#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/16/2011672.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_2011672
loop_
_publ_author_name
'Chandrasekar, S.'
'Panchanatheswaran, K.'
_publ_section_title
;
 N-(3-Chlorophenyl)-α-phenylnitrone: association with benzoic
 acid through hydrogen bonding
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1442
_journal_page_last               1443
_journal_paper_doi               10.1107/S0108270100011379
_journal_volume                  56
_journal_year                    2000
_chemical_formula_analytical     'C20 H16 Cl N O3'
_chemical_formula_moiety         'C13 H10 Cl N O , C7 H6 O2'
_chemical_formula_structural     'C6H5CH\\db N(O)-C6H4Cl.C6H5COOH'
_chemical_formula_sum            'C20 H16 Cl N O3'
_chemical_formula_weight         353.79
_chemical_melting_point          112
_chemical_name_common            3-Chlorophenyl-N-phenylnitrone
_chemical_name_systematic
;
 N-(benzylidene)(3-chlorophenyl)N-oxide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                110.140(10)
_cell_angle_beta                 94.80(2)
_cell_angle_gamma                96.83(2)
_cell_formula_units_Z            2
_cell_length_a                   7.609(3)
_cell_length_b                   9.630(2)
_cell_length_c                   12.858(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      5
_cell_volume                     870.4(4)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf Nonius, 1989)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'ZORTEP (Zsolnai, 1997)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf Nonius CAD-4'
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  .0104
_diffrn_reflns_av_sigmaI/netI    .0209
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3424
_diffrn_reflns_theta_max         67.88
_diffrn_reflns_theta_min         3.69
_diffrn_standards_decay_%        negligible
_diffrn_standards_interval_count 100
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    2.098
_exptl_absorpt_correction_T_max  .811
_exptl_absorpt_correction_T_min  .594
_exptl_absorpt_correction_type   \y-scans
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            'Light yellow'
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             368
_exptl_crystal_size_max          .20
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .10
_refine_diff_density_max         .265
_refine_diff_density_min         -.270
_refine_ls_extinction_coef       .0045(9)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.052
_refine_ls_goodness_of_fit_obs   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3163
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_restrained_S_obs      1.103
_refine_ls_R_factor_all          .0638
_refine_ls_R_factor_obs          .0512
_refine_ls_shift/esd_max         <0.001
_refine_ls_shift/esd_mean        .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0770P)²+0.2612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         .1457
_refine_ls_wR_factor_obs         .1352
_reflns_number_observed          2515
_reflns_number_total             3163
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            vj1113.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0770P)^2^+0.2612P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0770P)^2^+0.2612P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        870.5(4)
