# 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_M1_100Kv2
_database_code_depnum_ccdc_archive 'CCDC 1049864'
_audit_update_record
;
2015-02-16 deposited with the CCDC.
2016-09-07 downloaded from the CCDC.
;
_audit_creation_date 2015-02-16
_audit_creation_method
;
Olex2 1.2
(compiled 2014.12.26 svn.r3119 for OlexSys, GUI svn.r4975)
;
_chemical_name_systematic
"4-ethenylbenzyl N'-[(E)-phenylmethylidene]carbamohydrazonothioate"
_chemical_formula_moiety 'C17 H17 N3 S'
_chemical_formula_sum 'C17 H17 N3 S'
_chemical_formula_weight 295.41
_chemical_oxdiff_formula 'C17 H17 N3 S1'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
_symmetry_Int_Tables_number 2
_cell_length_a 8.66567(19)
_cell_length_b 9.3865(3)
_cell_length_c 10.4897(3)
_cell_angle_alpha 84.169(2)
_cell_angle_beta 87.2611(19)
_cell_angle_gamma 64.997(2)
_cell_volume 769.26(4)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 15114
_cell_measurement_temperature 100
_cell_measurement_theta_max 37.4150
_cell_measurement_theta_min 3.1790
_exptl_absorpt_coefficient_mu 0.207
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.77898
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour 'clear light colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier light
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.2753
_exptl_crystal_description plate
_exptl_crystal_F_000 312.3441
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max 0.4844
_exptl_crystal_size_mid 0.422
_exptl_crystal_size_min 0.04
_diffrn_reflns_av_R_equivalents 0.0412
_diffrn_reflns_av_unetI/netI 0.0269
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_number 37171
_diffrn_reflns_theta_full 26.0000
_diffrn_reflns_theta_max 36.31
_diffrn_reflns_theta_min 2.96
_diffrn_ambient_temperature 100
_diffrn_ambient_environment N~2~
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type Atlas
_diffrn_measured_fraction_theta_full 0.9921
_diffrn_measured_fraction_theta_max 0.9965
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
1 omega -112.00 -42.00 1.0000 22.6950
omega____ theta____ kappa____ phi______ frames
- -31.8965 160.0000 -35.0000 70
#__ type_ start__ end____ width___ exp.time_
2 omega -85.00 -18.00 1.0000 22.6950
omega____ theta____ kappa____ phi______ frames
- -31.8965 118.0000 171.0000 67
#__ type_ start__ end____ width___ exp.time_
3 omega 50.00 111.00 1.0000 22.6950
omega____ theta____ kappa____ phi______ frames
- 32.5215 160.0000 -35.0000 61
#__ type_ start__ end____ width___ exp.time_
4 omega -4.00 85.00 1.0000 22.6950
omega____ theta____ kappa____ phi______ frames
- 32.5215 -118.0000 85.0000 89
#__ type_ start__ end____ width___ exp.time_
5 omega 21.00 112.00 1.0000 22.6950
omega____ theta____ kappa____ phi______ frames
- 32.5215 -160.0000 -66.0000 91
#__ type_ start__ end____ width___ exp.time_
6 omega -122.00 -57.00 1.0000 22.6950
omega____ theta____ kappa____ phi______ frames
- -31.8965 -178.0000 -120.0000 65
#__ type_ start__ end____ width___ exp.time_
7 omega -120.00 -55.00 1.0000 22.6950
omega____ theta____ kappa____ phi______ frames
- -31.8965 178.0000 -180.0000 65
#__ type_ start__ end____ width___ exp.time_
8 omega -43.00 59.00 1.0000 22.6950
omega____ theta____ kappa____ phi______ frames
- 32.5215 -38.0000 60.0000 102
#__ type_ start__ end____ width___ exp.time_
9 omega -43.00 59.00 1.0000 22.6950
omega____ theta____ kappa____ phi______ frames
- 32.5215 -38.0000 150.0000 102
#__ type_ start__ end____ width___ exp.time_
10 omega 6.00 108.00 1.0000 22.6950
omega____ theta____ kappa____ phi______ frames
- 32.5215 38.0000 -120.0000 102
#__ type_ start__ end____ width___ exp.time_
11 omega -43.00 59.00 1.0000 22.6950
omega____ theta____ kappa____ phi______ frames
- 32.5215 -38.0000 -90.0000 102
#__ type_ start__ end____ width___ exp.time_
12 omega 3.00 106.00 1.0000 22.6950
omega____ theta____ kappa____ phi______ frames
- 32.5215 57.0000 -60.0000 103
#__ type_ start__ end____ width___ exp.time_
13 omega 3.00 106.00 1.0000 22.6950
omega____ theta____ kappa____ phi______ frames
- 32.5215 57.0000 150.0000 103
#__ type_ start__ end____ width___ exp.time_
14 omega -1.00 63.00 1.0000 22.6950
omega____ theta____ kappa____ phi______ frames
- 32.5215 77.0000 -180.0000 64
#__ type_ start__ end____ width___ exp.time_
15 omega -1.00 111.00 1.0000 22.6950
omega____ theta____ kappa____ phi______ frames
- 32.5215 77.0000 30.0000 112
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'SuperNova, Dual, Mo at zero, Atlas'
_diffrn_measurement_method '\w and \f scans'
_diffrn_orient_matrix_UB_11 -0.0048627000
_diffrn_orient_matrix_UB_12 0.0654832000
_diffrn_orient_matrix_UB_13 -0.0425682000
_diffrn_orient_matrix_UB_21 0.0112070000
_diffrn_orient_matrix_UB_22 0.0371446000
_diffrn_orient_matrix_UB_23 0.0521835000
_diffrn_orient_matrix_UB_31 0.0894868000
_diffrn_orient_matrix_UB_32 -0.0366206000
_diffrn_orient_matrix_UB_33 -0.0092173000
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'sealed tube'
_diffrn_special_details ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number ?
_reflns_Friedel_coverage 0.0
_reflns_limit_h_max 14
_reflns_limit_h_min -14
_reflns_limit_k_max 15
_reflns_limit_k_min -15
_reflns_limit_l_max 17
_reflns_limit_l_min 0
_reflns_number_gt 6205
_reflns_number_total 7441
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 36.23
_reflns_threshold_expression I>=2u(I)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution 'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max 0.6580
_refine_diff_density_min -0.3046
_refine_diff_density_rms 0.0726
_refine_ls_d_res_high 0.6001
_refine_ls_d_res_low 6.8875
_refine_ls_goodness_of_fit_ref 1.0978
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_constraints 25
_refine_ls_number_parameters 205
_refine_ls_number_reflns 7441
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0519
_refine_ls_R_factor_gt 0.0404
_refine_ls_restrained_S_all 1.0978
_refine_ls_shift/su_max 0.0001
_refine_ls_shift/su_mean 0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0514P)^2^+0.2149P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1062
_refine_ls_wR_factor_ref 0.1179
_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:
C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C11(H11), C13(H13), C14(H14),
C15(H15), C16(H16), C17(H17)
;
_atom_sites_solution_primary iterative
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_refinement_flags_posn
S1 S 0.47726(3) 0.19389(3) 0.31875(2) 0.02082(6) Uani 1.000000 .
