# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_igl8919a
_database_code_depnum_ccdc_archive 'CCDC 2050078'
loop_
_audit_author_name
_audit_author_address
'Javier Iglesias-Siguenza'
;University of Seville
Spain
;
_audit_update_record             
;
2020-12-14 deposited with the CCDC.	2021-04-30 downloaded from the CCDC.
;

_vrf_PLAT029_igl8919a            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low . 0.936 
RESPONSE: Crystals employed to collect diffraction images diffracted very
weak and they were decaying during the experiment. However, collected
data had sufficient quality and completeness has been optimal to elucidate
structure and absolute configuration of the compound. 
;


_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H21 N3 O3'
_chemical_formula_weight         387.43

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   12.9810(6)
_cell_length_b                   5.8251(2)
_cell_length_c                   13.4539(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.041(2)
_cell_angle_gamma                90
_cell_volume                     1015.89(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9938
_cell_measurement_theta_min      4.61
_cell_measurement_theta_max      65.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.692
_shelx_estimated_absorpt_T_min   0.846
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6108
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_process_details   
; 
 SADABS, Bruker (2006). APEX 2. Version 2.1. Bruker Analytical 
 X-ray Solutions, Madison, Wisconsin, USA. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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            11799
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.289
_diffrn_reflns_theta_max         64.972
_diffrn_reflns_theta_full        64.972
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measured_fraction_theta_full 0.936
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_Laue_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_point_group_measured_fraction_full 0.915
_reflns_number_total             3173
_reflns_number_gt                3156
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_max     0.888
_reflns_Friedel_fraction_full    0.889

_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-2018/1 (Sheldrick, 2018)'
_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)+(0.1000P)²+0.2766P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1358 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.04(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3173
_refine_ls_number_parameters     262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0259
_refine_ls_wR_factor_ref         0.0786
_refine_ls_wR_factor_gt          0.0784
_refine_ls_goodness_of_fit_ref   0.647
_refine_ls_restrained_S_all      0.647
_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
O1 O 0.27638(8) 1.2596(2) 0.86054(8) 0.0204(3) Uani 1 1 d . . . . .
O2 O 0.52322(13) 1.6615(3) 0.62210(11) 0.0389(4) Uani 1 1 d . . . . .
O3 O 0.64155(14) 1.4213(4) 0.5897(2) 0.0717(7) Uani 1 1 d . . . . .
N1 N 0.11983(10) 0.6140(3) 0.72219(10) 0.0167(3) Uani 1 1 d . . . . .
N2 N 0.19390(10) 0.7731(3) 0.73213(9) 0.0161(3) Uani 1 1 d . . . . .
N3 N 0.55434(13) 1.4661(3) 0.61077(12) 0.0301(4) Uani 1 1 d . . . . .
C1 C 0.12646(12) 0.4593(3) 0.64176(12) 0.0165(4) Uani 1 1 d . . . . .
C2 C 0.19787(13) 0.4961(3) 0.56875(13) 0.0202(4) Uani 1 1 d . . . . .
H2A H 0.240177 0.629317 0.571206 0.024 Uiso 1 1 calc R U . . .
C3 C 0.20635(13) 0.3372(3) 0.49302(13) 0.0228(4) Uani 1 1 d . . . . .
H3 H 0.255270 0.361500 0.444010 0.027 Uiso 1 1 calc R U . . .
C4 C 0.14433(13) 0.1430(3) 0.48775(12) 0.0218(4) Uani 1 1 d . . . . .
H4 H 0.151946 0.033010 0.436525 0.026 Uiso 1 1 calc R U . . .
C5 C 0.07095(13) 0.1108(3) 0.55814(12) 0.0206(4) Uani 1 1 d . . . . .
H5 H 0.026633 -0.018971 0.553615 0.025 Uiso 1 1 calc R U . . .
C6 C 0.06218(12) 0.2676(3) 0.63502(12) 0.0187(4) Uani 1 1 d . . . . .
H6 H 0.012236 0.244172 0.683139 0.022 Uiso 1 1 calc R U . . .
