#------------------------------------------------------------------------------
#$Date: 2018-02-24 09:34:03 +0200 (Sat, 24 Feb 2018) $
#$Revision: 206647 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/23/2242397.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_2242397
loop_
_publ_author_name
'Girisha, Marisiddaiah'
'Yathirajan, Hemmige S.'
'Rathore, Ravindranath S.'
'Glidewell, Christopher'
_publ_section_title
;
 Reinvestigation of the crystal structure of
 N-(4-chlorobenzylidene)-2-hydroxyaniline: a three-dimensional
 structure containing O---H···N,
 O---H···O and C---H···π(arene)
 hydrogen bonds
;
_journal_coeditor_code           ZL2725
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              376
_journal_page_last               379
_journal_paper_doi               10.1107/S205698901800244X
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C13 H10 Cl N O'
_chemical_formula_moiety         'C13 H10 Cl N O'
_chemical_formula_sum            'C13 H10 Cl N O'
_chemical_formula_weight         231.67
_chemical_name_systematic
;
N-(4-chlorobenzylidene)-2-hydroxyaniline
;
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 101.521(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0830(17)
_cell_length_b                   5.8746(6)
_cell_length_c                   14.825(2)
_cell_measurement_reflns_used    2571
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.554
_cell_measurement_theta_min      2.319
_cell_volume                     1116.5(2)
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII'
_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  0.0321
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.319
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.214
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2565
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0421
_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)+(0.0322P)²+0.4436P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.1058
_reflns_number_gt                1556
_reflns_number_total             2565
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zl2725sup1.cif
_cod_data_source_block           I
_cod_database_code               2242397
_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   0.928
_shelx_estimated_absorpt_t_max   0.957
_shelxl_version_number           2.014
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
C C1 0.65441(13) 0.6411(3) 0.62783(12) 0.0374(4) Uani d 1
C C2 0.68202(15) 0.8448(3) 0.59096(13) 0.0423(5) Uani d 1
O O2 0.60543(11) 0.9939(2) 0.55382(11) 0.0604(4) Uani d 1
H H2 0.5507(19) 0.928(5) 0.5621(18) 0.091 Uiso d 1
C C3 0.78503(15) 0.8963(4) 0.59195(14) 0.0494(5) Uani d 1
H H3 0.8029 1.0334 0.5678 0.059 Uiso calc 1
C C4 0.86113(15) 0.7427(4) 0.62911(14) 0.0523(5) Uani d 1
H H4 0.9307 0.7753 0.6290 0.063 Uiso calc 1
C C5 0.83542(15) 0.5410(4) 0.66645(14) 0.0500(5) Uani d 1
H H5 0.8876 0.4392 0.6921 0.060 Uiso calc 1
C C6 0.73255(14) 0.4898(3) 0.66596(13) 0.0436(5) Uani d 1
H H6 0.7155 0.3535 0.6912 0.052 Uiso calc 1
