# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_TEST5_a
_database_code_depnum_ccdc_archive 'CCDC 2170211'
loop_
_audit_author_name
_audit_author_address
'Mr Partha Mitra' IACS
_audit_update_record             
;
2022-05-03 deposited with the CCDC.	2022-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H20 N2 O4 S'
_chemical_formula_weight         444.49

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                   12.7003(9)
_cell_length_b                   10.7468(7)
_cell_length_c                   16.0028(11)
_cell_angle_alpha                90
_cell_angle_beta                 105.880(2)
_cell_angle_gamma                90
_cell_volume                     2100.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      25.05

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   .5553
_exptl_transmission_factor_max   .7452
_exptl_crystal_size_max          .20
_exptl_crystal_size_mid          .18
_exptl_crystal_size_min          .16
_exptl_absorpt_coefficient_mu    0.191
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18977
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.311
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3670
_reflns_number_gt                3256
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0349P)²+1.1962P] 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         3670
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0958
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_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
S001 S 0.82159(3) 0.81011(4) 0.92716(3) 0.02089(13) Uani 1 1 d . . . . .
O002 O 0.92344(9) 0.63993(10) 0.75211(7) 0.0210(3) Uani 1 1 d . . . . .
O003 O 0.81904(9) 0.54140(11) 0.98366(7) 0.0193(3) Uani 1 1 d . . . . .
H003 H 0.882859 0.543485 1.017021 0.029 Uiso 1 1 calc R U . . .
O004 O 0.97931(9) 0.41369(11) 0.90506(7) 0.0207(3) Uani 1 1 d . . . . .
O005 O 0.74750(9) 0.98552(11) 0.80987(8) 0.0264(3) Uani 1 1 d . . . . .
N006 N 0.82819(10) 0.81529(12) 0.76585(8) 0.0177(3) Uani 1 1 d . . . . .
N007 N 0.81382(10) 0.38204(12) 0.80439(8) 0.0157(3) Uani 1 1 d . . . . .
C008 C 0.88246(12) 0.70658(14) 0.79541(10) 0.0170(3) Uani 1 1 d . . . . .
C009 C 0.70959(12) 0.44004(15) 0.78157(10) 0.0164(3) Uani 1 1 d . . . . .
C00A C 0.88420(12) 0.44354(14) 0.87003(9) 0.0159(3) Uani 1 1 d . . . . .
C00B C 0.71019(12) 0.54268(14) 0.83488(10) 0.0166(3) Uani 1 1 d . . . . .
C00C C 0.84571(12) 0.29659(15) 0.67016(10) 0.0170(3) Uani 1 1 d . . . . .
C00D C 0.90915(13) 0.39485(15) 0.65470(10) 0.0180(3) Uani 1 1 d . . . . .
H00D H 0.950491 0.443292 0.702017 0.022 Uiso 1 1 calc R U . . .
C00E C 0.82314(12) 0.55553(14) 0.89683(10) 0.0164(3) Uani 1 1 d . . . . .
C00F C 0.79235(13) 0.88554(15) 0.82549(11) 0.0198(3) Uani 1 1 d . . . . .
C00G C 0.80741(13) 0.85544(16) 0.67453(10) 0.0219(4) Uani 1 1 d . . . . .
H00A H 0.866803 0.824521 0.650812 0.026 Uiso 1 1 calc R U . . .
H00B H 0.807419 0.947475 0.671849 0.026 Uiso 1 1 calc R U . . .
C00H C 0.88389(13) 0.67807(15) 0.88858(10) 0.0174(3) Uani 1 1 d . . . . .
H00H H 0.961688 0.670780 0.924290 0.021 Uiso 1 1 calc R U . . .
C00I C 0.84105(13) 0.27034(15) 0.76218(10) 0.0180(3) Uani 1 1 d . . . . .
H00C H 0.785387 0.205378 0.760968 0.022 Uiso 1 1 calc R U . . .
H00E H 0.912857 0.238007 0.796519 0.022 Uiso 1 1 calc R U . . .
C00J C 0.69904(13) 0.80674(15) 0.62008(10) 0.0204(4) Uani 1 1 d . . . . .
C00K C 0.61711(13) 0.40319(16) 0.71843(10) 0.0206(3) Uani 1 1 d . . . . .
