# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_mo_ColourChem_DZ025b_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1913653'
loop_
_audit_author_name
_audit_author_address
'Craig Rice'
;University of Huddersfield
United Kingdom
;
_audit_update_record             
;
2019-05-02 deposited with the CCDC.	2019-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 N4 O2'
_chemical_formula_weight         400.47

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.145(6)
_cell_length_b                   11.501(7)
_cell_length_c                   11.649(8)
_cell_angle_alpha                117.55(2)
_cell_angle_beta                 94.48(3)
_cell_angle_gamma                91.05(2)
_cell_volume                     1080.9(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9960
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      33.12

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.81
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31525
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.981
_diffrn_reflns_theta_max         29.984
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6260
_reflns_number_gt                4483
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0783P)²+0.3250P] 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         6260
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.1621
_refine_ls_wR_factor_gt          0.1456
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
N1 N 0.22633(17) 0.86900(13) 0.87556(14) 0.0358(3) Uani 1 1 d . . . . .
N2 N 0.17585(18) 0.86527(13) 0.57232(15) 0.0403(4) Uani 1 1 d . . . . .
N3 N 0.93919(15) 0.79233(13) 0.14506(14) 0.0303(3) Uani 1 1 d . . . . .
N4 N 0.67974(15) 0.79031(12) 0.09774(14) 0.0282(3) Uani 1 1 d . . . . .
O1 O 0.27968(15) 0.58816(11) 0.90488(11) 0.0355(3) Uani 1 1 d . . . . .
O2 O 0.16271(13) 0.58061(11) 0.28241(11) 0.0314(3) Uani 1 1 d . . . . .
C1 C 0.29837(16) 0.39986(13) 0.70357(14) 0.0210(3) Uani 1 1 d . . . . .
C2 C 0.44223(17) 0.36021(15) 0.69642(16) 0.0290(3) Uani 1 1 d . . . . .
H2 H 0.5218 0.4234 0.7421 0.035 Uiso 1 1 calc R U . . .
C3 C 0.46946(19) 0.22936(16) 0.62318(19) 0.0355(4) Uani 1 1 d . . . . .
H3 H 0.5675 0.2028 0.6173 0.043 Uiso 1 1 calc R U . . .
C4 C 0.3524(2) 0.13691(16) 0.55817(18) 0.0371(4) Uani 1 1 d . . . . .
H4 H 0.3708 0.0469 0.5083 0.045 Uiso 1 1 calc R U . . .
C5 C 0.2096(2) 0.17512(15) 0.56558(18) 0.0349(4) Uani 1 1 d . . . . .
H5 H 0.1302 0.1113 0.5217 0.042 Uiso 1 1 calc R U . . .
C6 C 0.18203(17) 0.30673(14) 0.63721(15) 0.0267(3) Uani 1 1 d . . . . .
H6 H 0.0840 0.3332 0.6410 0.032 Uiso 1 1 calc R U . . .
C7 C 0.27246(15) 0.54258(14) 0.78565(14) 0.0218(3) Uani 1 1 d . . . . .
C8 C 0.24451(15) 0.62264(13) 0.72061(13) 0.0195(3) Uani 1 1 d . . . . .
C9 C 0.23426(16) 0.75972(14) 0.80480(14) 0.0233(3) Uani 1 1 d . . . . .
C10 C 0.23282(15) 0.56760(13) 0.58550(14) 0.0186(3) Uani 1 1 d . . . . .
H10 H 0.2411 0.4752 0.5433 0.022 Uiso 1 1 calc R U . . .
C11 C 0.21157(15) 0.62004(13) 0.49963(14) 0.0202(3) Uani 1 1 d . . . . .
C12 C 0.20035(15) 0.53803(13) 0.35935(14) 0.0212(3) Uani 1 1 d . . . . .
C13 C 0.23455(15) 0.39605(13) 0.30553(13) 0.0195(3) Uani 1 1 d . . . . .
C14 C 0.36890(16) 0.35686(14) 0.33689(14) 0.0233(3) Uani 1 1 d . . . . .
H14 H 0.4395 0.4205 0.3998 0.028 Uiso 1 1 calc R U . . .
C15 C 0.39976(17) 0.22559(15) 0.27670(16) 0.0283(3) Uani 1 1 d . . . . .
H15 H 0.4914 0.1994 0.2983 0.034 Uiso 1 1 calc R U . . .
C16 C 0.29695(19) 0.13253(15) 0.18498(17) 0.0313(4) Uani 1 1 d . . . . .
H16 H 0.3186 0.0426 0.1431 0.038 Uiso 1 1 calc R U . . .
C17 C 0.16232(18) 0.17028(15) 0.15413(16) 0.0311(4) Uani 1 1 d . . . . .
H17 H 0.0913 0.1060 0.0924 0.037 Uiso 1 1 calc R U . . .
C18 C 0.13164(16) 0.30139(14) 0.21318(15) 0.0244(3) Uani 1 1 d . . . . .
H18 H 0.0401 0.3272 0.1908 0.029 Uiso 1 1 calc R U . . .
C19 C 1.0671(2) 0.8761(2) 0.2278(3) 0.0605(6) Uani 1 1 d . . . . .
H19A H 1.0385 0.9665 0.2770 0.091 Uiso 1 1 calc R U . . .
H19B H 1.1444 0.8741 0.1732 0.091 Uiso 1 1 calc R U . . .
H19C H 1.1040 0.8438 0.2883 0.091 Uiso 1 1 calc R U . . .
C20 C 0.9709(2) 0.65479(17) 0.06812(18) 0.0384(4) Uani 1 1 d . . . . .
H20A H 0.9571 0.6076 0.1186 0.058 Uiso 1 1 calc R U . . .
H20B H 1.0728 0.6498 0.0463 0.058 Uiso 1 1 calc R U . . .
H20C H 0.9043 0.6148 -0.0121 0.058 Uiso 1 1 calc R U . . .
C21 C 0.81072(18) 0.84405(15) 0.15347(16) 0.0284(3) Uani 1 1 d . . . . .
H21 H 0.8134 0.9360 0.2095 0.034 Uiso 1 1 calc R U . . .
C22 C 0.6391(2) 0.65189(16) 0.00904(17) 0.0356(4) Uani 1 1 d . . . . .
H22A H 0.6658 0.6307 -0.0780 0.053 Uiso 1 1 calc R U . . .
H22B H 0.5329 0.6353 0.0052 0.053 Uiso 1 1 calc R U . . .
H22C H 0.6913 0.5969 0.0405 0.053 Uiso 1 1 calc R U . . .
C23 C 0.5575(2) 0.8766(2) 0.1195(2) 0.0481(5) Uani 1 1 d . . . . .
H23A H 0.5920 0.9668 0.1821 0.072 Uiso 1 1 calc R U . . .
H23B H 0.4788 0.8469 0.1541 0.072 Uiso 1 1 calc R U . . .
H23C H 0.5201 0.8736 0.0370 0.072 Uiso 1 1 calc R U . . .
C24 C 0.19125(17) 0.75654(14) 0.54169(15) 0.0256(3) 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 C9 1.148(2) . ?
N2 C24 1.146(2) . ?
N3 C21 1.317(2) . ?
N3 C20 1.461(2) . ?
N3 C19 1.466(2) . ?
N4 C21 1.311(2) . ?
N4 C22 1.462(2) . ?
N4 C23 1.466(2) . ?
O1 C7 1.233(2) . ?
O2 C12 1.2353(18) . ?
C1 C6 1.393(2) . ?
C1 C2 1.396(2) . ?
C1 C7 1.504(2) . ?
C2 C3 1.383(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.453(2) . ?
C8 C10 1.392(2) . ?
C8 C9 1.430(2) . ?
C10 C11 1.391(2) . ?
C10 H10 0.9500 . ?
C11 C24 1.433(2) . ?
C11 C12 1.454(2) . ?
C12 C13 1.503(2) . ?
C13 C14 1.396(2) . ?
C13 C18 1.396(2) . ?
C14 C15 1.385(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 N3 C20 127.58(14) . . ?
C21 N3 C19 118.74(16) . . ?
C20 N3 C19 113.52(15) . . ?
C21 N4 C22 127.70(14) . . ?
C21 N4 C23 118.17(15) . . ?
C22 N4 C23 114.06(15) . . ?
C6 C1 C2 119.64(14) . . ?
C6 C1 C7 121.41(14) . . ?
C2 C1 C7 118.94(13) . . ?
C3 C2 C1 120.30(15) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.62(16) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.47(16) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.05(15) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 119.92(15) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
O1 C7 C8 122.47(14) . . ?
O1 C7 C1 119.31(13) . . ?
C8 C7 C1 118.19(13) . . ?
C10 C8 C9 123.46(13) . . ?
C10 C8 C7 121.15(13) . . ?
C9 C8 C7 115.37(13) . . ?
N1 C9 C8 177.91(16) . . ?
C11 C10 C8 133.22(13) . . ?
C11 C10 H10 113.4 . . ?
C8 C10 H10 113.4 . . ?
C10 C11 C24 122.93(13) . . ?
C10 C11 C12 121.94(13) . . ?
C24 C11 C12 115.05(12) . . ?
O2 C12 C11 122.34(14) . . ?
O2 C12 C13 118.59(13) . . ?
C11 C12 C13 119.07(12) . . ?
C14 C13 C18 119.24(13) . . ?
C14 C13 C12 122.49(12) . . ?
C18 C13 C12 118.08(13) . . ?
C15 C14 C13 120.31(13) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.96(15) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C17 120.20(15) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 120.00(14) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C13 120.29(14) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N4 C21 N3 130.99(15) . . ?
N4 C21 H21 114.5 . . ?
N3 C21 H21 114.5 . . ?
N4 C22 H22A 109.5 . . ?
N4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N4 C23 H23A 109.5 . . ?
N4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C24 C11 178.27(18) . . ?

