#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/77/2217700.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_2217700
loop_
_publ_author_name
'Liu, Hai-Lian'
'Du, Zhi-Qiang'
_publ_section_title
;
 2,4-Dichloro-6-nitrobenzoic acid
;
_journal_coeditor_code           XU2399
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o536
_journal_page_last               o536
_journal_paper_doi               10.1107/S1600536808002560
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C7 H3 Cl2 N O4'
_chemical_formula_moiety         'C7 H3 Cl2 N O4'
_chemical_formula_sum            'C7 H3 Cl2 N O4'
_chemical_formula_weight         236.00
_chemical_name_systematic
;
2,4-Dichloro-6-nitrobenzoic 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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.120(2)
_cell_angle_beta                 95.267(2)
_cell_angle_gamma                100.631(2)
_cell_formula_units_Z            2
_cell_length_a                   4.6930(7)
_cell_length_b                   7.5590(11)
_cell_length_c                   13.0721(19)
_cell_measurement_reflns_used    2069
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.77
_cell_volume                     449.11(11)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0111
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2415
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.77
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  0.8715
_exptl_absorpt_correction_T_min  0.7651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.340
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0319
_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)+(0.0463P)²+0.1228P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0865
_reflns_number_gt                1457
_reflns_number_total             1641
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2399.cif
_cod_data_source_block           I
_cod_database_code               2217700
_cod_database_fobs_code          2217700
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
Cl Cl1 0.66419(15) 0.23838(7) 0.04930(4) 0.0620(2) Uani d . 1
Cl Cl2 0.19170(13) 0.45919(8) 0.38873(4) 0.0611(2) Uani d . 1
N N1 0.8796(4) 0.9077(2) 0.20929(13) 0.0425(4) Uani d . 1
O O1 0.8119(3) 1.03193(18) 0.26405(12) 0.0542(4) Uani d . 1
O O2 1.0647(4) 0.9276(2) 0.15015(13) 0.0651(5) Uani d . 1
O O3 0.7264(3) 0.86356(19) 0.45830(10) 0.0456(3) Uani d . 1
O O4 0.3076(3) 0.9004(2) 0.37628(11) 0.0540(4) Uani d . 1
H H4A 0.2886 0.9850 0.4282 0.081 Uiso d R 1
C C1 0.5569(4) 0.6891(2) 0.29482(13) 0.0335(4) Uani d . 1
C C2 0.4126(4) 0.5107(3) 0.29348(14) 0.0388(4) Uani d . 1
C C3 0.4410(4) 0.3708(2) 0.21800(15) 0.0428(5) Uani d . 1
H H5 0.3413 0.2525 0.2182 0.051 Uiso calc R 1
C C4 0.6193(4) 0.4107(3) 0.14305(15) 0.0413(4) Uani d . 1
C C5 0.7657(4) 0.5858(3) 0.14027(15) 0.0410(4) Uani d . 1
H H3 0.8852 0.6117 0.0889 0.049 Uiso calc R 1
C C6 0.7292(4) 0.7212(2) 0.21587(14) 0.0346(4) Uani d . 1
C C7 0.5340(4) 0.8318(2) 0.38368(14) 0.0352(4) 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
Cl1 0.0958(5) 0.0399(3) 0.0486(3) 0.0164(3) 0.0174(3) -0.0113(2)
Cl2 0.0633(4) 0.0609(4) 0.0532(3) -0.0092(3) 0.0264(3) 0.0033(3)
N1 0.0503(9) 0.0346(8) 0.0403(9) 0.0024(7) 0.0099(7) 0.0021(7)
O1 0.0708(10) 0.0309(7) 0.0605(9) 0.0096(6) 0.0189(7) -0.0021(6)
O2 0.0816(11) 0.0478(9) 0.0627(10) -0.0061(8) 0.0389(9) 0.0017(7)
O3 0.0431(7) 0.0502(8) 0.0388(7) 0.0098(6) -0.0012(6) -0.0080(6)
O4 0.0438(8) 0.0655(10) 0.0506(8) 0.0230(7) 0.0038(6) -0.0162(7)
C1 0.0319(9) 0.0341(9) 0.0326(9) 0.0062(7) 0.0029(7) -0.0017(7)
C2 0.0370(10) 0.0418(10) 0.0349(9) 0.0026(8) 0.0064(8) 0.0013(8)
C3 0.0490(11) 0.0306(9) 0.0442(11) 0.0003(8) 0.0042(9) 0.0003(8)
C4 0.0531(11) 0.0346(10) 0.0347(10) 0.0106(8) 0.0054(8) -0.0047(7)
C5 0.0496(11) 0.0385(10) 0.0354(10) 0.0088(8) 0.0131(8) 0.0008(8)
C6 0.0388(9) 0.0301(9) 0.0330(9) 0.0040(7) 0.0056(7) 0.0007(7)
C7 0.0327(9) 0.0372(10) 0.0341(9) 0.0048(7) 0.0077(7) -0.0009(7)
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
O2 N1 O1 124.25(16)
O2 N1 C6 117.96(16)
O1 N1 C6 117.79(16)
C7 O4 H4A 117.5
C6 C1 C2 116.50(16)
C6 C1 C7 124.11(16)
C2 C1 C7 119.26(16)
C3 C2 C1 122.11(17)
C3 C2 Cl2 118.41(15)
C1 C2 Cl2 119.48(14)
C4 C3 C2 118.60(17)
C4 C3 H5 120.7
C2 C3 H5 120.7
C3 C4 C5 121.65(17)
C3 C4 Cl1 119.64(15)
C5 C4 Cl1 118.71(15)
C6 C5 C4 117.98(18)
C6 C5 H3 121.0
C4 C5 H3 121.0
C5 C6 C1 123.15(17)
C5 C6 N1 117.00(16)
C1 C6 N1 119.84(15)
O3 C7 O4 126.27(17)
O3 C7 C1 117.77(15)
O4 C7 C1 115.83(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C4 1.7309(18) ?
Cl2 C2 1.7277(19) ?
N1 O2 1.216(2) ?
N1 O1 1.217(2) ?
N1 C6 1.472(2) ?
O3 C7 1.235(2) y
O4 C7 1.266(2) y
O4 H4A 0.8961 ?
C1 C6 1.386(3) ?
C1 C2 1.390(3) ?
C1 C7 1.510(2) ?
C2 C3 1.388(3) ?
C3 C4 1.372(3) ?
C3 H5 0.9300 ?
C4 C5 1.381(3) ?
C5 C6 1.377(2) ?
C5 H3 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
O4 H4A O3 2_676 0.90 1.77 2.664(2) 173
C3 H5 O2 1_445 0.93 2.56 3.453(2) 160
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21119180
