# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 2257609'
loop_
_audit_author_name
_audit_author_address
'Kenta Kato'
;Waseda University
Japan
;
_audit_update_record             
;
2023-04-20 deposited with the CCDC.	2023-05-23 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_SHFSU01_4a                  
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.20
RESPONSE: All measured crystals were of low quality. Therefore, not better data could be obtained. Additional refinement cycles do not improve the results. This structure is reported in order to support the Z-conformation of the molecule, and not the E-conformation, which can be assessed based on the available data.
;
_vrf_PLAT080_4a                  
;
PROBLEM: Maximum Shift/Error ............................       0.31 Why ?
RESPONSE: All measured crystals were of low quality. Therefore, not better data could be obtained. Additional refinement cycles do not improve the results. This structure is reported in order to support the Z-conformation of the molecule, and not the E-conformation, which can be assessed based on the available data.
;
_vrf_PLAT340_4a                  
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02294 Ang.
RESPONSE: All measured crystals were of low quality. Therefore, not better data could be obtained. Additional refinement cycles do not improve the results. This structure is reported in order to support the Z-conformation of the molecule, and not the E-conformation, which can be assessed based on the available data.
;
# Added during the CSD deposition process: Thursday 20 April 2023 02:52 AM
# end Validation Reply Form

_audit_creation_date             2022-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H24 B N3 O6 S'
_chemical_formula_sum            'C21 H24 B N3 O6 S'
_chemical_formula_weight         457.30
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
B B 0.0090 0.0039 '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'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           82
_space_group_name_H-M_alt        'I -4'
_space_group_name_Hall           'I -4'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'

_cell_length_a                   26.3367(14)
_cell_length_b                   26.3367(14)
_cell_length_c                   6.5069(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4513.3(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1126
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      63.0010
_cell_measurement_theta_min      3.3520
_shelx_estimated_absorpt_T_max   0.937
_shelx_estimated_absorpt_T_min   0.243
_exptl_absorpt_coefficient_mu    1.641
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.503
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1920
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-13 -11 0 0.0224
-13 11 0 0.0264
11 -13 0 0.0206
-11 -13 0 0.0246
13 11 0 0.0187
10 -11 2 0.1798
11 13 0 0.0151
-12 11 -1 0.0508

_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.05
_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
-13.0695 -11.0376 -0.0175 -0.0021 0.0099 0.9999
-12.6914 11.4456 -0.2021 -0.9830 0.1272 0.1324
10.9454 -13.1288 0.1931 0.9916 -0.1290 0.0091
-11.4646 -12.6726 0.1974 0.1383 0.0367 0.9897
13.0929 11.0038 0.0909 0.0075 0.0068 -0.9999
10.3754 -11.2280 1.8917 0.9574 0.2855 -0.0429
11.4626 12.6985 -0.0457 -0.1332 -0.0011 -0.9911
-12.4119 11.4916 -0.6331 -0.9925 0.0249 0.1196

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1468
_diffrn_reflns_av_unetI/netI     0.1417
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11055
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.107
_diffrn_reflns_theta_min         3.356
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00  64.00   0.50    0.05    --  108.01 -61.00   0.00   60
  2  ω     36.00  89.00   0.50    0.05    --  108.01 -77.00  60.00  106
  3  ω     37.00  68.00   0.50    0.05    --  108.01 -61.00 120.00   62
  4  ω     37.00  63.00   0.50    0.05    --  108.01 -61.00  60.00   52
  5  ω    112.00 169.00   0.50    0.05    --  108.01  54.00  60.00  114
  6  ω     35.00  60.00   0.50    0.05    --  108.01 -54.00 -82.00   50
  7  ω     34.00  59.00   0.50    0.05    --  108.01 -61.00-120.00   50
