# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_f1_a
_database_code_depnum_ccdc_archive 'CCDC 1997416'
loop_
_audit_author_name
_audit_author_address
'Pravin Kumar'
;IISER Bhopal
India
;
_audit_update_record             
;
2020-04-16 deposited with the CCDC.	2021-03-18 downloaded from the CCDC.
;
_audit_creation_date             2019-11-20
_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         'C24 H19 N O'
_chemical_formula_sum            'C24 H19 N O'
_chemical_formula_weight         337.40
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   14.2820(13)
_cell_length_b                   13.5704(9)
_cell_length_c                   10.3175(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.860(2)
_cell_angle_gamma                90
_cell_volume                     1868.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1775
_cell_measurement_temperature    287(2)
_cell_measurement_theta_max      23.40
_cell_measurement_theta_min      2.60
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          .57
_exptl_crystal_size_mid          .45
_exptl_crystal_size_min          .34
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1084
_diffrn_reflns_av_unetI/netI     0.1107
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18733
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.978
_diffrn_reflns_theta_min         2.591
_diffrn_ambient_temperature      287.55
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_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                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2189
_reflns_number_total             4495
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4463
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1752
_refine_ls_R_factor_gt           0.0701
_refine_ls_restrained_S_all      1.024
_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)+(0.0502P)²+0.4793P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1598
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N002(H002), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00H(H00H),
 C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N),
 C00O(H00O), C00P(H00P), C004(H004), C009(H009)
2.b Idealised Me refined as rotating group:
 C00Q(H00A,H00B,H00G)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O001 O 0.29224(14) 0.40370(11) 1.13838(16) 0.0663(5) Uani 1 1 d . . . . .
N002 N 0.26369(12) 0.29382(12) 0.74286(17) 0.0434(5) Uani 1 1 d . . . . .
H002 H 0.274463 0.240496 0.705348 0.052 Uiso 1 1 calc R . . . .
C00A C 0.13960(15) 0.36390(16) 0.5242(2) 0.0438(5) Uani 1 1 d . . . . .
C00B C 0.37528(16) 0.24765(16) 0.9807(2) 0.0452(6) Uani 1 1 d . . . . .
C00C C 0.11327(16) 0.27563(17) 0.4538(2) 0.0534(6) Uani 1 1 d . . . . .
H00C H 0.134341 0.216651 0.501102 0.064 Uiso 1 1 calc R . . . .
C00D C 0.2845(2) 0.62769(17) 0.9608(2) 0.0620(7) Uani 1 1 d . . . . .
H00D H 0.319505 0.607216 0.904859 0.074 Uiso 1 1 calc R . . . .
C00E C 0.10401(17) 0.45017(18) 0.4499(2) 0.0584(7) Uani 1 1 d . . . . .
H00E H 0.119551 0.510603 0.495022 0.070 Uiso 1 1 calc R . . . .
C00F C 0.45711(19) 0.28408(19) 1.0893(3) 0.0671(8) Uani 1 1 d . . . . .
H00F H 0.471646 0.351093 1.094629 0.081 Uiso 1 1 calc R . . . .
C00G C 0.41599(19) 0.08342(18) 1.0751(3) 0.0600(7) Uani 1 1 d . . . . .
C00H C 0.1997(2) 0.5897(2) 1.1163(3) 0.0676(7) Uani 1 1 d . . . . .
H00H H 0.179168 0.544234 1.168174 0.081 Uiso 1 1 calc R . . . .
C00I C 0.05599(19) 0.2739(2) 0.3138(3) 0.0681(8) Uani 1 1 d . . . . .
H00I H 0.040046 0.213762 0.267879 0.082 Uiso 1 1 calc R . . . .
C00J C 0.02245(19) 0.3596(2) 0.2421(3) 0.0736(8) Uani 1 1 d . . . . .
H00J H -0.015934 0.357912 0.147985 0.088 Uiso 1 1 calc R . . . .
C00K C 0.04609(19) 0.4477(2) 0.3105(3) 0.0711(8) Uani 1 1 d . . . . .
H00K H 0.023037 0.506206 0.262915 0.085 Uiso 1 1 calc R . . . .
C00L C 0.2655(3) 0.7261(2) 0.9696(3) 0.0894(11) Uani 1 1 d . . . . .
H00L H 0.289248 0.772263 0.922351 0.107 Uiso 1 1 calc R . . . .
C00M C 0.4955(2) 0.1220(2) 1.1823(3) 0.0822(9) Uani 1 1 d . . . . .
H00M H 0.535581 0.080361 1.251329 0.099 Uiso 1 1 calc R . . . .
