# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_cmpd_4i_XYL-797
_database_code_depnum_ccdc_archive 'CCDC 2466374'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2025-06-23 deposited with the CCDC.	2026-04-24 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT902_cmpd_4i_XYL-797     
;
PROBLEM: No (Interpretable) Reflections Found in FCF ....     Please Check
RESPONSE: Structure was subjected to HAR in Olex2 using NoSpherA2 and the cif file was well-interpreted by CheckCif on-line
;
# Added during the CSD deposition process: Monday 23 June 2025 10:14 AM
# end Validation Reply Form

_audit_creation_date             2024-12-02
_audit_creation_method           
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_chemical_formula_moiety         'C16 H11 N O2 S'
_chemical_formula_sum            'C16 H11 N O2 S'
_chemical_formula_weight         281.337

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
S 0.12485 0.12449 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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 2yn'
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                   14.6282(7)
_cell_length_b                   5.1309(2)
_cell_length_c                   17.2849(9)
_cell_angle_alpha                90
_cell_angle_beta                 106.392(5)
_cell_angle_gamma                90
_cell_volume                     1244.60(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8692
_cell_measurement_theta_max      31.9460
_cell_measurement_theta_min      2.4980
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.777
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.141a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_description       stick
_exptl_crystal_F_000             584
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 0 4 0.0212
5 0 -4 0.0200
2 -5 2 0.1384
-1 0 -1 0.0480
1 0 1 0.0120
4 3 -5 0.1204
-3 -2 5 0.1188

_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.9959 0.0021 4.0240 -0.0815 0.2064 0.1398
4.9959 -0.0021 -4.0240 0.0815 -0.2064 -0.1398
2.0113 -5.0038 1.9902 0.1175 -0.4002 0.5717
-1.0032 0.0007 -0.9958 -0.0748 0.0019 -0.0031
1.0032 -0.0007 0.9958 0.0748 -0.0019 0.0031
3.9897 3.0001 -5.0189 0.0260 0.0333 -0.4822
-2.9898 -2.0001 5.0147 0.0227 0.0222 0.3549

_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.9987
_diffrn_reflns_Laue_measured_fraction_max 0.9945
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_ambient_temperature      293(2)
_diffrn_reflns_number            25386
_diffrn_reflns_point_group_measured_fraction_full 0.9987
_diffrn_reflns_point_group_measured_fraction_max 0.9945
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         31.00
_diffrn_reflns_theta_min         2.90
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.9945
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  99.00   0.50    7.00    --    9.20  46.00 159.00  238
  2  ω    -29.00  45.00   0.50    7.00    --   -9.80  46.00 159.00  148
  3  ω      0.00  26.00   0.50    7.00    --    9.20  57.00   0.00   52
  4  ω      9.00  44.00   0.50    7.00    --    9.20  38.00 -90.00   70
  5  ω     52.00  84.00   0.50    7.00    --    9.20  38.00 -90.00   64
  6  ω    -18.00   7.00   0.50    7.00    --    9.20  38.00 -90.00   50
  7  ω    -39.00  80.00   0.50    7.00    --   -9.80  57.00-150.00  238
  8  ω    -35.00  80.00   0.50    7.00    --   -9.80  38.00  90.00  230
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0424291000
_diffrn_orient_matrix_UB_12      0.0064678000
_diffrn_orient_matrix_UB_13      0.0324107000
_diffrn_orient_matrix_UB_21      -0.0236040000
_diffrn_orient_matrix_UB_22      0.0792241000
_diffrn_orient_matrix_UB_23      0.0219548000
_diffrn_orient_matrix_UB_31      -0.0141374000
_diffrn_orient_matrix_UB_32      -0.1130780000
_diffrn_orient_matrix_UB_33      0.0172424000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -21
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              -13
_reflns_number_gt                2873
_reflns_number_total             3953
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.141a 64-bit (release 04-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  
'olex2.refine 1.5-ac6-020 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.3050
_refine_diff_density_min         -0.2508
_refine_diff_density_rms         0.0529
_refine_ls_d_res_high            0.6900
_refine_ls_d_res_low             7.0168
_refine_ls_goodness_of_fit_ref   1.0569
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3953
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0258
_refine_ls_restrained_S_all      1.0569
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0045P)²+0.0961P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0420
_refine_ls_wR_factor_ref         0.0480
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
;
_olex2_refine_details            
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing 
cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA 5.0
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         R2SCAN
   BASIS SET:      def2-TZVP
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2024-12-02_16-38-49
;
_atom_sites_solution_primary     dual
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 0.900908(14) 0.52036(4) 0.540817(13) 0.03875(6) Uani 1.000000 .
O1 O 0.61015(4) -0.18179(12) 0.59126(4) 0.04827(16) Uani 1.000000 .
O2 O 0.75927(4) -0.22180(12) 0.68195(4) 0.04898(16) Uani 1.000000 .
N1 N 0.72517(4) 0.53302(12) 0.45182(4) 0.03500(15) Uani 1.000000 .
C3 C 0.72557(5) 0.33803(14) 0.50789(4) 0.03195(16) Uani 1.000000 .
C11 C 0.65873(5) 0.65337(14) 0.38872(5) 0.03409(17) Uani 1.000000 .
C5 C 0.66996(5) 0.00061(14) 0.57428(5) 0.03463(17) Uani 1.000000 .
C10 C 0.70945(6) 0.83908(15) 0.35579(5) 0.03525(17) Uani 1.000000 .
C4 C 0.64882(6) 0.18032(15) 0.51253(5) 0.03536(17) Uani 1.000000 .
H4 H 0.5800(7) 0.1917(18) 0.4710(6) 0.057(3) Uani 1.000000 .
C9 C 0.80858(6) 0.83163(15) 0.40089(5) 0.03605(17) Uani 1.000000 .
C8 C 0.83642(6) 0.12305(16) 0.62363(5) 0.03654(18) Uani 1.000000 .
H8 H 0.9072(7) 0.0955(18) 0.6643(6) 0.057(3) Uani 1.000000 .
C7 C 0.75997(5) -0.02539(15) 0.62836(5) 0.03549(17) Uani 1.000000 .
C2 C 0.81685(5) 0.30804(15) 0.56173(5) 0.03316(16) Uani 1.000000 .
C1 C 0.81401(5) 0.64587(15) 0.45885(5) 0.03461(17) Uani 1.000000 .
C12 C 0.56049(6) 0.62237(17) 0.35961(5) 0.0419(2) Uani 1.000000 .
H12 H 0.5218(7) 0.4835(19) 0.3862(7) 0.065(3) Uani 1.000000 .
C15 C 0.65942(7) 0.99551(18) 0.29158(6) 0.0448(2) Uani 1.000000 .
H15 H 0.6975(8) 1.137(2) 0.2644(6) 0.070(3) Uani 1.000000 .
C16 C 0.88654(8) 0.9949(2) 0.38681(7) 0.0464(2) Uani 1.000000 .
H16A H 0.8948(11) 0.973(3) 0.3292(9) 0.112(6) Uani 1.000000 .
H16B H 0.9536(10) 0.953(3) 0.4295(11) 0.142(6) Uani 1.000000 .
H16C H 0.8737(11) 1.192(3) 0.3912(11) 0.118(6) Uani 1.000000 .
C13 C 0.51259(7) 0.78126(18) 0.29585(6) 0.0482(2) Uani 1.000000 .
H13 H 0.4352(7) 0.768(2) 0.2723(6) 0.075(3) Uani 1.000000 .
C14 C 0.56144(7) 0.96435(18) 0.26225(6) 0.0500(2) Uani 1.000000 .
H14 H 0.5221(8) 1.083(2) 0.2105(7) 0.087(4) Uani 1.000000 .
C6 C 0.66286(7) -0.3035(2) 0.66429(6) 0.0470(2) Uani 1.000000 .
H6A H 0.6340(8) -0.236(3) 0.7115(7) 0.093(4) Uani 1.000000 .
H6B H 0.6580(9) -0.514(2) 0.6571(8) 0.096(4) Uani 1.000000 .