_refine_diff_density_max         0.404
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_mo_ColourChem_OrlandoX_0m
_database_code_depnum_ccdc_archive 'CCDC 1913657'
loop_
_audit_author_name
_audit_author_address
'Craig Rice'
;University of Huddersfield
United Kingdom
;
_audit_update_record             
;
2019-05-02 deposited with the CCDC.	2019-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H12 O5 S2'
_chemical_formula_weight         360.39

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'
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/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                   8.7498(5)
_cell_length_b                   18.5113(11)
_cell_length_c                   9.4511(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.3488(19)
_cell_angle_gamma                90
_cell_volume                     1510.46(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9864
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      33.19

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.379
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.49
_exptl_absorpt_correction_T_max  0.53
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28749
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.200
_diffrn_reflns_theta_max         33.186
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5781
_reflns_number_gt                4611
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0531P)²+0.6228P] 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         5781
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1090
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.15933(4) 0.46625(2) 0.16526(3) 0.01557(8) Uani 1 1 d . . . . .
S2 S 0.11666(4) 0.22191(2) 0.27425(3) 0.01727(8) Uani 1 1 d . . . . .
O1 O 0.15137(13) 0.53925(5) 0.21079(12) 0.0230(2) Uani 1 1 d . . . . .
O2 O 0.15817(13) 0.45083(6) 0.01771(10) 0.0246(2) Uani 1 1 d . . . . .
O3 O 0.00828(11) 0.42900(5) 0.21290(10) 0.01742(18) Uani 1 1 d . . . . .
O4 O 0.24280(13) 0.19852(6) 0.38089(12) 0.0257(2) Uani 1 1 d . . . . .
O5 O 0.10065(14) 0.19068(6) 0.13300(11) 0.0256(2) Uani 1 1 d . . . . .
C1 C 0.46403(16) 0.45318(7) 0.30500(14) 0.0172(2) Uani 1 1 d . . . . .
C2 C 0.57318(17) 0.42442(8) 0.41510(14) 0.0210(3) Uani 1 1 d . . . . .
H2 H 0.5461 0.3844 0.4689 0.025 Uiso 1 1 calc R U . . .
C3 C 0.72036(18) 0.45375(9) 0.44635(16) 0.0266(3) Uani 1 1 d . . . . .
H3 H 0.7944 0.4328 0.5195 0.032 Uiso 1 1 calc R U . . .
C4 C 0.76028(19) 0.51322(9) 0.37193(18) 0.0296(3) Uani 1 1 d . . . . .
H4 H 0.8607 0.5338 0.3952 0.035 Uiso 1 1 calc R U . . .
C5 C 0.65312(19) 0.54284(9) 0.26300(19) 0.0298(3) Uani 1 1 d . . . . .
H5 H 0.6802 0.5837 0.2116 0.036 Uiso 1 1 calc R U . . .
C6 C 0.50669(18) 0.51282(8) 0.22903(16) 0.0244(3) Uani 1 1 d . . . . .
H6 H 0.4344 0.5329 0.1534 0.029 Uiso 1 1 calc R U . . .
C7 C 0.31174(15) 0.41850(7) 0.26872(13) 0.0162(2) Uani 1 1 d . . . . .
C8 C 0.28124(15) 0.34868(7) 0.29653(14) 0.0169(2) Uani 1 1 d . . . . .
H8 H 0.3641 0.3194 0.3420 0.020 Uiso 1 1 calc R U . . .
C9 C 0.13106(15) 0.31647(7) 0.26128(13) 0.0161(2) Uani 1 1 d . . . . .
C10 C -0.00111(15) 0.35445(7) 0.22176(13) 0.0150(2) Uani 1 1 d . . . . .
C11 C -0.15739(15) 0.32506(7) 0.19164(13) 0.0157(2) Uani 1 1 d . . . . .
C12 C -0.27645(16) 0.36367(7) 0.10768(14) 0.0194(2) Uani 1 1 d . . . . .
H12 H -0.2572 0.4107 0.0743 0.023 Uiso 1 1 calc R U . . .
C13 C -0.42260(17) 0.33322(8) 0.07327(15) 0.0228(3) Uani 1 1 d . . . . .
H13 H -0.5034 0.3594 0.0162 0.027 Uiso 1 1 calc R U . . .
C14 C -0.45109(17) 0.26455(9) 0.12207(16) 0.0243(3) Uani 1 1 d . . . . .
H14 H -0.5512 0.2438 0.0978 0.029 Uiso 1 1 calc R U . . .
C15 C -0.33358(17) 0.22595(8) 0.20640(15) 0.0228(3) Uani 1 1 d . . . . .
H15 H -0.3541 0.1790 0.2394 0.027 Uiso 1 1 calc R U . . .
C16 C -0.18624(16) 0.25559(7) 0.24274(13) 0.0175(2) Uani 1 1 d . . . . .
C17 C -0.06119(17) 0.21460(7) 0.33857(14) 0.0195(3) Uani 1 1 d . . . . .
H17A H -0.0909 0.1631 0.3418 0.023 Uiso 1 1 calc R U . . .
H17B H -0.0496 0.2342 0.4372 0.023 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 O2 1.4219(10) . ?
S1 O1 1.4234(10) . ?
S1 O3 1.6181(10) . ?
S1 C7 1.7584(13) . ?
S2 O4 1.4352(11) . ?
S2 O5 1.4406(11) . ?
S2 C9 1.7608(13) . ?
S2 C17 1.7654(14) . ?
O3 C10 1.3857(15) . ?
C1 C2 1.3984(19) . ?
C1 C6 1.4002(19) . ?
C1 C7 1.4687(19) . ?
C2 C3 1.384(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.3540(18) . ?
C8 C9 1.4322(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.3531(18) . ?
C10 C11 1.4561(18) . ?
C11 C12 1.3991(19) . ?
C11 C16 1.4107(18) . ?
C12 C13 1.387(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.3919(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.5071(19) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?

