#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/42/4124249.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_4124249
loop_
_publ_author_name
'Ghosh, Soumyajit'
'Mishra, Manish Kumar'
'Ganguly, Somnath'
'Desiraju, Gautam R.'
_publ_section_title
;
 Dual Stress and Thermally Driven Mechanical Properties of the Same
 Organic Crystal: 2,6-Dichlorobenzylidene-4-fluoro-3-nitroaniline.
;
_journal_issue                   31
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9912
_journal_page_last               9921
_journal_paper_doi               10.1021/jacs.5b05324
_journal_volume                  137
_journal_year                    2015
_chemical_formula_sum            'C13 H7 Cl2 F N2 O2'
_chemical_formula_weight         313.05
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.82(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.877(7)
_cell_length_b                   21.79(4)
_cell_length_c                   15.21(3)
_cell_measurement_temperature    248
_cell_volume                     1258(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      248
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.1217
_diffrn_reflns_av_sigmaI/netI    0.0845
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11357
_diffrn_reflns_theta_full        27.76
_diffrn_reflns_theta_max         27.76
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    0.530
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Acicular
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.684
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2912
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.1236
_refine_ls_R_factor_gt           0.1073
_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)+(0.0905P)²+9.0953P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3074
_refine_ls_wR_factor_ref         0.3191
_reflns_number_gt                2181
_reflns_number_total             2912
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ja5b05324_si_002.cif
_cod_data_source_block           -25
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 4124248--4124252.cif.
;
_cod_original_sg_symbol_H-M      'P 21/C'
_cod_database_code               4124249
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
Cl1 Cl 0.0869(6) 0.53321(9) 0.40607(13) 0.0546(6) Uani 1 1 d .
Cl2 Cl 0.4062(5) 0.42594(9) 0.11172(13) 0.0508(5) Uani 1 1 d .
F F 0.7263(16) 0.1770(2) 0.4981(3) 0.0661(15) Uani 1 1 d .
O1 O 0.761(2) 0.2275(4) 0.6514(4) 0.093(3) Uani 1 1 d .
O2 O 0.443(2) 0.3047(3) 0.6589(4) 0.091(3) Uani 1 1 d .
N2 N 0.5830(19) 0.2694(3) 0.6168(4) 0.0509(15) Uani 1 1 d .
N1 N 0.2129(15) 0.3996(3) 0.3591(4) 0.0404(13) Uani 1 1 d .
C11 C 0.6039(19) 0.2311(3) 0.4651(5) 0.0411(15) Uani 1 1 d .
C10 C 0.544(2) 0.2405(3) 0.3751(5) 0.0515(19) Uani 1 1 d .
H6 H 0.5857 0.2089 0.3373 0.062 Uiso 1 1 calc R
C9 C 0.425(2) 0.2957(3) 0.3396(4) 0.0437(16) Uani 1 1 d .
H5 H 0.3920 0.3020 0.2780 0.052 Uiso 1 1 calc R
C8 C 0.3507(16) 0.3424(3) 0.3942(4) 0.0346(13) Uani 1 1 d .
C13 C 0.3915(17) 0.3328(3) 0.4849(4) 0.0358(13) Uani 1 1 d .
H7 H 0.3298 0.3630 0.5220 0.043 Uiso 1 1 calc R
C12 C 0.5258(17) 0.2774(3) 0.5198(4) 0.0358(13) Uani 1 1 d .
C7 C 0.3634(17) 0.4251(3) 0.3035(5) 0.0400(14) Uani 1 1 d .
H4 H 0.5658 0.4068 0.2916 0.048 Uiso 1 1 calc R
C6 C 0.2406(17) 0.4820(3) 0.2560(4) 0.0370(14) Uani 1 1 d .
C1 C 0.2537(18) 0.4871(3) 0.1656(5) 0.0401(14) Uani 1 1 d .
C2 C 0.1420(18) 0.5390(3) 0.1158(5) 0.0441(16) Uani 1 1 d .
H1 H 0.1543 0.5411 0.0554 0.053 Uiso 1 1 calc R
C3 C 0.013(2) 0.5871(3) 0.1566(5) 0.0471(17) Uani 1 1 d .
H2 H -0.0645 0.6221 0.1234 0.056 Uiso 1 1 calc R
C4 C -0.004(2) 0.5849(3) 0.2454(5) 0.0458(16) Uani 1 1 d .
