# 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_BR-2-44A_exp_1233
_database_code_depnum_ccdc_archive 'CCDC 2287477'
loop_
_audit_author_name
_audit_author_address
'Julia Bruno'
;University College Dublin
Ireland
;
_audit_update_record             
;
2023-08-08 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;
_audit_creation_date             2023-05-16
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 N O4 S'
_chemical_formula_sum            'C18 H17 N O4 S'
_chemical_formula_weight         343.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H17NO4S
_chemical_oxdiff_usercomment     BR-2-44A_BhargavaReddy_McGarribleGroup
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   12.30520(10)
_cell_length_b                   7.33200(10)
_cell_length_c                   18.7530(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.2920(10)
_cell_angle_gamma                90
_cell_volume                     1653.14(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11707
_cell_measurement_temperature    104.4(5)
_cell_measurement_theta_max      72.6420
_cell_measurement_theta_min      3.6500
_shelx_estimated_absorpt_T_max   0.910
_shelx_estimated_absorpt_T_min   0.722
_exptl_absorpt_coefficient_mu    1.933
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.785
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.75a (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            'translucent intense colourless'
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 0 -11 0.0581
-3 4 2 0.0483
3 -4 1 0.0488
1 1 11 0.0879
4 4 0 0.0452
-4 -4 2 0.0520
-3 0 -10 0.0565
3 0 10 0.0825
8 0 -2 0.0235
-8 0 2 0.0217

_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
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
-1.6977 -0.1543 -11.0646 0.0343 0.1324 0.9906
-2.5350 4.4691 2.3752 -0.2337 -0.9712 0.0473
2.9603 -4.3721 0.6310 0.2215 0.9235 -0.3132
1.4016 0.6285 11.1493 -0.0587 -0.2340 -0.9705
4.0796 4.0603 -0.0167 0.5587 -0.8146 -0.1555
-3.7882 -4.1850 1.8096 -0.5659 0.8244 -0.0090
-2.6806 -0.2815 -10.3125 -0.0961 0.1442 0.9849
2.5789 0.1571 10.4132 0.0795 -0.1201 -0.9896
7.9782 0.0181 -1.9771 0.9487 0.0733 -0.3076
-7.9643 -0.0054 1.6536 -0.9401 -0.0726 0.3332

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22109
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.687
_diffrn_reflns_theta_min         3.676
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      104.4(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3196
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -17.00   1.00    4.34    --  -42.33 149.00 -59.00   87
  2  ω   -115.00 -62.00   1.00    4.34    --  -42.33-149.00-106.00   53
  3  ω    -85.00  -3.00   1.00    4.34    --  -42.33 122.00 137.00   82
  4  ω     39.00 114.00   1.00    4.34    --   42.33-149.00-106.00   75
  5  ω     39.00 129.00   1.00   17.34    --  104.49-149.00-106.00   90
  6  ω     99.00 176.00   1.00   17.34    --  104.49 122.00 137.00   77
  7  ω     33.00 111.00   1.00   17.34    --  104.49-122.00  56.00   78
  8  ω     83.00 167.00   1.00   17.34    --  104.49 149.00 -59.00   84
  9  ω   -115.00 -14.00   1.00    4.34    --  -42.33 -57.00-150.00  101
 10  ω   -117.00 -18.00   1.00    4.34    --  -42.33 -37.00 -60.00   99
 11  ω    103.00 178.00   1.00   17.34    --  104.49  77.00   0.00   75
 12  ω     31.00 109.00   1.00   17.34    --  104.49-111.00 150.00   78
 13  ω     28.00 137.00   1.00   17.34    --  104.49 -77.00  60.00  109
 14  ω    103.00 178.00   1.00   17.34    --  104.49  77.00-120.00   75
 15  ω    103.00 178.00   1.00   17.34    --  104.49  77.00-180.00   75
 16  ω    103.00 178.00   1.00   17.34    --  104.49  77.00 -30.00   75
 17  ω    103.00 178.00   1.00   17.34    --  104.49  77.00  30.00   75
 18  ω   -115.00 -14.00   1.00    4.34    --  -42.33 -57.00   0.00  101
 19  ω   -115.00 -14.00   1.00    4.34    --  -42.33 -57.00 -90.00  101
 20  ω   -115.00 -14.00   1.00    4.34    --  -42.33 -57.00  90.00  101
 21  ω   -115.00 -14.00   1.00    4.34    --  -42.33 -57.00 150.00  101
 22  ω    -67.00  32.00   1.00    4.34    --  -42.33  37.00   0.00   99
 23  ω     75.00 177.00   1.00   17.34    --  104.49  61.00 -60.00  102
 24  ω     76.00 178.00   1.00   17.34    --  104.49  30.00 120.00  102
 25  ω     76.00 178.00   1.00   17.34    --  104.49  30.00-150.00  102
 26  ω     31.00 109.00   1.00   17.34    --  104.49-111.00 -30.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1136838000
_diffrn_orient_matrix_UB_12      0.0232937000
_diffrn_orient_matrix_UB_13      -0.0208689000
_diffrn_orient_matrix_UB_21      0.0071415000
_diffrn_orient_matrix_UB_22      -0.2078534000
_diffrn_orient_matrix_UB_23      -0.0101651000
_diffrn_orient_matrix_UB_31      -0.0586322000
_diffrn_orient_matrix_UB_32      0.0202750000
_diffrn_orient_matrix_UB_33      -0.0808155000
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2873
_reflns_number_total             3235
_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 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.040
_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)+(0.0443P)²+0.8343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0877
_refine_special_details          ?
