#------------------------------------------------------------------------------
#$Date: 2021-01-02 17:15:11 +0100 (Sat 02 de Jan de 2021) $
#$Revision: 260375 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/83/4518393.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_4518393
loop_
_publ_author_name
'Peter, Aneeshma'
'Mohan, Midhun'
'Maris, Thierry'
'Wuest, James D.'
'Duong, Adam'
_publ_section_title
;
 Comparing Crystallizations in Three Dimensions and Two Dimensions:
 Behavior of Isomers of [2,2?-Bipyridine]dicarbonitrile and
 [1,10-Phenanthroline]dicarbonitrile
;
_journal_name_full               'Crystal Growth and Design'
_journal_page_first              5242
_journal_page_last               5248
_journal_paper_doi               10.1021/acs.cgd.7b00777
_journal_volume                  17
_journal_year                    2017
_chemical_formula_moiety         'C12 H6 N4'
_chemical_formula_sum            'C12 H6 N4'
_chemical_formula_weight         206.21
_chemical_name_systematic
;
(2,2'-bipyridine)-5,5'-dicarbonitrile
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-05-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                94.985(4)
_cell_angle_beta                 94.575(4)
_cell_angle_gamma                94.803(4)
_cell_formula_units_Z            1
_cell_length_a                   3.7577(2)
_cell_length_b                   5.8815(4)
_cell_length_c                   10.9271(7)
_cell_measurement_reflns_used    2233
_cell_measurement_temperature    150
_cell_measurement_theta_max      52.058
_cell_measurement_theta_min      3.547
_cell_volume                     238.82(3)
_computing_cell_refinement
;
SAINT (2013) V8.37A; Integration Software for Single Crystal Data. 
Bruker AXS Inc., Madison, WI 53719-1173.'
;
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2013) V8.37A; Integration Software for Single Crystal Data. 
Bruker AXS Inc., Madison, WI 53719-1173.'
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4672
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        52.092
_diffrn_reflns_theta_max         52.092
_diffrn_reflns_theta_min         6.601
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    0.477
_exptl_absorpt_correction_T_max  0.7503
_exptl_absorpt_correction_T_min  0.5214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1434 before and 0.0943 after correction. 
The Ratio of minimum to maximum transmission is 0.6949. 
The λ/2 correction factor is Not present.'
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       plate
_exptl_crystal_F_000             106
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       0.02(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         784
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0862
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1985P)²+0.0002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2565
_refine_ls_wR_factor_ref         0.2921
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                524
_reflns_number_total             784
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jw1897.cif
_cod_data_source_block           jw1897
_cod_database_code               4518393
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3165(8) 0.3803(5) 0.1305(3) 0.0509(11) Uani 1 1 d . . . . .
C1 C 0.4727(9) 0.5386(6) 0.0649(3) 0.0458(12) Uani 1 1 d . . . . .
N2 N 0.2348(8) 0.7603(6) 0.5309(3) 0.0571(12) Uani 1 1 d . . . . .
C2 C 0.5751(9) 0.7628(6) 0.1144(3) 0.0496(12) Uani 1 1 d . . . . .
H2 H 0.681842 0.870637 0.065206 0.059 Uiso 1 1 calc R . . . .
C3 C 0.5205(9) 0.8270(7) 0.2350(3) 0.0513(12) Uani 1 1 d . . . . .
H3 H 0.590120 0.978760 0.270859 0.062 Uiso 1 1 calc R . . . .
C4 C 0.3618(9) 0.6649(7) 0.3029(3) 0.0476(12) Uani 1 1 d . . . . .
C5 C 0.2628(10) 0.4420(7) 0.2473(3) 0.0511(12) Uani 1 1 d . . . . .
H5 H 0.153966 0.331617 0.294558 0.061 Uiso 1 1 calc R . . . .
C6 C 0.2931(10) 0.7190(7) 0.4299(4) 0.0511(12) Uani 1 1 d . . . . .
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
N1 0.0570(19) 0.070(2) 0.0240(18) -0.0061(14) 0.0131(13) -0.0007(15)
C1 0.047(2) 0.065(3) 0.023(2) -0.0054(17) 0.0063(15) -0.0015(17)
N2 0.065(2) 0.077(3) 0.026(2) -0.0105(15) 0.0163(15) -0.0060(17)
C2 0.058(2) 0.061(3) 0.028(2) -0.0058(16) 0.0104(16) -0.0026(17)
C3 0.056(2) 0.066(2) 0.029(2) -0.0109(17) 0.0104(17) -0.0001(18)
C4 0.051(2) 0.070(3) 0.019(2) -0.0066(16) 0.0097(15) -0.0026(17)
C5 0.057(2) 0.065(3) 0.029(2) -0.0046(17) 0.0098(16) 0.0009(18)
C6 0.050(2) 0.065(3) 0.035(2) -0.0053(18) 0.0074(17) -0.0041(18)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0140 0.0070 '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 0.0250 0.0140 '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
C5 N1 C1 118.3(3) . .
N1 C1 C1 116.3(4) . 2_665
N1 C1 C2 122.4(4) . .
C2 C1 C1 121.3(4) . 2_665
C1 C2 H2 120.3 . .
C3 C2 C1 119.4(4) . .
C3 C2 H2 120.3 . .
C2 C3 H3 120.8 . .
C2 C3 C4 118.3(4) . .
C4 C3 H3 120.8 . .
C3 C4 C5 119.5(3) . .
C3 C4 C6 121.7(3) . .
C5 C4 C6 118.8(3) . .
N1 C5 C4 122.1(4) . .
N1 C5 H5 119.0 . .
C4 C5 H5 119.0 . .
N2 C6 C4 179.2(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.348(5) .
N1 C5 1.332(5) .
C1 C1 1.487(7) 2_665
C1 C2 1.392(5) .
N2 C6 1.151(5) .
C2 H2 0.9500 .
C2 C3 1.376(5) .
C3 H3 0.9500 .
C3 C4 1.382(5) .
C4 C5 1.403(6) .
C4 C6 1.446(5) .
C5 H5 0.9500 .

_cod_database_fobs_code 4518393
