#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/56/2225676.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_2225676
loop_
_publ_author_name
'Khan, F. Nawaz'
'Mohana Roopan, S.'
'Hathwar, Venkatesha R.'
'Rajesh, R.'
'Khawar Rauf, M.'
_publ_section_title
;
 (2-Chlorobenzo[h]quinolin-3-yl)methanol
;
_journal_coeditor_code           PV2269
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o953
_journal_paper_doi               10.1107/S1600536810010767
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H10 Cl N O'
_chemical_formula_moiety         'C14 H10 Cl N O'
_chemical_formula_sum            'C14 H10 Cl N O'
_chemical_formula_weight         243.68
_chemical_name_systematic
;
(2-Chlorobenzo[h]quinolin-3-yl)methanol
;
_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                 95.123(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.6953(4)
_cell_length_b                   4.61459(11)
_cell_length_c                   14.5588(3)
_cell_measurement_reflns_used    11643
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.45
_cell_volume                     1117.16(4)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11643
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.45
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_T_max  0.9154
_exptl_absorpt_correction_T_min  0.8959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis Pro; Oxford Diffraction, 2009)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.224
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2200
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0343
_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)+(0.0447P)²+0.1644P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0928
_reflns_number_gt                1717
_reflns_number_total             2200
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2269.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        1117.16(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225676
_cod_database_fobs_code          2225676
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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.38036(3) 0.30225(12) 0.55246(3) 0.05783(19) Uani d . 1 . .
N N1 0.28031(8) 0.6236(3) 0.45110(8) 0.0350(3) Uani d . 1 . .
O O1 0.47139(8) 0.0886(3) 0.28368(8) 0.0497(3) Uani d . 1 . .
H H1 0.4911 0.2355 0.2633 0.074 Uiso calc R 1 . .
C C2 0.37487(9) 0.3556(3) 0.36689(10) 0.0315(3) Uani d . 1 . .
C C1 0.33981(9) 0.4434(3) 0.44662(10) 0.0331(4) Uani d . 1 . .
C C7 0.18191(9) 0.9418(4) 0.37325(11) 0.0366(4) Uani d . 1 . .
C C9 0.27796(9) 0.6741(3) 0.28570(10) 0.0333(4) Uani d . 1 . .
C C3 0.34176(9) 0.4759(3) 0.28642(10) 0.0339(4) Uani d . 1 . .
H H3 0.3619 0.4254 0.2311 0.041 Uiso calc R 1 . .
C C4 0.24384(10) 0.8084(4) 0.20323(11) 0.0426(4) Uani d . 1 . .
H H4 0.2637 0.7635 0.1472 0.051 Uiso calc R 1 . .
C C8 0.24801(9) 0.7420(3) 0.37074(10) 0.0309(3) Uani d . 1 . .
C C6 0.14987(10) 1.0709(4) 0.28978(12) 0.0417(4) Uani d . 1 . .
C C13 0.14771(10) 1.0095(4) 0.45516(12) 0.0478(4) Uani d . 1 . .
H H13 0.1685 0.9266 0.5105 0.057 Uiso calc R 1 . .
C C5 0.18321(11) 0.9994(4) 0.20550(12) 0.0477(5) Uani d . 1 . .
H H5 0.1625 1.0872 0.1510 0.057 Uiso calc R 1 . .
C C14 0.44481(9) 0.1482(4) 0.37137(11) 0.0395(4) Uani d . 1 . .
H H14A 0.4891 0.2296 0.4108 0.047 Uiso calc R 1 . .
H H14B 0.4291 -0.0321 0.3990 0.047 Uiso calc R 1 . .
C C10 0.08499(11) 1.2661(4) 0.29225(15) 0.0551(5) Uani d . 1 . .
H H10 0.0639 1.3552 0.2381 0.066 Uiso calc R 1 . .
C C11 0.05304(11) 1.3253(5) 0.37239(16) 0.0638(6) Uani d . 1 . .
H H11 0.0100 1.4531 0.3726 0.077 Uiso calc R 1 . .
C C12 0.08390(12) 1.1971(5) 0.45434(15) 0.0609(6) Uani d . 1 . .
H H12 0.0612 1.2386 0.5089 0.073 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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
C1 N1 C8 . . 117.39(13) ?
C14 O1 H1 . . 109.5 ?
C3 C2 C1 . . 115.09(14) ?
C3 C2 C14 . . 123.18(14) ?
C1 C2 C14 . . 121.71(14) ?
N1 C1 C2 . . 126.98(14) ?
N1 C1 Cl1 . . 115.47(11) ?
C2 C1 Cl1 . . 117.54(12) ?
C13 C7 C6 . . 119.02(16) ?
C13 C7 C8 . . 122.33(15) ?
C6 C7 C8 . . 118.64(15) ?
C3 C9 C8 . . 117.80(13) ?
C3 C9 C4 . . 122.41(14) ?
C8 C9 C4 . . 119.78(15) ?
C2 C3 C9 . . 121.29(14) ?
C2 C3 H3 . . 119.4 ?
C9 C3 H3 . . 119.4 ?
