# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_p
_database_code_depnum_ccdc_archive 'CCDC 1047606'
_audit_update_record             
;
2015-02-04 deposited with the CCDC.
2016-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 N O2 Rh'
_chemical_formula_weight         387.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Rh Rh 0.0927 3.6045 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   7.6555(3)
_cell_length_b                   13.0617(5)
_cell_length_c                   16.9622(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.793(3)
_cell_angle_gamma                90.00
_cell_volume                     1684.21(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3354
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      27.18

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    8.244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2324
_exptl_absorpt_correction_T_max  0.3034
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            19846
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.28
_diffrn_reflns_theta_max         67.09
_reflns_number_total             2989
_reflns_number_gt                2786
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0910P)²+0.8285P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2989
_refine_ls_number_parameters     199
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.029
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Rh1 Rh 0.45056(2) 0.271025(12) 0.308006(10) 0.01118(7) Uani 1 1 d . . .
N1 N 0.3301(3) 0.37345(16) 0.36810(13) 0.0165(5) Uani 1 1 d . . .
O1 O 0.2159(2) 0.44690(13) 0.32364(10) 0.0165(4) Uani 1 1 d . . .
O2 O 0.4202(3) 0.33801(18) 0.49583(12) 0.0352(6) Uani 1 1 d . . .
C18 C 0.2331(4) 0.4838(3) 0.47388(17) 0.0308(7) Uani 1 1 d . . .
H18A H 0.2484 0.4879 0.5308 0.046 Uiso 1 1 calc R . .
H18B H 0.1104 0.4757 0.4554 0.046 Uiso 1 1 calc R . .
H18C H 0.2762 0.5453 0.4521 0.046 Uiso 1 1 calc R . .
C1 C 0.1623(4) 0.3797(2) 0.08571(16) 0.0242(6) Uani 1 1 d . . .
H1A H 0.1473 0.3642 0.0318 0.029 Uiso 1 1 calc R . .
C2 C 0.0902(4) 0.4839(2) 0.19406(16) 0.0198(6) Uani 1 1 d . . .
H2A H 0.0294 0.5382 0.2134 0.024 Uiso 1 1 calc R . .
C3 C 0.0708(3) 0.4613(2) 0.11398(17) 0.0230(6) Uani 1 1 d . . .
H3A H -0.0036 0.5008 0.0788 0.028 Uiso 1 1 calc R . .
C4 C 0.2758(4) 0.3210(2) 0.13733(16) 0.0224(6) Uani 1 1 d . . .
H4A H 0.3368 0.2672 0.1173 0.027 Uiso 1 1 calc R . .
C5 C 0.3001(3) 0.34154(19) 0.21954(15) 0.0162(5) Uani 1 1 d . . .
C6 C 0.2027(3) 0.42366(19) 0.24523(15) 0.0157(5) Uani 1 1 d . . .
C7 C 0.6517(3) 0.1954(2) 0.25027(15) 0.0168(5) Uani 1 1 d . . .
C8 C 0.5148(3) 0.12513(18) 0.26167(15) 0.0166(5) Uani 1 1 d . . .
C9 C 0.6456(3) 0.1756(2) 0.38715(16) 0.0153(5) Uani 1 1 d . . .
C10 C 0.5110(3) 0.11369(18) 0.34660(15) 0.0154(5) Uani 1 1 d U . .
C11 C 0.7264(4) 0.22948(17) 0.32836(19) 0.0176(7) Uani 1 1 d . . .
C12 C 0.4016(4) 0.0669(2) 0.19918(17) 0.0257(7) Uani 1 1 d . . .
H12A H 0.4599 0.0046 0.1874 0.038 Uiso 1 1 calc R . .
H12B H 0.3809 0.1078 0.1520 0.038 Uiso 1 1 calc R . .
H12C H 0.2913 0.0510 0.2180 0.038 Uiso 1 1 calc R . .
C13 C 0.3337(3) 0.3934(2) 0.44786(16) 0.0197(6) Uani 1 1 d . . .
C14 C 0.8752(4) 0.3033(3) 0.3439(2) 0.0328(8) Uani 1 1 d . . .
H14A H 0.9845 0.2665 0.3506 0.049 Uiso 1 1 calc R . .
H14B H 0.8626 0.3414 0.3913 0.049 Uiso 1 1 calc R . .
H14C H 0.8742 0.3496 0.2999 0.049 Uiso 1 1 calc R . .
C15 C 0.3921(4) 0.0439(2) 0.38392(19) 0.0298(7) Uani 1 1 d . . .
H15A H 0.4500 -0.0206 0.3953 0.045 Uiso 1 1 calc R . .
H15B H 0.2866 0.0332 0.3483 0.045 Uiso 1 1 calc R . .
H15C H 0.3627 0.0737 0.4323 0.045 Uiso 1 1 calc R . .
C16 C 0.7160(5) 0.2253(2) 0.1739(2) 0.0309(8) Uani 1 1 d . . .
H16A H 0.8046 0.1779 0.1616 0.046 Uiso 1 1 calc R . .
H16B H 0.7652 0.2930 0.1787 0.046 Uiso 1 1 calc R . .
H16C H 0.6196 0.2245 0.1322 0.046 Uiso 1 1 calc R . .
C17 C 0.6962(4) 0.1785(2) 0.47478(16) 0.0282(7) Uani 1 1 d . . .
H17A H 0.7831 0.1268 0.4896 0.042 Uiso 1 1 calc R . .
H17B H 0.5943 0.1659 0.5013 0.042 Uiso 1 1 calc R . .
H17C H 0.7439 0.2446 0.4898 0.042 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
Rh1 N1 1.975(2) . ?
Rh1 C5 2.004(3) . ?
Rh1 C8 2.141(2) . ?
Rh1 C7 2.159(3) . ?
Rh1 C11 2.168(3) . ?
Rh1 C10 2.190(2) . ?
Rh1 C9 2.260(2) . ?
N1 C13 1.375(3) . ?
N1 O1 1.448(3) . ?
O1 C6 1.356(3) . ?
O2 C13 1.223(3) . ?
C18 C13 1.504(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C1 C4 1.389(4) . ?
C1 C3 1.392(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.381(4) . ?
C2 C6 1.391(4) . ?
C2 H2A 0.9300 . ?
