# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_170510_1_xiamin_green
_database_code_depnum_ccdc_archive 'CCDC 1551666'
_audit_update_record             
;
2017-05-23 deposited with the CCDC.
2017-10-26 downloaded from the CCDC.
;
_audit_creation_date             2017-05-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 N2 S'
_chemical_formula_sum            'C23 H20 N2 S'
_chemical_formula_weight         356.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.0528(7)
_cell_length_b                   7.5440(3)
_cell_length_c                   40.438(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.907(5)
_cell_angle_gamma                90
_cell_volume                     3676.4(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3932
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.2597
_cell_measurement_theta_min      2.8762
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.917
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91167
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            15110
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.882
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -38.00   51.25   0.7500    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   38.0000 -180.0000 119

#__ type_ start__ end____ width___ exp.time_
  2 omega  -87.00   15.00   0.7500    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -38.0000    0.0000 136
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0152844000
_diffrn_orient_matrix_UB_12      -0.0440296000
_diffrn_orient_matrix_UB_13      0.0147439000
_diffrn_orient_matrix_UB_21      -0.0561882000
_diffrn_orient_matrix_UB_22      -0.0004479000
_diffrn_orient_matrix_UB_23      -0.0054686000
_diffrn_orient_matrix_UB_31      0.0084227000
_diffrn_orient_matrix_UB_32      -0.0830988000
_diffrn_orient_matrix_UB_33      -0.0077804000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5358
_reflns_number_total             6696
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         6696
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      1.059
_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)+(0.0501P)²+1.6174P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1334
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C24(H24), C25(H25),
  C26(H26), C27(H27), C32(H32), C33(H33), C34(H34), C35(H35), C37(H37),
 C38(H38), C40(H40), C41(H41), C43(H43), C44(H44)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C45(H45A,H45B,H45C), C46(H46A,H46B,
 H46C)
;
_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
S1 S 0.83245(5) 0.30314(8) 0.17443(2) 0.02842(17) Uani 1 1 d . . . . .
N1 N 0.81261(16) 0.1584(2) 0.23237(5) 0.0263(4) Uani 1 1 d . . . . .
N2 N 0.61903(17) 0.1373(3) -0.00949(5) 0.0339(5) Uani 1 1 d . . . . .
C1 C 1.0067(2) 0.0752(3) 0.24459(6) 0.0317(6) Uani 1 1 d . . . . .
H1 H 0.988795 0.021443 0.265059 0.038 Uiso 1 1 calc R . . . .
C2 C 1.1150(2) 0.0818(3) 0.23423(6) 0.0334(6) Uani 1 1 d . . . . .
H2 H 1.172482 0.034132 0.247919 0.040 Uiso 1 1 calc R . . . .
C3 C 1.1413(2) 0.1577(3) 0.20382(6) 0.0321(6) Uani 1 1 d . . . . .
H3 H 1.216538 0.160821 0.197181 0.038 Uiso 1 1 calc R . . . .
C4 C 1.0604(2) 0.2281(3) 0.18326(6) 0.0289(6) Uani 1 1 d . . . . .
H4 H 1.078490 0.278141 0.162478 0.035 Uiso 1 1 calc R . . . .
C5 C 0.95127(19) 0.2234(3) 0.19398(6) 0.0236(5) Uani 1 1 d . . . . .
C6 C 0.92411(19) 0.1490(3) 0.22448(6) 0.0253(5) Uani 1 1 d . . . . .
C7 C 0.7556(2) 0.2357(3) 0.20883(6) 0.0254(5) Uani 1 1 d . . . . .
C8 C 0.6374(2) 0.2829(3) 0.21241(6) 0.0258(5) Uani 1 1 d . . . . .
C9 C 0.6061(2) 0.3396(3) 0.24405(6) 0.0291(6) Uani 1 1 d . . . . .
H9 H 0.659205 0.338254 0.261659 0.035 Uiso 1 1 calc R . . . .
C10 C 0.4998(2) 0.3972(3) 0.24991(7) 0.0336(6) Uani 1 1 d . . . . .
H10 H 0.480291 0.438527 0.271231 0.040 Uiso 1 1 calc R . . . .
C11 C 0.4219(2) 0.3943(3) 0.22451(7) 0.0356(6) Uani 1 1 d . . . . .
