#------------------------------------------------------------------------------
#$Date: 2022-03-25 10:30:06 +0200 (Fri, 25 Mar 2022) $
#$Revision: 273979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/48/8104865.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_8104865
loop_
_publ_author_name
'Hosten, Eric C.'
'Betz, Richard'
_publ_section_title
;
 The crystal structure of 2-methyl-β-naphthothiazole, C12H9NS
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              483
_journal_page_last               485
_journal_paper_doi               10.1515/ncrs-2020-0563
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C12 H9 N S'
_chemical_formula_sum            'C12 H9 N S'
_chemical_formula_weight         199.26
_chemical_name_common            2-methyl-β-naphthothiazole
_chemical_name_systematic        2-methyl-β-naphthothiazole
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     SHELXS
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 91.102(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0743(5)
_cell_length_b                   14.0545(13)
_cell_length_c                   13.3319(17)
_cell_measurement_reflns_used    4594
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.90
_cell_volume                     950.61(18)
_computing_cell_refinement       'SAINT [1]'
_computing_data_collection       'APEX2 [1]'
_computing_data_reduction        'SAINT [1]'
_computing_molecular_graphics    'ORTEP3 [3], Mercury [4]'
_computing_publication_material  'SHELXL-97 [2], PLATON [5]'
_computing_structure_refinement  'SHELXL-97 [2]'
_computing_structure_solution    'SHELXS-97 [2]'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8686
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.344
_diffrn_reflns_theta_min         2.106
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8937
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;                                                              
SADABS [6]                                         
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       rod
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.511
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.145
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2362
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0322
_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)+(0.0440P)²+0.3222P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0908
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1970
_reflns_number_total             2362
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0563_suppl.cif
_cod_data_source_block           g
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8104865
_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_min   0.819
_shelx_estimated_absorpt_t_max   0.959
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'
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 0.07674(7) 0.54027(2) 0.34013(3) 0.03267(12) Uani 1 1 d . . . . .
N1 N 0.3017(2) 0.65777(8) 0.21966(8) 0.0284(2) Uani 1 1 d . . . . .
C1 C 0.3210(3) 0.61354(9) 0.38975(10) 0.0277(3) Uani 1 1 d . . . . .
C2 C 0.4172(2) 0.67089(9) 0.31371(9) 0.0253(3) Uani 1 1 d . . . . .
C3 C 0.6188(2) 0.73913(9) 0.33517(9) 0.0257(3) Uani 1 1 d . . . . .
C4 C 0.7265(3) 0.79895(9) 0.26118(10) 0.0319(3) Uani 1 1 d . . . . .
H4 H 0.662560 0.795418 0.193841 0.038 Uiso 1 1 calc R U . . .
C5 C 0.9229(3) 0.86201(10) 0.28632(12) 0.0378(3) Uani 1 1 d . . . . .
H5 H 0.995423 0.901586 0.236096 0.045 Uiso 1 1 calc R U . . .
C6 C 1.0178(3) 0.86860(10) 0.38565(12) 0.0386(3) Uani 1 1 d . . . . .
H6 H 1.153997 0.912616 0.402151 0.046 Uiso 1 1 calc R U . . .
C7 C 0.9158(3) 0.81215(10) 0.45886(11) 0.0350(3) Uani 1 1 d . . . . .
H7 H 0.980988 0.817627 0.525882 0.042 Uiso 1 1 calc R U . . .
C8 C 0.7141(3) 0.74565(9) 0.43589(10) 0.0285(3) Uani 1 1 d . . . . .
C9 C 0.6072(3) 0.68570(10) 0.51133(10) 0.0346(3) Uani 1 1 d . . . . .
H9 H 0.671240 0.691425 0.578481 0.041 Uiso 1 1 calc R U . . .
C10 C 0.4157(3) 0.62047(10) 0.48966(11) 0.0344(3) Uani 1 1 d . . . . .
H10 H 0.347748 0.580634 0.540592 0.041 Uiso 1 1 calc R U . . .
C11 C 0.1199(3) 0.59290(9) 0.22273(10) 0.0295(3) Uani 1 1 d . . . . .
C12 C -0.0522(3) 0.56580(12) 0.13503(12) 0.0393(3) Uani 1 1 d . . . . .
H12A H 0.021903 0.591642 0.073401 0.059 Uiso 1 1 calc R U . . .