C3 H3A 0.9300 . ?
C4 C5 1.411(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.405(4) . ?
C7 C8 1.423(4) . ?
C7 C11 1.449(4) . ?
C7 C16 1.491(4) . ?
C8 C10 1.452(4) . ?
C8 C12 1.495(4) . ?
C9 C11 1.421(4) . ?
C9 C10 1.422(4) . ?
C9 C17 1.492(4) . ?
C10 C15 1.482(4) . ?
C11 C14 1.492(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
N1 Rh1 C5 79.23(10) . . ?
N1 Rh1 C8 159.06(10) . . ?
C5 Rh1 C8 105.71(10) . . ?
N1 Rh1 C7 160.98(10) . . ?
C5 Rh1 C7 104.36(10) . . ?
C8 Rh1 C7 38.66(10) . . ?
N1 Rh1 C11 126.35(10) . . ?
C5 Rh1 C11 134.16(11) . . ?
C8 Rh1 C11 64.78(10) . . ?
C7 Rh1 C11 39.13(11) . . ?
N1 Rh1 C10 125.20(9) . . ?
C5 Rh1 C10 137.51(10) . . ?
C8 Rh1 C10 39.17(10) . . ?
C7 Rh1 C10 64.50(9) . . ?
C11 Rh1 C10 63.27(9) . . ?
N1 Rh1 C9 112.51(9) . . ?
C5 Rh1 C9 168.11(10) . . ?
C8 Rh1 C9 64.09(9) . . ?
C7 Rh1 C9 63.95(10) . . ?
C11 Rh1 C9 37.35(10) . . ?
C10 Rh1 C9 37.23(10) . . ?
C13 N1 O1 109.14(19) . . ?
C13 N1 Rh1 132.81(17) . . ?
O1 N1 Rh1 118.03(14) . . ?
C6 O1 N1 109.45(18) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C1 C3 120.5(3) . . ?
C4 C1 H1A 119.7 . . ?
C3 C1 H1A 119.7 . . ?
C3 C2 C6 118.7(3) . . ?
C3 C2 H2A 120.6 . . ?
C6 C2 H2A 120.6 . . ?
C2 C3 C1 120.1(3) . . ?
C2 C3 H3A 119.9 . . ?
C1 C3 H3A 119.9 . . ?
C1 C4 C5 121.2(3) . . ?
C1 C4 H4A 119.4 . . ?
C5 C4 H4A 119.4 . . ?
C6 C5 C4 116.0(2) . . ?
C6 C5 Rh1 113.43(18) . . ?
C4 C5 Rh1 130.5(2) . . ?
O1 C6 C2 117.0(2) . . ?
O1 C6 C5 119.6(2) . . ?
C2 C6 C5 123.4(2) . . ?
C8 C7 C11 106.9(2) . . ?
C8 C7 C16 127.7(3) . . ?
C11 C7 C16 125.3(3) . . ?
C8 C7 Rh1 69.96(14) . . ?
C11 C7 Rh1 70.77(15) . . ?
C16 C7 Rh1 126.89(19) . . ?
C7 C8 C10 107.6(2) . . ?
C7 C8 C12 127.3(2) . . ?
C10 C8 C12 125.0(2) . . ?
C7 C8 Rh1 71.38(14) . . ?
C10 C8 Rh1 72.24(14) . . ?
C12 C8 Rh1 125.02(18) . . ?
C11 C9 C10 107.0(2) . . ?
C11 C9 C17 127.1(3) . . ?
C10 C9 C17 125.8(2) . . ?
C11 C9 Rh1 67.81(15) . . ?
C10 C9 Rh1 68.68(14) . . ?
C17 C9 Rh1 130.82(19) . . ?
C9 C10 C8 108.8(2) . . ?
C9 C10 C15 126.2(2) . . ?
C8 C10 C15 124.9(2) . . ?
C9 C10 Rh1 74.09(14) . . ?
C8 C10 Rh1 68.60(13) . . ?
C15 C10 Rh1 125.91(19) . . ?
C9 C11 C7 109.4(2) . . ?
C9 C11 C14 125.6(3) . . ?
C7 C11 C14 124.8(3) . . ?
C9 C11 Rh1 74.84(16) . . ?
C7 C11 Rh1 70.10(15) . . ?
C14 C11 Rh1 125.10(19) . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 N1 119.3(2) . . ?
O2 C13 C18 121.6(2) . . ?
N1 C13 C18 119.1(2) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 C16 H16A 109.5 . . ?
C7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C9 C17 H17A 109.5 . . ?
C9 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C9 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        67.09
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.296
_refine_diff_density_min         -1.656
_refine_diff_density_rms         0.187
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1426755'
_audit_update_record             
;
2015-09-23 deposited with the CCDC.
2016-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H12 N2 O S2'
_chemical_formula_weight         360.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   7.38990(10)
_cell_length_b                   13.5531(2)
_cell_length_c                   32.123(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3217.3(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11673
_cell_measurement_theta_min      6.50
_cell_measurement_theta_max      68.20

_exptl_crystal_description       chip
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    3.082
_shelx_estimated_absorpt_T_min   0.578
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.309
_exptl_absorpt_correction_T_max  0.540
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19105
_diffrn_reflns_av_unetI/netI     0.0721
_diffrn_reflns_av_R_equivalents  0.1139
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         6.532
_diffrn_reflns_theta_max         68.345
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2903
_reflns_number_gt                1662
_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       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'

_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)+(0.1130P)²+0.4419P] 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         2903
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.2246
_refine_ls_wR_factor_gt          0.1715
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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
S1 S 0.19010(18) 0.14804(9) 0.15627(3) 0.0599(4) Uani 1 1 d . . . . .
S2 S 0.03998(19) -0.11502(9) 0.34714(4) 0.0630(4) Uani 1 1 d . . . . .
O3 O 0.1726(5) 0.0836(2) 0.23537(9) 0.0688(10) Uani 1 1 d . . . . .
H3 H 0.1806 0.0939 0.2605 0.083 Uiso 1 1 calc R U . . .
N5 N 0.1525(5) 0.0485(3) 0.31481(12) 0.0577(10) Uani 1 1 d . . . . .
N7 N 0.1109(6) -0.0081(3) 0.11338(12) 0.0615(11) Uani 1 1 d . . . . .