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 C2 1.7550(8) . ?
S1 C1 1.7383(8) . ?
O1 C5 1.3683(9) . ?
O1 C6 1.4243(11) . ?
O2 C7 1.3708(9) . ?
O2 C6 1.4195(11) . ?
N1 C3 1.3918(9) . ?
N1 C11 1.3847(9) . ?
N1 C1 1.3963(9) . ?
C3 C4 1.4045(11) . ?
C3 C2 1.4040(10) . ?
C11 C10 1.4216(11) . ?
C11 C12 1.3912(11) . ?
C5 C4 1.3779(11) . ?
C5 C7 1.3896(11) . ?
C10 C9 1.4400(11) . ?
C10 C15 1.3976(12) . ?
C4 H4 1.060(9) . ?
C9 C1 1.3688(11) . ?
C9 C16 1.4894(12) . ?
C8 H8 1.084(9) . ?
C8 C7 1.3744(11) . ?
C8 C2 1.3982(11) . ?
C12 H12 1.088(9) . ?
C12 C13 1.3909(12) . ?
C15 H15 1.097(10) . ?
C15 C14 1.3880(13) . ?
C16 H16A 1.042(14) . ?
C16 H16B 1.070(14) . ?
C16 H16C 1.034(13) . ?
C13 H13 1.091(9) . ?
C13 C14 1.4017(14) . ?
C14 H14 1.099(10) . ?
C6 H6A 1.076(12) . ?
C6 H6B 1.089(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C2 90.24(4) . . ?
C6 O1 C5 105.72(6) . . ?
C6 O2 C7 105.56(6) . . ?
C11 N1 C3 137.15(6) . . ?
C1 N1 C3 114.62(6) . . ?
C1 N1 C11 108.22(6) . . ?
C4 C3 N1 127.41(7) . . ?
C2 C3 N1 110.89(6) . . ?
C2 C3 C4 121.68(7) . . ?
C10 C11 N1 106.54(7) . . ?
C12 C11 N1 131.12(8) . . ?
C12 C11 C10 122.31(7) . . ?
C4 C5 O1 127.34(7) . . ?
C7 C5 O1 109.39(7) . . ?
C7 C5 C4 123.25(7) . . ?
C9 C10 C11 108.97(7) . . ?
C15 C10 C11 119.17(8) . . ?
C15 C10 C9 131.82(8) . . ?
C5 C4 C3 114.93(7) . . ?
H4 C4 C3 123.4(5) . . ?
H4 C4 C5 121.6(5) . . ?
C1 C9 C10 104.85(7) . . ?
C16 C9 C10 126.67(8) . . ?
C16 C9 C1 128.48(8) . . ?
C7 C8 H8 122.2(5) . . ?
C2 C8 H8 122.4(5) . . ?
C2 C8 C7 115.31(7) . . ?
C5 C7 O2 109.80(7) . . ?
C8 C7 O2 127.52(7) . . ?
C8 C7 C5 122.63(7) . . ?
C3 C2 S1 112.71(6) . . ?
C8 C2 S1 125.10(6) . . ?
C8 C2 C3 122.18(7) . . ?
N1 C1 S1 111.46(5) . . ?
C9 C1 S1 137.10(6) . . ?
C9 C1 N1 111.39(7) . . ?
H12 C12 C11 121.9(5) . . ?
C13 C12 C11 117.23(9) . . ?
C13 C12 H12 120.8(5) . . ?
H15 C15 C10 120.3(5) . . ?
C14 C15 C10 118.64(9) . . ?
C14 C15 H15 121.1(5) . . ?
H16A C16 C9 113.3(7) . . ?
H16B C16 C9 111.7(7) . . ?
H16B C16 H16A 107.8(13) . . ?
H16C C16 C9 112.0(7) . . ?
H16C C16 H16A 104.4(12) . . ?
H16C C16 H16B 107.1(12) . . ?
H13 C13 C12 119.8(5) . . ?
C14 C13 C12 121.29(9) . . ?
C14 C13 H13 118.9(5) . . ?
C13 C14 C15 121.36(9) . . ?
H14 C14 C15 118.8(6) . . ?
H14 C14 C13 119.8(6) . . ?
O2 C6 O1 108.52(7) . . ?
H6A C6 O1 107.6(6) . . ?
H6A C6 O2 108.7(7) . . ?
H6B C6 O1 109.5(6) . . ?
H6B C6 O2 110.3(7) . . ?
H6B C6 H6A 112.2(10) . . ?

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
S1 C2 C3 N1 -0.75(6) . . . . ?
S1 C2 C3 C4 177.80(5) . . . . ?
S1 C2 C8 C7 -179.12(7) . . . . ?
S1 C1 N1 C3 -3.24(6) . . . . ?
S1 C1 N1 C11 176.31(6) . . . . ?
S1 C1 C9 C10 -176.03(9) . . . . ?
S1 C1 C9 C16 3.32(12) . . . . ?
O1 C5 C4 C3 -177.80(8) . . . . ?
O1 C5 C7 O2 -1.06(7) . . . . ?
O1 C5 C7 C8 176.62(6) . . . . ?
O1 C6 O2 C7 9.47(10) . . . . ?
O2 C7 C5 C4 -179.17(6) . . . . ?
O2 C7 C8 C2 178.94(9) . . . . ?
N1 C3 C4 C5 179.50(8) . . . . ?
N1 C3 C2 C8 -179.53(6) . . . . ?
N1 C11 C10 C9 -0.63(7) . . . . ?
N1 C11 C10 C15 -178.55(6) . . . . ?
N1 C11 C12 C13 177.85(10) . . . . ?
N1 C1 C9 C10 1.27(7) . . . . ?
N1 C1 C9 C16 -179.38(8) . . . . ?
C3 C4 C5 C7 -0.04(9) . . . . ?
C3 C2 C8 C7 -0.49(9) . . . . ?
C11 C10 C9 C1 -0.38(7) . . . . ?
C11 C10 C9 C16 -179.75(7) . . . . ?
C11 C10 C15 C14 0.19(9) . . . . ?
C11 C12 C13 C14 0.19(10) . . . . ?
C5 C7 C8 C2 1.69(9) . . . . ?
C10 C15 C14 C13 0.22(10) . . . . ?
C12 C13 C14 C15 -0.42(11) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.425
_oxdiff_exptl_absorpt_empirical_full_min 0.732




####################################################################### 
# 
# 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_cmpd_4y_XYL-765
_database_code_depnum_ccdc_archive 'CCDC 2466375'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2025-06-23 deposited with the CCDC.	2026-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_chemical_name_systematic        2-fluorobenzo[4,5]thiazolo[3,2-a]indole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H8 F N S'
_chemical_formula_sum            'C14 H8 F N S'
_chemical_formula_weight         241.27

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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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'

_cell_length_a                   10.7774(8)
_cell_length_b                   24.6512(14)
_cell_length_c                   4.0427(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1074.05(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4264
_cell_measurement_theta_min      3.2740
_cell_measurement_theta_max      29.9940

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -5 0 0.0265
-4 5 0 0.0331
1 5 -1 0.1407
-1 -5 1 0.1223
1 5 0 0.0339
-1 -5 0 0.0241
-3 3 -5 0.1543
2 5 1 0.1240
14 2 -2 0.0778
4 -26 3 0.0967
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.286
_shelx_estimated_absorpt_T_min   0.909
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_T_min  0.713
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.141a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            9408
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         3.117
_diffrn_reflns_theta_max         29.558
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_point_group_measured_fraction_full 0.918
_reflns_number_total             2520
_reflns_number_gt                2126
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.527
_reflns_Friedel_fraction_max     0.665
_reflns_Friedel_fraction_full    0.818