C7 C 0.03381(12) 0.6103(3) 0.78590(12) 0.0181(4) Uani 1 1 d . . . . .
C8 C -0.05362(13) 0.7364(4) 0.75831(12) 0.0238(4) Uani 1 1 d . . . . .
H8 H -0.056470 0.823458 0.698509 0.029 Uiso 1 1 calc R U . . .
C9 C -0.13719(14) 0.7345(4) 0.81896(15) 0.0310(5) Uani 1 1 d . . . . .
H9 H -0.197461 0.820212 0.800519 0.037 Uiso 1 1 calc R U . . .
C10 C -0.13261(14) 0.6079(4) 0.90604(14) 0.0281(4) Uani 1 1 d . . . . .
H10 H -0.189767 0.606111 0.947305 0.034 Uiso 1 1 calc R U . . .
C11 C -0.04424(14) 0.4832(3) 0.93307(14) 0.0273(4) Uani 1 1 d . . . . .
H11 H -0.041293 0.396482 0.992949 0.033 Uiso 1 1 calc R U . . .
C12 C 0.03998(14) 0.4843(3) 0.87323(13) 0.0222(4) Uani 1 1 d . . . . .
H12 H 0.100612 0.400151 0.892000 0.027 Uiso 1 1 calc R U . . .
C13 C 0.19294(12) 0.9282(3) 0.80002(12) 0.0169(4) Uani 1 1 d . . . . .
H13 H 0.141990 0.929277 0.848159 0.020 Uiso 1 1 calc R U . . .
C14 C 0.27394(12) 1.1034(3) 0.79985(11) 0.0160(3) Uani 1 1 d . . . . .
C15 C 0.35049(12) 1.0853(3) 0.71860(12) 0.0184(4) Uani 1 1 d . . . . .
H15A H 0.312029 1.082118 0.653067 0.022 Uiso 1 1 calc R U . . .
H15B H 0.388503 0.938547 0.726509 0.022 Uiso 1 1 calc R U . . .
C16 C 0.42808(12) 1.2826(3) 0.71971(12) 0.0172(4) Uani 1 1 d . . . . .
H16 H 0.389248 1.430508 0.722518 0.021 Uiso 1 1 calc R U . . .
C17 C 0.48042(14) 1.2720(3) 0.62033(12) 0.0218(4) Uani 1 1 d . . . . .
H17A H 0.517789 1.124604 0.615612 0.026 Uiso 1 1 calc R U . . .
H17B H 0.427225 1.278482 0.564877 0.026 Uiso 1 1 calc R U . . .
C18 C 0.50673(12) 1.2746(3) 0.80788(11) 0.0172(4) Uani 1 1 d . . . . .
C19 C 0.51554(13) 1.4582(3) 0.87358(12) 0.0198(4) Uani 1 1 d . . . . .
H19 H 0.473471 1.589975 0.862122 0.024 Uiso 1 1 calc R U . . .
C20 C 0.58483(13) 1.4522(3) 0.95573(13) 0.0231(4) Uani 1 1 d . . . . .
H20 H 0.590000 1.579185 1.000019 0.028 Uiso 1 1 calc R U . . .
C21 C 0.64648(13) 1.2605(4) 0.97302(13) 0.0249(4) Uani 1 1 d . . . . .
H21 H 0.693960 1.255387 1.029194 0.030 Uiso 1 1 calc R U . . .
C22 C 0.63841(13) 1.0755(4) 0.90757(14) 0.0248(4) Uani 1 1 d . . . . .
H22 H 0.680162 0.943318 0.919418 0.030 Uiso 1 1 calc R U . . .
C23 C 0.56965(13) 1.0833(3) 0.82513(13) 0.0207(4) Uani 1 1 d . . . . .
H23 H 0.565422 0.957517 0.780150 0.025 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
O1 C14 1.222(2) . ?
O2 N3 1.220(2) . ?
O3 N3 1.210(3) . ?
N1 N2 1.337(2) . ?
N1 C1 1.414(2) . ?
N1 C7 1.443(2) . ?
N2 C13 1.285(2) . ?
