#------------------------------------------------------------------------------
#$Date: 2023-01-31 10:51:16 +0200 (Tue, 31 Jan 2023) $
#$Revision: 280690 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/66/8106629.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106629
loop_
_publ_author_name
'Linxin, Deng'
'Hui, Liu'
'Song, Li'
_publ_section_title
;
 Crystal structure of 4-(chloromethyl)-3-nitrobenzoic acid, C8H6ClNO4
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              647
_journal_page_last               648
_journal_paper_doi               10.1515/ncrs-2016-0389
_journal_volume                  232
_journal_year                    2017
_chemical_formula_sum            'C8 H6 Cl N O4'
_chemical_formula_weight         215.59
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 100.6050(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.5316(7)
_cell_length_b                   17.0508(15)
_cell_length_c                   14.1080(13)
_cell_measurement_reflns_used    2558
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.956
_cell_measurement_theta_min      2.389
_cell_volume                     1780.8(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0602
_diffrn_reflns_av_sigmaI/netI    0.0725
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8611
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  0.8385
_exptl_absorpt_correction_T_min  0.8257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.44
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1020
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0671P)²+1.2136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1692
_reflns_number_gt                1891
_reflns_number_total             3133
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0389_suppl.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               8106629
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.16472(18) 0.42402(8) 0.57674(8) 0.0696(4) Uani 1 1 d . . .
Cl2 Cl -0.2314(2) 0.26840(10) 0.31791(10) 0.0961(6) Uani 1 1 d . . .
N1 N 0.5049(5) 0.3612(2) 0.4792(2) 0.0551(10) Uani 1 1 d . . .
N2 N 0.2159(7) 0.2186(3) 0.2585(3) 0.0646(11) Uani 1 1 d . . .
O1 O 0.6652(4) 0.49873(18) 0.1957(2) 0.0564(8) Uani 1 1 d . . .
O2 O 0.4115(4) 0.55254(17) 0.11810(19) 0.0555(8) Uani 1 1 d . . .
H2 H 0.4798 0.5682 0.0831 0.083 Uiso 1 1 calc R . .
O3 O 0.6561(4) 0.3842(2) 0.5098(3) 0.0918(13) Uani 1 1 d . . .
O4 O 0.4398(4) 0.3034(2) 0.5091(3) 0.0786(11) Uani 1 1 d . . .
O5 O 0.4032(4) 0.38874(17) 0.00531(19) 0.0542(8) Uani 1 1 d . . .
O6 O 0.1500(4) 0.44530(17) -0.0706(2) 0.0572(8) Uani 1 1 d . . .
H6 H 0.2215 0.4670 -0.0994 0.086 Uiso 1 1 calc R . .
O7 O 0.1613(10) 0.2150(8) 0.3334(6) 0.090(4) Uani 0.66(2) 1 d P A 1
O8 O 0.366(2) 0.1914(8) 0.2496(10) 0.077(3) Uani 0.66(2) 1 d P A 1
O7' O 0.114(2) 0.1599(13) 0.2839(15) 0.084(8) Uani 0.34(2) 1 d P A 2
O8' O 0.360(5) 0.2245(18) 0.277(2) 0.095(8) Uani 0.34(2) 1 d P A 2
C1 C 0.4999(5) 0.5120(2) 0.1861(3) 0.0426(9) Uani 1 1 d . . .
C2 C 0.3991(5) 0.4789(2) 0.2567(2) 0.0378(9) Uani 1 1 d . . .
C3 C 0.4892(5) 0.4382(2) 0.3348(3) 0.0424(10) Uani 1 1 d . . .
H3 H 0.6140 0.4327 0.3438 0.051 Uiso 1 1 calc R . .
C4 C 0.3957(5) 0.4056(2) 0.3998(3) 0.0406(9) Uani 1 1 d . . .
C5 C 0.2088(5) 0.4125(2) 0.3905(3) 0.0400(9) Uani 1 1 d . . .
C6 C 0.1213(5) 0.4543(2) 0.3117(3) 0.0458(10) Uani 1 1 d . . .
H6A H -0.0033 0.4605 0.3030 0.055 Uiso 1 1 calc R . .
C7 C 0.2127(5) 0.4869(2) 0.2461(3) 0.0440(10) Uani 1 1 d . . .
H7 H 0.1494 0.5148 0.1939 0.053 Uiso 1 1 calc R . .
C8 C 0.1022(5) 0.3800(3) 0.4607(3) 0.0490(10) Uani 1 1 d . . .
