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#$Date: 2022-06-30 12:17:22 +0300 (Thu, 30 Jun 2022) $
#$Revision: 276443 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/55/8105588.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8105588
loop_
_publ_author_name
'Li, Da'
'Zhang, Hua'
'Zhang, Qing'
'Zhou, Yan'
'Zhou, Sheng'
_publ_section_title
;
 The crystal structure of
 6-amino-2-methyl-8-(4-(methylthio)phenyl)-2,3,8,8a-tetrahydroisoquinoline-5,7,7(1H)-tricarbonitrile
 -- ethanol (1/1), C20H19N5S
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              197
_journal_page_last               198
_journal_paper_doi               10.1515/ncrs-2018-0167
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C20 H19 N5 S, C2 H6 O'
_chemical_formula_sum            'C22 H25 N5 O S'
_chemical_formula_weight         407.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 95.948(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1257(14)
_cell_length_b                   11.0862(14)
_cell_length_c                   16.0280(19)
_cell_measurement_reflns_used    3831
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.24
_cell_volume                     2143.0(4)
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2( Bruker Apex-II, 2009)'
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10647
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.238
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_meas      .
_exptl_crystal_description       needle
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0486
_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)+(0.0770P)²+0.6272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1487
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2904
_reflns_number_total             3772
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0167_suppl.cif
_cod_data_source_block           a
_cod_database_code               8105588
_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.
;
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.946
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C22(H22A,H22B)
2.c Me refined with riding coordinates:
 C1(H1A,H1B,H1C), C20(H20A,H20B,H20C), C23(H23A,H23B,H23C)
2.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C15(H15), C16(H16), C18(H18), C19(H19)
2.e X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
;
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'
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 0.89482(6) 1.10345(6) 0.22381(5) 0.0652(3) Uani 1 1 d . . . . .
N1 N 0.57570(17) 0.50479(16) 0.27338(12) 0.0492(5) Uani 1 1 d . . . . .
N2 N 0.5577(2) 0.1983(2) -0.02611(17) 0.0821(8) Uani 1 1 d . . . . .
N3 N 0.76031(18) 0.40614(19) -0.08169(12) 0.0603(6) Uani 1 1 d . . . . .
H3A H 0.734137 0.339881 -0.103500 0.072 Uiso 1 1 calc R . . . .
H3B H 0.810033 0.445319 -0.105089 0.072 Uiso 1 1 calc R . . . .
N4 N 0.7876(3) 0.7167(2) -0.10089(15) 0.0916(9) Uani 1 1 d . . . . .
N5 N 0.97092(18) 0.5070(2) 0.09582(14) 0.0656(6) Uani 1 1 d . . . . .
C1 C 0.5334(2) 0.5594(2) 0.34675(16) 0.0630(7) Uani 1 1 d . . . . .
H1A H 0.590729 0.606709 0.376800 0.094 Uiso 1 1 calc R . . . .
H1B H 0.471288 0.610207 0.328924 0.094 Uiso 1 1 calc R . . . .
H1C H 0.510326 0.497012 0.382715 0.094 Uiso 1 1 calc R . . . .
C2 C 0.4906(2) 0.4326(2) 0.22672(17) 0.0609(7) Uani 1 1 d . . . . .
H2A H 0.423058 0.479650 0.216974 0.073 Uiso 1 1 calc R . . . .
H2B H 0.474891 0.362532 0.259741 0.073 Uiso 1 1 calc R . . . .
C3 C 0.5251(2) 0.3924(2) 0.14502(16) 0.0534(6) Uani 1 1 d . . . . .
H3 H 0.484219 0.331630 0.116215 0.064 Uiso 1 1 calc R . . . .
C4 C 0.61121(18) 0.43824(18) 0.11060(13) 0.0422(5) Uani 1 1 d . . . . .
C5 C 0.67724(17) 0.53988(17) 0.15213(13) 0.0390(5) Uani 1 1 d . . . . .
H5 H 0.747030 0.507255 0.179306 0.047 Uiso 1 1 calc R . . . .
C6 C 0.61451(19) 0.59728(18) 0.21851(14) 0.0454(5) Uani 1 1 d . . . . .
H6A H 0.662518 0.653421 0.251425 0.054 Uiso 1 1 calc R . . . .
H6B H 0.551644 0.641968 0.191915 0.054 Uiso 1 1 calc R . . . .
C7 C 0.64592(18) 0.39480(19) 0.03105(14) 0.0431(5) Uani 1 1 d . . . . .
