#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/16/2221674.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_2221674
loop_
_publ_author_name
'He, Xiao'
'Qu, Gui-Rong'
'Deng, Dongsheng'
'Ji, Baoming'
_publ_section_title
;
 Dimethyl 6,6'-dicyano-2,2'-bipyridine-3,3'-dicarboxylate
;
_journal_coeditor_code           GK2200
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o985
_journal_paper_doi               10.1107/S1600536809012446
_journal_volume                  65
_journal_year                    2009
_chemical_formula_moiety         'C16 H10 N4 O4'
_chemical_formula_sum            'C16 H10 N4 O4'
_chemical_formula_weight         322.28
_chemical_name_systematic
;
 ?
;
_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                109.148(4)
_cell_angle_beta                 106.091(3)
_cell_angle_gamma                100.404(5)
_cell_formula_units_Z            2
_cell_length_a                   8.201(3)
_cell_length_b                   10.302(6)
_cell_length_c                   10.768(3)
_cell_measurement_reflns_used    2697
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      2.38
_cell_volume                     787.9(6)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXS97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega 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  0.0138
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5613
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.38
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9597
_exptl_absorpt_correction_T_min  0.9521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.41
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.115
_refine_ls_extinction_coef       0.044(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0335
_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)+(0.0434P)²+0.1400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0942
_reflns_number_gt                2391
_reflns_number_total             2845
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2200.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.

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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2221674
_cod_database_fobs_code          2221674
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
N N1 0.24082(14) 0.31796(12) 0.50125(12) 0.0430(3) Uani d . 1 . .
N N2 0.10699(15) -0.04177(12) 0.29318(12) 0.0441(3) Uani d . 1 . .
N N3 0.2207(3) 0.64855(17) 0.68504(19) 0.0880(5) Uani d . 1 . .
N N4 -0.1464(3) -0.37966(17) 0.06250(18) 0.0918(6) Uani d . 1 . .
O O1 0.21123(14) 0.07920(12) 0.04429(10) 0.0584(3) Uani d . 1 . .
O O3 0.39330(14) 0.18868(11) 0.78250(10) 0.0537(3) Uani d . 1 . .
O O4 0.55513(13) 0.24358(11) 0.65966(11) 0.0589(3) Uani d . 1 . .
O O2 0.41072(15) 0.03548(12) 0.20273(11) 0.0611(3) Uani d . 1 . .
C C2 0.28278(17) 0.22264(15) 0.28064(14) 0.0425(3) Uani d . 1 . .
C C1 0.25460(16) 0.20947(14) 0.39931(14) 0.0392(3) Uani d . 1 . .
C C12 0.30974(18) 0.10132(15) 0.17406(14) 0.0448(3) Uani d . 1 . .
C C3 0.2918(2) 0.35319(16) 0.26803(16) 0.0520(4) Uani d . 1 . .
H H3A 0.3070 0.3642 0.1892 0.062 Uiso calc R 1 . .
C C4 0.2783(2) 0.46654(16) 0.37267(17) 0.0534(4) Uani d . 1 . .
H H4A 0.2850 0.5553 0.3668 0.064 Uiso calc R 1 . .
C C5 0.25452(18) 0.44348(14) 0.48638(16) 0.0461(3) Uani d . 1 . .
C C11 0.2373(2) 0.55804(17) 0.59939(19) 0.0585(4) Uani d . 1 . .
C C15 0.2181(3) -0.0415(2) -0.06874(17) 0.0693(5) Uani d . 1 . .
H H15A 0.1425 -0.0479 -0.1578 0.104 Uiso calc R 1 . .
H H15B 0.1782 -0.1288 -0.0572 0.104 Uiso calc R 1 . .
H H15C 0.3381 -0.0277 -0.0661 0.104 Uiso calc R 1 . .
C C9 0.10581(18) -0.19269(14) 0.42201(15) 0.0448(3) Uani d . 1 . .