H11 H 0.348255 0.432870 0.228401 0.043 Uiso 1 1 calc R . . . .
C12 C 0.4509(2) 0.3353(3) 0.19337(6) 0.0319(6) Uani 1 1 d . . . . .
H12 H 0.395789 0.330654 0.176341 0.038 Uiso 1 1 calc R . . . .
C13 C 0.5597(2) 0.2821(3) 0.18635(6) 0.0264(5) Uani 1 1 d . . . . .
C14 C 0.5880(2) 0.2278(3) 0.15266(6) 0.0271(5) Uani 1 1 d . . . . .
H14 H 0.641634 0.136818 0.150085 0.033 Uiso 1 1 calc R . . . .
C15 C 0.5425(2) 0.2991(3) 0.12542(6) 0.0279(5) Uani 1 1 d . . . . .
H15 H 0.488202 0.388226 0.128850 0.033 Uiso 1 1 calc R . . . .
C16 C 0.56605(19) 0.2565(3) 0.09092(6) 0.0262(5) Uani 1 1 d . . . . .
C17 C 0.6568(2) 0.1552(3) 0.08103(6) 0.0289(6) Uani 1 1 d . . . . .
H17 H 0.707258 0.111575 0.097371 0.035 Uiso 1 1 calc R . . . .
C18 C 0.6751(2) 0.1167(3) 0.04820(6) 0.0281(5) Uani 1 1 d . . . . .
H18 H 0.738153 0.048565 0.042434 0.034 Uiso 1 1 calc R . . . .
C19 C 0.6018(2) 0.1767(3) 0.02306(6) 0.0265(5) Uani 1 1 d . . . . .
C20 C 0.5100(2) 0.2774(3) 0.03292(6) 0.0292(6) Uani 1 1 d . . . . .
H20 H 0.458055 0.318939 0.016778 0.035 Uiso 1 1 calc R . . . .
C21 C 0.4946(2) 0.3164(3) 0.06587(6) 0.0286(6) Uani 1 1 d . . . . .
H21 H 0.432763 0.387061 0.071739 0.034 Uiso 1 1 calc R . . . .
C22 C 0.5470(2) 0.2102(3) -0.03518(6) 0.0376(6) Uani 1 1 d . . . . .
H22A H 0.470010 0.176512 -0.030933 0.056 Uiso 1 1 calc GR . . . .
H22B H 0.569012 0.163700 -0.056733 0.056 Uiso 1 1 calc GR . . . .
H22C H 0.553346 0.339751 -0.035227 0.056 Uiso 1 1 calc GR . . . .
C23 C 0.7204(2) 0.0496(4) -0.01946(7) 0.0380(6) Uani 1 1 d . . . . .
H23A H 0.784506 0.122049 -0.012850 0.057 Uiso 1 1 calc GR . . . .
H23B H 0.719496 0.034252 -0.043530 0.057 Uiso 1 1 calc GR . . . .
H23C H 0.725637 -0.066639 -0.008737 0.057 Uiso 1 1 calc GR . . . .
S2 S 1.07366(5) -0.29061(8) 0.17431(2) 0.02956(17) Uani 1 1 d . . . . .
N3 N 1.02121(16) -0.0789(2) 0.12591(5) 0.0248(4) Uani 1 1 d . . . . .
N4 N 0.93909(18) -0.3709(3) -0.06547(5) 0.0348(5) Uani 1 1 d . . . . .
C24 C 1.2068(2) 0.0214(3) 0.10928(6) 0.0290(6) Uani 1 1 d . . . . .
H24 H 1.177786 0.096103 0.092314 0.035 Uiso 1 1 calc R . . . .
C25 C 1.3191(2) 0.0105(3) 0.11527(7) 0.0351(6) Uani 1 1 d . . . . .
H25 H 1.368103 0.078624 0.102181 0.042 Uiso 1 1 calc R . . . .
C26 C 1.3627(2) -0.0977(3) 0.14003(7) 0.0369(6) Uani 1 1 d . . . . .
H26 H 1.440708 -0.101674 0.143635 0.044 Uiso 1 1 calc R . . . .
C27 C 1.2947(2) -0.1996(3) 0.15947(6) 0.0343(6) Uani 1 1 d . . . . .