N3 C17 1.493(2) . ?
C1 C6 1.394(3) . ?
C1 C2 1.402(2) . ?
C2 C3 1.385(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.384(3) . ?
C7 C8 1.386(3) . ?
C8 C9 1.392(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.465(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.519(2) . ?
C15 C16 1.528(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C18 1.524(2) . ?
C16 C17 1.533(2) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.388(3) . ?
C18 C23 1.394(3) . ?
C19 C20 1.388(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.392(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(3) . ?
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
N2 N1 C1 116.46(12) . . ?
N2 N1 C7 121.73(13) . . ?
C1 N1 C7 121.68(13) . . ?
C13 N2 N1 121.63(13) . . ?
O3 N3 O2 123.42(19) . . ?
O3 N3 C17 118.05(19) . . ?
O2 N3 C17 118.50(16) . . ?
C6 C1 C2 119.52(16) . . ?
C6 C1 N1 119.97(14) . . ?
C2 C1 N1 120.51(15) . . ?
C3 C2 C1 119.61(16) . . ?
C3 C2 H2A 120.2 . . ?
C1 C2 H2A 120.2 . . ?
C2 C3 C4 120.91(15) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 119.42(16) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.29(17) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.17(15) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C12 C7 C8 121.20(15) . . ?
C12 C7 N1 120.02(15) . . ?
C8 C7 N1 118.77(14) . . ?
C7 C8 C9 119.43(17) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 120.08(18) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 119.87(16) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 120.61(17) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C7 C12 C11 118.80(16) . . ?
C7 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
N2 C13 C14 117.04(13) . . ?
N2 C13 H13 121.5 . . ?
C14 C13 H13 121.5 . . ?
O1 C14 C13 120.71(14) . . ?
O1 C14 C15 122.54(15) . . ?
C13 C14 C15 116.70(14) . . ?
C14 C15 C16 113.37(14) . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C18 C16 C15 113.49(14) . . ?
C18 C16 C17 111.60(13) . . ?
C15 C16 C17 106.49(14) . . ?
C18 C16 H16 108.4 . . ?
C15 C16 H16 108.4 . . ?
C17 C16 H16 108.4 . . ?
N3 C17 C16 111.19(15) . . ?
N3 C17 H17A 109.4 . . ?
C16 C17 H17A 109.4 . . ?
N3 C17 H17B 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C19 C18 C23 118.83(15) . . ?
C19 C18 C16 120.06(16) . . ?
C23 C18 C16 121.10(16) . . ?
C20 C19 C18 121.04(17) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C21 C20 C19 119.85(17) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 119.61(16) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C23 C22 C21 120.26(17) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C18 120.40(17) . . ?
C22 C23 H23 119.8 . . ?
C18 C23 H23 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C13 176.99(15) . . . . ?
C7 N1 N2 C13 1.2(2) . . . . ?
N2 N1 C1 C6 170.09(14) . . . . ?
C7 N1 C1 C6 -14.1(2) . . . . ?
N2 N1 C1 C2 -9.5(2) . . . . ?
C7 N1 C1 C2 166.34(15) . . . . ?
C6 C1 C2 C3 -2.4(2) . . . . ?
N1 C1 C2 C3 177.13(15) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C3 C4 C5 1.6(2) . . . . ?
C3 C4 C5 C6 -2.2(2) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
C2 C1 C6 C5 1.9(2) . . . . ?
N1 C1 C6 C5 -177.69(15) . . . . ?
N2 N1 C7 C12 -90.8(2) . . . . ?
C1 N1 C7 C12 93.6(2) . . . . ?
N2 N1 C7 C8 88.5(2) . . . . ?
C1 N1 C7 C8 -87.1(2) . . . . ?
C12 C7 C8 C9 -0.7(3) . . . . ?
N1 C7 C8 C9 179.98(17) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C8 C7 C12 C11 0.9(3) . . . . ?
N1 C7 C12 C11 -179.79(16) . . . . ?
C10 C11 C12 C7 -0.5(3) . . . . ?
N1 N2 C13 C14 -175.90(14) . . . . ?