_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       'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2015b)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0644P)²+0.0629P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_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 682 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2515
_refine_ls_number_parameters     284
_refine_ls_number_restraints     203
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1088
_refine_ls_wR_factor_gt          0.1045
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.045
_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
F1 F 0.7077(2) 0.29415(10) 0.0812(9) 0.0906(8) Uani 0.870(3) 1 d D . P A 1
S1 S 0.24240(8) 0.47840(4) 0.9144(4) 0.0545(3) Uani 0.870(3) 1 d D . P A 1
N1 N 0.2972(4) 0.3904(2) 0.5959(13) 0.0429(11) Uani 0.870(3) 1 d D . P A 1
C1 C 0.3527(5) 0.4365(3) 0.7326(14) 0.0444(11) Uani 0.870(3) 1 d D . P A 1
C2 C 0.1246(4) 0.43157(16) 0.8225(12) 0.0468(10) Uani 0.870(3) 1 d D . P A 1
C3 C 0.1693(4) 0.38596(19) 0.6537(13) 0.0423(10) Uani 0.870(3) 1 d D . P A 1
C4 C 0.3886(4) 0.35789(19) 0.4502(15) 0.0457(11) Uani 0.870(3) 1 d D . P A 1
C5 C 0.5010(4) 0.3874(2) 0.4969(14) 0.0479(11) Uani 0.870(3) 1 d D . P A 1
C6 C 0.4758(6) 0.4361(3) 0.668(3) 0.0569(18) Uani 0.870(3) 1 d D . P A 1
H6 H 0.532881 0.462798 0.726155 0.068 Uiso 0.870(3) 1 calc R U P A 1
C7 C 0.0005(4) 0.43588(19) 0.8976(14) 0.0552(11) Uani 0.870(3) 1 d D . P A 1
H7 H -0.029915 0.466241 1.007471 0.066 Uiso 0.870(3) 1 calc R U P A 1
C8 C -0.0776(4) 0.3945(2) 0.8071(12) 0.0592(12) Uani 0.870(3) 1 d D . P A 1
H8 H -0.161562 0.396839 0.857733 0.071 Uiso 0.870(3) 1 calc R U P A 1
C9 C -0.0338(5) 0.34946(19) 0.6425(13) 0.0559(12) Uani 0.870(3) 1 d D . P A 1
H9 H -0.088802 0.322065 0.583543 0.067 Uiso 0.870(3) 1 calc R U P A 1
C10 C 0.0903(5) 0.34420(18) 0.5635(14) 0.0516(11) Uani 0.870(3) 1 d D . P A 1
H10 H 0.119708 0.313677 0.453453 0.062 Uiso 0.870(3) 1 calc R U P A 1
C11 C 0.3855(6) 0.3083(2) 0.286(2) 0.0598(17) Uani 0.870(3) 1 d D . P A 1
H11 H 0.311525 0.289348 0.259901 0.072 Uiso 0.870(3) 1 calc R U P A 1
C12 C 0.4962(7) 0.2882(2) 0.164(2) 0.0652(16) Uani 0.870(3) 1 d D . P A 1
H12 H 0.498108 0.255331 0.051450 0.078 Uiso 0.870(3) 1 calc R U P A 1
C13 C 0.6038(5) 0.3176(3) 0.2114(19) 0.0632(13) Uani 0.870(3) 1 d D . P A 1
C14 C 0.6117(4) 0.3657(2) 0.3668(16) 0.0562(11) Uani 0.870(3) 1 d D . P A 1
H14 H 0.686922 0.383859 0.387595 0.067 Uiso 0.870(3) 1 calc R U P A 1
F1A F -0.1771(15) 0.4032(8) 0.891(7) 0.107(6) Uani 0.130(3) 1 d D U P A 2
S1A S 0.5118(13) 0.4447(6) 0.680(4) 0.060(3) Uani 0.130(3) 1 d D U P A 2
N1A N 0.316(2) 0.3842(17) 0.651(10) 0.048(6) Uani 0.130(3) 1 d D U P A 2
C1A C 0.351(3) 0.438(2) 0.674(13) 0.061(7) Uani 0.130(3) 1 d D U P A 2
C5A C 0.152(2) 0.4274(13) 0.864(11) 0.067(7) Uani 0.130(3) 1 d DG U P A 2
C4A C 0.191(2) 0.3813(17) 0.696(11) 0.056(6) Uani 0.130(3) 1 d DG U P A 2
C11A C 0.108(3) 0.3400(14) 0.626(9) 0.065(8) Uani 0.130(3) 1 d DG U P A 2
H11A H 0.133983 0.309089 0.514253 0.078 Uiso 0.130(3) 1 calc R U P A 2
C12A C -0.016(3) 0.3448(13) 0.724(9) 0.061(7) Uani 0.130(3) 1 d DG U P A 2
H12A H -0.071658 0.317129 0.676687 0.073 Uiso 0.130(3) 1 calc R U P A 2
C13A C -0.0551(18) 0.3909(16) 0.891(8) 0.070(7) Uani 0.130(3) 1 d DG U P A 2
C14A C 0.029(3) 0.4322(13) 0.961(8) 0.063(7) Uani 0.130(3) 1 d DG U P A 2
H14A H 0.002237 0.463093 1.072927 0.075 Uiso 0.130(3) 1 calc R U P A 2
C3A C 0.412(3) 0.3664(15) 0.459(11) 0.054(6) Uani 0.130(3) 1 d DG U P A 2
C2A C 0.534(3) 0.3843(12) 0.450(11) 0.050(6) Uani 0.130(3) 1 d DG U P A 2
C7A C 0.625(2) 0.3525(15) 0.303(12) 0.065(8) Uani 0.130(3) 1 d DG U P A 2
H7A H 0.707085 0.364526 0.296877 0.078 Uiso 0.130(3) 1 calc R U P A 2
C8A C 0.594(3) 0.3027(15) 0.164(14) 0.066(9) Uani 0.130(3) 1 d DG U P A 2
H8A H 0.654973 0.281458 0.065656 0.079 Uiso 0.130(3) 1 calc R U P A 2
C9A C 0.472(4) 0.2848(13) 0.173(13) 0.068(9) Uani 0.130(3) 1 d DG U P A 2
H9A H 0.450980 0.251500 0.080416 0.081 Uiso 0.130(3) 1 calc R U P A 2
C10A C 0.381(3) 0.3166(16) 0.320(12) 0.048(7) Uani 0.130(3) 1 d DG U P A 2
H10A H 0.299099 0.304610 0.326400 0.058 Uiso 0.130(3) 1 calc R U P A 2
C6A C 0.269(2) 0.4533(13) 0.904(10) 0.075(6) Uani 0.130(3) 1 d D U P A 2
H6A H 0.286734 0.478109 1.071060 0.090 Uiso 0.130(3) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C13 1.366(6) . ?
S1 C1 1.738(6) . ?
S1 C2 1.756(4) . ?
N1 C1 1.398(5) . ?
N1 C4 1.399(5) . ?
N1 C3 1.403(5) . ?
C1 C6 1.352(9) . ?
C2 C7 1.376(5) . ?
C2 C3 1.400(5) . ?
C3 C10 1.385(5) . ?
C4 C11 1.391(5) . ?
C4 C5 1.426(5) . ?
C5 C14 1.409(5) . ?
C5 C6 1.412(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.373(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.380(6) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.383(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.344(6) . ?
C14 H14 0.9300 . ?
F1A C13A 1.35(2) . ?
S1A C1A 1.74(3) . ?
S1A C2A 1.77(2) . ?
N1A C3A 1.362(19) . ?
N1A C4A 1.363(18) . ?
N1A C1A 1.37(2) . ?
C1A C6A 1.34(3) . ?
C5A C4A 1.3900 . ?
C5A C14A 1.3900 . ?
C5A C6A 1.43(2) . ?
C4A C11A 1.3900 . ?
C11A C12A 1.3900 . ?
C11A H11A 0.9300 . ?
C12A C13A 1.3900 . ?
C12A H12A 0.9300 . ?
C13A C14A 1.3900 . ?
C14A H14A 0.9300 . ?
C3A C2A 1.3900 . ?
C3A C10A 1.3900 . ?
C2A C7A 1.3900 . ?
C7A C8A 1.3900 . ?
C7A H7A 0.9300 . ?
C8A C9A 1.3900 . ?
C8A H8A 0.9300 . ?
C9A C10A 1.3900 . ?
C9A H9A 0.9300 . ?
C10A H10A 0.9300 . ?
C6A H6A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C2 90.8(2) . . ?
C1 N1 C4 109.3(4) . . ?
C1 N1 C3 114.7(4) . . ?
C4 N1 C3 135.9(5) . . ?
C6 C1 N1 109.8(5) . . ?
C6 C1 S1 139.1(5) . . ?
N1 C1 S1 111.0(3) . . ?
C7 C2 C3 120.3(3) . . ?
C7 C2 S1 127.3(3) . . ?
C3 C2 S1 112.5(3) . . ?
C10 C3 C2 120.9(3) . . ?
C10 C3 N1 128.2(4) . . ?
C2 C3 N1 110.9(4) . . ?
C11 C4 N1 133.3(4) . . ?
C11 C4 C5 122.2(3) . . ?
N1 C4 C5 104.5(4) . . ?
C14 C5 C6 132.0(4) . . ?
C14 C5 C4 118.4(4) . . ?
C6 C5 C4 109.6(4) . . ?
C1 C6 C5 106.8(5) . . ?
C1 C6 H6 126.6 . . ?
C5 C6 H6 126.6 . . ?
C8 C7 C2 118.7(4) . . ?
C8 C7 H7 120.7 . . ?
C2 C7 H7 120.7 . . ?
C7 C8 C9 121.2(4) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C10 121.3(3) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C3 117.7(3) . . ?
C9 C10 H10 121.1 . . ?
C3 C10 H10 121.1 . . ?
C12 C11 C4 117.6(4) . . ?
C12 C11 H11 121.2 . . ?
C4 C11 H11 121.2 . . ?
C13 C12 C11 119.1(4) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 F1 120.1(5) . . ?
C14 C13 C12 125.5(4) . . ?
F1 C13 C12 114.4(5) . . ?
C13 C14 C5 117.1(4) . . ?
C13 C14 H14 121.4 . . ?
C5 C14 H14 121.4 . . ?
C1A S1A C2A 92.5(19) . . ?
C3A N1A C4A 144(4) . . ?
C3A N1A C1A 98(3) . . ?
C4A N1A C1A 108(3) . . ?
C6A C1A N1A 98(3) . . ?
C6A C1A S1A 128(3) . . ?
N1A C1A S1A 112(3) . . ?
C4A C5A C14A 120.0 . . ?
C4A C5A C6A 99(3) . . ?
C14A C5A C6A 141(3) . . ?
N1A C4A C5A 109(3) . . ?
N1A C4A C11A 131(3) . . ?
C5A C4A C11A 120.0 . . ?
C4A C11A C12A 120.0 . . ?
C4A C11A H11A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
C13A C12A C11A 120.0 . . ?
C13A C12A H12A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
F1A C13A C12A 119(3) . . ?
F1A C13A C14A 118(3) . . ?
C12A C13A C14A 120.0 . . ?
C13A C14A C5A 120.0 . . ?
C13A C14A H14A 120.0 . . ?
C5A C14A H14A 120.0 . . ?
N1A C3A C2A 129(3) . . ?
N1A C3A C10A 109(3) . . ?
C2A C3A C10A 120.0 . . ?
C3A C2A C7A 120.0 . . ?
C3A C2A S1A 97(2) . . ?
C7A C2A S1A 143(2) . . ?
C8A C7A C2A 120.0 . . ?
C8A C7A H7A 120.0 . . ?
C2A C7A H7A 120.0 . . ?
C9A C8A C7A 120.0 . . ?
C9A C8A H8A 120.0 . . ?
C7A C8A H8A 120.0 . . ?
C8A C9A C10A 120.0 . . ?
C8A C9A H9A 120.0 . . ?
C10A C9A H9A 120.0 . . ?
C9A C10A C3A 120.0 . . ?
C9A C10A H10A 120.0 . . ?
C3A C10A H10A 120.0 . . ?
C1A C6A C5A 112(3) . . ?
C1A C6A H6A 124.0 . . ?
C5A C6A H6A 124.0 . . ?

