#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/24/2222481.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_2222481
loop_
_publ_author_name
'Kee, Chin Hui'
'Thomas, Noel F.'
'Ariffin, Azhar'
'Awang, Khalijah'
'Ng, Seik Weng'
_publ_section_title
;
 N,N'-(Biphenyl-2,2'-diyl)bis(furan-2-carboxamide)
;
_journal_coeditor_code           TK2474
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1556
_journal_paper_doi               10.1107/S1600536809021874
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C22 H16 N2 O4'
_chemical_formula_moiety         'C22 H16 N2 O4'
_chemical_formula_sum            'C22 H16 N2 O4'
_chemical_formula_weight         372.37
_chemical_name_systematic
;
N,N'-(Biphenyl-2,2'-diyl)bis(furan-2-carboxamide)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.9380(10)
_cell_angle_beta                 107.5210(10)
_cell_angle_gamma                92.4390(10)
_cell_formula_units_Z            2
_cell_length_a                   8.1784(2)
_cell_length_b                   10.1399(2)
_cell_length_c                   11.1475(2)
_cell_measurement_reflns_used    3508
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.6
_cell_volume                     863.92(3)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       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  0.015
_diffrn_reflns_av_sigmaI/netI    0.025
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6080
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.0
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3836
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.043
_refine_ls_R_factor_gt           0.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0627P)²+0.3539P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.103
_refine_ls_wR_factor_ref         0.111
_reflns_number_gt                3349
_reflns_number_total             3836
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2474.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2222481
_cod_database_fobs_code          2222481
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_disorder_assembly
_atom_site_disorder_group
O O1 0.37952(12) 0.28756(9) 0.22024(9) 0.0174(2) Uani d . 1 . .
O O2 0.32912(12) 0.61791(9) 0.36569(9) 0.0186(2) Uani d . 1 . .
O O3 0.42615(12) 0.02447(10) 0.82668(9) 0.0213(2) Uani d . 1 . .
O O4 0.80281(12) 0.23741(9) 0.86550(9) 0.0191(2) Uani d . 1 . .
N N1 0.29107(14) 0.41257(11) 0.42005(10) 0.0156(2) Uani d D 1 . .
H H1 0.295(2) 0.3271(10) 0.3921(17) 0.028(5) Uiso d D 1 . .
N N2 0.47787(14) 0.16551(11) 0.70037(10) 0.0148(2) Uani d D 1 . .
H H2 0.5491(17) 0.2298(13) 0.6951(15) 0.016(4) Uiso d D 1 . .
C C1 0.40891(17) 0.24580(13) 0.10565(13) 0.0190(3) Uani d . 1 . .
H H1a 0.4304 0.1570 0.0749 0.023 Uiso calc R 1 . .
C C2 0.40293(17) 0.34894(14) 0.04255(13) 0.0190(3) Uani d . 1 . .
H H2a 0.4180 0.3456 -0.0391 0.023 Uiso calc R 1 . .
C C3 0.36958(16) 0.46370(13) 0.12235(12) 0.0173(3) Uani d . 1 . .
H H3 0.3581 0.5517 0.1044 0.021 Uiso calc R 1 . .
C C4 0.35755(16) 0.42216(12) 0.22885(12) 0.0155(3) Uani d . 1 . .
C C5 0.32496(16) 0.49452(12) 0.34438(12) 0.0145(2) Uani d . 1 . .
C C6 0.24862(16) 0.44495(13) 0.53444(12) 0.0144(2) Uani d . 1 . .
C C7 0.23946(17) 0.57726(13) 0.59222(12) 0.0169(3) Uani d . 1 . .
H H7 0.2603 0.6501 0.5537 0.020 Uiso calc R 1 . .
C C8 0.19978(17) 0.60133(13) 0.70591(12) 0.0182(3) Uani d . 1 . .
H H8 0.1950 0.6913 0.7455 0.022 Uiso calc R 1 . .
C C9 0.16695(17) 0.49624(14) 0.76291(12) 0.0192(3) Uani d . 1 . .
H H9 0.1386 0.5138 0.8404 0.023 Uiso calc R 1 . .
C C10 0.17609(17) 0.36502(13) 0.70536(12) 0.0174(3) Uani d . 1 . .
H H10 0.1539 0.2928 0.7443 0.021 Uiso calc R 1 . .
C C11 0.21726(16) 0.33732(12) 0.59167(12) 0.0142(2) Uani d . 1 . .
C C12 0.21741(16) 0.19410(12) 0.53056(12) 0.0142(3) Uani d . 1 . .
C C13 0.08880(17) 0.13778(13) 0.41514(12) 0.0164(3) Uani d . 1 . .
H H13 0.0094 0.1937 0.3731 0.020 Uiso calc R 1 . .
C C14 0.07515(17) 0.00244(13) 0.36117(12) 0.0182(3) Uani d . 1 . .
H H14 -0.0121 -0.0337 0.2825 0.022 Uiso calc R 1 . .
C C15 0.18976(17) -0.08003(13) 0.42285(12) 0.0178(3) Uani d . 1 . .