_cod_database_code               2011672
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_disorder_group
_atom_site_type_symbol
Cl1 .28501(12) .83929(9) .86866(6) .0874(3) Uani d . 1 . Cl
C2 .2404(3) .8297(3) .7310(2) .0555(6) Uani d . 1 . C
C3 .2356(3) .6936(2) .6463(2) .0500(5) Uani d . 1 . C
C4 .1973(3) .6860(2) .5369(2) .0439(5) Uani d . 1 . C
C5 .1630(3) .8119(3) .5142(2) .0556(6) Uani d . 1 . C
C6 .1677(4) .9452(3) .6016(2) .0683(7) Uani d . 1 . C
C7 .2076(4) .9563(3) .7113(2) .0633(7) Uani d . 1 . C
N8 .1907(2) .5471(2) .44268(14) .0433(4) Uani d . 1 . N
O9 .1157(2) .5455(2) .34595(12) .0513(4) Uani d . 1 . O
O10 .5424(3) .5716(3) .3216(2) .0782(6) Uani d . 1 . O
C11 .2562(3) .4333(2) .4541(2) .0484(5) Uani d . 1 . C
C12 .2563(3) .2880(2) .3697(2) .0488(5) Uani d . 1 . C
C13 .3261(4) .1836(3) .4092(2) .0627(6) Uani d . 1 . C
C14 .3325(4) .0413(3) .3374(3) .0739(8) Uani d . 1 . C
C15 .2705(4) -.0012(3) .2253(3) .0788(9) Uani d . 1 . C
C16 .2029(4) .0993(3) .1849(2) .0734(8) Uani d . 1 . C
C17 .1949(4) .2436(3) .2558(2) .0590(6) Uani d . 1 . C
O18 .3283(2) .6305(2) .22562(14) .0617(5) Uani d . 1 . O
C19 .4938(3) .6108(2) .2455(2) .0481(5) Uani d . 1 . C
C20 .6142(3) .6410(2) .1684(2) .0452(5) Uani d . 1 . C
C21 .5518(3) .6805(2) .0790(2) .0499(5) Uani d . 1 . C
C22 .6679(4) .7053(3) .0079(2) .0592(6) Uani d . 1 . C
C23 .8447(4) .6900(3) .0237(2) .0662(7) Uani d . 1 . C
C24 .9080(4) .6500(3) .1121(3) .0684(7) Uani d . 1 . C
C25 .7930(3) .6262(3) .1843(2) .0587(6) Uani d . 1 . C
H3 .2604 .6042 .6600 .055 Uiso d . 1 . H
H5 .1253 .8016 .4400 .047 Uiso d . 1 . H
H6 .1407 1.0346 .5800 .087 Uiso d . 1 . H
H7 .2121 1.0576 .7800 .068 Uiso d . 1 . H
H11 .3079 .4500 .5400 .055 Uiso d . 1 . H
H13 .3758 .2254 .5000 .068 Uiso d . 1 . H
H14 .3929 -.0258 .3800 .078 Uiso d . 1 . H
H15 .2598 -.1134 .1600 .079 Uiso d . 1 . H
H16 .1511 .0583 .1000 .092 Uiso d . 1 . H
H17 .1486 .3179 .2200 .069 Uiso d . 1 . H
H18 .2458 .6059 .2800 .084 Uiso d . 1 . H
H21 .4125 .6840 .0600 .068 Uiso d . 1 . H
H22 .6142 .7318 -.0600 .068 Uiso d . 1 . H
H23 .9232 .7001 -.0400 .068 Uiso d . 1 . H
H24 1.0395 .6316 .1200 .063 Uiso d . 1 . H
H25 .8332 .5847 .2400 .061 Uiso d . 1 . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl .3639 .7018 '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
C7 C2 C3 122.8(2) ?
C7 C2 Cl1 118.9(2) yes
C3 C2 Cl1 118.3(2) yes
C2 C3 C4 118.1(2) ?
C2 C3 H3 123 ?
C4 C3 H3 119 ?
C3 C4 C5 120.6(2) ?
C3 C4 N8 121.6(2) ?
C5 C4 N8 117.9(2) ?
C6 C5 C4 119.3(2) ?
C6 C5 H5 121 ?
C4 C5 H5 119 ?
C5 C6 C7 121.3(2) ?
C5 C6 H6 116 ?
C7 C6 H6 123 ?
C2 C7 C6 118.0(2) ?
C2 C7 H7 119 ?
C6 C7 H7 123 ?
C11 N8 O9 122.9(2) yes
C11 N8 C4 121.7(2) yes
O9 N8 C4 115.4(2) yes
N8 C11 C12 128.2(2) ?
N8 C11 H11 114 ?
C12 C11 H11 118 ?
C17 C12 C13 118.4(2) ?
C17 C12 C11 126.5(2) ?
C13 C12 C11 115.0(2) ?
C14 C13 C12 120.7(3) ?
C14 C13 H13 124 ?
C12 C13 H13 116 ?
C13 C14 C15 120.2(3) ?
C13 C14 H14 112 ?
C15 C14 H14 128 ?
C16 C15 C14 120.1(3) ?
C16 C15 H15 112 ?
C14 C15 H15 128 ?
C15 C16 C17 120.7(3) ?
C15 C16 H16 116 ?
C17 C16 H16 123 ?
C16 C17 C12 119.9(2) ?
C16 C17 H17 118 ?
C12 C17 H17 122 ?
C19 O18 H18 113 yes
O10 C19 O18 121.9(2) yes
O10 C19 C20 123.3(2) yes
O18 C19 C20 114.8(2) yes
C25 C20 C21 119.3(2) ?
C25 C20 C19 119.0(2) ?
C21 C20 C19 121.7(2) ?
C22 C21 C20 119.9(2) ?
C22 C21 H21 119 ?