N1 N 0.34103(10) 0.14907(10) 0.10691(8) 0.02074(14) Uani 1.000000 .
H1A H 0.354(2) 0.092(2) 0.0404(18) 0.046(5) Uiso 1.000000 .
H1B H 0.247(2) 0.178(2) 0.1501(17) 0.044(5) Uiso 1.000000 .
N2 N 0.63283(9) 0.03030(9) 0.11915(7) 0.01839(13) Uani 1.000000 .
N3 N 0.76886(9) 0.01716(9) 0.19252(7) 0.01783(13) Uani 1.000000 .
C1 C 0.22975(10) 0.38878(10) 0.46319(8) 0.01859(14) Uani 1.000000 .
C2 C 0.17639(11) 0.32637(11) 0.57437(9) 0.02037(15) Uani 1.000000 .
H2 H 0.15034(11) 0.23818(11) 0.57088(9) 0.02445(18) Uiso 1.000000 R
C3 C 0.16104(11) 0.39183(11) 0.68981(9) 0.02084(15) Uani 1.000000 .
H3 H 0.12421(11) 0.34819(11) 0.76434(9) 0.02500(18) Uiso 1.000000 R
C4 C 0.19928(11) 0.52148(10) 0.69750(9) 0.01971(15) Uani 1.000000 .
C5 C 0.25187(12) 0.58408(11) 0.58593(9) 0.02154(15) Uani 1.000000 .
H5 H 0.27738(12) 0.67261(11) 0.58924(9) 0.02585(18) Uiso 1.000000 R
C6 C 0.26740(12) 0.51836(11) 0.46986(9) 0.02140(15) Uani 1.000000 .
H6 H 0.30375(12) 0.56205(11) 0.39511(9) 0.02568(18) Uiso 1.000000 R
C7 C 0.18817(14) 0.59282(12) 0.81871(10) 0.02578(18) Uani 1.000000 .
H7 H 0.19524(14) 0.69153(12) 0.81344(10) 0.0309(2) Uiso 1.000000 R
C8 C 0.1691(2) 0.53034(17) 0.93447(12) 0.0435(3) Uani 1.000000 .
H8A H 0.166(2) 0.583(2) 1.0115(18) 0.049(5) Uiso 1.000000 .
H8B H 0.161(3) 0.431(3) 0.946(2) 0.063(6) Uiso 1.000000 .
C9 C 0.24948(11) 0.31572(11) 0.33854(9) 0.02119(15) Uani 1.000000 .
H9A H 0.20671(11) 0.39877(11) 0.26642(9) 0.02543(19) Uiso 1.000000 R
H9B H 0.18484(11) 0.25012(11) 0.34133(9) 0.02543(19) Uiso 1.000000 R
C10 C 0.48612(10) 0.11670(10) 0.17059(8) 0.01747(14) Uani 1.000000 .
C11 C 0.91564(10) -0.06398(10) 0.14403(8) 0.01743(14) Uani 1.000000 .
H11 H 0.92117(10) -0.10607(10) 0.06444(8) 0.02092(16) Uiso 1.000000 R
C12 C 1.07474(10) -0.09359(10) 0.20775(8) 0.01673(13) Uani 1.000000 .
C13 C 1.07641(11) -0.03524(11) 0.32584(8) 0.01858(14) Uani 1.000000 .
H13 H 0.97228(11) 0.02784(11) 0.36572(8) 0.02229(17) Uiso 1.000000 R
C14 C 1.23075(11) -0.07003(11) 0.38417(9) 0.02091(15) Uani 1.000000 .
H14 H 1.23144(11) -0.03093(11) 0.46409(9) 0.02509(18) Uiso 1.000000 R
C15 C 1.38470(11) -0.16206(12) 0.32598(9) 0.02266(16) Uani 1.000000 .
H15 H 1.48954(11) -0.18663(12) 0.36686(9) 0.02720(19) Uiso 1.000000 R
C16 C 1.38410(11) -0.21752(12) 0.20830(9) 0.02300(16) Uani 1.000000 .
H16 H 1.48862(11) -0.27887(12) 0.16802(9) 0.0276(2) Uiso 1.000000 R
C17 C 1.23009(11) -0.18314(11) 0.14928(8) 0.01996(15) Uani 1.000000 .
H17 H 1.23042(11) -0.22082(11) 0.06852(8) 0.02395(18) Uiso 1.000000 R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.01376(9) 0.02827(11) 0.02005(10) -0.00661(7) -0.00216(6) -0.00962(8)
N1 0.0144(3) 0.0288(4) 0.0188(3) -0.0076(3) -0.0035(2) -0.0060(3)
N2 0.0139(3) 0.0257(3) 0.0162(3) -0.0082(2) -0.0018(2) -0.0048(2)
N3 0.0142(3) 0.0230(3) 0.0171(3) -0.0080(2) -0.0021(2) -0.0039(2)
C1 0.0136(3) 0.0201(3) 0.0206(3) -0.0048(3) -0.0015(2) -0.0047(3)
C2 0.0172(3) 0.0195(3) 0.0250(4) -0.0076(3) 0.0015(3) -0.0060(3)
C3 0.0201(3) 0.0196(3) 0.0230(4) -0.0082(3) 0.0031(3) -0.0049(3)
C4 0.0182(3) 0.0183(3) 0.0214(3) -0.0060(3) -0.0001(3) -0.0042(3)
C5 0.0225(4) 0.0201(4) 0.0239(4) -0.0103(3) -0.0013(3) -0.0032(3)
C6 0.0214(4) 0.0225(4) 0.0218(4) -0.0105(3) -0.0012(3) -0.0026(3)
C7 0.0311(4) 0.0216(4) 0.0251(4) -0.0104(3) 0.0006(3) -0.0076(3)
C8 0.0750(10) 0.0367(6) 0.0256(5) -0.0290(7) 0.0078(5) -0.0111(4)
C9 0.0147(3) 0.0258(4) 0.0221(4) -0.0062(3) -0.0020(3) -0.0075(3)
C10 0.0147(3) 0.0221(3) 0.0166(3) -0.0081(3) -0.0019(2) -0.0038(3)
C11 0.0151(3) 0.0218(3) 0.0161(3) -0.0079(3) -0.0012(2) -0.0038(3)
C12 0.0140(3) 0.0196(3) 0.0165(3) -0.0067(2) -0.0012(2) -0.0021(2)
C13 0.0157(3) 0.0222(4) 0.0171(3) -0.0068(3) -0.0014(2) -0.0035(3)
C14 0.0193(3) 0.0251(4) 0.0189(3) -0.0096(3) -0.0040(3) -0.0016(3)
C15 0.0161(3) 0.0280(4) 0.0229(4) -0.0087(3) -0.0048(3) 0.0013(3)
C16 0.0140(3) 0.0273(4) 0.0238(4) -0.0051(3) -0.0004(3) -0.0014(3)
C17 0.0159(3) 0.0230(4) 0.0189(3) -0.0059(3) 0.0002(2) -0.0037(3)
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 1.8298(9) . ?