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 119.61(7) . . ?
O2 S1 O3 108.14(6) . . ?
O1 S1 O3 103.78(6) . . ?
O2 S1 C7 109.17(6) . . ?
O1 S1 C7 112.28(6) . . ?
O3 S1 C7 102.18(6) . . ?
O4 S2 O5 118.53(7) . . ?
O4 S2 C9 107.05(6) . . ?
O5 S2 C9 109.37(6) . . ?
O4 S2 C17 110.82(7) . . ?
O5 S2 C17 109.26(7) . . ?
C9 S2 C17 100.21(6) . . ?
C10 O3 S1 120.02(8) . . ?
C2 C1 C6 118.36(13) . . ?
C2 C1 C7 119.43(12) . . ?
C6 C1 C7 122.16(12) . . ?
C3 C2 C1 120.57(13) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 120.48(15) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.76(14) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.09(15) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.72(14) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
C8 C7 C1 124.88(12) . . ?
C8 C7 S1 115.61(10) . . ?
C1 C7 S1 119.17(9) . . ?
C7 C8 C9 123.68(12) . . ?
C7 C8 H8 118.2 . . ?
C9 C8 H8 118.2 . . ?
C10 C9 C8 123.96(12) . . ?
C10 C9 S2 117.92(10) . . ?
C8 C9 S2 118.10(10) . . ?
C9 C10 O3 118.54(11) . . ?
C9 C10 C11 126.38(12) . . ?
O3 C10 C11 115.04(11) . . ?
C12 C11 C16 120.11(12) . . ?
C12 C11 C10 120.60(12) . . ?
C16 C11 C10 119.23(11) . . ?
C13 C12 C11 119.91(13) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.17(13) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 120.29(13) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 120.50(13) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 119.01(12) . . ?
C15 C16 C17 120.18(12) . . ?
C11 C16 C17 120.79(12) . . ?
C16 C17 S2 110.43(9) . . ?
C16 C17 H17A 109.6 . . ?
S2 C17 H17A 109.6 . . ?
C16 C17 H17B 109.6 . . ?
S2 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?

_refine_diff_density_max         0.547
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.079

####################################################################### 
# 
# 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_cu_ColourChem_ID0176_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1913654'
loop_
_audit_author_name
_audit_author_address
'Craig Rice'
;University of Huddersfield
United Kingdom
;
_audit_update_record             
;
2019-05-02 deposited with the CCDC.	2019-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H23 N3 O2'
_chemical_formula_weight         373.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'

_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'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   38.315(3)
_cell_length_b                   38.315
_cell_length_c                   5.5470(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8143.4(16)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6514
_cell_measurement_theta_min      3.26
_cell_measurement_theta_max      74.54

