#------------------------------------------------------------------------------
#$Date: 2023-05-06 13:49:18 +0300 (Sat, 06 May 2023) $
#$Revision: 283597 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/42/2244242.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2244242
loop_
_publ_author_name
'Hebishy, Ali M. S.'
'Elgemeie, Galal H.'
'Gouda, Lobna M.'
'Jones, Peter G.'
_publ_section_title
;
 Crystal structures of three homologues with increasing ring size:
 2-meth-oxy-4-(thio-phen-2-yl)-5,6,7,8-tetra-hydro-quinoline-3-carbo-nitrile,
 2-meth-oxy-4-(thio-phen-2-yl)-6,7,8,9-tetra-hydro-5H-cyclo-hepta-[b]pyridine-3-carbo-nitrile
 and
 2-meth-oxy-4-(thio-phen-2-yl)-5,6,7,8,9,10-hexa-hydrocyclo-octa[b]pyridine-3-carbo-nitrile.
;
_journal_coeditor_code           YZ2030
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              335
_journal_page_last               340
_journal_paper_doi               10.1107/S2056989023001883
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C15 H14 N2 O S'
_chemical_formula_moiety         'C15 H14 N2 O S'
_chemical_formula_sum            'C15 H14 N2 O S'
_chemical_formula_weight         270.34
_chemical_name_systematic
;
2-Methoxy-4-(thiophen-2-yl)-5,6,7,8-tetrahydroquinoline-3-carbonitrile
;
_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     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 98.7757(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.85636(13)
_cell_length_b                   9.18570(10)
_cell_length_c                   13.31001(16)
_cell_measurement_reflns_used    35765
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.0990
_cell_measurement_theta_min      4.9090
_cell_volume                     1311.78(3)
_computing_cell_refinement
;
CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)
;
_computing_data_collection
;
CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)
;
_computing_data_reduction
;
CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)
;
_computing_molecular_graphics
;
XP (Siemens, 1994)
;
_computing_publication_material
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'XtaLAB Synergy'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0107
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            59253
_diffrn_reflns_theta_full        77.000
_diffrn_reflns_theta_max         77.661
_diffrn_reflns_theta_min         4.906
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82009
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2022)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       irregular
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.236
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2774
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0263
_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)+(0.0343P)²+0.5681P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0714
_reflns_number_gt                2663
_reflns_number_total             2774
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yz2030sup1.cif
_cod_data_source_block           1a
_cod_depositor_comments
'Adding full bibliography for 2244242--2244244.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2244242
_cod_database_fobs_code          2244242
_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   0.815
_shelx_estimated_absorpt_t_max   0.939
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.41901(8) 0.65182(10) 0.62167(7) 0.01531(18) Uani d 1 . .
C C2 0.49881(9) 0.69755(11) 0.56350(8) 0.0145(2) Uani d 1 . .
C C3 0.61817(9) 0.63623(11) 0.56496(8) 0.0145(2) Uani d 1 . .
C C4 0.65292(9) 0.51730(11) 0.62923(8) 0.0143(2) Uani d 1 . .
C C4A 0.56608(10) 0.46444(11) 0.68941(8) 0.0156(2) Uani d 1 . .
C C5 0.59305(10) 0.33045(13) 0.75609(8) 0.0201(2) Uani d 1 . .
H H5A 0.649271 0.357815 0.818958 0.024 Uiso calc 1 . .
H H5B 0.636738 0.257414 0.719674 0.024 Uiso calc 1 . .
C C6 0.47503(11) 0.26226(13) 0.78460(9) 0.0235(2) Uani d 1 . .
H H6A 0.425966 0.217090 0.723760 0.028 Uiso calc 1 . .
H H6B 0.497721 0.185108 0.836031 0.028 Uiso calc 1 . .
C C7 0.39682(12) 0.37797(14) 0.82721(9) 0.0261(3) Uani d 1 . .
H H7A 0.446984 0.425907 0.886394 0.031 Uiso calc 1 . .
H H7B 0.323728 0.331799 0.850455 0.031 Uiso calc 1 . .
C C8 0.35304(10) 0.49113(13) 0.74576(9) 0.0204(2) Uani d 1 . .
