#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/64/2236415.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_2236415
loop_
_publ_author_name
'Manjunath, B. C.'
'Abdoh, M. M. M'
'Mallesha, L.'
'Mohana, K. N.'
'Lokanath, N. K.'
_publ_section_title
;
 4-[(3-Chloro-2-methylphenyl)iminomethyl]phenol
;
_journal_coeditor_code           KJ2211
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3191
_journal_paper_doi               10.1107/S1600536812043140
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C14 H12 Cl N O'
_chemical_formula_moiety         'C14 H12 Cl N O'
_chemical_formula_sum            'C14 H12 Cl N O'
_chemical_formula_weight         245.70
_chemical_name_systematic
;
4-[(3-Chloro-2-methylphenyl)iminomethyl]phenol
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5271(9)
_cell_length_b                   12.4095(15)
_cell_length_c                   12.5800(14)
_cell_measurement_reflns_used    2042
_cell_measurement_temperature    103
_cell_measurement_theta_max      30.6
_cell_measurement_theta_min      2.3
_cell_volume                     1175.1(2)
_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    'Mercury (Macrae et al., 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103
_diffrn_detector_area_resol_mean 16.0839
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       'ω scans'
_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  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6050
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        30.56
_diffrn_reflns_theta_max         30.56
_diffrn_reflns_theta_min         2.31
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.710
_refine_diff_density_min         -0.462
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2042
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0838P)²+0.0338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1231
_reflns_number_gt                1856
_reflns_number_total             2042
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kj2211.cif
_cod_data_source_block           I
_cod_database_code               2236415
_cod_database_fobs_code          2236415
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Cl Cl1 0.20725(8) 0.07415(5) 0.21487(5) 0.0206(2) Uani . . 1.000
O O2 -0.2400(2) 0.06296(14) 1.08991(14) 0.0200(5) Uani . . 1.000
N N3 -0.0186(3) 0.11403(16) 0.60025(16) 0.0151(5) Uani . . 1.000
C C4 0.0219(3) 0.16256(18) 0.50001(19) 0.0142(6) Uani . . 1.000
C C5 0.0934(3) 0.09792(18) 0.41844(19) 0.0144(6) Uani . . 1.000
C C6 0.1173(3) 0.1473(2) 0.31955(19) 0.0147(6) Uani . . 1.000
C C7 0.0749(3) 0.2551(2) 0.3006(2) 0.0182(7) Uani . . 1.000
C C8 0.0060(3) 0.3171(2) 0.3831(2) 0.0192(7) Uani . . 1.000
C C9 -0.0203(3) 0.27089(18) 0.4822(2) 0.0165(6) Uani . . 1.000
C C10 0.0205(3) 0.16597(19) 0.68499(19) 0.0157(6) Uani . . 1.000
C C11 -0.0336(3) 0.13243(19) 0.79125(19) 0.0146(6) Uani . . 1.000
C C12 -0.1136(3) 0.03193(19) 0.81002(19) 0.0162(6) Uani . . 1.000
C C13 -0.1794(3) 0.00693(19) 0.91011(19) 0.0154(6) Uani . . 1.000
C C14 -0.1689(3) 0.08211(19) 0.99228(18) 0.0148(6) Uani . . 1.000
C C15 -0.0820(3) 0.18052(19) 0.9758(2) 0.0170(6) Uani . . 1.000
C C16 -0.0153(3) 0.20481(19) 0.8757(2) 0.0161(6) Uani . . 1.000
C C17 0.1424(3) -0.01811(19) 0.4369(2) 0.0191(7) Uani . . 1.000
H H2 -0.28810 0.00190 1.09040 0.0300 Uiso calc R 1.000
H H7 0.09280 0.28580 0.23230 0.0220 Uiso calc R 1.000