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_F_000             3168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.631
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.51
_exptl_absorpt_correction_T_max  0.68
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15925
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.306
_diffrn_reflns_theta_max         74.521
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4122
_reflns_number_gt                3134
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0437P)²+5.9308P] 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         4122
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1205
_refine_ls_wR_factor_gt          0.1101
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
N1 N 0.78086(4) 0.72105(4) 0.1826(4) 0.0483(5) Uani 1 1 d . . . . .
N2 N 0.76381(4) 0.65135(5) 0.5420(3) 0.0397(4) Uani 1 1 d . . . . .
N3 N 0.94297(4) 0.55988(4) 0.1676(3) 0.0263(3) Uani 1 1 d . . . . .
O1 O 0.85686(4) 0.72970(4) -0.1204(3) 0.0665(6) Uani 1 1 d . . . . .
O2 O 0.87716(3) 0.60387(3) 0.5445(2) 0.0317(3) Uani 1 1 d . . . . .
C1 C 0.90302(4) 0.69587(4) 0.0312(3) 0.0265(4) Uani 1 1 d . . . . .
C2 C 0.91778(5) 0.67742(5) -0.1588(4) 0.0372(5) Uani 1 1 d . . . . .
H2 H 0.9036 0.6697 -0.2886 0.045 Uiso 1 1 calc R U . . .
C3 C 0.95313(6) 0.67033(5) -0.1586(4) 0.0404(5) Uani 1 1 d . . . . .
H3 H 0.9630 0.6573 -0.2872 0.048 Uiso 1 1 calc R U . . .
C4 C 0.97405(5) 0.68192(5) 0.0256(4) 0.0365(4) Uani 1 1 d . . . . .
H4 H 0.9984 0.6775 0.0222 0.044 Uiso 1 1 calc R U . . .
C5 C 0.95947(5) 0.70001(5) 0.2158(4) 0.0362(4) Uani 1 1 d . . . . .
H5 H 0.9738 0.7079 0.3444 0.043 Uiso 1 1 calc R U . . .
C6 C 0.92401(5) 0.70675(5) 0.2197(3) 0.0324(4) Uani 1 1 d . . . . .
H6 H 0.9140 0.7189 0.3522 0.039 Uiso 1 1 calc R U . . .
C7 C 0.86546(5) 0.70689(5) 0.0244(4) 0.0345(4) Uani 1 1 d . . . . .
C8 C 0.84093(4) 0.69101(4) 0.1895(3) 0.0261(4) Uani 1 1 d . . . . .
C9 C 0.84955(4) 0.66263(4) 0.3317(3) 0.0227(3) Uani 1 1 d . . . . .
H9 H 0.8733 0.6557 0.3186 0.027 Uiso 1 1 calc R U . . .
C10 C 0.82997(4) 0.64229(4) 0.4908(3) 0.0227(3) Uani 1 1 d . . . . .
C11 C 0.80706(5) 0.70668(4) 0.1882(4) 0.0316(4) Uani 1 1 d . . . . .
C12 C 0.79351(4) 0.64776(4) 0.5224(3) 0.0269(4) Uani 1 1 d . . . . .
C13 C 0.84674(4) 0.61179(4) 0.5966(3) 0.0238(4) Uani 1 1 d . . . . .
C14 C 0.82723(4) 0.58887(4) 0.7695(3) 0.0243(4) Uani 1 1 d . . . . .
C15 C 0.83252(5) 0.55283(5) 0.7563(3) 0.0319(4) Uani 1 1 d . . . . .
H15 H 0.8473 0.5434 0.6348 0.038 Uiso 1 1 calc R U . . .
C16 C 0.81642(5) 0.53074(5) 0.9194(4) 0.0378(5) Uani 1 1 d . . . . .
H16 H 0.8198 0.5062 0.9078 0.045 Uiso 1 1 calc R U . . .
C17 C 0.79540(5) 0.54442(5) 1.1001(3) 0.0351(4) Uani 1 1 d . . . . .
H17 H 0.7846 0.5293 1.2133 0.042 Uiso 1 1 calc R U . . .
C18 C 0.79024(5) 0.57997(5) 1.1151(3) 0.0329(4) Uani 1 1 d . . . . .
H18 H 0.7758 0.5893 1.2387 0.039 Uiso 1 1 calc R U . . .
C19 C 0.80599(4) 0.60218(5) 0.9503(3) 0.0277(4) Uani 1 1 d . . . . .
H19 H 0.8022 0.6266 0.9611 0.033 Uiso 1 1 calc R U . . .
C20 C 0.92033(6) 0.57651(6) -0.0173(4) 0.0452(5) Uani 1 1 d . . . . .
H20A H 0.9021 0.5902 0.0627 0.068 Uiso 1 1 calc R U . . .
H20B H 0.9095 0.5584 -0.1172 0.068 Uiso 1 1 calc R U . . .
H20C H 0.9345 0.5919 -0.1191 0.068 Uiso 1 1 calc R U . . .
C21 C 0.92112(6) 0.53680(5) 0.3234(4) 0.0429(5) Uani 1 1 d . . . . .
H21A H 0.9036 0.5509 0.4073 0.064 Uiso 1 1 calc R U . . .
H21B H 0.9360 0.5251 0.4420 0.064 Uiso 1 1 calc R U . . .
H21C H 0.9094 0.5193 0.2232 0.064 Uiso 1 1 calc R U . . .
C22 C 0.97040(5) 0.53841(5) 0.0450(4) 0.0359(4) Uani 1 1 d . . . . .
H22A H 0.9592 0.5209 -0.0577 0.054 Uiso 1 1 calc R U . . .
H22B H 0.9848 0.5267 0.1667 0.054 Uiso 1 1 calc R U . . .
H22C H 0.9851 0.5536 -0.0542 0.054 Uiso 1 1 calc R U . . .
C23 C 0.95966(5) 0.58746(5) 0.3180(4) 0.0398(5) Uani 1 1 d . . . . .
H23A H 0.9748 0.6019 0.2164 0.060 Uiso 1 1 calc R U . . .
H23B H 0.9736 0.5765 0.4451 0.060 Uiso 1 1 calc R U . . .
H23C H 0.9415 0.6021 0.3912 0.060 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 C11 1.146(2) . ?
N2 C12 1.151(2) . ?
N3 C20 1.487(2) . ?
N3 C23 1.491(2) . ?
N3 C21 1.493(2) . ?
N3 C22 1.498(2) . ?
O1 C7 1.232(2) . ?
O2 C13 1.239(2) . ?
C1 C6 1.383(2) . ?
C1 C2 1.389(3) . ?
C1 C7 1.500(2) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.446(3) . ?
C8 C9 1.383(2) . ?
C8 C11 1.430(2) . ?
C9 C10 1.396(2) . ?
C9 H9 0.9500 . ?
C10 C12 1.423(2) . ?
C10 C13 1.458(2) . ?
C13 C14 1.500(2) . ?
C14 C19 1.389(2) . ?
C14 C15 1.397(2) . ?
C15 C16 1.384(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 N3 C23 109.40(15) . . ?
C20 N3 C21 109.04(16) . . ?
C23 N3 C21 109.66(15) . . ?
C20 N3 C22 109.37(15) . . ?
C23 N3 C22 110.02(15) . . ?
C21 N3 C22 109.32(14) . . ?
C6 C1 C2 119.33(17) . . ?
C6 C1 C7 119.47(17) . . ?
C2 C1 C7 120.97(17) . . ?
C3 C2 C1 119.91(18) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 120.64(19) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.66(18) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 120.20(18) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 120.21(18) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
O1 C7 C8 122.52(17) . . ?
O1 C7 C1 118.19(17) . . ?
C8 C7 C1 119.28(15) . . ?
C9 C8 C11 123.34(16) . . ?
C9 C8 C7 122.45(15) . . ?
C11 C8 C7 114.20(15) . . ?
C8 C9 C10 132.13(16) . . ?
C8 C9 H9 113.9 . . ?
C10 C9 H9 113.9 . . ?
C9 C10 C12 121.55(15) . . ?
C9 C10 C13 117.73(15) . . ?
C12 C10 C13 120.08(15) . . ?
N1 C11 C8 175.87(19) . . ?
N2 C12 C10 177.7(2) . . ?
O2 C13 C10 121.15(15) . . ?
O2 C13 C14 118.36(15) . . ?
C10 C13 C14 120.48(14) . . ?
C19 C14 C15 119.05(16) . . ?
C19 C14 C13 122.60(15) . . ?
C15 C14 C13 118.22(15) . . ?
C16 C15 C14 120.37(17) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.97(18) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 119.97(17) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.26(18) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 120.37(17) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N3 C23 H23A 109.5 . . ?
N3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_refine_diff_density_max         0.151
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_mo_Ross_SO2_0m
_database_code_depnum_ccdc_archive 'CCDC 1913658'
loop_
_audit_author_name
_audit_author_address
'Craig Rice'
;University of Huddersfield
United Kingdom
;
_audit_update_record             
;
2019-05-02 deposited with the CCDC.	2019-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H25 N O4 S'
_chemical_formula_weight         411.50

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                   11.6856(9)
_cell_length_b                   14.0485(11)
_cell_length_c                   13.2869(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.0216(18)
_cell_angle_gamma                90
_cell_volume                     2169.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7419
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      30.21