C8 C 0.59795(19) 0.2859(2) -0.00151(16) 0.0537(6) Uani 1 1 d . . . . .
C9 C 0.72355(18) 0.44844(19) -0.01111(13) 0.0433(5) Uani 1 1 d . . . . .
C10 C 0.77639(17) 0.56668(18) 0.02273(12) 0.0406(5) Uani 1 1 d . . . . .
C11 C 0.7878(2) 0.6509(2) -0.04701(15) 0.0543(6) Uani 1 1 d . . . . .
C12 C 0.8876(2) 0.5362(2) 0.06428(14) 0.0455(5) Uani 1 1 d . . . . .
C13 C 0.70411(17) 0.63056(18) 0.08542(12) 0.0382(5) Uani 1 1 d . . . . .
H13 H 0.633461 0.651058 0.053214 0.046 Uiso 1 1 calc R . . . .
C14 C 0.75411(17) 0.74777(18) 0.11844(12) 0.0374(5) Uani 1 1 d . . . . .
C15 C 0.71569(17) 0.85529(19) 0.08292(13) 0.0426(5) Uani 1 1 d . . . . .
H15 H 0.660657 0.853561 0.037984 0.051 Uiso 1 1 calc R . . . .
C16 C 0.75650(18) 0.96485(19) 0.11212(14) 0.0456(5) Uani 1 1 d . . . . .
H16 H 0.729492 1.035819 0.086666 0.055 Uiso 1 1 calc R . . . .
C17 C 0.83741(17) 0.96949(18) 0.17908(13) 0.0419(5) Uani 1 1 d . . . . .
C18 C 0.87637(18) 0.8623(2) 0.21550(13) 0.0449(5) Uani 1 1 d . . . . .
H18 H 0.930894 0.864115 0.260780 0.054 Uiso 1 1 calc R . . . .
C19 C 0.83568(18) 0.75372(18) 0.18571(13) 0.0422(5) Uani 1 1 d . . . . .
H19 H 0.863133 0.682793 0.210951 0.051 Uiso 1 1 calc R . . . .
C20 C 0.8239(3) 1.2197(2) 0.1632(2) 0.0882(10) Uani 1 1 d . . . . .
H20A H 0.850519 1.296898 0.183637 0.132 Uiso 1 1 calc R . . . .
H20B H 0.837271 1.211054 0.105517 0.132 Uiso 1 1 calc R . . . .
H20C H 0.745817 1.213823 0.167825 0.132 Uiso 1 1 calc R . . . .
O1 O 0.7477(2) 0.3411(2) 0.34547(17) 0.0901(7) Uani 1 1 d . . . . .
C22 C 0.8390(5) 0.4212(6) 0.3735(4) 0.161(2) Uani 1 1 d . . . . .
H22A H 0.874582 0.446942 0.325001 0.193 Uiso 1 1 calc R . . . .
H22B H 0.809185 0.492522 0.398122 0.193 Uiso 1 1 calc R . . . .
C23 C 0.9188(5) 0.3705(7) 0.4316(4) 0.187(3) Uani 1 1 d . . . . .
H23A H 0.975949 0.428742 0.446936 0.280 Uiso 1 1 calc R . . . .
H23B H 0.885014 0.346760 0.480661 0.280 Uiso 1 1 calc R . . . .
H23C H 0.950508 0.301113 0.407431 0.280 Uiso 1 1 calc R . . . .
H1 H 0.689(3) 0.385(4) 0.321(2) 0.115(13) Uiso 1 1 d . . . . .
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'
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
C17 S1 C20 103.90(12) . .
C2 N1 C1 110.7(2) . .
C2 N1 C6 109.47(18) . .
C6 N1 C1 110.84(17) . .
H3A N3 H3B 120.0 . .
C9 N3 H3A 120.0 . .
C9 N3 H3B 120.0 . .
N1 C1 H1A 109.5 . .
N1 C1 H1B 109.5 . .
N1 C1 H1C 109.5 . .
H1A C1 H1B 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
N1 C2 H2A 109.3 . .
N1 C2 H2B 109.3 . .
N1 C2 C3 111.7(2) . .
H2A C2 H2B 107.9 . .
C3 C2 H2A 109.3 . .
C3 C2 H2B 109.3 . .
C2 C3 H3 118.1 . .
C4 C3 C2 123.8(2) . .
C4 C3 H3 118.1 . .
