#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/94/2219478.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_2219478
loop_
_publ_author_name
'Guo, Xin-Hong'
_publ_section_title
;
 3,7-Dichloroquinoline-8-carboxylic acid
;
_journal_coeditor_code           ZL2136
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1786
_journal_paper_doi               10.1107/S1600536808026238
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C10 H5 Cl2 N O2'
_chemical_formula_moiety         'C10 H5 Cl2 N O2'
_chemical_formula_sum            'C10 H5 Cl2 N O2'
_chemical_formula_weight         242.05
_chemical_name_common            quinclorac
_chemical_name_systematic
;
3,7-Dichloroquinoline-8-carboxylic acid
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                102.529(6)
_cell_angle_beta                 93.439(6)
_cell_angle_gamma                116.479(4)
_cell_formula_units_Z            2
_cell_length_a                   7.5002(12)
_cell_length_b                   8.4016(14)
_cell_length_c                   8.732(3)
_cell_measurement_reflns_used    958
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.45
_cell_measurement_theta_min      2.11
_cell_volume                     473.0(2)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       ω
_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  0.0674
_diffrn_reflns_av_sigmaI/netI    0.1041
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5948
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.43
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.659
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismlike
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.432
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1834
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0631
_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)+(0.062P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1404
_reflns_number_gt                1102
_reflns_number_total             1834
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zl2136.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 
;
_cod_original_cell_volume        472.98(17)
_cod_database_code               2219478
_cod_database_fobs_code          2219478
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.3476(6) 0.5471(6) 0.2465(5) 0.0354(10) Uani d . 1
H H1 0.3861 0.5957 0.1583 0.043 Uiso calc R 1
C C2 0.2932(6) 0.3616(6) 0.2276(5) 0.0324(9) Uani d . 1
C C3 0.2343(6) 0.2876(6) 0.3515(5) 0.0337(10) Uani d . 1
H H3 0.1963 0.1613 0.3413 0.040 Uiso calc R 1
C C4 0.1686(6) 0.3342(6) 0.6269(5) 0.0369(10) Uani d . 1
H H4 0.1286 0.2086 0.6220 0.044 Uiso calc R 1
C C5 0.1655(7) 0.4475(6) 0.7605(5) 0.0363(10) Uani d . 1
H H5 0.1215 0.4011 0.8489 0.044 Uiso calc R 1
C C6 0.2272(6) 0.6342(6) 0.7699(5) 0.0308(9) Uani d . 1
C C7 0.2918(6) 0.7078(5) 0.6455(5) 0.0253(8) Uani d . 1
C C8 0.2910(5) 0.5882(5) 0.5036(5) 0.0261(8) Uani d . 1
C C9 0.2304(6) 0.4002(5) 0.4943(5) 0.0261(8) Uani d . 1
C C10 0.3645(6) 0.9105(5) 0.6610(4) 0.0293(9) Uani d . 1
Cl Cl1 0.29545(15) 0.22889(15) 0.04666(12) 0.0385(3) Uani d . 1
Cl Cl2 0.23077(17) 0.77619(16) 0.94953(12) 0.0422(3) Uani d . 1
N N1 0.3496(5) 0.6591(4) 0.3774(4) 0.0283(7) Uani d . 1
O O1 0.5586(4) 0.9997(4) 0.6659(3) 0.0302(6) Uani d . 1
H H1A 0.597(7) 1.106(7) 0.652(5) 0.036 Uiso d . 1
O O2 0.2510(5) 0.9766(4) 0.6634(5) 0.0519(9) Uani d . 1
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
C1 0.038(2) 0.041(3) 0.032(2) 0.021(2) 0.0079(18) 0.012(2)
C2 0.027(2) 0.032(2) 0.039(2) 0.0174(19) 0.0036(17) 0.0030(19)
C3 0.033(2) 0.021(2) 0.049(2) 0.016(2) 0.0051(19) 0.008(2)
C4 0.037(2) 0.025(2) 0.053(3) 0.014(2) 0.006(2) 0.022(2)
C5 0.043(2) 0.035(3) 0.036(2) 0.019(2) 0.0106(19) 0.017(2)
C6 0.0262(19) 0.035(2) 0.033(2) 0.0165(18) 0.0041(16) 0.0098(19)
C7 0.028(2) 0.020(2) 0.032(2) 0.0138(17) 0.0062(16) 0.0073(17)
C8 0.0180(18) 0.024(2) 0.034(2) 0.0095(16) 0.0014(15) 0.0050(17)
C9 0.0258(18) 0.020(2) 0.036(2) 0.0126(16) 0.0030(16) 0.0091(17)
C10 0.034(2) 0.025(2) 0.0246(19) 0.0119(18) 0.0010(15) 0.0038(18)
Cl1 0.0372(6) 0.0432(7) 0.0423(6) 0.0303(5) 0.0101(5) -0.0006(5)
Cl2 0.0548(7) 0.0433(7) 0.0343(6) 0.0280(6) 0.0144(5) 0.0089(5)
N1 0.0318(18) 0.0235(18) 0.0295(17) 0.0130(15) 0.0066(13) 0.0069(15)
O1 0.0319(16) 0.0189(15) 0.0364(16) 0.0071(13) 0.0056(12) 0.0120(13)
O2 0.048(2) 0.0257(17) 0.092(3) 0.0240(16) 0.0204(18) 0.0171(18)
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'
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'
Cl Cl 0.1484 0.1585 '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
N1 C1 C2 124.6(4)
N1 C1 H1 117.7
C2 C1 H1 117.7
C3 C2 C1 118.9(4)
C3 C2 Cl1 121.5(3)
C1 C2 Cl1 119.6(3)
C2 C3 C9 119.2(4)
C2 C3 H3 120.4
C9 C3 H3 120.4
C5 C4 C9 120.5(4)
C5 C4 H4 119.7
C9 C4 H4 119.7
C4 C5 C6 120.2(4)
C4 C5 H5 119.9
C6 C5 H5 119.9
C7 C6 C5 122.1(4)
C7 C6 Cl2 119.9(3)
C5 C6 Cl2 118.0(3)
C6 C7 C8 117.8(4)
C6 C7 C10 121.0(3)
C8 C7 C10 121.2(3)
N1 C8 C7 118.2(4)
N1 C8 C9 121.6(3)
C7 C8 C9 120.2(4)
C3 C9 C4 122.9(4)
C3 C9 C8 118.0(4)
C4 C9 C8 119.1(3)
O2 C10 O1 125.4(4)
O2 C10 C7 122.5(3)
O1 C10 C7 112.1(3)
C1 N1 C8 117.7(3)
C10 O1 H1A 113(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.308(5)
C1 C2 1.391(6)
C1 H1 0.9500
C2 C3 1.362(6)
C2 Cl1 1.731(4)
C3 C9 1.403(6)
C3 H3 0.9500
C4 C5 1.345(6)
C4 C9 1.405(5)
C4 H4 0.9500
C5 C6 1.405(6)
C5 H5 0.9500
C6 C7 1.373(6)
C6 Cl2 1.743(4)
C7 C8 1.414(5)
C7 C10 1.510(5)
C8 N1 1.369(5)
C8 C9 1.417(5)
C10 O2 1.206(5)
C10 O1 1.299(5)
O1 H1A 0.84(5)
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
O1 H1A N1 2_676 0.84(5) 1.91(5) 2.753(4) 173(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 82837
