#------------------------------------------------------------------------------
#$Date: 2016-10-05 04:54:15 +0300 (Wed, 05 Oct 2016) $
#$Revision: 186917 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/42/1544244.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_1544244
loop_
_publ_author_name
'Rillema, D. Paul'
'Moore, Curtis'
'KomReddy, Venugopal'
_publ_section_title
;
 Diethyl 2,2'-bipyridine-4,4'-dicarboxylate
;
_journal_issue                   10
_journal_name_full               IUCrData
_journal_page_first              x161547
_journal_paper_doi               10.1107/S2414314616015479
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'C16 H16 N2 O4'
_chemical_formula_moiety         'C16 H16 N2 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31
_chemical_name_systematic
;
Diethyl 2,2'-bipyridine-4,4'-dicarboxylate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
;
Olex2 1.2-beta
(compiled 2014.01.22 svn.r2872 for OlexSys, GUI svn.r4747)
;
_cell_angle_alpha                92.212(7)
_cell_angle_beta                 93.163(7)
_cell_angle_gamma                93.016(7)
_cell_formula_units_Z            2
_cell_length_a                   3.9059(8)
_cell_length_b                   13.493(3)
_cell_length_c                   13.767(3)
_cell_measurement_reflns_used    2248
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.027
_cell_measurement_theta_min      2.966
_cell_volume                     722.8(3)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009) and Mercury (Macrae et
al.,  2008)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHEXLS2014 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 7.9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEXII Ultra'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10150
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.399
_diffrn_reflns_theta_min         1.483
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.0916
_exptl_absorpt_correction_T_min  0.0659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       Plate
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.131
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.261
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0568
_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)+(0.0623P)²+0.3520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1413
_reflns_number_gt                1699
_reflns_number_total             2664
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su4079sup1.cif
_cod_data_source_block           I
_cod_database_code               1544244
_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   0.994
_shelxl_version_number           .2013
loop_
_space_group_symop_operation_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_occupancy
N N1 0.6443(6) -0.08269(16) 0.09213(16) 0.0229(6) Uani d 1
O O1 0.1227(5) 0.21648(14) 0.24091(14) 0.0322(5) Uani d 1
O O2 0.2666(5) 0.12418(13) 0.36775(13) 0.0267(5) Uani d 1
C C1 0.5052(6) -0.00246(18) 0.05424(19) 0.0213(6) Uani d 1
C C2 0.3798(7) 0.0728(2) 0.1117(2) 0.0227(6) Uani d 1
H H2 0.2878 0.1291 0.0827 0.027 Uiso calc 1
C C3 0.3909(7) 0.06454(19) 0.2116(2) 0.0230(7) Uani d 1
C C4 0.5353(7) -0.0181(2) 0.2512(2) 0.0250(7) Uani d 1
H H4 0.5496 -0.0255 0.3196 0.030 Uiso calc 1
C C5 0.6573(7) -0.0889(2) 0.1889(2) 0.0243(7) Uani d 1
H H5 0.7558 -0.1452 0.2163 0.029 Uiso calc 1
C C6 0.2460(7) 0.1439(2) 0.2732(2) 0.0238(7) Uani d 1
C C7 0.1308(7) 0.1979(2) 0.43362(19) 0.0268(7) Uani d 1
H H7A -0.1157 0.2057 0.4167 0.032 Uiso calc 1
H H7B 0.2562 0.2631 0.4290 0.032 Uiso calc 1
C C8 0.1788(8) 0.1608(2) 0.5350(2) 0.0322(8) Uani d 1
