#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/59/2215966.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_2215966
loop_
_publ_author_name
'Zhao, Yun-Feng'
_publ_section_title
;
 2,4-Dichloro-5-fluorobenzoic acid
;
_journal_coeditor_code           HB2604
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4449
_journal_page_last               o4449
_journal_paper_doi               10.1107/S1600536807052130
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C7 H3 Cl2 F O2'
_chemical_formula_moiety         'C7 H3 Cl2 F O2'
_chemical_formula_sum            'C7 H3 Cl2 F O2'
_chemical_formula_weight         208.99
_chemical_name_systematic
;
2,4-Dichloro-5-fluorobenzoic 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_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.515(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.0438(19)
_cell_length_b                   10.632(4)
_cell_length_c                   15.550(6)
_cell_measurement_reflns_used    1959
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      2.32
_cell_volume                     830.0(5)
_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  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_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  0.0558
_diffrn_reflns_av_sigmaI/netI    0.0582
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5973
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.32
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_correction_T_min  0.779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.373
_refine_ls_extinction_coef       0.151(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1540
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0516
_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)+(0.0612P)²+0.7105P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1416
_reflns_number_gt                1293
_reflns_number_total             1540
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2604.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2215966
_cod_database_fobs_code          2215966
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.5167(5) 0.9568(3) 0.36752(18) 0.0333(7) Uani d . 1
C C2 0.5453(5) 0.9186(3) 0.27613(17) 0.0304(6) Uani d . 1
C C3 0.3990(6) 0.8225(3) 0.23460(18) 0.0339(7) Uani d . 1
C C4 0.4315(7) 0.7892(3) 0.1506(2) 0.0443(8) Uani d . 1
H H9 0.3323 0.7236 0.1242 0.053 Uiso calc R 1
C C5 0.6115(7) 0.8534(3) 0.1059(2) 0.0481(9) Uani d . 1
C C6 0.7558(7) 0.9497(3) 0.1461(2) 0.0468(8) Uani d . 1
C C7 0.7278(6) 0.9821(3) 0.2299(2) 0.0389(7) Uani d . 1
H H7 0.8306 1.0466 0.2561 0.047 Uiso calc R 1
O O1 0.2963(4) 0.9777(2) 0.39280(13) 0.0423(6) Uani d . 1
O O2 0.7417(5) 0.9684(3) 0.41719(17) 0.0760(10) Uani d . 1
H H1 0.7099 0.9894 0.4659 0.114 Uiso calc R 1
F F1 0.9320(5) 1.0123(2) 0.10281(14) 0.0758(8) Uani d . 1
Cl Cl1 0.17719(18) 0.73365(8) 0.28805(5) 0.0506(4) Uani d . 1
Cl Cl2 0.6602(3) 0.81275(13) 0.00154(6) 0.0861(5) 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 0.0266(14) 0.0421(16) 0.0310(15) -0.0001(12) 0.0018(11) -0.0062(12)
C2 0.0286(14) 0.0331(15) 0.0294(14) 0.0048(11) 0.0024(11) -0.0023(11)
C3 0.0369(15) 0.0327(15) 0.0320(15) 0.0015(12) 0.0035(12) 0.0039(12)
C4 0.058(2) 0.0380(17) 0.0367(17) -0.0063(15) 0.0041(14) -0.0066(13)
C5 0.066(2) 0.0504(19) 0.0286(16) 0.0005(17) 0.0110(15) -0.0039(14)
C6 0.0483(19) 0.053(2) 0.0417(18) -0.0052(15) 0.0167(15) 0.0051(15)
C7 0.0362(16) 0.0397(16) 0.0417(17) -0.0039(13) 0.0085(13) -0.0061(13)
O1 0.0242(11) 0.0667(15) 0.0365(11) 0.0027(9) 0.0053(8) -0.0130(10)
O2 0.0477(16) 0.129(3) 0.0509(16) 0.0006(16) 0.0015(12) -0.0256(16)
F1 0.0881(17) 0.0890(17) 0.0564(14) -0.0316(14) 0.0390(12) -0.0013(12)
Cl1 0.0604(6) 0.0461(5) 0.0470(5) -0.0165(4) 0.0143(4) 0.0011(3)
Cl2 0.1285(11) 0.0979(9) 0.0369(6) -0.0234(7) 0.0330(6) -0.0179(5)
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
O1 C1 O2 123.3(3)
O1 C1 C2 121.5(2)
O2 C1 C2 115.2(2)
C3 C2 C7 117.8(3)
C3 C2 C1 123.2(3)
C7 C2 C1 119.1(2)
C4 C3 C2 121.7(3)
C4 C3 Cl1 117.0(2)
C2 C3 Cl1 121.2(2)
C5 C4 C3 119.6(3)
C5 C4 H9 120.2
C3 C4 H9 120.2
C6 C5 C4 119.2(3)
C6 C5 Cl2 120.0(3)
C4 C5 Cl2 120.8(3)
F1 C6 C7 119.1(3)
F1 C6 C5 119.3(3)
C7 C6 C5 121.6(3)
C6 C7 C2 120.1(3)
C6 C7 H7 119.9
C2 C7 H7 119.9
C1 O2 H1 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.234(3)
C1 O2 1.316(4)
C1 C2 1.498(4)
C2 C3 1.383(4)
C2 C7 1.395(4)
C3 C4 1.378(4)
C3 Cl1 1.736(3)
C4 C5 1.377(5)
C4 H9 0.9300
C5 C6 1.371(5)
C5 Cl2 1.720(3)
C6 F1 1.342(4)
C6 C7 1.368(4)
C7 H7 0.9300
O2 H1 0.8200
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
O2 H1 O1 3_676 0.82 2.23 3.034(3) 167
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
O1 C1 C2 C3 -49.8(4)
O2 C1 C2 C3 131.5(3)
O1 C1 C2 C7 130.3(3)
O2 C1 C2 C7 -48.5(4)
C7 C2 C3 C4 0.4(4)
C1 C2 C3 C4 -179.6(3)
C7 C2 C3 Cl1 177.3(2)
C1 C2 C3 Cl1 -2.7(4)
C2 C3 C4 C5 -0.8(5)
Cl1 C3 C4 C5 -177.8(3)
C3 C4 C5 C6 0.1(5)
C3 C4 C5 Cl2 179.1(3)
C4 C5 C6 F1 179.8(3)
Cl2 C5 C6 F1 0.8(5)
C4 C5 C6 C7 1.0(5)
Cl2 C5 C6 C7 -178.0(3)
F1 C6 C7 C2 179.8(3)
C5 C6 C7 C2 -1.3(5)
C3 C2 C7 C6 0.6(4)
C1 C2 C7 C6 -179.4(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 599623