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.177
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.48
_exptl_absorpt_correction_T_max  0.61
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31491
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.116
_diffrn_reflns_theta_max         30.568
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6623
_reflns_number_gt                4378
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0502P)²+1.1917P] 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         6623
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1333
_refine_ls_wR_factor_gt          0.1082
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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 0.97766(4) 0.07542(3) 0.29573(3) 0.03426(12) Uani 1 1 d . . . . .
N1 N 0.75391(11) 0.21919(11) 0.44936(11) 0.0322(3) Uani 1 1 d . . . . .
O1 O 1.04133(11) 0.02188(10) 0.37326(11) 0.0475(3) Uani 1 1 d . . . . .
O2 O 0.96862(12) 0.04202(11) 0.19415(10) 0.0490(4) Uani 1 1 d . . . . .
O3 O 1.03274(10) 0.17906(9) 0.28999(9) 0.0349(3) Uani 1 1 d . . . . .
O4 O 1.10463(10) 0.31072(10) 0.56374(9) 0.0384(3) Uani 1 1 d . . . . .
C1 C 1.13518(13) 0.29927(12) 0.38926(13) 0.0309(3) Uani 1 1 d . . . . .
C2 C 1.16317(14) 0.33859(13) 0.48474(13) 0.0331(4) Uani 1 1 d . . . . .
C3 C 1.25553(15) 0.40019(15) 0.50284(16) 0.0427(4) Uani 1 1 d . . . . .
H3 H 1.2752 0.4249 0.5673 0.051 Uiso 1 1 calc R U . . .
C4 C 1.31800(16) 0.42449(16) 0.42401(18) 0.0492(5) Uani 1 1 d . . . . .
H4 H 1.3797 0.4663 0.4356 0.059 Uiso 1 1 calc R U . . .
C5 C 1.29024(16) 0.38773(16) 0.32860(17) 0.0482(5) Uani 1 1 d . . . . .
H5 H 1.3321 0.4057 0.2759 0.058 Uiso 1 1 calc R U . . .
C6 C 1.19990(15) 0.32397(14) 0.31101(15) 0.0398(4) Uani 1 1 d . . . . .
H6 H 1.1825 0.2977 0.2470 0.048 Uiso 1 1 calc R U . . .
C7 C 1.03802(13) 0.23420(12) 0.37930(12) 0.0288(3) Uani 1 1 d . . . . .
C8 C 0.96119(13) 0.22833(11) 0.44598(12) 0.0276(3) Uani 1 1 d . . . . .
C9 C 0.98140(14) 0.29105(13) 0.54054(13) 0.0318(4) Uani 1 1 d . . . . .
C10 C 0.95104(18) 0.24020(16) 0.63510(14) 0.0450(5) Uani 1 1 d . . . . .
H10A H 0.9909 0.1804 0.6417 0.067 Uiso 1 1 calc R U . . .
H10B H 0.8696 0.2291 0.6300 0.067 Uiso 1 1 calc R U . . .
H10C H 0.9734 0.2789 0.6934 0.067 Uiso 1 1 calc R U . . .
C11 C 0.92063(17) 0.38658(14) 0.52766(16) 0.0429(4) Uani 1 1 d . . . . .
H11A H 0.9421 0.4256 0.5859 0.064 Uiso 1 1 calc R U . . .
H11B H 0.8389 0.3768 0.5207 0.064 Uiso 1 1 calc R U . . .
H11C H 0.9425 0.4177 0.4683 0.064 Uiso 1 1 calc R U . . .
C12 C 0.85579(13) 0.16384(12) 0.43462(12) 0.0283(3) Uani 1 1 d . . . . .
H12 H 0.8657 0.1164 0.4889 0.034 Uiso 1 1 calc R U . . .
C13 C 0.84141(13) 0.10882(12) 0.33208(12) 0.0289(3) Uani 1 1 d . . . . .
H13 H 0.8072 0.1534 0.2807 0.035 Uiso 1 1 calc R U . . .
C14 C 0.76103(14) 0.02461(12) 0.33194(13) 0.0317(3) Uani 1 1 d . . . . .
C15 C 0.78050(17) -0.04958(14) 0.40015(16) 0.0452(5) Uani 1 1 d . . . . .
H15 H 0.8470 -0.0504 0.4452 0.054 Uiso 1 1 calc R U . . .
C16 C 0.7012(2) -0.12251(16) 0.40139(19) 0.0547(6) Uani 1 1 d . . . . .
H16 H 0.7149 -0.1723 0.4471 0.066 Uiso 1 1 calc R U . . .
C17 C 0.60224(19) -0.12197(17) 0.33557(18) 0.0543(6) Uani 1 1 d . . . . .
H17 H 0.5489 -0.1709 0.3372 0.065 Uiso 1 1 calc R U . . .
C18 C 0.58245(17) -0.04897(17) 0.26750(16) 0.0503(5) Uani 1 1 d . . . . .
H18 H 0.5155 -0.0485 0.2230 0.060 Uiso 1 1 calc R U . . .
C19 C 0.66147(15) 0.02385(15) 0.26466(14) 0.0389(4) Uani 1 1 d . . . . .
H19 H 0.6480 0.0726 0.2175 0.047 Uiso 1 1 calc R U . . .
C20 C 0.65709(17) 0.17435(16) 0.49236(17) 0.0461(5) Uani 1 1 d . . . . .
H20A H 0.6786 0.1544 0.5617 0.055 Uiso 1 1 calc R U . . .
H20B H 0.6290 0.1196 0.4527 0.055 Uiso 1 1 calc R U . . .
C21 C 0.5684(2) 0.2524(2) 0.4874(3) 0.0944(11) Uani 1 1 d . . . . .
H21A H 0.4928 0.2270 0.4652 0.113 Uiso 1 1 calc R U . . .
H21B H 0.5661 0.2810 0.5536 0.113 Uiso 1 1 calc R U . . .
C22 C 0.60240(18) 0.32540(18) 0.41317(19) 0.0551(6) Uani 1 1 d . . . . .
H22A H 0.6228 0.3851 0.4470 0.066 Uiso 1 1 calc R U . . .
H22B H 0.5400 0.3367 0.3604 0.066 Uiso 1 1 calc R U . . .
C23 C 0.70550(15) 0.28263(14) 0.36936(15) 0.0395(4) Uani 1 1 d . . . . .
H23A H 0.6822 0.2477 0.3076 0.047 Uiso 1 1 calc R U . . .
H23B H 0.7603 0.3315 0.3552 0.047 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 O1 1.4211(14) . ?
S1 O2 1.4223(14) . ?
S1 O3 1.5970(13) . ?
S1 C13 1.7748(16) . ?
N1 C12 1.452(2) . ?
N1 C23 1.455(2) . ?
N1 C20 1.463(2) . ?
O3 C7 1.4130(19) . ?
O4 C2 1.369(2) . ?
O4 C9 1.467(2) . ?
C1 C2 1.391(2) . ?
C1 C6 1.392(2) . ?
C1 C7 1.453(2) . ?
C2 C3 1.385(2) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.328(2) . ?
C8 C12 1.524(2) . ?
C8 C9 1.532(2) . ?
C9 C10 1.519(3) . ?
C9 C11 1.520(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.560(2) . ?
C12 H12 0.9800 . ?
C13 C14 1.510(2) . ?
C13 H13 0.9800 . ?
C14 C15 1.384(3) . ?
C14 C19 1.391(2) . ?
C15 C16 1.383(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.371(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.381(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.506(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.505(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.516(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?

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
O1 S1 O2 119.63(9) . . ?
O1 S1 O3 109.52(8) . . ?
O2 S1 O3 104.22(8) . . ?
O1 S1 C13 111.04(8) . . ?
O2 S1 C13 111.48(8) . . ?
O3 S1 C13 98.60(7) . . ?
C12 N1 C23 119.39(13) . . ?
C12 N1 C20 120.05(15) . . ?
C23 N1 C20 106.96(14) . . ?
C7 O3 S1 116.23(10) . . ?
C2 O4 C9 116.82(13) . . ?
C2 C1 C6 119.21(16) . . ?
C2 C1 C7 116.09(15) . . ?
C6 C1 C7 124.70(16) . . ?
O4 C2 C3 119.25(16) . . ?
O4 C2 C1 119.82(15) . . ?
C3 C2 C1 120.74(17) . . ?
C4 C3 C2 119.16(18) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 120.92(18) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.99(19) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 119.95(18) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C8 C7 O3 123.58(14) . . ?
C8 C7 C1 123.68(15) . . ?
O3 C7 C1 112.73(14) . . ?
C7 C8 C12 124.52(15) . . ?
C7 C8 C9 117.02(14) . . ?
C12 C8 C9 118.46(13) . . ?
O4 C9 C10 102.94(13) . . ?
O4 C9 C11 107.10(14) . . ?
C10 C9 C11 111.19(16) . . ?
O4 C9 C8 110.13(13) . . ?
C10 C9 C8 112.24(15) . . ?
C11 C9 C8 112.67(14) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C8 109.50(13) . . ?
N1 C12 C13 111.61(13) . . ?
C8 C12 C13 113.14(13) . . ?
N1 C12 H12 107.4 . . ?
C8 C12 H12 107.4 . . ?
C13 C12 H12 107.4 . . ?
C14 C13 C12 113.53(14) . . ?
C14 C13 S1 111.60(12) . . ?
C12 C13 S1 110.56(10) . . ?
C14 C13 H13 106.9 . . ?
C12 C13 H13 106.9 . . ?
S1 C13 H13 106.9 . . ?
C15 C14 C19 118.94(16) . . ?
C15 C14 C13 121.97(15) . . ?
C19 C14 C13 119.01(16) . . ?
C16 C15 C14 120.09(18) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 120.6(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 119.75(19) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.34(18) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 120.31(18) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
N1 C20 C21 103.09(18) . . ?
N1 C20 H20A 111.1 . . ?
C21 C20 H20A 111.1 . . ?
N1 C20 H20B 111.1 . . ?
C21 C20 H20B 111.1 . . ?
H20A C20 H20B 109.1 . . ?
C22 C21 C20 107.27(18) . . ?
C22 C21 H21A 110.3 . . ?
C20 C21 H21A 110.3 . . ?
C22 C21 H21B 110.3 . . ?
C20 C21 H21B 110.3 . . ?
H21A C21 H21B 108.5 . . ?
C21 C22 C23 104.88(18) . . ?
C21 C22 H22A 110.8 . . ?
C23 C22 H22A 110.8 . . ?
C21 C22 H22B 110.8 . . ?
C23 C22 H22B 110.8 . . ?
H22A C22 H22B 108.8 . . ?
N1 C23 C22 103.06(16) . . ?
N1 C23 H23A 111.2 . . ?
C22 C23 H23A 111.2 . . ?
N1 C23 H23B 111.2 . . ?
C22 C23 H23B 111.2 . . ?
H23A C23 H23B 109.1 . . ?