  8  ω      1.00  33.00   0.50    0.05    --   43.05 -19.00-180.00   64
  9  ω     73.00 100.00   0.50    0.05    --  108.01 -95.00  60.00   54
 10  ω     44.00  95.00   0.50    0.05    --   43.05-133.00  45.00  102
 11  ω     81.00 117.00   0.50    0.05    --  108.01-133.00  45.00   72
 12  ω     35.00  60.00   0.50    0.05    --  108.01 -95.00  60.00   50
 13  ω     34.00  60.00   0.50    0.05    --  108.01 -95.00-150.00   52
 14  ω     63.00 104.00   0.50    0.05    --  108.01 -95.00-150.00   82
 15  ω     -4.00  34.00   0.50    0.05    --  -43.05  38.00 120.00   76
 16  ω    -43.00  -8.00   0.50    0.05    --  -43.05  38.00 120.00   70
 17  ω    -86.00 -28.00   0.50    0.05    --  -96.00 137.00 -68.00  116
 18  ω    -67.00 -40.00   0.50    0.05    --  -43.05 125.00-150.00   54
 19  ω    -92.00 -27.00   0.50    0.05    --  -96.00  77.00 -60.00  130
 20  ω   -164.00-115.00   0.50    0.05    --  -96.00 -54.00 -82.00   98
 21  ω   -112.00 -66.00   0.50    0.05    --  -43.05-137.00-131.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0371914000
_diffrn_orient_matrix_UB_12      -0.0439127000
_diffrn_orient_matrix_UB_13      0.0414942000
_diffrn_orient_matrix_UB_21      -0.0071980000
_diffrn_orient_matrix_UB_22      0.0072541000
_diffrn_orient_matrix_UB_23      0.2334433000
_diffrn_orient_matrix_UB_31      -0.0445273000
_diffrn_orient_matrix_UB_32      -0.0378655000
_diffrn_orient_matrix_UB_33      -0.0031977000
_diffrn_oxdiff_digest_frames     
;
011ee156908676283d01c48753d983e65201606345a
;
_diffrn_oxdiff_digest_hkl        
;
01a6c3d58342d63a1793c850bbdf658920f0be
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.896
_reflns_number_gt                2087
_reflns_number_total             4368
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details 
;
 Flack x determined using 554 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4368
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1709
_refine_ls_R_factor_gt           0.1006
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.306
_refine_ls_shift/su_mean         0.055
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1640P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2509
_refine_ls_wR_factor_ref         0.3332
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C10(H10A,H10B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C5(H5), C17(H17), C3(H3), C20(H20), C19(H19), C21(H21),
 C18(H18)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.30881(15) 0.73527(13) 0.6814(5) 0.0654(10) Uani 1 1 d . . . . .
O3 O 0.3688(3) 0.5537(3) 0.5542(11) 0.0497(19) Uani 1 1 d . . . . .
O5 O 0.3148(3) 0.5218(3) 0.2799(13) 0.059(2) Uani 1 1 d . . . . .
O1 O 0.2719(4) 0.7749(3) 0.6858(15) 0.072(3) Uani 1 1 d . . . . .
O6 O 0.3349(4) 0.4678(4) 0.0256(16) 0.077(3) Uani 1 1 d . . . . .
O2 O 0.3313(4) 0.7185(4) 0.8698(12) 0.073(3) Uani 1 1 d . . . . .
O4 O 0.4472(4) 0.5666(4) 0.6696(14) 0.078(3) Uani 1 1 d . . . . .
N2 N 0.3107(4) 0.6447(4) 0.5445(15) 0.056(3) Uani 1 1 d . . . . .
N3 N 0.3767(4) 0.5870(4) 0.2143(12) 0.053(2) Uani 1 1 d . . . . .
N1 N 0.2786(4) 0.6876(4) 0.5777(15) 0.059(3) Uani 1 1 d . . . . .
H1 H 0.250577 0.679603 0.643746 0.070 Uiso 1 1 d R . . . .
C9 C 0.4140(5) 0.5724(5) 0.5381(17) 0.054(3) Uani 1 1 d . . . . .
C1 C 0.3571(6) 0.7519(5) 0.5123(17) 0.058(3) Uani 1 1 d . . . . .
C12 C 0.3439(5) 0.5052(5) 0.1253(17) 0.059(3) Uani 1 1 d . . . . .
C8 C 0.2938(5) 0.6086(5) 0.4270(17) 0.053(3) Uani 1 1 d . . . . .
C11 C 0.3895(6) 0.5383(5) 0.0982(16) 0.058(3) Uani 1 1 d . . . . .
H11A H 0.395567 0.545447 -0.049142 0.069 Uiso 1 1 calc R . . . .
H11B H 0.420099 0.521949 0.156676 0.069 Uiso 1 1 calc R . . . .
C10 C 0.4201(5) 0.6042(6) 0.3445(19) 0.066(4) Uani 1 1 d . . . . .
H10A H 0.417693 0.640951 0.375484 0.080 Uiso 1 1 calc R . . . .
H10B H 0.453067 0.597322 0.276544 0.080 Uiso 1 1 calc R . . . .
C4 C 0.4343(6) 0.7763(5) 0.234(2) 0.064(4) Uani 1 1 d . . . . .
C6 C 0.4075(6) 0.7372(5) 0.552(2) 0.067(4) Uani 1 1 d . . . . .
H6 H 0.415801 0.719615 0.674729 0.081 Uiso 1 1 calc R . . . .
C14 C 0.2404(5) 0.6069(5) 0.341(2) 0.062(3) Uani 1 1 d . . . . .
H14A H 0.239492 0.582789 0.223923 0.074 Uiso 1 1 calc R . . . .
H14B H 0.231356 0.640894 0.287520 0.074 Uiso 1 1 calc R . . . .
C13 C 0.3589(6) 0.6264(5) 0.0692(18) 0.066(4) Uani 1 1 d . . . . .