C20 C21 H21 121 ?
C23 C22 C21 120.6(2) ?
C23 C22 H22 122 ?
C21 C22 H22 117 ?
C22 C23 C24 120.0(2) ?
C22 C23 H23 116 ?
C24 C23 H23 124 ?
C25 C24 C23 119.8(2) ?
C25 C24 H24 121 ?
C23 C24 H24 119 ?
C24 C25 C20 120.4(2) ?
C24 C25 H25 120 ?
C20 C25 H25 119 ?
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 C2 . 1.743(2) yes
C2 C7 . 1.374(4) ?
C2 C3 . 1.380(3) ?
C3 C4 . 1.386(3) ?
C3 H3 . .97 ?
C4 C5 . 1.390(3) ?
C4 N8 . 1.455(3) yes
C5 C6 . 1.379(4) ?
C5 H5 . .94 ?
C6 C7 . 1.382(4) ?
C6 H6 . 1.03 ?
C7 H7 . 1.06 ?
N8 C11 . 1.304(3) yes
N8 O9 . 1.318(2) yes
O10 C19 . 1.209(3) yes
C11 C12 . 1.446(3) yes
C11 H11 . 1.09 ?
C12 C17 . 1.397(3) ?
C12 C13 . 1.409(3) ?
C13 C14 . 1.373(4) ?
C13 H13 . 1.11 ?
C14 C15 . 1.379(5) ?
C14 H14 . 1.10 ?
C15 C16 . 1.375(4) ?
C15 H15 . 1.11 ?
C16 C17 . 1.387(3) ?
C16 H16 . 1.05 ?
C17 H17 . 1.05 ?
O18 C19 . 1.313(3) yes
O18 H18 . 1.05 yes
C19 C20 . 1.482(3) ?
C20 C25 . 1.390(3) ?
C20 C21 . 1.395(3) ?
C21 C22 . 1.381(3) ?
C21 H21 . 1.08 ?
C22 C23 . 1.377(4) ?
C22 H22 . 1.06 ?
C23 C24 . 1.388(4) ?
C23 H23 . 1.08 ?
C24 C25 . 1.384(4) ?
C24 H24 . 1.04 ?
C25 H25 . .98 ?
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
C7 C2 C3 C4 .5(4) ?
Cl1 C2 C3 C4 179.0(2) ?
C2 C3 C4 C5 -.6(3) ?
C2 C3 C4 N8 179.6(2) ?
C3 C4 C5 C6 .1(4) ?
N8 C4 C5 C6 179.8(2) ?
C4 C5 C6 C7 .6(4) ?
C3 C2 C7 C6 .3(4) ?
Cl1 C2 C7 C6 -178.3(2) ?
C5 C6 C7 C2 -.8(4) ?
C3 C4 N8 C11 -14.7(3) ?
C5 C4 N8 C11 165.5(2) ?
C3 C4 N8 O9 165.8(2) ?
C5 C4 N8 O9 -14.0(3) ?
O9 N8 C11 C12 -2.0(4) ?
C4 N8 C11 C12 178.6(2) yes
N8 C11 C12 C17 4.3(4) ?
N8 C11 C12 C13 -175.6(2) ?
C17 C12 C13 C14 -.3(4) ?
C11 C12 C13 C14 179.6(2) ?
C12 C13 C14 C15 .0(4) ?
C13 C14 C15 C16 .4(5) ?
C14 C15 C16 C17 -.5(5) ?
C15 C16 C17 C12 .1(4) ?
C13 C12 C17 C16 .3(4) ?
C11 C12 C17 C16 -179.6(2) ?
O10 C19 C20 C25 -1.0(3) ?
O18 C19 C20 C25 178.7(2) ?
O10 C19 C20 C21 177.5(2) ?
O18 C19 C20 C21 -2.8(3) ?
C25 C20 C21 C22 -.4(3) ?
C19 C20 C21 C22 -178.9(2) ?
C20 C21 C22 C23 .6(4) ?
C21 C22 C23 C24 -.3(4) ?
C22 C23 C24 C25 -.2(4) ?
C23 C24 C25 C20 .4(4) ?
C21 C20 C25 C24 -.1(4) ?
C19 C20 C25 C24 178.4(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21135408
