# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_mc1
_database_code_depnum_ccdc_archive 'CCDC 1418905'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;
_audit_creation_date             2014-11-05
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.10.22 svn.r3046 for OlexSys, GUI svn.r4928)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
N'-(2-oxoindolin-3-ylidene)pyrrolidine-1-carbothiohydrazide
_chemical_formula_moiety         'C13 H14 N4 O S, H2 O'
_chemical_formula_sum            'C13 H16 N4 O2 S'
_chemical_formula_weight         292.36
_chemical_melting_point          424K
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'

_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                   12.365(9)
_cell_length_b                   15.377(11)
_cell_length_c                   7.396(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.715(8)
_cell_angle_gamma                90
_cell_volume                     1360.2(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6584
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      27.463
_cell_measurement_theta_min      2.649
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.904
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0589 before and 0.0483 after correction.
 The Ratio of minimum to maximum transmission is 0.89.
 The λ/2 correction factor is Not present

Final HKLF 4 output contains 59132 reflections, Rint = 0.0599
 (26450 with I > 3sig(I), Rint = 0.0462)
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5952
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.528
_diffrn_reflns_theta_min         2.157
_diffrn_ambient_temperature      110.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2616
_reflns_number_total             3083
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3083
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.034
_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)+(0.0419P)²+0.8526P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0974
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C2(H2), C3(H3A), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.12562(4) 0.13922(3) 0.38536(5) 0.02011(12) Uani 1 1 d . . . . .
O1 O 0.39945(10) 0.39718(7) 0.70238(14) 0.0208(3) Uani 1 1 d . . . . .
N1 N 0.55929(11) 0.33917(9) 0.89657(17) 0.0185(3) Uani 1 1 d . . . . .
H1 H 0.5936 0.3877 0.9413 0.022 Uiso 1 1 calc R . . . .
N2 N 0.34327(11) 0.20811(8) 0.62617(16) 0.0167(3) Uani 1 1 d . . . . .
N3 N 0.26725(11) 0.26713(8) 0.53871(17) 0.0172(3) Uani 1 1 d . . . . .
H3 H 0.2839 0.3228 0.5516 0.021 Uiso 1 1 calc R . . . .
N4 N 0.09948(11) 0.31031(8) 0.36426(17) 0.0174(3) Uani 1 1 d . . . . .
C1 C 0.60181(13) 0.25570(10) 0.9451(2) 0.0177(3) Uani 1 1 d . . . . .
C2 C 0.70095(14) 0.23304(11) 1.0683(2) 0.0216(3) Uani 1 1 d . . . . .
H2 H 0.7512 0.2759 1.1338 0.026 Uiso 1 1 calc R . . . .
C3 C 0.72490(15) 0.14494(11) 1.0932(2) 0.0247(4) Uani 1 1 d . . . . .
H3A H 0.7928 0.1272 1.1775 0.030 Uiso 1 1 calc R . . . .
C4 C 0.65163(15) 0.08240(11) 0.9977(2) 0.0251(4) Uani 1 1 d . . . . .
H4 H 0.6701 0.0226 1.0175 0.030 Uiso 1 1 calc R . . . .
C5 C 0.55182(14) 0.10582(11) 0.8736(2) 0.0205(3) Uani 1 1 d . . . . .
H5 H 0.5017 0.0629 0.8080 0.025 Uiso 1 1 calc R . . . .
C6 C 0.52717(13) 0.19297(10) 0.84806(19) 0.0167(3) Uani 1 1 d . . . . .
C7 C 0.43268(13) 0.24089(10) 0.73417(19) 0.0160(3) Uani 1 1 d . . . . .
C8 C 0.45910(13) 0.33531(10) 0.7725(2) 0.0173(3) Uani 1 1 d . . . . .
C9 C 0.16479(13) 0.24269(10) 0.43035(19) 0.0162(3) Uani 1 1 d . . . . .
C10 C -0.01702(14) 0.30209(11) 0.2568(2) 0.0208(3) Uani 1 1 d . . . . .
H10A H -0.0569 0.2573 0.3114 0.025 Uiso 1 1 calc R . . . .
H10B H -0.0220 0.2871 0.1248 0.025 Uiso 1 1 calc R . . . .
C11 C -0.06379(15) 0.39203(12) 0.2733(3) 0.0297(4) Uani 1 1 d . . . . .
H11A H -0.1270 0.4051 0.1645 0.036 Uiso 1 1 calc R . . . .
H11B H -0.0895 0.3974 0.3891 0.036 Uiso 1 1 calc R . . . .
C12 C 0.03414(15) 0.45201(11) 0.2785(2) 0.0240(4) Uani 1 1 d . . . . .
H12A H 0.0254 0.5077 0.3404 0.029 Uiso 1 1 calc R . . . .
H12B H 0.0415 0.4642 0.1507 0.029 Uiso 1 1 calc R . . . .
C13 C 0.13466(14) 0.40173(10) 0.3908(2) 0.0193(3) Uani 1 1 d . . . . .
H13A H 0.2013 0.4126 0.3429 0.023 Uiso 1 1 calc R . . . .
H13B H 0.1521 0.4180 0.5246 0.023 Uiso 1 1 calc R . . . .
O1W O 0.33914(12) 0.50304(8) 0.97691(18) 0.0323(3) Uani 1 1 d . . . . .
H1WA H 0.3650 0.4846 0.8879 0.048 Uiso 1 1 d G . . . .
H1WB H 0.2952 0.4652 1.0026 0.048 Uiso 1 1 d G . . . .


_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 1.6718(19) . ?
O1 C8 1.234(2) . ?
N1 H1 0.8800 . ?
N1 C1 1.399(2) . ?
N1 C8 1.343(2) . ?
N2 N3 1.3479(18) . ?
N2 C7 1.291(2) . ?
N3 H3 0.8800 . ?
N3 C9 1.369(2) . ?
N4 C9 1.331(2) . ?
N4 C10 1.463(2) . ?
N4 C13 1.470(2) . ?
C1 C2 1.374(2) . ?
C1 C6 1.400(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(3) . ?
C3 H3A 0.9500 . ?
C3 C4 1.386(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.377(2) . ?
C6 C7 1.455(2) . ?
C7 C8 1.499(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.516(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.515(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.519(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
O1W H1WA 0.8499 . ?
O1W H1WB 0.8500 . ?

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 N1 H1 124.6 . . ?
C8 N1 H1 124.6 . . ?
C8 N1 C1 110.87(13) . . ?
C7 N2 N3 114.68(14) . . ?
N2 N3 H3 119.2 . . ?
N2 N3 C9 121.68(13) . . ?
C9 N3 H3 119.2 . . ?
C9 N4 C10 123.63(14) . . ?
C9 N4 C13 124.51(14) . . ?
C10 N4 C13 111.86(12) . . ?
N1 C1 C6 110.17(14) . . ?
C2 C1 N1 128.09(14) . . ?
C2 C1 C6 121.75(15) . . ?
C1 C2 H2 121.3 . . ?
C1 C2 C3 117.37(15) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 H3A 119.4 . . ?
C4 C3 C2 121.29(16) . . ?
C4 C3 H3A 119.4 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 120.96(16) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.9 . . ?
C6 C5 C4 118.22(15) . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C7 106.00(14) . . ?
C5 C6 C1 120.40(15) . . ?
C5 C6 C7 133.60(15) . . ?
N2 C7 C6 126.60(15) . . ?
N2 C7 C8 127.33(14) . . ?
C6 C7 C8 106.05(13) . . ?
O1 C8 N1 127.02(15) . . ?
O1 C8 C7 126.06(15) . . ?
N1 C8 C7 106.91(13) . . ?
N3 C9 S1 123.80(12) . . ?
N4 C9 S1 123.52(13) . . ?
N4 C9 N3 112.68(14) . . ?
N4 C10 H10A 111.2 . . ?
N4 C10 H10B 111.2 . . ?
N4 C10 C11 102.74(13) . . ?
H10A C10 H10B 109.1 . . ?
C11 C10 H10A 111.2 . . ?
C11 C10 H10B 111.2 . . ?
C10 C11 H11A 111.0 . . ?
C10 C11 H11B 111.0 . . ?
H11A C11 H11B 109.0 . . ?
C12 C11 C10 103.81(15) . . ?
C12 C11 H11A 111.0 . . ?
C12 C11 H11B 111.0 . . ?
C11 C12 H12A 111.0 . . ?
C11 C12 H12B 111.0 . . ?
C11 C12 C13 103.98(14) . . ?
H12A C12 H12B 109.0 . . ?
C13 C12 H12A 111.0 . . ?
C13 C12 H12B 111.0 . . ?
N4 C13 C12 103.91(13) . . ?
N4 C13 H13A 111.0 . . ?
N4 C13 H13B 111.0 . . ?
C12 C13 H13A 111.0 . . ?
C12 C13 H13B 111.0 . . ?
H13A C13 H13B 109.0 . . ?
H1WA O1W H1WB 109.5 . . ?