H27 H 1.324629 -0.274686 0.176230 0.041 Uiso 1 1 calc R . . . .
C28 C 1.1804(2) -0.1886(3) 0.15371(6) 0.0262(5) Uani 1 1 d . . . . .
C29 C 1.13634(19) -0.0800(3) 0.12874(6) 0.0251(5) Uani 1 1 d . . . . .
C30 C 0.9782(2) -0.1814(3) 0.14811(6) 0.0242(5) Uani 1 1 d . . . . .
C31 C 0.8589(2) -0.2142(3) 0.15270(6) 0.0250(5) Uani 1 1 d . . . . .
C32 C 0.8202(2) -0.2207(3) 0.18508(6) 0.0284(6) Uani 1 1 d . . . . .
H32 H 0.870070 -0.198990 0.203050 0.034 Uiso 1 1 calc R . . . .
C33 C 0.7103(2) -0.2583(3) 0.19124(6) 0.0315(6) Uani 1 1 d . . . . .
H33 H 0.684684 -0.261690 0.213335 0.038 Uiso 1 1 calc R . . . .
C34 C 0.6376(2) -0.2909(3) 0.16510(7) 0.0330(6) Uani 1 1 d . . . . .
H34 H 0.561987 -0.317358 0.169230 0.040 Uiso 1 1 calc R . . . .
C35 C 0.6750(2) -0.2849(3) 0.13299(6) 0.0309(6) Uani 1 1 d . . . . .
H35 H 0.623998 -0.306313 0.115295 0.037 Uiso 1 1 calc R . . . .
C36 C 0.7859(2) -0.2482(3) 0.12575(6) 0.0252(5) Uani 1 1 d . . . . .
C37 C 0.8250(2) -0.2504(3) 0.09161(6) 0.0273(5) Uani 1 1 d . . . . .
H37 H 0.890259 -0.184180 0.087309 0.033 Uiso 1 1 calc R . . . .
C38 C 0.77911(19) -0.3350(3) 0.06604(6) 0.0270(5) Uani 1 1 d . . . . .
H38 H 0.712830 -0.399119 0.070070 0.032 Uiso 1 1 calc R . . . .
C39 C 0.82077(19) -0.3390(3) 0.03227(6) 0.0251(5) Uani 1 1 d . . . . .
C40 C 0.91599(19) -0.2478(3) 0.02238(6) 0.0271(5) Uani 1 1 d . . . . .
H40 H 0.955182 -0.177341 0.038139 0.033 Uiso 1 1 calc R . . . .
C41 C 0.9545(2) -0.2571(3) -0.00939(6) 0.0272(5) Uani 1 1 d . . . . .
H41 H 1.018858 -0.191914 -0.015076 0.033 Uiso 1 1 calc R . . . .
C42 C 0.9007(2) -0.3610(3) -0.03368(6) 0.0265(5) Uani 1 1 d . . . . .
C43 C 0.8051(2) -0.4519(3) -0.02392(6) 0.0295(6) Uani 1 1 d . . . . .
H43 H 0.765395 -0.522146 -0.039621 0.035 Uiso 1 1 calc R . . . .
C44 C 0.7677(2) -0.4410(3) 0.00811(6) 0.0272(5) Uani 1 1 d . . . . .
H44 H 0.703162 -0.505686 0.013876 0.033 Uiso 1 1 calc R . . . .
C45 C 0.8920(3) -0.4991(3) -0.08830(7) 0.0439(7) Uani 1 1 d . . . . .
H45A H 0.933734 -0.497500 -0.108906 0.066 Uiso 1 1 calc GR . . . .
H45B H 0.814285 -0.468973 -0.093018 0.066 Uiso 1 1 calc GR . . . .
H45C H 0.896197 -0.617605 -0.078439 0.066 Uiso 1 1 calc GR . . . .
C46 C 1.0433(2) -0.2876(3) -0.07374(6) 0.0366(6) Uani 1 1 d . . . . .
H46A H 1.036778 -0.158887 -0.071135 0.055 Uiso 1 1 calc GR . . . .
H46B H 1.061440 -0.315374 -0.096707 0.055 Uiso 1 1 calc GR . . . .
H46C H 1.102248 -0.332190 -0.058985 0.055 Uiso 1 1 calc GR . . . .


