#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/06/2230682.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_2230682
loop_
_publ_author_name
'Al-Dajani, Mohammad T. M.'
'Talaat, Jamal'
'Mohamed, Nornisah'
'Hemamalini, Madhukar'
'Fun, Hoong-Kun'
_publ_section_title
;
 N,N'-[4,4'-Methylenebis(4,1-phenylene)]bis(2,6-difluorobenzamide)
;
_journal_coeditor_code           HB5924
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1832
_journal_paper_doi               10.1107/S1600536811024524
_journal_volume                  67
_journal_year                    2011
_chemical_formula_moiety         'C27 H18 F4 N2 O2'
_chemical_formula_sum            'C27 H18 F4 N2 O2'
_chemical_formula_weight         478.43
_chemical_name_common
;
N,N'-[4,4'-Methylenebis(4,1-phenylene)]bis(2,6-difluorobenzamide)
;
_chemical_name_systematic
;
N-{4-[4-(2,6-difluorobenzamido)benzyl]phenyl}-2,6-difluorobenzamide
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 92.522(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   42.0478(10)
_cell_length_b                   5.29800(10)
_cell_length_c                   9.5643(2)
_cell_measurement_reflns_used    8910
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      32.52
_cell_measurement_theta_min      2.91
_cell_volume                     2128.57(8)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(10)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEXII DUO 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  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_max       63
_diffrn_reflns_limit_h_min       -63
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            26445
_diffrn_reflns_theta_full        32.63
_diffrn_reflns_theta_max         32.63
_diffrn_reflns_theta_min         1.94
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.214
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3871
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0569P)²+1.3081P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1144
_reflns_number_gt                3172
_reflns_number_total             3871
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5924.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2230682
_cod_database_fobs_code          2230682
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.131371(14) 0.52803(12) 0.04350(6) 0.02016(14) Uani d . 1 1 . .
F F2 0.201443(15) 1.06377(13) 0.30050(7) 0.02303(15) Uani d . 1 1 . .
O O1 0.136883(18) 0.97437(15) 0.36217(7) 0.02009(16) Uani d . 1 1 . .
N N1 0.113987(19) 1.00956(16) 0.14156(8) 0.01541(16) Uani d . 1 1 . .
C C1 0.16118(2) 0.60034(18) 0.08307(9) 0.01554(17) Uani d . 1 1 . .
C C2 0.18629(3) 0.4631(2) 0.03344(10) 0.01989(19) Uani d . 1 1 . .
H H2A 0.1826 0.3219 -0.0264 0.024 Uiso calc R 1 1 . .
C C3 0.21695(2) 0.5379(2) 0.07365(11) 0.0223(2) Uani d . 1 1 . .
H H3A 0.2346 0.4482 0.0398 0.027 Uiso calc R 1 1 . .
C C4 0.22225(2) 0.7422(2) 0.16280(11) 0.0207(2) Uani d . 1 1 . .
H H4A 0.2433 0.7941 0.1895 0.025 Uiso calc R 1 1 . .
C C5 0.19617(2) 0.86802(19) 0.21155(10) 0.01656(18) Uani d . 1 1 . .
C C6 0.16482(2) 0.80494(17) 0.17353(9) 0.01396(16) Uani d . 1 1 . .
C C7 0.13715(2) 0.93935(17) 0.23513(9) 0.01430(17) Uani d . 1 1 . .
C C8 0.08569(2) 1.13880(18) 0.17534(9) 0.01475(17) Uani d . 1 1 . .
C C9 0.08638(2) 1.33660(19) 0.27115(10) 0.01791(18) Uani d . 1 1 . .
H H9A 0.1058 1.3826 0.3189 0.021 Uiso calc R 1 1 . .
C C10 0.05852(2) 1.46660(19) 0.29678(10) 0.01816(18) Uani d . 1 1 . .
H H10A 0.0591 1.6004 0.3630 0.022 Uiso calc R 1 1 . .
C C11 0.02971(2) 1.40427(18) 0.22709(10) 0.01674(18) Uani d . 1 1 . .
C C12 0.02942(2) 1.20383(19) 0.13243(11) 0.01962(19) Uani d . 1 1 . .
H H12A 0.0100 1.1570 0.0852 0.024 Uiso calc R 1 1 . .
C C13 0.05708(2) 1.07101(19) 0.10588(10) 0.01794(18) Uani d . 1 1 . .
H H13A 0.0565 0.9352 0.0409 0.022 Uiso calc R 1 1 . .
C C14 0.0000 1.5573(3) 0.2500 0.0213(3) Uani d S 1 2 . .
H H14A -0.0040 1.6645 0.1702 0.026 Uiso d R 1 1 . .
H H1N1 0.1173(3) 0.984(3) 0.0566(16) 0.023(4) 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 0.0000 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'
F F 0.0171 0.0103 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 C8 . . 124.77(8) ?
C7 N1 H1N1 . . 116.8(10) ?
C8 N1 H1N1 . . 118.2(10) ?
F1 C1 C2 . . 117.93(9) ?
F1 C1 C6 . . 118.10(8) ?
C2 C1 C6 . . 123.96(9) ?
C1 C2 C3 . . 117.96(9) ?
C1 C2 H2A . . 121.0 ?
C3 C2 H2A . . 121.0 ?
C2 C3 C4 . . 120.98(9) ?