_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
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C13(H13), C14(H14),
 C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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 0.66362(3) 0.57758(5) 0.38242(2) 0.01979(11) Uani 1 1 d . . . . .
O1 O 0.47133(8) 0.92584(14) 0.33631(6) 0.0219(2) Uani 1 1 d . . . . .
O2 O 0.40758(9) 1.20564(15) 0.36025(7) 0.0323(3) Uani 1 1 d . . . . .
O3 O 0.71977(8) 0.74922(15) 0.38139(6) 0.0257(2) Uani 1 1 d . . . . .
O4 O 0.66137(9) 0.49670(16) 0.45226(6) 0.0276(3) Uani 1 1 d . . . . .
N1 N 0.38814(9) 0.94616(18) 0.42854(7) 0.0214(3) Uani 1 1 d . . . . .
C1 C 0.20152(12) 0.9967(2) 0.45452(8) 0.0226(3) Uani 1 1 d . . . . .
C2 C 0.15296(13) 0.8291(2) 0.46237(9) 0.0262(3) Uani 1 1 d . . . . .
H2 H 0.197375 0.730953 0.485390 0.031 Uiso 1 1 calc R U . . .
C3 C 0.03895(13) 0.8047(2) 0.43646(9) 0.0304(4) Uani 1 1 d . . . . .
H3 H 0.005957 0.689710 0.441728 0.036 Uiso 1 1 calc R U . . .
C4 C -0.02609(12) 0.9469(3) 0.40324(9) 0.0321(4) Uani 1 1 d . . . . .
H4 H -0.103623 0.929639 0.385330 0.038 Uiso 1 1 calc R U . . .
C5 C 0.02206(14) 1.1149(3) 0.39606(9) 0.0324(4) Uani 1 1 d . . . . .
H5 H -0.022582 1.213260 0.373407 0.039 Uiso 1 1 calc R U . . .
C6 C 0.13550(13) 1.1397(2) 0.42196(9) 0.0270(3) Uani 1 1 d . . . . .
H6 H 0.168060 1.255441 0.417340 0.032 Uiso 1 1 calc R U . . .
C7 C 0.32546(12) 1.0236(2) 0.47996(8) 0.0262(3) Uani 1 1 d . . . . .
H7A H 0.341630 1.155705 0.485749 0.031 Uiso 1 1 calc R U . . .
H7B H 0.350466 0.965166 0.528259 0.031 Uiso 1 1 calc R U . . .
C8 C 0.41912(11) 1.0451(2) 0.37483(9) 0.0226(3) Uani 1 1 d . . . . .
C9 C 0.46804(11) 0.7530(2) 0.36665(8) 0.0200(3) Uani 1 1 d . . . . .
C10 C 0.41775(11) 0.7641(2) 0.42273(8) 0.0223(3) Uani 1 1 d . . . . .
H10 H 0.404552 0.666412 0.453071 0.027 Uiso 1 1 calc R U . . .
C11 C 0.52165(12) 0.6034(2) 0.33402(8) 0.0225(3) Uani 1 1 d . . . . .
H11A H 0.519571 0.630762 0.282050 0.027 Uiso 1 1 calc R U . . .
H11B H 0.480625 0.488216 0.336471 0.027 Uiso 1 1 calc R U . . .
C12 C 0.71795(11) 0.4196(2) 0.32874(8) 0.0199(3) Uani 1 1 d . . . . .