_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 C5 1.733(2) . ?
S1 C7 1.759(2) . ?
N1 C6 1.388(3) . ?
N1 C7 1.303(3) . ?
N2 C19 1.369(3) . ?
N2 C22 1.452(3) . ?
N2 C23 1.452(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.378(3) . ?
C1 C6 1.391(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.397(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.378(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(3) . ?
C5 C6 1.399(3) . ?
C7 C8 1.478(3) . ?
C8 C9 1.406(3) . ?
C8 C13 1.398(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.377(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.381(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.405(3) . ?
C13 C14 1.468(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.336(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.463(3) . ?
C16 C17 1.398(3) . ?
C16 C21 1.394(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.380(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.410(3) . ?
C19 C20 1.406(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.380(3) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
S2 C28 1.725(2) . ?
S2 C30 1.757(2) . ?
N3 C29 1.391(3) . ?
N3 C30 1.299(3) . ?
N4 C42 1.375(3) . ?
N4 C45 1.447(3) . ?
N4 C46 1.448(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.374(3) . ?
C24 C29 1.395(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.389(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.378(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.396(3) . ?
C28 C29 1.398(3) . ?
C30 C31 1.473(3) . ?
C31 C32 1.398(3) . ?
C31 C36 1.413(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.381(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.385(4) . ?
C34 H34 0.9500 . ?
C34 C35 1.382(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.401(3) . ?
C36 C37 1.466(3) . ?
C37 H37 0.9500 . ?
C37 C38 1.329(3) . ?
C38 H38 0.9500 . ?
C38 C39 1.463(3) . ?
C39 C40 1.402(3) . ?
C39 C44 1.392(3) . ?
C40 H40 0.9500 . ?
C40 C41 1.375(3) . ?
C41 H41 0.9500 . ?
C41 C42 1.406(3) . ?
C42 C43 1.403(3) . ?
C43 H43 0.9500 . ?
C43 C44 1.381(3) . ?
C44 H44 0.9500 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 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
C5 S1 C7 88.88(11) . . ?
C7 N1 C6 110.9(2) . . ?
C19 N2 C22 120.5(2) . . ?
C19 N2 C23 120.5(2) . . ?
C22 N2 C23 118.1(2) . . ?
C2 C1 H1 120.6 . . ?
C2 C1 C6 118.7(2) . . ?
C6 C1 H1 120.6 . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.7(2) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 121.1 . . ?
C3 C4 C5 117.7(2) . . ?
C5 C4 H4 121.1 . . ?
C4 C5 S1 128.85(19) . . ?
C4 C5 C6 121.4(2) . . ?
C6 C5 S1 109.78(17) . . ?
N1 C6 C1 124.9(2) . . ?
N1 C6 C5 115.0(2) . . ?
C1 C6 C5 120.0(2) . . ?
N1 C7 S1 115.38(18) . . ?
N1 C7 C8 122.3(2) . . ?
C8 C7 S1 121.90(17) . . ?
C9 C8 C7 115.8(2) . . ?
C13 C8 C7 124.1(2) . . ?
C13 C8 C9 120.1(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.1(2) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.2 . . ?
C11 C12 C13 121.7(2) . . ?
C13 C12 H12 119.2 . . ?
C8 C13 C12 117.5(2) . . ?
C8 C13 C14 122.6(2) . . ?
C12 C13 C14 119.9(2) . . ?
C13 C14 H14 118.2 . . ?
C15 C14 C13 123.7(2) . . ?
C15 C14 H14 118.2 . . ?
C14 C15 H15 116.0 . . ?
C14 C15 C16 127.9(2) . . ?
C16 C15 H15 116.0 . . ?
C17 C16 C15 123.9(2) . . ?
C21 C16 C15 119.7(2) . . ?
C21 C16 C17 116.5(2) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.9(2) . . ?
C18 C17 H17 119.1 . . ?
C17 C18 H18 119.4 . . ?
C17 C18 C19 121.2(2) . . ?
C19 C18 H18 119.4 . . ?
N2 C19 C18 121.4(2) . . ?
N2 C19 C20 121.5(2) . . ?
C20 C19 C18 117.1(2) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.5(2) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 H21 118.6 . . ?
C20 C21 C16 122.8(2) . . ?