H H15 0.1790 -0.1734 0.3877 0.021 Uiso calc R 1 . .
C C16 0.31983(16) -0.02613(13) 0.53571(12) 0.0161(3) Uani d . 1 . .
H H16 0.3991 -0.0826 0.5770 0.019 Uiso calc R 1 . .
C C17 0.33501(16) 0.11065(12) 0.58905(12) 0.0141(2) Uani d . 1 . .
C C18 0.52125(16) 0.10827(12) 0.80562(12) 0.0150(3) Uani d . 1 . .
C C19 0.69553(16) 0.15138(12) 0.89706(12) 0.0155(3) Uani d . 1 . .
C C20 0.77797(18) 0.11564(13) 1.01001(13) 0.0195(3) Uani d . 1 . .
H H20 0.7319 0.0577 1.0529 0.023 Uiso calc R 1 . .
C C21 0.94791(18) 0.18268(15) 1.05134(13) 0.0226(3) Uani d . 1 . .
H H21 1.0380 0.1779 1.1272 0.027 Uiso calc R 1 . .
C C22 0.95558(18) 0.25413(15) 0.96175(13) 0.0226(3) Uani d . 1 . .
H H22 1.0546 0.3090 0.9652 0.027 Uiso calc R 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'
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
C1 O1 C4 . . 106.32(10) ?
C22 O4 C19 . . 105.90(10) ?
C5 N1 C6 . . 129.64(11) ?
C5 N1 H1 . . 114.1(12) ?
C6 N1 H1 . . 116.3(12) ?
C18 N2 C17 . . 122.19(10) ?
C18 N2 H2 . . 118.8(10) ?
C17 N2 H2 . . 118.2(10) ?
C2 C1 O1 . . 110.34(11) ?
C2 C1 H1a . . 124.8 ?
O1 C1 H1a . . 124.8 ?
C1 C2 C3 . . 106.73(12) ?
C1 C2 H2a . . 126.6 ?
C3 C2 H2a . . 126.6 ?
C4 C3 C2 . . 106.31(12) ?
C4 C3 H3 . . 126.8 ?
C2 C3 H3 . . 126.8 ?
C3 C4 O1 . . 110.30(11) ?
C3 C4 C5 . . 131.50(12) ?
O1 C4 C5 . . 118.19(11) ?
O2 C5 N1 . . 125.53(12) ?
O2 C5 C4 . . 120.77(11) ?
N1 C5 C4 . . 113.70(11) ?
C7 C6 C11 . . 120.02(11) ?
C7 C6 N1 . . 122.95(11) ?
C11 C6 N1 . . 117.03(11) ?
C8 C7 C6 . . 119.61(12) ?
C8 C7 H7 . . 120.2 ?
C6 C7 H7 . . 120.2 ?
C9 C8 C7 . . 121.07(12) ?
C9 C8 H8 . . 119.5 ?
C7 C8 H8 . . 119.5 ?
C8 C9 C10 . . 119.20(12) ?
C8 C9 H9 . . 120.4 ?
C10 C9 H9 . . 120.4 ?
C9 C10 C11 . . 121.23(12) ?
C9 C10 H10 . . 119.4 ?
C11 C10 H10 . . 119.4 ?
C10 C11 C6 . . 118.87(12) ?
C10 C11 C12 . . 119.07(11) ?
C6 C11 C12 . . 121.97(11) ?
C17 C12 C13 . . 118.24(11) ?
C17 C12 C11 . . 122.04(11) ?
C13 C12 C11 . . 119.58(11) ?
C14 C13 C12 . . 121.42(12) ?
C14 C13 H13 . . 119.3 ?
C12 C13 H13 . . 119.3 ?
C13 C14 C15 . . 119.56(12) ?
C13 C14 H14 . . 120.2 ?
C15 C14 H14 . . 120.2 ?
C16 C15 C14 . . 120.02(12) ?
C16 C15 H15 . . 120.0 ?
C14 C15 H15 . . 120.0 ?
C15 C16 C17 . . 120.36(12) ?
C15 C16 H16 . . 119.8 ?
C17 C16 H16 . . 119.8 ?
C12 C17 C16 . . 120.35(11) ?
C12 C17 N2 . . 120.43(11) ?
C16 C17 N2 . . 119.14(11) ?
O3 C18 N2 . . 124.03(12) ?
O3 C18 C19 . . 119.98(12) ?
N2 C18 C19 . . 115.98(11) ?
C20 C19 O4 . . 110.52(11) ?
C20 C19 C18 . . 131.14(12) ?
O4 C19 C18 . . 118.26(11) ?
C19 C20 C21 . . 106.02(12) ?
C19 C20 H20 . . 127.0 ?
C21 C20 H20 . . 127.0 ?
C22 C21 C20 . . 106.47(12) ?
C22 C21 H21 . . 126.8 ?
C20 C21 H21 . . 126.8 ?
C21 C22 O4 . . 111.09(12) ?
C21 C22 H22 . . 124.5 ?
O4 C22 H22 . . 124.5 ?
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
O1 C1 . 1.3695(16) ?
O1 C4 . 1.3749(15) ?
