#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/38/2003836.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_2003836
loop_
_publ_author_name
'Mansilla-Koblavi, F.'
'Tenon, J. A.'
'Toure, S.'
'Ebby, N.'
'Lapasset, J.'
'Carles, M.'
_publ_section_title
;
 Une Serie de N-(2,3-Dihydroxybenzilidene)amines: Manifestation
 d'Equilibres Tautomères
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1595
_journal_page_last               1602
_journal_paper_doi               10.1107/S0108270194002945
_journal_volume                  51
_journal_year                    1995
_chemical_compound_source        synthesis
_chemical_formula_sum            'C13 H10 Cl N O2'
_chemical_formula_weight         247.5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_type_scat_source           SHELX76
_cell_angle_alpha                90
_cell_angle_beta                 112.34(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.236(7)
_cell_length_b                   7.714(3)
_cell_length_c                   21.663(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      16.87
_cell_measurement_theta_min      6.64
_cell_volume                     1118.4(13)
_diffrn_measurement_device       CAD-4
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            2625
_diffrn_reflns_theta_max         17
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_number         '3 (1\=35, 12\=4, 01\=6)'
_exptl_absorpt_coefficient_mu    0.325
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.47
_exptl_crystal_description       prisme
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.269
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.34
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     154
_refine_ls_number_reflns         809
_refine_ls_R_factor_obs          0.046
_refine_ls_shift/esd_max         0.043
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      unit
_refine_ls_wR_factor_obs         0.046
_reflns_number_observed          809
_reflns_number_total             2434
_reflns_observed_criterion       I>2.5\s(I)
_cod_data_source_file            pa1059.cif
_cod_data_source_block           pa1059c
_cod_original_cell_volume        1118.0(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C13 H10 Cl1 N1 O2'
_cod_database_code               2003836
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_B_iso_or_equiv
C(1) .7793(10) .0995(7) .5956(3) 2.2(6)
C(2) .7147(10) .2703(8) .5727(3) 2.5(6)
C(3) .7228(10) .3977(8) .6213(3) 2.8(6)
C(4) .7890(10) .3525(9) .6877(3) 3.0(6)
C(5) .8481(10) .1845(8) .7096(3) 3.0(6)
C(6) .8434(10) .0592(9) .6647(3) 3.1(7)
C(7) .7834(11) -.0323(8) .5500(3) 2.7(7)
C(8) .7410(10) -.1265(9) .4394(3) 2.5(6)
C(9) .6992(11) -.0741(8) .3727(3) 3.1(7)
C(10) .6861(11) -.1907(10) .3239(4) 3.8(8)
C(11) .7370(12) -.3618(11) .3412(4) 4.4(8)
C(12) .7928(12) -.4166(9) .4066(4) 4.3(9)
C(13) .7922(11) -.3006(9) .4547(4) 3.5(8)
N .7365(9) -.0017(7) .4866(3) 2.6(5)
O(2) .6480(7) .3141(5) .5089(2) 3.4(4)
O(3) .6696(8) .5664(6) .6018(2) 3.8(5)
Cl .6297(4) .1419(2) .3513(1) 1.9(2)
H(2) .6492 .2191 .4841 ?
H(3) .5688 .5755 .5535 ?
H(4) .7909 .4363 .7183 ?
H(5) .9045 .1648 .7635 ?
H(6) .9076 -.0551 .6765 ?
H(7) .8469 -.1515 .5715 ?
H(10) .6304 -.1509 .2761 ?
H(11) .7551 -.4298 .3070 ?
H(12) .8609 -.5394 .4242 ?
H(13) .8384 -.3358 .4986 ?
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
C(6) C(1) C(2) 120.1(6) no
C(7) C(1) C(2) 120.6(6) no
C(7) C(1) C(6) 119.3(6) no
C(3) C(2) C(1) 117.7(6) no
O(2) C(2) C(1) 122.8(6) no
O(2) C(2) C(3) 119.5(6) no
C(4) C(3) C(2) 119.8(6) no
O(3) C(3) C(2) 119.7(6) no
O(3) C(3) C(4) 120.4(6) no
C(5) C(4) C(3) 122.2(6) no
C(6) C(5) C(4) 119.7(6) no
C(5) C(6) C(1) 120.4(6) no
N C(7) C(1) 122.3(6) no
C(8) N C(7) 124.8(5) no
C(9) C(8) C(13) 116.7(6) no
C(9) C(8) N 119.2(6) no
C(13) C(8) N 124.0(6) no
C(8) C(9) C(10) 121.8(6) no
C(8) C(9) Cl 118.0(5) no
C(10) C(9) Cl 119.6(6) no
C(9) C(10) C(11) 119.2(7) no
C(10) C(11) C(12) 120.8(7) no
C(11) C(12) C(13) 119.8(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C(1) C(2) 1.423(8) no
C(2) C(3) 1.425(8) no
C(3) C(4) 1.376(9) no
C(4) C(5) 1.391(9) no
C(5) C(6) 1.363(9) no
C(6) C(1) 1.423(9) no
C(1) C(7) 1.426(9) no
C(7) N 1.303(8) no
N C(8) 1.415(7) no
C(8) C(9) 1.418(9) no
C(9) C(10) 1.364(11) no
C(10) C(11) 1.384(10) no
C(11) C(12) 1.385(11) no
C(12) C(13) 1.375(12) no
C(13) C(8) 1.399(9) no
C(9) Cl 1.751(6) no
C(2) O(2) 1.323(7) no
O(2) H(2) 0.911(4) no
N H(N) 1.105(6) no
C(3) O(3) 1.378(7) no
O(3) H(3) 1.025(4) no
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
C(1) C(2) O(2) H(2) 1 no
C(2) C(3) O(3) H(3) 27 no
C(2) C(1) C(7) N 3 no
C(1) C(7) N C(8) 179 no
C(7) N C(8) C(9) -176 no
C(7) N C(8) C(13) 2 no