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
C4 N1 C1 C6 2.6(8) . . . . ?
C3 N1 C1 C6 178.7(6) . . . . ?
C4 N1 C1 S1 179.6(4) . . . . ?
C3 N1 C1 S1 -4.3(7) . . . . ?
C2 S1 C1 C6 178.6(10) . . . . ?
C2 S1 C1 N1 2.9(5) . . . . ?
C1 S1 C2 C7 179.2(4) . . . . ?
C1 S1 C2 C3 -0.9(4) . . . . ?
C7 C2 C3 C10 -0.9(6) . . . . ?
S1 C2 C3 C10 179.2(4) . . . . ?
C7 C2 C3 N1 178.6(5) . . . . ?
S1 C2 C3 N1 -1.3(5) . . . . ?
C1 N1 C3 C10 -177.0(5) . . . . ?
C4 N1 C3 C10 -2.2(10) . . . . ?
C1 N1 C3 C2 3.6(6) . . . . ?
C4 N1 C3 C2 178.3(6) . . . . ?
C1 N1 C4 C11 179.1(6) . . . . ?
C3 N1 C4 C11 4.2(11) . . . . ?
C1 N1 C4 C5 -1.7(6) . . . . ?
C3 N1 C4 C5 -176.7(6) . . . . ?
C11 C4 C5 C14 1.1(5) . . . . ?
N1 C4 C5 C14 -178.2(6) . . . . ?
C11 C4 C5 C6 179.6(7) . . . . ?
N1 C4 C5 C6 0.4(7) . . . . ?
N1 C1 C6 C5 -2.3(9) . . . . ?
S1 C1 C6 C5 -178.0(6) . . . . ?
C14 C5 C6 C1 179.5(6) . . . . ?
C4 C5 C6 C1 1.2(9) . . . . ?
C3 C2 C7 C8 0.7(6) . . . . ?
S1 C2 C7 C8 -179.4(4) . . . . ?
C2 C7 C8 C9 -0.4(7) . . . . ?
C7 C8 C9 C10 0.2(7) . . . . ?
C8 C9 C10 C3 -0.4(7) . . . . ?
C2 C3 C10 C9 0.7(6) . . . . ?
N1 C3 C10 C9 -178.7(5) . . . . ?
N1 C4 C11 C12 178.4(8) . . . . ?
C5 C4 C11 C12 -0.7(6) . . . . ?
C4 C11 C12 C13 0.5(6) . . . . ?
C11 C12 C13 C14 -0.7(7) . . . . ?
C11 C12 C13 F1 180.0(7) . . . . ?
F1 C13 C14 C5 -179.6(6) . . . . ?
C12 C13 C14 C5 1.1(7) . . . . ?
C6 C5 C14 C13 -179.4(9) . . . . ?
C4 C5 C14 C13 -1.2(5) . . . . ?
C3A N1A C1A C6A -171(4) . . . . ?
C4A N1A C1A C6A 35(5) . . . . ?
C3A N1A C1A S1A -34(5) . . . . ?
C4A N1A C1A S1A 171(3) . . . . ?
C2A S1A C1A C6A 148(5) . . . . ?
C2A S1A C1A N1A 28(4) . . . . ?
C3A N1A C4A C5A -156(6) . . . . ?
C1A N1A C4A C5A -22(4) . . . . ?
C3A N1A C4A C11A 29(8) . . . . ?
C1A N1A C4A C11A 164(3) . . . . ?
C14A C5A C4A N1A -175(3) . . . . ?
C6A C5A C4A N1A -1(3) . . . . ?
C14A C5A C4A C11A 0.0 . . . . ?
C6A C5A C4A C11A 174(3) . . . . ?
N1A C4A C11A C12A 174(4) . . . . ?
C5A C4A C11A C12A 0.0 . . . . ?
C4A C11A C12A C13A 0.0 . . . . ?
C11A C12A C13A F1A 159(3) . . . . ?
C11A C12A C13A C14A 0.0 . . . . ?
F1A C13A C14A C5A -159(3) . . . . ?
C12A C13A C14A C5A 0.0 . . . . ?
C4A C5A C14A C13A 0.0 . . . . ?
C6A C5A C14A C13A -171(4) . . . . ?
C4A N1A C3A C2A 169(5) . . . . ?
C1A N1A C3A C2A 32(5) . . . . ?
C4A N1A C3A C10A -26(8) . . . . ?
C1A N1A C3A C10A -163(4) . . . . ?
N1A C3A C2A C7A 163(5) . . . . ?
C10A C3A C2A C7A 0.0 . . . . ?
N1A C3A C2A S1A -13(4) . . . . ?
C10A C3A C2A S1A -177(3) . . . . ?
C1A S1A C2A C3A -9(3) . . . . ?
C1A S1A C2A C7A 176(5) . . . . ?
C3A C2A C7A C8A 0.0 . . . . ?
S1A C2A C7A C8A 174(5) . . . . ?
C2A C7A C8A C9A 0.0 . . . . ?
C7A C8A C9A C10A 0.0 . . . . ?
C8A C9A C10A C3A 0.0 . . . . ?
N1A C3A C10A C9A -166(4) . . . . ?
C2A C3A C10A C9A 0.0 . . . . ?
N1A C1A C6A C5A -37(5) . . . . ?
S1A C1A C6A C5A -163(4) . . . . ?
C4A C5A C6A C1A 25(4) . . . . ?
C14A C5A C6A C1A -163(4) . . . . ?

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_cmpd_5a_XYL-810
_database_code_depnum_ccdc_archive 'CCDC 2466376'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2025-06-23 deposited with the CCDC.	2026-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3

_chemical_name_systematic        
;
'11-methyl-7-(1-(3,4,5-trimethoxyphenyl)vinyl)benzo[4,5]thiazolo[3,2-a]indole'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C26 H23 N O3 S), C H Cl3 '
_chemical_formula_sum            'C53 H47 Cl3 N2 O6 S2'
_chemical_formula_weight         978.40

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'
Cl Cl 0.1484 0.1585 '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/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                   32.1651(13)
_cell_length_b                   7.2605(3)
_cell_length_c                   21.6128(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.122(4)
_cell_angle_gamma                90
_cell_volume                     4872.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    14179
_cell_measurement_theta_min      3.6910
_cell_measurement_theta_max      28.6320

