#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/66/1546681.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_1546681
loop_
_publ_author_name
'Medjroubi, Mohamed Larbi'
'Boudjada, Ali'
'Hamdouni, Noudjoud'
'Jeannin, Olivier'
'Meinnel, Jean'
_publ_section_title
;
 2,6-Dichloro-4-nitrotoluene
;
_journal_coeditor_code           LH4019
_journal_issue                   5
_journal_name_full               IUCrData
_journal_page_first              x170672
_journal_paper_doi               10.1107/S2414314617006721
_journal_volume                  2
_journal_year                    2017
_chemical_formula_iupac          'C7 H5 Cl2 N1 O2'
_chemical_formula_moiety         'C7 H5 Cl2 N1 O2'
_chemical_formula_structural     'C7 H5 Cl2 N1 O2'
_chemical_formula_sum            'C7 H5 Cl2 N O2'
_chemical_formula_weight         206.02
_chemical_name_common
;
2,6-Dichloro-4-nitrotoluene
;
_chemical_name_systematic
;
1,3-Dichloro-2-methyl-5-nitrobenzene
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8145(3)
_cell_length_b                   12.4829(10)
_cell_length_c                   17.4438(15)
_cell_measurement_reflns_used    2377
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.28
_cell_measurement_theta_min      2.85
_cell_volume                     830.60(12)
_computing_cell_refinement
;
SAINT (Bruker, 2006)
;
_computing_data_collection
;
APEX2 (Bruker, 2006)
;
_computing_data_reduction
;
SAINT (Bruker, 2006)
;
_computing_molecular_graphics
;
CAMERON (Watkin et al.,  1996) and Mercury (Macrae et al.,
 2008)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR2003 (Burla et al.,  2005)
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4472
_diffrn_reflns_theta_full        25.241
_diffrn_reflns_theta_max         27.582
_diffrn_reflns_theta_min         2.849
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.195
_refine_ls_abs_structure_details
;
Flack x determined using 640 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1879
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0243P)²+0.1882P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0645
_refine_ls_wR_factor_ref         0.0659
_reflns_number_gt                1756
_reflns_number_total             1879
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lh4019sup1.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C7 H5 Cl2 N1 O2'
_cod_database_code               1546681
_cod_database_fobs_code          1546681
_shelxl_version_number           2.013
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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_occupancy
Cl Cl21 0.9157(2) 0.39246(5) 0.72626(4) 0.0367(2) Uani d 1
Cl Cl61 0.36788(19) 0.75690(4) 0.60731(4) 0.03019(17) Uani d 1
O O41 0.3055(7) 0.4621(2) 0.40010(12) 0.0573(7) Uani d 1
O O42 0.6101(8) 0.32613(16) 0.43872(12) 0.0550(7) Uani d 1
N N4 0.4803(7) 0.41449(19) 0.44804(14) 0.0377(6) Uani d 1
C C1 0.6402(7) 0.57082(18) 0.66257(13) 0.0192(5) Uani d 1
C C2 0.7342(7) 0.46378(18) 0.65064(14) 0.0225(5) Uani d 1
C C3 0.6879(7) 0.41103(18) 0.58177(15) 0.0256(6) Uani d 1
H H3 0.7561 0.3384 0.5755 0.031 Uiso calc 1
C C4 0.5384(7) 0.4682(2) 0.52239(14) 0.0248(6) Uani d 1
C C5 0.4406(7) 0.57402(19) 0.52939(14) 0.0226(5) Uani d 1
H H5 0.3402 0.6119 0.4875 0.027 Uiso calc 1
C C6 0.4937(6) 0.62324(17) 0.59953(14) 0.0195(5) Uani d 1
C C7 0.6911(7) 0.6243(2) 0.73951(14) 0.0285(6) Uani d 1
H H7A 0.6030 0.6980 0.7371 0.043 Uiso calc 1
H H7B 0.9411 0.6252 0.7524 0.043 Uiso calc 1
H H7C 0.5621 0.5845 0.7789 0.043 Uiso calc 1
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
O42 N4 O41 124.7(2)
O42 N4 C4 117.8(3)
O41 N4 C4 117.5(2)
C6 C1 C2 115.7(2)
C6 C1 C7 122.9(2)
C2 C1 C7 121.4(2)
C3 C2 C1 123.5(2)
C3 C2 Cl21 117.87(18)
C1 C2 Cl21 118.63(19)
C2 C3 C4 117.3(2)
C2 C3 H3 121.4
C4 C3 H3 121.4
C5 C4 C3 122.7(2)
C5 C4 N4 118.2(2)
C3 C4 N4 119.0(2)
C4 C5 C6 117.7(2)
C4 C5 H5 121.2
C6 C5 H5 121.2
C5 C6 C1 123.1(2)
C5 C6 Cl61 116.99(18)
C1 C6 Cl61 119.87(18)
C1 C7 H7A 109.5
C1 C7 H7B 109.5
H7A C7 H7B 109.5
C1 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl21 C2 1.735(2)
Cl61 C6 1.741(2)
O41 N4 1.224(3)
O42 N4 1.220(3)
N4 C4 1.477(3)
C1 C6 1.396(3)
C1 C2 1.399(3)
C1 C7 1.512(3)
C2 C3 1.381(3)
C3 C4 1.381(4)
C3 H3 0.9500
C4 C5 1.378(3)
C5 C6 1.384(3)
C5 H5 0.9500
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
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
C3 H3 O42 3_556 0.95 2.47 3.389(3) 163
C5 H5 Cl61 3_466 0.95 2.94 3.862(3) 163
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
C6 C1 C2 C3 -0.1(4)
C7 C1 C2 C3 179.0(3)
C6 C1 C2 Cl21 -179.59(19)
C7 C1 C2 Cl21 -0.5(3)
C1 C2 C3 C4 -0.4(4)
Cl21 C2 C3 C4 179.05(19)
C2 C3 C4 C5 0.8(4)
C2 C3 C4 N4 -179.3(2)
O42 N4 C4 C5 170.1(3)
O41 N4 C4 C5 -9.8(4)
O42 N4 C4 C3 -9.8(4)
O41 N4 C4 C3 170.3(3)
C3 C4 C5 C6 -0.6(4)
N4 C4 C5 C6 179.5(2)
C4 C5 C6 C1 0.0(4)
C4 C5 C6 Cl61 -179.92(19)
C2 C1 C6 C5 0.3(4)
C7 C1 C6 C5 -178.8(2)
C2 C1 C6 Cl61 -179.73(18)
C7 C1 C6 Cl61 1.2(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 251670