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
N1 H1 O1W 0.88 1.90 2.783(2) 175.8 3_667
N3 H3 O1 0.88 1.94 2.670(2) 138.8 .
O1W H1WA O1 0.85 2.04 2.846(2) 157.4 .
O1W H1WB S1 0.85 2.61 3.363(2) 148.5 4_566

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
N1 C1 C2 C3 179.97(15) . . . . ?
N1 C1 C6 C5 179.90(14) . . . . ?
N1 C1 C6 C7 -0.46(16) . . . . ?
N2 N3 C9 S1 -3.4(2) . . . . ?
N2 N3 C9 N4 176.61(13) . . . . ?
N2 C7 C8 O1 -1.7(3) . . . . ?
N2 C7 C8 N1 178.35(14) . . . . ?
N3 N2 C7 C6 178.73(14) . . . . ?
N3 N2 C7 C8 0.7(2) . . . . ?
N4 C10 C11 C12 33.56(16) . . . . ?
C1 N1 C8 O1 179.76(15) . . . . ?
C1 N1 C8 C7 -0.27(16) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C1 C6 C7 N2 -178.09(15) . . . . ?
C1 C6 C7 C8 0.29(15) . . . . ?
C2 C1 C6 C5 -0.2(2) . . . . ?
C2 C1 C6 C7 179.43(14) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C4 C5 C6 C7 -179.30(16) . . . . ?
C5 C6 C7 N2 1.5(3) . . . . ?
C5 C6 C7 C8 179.86(16) . . . . ?
C6 C1 C2 C3 0.1(2) . . . . ?
C6 C7 C8 O1 179.95(14) . . . . ?
C6 C7 C8 N1 -0.02(16) . . . . ?
C7 N2 N3 C9 -175.14(13) . . . . ?
C8 N1 C1 C2 -179.40(16) . . . . ?
C8 N1 C1 C6 0.47(17) . . . . ?
C9 N4 C10 C11 161.29(14) . . . . ?
C9 N4 C13 C12 176.05(14) . . . . ?
C10 N4 C9 S1 5.0(2) . . . . ?
C10 N4 C9 N3 -175.10(13) . . . . ?
C10 N4 C13 C12 -4.35(16) . . . . ?
C10 C11 C12 C13 -36.88(16) . . . . ?
C11 C12 C13 N4 25.34(16) . . . . ?
C13 N4 C9 S1 -175.49(11) . . . . ?
C13 N4 C9 N3 4.5(2) . . . . ?
C13 N4 C10 C11 -18.31(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: METHANOL/ACETONITRILE'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_mc1a
_database_code_depnum_ccdc_archive 'CCDC 1418933'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;
_audit_creation_date             2014-10-31
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.10.22 svn.r3046 for OlexSys, GUI svn.r4928)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
(Z)-N'-(1-allyl-2-oxoindolin-3-ylidene)pyrrolidine-1-carbothiohydrazide
_chemical_formula_moiety         'C16 H18 N4 O S'
_chemical_formula_sum            'C16 H18 N4 O S'
_chemical_formula_weight         314.40
_chemical_melting_point          433K
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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.514(19)
_cell_length_b                   9.287(7)
_cell_length_c                   15.869(12)
_cell_angle_alpha                90
_cell_angle_beta                 107.718(14)
_cell_angle_gamma                90
_cell_volume                     3020(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5230
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      27.715
_cell_measurement_theta_min      2.408
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.886
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0864 before and 0.0577 after correction.
The Ratio of minimum to maximum transmission is 0.8800.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.27
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16848
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.777
_diffrn_reflns_theta_min         1.987
_diffrn_ambient_temperature      110.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2831
_reflns_number_total             3505
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0023(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3505
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.031
_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)+(0.0309P)²+3.0922P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0920
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Riding coordinates:
 C11(H11A,H11B)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C3(H3A), C4(H4), C5(H5), C10(H10)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.45003(2) 0.71211(4) 0.57172(3) 0.02343(13) Uani 1 1 d . . . . .
O1 O 0.21403(5) 0.51099(12) 0.38734(8) 0.0248(3) Uani 1 1 d . . . . .
N1 N 0.15471(6) 0.69283(14) 0.29974(9) 0.0193(3) Uani 1 1 d . . . . .
N2 N 0.31425(6) 0.74846(14) 0.44485(8) 0.0180(3) Uani 1 1 d . . . . .
N3 N 0.33150(6) 0.61544(14) 0.47797(9) 0.0193(3) Uani 1 1 d . . . . .
H3 H 0.3026 0.5455 0.4635 0.023 Uiso 1 1 calc R . . . .
N4 N 0.40170(6) 0.44690(14) 0.55406(8) 0.0193(3) Uani 1 1 d . . . . .
C1 C 0.16430(7) 0.84013(17) 0.28576(10) 0.0174(3) Uani 1 1 d . . . . .
C2 C 0.12356(8) 0.93396(17) 0.22673(10) 0.0203(3) Uani 1 1 d . . . . .
H2 H 0.0829 0.9029 0.1877 0.024 Uiso 1 1 calc R . . . .
C3 C 0.14444(8) 1.07589(18) 0.22666(11) 0.0224(4) Uani 1 1 d . . . . .
H3A H 0.1176 1.1426 0.1863 0.027 Uiso 1 1 calc R . . . .
C4 C 0.20357(8) 1.12230(18) 0.28408(11) 0.0222(3) Uani 1 1 d . . . . .
H4 H 0.2161 1.2203 0.2835 0.027 Uiso 1 1 calc R . . . .
C5 C 0.24437(8) 1.02643(17) 0.34228(10) 0.0197(3) Uani 1 1 d . . . . .
H5 H 0.2849 1.0577 0.3815 0.024 Uiso 1 1 calc R . . . .
C6 C 0.22497(7) 0.88466(16) 0.34221(10) 0.0168(3) Uani 1 1 d . . . . .
C7 C 0.25561(8) 0.75699(16) 0.39088(10) 0.0177(3) Uani 1 1 d . . . . .
C8 C 0.20752(7) 0.63722(17) 0.36146(10) 0.0194(3) Uani 1 1 d . . . . .
C9 C 0.09617(7) 0.60713(17) 0.25952(11) 0.0199(3) Uani 1 1 d . . . . .
H9A H 0.0598 0.6721 0.2290 0.024 Uiso 1 1 calc R . . . .
H9B H 0.0837 0.5555 0.3065 0.024 Uiso 1 1 calc R . . . .
C10 C 0.10664(8) 0.50025(17) 0.19460(11) 0.0212(3) Uani 1 1 d . . . . .
H10 H 0.1445 0.4415 0.2128 0.025 Uiso 1 1 calc R . . . .
C11 C 0.06705(8) 0.48224(18) 0.11423(11) 0.0256(4) Uani 1 1 d . . . . .
H11A H 0.0759 0.4079 0.0784 0.031 Uiso 1 1 d R . . . .
H11B H 0.0296 0.5422 0.0945 0.031 Uiso 1 1 d R . . . .
C12 C 0.39291(7) 0.58614(17) 0.53372(10) 0.0176(3) Uani 1 1 d . . . . .
C13 C 0.46102(8) 0.39182(18) 0.61887(11) 0.0230(4) Uani 1 1 d . . . . .
H13A H 0.4731 0.4507 0.6735 0.028 Uiso 1 1 calc R . . . .
H13B H 0.4981 0.3902 0.5941 0.028 Uiso 1 1 calc R . . . .
C14 C 0.44148(9) 0.24034(18) 0.63671(11) 0.0254(4) Uani 1 1 d . . . . .
H14A H 0.4188 0.2405 0.6825 0.030 Uiso 1 1 calc R . . . .
H14B H 0.4800 0.1762 0.6559 0.030 Uiso 1 1 calc R . . . .
C15 C 0.39575(9) 0.19439(18) 0.54738(12) 0.0272(4) Uani 1 1 d . . . . .
H15A H 0.3676 0.1134 0.5537 0.033 Uiso 1 1 calc R . . . .
H15B H 0.4204 0.1656 0.5066 0.033 Uiso 1 1 calc R . . . .
C16 C 0.35571(8) 0.32972(17) 0.51476(11) 0.0221(4) Uani 1 1 d . . . . .
H16A H 0.3414 0.3350 0.4494 0.027 Uiso 1 1 calc R . . . .
H16B H 0.3169 0.3331 0.5357 0.027 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
S1 C12 1.6708(18) . ?
O1 C8 1.236(2) . ?
N1 C1 1.411(2) . ?
N1 C8 1.356(2) . ?
N1 C9 1.462(2) . ?
N2 N3 1.350(2) . ?
N2 C7 1.294(2) . ?
N3 H3 0.8800 . ?
N3 C12 1.375(2) . ?
N4 C12 1.332(2) . ?
N4 C13 1.466(2) . ?
N4 C16 1.475(2) . ?
C1 C2 1.380(2) . ?
C1 C6 1.402(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(2) . ?
C3 H3A 0.9500 . ?
C3 C4 1.389(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(2) . ?
C6 C7 1.458(2) . ?
C7 C8 1.494(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.496(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.311(2) . ?
C11 H11A 0.9500 . ?
C11 H11B 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.519(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.520(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.523(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