H H8A 0.0535 0.0963 0.5385 0.048 Uiso calc 1
H H8B 0.0904 0.2084 0.5817 0.048 Uiso calc 1
H H8C 0.4237 0.1535 0.5508 0.048 Uiso calc 1
N N1' 0.6531(6) 0.41872(16) 0.40638(16) 0.0225(6) Uani d 1
O O1' 0.1233(5) 0.71739(14) 0.26347(13) 0.0307(5) Uani d 1
O O2' 0.2484(5) 0.62205(13) 0.13410(13) 0.0257(5) Uani d 1
C C1' 0.5100(6) 0.49830(18) 0.44587(19) 0.0210(6) Uani d 1
C C2' 0.3829(7) 0.57364(19) 0.39046(19) 0.0214(6) Uani d 1
H H2' 0.2889 0.6296 0.4209 0.026 Uiso calc 1
C C3' 0.3960(7) 0.56565(19) 0.2899(2) 0.0213(6) Uani d 1
C C4' 0.5453(7) 0.4843(2) 0.2487(2) 0.0231(7) Uani d 1
H H4' 0.5623 0.4774 0.1803 0.028 Uiso calc 1
C C5' 0.6691(7) 0.4135(2) 0.3096(2) 0.0241(7) Uani d 1
H H5' 0.7713 0.3580 0.2810 0.029 Uiso calc 1
C C6' 0.2446(7) 0.6440(2) 0.2295(2) 0.0219(6) Uani d 1
C C7' 0.0956(8) 0.6935(2) 0.0684(2) 0.0325(7) Uani d 1
H H7'A 0.2167 0.7597 0.0789 0.039 Uiso calc 1
H H7'B -0.1497 0.6999 0.0808 0.039 Uiso calc 1
C C8' 0.1316(9) 0.6543(2) -0.0342(2) 0.0401(8) Uani d 1
H H8'A 0.0362 0.7007 -0.0802 0.060 Uiso calc 1
H H8'B 0.0070 0.5894 -0.0441 0.060 Uiso calc 1
H H8'C 0.3750 0.6473 -0.0452 0.060 Uiso calc 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_3
_geom_angle
C5 N1 C1 . 117.6(2)
C6 O2 C7 . 115.9(2)
N1 C1 C1 2_655 116.4(3)
N1 C1 C2 . 122.5(2)
C2 C1 C1 2_655 121.1(3)
C1 C2 H2 . 120.4
C3 C2 C1 . 119.1(2)
C3 C2 H2 . 120.4
C2 C3 C4 . 118.6(2)
C2 C3 C6 . 119.1(2)
C4 C3 C6 . 122.3(3)
C3 C4 H4 . 120.7
C5 C4 C3 . 118.5(3)
C5 C4 H4 . 120.7
N1 C5 C4 . 123.5(2)
N1 C5 H5 . 118.2
C4 C5 H5 . 118.2
O1 C6 O2 . 124.3(3)
O1 C6 C3 . 123.6(3)
O2 C6 C3 . 112.1(2)
O2 C7 H7A . 110.3
O2 C7 H7B . 110.3
O2 C7 C8 . 106.9(2)
H7A C7 H7B . 108.6
C8 C7 H7A . 110.3
C8 C7 H7B . 110.3
C7 C8 H8A . 109.5
C7 C8 H8B . 109.5
C7 C8 H8C . 109.5
H8A C8 H8B . 109.5
H8A C8 H8C . 109.5
H8B C8 H8C . 109.5
C5' N1' C1' . 117.3(2)
C6' O2' C7' . 116.5(2)
N1' C1' C1' 2_666 116.4(3)
N1' C1' C2' . 122.8(2)
C2' C1' C1' 2_666 120.8(3)
C1' C2' H2' . 120.6
C3' C2' C1' . 118.8(2)
C3' C2' H2' . 120.6
C2' C3' C6' . 119.1(2)
C4' C3' C2' . 118.7(2)
C4' C3' C6' . 122.1(2)
C3' C4' H4' . 120.8
C5' C4' C3' . 118.5(3)
C5' C4' H4' . 120.8
N1' C5' C4' . 123.8(3)
N1' C5' H5' . 118.1
C4' C5' H5' . 118.1
O1' C6' O2' . 123.9(2)
O1' C6' C3' . 123.6(2)
O2' C6' C3' . 112.4(2)
O2' C7' H7'A . 110.3
O2' C7' H7'B . 110.3
O2' C7' C8' . 107.2(2)
H7'A C7' H7'B . 108.5
C8' C7' H7'A . 110.3
C8' C7' H7'B . 110.3
C7' C8' H8'A . 109.5
C7' C8' H8'B . 109.5
C7' C8' H8'C . 109.5
H8'A C8' H8'B . 109.5
H8'A C8' H8'C . 109.5
H8'B C8' H8'C . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C1 . 1.347(3)
N1 C5 . 1.336(3)
O1 C6 . 1.203(3)
O2 C6 . 1.338(3)
O2 C7 . 1.460(3)
C1 C1 2_655 1.496(5)
C1 C2 . 1.389(4)
C2 H2 . 0.9500
C2 C3 . 1.382(4)
C3 C4 . 1.392(4)
C3 C6 . 1.494(4)
C4 H4 . 0.9500
C4 C5 . 1.381(4)
C5 H5 . 0.9500
C7 H7A . 0.9900
C7 H7B . 0.9900
C7 C8 . 1.507(4)
C8 H8A . 0.9800
C8 H8B . 0.9800
C8 H8C . 0.9800
N1' C1' . 1.346(3)
N1' C5' . 1.336(3)
O1' C6' . 1.209(3)
O2' C6' . 1.336(3)
O2' C7' . 1.474(3)
C1' C1' 2_666 1.496(5)
C1' C2' . 1.390(4)
C2' H2' . 0.9500
C2' C3' . 1.388(4)
C3' C4' . 1.386(4)
C3' C6' . 1.496(4)
C4' H4' . 0.9500
C4' C5' . 1.384(4)
C5' H5' . 0.9500
C7' H7'A . 0.9900
C7' H7'B . 0.9900
C7' C8' . 1.505(4)
C8' H8'A . 0.9800
C8' H8'B . 0.9800
C8' H8'C . 0.9800
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
C5 H5 O1' 1_645 0.95 2.49 3.421(3) 167 yes
C8 H8B O1' 2_566 0.98 2.52 3.465(3) 161 yes
C5' H5' O1 1_655 0.95 2.47 3.404(3) 167 yes
C8' H8'A O1 2_565 0.98 2.58 3.518(3) 161 yes
C7 H7B N1' . 0.99 2.58 3.565(4) 172 yes

_cod_database_fobs_code 1544244