C4 C 0.0750(6) -0.0742(3) 0.26190(14) 0.0534(11) Uani 1 1 d . . . . .
C6 C 0.1277(6) 0.0248(4) 0.15147(14) 0.0541(12) Uani 1 1 d . . . . .
C8 C 0.0975(6) -0.0211(4) 0.38045(14) 0.0565(12) Uani 1 1 d . . . . .
C9 C 0.1453(7) 0.0663(4) 0.08521(14) 0.0592(13) Uani 1 1 d . . . . .
C10 C 0.0920(6) -0.0406(3) 0.18754(14) 0.0527(11) Uani 1 1 d . . . . .
C11 C 0.2063(7) 0.1477(4) 0.37814(16) 0.0665(14) Uani 1 1 d . . . . .
H11 H 0.2463 0.2024 0.3632 0.080 Uiso 1 1 calc R U . . .
C12 C 0.1145(7) -0.0094(3) 0.22891(14) 0.0536(12) Uani 1 1 d . . . . .
C13 C 0.2300(7) 0.2403(4) 0.07805(15) 0.0692(14) Uani 1 1 d . . . . .
H13 H 0.2608 0.3006 0.0898 0.083 Uiso 1 1 calc R U . . .
C14 C 0.0368(7) -0.1369(4) 0.18026(16) 0.0637(13) Uani 1 1 d . . . . .
H14 H 0.0237 -0.1586 0.1530 0.076 Uiso 1 1 calc R U . . .
C15 C 0.1917(7) 0.1575(4) 0.10267(14) 0.0575(12) Uani 1 1 d . . . . .
C16 C 0.1541(6) 0.0620(4) 0.35761(14) 0.0565(12) Uani 1 1 d . . . . .
C17 C 0.0205(7) -0.1692(4) 0.25287(16) 0.0635(13) Uani 1 1 d . . . . .
H17 H -0.0035 -0.2126 0.2746 0.076 Uiso 1 1 calc R U . . .
C18 C 0.1979(8) 0.1502(5) 0.42102(16) 0.0783(17) Uani 1 1 d . . . . .
H18 H 0.2307 0.2074 0.4351 0.094 Uiso 1 1 calc R U . . .
C19 C 0.2198(8) 0.2278(4) 0.03534(16) 0.0799(16) Uani 1 1 d . . . . .
H19 H 0.2436 0.2814 0.0181 0.096 Uiso 1 1 calc R U . . .
C20 C 0.1396(7) 0.0574(4) 0.04193(16) 0.0737(15) Uani 1 1 d . . . . .
H20 H 0.1117 -0.0029 0.0297 0.088 Uiso 1 1 calc R U . . .
C21 C 0.0952(6) -0.0406(3) 0.30492(14) 0.0545(12) Uani 1 1 d . . . . .
C22 C 0.1414(8) 0.0690(5) 0.44325(17) 0.0789(16) Uani 1 1 d . . . . .
H22 H 0.1385 0.0723 0.4722 0.095 Uiso 1 1 calc R U . . .
C23 C 0.0010(7) -0.2011(4) 0.21252(15) 0.0664(14) Uani 1 1 d . . . . .
H23 H -0.0359 -0.2654 0.2070 0.080 Uiso 1 1 calc R U . . .
C24 C 0.0891(8) -0.0169(4) 0.42382(16) 0.0716(15) Uani 1 1 d . . . . .
H24 H 0.0492 -0.0708 0.4392 0.086 Uiso 1 1 calc R U . . .
C25 C 0.1752(8) 0.1379(5) 0.01761(17) 0.0798(17) Uani 1 1 d . . . . .
H25 H 0.1694 0.1322 -0.0112 0.096 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C15 1.727(5) . ?
S1 C6 1.739(5) . ?
S2 C8 1.716(5) . ?
S2 C21 1.739(5) . ?
O3 C12 1.348(5) . ?
O3 H3 0.8200 . ?
N5 C21 1.318(6) . ?
N5 C16 1.387(6) . ?
N7 C6 1.308(6) . ?
N7 C9 1.378(6) . ?
C4 C17 1.379(6) . ?
C4 C12 1.408(6) . ?
C4 C21 1.463(6) . ?
C6 C10 1.483(6) . ?
C8 C24 1.396(7) . ?
C8 C16 1.409(6) . ?
C9 C20 1.396(6) . ?
C9 C15 1.401(7) . ?
C10 C14 1.387(6) . ?
C10 C12 1.404(6) . ?
C11 C18 1.379(6) . ?
C11 C16 1.390(6) . ?
C11 H11 0.9300 . ?
C13 C19 1.384(6) . ?
C13 C15 1.401(6) . ?
C13 H13 0.9300 . ?
C14 C23 1.379(6) . ?
C14 H14 0.9300 . ?
C17 C23 1.374(7) . ?
C17 H17 0.9300 . ?
C18 C22 1.376(8) . ?
C18 H18 0.9300 . ?
C19 C25 1.385(7) . ?
C19 H19 0.9300 . ?
C20 C25 1.367(7) . ?
C20 H20 0.9300 . ?
C22 C24 1.377(7) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25 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
C15 S1 C6 89.1(2) . . ?
C8 S2 C21 89.9(2) . . ?
C12 O3 H3 109.5 . . ?
C21 N5 C16 111.3(4) . . ?
C6 N7 C9 110.3(4) . . ?
C17 C4 C12 119.0(4) . . ?
C17 C4 C21 121.3(4) . . ?
C12 C4 C21 119.7(4) . . ?
N7 C6 C10 120.7(4) . . ?
N7 C6 S1 115.8(4) . . ?
C10 C6 S1 123.5(3) . . ?
C24 C8 C16 120.0(5) . . ?
C24 C8 S2 129.9(4) . . ?
C16 C8 S2 110.0(3) . . ?
N7 C9 C20 125.8(5) . . ?
N7 C9 C15 115.4(4) . . ?
C20 C9 C15 118.8(5) . . ?
C14 C10 C12 118.5(4) . . ?
C14 C10 C6 118.9(4) . . ?
C12 C10 C6 122.6(4) . . ?
C18 C11 C16 118.8(5) . . ?
C18 C11 H11 120.6 . . ?
