 Uiso 0.6904(10) 1 calc R U P A 1
C22A C 0.9896(3) 0.5103(4) 1.2720(6) 0.0185(4) Uani 0.6904(10) 1 d D . P A 1
H22A H 1.0284 0.5537 1.3036 0.022 Uiso 0.6904(10) 1 calc R U P A 1
S1A S 0.96903(18) 0.3787(4) 1.3478(3) 0.0242(5) Uani 0.6904(10) 1 d D . P A 1
C23A C 0.8975(3) 0.3730(4) 1.2241(6) 0.0185(4) Uani 0.6904(10) 1 d D . P A 1
Br1A Br 0.84332(3) 0.24450(5) 1.23291(8) 0.03192(17) Uani 0.6904(10) 1 d D . P
A 1
C20B C 0.8698(5) 0.4093(9) 1.1425(13) 0.0185(4) Uani 0.3096(10) 1 d D . P A 2
C21B C 0.8598(5) 0.3090(10) 1.2212(12) 0.0185(4) Uani 0.3096(10) 1 d D . P A 2
H21B H 0.8184 0.2692 1.2069 0.022 Uiso 0.3096(10) 1 calc R U P A 2
C22B C 0.9106(5) 0.2695(9) 1.3188(13) 0.0185(4) Uani 0.3096(10) 1 d D . P A 2
H22B H 0.9103 0.2008 1.3763 0.022 Uiso 0.3096(10) 1 calc R U P A 2
S1B S 0.9767(5) 0.3663(9) 1.3210(9) 0.0242(5) Uani 0.3096(10) 1 d D . P A 2
C23B C 0.9303(5) 0.4513(8) 1.1927(12) 0.0185(4) Uani 0.3096(10) 1 d D . P A 2
Br1B Br 0.96743(8) 0.59215(12) 1.15734(17) 0.03192(17) Uani 0.3096(10) 1 d D .
P A 2


_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
O1 C1 1.340(4) . ?
O1 C9 1.480(4) . ?
O2 N2 1.231(4) . ?
O3 N2 1.229(4) . ?
N1 C10 1.390(4) . ?
N1 C9 1.447(4) . ?
N1 C17 1.455(4) . ?
N2 C4 1.455(4) . ?
C1 C2 1.392(4) . ?
C1 C6 1.410(4) . ?
C2 C3 1.380(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(4) . ?
C5 C6 1.386(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.457(4) . ?
C7 C8 1.334(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.495(4) . ?
C8 H8 0.9500 . ?
C9 C16 1.557(4) . ?
C10 C11 1.388(4) . ?
C10 C15 1.397(4) . ?
C11 C12 1.398(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.397(6) . ?
C13 C20A 1.500(6) . ?
C13 C20B 1.555(11) . ?
C14 C15 1.376(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.519(5) . ?
C16 C18 1.524(5) . ?
C16 C19 1.537(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20A C23A 1.357(7) . ?
C20A C21A 1.397(7) . ?
C21A C22A 1.329(7) . ?
C21A H21A 0.9500 . ?
C22A S1A 1.743(7) . ?
C22A H22A 0.9500 . ?
S1A C23A 1.716(6) . ?
C23A Br1A 1.864(5) . ?
C20B C23B 1.345(12) . ?
C20B C21B 1.385(13) . ?
C21B C22B 1.348(12) . ?
C21B H21B 0.9500 . ?
C22B S1B 1.742(14) . ?
C22B H22B 0.9500 . ?
S1B C23B 1.710(12) . ?
C23B Br1B 1.850(10) . ?