S1 C10 1.7654(8) . ?
N1 H1A 0.897(19) . ?
N1 H1B 0.863(18) . ?
N1 C10 1.3548(11) . ?
N2 N3 1.3934(10) . ?
N2 C10 1.3103(11) . ?
N3 C11 1.2864(11) . ?
C1 C2 1.3985(13) . ?
C1 C6 1.3949(13) . ?
C1 C9 1.5069(12) . ?
C2 H2 0.9500 . ?
C2 C3 1.3885(13) . ?
C3 H3 0.9500 . ?
C3 C4 1.4003(13) . ?
C4 C5 1.3994(13) . ?
C4 C7 1.4768(13) . ?
C5 H5 0.9500 . ?
C5 C6 1.3955(13) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.3280(17) . ?
C8 H8A 0.986(19) . ?
C8 H8B 0.96(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 H11 0.9500 . ?
C11 C12 1.4668(11) . ?
C12 C13 1.4074(12) . ?
C12 C17 1.4015(12) . ?
C13 H13 0.9500 . ?
C13 C14 1.3922(12) . ?
C14 H14 0.9500 . ?
C14 C15 1.3978(13) . ?
C15 H15 0.9500 . ?
C15 C16 1.3886(14) . ?
C16 H16 0.9500 . ?
C16 C17 1.3939(12) . ?
C17 H17 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
C10 S1 C9 102.69(4) . . ?
H1B N1 H1A 118.4(16) . . ?
C10 N1 H1A 115.0(11) . . ?
C10 N1 H1B 118.1(12) . . ?
C10 N2 N3 111.62(7) . . ?
C11 N3 N2 113.72(7) . . ?
C6 C1 C2 118.93(8) . . ?
C9 C1 C2 120.69(8) . . ?
C9 C1 C6 120.37(8) . . ?
H2 C2 C1 119.62(5) . . ?
C3 C2 C1 120.76(8) . . ?
C3 C2 H2 119.62(5) . . ?
H3 C3 C2 119.65(5) . . ?
C4 C3 C2 120.69(8) . . ?
C4 C3 H3 119.65(5) . . ?
C5 C4 C3 118.39(8) . . ?
C7 C4 C3 122.54(8) . . ?
C7 C4 C5 119.07(8) . . ?
H5 C5 C4 119.51(5) . . ?
C6 C5 C4 120.97(8) . . ?
C6 C5 H5 119.51(5) . . ?
C5 C6 C1 120.25(8) . . ?
H6 C6 C1 119.87(5) . . ?
H6 C6 C5 119.87(5) . . ?
H7 C7 C4 117.31(5) . . ?
C8 C7 C4 125.37(10) . . ?
C8 C7 H7 117.31(7) . . ?
H8A C8 C7 120.8(11) . . ?
H8B C8 C7 121.0(13) . . ?
H8B C8 H8A 118.2(16) . . ?
C1 C9 S1 106.42(6) . . ?
H9A C9 S1 110.44(3) . . ?
H9A C9 C1 110.44(5) . . ?
H9B C9 S1 110.44(3) . . ?
H9B C9 C1 110.44(5) . . ?
H9B C9 H9A 108.6 . . ?
N1 C10 S1 120.35(6) . . ?
N2 C10 S1 120.66(6) . . ?
N2 C10 N1 118.97(8) . . ?
H11 C11 N3 118.96(5) . . ?
C12 C11 N3 122.07(7) . . ?
C12 C11 H11 118.96(4) . . ?
C13 C12 C11 122.11(7) . . ?
C17 C12 C11 118.93(7) . . ?
C17 C12 C13 118.95(7) . . ?
H13 C13 C12 120.02(5) . . ?
C14 C13 C12 119.96(8) . . ?
C14 C13 H13 120.02(5) . . ?
H14 C14 C13 119.76(5) . . ?
C15 C14 C13 120.48(8) . . ?
C15 C14 H14 119.76(5) . . ?
H15 C15 C14 120.07(5) . . ?
C16 C15 C14 119.87(8) . . ?
C16 C15 H15 120.07(5) . . ?
H16 C16 C15 120.01(5) . . ?
C17 C16 C15 119.98(8) . . ?
C17 C16 H16 120.01(5) . . ?
C16 C17 C12 120.73(8) . . ?
H17 C17 C12 119.63(5) . . ?
H17 C17 C16 119.63(5) . . ?