C16 C11 H11 120.6 . . ?
O3 C12 C10 117.7(4) . . ?
O3 C12 C4 122.3(4) . . ?
C10 C12 C4 120.0(4) . . ?
C19 C13 C15 116.8(5) . . ?
C19 C13 H13 121.6 . . ?
C15 C13 H13 121.6 . . ?
C23 C14 C10 121.6(5) . . ?
C23 C14 H14 119.2 . . ?
C10 C14 H14 119.2 . . ?
C9 C15 C13 122.0(5) . . ?
C9 C15 S1 109.4(4) . . ?
C13 C15 S1 128.6(4) . . ?
N5 C16 C11 125.7(5) . . ?
N5 C16 C8 114.1(4) . . ?
C11 C16 C8 120.2(5) . . ?
C23 C17 C4 121.6(5) . . ?
C23 C17 H17 119.2 . . ?
C4 C17 H17 119.2 . . ?
C22 C18 C11 120.9(5) . . ?
C22 C18 H18 119.6 . . ?
C11 C18 H18 119.6 . . ?
C13 C19 C25 121.8(5) . . ?
C13 C19 H19 119.1 . . ?
C25 C19 H19 119.1 . . ?
C25 C20 C9 119.6(5) . . ?
C25 C20 H20 120.2 . . ?
C9 C20 H20 120.2 . . ?
N5 C21 C4 123.1(4) . . ?
N5 C21 S2 114.8(3) . . ?
C4 C21 S2 122.1(4) . . ?
C18 C22 C24 121.7(5) . . ?
C18 C22 H22 119.1 . . ?
C24 C22 H22 119.1 . . ?
C17 C23 C14 119.3(5) . . ?
C17 C23 H23 120.4 . . ?
C14 C23 H23 120.4 . . ?
C22 C24 C8 118.3(5) . . ?
C22 C24 H24 120.8 . . ?
C8 C24 H24 120.8 . . ?
C20 C25 C19 120.9(5) . . ?
C20 C25 H25 119.6 . . ?
C19 C25 H25 119.6 . . ?

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
C9 N7 C6 C10 178.1(4) . . . . ?
C9 N7 C6 S1 -1.0(5) . . . . ?
C15 S1 C6 N7 0.7(4) . . . . ?
C15 S1 C6 C10 -178.4(4) . . . . ?
C21 S2 C8 C24 178.1(5) . . . . ?
C21 S2 C8 C16 0.5(4) . . . . ?
C6 N7 C9 C20 -179.9(5) . . . . ?
C6 N7 C9 C15 0.8(6) . . . . ?
N7 C6 C10 C14 -1.2(7) . . . . ?
S1 C6 C10 C14 177.8(4) . . . . ?
N7 C6 C10 C12 177.7(4) . . . . ?
S1 C6 C10 C12 -3.3(7) . . . . ?
C14 C10 C12 O3 178.3(4) . . . . ?
C6 C10 C12 O3 -0.7(7) . . . . ?
C14 C10 C12 C4 -2.3(7) . . . . ?
C6 C10 C12 C4 178.8(4) . . . . ?
C17 C4 C12 O3 -178.4(4) . . . . ?
C21 C4 C12 O3 0.6(7) . . . . ?
C17 C4 C12 C10 2.3(7) . . . . ?
C21 C4 C12 C10 -178.7(4) . . . . ?
C12 C10 C14 C23 1.2(7) . . . . ?
C6 C10 C14 C23 -179.8(5) . . . . ?
N7 C9 C15 C13 -179.8(5) . . . . ?
C20 C9 C15 C13 0.9(8) . . . . ?
N7 C9 C15 S1 -0.3(5) . . . . ?
C20 C9 C15 S1 -179.6(4) . . . . ?
C19 C13 C15 C9 0.0(8) . . . . ?
C19 C13 C15 S1 -179.4(4) . . . . ?
C6 S1 C15 C9 -0.2(4) . . . . ?
C6 S1 C15 C13 179.3(5) . . . . ?
C21 N5 C16 C11 -179.6(5) . . . . ?
C21 N5 C16 C8 0.7(6) . . . . ?
C18 C11 C16 N5 179.0(5) . . . . ?
C18 C11 C16 C8 -1.3(7) . . . . ?
C24 C8 C16 N5 -178.7(4) . . . . ?
S2 C8 C16 N5 -0.8(5) . . . . ?
C24 C8 C16 C11 1.7(7) . . . . ?
S2 C8 C16 C11 179.6(4) . . . . ?
C12 C4 C17 C23 -1.1(8) . . . . ?
C21 C4 C17 C23 179.9(5) . . . . ?
C16 C11 C18 C22 1.0(8) . . . . ?
C15 C13 C19 C25 -0.4(8) . . . . ?
N7 C9 C20 C25 179.4(5) . . . . ?
C15 C9 C20 C25 -1.4(8) . . . . ?
C16 N5 C21 C4 178.3(4) . . . . ?
C16 N5 C21 S2 -0.3(5) . . . . ?
C17 C4 C21 N5 177.7(5) . . . . ?
C12 C4 C21 N5 -1.2(7) . . . . ?
C17 C4 C21 S2 -3.7(7) . . . . ?
C12 C4 C21 S2 177.3(4) . . . . ?
C8 S2 C21 N5 -0.1(4) . . . . ?
C8 S2 C21 C4 -178.7(4) . . . . ?
C11 C18 C22 C24 -0.9(9) . . . . ?
C4 C17 C23 C14 0.0(8) . . . . ?
C10 C14 C23 C17 0.0(8) . . . . ?
C18 C22 C24 C8 1.2(9) . . . . ?
C16 C8 C24 C22 -1.5(8) . . . . ?
S2 C8 C24 C22 -179.0(4) . . . . ?
C9 C20 C25 C19 1.1(9) . . . . ?
C13 C19 C25 C20 -0.1(9) . . . . ?

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
O3 H3 N5 0.82 1.86 2.600(5) 149.0 .
C11 H11 S2 0.93 2.98 3.853(6) 156.7 2

_refine_diff_density_max         0.296
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.082

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_A
_database_code_depnum_ccdc_archive 'CCDC 1438599'
_audit_update_record             
;
2015-11-24 deposited with the CCDC.
