# 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_sust_3631_0m_sq
_database_code_depnum_ccdc_archive 'CCDC 2286138'
loop_
_audit_author_name
_audit_author_address
MeS
;sust
China
;
_audit_update_record             
;
2023-08-02 deposited with the CCDC.	2023-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 N O4 S'
_chemical_formula_weight         339.35

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           114
_space_group_name_H-M_alt        'P -4 21 c'
_space_group_name_Hall           'P -4 2n'

_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, z'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, x+1/2, z+1/2'

_cell_length_a                   18.3299(18)
_cell_length_b                   18.3299(18)
_cell_length_c                   10.8617(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3649.4(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    276(2)
_cell_measurement_reflns_used    9960
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      26.32

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.197
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      276(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            77247
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_av_R_equivalents  0.1204
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.179
_diffrn_reflns_theta_max         27.546
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4212
_reflns_number_gt                2727
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.795
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1000P)²+0.1055P] 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_abs_structure_details 
;
 Flack x determined using 920 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4212
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1670
_refine_ls_wR_factor_gt          0.1443
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.004

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
C1 C 0.3486(2) 0.4616(2) 0.4768(4) 0.0437(9) Uani 1 1 d . . . . .
C2 C 0.2906(2) 0.4074(2) 0.4982(4) 0.0451(10) Uani 1 1 d . . . . .
C3 C 0.2678(3) 0.3497(3) 0.4252(5) 0.0621(13) Uani 1 1 d . . . . .
H3 H 0.288953 0.341224 0.348713 0.075 Uiso 1 1 calc R U . . .
C4 C 0.2138(3) 0.3060(3) 0.4683(5) 0.0686(14) Uani 1 1 d . . . . .
H4 H 0.198661 0.266118 0.421895 0.082 Uiso 1 1 calc R U . . .
C5 C 0.1811(3) 0.3199(3) 0.5799(5) 0.0684(15) Uani 1 1 d . . . . .
H5 H 0.143491 0.289685 0.606537 0.082 Uiso 1 1 calc R U . . .
C6 C 0.2026(2) 0.3779(3) 0.6540(5) 0.0555(12) Uani 1 1 d . . . . .
H6 H 0.180255 0.387125 0.729243 0.067 Uiso 1 1 calc R U . . .
C7 C 0.2586(2) 0.4213(2) 0.6110(4) 0.0426(9) Uani 1 1 d . . . . .
C8 C 0.2960(2) 0.4866(2) 0.6721(4) 0.0427(9) Uani 1 1 d . . . . .
C9 C 0.3401(2) 0.4617(2) 0.7792(4) 0.0424(9) Uani 1 1 d . . . . .
C10 C 0.4102(2) 0.4497(3) 0.7943(4) 0.0510(11) Uani 1 1 d . . . . .
H10 H 0.446087 0.458407 0.735584 0.061 Uiso 1 1 calc R U . . .
C11 C 0.3565(3) 0.4191(2) 0.9677(5) 0.0522(11) Uani 1 1 d . . . . .