C00N C 0.2116(3) 0.7556(3) 1.0480(4) 0.1049(14) Uani 1 1 d . . . . .
H00N H 0.197376 0.822173 1.052103 0.126 Uiso 1 1 calc R . . . .
C00O C 0.5166(2) 0.2208(2) 1.1890(3) 0.0877(10) Uani 1 1 d . . . . .
H00O H 0.571423 0.245186 1.261466 0.105 Uiso 1 1 calc R . . . .
C00P C 0.1778(2) 0.6886(3) 1.1212(4) 0.0935(11) Uani 1 1 d . . . . .
H00P H 0.140415 0.709617 1.173702 0.112 Uiso 1 1 calc R . . . .
C00Q C 0.3912(2) -0.02494(19) 1.0695(3) 0.0891(10) Uani 1 1 d . . . . .
H00A H 0.349421 -0.037273 1.122848 0.134 Uiso 1 1 calc GR . . . .
H00B H 0.452017 -0.062296 1.107149 0.134 Uiso 1 1 calc GR . . . .
H00G H 0.356475 -0.044191 0.974929 0.134 Uiso 1 1 calc GR . . . .
C003 C 0.25213(17) 0.55862(16) 1.0343(2) 0.0479(6) Uani 1 1 d . . . . .
C004 C 0.20545(16) 0.44019(15) 0.7671(2) 0.0460(6) Uani 1 1 d . . . . .
H004 H 0.171801 0.500179 0.748304 0.055 Uiso 1 1 calc R . . . .
C005 C 0.27014(16) 0.40776(15) 0.9000(2) 0.0439(6) Uani 1 1 d . . . . .
C006 C 0.27528(16) 0.45206(16) 1.0312(2) 0.0465(6) Uani 1 1 d . . . . .
C007 C 0.30625(15) 0.31558(15) 0.8802(2) 0.0420(5) Uani 1 1 d . . . . .
C008 C 0.20086(16) 0.36876(15) 0.6716(2) 0.0430(5) Uani 1 1 d . . . . .
C009 C 0.35699(16) 0.14723(16) 0.9738(2) 0.0472(6) Uani 1 1 d . . . . .
H009 H 0.303906 0.121981 0.899617 0.057 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
O001 C006 1.234(2) . ?
N002 H002 0.8600 . ?
N002 C007 1.360(3) . ?
N002 C008 1.382(3) . ?
C00A C00C 1.382(3) . ?
C00A C00E 1.393(3) . ?
C00A C008 1.461(3) . ?
C00B C00F 1.391(3) . ?
C00B C007 1.473(3) . ?
C00B C009 1.385(3) . ?
C00C H00C 0.9300 . ?
C00C C00I 1.383(3) . ?
C00D H00D 0.9300 . ?
C00D C00L 1.372(4) . ?
C00D C003 1.385(3) . ?
C00E H00E 0.9300 . ?
C00E C00K 1.381(3) . ?
C00F H00F 0.9300 . ?
C00F C00O 1.377(3) . ?
C00G C00M 1.376(4) . ?
C00G C00Q 1.509(3) . ?
C00G C009 1.387(3) . ?
C00H H00H 0.9300 . ?
C00H C00P 1.383(4) . ?
C00H C003 1.381(3) . ?
C00I H00I 0.9300 . ?
C00I C00J 1.371(4) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.368(4) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00L C00N 1.360(5) . ?
C00M H00M 0.9300 . ?
C00M C00O 1.370(4) . ?
C00N H00N 0.9300 . ?
C00N C00P 1.375(5) . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9300 . ?
C00Q H00A 0.9600 . ?
C00Q H00B 0.9600 . ?
C00Q H00G 0.9600 . ?
C003 C006 1.486(3) . ?
C004 H004 0.9300 . ?
C004 C005 1.423(3) . ?
C004 C008 1.367(3) . ?
C005 C006 1.459(3) . ?
C005 C007 1.396(3) . ?
C009 H009 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
C007 N002 H002 124.5 . . ?
C007 N002 C008 111.04(17) . . ?
C008 N002 H002 124.5 . . ?
C00C C00A C00E 117.5(2) . . ?
C00C C00A C008 122.4(2) . . ?
C00E C00A C008 120.1(2) . . ?
C00F C00B C007 120.3(2) . . ?
C009 C00B C00F 118.7(2) . . ?
C009 C00B C007 120.89(19) . . ?
C00A C00C H00C 119.6 . . ?
C00A C00C C00I 120.9(2) . . ?
C00I C00C H00C 119.6 . . ?
C00L C00D H00D 119.7 . . ?