N2 C13 C14 O1 178.12(15) . . . . ?
N2 C13 C14 C15 0.6(2) . . . . ?
O1 C14 C15 C16 -1.1(2) . . . . ?
C13 C14 C15 C16 176.35(14) . . . . ?
C14 C15 C16 C18 70.62(19) . . . . ?
C14 C15 C16 C17 -166.21(14) . . . . ?
O3 N3 C17 C16 128.0(2) . . . . ?
O2 N3 C17 C16 -53.8(2) . . . . ?
C18 C16 C17 N3 -58.7(2) . . . . ?
C15 C16 C17 N3 176.90(14) . . . . ?
C15 C16 C18 C19 -121.78(17) . . . . ?
C17 C16 C18 C19 117.90(17) . . . . ?
C15 C16 C18 C23 57.20(19) . . . . ?
C17 C16 C18 C23 -63.1(2) . . . . ?
C23 C18 C19 C20 -0.6(2) . . . . ?
C16 C18 C19 C20 178.39(16) . . . . ?
C18 C19 C20 C21 0.0(2) . . . . ?
C19 C20 C21 C22 0.1(3) . . . . ?
C20 C21 C22 C23 0.5(3) . . . . ?
C21 C22 C23 C18 -1.1(3) . . . . ?
C19 C18 C23 C22 1.2(2) . . . . ?
C16 C18 C23 C22 -177.83(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C12 H12 O1 0.95 2.48 3.349(2) 151.8 1_545 yes

_refine_diff_density_max         0.145
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.033



####################################################################### 
# 
# 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_igl9919a
_database_code_depnum_ccdc_archive 'CCDC 2050079'
loop_
_audit_author_name
_audit_author_address
'Javier Iglesias-Siguenza'
;University of Seville
Spain
;
_audit_update_record             
;
2020-12-14 deposited with the CCDC.	2021-04-30 downloaded from the CCDC.
;

_vrf_PLAT230_igl9919a            
;
PROBLEM: Hirshfeld Test Diff for C2 -- C3 .. 11.5 s.u.  
      
RESPONSE: The atoms have not ideally shaped, however, this does not indicate
an incorrect atom-type assignment.This difference could be caused by
vibration of the aromatic group.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H40 N4 O3 S'
_chemical_formula_weight         512.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   22.1515(7)
_cell_length_b                   19.9640(7)
_cell_length_c                   12.7910(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.854(2)
_cell_angle_gamma                90
_cell_volume                     5643.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      6.40
_cell_measurement_theta_max      64.81

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_F_000             2208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.292
_shelx_estimated_absorpt_T_min   0.690
_shelx_estimated_absorpt_T_max   0.820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6086
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   
; 
 SADABS, Bruker (2006). APEX 2. Version 2.1. Bruker Analytical 
 X-ray Solutions, Madison, Wisconsin, USA. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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            14189
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         6.404
_diffrn_reflns_theta_max         65.394
_diffrn_reflns_theta_full        65.394
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             4698
_reflns_number_gt                4485
_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-2018/1 (Sheldrick, 2018)'
_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)+(0.1000P)²+0.1211P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4698
_refine_ls_number_parameters     349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1502
_refine_ls_wR_factor_gt          0.1471
_refine_ls_goodness_of_fit_ref   1.331
_refine_ls_restrained_S_all      1.331
_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 0.12111(2) 0.20828(2) 0.74092(2) 0.02745(17) Uani 1 1 d . . . . .
O1 O 0.07700(4) 0.21908(5) 0.42355(8) 0.0304(3) Uani 1 1 d . . . . .
N1 N 0.01468(5) 0.15023(6) 0.50354(9) 0.0276(3) Uani 1 1 d . . . . .
N2 N 0.08687(5) 0.30189(6) 0.59931(9) 0.0258(3) Uani 1 1 d . . . . .
N3 N 0.18056(5) 0.31581(6) 0.67610(9) 0.0241(3) Uani 1 1 d . . . . .
N4 N 0.29862(6) 0.29811(6) 0.59996(9) 0.0237(3) Uani 1 1 d . . . . .