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 N1 C9 127.36(13) . . ?
C8 N1 C1 110.63(13) . . ?
C8 N1 C9 121.94(14) . . ?
C7 N2 N3 114.27(13) . . ?
N2 N3 H3 119.1 . . ?
N2 N3 C12 121.88(13) . . ?
C12 N3 H3 119.1 . . ?
C12 N4 C13 122.53(13) . . ?
C12 N4 C16 125.87(13) . . ?
C13 N4 C16 111.58(14) . . ?
C2 C1 N1 128.74(14) . . ?
C2 C1 C6 121.52(15) . . ?
C6 C1 N1 109.74(13) . . ?
C1 C2 H2 121.3 . . ?
C1 C2 C3 117.37(15) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 H3A 119.2 . . ?
C4 C3 C2 121.63(15) . . ?
C4 C3 H3A 119.2 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.37(16) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.79(15) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C7 106.35(14) . . ?
C5 C6 C1 120.28(14) . . ?
C5 C6 C7 133.37(15) . . ?
N2 C7 C6 126.37(14) . . ?
N2 C7 C8 127.19(15) . . ?
C6 C7 C8 106.34(14) . . ?
O1 C8 N1 125.90(15) . . ?
O1 C8 C7 127.21(15) . . ?
N1 C8 C7 106.89(14) . . ?
N1 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
N1 C9 C10 111.81(13) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C9 C10 H10 117.8 . . ?
C11 C10 C9 124.41(16) . . ?
C11 C10 H10 117.8 . . ?
C10 C11 H11A 119.0 . . ?
C10 C11 H11B 118.7 . . ?
H11A C11 H11B 122.3 . . ?
N3 C12 S1 123.42(13) . . ?
N4 C12 S1 123.89(12) . . ?
N4 C12 N3 112.69(13) . . ?
N4 C13 H13A 111.2 . . ?
N4 C13 H13B 111.2 . . ?
N4 C13 C14 102.87(14) . . ?
H13A C13 H13B 109.1 . . ?
C14 C13 H13A 111.2 . . ?
C14 C13 H13B 111.2 . . ?
C13 C14 H14A 111.2 . . ?
C13 C14 H14B 111.2 . . ?
C13 C14 C15 102.91(14) . . ?
H14A C14 H14B 109.1 . . ?
C15 C14 H14A 111.2 . . ?
C15 C14 H14B 111.2 . . ?
C14 C15 H15A 111.2 . . ?
C14 C15 H15B 111.2 . . ?
C14 C15 C16 102.94(14) . . ?
H15A C15 H15B 109.1 . . ?
C16 C15 H15A 111.2 . . ?
C16 C15 H15B 111.2 . . ?
N4 C16 C15 103.17(14) . . ?
N4 C16 H16A 111.1 . . ?
N4 C16 H16B 111.1 . . ?
C15 C16 H16A 111.1 . . ?
C15 C16 H16B 111.1 . . ?
H16A C16 H16B 109.1 . . ?

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
N3 H3 O1 0.88 1.95 2.680(2) 139.8 .

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
N1 C1 C2 C3 179.41(15) . . . . ?
N1 C1 C6 C5 -178.12(14) . . . . ?
N1 C1 C6 C7 2.46(17) . . . . ?
N1 C9 C10 C11 -130.99(17) . . . . ?
N2 N3 C12 S1 4.6(2) . . . . ?
N2 N3 C12 N4 -175.51(13) . . . . ?
N2 C7 C8 O1 4.4(3) . . . . ?
N2 C7 C8 N1 -175.15(15) . . . . ?
N3 N2 C7 C6 -177.04(14) . . . . ?
N3 N2 C7 C8 -1.4(2) . . . . ?
N4 C13 C14 C15 34.39(16) . . . . ?
C1 N1 C8 O1 -179.34(15) . . . . ?
C1 N1 C8 C7 0.27(17) . . . . ?
C1 N1 C9 C10 109.77(18) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C1 C6 C7 N2 174.19(15) . . . . ?
C1 C6 C7 C8 -2.23(16) . . . . ?
C2 C1 C6 C5 2.5(2) . . . . ?
C2 C1 C6 C7 -176.91(14) . . . . ?
C2 C3 C4 C5 1.4(2) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C1 -1.6(2) . . . . ?
C4 C5 C6 C7 177.59(16) . . . . ?
C5 C6 C7 N2 -5.1(3) . . . . ?
C5 C6 C7 C8 178.45(16) . . . . ?
C6 C1 C2 C3 -1.3(2) . . . . ?
C6 C7 C8 O1 -179.18(16) . . . . ?
C6 C7 C8 N1 1.23(17) . . . . ?
C7 N2 N3 C12 177.53(14) . . . . ?
C8 N1 C1 C2 177.56(15) . . . . ?
C8 N1 C1 C6 -1.75(18) . . . . ?
C8 N1 C9 C10 -73.75(19) . . . . ?
C9 N1 C1 C2 -5.6(3) . . . . ?
C9 N1 C1 C6 175.05(14) . . . . ?
C9 N1 C8 O1 3.7(2) . . . . ?
C9 N1 C8 C7 -176.74(13) . . . . ?
C12 N4 C13 C14 165.91(14) . . . . ?
C12 N4 C16 C15 168.79(15) . . . . ?
C13 N4 C12 S1 5.7(2) . . . . ?
C13 N4 C12 N3 -174.15(13) . . . . ?
C13 N4 C16 C15 -9.87(17) . . . . ?
C13 C14 C15 C16 -40.94(17) . . . . ?
C14 C15 C16 N4 31.08(16) . . . . ?
C16 N4 C12 S1 -172.79(12) . . . . ?
C16 N4 C12 N3 7.3(2) . . . . ?
C16 N4 C13 C14 -15.38(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_preparation       Luminescent
_chemical_compound_source        433K
####################################################################### 
# 
# 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_mc1b
_database_code_depnum_ccdc_archive 'CCDC 1418934'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;
_audit_creation_date             2014-12-15
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.10.22 svn.r3046 for OlexSys, GUI svn.r4928)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
"N'-(1-benzyl-2-oxoindolin-3-ylidene)pyrrolidine-1-carbothiohydrazide "
_chemical_formula_moiety         'C20 H20 N4 O S'
_chemical_formula_sum            'C20 H20 N4 O S'
_chemical_formula_weight         364.46
_chemical_melting_point          444K
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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.0090(17)
_cell_length_b                   19.621(4)
_cell_length_c                   11.510(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.636(2)
_cell_angle_gamma                90
_cell_volume                     1802.8(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5752
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      27.450
_cell_measurement_theta_min      2.732
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.898
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1278 before and 0.0492 after correction.
The Ratio of minimum to maximum transmission is 0.8719.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15627
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.553
_diffrn_reflns_theta_min         2.056
_diffrn_ambient_temperature      110.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3286
_reflns_number_total             4123
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4123
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.023
_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)+(0.0365P)²+0.7122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0962
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C3(H3A), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.98359(5) 0.42165(2) 0.70746(4) 0.02561(12) Uani 1 1 d . . . . .
O1 O 0.65855(14) 0.63256(6) 0.47776(9) 0.0277(3) Uani 1 1 d . . . . .
N1 N 0.52478(16) 0.58796(7) 0.30828(11) 0.0223(3) Uani 1 1 d . . . . .
N2 N 0.76628(16) 0.48407(7) 0.51228(11) 0.0227(3) Uani 1 1 d . . . . .
N3 N 0.83470(16) 0.52783(7) 0.59309(11) 0.0236(3) Uani 1 1 d . . . . .
H3 H 0.8140 0.5717 0.5858 0.028 Uiso 1 1 calc R . . . .
N4 N 0.99367(16) 0.55377(7) 0.75956(11) 0.0214(3) Uani 1 1 d . . . . .
C1 C 0.50374(19) 0.52257(8) 0.25819(13) 0.0213(3) Uani 1 1 d . . . . .
C2 C 0.4176(2) 0.50473(9) 0.15358(14) 0.0272(4) Uani 1 1 d . . . . .
H2 H 0.3627 0.5380 0.1042 0.033 Uiso 1 1 calc R . . . .
C3 C 0.4146(2) 0.43574(9) 0.12363(14) 0.0315(4) Uani 1 1 d . . . . .
H3A H 0.3577 0.4219 0.0519 0.038 Uiso 1 1 calc R . . . .
C4 C 0.4932(2) 0.38687(9) 0.19647(15) 0.0311(4) Uani 1 1 d . . . . .
H4 H 0.4869 0.3402 0.1747 0.037 Uiso 1 1 calc R . . . .
C5 C 0.5811(2) 0.40557(8) 0.30122(14) 0.0265(4) Uani 1 1 d . . . . .
H5 H 0.6352 0.3722 0.3509 0.032 Uiso 1 1 calc R . . . .
C6 C 0.58754(19) 0.47400(8) 0.33083(13) 0.0218(3) Uani 1 1 d . . . . .
C7 C 0.66962(19) 0.51098(8) 0.42926(13) 0.0210(3) Uani 1 1 d . . . . .
C8 C 0.62194(19) 0.58457(8) 0.41189(13) 0.0218(3) Uani 1 1 d . . . . .
C9 C 0.4366(2) 0.64925(8) 0.26644(14) 0.0257(4) Uani 1 1 d . . . . .
H9A H 0.4330 0.6814 0.3324 0.031 Uiso 1 1 calc R . . . .
H9B H 0.3196 0.6368 0.2408 0.031 Uiso 1 1 calc R . . . .
C10 C 0.51182(19) 0.68568(8) 0.16711(13) 0.0218(3) Uani 1 1 d . . . . .
C11 C 0.6833(2) 0.68812(9) 0.15949(14) 0.0284(4) Uani 1 1 d . . . . .
H11 H 0.7558 0.6629 0.2128 0.034 Uiso 1 1 calc R . . . .
C12 C 0.7497(2) 0.72750(9) 0.07379(16) 0.0341(4) Uani 1 1 d . . . . .
H12 H 0.8675 0.7291 0.0691 0.041 Uiso 1 1 calc R . . . .
C13 C 0.6453(3) 0.76432(9) -0.00464(15) 0.0349(4) Uani 1 1 d . . . . .
H13 H 0.6914 0.7917 -0.0621 0.042 Uiso 1 1 calc R . . . .
C14 C 0.4747(2) 0.76112(9) 0.00086(14) 0.0309(4) Uani 1 1 d . . . . .
H14 H 0.4025 0.7856 -0.0538 0.037 Uiso 1 1 calc R . . . .
C15 C 0.4083(2) 0.72219(8) 0.08624(13) 0.0260(4) Uani 1 1 d . . . . .
H15 H 0.2903 0.7203 0.0898 0.031 Uiso 1 1 calc R . . . .
C16 C 0.93677(18) 0.50449(8) 0.68693(12) 0.0202(3) Uani 1 1 d . . . . .
C17 C 1.0902(2) 0.53995(8) 0.87134(12) 0.0224(3) Uani 1 1 d . . . . .
H17A H 1.2093 0.5307 0.8600 0.027 Uiso 1 1 calc R . . . .
H17B H 1.0430 0.5008 0.9119 0.027 Uiso 1 1 calc R . . . .
C18 C 1.0709(2) 0.60600(8) 0.93865(14) 0.0305(4) Uani 1 1 d . . . . .
H18A H 1.1685 0.6136 0.9957 0.037 Uiso 1 1 calc R . . . .
H18B H 0.9677 0.6052 0.9805 0.037 Uiso 1 1 calc R . . . .
C19 C 1.0609(2) 0.66110(9) 0.84455(14) 0.0299(4) Uani 1 1 d . . . . .
H19A H 1.0021 0.7020 0.8706 0.036 Uiso 1 1 calc R . . . .
H19B H 1.1741 0.6744 0.8241 0.036 Uiso 1 1 calc R . . . .
C20 C 0.9616(2) 0.62729(8) 0.74124(14) 0.0259(4) Uani 1 1 d . . . . .
H20A H 0.8406 0.6376 0.7414 0.031 Uiso 1 1 calc R . . . .
H20B H 1.0017 0.6427 0.6665 0.031 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
S1 C16 1.6804(16) . ?
O1 C8 1.2294(18) . ?
N1 C1 1.411(2) . ?
N1 C8 1.3720(19) . ?
N1 C9 1.457(2) . ?
N2 N3 1.3491(18) . ?
N2 C7 1.2928(19) . ?
N3 H3 0.8800 . ?
N3 C16 1.3791(19) . ?
N4 C16 1.334(2) . ?
N4 C17 1.4716(18) . ?
N4 C20 1.477(2) . ?
C1 C2 1.384(2) . ?
C1 C6 1.403(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.397(2) . ?
C3 H3A 0.9500 . ?
C3 C4 1.390(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.395(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(2) . ?
C6 C7 1.457(2) . ?
C7 C8 1.503(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.514(2) . ?
C10 C11 1.384(2) . ?
C10 C15 1.393(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.392(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.374(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(2) . ?
C15 H15 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.524(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.528(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.527(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?