2016-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        cy-P3-NHAc-thiazole
_chemical_name_common            chenying
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 N2 O2 S'
_chemical_formula_sum            'C3.53 H2.82 N0.47 O0.47 S0.24'
_chemical_formula_weight         66.90

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   4.7941(7)
_cell_length_b                   15.333(2)
_cell_length_c                   17.698(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1301.0(3)
_cell_formula_units_Z            17
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6071
_cell_measurement_theta_min      3.455
_cell_measurement_theta_max      27.565

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.186
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.053
_exptl_absorpt_coefficient_mu    0.251
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IP'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7897
_diffrn_reflns_av_unetI/netI     0.0909
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.516
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             2850
_reflns_number_gt                1950
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.626
_reflns_Friedel_fraction_max     0.898
_reflns_Friedel_fraction_full    0.933

_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       'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0578P)²] 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 524 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2850
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1374
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
S1 S 0.9265(3) 0.41953(9) 0.84670(6) 0.0332(3) Uani 1 1 d . . . . .
N1 N 1.1126(9) 0.5753(3) 0.8778(2) 0.0334(10) Uani 1 1 d . . . . .
N2 N 0.4341(9) 0.4046(3) 0.6778(2) 0.0331(10) Uani 1 1 d . . . . .
H2B H 0.2605 0.4090 0.6621 0.040 Uiso 1 1 calc R U . . .
O1 O 0.5315(8) 0.4508(2) 0.74160(16) 0.0332(8) Uani 1 1 d . . . . .
O2 O 0.8747(8) 0.3577(2) 0.6546(2) 0.0429(9) Uani 1 1 d . . . . .
C1 C 1.1782(11) 0.4297(3) 0.9166(2) 0.0315(11) Uani 1 1 d . . . . .
C2 C 1.3001(11) 0.3643(4) 0.9611(3) 0.0364(12) Uani 1 1 d . . . . .
H2A H 1.2470 0.3049 0.9556 0.044 Uiso 1 1 calc R U . . .
C3 C 1.5006(12) 0.3889(4) 1.0135(3) 0.0381(13) Uani 1 1 d . . . . .
H3A H 1.5859 0.3459 1.0443 0.046 Uiso 1 1 calc R U . . .
C4 C 1.5791(12) 0.4766(3) 1.0214(3) 0.0363(12) Uani 1 1 d . . . . .
H4A H 1.7200 0.4917 1.0568 0.044 Uiso 1 1 calc R U . . .
C5 C 1.4555(11) 0.5415(4) 0.9786(2) 0.0351(12) Uani 1 1 d . . . . .
H5A H 1.5061 0.6009 0.9853 0.042 Uiso 1 1 calc R U . . .
C6 C 1.2535(11) 0.5174(3) 0.9253(2) 0.0318(11) Uani 1 1 d . . . . .
C7 C 0.9395(11) 0.5335(3) 0.8334(2) 0.0318(11) Uani 1 1 d . . . . .
C8 C 0.7706(10) 0.5800(4) 0.7760(2) 0.0298(10) Uani 1 1 d . . . . .
C9 C 0.8101(11) 0.6702(3) 0.7666(3) 0.0349(12) Uani 1 1 d . . . . .
H9A H 0.9410 0.6996 0.7979 0.042 Uiso 1 1 calc R U . . .
C10 C 0.6637(12) 0.7170(4) 0.7133(3) 0.0380(13) Uani 1 1 d . . . . .
H10A H 0.6947 0.7779 0.7080 0.046 Uiso 1 1 calc R U . . .
C11 C 0.4699(12) 0.6750(4) 0.6671(3) 0.0384(13) Uani 1 1 d . . . . .
H11A H 0.3677 0.7074 0.6306 0.046 Uiso 1 1 calc R U . . .
C12 C 0.4263(11) 0.5855(3) 0.6746(2) 0.0337(11) Uani 1 1 d . . . . .
H12A H 0.2955 0.5564 0.6431 0.040 Uiso 1 1 calc R U . . .
C13 C 0.5759(11) 0.5393(3) 0.7285(2) 0.0295(11) Uani 1 1 d . . . . .
C14 C 0.6222(11) 0.3531(3) 0.6419(3) 0.0328(11) Uani 1 1 d . . . . .
C15 C 0.5002(12) 0.2943(4) 0.5826(2) 0.0395(14) Uani 1 1 d . . . . .
H15A H 0.2968 0.3007 0.5821 0.059 Uiso 1 1 calc R U . . .
H15B H 0.5756 0.3101 0.5330 0.059 Uiso 1 1 calc R U . . .
H15C H 0.5485 0.2336 0.5940 0.059 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.734(5) . ?
S1 C7 1.764(5) . ?
N1 C7 1.310(6) . ?
N1 C6 1.397(6) . ?
N2 C14 1.356(6) . ?
N2 O1 1.413(5) . ?
N2 H2B 0.8800 . ?
O1 C13 1.394(6) . ?
O2 C14 1.233(6) . ?
C1 C6 1.402(7) . ?
C1 C2 1.403(7) . ?
C2 C3 1.388(7) . ?
C2 H2A 0.9500 . ?
C3 C4 1.403(8) . ?
C3 H3A 0.9500 . ?
C4 C5 1.384(7) . ?
C4 H4A 0.9500 . ?
C5 C6 1.402(7) . ?
C5 H5A 0.9500 . ?
C7 C8 1.481(7) . ?
C8 C13 1.402(7) . ?
C8 C9 1.406(7) . ?
C9 C10 1.379(7) . ?
C9 H9A 0.9500 . ?
C10 C11 1.395(7) . ?
C10 H10A 0.9500 . ?
C11 C12 1.395(8) . ?
C11 H11A 0.9500 . ?
C12 C13 1.388(7) . ?
C12 H12A 0.9500 . ?
C14 C15 1.503(7) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C1 S1 C7 89.0(2) . . ?
C7 N1 C6 110.9(4) . . ?
C14 N2 O1 116.5(4) . . ?
C14 N2 H2B 121.8 . . ?
O1 N2 H2B 121.8 . . ?
C13 O1 N2 113.9(3) . . ?
C6 C1 C2 121.1(5) . . ?
C6 C1 S1 110.1(4) . . ?
C2 C1 S1 128.8(4) . . ?