H H9A 0.0618 -0.2823 0.4223 0.054 Uiso calc R 1 . .
C C7 0.28339(16) 0.05361(13) 0.54006(13) 0.0379(3) Uani d . 1 . .
C C6 0.21790(16) 0.06783(13) 0.41195(14) 0.0382(3) Uani d . 1 . .
C C8 0.22261(18) -0.07911(14) 0.54392(15) 0.0432(3) Uani d . 1 . .
H H8A 0.2603 -0.0914 0.6280 0.052 Uiso calc R 1 . .
C C10 0.05610(17) -0.16976(14) 0.29983(14) 0.0436(3) Uani d . 1 . .
C C14 0.42572(18) 0.17362(14) 0.66546(14) 0.0416(3) Uani d . 1 . .
C C13 -0.0581(2) -0.28668(17) 0.16696(18) 0.0595(4) Uani d . 1 . .
C C16 0.5312(3) 0.2948(2) 0.91195(18) 0.0781(6) Uani d . 1 . .
H H16D 0.4957 0.2978 0.9904 0.117 Uiso calc R 1 . .
H H16A 0.5497 0.3878 0.9077 0.117 Uiso calc R 1 . .
H H16B 0.6398 0.2692 0.9235 0.117 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 N1 C5 . . 117.06(12) ?
C6 N2 C10 . . 117.28(12) ?
C12 O1 C15 . . 116.20(12) ?
C14 O3 C16 . . 115.67(13) ?
C3 C2 C1 . . 118.21(13) ?
C3 C2 C12 . . 120.91(12) ?
C1 C2 C12 . . 120.83(12) ?
N1 C1 C2 . . 122.74(12) ?
N1 C1 C6 . . 115.11(11) ?
C2 C1 C6 . . 121.83(12) ?
O2 C12 O1 . . 124.85(14) ?
O2 C12 C2 . . 124.19(13) ?
O1 C12 C2 . . 110.93(12) ?
C4 C3 C2 . . 119.75(13) ?
C4 C3 H3A . . 120.1 ?
C2 C3 H3A . . 120.1 ?
C3 C4 C5 . . 117.53(13) ?
C3 C4 H4A . . 121.2 ?
C5 C4 H4A . . 121.2 ?
N1 C5 C4 . . 124.68(13) ?
N1 C5 C11 . . 115.08(13) ?
C4 C5 C11 . . 120.23(13) ?
N3 C11 C5 . . 178.05(19) ?
O1 C15 H15A . . 109.5 ?
O1 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O1 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C10 C9 C8 . . 118.15(12) ?
C10 C9 H9A . . 120.9 ?
C8 C9 H9A . . 120.9 ?
C8 C7 C6 . . 118.08(12) ?
C8 C7 C14 . . 120.67(12) ?
C6 C7 C14 . . 121.05(11) ?
N2 C6 C7 . . 122.92(12) ?
N2 C6 C1 . . 114.08(11) ?
C7 C6 C1 . . 122.83(12) ?
C9 C8 C7 . . 119.38(13) ?
C9 C8 H8A . . 120.3 ?
C7 C8 H8A . . 120.3 ?
N2 C10 C9 . . 124.06(12) ?
N2 C10 C13 . . 115.18(13) ?
C9 C10 C13 . . 120.76(13) ?
O4 C14 O3 . . 125.10(13) ?
O4 C14 C7 . . 123.42(13) ?
O3 C14 C7 . . 111.43(11) ?
N4 C13 C10 . . 179.1(2) ?
O3 C16 H16D . . 109.5 ?
O3 C16 H16A . . 109.5 ?
H16D C16 H16A . . 109.5 ?
O3 C16 H16B . . 109.5 ?
H16D C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
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
N1 C1 . 1.3328(17) ?
N1 C5 . 1.3430(18) ?
N2 C6 . 1.3322(17) ?
N2 C10 . 1.3406(18) ?