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 N1 C9 125.23(13) . . ?
C8 N1 C1 110.59(13) . . ?
C8 N1 C9 123.58(13) . . ?
C7 N2 N3 115.81(13) . . ?
N2 N3 H3 119.6 . . ?
N2 N3 C16 120.71(13) . . ?
C16 N3 H3 119.6 . . ?
C16 N4 C17 122.89(13) . . ?
C16 N4 C20 124.86(13) . . ?
C17 N4 C20 112.19(12) . . ?
C2 C1 N1 128.34(15) . . ?
C2 C1 C6 121.86(15) . . ?
C6 C1 N1 109.80(13) . . ?
C1 C2 H2 121.4 . . ?
C1 C2 C3 117.22(16) . . ?
C3 C2 H2 121.4 . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 C2 121.46(15) . . ?
C4 C3 H3A 119.3 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.78(16) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.9 . . ?
C6 C5 C4 118.28(16) . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C7 106.81(13) . . ?
C5 C6 C1 120.36(14) . . ?
C5 C6 C7 132.82(15) . . ?
N2 C7 C6 125.25(15) . . ?
N2 C7 C8 128.40(14) . . ?
C6 C7 C8 106.34(13) . . ?
O1 C8 N1 126.10(15) . . ?
O1 C8 C7 127.49(14) . . ?
N1 C8 C7 106.40(13) . . ?
N1 C9 H9A 108.4 . . ?
N1 C9 H9B 108.4 . . ?
N1 C9 C10 115.33(13) . . ?
H9A C9 H9B 107.5 . . ?
C10 C9 H9A 108.4 . . ?
C10 C9 H9B 108.4 . . ?
C11 C10 C9 121.43(14) . . ?
C11 C10 C15 118.66(15) . . ?
C15 C10 C9 119.72(14) . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.12(16) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.46(17) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.80(16) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.88(16) . . ?
C15 C14 H14 120.1 . . ?
C10 C15 H15 119.5 . . ?
C14 C15 C10 121.07(16) . . ?
C14 C15 H15 119.5 . . ?
N3 C16 S1 122.87(12) . . ?
N4 C16 S1 123.50(12) . . ?
N4 C16 N3 113.63(14) . . ?
N4 C17 H17A 111.2 . . ?
N4 C17 H17B 111.2 . . ?
N4 C17 C18 102.72(12) . . ?
H17A C17 H17B 109.1 . . ?
C18 C17 H17A 111.2 . . ?
C18 C17 H17B 111.2 . . ?
C17 C18 H18A 110.9 . . ?
C17 C18 H18B 110.9 . . ?
C17 C18 C19 104.06(13) . . ?
H18A C18 H18B 109.0 . . ?
C19 C18 H18A 110.9 . . ?
C19 C18 H18B 110.9 . . ?
C18 C19 H19A 111.0 . . ?
C18 C19 H19B 111.0 . . ?
H19A C19 H19B 109.0 . . ?
C20 C19 C18 103.82(13) . . ?
C20 C19 H19A 111.0 . . ?
C20 C19 H19B 111.0 . . ?
N4 C20 C19 103.84(12) . . ?
N4 C20 H20A 111.0 . . ?
N4 C20 H20B 111.0 . . ?
C19 C20 H20A 111.0 . . ?
C19 C20 H20B 111.0 . . ?
H20A C20 H20B 109.0 . . ?

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
N3 H3 O1 0.88 2.07 2.7699(18) 136.2 .

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
N1 C1 C2 C3 -179.67(15) . . . . ?
N1 C1 C6 C5 178.31(14) . . . . ?
N1 C1 C6 C7 -1.93(17) . . . . ?
N1 C9 C10 C11 -35.2(2) . . . . ?
N1 C9 C10 C15 149.94(14) . . . . ?
N2 N3 C16 S1 0.2(2) . . . . ?
N2 N3 C16 N4 -179.51(13) . . . . ?
N2 C7 C8 O1 -4.7(3) . . . . ?
N2 C7 C8 N1 176.72(15) . . . . ?
N3 N2 C7 C6 177.68(13) . . . . ?
N3 N2 C7 C8 -0.8(2) . . . . ?
N4 C17 C18 C19 -32.56(17) . . . . ?
C1 N1 C8 O1 -177.71(15) . . . . ?
C1 N1 C8 C7 0.86(16) . . . . ?
C1 N1 C9 C10 -83.44(18) . . . . ?
C1 C2 C3 C4 0.8(2) . . . . ?
C1 C6 C7 N2 -176.40(15) . . . . ?
C1 C6 C7 C8 2.37(16) . . . . ?
C2 C1 C6 C5 -2.3(2) . . . . ?
C2 C1 C6 C7 177.43(14) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 C1 1.6(2) . . . . ?
C4 C5 C6 C7 -178.08(16) . . . . ?
C5 C6 C7 N2 3.3(3) . . . . ?
C5 C6 C7 C8 -177.91(17) . . . . ?
C6 C1 C2 C3 1.1(2) . . . . ?
C6 C7 C8 O1 176.54(15) . . . . ?
C6 C7 C8 N1 -2.00(16) . . . . ?
C7 N2 N3 C16 178.52(13) . . . . ?
C8 N1 C1 C2 -178.65(15) . . . . ?
C8 N1 C1 C6 0.66(17) . . . . ?
C8 N1 C9 C10 106.22(17) . . . . ?
C9 N1 C1 C2 9.9(2) . . . . ?
C9 N1 C1 C6 -170.75(14) . . . . ?
C9 N1 C8 O1 -6.1(2) . . . . ?
C9 N1 C8 C7 172.44(13) . . . . ?
C9 C10 C11 C12 -173.70(15) . . . . ?
C9 C10 C15 C14 174.01(14) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C11 C10 C15 C14 -1.0(2) . . . . ?
C11 C12 C13 C14 -1.1(3) . . . . ?
C12 C13 C14 C15 1.3(3) . . . . ?
C13 C14 C15 C10 -0.2(2) . . . . ?
C15 C10 C11 C12 1.2(2) . . . . ?
C16 N4 C17 C18 -160.42(14) . . . . ?
C16 N4 C20 C19 -177.08(14) . . . . ?
C17 N4 C16 S1 -6.1(2) . . . . ?
C17 N4 C16 N3 173.57(13) . . . . ?
C17 N4 C20 C19 5.71(17) . . . . ?
C17 C18 C19 C20 36.70(18) . . . . ?
C18 C19 C20 N4 -25.94(17) . . . . ?
C20 N4 C16 S1 176.93(12) . . . . ?
C20 N4 C16 N3 -3.4(2) . . . . ?
C20 N4 C17 C18 16.85(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_compound_source        'METHANOL / ACEONITRILE'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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. 
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#######################################################################