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-12 -2 -1 0.2001 -11.9845 -1.9714 -1.0201 -0.0274 -0.2608 -0.9909
0 -9 9 0.0390 -0.0295 -9.0085 8.9920 -0.9725 0.1343 0.2444
0 9 -9 0.0010 0.0295 9.0085 -8.9920 0.9725 -0.1343 -0.2444
2 9 11 0.2252 2.0043 8.9825 11.0037 0.1101 0.9303 -0.2510
-2 -9 -11 0.2252 -2.0043 -8.9825 -11.0037 -0.1101 -0.9303 0.2510
11 1 0 0.1737 11.0048 1.0051 0.0104 0.0119 0.1612 0.9479
-9 3 6 0.1960 -9.0166 3.0079 5.9722 -0.0134 0.3223 -0.9721
_iucr_refine_instructions_details
;
TITL
CELL 0.71073 8.665667 9.386502 10.489674 84.1695 87.2611 64.9971
ZERR 2 0.000187 0.000257 0.000265 0.0022 0.0019 0.0024
LATT 1
SFAC C H N S
UNIT 34 34 6 2
L.S. 4
PLAN 20
TEMP -173.15
MORE -1
BOND $H
CONF
fmap 2
acta 52
OMIT -3 -9 6
OMIT 0 -3 3
OMIT -3 -6 6
OMIT 3 6 0
OMIT 0 0 7
OMIT 3 9 0
OMIT -6 -6 3
OMIT 3 -3 3
OMIT -3 -6 3
OMIT 3 9 12
OMIT 2 4 9
OMIT -4 -8 8
OMIT 6 -3 3
OMIT 6 0 0
OMIT 3 -3 6
OMIT 10 0 0
OMIT 1 5 8
OMIT -3 6 6
OMIT 3 6 9
OMIT 4 8 4
OMIT -5 1 3
OMIT 0 -1 5
WGHT 0.0514 0.2149
FVAR 8.647057
REM
REM
REM
S1 4 0.47726 0.19389 0.31875 11.00000 0.01376 0.02827 0.02005 =
-0.00962 -0.00216 -0.00661
N1 3 0.34103 0.14907 0.10691 11.00000 0.01441 0.02877 0.01879 =
-0.00604 -0.00354 -0.00762
H1A 2 0.35400 0.09185 0.04041 11.00000 0.04565
H1B 2 0.24711 0.17763 0.15008 11.00000 0.04446
N2 3 0.63283 0.03030 0.11915 11.00000 0.01387 0.02575 0.01622 =
-0.00478 -0.00178 -0.00815
N3 3 0.76886 0.01716 0.19252 11.00000 0.01424 0.02301 0.01709 =
-0.00385 -0.00213 -0.00800
C1 1 0.22975 0.38878 0.46319 11.00000 0.01356 0.02007 0.02061 =
-0.00466 -0.00154 -0.00483
C2 1 0.17639 0.32637 0.57437 11.00000 0.01719 0.01951 0.02500 =
-0.00604 0.00150 -0.00755
AFIX 43
H2 2 0.15034 0.23818 0.57088 11.00000 -1.20000
AFIX 0
C3 1 0.16104 0.39183 0.68981 11.00000 0.02008 0.01956 0.02303 =
-0.00493 0.00311 -0.00817
AFIX 43
H3 2 0.12421 0.34819 0.76434 11.00000 -1.20000
AFIX 0
C4 1 0.19928 0.52148 0.69750 11.00000 0.01823 0.01829 0.02143 =
-0.00422 -0.00011 -0.00600
C5 1 0.25187 0.58408 0.58593 11.00000 0.02245 0.02009 0.02392 =
-0.00319 -0.00130 -0.01033
AFIX 43
H5 2 0.27738 0.67261 0.58924 11.00000 -1.20000
AFIX 0
C6 1 0.26740 0.51836 0.46986 11.00000 0.02139 0.02254 0.02181 =
-0.00262 -0.00117 -0.01048
AFIX 43
H6 2 0.30375 0.56205 0.39511 11.00000 -1.20000
AFIX 0
C7 1 0.18817 0.59282 0.81871 11.00000 0.03107 0.02161 0.02512 =
-0.00756 0.00062 -0.01040
AFIX 43
H7 2 0.19524 0.69153 0.81344 11.00000 -1.20000
AFIX 0
C8 1 0.16911 0.53034 0.93447 11.00000 0.07500 0.03666 0.02558 =
-0.01114 0.00780 -0.02898
H8A 2 0.16619 0.58350 1.01154 11.00000 0.04876
H8B 2 0.16084 0.43061 0.94566 11.00000 0.06270
C9 1 0.24948 0.31572 0.33854 11.00000 0.01469 0.02580 0.02206 =
-0.00752 -0.00198 -0.00616
AFIX 23
H9A 2 0.20671 0.39877 0.26642 11.00000 -1.20000
H9B 2 0.18484 0.25012 0.34133 11.00000 -1.20000
AFIX 0
C10 1 0.48612 0.11670 0.17059 11.00000 0.01466 0.02211 0.01661 =
-0.00375 -0.00191 -0.00805
C11 1 0.91564 -0.06398 0.14403 11.00000 0.01514 0.02179 0.01608 =
-0.00381 -0.00118 -0.00788
AFIX 43
H11 2 0.92117 -0.10607 0.06444 11.00000 -1.20000
AFIX 0
C12 1 1.07474 -0.09359 0.20775 11.00000 0.01396 0.01962 0.01645 =
-0.00206 -0.00120 -0.00669
C13 1 1.07641 -0.03524 0.32584 11.00000 0.01573 0.02222 0.01712 =
-0.00354 -0.00143 -0.00681
AFIX 43
H13 2 0.97228 0.02784 0.36572 11.00000 -1.20000
AFIX 0
C14 1 1.23075 -0.07003 0.38417 11.00000 0.01932 0.02508 0.01894 =
-0.00165 -0.00395 -0.00961
AFIX 43
H14 2 1.23144 -0.03093 0.46409 11.00000 -1.20000
AFIX 0
C15 1 1.38470 -0.16206 0.32598 11.00000 0.01609 0.02804 0.02294 =
0.00133 -0.00484 -0.00869
AFIX 43
H15 2 1.48954 -0.18663 0.36686 11.00000 -1.20000
AFIX 0
C16 1 1.38410 -0.21752 0.20830 11.00000 0.01399 0.02732 0.02381 =
-0.00145 -0.00039 -0.00510
AFIX 43
H16 2 1.48862 -0.27887 0.16802 11.00000 -1.20000
AFIX 0
C17 1 1.23009 -0.18314 0.14928 11.00000 0.01591 0.02304 0.01893 =
-0.00370 0.00019 -0.00588
AFIX 43
H17 2 1.23042 -0.22082 0.06852 11.00000 -1.20000
AFIX 0
Q1 1 0.17500 0.45000 0.68889 11.00000 0.06000 0.660
HKLF 4
END
REM The information below was added by Olex2.
REM
REM R1 = 0.0404 for 6205 Fo > 4sig(Fo) and 0.0519 for all 7441 data
REM 205 parameters refined using 0 restraints
REM Highest difference peak 0.6580, deepest hole -0.3046
REM Mean Shift 0.0000, Max Shift 0.0001.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0519
REM R1_gt = 0.0404
REM wR_ref = 0.1179
REM GOOF = 1.0978
REM Shift_max = 0.0001
REM Shift_mean = 0.0000
REM Reflections_all = 7441
REM Reflections_gt = 6205
REM Parameters = 205
REM Hole = -0.3046
REM Peak = 0.6580
REM Flack = n/a
;
_olex2_submission_original_sample_id M1
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_exp_2220
_database_code_depnum_ccdc_archive 'CCDC 1049967'
_audit_update_record
;
2015-02-16 deposited with the CCDC.
2016-09-07 downloaded from the CCDC.
;
_audit_creation_date 2015-02-16
_audit_creation_method
;
Olex2 1.2
(compiled 2014.12.26 svn.r3119 for OlexSys, GUI svn.r4975)
;
_chemical_name_common ?
_chemical_name_systematic
'(1E,2E)-1-{amino[(4-ethenylbenzyl)sulfanyl]methylidene}-2-benzylidenehydrazinium chloride - methanol (1:1:1)'
_chemical_formula_moiety 'C17 H18 N3 S, C H4 O, Cl'
_chemical_formula_sum 'C18 H22 Cl N3 O S'
_chemical_formula_weight 363.90
_chemical_melting_point ?