C3 C2 C1 118.0(5) . . ?
C3 C2 H2A 121.0 . . ?
C1 C2 H2A 121.0 . . ?
C2 C3 C4 120.9(5) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C5 C4 C3 121.3(5) . . ?
C5 C4 H4A 119.4 . . ?
C3 C4 H4A 119.4 . . ?
C4 C5 C6 118.3(5) . . ?
C4 C5 H5A 120.8 . . ?
C6 C5 H5A 120.8 . . ?
N1 C6 C1 114.8(4) . . ?
N1 C6 C5 124.9(5) . . ?
C1 C6 C5 120.3(5) . . ?
N1 C7 C8 121.5(4) . . ?
N1 C7 S1 115.3(4) . . ?
C8 C7 S1 123.3(4) . . ?
C13 C8 C9 117.1(5) . . ?
C13 C8 C7 124.2(5) . . ?
C9 C8 C7 118.7(5) . . ?
C10 C9 C8 121.7(5) . . ?
C10 C9 H9A 119.2 . . ?
C8 C9 H9A 119.2 . . ?
C9 C10 C11 120.0(5) . . ?
C9 C10 H10A 120.0 . . ?
C11 C10 H10A 120.0 . . ?
C10 C11 C12 119.9(5) . . ?
C10 C11 H11A 120.0 . . ?
C12 C11 H11A 120.0 . . ?
C13 C12 C11 119.3(5) . . ?
C13 C12 H12A 120.3 . . ?
C11 C12 H12A 120.3 . . ?
C12 C13 O1 122.2(4) . . ?
C12 C13 C8 122.0(4) . . ?
O1 C13 C8 115.8(4) . . ?
O2 C14 N2 122.3(5) . . ?
O2 C14 C15 123.0(5) . . ?
N2 C14 C15 114.7(4) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C14 N2 O1 C13 104.7(5) . . . . ?
C7 S1 C1 C6 0.2(4) . . . . ?
C7 S1 C1 C2 179.9(5) . . . . ?
C6 C1 C2 C3 -0.8(7) . . . . ?
S1 C1 C2 C3 179.5(4) . . . . ?
C1 C2 C3 C4 -0.1(7) . . . . ?
C2 C3 C4 C5 1.4(8) . . . . ?
C3 C4 C5 C6 -1.7(8) . . . . ?
C7 N1 C6 C1 -1.1(6) . . . . ?
C7 N1 C6 C5 179.1(5) . . . . ?
C2 C1 C6 N1 -179.2(4) . . . . ?
S1 C1 C6 N1 0.4(5) . . . . ?
C2 C1 C6 C5 0.6(7) . . . . ?
S1 C1 C6 C5 -179.8(4) . . . . ?
C4 C5 C6 N1 -179.5(5) . . . . ?
C4 C5 C6 C1 0.7(7) . . . . ?
C6 N1 C7 C8 -178.2(4) . . . . ?
C6 N1 C7 S1 1.3(5) . . . . ?
C1 S1 C7 N1 -0.9(4) . . . . ?
C1 S1 C7 C8 178.6(4) . . . . ?
N1 C7 C8 C13 -178.0(4) . . . . ?
S1 C7 C8 C13 2.6(7) . . . . ?
N1 C7 C8 C9 3.6(7) . . . . ?
S1 C7 C8 C9 -175.9(4) . . . . ?
C13 C8 C9 C10 0.2(7) . . . . ?
C7 C8 C9 C10 178.7(5) . . . . ?
C8 C9 C10 C11 0.2(8) . . . . ?
C9 C10 C11 C12 -0.5(8) . . . . ?
C10 C11 C12 C13 0.4(7) . . . . ?
C11 C12 C13 O1 176.5(4) . . . . ?
C11 C12 C13 C8 0.0(7) . . . . ?
N2 O1 C13 C12 28.4(6) . . . . ?
N2 O1 C13 C8 -155.0(4) . . . . ?
C9 C8 C13 C12 -0.3(7) . . . . ?
C7 C8 C13 C12 -178.8(4) . . . . ?
C9 C8 C13 O1 -177.0(4) . . . . ?
C7 C8 C13 O1 4.5(6) . . . . ?
O1 N2 C14 O2 -13.1(7) . . . . ?
O1 N2 C14 C15 170.5(4) . . . . ?

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.068


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_chemical_properties_physical    'Hygroscopic, Heat-sensitive'
####################################################################### 
# 
# 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_A
_database_code_depnum_ccdc_archive 'CCDC 1442845'
_audit_update_record             
;
2015-12-16 deposited with the CCDC.
2016-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        cy-hybrid-P2
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4.40 H0 N0.20 O0.20 S0.40'
_chemical_formula_weight         71.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   4.6897(7)
_cell_length_b                   12.449(3)
_cell_length_c                   15.119(4)
_cell_angle_alpha                109.35(2)
_cell_angle_beta                 96.794(16)
_cell_angle_gamma                99.101(16)
_cell_volume                     808.4(3)
_cell_formula_units_Z            10
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_F_000             358
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    3.066
_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      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3871
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.151
_diffrn_reflns_theta_max         61.992
_diffrn_reflns_theta_full        61.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2528
_reflns_number_gt                1738
_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)+(0.1776P)²+1.8766P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2528
_refine_ls_number_parameters     236
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1509
_refine_ls_R_factor_gt           0.1127
_refine_ls_wR_factor_ref         0.3289
_refine_ls_wR_factor_gt          0.2996
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_restrained_S_all      1.203
_refine_ls_shift/su_max          0.570
_refine_ls_shift/su_mean         0.022

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.7132(4) 0.33417(18) 0.20185(15) 0.0445(7) Uani 1 1 d . . . . .
N1 N 0.7834(10) 0.1277(4) 0.1112(4) 0.0199(12) Uani 1 1 d . . . . .
O2 O -0.1544(9) 0.1306(4) 0.4630(3) 0.0280(11) Uani 1 1 d . . . . .
O1 O 0.3829(9) 0.3056(4) 0.3293(3) 0.0285(12) Uani 1 1 d . . . . .
H1A H 0.2888 0.3281 0.3745 0.034 Uiso 1 1 d R U . . .
N2 N 0.0541(9) 0.3263(4) 0.4656(3) 0.0134(10) Uani 1 1 d . U . . .