H H8A 0.281165 0.451055 0.699260 0.024 Uiso calc 1 . .
H H8B 0.323737 0.578340 0.778891 0.024 Uiso calc 1 . .
C C8A 0.45209(10) 0.53687(12) 0.68392(8) 0.0156(2) Uani d 1 . .
C C9 0.35965(10) 0.89244(12) 0.50857(9) 0.0206(2) Uani d 1 . .
H H9A 0.350748 0.972299 0.459164 0.031 Uiso calc 1 . .
H H9B 0.365752 0.932339 0.577434 0.031 Uiso calc 1 . .
H H9C 0.286883 0.828279 0.495114 0.031 Uiso calc 1 . .
O O1 0.47092(7) 0.81060(8) 0.49971(6) 0.01807(17) Uani d 1 . .
C C10 0.70092(10) 0.70570(11) 0.50540(8) 0.0164(2) Uani d 1 . .
N N2 0.76402(9) 0.76686(11) 0.45769(8) 0.0230(2) Uani d 1 . .
S S1 0.87568(2) 0.41082(3) 0.74141(2) 0.02107(9) Uani d 1 . .
C C11 0.77753(9) 0.45283(11) 0.63009(8) 0.0152(2) Uani d 1 . .
C C12 0.83478(10) 0.42163(11) 0.54747(8) 0.0171(2) Uani d 1 . .
H H12 0.796800 0.437646 0.479223 0.021 Uiso calc 1 . .
C C13 0.95620(10) 0.36312(12) 0.57419(9) 0.0199(2) Uani d 1 . .
H H13 1.007563 0.334334 0.525951 0.024 Uiso calc 1 . .
C C14 0.99099(10) 0.35277(12) 0.67641(9) 0.0218(2) Uani d 1 . .
H H14 1.069755 0.317592 0.707976 0.026 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C8A . . 118.12(9) ?
N1 C2 O1 . . 120.82(9) ?
N1 C2 C3 . . 123.40(10) ?
O1 C2 C3 . . 115.75(9) ?
C4 C3 C2 . . 118.70(9) ?
C4 C3 C10 . . 123.38(9) ?
C2 C3 C10 . . 117.78(9) ?
C3 C4 C4A . . 118.20(9) ?
C3 C4 C11 . . 118.57(9) ?
C4A C4 C11 . . 123.23(9) ?
C8A C4A C4 . . 117.96(9) ?
C8A C4A C5 . . 120.43(9) ?
C4 C4A C5 . . 121.58(9) ?
C4A C5 C6 . . 112.56(9) ?
C4A C5 H5A . . 109.1 ?
C6 C5 H5A . . 109.1 ?
C4A C5 H5B . . 109.1 ?
C6 C5 H5B . . 109.1 ?
H5A C5 H5B . . 107.8 ?
C7 C6 C5 . . 110.08(10) y
C7 C6 H6A . . 109.6 ?
C5 C6 H6A . . 109.6 ?
C7 C6 H6B . . 109.6 ?
C5 C6 H6B . . 109.6 ?
H6A C6 H6B . . 108.2 ?
C6 C7 C8 . . 110.00(9) y
C6 C7 H7A . . 109.7 ?
C8 C7 H7A . . 109.7 ?
C6 C7 H7B . . 109.7 ?
C8 C7 H7B . . 109.7 ?
H7A C7 H7B . . 108.2 ?
C8A C8 C7 . . 113.99(9) ?
C8A C8 H8A . . 108.8 ?
C7 C8 H8A . . 108.8 ?
C8A C8 H8B . . 108.8 ?
C7 C8 H8B . . 108.8 ?
H8A C8 H8B . . 107.6 ?
N1 C8A C4A . . 123.55(9) ?
N1 C8A C8 . . 113.91(9) y
C4A C8A C8 . . 122.53(10) ?
O1 C9 H9A . . 109.5 ?
O1 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
O1 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C2 O1 C9 . . 117.45(8) ?
N2 C10 C3 . . 176.95(11) ?
C14 S1 C11 . . 92.23(5) ?
C12 C11 C4 . . 127.16(10) ?