C12 C 0.2444(2) 0.5497(2) 0.6998(4) 0.0436(9) Uani 1 1 d . . . . .
C13 C 0.2552(3) 0.5959(2) 0.7990(4) 0.0570(12) Uani 1 1 d . . . . .
H13 H 0.292928 0.585856 0.853722 0.068 Uiso 1 1 calc R U . . .
C14 C 0.2124(3) 0.6556(3) 0.8193(5) 0.0630(13) Uani 1 1 d . . . . .
H14 H 0.221609 0.685618 0.886537 0.076 Uiso 1 1 calc R U . . .
C15 C 0.1554(3) 0.6716(3) 0.7409(4) 0.0598(12) Uani 1 1 d . . . . .
C16 C 0.1440(3) 0.6257(3) 0.6432(5) 0.0801(17) Uani 1 1 d . . . . .
H16 H 0.105460 0.635109 0.589924 0.096 Uiso 1 1 calc R U . . .
C17 C 0.1876(3) 0.5664(3) 0.6216(5) 0.0685(14) Uani 1 1 d . . . . .
H17 H 0.178785 0.537124 0.553321 0.082 Uiso 1 1 calc R U . . .
C00P C 0.0260(4) 0.7427(5) 0.6849(8) 0.128(3) Uani 1 1 d . . . . .
H00A H 0.038280 0.728310 0.602468 0.191 Uiso 1 1 calc R U . . .
H00B H 0.000493 0.788436 0.682899 0.191 Uiso 1 1 calc R U . . .
H00C H -0.004682 0.706198 0.721558 0.191 Uiso 1 1 calc R U . . .
N1 N 0.34844(19) 0.5066(2) 0.5743(3) 0.0470(8) Uani 1 1 d . . . . .
H1 H 0.376561 0.543998 0.579445 0.056 Uiso 1 1 calc R U . . .
O1 O 0.39070(17) 0.46489(17) 0.3892(3) 0.0559(8) Uani 1 1 d . . . . .
O2 O 0.42217(17) 0.42215(19) 0.9112(3) 0.0608(8) Uani 1 1 d . . . . .
O3 O 0.30468(15) 0.44269(15) 0.8880(3) 0.0496(7) Uani 1 1 d . . . . .
O4 O 0.3466(2) 0.3980(2) 1.0685(3) 0.0803(11) Uani 1 1 d . . . . .
S1 S 0.10561(11) 0.75200(9) 0.77163(18) 0.1002(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.227(5) . ?
C1 N1 1.341(5) . ?
C1 C2 1.475(6) . ?
C2 C7 1.381(6) . ?
C2 C3 1.385(6) . ?
C3 C4 1.358(7) . ?
C4 C5 1.376(8) . ?
C5 C6 1.391(7) . ?
C6 C7 1.380(6) . ?
C7 C8 1.531(6) . ?
C8 N1 1.479(5) . ?
C8 C9 1.489(6) . ?
C8 C12 1.524(6) . ?
C9 C10 1.312(6) . ?
C9 O3 1.393(5) . ?
C10 O2 1.385(6) . ?
C11 O4 1.175(5) . ?
C11 O2 1.352(6) . ?
C11 O3 1.357(5) . ?
C12 C13 1.385(6) . ?
C12 C17 1.378(6) . ?
C13 C14 1.365(6) . ?
C14 C15 1.379(7) . ?
C15 C16 1.370(7) . ?
C15 S1 1.765(5) . ?
C16 C17 1.369(7) . ?
C00P S1 1.746(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 125.7(4) . . ?
O1 C1 C2 127.5(4) . . ?
N1 C1 C2 106.8(3) . . ?
C7 C2 C3 121.4(4) . . ?
C7 C2 C1 108.7(4) . . ?
C3 C2 C1 129.9(4) . . ?
C4 C3 C2 118.2(5) . . ?
C3 C4 C5 120.8(5) . . ?
C4 C5 C6 121.8(5) . . ?
C5 C6 C7 117.1(5) . . ?
C2 C7 C6 120.6(4) . . ?
C2 C7 C8 109.9(3) . . ?
C6 C7 C8 129.5(4) . . ?
N1 C8 C9 106.5(3) . . ?
N1 C8 C12 110.9(3) . . ?
C9 C8 C12 114.5(3) . . ?
N1 C8 C7 99.9(3) . . ?
C9 C8 C7 110.1(3) . . ?
C12 C8 C7 113.7(3) . . ?
C10 C9 O3 108.0(4) . . ?
C10 C9 C8 132.9(4) . . ?
O3 C9 C8 119.1(3) . . ?
C9 C10 O2 109.3(4) . . ?
O4 C11 O2 125.0(4) . . ?
O4 C11 O3 126.3(5) . . ?
O2 C11 O3 108.7(4) . . ?
C13 C12 C17 116.9(4) . . ?
C13 C12 C8 121.9(4) . . ?
C17 C12 C8 121.1(4) . . ?
C14 C13 C12 122.2(4) . . ?
C13 C14 C15 120.4(4) . . ?
C14 C15 C16 117.6(4) . . ?
C14 C15 S1 116.9(4) . . ?
C16 C15 S1 125.5(4) . . ?
C17 C16 C15 122.1(5) . . ?
C16 C17 C12 120.8(4) . . ?
C1 N1 C8 114.6(3) . . ?
C11 O2 C10 106.9(3) . . ?
C11 O3 C9 107.1(3) . . ?
C00P S1 C15 104.4(3) . . ?