C13 C 0.78597(12) 0.4780(2) 0.28268(8) 0.0231(3) Uani 1 1 d . . . . .
H13 H 0.805987 0.602867 0.281154 0.028 Uiso 1 1 calc R U . . .
C14 C 0.82409(12) 0.3502(2) 0.23894(9) 0.0252(3) Uani 1 1 d . . . . .
H14 H 0.871167 0.388342 0.207660 0.030 Uiso 1 1 calc R U . . .
C15 C 0.79421(13) 0.1669(2) 0.24033(9) 0.0256(3) Uani 1 1 d . . . . .
C16 C 0.72438(12) 0.1130(2) 0.28613(9) 0.0248(3) Uani 1 1 d . . . . .
H16 H 0.702565 -0.011199 0.286806 0.030 Uiso 1 1 calc R U . . .
C17 C 0.68649(12) 0.2375(2) 0.33050(8) 0.0233(3) Uani 1 1 d . . . . .
H17 H 0.639522 0.199404 0.361846 0.028 Uiso 1 1 calc R U . . .
C18 C 0.83604(16) 0.0266(3) 0.19414(10) 0.0372(4) Uani 1 1 d . . . . .
H18A H 0.776585 -0.060867 0.175373 0.056 Uiso 1 1 calc R U . . .
H18B H 0.899672 -0.037935 0.223785 0.056 Uiso 1 1 calc R U . . .
H18C H 0.859115 0.087061 0.153173 0.056 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 O3 1.4378(11) . ?
S1 O4 1.4433(11) . ?
S1 C11 1.7990(14) . ?
S1 C12 1.7574(15) . ?
O1 C8 1.3773(18) . ?
O1 C9 1.3933(17) . ?
O2 C8 1.2098(19) . ?
N1 C7 1.4710(18) . ?
N1 C8 1.360(2) . ?
N1 C10 1.3940(19) . ?
C1 C2 1.388(2) . ?
C1 C6 1.386(2) . ?
C1 C7 1.5109(19) . ?
C2 C3 1.395(2) . ?
C3 C4 1.379(3) . ?
C4 C5 1.386(3) . ?
C5 C6 1.389(2) . ?
C9 C10 1.332(2) . ?
C9 C11 1.478(2) . ?
C12 C13 1.392(2) . ?
C12 C17 1.392(2) . ?
C13 C14 1.391(2) . ?
C14 C15 1.395(2) . ?
C15 C16 1.395(2) . ?
C15 C18 1.505(2) . ?
C16 C17 1.382(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O4 118.29(7) . . ?
O3 S1 C11 108.59(7) . . ?
O3 S1 C12 109.07(7) . . ?
O4 S1 C11 107.27(7) . . ?
O4 S1 C12 109.40(7) . . ?
C12 S1 C11 103.14(7) . . ?
C8 O1 C9 107.83(11) . . ?
C8 N1 C7 123.24(13) . . ?
C8 N1 C10 109.50(12) . . ?
C10 N1 C7 127.10(13) . . ?
C2 C1 C7 120.73(14) . . ?
C6 C1 C2 119.43(14) . . ?
C6 C1 C7 119.83(15) . . ?
C1 C2 C3 120.03(15) . . ?
C4 C3 C2 120.28(16) . . ?
C3 C4 C5 119.78(15) . . ?
C4 C5 C6 120.06(16) . . ?
C1 C6 C5 120.40(16) . . ?
N1 C7 C1 112.17(12) . . ?
O2 C8 O1 123.00(14) . . ?
O2 C8 N1 130.43(15) . . ?
N1 C8 O1 106.57(13) . . ?
O1 C9 C11 116.85(12) . . ?
C10 C9 O1 109.00(13) . . ?
C10 C9 C11 134.10(14) . . ?
C9 C10 N1 107.07(13) . . ?
C9 C11 S1 109.90(10) . . ?
C13 C12 S1 120.32(12) . . ?
C17 C12 S1 118.48(11) . . ?
C17 C12 C13 121.11(14) . . ?
C14 C13 C12 118.78(14) . . ?
C13 C14 C15 120.97(14) . . ?
C14 C15 C16 118.95(15) . . ?
C14 C15 C18 121.62(15) . . ?
C16 C15 C18 119.42(15) . . ?
C17 C16 C15 120.94(14) . . ?
C16 C17 C12 119.23(14) . . ?