_chemical_oxdiff_formula 'C18 H22 N3 S1 Cl1 O1'
_chemical_oxdiff_usercomment 100K
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
_cell_length_a 9.4176(2)
_cell_length_b 10.2256(2)
_cell_length_c 11.8640(3)
_cell_angle_alpha 67.799(2)
_cell_angle_beta 68.787(2)
_cell_angle_gamma 66.310(2)
_cell_volume 938.49(4)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 13960
_cell_measurement_temperature 100.1(6)
_cell_measurement_theta_max 36.9700
_cell_measurement_theta_min 3.3560
_exptl_absorpt_coefficient_mu 0.324
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.74865
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour 'clear light colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier light
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.288
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description irregular
_exptl_crystal_F_000 384
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max 0.2984
_exptl_crystal_size_mid 0.2133
_exptl_crystal_size_min 0.0934
_exptl_special_details
;
?
;
_diffrn_reflns_av_R_equivalents 0.0463
_diffrn_reflns_av_unetI/netI 0.0338
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_k_max 17
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_number 45409
_diffrn_reflns_theta_full 26.00
_diffrn_reflns_theta_max 36.32
_diffrn_reflns_theta_min 2.77
_diffrn_ambient_environment N~2~
_diffrn_ambient_temperature 100.1(6)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 8
_diffrn_detector_type Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
1 omega -61.00 42.00 1.0000 27.1850
omega____ theta____ kappa____ phi______ frames
- -31.5329 57.0000 -90.0000 103
#__ type_ start__ end____ width___ exp.time_
2 omega -61.00 42.00 1.0000 27.1850
omega____ theta____ kappa____ phi______ frames
- -31.5329 57.0000 -30.0000 103
#__ type_ start__ end____ width___ exp.time_
3 omega -1.00 111.00 1.0000 27.1850
omega____ theta____ kappa____ phi______ frames
- 32.1579 77.0000 0.0000 112
#__ type_ start__ end____ width___ exp.time_
4 omega -1.00 111.00 1.0000 27.1850
omega____ theta____ kappa____ phi______ frames
- 32.1579 77.0000 60.0000 112
#__ type_ start__ end____ width___ exp.time_
5 omega 3.00 106.00 1.0000 27.1850
omega____ theta____ kappa____ phi______ frames
- 32.1579 57.0000 150.0000 103
#__ type_ start__ end____ width___ exp.time_
6 omega -1.00 111.00 1.0000 27.1850
omega____ theta____ kappa____ phi______ frames
- 32.1579 77.0000 -150.0000 112
#__ type_ start__ end____ width___ exp.time_
7 omega 3.00 106.00 1.0000 27.1850
omega____ theta____ kappa____ phi______ frames
- 32.1579 57.0000 -60.0000 103
#__ type_ start__ end____ width___ exp.time_
8 omega -1.00 111.00 1.0000 27.1850
omega____ theta____ kappa____ phi______ frames
- 32.1579 77.0000 -180.0000 112
#__ type_ start__ end____ width___ exp.time_
9 omega -1.00 111.00 1.0000 27.1850
omega____ theta____ kappa____ phi______ frames
- 32.1579 77.0000 -30.0000 112
#__ type_ start__ end____ width___ exp.time_
10 omega -65.00 47.00 1.0000 27.1850
omega____ theta____ kappa____ phi______ frames
- -31.5329 77.0000 30.0000 112
#__ type_ start__ end____ width___ exp.time_
11 omega -65.00 44.00 1.0000 27.1850
omega____ theta____ kappa____ phi______ frames
- -31.5329 77.0000 -180.0000 109
#__ type_ start__ end____ width___ exp.time_
12 omega -61.00 42.00 1.0000 27.1850
omega____ theta____ kappa____ phi______ frames
- -31.5329 57.0000 120.0000 103
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'SuperNova, Dual, Mo at zero, Atlas'
_diffrn_measurement_method '\w and \f scans'
_diffrn_orient_matrix_UB_11 -0.0561667000
_diffrn_orient_matrix_UB_12 0.0071129000
_diffrn_orient_matrix_UB_13 -0.0304502000
_diffrn_orient_matrix_UB_21 0.0485267000
_diffrn_orient_matrix_UB_22 0.0280819000
_diffrn_orient_matrix_UB_23 -0.0589767000
_diffrn_orient_matrix_UB_31 0.0411974000
_diffrn_orient_matrix_UB_32 -0.0731994000
_diffrn_orient_matrix_UB_33 -0.0060650000
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'sealed tube'
_diffrn_standards_decay_% ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number ?
_reflns_number_gt 6918
_reflns_number_total 9081
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 36.23
_reflns_threshold_expression >2sigma(I)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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 'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max 0.716
_refine_diff_density_min -0.342
_refine_diff_density_rms 0.074
_refine_ls_extinction_coef ?
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.034
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 230
_refine_ls_number_reflns 9081
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0656
_refine_ls_R_factor_gt 0.0446
_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
'calc w=1/[\s^2^(Fo^2^)+(0.0579P)^2^+0.3447P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1116
_refine_ls_wR_factor_ref 0.1258
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
At 1.5 times of:
All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
N2(H2A), C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C11(H11), C13(H13), C14(H14),
C15(H15), C16(H16), C17(H17)
2.c X=CH2 refined with riding coordinates:
N1(H1A,H1B)
2.d Idealised Me refined as rotating group:
C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary iterative
_atom_sites_solution_secondary difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.48296(3) 0.60805(4) 0.33087(3) 0.02340(7) Uani 1 d . . .
N1 N 0.18054(12) 0.60426(11) 0.45776(9) 0.02069(17) Uani 1 d . . .
H1A H 0.0889 0.6370 0.5060 0.025 Uiso 1 calc . . R
H1B H 0.1982 0.5321 0.4289 0.025 Uiso 1 calc . . R
N2 N 0.27088(11) 0.77615(10) 0.47089(9) 0.01850(16) Uani 1 d . . .
H2A H 0.3382 0.8254 0.4403 0.022 Uiso 1 calc . . R
N3 N 0.13599(11) 0.81070(10) 0.56589(9) 0.01797(15) Uani 1 d . . .
C1 C 0.59130(13) 0.50099(13) 0.12985(10) 0.01985(18) Uani 1 d . . .
C2 C 0.72763(16) 0.38025(16) 0.14429(11) 0.0291(2) Uani 1 d . . .
H2 H 0.7311 0.3128 0.2229 0.035 Uiso 1 calc . . R
C3 C 0.85903(15) 0.35884(16) 0.04286(12) 0.0296(3) Uani 1 d . . .
H3 H 0.9494 0.2774 0.0544 0.035 Uiso 1 calc . . R
C4 C 0.85680(14) 0.45864(13) -0.07650(11) 0.0217(2) Uani 1 d . . .
C5 C 0.71885(15) 0.57981(13) -0.09034(11) 0.0231(2) Uani 1 d . . .
H5 H 0.7145 0.6471 -0.1689 0.028 Uiso 1 calc . . R
C6 C 0.58855(14) 0.60103(13) 0.01148(11) 0.0228(2) Uani 1 d . . .
H6 H 0.4984 0.6829 0.0006 0.027 Uiso 1 calc . . R
C7 C 0.98992(15) 0.43845(15) -0.18865(12) 0.0278(2) Uani 1 d . . .
