#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/42/2234226.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_2234226
loop_
_publ_author_name
'Kassem, Mohamed G.'
'Ghabbour, Hazem A.'
'Abdel-Aziz, Hatem A.'
'Fun, Hoong-Kun'
'Ooi, Chin Wei'
_publ_section_title
;
 3-Chloro-4-methylquinolin-2(1H)-one
;
_journal_coeditor_code           HB6671
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1043
_journal_paper_doi               10.1107/S1600536812009889
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C10 H8 Cl N O'
_chemical_formula_moiety         'C10 H8 Cl N O'
_chemical_formula_sum            'C10 H8 Cl N O'
_chemical_formula_weight         193.62
_chemical_name_systematic
;
3-Chloro-4-methylquinolin-2(1H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.197(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.9361(2)
_cell_length_b                   12.9239(6)
_cell_length_c                   17.1019(7)
_cell_measurement_reflns_used    615
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      63.55
_cell_measurement_theta_min      4.31
_cell_volume                     856.23(7)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5522
_diffrn_reflns_theta_full        64.92
_diffrn_reflns_theta_max         64.92
_diffrn_reflns_theta_min         4.31
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.560
_exptl_absorpt_correction_T_max  0.7195
_exptl_absorpt_correction_T_min  0.1382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.92
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.208
_refine_ls_extinction_coef       0.0031(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0755P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1049
_reflns_number_gt                1178
_reflns_number_total             1434
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6671.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2234226
_cod_database_fobs_code          2234226
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Cl Cl1 1.04066(14) 0.51266(4) 0.76645(3) 0.0516(2) Uani d . 1 1
O O1 1.0673(4) 0.46152(12) 0.60239(9) 0.0560(4) Uani d . 1 1
N N1 0.7804(4) 0.60196(13) 0.54512(9) 0.0422(4) Uani d . 1 1
H H1 0.7928 0.5780 0.4947 0.051 Uiso d R 1 1
C C1 0.9152(5) 0.54435(15) 0.60939(12) 0.0414(4) Uani d . 1 1
C C2 0.8689(5) 0.58782(15) 0.68546(11) 0.0386(4) Uani d . 1 1
C C3 0.7149(4) 0.68001(14) 0.69302(11) 0.0371(4) Uani d . 1 1
C C4 0.5836(5) 0.73765(14) 0.62192(11) 0.0368(4) Uani d . 1 1
C C5 0.4234(5) 0.83478(16) 0.62245(12) 0.0446(5) Uani d . 1 1
H H5A 0.3935 0.8637 0.6706 0.054 Uiso calc R 1 1
C C6 0.3104(6) 0.88763(17) 0.55307(14) 0.0529(6) Uani d . 1 1
H H6A 0.2094 0.9525 0.5546 0.064 Uiso calc R 1 1
C C7 0.3468(6) 0.84441(18) 0.48054(14) 0.0552(6) Uani d . 1 1
H H7A 0.2690 0.8804 0.4337 0.066 Uiso calc R 1 1
C C8 0.4965(5) 0.74913(17) 0.47760(12) 0.0477(5) Uani d . 1 1
H H8A 0.5166 0.7198 0.4290 0.057 Uiso calc R 1 1
C C9 0.6184(5) 0.69643(15) 0.54803(11) 0.0385(4) Uani d . 1 1
C C10 0.6782(6) 0.72335(16) 0.77284(11) 0.0468(5) Uani d . 1 1
H H10A 0.7537 0.6728 0.8133 0.070 Uiso calc R 1 1
H H10B 0.4407 0.7403 0.7728 0.070 Uiso calc R 1 1
H H10C 0.8168 0.7846 0.7833 0.070 Uiso calc R 1 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'
Cl Cl 0.3639 0.7018 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C9 124.95(17)
C1 N1 H1 119.6
C9 N1 H1 115.4
O1 C1 N1 121.42(18)
O1 C1 C2 123.80(19)
N1 C1 C2 114.78(17)
C3 C2 C1 123.60(18)
C3 C2 Cl1 122.45(15)
C1 C2 Cl1 113.93(15)
C2 C3 C4 118.30(17)
C2 C3 C10 122.04(18)
C4 C3 C10 119.65(17)
C9 C4 C5 117.48(18)
C9 C4 C3 119.13(18)
C5 C4 C3 123.38(18)
C6 C5 C4 121.0(2)
C6 C5 H5A 119.5
C4 C5 H5A 119.5
C5 C6 C7 120.2(2)
C5 C6 H6A 119.9
C7 C6 H6A 119.9
C8 C7 C6 120.4(2)
C8 C7 H7A 119.8
C6 C7 H7A 119.8
C7 C8 C9 119.5(2)
C7 C8 H8A 120.3
C9 C8 H8A 120.3
N1 C9 C8 119.43(18)
N1 C9 C4 119.21(18)
C8 C9 C4 121.37(19)
C3 C10 H10A 109.5
C3 C10 H10B 109.5
H10A C10 H10B 109.5
C3 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C2 1.728(2)
O1 C1 1.243(3)
N1 C1 1.355(3)
N1 C9 1.382(3)
N1 H1 0.9256
C1 C2 1.458(3)
C2 C3 1.353(3)
C3 C4 1.442(3)
C3 C10 1.506(2)
C4 C9 1.400(3)
C4 C5 1.406(3)
C5 C6 1.373(3)
C5 H5A 0.9300
C6 C7 1.391(3)
C6 H6A 0.9300
C7 C8 1.370(3)
C7 H7A 0.9300
C8 C9 1.393(3)
C8 H8A 0.9300
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
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
N1 H1 O1 3_766 0.93 1.91 2.816(2) 166 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
C9 N1 C1 O1 -177.64(19)
C9 N1 C1 C2 1.9(3)
O1 C1 C2 C3 177.3(2)
N1 C1 C2 C3 -2.2(3)
O1 C1 C2 Cl1 -0.8(3)
N1 C1 C2 Cl1 179.65(14)
C1 C2 C3 C4 1.2(3)
Cl1 C2 C3 C4 179.19(13)
C1 C2 C3 C10 -178.76(18)
Cl1 C2 C3 C10 -0.7(3)
C2 C3 C4 C9 0.2(3)
C10 C3 C4 C9 -179.84(16)
C2 C3 C4 C5 -179.06(18)
C10 C3 C4 C5 0.9(3)
C9 C4 C5 C6 -0.9(3)
C3 C4 C5 C6 178.36(19)
C4 C5 C6 C7 1.4(3)
C5 C6 C7 C8 -0.3(3)
C6 C7 C8 C9 -1.2(3)
C1 N1 C9 C8 178.74(18)
C1 N1 C9 C4 -0.6(3)
C7 C8 C9 N1 -177.72(19)
C7 C8 C9 C4 1.6(3)
C5 C4 C9 N1 178.79(17)
C3 C4 C9 N1 -0.5(3)
C5 C4 C9 C8 -0.5(3)
C3 C4 C9 C8 -179.88(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 276479