H3 H -0.0883 0.6183 0.2726 0.055 Uiso 1 1 calc R
C5 C 0.1046(17) 0.5326(3) 0.2939(4) 0.0376(14) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.1480 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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 N2 O1 122.4(7)
O2 N2 C12 118.2(6)
O1 N2 C12 119.4(7)
C7 N1 C8 116.9(6)
F C11 C10 119.2(6)
F C11 C12 121.7(6)
C10 C11 C12 119.1(6)
C11 C10 C9 120.4(6)
C11 C10 H6 119.8
C9 C10 H6 119.8
C10 C9 C8 120.7(6)
C10 C9 H5 119.7
C8 C9 H5 119.7
C13 C8 C9 119.8(6)
C13 C8 N1 118.0(6)
C9 C8 N1 122.1(6)
C8 C13 C12 118.6(6)
C8 C13 H7 120.7
C12 C13 H7 120.7
C13 C12 C11 121.3(6)
C13 C12 N2 117.6(6)
C11 C12 N2 121.1(6)
N1 C7 C6 124.0(6)
N1 C7 H4 118.0
C6 C7 H4 118.0
C1 C6 C5 116.0(6)
C1 C6 C7 118.8(6)
C5 C6 C7 125.2(6)
C2 C1 C6 122.5(7)
C2 C1 Cl2 118.1(6)
C6 C1 Cl2 119.4(5)
C3 C2 C1 118.9(7)
C3 C2 H1 120.6
C1 C2 H1 120.6
C2 C3 C4 121.3(7)
C2 C3 H2 119.3
C4 C3 H2 119.3
C3 C4 C5 119.2(7)
C3 C4 H3 120.4
C5 C4 H3 120.4
C4 C5 C6 122.1(7)
C4 C5 Cl1 117.1(5)
C6 C5 Cl1 120.7(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C5 1.721(8)
Cl2 C1 1.731(8)
F C11 1.331(8)
O1 N2 1.199(9)
O2 N2 1.198(9)
N2 C12 1.456(9)
N1 C7 1.252(9)
N1 C8 1.417(8)
C11 C10 1.356(10)
C11 C12 1.380(9)
C10 C9 1.362(10)
C10 H6 0.9300
C9 C8 1.379(9)
C9 H5 0.9300
C8 C13 1.372(9)
C13 C12 1.378(9)
C13 H7 0.9300
C7 C6 1.464(9)
C7 H4 0.9300
C6 C1 1.391(10)
C6 C5 1.398(10)
C1 C2 1.380(9)
C2 C3 1.364(11)
C2 H1 0.9300
C3 C4 1.366(11)
C3 H2 0.9300
C4 C5 1.376(9)
C4 H3 0.9300
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
F C11 C10 C9 -179.0(7)
C12 C11 C10 C9 3.0(12)
C11 C10 C9 C8 -2.1(13)
C10 C9 C8 C13 -1.3(11)
C10 C9 C8 N1 -177.5(7)
C7 N1 C8 C13 135.5(7)
C7 N1 C8 C9 -48.3(9)
C9 C8 C13 C12 3.8(10)
N1 C8 C13 C12 -179.9(6)
C8 C13 C12 C11 -2.9(10)
C8 C13 C12 N2 177.0(6)
F C11 C12 C13 -178.5(7)
C10 C11 C12 C13 -0.5(11)
F C11 C12 N2 1.6(11)
C10 C11 C12 N2 179.6(7)
O2 N2 C12 C13 15.9(11)
O1 N2 C12 C13 -165.4(8)
O2 N2 C12 C11 -164.1(8)
O1 N2 C12 C11 14.5(12)
C8 N1 C7 C6 175.4(6)
N1 C7 C6 C1 -139.3(7)
N1 C7 C6 C5 40.0(11)
C5 C6 C1 C2 0.4(10)
C7 C6 C1 C2 179.7(6)
C5 C6 C1 Cl2 -178.1(5)
C7 C6 C1 Cl2 1.2(9)
C6 C1 C2 C3 -0.1(11)
Cl2 C1 C2 C3 178.4(6)
C1 C2 C3 C4 0.5(11)
C2 C3 C4 C5 -1.3(11)
C3 C4 C5 C6 1.6(11)
C3 C4 C5 Cl1 178.4(6)
C1 C6 C5 C4 -1.1(10)
C7 C6 C5 C4 179.5(6)
C1 C6 C5 Cl1 -177.9(5)
C7 C6 C5 Cl1 2.8(9)