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 O1 C9 120.8(2) . . ?
C10 N1 C9 107.2(2) . . ?
C10 N1 C17 121.4(3) . . ?
C9 N1 C17 120.7(3) . . ?
O3 N2 O2 123.3(3) . . ?
O3 N2 C4 118.1(3) . . ?
O2 N2 C4 118.6(3) . . ?
O1 C1 C2 116.9(3) . . ?
O1 C1 C6 121.5(3) . . ?
C2 C1 C6 121.5(3) . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 119.0(3) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 122.4(3) . . ?
C5 C4 N2 119.2(3) . . ?
C3 C4 N2 118.3(3) . . ?
C6 C5 C4 119.0(3) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 118.7(3) . . ?
C5 C6 C7 124.0(3) . . ?
C1 C6 C7 117.3(3) . . ?
C8 C7 C6 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 121.9(3) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
N1 C9 O1 108.2(2) . . ?
N1 C9 C8 112.3(3) . . ?
O1 C9 C8 110.8(2) . . ?
N1 C9 C16 102.9(2) . . ?
O1 C9 C16 103.7(2) . . ?
C8 C9 C16 118.1(3) . . ?
C11 C10 N1 129.3(3) . . ?
C11 C10 C15 121.0(3) . . ?
N1 C10 C15 109.7(3) . . ?
C10 C11 C12 117.7(3) . . ?
C10 C11 H11 121.1 . . ?
C12 C11 H11 121.1 . . ?
C13 C12 C11 121.5(3) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 119.8(3) . . ?
C12 C13 C20A 125.1(4) . . ?
C14 C13 C20A 114.4(4) . . ?
C12 C13 C20B 106.5(5) . . ?
C14 C13 C20B 131.4(5) . . ?
C15 C14 C13 119.2(3) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C10 120.8(3) . . ?
C14 C15 C16 130.7(3) . . ?
C10 C15 C16 108.5(3) . . ?
C15 C16 C18 114.9(3) . . ?
C15 C16 C19 108.6(3) . . ?
C18 C16 C19 109.6(3) . . ?
C15 C16 C9 99.5(2) . . ?
C18 C16 C9 113.2(3) . . ?
C19 C16 C9 110.5(3) . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C23A C20A C21A 108.8(5) . . ?
C23A C20A C13 122.9(5) . . ?
C21A C20A C13 128.2(4) . . ?
C22A C21A C20A 117.7(5) . . ?
C22A C21A H21A 121.1 . . ?
C20A C21A H21A 121.1 . . ?
C21A C22A S1A 109.1(4) . . ?
C21A C22A H22A 125.4 . . ?
S1A C22A H22A 125.4 . . ?
C23A S1A C22A 90.5(3) . . ?
C20A C23A S1A 113.8(4) . . ?
C20A C23A Br1A 128.6(4) . . ?
S1A C23A Br1A 117.5(3) . . ?
C23B C20B C21B 108.3(9) . . ?
C23B C20B C13 116.4(8) . . ?
C21B C20B C13 135.1(9) . . ?
C22B C21B C20B 118.1(10) . . ?
C22B C21B H21B 120.9 . . ?
C20B C21B H21B 120.9 . . ?
C21B C22B S1B 108.2(8) . . ?
C21B C22B H22B 125.9 . . ?
S1B C22B H22B 125.9 . . ?
C23B S1B C22B 90.3(6) . . ?
C20B C23B S1B 114.9(8) . . ?
C20B C23B Br1B 129.6(8) . . ?
S1B C23B Br1B 115.3(7) . . ?