C1 C 0.09271(10) 0.02265(8) 0.34038(17) 0.0541(5) Uani 1 1 d . . . . .
H1 H 0.064668 0.018996 0.283211 0.065 Uiso 1 1 calc R U . . .
C2 C 0.14601(13) -0.01200(10) 0.3410(3) 0.0740(8) Uani 1 1 d . . . . .
H2 H 0.154008 -0.039144 0.284459 0.089 Uiso 1 1 calc R U . . .
C3 C 0.18794(11) -0.00669(10) 0.4254(3) 0.0806(10) Uani 1 1 d . . . . .
H3 H 0.224240 -0.030096 0.425403 0.097 Uiso 1 1 calc R U . . .
C4 C 0.17614(8) 0.03359(10) 0.5108(2) 0.0617(6) Uani 1 1 d . . . . .
H4 H 0.204431 0.037177 0.567658 0.074 Uiso 1 1 calc R U . . .
C5 C 0.12152(7) 0.06846(8) 0.51025(15) 0.0425(4) Uani 1 1 d . . . . .
H5 H 0.113033 0.095008 0.567187 0.051 Uiso 1 1 calc R U . . .
C6 C 0.08003(7) 0.06348(7) 0.42488(13) 0.0376(4) Uani 1 1 d . . . . .
C7 C 0.02096(7) 0.10161(8) 0.41928(12) 0.0363(4) Uani 1 1 d . . . . .
H7A H 0.016712 0.125053 0.352770 0.044 Uiso 1 1 calc R U . . .
H7B H -0.011961 0.069636 0.420330 0.044 Uiso 1 1 calc R U . . .
C8 C -0.01656(6) 0.12700(8) 0.59364(11) 0.0321(3) Uani 1 1 d . . . . .
H8A H -0.013009 0.160164 0.648053 0.048 Uiso 1 1 calc R U . . .
H8B H 0.001316 0.085806 0.619071 0.048 Uiso 1 1 calc R U . . .
H8C H -0.058524 0.119746 0.573067 0.048 Uiso 1 1 calc R U . . .
C9 C 0.04318(6) 0.20941(7) 0.49515(11) 0.0254(3) Uani 1 1 d . . . . .
C10 C 0.03095(6) 0.26722(7) 0.57003(10) 0.0238(3) Uani 1 1 d . . . . .
H10 H 0.014748 0.248700 0.633338 0.029 Uiso 1 1 calc R U . . .
C11 C -0.01639(6) 0.31750(7) 0.51784(10) 0.0262(3) Uani 1 1 d . . . . .
C12 C -0.03406(6) 0.36674(8) 0.60236(12) 0.0332(3) Uani 1 1 d . . . . .
H12A H -0.063483 0.397814 0.572555 0.050 Uiso 1 1 calc R U . . .
H12B H 0.001181 0.390770 0.629237 0.050 Uiso 1 1 calc R U . . .
H12C H -0.050952 0.342508 0.658280 0.050 Uiso 1 1 calc R U . . .
C13 C -0.07259(6) 0.27853(8) 0.47777(12) 0.0318(3) Uani 1 1 d . . . . .
H13A H -0.103284 0.309314 0.451580 0.048 Uiso 1 1 calc R U . . .
H13B H -0.087442 0.252831 0.534048 0.048 Uiso 1 1 calc R U . . .
H13C H -0.062364 0.248954 0.422482 0.048 Uiso 1 1 calc R U . . .
C14 C 0.00852(7) 0.35594(8) 0.42575(12) 0.0370(4) Uani 1 1 d . . . . .
H14A H 0.023278 0.324662 0.376498 0.055 Uiso 1 1 calc R U . . .
H14B H 0.040965 0.384634 0.451534 0.055 Uiso 1 1 calc R U . . .
H14C H -0.023159 0.382521 0.391782 0.055 Uiso 1 1 calc R U . . .
C15 C 0.13039(6) 0.27831(6) 0.66929(10) 0.0229(3) Uani 1 1 d . . . . .
