# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_kv
_database_code_depnum_ccdc_archive 'CCDC 2091448'
loop_
_audit_author_name
_audit_author_address
'Krishnan Venkatasubbaiah'
;NISER
India
;
_audit_update_record             
;
2021-06-22 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;
_audit_creation_date             2017-06-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H34 B2 S2'
_chemical_formula_sum            'C30 H34 B2 S2'
_chemical_formula_weight         480.31
_chemical_melting_point          ?
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'
B B 0.0013 0.0007 '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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.3621(3)
_cell_length_b                   16.4766(7)
_cell_length_c                   11.3205(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.878(2)
_cell_angle_gamma                90
_cell_volume                     1370.06(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5550
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      2.19
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0582 before and 0.0415 after correction.
The Ratio of minimum to maximum transmission is 0.9368.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22133
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.357
_diffrn_reflns_theta_min         2.186
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2663
_reflns_number_total             3394
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         3394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0802P)²+0.3647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1429
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C9(H9)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C3(H3A,H3B,H3C), C6(H6A,H6B,H6C), C13(H13A,H13B,H13C),
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.059
;
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 -0.23539(7) 1.01756(3) 0.78546(4) 0.04829(17) Uani 1 1 d . . . . .
C10 C 0.1929(3) 0.65514(10) 0.59707(16) 0.0460(4) Uani 1 1 d . . . . .
C11 C 0.0293(2) 0.67846(10) 0.53933(15) 0.0427(4) Uani 1 1 d . . . . .
H11 H -0.052463 0.638732 0.511473 0.051 Uiso 1 1 calc R . . . .
C12 C -0.0158(2) 0.75993(9) 0.52190(14) 0.0367(3) Uani 1 1 d . . . . .
C7 C 0.1071(2) 0.82076(9) 0.56098(13) 0.0343(3) Uani 1 1 d . . . . .
C4 C 0.1127(2) 0.95301(9) 0.41714(14) 0.0358(3) Uani 1 1 d . . . . .
C2 C -0.0501(2) 0.96557(9) 0.61732(14) 0.0350(3) Uani 1 1 d . . . . .
C8 C 0.2731(2) 0.79735(10) 0.62019(15) 0.0412(4) Uani 1 1 d . . . . .
C9 C 0.3122(3) 0.71535(11) 0.63610(16) 0.0470(4) Uani 1 1 d . . . . .
H9 H 0.423023 0.700615 0.674479 0.056 Uiso 1 1 calc R . . . .
C15 C -0.1979(3) 0.78220(13) 0.46213(19) 0.0539(5) Uani 1 1 d . . . . .
H15A H -0.237604 0.739936 0.407984 0.081 Uiso 1 1 calc GR . . . .
H15B H -0.187174 0.832164 0.419549 0.081 Uiso 1 1 calc GR . . . .
H15C H -0.285141 0.788685 0.520747 0.081 Uiso 1 1 calc GR . . . .
C5 C 0.2162(2) 0.91852(10) 0.33310(15) 0.0430(4) Uani 1 1 d . . . . .
C1 C -0.1053(2) 0.94313(10) 0.72653(15) 0.0398(4) Uani 1 1 d . . . . .
C3 C -0.0666(3) 0.86906(12) 0.80059(19) 0.0596(5) Uani 1 1 d . . . . .
H3A H -0.051824 0.823122 0.749966 0.089 Uiso 1 1 calc GR . . . .
H3B H -0.166144 0.859363 0.849305 0.089 Uiso 1 1 calc GR . . . .
H3C H 0.043089 0.877199 0.850003 0.089 Uiso 1 1 calc GR . . . .
C6 C 0.3101(3) 0.83761(12) 0.3284(2) 0.0629(6) Uani 1 1 d . . . . .
H6A H 0.226781 0.795358 0.346842 0.094 Uiso 1 1 calc GR . . . .
H6B H 0.413248 0.836811 0.385024 0.094 Uiso 1 1 calc GR . . . .