H13A H 0.386486 0.635402 -0.024998 0.100 Uiso 1 1 calc GR . . . .
H13B H 0.348343 0.656623 0.146109 0.100 Uiso 1 1 calc GR . . . .
H13C H 0.330004 0.613317 -0.009633 0.100 Uiso 1 1 calc GR . . . .
C16 C 0.1468(6) 0.5897(6) 0.426(3) 0.074(4) Uani 1 1 d . . . . .
C15 C 0.2010(5) 0.5907(6) 0.500(2) 0.070(4) Uani 1 1 d . . . . .
H15A H 0.209974 0.556397 0.549637 0.084 Uiso 1 1 calc R . . . .
H15B H 0.203150 0.614192 0.618058 0.084 Uiso 1 1 calc R . . . .
C2 C 0.3472(6) 0.7790(6) 0.3329(19) 0.073(4) Uani 1 1 d . . . . .
H2 H 0.313322 0.789306 0.304041 0.088 Uiso 1 1 calc R . . . .
B1 B 0.3364(5) 0.5674(5) 0.3781(16) 0.046(3) Uani 1 1 d . . . . .
C5 C 0.4453(6) 0.7488(5) 0.410(3) 0.071(4) Uani 1 1 d . . . . .
H5 H 0.479041 0.737600 0.433445 0.086 Uiso 1 1 calc R . . . .
C17 C 0.1324(6) 0.6079(6) 0.236(3) 0.077(4) Uani 1 1 d . . . . .
H17 H 0.157316 0.619602 0.141346 0.092 Uiso 1 1 calc R . . . .
C3 C 0.3847(6) 0.7912(6) 0.198(2) 0.076(4) Uani 1 1 d . . . . .
H3 H 0.376762 0.810127 0.078173 0.091 Uiso 1 1 calc R . . . .
C20 C 0.0587(7) 0.5713(8) 0.503(4) 0.103(6) Uani 1 1 d . . . . .
H20 H 0.033984 0.559023 0.596737 0.124 Uiso 1 1 calc R . . . .
C7 C 0.4760(7) 0.7877(6) 0.085(3) 0.087(5) Uani 1 1 d . . . . .
H7A H 0.494501 0.817926 0.130289 0.130 Uiso 1 1 calc GR . . . .
H7B H 0.461440 0.793850 -0.051607 0.130 Uiso 1 1 calc GR . . . .
H7C H 0.499308 0.758744 0.078034 0.130 Uiso 1 1 calc GR . . . .
C19 C 0.0436(7) 0.5900(7) 0.309(4) 0.101(6) Uani 1 1 d . . . . .
H19 H 0.008952 0.589342 0.269278 0.121 Uiso 1 1 calc R . . . .
C21 C 0.1093(6) 0.5710(6) 0.555(4) 0.093(5) Uani 1 1 d . . . . .
H21 H 0.118950 0.557505 0.685037 0.112 Uiso 1 1 calc R . . . .
C18 C 0.0794(7) 0.6090(6) 0.181(4) 0.097(6) Uani 1 1 d . . . . .
H18 H 0.069346 0.623289 0.053703 0.117 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.425(9) . ?
S1 O2 1.431(9) . ?
S1 N1 1.633(11) . ?
S1 C1 1.737(15) . ?
O3 C9 1.293(15) . ?
O3 B1 1.474(14) . ?
O5 C12 1.338(13) . ?
O5 B1 1.473(15) . ?
O6 C12 1.203(16) . ?
O4 C9 1.233(15) . ?
N2 N1 1.425(14) . ?
N2 C8 1.300(16) . ?
N3 C11 1.527(15) . ?
N3 C10 1.494(16) . ?
N3 C13 1.479(14) . ?
N3 B1 1.592(16) . ?
C9 C10 1.521(15) . ?
C1 C6 1.41(2) . ?
C1 C2 1.394(16) . ?
C12 C11 1.49(2) . ?
C8 C14 1.516(18) . ?
C8 B1 1.592(19) . ?
C4 C5 1.385(19) . ?
C4 C3 1.38(2) . ?
C4 C7 1.49(2) . ?
C6 C5 1.39(2) . ?
C14 C15 1.525(18) . ?
C16 C15 1.51(2) . ?
C16 C17 1.38(2) . ?
C16 C21 1.39(2) . ?
C2 C3 1.36(2) . ?
C17 C18 1.44(2) . ?
C20 C19 1.41(3) . ?
C20 C21 1.38(3) . ?
C19 C18 1.35(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 119.4(6) . . ?
O1 S1 N1 103.9(6) . . ?
O1 S1 C1 109.1(6) . . ?
O2 S1 N1 108.6(6) . . ?
O2 S1 C1 108.5(6) . . ?
N1 S1 C1 106.7(6) . . ?
C9 O3 B1 112.2(9) . . ?
C12 O5 B1 111.9(10) . . ?
C8 N2 N1 117.8(10) . . ?