C5 C4 C9 . . 120.65(16) ?
C5 C4 H4 . . 119.7 ?
C9 C4 H4 . . 119.7 ?
N1 C8 C9 . . 121.44(14) ?
N1 C8 C7 . . 118.79(13) ?
C9 C8 C7 . . 119.77(13) ?
C10 C6 C7 . . 118.61(17) ?
C10 C6 C5 . . 121.83(17) ?
C7 C6 C5 . . 119.57(16) ?
C12 C13 C7 . . 120.52(18) ?
C12 C13 H13 . . 119.7 ?
C7 C13 H13 . . 119.7 ?
C4 C5 C6 . . 121.58(16) ?
C4 C5 H5 . . 119.2 ?
C6 C5 H5 . . 119.2 ?
O1 C14 C2 . . 112.85(13) ?
O1 C14 H14A . . 109.0 ?
C2 C14 H14A . . 109.0 ?
O1 C14 H14B . . 109.0 ?
C2 C14 H14B . . 109.0 ?
H14A C14 H14B . . 107.8 ?
C11 C10 C6 . . 120.88(18) ?
C11 C10 H10 . . 119.6 ?
C6 C10 H10 . . 119.6 ?
C10 C11 C12 . . 120.66(18) ?
C10 C11 H11 . . 119.7 ?
C12 C11 H11 . . 119.7 ?
C13 C12 C11 . . 120.30(19) ?
C13 C12 H12 . . 119.8 ?
C11 C12 H12 . . 119.8 ?
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
Cl1 C1 . 1.7525(15) ?
N1 C1 . 1.3014(19) ?
N1 C8 . 1.3585(19) ?
O1 C14 . 1.4155(19) ?
O1 H1 . 0.8200 ?
C2 C3 . 1.368(2) ?
C2 C1 . 1.405(2) ?
C2 C14 . 1.507(2) ?
C7 C13 . 1.402(2) ?
C7 C6 . 1.415(2) ?
C7 C8 . 1.441(2) ?
C9 C3 . 1.403(2) ?
C9 C8 . 1.411(2) ?
C9 C4 . 1.424(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.345(2) ?
C4 H4 . 0.9300 ?
C6 C10 . 1.412(2) ?
C6 C5 . 1.430(2) ?
C13 C12 . 1.372(2) ?
C13 H13 . 0.9300 ?
C5 H5 . 0.9300 ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C10 C11 . 1.353(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.389(3) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
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
O1 H1 O1 2_655 0.82 1.90 2.7154(12) 175
C3 H3 O1 . 0.93 2.47 2.809(2) 102
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
C8 N1 C1 C2 . . . . -0.2(2) ?
C8 N1 C1 Cl1 . . . . 178.89(11) ?
C3 C2 C1 N1 . . . . 0.1(2) ?
C14 C2 C1 N1 . . . . 178.96(15) ?
C3 C2 C1 Cl1 . . . . -178.97(11) ?
C14 C2 C1 Cl1 . . . . -0.1(2) ?
C1 C2 C3 C9 . . . . 0.6(2) ?
C14 C2 C3 C9 . . . . -178.32(14) ?
C8 C9 C3 C2 . . . . -1.0(2) ?
C4 C9 C3 C2 . . . . 178.28(15) ?
C3 C9 C4 C5 . . . . -179.35(15) ?
C8 C9 C4 C5 . . . . 0.0(2) ?
C1 N1 C8 C9 . . . . -0.4(2) ?
C1 N1 C8 C7 . . . . 179.86(14) ?
C3 C9 C8 N1 . . . . 0.9(2) ?
C4 C9 C8 N1 . . . . -178.40(14) ?
C3 C9 C8 C7 . . . . -179.28(13) ?
C4 C9 C8 C7 . . . . 1.4(2) ?
C13 C7 C8 N1 . . . . -2.6(2) ?
C6 C7 C8 N1 . . . . 178.27(14) ?
C13 C7 C8 C9 . . . . 177.63(15) ?
C6 C7 C8 C9 . . . . -1.5(2) ?
C13 C7 C6 C10 . . . . 0.7(2) ?
C8 C7 C6 C10 . . . . 179.84(15) ?
C13 C7 C6 C5 . . . . -178.81(16) ?
C8 C7 C6 C5 . . . . 0.4(2) ?
C6 C7 C13 C12 . . . . 0.3(3) ?
C8 C7 C13 C12 . . . . -178.85(16) ?
C9 C4 C5 C6 . . . . -1.2(3) ?
C10 C6 C5 C4 . . . . -178.47(16) ?
C7 C6 C5 C4 . . . . 1.0(3) ?
C3 C2 C14 O1 . . . . -0.9(2) ?
C1 C2 C14 O1 . . . . -179.73(13) ?
C7 C6 C10 C11 . . . . -1.1(3) ?
C5 C6 C10 C11 . . . . 178.35(18) ?
C6 C10 C11 C12 . . . . 0.6(3) ?
C7 C13 C12 C11 . . . . -0.8(3) ?
C10 C11 C12 C13 . . . . 0.4(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744747