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
O1 C1 C2 C7 176.8(4) . . . . ?
N1 C1 C2 C7 -1.5(4) . . . . ?
O1 C1 C2 C3 -2.5(7) . . . . ?
N1 C1 C2 C3 179.2(4) . . . . ?
C7 C2 C3 C4 -1.1(7) . . . . ?
C1 C2 C3 C4 178.1(5) . . . . ?
C2 C3 C4 C5 1.9(7) . . . . ?
C3 C4 C5 C6 -1.3(8) . . . . ?
C4 C5 C6 C7 -0.1(7) . . . . ?
C3 C2 C7 C6 -0.3(6) . . . . ?
C1 C2 C7 C6 -179.6(4) . . . . ?
C3 C2 C7 C8 178.5(4) . . . . ?
C1 C2 C7 C8 -0.9(4) . . . . ?
C5 C6 C7 C2 0.9(6) . . . . ?
C5 C6 C7 C8 -177.6(4) . . . . ?
C2 C7 C8 N1 2.6(4) . . . . ?
C6 C7 C8 N1 -178.8(4) . . . . ?
C2 C7 C8 C9 -109.2(4) . . . . ?
C6 C7 C8 C9 69.5(5) . . . . ?
C2 C7 C8 C12 120.8(4) . . . . ?
C6 C7 C8 C12 -60.5(6) . . . . ?
N1 C8 C9 C10 -6.8(6) . . . . ?
C12 C8 C9 C10 -129.8(5) . . . . ?
C7 C8 C9 C10 100.6(5) . . . . ?
N1 C8 C9 O3 176.9(3) . . . . ?
C12 C8 C9 O3 53.9(5) . . . . ?
C7 C8 C9 O3 -75.6(4) . . . . ?
O3 C9 C10 O2 0.6(5) . . . . ?
C8 C9 C10 O2 -176.0(4) . . . . ?
N1 C8 C12 C13 -99.1(5) . . . . ?
C9 C8 C12 C13 21.5(5) . . . . ?
C7 C8 C12 C13 149.2(4) . . . . ?
N1 C8 C12 C17 76.1(5) . . . . ?
C9 C8 C12 C17 -163.3(4) . . . . ?
C7 C8 C12 C17 -35.6(6) . . . . ?
C17 C12 C13 C14 -0.3(7) . . . . ?
C8 C12 C13 C14 175.1(5) . . . . ?
C12 C13 C14 C15 0.7(8) . . . . ?
C13 C14 C15 C16 0.0(8) . . . . ?
C13 C14 C15 S1 -177.6(4) . . . . ?
C14 C15 C16 C17 -1.0(9) . . . . ?
S1 C15 C16 C17 176.3(5) . . . . ?
C15 C16 C17 C12 1.4(9) . . . . ?
C13 C12 C17 C16 -0.7(8) . . . . ?
C8 C12 C17 C16 -176.2(5) . . . . ?
O1 C1 N1 C8 -174.9(4) . . . . ?
C2 C1 N1 C8 3.4(5) . . . . ?
C9 C8 N1 C1 110.8(4) . . . . ?
C12 C8 N1 C1 -124.0(4) . . . . ?
C7 C8 N1 C1 -3.7(4) . . . . ?
O4 C11 O2 C10 179.8(5) . . . . ?
O3 C11 O2 C10 1.1(5) . . . . ?
C9 C10 O2 C11 -1.1(5) . . . . ?
O4 C11 O3 C9 -179.4(5) . . . . ?
O2 C11 O3 C9 -0.7(5) . . . . ?
C10 C9 O3 C11 0.1(5) . . . . ?
C8 C9 O3 C11 177.2(3) . . . . ?
C14 C15 S1 C00P -164.6(5) . . . . ?
C16 C15 S1 C00P 18.1(6) . . . . ?