N N1 0.54588(11) 0.6144(3) 0.62148(10) 0.0422(4) Uani d 1
C C11 0.39586(13) 0.3955(3) 0.63857(12) 0.0390(4) Uani d 1
C C12 0.32219(14) 0.5524(3) 0.59676(13) 0.0452(5) Uani d 1
H H12 0.3437 0.6879 0.5740 0.054 Uiso calc 1
C C13 0.21690(15) 0.5086(4) 0.58864(14) 0.0507(5) Uani d 1
H H13 0.1675 0.6142 0.5609 0.061 Uiso calc 1
C C14 0.18611(14) 0.3071(4) 0.62218(14) 0.0479(5) Uani d 1
Cl Cl14 0.05422(4) 0.24857(13) 0.60947(5) 0.0861(3) Uani d 1
C C15 0.25681(16) 0.1493(4) 0.66378(14) 0.0520(5) Uani d 1
H H15 0.2347 0.0140 0.6863 0.062 Uiso calc 1
C C16 0.36183(15) 0.1950(3) 0.67172(14) 0.0496(5) Uani d 1
H H16 0.4106 0.0889 0.6999 0.059 Uiso calc 1
C C17 0.50747(14) 0.4332(3) 0.64610(13) 0.0429(5) Uani d 1
H H17 0.5529 0.3169 0.6705 0.052 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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
C6 C1 C2 118.87(17)
C6 C1 N1 127.23(18)
C2 C1 N1 113.90(16)
O2 C2 C3 120.15(18)
O2 C2 C1 118.93(17)
C3 C2 C1 120.92(17)
C2 O2 H2 103.0(18)
C4 C3 C2 119.24(19)
C4 C3 H3 120.4
C2 C3 H3 120.4
C3 C4 C5 120.68(18)
C3 C4 H4 119.7
C5 C4 H4 119.7
C4 C5 C6 120.16(19)
C4 C5 H5 119.9
C6 C5 H5 119.9
C5 C6 C1 120.12(19)
C5 C6 H6 119.9
C1 C6 H6 119.9
C17 N1 C1 121.83(16)
C16 C11 C12 118.69(17)
C16 C11 C17 119.35(17)
C12 C11 C17 121.94(17)
C13 C12 C11 120.45(19)
C13 C12 H12 119.8
C11 C12 H12 119.8
C14 C13 C12 119.16(18)
C14 C13 H13 120.4
C12 C13 H13 120.4
C15 C14 C13 121.77(18)
C15 C14 Cl14 118.96(17)
C13 C14 Cl14 119.26(16)
C14 C15 C16 118.58(19)
C14 C15 H15 120.7
C16 C15 H15 120.7
C15 C16 C11 121.36(18)
C15 C16 H16 119.3
C11 C16 H16 119.3
N1 C17 C11 123.79(17)
N1 C17 H17 118.1
C11 C17 H17 118.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.387(2)
C1 C2 1.393(3)
C1 N1 1.413(2)
C2 O2 1.361(2)
C2 C3 1.379(3)
O2 H2 0.84(3)
C3 C4 1.375(3)
C3 H3 0.9300
C4 C5 1.377(3)
C4 H4 0.9300
C5 C6 1.378(3)
C5 H5 0.9300
C6 H6 0.9300
N1 C17 1.262(2)
C11 C16 1.384(3)
C11 C12 1.387(2)
C11 C17 1.459(2)
C12 C13 1.383(3)
C12 H12 0.9300
C13 C14 1.375(3)
C13 H13 0.9300
C14 C15 1.366(3)
C14 Cl14 1.7324(19)
C15 C16 1.382(3)
C15 H15 0.9300
C16 H16 0.9300
C17 H17 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
_geom_hbond_publ_flag
O2 H2 N1 . 0.84(3) 2.05(3) 2.626(2) 125(2) y
O2 H2 O2 3_676 0.84(3) 2.44(3) 2.899(2) 115(2) y
C6 H6 Cg1 2_646 0.93 2.79 3.491(2) 133 y
C15 H15 Cg2 2_546 0.93 2.96 3.675(2) 135 y
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
C6 C1 C2 O2 -179.76(17)
N1 C1 C2 O2 0.1(2)
C6 C1 C2 C3 0.1(3)
N1 C1 C2 C3 179.96(17)
O2 C2 C3 C4 -179.48(18)
C1 C2 C3 C4 0.7(3)
C2 C3 C4 C5 -1.1(3)
C3 C4 C5 C6 0.8(3)
C4 C5 C6 C1 0.0(3)
C2 C1 C6 C5 -0.4(3)
N1 C1 C6 C5 179.72(18)
C6 C1 N1 C17 -4.9(3)
C2 C1 N1 C17 175.25(17)
C16 C11 C12 C13 0.1(3)
C17 C11 C12 C13 178.31(18)
C11 C12 C13 C14 -0.3(3)
C12 C13 C14 C15 0.4(3)
C12 C13 C14 Cl14 -178.35(15)
C13 C14 C15 C16 -0.2(3)
Cl14 C14 C15 C16 178.52(16)
C14 C15 C16 C11 0.0(3)
C12 C11 C16 C15 0.1(3)
C17 C11 C16 C15 -178.19(18)
C1 N1 C17 C11 -178.31(16)
C16 C11 C17 N1 -176.83(18)
C12 C11 C17 N1 5.0(3)

_cod_database_fobs_code 2242397