_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 1.670
_oxdiff_exptl_absorpt_empirical_full_min 0.432
####################################################################### 
# 
# 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_exp_1231_BR-2-66A
_database_code_depnum_ccdc_archive 'CCDC 2287478'
loop_
_audit_author_name
_audit_author_address
'Julia Bruno'
;University College Dublin
Ireland
;
_audit_update_record             
;
2023-08-08 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;
_audit_creation_date             2023-05-15
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 N O4 S'
_chemical_formula_sum            'C19 H19 N O4 S'
_chemical_formula_weight         357.41
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H19NO4S
_chemical_oxdiff_usercomment     BR-2-66A_BhargavaReddy_McGarribleGroup
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.37430(10)
_cell_length_b                   15.0097(2)
_cell_length_c                   15.6382(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1730.93(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10586
_cell_measurement_temperature    104.60(14)
_cell_measurement_theta_max      72.5330
_cell_measurement_theta_min      2.8060
_shelx_estimated_absorpt_T_max   0.767
_shelx_estimated_absorpt_T_min   0.569
_exptl_absorpt_coefficient_mu    1.867
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.426
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.75a (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            'metallic dark yellow'
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -3 6 0.1196
-1 2 -10 0.0802
0 -2 10 0.1194
3 -1 8 0.1373
5 1 0 0.1326
-3 -6 3 0.1117
-3 6 -5 0.1259
1 -8 6 0.1358
3 -6 5 0.1367
3 7 -4 0.0714
-1 -9 -4 0.0794
-2 8 3 0.0865
1 9 4 0.0723
4 6 2 0.1134

_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
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
-3.5374 -2.5300 6.3123 0.1631 0.6703 0.7239
-0.9955 2.1201 -9.6792 -0.2266 -0.9439 0.2402
0.3368 -2.3374 9.8278 0.2326 0.9672 -0.1022
2.9369 -1.1541 7.9238 0.1777 0.7450 -0.6430
4.7333 1.4010 -0.4199 -0.0273 -0.1034 -0.9943
-3.2408 -6.3953 3.3967 0.5683 0.3880 0.7256
-2.7370 6.3016 -5.1252 -0.7014 -0.4830 0.5242
0.5941 -8.0094 5.6492 0.8227 0.5649 -0.0635
2.7362 -6.3026 5.1257 0.7015 0.4831 -0.5240
2.7005 7.0683 -4.0184 -0.6492 -0.4437 -0.6178
-0.7004 -9.0133 -3.5588 0.9065 -0.3224 0.2725
-1.8568 8.4302 3.2140 -0.9087 0.3217 0.2661
0.8368 8.9692 3.5478 -0.8987 0.3197 -0.3002
3.6924 5.7542 2.4201 -0.5002 0.1798 -0.8470

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16147
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.637
_diffrn_reflns_theta_min         4.082
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      104.60(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3196
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -126.00  37.00   1.00    1.00    --  -42.33 -10.00-114.00  163
  2  ω    100.00 177.00   1.00    1.98    --  104.49 120.00-136.00   77
  3  ω     97.00 177.00   1.00    1.98    --  104.49 126.00 129.00   80
  4  ω   -116.00 -58.00   1.00    1.00    --  -42.33-153.00 -19.00   58
  5  ω     27.00  96.00   1.00    1.00    --   42.33-125.00-120.00   69
  6  ω     31.00 109.00   1.00    1.98    --  104.49-111.00  90.00   78
  7  ω    104.00 178.00   1.00    1.98    --  104.49 111.00 -90.00   74
  8  ω     31.00 109.00   1.00    1.98    --  104.49-111.00  60.00   78
  9  ω     31.00 130.00   1.00    1.98    --  104.49 -45.00-150.00   99
 10  ω     25.00 178.00   1.00    1.98    --  104.49  10.00  59.00  153
 11  ω   -115.00 -14.00   1.00    1.00    --  -42.33 -57.00 150.00  101
 12  ω   -115.00 -14.00   1.00    1.00    --  -42.33 -57.00-150.00  101
 13  ω   -115.00 -65.00   1.00    1.00    --  -42.33-143.00-116.00   50
 14  ω   -115.00 -14.00   1.00    1.00    --  -42.33 -57.00  60.00  101
 15  ω     31.00 109.00   1.00    1.98    --  104.49-111.00-120.00   78
 16  ω     79.00 127.00   1.00    1.98    --  104.49  45.00 120.00   48
 17  ω     76.00 178.00   1.00    1.98    --  104.49  30.00-150.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0242635000
_diffrn_orient_matrix_UB_12      -0.1019095000
_diffrn_orient_matrix_UB_13      -0.0014049000
_diffrn_orient_matrix_UB_21      -0.0125053000
_diffrn_orient_matrix_UB_22      -0.0020915000
_diffrn_orient_matrix_UB_23      0.0983457000
_diffrn_orient_matrix_UB_31      -0.2071235000
_diffrn_orient_matrix_UB_32      -0.0117318000
_diffrn_orient_matrix_UB_33      -0.0060875000
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                3225
_reflns_number_total             3386
_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 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 1313 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3386
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0270
_refine_ls_restrained_S_all      1.064
_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)+(0.0376P)²+0.2550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0703
_refine_special_details          ?