H8A H 0.1214 0.3238 0.4664 0.059 Uiso 1 1 calc R . .
H8B H -0.0254 0.3890 0.4368 0.059 Uiso 1 1 calc R . .
C9 C 0.2356(5) 0.3985(2) -0.0077(3) 0.0401(9) Uani 1 1 d . . .
C10 C 0.1276(5) 0.3541(2) 0.0514(2) 0.0374(9) Uani 1 1 d . A .
C11 C 0.2140(5) 0.3066(2) 0.1250(3) 0.0426(10) Uani 1 1 d . . .
H11 H 0.3393 0.3028 0.1378 0.051 Uiso 1 1 calc R A .
C12 C 0.1125(6) 0.2652(2) 0.1790(3) 0.0442(10) Uani 1 1 d . A .
C13 C -0.0747(6) 0.2661(2) 0.1611(3) 0.0478(10) Uani 1 1 d . . .
C14 C -0.1566(6) 0.3135(3) 0.0860(3) 0.0526(11) Uani 1 1 d . A .
H14 H -0.2821 0.3159 0.0715 0.063 Uiso 1 1 calc R . .
C15 C -0.0586(6) 0.3569(3) 0.0324(3) 0.0521(11) Uani 1 1 d . . .
H15 H -0.1179 0.3886 -0.0172 0.063 Uiso 1 1 calc R A .
C16 C -0.1926(7) 0.2198(3) 0.2140(3) 0.0637(13) Uani 1 1 d . A .
H16A H -0.1363 0.1695 0.2321 0.076 Uiso 1 1 calc R . .
H16B H -0.3073 0.2100 0.1717 0.076 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O3 N1 O4 123.8(3) . .
O3 N1 C4 117.6(3) . .
O4 N1 C4 118.6(4) . .
O8' N2 O7 106.4(18) . .
O8' N2 O8 33.6(15) . .
O7 N2 O8 122.1(8) . .
O8' N2 O7' 127.0(17) . .
O7 N2 O7' 55.0(6) . .
O8 N2 O7' 108.6(8) . .
O8' N2 C12 120.4(16) . .
O7 N2 C12 118.5(5) . .
O8 N2 C12 119.0(7) . .
O7' N2 C12 110.8(8) . .
C1 O2 H2 109.5 . .
C9 O6 H6 109.5 . .
O1 C1 O2 123.7(4) . .
O1 C1 C2 119.0(3) . .
O2 C1 C2 117.2(3) . .
C3 C2 C7 118.5(3) . .
C3 C2 C1 119.8(3) . .
C7 C2 C1 121.7(3) . .
C2 C3 C4 120.2(3) . .
C2 C3 H3 119.9 . .
C4 C3 H3 119.9 . .
C3 C4 C5 122.4(3) . .
C3 C4 N1 115.7(3) . .
C5 C4 N1 121.9(3) . .
C6 C5 C4 116.3(3) . .
C6 C5 C8 119.4(3) . .
C4 C5 C8 124.3(3) . .
C7 C6 C5 121.9(4) . .
C7 C6 H6A 119.0 . .
C5 C6 H6A 119.0 . .
C6 C7 C2 120.7(3) . .
C6 C7 H7 119.7 . .
C2 C7 H7 119.7 . .
C5 C8 Cl1 111.7(3) . .
C5 C8 H8A 109.3 . .
Cl1 C8 H8A 109.3 . .
C5 C8 H8B 109.3 . .
Cl1 C8 H8B 109.3 . .
H8A C8 H8B 107.9 . .
O5 C9 O6 123.4(4) . .
O5 C9 C10 119.7(3) . .
O6 C9 C10 116.9(3) . .
C15 C10 C11 119.2(4) . .
C15 C10 C9 121.3(3) . .
C11 C10 C9 119.5(3) . .
C12 C11 C10 119.1(4) . .
C12 C11 H11 120.5 . .
C10 C11 H11 120.5 . .
C11 C12 C13 123.1(4) . .
C11 C12 N2 115.5(4) . .
C13 C12 N2 121.4(4) . .
C14 C13 C12 116.2(4) . .
C14 C13 C16 118.1(4) . .
C12 C13 C16 125.7(4) . .
C15 C14 C13 122.0(4) . .
C15 C14 H14 119.0 . .
C13 C14 H14 119.0 . .
C14 C15 C10 120.4(4) . .
C14 C15 H15 119.8 . .
C10 C15 H15 119.8 . .
C13 C16 Cl2 112.0(3) . .
