#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/57/2105749.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_2105749
loop_
_publ_author_name
'Omondi, Bernard'
'Lemmerer, Andreas'
'Fernandes, Manuel A.'
'Levendis, Demetrius C.'
'Layh, Marcus'
_publ_section_title
;
 Formation of isostructural solid solutions in 2,6-disubstituted
 N-phenylformamides and N-phenylthioamides
;
_journal_coeditor_code           GP5066
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              106
_journal_page_last               114
_journal_paper_doi               10.1107/S2052520613022129
_journal_volume                  70
_journal_year                    2014
_chemical_formula_moiety         'C7 H5 Cl1.46 F0.54 N O'
_chemical_formula_sum            'C7 H5 Cl1.46 F0.54 N O'
_chemical_formula_weight         181.07
_chemical_name_systematic
;
 (N-(2,6-difluorophenyl)formamide).(N-(2,6-dichlorophenyl)formamide) 0.73:0.27
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.5220(2)
_cell_length_b                   12.2910(3)
_cell_length_c                   14.3090(4)
_cell_measurement_reflns_used    5727
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.43
_cell_measurement_theta_min      2.85
_cell_volume                     1498.78(7)
_computing_cell_refinement       'Bruker SAINT+, Bruker (1999)'
_computing_data_collection       'Bruker SMART, Bruker (1998)'
_computing_data_reduction        'Bruker SAINT+'
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17793
_diffrn_reflns_theta_full        28
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_min         2.85
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_T_max  0.895
_exptl_absorpt_correction_T_min  0.765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             733.2
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.217
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.254
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1811
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.323
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0212P)²+1.2505P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.089
_refine_ls_wR_factor_ref         0.0899
_reflns_number_gt                1706
_reflns_number_total             1811
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            gp5066sup1.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               2105749
_cod_database_fobs_code          2105749
loop_
_symmetry_equiv_pos_as_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'
'-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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.55412(18) 0.41372(14) 0.65058(12) 0.0238(4) Uani d D 1 1 A .
C C2 0.56802(18) 0.36432(14) 0.56340(13) 0.0264(4) Uani d D 1 1 . .
C C3 0.6658(2) 0.40402(18) 0.49453(14) 0.0350(5) Uani d D 1 1 A .
H H3 0.6718 0.369 0.4354 0.042 Uiso calc R 1 1 . .
C C4 0.7549(3) 0.4955(2) 0.51292(15) 0.0392(5) Uani d D 1 1 . .
H H4 0.823 0.5235 0.4662 0.047 Uiso calc R 1 1 A .
C C5 0.7456(2) 0.54661(18) 0.59882(15) 0.0368(5) Uani d D 1 1 A .
H H5 0.8084 0.6087 0.6116 0.044 Uiso calc R 1 1 . .
C C6 0.6446(2) 0.50675(16) 0.66595(13) 0.0294(4) Uani d D 1 1 . .
C C7 0.4956(2) 0.33346(17) 0.80107(13) 0.0295(4) Uani d . 1 1 A .
H H7 0.4162 0.3066 0.8416 0.035 Uiso calc R 1 1 . .
O O1 0.63083(16) 0.32872(14) 0.82907(10) 0.0367(4) Uani d . 1 1 . .
Cl Cl1 0.45573(16) 0.25127(11) 0.53968(7) 0.0273(2) Uani d PD 0.728(4) 1 A 1
Cl Cl2 0.62585(16) 0.57954(10) 0.76865(9) 0.0347(3) Uani d PD 0.728(4) 1 A 1
F F1 0.4829(10) 0.2728(5) 0.5474(6) 0.062(4) Uani d PD 0.272(4) 1 A 2
F F2 0.6341(11) 0.5535(7) 0.7512(4) 0.065(4) Uani d PD 0.272(4) 1 A 2
N N1 0.44897(18) 0.37314(14) 0.71833(11) 0.0263(3) Uani d . 1 1 . .
H H1 0.351(3) 0.3664(19) 0.7027(16) 0.032 Uiso d . 1 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 0 '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 0.006 '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
C2 C1 C6 116.82(17)
C2 C1 N1 121.02(16)
C6 C1 N1 122.12(16)
F1 C2 C3 119.7(4)
F1 C2 C1 117.8(4)
C3 C2 C1 122.48(18)
C3 C2 Cl1 118.72(16)
C1 C2 Cl1 118.78(15)
C2 C3 C4 118.92(19)
C2 C3 H3 120.5
C4 C3 H3 120.5
C3 C4 C5 120.48(19)
C3 C4 H4 119.8
C5 C4 H4 119.8
C6 C5 C4 119.6(2)
C6 C5 H5 120.2
C4 C5 H5 120.2
F2 C6 C5 121.2(4)
F2 C6 C1 117.0(4)
C5 C6 C1 121.70(18)
C5 C6 Cl2 117.76(16)
C1 C6 Cl2 120.47(15)
O1 C7 N1 125.91(18)
O1 C7 H7 117
N1 C7 H7 117
C7 N1 C1 123.17(15)
C7 N1 H1 118.5(15)
C1 N1 H1 117.9(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.392(2)
C1 C6 1.396(3)
C1 N1 1.411(2)
C2 F1 1.358(5)
C2 C3 1.380(3)
C2 Cl1 1.721(2)
C3 C4 1.382(3)
C3 H3 0.95
C4 C5 1.382(3)
C4 H4 0.95
C5 C6 1.380(3)
C5 H5 0.95
C6 F2 1.351(5)
C6 Cl2 1.728(2)
C7 O1 1.222(2)
C7 N1 1.341(2)
C7 H7 0.95
N1 H1 0.87(3)
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
N1 H1 O1 6_557 0.87(3) 1.98(3) 2.848(2) 172(2)
C4 H4 O1 2_664 0.95 2.70 3.540(3) 148
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 F1 179.1(5)
N1 C1 C2 F1 -3.2(5)
C6 C1 C2 C3 0.03(16)
N1 C1 C2 C3 177.82(16)
C6 C1 C2 Cl1 -178.47(14)
N1 C1 C2 Cl1 -0.69(18)
F1 C2 C3 C4 -178.2(5)
C1 C2 C3 C4 0.77(19)
Cl1 C2 C3 C4 179.27(16)
C2 C3 C4 C5 -0.2(3)
C3 C4 C5 C6 -1.1(3)
C4 C5 C6 F2 178.9(5)
C4 C5 C6 C1 1.9(3)
C4 C5 C6 Cl2 -175.03(17)
C2 C1 C6 F2 -178.5(5)
N1 C1 C6 F2 3.7(5)
C2 C1 C6 C5 -1.4(2)
N1 C1 C6 C5 -179.16(17)
C2 C1 C6 Cl2 175.49(12)
N1 C1 C6 Cl2 -2.3(2)
O1 C7 N1 C1 1.3(3)
C2 C1 N1 C7 116.98(18)
C6 C1 N1 C7 -65.4(2)