C3 C4 C5 120.6(2) . .
C3 C4 C7 122.9(2) . .
C7 C4 C5 116.46(18) . .
C4 C5 H5 108.5 . .
C4 C5 C6 110.17(17) . .
C4 C5 C13 109.09(16) . .
C6 C5 H5 108.5 . .
C6 C5 C13 112.04(16) . .
C13 C5 H5 108.5 . .
N1 C6 C5 110.21(17) . .
N1 C6 H6A 109.6 . .
N1 C6 H6B 109.6 . .
C5 C6 H6A 109.6 . .
C5 C6 H6B 109.6 . .
H6A C6 H6B 108.1 . .
C8 C7 C4 117.2(2) . .
C9 C7 C4 124.62(19) . .
C9 C7 C8 118.1(2) . .
N2 C8 C7 178.3(3) . .
N3 C9 C7 125.2(2) . .
N3 C9 C10 115.69(19) . .
C7 C9 C10 119.10(18) . .
C9 C10 C13 111.82(17) . .
C11 C10 C9 110.00(17) . .
C11 C10 C12 109.48(19) . .
C11 C10 C13 107.58(17) . .
C12 C10 C9 106.98(17) . .
C12 C10 C13 110.99(16) . .
N4 C11 C10 174.5(3) . .
N5 C12 C10 176.5(2) . .
C5 C13 C10 108.97(16) . .
C5 C13 H13 106.4 . .
C10 C13 H13 106.4 . .
C14 C13 C5 115.42(16) . .
C14 C13 C10 112.53(16) . .
C14 C13 H13 106.4 . .
C15 C14 C13 119.57(18) . .
C15 C14 C19 117.53(19) . .
C19 C14 C13 122.87(18) . .
C14 C15 H15 119.1 . .
C16 C15 C14 121.9(2) . .
C16 C15 H15 119.1 . .
C15 C16 H16 120.0 . .
C15 C16 C17 120.0(2) . .
C17 C16 H16 120.0 . .
C16 C17 S1 124.62(16) . .
C16 C17 C18 118.70(19) . .
C18 C17 S1 116.67(16) . .
C17 C18 H18 119.6 . .
C19 C18 C17 120.9(2) . .
C19 C18 H18 119.6 . .
C14 C19 H19 119.5 . .
C18 C19 C14 121.04(19) . .
C18 C19 H19 119.5 . .
S1 C20 H20A 109.5 . .
S1 C20 H20B 109.5 . .
S1 C20 H20C 109.5 . .
H20A C20 H20B 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C22 O1 H1 110(2) . .
O1 C22 H22A 108.6 . .
O1 C22 H22B 108.6 . .
H22A C22 H22B 107.6 . .
C23 C22 O1 114.5(5) . .
C23 C22 H22A 108.6 . .
C23 C22 H22B 108.6 . .
C22 C23 H23A 109.5 . .
C22 C23 H23B 109.5 . .
C22 C23 H23C 109.5 . .
H23A C23 H23B 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C17 1.761(2) .
S1 C20 1.780(3) .
N1 C1 1.462(3) .
N1 C2 1.451(3) .
N1 C6 1.460(3) .
N2 C8 1.139(3) .
N3 H3A 0.8600 .
N3 H3B 0.8600 .
N3 C9 1.343(3) .
N4 C11 1.130(3) .
N5 C12 1.130(3) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C2 C3 1.484(3) .
C3 H3 0.9300 .
C3 C4 1.331(3) .
C4 C5 1.498(3) .
C4 C7 1.465(3) .
C5 H5 0.9800 .
C5 C6 1.511(3) .
C5 C13 1.527(3) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C8 1.416(3) .
C7 C9 1.352(3) .
C9 C10 1.533(3) .
C10 C11 1.474(3) .
C10 C12 1.480(3) .
C10 C13 1.569(3) .
C13 H13 0.9800 .
C13 C14 1.506(3) .
C14 C15 1.381(3) .
C14 C19 1.387(3) .
C15 H15 0.9300 .
C15 C16 1.375(3) .
C16 H16 0.9300 .
C16 C17 1.378(3) .
C17 C18 1.386(3) .
C18 H18 0.9300 .
C18 C19 1.368(3) .
C19 H19 0.9300 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
O1 C22 1.454(6) .
O1 H1 0.91(4) .
C22 H22A 0.9700 .
C22 H22B 0.9700 .
C22 C23 1.390(7) .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
