#------------------------------------------------------------------------------
#$Date: 2016-03-23 23:36:17 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179508 $
#$URL: svn://www.crystallography.net/cod/cif/4/34/05/4340554.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_4340554
loop_
_publ_author_name
'Hurley, Nicholas J.'
'Hayward, John J.'
'Rawson, Jeremy M.'
'Murrie, Mark'
'Pilkington, Melanie'
_publ_section_title
;
 Exploring the Coordination Chemistry of
 3,3'-Di(picolinamoyl)-2,2'-bipyridine: One Ligand, Multiple Nuclearities.
;
_journal_issue                   16
_journal_name_full               'Inorganic chemistry'
_journal_page_first              8610
_journal_page_last               8623
_journal_paper_doi               10.1021/ic501224q
_journal_volume                  53
_journal_year                    2014
_chemical_formula_moiety         'C22 H16 N6 O2'
_chemical_formula_sum            'C22 H16 N6 O2'
_chemical_formula_weight         396.41
_chemical_name_systematic
;
 ?
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 94.593(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.1606(13)
_cell_length_b                   3.9083(3)
_cell_length_c                   16.1931(13)
_cell_measurement_reflns_used    2283
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.22
_cell_measurement_theta_min      2.52
_cell_volume                     893.31(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7800
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.524
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_description       plate
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.658
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0719
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1168P)²+1.5828P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1918
_refine_ls_wR_factor_ref         0.2122
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1572
_reflns_number_total             2036
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic501224q_si_003.cif
_cod_data_source_block           sv3feb09
_cod_depositor_comments
'Adding full bibliography for 4340554--4340557.cif.'
_cod_database_code               4340554
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelxl_version_number           2013-3
#END Tags that were not found in dictionaries
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
C1 C 0.52547(17) 0.4112(6) 1.03620(13) 0.0191(5) Uani 1 1 d . .
C2 C 0.62516(17) 0.3655(6) 1.04751(14) 0.0198(5) Uani 1 1 d . .
C3 C 0.66188(18) 0.1925(7) 1.11864(15) 0.0232(6) Uani 1 1 d . .
H3 H 0.7268 0.1551 1.1273 0.028 Uiso 1 1 calc R U
C4 C 0.60196(19) 0.0766(7) 1.17625(15) 0.0245(6) Uani 1 1 d . .
H4 H 0.6259 -0.0333 1.2244 0.029 Uiso 1 1 calc R U
C5 C 0.50612(18) 0.1286(7) 1.16026(14) 0.0234(6) Uani 1 1 d . .
H5 H 0.4654 0.0472 1.1981 0.028 Uiso 1 1 calc R U
C6 C 0.77981(18) 0.5391(7) 1.00027(16) 0.0257(6) Uani 1 1 d . .
C7 C 0.82092(17) 0.6911(7) 0.92475(15) 0.0232(6) Uani 1 1 d . .
C8 C 0.91594(19) 0.7795(7) 0.93092(17) 0.0281(6) Uani 1 1 d . .
H8 H 0.9533 0.7456 0.9801 0.034 Uiso 1 1 calc R U
C9 C 0.95450(19) 0.9204(8) 0.86184(18) 0.0308(6) Uani 1 1 d . .
H9 H 1.0178 0.9863 0.8641 0.037 Uiso 1 1 calc R U
C10 C 0.8962(2) 0.9587(8) 0.79034(17) 0.0327(7) Uani 1 1 d . .
H10 H 0.9197 1.0483 0.7429 0.039 Uiso 1 1 calc R U
C11 C 0.8024(2) 0.8626(8) 0.78996(17) 0.0329(7) Uani 1 1 d . .
H11 H 0.7638 0.8903 0.7412 0.040 Uiso 1 1 calc R U
H2 H 0.648(3) 0.577(11) 0.944(3) 0.062(12) Uiso 1 1 d . .
N1 N 0.46930(15) 0.2905(6) 1.09287(12) 0.0213(5) Uani 1 1 d . .
N2 N 0.68515(15) 0.4871(6) 0.98944(12) 0.0227(5) Uani 1 1 d . .
N3 N 0.76363(15) 0.7314(6) 0.85593(13) 0.0279(5) Uani 1 1 d . .
O1 O 0.83054(14) 0.4813(7) 1.06341(13) 0.0441(7) Uani 1 1 d . .
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_3
N1 C1 C2 120.2(2) .
N1 C1 C1 115.0(3) 3_667
C2 C1 C1 124.8(3) 3_667
C3 C2 N2 120.8(2) .
C3 C2 C1 117.8(2) .
N2 C2 C1 121.4(2) .
C4 C3 C2 120.3(2) .
C5 C4 C3 118.2(2) .
N1 C5 C4 122.7(2) .
O1 C6 N2 126.2(2) .
O1 C6 C7 120.6(2) .
N2 C6 C7 113.2(2) .
N3 C7 C8 123.6(2) .
N3 C7 C6 118.2(2) .
C8 C7 C6 118.2(2) .
C7 C8 C9 118.7(2) .
C10 C9 C8 118.1(2) .
C9 C10 C11 119.1(3) .
N3 C11 C10 123.8(3) .
C5 N1 C1 120.7(2) .
C6 N2 C2 127.7(2) .
C7 N3 C11 116.7(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.347(3) .
C1 C2 1.420(3) .
C1 C1 1.497(5) 3_667
C2 C3 1.399(3) .
C2 N2 1.400(3) .
C3 C4 1.386(3) .
C4 C5 1.376(4) .
C5 N1 1.331(3) .
C6 O1 1.223(3) .
C6 N2 1.353(3) .
C6 C7 1.517(4) .
C7 N3 1.334(3) .
C7 C8 1.385(4) .
C8 C9 1.397(4) .
C9 C10 1.375(4) .
C10 C11 1.380(4) .
C11 N3 1.341(3) .