_refine_diff_density_max         0.328
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_mo_CC_KAA9R_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1913656'
loop_
_audit_author_name
_audit_author_address
'Craig Rice'
;University of Huddersfield
United Kingdom
;
_audit_update_record             
;
2019-05-02 deposited with the CCDC.	2019-10-31 downloaded from the CCDC.
;
_audit_creation_date             2017-03-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5318)
;
_chemical_formula_moiety         'C22 H16 O3 S'
_chemical_formula_sum            'C22 H16 O3 S'
_chemical_formula_weight         360.44
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.8058(9)
_cell_length_b                   20.394(2)
_cell_length_c                   9.6437(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.794(4)
_cell_angle_gamma                90
_cell_volume                     1706.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7244
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.09
_cell_measurement_theta_min      2.36
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.4027
_exptl_crystal_description       block
_exptl_crystal_F_000             752.8599
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_unetI/netI     0.0836
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19217
_diffrn_reflns_theta_full        30.5065
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         2.36
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.9996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -12
_reflns_limit_k_max              29
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              -7
_reflns_number_gt                3595
_reflns_number_total             5218
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.9287
_refine_diff_density_min         -0.9851
_refine_diff_density_rms         0.1864
_refine_ls_d_res_high            0.7000
_refine_ls_d_res_low             8.6139
_refine_ls_goodness_of_fit_ref   1.0557
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     235
_refine_ls_number_reflns         5218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0686
_refine_ls_restrained_S_all      1.0557
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0488P)²+1.5819P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1417
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
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_refinement_flags_posn
S1 S 0.37759(6) 0.54496(3) 0.26949(6) 0.01528(13) Uani 1.000000 .
O1 O 0.49207(17) 0.57946(7) 0.39429(17) 0.0179(3) Uani 1.000000 .
O2 O 0.39362(19) 0.57576(8) 0.14084(17) 0.0247(4) Uani 1.000000 .
O3 O 0.41212(18) 0.47694(8) 0.28776(18) 0.0224(4) Uani 1.000000 .
C1 C 0.1984(2) 0.56549(11) 0.3134(2) 0.0153(4) Uani 1.000000 .
C2 C 0.1938(2) 0.62446(11) 0.3757(2) 0.0171(4) Uani 1.000000 .
H2 H 0.0955(2) 0.63959(11) 0.3898(2) 0.0205(5) Uiso 1.000000 R
C3 C 0.3241(2) 0.66709(10) 0.4234(2) 0.0156(4) Uani 1.000000 .
C4 C 0.4692(2) 0.64524(10) 0.4293(2) 0.0149(4) Uani 1.000000 .
C5 C 0.0654(2) 0.52092(10) 0.2725(2) 0.0161(4) Uani 1.000000 .
C6 C 0.0602(3) 0.47481(11) 0.1654(2) 0.0189(5) Uani 1.000000 .
H6 H 0.1464(3) 0.46950(11) 0.1191(2) 0.0226(6) Uiso 1.000000 R
C7 C -0.0705(3) 0.43649(12) 0.1259(3) 0.0238(5) Uani 1.000000 .
H7 H -0.0733(3) 0.40543(12) 0.0521(3) 0.0285(6) Uiso 1.000000 R
C8 C -0.1966(3) 0.44315(12) 0.1930(3) 0.0249(5) Uani 1.000000 .
H8 H -0.2863(3) 0.41737(12) 0.1642(3) 0.0299(6) Uiso 1.000000 R
C9 C -0.1912(3) 0.48767(12) 0.3024(3) 0.0230(5) Uani 1.000000 .
H9 H -0.2765(3) 0.49162(12) 0.3504(3) 0.0276(6) Uiso 1.000000 R
C10 C -0.0618(3) 0.52637(11) 0.3418(3) 0.0201(5) Uani 1.000000 .
H10 H -0.0591(3) 0.55694(11) 0.4165(3) 0.0242(6) Uiso 1.000000 R
C11 C 0.2890(2) 0.73405(10) 0.4728(2) 0.0151(4) Uani 1.000000 .
C12 C 0.2089(3) 0.77886(11) 0.3789(2) 0.0185(5) Uani 1.000000 .
H12 H 0.1754(3) 0.76660(11) 0.2836(2) 0.0222(6) Uiso 1.000000 R
C13 C 0.1774(3) 0.84143(12) 0.4237(3) 0.0248(5) Uani 1.000000 .
H13 H 0.1236(3) 0.87195(12) 0.3588(3) 0.0297(6) Uiso 1.000000 R
C14 C 0.2244(3) 0.85919(12) 0.5626(3) 0.0262(6) Uani 1.000000 .
H14 H 0.2041(3) 0.90210(12) 0.5931(3) 0.0315(7) Uiso 1.000000 R
C15 C 0.3011(3) 0.81435(12) 0.6572(3) 0.0244(5) Uani 1.000000 .
H15 H 0.3320(3) 0.82640(12) 0.7530(3) 0.0293(6) Uiso 1.000000 R
C16 C 0.3333(3) 0.75175(12) 0.6128(2) 0.0199(5) Uani 1.000000 .
H16 H 0.3856(3) 0.72113(12) 0.6784(2) 0.0239(6) Uiso 1.000000 R
C17 C 0.6178(2) 0.67820(10) 0.4784(2) 0.0141(4) Uani 1.000000 .
C18 C 0.7434(2) 0.64206(11) 0.5459(2) 0.0165(4) Uani 1.000000 .
H18 H 0.7328(2) 0.59633(11) 0.5603(2) 0.0198(5) Uiso 1.000000 R
C19 C 0.8837(3) 0.67249(11) 0.5921(2) 0.0187(5) Uani 1.000000 .
H19 H 0.9687(3) 0.64755(11) 0.6382(2) 0.0225(6) Uiso 1.000000 R
C20 C 0.9005(3) 0.73931(12) 0.5713(2) 0.0204(5) Uani 1.000000 .
H20 H 0.9963(3) 0.76025(12) 0.6040(2) 0.0245(6) Uiso 1.000000 R
C21 C 0.7768(3) 0.77522(11) 0.5027(2) 0.0208(5) Uani 1.000000 .
H21 H 0.7886(3) 0.82081(11) 0.4873(2) 0.0249(6) Uiso 1.000000 R
C22 C 0.6360(3) 0.74545(11) 0.4561(2) 0.0179(5) Uani 1.000000 .
H22 H 0.5519(3) 0.77058(11) 0.4091(2) 0.0215(5) Uiso 1.000000 R