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.041




####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2286210'
loop_
_audit_author_name
_audit_author_address
Me
;sust
China
;
_audit_update_record             
;
2023-08-02 deposited with the CCDC.	2023-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 N O2'
_chemical_formula_weight         263.28

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.5438(13)
_cell_length_b                   9.2653(16)
_cell_length_c                   10.844(2)
_cell_angle_alpha                95.635(6)
_cell_angle_beta                 103.483(6)
_cell_angle_gamma                110.434(5)
_cell_volume                     677.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    8130
_cell_measurement_theta_min      5.523
_cell_measurement_theta_max      55.090

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             276
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.085
_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      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24188
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.393
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2654
_reflns_number_gt                2024
_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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1561P)²+3.9949P] 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         2654
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1397
_refine_ls_R_factor_gt           0.1189
_refine_ls_wR_factor_ref         0.3955
_refine_ls_wR_factor_gt          0.3796
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_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 0.5930(7) 0.2429(6) 0.1631(5) 0.0504(13) Uani 1 1 d . . . . .
C4 C 0.7532(9) 0.0857(6) 0.2778(6) 0.0329(13) Uani 1 1 d . . . . .
N1 N 0.8822(7) 0.3721(5) 0.3383(5) 0.0328(11) Uani 1 1 d . . . . .
H1 H 0.8404 0.3810 0.4049 0.039 Uiso 1 1 calc R U . . .
C16 C 1.0470(9) 0.4813(7) 0.3243(6) 0.0346(13) Uani 1 1 d . . . . .
C9 C 0.7823(9) 0.2391(7) 0.2315(6) 0.0341(13) Uani 1 1 d . . . . .
C2 C 0.5630(10) -0.1174(8) 0.3681(7) 0.0444(16) Uani 1 1 d . . . . .
H2 H 0.4514 -0.1632 0.3952 0.053 Uiso 1 1 calc R U . . .
C3 C 0.5857(8) 0.0167(7) 0.3161(6) 0.0360(14) Uani 1 1 d . . . . .
C1 C 0.7022(10) -0.1845(7) 0.3809(6) 0.0403(15) Uani 1 1 d . . . . .
C6 C 0.8681(11) -0.1135(8) 0.3421(7) 0.0456(16) Uani 1 1 d . . . . .
H6 H 0.9636 -0.1566 0.3507 0.055 Uiso 1 1 calc R U . . .
C10 C 0.9105(10) 0.2792(7) 0.1434(6) 0.0408(15) Uani 1 1 d . . . . .
C5 C 0.8948(10) 0.0202(7) 0.2909(6) 0.0394(14) Uani 1 1 d . . . . .
H5 H 1.0075 0.0666 0.2650 0.047 Uiso 1 1 calc R U . . .
C7 C 0.4380(10) 0.0846(8) 0.2960(8) 0.0482(17) Uani 1 1 d . . . . .
H7 H 0.3384 0.0554 0.3363 0.058 Uiso 1 1 calc R U . . .
C14 C 1.2057(11) 0.4889(9) 0.1352(7) 0.0483(17) Uani 1 1 d . . . . .
H14 H 1.3087 0.5857 0.1717 0.058 Uiso 1 1 calc R U . . .
C15 C 1.0661(9) 0.4232(7) 0.1974(6) 0.0372(14) Uani 1 1 d . . . . .
C8 C 0.4451(10) 0.1883(8) 0.2200(8) 0.0505(18) Uani 1 1 d . . . . .
H8 H 0.3444 0.2260 0.2044 0.061 Uiso 1 1 calc R U . . .
C11 C 0.8933(13) 0.1978(9) 0.0244(7) 0.055(2) Uani 1 1 d . . . . .
H11 H 0.7907 0.1010 -0.0127 0.066 Uiso 1 1 calc R U . . .
C13 C 1.1873(14) 0.4056(11) 0.0162(8) 0.063(2) Uani 1 1 d . . . . .
H13 H 1.2806 0.4458 -0.0274 0.076 Uiso 1 1 calc R U . . .
C12 C 1.0326(16) 0.2643(11) -0.0374(8) 0.070(3) Uani 1 1 d . . . . .
H12 H 1.0215 0.2118 -0.1181 0.084 Uiso 1 1 calc R U . . .
C17 C 0.6740(13) -0.3317(9) 0.4373(9) 0.062(2) Uani 1 1 d . . . . .
H17A H 0.7066 -0.4036 0.3858 0.093 Uiso 1 1 calc R U . . .
H17B H 0.5389 -0.3803 0.4374 0.093 Uiso 1 1 calc R U . . .
H17C H 0.7587 -0.3044 0.5243 0.093 Uiso 1 1 calc R U . . .
O2 O 1.1566(7) 0.6020(5) 0.4020(5) 0.0477(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.368(9) . ?
O1 C9 1.462(7) . ?
C4 C3 1.382(8) . ?
C4 C5 1.388(8) . ?
C4 C9 1.515(8) . ?
N1 C16 1.354(7) . ?
N1 C9 1.447(7) . ?
C16 O2 1.220(7) . ?
C16 C15 1.485(8) . ?
C9 C10 1.495(9) . ?
C2 C1 1.384(9) . ?
C2 C3 1.388(9) . ?
C3 C7 1.445(9) . ?
C1 C6 1.379(10) . ?
C1 C17 1.517(9) . ?
C6 C5 1.378(9) . ?
C10 C11 1.383(9) . ?
C10 C15 1.391(9) . ?
C7 C8 1.321(10) . ?
C14 C15 1.378(9) . ?
C14 C13 1.387(11) . ?
C11 C12 1.374(12) . ?
C13 C12 1.372(13) . ?