C13 C16 H16A 109.2 . .
Cl2 C16 H16A 109.2 . .
C13 C16 H16B 109.2 . .
Cl2 C16 H16B 109.2 . .
H16A C16 H16B 107.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C8 1.783(4) .
Cl2 C16 1.755(4) .
N1 O3 1.207(4) .
N1 O4 1.209(4) .
N1 C4 1.472(5) .
N2 O8' 1.07(3) .
N2 O7 1.203(8) .
N2 O8 1.250(16) .
N2 O7' 1.350(17) .
N2 C12 1.474(5) .
O1 C1 1.248(4) .
O2 C1 1.268(4) .
O2 H2 0.8200 .
O5 C9 1.252(4) .
O6 C9 1.277(4) .
O6 H6 0.8200 .
C1 C2 1.472(5) .
C2 C3 1.371(5) .
C2 C7 1.391(5) .
C3 C4 1.372(5) .
C3 H3 0.9300 .
C4 C5 1.394(5) .
C5 C6 1.382(5) .
C5 C8 1.492(5) .
C6 C7 1.368(5) .
C6 H6A 0.9300 .
C7 H7 0.9300 .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C10 1.476(5) .
C10 C15 1.379(5) .
C10 C11 1.382(5) .
C11 C12 1.370(6) .
C11 H11 0.9300 .
C12 C13 1.386(6) .
C13 C14 1.384(6) .
C13 C16 1.487(6) .
C14 C15 1.367(6) .
C14 H14 0.9300 .
C15 H15 0.9300 .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O1 C1 C2 C3 4.0(6) . . . .
O2 C1 C2 C3 -176.4(3) . . . .
O1 C1 C2 C7 -175.4(4) . . . .
O2 C1 C2 C7 4.3(5) . . . .
C7 C2 C3 C4 0.8(6) . . . .
C1 C2 C3 C4 -178.5(4) . . . .
C2 C3 C4 C5 -0.5(6) . . . .
C2 C3 C4 N1 178.2(3) . . . .
O3 N1 C4 C3 34.3(6) . . . .
O4 N1 C4 C3 -144.7(4) . . . .
O3 N1 C4 C5 -147.0(4) . . . .
O4 N1 C4 C5 34.0(6) . . . .
C3 C4 C5 C6 -0.1(6) . . . .
N1 C4 C5 C6 -178.7(4) . . . .
C3 C4 C5 C8 -178.2(4) . . . .
N1 C4 C5 C8 3.2(6) . . . .
C4 C5 C6 C7 0.3(6) . . . .
C8 C5 C6 C7 178.5(4) . . . .
C5 C6 C7 C2 0.0(6) . . . .
C3 C2 C7 C6 -0.6(6) . . . .
C1 C2 C7 C6 178.7(4) . . . .
C6 C5 C8 Cl1 -115.3(3) . . . .
C4 C5 C8 Cl1 62.7(5) . . . .
O5 C9 C10 C15 -173.1(4) . . . .
O6 C9 C10 C15 6.7(5) . . . .
O5 C9 C10 C11 4.7(5) . . . .
O6 C9 C10 C11 -175.5(3) . . . .
C15 C10 C11 C12 -1.7(5) . . . .
C9 C10 C11 C12 -179.5(3) . . . .
C10 C11 C12 C13 2.5(6) . . . .
C10 C11 C12 N2 -177.6(4) . . . .
O8' N2 C12 C11 8(2) . . . .
O7 N2 C12 C11 141.9(9) . . . .
O8 N2 C12 C11 -30.6(10) . . . .
O7' N2 C12 C11 -157.6(11) . . . .
O8' N2 C12 C13 -172(2) . . . .
O7 N2 C12 C13 -38.1(10) . . . .
O8 N2 C12 C13 149.3(9) . . . .
O7' N2 C12 C13 22.4(12) . . . .
C11 C12 C13 C14 -1.6(6) . . . .
N2 C12 C13 C14 178.4(4) . . . .
C11 C12 C13 C16 177.1(4) . . . .
N2 C12 C13 C16 -2.9(6) . . . .
C12 C13 C14 C15 0.0(6) . . . .
C16 C13 C14 C15 -178.8(4) . . . .
C13 C14 C15 C10 0.6(7) . . . .
C11 C10 C15 C14 0.2(6) . . . .
C9 C10 C15 C14 178.0(4) . . . .
C14 C13 C16 Cl2 -94.8(4) . . . .
C12 C13 C16 Cl2 86.5(5) . . . .