C16 C 0.23263(6) 0.30506(6) 0.74931(10) 0.0225(3) Uani 1 1 d . . . . .
H16 H 0.237835 0.256767 0.760336 0.027 Uiso 1 1 calc R U . . .
C17 C 0.28920(6) 0.33260(6) 0.70182(10) 0.0217(3) Uani 1 1 d . . . . .
H17 H 0.283418 0.380569 0.688355 0.026 Uiso 1 1 calc R U . . .
C18 C 0.34494(6) 0.32336(7) 0.77658(10) 0.0249(3) Uani 1 1 d . . . . .
H18A H 0.379958 0.342274 0.745755 0.030 Uiso 1 1 calc R U . . .
H18B H 0.352301 0.275948 0.788095 0.030 Uiso 1 1 calc R U . . .
C19 C 0.33607(6) 0.35771(7) 0.88130(11) 0.0286(3) Uani 1 1 d . . . . .
H19A H 0.371679 0.350884 0.928483 0.034 Uiso 1 1 calc R U . . .
H19B H 0.330925 0.405499 0.870322 0.034 Uiso 1 1 calc R U . . .
C20 C 0.28071(6) 0.32934(8) 0.93031(11) 0.0305(3) Uani 1 1 d . . . . .
H20A H 0.274961 0.352219 0.995805 0.037 Uiso 1 1 calc R U . . .
H20B H 0.286868 0.282112 0.945325 0.037 Uiso 1 1 calc R U . . .
C21 C 0.22446(6) 0.33837(7) 0.85547(10) 0.0280(3) Uani 1 1 d . . . . .
H21A H 0.216650 0.385790 0.845009 0.034 Uiso 1 1 calc R U . . .
H21B H 0.189749 0.318876 0.886453 0.034 Uiso 1 1 calc R U . . .
O2 O 0.27201(4) 0.16444(5) 0.57762(8) 0.0302(3) Uani 1 1 d . . . . .
O3 O 0.33255(5) 0.09668(5) 0.49289(7) 0.0340(3) Uani 1 1 d . . . . .
C22 C 0.31050(6) 0.11754(6) 0.57448(10) 0.0259(3) Uani 1 1 d . . . . .
C23 C 0.33136(6) 0.08437(7) 0.67648(10) 0.0265(3) Uani 1 1 d . . . . .
C24 C 0.37107(8) 0.03062(8) 0.67630(12) 0.0383(4) Uani 1 1 d . . . . .
H24 H 0.384362 0.015230 0.613175 0.046 Uiso 1 1 calc R U . . .
C25 C 0.39113(9) -0.00038(9) 0.76917(13) 0.0448(4) Uani 1 1 d . . . . .
H25 H 0.417137 -0.036900 0.767954 0.054 Uiso 1 1 calc R U . . .
C26 C 0.37269(8) 0.02269(8) 0.86288(12) 0.0401(4) Uani 1 1 d . . . . .
H26 H 0.386668 0.002335 0.925286 0.048 Uiso 1 1 calc R U . . .
C27 C 0.33312(7) 0.07648(8) 0.86422(11) 0.0372(4) Uani 1 1 d . . . . .
H27 H 0.320667 0.092236 0.927720 0.045 Uiso 1 1 calc R U . . .
C28 C 0.31211(6) 0.10680(7) 0.77169(11) 0.0309(3) Uani 1 1 d . . . . .
H28 H 0.285011 0.142314 0.773076 0.037 Uiso 1 1 calc R U . . .
H4NO H 0.2916(7) 0.2533(10) 0.6035(13) 0.033(4) Uiso 1 1 d . . . . .
H4NA H 0.3368(10) 0.3018(9) 0.5826(15) 0.038(5) Uiso 1 1 d . . . . .
H4NB H 0.2745(9) 0.3139(10) 0.5440(16) 0.041(5) Uiso 1 1 d . . . . .
H2N H 0.0983(8) 0.3355(9) 0.5571(14) 0.031(4) Uiso 1 1 d . . . . .
H3N H 0.1800(8) 0.3479(9) 0.6332(15) 0.033(4) Uiso 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C15 1.6918(13) . ?