C11 N3 B1 101.9(9) . . ?
C10 N3 C11 111.5(10) . . ?
C10 N3 B1 103.3(8) . . ?
C13 N3 C11 110.1(9) . . ?
C13 N3 C10 113.1(10) . . ?
C13 N3 B1 116.4(10) . . ?
N2 N1 S1 112.5(9) . . ?
O3 C9 C10 112.0(10) . . ?
O4 C9 O3 123.3(11) . . ?
O4 C9 C10 124.6(12) . . ?
C6 C1 S1 120.5(10) . . ?
C2 C1 S1 121.4(11) . . ?
C2 C1 C6 118.1(14) . . ?
O5 C12 C11 111.0(11) . . ?
O6 C12 O5 124.1(13) . . ?
O6 C12 C11 125.0(11) . . ?
N2 C8 C14 123.8(12) . . ?
N2 C8 B1 112.2(10) . . ?
C14 C8 B1 124.0(10) . . ?
C12 C11 N3 104.8(10) . . ?
N3 C10 C9 102.8(10) . . ?
C5 C4 C7 119.2(14) . . ?
C3 C4 C5 118.9(13) . . ?
C3 C4 C7 121.9(13) . . ?
C5 C6 C1 119.5(13) . . ?
C8 C14 C15 112.9(10) . . ?
C17 C16 C15 122.6(15) . . ?
C17 C16 C21 118.3(16) . . ?
C21 C16 C15 119.1(15) . . ?
C16 C15 C14 115.7(12) . . ?
C3 C2 C1 121.6(14) . . ?
O3 B1 O5 111.2(10) . . ?
O3 B1 N3 102.3(9) . . ?
O3 B1 C8 114.8(8) . . ?
O5 B1 N3 103.4(8) . . ?
O5 B1 C8 111.8(10) . . ?
C8 B1 N3 112.4(10) . . ?
C4 C5 C6 121.0(14) . . ?
C16 C17 C18 119.5(17) . . ?
C2 C3 C4 120.8(12) . . ?
C21 C20 C19 120(2) . . ?
C18 C19 C20 118.9(19) . . ?
C20 C21 C16 122(2) . . ?
C19 C18 C17 121(2) . . ?

_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 4.432
_oxdiff_exptl_absorpt_empirical_full_min 0.441
####################################################################### 
# 
# 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_CMBT
_database_code_depnum_ccdc_archive 'CCDC 2257615'
loop_
_audit_author_name
_audit_author_address
'Kenta Kato'
;Waseda University
Japan
;
_audit_update_record             
;
2023-04-20 deposited with the CCDC.	2023-05-23 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT414_CMBT                
;
PROBLEM: Short Intra D-H..H-X       H3       ..H7B      .       1.84 Ang.
RESPONSE: H3 and H7B atoms are amine group and methylene group hydrogens which were added with a HFIX command suitable for atoms involved in hydrogen bonding. The conformation they were assigned is not entirely correct and brings them in close proximity to nearby each other. The conformational freedom in the actual structure allows for a slightly different location of hydroxyl hydrogens and excludes any possibility of clashes.
;
# Added during the CSD deposition process: Thursday 20 April 2023 03:19 AM
# end Validation Reply Form

_audit_creation_date             2022-10-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H17 B Cl N3 O6 S, C4 H8 O2'
_chemical_formula_sum            'C18 H25 B Cl N3 O8 S'
_chemical_formula_weight         489.73
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H17 B Cl N3 O6 S'
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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   13.2505(2)
_cell_length_b                   15.1794(2)
_cell_length_c                   11.4864(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.823(2)
_cell_angle_gamma                90
_cell_volume                     2310.07(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7933
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.4350
_cell_measurement_theta_min      3.3280
_shelx_estimated_absorpt_T_max   0.898
_shelx_estimated_absorpt_T_min   0.514
_exptl_absorpt_coefficient_mu    2.742
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.366
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-8 2 0 0.0386
1 10 0 0.0150
-1 -10 0 0.0243
-1 2 -7 0.1120
9 -1 1 0.0160
-9 0 0 0.0435
-8 2 -1 0.0403
-1 1 7 0.1497
8 -2 1 0.0136

_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.06
_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
-8.4324 1.8350 -0.4217 0.0877 0.3867 0.9180
1.2756 9.7403 0.1296 -0.9432 0.3322 -0.0092
-1.2756 -9.7403 -0.1296 0.9432 -0.3322 0.0092
-0.6814 1.9649 -7.2725 -0.4353 -0.7180 0.5432
8.5071 -0.6492 0.9037 -0.1822 -0.2900 -0.9395
-8.5824 0.4871 -0.2799 0.2233 0.3577 0.9068
-8.4226 1.8191 -0.5554 0.0838 0.3706 0.9250
-0.8121 0.9419 7.3969 0.2180 0.9078 -0.3583
8.3157 -1.7178 1.3087 -0.0613 -0.2769 -0.9590

