#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:16:36 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180420 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/89/7208995.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_7208995
loop_
_publ_author_name
'Curtis, Scott'
'Ilkun, Olesya'
'Brown, Amy'
'Silchenko, Svitlana'
'Gerasimchuk, Nikolay'
_publ_section_title
;
 Synthesis, spectroscopic and structural characterization of the first
 phenyl bis-cyanoximes: non-chelating extended ionisable building block
 ligands for new MOFs
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              152
_journal_paper_doi               10.1039/c2ce26395e
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C10 H6 N4 O2'
_chemical_formula_sum            'C10 H6 N4 O2'
_chemical_formula_weight         214.19
_chemical_name_common            1,4-bis(cyanoxime)benzene
_chemical_name_systematic
;
1,4-bis(cyanoxime)benzene
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.1519(9)
_cell_length_b                   11.244(2)
_cell_length_c                   16.370(3)
_cell_measurement_reflns_used    23
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.06
_cell_volume                     948.3(3)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX2 CCD area detector'
_diffrn_measurement_method       'omega and phi scans'
_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  0.0677
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21292
_diffrn_reflns_theta_full        30.48
_diffrn_reflns_theta_max         30.48
_diffrn_reflns_theta_min         3.62
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9782
_exptl_absorpt_correction_T_min  0.9676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.015(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     75
_refine_ls_number_reflns         1441
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0635
_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)+(0.1182P)²+0.0975P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1809
_refine_ls_wR_factor_ref         0.2028
_reflns_number_gt                975
_reflns_number_total             1441
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce26395e.txt
_cod_data_source_block           new-1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        948.2(3)
_cod_original_sg_symbol_H-M      'P bca'
_cod_database_code               7208995
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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
C2 C 0.0311(4) -0.10329(17) 0.66194(11) 0.0332(4) Uani 1 1 d .
C1 C 0.1007(4) 0.00790(15) 0.62302(11) 0.0317(5) Uani 1 1 d .
C3 C 0.3066(3) 0.00482(14) 0.56002(10) 0.0282(4) Uani 1 1 d .
C4 C 0.5331(4) 0.09558(14) 0.44708(11) 0.0306(4) Uani 1 1 d .
H4 H 0.5554 0.1608 0.4109 0.037 Uiso 1 1 calc R
C5 C 0.3420(4) 0.09982(14) 0.50684(12) 0.0318(4) Uani 1 1 d .
H5 H 0.2346 0.1682 0.5114 0.038 Uiso 1 1 calc R
N2 N -0.0249(3) -0.19368(15) 0.68897(11) 0.0415(5) Uani 1 1 d .
N1 N -0.0285(3) 0.10393(15) 0.63722(10) 0.0372(5) Uani 1 1 d .
O1 O -0.2170(3) 0.08600(12) 0.69587(9) 0.0429(4) Uani 1 1 d .
H1 H -0.3027 0.1489 0.7023 0.064 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C2 0.0346(9) 0.0298(10) 0.0352(9) -0.0006(7) -0.0004(8) 0.0008(7)
C1 0.0347(9) 0.0267(9) 0.0336(9) 0.0003(7) -0.0026(7) -0.0029(7)
C3 0.0312(9) 0.0241(8) 0.0294(8) -0.0013(6) -0.0032(6) -0.0023(6)
C4 0.0363(9) 0.0222(8) 0.0333(9) 0.0024(6) -0.0030(7) -0.0015(6)
C5 0.0349(9) 0.0223(8) 0.0381(10) -0.0002(6) -0.0024(7) 0.0008(7)
N2 0.0419(10) 0.0331(9) 0.0494(11) 0.0066(7) 0.0026(7) -0.0014(7)
N1 0.0404(9) 0.0340(9) 0.0372(8) -0.0014(6) 0.0015(7) -0.0009(7)
O1 0.0465(9) 0.0363(8) 0.0459(8) 0.0017(6) 0.0084(6) 0.0054(6)
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N2 C2 C1 176.6(2) . .
N1 C1 C2 121.06(17) . .
N1 C1 C3 121.01(16) . .
C2 C1 C3 117.63(15) . .
C5 C3 C4 119.26(16) . 5_656
C5 C3 C1 120.84(16) . .
C4 C3 C1 119.89(15) 5_656 .
C5 C4 C3 120.21(15) . 5_656
C5 C4 H4 119.9 . .
C3 C4 H4 119.9 5_656 .
C4 C5 C3 120.52(16) . .
C4 C5 H5 119.7 . .
C3 C5 H5 119.7 . .
C1 N1 O1 111.48(16) . .
N1 O1 H1 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C2 N2 1.145(2) .
C2 C1 1.448(3) .
C1 N1 1.289(2) .
C1 C3 1.480(3) .
C3 C5 1.390(2) .
C3 C4 1.404(2) 5_656
C4 C5 1.389(3) .
C4 C3 1.404(2) 5_656
C4 H4 0.9500 .
C5 H5 0.9500 .
N1 O1 1.380(2) .
O1 H1 0.8400 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N2 0.84 1.99 2.814(2) 165.6 6_565
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N2 C2 C1 N1 124(4) . .
N2 C2 C1 C3 -50(4) . .
N1 C1 C3 C5 -9.0(3) . .
C2 C1 C3 C5 164.67(17) . .
N1 C1 C3 C4 171.73(17) . 5_656
C2 C1 C3 C4 -14.6(2) . 5_656
C3 C4 C5 C3 -0.2(3) 5_656 .
C4 C3 C5 C4 0.2(3) 5_656 .
C1 C3 C5 C4 -179.05(16) . .
C2 C1 N1 O1 4.2(2) . .
C3 C1 N1 O1 177.69(15) . .