data_mc1bp
_database_code_depnum_ccdc_archive 'CCDC 1418935'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;
_audit_creation_date             2014-12-12
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.10.22 svn.r3046 for OlexSys, GUI svn.r4928)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
"N'-(2-oxo-1-pentylindolin-3-ylidene)pyrrolidine-1-carbothiohydrazide "
_chemical_formula_moiety         'C18 H24 N4 O S'
_chemical_formula_sum            'C18 H24 N4 O S'
_chemical_formula_weight         344.47
_chemical_melting_point          422K
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.352(6)
_cell_length_b                   8.874(6)
_cell_length_c                   13.617(9)
_cell_angle_alpha                79.406(7)
_cell_angle_beta                 81.424(7)
_cell_angle_gamma                64.639(7)
_cell_volume                     893.5(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3532
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      27.258
_cell_measurement_theta_min      2.563
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.901
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1437 before and 0.0636 after correction.
The Ratio of minimum to maximum transmission is 0.6537.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_unetI/netI     0.0743
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10379
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.617
_diffrn_reflns_theta_min         1.526
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2991
_reflns_number_total             4057
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4057
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0501
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0543P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1284
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C15(H15A,H15B),
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C3(H3A), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.92096(6) 0.31681(6) 0.67012(4) 0.02696(16) Uani 1 1 d . . . . .
O1 O 0.56320(16) 0.75695(15) 0.36121(9) 0.0256(3) Uani 1 1 d . . . . .
N1 N 0.5303(2) 0.60346(18) 0.25055(11) 0.0219(4) Uani 1 1 d . . . . .
N2 N 0.74073(19) 0.40797(18) 0.47780(11) 0.0198(3) Uani 1 1 d . . . . .
N3 N 0.74179(18) 0.53652(18) 0.51697(10) 0.0199(4) Uani 1 1 d . . . . .
H3 H 0.6878 0.6403 0.4875 0.024 Uiso 1 1 calc R . . . .
N4 N 0.82512(19) 0.64828(19) 0.62726(10) 0.0197(3) Uani 1 1 d . . . . .
C1 C 0.5683(2) 0.4325(2) 0.24831(13) 0.0194(4) Uani 1 1 d . . . . .
C2 C 0.5357(2) 0.3611(2) 0.17603(14) 0.0259(4) Uani 1 1 d . . . . .
H2 H 0.4790 0.4282 0.1179 0.031 Uiso 1 1 calc R . . . .
C3 C 0.5887(3) 0.1871(2) 0.19095(14) 0.0277(5) Uani 1 1 d . . . . .
H3A H 0.5677 0.1353 0.1420 0.033 Uiso 1 1 calc R . . . .
C4 C 0.6720(2) 0.0874(2) 0.27619(14) 0.0255(4) Uani 1 1 d . . . . .
H4 H 0.7080 -0.0310 0.2843 0.031 Uiso 1 1 calc R . . . .
C5 C 0.7022(2) 0.1610(2) 0.34933(14) 0.0223(4) Uani 1 1 d . . . . .
H5 H 0.7575 0.0938 0.4078 0.027 Uiso 1 1 calc R . . . .
C6 C 0.6505(2) 0.3344(2) 0.33566(13) 0.0184(4) Uani 1 1 d . . . . .
C7 C 0.6630(2) 0.4502(2) 0.39460(13) 0.0184(4) Uani 1 1 d . . . . .
C8 C 0.5807(2) 0.6230(2) 0.33655(13) 0.0207(4) Uani 1 1 d . . . . .
C9 C 0.4494(3) 0.7418(2) 0.17145(14) 0.0284(5) Uani 1 1 d . . . . .
H9A H 0.4106 0.8500 0.1978 0.034 Uiso 1 1 calc R . . . .
H9B H 0.3425 0.7352 0.1532 0.034 Uiso 1 1 calc R . . . .
C10 C 0.5749(3) 0.7400(3) 0.07727(14) 0.0315(5) Uani 1 1 d . . . . .
H10A H 0.5992 0.6398 0.0455 0.038 Uiso 1 1 calc R . . . .
H10B H 0.5143 0.8409 0.0293 0.038 Uiso 1 1 calc R . . . .
C11 C 0.7505(3) 0.7375(3) 0.09604(14) 0.0313(5) Uani 1 1 d . . . . .
H11A H 0.8190 0.6288 0.1360 0.038 Uiso 1 1 calc R . . . .
H11B H 0.7264 0.8280 0.1365 0.038 Uiso 1 1 calc R . . . .
C12 C 0.8643(3) 0.7605(3) 0.00094(16) 0.0441(6) Uani 1 1 d . . . . .
H12A H 0.8852 0.6722 -0.0406 0.053 Uiso 1 1 calc R . . . .
H12B H 0.7976 0.8709 -0.0380 0.053 Uiso 1 1 calc R . . . .
C13 C 1.0420(3) 0.7520(4) 0.0205(2) 0.0623(8) Uani 1 1 d . . . . .
H13A H 1.1092 0.7651 -0.0436 0.093 Uiso 1 1 calc GR . . . .
H13B H 1.1093 0.6430 0.0588 0.093 Uiso 1 1 calc GR . . . .
H13C H 1.0227 0.8425 0.0588 0.093 Uiso 1 1 calc GR . . . .
C14 C 0.8269(2) 0.5072(2) 0.60310(13) 0.0197(4) Uani 1 1 d . . . . .
C15 C 0.8979(3) 0.6491(2) 0.71905(13) 0.0243(4) Uani 1 1 d . . . . .
H15A H 1.0283 0.5827 0.7162 0.029 Uiso 1 1 calc R . . . .
H15B H 0.8423 0.6028 0.7791 0.029 Uiso 1 1 calc R . . . .
C16 C 0.8505(3) 0.8356(2) 0.72017(14) 0.0283(5) Uani 1 1 d . . . . .
H16A H 0.7336 0.8898 0.7573 0.034 Uiso 1 1 calc R . . . .
H16B H 0.9417 0.8499 0.7515 0.034 Uiso 1 1 calc R . . . .
C17 C 0.8449(3) 0.9099(2) 0.60945(14) 0.0256(4) Uani 1 1 d . . . . .
H17A H 0.7707 1.0326 0.6012 0.031 Uiso 1 1 calc R . . . .
H17B H 0.9658 0.8887 0.5777 0.031 Uiso 1 1 calc R . . . .
C18 C 0.7620(2) 0.8165(2) 0.56500(13) 0.0219(4) Uani 1 1 d . . . . .
H18A H 0.6307 0.8742 0.5709 0.026 Uiso 1 1 calc R . . . .
H18B H 0.8042 0.8067 0.4936 0.026 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
S1 C14 1.678(2) . ?
O1 C8 1.237(2) . ?
N1 C1 1.416(2) . ?
N1 C8 1.365(2) . ?
N1 C9 1.464(2) . ?
N2 N3 1.349(2) . ?
N2 C7 1.304(2) . ?
N3 H3 0.8800 . ?
N3 C14 1.388(2) . ?
N4 C14 1.345(2) . ?
N4 C15 1.472(2) . ?
N4 C18 1.490(2) . ?
C1 C2 1.379(3) . ?
C1 C6 1.412(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.395(3) . ?
C3 H3A 0.9500 . ?
C3 C4 1.396(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(3) . ?
C6 C7 1.459(3) . ?
C7 C8 1.504(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.528(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.516(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.524(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.515(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.530(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.529(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.527(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?

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 N1 C9 125.12(15) . . ?
C8 N1 C1 110.90(15) . . ?
C8 N1 C9 123.97(16) . . ?
C7 N2 N3 115.33(15) . . ?
N2 N3 H3 119.6 . . ?
N2 N3 C14 120.85(15) . . ?
C14 N3 H3 119.6 . . ?
C14 N4 C15 122.12(15) . . ?
C14 N4 C18 125.97(15) . . ?
C15 N4 C18 111.82(15) . . ?
C2 C1 N1 129.00(17) . . ?
C2 C1 C6 121.61(17) . . ?
C6 C1 N1 109.40(15) . . ?
C1 C2 H2 121.0 . . ?
C1 C2 C3 117.90(18) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3A 119.3 . . ?
C2 C3 C4 121.49(18) . . ?
C4 C3 H3A 119.3 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.15(18) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.17(17) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C7 106.69(16) . . ?
C5 C6 C1 119.67(17) . . ?
C5 C6 C7 133.64(17) . . ?
N2 C7 C6 125.88(16) . . ?
N2 C7 C8 127.64(17) . . ?
C6 C7 C8 106.36(16) . . ?
O1 C8 N1 126.47(17) . . ?
O1 C8 C7 126.90(17) . . ?
N1 C8 C7 106.63(16) . . ?
N1 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
N1 C9 C10 113.29(15) . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C9 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 C9 114.32(17) . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C10 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
C10 C11 C12 114.13(17) . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C11 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 C11 113.7(2) . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 S1 123.70(14) . . ?
N4 C14 S1 123.64(14) . . ?
N4 C14 N3 112.66(15) . . ?
N4 C15 H15A 111.0 . . ?
N4 C15 H15B 111.0 . . ?
N4 C15 C16 103.55(15) . . ?
H15A C15 H15B 109.0 . . ?
C16 C15 H15A 111.0 . . ?
C16 C15 H15B 111.0 . . ?
C15 C16 H16A 110.9 . . ?
C15 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
C17 C16 C15 104.20(15) . . ?
C17 C16 H16A 110.9 . . ?
C17 C16 H16B 110.9 . . ?
C16 C17 H17A 111.1 . . ?
C16 C17 H17B 111.1 . . ?
H17A C17 H17B 109.1 . . ?
C18 C17 C16 103.25(15) . . ?
C18 C17 H17A 111.1 . . ?
C18 C17 H17B 111.1 . . ?
N4 C18 C17 103.13(15) . . ?
N4 C18 H18A 111.1 . . ?
N4 C18 H18B 111.1 . . ?
C17 C18 H18A 111.1 . . ?
C17 C18 H18B 111.1 . . ?
H18A C18 H18B 109.1 . . ?

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
N3 H3 O1 0.88 2.02 2.733(2) 137.6 .