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19672
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.175
_diffrn_reflns_theta_min         3.336
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00  35.00   0.50    1.79    --  -42.99  37.00 -49.00  148
  2  ω   -104.00 -30.00   0.50    1.79    --  -42.99 -37.00 155.00  148
  3  ω     61.00  86.00   0.50    1.79    --   42.99-159.00 141.00   50
  4  ω   -170.00 -79.00   0.50    7.17    --  -96.00 -37.00 155.00  182
  5  ω    -83.00 -42.00   0.50    7.17    --  -96.00 119.00  20.00   82
  6  ω     67.00 134.00   0.50    7.17    --  108.01-159.00 141.00  134
  7  ω    109.00 154.00   0.50    7.17    --  108.01  86.00 130.00   90
  8  ω     85.00 114.00   0.50    7.17    --  108.01  37.00 -49.00   58
  9  ω     37.00 109.00   0.50    7.17    --  108.01-119.00 -65.00  144
 10  ω     75.00 121.00   0.50    1.79    --   42.99 178.00  60.00   92
 11  ω    -71.00 -28.00   0.50    7.17    --  -96.00 125.00  60.00   86
 12  ω    -50.00 -24.00   0.50    7.17    --  -96.00  45.00 120.00   52
 13  ω    -86.00 -61.00   0.50    7.17    --  -96.00 125.00 -30.00   50
 14  ω    -55.00 -24.00   0.50    7.17    --  -96.00  61.00  30.00   62
 15  ω   -138.00 -88.00   0.50    7.17    --  -96.00-125.00  90.00  100
 16  ω     84.00 172.00   0.50    7.17    --  108.01  30.00  60.00  176
 17  ω     36.00  88.00   0.50    7.17    --  108.01 -77.00  90.00  104
 18  ω     41.00  97.00   0.50    7.17    --  108.01 -77.00 150.00  112
 19  ω     49.00 106.00   0.50    7.17    --  108.01 -95.00 150.00  114
 20  ω     80.00 112.00   0.50    7.17    --  108.01-125.00   0.00   64
 21  ω     99.00 164.00   0.50    7.17    --  108.01 125.00 -30.00  130
 22  ω     48.00  74.00   0.50    7.17    --  108.01-125.00   0.00   52
 23  ω     92.00 118.00   0.50    7.17    --  108.01 -83.00  10.00   52
 24  ω    -51.00 -26.00   0.50    7.17    --  -96.00  45.00 -30.00   50
 25  ω   -132.00 -97.00   0.50    7.17    --  -96.00 -30.00-180.00   70
 26  ω   -160.00-134.00   0.50    7.17    --  -96.00 -30.00-180.00   52
 27  ω    -51.00 -25.00   0.50    7.17    --  -96.00  45.00  60.00   52
 28  ω    -51.00 -26.00   0.50    7.17    --  -96.00  45.00  30.00   50
 29  ω    -51.00 -26.00   0.50    7.17    --  -96.00  45.00  90.00   50
 30  ω     48.00  74.00   0.50    7.17    --  108.01 -95.00-120.00   52
 31  ω     79.00 105.00   0.50    7.17    --  108.01 -95.00 -30.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0325367000
_diffrn_orient_matrix_UB_12      -0.0930720000
_diffrn_orient_matrix_UB_13      0.0377560000
_diffrn_orient_matrix_UB_21      -0.0431904000
_diffrn_orient_matrix_UB_22      0.0382586000
_diffrn_orient_matrix_UB_23      0.1131102000
_diffrn_orient_matrix_UB_31      -0.1028918000
_diffrn_orient_matrix_UB_32      0.0133501000
_diffrn_orient_matrix_UB_33      -0.0614383000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3990
_reflns_number_total             4601
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.658
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4601
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0496
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0725P)²+1.2179P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1320
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C4(H4A,H4B), C2(H2A,H2B), C17(H17A,H17B)
1.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C13(H13), C9(H9), C10(H10), C12(H12)
1.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C14(H14A,H14B,H14C), C18(H18A,H18B,H18C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.35897(4) 0.56947(3) 0.07238(4) 0.02509(15) Uani 1 1 d . . . . .
Cl1 Cl 0.66532(4) 0.44789(4) 0.38848(5) 0.03219(16) Uani 1 1 d . . . . .
O3 O 0.76855(11) 0.64243(10) 0.31283(13) 0.0263(3) Uani 1 1 d . . . . .
O1 O 0.63995(12) 0.73998(10) 0.23002(12) 0.0251(3) Uani 1 1 d . . . . .
O5 O 0.31098(12) 0.49274(11) 0.02519(13) 0.0301(4) Uani 1 1 d . . . . .
O2 O 0.58547(14) 0.87726(10) 0.25209(14) 0.0323(4) Uani 1 1 d . . . . .