C20 C21 H21 118.6 . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C28 S2 C30 89.20(11) . . ?
C30 N3 C29 110.4(2) . . ?
C42 N4 C45 119.9(2) . . ?
C42 N4 C46 119.9(2) . . ?
C45 N4 C46 118.4(2) . . ?
C25 C24 H24 120.8 . . ?
C25 C24 C29 118.3(2) . . ?
C29 C24 H24 120.8 . . ?
C24 C25 H25 119.3 . . ?
C24 C25 C26 121.5(2) . . ?
C26 C25 H25 119.3 . . ?
C25 C26 H26 119.4 . . ?
C27 C26 C25 121.2(2) . . ?
C27 C26 H26 119.4 . . ?
C26 C27 H27 121.1 . . ?
C26 C27 C28 117.7(2) . . ?
C28 C27 H27 121.1 . . ?
C27 C28 S2 129.4(2) . . ?
C27 C28 C29 121.2(2) . . ?
C29 C28 S2 109.42(18) . . ?
N3 C29 C24 124.4(2) . . ?
N3 C29 C28 115.5(2) . . ?
C24 C29 C28 120.1(2) . . ?
N3 C30 S2 115.52(18) . . ?
N3 C30 C31 126.0(2) . . ?
C31 C30 S2 118.45(16) . . ?
C32 C31 C30 117.7(2) . . ?
C32 C31 C36 120.2(2) . . ?
C36 C31 C30 122.0(2) . . ?
C31 C32 H32 119.6 . . ?
C33 C32 C31 120.8(2) . . ?
C33 C32 H32 119.6 . . ?
C32 C33 H33 120.1 . . ?
C32 C33 C34 119.7(2) . . ?
C34 C33 H33 120.1 . . ?
C33 C34 H34 120.0 . . ?
C35 C34 C33 120.0(2) . . ?
C35 C34 H34 120.0 . . ?
C34 C35 H35 119.0 . . ?
C34 C35 C36 122.0(2) . . ?
C36 C35 H35 119.0 . . ?
C31 C36 C37 121.5(2) . . ?
C35 C36 C31 117.3(2) . . ?
C35 C36 C37 121.1(2) . . ?
C36 C37 H37 116.5 . . ?
C38 C37 C36 127.0(2) . . ?
C38 C37 H37 116.5 . . ?
C37 C38 H38 116.9 . . ?
C37 C38 C39 126.3(2) . . ?
C39 C38 H38 116.9 . . ?
C40 C39 C38 123.4(2) . . ?
C44 C39 C38 120.4(2) . . ?
C44 C39 C40 116.1(2) . . ?
C39 C40 H40 118.9 . . ?
C41 C40 C39 122.1(2) . . ?
C41 C40 H40 118.9 . . ?
C40 C41 H41 119.3 . . ?
C40 C41 C42 121.5(2) . . ?
C42 C41 H41 119.3 . . ?
N4 C42 C41 121.7(2) . . ?
N4 C42 C43 121.7(2) . . ?
C43 C42 C41 116.6(2) . . ?
C42 C43 H43 119.5 . . ?
C44 C43 C42 121.1(2) . . ?
C44 C43 H43 119.5 . . ?
C39 C44 H44 118.7 . . ?
C43 C44 C39 122.6(2) . . ?
C43 C44 H44 118.7 . . ?
N4 C45 H45A 109.5 . . ?
N4 C45 H45B 109.5 . . ?
N4 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
N4 C46 H46A 109.5 . . ?
N4 C46 H46B 109.5 . . ?
N4 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?

_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_170411_d_ph_a
_database_code_depnum_ccdc_archive 'CCDC 1551667'
_audit_update_record             
;
2017-05-23 deposited with the CCDC.
2017-10-26 downloaded from the CCDC.