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
N1 C1 C2 C3 179.12(17) . . . . ?
N1 C1 C6 C5 -179.22(15) . . . . ?
N1 C1 C6 C7 0.27(19) . . . . ?
N1 C9 C10 C11 -54.6(2) . . . . ?
N2 N3 C14 S1 -4.7(2) . . . . ?
N2 N3 C14 N4 175.62(14) . . . . ?
N2 C7 C8 O1 -4.8(3) . . . . ?
N2 C7 C8 N1 174.72(16) . . . . ?
N3 N2 C7 C6 177.41(15) . . . . ?
N3 N2 C7 C8 2.1(2) . . . . ?
N4 C15 C16 C17 -28.64(19) . . . . ?
C1 N1 C8 O1 -179.00(17) . . . . ?
C1 N1 C8 C7 1.51(19) . . . . ?
C1 N1 C9 C10 -72.2(2) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C1 C6 C7 N2 -175.50(16) . . . . ?
C1 C6 C7 C8 0.62(18) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C2 C1 C6 C7 -179.80(16) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C4 C5 C6 C7 -179.22(18) . . . . ?
C5 C6 C7 N2 3.9(3) . . . . ?
C5 C6 C7 C8 180.00(18) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
C6 C7 C8 O1 179.20(17) . . . . ?
C6 C7 C8 N1 -1.31(18) . . . . ?
C7 N2 N3 C14 -177.30(14) . . . . ?
C8 N1 C1 C2 178.91(18) . . . . ?
C8 N1 C1 C6 -1.2(2) . . . . ?
C8 N1 C9 C10 107.1(2) . . . . ?
C9 N1 C1 C2 -1.7(3) . . . . ?
C9 N1 C1 C6 178.25(15) . . . . ?
C9 N1 C8 O1 1.6(3) . . . . ?
C9 N1 C8 C7 -177.91(15) . . . . ?
C9 C10 C11 C12 -171.87(17) . . . . ?
C10 C11 C12 C13 -178.1(2) . . . . ?
C14 N4 C15 C16 -174.52(15) . . . . ?
C14 N4 C18 C17 -161.99(16) . . . . ?
C15 N4 C14 S1 -3.5(2) . . . . ?
C15 N4 C14 N3 176.19(14) . . . . ?
C15 N4 C18 C17 14.61(18) . . . . ?
C15 C16 C17 C18 37.91(19) . . . . ?
C16 C17 C18 N4 -31.82(17) . . . . ?
C18 N4 C14 S1 172.74(13) . . . . ?
C18 N4 C14 N3 -7.5(2) . . . . ?
C18 N4 C15 C16 8.73(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: METHANOL / ACETONITRILE'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_mc1p
_database_code_depnum_ccdc_archive 'CCDC 1418936'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;
_audit_creation_date             2014-12-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_name_common            ?
_chemical_name_systematic        
"N'-(2-oxo-1-(prop-2-yn-1-yl)indolin-3-ylidene)pyrrolidine-1-carbothiohydrazide "
_chemical_formula_moiety         'C16 H16 N4 O S'
_chemical_formula_sum            'C16 H16 N4 O S'
_chemical_formula_weight         312.39
_chemical_melting_point          440
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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.496(8)
_cell_length_b                   9.118(3)
_cell_length_c                   15.908(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.156(6)
_cell_angle_gamma                90
_cell_volume                     2962.7(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8954
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      27.559
_cell_measurement_theta_min      2.446
_shelx_estimated_absorpt_T_max   0.931
_shelx_estimated_absorpt_T_min   0.882
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0848 before and 0.0488 after correction.
The Ratio of minimum to maximum transmission is 0.9312.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.32
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16644
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.600
_diffrn_reflns_theta_min         2.446
_diffrn_ambient_temperature      110.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3090
_reflns_number_total             3412
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3412
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0304
_refine_ls_restrained_S_all      1.023
_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)+(0.0308P)²+3.2006P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0777
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C14(H14A,H14B), C16(H16A,H16B), C13(H13A,H13B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C5(H5), C4(H4), C2(H2), C3(H3A)
2.c :
 C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.45087(2) 0.28559(3) 0.56965(2) 0.01773(9) Uani 1 1 d . . . . .
O1 O 0.21174(4) 0.48857(9) 0.38401(6) 0.02018(19) Uani 1 1 d . . . . .
N2 N 0.31371(5) 0.24906(11) 0.44479(6) 0.0151(2) Uani 1 1 d . . . . .
N1 N 0.15286(5) 0.29949(11) 0.29791(7) 0.0155(2) Uani 1 1 d . . . . .
N4 N 0.40231(5) 0.55663(11) 0.55374(6) 0.0158(2) Uani 1 1 d . . . . .
N3 N 0.33092(5) 0.38519(11) 0.47736(7) 0.0162(2) Uani 1 1 d . . . . .
H3 H 0.3018 0.4563 0.4628 0.019 Uiso 1 1 calc R . . . .
C9 C 0.09164(6) 0.37882(13) 0.26008(8) 0.0171(2) Uani 1 1 d . . . . .
H9A H 0.0843 0.4438 0.3060 0.020 Uiso 1 1 calc R . . . .
H9B H 0.0552 0.3074 0.2428 0.020 Uiso 1 1 calc R . . . .
C1 C 0.16336(6) 0.14958(13) 0.28492(8) 0.0143(2) Uani 1 1 d . . . . .
C10 C 0.09028(6) 0.46750(13) 0.18264(8) 0.0172(2) Uani 1 1 d . . . . .
C12 C 0.39300(6) 0.41507(13) 0.53285(7) 0.0147(2) Uani 1 1 d . . . . .
C11 C 0.08730(6) 0.54170(14) 0.11995(9) 0.0217(3) Uani 1 1 d . . . . .
H11 H 0.0849 0.6009 0.0699 0.026 Uiso 1 1 calc R . . . .
C5 C 0.24555(6) -0.03759(13) 0.34219(8) 0.0164(2) Uani 1 1 d . . . . .
H5 H 0.2869 -0.0678 0.3808 0.020 Uiso 1 1 calc R . . . .
C6 C 0.22489(6) 0.10707(13) 0.34157(7) 0.0142(2) Uani 1 1 d . . . . .
C7 C 0.25516(6) 0.23848(13) 0.38946(8) 0.0143(2) Uani 1 1 d . . . . .
C8 C 0.20595(6) 0.35978(13) 0.35909(8) 0.0155(2) Uani 1 1 d . . . . .
C4 C 0.20410(6) -0.13732(13) 0.28475(8) 0.0188(2) Uani 1 1 d . . . . .
H4 H 0.2169 -0.2370 0.2849 0.023 Uiso 1 1 calc R . . . .
C14 C 0.44417(6) 0.76898(14) 0.63498(8) 0.0203(3) Uani 1 1 d . . . . .
H14A H 0.4832 0.8332 0.6535 0.024 Uiso 1 1 calc R . . . .
H14B H 0.4218 0.7717 0.6807 0.024 Uiso 1 1 calc R . . . .
C2 C 0.12233(6) 0.05306(13) 0.22599(8) 0.0173(2) Uani 1 1 d . . . . .
H2 H 0.0814 0.0837 0.1866 0.021 Uiso 1 1 calc R . . . .
C16 C 0.35628(6) 0.67684(13) 0.51379(8) 0.0187(2) Uani 1 1 d . . . . .
H16A H 0.3180 0.6761 0.5358 0.022 Uiso 1 1 calc R . . . .
H16B H 0.3409 0.6696 0.4484 0.022 Uiso 1 1 calc R . . . .
C13 C 0.46264(6) 0.61233(14) 0.61840(8) 0.0186(2) Uani 1 1 d . . . . .
H13A H 0.4996 0.6113 0.5938 0.022 Uiso 1 1 calc R . . . .
H13B H 0.4746 0.5537 0.6735 0.022 Uiso 1 1 calc R . . . .
C3 C 0.14407(6) -0.09181(14) 0.22727(8) 0.0190(2) Uani 1 1 d . . . . .
H3A H 0.1171 -0.1611 0.1878 0.023 Uiso 1 1 calc R . . . .
C15 C 0.39797(6) 0.81412(14) 0.54456(9) 0.0213(3) Uani 1 1 d . . . . .
H15A H 0.4226 0.8395 0.5034 0.026 Uiso 1 1 calc R . . . .
H15B H 0.3706 0.8988 0.5497 0.026 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
S1 C12 1.6823(13) . ?
O1 C8 1.2333(15) . ?
N2 N3 1.3515(14) . ?
N2 C7 1.2952(16) . ?
N1 C9 1.4572(15) . ?
N1 C1 1.4110(16) . ?
N1 C8 1.3636(15) . ?
N4 C12 1.3324(16) . ?
N4 C16 1.4807(15) . ?
N4 C13 1.4717(15) . ?
N3 H3 0.8800 . ?
N3 C12 1.3784(15) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.4663(17) . ?
C1 C6 1.4033(16) . ?
C1 C2 1.3842(17) . ?
C10 C11 1.1902(18) . ?
C11 H11 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.3908(17) . ?
C5 C4 1.3959(17) . ?
C6 C7 1.4596(16) . ?
C7 C8 1.5025(16) . ?
C4 H4 0.9500 . ?
C4 C3 1.3921(18) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.5273(18) . ?
C14 C15 1.5279(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.3992(18) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C15 1.5285(18) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C3 H3A 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N2 N3 114.89(10) . . ?
C1 N1 C9 125.83(10) . . ?
C8 N1 C9 122.81(10) . . ?
C8 N1 C1 111.01(10) . . ?
C12 N4 C16 125.56(10) . . ?
C12 N4 C13 122.67(10) . . ?
C13 N4 C16 111.72(10) . . ?
N2 N3 H3 119.3 . . ?
N2 N3 C12 121.45(10) . . ?
C12 N3 H3 119.3 . . ?
N1 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
N1 C9 C10 113.56(10) . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C6 C1 N1 109.59(10) . . ?
C2 C1 N1 128.16(11) . . ?
C2 C1 C6 122.24(11) . . ?
C11 C10 C9 177.78(13) . . ?
N4 C12 S1 123.76(9) . . ?
N4 C12 N3 113.05(10) . . ?
N3 C12 S1 123.19(9) . . ?
C10 C11 H11 180.0 . . ?
C6 C5 H5 120.8 . . ?
C6 C5 C4 118.42(11) . . ?
C4 C5 H5 120.8 . . ?
C1 C6 C7 106.63(10) . . ?
C5 C6 C1 120.10(11) . . ?
C5 C6 C7 133.27(11) . . ?
N2 C7 C6 126.62(11) . . ?
N2 C7 C8 126.97(11) . . ?
C6 C7 C8 106.36(10) . . ?
O1 C8 N1 126.26(11) . . ?
O1 C8 C7 127.38(11) . . ?
N1 C8 C7 106.36(10) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.51(11) . . ?
C3 C4 H4 119.7 . . ?
H14A C14 H14B 109.2 . . ?
C13 C14 H14A 111.3 . . ?
C13 C14 H14B 111.3 . . ?
C13 C14 C15 102.53(10) . . ?
C15 C14 H14A 111.3 . . ?
C15 C14 H14B 111.3 . . ?
C1 C2 H2 121.6 . . ?
C1 C2 C3 116.81(11) . . ?
C3 C2 H2 121.6 . . ?
N4 C16 H16A 111.2 . . ?
N4 C16 H16B 111.2 . . ?
N4 C16 C15 102.83(10) . . ?
H16A C16 H16B 109.1 . . ?
C15 C16 H16A 111.2 . . ?
C15 C16 H16B 111.2 . . ?
N4 C13 C14 102.92(10) . . ?
N4 C13 H13A 111.2 . . ?
N4 C13 H13B 111.2 . . ?
C14 C13 H13A 111.2 . . ?
C14 C13 H13B 111.2 . . ?
H13A C13 H13B 109.1 . . ?
C4 C3 C2 121.87(11) . . ?
C4 C3 H3A 119.1 . . ?
C2 C3 H3A 119.1 . . ?
C14 C15 C16 103.01(10) . . ?
C14 C15 H15A 111.2 . . ?
C14 C15 H15B 111.2 . . ?
C16 C15 H15A 111.2 . . ?
C16 C15 H15B 111.2 . . ?
H15A C15 H15B 109.1 . . ?

