# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 2014380'
loop_
_audit_author_name
_audit_author_address
'zhongan li'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2020-07-06 deposited with the CCDC.	2020-11-20 downloaded from the CCDC.
;
_audit_creation_date             2020-01-07
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 Br N3 O S'
_chemical_formula_sum            'C14 H14 Br N3 O S'
_chemical_formula_weight         352.25
_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 0.0030 0.0020 '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'
Br Br -0.2900 2.4600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 '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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   15.716(4)
_cell_length_b                   7.1522(17)
_cell_length_c                   12.863(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1445.9(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1456
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.40
_cell_measurement_theta_min      2.59
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.986
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10242
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         2.046
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1039
_reflns_number_total             1461
_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         1461
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.062
_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)+(0.0976P)²+0.9067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1476
_refine_ls_wR_factor_ref         0.1661
_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. Restrained distances 
 C6-C5 = C5-C4 = C4-C3 
 1.51 with sigma of 0.02 
3. Others 
 Fixed Sof: H4A(0.5) H4B(0.5) C5(0.5) H5A(0.5) H5B(0.5) C13(0.5) H13A(0.5) 
 H13B(0.5) C14(0.5) H14A(0.5) H14B(0.5) H14C(0.5) O1(0.5) 
4.a Secondary CH2 refined with riding coordinates: 
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C13(H13A,H13B) 
4.b Aromatic/amide H refined with riding coordinates: 
 C2(H2) 
4.c Idealised Me refined as rotating group: 
 C14(H14A,H14B,H14C) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Br1 Br 1.20787(5) 0.7500 0.41964(7) 0.0742(4) Uani 1 2 d S T P . .
C1 C 0.9437(4) 0.7500 0.4112(5) 0.0396(15) Uani 1 2 d S T P A .
C2 C 1.0324(4) 0.7500 0.4412(5) 0.0424(15) Uani 1 2 d S T P . .
H2 H 1.0458 0.7500 0.5116 0.051 Uiso 1 2 calc RS T P . .
C3 C 1.0946(4) 0.7500 0.3734(5) 0.0450(16) Uani 1 2 d DS T P A .
C4 C 1.0833(4) 0.7500 0.2592(5) 0.0575(19) Uani 1 2 d DS T P . .
H4A H 1.1263 0.6714 0.2273 0.069 Uiso 0.5 1 calc R . . A .
H4B H 1.0902 0.8760 0.2326 0.069 Uiso 0.5 1 calc R . . . .
C5 C 0.9964(5) 0.6782(14) 0.2319(7) 0.053(3) Uani 0.5 1 d D . . A -1
H5A H 0.9842 0.7107 0.1602 0.064 Uiso 0.5 1 calc R . . A -1
H5B H 0.9968 0.5428 0.2368 0.064 Uiso 0.5 1 calc R . . A -1
C6 C 0.9281(4) 0.7500 0.2975(5) 0.0580(19) Uani 1 2 d DS T P . .
H6A H 0.8774 0.6766 0.2840 0.070 Uiso 1 1 calc R . . A .
H6B H 0.9160 0.8774 0.2761 0.070 Uiso 1 1 calc R . . . .
C7 C 0.8823(4) 0.7500 0.4823(5) 0.0408(15) Uani 1 2 d S T P . .
C8 C 0.7915(4) 0.7500 0.4643(6) 0.071(3) Uani 1 2 d S T P A .
C9 C 0.7942(4) 0.7500 0.6445(5) 0.0449(16) Uani 1 2 d S T P . .
C10 C 0.7684(4) 0.7500 0.7464(5) 0.0456(15) Uani 1 2 d S T P A .
C11 C 0.6835(4) 0.7500 0.7820(5) 0.0526(18) Uani 1 2 d S T P . .
C12 C 0.8317(4) 0.7500 0.8250(5) 0.0453(16) Uani 1 2 d S T P . .
C13 C 0.6525(7) 0.8221(15) 0.5556(7) 0.050(3) Uani 0.5 1 d . . . A -1
H13A H 0.6393 0.8967 0.6165 0.060 Uiso 0.5 1 calc R . . A -1
H13B H 0.6411 0.8946 0.4935 0.060 Uiso 0.5 1 calc R . . A -1
C14 C 0.6042(7) 0.642(2) 0.5555(11) 0.079(4) Uani 0.5 1 d . . . A -1
H14A H 0.6213 0.5677 0.4968 0.119 Uiso 0.5 1 calc GR . . A -1
H14B H 0.5443 0.6670 0.5513 0.119 Uiso 0.5 1 calc GR . . A -1
H14C H 0.6160 0.5742 0.6184 0.119 Uiso 0.5 1 calc GR . . A -1
N1 N 0.7469(4) 0.7500 0.5581(4) 0.070(2) Uani 1 2 d S T P A .
N2 N 0.6167(4) 0.7500 0.8159(5) 0.075(2) Uani 1 2 d S T P A .
N3 N 0.8820(5) 0.7500 0.8879(6) 0.076(2) Uani 1 2 d S T P A .
O1 O 0.7554(4) 0.6945(13) 0.3812(4) 0.063(4) Uani 0.5 1 d . . . . .
S1 S 0.90172(10) 0.7500 0.61637(12) 0.0383(4) Uani 1 2 d S T P A .