_exptl_crystal_description       'rectangular plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             2040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 0 -4 0.0684
-3 0 4 0.0519
-2 -3 1 0.1185
4 5 -3 0.1120
1 -1 -2 0.1300
-1 0 0 0.0283
1 0 0 0.0243
0 0 -3 0.0949
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.326
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_T_min  0.424
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.141a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            53071
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.621
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             9862
_reflns_number_gt                7147
_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       'CrysAlisPro system (CCD 43.141a 64-bit )'
_computing_cell_refinement       'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0688P)²+1.3956P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9856
_refine_ls_number_parameters     656
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1403
_refine_ls_wR_factor_gt          0.1281
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.71813(2) 0.55203(8) 0.54735(3) 0.05719(16) Uani 1 1 d . . . . .
S1B S 0.69992(2) 0.44962(8) 0.98100(3) 0.05888(17) Uani 1 1 d . . . . .
Cl1 Cl 0.4759(2) 0.5475(15) 0.3460(3) 0.1240(19) Uani 0.508(12) 1 d D . P A 1
Cl2 Cl 0.55052(14) 0.484(2) 0.3092(3) 0.232(4) Uani 0.508(12) 1 d D . P A 1
O2 O 0.97416(5) 0.9148(2) 0.90876(7) 0.0568(4) Uani 1 1 d . . . . .
O1 O 0.91746(5) 1.09229(19) 0.81489(7) 0.0593(4) Uani 1 1 d . . . . .
O3B O 0.57927(5) 0.3889(2) 0.48748(7) 0.0615(4) Uani 1 1 d . . . . .
O2B O 0.56484(5) 0.7415(2) 0.50619(7) 0.0700(4) Uani 1 1 d . . . . .
O3 O 1.00057(6) 0.5738(2) 0.89163(8) 0.0746(5) Uani 1 1 d . . . . .
Cl3 Cl 0.5323(4) 0.8566(15) 0.3399(3) 0.212(4) Uani 0.508(12) 1 d D . P A 1
O1B O 0.60112(6) 0.9083(2) 0.61930(8) 0.0758(5) Uani 1 1 d . . . . .
N1 N 0.77693(5) 0.5828(2) 0.48534(8) 0.0454(4) Uani 1 1 d . . . . .
N1B N 0.76425(5) 0.4027(2) 0.93034(8) 0.0484(4) Uani 1 1 d . . . . .
C5 C 0.86153(6) 0.5699(2) 0.64099(9) 0.0416(4) Uani 1 1 d . . . . .
C18B C 0.65045(6) 0.4480(3) 0.65011(9) 0.0457(4) Uani 1 1 d . . . . .
C3 C 0.80045(6) 0.5736(2) 0.54940(9) 0.0403(4) Uani 1 1 d . . . . .
C2 C 0.77283(6) 0.5577(3) 0.58992(9) 0.0436(4) Uani 1 1 d . . . . .
C23B C 0.62991(6) 0.3631(3) 0.59254(9) 0.0468(4) Uani 1 1 d . . . . .
H H 0.635384 0.239908 0.585922 0.056 Uiso 1 1 calc R U . . .
C7 C 0.78928(6) 0.5531(3) 0.65539(9) 0.0466(5) Uani 1 1 d . . . . .
HA H 0.771011 0.544642 0.682281 0.056 Uiso 1 1 calc R U . . .
C6 C 0.83338(6) 0.5612(3) 0.68055(9) 0.0453(4) Uani 1 1 d . . . . .
HB H 0.844620 0.560818 0.724798 0.054 Uiso 1 1 calc R U . . .
C4 C 0.84432(6) 0.5781(2) 0.57464(9) 0.0426(4) Uani 1 1 d . . . . .
HC H 0.862504 0.586490 0.547631 0.051 Uiso 1 1 calc R U . . .
C16B C 0.68384(6) 0.3466(3) 0.69920(9) 0.0475(5) Uani 1 1 d . . . . .
C20 C 0.92869(6) 0.9183(3) 0.80116(10) 0.0454(4) Uani 1 1 d . . . . .
C22B C 0.60136(6) 0.4615(3) 0.54510(9) 0.0476(5) Uani 1 1 d . . . . .
C16 C 0.90893(6) 0.5631(3) 0.66920(10) 0.0465(5) Uani 1 1 d . . . . .
C5B C 0.68636(6) 0.3789(3) 0.76837(9) 0.0458(4) Uani 1 1 d . . . . .
C3B C 0.72794(6) 0.3994(2) 0.87805(9) 0.0444(4) Uani 1 1 d . . . . .
C21 C 0.95797(6) 0.8281(3) 0.85094(9) 0.0472(5) Uani 1 1 d . . . . .
C18 C 0.92641(6) 0.6547(3) 0.73269(9) 0.0460(4) Uani 1 1 d . . . . .
C8 C 0.78557(7) 0.6057(3) 0.42598(9) 0.0471(5) Uani 1 1 d . . . . .
C19 C 0.91259(6) 0.8311(3) 0.74284(9) 0.0463(5) Uani 1 1 d . . . . .
HD H 0.892427 0.890752 0.710289 0.056 Uiso 1 1 calc R U . . .
C2B C 0.69022(7) 0.4238(3) 0.89755(9) 0.0482(5) Uani 1 1 d . . . . .
C4B C 0.72622(6) 0.3775(3) 0.81361(9) 0.0459(4) Uani 1 1 d . . . . .
HE H 0.751414 0.361936 0.800724 0.055 Uiso 1 1 calc R U . . .
C8B C 0.80864(7) 0.3907(3) 0.94105(10) 0.0505(5) Uani 1 1 d . . . . .
C19B C 0.64105(7) 0.6305(3) 0.66017(10) 0.0522(5) Uani 1 1 d . . . . .
HF H 0.654275 0.687460 0.698842 0.063 Uiso 1 1 calc R U . . .
C21B C 0.59263(7) 0.6449(3) 0.55473(10) 0.0525(5) Uani 1 1 d . . . . .
C1 C 0.73252(6) 0.5703(3) 0.47544(10) 0.0495(5) Uani 1 1 d . . . . .
C10B C 0.79172(7) 0.4346(3) 1.03816(10) 0.0534(5) Uani 1 1 d . . . . .
C6B C 0.64916(7) 0.4052(3) 0.78887(10) 0.0524(5) Uani 1 1 d . . . . .
HG H 0.622626 0.408056 0.758638 0.063 Uiso 1 1 calc R U . . .
C1B C 0.75501(7) 0.4296(3) 0.98973(10) 0.0500(5) Uani 1 1 d . . . . .
C20B C 0.61211(7) 0.7280(3) 0.61295(10) 0.0538(5) Uani 1 1 d . . . . .
C9B C 0.82614(7) 0.4111(3) 1.00812(10) 0.0538(5) Uani 1 1 d . . . . .
C9 C 0.74527(7) 0.6036(3) 0.37990(10) 0.0532(5) Uani 1 1 d . . . . .
C22 C 0.97168(6) 0.6519(3) 0.84050(10) 0.0533(5) Uani 1 1 d . . . . .
C7B C 0.65062(7) 0.4270(3) 0.85282(10) 0.0542(5) Uani 1 1 d . . . . .
HH H 0.625430 0.443539 0.865640 0.065 Uiso 1 1 calc R U . . .
C17B C 0.71028(8) 0.2305(4) 0.68167(12) 0.0622(6) Uani 1 1 d . . . . .
C10 C 0.71190(7) 0.5813(3) 0.41188(11) 0.0555(5) Uani 1 1 d . . . . .
C23 C 0.95620(6) 0.5668(3) 0.78147(11) 0.0544(5) Uani 1 1 d . . . . .
HI H 0.965941 0.449852 0.774696 0.065 Uiso 1 1 calc R U . . .
C15 C 0.82400(8) 0.6306(3) 0.40978(10) 0.0596(6) Uani 1 1 d . . . . .
HJ H 0.850139 0.633705 0.440911 0.072 Uiso 1 1 calc R U . . .
C24 C 0.88503(8) 1.1827(3) 0.76720(11) 0.0663(6) Uani 1 1 d . . . . .
HK H 0.894479 1.195454 0.728799 0.099 Uiso 1 1 calc R U . . .
HL H 0.879685 1.302415 0.782371 0.099 Uiso 1 1 calc R U . . .
HM H 0.859010 1.111362 0.758230 0.099 Uiso 1 1 calc R U . . .
C15B C 0.83429(7) 0.3660(3) 0.89951(12) 0.0643(6) Uani 1 1 d . . . . .
HN H 0.822403 0.353507 0.855626 0.077 Uiso 1 1 calc R U . . .