C12 C11 S1 . . 110.13(8) ?
C4 C11 S1 . . 122.68(8) ?
C11 C12 C13 . . 113.28(10) ?
C11 C12 H12 . . 123.4 ?
C13 C12 H12 . . 123.4 ?
C14 C13 C12 . . 112.56(10) ?
C14 C13 H13 . . 123.7 ?
C12 C13 H13 . . 123.7 ?
C13 C14 S1 . . 111.79(8) ?
C13 C14 H14 . . 124.1 ?
S1 C14 H14 . . 124.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.3156(14) ?
N1 C8A . 1.3563(14) ?
C2 O1 . 1.3463(13) ?
C2 C3 . 1.4104(14) ?
C3 C4 . 1.4032(14) ?
C3 C10 . 1.4353(14) ?
C4 C4A . 1.4130(14) ?
C4 C11 . 1.4752(14) ?
C4A C8A . 1.3971(15) ?
C4A C5 . 1.5195(14) ?
C5 C6 . 1.5252(15) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 C7 . 1.5229(16) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C8 . 1.5246(16) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 C8A . 1.5102(14) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 O1 . 1.4427(12) ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 N2 . 1.1492(15) ?
S1 C14 . 1.7120(12) ?
S1 C11 . 1.7314(11) ?
C11 C12 . 1.3734(15) ?
C12 C13 . 1.4177(15) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.3586(17) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C12 H12 N1 3_666 0.95 2.65 3.3499(14) 131.2 yes
C13 H13 N2 3_766 0.95 2.63 3.3503(14) 133.4 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8A N1 C2 O1 . . . . 179.60(9) ?
C8A N1 C2 C3 . . . . -2.09(15) ?
N1 C2 C3 C4 . . . . 2.08(16) ?
O1 C2 C3 C4 . . . . -179.53(9) ?
N1 C2 C3 C10 . . . . -173.74(9) ?
O1 C2 C3 C10 . . . . 4.65(14) ?
C2 C3 C4 C4A . . . . 0.13(15) ?
C10 C3 C4 C4A . . . . 175.70(9) ?
C2 C3 C4 C11 . . . . 179.62(9) ?
C10 C3 C4 C11 . . . . -4.81(15) ?
C3 C4 C4A C8A . . . . -2.10(15) ?
C11 C4 C4A C8A . . . . 178.44(9) ?
C3 C4 C4A C5 . . . . 176.16(10) ?
C11 C4 C4A C5 . . . . -3.30(16) ?
C8A C4A C5 C6 . . . . 18.12(15) y
C4 C4A C5 C6 . . . . -160.09(10) ?
C4A C5 C6 C7 . . . . -50.80(13) y
C5 C6 C7 C8 . . . . 63.65(13) y
C6 C7 C8 C8A . . . . -42.62(14) y
C2 N1 C8A C4A . . . . -0.11(15) ?
C2 N1 C8A C8 . . . . -178.79(9) ?
C4 C4A C8A N1 . . . . 2.20(16) ?
C5 C4A C8A N1 . . . . -176.07(10) ?
C4 C4A C8A C8 . . . . -179.22(9) ?
C5 C4A C8A C8 . . . . 2.50(16) y
C7 C8 C8A N1 . . . . -171.09(10) ?
C7 C8 C8A C4A . . . . 10.21(15) y
N1 C2 O1 C9 . . . . 9.04(14) ?
C3 C2 O1 C9 . . . . -169.39(9) ?
C3 C4 C11 C12 . . . . -44.17(16) ?
C4A C4 C11 C12 . . . . 135.29(12) ?
C3 C4 C11 S1 . . . . 133.63(9) ?
C4A C4 C11 S1 . . . . -46.91(14) ?
C14 S1 C11 C12 . . . . 0.06(9) ?
C14 S1 C11 C4 . . . . -178.08(9) ?
C4 C11 C12 C13 . . . . 178.59(10) ?
S1 C11 C12 C13 . . . . 0.56(12) ?
C11 C12 C13 C14 . . . . -1.09(14) ?
C12 C13 C14 S1 . . . . 1.11(13) ?
C11 S1 C14 C13 . . . . -0.68(9) ?