_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
Br1 C3 1.878(6) . ?
C1 C2 1.446(9) . ?
C1 C6 1.484(9) . ?
C1 C7 1.330(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.311(9) . ?
C3 C4 1.479(9) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.502(10) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.458(10) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.445(9) . ?
C7 S1 1.751(6) . ?
C8 N1 1.396(9) . ?
C8 O1 1.273(9) . ?
C8 O1 1.273(9) 8_575 ?
C9 C10 1.372(9) . ?
C9 N1 1.337(9) . ?
C9 S1 1.728(6) . ?
C10 C11 1.410(9) . ?
C10 C12 1.419(9) . ?
C11 N2 1.136(9) . ?
C12 N3 1.132(9) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.498(15) . ?
C13 N1 1.571(12) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O1 O1 0.793(19) 8_575 ?

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
C2 C1 C6 115.0(5) . . ?
C7 C1 C2 121.1(5) . . ?
C7 C1 C6 124.0(6) . . ?
C1 C2 H2 118.6 . . ?
C3 C2 C1 122.7(6) . . ?
C3 C2 H2 118.6 . . ?
C2 C3 Br1 119.7(5) . . ?
C2 C3 C4 124.9(6) . . ?
C4 C3 Br1 115.3(5) . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
C3 C4 C5 109.9(6) . . ?
H4A C4 H4B 108.2 . . ?
C5 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C4 C5 H5A 108.6 . . ?
C4 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
C6 C5 C4 114.5(7) . . ?
C6 C5 H5A 108.6 . . ?
C6 C5 H5B 108.6 . . ?
C1 C6 H6A 108.1 . . ?
C1 C6 H6B 108.1 . . ?
C5 C6 C1 116.7(6) . . ?
C5 C6 H6A 108.1 . . ?
C5 C6 H6B 108.1 . . ?
H6A C6 H6B 107.3 . . ?
C1 C7 C8 127.3(6) . . ?
C1 C7 S1 123.4(5) . . ?
C8 C7 S1 109.3(5) . . ?
N1 C8 C7 110.9(6) . . ?
O1 C8 C7 125.1(6) 8_575 . ?
O1 C8 C7 125.1(6) . . ?
O1 C8 N1 120.1(6) . . ?
O1 C8 N1 120.1(6) 8_575 . ?
O1 C8 O1 36.3(8) 8_575 . ?
C10 C9 S1 119.3(5) . . ?
N1 C9 C10 129.0(6) . . ?
N1 C9 S1 111.7(5) . . ?
C9 C10 C11 126.2(6) . . ?
C9 C10 C12 118.2(6) . . ?
C11 C10 C12 115.6(6) . . ?
N2 C11 C10 176.5(8) . . ?
N3 C12 C10 179.8(7) . . ?
H13A C13 H13B 109.3 . . ?
C14 C13 H13A 111.5 . . ?
C14 C13 H13B 111.5 . . ?
C14 C13 N1 101.3(7) . . ?
N1 C13 H13A 111.5 . . ?
N1 C13 H13B 111.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 N1 C13 117.2(5) . . ?
C9 N1 C8 116.1(5) . . ?
C9 N1 C13 122.8(6) . . ?
O1 O1 C8 71.8(4) 8_575 . ?
C9 S1 C7 92.0(3) . . ?

_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_190114a_0m
_database_code_depnum_ccdc_archive 'CCDC 2014381'
loop_
_audit_author_name
_audit_author_address
'zhongan li'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2020-07-06 deposited with the CCDC.	2020-11-20 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            'C14 H17 Cl N2 O2 S'
_chemical_formula_weight         312.80

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'
Cl Cl 0.1484 0.1585 '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      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                   9.049(3)
_cell_length_b                   9.739(3)
_cell_length_c                   9.862(3)
_cell_angle_alpha                67.129(5)
_cell_angle_beta                 82.299(5)
_cell_angle_gamma                67.966(5)
_cell_volume                     742.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1901
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      26.52