_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
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C14(H14), C15(H15), C17(H17),
 C18(H18)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_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 0.51881(8) 0.63608(3) 0.35197(3) 0.03005(14) Uani 1 1 d . . . . .
O1 O 0.8680(2) 0.63138(9) 0.49913(10) 0.0287(3) Uani 1 1 d . . . . .
O2 O 1.1490(2) 0.62799(10) 0.54713(11) 0.0324(4) Uani 1 1 d . . . . .
O3 O 0.4189(3) 0.55410(11) 0.34536(11) 0.0422(4) Uani 1 1 d . . . . .
O4 O 0.6875(2) 0.64362(12) 0.30585(11) 0.0422(4) Uani 1 1 d . . . . .
N1 N 0.9678(2) 0.51078(11) 0.57941(11) 0.0259(4) Uani 1 1 d . . . . .
C1 C 1.2309(3) 0.40706(13) 0.57553(14) 0.0267(5) Uani 1 1 d . . . . .
C2 C 1.2343(3) 0.40925(14) 0.48703(14) 0.0285(5) Uani 1 1 d . . . . .
H2 H 1.155846 0.448626 0.457126 0.034 Uiso 1 1 calc R U . . .
C3 C 1.3515(3) 0.35431(15) 0.44158(16) 0.0350(5) Uani 1 1 d . . . . .
H3 H 1.353042 0.356466 0.380869 0.042 Uiso 1 1 calc R U . . .
C4 C 1.4659(4) 0.29651(15) 0.48444(19) 0.0422(6) Uani 1 1 d . . . . .
H4 H 1.545850 0.258924 0.453352 0.051 Uiso 1 1 calc R U . . .
C5 C 1.4631(4) 0.29379(16) 0.57259(19) 0.0440(6) Uani 1 1 d . . . . .
H5 H 1.541031 0.253967 0.602240 0.053 Uiso 1 1 calc R U . . .
C6 C 1.3471(3) 0.34888(15) 0.61817(16) 0.0360(5) Uani 1 1 d . . . . .
H6 H 1.346841 0.346933 0.678887 0.043 Uiso 1 1 calc R U . . .
C7 C 1.1126(3) 0.46821(16) 0.62780(14) 0.0313(5) Uani 1 1 d . . . . .
H7A H 1.058042 0.433564 0.675120 0.038 Uiso 1 1 calc R U . . .
H7B H 1.189720 0.515077 0.653543 0.038 Uiso 1 1 calc R U . . .
C8 C 0.8024(3) 0.45941(15) 0.56844(16) 0.0333(5) Uani 1 1 d . . . . .
H8A H 0.761294 0.436700 0.624629 0.040 Uiso 1 1 calc R U . . .
H8B H 0.826611 0.407637 0.530926 0.040 Uiso 1 1 calc R U . . .
C9 C 0.6584(3) 0.51536(14) 0.53014(14) 0.0285(4) Uani 1 1 d . . . . .
H9 H 0.538058 0.492953 0.527521 0.034 Uiso 1 1 calc R U . . .
C10 C 0.6927(3) 0.59542(14) 0.49958(13) 0.0244(4) Uani 1 1 d . . . . .
C11 C 1.0042(3) 0.59004(13) 0.54316(13) 0.0257(4) Uani 1 1 d . . . . .
C12 C 0.5592(3) 0.65888(13) 0.46271(13) 0.0258(4) Uani 1 1 d . . . . .
H12A H 0.605366 0.720465 0.468988 0.031 Uiso 1 1 calc R U . . .
H12B H 0.443583 0.654449 0.494625 0.031 Uiso 1 1 calc R U . . .
C13 C 0.3753(3) 0.72464(14) 0.31997(13) 0.0282(5) Uani 1 1 d . . . . .