H H8 -0.02280 0.39070 0.37150 0.0230 Uiso calc R 1.000
H H9 -0.06730 0.31310 0.53850 0.0200 Uiso calc R 1.000
H H10 0.08860 0.23010 0.67830 0.0190 Uiso calc R 1.000
H H12 -0.12270 -0.01910 0.75400 0.0190 Uiso calc R 1.000
H H13 -0.23160 -0.06160 0.92270 0.0180 Uiso calc R 1.000
H H15 -0.06890 0.23030 1.03260 0.0200 Uiso calc R 1.000
H H16 0.04360 0.27160 0.86450 0.0190 Uiso calc R 1.000
H H17A 0.09600 -0.06240 0.37870 0.0290 Uiso calc R 1.000
H H17B 0.09100 -0.04250 0.50440 0.0290 Uiso calc R 1.000
H H17C 0.27200 -0.02500 0.43980 0.0290 Uiso calc R 1.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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_publ_flag
C14 O2 H2 109.00 no
C4 N3 C10 118.2(2) no
N3 C4 C5 118.9(2) no
C5 C4 C9 121.1(2) no
N3 C4 C9 119.8(2) no
C4 C5 C6 116.6(2) no
C4 C5 C17 121.7(2) no
C6 C5 C17 121.7(2) no
Cl1 C6 C5 119.71(18) no
Cl1 C6 C7 117.42(18) no
C5 C6 C7 122.9(2) no
C6 C7 C8 119.2(2) no
C7 C8 C9 119.7(2) no
C4 C9 C8 120.6(2) no
N3 C10 C11 123.8(2) no
C10 C11 C16 119.1(2) no
C12 C11 C16 119.0(2) no
C10 C11 C12 121.8(2) no
C11 C12 C13 120.3(2) no
C12 C13 C14 120.2(2) no
O2 C14 C13 122.0(2) no
O2 C14 C15 118.0(2) no
C13 C14 C15 120.0(2) no
C14 C15 C16 119.5(2) no
C11 C16 C15 120.9(2) no
C6 C7 H7 120.00 no
C8 C7 H7 120.00 no
C7 C8 H8 120.00 no
C9 C8 H8 120.00 no
C4 C9 H9 120.00 no
C8 C9 H9 120.00 no
N3 C10 H10 118.00 no
C11 C10 H10 118.00 no
C11 C12 H12 120.00 no
C13 C12 H12 120.00 no
C12 C13 H13 120.00 no
C14 C13 H13 120.00 no
C14 C15 H15 120.00 no
C16 C15 H15 120.00 no
C11 C16 H16 120.00 no
C15 C16 H16 119.00 no
C5 C17 H17A 110.00 no
C5 C17 H17B 109.00 no
C5 C17 H17C 109.00 no
H17A C17 H17B 109.00 no
H17A C17 H17C 109.00 no
H17B C17 H17C 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C6 1.737(2) no
O2 C14 1.361(3) no
O2 H2 0.8400 no
N3 C4 1.430(3) no
N3 C10 1.280(3) no
C4 C9 1.399(3) no
C4 C5 1.409(3) no
C5 C6 1.398(3) no
C5 C17 1.504(3) no
C6 C7 1.396(3) no
C7 C8 1.392(3) no
C8 C9 1.386(4) no
C10 C11 1.458(3) no
C11 C16 1.398(3) no
C11 C12 1.405(3) no
C12 C13 1.388(3) no
C13 C14 1.395(3) no
C14 C15 1.401(3) no
C15 C16 1.389(4) no
C7 H7 0.9500 no
C8 H8 0.9500 no
C9 H9 0.9500 no
C10 H10 0.9500 no
C12 H12 0.9500 no
C13 H13 0.9500 no
C15 H15 0.9500 no
C16 H16 0.9500 no
C17 H17A 0.9800 no
C17 H17B 0.9800 no
C17 H17C 0.9800 no
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
O2 H2 N3 2_455 0.8400 2.0500 2.854(3) 160.00 yes
C12 H12 O2 2_454 0.9500 2.3700 3.204(3) 146.00 no
C17 H17B N3 . 0.9800 2.4300 2.895(3) 108.00 no
C17 H17C Cg 2_554 0.98 2.73 3.649(2) 157 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
_geom_torsion_publ_flag
C10 N3 C4 C5 138.4(2) no
C10 N3 C4 C9 -45.7(3) no
C4 N3 C10 C11 171.9(2) no
N3 C4 C5 C6 175.1(2) no
N3 C4 C5 C17 -5.2(3) no
C9 C4 C5 C6 -0.8(3) no
C9 C4 C5 C17 178.9(2) no
N3 C4 C9 C8 -175.3(2) no
C5 C4 C9 C8 0.6(3) no
C4 C5 C6 Cl1 179.21(17) no
C4 C5 C6 C7 0.5(3) no
C17 C5 C6 Cl1 -0.5(3) no
C17 C5 C6 C7 -179.2(2) no
Cl1 C6 C7 C8 -178.66(18) no
C5 C6 C7 C8 0.1(3) no
C6 C7 C8 C9 -0.4(3) no
C7 C8 C9 C4 0.0(3) no
N3 C10 C11 C12 8.7(4) no
N3 C10 C11 C16 -167.4(2) no
C10 C11 C12 C13 -173.6(2) no
C16 C11 C12 C13 2.5(3) no
C10 C11 C16 C15 173.2(2) no
C12 C11 C16 C15 -2.9(3) no
C11 C12 C13 C14 1.0(3) no
C12 C13 C14 O2 176.5(2) no
C12 C13 C14 C15 -4.0(3) no
O2 C14 C15 C16 -177.0(2) no
C13 C14 C15 C16 3.5(3) no
C14 C15 C16 C11 0.0(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12551772