H7 H 0.9749 0.5086 -0.2644 0.033 Uiso 1 calc . . R
C8 C 1.12788(17) 0.33161(19) -0.19301(15) 0.0357(3) Uani 1 d . . .
H8A H 1.208(2) 0.326(2) -0.2707(19) 0.039(5) Uiso 1 d . . .
H8B H 1.155(3) 0.256(3) -0.117(2) 0.049(6) Uiso 1 d . . .
C9 C 0.44714(14) 0.52080(14) 0.23883(11) 0.0234(2) Uani 1 d . . .
H9A H 0.4323 0.4254 0.2901 0.028 Uiso 1 calc . . R
H9B H 0.3518 0.5832 0.2087 0.028 Uiso 1 calc . . R
C10 C 0.29342(12) 0.66434(12) 0.42820(10) 0.01769(17) Uani 1 d . . .
C11 C 0.11741(13) 0.92485(12) 0.59795(10) 0.01811(17) Uani 1 d . . .
H11 H 0.1873 0.9810 0.5540 0.022 Uiso 1 calc . . R
C12 C -0.01454(13) 0.96566(11) 0.70399(10) 0.01776(17) Uani 1 d . . .
C13 C -0.13592(14) 0.89842(13) 0.75951(12) 0.0235(2) Uani 1 d . . .
H13 H -0.1382 0.8306 0.7261 0.028 Uiso 1 calc . . R
C14 C -0.25274(15) 0.93348(14) 0.86454(13) 0.0276(2) Uani 1 d . . .
H14 H -0.3333 0.8887 0.9016 0.033 Uiso 1 calc . . R
C15 C -0.25060(15) 1.03522(14) 0.91518(12) 0.0264(2) Uani 1 d . . .
H15 H -0.3286 1.0571 0.9864 0.032 Uiso 1 calc . . R
C16 C -0.13206(16) 1.10378(13) 0.85921(12) 0.0256(2) Uani 1 d . . .
H16 H -0.1307 1.1720 0.8926 0.031 Uiso 1 calc . . R
C17 C -0.01499(14) 1.07050(13) 0.75292(11) 0.02173(19) Uani 1 d . . .
H17 H 0.0631 1.1182 0.7144 0.026 Uiso 1 calc . . R
O1 O 0.48775(12) 0.10804(13) 0.58667(10) 0.0320(2) Uani 1 d . . .
H1 H 0.413(3) 0.157(3) 0.550(2) 0.066(8) Uiso 1 d . . .
C18 C 0.44511(17) -0.00600(18) 0.69190(14) 0.0333(3) Uani 1 d . . .
H18A H 0.4072 -0.0628 0.6672 0.050 Uiso 1 calc . . GR
H18B H 0.3621 0.0369 0.7556 0.050 Uiso 1 calc . . GR
H18C H 0.5370 -0.0697 0.7245 0.050 Uiso 1 calc . . GR
Cl1 Cl 0.21172(3) 0.28172(3) 0.45330(3) 0.02139(6) Uani 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.01556(11) 0.03363(15) 0.02290(13) -0.01520(11) 0.00013(9) -0.00674(10)
N1 0.0188(4) 0.0206(4) 0.0223(4) -0.0098(3) 0.0017(3) -0.0081(3)
N2 0.0160(4) 0.0208(4) 0.0189(4) -0.0076(3) -0.0008(3) -0.0070(3)
N3 0.0163(4) 0.0193(4) 0.0176(4) -0.0067(3) -0.0019(3) -0.0051(3)
C1 0.0194(4) 0.0223(5) 0.0186(4) -0.0092(4) 0.0002(3) -0.0082(4)
C2 0.0264(6) 0.0336(6) 0.0176(5) -0.0059(4) -0.0036(4) -0.0022(5)
C3 0.0223(5) 0.0332(6) 0.0231(5) -0.0092(5) -0.0036(4) 0.0008(5)
C4 0.0211(5) 0.0243(5) 0.0209(4) -0.0108(4) 0.0015(4) -0.0096(4)
C5 0.0260(5) 0.0191(4) 0.0205(5) -0.0045(4) 0.0005(4) -0.0097(4)
C6 0.0221(5) 0.0177(4) 0.0241(5) -0.0061(4) -0.0001(4) -0.0063(4)
C7 0.0248(5) 0.0310(6) 0.0240(5) -0.0109(4) 0.0039(4) -0.0107(5)
C8 0.0238(6) 0.0438(8) 0.0354(7) -0.0193(6) 0.0048(5) -0.0094(5)
C9 0.0219(5) 0.0288(5) 0.0213(5) -0.0125(4) 0.0029(4) -0.0114(4)
C10 0.0159(4) 0.0196(4) 0.0161(4) -0.0056(3) -0.0024(3) -0.0048(3)
C11 0.0176(4) 0.0181(4) 0.0184(4) -0.0050(3) -0.0034(3) -0.0062(3)
C12 0.0181(4) 0.0158(4) 0.0190(4) -0.0051(3) -0.0036(3) -0.0054(3)
C13 0.0208(5) 0.0237(5) 0.0280(5) -0.0124(4) 0.0003(4) -0.0095(4)
C14 0.0229(5) 0.0266(5) 0.0324(6) -0.0140(5) 0.0043(4) -0.0111(4)
C15 0.0265(5) 0.0223(5) 0.0260(5) -0.0112(4) 0.0020(4) -0.0066(4)
C16 0.0294(6) 0.0216(5) 0.0269(5) -0.0123(4) -0.0015(4) -0.0086(4)
C17 0.0231(5) 0.0196(4) 0.0239(5) -0.0087(4) -0.0019(4) -0.0089(4)
O1 0.0249(4) 0.0397(5) 0.0376(5) -0.0093(4) -0.0097(4) -0.0152(4)
C18 0.0253(6) 0.0391(7) 0.0322(6) -0.0100(5) -0.0054(5) -0.0079(5)
Cl1 0.02019(11) 0.01859(11) 0.02330(12) -0.00515(9) -0.00135(9) -0.00802(9)
_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 1.8295(12) . ?
S1 C10 1.7424(11) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C10 1.3125(14) . ?
N2 H2A 0.8600 . ?
N2 N3 1.3831(13) . ?
N2 C10 1.3318(14) . ?
N3 C11 1.2887(14) . ?
C1 C2 1.3884(17) . ?
C1 C6 1.3924(16) . ?
C1 C9 1.5041(15) . ?
C2 H2 0.9300 . ?
C2 C3 1.3897(17) . ?
C3 H3 0.9300 . ?
C3 C4 1.3998(18) . ?
C4 C5 1.3990(17) . ?
C4 C7 1.4755(16) . ?
C5 H5 0.9300 . ?
C5 C6 1.3869(16) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.318(2) . ?
C8 H8A 0.96(2) . ?