O6 O 0.38120(13) 0.64260(11) -0.00193(14) 0.0320(4) Uani 1 1 d . . . . .
N1 N 0.62703(13) 0.68833(12) 0.42981(14) 0.0216(4) Uani 1 1 d . . . . .
O4 O 0.88454(13) 0.62534(15) 0.45456(17) 0.0457(5) Uani 1 1 d . . . . .
N2 N 0.52089(13) 0.59790(12) 0.18464(15) 0.0230(4) Uani 1 1 d . . . . .
O8 O 0.97173(14) 0.87104(14) 0.44447(18) 0.0462(5) Uani 1 1 d . . . . .
N3 N 0.46662(14) 0.53287(12) 0.12690(15) 0.0244(4) Uani 1 1 d . . . . .
H3 H 0.487369 0.478061 0.120113 0.029 Uiso 1 1 calc R U . . .
O7 O 0.83174(17) 0.83527(15) 0.3465(2) 0.0572(6) Uani 1 1 d . . . . .
C5 C 0.52858(16) 0.65133(16) 0.46829(19) 0.0271(4) Uani 1 1 d . . . . .
H5A H 0.532952 0.586913 0.471045 0.041 Uiso 1 1 calc R U . . .
H5B H 0.475114 0.668841 0.413178 0.041 Uiso 1 1 calc R U . . .
H5C H 0.513045 0.673950 0.545911 0.041 Uiso 1 1 calc R U . . .
C6 C 0.60315(16) 0.57767(14) 0.23893(18) 0.0231(4) Uani 1 1 d . . . . .
C8 C 0.29040(16) 0.60803(15) 0.1916(2) 0.0274(5) Uani 1 1 d . . . . .
C7 C 0.64908(18) 0.48674(14) 0.24058(19) 0.0269(4) Uani 1 1 d . . . . .
H7A H 0.715371 0.488225 0.201955 0.032 Uiso 1 1 calc R U . . .
H7B H 0.604731 0.445623 0.196735 0.032 Uiso 1 1 calc R U . . .
C4 C 0.71351(16) 0.65889(15) 0.50524(19) 0.0268(4) Uani 1 1 d . . . . .
H4A H 0.695671 0.604744 0.548367 0.032 Uiso 1 1 calc R U . . .
H4B H 0.732214 0.705358 0.562052 0.032 Uiso 1 1 calc R U . . .
C1 C 0.61220(17) 0.80737(14) 0.29412(18) 0.0252(4) Uani 1 1 d . . . . .
C3 C 0.79971(17) 0.64123(16) 0.4234(2) 0.0297(5) Uani 1 1 d . . . . .
C2 C 0.61880(18) 0.78688(14) 0.42259(18) 0.0260(4) Uani 1 1 d . . . . .
H2A H 0.678823 0.815290 0.458590 0.031 Uiso 1 1 calc R U . . .
H2B H 0.557727 0.807841 0.462794 0.031 Uiso 1 1 calc R U . . .
C13 C 0.29540(18) 0.69674(17) 0.2218(2) 0.0346(5) Uani 1 1 d . . . . .
H13 H 0.332819 0.737188 0.176333 0.042 Uiso 1 1 calc R U . . .
C9 C 0.23711(18) 0.54773(16) 0.2581(2) 0.0313(5) Uani 1 1 d . . . . .
H9 H 0.235372 0.487210 0.237166 0.038 Uiso 1 1 calc R U . . .
C10 C 0.18672(19) 0.57720(19) 0.3553(2) 0.0375(6) Uani 1 1 d . . . . .
H10 H 0.149710 0.536597 0.400890 0.045 Uiso 1 1 calc R U . . .
C11 C 0.18962(19) 0.6661(2) 0.3871(2) 0.0396(6) Uani 1 1 d . . . . .
C12 C 0.24438(19) 0.72471(18) 0.3199(3) 0.0410(6) Uani 1 1 d . . . . .
H12 H 0.246999 0.785099 0.341460 0.049 Uiso 1 1 calc R U . . .
C16 C 0.9201(2) 0.85134(19) 0.3485(3) 0.0454(7) Uani 1 1 d . . . . .
B1 B 0.66069(18) 0.65930(15) 0.29726(19) 0.0220(5) Uani 1 1 d . . . . .
C17 C 0.9164(2) 0.8703(2) 0.5527(3) 0.0470(7) Uani 1 1 d . . . . .
H17A H 0.889261 0.810656 0.567906 0.056 Uiso 1 1 calc R U . . .
H17B H 0.859378 0.912301 0.548547 0.056 Uiso 1 1 calc R U . . .
C14 C 0.1333(2) 0.6972(3) 0.4922(3) 0.0539(8) Uani 1 1 d . . . . .
H14A H 0.060879 0.687268 0.480067 0.081 Uiso 1 1 calc R U . . .