H12B H -0.229527 0.591685 0.144048 0.059 Uiso 1 1 calc R U . . .
H12C H -0.061872 0.496305 0.130160 0.059 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C1 S1 C11 89.39(6) . .
C11 N1 C2 110.69(11) . .
C2 C1 C10 122.00(13) . .
C2 C1 S1 108.95(10) . .
C10 C1 S1 129.04(11) . .
N1 C2 C1 115.71(12) . .
N1 C2 C3 124.03(11) . .
C1 C2 C3 120.24(12) . .
C4 C3 C8 119.44(12) . .
C4 C3 C2 123.02(12) . .
C8 C3 C2 117.53(12) . .
C5 C4 C3 120.20(13) . .
C5 C4 H4 119.9 . .
C3 C4 H4 119.9 . .
C4 C5 C6 120.55(14) . .
C4 C5 H5 119.7 . .
C6 C5 H5 119.7 . .
C7 C6 C5 120.49(13) . .
C7 C6 H6 119.8 . .
C5 C6 H6 119.8 . .
C6 C7 C8 120.73(14) . .
C6 C7 H7 119.6 . .
C8 C7 H7 119.6 . .
C7 C8 C3 118.59(13) . .
C7 C8 C9 121.37(13) . .
C3 C8 C9 120.04(12) . .
C10 C9 C8 121.80(13) . .
C10 C9 H9 119.1 . .
C8 C9 H9 119.1 . .
C9 C10 C1 118.37(13) . .
C9 C10 H10 120.8 . .
C1 C10 H10 120.8 . .
N1 C11 C12 123.99(13) . .
N1 C11 S1 115.25(10) . .
C12 C11 S1 120.72(10) . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.7328(14) .
S1 C11 1.7487(14) .
N1 C11 1.2984(17) .
N1 C2 1.3861(17) .
C1 C2 1.3911(18) .
C1 C10 1.411(2) .
C2 C3 1.4270(18) .
C3 C4 1.4140(18) .
C3 C8 1.4214(18) .
C4 C5 1.370(2) .
C4 H4 0.9500 .
C5 C6 1.403(2) .
C5 H5 0.9500 .
C6 C7 1.367(2) .
C6 H6 0.9500 .
C7 C8 1.4150(19) .
C7 H7 0.9500 .
C8 C9 1.4272(19) .
C9 C10 1.363(2) .
C9 H9 0.9500 .
C10 H10 0.9500 .
C11 C12 1.4953(19) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
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
C11 S1 C1 C2 -0.67(9) . . . .
C11 S1 C1 C10 178.05(13) . . . .
C11 N1 C2 C1 0.56(16) . . . .
C11 N1 C2 C3 -178.28(11) . . . .
C10 C1 C2 N1 -178.60(12) . . . .
S1 C1 C2 N1 0.23(14) . . . .
C10 C1 C2 C3 0.28(19) . . . .
S1 C1 C2 C3 179.11(9) . . . .
N1 C2 C3 C4 -1.76(19) . . . .
C1 C2 C3 C4 179.45(11) . . . .
N1 C2 C3 C8 178.69(11) . . . .
C1 C2 C3 C8 -0.10(18) . . . .
C8 C3 C4 C5 0.61(19) . . . .
C2 C3 C4 C5 -178.93(13) . . . .
C3 C4 C5 C6 -0.5(2) . . . .
C4 C5 C6 C7 0.0(2) . . . .
C5 C6 C7 C8 0.4(2) . . . .
C6 C7 C8 C3 -0.3(2) . . . .
C6 C7 C8 C9 179.48(13) . . . .
C4 C3 C8 C7 -0.17(18) . . . .
C2 C3 C8 C7 179.40(11) . . . .
C4 C3 C8 C9 -179.99(12) . . . .
C2 C3 C8 C9 -0.42(18) . . . .
C7 C8 C9 C10 -179.01(13) . . . .
C3 C8 C9 C10 0.8(2) . . . .
C8 C9 C10 C1 -0.6(2) . . . .
C2 C1 C10 C9 0.1(2) . . . .
S1 C1 C10 C9 -178.50(10) . . . .
C2 N1 C11 C12 176.44(12) . . . .
C2 N1 C11 S1 -1.11(14) . . . .
C1 S1 C11 N1 1.07(10) . . . .
C1 S1 C11 C12 -176.57(12) . . . .