C14 C 0.4474(3) 0.79504(15) 0.27430(13) 0.0293(5) Uani 1 1 d . . . . .
H14 H 0.573097 0.796308 0.261106 0.035 Uiso 1 1 calc R U . . .
C15 C 0.3352(3) 0.86373(16) 0.24787(13) 0.0321(5) Uani 1 1 d . . . . .
H15 H 0.384729 0.911972 0.216211 0.039 Uiso 1 1 calc R U . . .
C16 C 0.1507(3) 0.86301(17) 0.26711(14) 0.0330(5) Uani 1 1 d . . . . .
C17 C 0.0815(3) 0.79159(17) 0.31383(14) 0.0350(5) Uani 1 1 d . . . . .
H17 H -0.043891 0.790535 0.327821 0.042 Uiso 1 1 calc R U . . .
C18 C 0.1916(3) 0.72224(16) 0.34020(14) 0.0330(5) Uani 1 1 d . . . . .
H18 H 0.142581 0.673729 0.371636 0.040 Uiso 1 1 calc R U . . .
C19 C 0.0312(4) 0.93870(18) 0.23844(17) 0.0453(6) Uani 1 1 d . . . . .
H19A H -0.080631 0.914726 0.213646 0.068 Uiso 1 1 calc R U . . .
H19B H 0.095224 0.974238 0.195393 0.068 Uiso 1 1 calc R U . . .
H19C H 0.001357 0.976391 0.287637 0.068 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 O3 1.4377(17) . ?
S1 O4 1.4424(18) . ?
S1 C12 1.790(2) . ?
S1 C13 1.771(2) . ?
O1 C10 1.401(3) . ?
O1 C11 1.367(3) . ?
O2 C11 1.212(3) . ?
N1 C7 1.456(3) . ?
N1 C8 1.453(3) . ?
N1 C11 1.345(3) . ?
C1 C2 1.385(3) . ?
C1 C6 1.393(3) . ?
C1 C7 1.507(3) . ?
C2 C3 1.390(3) . ?
C3 C4 1.383(4) . ?
C4 C5 1.379(4) . ?
C5 C6 1.387(4) . ?
C8 C9 1.480(3) . ?
C9 C10 1.318(3) . ?
C10 C12 1.487(3) . ?
C13 C14 1.382(3) . ?
C13 C18 1.391(3) . ?
C14 C15 1.385(3) . ?
C15 C16 1.393(3) . ?
C16 C17 1.394(3) . ?
C16 C19 1.506(3) . ?
C17 C18 1.383(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
O3 S1 O4 118.24(11) . . ?
O3 S1 C12 108.56(10) . . ?
O3 S1 C13 108.41(11) . . ?
O4 S1 C12 108.99(11) . . ?
O4 S1 C13 108.37(10) . . ?
C13 S1 C12 103.24(10) . . ?
C11 O1 C10 120.05(16) . . ?
C8 N1 C7 116.37(17) . . ?
C11 N1 C7 117.42(18) . . ?
C11 N1 C8 125.96(19) . . ?
C2 C1 C6 118.8(2) . . ?
C2 C1 C7 122.5(2) . . ?
C6 C1 C7 118.6(2) . . ?
C1 C2 C3 120.5(2) . . ?
C4 C3 C2 120.2(2) . . ?
C5 C4 C3 119.6(2) . . ?
C4 C5 C6 120.3(2) . . ?
C5 C6 C1 120.5(2) . . ?
N1 C7 C1 114.19(18) . . ?
N1 C8 C9 110.42(17) . . ?
C10 C9 C8 121.8(2) . . ?
O1 C10 C12 111.26(17) . . ?
C9 C10 O1 122.0(2) . . ?
C9 C10 C12 126.7(2) . . ?
O2 C11 O1 117.38(18) . . ?
O2 C11 N1 124.8(2) . . ?
N1 C11 O1 117.85(19) . . ?
C10 C12 S1 111.27(14) . . ?
C14 C13 S1 119.34(18) . . ?
C14 C13 C18 120.8(2) . . ?
C18 C13 S1 119.87(17) . . ?
C13 C14 C15 119.6(2) . . ?
C14 C15 C16 120.8(2) . . ?
C15 C16 C17 118.5(2) . . ?
C15 C16 C19 120.1(2) . . ?
C17 C16 C19 121.4(2) . . ?
C18 C17 C16 121.3(2) . . ?
C17 C18 C13 119.0(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 1.967
_oxdiff_exptl_absorpt_empirical_full_min 0.574