H00K H 0.618130 0.333062 0.682517 0.025 Uiso 1 1 calc R U . . .
C00L C 0.78799(13) 0.22466(15) 0.60066(10) 0.0205(3) Uani 1 1 d . . . . .
H00L H 0.745184 0.156556 0.610464 0.025 Uiso 1 1 calc R U . . .
C00M C 0.61472(13) 0.61039(16) 0.82625(11) 0.0209(4) Uani 1 1 d . . . . .
H00M H 0.613323 0.679396 0.863035 0.025 Uiso 1 1 calc R U . . .
C00N C 0.79250(14) 0.25186(17) 0.51655(11) 0.0250(4) Uani 1 1 d . . . . .
H00N H 0.753274 0.201809 0.469333 0.030 Uiso 1 1 calc R U . . .
C00O C 0.52217(13) 0.47313(17) 0.70956(11) 0.0241(4) Uani 1 1 d . . . . .
H00O H 0.457226 0.450576 0.666516 0.029 Uiso 1 1 calc R U . . .
C00P C 0.91265(14) 0.42279(16) 0.57099(11) 0.0224(4) Uani 1 1 d . . . . .
H00P H 0.955347 0.490902 0.561039 0.027 Uiso 1 1 calc R U . . .
C00Q C 0.52091(14) 0.57478(17) 0.76234(11) 0.0256(4) Uani 1 1 d . . . . .
H00Q H 0.455213 0.620977 0.754936 0.031 Uiso 1 1 calc R U . . .
C00R C 0.60593(14) 0.88082(17) 0.60119(11) 0.0268(4) Uani 1 1 d . . . . .
H00R H 0.610537 0.963856 0.622253 0.032 Uiso 1 1 calc R U . . .
C00S C 0.85374(14) 0.35122(17) 0.50162(11) 0.0253(4) Uani 1 1 d . . . . .
H00S H 0.855604 0.370596 0.444121 0.030 Uiso 1 1 calc R U . . .
C00T C 0.59182(15) 0.63958(17) 0.53917(11) 0.0275(4) Uani 1 1 d . . . . .
H00T H 0.587155 0.556819 0.517597 0.033 Uiso 1 1 calc R U . . .
C00U C 0.69080(14) 0.68523(16) 0.58907(11) 0.0234(4) Uani 1 1 d . . . . .
H00U H 0.753688 0.633221 0.602294 0.028 Uiso 1 1 calc R U . . .
C00V C 0.49919(15) 0.71434(18) 0.52048(11) 0.0295(4) Uani 1 1 d . . . . .
H00V H 0.431173 0.682803 0.486219 0.035 Uiso 1 1 calc R U . . .
C00W C 0.50613(15) 0.83471(18) 0.55181(12) 0.0313(4) Uani 1 1 d . . . . .
H00W H 0.442734 0.885856 0.539590 0.038 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
S001 C00F 1.7640(17) . ?
S001 C00H 1.8133(16) . ?
O002 C008 1.2088(19) . ?
O003 C00E 1.4129(18) . ?
O003 H003 0.8400 . ?
O004 C00A 1.2271(19) . ?
O005 C00F 1.210(2) . ?
N006 C008 1.373(2) . ?
N006 C00F 1.388(2) . ?
N006 C00G 1.477(2) . ?
N007 C00A 1.351(2) . ?
N007 C009 1.418(2) . ?
N007 C00I 1.465(2) . ?
C008 C00H 1.517(2) . ?
C009 C00K 1.381(2) . ?
C009 C00B 1.393(2) . ?
C00A C00E 1.554(2) . ?
C00B C00M 1.388(2) . ?
C00B C00E 1.510(2) . ?
C00C C00L 1.388(2) . ?
C00C C00D 1.391(2) . ?
C00C C00I 1.516(2) . ?
C00D C00P 1.385(2) . ?
C00D H00D 0.9500 . ?
C00E C00H 1.550(2) . ?
C00G C00J 1.507(2) . ?
C00G H00A 0.9900 . ?
C00G H00B 0.9900 . ?
C00H H00H 1.0000 . ?
C00I H00C 0.9900 . ?
C00I H00E 0.9900 . ?