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 O1 1.5959(16) . ?
S1 O2 1.4189(17) . ?
S1 O3 1.4248(16) . ?
S1 C1 1.753(2) . ?
O1 C4 1.406(2) . ?
C1 C2 1.348(3) . ?
C1 C5 1.482(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.451(3) . ?
C3 C4 1.345(3) . ?
C3 C11 1.496(3) . ?
C4 C17 1.476(3) . ?
C5 C6 1.392(3) . ?
C5 C10 1.403(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.389(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.384(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.385(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(3) . ?
C11 C16 1.389(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.390(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.391(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.395(3) . ?
C17 C22 1.402(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.384(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.385(3) . ?
C22 H22 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
O2 S1 O1 108.68(9) . . ?
O3 S1 O1 104.00(9) . . ?
O3 S1 O2 119.22(10) . . ?
C1 S1 O1 101.06(9) . . ?
C1 S1 O2 109.45(10) . . ?
C1 S1 O3 112.62(10) . . ?
C4 O1 S1 120.25(14) . . ?
C2 C1 S1 114.65(16) . . ?
C5 C1 S1 119.50(16) . . ?
C5 C1 C2 125.7(2) . . ?
H2 C2 C1 116.78(13) . . ?
C3 C2 C1 126.4(2) . . ?
C3 C2 H2 116.78(12) . . ?
C4 C3 C2 120.6(2) . . ?
C11 C3 C2 116.93(19) . . ?
C11 C3 C4 122.37(19) . . ?
C3 C4 O1 118.69(19) . . ?
C17 C4 O1 110.86(17) . . ?
C17 C4 C3 130.29(19) . . ?
C6 C5 C1 122.47(19) . . ?
C10 C5 C1 118.9(2) . . ?
C10 C5 C6 118.6(2) . . ?
H6 C6 C5 119.85(13) . . ?
C7 C6 C5 120.3(2) . . ?
C7 C6 H6 119.85(14) . . ?
H7 C7 C6 119.68(14) . . ?
C8 C7 C6 120.6(2) . . ?
C8 C7 H7 119.68(14) . . ?
H8 C8 C7 120.19(14) . . ?
C9 C8 C7 119.6(2) . . ?
C9 C8 H8 120.19(14) . . ?
H9 C9 C8 119.96(14) . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 119.96(14) . . ?
C9 C10 C5 120.7(2) . . ?
H10 C10 C5 119.65(13) . . ?
H10 C10 C9 119.65(14) . . ?
C12 C11 C3 120.1(2) . . ?
C16 C11 C3 120.5(2) . . ?
C16 C11 C12 119.3(2) . . ?
H12 C12 C11 119.76(13) . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.76(15) . . ?
H13 C13 C12 120.04(15) . . ?
C14 C13 C12 119.9(2) . . ?
C14 C13 H13 120.04(14) . . ?
H14 C14 C13 120.06(14) . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 H14 120.06(14) . . ?
H15 C15 C14 119.79(14) . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.79(15) . . ?
C15 C16 C11 120.0(2) . . ?
H16 C16 C11 120.01(13) . . ?
H16 C16 C15 120.01(15) . . ?
C18 C17 C4 119.90(19) . . ?
C22 C17 C4 121.0(2) . . ?
C22 C17 C18 119.1(2) . . ?
H18 C18 C17 119.80(12) . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18 119.80(13) . . ?
H19 C19 C18 119.89(13) . . ?
C20 C19 C18 120.2(2) . . ?
C20 C19 H19 119.89(13) . . ?
H20 C20 C19 120.21(13) . . ?
C21 C20 C19 119.6(2) . . ?
C21 C20 H20 120.21(13) . . ?
H21 C21 C20 119.62(13) . . ?
C22 C21 C20 120.8(2) . . ?
C22 C21 H21 119.62(13) . . ?
C21 C22 C17 119.9(2) . . ?
H22 C22 C17 120.04(13) . . ?
H22 C22 C21 120.04(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_CC_KAA4R_0m
_database_code_depnum_ccdc_archive 'CCDC 1913655'
loop_
_audit_author_name
_audit_author_address
'Craig Rice'
;University of Huddersfield
United Kingdom
;
_audit_update_record             
;
2019-05-02 deposited with the CCDC.	2019-10-31 downloaded from the CCDC.
;
_audit_creation_date             2017-02-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_chemical_formula_moiety         'C24 H23 N O3 S'
_chemical_formula_sum            'C24 H23 N O3 S'
_chemical_formula_weight         405.52
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   9.6018(7)
_cell_length_b                   12.4113(10)
_cell_length_c                   16.8115(14)
_cell_angle_alpha                90
_cell_angle_beta                 96.978(3)
_cell_angle_gamma                90
_cell_volume                     1988.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9037
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      2.44
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3544
_exptl_crystal_description       block
_exptl_crystal_F_000             856.8844
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            27462
_diffrn_reflns_theta_full        30.5141
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         2.33
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.9952
_diffrn_measured_fraction_theta_max 0.9952
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -13
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              -10
_reflns_number_gt                5031
_reflns_number_total             6044
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.4326
_refine_diff_density_min         -0.5538
_refine_diff_density_rms         0.0762
_refine_ls_d_res_high            0.6999
_refine_ls_d_res_low             8.7462
_refine_ls_goodness_of_fit_ref   1.0519
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    42
_refine_ls_number_parameters     263
_refine_ls_number_reflns         6044
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.0519
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0548P)²+0.8103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1086
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C23(H23a,H23b,H23c), C24(H24a,H24b,H24c)
;
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_refinement_flags_posn
S1 S 1.14140(3) 0.36923(2) 0.046669(17) 0.01435(8) Uani 1.000000 .
N1 N 0.77820(11) 0.21736(8) 0.06829(6) 0.0163(2) Uani 1.000000 .
O1 O 1.08502(9) 0.43516(7) 0.11789(5) 0.01633(17) Uani 1.000000 .
O2 O 1.17451(10) 0.45104(7) -0.00761(5) 0.02068(19) Uani 1.000000 .
O3 O 1.24785(10) 0.29512(7) 0.07856(6) 0.02125(19) Uani 1.000000 .
C1 C 0.98459(12) 0.30018(9) 0.01037(7) 0.0134(2) Uani 1.000000 .
H1 H 0.91200(12) 0.35617(9) -0.00634(7) 0.0161(2) Uiso 1.000000 R
C2 C 0.93048(12) 0.23318(9) 0.07992(6) 0.0133(2) Uani 1.000000 .
H2 H 0.97378(12) 0.16003(9) 0.07849(6) 0.0160(2) Uiso 1.000000 R
C3 C 0.97274(12) 0.27775(9) 0.16422(7) 0.0133(2) Uani 1.000000 .
C4 C 1.03573(12) 0.37295(9) 0.17958(7) 0.0140(2) Uani 1.000000 .
C5 C 1.00769(12) 0.23687(9) -0.06424(7) 0.0145(2) Uani 1.000000 .
C6 C 1.07693(13) 0.13767(10) -0.05995(7) 0.0187(2) Uani 1.000000 .
H6 H 1.11315(13) 0.10880(10) -0.00930(7) 0.0225(3) Uiso 1.000000 R
C7 C 1.09299(14) 0.08101(10) -0.12972(8) 0.0219(3) Uani 1.000000 .
H7 H 1.13960(14) 0.01335(10) -0.12646(8) 0.0263(3) Uiso 1.000000 R
C8 C 1.04128(15) 0.12284(11) -0.20397(8) 0.0237(3) Uani 1.000000 .
H8 H 1.05140(15) 0.08347(11) -0.25139(8) 0.0284(3) Uiso 1.000000 R
C9 C 0.97480(15) 0.22219(12) -0.20889(7) 0.0233(3) Uani 1.000000 .
H9 H 0.94046(15) 0.25139(12) -0.25974(7) 0.0280(3) Uiso 1.000000 R
C10 C 0.95837(13) 0.27914(10) -0.13932(7) 0.0181(2) Uani 1.000000 .
H10 H 0.91320(13) 0.34737(10) -0.14298(7) 0.0217(3) Uiso 1.000000 R
C11 C 0.95083(12) 0.20715(9) 0.23379(7) 0.0138(2) Uani 1.000000 .
C12 C 0.81967(13) 0.17046(10) 0.25024(7) 0.0183(2) Uani 1.000000 .
H12 H 0.73820(13) 0.18655(10) 0.21427(7) 0.0220(3) Uiso 1.000000 R
C13 C 0.80780(15) 0.11035(11) 0.31919(8) 0.0225(3) Uani 1.000000 .
H13 H 0.71796(15) 0.08732(11) 0.33057(8) 0.0270(3) Uiso 1.000000 R
C14 C 0.92629(15) 0.08390(11) 0.37134(7) 0.0226(3) Uani 1.000000 .
H14 H 0.91757(15) 0.04363(11) 0.41854(7) 0.0271(3) Uiso 1.000000 R
C15 C 1.05750(14) 0.11665(10) 0.35409(7) 0.0207(2) Uani 1.000000 .
H15 H 1.13917(14) 0.09685(10) 0.38867(7) 0.0248(3) Uiso 1.000000 R
C16 C 1.06961(13) 0.17846(10) 0.28622(7) 0.0170(2) Uani 1.000000 .
H16 H 1.15972(13) 0.20151(10) 0.27531(7) 0.0204(3) Uiso 1.000000 R
C17 C 1.05955(13) 0.43328(9) 0.25571(7) 0.0144(2) Uani 1.000000 .
C18 C 1.18392(13) 0.49083(10) 0.27539(7) 0.0182(2) Uani 1.000000 .
H18 H 1.25697(13) 0.48577(10) 0.24219(7) 0.0218(3) Uiso 1.000000 R
C19 C 1.20123(14) 0.55543(10) 0.34330(8) 0.0213(3) Uani 1.000000 .
H19 H 1.28615(14) 0.59429(10) 0.35645(8) 0.0256(3) Uiso 1.000000 R
C20 C 1.09498(15) 0.56345(10) 0.39206(7) 0.0211(3) Uani 1.000000 .
H20 H 1.10641(15) 0.60859(10) 0.43802(7) 0.0254(3) Uiso 1.000000 R
C21 C 0.97202(14) 0.50526(11) 0.37337(8) 0.0235(3) Uani 1.000000 .
H21 H 0.89983(14) 0.50971(11) 0.40720(8) 0.0281(3) Uiso 1.000000 R
C22 C 0.95381(13) 0.44055(10) 0.30554(8) 0.0201(2) Uani 1.000000 .
H22 H 0.86917(13) 0.40114(10) 0.29302(8) 0.0241(3) Uiso 1.000000 R
C23 C 0.72735(14) 0.15848(11) -0.00477(7) 0.0219(3) Uani 1.000000 .
H23a H 0.7378(11) 0.2035(3) -0.05157(8) 0.0329(4) Uiso 1.000000 GR
H23b H 0.7820(8) 0.0922(4) -0.0075(3) 0.0329(4) Uiso 1.000000 GR
H23c H 0.6282(3) 0.1403(8) -0.0042(3) 0.0329(4) Uiso 1.000000 GR
C24 C 0.69509(14) 0.31446(11) 0.07681(8) 0.0217(3) Uani 1.000000 .
H24a H 0.7278(7) 0.3498(5) 0.1278(3) 0.0325(4) Uiso 1.000000 GR
H24b H 0.7057(9) 0.3639(4) 0.0325(4) 0.0325(4) Uiso 1.000000 GR
H24c H 0.5960(2) 0.29481(14) 0.0758(6) 0.0325(4) Uiso 1.000000 GR