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.400
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.961
_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      293(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            6100
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.242
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3205
_reflns_number_gt                2254
_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0968P)²+0.1200P] 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         3205
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1572
_refine_ls_wR_factor_gt          0.1365
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_restrained_S_all      0.941
_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
C1 C 0.5358(2) 0.1675(2) 0.6890(2) 0.0421(5) Uani 1 1 d . . . . .
C2 C 0.4279(3) 0.1144(3) 0.8015(2) 0.0474(5) Uani 1 1 d . . . . .
H2 H 0.4108 0.0219 0.8138 0.057 Uiso 1 1 calc R U . . .
C3 C 0.3526(3) 0.1956(3) 0.8877(3) 0.0516(6) Uani 1 1 d . . . . .
C4 C 0.3815(4) 0.3321(3) 0.8952(3) 0.0672(7) Uani 1 1 d . . . . .
H4A H 0.3857 0.3199 0.9971 0.081 Uiso 1 1 calc R U . . .
H4B H 0.2951 0.4302 0.8459 0.081 Uiso 1 1 calc R U . . .
C5 C 0.5362(3) 0.3396(3) 0.8224(3) 0.0602(7) Uani 1 1 d . . . . .
H5A H 0.6240 0.2554 0.8859 0.072 Uiso 1 1 calc R U . . .
H5B H 0.5443 0.4408 0.8084 0.072 Uiso 1 1 calc R U . . .
C6 C 0.5497(3) 0.3217(3) 0.6749(3) 0.0494(5) Uani 1 1 d . . . . .
H6A H 0.4664 0.4101 0.6091 0.059 Uiso 1 1 calc R U . . .
H6B H 0.6517 0.3257 0.6319 0.059 Uiso 1 1 calc R U . . .
C7 C 0.6178(2) 0.0860(2) 0.5999(2) 0.0394(5) Uani 1 1 d . . . . .
C8 C 0.6960(2) 0.1623(3) 0.4679(2) 0.0429(5) Uani 1 1 d . . . . .
C9 C 0.6298(3) -0.0772(2) 0.6295(2) 0.0424(5) Uani 1 1 d . . . . .
C10 C 0.8470(2) -0.0972(3) 0.4499(2) 0.0453(5) Uani 1 1 d . . . . .
C11 C 0.8988(3) 0.1446(3) 0.2818(3) 0.0528(6) Uani 1 1 d . . . . .
H11A H 1.0063 0.0725 0.2776 0.063 Uiso 1 1 calc R U . . .
H11B H 0.9061 0.2352 0.2957 0.063 Uiso 1 1 calc R U . . .
C12 C 0.8130(3) 0.2013(4) 0.1387(3) 0.0678(7) Uani 1 1 d . . . . .
H12A H 0.8184 0.1110 0.1180 0.102 Uiso 1 1 calc R U . . .
H12B H 0.8625 0.2649 0.0607 0.102 Uiso 1 1 calc R U . . .
H12C H 0.7035 0.2640 0.1460 0.102 Uiso 1 1 calc R U . . .
C13 C 0.7690(3) -0.3303(3) 0.5978(3) 0.0559(6) Uani 1 1 d . . . . .
H13A H 0.8117 -0.3641 0.5157 0.067 Uiso 1 1 calc R U . . .
H13B H 0.6657 -0.3419 0.6210 0.067 Uiso 1 1 calc R U . . .
C14 C 0.8791(4) -0.4356(3) 0.7292(4) 0.0770(9) Uani 1 1 d . . . . .
H14A H 0.9859 -0.4386 0.7015 0.115 Uiso 1 1 calc R U . . .
H14B H 0.8765 -0.5414 0.7634 0.115 Uiso 1 1 calc R U . . .
H14C H 0.8452 -0.3938 0.8063 0.115 Uiso 1 1 calc R U . . .
Cl1 Cl 0.20490(8) 0.14131(9) 1.00266(7) 0.0699(3) Uani 1 1 d . . . . .
S1 S 0.99196(8) -0.20783(9) 0.37516(9) 0.0703(3) Uani 1 1 d . . . . .
N1 N 0.8158(2) 0.0620(2) 0.4084(2) 0.0429(4) Uani 1 1 d . . . . .
N2 N 0.7492(2) -0.1607(2) 0.5545(2) 0.0444(4) Uani 1 1 d . . . . .
O1 O 0.6610(2) 0.30460(18) 0.40721(18) 0.0575(5) Uani 1 1 d . . . . .
O2 O 0.5481(2) -0.1454(2) 0.7147(2) 0.0601(5) 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 C7 1.370(3) . ?
C1 C2 1.447(3) . ?
C1 C6 1.506(3) . ?
C2 C3 1.333(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.478(4) . ?
C3 Cl1 1.735(2) . ?
C4 C5 1.499(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.514(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.464(3) . ?
C7 C9 1.464(3) . ?
C8 O1 1.206(3) . ?
C8 N1 1.398(3) . ?
C9 O2 1.209(3) . ?
C9 N2 1.403(3) . ?
C10 N1 1.364(3) . ?
C10 N2 1.379(3) . ?
C10 S1 1.649(2) . ?
C11 N1 1.480(3) . ?
C11 C12 1.505(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N2 1.481(3) . ?
C13 C14 1.506(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C1 C2 123.1(2) . . ?
C7 C1 C6 122.0(2) . . ?
C2 C1 C6 114.86(18) . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 126.0(2) . . ?
C2 C3 Cl1 118.8(2) . . ?
C4 C3 Cl1 115.17(18) . . ?
C3 C4 C5 109.4(2) . . ?
C3 C4 H4A 109.8 . . ?
C5 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 . . ?
C5 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
C4 C5 C6 111.6(2) . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C1 C6 C5 111.88(19) . . ?
C1 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C1 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C1 C7 C8 120.25(19) . . ?
C1 C7 C9 122.57(19) . . ?
C8 C7 C9 117.17(18) . . ?
O1 C8 N1 118.98(19) . . ?
O1 C8 C7 124.05(19) . . ?
N1 C8 C7 116.95(18) . . ?
O2 C9 N2 118.27(19) . . ?
O2 C9 C7 125.30(19) . . ?
N2 C9 C7 116.41(18) . . ?
N1 C10 N2 116.87(18) . . ?
N1 C10 S1 121.60(17) . . ?
N2 C10 S1 121.51(17) . . ?
N1 C11 C12 111.7(2) . . ?
N1 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N1 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C14 111.7(2) . . ?
N2 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N2 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 N1 C8 124.59(18) . . ?
C10 N1 C11 120.46(18) . . ?
C8 N1 C11 114.63(18) . . ?
C10 N2 C9 124.97(18) . . ?
C10 N2 C13 119.92(18) . . ?
C9 N2 C13 115.10(19) . . ?