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
N3 H3 O1 0.88 1.97 2.6993(15) 138.8 .

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
N2 N3 C12 S1 -3.76(16) . . . . ?
N2 N3 C12 N4 175.94(10) . . . . ?
N2 C7 C8 O1 -3.1(2) . . . . ?
N2 C7 C8 N1 176.99(11) . . . . ?
N1 C1 C6 C5 178.47(10) . . . . ?
N1 C1 C6 C7 -2.38(12) . . . . ?
N1 C1 C2 C3 -179.01(11) . . . . ?
N4 C16 C15 C14 -32.08(12) . . . . ?
N3 N2 C7 C6 177.27(10) . . . . ?
N3 N2 C7 C8 -0.11(17) . . . . ?
C9 N1 C1 C6 -171.42(10) . . . . ?
C9 N1 C1 C2 9.57(19) . . . . ?
C9 N1 C8 O1 -6.98(19) . . . . ?
C9 N1 C8 C7 172.96(10) . . . . ?
C1 N1 C9 C10 -100.81(13) . . . . ?
C1 N1 C8 O1 179.43(11) . . . . ?
C1 N1 C8 C7 -0.63(13) . . . . ?
C1 C6 C7 N2 -175.88(11) . . . . ?
C1 C6 C7 C8 1.94(12) . . . . ?
C1 C2 C3 C4 -0.15(18) . . . . ?
C12 N4 C16 C15 -166.65(11) . . . . ?
C12 N4 C13 C14 -167.64(11) . . . . ?
C5 C6 C7 N2 3.1(2) . . . . ?
C5 C6 C7 C8 -179.06(12) . . . . ?
C5 C4 C3 C2 -1.46(18) . . . . ?
C6 C1 C2 C3 2.09(17) . . . . ?
C6 C5 C4 C3 1.12(17) . . . . ?
C6 C7 C8 O1 179.12(11) . . . . ?
C6 C7 C8 N1 -0.82(12) . . . . ?
C7 N2 N3 C12 -176.13(10) . . . . ?
C8 N1 C9 C10 86.57(14) . . . . ?
C8 N1 C1 C6 1.94(13) . . . . ?
C8 N1 C1 C2 -177.08(11) . . . . ?
C4 C5 C6 C1 0.77(17) . . . . ?
C4 C5 C6 C7 -178.12(12) . . . . ?
C2 C1 C6 C5 -2.45(17) . . . . ?
C2 C1 C6 C7 176.71(10) . . . . ?
C16 N4 C12 S1 171.24(9) . . . . ?
C16 N4 C12 N3 -8.45(16) . . . . ?
C16 N4 C13 C14 14.74(13) . . . . ?
C13 N4 C12 S1 -6.04(16) . . . . ?
C13 N4 C12 N3 174.27(10) . . . . ?
C13 N4 C16 C15 10.89(13) . . . . ?
C13 C14 C15 C16 41.52(12) . . . . ?
C15 C14 C13 N4 -34.28(12) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: METHANOL / ACETONITRILE'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_mc1acu
_database_code_depnum_ccdc_archive 'CCDC 1418937'
_audit_update_record             
;
2015-08-16 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;
_audit_creation_date             2014-11-05
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.10.22 svn.r3046 for OlexSys, GUI svn.r4928)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
"N'-(1-allyl-2-oxoindolin-3-ylidene)pyrrolidine-1-carbothiohydrazide) copper(II) complex"
_chemical_formula_moiety         'C16 H17 Cl Cu N4 O S'
_chemical_formula_sum            'C16 H17 Cl Cu N4 O S'
_chemical_formula_weight         412.38
_chemical_melting_point          519
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.984(3)
_cell_length_b                   9.757(4)
_cell_length_c                   10.524(4)
_cell_angle_alpha                105.822(4)
_cell_angle_beta                 98.341(4)
_cell_angle_gamma                108.844(4)
_cell_volume                     812.0(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5043
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      27.530
_cell_measurement_theta_min      2.346
_shelx_estimated_absorpt_T_max   0.866
_shelx_estimated_absorpt_T_min   0.487
_exptl_absorpt_coefficient_mu    1.649
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0935 before and 0.0516 after correction.
The Ratio of minimum to maximum transmission is 0.6804.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             422
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9526
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_min         2.081
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3261
_reflns_number_total             3682
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3682
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.063
_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)+(0.0458P)²+0.2724P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0913
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C15(H15A,H15B), C9(H9A,H9B), C14(H14A,H14B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C10(H10), C8(H8), C6(H6), C7(H7)
2.c X=CH2 refined with riding coordinates:
 C11(H11A,H11B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Cu1 Cu 0.29812(3) 0.31034(3) 0.31347(2) 0.01373(10) Uani 1 1 d . . . . .
Cl1 Cl 0.30030(7) 0.17953(6) 0.11011(5) 0.02136(14) Uani 1 1 d . . . . .
S1 S 0.37882(6) 0.17543(6) 0.43142(5) 0.01503(13) Uani 1 1 d . . . . .
O1 O 0.17755(18) 0.44165(16) 0.24842(14) 0.0161(3) Uani 1 1 d . . . . .
N1 N 0.3096(2) 0.44439(19) 0.49602(17) 0.0114(3) Uani 1 1 d . . . . .
N2 N 0.3722(2) 0.43386(19) 0.61462(17) 0.0138(4) Uani 1 1 d . . . . .
N3 N 0.0922(2) 0.6301(2) 0.36610(17) 0.0138(4) Uani 1 1 d . . . . .
N4 N 0.4639(2) 0.27803(19) 0.70201(18) 0.0146(4) Uani 1 1 d . . . . .
C3 C 0.2116(2) 0.6623(2) 0.5876(2) 0.0128(4) Uani 1 1 d . . . . .
C4 C 0.1141(2) 0.7098(2) 0.5059(2) 0.0141(4) Uani 1 1 d . . . . .
C12 C 0.4067(2) 0.3043(2) 0.5919(2) 0.0128(4) Uani 1 1 d . . . . .
C5 C 0.2515(3) 0.7254(2) 0.7288(2) 0.0168(4) Uani 1 1 d . . . . .
H5 H 0.3193 0.6955 0.7844 0.020 Uiso 1 1 calc R . . . .
C2 C 0.2473(2) 0.5470(2) 0.4932(2) 0.0128(4) Uani 1 1 d . . . . .
C1 C 0.1712(2) 0.5324(2) 0.3540(2) 0.0128(4) Uani 1 1 d . . . . .
C10 C 0.0420(3) 0.7758(2) 0.2171(2) 0.0181(4) Uani 1 1 d . . . . .
H10 H 0.1048 0.8704 0.2891 0.022 Uiso 1 1 calc R . . . .
C8 C 0.0535(3) 0.8184(2) 0.5631(2) 0.0181(4) Uani 1 1 d . . . . .
H8 H -0.0119 0.8505 0.5078 0.022 Uiso 1 1 calc R . . . .
C16 C 0.4975(3) 0.3812(2) 0.8433(2) 0.0177(4) Uani 1 1 d . . . . .
H16A H 0.3965 0.3665 0.8745 0.021 Uiso 1 1 calc R . . . .
H16B H 0.5501 0.4906 0.8517 0.021 Uiso 1 1 calc R . . . .
C6 C 0.1886(3) 0.8347(2) 0.7871(2) 0.0194(5) Uani 1 1 d . . . . .
H6 H 0.2127 0.8786 0.8836 0.023 Uiso 1 1 calc R . . . .
C15 C 0.6122(3) 0.3313(3) 0.9233(2) 0.0201(5) Uani 1 1 d . . . . .
H15A H 0.6059 0.3541 1.0196 0.024 Uiso 1 1 calc R . . . .
H15B H 0.7260 0.3828 0.9212 0.024 Uiso 1 1 calc R . . . .
C9 C -0.0213(3) 0.6334(2) 0.2532(2) 0.0166(4) Uani 1 1 d . . . . .
H9A H -0.1249 0.6260 0.2784 0.020 Uiso 1 1 calc R . . . .
H9B H -0.0448 0.5423 0.1718 0.020 Uiso 1 1 calc R . . . .
C14 C 0.5493(3) 0.1582(3) 0.8482(2) 0.0194(5) Uani 1 1 d . . . . .
H14A H 0.6343 0.1171 0.8670 0.023 Uiso 1 1 calc R . . . .
H14B H 0.4524 0.1030 0.8751 0.023 Uiso 1 1 calc R . . . .
C13 C 0.5061(3) 0.1428(2) 0.6983(2) 0.0170(4) Uani 1 1 d . . . . .
H13A H 0.5998 0.1459 0.6582 0.020 Uiso 1 1 calc R . . . .
H13B H 0.4125 0.0455 0.6447 0.020 Uiso 1 1 calc R . . . .
C7 C 0.0920(3) 0.8792(3) 0.7054(2) 0.0209(5) Uani 1 1 d . . . . .
H7 H 0.0506 0.9532 0.7474 0.025 Uiso 1 1 calc R . . . .
C11 C 0.0158(3) 0.7775(3) 0.0919(2) 0.0250(5) Uani 1 1 d . . . . .
H11A H -0.0466 0.6847 0.0178 0.030 Uiso 1 1 calc R . . . .
H11B H 0.0591 0.8716 0.0751 0.030 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
Cu1 Cl1 2.1791(9) . ?
Cu1 S1 2.2463(7) . ?
Cu1 O1 2.1079(15) . ?
Cu1 N1 1.9743(18) . ?
S1 C12 1.735(2) . ?
O1 C1 1.240(3) . ?
N1 N2 1.337(2) . ?
N1 C2 1.300(3) . ?
N2 C12 1.364(3) . ?
N3 C4 1.415(3) . ?
N3 C1 1.351(3) . ?
N3 C9 1.464(3) . ?
N4 C12 1.322(3) . ?
N4 C16 1.474(3) . ?
N4 C13 1.479(3) . ?
C3 C4 1.408(3) . ?
C3 C5 1.386(3) . ?
C3 C2 1.439(3) . ?
C4 C8 1.378(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.402(3) . ?
C2 C1 1.471(3) . ?
C10 H10 0.9500 . ?
C10 C9 1.496(3) . ?
C10 C11 1.311(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.396(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C15 1.518(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.382(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C14 1.524(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.523(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C7 H7 0.9500 . ?
C11 H11A 0.9500 . ?
C11 H11B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Cu1 S1 99.05(3) . . ?
O1 Cu1 Cl1 95.89(5) . . ?
O1 Cu1 S1 161.66(5) . . ?
N1 Cu1 Cl1 175.13(5) . . ?
N1 Cu1 S1 83.51(6) . . ?
N1 Cu1 O1 82.42(7) . . ?
C12 S1 Cu1 95.78(7) . . ?
C1 O1 Cu1 105.87(13) . . ?
N2 N1 Cu1 125.16(13) . . ?
C2 N1 Cu1 113.91(13) . . ?
C2 N1 N2 120.93(17) . . ?
N1 N2 C12 110.29(16) . . ?
C4 N3 C9 124.68(17) . . ?
C1 N3 C4 109.72(16) . . ?
C1 N3 C9 124.82(18) . . ?
C12 N4 C16 124.47(17) . . ?
C12 N4 C13 123.94(18) . . ?
C16 N4 C13 111.58(16) . . ?
C4 C3 C2 105.45(18) . . ?
C5 C3 C4 120.6(2) . . ?
C5 C3 C2 133.92(19) . . ?
C3 C4 N3 109.86(18) . . ?
C8 C4 N3 128.66(19) . . ?
C8 C4 C3 121.5(2) . . ?
N2 C12 S1 124.54(15) . . ?
N4 C12 S1 119.47(16) . . ?
N4 C12 N2 115.98(18) . . ?
C3 C5 H5 121.0 . . ?
C3 C5 C6 117.9(2) . . ?
C6 C5 H5 121.0 . . ?
N1 C2 C3 138.45(19) . . ?
N1 C2 C1 113.27(18) . . ?
C3 C2 C1 107.71(17) . . ?
O1 C1 N3 128.47(19) . . ?
O1 C1 C2 124.27(18) . . ?
N3 C1 C2 107.23(17) . . ?
C9 C10 H10 118.1 . . ?
C11 C10 H10 118.1 . . ?
C11 C10 C9 123.7(2) . . ?
C4 C8 H8 121.3 . . ?
C4 C8 C7 117.4(2) . . ?
C7 C8 H8 121.3 . . ?
N4 C16 H16A 111.2 . . ?
N4 C16 H16B 111.2 . . ?
N4 C16 C15 102.73(17) . . ?
H16A C16 H16B 109.1 . . ?
C15 C16 H16A 111.2 . . ?
C15 C16 H16B 111.2 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 H6 119.7 . . ?
C16 C15 H15A 111.2 . . ?
C16 C15 H15B 111.2 . . ?
C16 C15 C14 102.94(18) . . ?
H15A C15 H15B 109.1 . . ?
C14 C15 H15A 111.2 . . ?
C14 C15 H15B 111.2 . . ?
N3 C9 C10 113.20(17) . . ?
N3 C9 H9A 108.9 . . ?
N3 C9 H9B 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.8 . . ?
C15 C14 H14A 111.0 . . ?
C15 C14 H14B 111.0 . . ?
H14A C14 H14B 109.0 . . ?
C13 C14 C15 103.71(17) . . ?
C13 C14 H14A 111.0 . . ?
C13 C14 H14B 111.0 . . ?
N4 C13 C14 103.31(17) . . ?
N4 C13 H13A 111.1 . . ?
N4 C13 H13B 111.1 . . ?
C14 C13 H13A 111.1 . . ?
C14 C13 H13B 111.1 . . ?
H13A C13 H13B 109.1 . . ?
C8 C7 H7 119.1 . . ?
C6 C7 C8 121.9(2) . . ?
C6 C7 H7 119.1 . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?