N3 C11 . 1.136(2) ?
N4 C13 . 1.139(2) ?
O1 C12 . 1.3252(17) ?
O1 C15 . 1.4495(19) ?
O3 C14 . 1.3249(17) ?
O3 C16 . 1.4483(19) ?
O4 C14 . 1.1999(16) ?
O2 C12 . 1.1997(17) ?
C2 C3 . 1.386(2) ?
C2 C1 . 1.4038(19) ?
C2 C12 . 1.492(2) ?
C1 C6 . 1.4942(19) ?
C3 C4 . 1.378(2) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.378(2) ?
C4 H4A . 0.9300 ?
C5 C11 . 1.451(2) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C9 C10 . 1.376(2) ?
C9 C8 . 1.3786(19) ?
C9 H9A . 0.9300 ?
C7 C8 . 1.3864(19) ?
C7 C6 . 1.4011(18) ?
C7 C14 . 1.4913(19) ?
C8 H8A . 0.9300 ?
C10 C13 . 1.447(2) ?
C16 H16D . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
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
C4 H4A O4 2_666 0.93 2.39 3.222(3) 149
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
C5 N1 C1 C2 . . . . 0.20(19) ?
C5 N1 C1 C6 . . . . -173.30(11) ?
C3 C2 C1 N1 . . . . -1.7(2) ?
C12 C2 C1 N1 . . . . 175.79(12) ?
C3 C2 C1 C6 . . . . 171.35(12) ?
C12 C2 C1 C6 . . . . -11.14(19) ?
C15 O1 C12 O2 . . . . 5.1(2) ?
C15 O1 C12 C2 . . . . -176.63(12) ?
C3 C2 C12 O2 . . . . 129.19(16) ?
C1 C2 C12 O2 . . . . -48.3(2) ?
C3 C2 C12 O1 . . . . -49.07(17) ?
C1 C2 C12 O1 . . . . 133.48(13) ?
C1 C2 C3 C4 . . . . 1.8(2) ?
C12 C2 C3 C4 . . . . -175.66(13) ?
C2 C3 C4 C5 . . . . -0.5(2) ?
C1 N1 C5 C4 . . . . 1.3(2) ?
C1 N1 C5 C11 . . . . 179.56(13) ?
C3 C4 C5 N1 . . . . -1.1(2) ?
C3 C4 C5 C11 . . . . -179.31(14) ?
C10 N2 C6 C7 . . . . 0.86(19) ?
C10 N2 C6 C1 . . . . -174.43(11) ?
C8 C7 C6 N2 . . . . -3.22(19) ?
C14 C7 C6 N2 . . . . 171.65(12) ?
C8 C7 C6 C1 . . . . 171.66(11) ?
C14 C7 C6 C1 . . . . -13.47(18) ?
N1 C1 C6 N2 . . . . 132.04(13) ?
C2 C1 C6 N2 . . . . -41.53(17) ?
N1 C1 C6 C7 . . . . -43.25(17) ?
C2 C1 C6 C7 . . . . 143.18(13) ?
C10 C9 C8 C7 . . . . 0.99(19) ?
C6 C7 C8 C9 . . . . 2.17(19) ?
C14 C7 C8 C9 . . . . -172.72(12) ?
C6 N2 C10 C9 . . . . 2.6(2) ?
C6 N2 C10 C13 . . . . -177.41(12) ?
C8 C9 C10 N2 . . . . -3.6(2) ?
C8 C9 C10 C13 . . . . 176.48(13) ?
C16 O3 C14 O4 . . . . -2.7(2) ?
C16 O3 C14 C7 . . . . 175.13(13) ?
C8 C7 C14 O4 . . . . 130.87(15) ?
C6 C7 C14 O4 . . . . -43.86(19) ?
C8 C7 C14 O3 . . . . -46.97(16) ?
C6 C7 C14 O3 . . . . 138.30(12) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742111