C00J C00R 1.389(2) . ?
C00J C00U 1.391(2) . ?
C00K C00O 1.395(2) . ?
C00K H00K 0.9500 . ?
C00L C00N 1.394(2) . ?
C00L H00L 0.9500 . ?
C00M C00Q 1.395(2) . ?
C00M H00M 0.9500 . ?
C00N C00S 1.380(3) . ?
C00N H00N 0.9500 . ?
C00O C00Q 1.384(2) . ?
C00O H00O 0.9500 . ?
C00P C00S 1.389(3) . ?
C00P H00P 0.9500 . ?
C00Q H00Q 0.9500 . ?
C00R C00W 1.389(3) . ?
C00R H00R 0.9500 . ?
C00S H00S 0.9500 . ?
C00T C00U 1.382(2) . ?
C00T C00V 1.388(3) . ?
C00T H00T 0.9500 . ?
C00U H00U 0.9500 . ?
C00V C00W 1.381(3) . ?
C00V H00V 0.9500 . ?
C00W H00W 0.9500 . ?

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
C00F S001 C00H 92.69(7) . . ?
C00E O003 H003 109.5 . . ?
C008 N006 C00F 117.01(13) . . ?
C008 N006 C00G 121.78(13) . . ?
C00F N006 C00G 121.21(13) . . ?
C00A N007 C009 110.96(13) . . ?
C00A N007 C00I 124.76(13) . . ?
C009 N007 C00I 124.28(13) . . ?
O002 C008 N006 124.12(14) . . ?
O002 C008 C00H 123.53(14) . . ?
N006 C008 C00H 112.35(13) . . ?
C00K C009 C00B 122.41(15) . . ?
C00K C009 N007 127.56(15) . . ?
C00B C009 N007 110.00(13) . . ?
O004 C00A N007 125.90(15) . . ?
O004 C00A C00E 125.41(14) . . ?
N007 C00A C00E 108.63(12) . . ?
C00M C00B C009 119.72(14) . . ?
C00M C00B C00E 131.62(14) . . ?
C009 C00B C00E 108.62(13) . . ?
C00L C00C C00D 119.02(15) . . ?
C00L C00C C00I 121.48(14) . . ?
C00D C00C C00I 119.50(14) . . ?
C00P C00D C00C 120.66(15) . . ?
C00P C00D H00D 119.7 . . ?
C00C C00D H00D 119.7 . . ?
O003 C00E C00B 110.60(12) . . ?
O003 C00E C00H 109.16(12) . . ?
C00B C00E C00H 115.29(13) . . ?
O003 C00E C00A 110.10(12) . . ?
C00B C00E C00A 101.77(12) . . ?
C00H C00E C00A 109.68(12) . . ?
O005 C00F N006 124.45(15) . . ?
O005 C00F S001 124.55(13) . . ?
N006 C00F S001 111.01(12) . . ?
N006 C00G C00J 111.00(13) . . ?
N006 C00G H00A 109.4 . . ?
C00J C00G H00A 109.4 . . ?
N006 C00G H00B 109.4 . . ?
C00J C00G H00B 109.4 . . ?
H00A C00G H00B 108.0 . . ?
C008 C00H C00E 112.51(12) . . ?
C008 C00H S001 106.71(11) . . ?
C00E C00H S001 111.23(10) . . ?
C008 C00H H00H 108.8 . . ?
C00E C00H H00H 108.8 . . ?
S001 C00H H00H 108.8 . . ?
N007 C00I C00C 111.86(13) . . ?
N007 C00I H00C 109.2 . . ?
C00C C00I H00C 109.2 . . ?
N007 C00I H00E 109.2 . . ?
C00C C00I H00E 109.2 . . ?
H00C C00I H00E 107.9 . . ?
C00R C00J C00U 118.96(16) . . ?
C00R C00J C00G 121.02(15) . . ?
C00U C00J C00G 120.01(15) . . ?
C009 C00K C00O 117.28(15) . . ?
C009 C00K H00K 121.4 . . ?
C00O C00K H00K 121.4 . . ?
C00C C00L C00N 120.32(16) . . ?
C00C C00L H00L 119.8 . . ?
C00N C00L H00L 119.8 . . ?
C00B C00M C00Q 118.48(15) . . ?