H6C H 0.350147 0.829028 0.250444 0.094 Uiso 1 1 calc GR . . . .
C13 C 0.4062(3) 0.86154(14) 0.6665(2) 0.0627(6) Uani 1 1 d . . . . .
H13A H 0.507323 0.836054 0.709851 0.094 Uiso 1 1 calc GR . . . .
H13B H 0.346641 0.897818 0.717822 0.094 Uiso 1 1 calc GR . . . .
H13C H 0.449294 0.891523 0.601273 0.094 Uiso 1 1 calc GR . . . .
C14 C 0.2369(4) 0.56615(12) 0.6172(2) 0.0727(7) Uani 1 1 d . . . . .
H14A H 0.348874 0.553267 0.582602 0.109 Uiso 1 1 calc GR . . . .
H14B H 0.140422 0.533520 0.581023 0.109 Uiso 1 1 calc GR . . . .
H14C H 0.249241 0.555284 0.700650 0.109 Uiso 1 1 calc GR . . . .
B1 B 0.0605(2) 0.91286(10) 0.53403(16) 0.0350(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C5 1.7194(17) 3_576 ?
S1 C1 1.7182(17) . ?
C10 C11 1.385(3) . ?
C10 C9 1.378(3) . ?
C10 C14 1.516(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.394(2) . ?
C12 C7 1.402(2) . ?
C12 C15 1.506(3) . ?
C7 C8 1.407(2) . ?
C7 B1 1.581(2) . ?
C4 C2 1.463(2) 3_576 ?
C4 C5 1.381(2) . ?
C4 B1 1.551(2) . ?
C2 C4 1.463(2) 3_576 ?
C2 C1 1.378(2) . ?
C2 B1 1.552(2) . ?
C8 C9 1.391(2) . ?
C8 C13 1.512(3) . ?
C9 H9 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C5 S1 1.7194(17) 3_576 ?
C5 C6 1.504(2) . ?
C1 C3 1.497(2) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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 C5 93.26(8) . 3_576 ?
C11 C10 C14 120.63(19) . . ?
C9 C10 C11 117.82(15) . . ?
C9 C10 C14 121.55(18) . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.70(16) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C7 120.09(16) . . ?
C11 C12 C15 119.66(16) . . ?
C7 C12 C15 120.25(15) . . ?
C12 C7 C8 118.39(14) . . ?
C12 C7 B1 119.89(14) . . ?
C8 C7 B1 121.68(15) . . ?
C2 C4 B1 121.80(13) 3_576 . ?
C5 C4 C2 111.86(14) . 3_576 ?
C5 C4 B1 126.32(14) . . ?
C4 C2 B1 121.32(13) 3_576 . ?
C1 C2 C4 112.23(13) . 3_576 ?
C1 C2 B1 126.42(14) . . ?
C7 C8 C13 119.69(16) . . ?
C9 C8 C7 119.59(16) . . ?
C9 C8 C13 120.72(17) . . ?
C10 C9 C8 122.39(16) . . ?
C10 C9 H9 118.8 . . ?
C8 C9 H9 118.8 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C5 S1 111.35(12) . 3_576 ?
C4 C5 C6 131.70(16) . . ?
C6 C5 S1 116.95(13) . 3_576 ?
C2 C1 S1 111.29(12) . . ?
C2 C1 C3 131.64(16) . . ?
C3 C1 S1 117.03(12) . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 B1 C7 120.75(13) . . ?
C4 B1 C2 116.73(13) . . ?
C2 B1 C7 122.38(14) . . ?

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
C10 C11 C12 C7 1.3(3) . . . . ?
C10 C11 C12 C15 -178.00(16) . . . . ?
C11 C10 C9 C8 0.5(3) . . . . ?
C11 C12 C7 C8 -1.6(2) . . . . ?
C11 C12 C7 B1 176.22(15) . . . . ?
C12 C7 C8 C9 1.3(2) . . . . ?