C12B C 0.87082(8) 0.4056(3) 1.03220(12) 0.0664(6) Uani 1 1 d . . . . .
HO H 0.883214 0.418931 1.075923 0.080 Uiso 1 1 calc R U . . .
C11B C 0.79588(9) 0.4566(3) 1.10829(10) 0.0669(6) Uani 1 1 d . . . . .
HP H 0.768580 0.492209 1.114774 0.100 Uiso 1 1 calc R U . . .
HQ H 0.816905 0.549818 1.125392 0.100 Uiso 1 1 calc R U . . .
HR H 0.804822 0.341913 1.129752 0.100 Uiso 1 1 calc R U . . .
C17 C 0.93473(8) 0.4778(4) 0.64003(13) 0.0629(6) Uani 1 1 d . . . . .
C12 C 0.74498(9) 0.6241(3) 0.31514(11) 0.0676(7) Uani 1 1 d . . . . .
HS H 0.719112 0.622558 0.283428 0.081 Uiso 1 1 calc R U . . .
C14 C 0.82207(10) 0.6505(4) 0.34545(12) 0.0726(7) Uani 1 1 d . . . . .
HT H 0.847391 0.667120 0.332977 0.087 Uiso 1 1 calc R U . . .
C13B C 0.89618(8) 0.3806(4) 0.99128(14) 0.0771(7) Uani 1 1 d . . . . .
HU H 0.925941 0.376725 1.007494 0.093 Uiso 1 1 calc R U . . .
C13 C 0.78300(11) 0.6462(4) 0.29926(12) 0.0772(8) Uani 1 1 d . . . . .
HV H 0.782724 0.658730 0.256332 0.093 Uiso 1 1 calc R U . . .
C14B C 0.87835(8) 0.3606(4) 0.92570(13) 0.0766(7) Uani 1 1 d . . . . .
HW H 0.896434 0.343339 0.898914 0.092 Uiso 1 1 calc R U . . .
C26B C 0.58498(9) 0.1978(4) 0.47753(12) 0.0798(8) Uani 1 1 d . . . . .
HX H 0.565765 0.160374 0.437620 0.120 Uiso 1 1 calc R U . . .
HY H 0.578830 0.128467 0.511931 0.120 Uiso 1 1 calc R U . . .
HZ H 0.614179 0.175580 0.476344 0.120 Uiso 1 1 calc R U . . .
C11 C 0.66423(8) 0.5738(4) 0.38246(14) 0.0779(8) Uani 1 1 d . . . . .
H1 H 0.649521 0.567078 0.415752 0.117 Uiso 1 1 calc R U . . .
H2 H 0.657406 0.466900 0.355565 0.117 Uiso 1 1 calc R U . . .
H3 H 0.655259 0.682495 0.357235 0.117 Uiso 1 1 calc R U . . .
C26 C 1.01389(10) 0.3897(4) 0.88386(15) 0.0954(10) Uani 1 1 d . . . . .
H4 H 1.025631 0.383728 0.847381 0.143 Uiso 1 1 calc R U . . .
H5 H 0.989553 0.308600 0.877391 0.143 Uiso 1 1 calc R U . . .
H6 H 1.035430 0.352853 0.921580 0.143 Uiso 1 1 calc R U . . .
C25 C 0.94867(10) 0.8958(5) 0.95236(13) 0.0980(10) Uani 1 1 d . . . . .
H7 H 0.921531 0.956346 0.935595 0.147 Uiso 1 1 calc R U . . .
H8 H 0.963252 0.950579 0.992592 0.147 Uiso 1 1 calc R U . . .
H9 H 0.943842 0.767439 0.958626 0.147 Uiso 1 1 calc R U . . .
C24B C 0.60543(11) 0.9746(4) 0.68178(14) 0.0866(8) Uani 1 1 d . . . . .
H10 H 0.591859 1.092968 0.679787 0.130 Uiso 1 1 calc R U . . .
H11 H 0.635429 0.985781 0.703496 0.130 Uiso 1 1 calc R U . . .
H12 H 0.591953 0.890186 0.704737 0.130 Uiso 1 1 calc R U . . .
C25B C 0.52315(9) 0.7648(4) 0.51543(16) 0.0936(9) Uani 1 1 d . . . . .
H13 H 0.505084 0.826914 0.479019 0.140 Uiso 1 1 calc R U . . .
H14 H 0.525055 0.836940 0.553305 0.140 Uiso 1 1 calc R U . . .
H15 H 0.511058 0.646483 0.520243 0.140 Uiso 1 1 calc R U . . .
C27B C 0.5285(3) 0.6151(16) 0.3555(3) 0.091(4) Uani 0.508(12) 1 d D . P A 1
H27B H 0.544170 0.592471 0.400189 0.109 Uiso 0.508(12) 1 calc R U P A 1
Cl3A Cl 0.54462(19) 0.7807(9) 0.3211(4) 0.154(2) Uani 0.492(12) 1 d D . P A 2
C27C C 0.5290(4) 0.5724(17) 0.3523(7) 0.142(7) Uani 0.492(12) 1 d D . P A 2
H27C H 0.543780 0.567597 0.398016 0.170 Uiso 0.492(12) 1 calc R U P A 2
Cl2A Cl 0.54893(17) 0.4000(6) 0.3157(2) 0.1288(14) Uani 0.492(12) 1 d D . P A 2
Cl1A Cl 0.4745(2) 0.5876(16) 0.3457(4) 0.147(3) Uani 0.492(12) 1 d D . P A 2
H16 H 0.7317(8) 0.166(3) 0.7121(12) 0.063(6) Uiso 1 1 d . . . . .
H17 H 0.7084(7) 0.211(3) 0.6383(11) 0.059(6) Uiso 1 1 d . . . . .
H18 H 0.9255(8) 0.416(3) 0.6011(12) 0.064(7) Uiso 1 1 d . . . . .
H19 H 0.9629(9) 0.477(3) 0.6602(12) 0.069(7) 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 C1 1.739(2) . ?
S1 C2 1.7604(19) . ?
S1B C1B 1.739(2) . ?
S1B C2B 1.758(2) . ?
Cl1 C27B 1.722(8) . ?
Cl2 C27B 1.667(10) . ?
O2 C21 1.374(2) . ?
O2 C25 1.408(3) . ?
O1 C20 1.368(2) . ?
O1 C24 1.422(3) . ?
O3B C22B 1.368(2) . ?
O3B C26B 1.423(3) . ?
O2B C21B 1.379(2) . ?
O2B C25B 1.417(3) . ?
O3 C22 1.368(2) . ?
O3 C26 1.427(3) . ?
Cl3 C27B 1.795(10) . ?
O1B C20B 1.373(3) . ?
O1B C24B 1.406(3) . ?
N1 C1 1.391(3) . ?
N1 C8 1.392(3) . ?
N1 C3 1.396(2) . ?
N1B C8B 1.388(3) . ?
N1B C3B 1.397(2) . ?
N1B C1B 1.405(3) . ?
C5 C4 1.397(3) . ?
C5 C6 1.400(3) . ?
C5 C16 1.488(3) . ?
C18B C19B 1.389(3) . ?
C18B C23B 1.391(3) . ?
C18B C16B 1.492(3) . ?
C3 C4 1.374(3) . ?
C3 C2 1.405(3) . ?
C2 C7 1.376(3) . ?
C23B C22B 1.383(3) . ?
C23B H 0.9300 . ?
C7 C6 1.382(3) . ?
C7 HA 0.9300 . ?
C6 HB 0.9300 . ?
C4 HC 0.9300 . ?
C16B C17B 1.321(3) . ?
C16B C5B 1.494(3) . ?
C20 C19 1.384(3) . ?
C20 C21 1.394(3) . ?
C22B C21B 1.387(3) . ?
C16 C17 1.320(3) . ?
C16 C18 1.496(3) . ?
C5B C6B 1.393(3) . ?
C5B C4B 1.395(3) . ?
C3B C4B 1.389(3) . ?
C3B C2B 1.396(3) . ?
C21 C22 1.391(3) . ?
C18 C23 1.382(3) . ?
C18 C19 1.392(3) . ?
C8 C15 1.381(3) . ?
C8 C9 1.414(3) . ?
C19 HD 0.9300 . ?
C2B C7B 1.384(3) . ?
C4B HE 0.9300 . ?
C8B C15B 1.380(3) . ?
C8B C9B 1.419(3) . ?
C19B C20B 1.383(3) . ?
C19B HF 0.9300 . ?
C21B C20B 1.389(3) . ?
C1 C10 1.363(3) . ?
C10B C1B 1.359(3) . ?
C10B C9B 1.432(3) . ?
C10B C11B 1.495(3) . ?
C6B C7B 1.380(3) . ?
C6B HG 0.9300 . ?
C9B C12B 1.396(3) . ?
C9 C12 1.405(3) . ?
C9 C10 1.429(3) . ?
C22 C23 1.388(3) . ?
C7B HH 0.9300 . ?
C17B H16 0.94(2) . ?
C17B H17 0.93(2) . ?
C10 C11 1.500(3) . ?
C23 HI 0.9300 . ?
C15 C14 1.383(3) . ?
C15 HJ 0.9300 . ?
C24 HK 0.9600 . ?
C24 HL 0.9600 . ?
C24 HM 0.9600 . ?
C15B C14B 1.383(3) . ?
C15B HN 0.9300 . ?
C12B C13B 1.363(4) . ?
C12B HO 0.9300 . ?
C11B HP 0.9600 . ?
C11B HQ 0.9600 . ?
C11B HR 0.9600 . ?
C17 H18 0.93(3) . ?
C17 H19 0.90(3) . ?
C12 C13 1.363(4) . ?
C12 HS 0.9300 . ?
C14 C13 1.387(4) . ?
C14 HT 0.9300 . ?
C13B C14B 1.391(4) . ?
C13B HU 0.9300 . ?
C13 HV 0.9300 . ?
C14B HW 0.9300 . ?
C26B HX 0.9600 . ?
C26B HY 0.9600 . ?
C26B HZ 0.9600 . ?
C11 H1 0.9600 . ?
C11 H2 0.9600 . ?
C11 H3 0.9600 . ?
C26 H4 0.9600 . ?
C26 H5 0.9600 . ?
C26 H6 0.9600 . ?
