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#$Date: 2023-04-03 10:29:16 +0300 (Mon, 03 Apr 2023) $
#$Revision: 282199 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/69/8106992.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_8106992
loop_
_publ_author_name
'Gichumbi, Joel M.'
'Friedrich, Holger B.'
'Omondi, Bernard'
_publ_section_title
;
 Crystal structure of 3,6-di-2-pyridinyl-4-pyridazine carbonitrile,
 C15H9N5
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              741
_journal_page_last               743
_journal_paper_doi               10.1515/ncrs-2015-0253
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C15 H9 N5'
_chemical_formula_sum            'C15 H9 N5'
_chemical_formula_weight         259.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 102.289(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9817(14)
_cell_length_b                   11.5791(19)
_cell_length_c                   12.065(2)
_cell_measurement_reflns_used    9747
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.387
_cell_measurement_theta_min      2.321
_cell_volume                     1226.0(3)
_computing_cell_refinement
'SAINT (7.60a,Bruker AXS Inc.,Madison,WI,USA,2006)'
_computing_data_collection
'SAINT (7.60a,Bruker AXS Inc.,Madison,WI,USA,2006)'
_computing_data_reduction
'SAINT (7.60a, Bruker AXS Inc.,Madison,WI,USA,2006)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Kappa Duo Apex II Diffractometer'
_diffrn_measurement_method       '0.5° φ scans and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9747
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.387
_diffrn_reflns_theta_min         2.321
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2001)'
_exptl_crystal_colour            gold
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      1.405
_exptl_crystal_description       rod
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_exptl_transmission_factor_max   1.000
_exptl_transmission_factor_min   0.932
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3043
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0533
_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)+(0.0682P)²+0.1585P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1512
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1947
_reflns_number_total             3043
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2015-0253_suppl.cif
_cod_data_source_block           joelmg5
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8106992
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.987
_shelx_estimated_absorpt_t_max   0.990
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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_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 0.50551(18) 0.76786(14) 0.00776(13) 0.0367(4) Uani 1 1 d . . . . .
N2 N 0.7960(2) 0.48758(15) -0.27662(14) 0.0492(5) Uani 1 1 d . . . . .
N3 N 0.79708(19) 0.43609(13) 0.12491(12) 0.0363(4) Uani 1 1 d . . . . .
N4 N 0.70951(18) 0.52356(13) 0.14521(12) 0.0343(4) Uani 1 1 d . . . . .
N5 N 0.97483(19) 0.30412(14) -0.08206(13) 0.0401(4) Uani 1 1 d . . . . .
C1 C 0.4149(2) 0.85299(17) 0.02911(16) 0.0420(5) Uani 1 1 d . . . . .
H1 H 0.3805 0.9085 -0.0286 0.050 Uiso 1 1 calc R U . . .
C2 C 0.3685(2) 0.86441(18) 0.13100(16) 0.0417(5) Uani 1 1 d . . . . .
H2 H 0.3032 0.9258 0.1423 0.050 Uiso 1 1 calc R U . . .
C3 C 0.4191(2) 0.78505(17) 0.21541(16) 0.0391(5) Uani 1 1 d . . . . .
H3 H 0.3891 0.7906 0.2861 0.047 Uiso 1 1 calc R U . . .
C4 C 0.5142(2) 0.69726(16) 0.19583(15) 0.0350(4) Uani 1 1 d . . . . .
H4 H 0.5513 0.6418 0.2530 0.042 Uiso 1 1 calc R U . . .
C5 C 0.5546(2) 0.69141(15) 0.09094(14) 0.0296(4) Uani 1 1 d . . . . .
C6 C 0.6524(2) 0.59737(15) 0.06280(14) 0.0289(4) Uani 1 1 d . . . . .
C7 C 0.6809(2) 0.58705(15) -0.04750(14) 0.0314(4) Uani 1 1 d . . . . .
H7 H 0.6408 0.6412 -0.1053 0.038 Uiso 1 1 calc R U . . .
C8 C 0.7703(2) 0.49438(14) -0.06827(14) 0.0288(4) Uani 1 1 d . . . . .
C9 C 0.7925(2) 0.48344(15) -0.18241(15) 0.0347(4) Uani 1 1 d . . . . .
C10 C 0.8286(2) 0.41904(15) 0.02180(14) 0.0299(4) Uani 1 1 d . . . . .
C11 C 0.9257(2) 0.31746(14) 0.01420(14) 0.0305(4) Uani 1 1 d . . . . .
C12 C 0.9624(2) 0.24220(17) 0.10359(15) 0.0405(5) Uani 1 1 d . . . . .
H12 H 0.9249 0.2542 0.1706 0.049 Uiso 1 1 calc R U . . .
C13 C 1.0541(3) 0.14937(19) 0.09490(18) 0.0499(6) Uani 1 1 d . . . . .
H13 H 1.0813 0.0965 0.1560 0.060 Uiso 1 1 calc R U . . .
C14 C 1.1063(2) 0.13368(17) -0.00375(18) 0.0445(5) Uani 1 1 d . . . . .
H14 H 1.1704 0.0703 -0.0118 0.053 Uiso 1 1 calc R U . . .
C15 C 1.0631(2) 0.21215(18) -0.08973(17) 0.0435(5) Uani 1 1 d . . . . .
H15 H 1.0974 0.2009 -0.1582 0.052 Uiso 1 1 calc R U . . .
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'
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
C1 N1 C5 117.33(15) . .
N4 N3 C10 121.84(15) . .