C12 C7 C8 C13 -178.27(16) . . . . ?
C12 C7 B1 C4 -87.90(19) . . . . ?
C12 C7 B1 C2 87.7(2) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C4 C2 C1 S1 1.50(19) 3_576 . . . ?
C4 C2 C1 C3 -176.07(19) 3_576 . . . ?
C4 C2 B1 C7 -171.58(15) 3_576 . . . ?
C4 C2 B1 C4 4.2(3) 3_576 . . . ?
C2 C4 C5 S1 -0.66(19) 3_576 . . 3_576 ?
C2 C4 C5 C6 179.6(2) 3_576 . . . ?
C2 C4 B1 C7 171.63(15) 3_576 . . . ?
C2 C4 B1 C2 -4.2(3) 3_576 . . . ?
C8 C7 B1 C4 89.8(2) . . . . ?
C8 C7 B1 C2 -94.5(2) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C15 C12 C7 C8 177.75(16) . . . . ?
C15 C12 C7 B1 -4.5(2) . . . . ?
C5 S1 C1 C2 -0.97(14) 3_576 . . . ?
C5 S1 C1 C3 176.99(16) 3_576 . . . ?
C5 C4 B1 C7 -6.9(3) . . . . ?
C5 C4 B1 C2 177.23(16) . . . . ?
C1 C2 B1 C7 6.4(3) . . . . ?
C1 C2 B1 C4 -177.79(16) . . . . ?
C13 C8 C9 C10 178.79(18) . . . . ?
C14 C10 C11 C12 178.68(18) . . . . ?
C14 C10 C9 C8 -178.93(19) . . . . ?
B1 C7 C8 C9 -176.44(15) . . . . ?
B1 C7 C8 C13 4.0(2) . . . . ?
B1 C4 C5 S1 177.99(13) . . . 3_576 ?
B1 C4 C5 C6 -1.7(3) . . . . ?
B1 C2 C1 S1 -176.64(13) . . . . ?
B1 C2 C1 C3 5.8(3) . . . . ?

_shelx_SHELXL_version_number     2016/4
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_kv-sns-tbxyl
_database_code_depnum_ccdc_archive 'CCDC 2091449'
loop_
_audit_author_name
_audit_author_address
'Krishnan Venkatasubbaiah'
;NISER
India
;
_audit_update_record             
;
2021-06-22 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;
_audit_creation_date             2019-01-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H30 B2 S2'
_chemical_formula_sum            'C28 H30 B2 S2'
_chemical_formula_weight         452.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C56 H60 B4 S4 '
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'
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                   10.54815(16)
_cell_length_b                   14.5492(2)
_cell_length_c                   8.34333(15)
_cell_angle_alpha                90
_cell_angle_beta                 97.4946(16)
_cell_angle_gamma                90
_cell_volume                     1269.49(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5648
_cell_measurement_temperature    297.6(8)
_cell_measurement_theta_max      74.9310
_cell_measurement_theta_min      4.2070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.979
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
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    1.183
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0963
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9588
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.394
_diffrn_reflns_theta_min         4.227
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.6(8)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00 -35.00   0.50    5.30    --  -38.50 -37.00-155.00  140
  2  ω    -42.00  28.00   0.50    5.30    --  -38.50  37.00   0.00  140
  3  ω    -17.00  53.00   0.50    5.30    --   49.56 -37.00-155.00  140
  4  ω     46.00 116.00   0.50    5.30    --   49.56  37.00   0.00  140
  5  ω     36.00 106.00   0.50   21.19    --  102.63 -37.00-155.00  140
  6  ω    100.00 169.00   0.50   21.19    --  102.63  37.00   0.00  138