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
Cu1 S1 C12 N2 3.66(18) . . . . ?
Cu1 S1 C12 N4 -176.96(16) . . . . ?
Cu1 O1 C1 N3 -173.00(18) . . . . ?
Cu1 O1 C1 C2 4.5(2) . . . . ?
Cu1 N1 N2 C12 -8.4(2) . . . . ?
Cu1 N1 C2 C3 174.3(2) . . . . ?
Cu1 N1 C2 C1 4.4(2) . . . . ?
N1 N2 C12 S1 1.9(2) . . . . ?
N1 N2 C12 N4 -177.55(17) . . . . ?
N1 C2 C1 O1 -6.4(3) . . . . ?
N1 C2 C1 N3 171.52(17) . . . . ?
N2 N1 C2 C3 -4.9(4) . . . . ?
N2 N1 C2 C1 -174.76(17) . . . . ?
N3 C4 C8 C7 179.35(19) . . . . ?
N4 C16 C15 C14 -34.9(2) . . . . ?
C3 C4 C8 C7 -0.2(3) . . . . ?
C3 C5 C6 C7 -0.9(3) . . . . ?
C3 C2 C1 O1 -179.38(19) . . . . ?
C3 C2 C1 N3 -1.5(2) . . . . ?
C4 N3 C1 O1 178.6(2) . . . . ?
C4 N3 C1 C2 0.8(2) . . . . ?
C4 N3 C9 C10 79.5(3) . . . . ?
C4 C3 C5 C6 1.5(3) . . . . ?
C4 C3 C2 N1 -168.7(2) . . . . ?
C4 C3 C2 C1 1.6(2) . . . . ?
C4 C8 C7 C6 0.8(3) . . . . ?
C12 N4 C16 C15 -160.7(2) . . . . ?
C12 N4 C13 C14 -174.79(19) . . . . ?
C5 C3 C4 N3 179.43(18) . . . . ?
C5 C3 C4 C8 -0.9(3) . . . . ?
C5 C3 C2 N1 10.6(4) . . . . ?
C5 C3 C2 C1 -179.1(2) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C2 N1 N2 C12 170.62(18) . . . . ?
C2 C3 C4 N3 -1.1(2) . . . . ?
C2 C3 C4 C8 178.54(19) . . . . ?
C2 C3 C5 C6 -177.8(2) . . . . ?
C1 N3 C4 C3 0.2(2) . . . . ?
C1 N3 C4 C8 -179.4(2) . . . . ?
C1 N3 C9 C10 -111.6(2) . . . . ?
C16 N4 C12 S1 178.00(16) . . . . ?
C16 N4 C12 N2 -2.6(3) . . . . ?
C16 N4 C13 C14 6.7(2) . . . . ?
C16 C15 C14 C13 39.8(2) . . . . ?
C15 C14 C13 N4 -28.5(2) . . . . ?
C9 N3 C4 C3 170.51(18) . . . . ?
C9 N3 C4 C8 -9.1(3) . . . . ?
C9 N3 C1 O1 8.3(3) . . . . ?
C9 N3 C1 C2 -169.50(18) . . . . ?
C13 N4 C12 S1 -0.3(3) . . . . ?
C13 N4 C12 N2 179.11(18) . . . . ?
C13 N4 C16 C15 17.8(2) . . . . ?
C11 C10 C9 N3 143.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: METHANOL / ACETONITRILE'