C00B C00M H00M 120.8 . . ?
C00Q C00M H00M 120.8 . . ?
C00S C00N C00L 120.24(16) . . ?
C00S C00N H00N 119.9 . . ?
C00L C00N H00N 119.9 . . ?
C00Q C00O C00K 121.16(15) . . ?
C00Q C00O H00O 119.4 . . ?
C00K C00O H00O 119.4 . . ?
C00D C00P C00S 120.00(16) . . ?
C00D C00P H00P 120.0 . . ?
C00S C00P H00P 120.0 . . ?
C00O C00Q C00M 120.93(16) . . ?
C00O C00Q H00Q 119.5 . . ?
C00M C00Q H00Q 119.5 . . ?
C00J C00R C00W 120.64(17) . . ?
C00J C00R H00R 119.7 . . ?
C00W C00R H00R 119.7 . . ?
C00N C00S C00P 119.73(15) . . ?
C00N C00S H00S 120.1 . . ?
C00P C00S H00S 120.1 . . ?
C00U C00T C00V 120.16(17) . . ?
C00U C00T H00T 119.9 . . ?
C00V C00T H00T 119.9 . . ?
C00T C00U C00J 120.49(16) . . ?
C00T C00U H00U 119.8 . . ?
C00J C00U H00U 119.8 . . ?
C00W C00V C00T 119.85(17) . . ?
C00W C00V H00V 120.1 . . ?
C00T C00V H00V 120.1 . . ?
C00V C00W C00R 119.89(17) . . ?
C00V C00W H00W 120.1 . . ?
C00R C00W H00W 120.1 . . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_TEST7_a
_database_code_depnum_ccdc_archive 'CCDC 2170212'
loop_
_audit_author_name
_audit_author_address
'Mr Partha Mitra' IACS
_audit_update_record             
;
2022-05-03 deposited with the CCDC.	2022-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 N2 O3'
_chemical_formula_weight         308.33

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'

_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                   11.9951(3)
_cell_length_b                   8.5493(2)
_cell_length_c                   15.5588(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.0350(10)
_cell_angle_gamma                90
_cell_volume                     1508.30(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    111(2)
_cell_measurement_reflns_used    6312
_cell_measurement_theta_min      3.53
_cell_measurement_theta_max      25.03

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   .7003
_exptl_transmission_factor_max   .7452
_exptl_crystal_size_max          .20
_exptl_crystal_size_mid          .16
_exptl_crystal_size_min          .14
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      111(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12703
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.528
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2637
_reflns_number_gt                2275
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0347P)²+0.8674P] 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         2637
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0947
_refine_ls_wR_factor_gt          0.0881
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
O1 O 0.12071(9) 0.69179(13) 0.50317(7) 0.0258(3) Uani 1 1 d . . . . .
H1 H 0.048748 0.669552 0.488964 0.039 Uiso 1 1 calc R U . . .
O002 O 0.22807(10) 0.41195(13) 0.75377(7) 0.0288(3) Uani 1 1 d . . . . .
O003 O 0.11289(9) 0.34475(13) 0.52972(7) 0.0276(3) Uani 1 1 d . . . . .
N004 N 0.22361(11) 0.65850(15) 0.81146(8) 0.0225(3) Uani 1 1 d . . . . .
N005 N 0.31024(11) 0.40219(15) 0.57699(9) 0.0238(3) Uani 1 1 d . . . . .
C006 C 0.31152(13) 0.66205(18) 0.61509(10) 0.0205(3) Uani 1 1 d . . . . .
C007 C 0.19618(13) 0.54764(17) 0.74477(10) 0.0206(3) Uani 1 1 d . . . . .
C008 C 0.17363(13) 0.80428(17) 0.77792(10) 0.0213(3) Uani 1 1 d . . . . .
C009 C 0.12210(13) 0.62642(17) 0.65611(10) 0.0206(3) Uani 1 1 d . . . . .
H009 H 0.042369 0.576676 0.633424 0.025 Uiso 1 1 calc R U . . .
C00A C 0.11102(13) 0.79215(17) 0.68542(10) 0.0210(3) Uani 1 1 d . . . . .