  7  ω   -105.00 -35.00   0.50    5.30    --  -38.50 -37.00-120.00  140
  8  ω    -13.00  61.00   0.50    5.30    --   49.56 -57.00  90.00  148
  9  ω     46.00 116.00   0.50    5.30    --   49.56  37.00  60.00  140
 10  ω     40.00 116.00   0.50   21.19    --  102.63 -61.00 -60.00  152
 11  ω     38.00 107.00   0.50   21.19    --  102.63 -45.00-120.00  138
 12  ω     38.00 107.00   0.50   21.19    --  102.63 -45.00 -60.00  138
 13  ω     94.00 168.00   0.50   21.19    --  102.63 125.00-120.00  148
 14  ω     98.00 167.00   0.50   21.19    --  102.63  45.00-120.00  138
 15  ω     40.00 116.00   0.50   21.19    --  102.63 -61.00   0.00  152
 16  ω     38.00 118.00   0.50   21.19    --  102.63-125.00 -90.00  160
 17  ω     72.00 102.00   0.50   21.19    --  102.63 -45.00   0.00   60
 18  ω     38.00  68.00   0.50   21.19    --  102.63 -45.00   0.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0295865000
_diffrn_orient_matrix_UB_12      0.0113129000
_diffrn_orient_matrix_UB_13      -0.1846826000
_diffrn_orient_matrix_UB_21      0.1264900000
_diffrn_orient_matrix_UB_22      -0.0486468000
_diffrn_orient_matrix_UB_23      -0.0210566000
_diffrn_orient_matrix_UB_31      -0.0695305000
_diffrn_orient_matrix_UB_32      -0.0933546000
_diffrn_orient_matrix_UB_33      -0.0113645000
_diffrn_oxdiff_ac3_digest_frames 
;
018cf0367350379a05b5496a546e0fb5d800026d88d
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01dea1d8df717f085386a6005ef694e91d1f89
;
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2191
_reflns_number_total             2563
_reflns_odcompleteness_completeness 99.96
_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 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2563
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0680
_refine_ls_restrained_S_all      1.112
_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)+(0.1279P)²+0.2218P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1955
_refine_ls_wR_factor_ref         0.2030
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C10(H10)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.35511(6) 0.26323(4) 0.51372(9) 0.0572(3) Uani 1 1 d . . . . .
C3 C 0.50639(19) 0.40124(14) 0.5562(3) 0.0381(5) Uani 1 1 d . . . . .
C7 C 0.7496(2) 0.43060(14) 0.7080(3) 0.0396(5) Uani 1 1 d . . . . .
C2 C 0.39219(19) 0.43310(14) 0.4535(3) 0.0386(5) Uani 1 1 d . . . . .
C8 C 0.8472(2) 0.39500(16) 0.6281(3) 0.0465(6) Uani 1 1 d . . . . .
C1 C 0.3030(2) 0.36447(15) 0.4199(3) 0.0452(5) Uani 1 1 d . . . . .
C4 C 0.4976(2) 0.31016(15) 0.5991(3) 0.0456(6) Uani 1 1 d . . . . .
C12 C 0.7670(2) 0.43472(16) 0.8769(3) 0.0486(6) Uani 1 1 d . . . . .
C5 C 0.5905(3) 0.24830(17) 0.6986(4) 0.0588(7) Uani 1 1 d . . . . .
H5A H 0.548904 0.191612 0.719094 0.088 Uiso 1 1 calc GR . . . .
H5B H 0.620349 0.277780 0.799479 0.088 Uiso 1 1 calc GR . . . .
H5C H 0.661768 0.235910 0.641147 0.088 Uiso 1 1 calc GR . . . .
C6 C 0.1737(2) 0.36369(19) 0.3206(4) 0.0603(7) Uani 1 1 d . . . . .
H6A H 0.134727 0.304579 0.329082 0.091 Uiso 1 1 calc GR . . . .
H6B H 0.182873 0.375766 0.209535 0.091 Uiso 1 1 calc GR . . . .
H6C H 0.120923 0.410218 0.359524 0.091 Uiso 1 1 calc GR . . . .
C9 C 0.9601(3) 0.3644(2) 0.7165(4) 0.0632(8) Uani 1 1 d . . . . .