C25 H7 0.9600 . ?
C25 H8 0.9600 . ?
C25 H9 0.9600 . ?
C24B H10 0.9600 . ?
C24B H11 0.9600 . ?
C24B H12 0.9600 . ?
C25B H13 0.9600 . ?
C25B H14 0.9600 . ?
C25B H15 0.9600 . ?
C27B H27B 0.9800 . ?
Cl3A C27C 1.781(12) . ?
C27C Cl2A 1.693(12) . ?
C27C Cl1A 1.726(11) . ?
C27C H27C 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
C1 S1 C2 90.14(9) . . ?
C1B S1B C2B 90.31(10) . . ?
C21 O2 C25 114.52(17) . . ?
C20 O1 C24 117.04(16) . . ?
C22B O3B C26B 117.16(17) . . ?
C21B O2B C25B 113.77(19) . . ?
C22 O3 C26 117.06(18) . . ?
C20B O1B C24B 117.31(19) . . ?
C1 N1 C8 108.07(16) . . ?
C1 N1 C3 114.74(16) . . ?
C8 N1 C3 137.18(17) . . ?
C8B N1B C3B 137.73(18) . . ?
C8B N1B C1B 108.05(16) . . ?
C3B N1B C1B 114.20(17) . . ?
C4 C5 C6 118.85(17) . . ?
C4 C5 C16 120.76(17) . . ?
C6 C5 C16 120.34(17) . . ?
C19B C18B C23B 119.38(18) . . ?
C19B C18B C16B 120.34(18) . . ?
C23B C18B C16B 120.22(18) . . ?
C4 C3 N1 128.87(17) . . ?
C4 C3 C2 120.34(17) . . ?
N1 C3 C2 110.79(16) . . ?
C7 C2 C3 120.46(18) . . ?
C7 C2 S1 126.91(15) . . ?
C3 C2 S1 112.61(14) . . ?
C22B C23B C18B 120.18(19) . . ?
C22B C23B H 119.9 . . ?
C18B C23B H 119.9 . . ?
C2 C7 C6 118.92(18) . . ?
C2 C7 HA 120.5 . . ?
C6 C7 HA 120.5 . . ?
C7 C6 C5 121.53(18) . . ?
C7 C6 HB 119.2 . . ?
C5 C6 HB 119.2 . . ?
C3 C4 C5 119.83(17) . . ?
C3 C4 HC 120.1 . . ?
C5 C4 HC 120.1 . . ?
C17B C16B C18B 120.58(19) . . ?
C17B C16B C5B 121.07(19) . . ?
C18B C16B C5B 118.35(18) . . ?
O1 C20 C19 124.23(17) . . ?
O1 C20 C21 115.44(17) . . ?
C19 C20 C21 120.33(18) . . ?
O3B C22B C23B 124.20(19) . . ?
O3B C22B C21B 115.40(17) . . ?
C23B C22B C21B 120.38(18) . . ?
C17 C16 C5 121.6(2) . . ?
C17 C16 C18 120.93(19) . . ?
C5 C16 C18 117.44(16) . . ?
C6B C5B C4B 119.11(18) . . ?
C6B C5B C16B 120.86(17) . . ?
C4B C5B C16B 120.00(18) . . ?
C4B C3B C2B 120.47(18) . . ?
C4B C3B N1B 128.27(19) . . ?
C2B C3B N1B 111.26(17) . . ?
O2 C21 C22 120.51(17) . . ?
O2 C21 C20 120.40(18) . . ?
C22 C21 C20 119.05(18) . . ?
C23 C18 C19 119.41(18) . . ?
C23 C18 C16 120.94(18) . . ?
C19 C18 C16 119.65(17) . . ?
C15 C8 N1 131.01(19) . . ?
C15 C8 C9 122.6(2) . . ?
N1 C8 C9 106.33(18) . . ?
C20 C19 C18 120.34(18) . . ?
C20 C19 HD 119.8 . . ?
C18 C19 HD 119.8 . . ?
C7B C2B C3B 120.36(19) . . ?
C7B C2B S1B 126.84(17) . . ?
C3B C2B S1B 112.80(15) . . ?
C3B C4B C5B 119.41(19) . . ?
C3B C4B HE 120.3 . . ?
C5B C4B HE 120.3 . . ?
C15B C8B N1B 131.52(19) . . ?
C15B C8B C9B 122.2(2) . . ?
N1B C8B C9B 106.28(19) . . ?
C20B C19B C18B 120.31(19) . . ?
C20B C19B HF 119.8 . . ?
C18B C19B HF 119.8 . . ?
O2B C21B C22B 119.35(19) . . ?
O2B C21B C20B 121.2(2) . . ?
C22B C21B C20B 119.44(18) . . ?
C10 C1 N1 111.18(19) . . ?
C10 C1 S1 137.08(17) . . ?
N1 C1 S1 111.70(14) . . ?
C1B C10B C9B 105.47(19) . . ?
C1B C10B C11B 127.9(2) . . ?
C9B C10B C11B 126.7(2) . . ?
C7B C6B C5B 121.79(19) . . ?
C7B C6B HG 119.1 . . ?
C5B C6B HG 119.1 . . ?
C10B C1B N1B 111.0(2) . . ?
C10B C1B S1B 137.54(18) . . ?
N1B C1B S1B 111.41(14) . . ?
O1B C20B C19B 123.8(2) . . ?
O1B C20B C21B 115.96(19) . . ?
C19B C20B C21B 120.3(2) . . ?
C12B C9B C8B 118.3(2) . . ?
C12B C9B C10B 132.6(2) . . ?
C8B C9B C10B 109.14(19) . . ?
C12 C9 C8 117.8(2) . . ?
C12 C9 C10 133.1(2) . . ?
C8 C9 C10 109.07(19) . . ?
O3 C22 C23 124.3(2) . . ?
O3 C22 C21 115.33(18) . . ?
C23 C22 C21 120.38(18) . . ?
C6B C7B C2B 118.9(2) . . ?
C6B C7B HH 120.6 . . ?
C2B C7B HH 120.6 . . ?
C16B C17B H16 121.7(14) . . ?
C16B C17B H17 120.4(14) . . ?
H16 C17B H17 118(2) . . ?
C1 C10 C9 105.35(18) . . ?
C1 C10 C11 126.9(2) . . ?
C9 C10 C11 127.8(2) . . ?
C18 C23 C22 120.5(2) . . ?
C18 C23 HI 119.8 . . ?
C22 C23 HI 119.8 . . ?
C8 C15 C14 117.4(2) . . ?
C8 C15 HJ 121.3 . . ?
C14 C15 HJ 121.3 . . ?
O1 C24 HK 109.5 . . ?
O1 C24 HL 109.5 . . ?
HK C24 HL 109.5 . . ?
O1 C24 HM 109.5 . . ?
HK C24 HM 109.5 . . ?
HL C24 HM 109.5 . . ?
C8B C15B C14B 117.4(2) . . ?
C8B C15B HN 121.3 . . ?
C14B C15B HN 121.3 . . ?
C13B C12B C9B 119.6(2) . . ?
C13B C12B HO 120.2 . . ?
C9B C12B HO 120.2 . . ?
C10B C11B HP 109.5 . . ?
C10B C11B HQ 109.5 . . ?
HP C11B HQ 109.5 . . ?
C10B C11B HR 109.5 . . ?
HP C11B HR 109.5 . . ?
HQ C11B HR 109.5 . . ?
C16 C17 H18 124.5(15) . . ?
C16 C17 H19 116.9(16) . . ?
H18 C17 H19 118(2) . . ?
C13 C12 C9 119.4(2) . . ?
C13 C12 HS 120.3 . . ?
C9 C12 HS 120.3 . . ?
C15 C14 C13 121.1(3) . . ?
C15 C14 HT 119.5 . . ?
C13 C14 HT 119.5 . . ?
C12B C13B C14B 121.2(2) . . ?
C12B C13B HU 119.4 . . ?
C14B C13B HU 119.4 . . ?
C12 C13 C14 121.7(2) . . ?
C12 C13 HV 119.1 . . ?
C14 C13 HV 119.1 . . ?
C15B C14B C13B 121.4(3) . . ?
C15B C14B HW 119.3 . . ?
C13B C14B HW 119.3 . . ?
O3B C26B HX 109.5 . . ?
O3B C26B HY 109.5 . . ?
HX C26B HY 109.5 . . ?
O3B C26B HZ 109.5 . . ?
HX C26B HZ 109.5 . . ?
HY C26B HZ 109.5 . . ?
C10 C11 H1 109.5 . . ?
C10 C11 H2 109.5 . . ?
H1 C11 H2 109.5 . . ?
C10 C11 H3 109.5 . . ?
H1 C11 H3 109.5 . . ?
H2 C11 H3 109.5 . . ?
O3 C26 H4 109.5 . . ?
O3 C26 H5 109.5 . . ?
H4 C26 H5 109.5 . . ?
O3 C26 H6 109.5 . . ?
H4 C26 H6 109.5 . . ?
H5 C26 H6 109.5 . . ?
O2 C25 H7 109.5 . . ?
O2 C25 H8 109.5 . . ?
H7 C25 H8 109.5 . . ?
O2 C25 H9 109.5 . . ?
H7 C25 H9 109.5 . . ?
H8 C25 H9 109.5 . . ?
O1B C24B H10 109.5 . . ?
O1B C24B H11 109.5 . . ?
H10 C24B H11 109.5 . . ?
O1B C24B H12 109.5 . . ?
H10 C24B H12 109.5 . . ?
H11 C24B H12 109.5 . . ?
O2B C25B H13 109.5 . . ?
O2B C25B H14 109.5 . . ?
H13 C25B H14 109.5 . . ?
O2B C25B H15 109.5 . . ?
H13 C25B H15 109.5 . . ?
H14 C25B H15 109.5 . . ?
Cl2 C27B Cl1 108.9(5) . . ?
Cl2 C27B Cl3 112.5(5) . . ?
Cl1 C27B Cl3 111.7(7) . . ?
Cl2 C27B H27B 107.8 . . ?
Cl1 C27B H27B 107.8 . . ?
Cl3 C27B H27B 107.8 . . ?
Cl2A C27C Cl1A 120.6(9) . . ?
Cl2A C27C Cl3A 105.8(7) . . ?
Cl1A C27C Cl3A 107.2(7) . . ?
Cl2A C27C H27C 107.5 . . ?