C2 C3 H3A . . 119.5 ?
C4 C3 H3A . . 119.5 ?
C5 C4 C3 . . 118.33(9) ?
C5 C4 H4A . . 120.8 ?
C3 C4 H4A . . 120.8 ?
F2 C5 C4 . . 118.12(8) ?
F2 C5 C6 . . 118.35(8) ?
C4 C5 C6 . . 123.53(9) ?
C1 C6 C5 . . 115.22(8) ?
C1 C6 C7 . . 123.11(8) ?
C5 C6 C7 . . 121.53(8) ?
O1 C7 N1 . . 125.27(9) ?
O1 C7 C6 . . 119.92(8) ?
N1 C7 C6 . . 114.80(8) ?
C9 C8 C13 . . 119.99(9) ?
C9 C8 N1 . . 121.25(8) ?
C13 C8 N1 . . 118.70(8) ?
C10 C9 C8 . . 119.73(9) ?
C10 C9 H9A . . 120.1 ?
C8 C9 H9A . . 120.1 ?
C9 C10 C11 . . 121.26(9) ?
C9 C10 H10A . . 119.4 ?
C11 C10 H10A . . 119.4 ?
C12 C11 C10 . . 118.18(9) ?
C12 C11 C14 . . 121.20(8) ?
C10 C11 C14 . . 120.57(8) ?
C13 C12 C11 . . 121.31(9) ?
C13 C12 H12A . . 119.3 ?
C11 C12 H12A . . 119.3 ?
C12 C13 C8 . . 119.51(9) ?
C12 C13 H13A . . 120.2 ?
C8 C13 H13A . . 120.2 ?
C11 C14 C11 . 2 115.22(11) ?
C11 C14 H14A . . 108.5 ?
C11 C14 H14A 2 . 108.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C1 . 1.3489(11) ?
F2 C5 . 1.3534(11) ?
O1 C7 . 1.2297(11) ?
N1 C7 . 1.3459(12) ?
N1 C8 . 1.4222(12) ?
N1 H1N1 . 0.842(15) ?
C1 C2 . 1.3828(13) ?
C1 C6 . 1.3911(13) ?
C2 C3 . 1.3870(15) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.3899(15) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.3815(13) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.3929(12) ?
C6 C7 . 1.5058(13) ?
C8 C9 . 1.3916(13) ?
C8 C13 . 1.3954(13) ?
C9 C10 . 1.3901(13) ?
C9 H9A . 0.9500 ?
C10 C11 . 1.3963(13) ?
C10 H10A . 0.9500 ?
C11 C12 . 1.3952(14) ?
C11 C14 . 1.5131(12) ?
C12 C13 . 1.3922(13) ?
C12 H12A . 0.9500 ?
C13 H13A . 0.9500 ?
C14 C11 2 1.5131(12) ?
C14 H14A . 0.9601 ?
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
_geom_hbond_publ_flag
N1 H1N1 O1 6_575 0.841(15) 2.078(15) 2.8811(11) 159.4(14) yes
C9 H9A F1 6_576 0.95 2.41 3.2318(11) 145 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
F1 C1 C2 C3 . . . . 179.76(9) ?
C6 C1 C2 C3 . . . . -1.62(15) ?
C1 C2 C3 C4 . . . . 0.95(16) ?
C2 C3 C4 C5 . . . . 0.57(16) ?
C3 C4 C5 F2 . . . . 178.73(9) ?
C3 C4 C5 C6 . . . . -1.60(15) ?
F1 C1 C6 C5 . . . . 179.29(8) ?
C2 C1 C6 C5 . . . . 0.68(14) ?
F1 C1 C6 C7 . . . . 3.47(13) ?
C2 C1 C6 C7 . . . . -175.14(9) ?
F2 C5 C6 C1 . . . . -179.35(8) ?
C4 C5 C6 C1 . . . . 0.98(14) ?
F2 C5 C6 C7 . . . . -3.46(13) ?
C4 C5 C6 C7 . . . . 176.87(9) ?
C8 N1 C7 O1 . . . . 0.91(16) ?
C8 N1 C7 C6 . . . . -179.94(8) ?
C1 C6 C7 O1 . . . . 128.72(10) ?
C5 C6 C7 O1 . . . . -46.84(13) ?
C1 C6 C7 N1 . . . . -50.49(12) ?
C5 C6 C7 N1 . . . . 133.95(9) ?
C7 N1 C8 C9 . . . . 42.34(14) ?
C7 N1 C8 C13 . . . . -140.39(10) ?
C13 C8 C9 C10 . . . . -0.27(15) ?
N1 C8 C9 C10 . . . . 176.96(9) ?
C8 C9 C10 C11 . . . . -0.61(15) ?
C9 C10 C11 C12 . . . . 1.22(15) ?
C9 C10 C11 C14 . . . . -176.46(9) ?
C10 C11 C12 C13 . . . . -0.98(15) ?
C14 C11 C12 C13 . . . . 176.68(9) ?
C11 C12 C13 C8 . . . . 0.14(15) ?
C9 C8 C13 C12 . . . . 0.50(15) ?
N1 C8 C13 C12 . . . . -176.80(9) ?
C12 C11 C14 C11 . . . 2 47.96(8) ?
C10 C11 C14 C11 . . . 2 -134.43(10) ?