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
C8 O1 C9 115.3(5) . . ?
C3 C4 C5 120.0(5) . . ?
C3 C4 C9 117.8(5) . . ?
C5 C4 C9 122.0(5) . . ?
C16 N1 C9 114.1(5) . . ?
O2 C16 N1 126.0(5) . . ?
O2 C16 C15 127.8(6) . . ?
N1 C16 C15 106.2(5) . . ?
N1 C9 O1 108.9(5) . . ?
N1 C9 C10 102.1(5) . . ?
O1 C9 C10 106.1(5) . . ?
N1 C9 C4 111.2(5) . . ?
O1 C9 C4 110.9(5) . . ?
C10 C9 C4 116.9(5) . . ?
C1 C2 C3 121.7(6) . . ?
C4 C3 C2 118.9(6) . . ?
C4 C3 C7 118.3(6) . . ?
C2 C3 C7 122.7(6) . . ?
C6 C1 C2 118.3(6) . . ?
C6 C1 C17 120.8(6) . . ?
C2 C1 C17 120.9(6) . . ?
C5 C6 C1 121.1(6) . . ?
C11 C10 C15 120.0(6) . . ?
C11 C10 C9 130.3(6) . . ?
C15 C10 C9 109.7(5) . . ?
C6 C5 C4 119.9(6) . . ?
C8 C7 C3 119.7(6) . . ?
C15 C14 C13 117.7(7) . . ?
C14 C15 C10 121.7(6) . . ?
C14 C15 C16 130.5(6) . . ?
C10 C15 C16 107.9(5) . . ?
C7 C8 O1 123.3(6) . . ?
C12 C11 C10 118.0(7) . . ?
C12 C13 C14 120.4(7) . . ?
C13 C12 C11 122.2(7) . . ?

_refine_diff_density_max         0.509
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.114