Cl1A C27C H27C 107.5 . . ?
Cl3A C27C H27C 107.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C3 C4 178.56(18) . . . . ?
C8 N1 C3 C4 -3.2(3) . . . . ?
C1 N1 C3 C2 -1.4(2) . . . . ?
C8 N1 C3 C2 176.9(2) . . . . ?
C4 C3 C2 C7 2.3(3) . . . . ?
N1 C3 C2 C7 -177.69(17) . . . . ?
C4 C3 C2 S1 -179.33(14) . . . . ?
N1 C3 C2 S1 0.67(19) . . . . ?
C1 S1 C2 C7 178.39(18) . . . . ?
C1 S1 C2 C3 0.16(15) . . . . ?
C19B C18B C23B C22B 1.9(3) . . . . ?
C16B C18B C23B C22B -175.10(18) . . . . ?
C3 C2 C7 C6 -1.1(3) . . . . ?
S1 C2 C7 C6 -179.17(14) . . . . ?
C2 C7 C6 C5 -1.4(3) . . . . ?
C4 C5 C6 C7 2.6(3) . . . . ?
C16 C5 C6 C7 -174.99(17) . . . . ?
N1 C3 C4 C5 178.93(17) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C6 C5 C4 C3 -1.3(3) . . . . ?
C16 C5 C4 C3 176.25(16) . . . . ?
C19B C18B C16B C17B -141.2(2) . . . . ?
C23B C18B C16B C17B 35.7(3) . . . . ?
C19B C18B C16B C5B 39.1(3) . . . . ?
C23B C18B C16B C5B -143.89(19) . . . . ?
C24 O1 C20 C19 4.3(3) . . . . ?
C24 O1 C20 C21 -174.93(19) . . . . ?
C26B O3B C22B C23B 2.8(3) . . . . ?
C26B O3B C22B C21B -175.6(2) . . . . ?
C18B C23B C22B O3B -179.01(18) . . . . ?
C18B C23B C22B C21B -0.7(3) . . . . ?
C4 C5 C16 C17 -33.7(3) . . . . ?
C6 C5 C16 C17 143.8(2) . . . . ?
C4 C5 C16 C18 147.08(18) . . . . ?
C6 C5 C16 C18 -35.4(3) . . . . ?
C17B C16B C5B C6B -142.6(2) . . . . ?
C18B C16B C5B C6B 37.0(3) . . . . ?
C17B C16B C5B C4B 35.4(3) . . . . ?
C18B C16B C5B C4B -144.96(19) . . . . ?
C8B N1B C3B C4B 1.2(4) . . . . ?
C1B N1B C3B C4B 179.31(19) . . . . ?
C8B N1B C3B C2B -178.2(2) . . . . ?
C1B N1B C3B C2B -0.1(2) . . . . ?
C25 O2 C21 C22 -95.3(3) . . . . ?
C25 O2 C21 C20 87.0(3) . . . . ?
O1 C20 C21 O2 -1.0(3) . . . . ?
C19 C20 C21 O2 179.67(17) . . . . ?
O1 C20 C21 C22 -178.79(18) . . . . ?
C19 C20 C21 C22 1.9(3) . . . . ?
C17 C16 C18 C23 -45.7(3) . . . . ?
C5 C16 C18 C23 133.5(2) . . . . ?
C17 C16 C18 C19 134.2(2) . . . . ?
C5 C16 C18 C19 -46.7(3) . . . . ?
C1 N1 C8 C15 177.7(2) . . . . ?
C3 N1 C8 C15 -0.6(4) . . . . ?
C1 N1 C8 C9 -0.9(2) . . . . ?
C3 N1 C8 C9 -179.30(19) . . . . ?
O1 C20 C19 C18 178.87(18) . . . . ?
C21 C20 C19 C18 -1.9(3) . . . . ?
C23 C18 C19 C20 0.3(3) . . . . ?
C16 C18 C19 C20 -179.53(18) . . . . ?
C4B C3B C2B C7B -0.2(3) . . . . ?
N1B C3B C2B C7B 179.27(18) . . . . ?
C4B C3B C2B S1B -179.80(15) . . . . ?
N1B C3B C2B S1B -0.3(2) . . . . ?
C1B S1B C2B C7B -179.04(19) . . . . ?
C1B S1B C2B C3B 0.50(15) . . . . ?
C2B C3B C4B C5B -0.4(3) . . . . ?
N1B C3B C4B C5B -179.75(18) . . . . ?
C6B C5B C4B C3B 1.0(3) . . . . ?
C16B C5B C4B C3B -177.13(17) . . . . ?
C3B N1B C8B C15B -1.4(4) . . . . ?
C1B N1B C8B C15B -179.5(2) . . . . ?
C3B N1B C8B C9B 178.1(2) . . . . ?
C1B N1B C8B C9B 0.0(2) . . . . ?
C23B C18B C19B C20B -1.1(3) . . . . ?
C16B C18B C19B C20B 175.86(19) . . . . ?
C25B O2B C21B C22B 102.6(3) . . . . ?
C25B O2B C21B C20B -77.5(3) . . . . ?
O3B C22B C21B O2B -3.0(3) . . . . ?
C23B C22B C21B O2B 178.48(19) . . . . ?
O3B C22B C21B C20B 177.14(19) . . . . ?
C23B C22B C21B C20B -1.3(3) . . . . ?
C8 N1 C1 C10 0.9(2) . . . . ?
C3 N1 C1 C10 179.68(16) . . . . ?
C8 N1 C1 S1 -177.20(13) . . . . ?
C3 N1 C1 S1 1.6(2) . . . . ?
C2 S1 C1 C10 -178.4(2) . . . . ?
C2 S1 C1 N1 -0.95(15) . . . . ?
C4B C5B C6B C7B -1.0(3) . . . . ?
C16B C5B C6B C7B 177.05(19) . . . . ?
C9B C10B C1B N1B 0.5(2) . . . . ?
C11B C10B C1B N1B -178.61(19) . . . . ?
C9B C10B C1B S1B -178.75(18) . . . . ?
C11B C10B C1B S1B 2.2(4) . . . . ?
C8B N1B C1B C10B -0.3(2) . . . . ?
C3B N1B C1B C10B -178.92(16) . . . . ?
C8B N1B C1B S1B 179.16(13) . . . . ?
C3B N1B C1B S1B 0.5(2) . . . . ?
C2B S1B C1B C10B 178.7(2) . . . . ?
C2B S1B C1B N1B -0.56(15) . . . . ?
C24B O1B C20B C19B -25.3(3) . . . . ?
C24B O1B C20B C21B 155.4(2) . . . . ?
C18B C19B C20B O1B 179.9(2) . . . . ?
C18B C19B C20B C21B -0.9(3) . . . . ?
O2B C21B C20B O1B 1.6(3) . . . . ?
C22B C21B C20B O1B -178.61(19) . . . . ?
O2B C21B C20B C19B -177.7(2) . . . . ?
C22B C21B C20B C19B 2.1(3) . . . . ?
C15B C8B C9B C12B 0.0(3) . . . . ?
N1B C8B C9B C12B -179.58(18) . . . . ?
C15B C8B C9B C10B 179.9(2) . . . . ?
N1B C8B C9B C10B 0.3(2) . . . . ?
C1B C10B C9B C12B 179.4(2) . . . . ?
C11B C10B C9B C12B -1.5(4) . . . . ?
C1B C10B C9B C8B -0.5(2) . . . . ?
C11B C10B C9B C8B 178.6(2) . . . . ?
C15 C8 C9 C12 1.3(3) . . . . ?
N1 C8 C9 C12 -179.85(17) . . . . ?
C15 C8 C9 C10 -178.16(19) . . . . ?
N1 C8 C9 C10 0.7(2) . . . . ?
C26 O3 C22 C23 -2.9(4) . . . . ?
C26 O3 C22 C21 177.1(2) . . . . ?
O2 C21 C22 O3 1.9(3) . . . . ?
C20 C21 C22 O3 179.62(19) . . . . ?
O2 C21 C22 C23 -178.16(19) . . . . ?
C20 C21 C22 C23 -0.4(3) . . . . ?
C5B C6B C7B C2B 0.4(3) . . . . ?
C3B C2B C7B C6B 0.2(3) . . . . ?
S1B C2B C7B C6B 179.70(16) . . . . ?
N1 C1 C10 C9 -0.5(2) . . . . ?
S1 C1 C10 C9 176.95(18) . . . . ?
N1 C1 C10 C11 -179.8(2) . . . . ?
S1 C1 C10 C11 -2.4(4) . . . . ?
C12 C9 C10 C1 -179.5(2) . . . . ?
C8 C9 C10 C1 -0.1(2) . . . . ?
C12 C9 C10 C11 -0.2(4) . . . . ?
C8 C9 C10 C11 179.2(2) . . . . ?
C19 C18 C23 C22 1.2(3) . . . . ?
C16 C18 C23 C22 -178.96(19) . . . . ?
O3 C22 C23 C18 178.8(2) . . . . ?
C21 C22 C23 C18 -1.1(3) . . . . ?
N1 C8 C15 C14 -179.7(2) . . . . ?
C9 C8 C15 C14 -1.2(3) . . . . ?
N1B C8B C15B C14B 179.8(2) . . . . ?
C9B C8B C15B C14B 0.3(3) . . . . ?
C8B C9B C12B C13B -0.2(3) . . . . ?
C10B C9B C12B C13B 179.9(2) . . . . ?
C8 C9 C12 C13 -0.5(3) . . . . ?
C10 C9 C12 C13 178.9(2) . . . . ?
C8 C15 C14 C13 0.2(4) . . . . ?
C9B C12B C13B C14B 0.1(4) . . . . ?
C9 C12 C13 C14 -0.5(4) . . . . ?
C15 C14 C13 C12 0.7(4) . . . . ?
C8B C15B C14B C13B -0.4(4) . . . . ?
C12B C13B C14B C15B 0.2(4) . . . . ?

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.040



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