H9 H 1.025010 0.341095 0.662746 0.076 Uiso 1 1 calc R . . . .
C11 C 0.8811(3) 0.4030(2) 0.9628(3) 0.0645(8) Uani 1 1 d . . . . .
H11 H 0.892690 0.405307 1.075113 0.077 Uiso 1 1 calc R . . . .
C13 C 0.8322(3) 0.3923(2) 0.4461(3) 0.0630(7) Uani 1 1 d . . . . .
H13A H 0.742942 0.391769 0.404560 0.095 Uiso 1 1 calc GR . . . .
H13B H 0.872252 0.337907 0.411353 0.095 Uiso 1 1 calc GR . . . .
H13C H 0.871859 0.445621 0.406476 0.095 Uiso 1 1 calc GR . . . .
C14 C 0.6639(3) 0.4743(2) 0.9658(4) 0.0695(8) Uani 1 1 d . . . . .
H14A H 0.650343 0.537665 0.936261 0.104 Uiso 1 1 calc GR . . . .
H14B H 0.689809 0.469883 1.080198 0.104 Uiso 1 1 calc GR . . . .
H14C H 0.585982 0.440592 0.937543 0.104 Uiso 1 1 calc GR . . . .
B1 B 0.6215(2) 0.46621(16) 0.6070(3) 0.0371(5) Uani 1 1 d . . . . .
C10 C 0.9767(3) 0.3682(2) 0.8822(4) 0.0718(9) Uani 1 1 d . . . . .
H10 H 1.052530 0.347350 0.940260 0.086 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 C1 1.724(2) . ?
S1 C4 1.719(2) . ?
C3 C2 1.460(3) . ?
C3 C4 1.379(3) . ?
C3 B1 1.553(3) . ?
C7 C8 1.397(3) . ?
C7 C12 1.398(3) . ?
C7 B1 1.584(3) . ?
C2 C1 1.376(3) . ?
C2 B1 1.550(3) 3_666 ?
C8 C9 1.390(3) . ?
C8 C13 1.506(4) . ?
C1 C6 1.500(3) . ?
C4 C5 1.499(3) . ?
C12 C11 1.396(4) . ?
C12 C14 1.508(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C9 H9 0.9300 . ?
C9 C10 1.372(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.379(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
B1 C2 1.550(3) 3_666 ?
C10 H10 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
C4 S1 C1 93.37(11) . . ?
C2 C3 B1 121.51(18) . . ?
C4 C3 C2 112.30(19) . . ?
C4 C3 B1 126.19(19) . . ?
C8 C7 C12 119.3(2) . . ?
C8 C7 B1 119.88(19) . . ?
C12 C7 B1 120.86(19) . . ?
C3 C2 B1 121.73(18) . 3_666 ?
C1 C2 C3 112.30(19) . . ?
C1 C2 B1 125.97(19) . 3_666 ?
C7 C8 C13 120.2(2) . . ?
C9 C8 C7 120.0(2) . . ?
C9 C8 C13 119.8(2) . . ?
C2 C1 S1 110.99(17) . . ?
C2 C1 C6 131.8(2) . . ?
C6 C1 S1 117.22(17) . . ?
C3 C4 S1 111.03(16) . . ?
C3 C4 C5 131.3(2) . . ?
C5 C4 S1 117.66(18) . . ?
C7 C12 C14 120.2(2) . . ?
C11 C12 C7 119.6(2) . . ?
C11 C12 C14 120.2(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 119.7 . . ?
C12 C11 H11 119.7 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.7 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 B1 C7 121.91(18) . . ?
C2 B1 C3 116.75(18) 3_666 . ?
C2 B1 C7 121.27(18) 3_666 . ?
C9 C10 C11 120.0(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?

_shelx_SHELXL_version_number     2016/4
_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 3.781
_oxdiff_exptl_absorpt_empirical_full_min 0.356