C8 H8B 0.98(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 H11 0.9300 . ?
C11 C12 1.4662(15) . ?
C12 C13 1.3992(15) . ?
C12 C17 1.3969(15) . ?
C13 H13 0.9300 . ?
C13 C14 1.3857(17) . ?
C14 H14 0.9300 . ?
C14 C15 1.3934(18) . ?
C15 H15 0.9300 . ?
C15 C16 1.3854(18) . ?
C16 H16 0.9300 . ?
C16 C17 1.3922(16) . ?
C17 H17 0.9300 . ?
O1 H1 0.85(3) . ?
O1 C18 1.4118(18) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 S1 C9 102.19(5) . . ?
H1A N1 H1B 120.0 . . ?
C10 N1 H1A 120.0 . . ?
C10 N1 H1B 120.0 . . ?
N3 N2 H2A 121.0 . . ?
C10 N2 H2A 121.0 . . ?
C10 N2 N3 118.04(9) . . ?
C11 N3 N2 114.69(9) . . ?
C2 C1 C6 118.72(10) . . ?
C2 C1 C9 120.73(11) . . ?
C6 C1 C9 120.51(11) . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 120.91(11) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.67(12) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C7 123.10(11) . . ?
C5 C4 C3 118.08(10) . . ?
C5 C4 C7 118.77(11) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.95(11) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.68(11) . . ?
C5 C6 H6 119.7 . . ?
C4 C7 H7 116.5 . . ?
C8 C7 C4 126.96(13) . . ?
C8 C7 H7 116.5 . . ?
C7 C8 H8A 121.6(12) . . ?
C7 C8 H8B 121.6(13) . . ?
H8A C8 H8B 116.8(17) . . ?
S1 C9 H9A 110.3 . . ?
S1 C9 H9B 110.3 . . ?
C1 C9 S1 107.25(8) . . ?
C1 C9 H9A 110.3 . . ?
C1 C9 H9B 110.3 . . ?
H9A C9 H9B 108.5 . . ?
N1 C10 S1 124.07(8) . . ?
N1 C10 N2 121.87(10) . . ?
N2 C10 S1 114.06(8) . . ?
N3 C11 H11 120.2 . . ?
N3 C11 C12 119.66(9) . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 121.58(10) . . ?
C17 C12 C11 118.75(9) . . ?
C17 C12 C13 119.63(10) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.65(11) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.63(11) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.86(11) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.01(11) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 H17 119.9 . . ?
C16 C17 C12 120.19(10) . . ?
C16 C17 H17 119.9 . . ?
C18 O1 H1 110.8(18) . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N3 C11 C12 -175.42(9) . . . . ?
N3 N2 C10 S1 -168.59(8) . . . . ?
N3 N2 C10 N1 11.73(16) . . . . ?
N3 C11 C12 C13 -10.06(16) . . . . ?
N3 C11 C12 C17 167.65(11) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C2 C1 C6 C5 0.60(18) . . . . ?
C2 C1 C9 S1 82.48(13) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C2 C3 C4 C7 -177.43(13) . . . . ?
C3 C4 C5 C6 0.48(18) . . . . ?
C3 C4 C7 C8 -2.8(2) . . . . ?
C4 C5 C6 C1 -0.77(18) . . . . ?
C5 C4 C7 C8 179.85(14) . . . . ?
C6 C1 C2 C3 -0.2(2) . . . . ?
C6 C1 C9 S1 -99.60(11) . . . . ?
C7 C4 C5 C6 177.98(11) . . . . ?
C9 S1 C10 N1 23.38(11) . . . . ?
C9 S1 C10 N2 -156.30(8) . . . . ?
C9 C1 C2 C3 177.80(12) . . . . ?
C9 C1 C6 C5 -177.37(11) . . . . ?
C10 S1 C9 C1 166.30(8) . . . . ?
C10 N2 N3 C11 -176.48(10) . . . . ?
C11 C12 C13 C14 175.91(12) . . . . ?
C11 C12 C17 C16 -175.33(11) . . . . ?
C12 C13 C14 C15 0.1(2) . . . . ?
C13 C12 C17 C16 2.43(18) . . . . ?
C13 C14 C15 C16 0.9(2) . . . . ?
C14 C15 C16 C17 -0.3(2) . . . . ?
C15 C16 C17 C12 -1.40(19) . . . . ?
C17 C12 C13 C14 -1.79(18) . . . . ?
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2 14 6 0.1307 2.0031 14.0104 6.0069 -0.1958 0.1364 -0.9795
-2 -14 -6 0.0767 -2.0031 -14.0104 -6.0069 0.1958 -0.1364 0.9795
13 1 3 0.0952 13.0061 1.0052 3.0117 -0.8151 0.4818 0.4440
-13 -1 -3 0.1512 -13.0061 -1.0052 -3.0117 0.8151 -0.4818 -0.4440
-1 1 -15 0.0406 -0.9884 1.0063 -15.0041 0.5195 0.8652 -0.0234
1 -1 15 0.0537 0.9884 -1.0063 15.0041 -0.5195 -0.8652 0.0234
0 -10 -13 0.0508 0.0055 -10.0034 -13.0058 0.3246 0.4864 0.8113
2 2 16 0.0544 1.9896 1.9963 16.0059 -0.5849 -0.7914 -0.1612
0 8 15 0.0668 -0.0080 8.0009 15.0057 -0.3996 -0.6607 -0.6770
1 3 16 0.0503 0.9895 2.9967 16.0054 -0.5216 -0.8118 -0.2757
-1 13 5 0.1055 -0.9984 13.0086 5.0039 -0.0038 0.0217 -1.0237
12 7 11 0.1148 12.0020 7.0067 11.0144 -0.9597 0.1296 -0.0852
0 0 -15 0.0297 0.0117 0.0059 -15.0035 0.4562 0.8856 0.0910
-5 -14 -5 0.0861 -5.0057 -14.0120 -5.0091 0.3340 -0.3410 0.8498
-6 -14 -10 0.0790 -6.0024 -14.0105 -10.0111 0.5423 -0.0943 0.8390
_iucr_refine_instructions_details
;
TITL
CELL 0.71073 9.417633 10.225647 11.863971 67.7993 68.7874 66.3097
ZERR 2 0.000235 0.000204 0.000268 0.002 0.0022 0.0021
LATT 1
SFAC C H N O S Cl
UNIT 36 44 6 2 2 2
L.S. 10
PLAN 1
MORE -1
BOND $H
CONF
fmap 2
acta 52
OMIT 2 5 1
OMIT 0 -6 3
OMIT 7 0 7
OMIT 4 -4 8
OMIT 6 0 6
OMIT 2 4 3
OMIT 0 -3 3
OMIT 5 5 1
OMIT -3 -2 2
REM
REM
REM
WGHT 0.057900 0.344700
FVAR 5.21127
