#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:08:28 +0200 (vie 13 de oct de 2017) $
#$Revision: 201955 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/61/2006141.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_2006141
loop_
_publ_author_name
'Hamazaki, Hiroshi'
'Ohba, Shigeru'
'Toda, Fumio'
'Takumi, Hideaki'
_publ_section_title
;
 (E)-o-Stilbenecarboxylic Acid and its p-Methyl,
 Chloro and Methoxy Derivatives
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              620
_journal_page_last               624
_journal_paper_doi               10.1107/S0108270196015673
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C15 H11 Cl O2'
_chemical_formula_structural     C6H4(COOH)(C2H2C6H4Cl)
_chemical_formula_sum            'C15 H11 Cl O2'
_chemical_formula_weight         258.70
_chemical_melting_point          424.5(15)
_chemical_name_systematic        'p-chloro-(E)-o-stilbenecarboxylic acid'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.00
_cell_angle_beta                 98.450(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.361(2)
_cell_length_b                   5.066(3)
_cell_length_c                   22.710(2)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    300
_cell_measurement_theta_max      13.8
_cell_measurement_theta_min      10.1
_cell_volume                     1292.9(8)
_computing_cell_refinement       'AFC/MSC Diffractometer Control System'
_computing_data_collection
'AFC/MSC Diffractometer Control System (Rigaku Corporation, 1993)'
_computing_data_reduction        'local programs'
_computing_molecular_graphics    CRYSTAN-GM
_computing_publication_material  CRYSTAN-GM
_computing_structure_refinement  CRYSTAN-GM
_computing_structure_solution
'CRYSTAN-GM (Edwards, Gilmore, Mackay & Stewart, 1995)'
_diffrn_ambient_temperature      300
_diffrn_measurement_device       'Rigaku AFC-5'
_diffrn_measurement_method       θ-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         xray_tube
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            2379
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         2.0
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            'colourless '
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.25
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         975
_refine_ls_R_factor_obs          .0699
_refine_ls_shift/esd_max         0.04
_refine_ls_shift/esd_mean        0.0040
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(F) + 0.000225F²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         .0531
_reflns_number_observed          975
_reflns_number_total             2258
_reflns_observed_criterion       '|F~o~| > 3\s(|F~o~|)'
_cod_data_source_file            oa1018.cif
_cod_data_source_block           sticp
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '423-426' was changed to '424.5(15)'
- the average value was taken and precision was
estimated.

'_atom_site_thermal_displace_type' tag value 'Uij' was
replaced with 'Uani' value 18 times.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '423-426' was changed to '424.5(15)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(F) + 0.000225F^2^]'
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^(F) +
0.000225F^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2006141
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
1/2-x,1/2+y,1/2-z
-x,-y,-z
1/2+x,1/2-y,1/2+z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 .085(3) .085(4) .093(3) -.035(3) .038(3) -.033(3)
O2 .100(3) .082(4) .083(3) -.033(3) .032(3) -.025(3)
C3 .067(4) .050(5) .073(4) .005(4) .017(4) -.005(4)
C4 .055(4) .039(4) .069(4) -.001(4) .004(3) .004(4)
C5 .063(4) .072(6) .077(5) -.012(5) .024(4) .007(5)
C6 .073(5) .108(7) .075(5) -.012(5) .023(5) .026(5)
C7 .068(5) .094(7) .082(5) -.032(5) -.001(4) .018(5)
C8 .080(5) .090(7) .057(5) -.018(5) -.004(4) .007(5)