O2 C5 . 1.2295(15) ?
O3 C18 . 1.2267(16) ?
O4 C22 . 1.3613(16) ?
O4 C19 . 1.3716(15) ?
N1 C5 . 1.3572(16) ?
N1 C6 . 1.4093(16) ?
N1 H1 . 0.875(9) ?
N2 C18 . 1.3569(16) ?
N2 C17 . 1.4311(16) ?
N2 H2 . 0.877(9) ?
C1 C2 . 1.3521(19) ?
C1 H1a . 0.9500 ?
C2 C3 . 1.4267(19) ?
C2 H2a . 0.9500 ?
C3 C4 . 1.3550(18) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.4715(18) ?
C6 C7 . 1.3999(17) ?
C6 C11 . 1.4067(17) ?
C7 C8 . 1.3851(18) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.3869(19) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.3893(18) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.3931(18) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.4941(17) ?
C12 C17 . 1.3957(18) ?
C12 C13 . 1.4030(17) ?
C13 C14 . 1.3853(17) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.3884(19) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.3858(18) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.3961(17) ?
C16 H16 . 0.9500 ?
C18 C19 . 1.4765(18) ?
C19 C20 . 1.3559(18) ?
C20 C21 . 1.4255(19) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.345(2) ?
C21 H21 . 0.9500 ?
C22 H22 . 0.9500 ?
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
N2 H2 O2 2_666 0.880(10) 2.120(10) 2.9700(10) 165.0(10) 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
C4 O1 C1 C2 . . . . -1.04(14) ?
O1 C1 C2 C3 . . . . 0.66(15) ?
C1 C2 C3 C4 . . . . 0.00(14) ?
C2 C3 C4 O1 . . . . -0.65(14) ?
C2 C3 C4 C5 . . . . 179.98(13) ?
C1 O1 C4 C3 . . . . 1.04(14) ?
C1 O1 C4 C5 . . . . -179.49(11) ?
C6 N1 C5 O2 . . . . 2.2(2) ?
C6 N1 C5 C4 . . . . -177.63(12) ?
C3 C4 C5 O2 . . . . -11.2(2) ?
O1 C4 C5 O2 . . . . 169.42(11) ?
C3 C4 C5 N1 . . . . 168.56(13) ?
O1 C4 C5 N1 . . . . -10.77(16) ?
C5 N1 C6 C7 . . . . -1.9(2) ?
C5 N1 C6 C11 . . . . 178.99(12) ?
C11 C6 C7 C8 . . . . 0.14(19) ?
N1 C6 C7 C8 . . . . -178.89(12) ?
C6 C7 C8 C9 . . . . -0.7(2) ?
C7 C8 C9 C10 . . . . 0.7(2) ?
C8 C9 C10 C11 . . . . -0.1(2) ?
C9 C10 C11 C6 . . . . -0.48(19) ?
C9 C10 C11 C12 . . . . -177.20(12) ?
C7 C6 C11 C10 . . . . 0.46(18) ?
N1 C6 C11 C10 . . . . 179.55(11) ?
C7 C6 C11 C12 . . . . 177.08(11) ?
N1 C6 C11 C12 . . . . -3.83(18) ?
C10 C11 C12 C17 . . . . -65.60(16) ?
C6 C11 C12 C17 . . . . 117.78(14) ?
C10 C11 C12 C13 . . . . 109.90(14) ?
C6 C11 C12 C13 . . . . -66.72(16) ?
C17 C12 C13 C14 . . . . 1.43(19) ?
C11 C12 C13 C14 . . . . -174.25(11) ?
C12 C13 C14 C15 . . . . 0.66(19) ?
C13 C14 C15 C16 . . . . -1.8(2) ?
C14 C15 C16 C17 . . . . 0.93(19) ?
C13 C12 C17 C16 . . . . -2.34(18) ?
C11 C12 C17 C16 . . . . 173.22(11) ?
C13 C12 C17 N2 . . . . 174.26(11) ?
C11 C12 C17 N2 . . . . -10.18(18) ?
C15 C16 C17 C12 . . . . 1.20(18) ?
C15 C16 C17 N2 . . . . -175.44(11) ?
C18 N2 C17 C12 . . . . 133.43(13) ?
C18 N2 C17 C16 . . . . -49.93(17) ?
C17 N2 C18 O3 . . . . -15.7(2) ?
C17 N2 C18 C19 . . . . 163.63(11) ?
C22 O4 C19 C20 . . . . 0.32(15) ?
C22 O4 C19 C18 . . . . -176.70(11) ?
O3 C18 C19 C20 . . . . -1.2(2) ?
N2 C18 C19 C20 . . . . 179.49(13) ?
O3 C18 C19 O4 . . . . 175.11(11) ?
N2 C18 C19 O4 . . . . -4.22(17) ?
O4 C19 C20 C21 . . . . -0.45(15) ?
C18 C19 C20 C21 . . . . 176.06(13) ?
C19 C20 C21 C22 . . . . 0.40(16) ?
C20 C21 C22 O4 . . . . -0.22(16) ?
C19 O4 C22 C21 . . . . -0.05(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 950495