;
_audit_creation_date             2017-04-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 N2 S'
_chemical_formula_sum            'C21 H18 N2 S'
_chemical_formula_weight         330.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 s1'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.1982(5)
_cell_length_b                   24.956(2)
_cell_length_c                   10.8550(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.234(8)
_cell_angle_gamma                90
_cell_volume                     1665.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2707
_cell_measurement_temperature    170
_cell_measurement_theta_max      29.3250
_cell_measurement_theta_min      3.3065
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.920
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_unetI/netI     0.0741
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6861
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         3.313
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean 5.1796
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -86.00   21.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -77.0000   90.0000 107

#__ type_ start__ end____ width___ exp.time_
  2 omega   -8.00   74.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       11.9371   38.0000   30.0000 82
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0068740000
_diffrn_orient_matrix_UB_12      0.0025616000
_diffrn_orient_matrix_UB_13      -0.0654313000
_diffrn_orient_matrix_UB_21      0.0128354000
_diffrn_orient_matrix_UB_22      0.0281544000
_diffrn_orient_matrix_UB_23      0.0063558000
_diffrn_orient_matrix_UB_31      0.1144423000
_diffrn_orient_matrix_UB_32      -0.0029921000
_diffrn_orient_matrix_UB_33      0.0036992000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2445
_reflns_number_total             3045
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3045
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0592
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0648P)²+0.4976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1526
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C16(H16), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_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
S1 S 0.02907(11) 0.31705(3) 0.39099(6) 0.0302(2) Uani 1 1 d . . . . .
N1 N 0.1062(3) 0.41466(9) 0.46596(19) 0.0302(5) Uani 1 1 d . . . . .
N2 N 0.1095(4) 0.10184(9) 0.4428(2) 0.0354(6) Uani 1 1 d . . . . .
C1 C -0.3596(4) 0.36027(12) 0.2645(2) 0.0349(6) Uani 1 1 d . . . . .
H1 H -0.406559 0.326525 0.230563 0.042 Uiso 1 1 calc R . . . .
C2 C -0.4855(4) 0.40549(12) 0.2404(2) 0.0370(7) Uani 1 1 d . . . . .
H2 H -0.621604 0.402730 0.189715 0.044 Uiso 1 1 calc R . . . .
C3 C -0.4168(4) 0.45528(12) 0.2893(3) 0.0382(7) Uani 1 1 d . . . . .
H3 H -0.506611 0.485818 0.271068 0.046 Uiso 1 1 calc R . . . .
C4 C -0.2207(4) 0.46082(12) 0.3636(3) 0.0363(7) Uani 1 1 d . . . . .
H4 H -0.174307 0.494816 0.396243 0.044 Uiso 1 1 calc R . . . .
C5 C -0.0917(4) 0.41539(11) 0.3897(2) 0.0285(6) Uani 1 1 d . . . . .
C6 C -0.1616(4) 0.36543(11) 0.3398(2) 0.0281(6) Uani 1 1 d . . . . .
C7 C 0.1870(4) 0.36648(11) 0.4747(2) 0.0273(6) Uani 1 1 d . . . . .
C8 C 0.4002(4) 0.35619(11) 0.5499(2) 0.0276(6) Uani 1 1 d . . . . .
C9 C 0.5182(4) 0.40153(11) 0.5943(2) 0.0317(6) Uani 1 1 d . . . . .
H9 H 0.457371 0.436053 0.576765 0.038 Uiso 1 1 calc R . . . .
C10 C 0.7207(4) 0.39735(12) 0.6631(2) 0.0364(7) Uani 1 1 d . . . . .
H10 H 0.797640 0.428640 0.692801 0.044 Uiso 1 1 calc R . . . .
C11 C 0.8105(4) 0.34709(12) 0.6883(2) 0.0358(7) Uani 1 1 d . . . . .
H11 H 0.949861 0.343772 0.735313 0.043 Uiso 1 1 calc R . . . .
C12 C 0.6972(4) 0.30190(12) 0.6451(2) 0.0326(6) Uani 1 1 d . . . . .
H12 H 0.760807 0.267669 0.662657 0.039 Uiso 1 1 calc R . . . .
C13 C 0.4910(4) 0.30515(11) 0.5762(2) 0.0279(6) Uani 1 1 d . . . . .
C14 C 0.3825(4) 0.25368(11) 0.5357(2) 0.0278(6) Uani 1 1 d . . . . .
C15 C 0.4600(4) 0.22166(11) 0.4461(2) 0.0331(6) Uani 1 1 d . . . . .
H15 H 0.577313 0.234335 0.405654 0.040 Uiso 1 1 calc R . . . .
C16 C 0.3717(4) 0.17196(11) 0.4141(2) 0.0329(6) Uani 1 1 d . . . . .