C1 C 0.3385(13) 0.1887(5) 0.3026(5) 0.0217(14) Uani 1 1 d . . . . .
C2 C 0.4717(13) 0.1272(5) 0.2278(5) 0.0226(14) Uani 1 1 d . . . . .
C3 C 0.4260(13) 0.0069(5) 0.2005(5) 0.0250(15) Uani 1 1 d . . . . .
H3A H 0.5132 -0.0351 0.1499 0.030 Uiso 1 1 calc R U . . .
C4 C 0.2585(14) -0.0531(5) 0.2445(5) 0.0268(15) Uani 1 1 d . . . . .
H4A H 0.2340 -0.1353 0.2249 0.032 Uiso 1 1 calc R U . . .
C5 C 0.1261(13) 0.0056(6) 0.3169(5) 0.0263(15) Uani 1 1 d . . . . .
H5A H 0.0089 -0.0365 0.3466 0.032 Uiso 1 1 calc R U . . .
C6 C 0.1628(13) 0.1280(5) 0.3473(5) 0.0227(14) Uani 1 1 d . . . . .
C7 C 0.6567(13) 0.1864(6) 0.1793(4) 0.0233(14) Uani 1 1 d . . . . .
C8 C 0.9347(13) 0.2034(5) 0.0751(5) 0.0240(15) Uani 1 1 d . . . . .
C9 C 0.9147(15) 0.3208(6) 0.1182(6) 0.0375(19) Uani 1 1 d . . . . .
C10 C 1.0546(19) 0.4060(7) 0.0856(8) 0.062(3) Uani 1 1 d . . . . .
H10A H 1.0428 0.4854 0.1130 0.074 Uiso 1 1 calc R U . . .
C11 C 1.2095(19) 0.3696(10) 0.0125(8) 0.061(3) Uani 1 1 d . . . . .
H11A H 1.3050 0.4256 -0.0104 0.074 Uiso 1 1 calc R U . . .
C12 C 1.2293(18) 0.2585(8) -0.0271(6) 0.051(2) Uani 1 1 d . . . . .
H12A H 1.3367 0.2378 -0.0775 0.061 Uiso 1 1 calc R U . . .
C13 C 1.0992(15) 0.1738(7) 0.0029(5) 0.0373(18) Uani 1 1 d . . . . .
H13A H 1.1205 0.0957 -0.0251 0.045 Uiso 1 1 calc R U . . .
C14 C 0.0223(13) 0.1896(5) 0.4219(4) 0.0208(14) Uani 1 1 d . . . . .
C15 C -0.2510(14) 0.2142(5) 0.5320(4) 0.0248(15) Uani 1 1 d . . . . .
C16 C -0.1259(17) 0.3243(6) 0.5308(6) 0.0394(19) Uani 1 1 d . . . . .
C17 C -0.166(2) 0.4258(8) 0.5920(7) 0.051(2) Uani 1 1 d . . . . .
H17A H -0.0778 0.4998 0.5916 0.062 Uiso 1 1 calc R U . . .
C18 C -0.337(2) 0.4132(7) 0.6520(7) 0.054(3) Uani 1 1 d . . . . .
H18A H -0.3720 0.4828 0.6953 0.064 Uiso 1 1 calc R U . . .
C19 C -0.4777(18) 0.3053(9) 0.6599(6) 0.055(3) Uani 1 1 d . . . . .
C20 C -0.4306(15) 0.1989(7) 0.5934(5) 0.0334(17) Uani 1 1 d . . . . .
H20A H -0.5177 0.1241 0.5924 0.040 Uiso 1 1 calc R U . . .
C21 C -0.645(2) 0.3045(8) 0.7345(7) 0.056(2) Uani 1 1 d . . . . .
H21A H -0.5261 0.3552 0.7965 0.084 Uiso 1 1 calc R U . . .
H21B H -0.6973 0.2249 0.7340 0.084 Uiso 1 1 calc R U . . .
H21C H -0.8242 0.3329 0.7234 0.084 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C9 1.647(9) . ?
S1 C7 1.726(7) . ?
N1 C7 1.316(8) . ?
N1 C8 1.383(8) . ?
O2 C14 1.358(8) . ?
O2 C15 1.386(7) . ?
O1 C1 1.349(7) . ?
O1 H1A 0.8501 . ?
N2 C16 1.374(10) . ?
N2 C14 1.584(7) . ?
C1 C6 1.407(9) . ?
C1 C2 1.414(9) . ?
C2 C3 1.388(9) . ?
C2 C7 1.463(9) . ?
C3 C4 1.373(9) . ?
C3 H3A 0.9500 . ?
C4 C5 1.375(9) . ?
C4 H4A 0.9500 . ?
C5 C6 1.413(9) . ?
C5 H5A 0.9500 . ?
C6 C14 1.435(9) . ?
C8 C13 1.395(10) . ?
C8 C9 1.412(10) . ?
C9 C10 1.415(13) . ?
C10 C11 1.385(15) . ?
C10 H10A 0.9500 . ?
C11 C12 1.336(14) . ?
C11 H11A 0.9500 . ?
C12 C13 1.367(11) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C15 C20 1.364(10) . ?
C15 C16 1.410(10) . ?
C16 C17 1.353(12) . ?
C17 C18 1.309(14) . ?
C17 H17A 0.9500 . ?
C18 C19 1.450(14) . ?
C18 H18A 0.9500 . ?
C19 C20 1.441(11) . ?
C19 C21 1.449(12) . ?
C20 H20A 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C9 S1 C7 90.7(3) . . ?
C7 N1 C8 109.3(5) . . ?
C14 O2 C15 106.0(5) . . ?
C1 O1 H1A 106.2 . . ?
C16 N2 C14 95.5(5) . . ?
O1 C1 C6 121.3(5) . . ?
O1 C1 C2 118.6(6) . . ?
C6 C1 C2 120.1(6) . . ?
C3 C2 C1 118.5(6) . . ?
C3 C2 C7 119.4(6) . . ?
C1 C2 C7 122.1(6) . . ?
C4 C3 C2 121.9(6) . . ?
C4 C3 H3A 119.0 . . ?
C2 C3 H3A 119.0 . . ?