C00L C00D C003 120.6(3) . . ?
C003 C00D H00D 119.7 . . ?
C00A C00E H00E 119.4 . . ?
C00K C00E C00A 121.3(2) . . ?
C00K C00E H00E 119.4 . . ?
C00B C00F H00F 120.1 . . ?
C00O C00F C00B 119.9(2) . . ?
C00O C00F H00F 120.1 . . ?
C00M C00G C00Q 121.1(2) . . ?
C00M C00G C009 118.3(2) . . ?
C009 C00G C00Q 120.6(2) . . ?
C00P C00H H00H 120.1 . . ?
C003 C00H H00H 120.1 . . ?
C003 C00H C00P 119.9(3) . . ?
C00C C00I H00I 119.6 . . ?
C00J C00I C00C 120.8(2) . . ?
C00J C00I H00I 119.6 . . ?
C00I C00J H00J 120.4 . . ?
C00K C00J C00I 119.2(2) . . ?
C00K C00J H00J 120.4 . . ?
C00E C00K H00K 119.8 . . ?
C00J C00K C00E 120.3(2) . . ?
C00J C00K H00K 119.8 . . ?
C00D C00L H00L 120.2 . . ?
C00N C00L C00D 119.6(3) . . ?
C00N C00L H00L 120.2 . . ?
C00G C00M H00M 119.4 . . ?
C00O C00M C00G 121.1(2) . . ?
C00O C00M H00M 119.4 . . ?
C00L C00N H00N 119.5 . . ?
C00L C00N C00P 121.0(3) . . ?
C00P C00N H00N 119.5 . . ?
C00F C00O H00O 119.8 . . ?
C00M C00O C00F 120.4(3) . . ?
C00M C00O H00O 119.8 . . ?
C00H C00P H00P 120.2 . . ?
C00N C00P C00H 119.5(3) . . ?
C00N C00P H00P 120.2 . . ?
C00G C00Q H00A 109.5 . . ?
C00G C00Q H00B 109.5 . . ?
C00G C00Q H00G 109.5 . . ?
H00A C00Q H00B 109.5 . . ?
H00A C00Q H00G 109.5 . . ?
H00B C00Q H00G 109.5 . . ?
C00D C003 C006 121.8(2) . . ?
C00H C003 C00D 119.3(2) . . ?
C00H C003 C006 118.9(2) . . ?
C005 C004 H004 125.6 . . ?
C008 C004 H004 125.6 . . ?
C008 C004 C005 108.86(19) . . ?
C004 C005 C006 124.6(2) . . ?
C007 C005 C004 106.44(19) . . ?
C007 C005 C006 127.3(2) . . ?
O001 C006 C003 118.2(2) . . ?
O001 C006 C005 122.8(2) . . ?
C005 C006 C003 118.9(2) . . ?
N002 C007 C00B 122.43(19) . . ?
N002 C007 C005 107.20(18) . . ?
C005 C007 C00B 130.4(2) . . ?
N002 C008 C00A 123.72(19) . . ?
C004 C008 N002 106.44(18) . . ?
C004 C008 C00A 129.8(2) . . ?
C00B C009 C00G 121.5(2) . . ?
C00B C009 H009 119.2 . . ?
C00G C009 H009 119.2 . . ?

_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_mo_pk06_1075_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2060949'
loop_
_audit_author_name
_audit_author_address
'Pravin Kumar'
;IISER Bhopal
India
;
_audit_update_record             
;
2021-02-04 deposited with the CCDC.	2021-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H14 N2 O2 S'
_chemical_formula_weight         250.31

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.912(3)
_cell_length_b                   15.262(4)
_cell_length_c                   8.115(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.518(10)
_cell_angle_gamma                90
_cell_volume                     1214.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    9937
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      30.04

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.258
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25098
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.314
_diffrn_reflns_theta_max         24.959
_diffrn_reflns_theta_full        24.959
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             2086
_reflns_number_gt                1913
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0579P)²+0.5052P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2086
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0946
_refine_ls_wR_factor_gt          0.0905
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S01 S 0.29347(4) 0.38188(2) 0.09146(4) 0.02436(17) Uani 1 1 d . . . . .
O002 O 0.40569(11) 0.32305(7) 0.13455(14) 0.0310(3) Uani 1 1 d . . . . .
O003 O 0.21567(12) 0.38157(8) -0.07110(14) 0.0335(3) Uani 1 1 d . . . . .
N004 N 0.36040(12) 0.48339(8) 0.11972(15) 0.0244(3) Uani 1 1 d . . . . .
N005 N 0.27846(13) 0.55222(9) 0.05290(16) 0.0275(3) Uani 1 1 d . . . . .