C9 .049(4) .058(5) .064(4) -.003(4) .001(3) .010(4)
C10 .084(5) .074(6) .070(4) -.040(5) .008(4) -.008(5)
C11 .085(6) .054(6) .093(6) -.020(5) .007(5) -.015(5)
C12 .068(4) .062(5) .062(4) .001(4) .017(3) .004(4)
C13 .119(7) .078(7) .085(6) -.023(6) .028(5) -.020(6)
C14 .120(7) .080(7) .064(5) .001(5) .018(5) -.015(5)
C15 .065(4) .087(6) .056(4) .007(4) -.003(3) .001(4)
C16 .067(5) .113(8) .088(5) -.024(6) .006(4) -.010(6)
C17 .081(5) .088(7) .077(5) -.021(5) .018(4) -.015(5)
Cl18 .0930(10) .157(2) .0720(10) .015(2) .0220(10) .0110(10)
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_occupancy
O1 .5392(3) -.2900(8) .0526(2) .092(2) Uani 1.000
O2 .6234(4) -.3382(9) -.0271(2) .092(2) Uani 1.000
C3 .6163(5) -.2260(10) .0237(3) .065(3) Uani 1.000
C4 .7088(5) -.0220(10) .0409(2) .055(2) Uani 1.000
C5 .7893(5) .025(2) .0021(3) .071(3) Uani 1.000
C6 .8773(6) .214(2) .0154(3) .084(3) Uani 1.000
C7 .8843(6) .351(2) .0669(3) .081(3) Uani 1.000
C8 .8055(6) .309(2) .1055(3) .076(3) Uani 1.000
C9 .7147(5) .1230(10) .0941(2) .057(3) Uani 1.000
C10 .6328(6) .085(2) .1379(3) .078(3) Uani 1.000
C11 .6216(7) .215(2) .1847(4) .080(4) Uani 1.000
C12 .5416(5) .1750(10) .2288(3) .065(3) Uani 1.000
C13 .5461(8) .331(2) .2788(4) .097(4) Uani 1.000
C14 .4697(8) .294(2) .3190(3) .091(4) Uani 1.000
C15 .3890(5) .101(2) .3122(3) .070(3) Uani 1.000
C16 .3821(7) -.059(2) .2636(3) .091(4) Uani 1.000
C17 .4575(6) -.021(2) .2218(3) .085(3) Uani 1.000
Cl18 .29260(10) .0475(5) .36348(7) .1080(10) Uani 1.000
H2 .57393 -.48943 -.03775 .12(3) Uiso 1.000
H5 .783(5) -.074(12) -.037(2) .12(3) Uiso 1.000
H6 .930(4) .233(9) -.011(2) .06(2) Uiso 1.000
H7 .948(4) .475(9) .076(2) .05(2) Uiso 1.000
H8 .813(4) .383(11) .140(2) .07(2) Uiso 1.000
H10 .588(4) -.059(11) .133(2) .08(2) Uiso 1.000
H11 .664(3) .339(9) .194(2) .03(2) Uiso 1.000
H13 .590(5) .455(12) .280(3) .08(3) Uiso 1.000
H14 .473(4) .394(11) .353(2) .08(2) Uiso 1.000
H16 .329(4) -.171(11) .257(2) .06(2) Uiso 1.000
H17 .447(5) -.125(12) .192(2) .10(3) Uiso 1.000
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
O1 C3 O2 120.5(6) yes
O1 C3 C4 125.7(6) yes
O2 C3 C4 113.8(6) yes
C3 C4 C5 117.5(6) yes
C3 C4 C9 122.2(5) yes
C5 C4 C9 120.4(6) ?
C4 C5 C6 120.2(7) ?
C5 C6 C7 119.5(7) ?
C6 C7 C8 121.1(7) ?
C7 C8 C9 121.7(7) ?
C4 C9 C8 117.0(6) ?
C4 C9 C10 123.8(6) ?
C8 C9 C10 119.2(6) ?
C9 C10 C11 130.4(7) yes
C10 C11 C12 130.4(8) yes
C11 C12 C13 122.2(7) ?
C11 C12 C17 121.0(7) ?
C13 C12 C17 116.8(7) ?
C12 C13 C14 121.6(8) ?
C13 C14 C15 121.2(8) ?
Cl18 C15 C14 121.9(6) ?
Cl18 C15 C16 119.0(6) ?
C14 C15 C16 119.1(7) ?
C15 C16 C17 120.4(8) ?
C12 C17 C16 120.8(8) ?
C3 O2 H2 117.5(5) ?
C4 C5 H5 120.(3) ?
C6 C5 H5 120.(3) ?
C5 C6 H6 117.(3) ?
C7 C6 H6 123.(3) ?
C6 C7 H7 119.(3) ?
C8 C7 H7 120.(3) ?
C7 C8 H8 122.(3) ?
C9 C8 H8 116.(3) ?
C9 C10 H10 116.(3) ?
C11 C10 H10 114.(3) ?
C10 C11 H11 119.(3) ?
C12 C11 H11 111.(3) ?
C12 C13 H13 116.(4) ?
C14 C13 H13 122.(4) ?
C13 C14 H14 123.(3) ?
C15 C14 H14 116.(3) ?
C15 C16 H16 120.(4) ?
C17 C16 H16 119.(4) ?
C12 C17 H17 124.(4) ?
C16 C17 H17 116.(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C3 . . 1.213(8) yes
O2 C3 . . 1.301(8) yes
C3 C4 . . 1.485(9) yes
C4 C5 . . 1.382(9) ?
C4 C9 . . 1.407(8) ?
C5 C6 . . 1.384(11) ?
C6 C7 . . 1.352(11) ?
C7 C8 . . 1.359(10) ?
C8 C9 . . 1.391(10) ?
C9 C10 . . 1.472(9) yes
C10 C11 . . 1.273(11) yes
C11 C12 . . 1.461(10) yes
C12 C13 . . 1.380(11) ?
C12 C17 . . 1.371(11) ?
C13 C14 . . 1.362(12) ?
C14 C15 . . 1.335(11) ?
C15 C16 . . 1.362(11) ?
C16 C17 . . 1.384(11) ?
Cl18 C15 . . 1.733(7) yes
O2 H2 . . .96 ?
C5 H5 . . 1.00(6) ?
C6 H6 . . .91(5) ?
C7 H7 . . .96(5) ?
C8 H8 . . .86(5) ?
C10 H10 . . .88(6) ?
C11 H11 . . .80(5) ?
C13 H13 . . .80(6) ?
C14 H14 . . .93(5) ?
C16 H16 . . .82(6) ?
C17 H17 . . .86(6) ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O(1) O(2) 2.642(6) 3_645.
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652165