C3 C4 C5 120.1(6) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C4 C5 C6 120.5(6) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.7 . . ?
C5 C6 C1 118.8(6) . . ?
C5 C6 C14 120.8(6) . . ?
C1 C6 C14 120.4(6) . . ?
N1 C7 C2 121.0(6) . . ?
N1 C7 S1 115.1(5) . . ?
C2 C7 S1 123.8(5) . . ?
N1 C8 C13 126.1(6) . . ?
N1 C8 C9 114.4(6) . . ?
C13 C8 C9 119.5(7) . . ?
C8 C9 C10 119.5(8) . . ?
C8 C9 S1 110.6(6) . . ?
C10 C9 S1 129.9(7) . . ?
C11 C10 C9 117.6(8) . . ?
C11 C10 H10A 121.2 . . ?
C9 C10 H10A 121.2 . . ?
C12 C11 C10 122.3(9) . . ?
C12 C11 H11A 118.9 . . ?
C10 C11 H11A 118.9 . . ?
C11 C12 C13 121.8(9) . . ?
C11 C12 H12A 119.1 . . ?
C13 C12 H12A 119.1 . . ?
C12 C13 C8 119.2(8) . . ?
C12 C13 H13A 120.4 . . ?
C8 C13 H13A 120.4 . . ?
O2 C14 C6 120.3(5) . . ?
O2 C14 N2 113.5(5) . . ?
C6 C14 N2 126.1(5) . . ?
C20 C15 O2 128.5(6) . . ?
C20 C15 C16 123.5(7) . . ?
O2 C15 C16 108.0(6) . . ?
C17 C16 N2 119.5(7) . . ?
C17 C16 C15 123.4(8) . . ?
N2 C16 C15 117.0(6) . . ?
C18 C17 C16 114.1(8) . . ?
C18 C17 H17A 122.9 . . ?
C16 C17 H17A 123.0 . . ?
C17 C18 C19 127.5(8) . . ?
C17 C18 H18A 116.3 . . ?
C19 C18 H18A 116.2 . . ?
C20 C19 C18 116.9(8) . . ?
C20 C19 C21 121.5(9) . . ?
C18 C19 C21 121.6(9) . . ?
C15 C20 C19 114.6(7) . . ?
C15 C20 H20A 122.7 . . ?
C19 C20 H20A 122.7 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
O1 C1 C2 C3 179.9(5) . . . . ?
C6 C1 C2 C3 -0.3(9) . . . . ?
O1 C1 C2 C7 0.4(9) . . . . ?
C6 C1 C2 C7 -179.9(6) . . . . ?
C1 C2 C3 C4 -0.6(10) . . . . ?
C7 C2 C3 C4 178.9(6) . . . . ?
C2 C3 C4 C5 1.1(10) . . . . ?
C3 C4 C5 C6 -0.6(10) . . . . ?
C4 C5 C6 C1 -0.4(10) . . . . ?
C4 C5 C6 C14 179.2(6) . . . . ?
O1 C1 C6 C5 -179.5(5) . . . . ?
C2 C1 C6 C5 0.8(9) . . . . ?
O1 C1 C6 C14 1.0(9) . . . . ?
C2 C1 C6 C14 -178.8(5) . . . . ?
C8 N1 C7 C2 177.6(5) . . . . ?
C8 N1 C7 S1 0.3(7) . . . . ?
C3 C2 C7 N1 -0.9(9) . . . . ?
C1 C2 C7 N1 178.6(6) . . . . ?
C3 C2 C7 S1 176.1(5) . . . . ?
C1 C2 C7 S1 -4.4(9) . . . . ?
C9 S1 C7 N1 -0.1(5) . . . . ?
C9 S1 C7 C2 -177.3(6) . . . . ?
C7 N1 C8 C13 179.2(6) . . . . ?
C7 N1 C8 C9 -0.5(8) . . . . ?
N1 C8 C9 C10 -178.5(6) . . . . ?
C13 C8 C9 C10 1.8(10) . . . . ?
N1 C8 C9 S1 0.4(7) . . . . ?
C13 C8 C9 S1 -179.3(5) . . . . ?
C7 S1 C9 C8 -0.2(5) . . . . ?
C7 S1 C9 C10 178.5(7) . . . . ?
C8 C9 C10 C11 -0.7(11) . . . . ?
S1 C9 C10 C11 -179.2(6) . . . . ?
C9 C10 C11 C12 0.0(13) . . . . ?
C10 C11 C12 C13 -0.5(14) . . . . ?
C11 C12 C13 C8 1.7(12) . . . . ?
N1 C8 C13 C12 178.0(6) . . . . ?
C9 C8 C13 C12 -2.3(10) . . . . ?
C15 O2 C14 C6 179.3(5) . . . . ?
C15 O2 C14 N2 0.2(6) . . . . ?
C5 C6 C14 O2 -1.6(9) . . . . ?
C1 C6 C14 O2 178.0(5) . . . . ?
C5 C6 C14 N2 177.5(5) . . . . ?
C1 C6 C14 N2 -3.0(9) . . . . ?
C16 N2 C14 O2 -0.1(6) . . . . ?
C16 N2 C14 C6 -179.2(6) . . . . ?
C14 O2 C15 C20 -179.2(7) . . . . ?
C14 O2 C15 C16 -0.2(7) . . . . ?
C14 N2 C16 C17 177.5(7) . . . . ?
C14 N2 C16 C15 0.0(7) . . . . ?
C20 C15 C16 C17 1.7(12) . . . . ?
O2 C15 C16 C17 -177.3(7) . . . . ?
C20 C15 C16 N2 179.1(6) . . . . ?
O2 C15 C16 N2 0.1(8) . . . . ?
N2 C16 C17 C18 -178.6(8) . . . . ?
C15 C16 C17 C18 -1.2(12) . . . . ?
C16 C17 C18 C19 1.1(14) . . . . ?
C17 C18 C19 C20 -1.2(13) . . . . ?
C17 C18 C19 C21 175.5(9) . . . . ?
O2 C15 C20 C19 177.2(6) . . . . ?
C16 C15 C20 C19 -1.7(10) . . . . ?
C18 C19 C20 C15 1.4(10) . . . . ?
C21 C19 C20 C15 -175.3(7) . . . . ?

_refine_diff_density_max         2.164
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.134