C00B C 0.38157(13) 0.53472(18) 0.60964(10) 0.0229(3) Uani 1 1 d . . . . .
C00C C 0.36337(13) 0.80506(18) 0.64482(10) 0.0233(3) Uani 1 1 d . . . . .
H00C H 0.316576 0.892750 0.648653 0.028 Uiso 1 1 calc R U . . .
C00D C 0.19474(13) 0.43603(18) 0.56107(10) 0.0224(3) Uani 1 1 d . . . . .
C00E C 0.05309(14) 0.92212(19) 0.63756(11) 0.0263(4) Uani 1 1 d . . . . .
H00E H 0.008476 0.914967 0.574812 0.032 Uiso 1 1 calc R U . . .
C00F C 0.18419(13) 0.61089(17) 0.58337(10) 0.0208(3) Uani 1 1 d . . . . .
C00G C 0.12594(14) 1.07292(19) 0.77671(12) 0.0295(4) Uani 1 1 d . . . . .
H00G H 0.130950 1.170253 0.807204 0.035 Uiso 1 1 calc R U . . .
C00H C 0.18172(14) 0.94392(19) 0.82474(11) 0.0265(4) Uani 1 1 d . . . . .
H00H H 0.224343 0.950466 0.887903 0.032 Uiso 1 1 calc R U . . .
C00I C 0.48550(14) 0.81846(19) 0.66909(11) 0.0270(4) Uani 1 1 d . . . . .
H00I H 0.522290 0.916297 0.689265 0.032 Uiso 1 1 calc R U . . .
C00J C 0.55403(14) 0.6897(2) 0.66402(11) 0.0293(4) Uani 1 1 d . . . . .
H00J H 0.637285 0.700575 0.681726 0.035 Uiso 1 1 calc R U . . .
C00K C 0.50274(14) 0.54497(19) 0.63343(11) 0.0279(4) Uani 1 1 d . . . . .
H00K H 0.549200 0.457187 0.629150 0.033 Uiso 1 1 calc R U . . .
C00L C 0.06243(15) 1.06354(19) 0.68445(12) 0.0307(4) Uani 1 1 d . . . . .
H00L H 0.024915 1.154392 0.652911 0.037 Uiso 1 1 calc R U . . .
C00M C 0.35399(15) 0.2481(2) 0.56470(13) 0.0343(4) Uani 1 1 d . . . . .
H00A H 0.287690 0.174955 0.543738 0.051 Uiso 1 1 calc R U . . .
H00B H 0.409160 0.211402 0.622669 0.051 Uiso 1 1 calc R U . . .
H00D H 0.394607 0.253977 0.519411 0.051 Uiso 1 1 calc R U . . .
C00N C 0.29264(15) 0.6255(2) 0.90544(11) 0.0310(4) Uani 1 1 d . . . . .
H00F H 0.242659 0.636836 0.943872 0.046 Uiso 1 1 calc R U . . .
H00M H 0.358756 0.699030 0.925602 0.046 Uiso 1 1 calc R U . . .
H00N H 0.323053 0.518308 0.910191 0.046 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
O1 C00F 1.4126(18) . ?
O1 H1 0.8400 . ?
O002 C007 1.2152(18) . ?
O003 C00D 1.2240(18) . ?
N004 C007 1.364(2) . ?
N004 C008 1.4074(19) . ?
N004 C00N 1.454(2) . ?
N005 C00D 1.357(2) . ?
N005 C00B 1.4108(19) . ?
N005 C00M 1.454(2) . ?
C006 C00C 1.381(2) . ?
C006 C00B 1.394(2) . ?
C006 C00F 1.509(2) . ?
C007 C009 1.532(2) . ?
C008 C00H 1.385(2) . ?
C008 C00A 1.393(2) . ?
C009 C00A 1.508(2) . ?
C009 C00F 1.550(2) . ?
C009 H009 1.0000 . ?
C00A C00E 1.391(2) . ?
C00B C00K 1.381(2) . ?
C00C C00I 1.393(2) . ?
C00C H00C 0.9500 . ?
C00D C00F 1.549(2) . ?
C00E C00L 1.398(2) . ?
C00E H00E 0.9500 . ?
C00G C00H 1.377(2) . ?
C00G C00L 1.391(2) . ?
C00G H00G 0.9500 . ?