O1 C9 1.2367(18) . ?
N1 C9 1.3472(18) . ?
N1 C8 1.4591(18) . ?
N1 C7 1.4641(18) . ?
N2 C15 1.3550(18) . ?
N2 C10 1.4461(17) . ?
N3 C15 1.3378(18) . ?
N3 C16 1.4521(17) . ?
N4 C17 1.5006(17) . ?
C1 C2 1.368(3) . ?
C1 C6 1.397(2) . ?
C2 C3 1.381(4) . ?
C3 C4 1.395(4) . ?
C4 C5 1.396(2) . ?
C5 C6 1.383(3) . ?
C6 C7 1.511(2) . ?
C9 C10 1.5355(18) . ?
C10 C11 1.5681(18) . ?
C11 C13 1.5269(19) . ?
C11 C12 1.5314(19) . ?
C11 C14 1.539(2) . ?
C16 C17 1.5309(18) . ?
C16 C21 1.5337(18) . ?
C17 C18 1.5213(18) . ?
C18 C19 1.5291(18) . ?
C19 C20 1.524(2) . ?
C20 C21 1.5299(18) . ?
O2 C22 1.2686(17) . ?
O3 C22 1.2529(17) . ?
C22 C23 1.5078(19) . ?
C23 C24 1.388(2) . ?
C23 C28 1.391(2) . ?
C24 C25 1.386(2) . ?
C25 C26 1.372(2) . ?
C26 C27 1.387(2) . ?
C27 C28 1.382(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C8 126.25(12) . . ?
C9 N1 C7 117.03(12) . . ?
C8 N1 C7 116.38(12) . . ?
C15 N2 C10 124.33(12) . . ?
C15 N3 C16 125.42(11) . . ?
C2 C1 C6 120.6(2) . . ?
C1 C2 C3 120.0(2) . . ?
C2 C3 C4 120.35(19) . . ?
C3 C4 C5 119.4(2) . . ?
C6 C5 C4 119.89(19) . . ?
C5 C6 C1 119.68(16) . . ?
C5 C6 C7 121.91(14) . . ?
C1 C6 C7 118.41(17) . . ?
N1 C7 C6 115.09(13) . . ?
O1 C9 N1 120.42(12) . . ?
O1 C9 C10 119.06(12) . . ?
N1 C9 C10 120.41(12) . . ?
N2 C10 C9 109.71(10) . . ?
N2 C10 C11 109.92(11) . . ?
C9 C10 C11 110.89(10) . . ?
C13 C11 C12 108.83(11) . . ?
C13 C11 C14 108.86(12) . . ?
C12 C11 C14 109.99(12) . . ?
C13 C11 C10 108.88(11) . . ?
C12 C11 C10 107.80(10) . . ?
C14 C11 C10 112.40(11) . . ?
N3 C15 N2 113.55(12) . . ?
N3 C15 S1 123.91(10) . . ?
N2 C15 S1 122.54(10) . . ?
N3 C16 C17 109.08(10) . . ?
N3 C16 C21 111.78(10) . . ?
C17 C16 C21 110.12(11) . . ?
N4 C17 C18 109.62(10) . . ?
N4 C17 C16 110.19(10) . . ?
C18 C17 C16 111.01(10) . . ?
C17 C18 C19 110.46(11) . . ?
C20 C19 C18 110.37(11) . . ?
C19 C20 C21 110.05(11) . . ?
C20 C21 C16 111.30(11) . . ?
O3 C22 O2 124.90(12) . . ?
O3 C22 C23 117.44(12) . . ?
O2 C22 C23 117.66(12) . . ?
C24 C23 C28 118.82(13) . . ?
C24 C23 C22 119.71(12) . . ?
C28 C23 C22 121.47(12) . . ?
C25 C24 C23 120.70(14) . . ?
C26 C25 C24 120.13(16) . . ?
C25 C26 C27 119.75(14) . . ?
C28 C27 C26 120.35(13) . . ?
C27 C28 C23 120.23(14) . . ?

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.043