H16 H 0.428186 0.151276 0.352064 0.039 Uiso 1 1 calc R . . . .
C17 C 0.1986(4) 0.15175(11) 0.4728(2) 0.0283(6) Uani 1 1 d . . . . .
C18 C 0.1192(4) 0.18425(11) 0.5623(2) 0.0307(6) Uani 1 1 d . . . . .
H18 H 0.000029 0.172222 0.602056 0.037 Uiso 1 1 calc R . . . .
C19 C 0.2119(4) 0.23347(11) 0.5935(2) 0.0311(6) Uani 1 1 d . . . . .
H19 H 0.157408 0.254154 0.656241 0.037 Uiso 1 1 calc R . . . .
C20 C 0.2263(5) 0.06401(12) 0.3757(3) 0.0485(8) Uani 1 1 d . . . . .
H20A H 0.237011 0.077835 0.292181 0.073 Uiso 1 1 calc GR . . . .
H20B H 0.148712 0.029710 0.369447 0.073 Uiso 1 1 calc GR . . . .
H20C H 0.372696 0.058760 0.419855 0.073 Uiso 1 1 calc GR . . . .
C21 C -0.0707(5) 0.08241(12) 0.5027(3) 0.0436(7) Uani 1 1 d . . . . .
H21A H -0.020110 0.074186 0.589832 0.065 Uiso 1 1 calc GR . . . .
H21B H -0.130059 0.049921 0.460502 0.065 Uiso 1 1 calc GR . . . .
H21C H -0.184059 0.109962 0.498387 0.065 Uiso 1 1 calc GR . . . .


_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 C6 1.731(3) . ?
S1 C7 1.755(3) . ?
N1 C5 1.391(3) . ?
N1 C7 1.301(3) . ?
N2 C17 1.385(3) . ?
N2 C20 1.442(4) . ?
N2 C21 1.445(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.378(4) . ?
C1 C6 1.392(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.396(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.378(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.396(4) . ?
C5 C6 1.406(4) . ?
C7 C8 1.486(4) . ?
C8 C9 1.400(4) . ?
C8 C13 1.407(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.381(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.400(4) . ?
C13 C14 1.490(4) . ?
C14 C15 1.390(4) . ?
C14 C19 1.390(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.382(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.408(3) . ?
C17 C18 1.402(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.380(4) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
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
C6 S1 C7 89.40(13) . . ?
C7 N1 C5 111.0(2) . . ?
C17 N2 C20 119.8(2) . . ?
C17 N2 C21 120.3(2) . . ?
C20 N2 C21 118.3(2) . . ?
C2 C1 H1 120.9 . . ?
C2 C1 C6 118.1(3) . . ?
C6 C1 H1 120.9 . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.2(3) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.5(3) . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 124.8(2) . . ?
N1 C5 C6 115.1(2) . . ?
C4 C5 C6 120.1(2) . . ?
C1 C6 S1 129.8(2) . . ?
C1 C6 C5 121.0(2) . . ?
C5 C6 S1 109.27(19) . . ?
N1 C7 S1 115.30(19) . . ?
N1 C7 C8 120.5(2) . . ?
C8 C7 S1 124.2(2) . . ?
C9 C8 C7 116.1(2) . . ?
C9 C8 C13 119.0(2) . . ?
C13 C8 C7 125.0(2) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.7(3) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.4(3) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.1 . . ?
C11 C12 C13 121.7(3) . . ?
C13 C12 H12 119.1 . . ?
C8 C13 C14 124.5(2) . . ?
C12 C13 C8 118.4(3) . . ?
C12 C13 C14 117.1(2) . . ?
C15 C14 C13 121.2(2) . . ?
C19 C14 C13 121.4(2) . . ?
C19 C14 C15 117.2(3) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 C14 122.1(2) . . ?
C16 C15 H15 119.0 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.5(2) . . ?
C17 C16 H16 119.7 . . ?
N2 C17 C16 121.3(2) . . ?
N2 C17 C18 121.3(2) . . ?
C18 C17 C16 117.4(3) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 120.9(2) . . ?
C19 C18 H18 119.5 . . ?
C14 C19 H19 119.0 . . ?
C18 C19 C14 121.9(2) . . ?
C18 C19 H19 119.0 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