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 O1 1.5980(9) . ?
S1 O2 1.4267(9) . ?
S1 O3 1.4300(9) . ?
S1 C1 1.7750(12) . ?
N1 C2 1.4647(16) . ?
N1 C23 1.4612(15) . ?
N1 C24 1.4621(16) . ?
O1 C4 1.4194(13) . ?
C1 C2 1.5736(15) . ?
C1 C5 1.5190(15) . ?
C2 C3 1.5295(15) . ?
C3 C4 1.3381(16) . ?
C3 C11 1.4967(15) . ?
C4 C17 1.4765(15) . ?
C5 C6 1.3970(16) . ?
C5 C10 1.3956(16) . ?
C6 C7 1.3921(17) . ?
C7 C8 1.3869(19) . ?
C8 C9 1.386(2) . ?
C9 C10 1.3918(17) . ?
C11 C12 1.3981(17) . ?
C11 C16 1.4001(16) . ?
C12 C13 1.3947(17) . ?
C13 C14 1.389(2) . ?
C14 C15 1.3875(19) . ?
C15 C16 1.3915(16) . ?
C17 C18 1.3964(17) . ?
C17 C22 1.3954(17) . ?
C18 C19 1.3885(17) . ?
C19 C20 1.3877(19) . ?
C20 C21 1.3871(19) . ?
C21 C22 1.3884(17) . ?

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 103.70(5) . . ?
O3 S1 O1 109.89(5) . . ?
O3 S1 O2 119.53(6) . . ?
C1 S1 O1 98.88(5) . . ?
C1 S1 O2 111.68(5) . . ?
C1 S1 O3 110.87(5) . . ?
C23 N1 C2 113.92(10) . . ?
C24 N1 C2 115.10(9) . . ?
C24 N1 C23 111.35(10) . . ?
C4 O1 S1 116.25(7) . . ?
C2 C1 S1 110.03(7) . . ?
C5 C1 S1 109.32(8) . . ?
C5 C1 C2 115.76(9) . . ?
C1 C2 N1 112.71(9) . . ?
C3 C2 N1 108.68(9) . . ?
C3 C2 C1 115.02(9) . . ?
C4 C3 C2 124.12(10) . . ?
C11 C3 C2 117.76(9) . . ?
C11 C3 C4 117.99(10) . . ?
C3 C4 O1 121.49(10) . . ?
C17 C4 O1 109.10(9) . . ?
C17 C4 C3 129.33(10) . . ?
C6 C5 C1 121.99(10) . . ?
C10 C5 C1 119.00(10) . . ?
C10 C5 C6 119.01(11) . . ?
C7 C6 C5 120.17(11) . . ?
C8 C7 C6 120.33(12) . . ?
C9 C8 C7 119.90(12) . . ?
C10 C9 C8 120.00(12) . . ?
C9 C10 C5 120.57(12) . . ?
C12 C11 C3 124.11(11) . . ?
C16 C11 C3 117.38(10) . . ?
C16 C11 C12 118.50(11) . . ?
C13 C12 C11 120.34(12) . . ?
C14 C13 C12 120.51(12) . . ?
C15 C14 C13 119.59(11) . . ?
C16 C15 C14 120.09(12) . . ?
C15 C16 C11 120.90(11) . . ?
C18 C17 C4 120.18(10) . . ?
C22 C17 C4 120.39(11) . . ?
C22 C17 C18 119.23(11) . . ?
C19 C18 C17 120.24(11) . . ?
C20 C19 C18 120.26(12) . . ?
C21 C20 C19 119.71(11) . . ?
C22 C21 C20 120.39(12) . . ?
C21 C22 C17 120.15(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