H14B H 0.145813 0.760258 0.504046 0.081 Uiso 1 1 calc R U . . .
H14C H 0.156674 0.664439 0.560974 0.081 Uiso 1 1 calc R U . . .
C18 C 0.9891(2) 0.8965(2) 0.6473(3) 0.0520(7) Uani 1 1 d . . . . .
H18A H 1.014282 0.956007 0.632131 0.078 Uiso 1 1 calc R U . . .
H18B H 1.045848 0.855039 0.649443 0.078 Uiso 1 1 calc R U . . .
H18C H 0.954859 0.895496 0.722353 0.078 Uiso 1 1 calc R U . . .
C15 C 0.9862(3) 0.8539(3) 0.2435(3) 0.0640(9) Uani 1 1 d . . . . .
H15A H 1.026618 0.907953 0.244924 0.096 Uiso 1 1 calc R U . . .
H15B H 0.943934 0.852857 0.172745 0.096 Uiso 1 1 calc R U . . .
H15C H 1.031048 0.802597 0.244209 0.096 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O5 1.4299(16) . ?
S1 O6 1.4335(17) . ?
S1 N3 1.6462(18) . ?
S1 C8 1.755(2) . ?
Cl1 C7 1.808(2) . ?
O3 C3 1.330(3) . ?
O3 B1 1.460(3) . ?
O1 C1 1.316(3) . ?
O1 B1 1.472(3) . ?
O2 C1 1.216(3) . ?
N1 C5 1.493(3) . ?
N1 C4 1.495(3) . ?
N1 C2 1.502(3) . ?
N1 B1 1.653(3) . ?
O4 C3 1.199(3) . ?
N2 N3 1.385(3) . ?
N2 C6 1.285(3) . ?
O8 C16 1.323(4) . ?
O8 C17 1.453(4) . ?
N3 H3 0.8800 . ?
O7 C16 1.196(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.508(3) . ?
C6 B1 1.597(3) . ?
C8 C13 1.392(3) . ?
C8 C9 1.391(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.513(3) . ?
C1 C2 1.509(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C13 H13 0.9500 . ?
C13 C12 1.389(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.399(4) . ?
C11 C12 1.389(4) . ?
C11 C14 1.504(4) . ?
C12 H12 0.9500 . ?
C16 C15 1.501(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.495(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
O5 S1 O6 119.95(10) . . ?
O5 S1 N3 104.33(9) . . ?
O5 S1 C8 109.57(11) . . ?
O6 S1 N3 107.67(10) . . ?
O6 S1 C8 108.63(11) . . ?
N3 S1 C8 105.74(10) . . ?
C3 O3 B1 114.15(17) . . ?
C1 O1 B1 113.88(16) . . ?
C5 N1 C4 112.44(17) . . ?
C5 N1 C2 109.14(17) . . ?
C5 N1 B1 114.90(16) . . ?
C4 N1 C2 112.59(17) . . ?
C4 N1 B1 103.86(15) . . ?
C2 N1 B1 103.59(15) . . ?
C6 N2 N3 119.53(18) . . ?
C16 O8 C17 116.8(2) . . ?
S1 N3 H3 123.7 . . ?
N2 N3 S1 112.50(14) . . ?
N2 N3 H3 123.7 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 C7 124.33(19) . . ?
N2 C6 B1 114.49(18) . . ?
C7 C6 B1 120.96(18) . . ?
C13 C8 S1 119.6(2) . . ?
C9 C8 S1 118.81(18) . . ?
C9 C8 C13 121.5(2) . . ?
Cl1 C7 H7A 109.5 . . ?
Cl1 C7 H7B 109.5 . . ?
C6 C7 Cl1 110.66(15) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
N1 C4 H4A 110.6 . . ?
N1 C4 H4B 110.6 . . ?
N1 C4 C3 105.79(17) . . ?
H4A C4 H4B 108.7 . . ?
C3 C4 H4A 110.6 . . ?
C3 C4 H4B 110.6 . . ?
O1 C1 C2 111.97(18) . . ?
O2 C1 O1 122.56(19) . . ?
O2 C1 C2 125.5(2) . . ?
O3 C3 C4 111.34(18) . . ?
O4 C3 O3 124.4(2) . . ?
O4 C3 C4 124.3(2) . . ?
N1 C2 C1 105.21(16) . . ?
N1 C2 H2A 110.7 . . ?
N1 C2 H2B 110.7 . . ?
C1 C2 H2A 110.7 . . ?
C1 C2 H2B 110.7 . . ?
H2A C2 H2B 108.8 . . ?
C8 C13 H13 120.8 . . ?
C12 C13 C8 118.4(3) . . ?
C12 C13 H13 120.8 . . ?
C8 C9 H9 120.5 . . ?
C10 C9 C8 119.0(2) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.7(3) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C14 120.0(3) . . ?
C12 C11 C10 119.0(2) . . ?