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
C9 O1 C1 C2 -163.4(3) . . . . ?
C9 O1 C1 C6 19.7(4) . . . . ?
O1 C1 C2 C3 -178.4(3) . . . . ?
C6 C1 C2 C3 -1.5(5) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C2 C3 C4 C5 1.1(5) . . . . ?
C2 C3 C4 N2 179.0(3) . . . . ?
O3 N2 C4 C5 -177.8(3) . . . . ?
O2 N2 C4 C5 2.8(5) . . . . ?
O3 N2 C4 C3 4.3(5) . . . . ?
O2 N2 C4 C3 -175.1(3) . . . . ?
C3 C4 C5 C6 -0.7(5) . . . . ?
N2 C4 C5 C6 -178.5(3) . . . . ?
C4 C5 C6 C1 -0.7(5) . . . . ?
C4 C5 C6 C7 175.6(3) . . . . ?
O1 C1 C6 C5 178.6(3) . . . . ?
C2 C1 C6 C5 1.9(5) . . . . ?
O1 C1 C6 C7 2.0(4) . . . . ?
C2 C1 C6 C7 -174.7(3) . . . . ?
C5 C6 C7 C8 173.8(3) . . . . ?
C1 C6 C7 C8 -9.8(5) . . . . ?
C6 C7 C8 C9 -4.2(5) . . . . ?
C10 N1 C9 O1 75.1(3) . . . . ?
C17 N1 C9 O1 -69.8(3) . . . . ?
C10 N1 C9 C8 -162.2(2) . . . . ?
C17 N1 C9 C8 52.8(4) . . . . ?
C10 N1 C9 C16 -34.2(3) . . . . ?
C17 N1 C9 C16 -179.2(3) . . . . ?
C1 O1 C9 N1 92.6(3) . . . . ?
C1 O1 C9 C8 -31.0(4) . . . . ?
C1 O1 C9 C16 -158.6(3) . . . . ?
C7 C8 C9 N1 -98.0(4) . . . . ?
C7 C8 C9 O1 23.2(4) . . . . ?
C7 C8 C9 C16 142.5(3) . . . . ?
C9 N1 C10 C11 -158.3(3) . . . . ?
C17 N1 C10 C11 -13.6(5) . . . . ?
C9 N1 C10 C15 22.1(3) . . . . ?
C17 N1 C10 C15 166.8(3) . . . . ?
N1 C10 C11 C12 -178.4(3) . . . . ?
C15 C10 C11 C12 1.2(5) . . . . ?
C10 C11 C12 C13 0.1(5) . . . . ?
C11 C12 C13 C14 -0.3(6) . . . . ?
C11 C12 C13 C20A 170.0(4) . . . . ?
C11 C12 C13 C20B -164.9(5) . . . . ?
C12 C13 C14 C15 -0.7(6) . . . . ?
C20A C13 C14 C15 -172.0(4) . . . . ?
C20B C13 C14 C15 159.4(6) . . . . ?
C13 C14 C15 C10 2.0(5) . . . . ?
C13 C14 C15 C16 178.5(3) . . . . ?
C11 C10 C15 C14 -2.2(5) . . . . ?
N1 C10 C15 C14 177.4(3) . . . . ?
C11 C10 C15 C16 -179.5(3) . . . . ?
N1 C10 C15 C16 0.2(3) . . . . ?
C14 C15 C16 C18 41.8(5) . . . . ?
C10 C15 C16 C18 -141.4(3) . . . . ?
C14 C15 C16 C19 -81.4(4) . . . . ?
C10 C15 C16 C19 95.5(3) . . . . ?
C14 C15 C16 C9 163.1(3) . . . . ?
C10 C15 C16 C9 -20.1(3) . . . . ?
N1 C9 C16 C15 31.9(3) . . . . ?
O1 C9 C16 C15 -80.8(3) . . . . ?
C8 C9 C16 C15 156.2(3) . . . . ?
N1 C9 C16 C18 154.4(3) . . . . ?
O1 C9 C16 C18 41.7(3) . . . . ?
C8 C9 C16 C18 -81.3(4) . . . . ?
N1 C9 C16 C19 -82.2(3) . . . . ?
O1 C9 C16 C19 165.1(3) . . . . ?
C8 C9 C16 C19 42.1(4) . . . . ?
C12 C13 C20A C23A 52.6(7) . . . . ?
C14 C13 C20A C23A -136.7(5) . . . . ?
C12 C13 C20A C21A -125.5(6) . . . . ?
C14 C13 C20A C21A 45.2(7) . . . . ?
C23A C20A C21A C22A -1.9(7) . . . . ?
C13 C20A C21A C22A 176.4(5) . . . . ?
C20A C21A C22A S1A 0.8(6) . . . . ?
C21A C22A S1A C23A 0.5(4) . . . . ?
C21A C20A C23A S1A 2.2(6) . . . . ?
C13 C20A C23A S1A -176.2(4) . . . . ?
C21A C20A C23A Br1A -178.6(4) . . . . ?
C13 C20A C23A Br1A 2.9(8) . . . . ?
C22A S1A C23A C20A -1.6(4) . . . . ?
C22A S1A C23A Br1A 179.2(3) . . . . ?
C12 C13 C20B C23B -140.4(9) . . . . ?
C14 C13 C20B C23B 57.4(12) . . . . ?
C12 C13 C20B C21B 35.1(14) . . . . ?
C14 C13 C20B C21B -127.0(12) . . . . ?
C23B C20B C21B C22B -4.5(15) . . . . ?
C13 C20B C21B C22B 179.8(11) . . . . ?
C20B C21B C22B S1B 2.2(14) . . . . ?
C21B C22B S1B C23B 0.5(9) . . . . ?
C21B C20B C23B S1B 4.7(13) . . . . ?
C13 C20B C23B S1B -178.7(7) . . . . ?
C21B C20B C23B Br1B -169.2(9) . . . . ?
C13 C20B C23B Br1B 7.5(16) . . . . ?
C22B S1B C23B C20B -3.1(10) . . . . ?
C22B S1B C23B Br1B 171.7(7) . . . . ?

_refine_diff_density_max         1.867
_refine_diff_density_min         -2.512
_refine_diff_density_rms         0.130


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate / hexanes'