C006 C 0.18339(16) 0.37477(9) 0.24273(19) 0.0230(3) Uani 1 1 d . . . . .
C007 C 0.34449(17) 0.62334(10) 0.11353(19) 0.0274(4) Uani 1 1 d . . . . .
C008 C 0.46592(16) 0.60213(11) 0.22155(19) 0.0283(4) Uani 1 1 d . . . . .
H008 H 0.529416 0.642311 0.278984 0.034 Uiso 1 1 calc R U . . .
C009 C 0.04836(16) 0.40150(11) 0.2033(2) 0.0289(4) Uani 1 1 d . . . . .
H009 H 0.013116 0.420361 0.093787 0.035 Uiso 1 1 calc R U . . .
C00A C 0.23519(16) 0.34516(10) 0.40150(19) 0.0270(4) Uani 1 1 d . . . . .
H00A H 0.326946 0.325580 0.426053 0.032 Uiso 1 1 calc R U . . .
C00B C 0.47412(14) 0.51271(10) 0.22720(18) 0.0248(3) Uani 1 1 d . . . . .
C00C C 0.01610(17) 0.37301(10) 0.4893(2) 0.0303(4) Uani 1 1 d . . . . .
C00D C 0.15101(17) 0.34462(10) 0.5235(2) 0.0301(4) Uani 1 1 d . . . . .
H00D H 0.185873 0.324546 0.632265 0.036 Uiso 1 1 calc R U . . .
C00E C -0.03373(17) 0.39995(11) 0.3280(2) 0.0338(4) Uani 1 1 d . . . . .
H00E H -0.126309 0.417739 0.302364 0.041 Uiso 1 1 calc R U . . .
C00F C 0.58055(16) 0.45508(11) 0.3206(2) 0.0318(4) Uani 1 1 d . . . . .
H00B H 0.539081 0.418154 0.398246 0.048 Uiso 1 1 calc R U . . .
H00C H 0.652185 0.491342 0.382995 0.048 Uiso 1 1 calc R U . . .
H00F H 0.620338 0.417864 0.241908 0.048 Uiso 1 1 calc R U . . .
C00G C 0.29109(19) 0.71237(12) 0.0622(2) 0.0391(4) Uani 1 1 d . . . . .
H00G H 0.349046 0.739051 -0.011993 0.059 Uiso 1 1 calc R U . . .
H00H H 0.291620 0.749158 0.161236 0.059 Uiso 1 1 calc R U . . .
H00I H 0.197600 0.707264 0.003576 0.059 Uiso 1 1 calc R U . . .
C00H C -0.0714(2) 0.37401(13) 0.6277(2) 0.0430(5) Uani 1 1 d . . . . .
H00J H -0.063653 0.317476 0.685595 0.065 Uiso 1 1 calc R U . . .
H00K H -0.166771 0.384359 0.580047 0.065 Uiso 1 1 calc R U . . .
H00L H -0.040199 0.420847 0.706883 0.065 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
S01 O003 1.4260(12) . ?
S01 O002 1.4319(12) . ?
S01 N004 1.6876(14) . ?
S01 C006 1.7625(15) . ?
N004 N005 1.3880(18) . ?
N004 C00B 1.3930(19) . ?
N005 C007 1.324(2) . ?
C006 C009 1.390(2) . ?
C006 C00A 1.390(2) . ?
C007 C008 1.418(2) . ?
C007 C00G 1.495(2) . ?
C008 C00B 1.368(2) . ?
C008 H008 0.9500 . ?
C009 C00E 1.389(2) . ?
C009 H009 0.9500 . ?
C00A C00D 1.386(2) . ?
C00A H00A 0.9500 . ?
C00B C00F 1.491(2) . ?
C00C C00E 1.392(3) . ?
C00C C00D 1.394(2) . ?
C00C C00H 1.517(2) . ?
C00D H00D 0.9500 . ?
C00E H00E 0.9500 . ?
C00F H00B 0.9800 . ?
C00F H00C 0.9800 . ?
C00F H00F 0.9800 . ?
C00G H00G 0.9800 . ?
C00G H00H 0.9800 . ?
C00G H00I 0.9800 . ?
C00H H00J 0.9800 . ?
C00H H00K 0.9800 . ?
C00H H00L 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
O003 S01 O002 121.20(7) . . ?
O003 S01 N004 106.06(7) . . ?
O002 S01 N004 105.48(7) . . ?
O003 S01 C006 109.78(8) . . ?
O002 S01 C006 109.26(7) . . ?
N004 S01 C006 103.50(6) . . ?