C12 C11 C14 120.9(3) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 C13 121.3(2) . . ?
C11 C12 H12 119.4 . . ?
O8 C16 C15 111.3(3) . . ?
O7 C16 O8 123.8(3) . . ?
O7 C16 C15 124.9(3) . . ?
O3 B1 O1 112.66(18) . . ?
O3 B1 N1 102.15(15) . . ?
O3 B1 C6 112.08(18) . . ?
O1 B1 N1 102.17(16) . . ?
O1 B1 C6 109.94(17) . . ?
C6 B1 N1 117.38(17) . . ?
O8 C17 H17A 110.3 . . ?
O8 C17 H17B 110.3 . . ?
O8 C17 C18 107.0(2) . . ?
H17A C17 H17B 108.6 . . ?
C18 C17 H17A 110.3 . . ?
C18 C17 H17B 110.3 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
S1 C8 C13 C12 -176.89(18) . . . . ?
S1 C8 C9 C10 177.09(17) . . . . ?
O1 C1 C2 N1 -15.6(2) . . . . ?
O5 S1 N3 N2 -175.58(14) . . . . ?
O5 S1 C8 C13 -153.99(18) . . . . ?
O5 S1 C8 C9 29.9(2) . . . . ?
O2 C1 C2 N1 165.0(2) . . . . ?
O6 S1 N3 N2 55.95(17) . . . . ?
O6 S1 C8 C13 -21.2(2) . . . . ?
O6 S1 C8 C9 162.71(17) . . . . ?
N1 C4 C3 O3 -10.5(3) . . . . ?
N1 C4 C3 O4 171.8(2) . . . . ?
N2 C6 C7 Cl1 -123.2(2) . . . . ?
N2 C6 B1 O3 -155.47(18) . . . . ?
N2 C6 B1 O1 -29.4(3) . . . . ?
N2 C6 B1 N1 86.8(2) . . . . ?
N3 S1 C8 C13 94.11(19) . . . . ?
N3 S1 C8 C9 -81.96(19) . . . . ?
N3 N2 C6 C7 2.8(3) . . . . ?
N3 N2 C6 B1 177.56(17) . . . . ?
C5 N1 C4 C3 140.25(19) . . . . ?
C5 N1 C2 C1 -105.41(19) . . . . ?
C5 N1 B1 O3 -138.77(17) . . . . ?
C5 N1 B1 O1 104.52(19) . . . . ?
C5 N1 B1 C6 -15.8(3) . . . . ?
C6 N2 N3 S1 175.03(16) . . . . ?
C8 S1 N3 N2 -60.03(17) . . . . ?
C8 C13 C12 C11 0.1(4) . . . . ?
C8 C9 C10 C11 -0.5(3) . . . . ?
C7 C6 B1 O3 19.5(3) . . . . ?
C7 C6 B1 O1 145.56(19) . . . . ?
C7 C6 B1 N1 -98.3(2) . . . . ?
C4 N1 C2 C1 128.99(19) . . . . ?
C4 N1 B1 O3 -15.5(2) . . . . ?
C4 N1 B1 O1 -132.25(17) . . . . ?
C4 N1 B1 C6 107.4(2) . . . . ?
C1 O1 B1 O3 -103.2(2) . . . . ?
C1 O1 B1 N1 5.7(2) . . . . ?
C1 O1 B1 C6 131.02(18) . . . . ?
C3 O3 B1 O1 119.0(2) . . . . ?
C3 O3 B1 N1 10.1(2) . . . . ?
C3 O3 B1 C6 -116.4(2) . . . . ?
C2 N1 C4 C3 -96.0(2) . . . . ?
C2 N1 B1 O3 102.28(17) . . . . ?
C2 N1 B1 O1 -14.44(19) . . . . ?
C2 N1 B1 C6 -134.74(19) . . . . ?
C13 C8 C9 C10 1.1(3) . . . . ?
C9 C8 C13 C12 -0.9(3) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
C9 C10 C11 C14 179.3(2) . . . . ?
C10 C11 C12 C13 0.5(4) . . . . ?
C16 O8 C17 C18 -178.6(3) . . . . ?
B1 O3 C3 O4 177.2(2) . . . . ?
B1 O3 C3 C4 -0.5(3) . . . . ?
B1 O1 C1 O2 -174.8(2) . . . . ?
B1 O1 C1 C2 5.7(3) . . . . ?
B1 N1 C4 C3 15.4(2) . . . . ?
B1 N1 C2 C1 17.4(2) . . . . ?
B1 C6 C7 Cl1 62.4(2) . . . . ?
C17 O8 C16 O7 1.7(4) . . . . ?
C17 O8 C16 C15 -179.6(3) . . . . ?
C14 C11 C12 C13 -179.1(2) . . . . ?

_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 1.906
_oxdiff_exptl_absorpt_empirical_full_min 0.537