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
C7 C1 C2 C3 178.7(2) . . . . ?
C6 C1 C2 C3 -2.2(3) . . . . ?
C1 C2 C3 C4 -8.2(4) . . . . ?
C1 C2 C3 Cl1 171.26(16) . . . . ?
C2 C3 C4 C5 -15.0(4) . . . . ?
Cl1 C3 C4 C5 165.53(18) . . . . ?
C3 C4 C5 C6 46.8(3) . . . . ?
C7 C1 C6 C5 -146.4(2) . . . . ?
C2 C1 C6 C5 34.5(3) . . . . ?
C4 C5 C6 C1 -58.2(3) . . . . ?
C2 C1 C7 C8 166.1(2) . . . . ?
C6 C1 C7 C8 -12.9(3) . . . . ?
C2 C1 C7 C9 -13.0(3) . . . . ?
C6 C1 C7 C9 168.1(2) . . . . ?
C1 C7 C8 O1 -20.8(3) . . . . ?
C9 C7 C8 O1 158.3(2) . . . . ?
C1 C7 C8 N1 160.65(19) . . . . ?
C9 C7 C8 N1 -20.2(3) . . . . ?
C1 C7 C9 O2 14.6(4) . . . . ?
C8 C7 C9 O2 -164.5(2) . . . . ?
C1 C7 C9 N2 -163.7(2) . . . . ?
C8 C7 C9 N2 17.1(3) . . . . ?
N2 C10 N1 C8 2.2(3) . . . . ?
S1 C10 N1 C8 -179.41(16) . . . . ?
N2 C10 N1 C11 -170.96(19) . . . . ?
S1 C10 N1 C11 7.4(3) . . . . ?
O1 C8 N1 C10 -167.8(2) . . . . ?
C7 C8 N1 C10 10.8(3) . . . . ?
O1 C8 N1 C11 5.7(3) . . . . ?
C7 C8 N1 C11 -175.69(18) . . . . ?
C12 C11 N1 C10 87.1(3) . . . . ?
C12 C11 N1 C8 -86.7(3) . . . . ?
N1 C10 N2 C9 -5.6(3) . . . . ?
S1 C10 N2 C9 175.99(16) . . . . ?
N1 C10 N2 C13 175.96(19) . . . . ?
S1 C10 N2 C13 -2.4(3) . . . . ?
O2 C9 N2 C10 177.2(2) . . . . ?
C7 C9 N2 C10 -4.4(3) . . . . ?
O2 C9 N2 C13 -4.3(3) . . . . ?
C7 C9 N2 C13 174.12(19) . . . . ?
C14 C13 N2 C10 92.6(3) . . . . ?
C14 C13 N2 C9 -86.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12B Cl1 0.96 2.94 3.535(3) 121.3 1_654
C2 H2 O2 0.93 2.13 2.772(3) 125.0 .

_refine_diff_density_max         0.330
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.070