C00H H00H 0.9500 . ?
C00I C00J 1.391(2) . ?
C00I H00I 0.9500 . ?
C00J C00K 1.395(2) . ?
C00J H00J 0.9500 . ?
C00K H00K 0.9500 . ?
C00L H00L 0.9500 . ?
C00M H00A 0.9800 . ?
C00M H00B 0.9800 . ?
C00M H00D 0.9800 . ?
C00N H00F 0.9800 . ?
C00N H00M 0.9800 . ?
C00N H00N 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
C00F O1 H1 109.5 . . ?
C007 N004 C008 111.43(12) . . ?
C007 N004 C00N 123.17(13) . . ?
C008 N004 C00N 125.37(13) . . ?
C00D N005 C00B 110.96(12) . . ?
C00D N005 C00M 124.07(13) . . ?
C00B N005 C00M 124.94(13) . . ?
C00C C006 C00B 119.80(14) . . ?
C00C C006 C00F 131.56(14) . . ?
C00B C006 C00F 108.64(13) . . ?
O002 C007 N004 125.94(14) . . ?
O002 C007 C009 126.28(14) . . ?
N004 C007 C009 107.74(12) . . ?
C00H C008 C00A 121.94(14) . . ?
C00H C008 N004 128.30(14) . . ?
C00A C008 N004 109.76(13) . . ?
C00A C009 C007 102.90(12) . . ?
C00A C009 C00F 114.34(12) . . ?
C007 C009 C00F 110.13(12) . . ?
C00A C009 H009 109.7 . . ?
C007 C009 H009 109.7 . . ?
C00F C009 H009 109.7 . . ?
C00E C00A C008 120.03(14) . . ?
C00E C00A C009 131.82(14) . . ?
C008 C00A C009 108.14(13) . . ?
C00K C00B C006 122.45(14) . . ?
C00K C00B N005 127.54(14) . . ?
C006 C00B N005 110.01(13) . . ?
C006 C00C C00I 118.84(14) . . ?
C006 C00C H00C 120.6 . . ?
C00I C00C H00C 120.6 . . ?
O003 C00D N005 125.12(14) . . ?
O003 C00D C00F 126.23(14) . . ?
N005 C00D C00F 108.54(12) . . ?
C00A C00E C00L 118.08(15) . . ?
C00A C00E H00E 121.0 . . ?
C00L C00E H00E 121.0 . . ?
O1 C00F C006 110.10(12) . . ?
O1 C00F C00D 109.54(12) . . ?
C006 C00F C00D 101.84(12) . . ?
O1 C00F C009 110.73(12) . . ?
C006 C00F C009 114.37(12) . . ?
C00D C00F C009 109.87(12) . . ?
C00H C00G C00L 121.31(15) . . ?
C00H C00G H00G 119.3 . . ?
C00L C00G H00G 119.3 . . ?
C00G C00H C008 117.80(15) . . ?
C00G C00H H00H 121.1 . . ?
C008 C00H H00H 121.1 . . ?
C00J C00I C00C 120.53(15) . . ?
C00J C00I H00I 119.7 . . ?
C00C C00I H00I 119.7 . . ?
C00I C00J C00K 121.22(14) . . ?
C00I C00J H00J 119.4 . . ?
C00K C00J H00J 119.4 . . ?
C00B C00K C00J 117.16(15) . . ?
C00B C00K H00K 121.4 . . ?
C00J C00K H00K 121.4 . . ?
C00G C00L C00E 120.82(15) . . ?
C00G C00L H00L 119.6 . . ?
C00E C00L H00L 119.6 . . ?
N005 C00M H00A 109.5 . . ?
N005 C00M H00B 109.5 . . ?
H00A C00M H00B 109.5 . . ?
N005 C00M H00D 109.5 . . ?
H00A C00M H00D 109.5 . . ?
H00B C00M H00D 109.5 . . ?
N004 C00N H00F 109.5 . . ?
N004 C00N H00M 109.5 . . ?
H00F C00N H00M 109.5 . . ?
N004 C00N H00N 109.5 . . ?
H00F C00N H00N 109.5 . . ?
H00M C00N H00N 109.5 . . ?

_refine_diff_density_max         0.296
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.039