N005 N004 C00B 111.96(13) . . ?
N005 N004 S01 116.50(10) . . ?
C00B N004 S01 130.19(11) . . ?
C007 N005 N004 104.29(13) . . ?
C009 C006 C00A 121.31(14) . . ?
C009 C006 S01 119.71(12) . . ?
C00A C006 S01 118.94(12) . . ?
N005 C007 C008 111.73(14) . . ?
N005 C007 C00G 120.42(15) . . ?
C008 C007 C00G 127.82(15) . . ?
C00B C008 C007 106.82(14) . . ?
C00B C008 H008 126.6 . . ?
C007 C008 H008 126.6 . . ?
C00E C009 C006 118.36(15) . . ?
C00E C009 H009 120.8 . . ?
C006 C009 H009 120.8 . . ?
C00D C00A C006 119.02(15) . . ?
C00D C00A H00A 120.5 . . ?
C006 C00A H00A 120.5 . . ?
C008 C00B N004 105.13(13) . . ?
C008 C00B C00F 129.76(15) . . ?
N004 C00B C00F 125.08(14) . . ?
C00E C00C C00D 118.37(15) . . ?
C00E C00C C00H 122.11(16) . . ?
C00D C00C C00H 119.52(16) . . ?
C00A C00D C00C 121.18(15) . . ?
C00A C00D H00D 119.4 . . ?
C00C C00D H00D 119.4 . . ?
C009 C00E C00C 121.72(15) . . ?
C009 C00E H00E 119.1 . . ?
C00C C00E H00E 119.1 . . ?
C00B C00F H00B 109.5 . . ?
C00B C00F H00C 109.5 . . ?
H00B C00F H00C 109.5 . . ?
C00B C00F H00F 109.5 . . ?
H00B C00F H00F 109.5 . . ?
H00C C00F H00F 109.5 . . ?
C007 C00G H00G 109.5 . . ?
C007 C00G H00H 109.5 . . ?
H00G C00G H00H 109.5 . . ?
C007 C00G H00I 109.5 . . ?
H00G C00G H00I 109.5 . . ?
H00H C00G H00I 109.5 . . ?
C00C C00H H00J 109.5 . . ?
C00C C00H H00K 109.5 . . ?
H00J C00H H00K 109.5 . . ?
C00C C00H H00L 109.5 . . ?
H00J C00H H00L 109.5 . . ?
H00K C00H H00L 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
O003 S01 N004 N005 36.95(12) . . . . ?
O002 S01 N004 N005 166.67(10) . . . . ?
C006 S01 N004 N005 -78.59(11) . . . . ?
O003 S01 N004 C00B -157.54(13) . . . . ?
O002 S01 N004 C00B -27.82(14) . . . . ?
C006 S01 N004 C00B 86.92(14) . . . . ?
C00B N004 N005 C007 2.53(16) . . . . ?
S01 N004 N005 C007 170.63(10) . . . . ?
O003 S01 C006 C009 -23.42(14) . . . . ?
O002 S01 C006 C009 -158.55(12) . . . . ?
N004 S01 C006 C009 89.44(13) . . . . ?
O003 S01 C006 C00A 158.77(12) . . . . ?
O002 S01 C006 C00A 23.64(14) . . . . ?
N004 S01 C006 C00A -88.37(12) . . . . ?
N004 N005 C007 C008 -1.43(17) . . . . ?
N004 N005 C007 C00G 176.80(13) . . . . ?
N005 C007 C008 C00B -0.12(18) . . . . ?
C00G C007 C008 C00B -178.19(15) . . . . ?
C00A C006 C009 C00E 1.5(2) . . . . ?
S01 C006 C009 C00E -176.27(12) . . . . ?
C009 C006 C00A C00D -1.7(2) . . . . ?
S01 C006 C00A C00D 176.06(12) . . . . ?
C007 C008 C00B N004 1.61(16) . . . . ?
C007 C008 C00B C00F 179.80(15) . . . . ?
N005 N004 C00B C008 -2.62(16) . . . . ?
S01 N004 C00B C008 -168.65(11) . . . . ?
N005 N004 C00B C00F 179.08(13) . . . . ?
S01 N004 C00B C00F 13.1(2) . . . . ?
C006 C00A C00D C00C 0.1(2) . . . . ?
C00E C00C C00D C00A 1.7(2) . . . . ?
C00H C00C C00D C00A -178.13(15) . . . . ?
C006 C009 C00E C00C 0.4(2) . . . . ?
C00D C00C C00E C009 -1.9(2) . . . . ?
C00H C00C C00E C009 177.88(15) . . . . ?

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.038