S1 5 0.482957 0.608048 0.330867 11.00000 0.01556 0.03363 =
0.02290 -0.01520 0.00013 -0.00674
N1 3 0.180538 0.604258 0.457760 11.00000 0.01885 0.02060 =
0.02234 -0.00984 0.00171 -0.00810
AFIX 93
H1A 2 0.088892 0.637009 0.505984 11.00000 -1.20000
H1B 2 0.198223 0.532141 0.428902 11.00000 -1.20000
AFIX 0
N2 3 0.270882 0.776147 0.470892 11.00000 0.01604 0.02079 =
0.01887 -0.00758 -0.00075 -0.00697
AFIX 43
H2A 2 0.338215 0.825414 0.440290 11.00000 -1.20000
AFIX 0
N3 3 0.135994 0.810701 0.565895 11.00000 0.01628 0.01926 =
0.01755 -0.00670 -0.00191 -0.00511
C1 1 0.591298 0.500989 0.129854 11.00000 0.01941 0.02231 =
0.01861 -0.00915 0.00024 -0.00821
C2 1 0.727627 0.380249 0.144293 11.00000 0.02638 0.03356 =
0.01759 -0.00593 -0.00364 -0.00219
AFIX 43
H2 2 0.731054 0.312771 0.222926 11.00000 -1.20000
AFIX 0
C3 1 0.859032 0.358840 0.042862 11.00000 0.02230 0.03325 =
0.02315 -0.00918 -0.00364 0.00083
AFIX 43
H3 2 0.949363 0.277387 0.054400 11.00000 -1.20000
AFIX 0
C4 1 0.856800 0.458637 -0.076498 11.00000 0.02105 0.02431 =
0.02086 -0.01080 0.00152 -0.00955
C5 1 0.718852 0.579813 -0.090335 11.00000 0.02605 0.01913 =
0.02046 -0.00451 0.00049 -0.00968
AFIX 43
H5 2 0.714457 0.647101 -0.168936 11.00000 -1.20000
AFIX 0
C6 1 0.588552 0.601035 0.011483 11.00000 0.02205 0.01766 =
0.02411 -0.00610 -0.00009 -0.00634
AFIX 43
H6 2 0.498419 0.682928 0.000585 11.00000 -1.20000
AFIX 0
C7 1 0.989923 0.438449 -0.188646 11.00000 0.02482 0.03103 =
0.02402 -0.01093 0.00385 -0.01068
AFIX 43
H7 2 0.974889 0.508605 -0.264353 11.00000 -1.20000
AFIX 0
C8 1 1.127885 0.331610 -0.193011 11.00000 0.02382 0.04377 =
0.03544 -0.01926 0.00484 -0.00941
H8A 2 1.207664 0.325536 -0.270714 11.00000 0.03862
H8B 2 1.155166 0.255933 -0.116707 11.00000 0.04876
C9 1 0.447138 0.520795 0.238826 11.00000 0.02187 0.02878 =
0.02130 -0.01250 0.00294 -0.01140
AFIX 23
H9A 2 0.432255 0.425401 0.290083 11.00000 -1.20000
H9B 2 0.351767 0.583209 0.208717 11.00000 -1.20000
AFIX 0
C10 1 0.293418 0.664337 0.428202 11.00000 0.01594 0.01961 =
0.01613 -0.00563 -0.00237 -0.00481
C11 1 0.117411 0.924845 0.597948 11.00000 0.01760 0.01812 =
0.01844 -0.00502 -0.00341 -0.00622
AFIX 43
H11 2 0.187337 0.981044 0.554047 11.00000 -1.20000
AFIX 0
C12 1 -0.014541 0.965656 0.703987 11.00000 0.01814 0.01579 =
0.01901 -0.00514 -0.00363 -0.00537
C13 1 -0.135918 0.898419 0.759509 11.00000 0.02076 0.02370 =
0.02797 -0.01235 0.00031 -0.00948
AFIX 43
H13 2 -0.138184 0.830559 0.726103 11.00000 -1.20000
AFIX 0
C14 1 -0.252736 0.933483 0.864542 11.00000 0.02289 0.02661 =
0.03243 -0.01396 0.00425 -0.01113
AFIX 43
H14 2 -0.333326 0.888684 0.901587 11.00000 -1.20000
AFIX 0
C15 1 -0.250600 1.035222 0.915176 11.00000 0.02650 0.02227 =
0.02602 -0.01116 0.00204 -0.00660
AFIX 43
H15 2 -0.328588 1.057063 0.986392 11.00000 -1.20000
AFIX 0
C16 1 -0.132056 1.103777 0.859212 11.00000 0.02941 0.02163 =
0.02691 -0.01232 -0.00145 -0.00859
AFIX 43
H16 2 -0.130683 1.172034 0.892649 11.00000 -1.20000
AFIX 0
C17 1 -0.014987 1.070497 0.752923 11.00000 0.02313 0.01956 =
0.02394 -0.00866 -0.00192 -0.00885
AFIX 43
H17 2 0.063147 1.118203 0.714388 11.00000 -1.20000
AFIX 0
O1 4 0.487752 0.108039 0.586672 11.00000 0.02488 0.03965 =
0.03764 -0.00931 -0.00971 -0.01524
H1 2 0.412992 0.156675 0.549514 11.00000 0.06624
C18 1 0.445106 -0.006001 0.691904 11.00000 0.02529 0.03909 =
0.03220 -0.01000 -0.00541 -0.00790
AFIX 137
H18A 2 0.407223 -0.062787 0.667169 11.00000 -1.50000
H18B 2 0.362124 0.036924 0.755566 11.00000 -1.50000
H18C 2 0.536975 -0.069687 0.724535 11.00000 -1.50000
AFIX 0
CL1 6 0.211719 0.281724 0.453300 11.00000 0.02019 0.01859 =
0.02330 -0.00515 -0.00135 -0.00802
HKLF 4
REM
REM R1 = 0.0446 for 6918 Fo > 4sig(Fo) and 0.0656 for all 9081 data
REM 230 parameters refined using 0 restraints
END
WGHT 0.0579 0.3447
REM Highest difference peak 0.716, deepest hole -0.342, 1-sigma level 0.074
Q1 1 0.8809 0.4004 -0.0262 11.00000 0.05 0.72
REM The information below was added by Olex2.
REM
REM R1 = 0.0446 for 6918 Fo > 4sig(Fo) and 0.0656 for all 45468 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.72, deepest hole -0.34
REM Mean Shift 0, Max Shift 0.000.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0656
REM R1_gt = 0.0446
REM wR_ref = 0.1258
REM GOOF = 1.034
REM Shift_max = 0.000
REM Shift_mean = 0
REM Reflections_all = 45468
REM Reflections_gt = 6918
REM Parameters = n/a
REM Hole = -0.34
REM Peak = 0.72
REM Flack = n/a
;
_olex2_submission_original_sample_id M2
_olex2_submission_special_instructions 'No special instructions were received'