C6 N4 N3 119.92(13) . .
C11 N5 C15 117.44(16) . .
N1 C1 C2 123.45(18) . .
N1 C1 H1 118.3 . .
C2 C1 H1 118.3 . .
C3 C2 C1 118.61(18) . .
C3 C2 H2 120.7 . .
C1 C2 H2 120.7 . .
C2 C3 C4 118.98(17) . .
C2 C3 H3 120.5 . .
C4 C3 H3 120.5 . .
C3 C4 C5 118.86(17) . .
C3 C4 H4 120.6 . .
C5 C4 H4 120.6 . .
N1 C5 C4 122.76(16) . .
N1 C5 C6 115.46(14) . .
C4 C5 C6 121.76(16) . .
N4 C6 C7 122.15(16) . .
N4 C6 C5 117.00(14) . .
C7 C6 C5 120.85(16) . .
C8 C7 C6 117.46(16) . .
C8 C7 H7 121.3 . .
C6 C7 H7 121.3 . .
C7 C8 C10 118.22(14) . .
C7 C8 C9 116.25(16) . .
C10 C8 C9 125.51(16) . .
N2 C9 C8 170.3(2) . .
N3 C10 C8 120.40(16) . .
N3 C10 C11 114.60(15) . .
C8 C10 C11 125.00(15) . .
N5 C11 C12 122.78(16) . .
N5 C11 C10 117.01(15) . .
C12 C11 C10 120.21(15) . .
C11 C12 C13 119.07(16) . .
C11 C12 H12 120.5 . .
C13 C12 H12 120.5 . .
C12 C13 C14 119.25(19) . .
C12 C13 H13 120.4 . .
C14 C13 H13 120.4 . .
C15 C14 C13 118.12(19) . .
C15 C14 H14 120.9 . .
C13 C14 H14 120.9 . .
N5 C15 C14 123.34(17) . .
N5 C15 H15 118.3 . .
C14 C15 H15 118.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.338(2) .
N1 C5 1.341(2) .
N2 C9 1.145(2) .
N3 N4 1.336(2) .
N3 C10 1.348(2) .
N4 C6 1.329(2) .
N5 C11 1.336(2) .
N5 C15 1.343(3) .
C1 C2 1.386(2) .
C1 H1 0.9500 .
C2 C3 1.375(3) .
C2 H2 0.9500 .
C3 C4 1.380(3) .
C3 H3 0.9500 .
C4 C5 1.391(2) .
C4 H4 0.9500 .
C5 C6 1.483(2) .
C6 C7 1.413(2) .
C7 C8 1.394(2) .
C7 H7 0.9500 .
C8 C10 1.405(2) .
C8 C9 1.439(2) .
C10 C11 1.479(2) .
C11 C12 1.371(2) .
C12 C13 1.372(3) .
C12 H12 0.9500 .
C13 C14 1.381(3) .
C13 H13 0.9500 .
C14 C15 1.371(3) .
C14 H14 0.9500 .
C15 H15 0.9500 .
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C10 N3 N4 C6 -0.8(3) . . . .
C5 N1 C1 C2 -1.0(3) . . . .
N1 C1 C2 C3 0.7(3) . . . .
C1 C2 C3 C4 0.1(3) . . . .
C2 C3 C4 C5 -0.5(3) . . . .
C1 N1 C5 C4 0.5(3) . . . .
C1 N1 C5 C6 178.93(16) . . . .
C3 C4 C5 N1 0.2(3) . . . .
C3 C4 C5 C6 -178.08(17) . . . .
N3 N4 C6 C7 0.0(3) . . . .
N3 N4 C6 C5 179.22(15) . . . .
N1 C5 C6 N4 176.60(16) . . . .
C4 C5 C6 N4 -5.0(3) . . . .
N1 C5 C6 C7 -4.2(2) . . . .
C4 C5 C6 C7 174.26(17) . . . .
N4 C6 C7 C8 1.1(3) . . . .
C5 C6 C7 C8 -178.13(16) . . . .
C6 C7 C8 C10 -1.3(2) . . . .
C6 C7 C8 C9 177.65(16) . . . .
N4 N3 C10 C8 0.5(3) . . . .
N4 N3 C10 C11 -179.33(15) . . . .
C7 C8 C10 N3 0.6(2) . . . .
C9 C8 C10 N3 -178.27(17) . . . .
C7 C8 C10 C11 -179.59(16) . . . .
C9 C8 C10 C11 1.5(3) . . . .
C15 N5 C11 C12 0.3(3) . . . .
C15 N5 C11 C10 179.98(16) . . . .
N3 C10 C11 N5 -172.50(16) . . . .
C8 C10 C11 N5 7.7(3) . . . .
N3 C10 C11 C12 7.1(2) . . . .
C8 C10 C11 C12 -172.67(17) . . . .
N5 C11 C12 C13 0.4(3) . . . .
C10 C11 C12 C13 -179.27(18) . . . .
C11 C12 C13 C14 -0.4(3) . . . .
C12 C13 C14 C15 -0.3(3) . . . .
C11 N5 C15 C14 -1.1(3) . . . .
C13 C14 C15 N5 1.1(3) . . . .
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{e2b6deec-0c89-409c-a54c-9e4bbfc34dfb} ? ? ?
{97e44dbc-58fb-47ba-a4e1-796b384c35cd} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{e2b6deec-0c89-409c-a54c-9e4bbfc34dfb} '_publcif_info_datablock.publ_exptl'
loop_
_publcif_info_cif.paper_type
EE
