#------------------------------------------------------------------------------
#$Date: 2021-05-26 12:10:36 +0300 (Wed, 26 May 2021) $
#$Revision: 265505 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/28/1562880.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_1562880
loop_
_publ_author_name
'Yang, Juan'
'Hu, Rui-Xiang'
'Zhang, Man-Bo'
_publ_section_title
;
 Construction of monomers and chains assembled by 3d/4f metals and
 4′-(4-carboxyphenyl)-2,2′:6′,2″-terpyridine
;
_journal_name_full               'Journal of Solid State Chemistry'
_journal_page_first              398
_journal_page_last               403
_journal_paper_doi               10.1016/j.jssc.2012.07.002
_journal_volume                  196
_journal_year                    2012
_chemical_formula_sum            'C22 H15 N3 O2'
_chemical_formula_weight         353.37
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.56(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.194(2)
_cell_length_b                   7.1491(14)
_cell_length_c                   22.340(5)
_cell_measurement_reflns_used    4811
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      29.1195
_cell_measurement_theta_min      2.7185
_cell_volume                     1628.0(6)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13770
_diffrn_reflns_theta_full        29.13
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_min         3.38
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_correction_T_min  0.9675
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Chunk
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4345
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0713P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1274
_reflns_number_gt                3242
_reflns_number_total             4345
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            JSSC-2012-196-398.cif
_cod_data_source_block           1
_cod_original_cell_volume        1627.9(6)
_cod_original_sg_symbol_H-M      P2(1)/C
_cod_database_code               1562880
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N 0.43004(11) 0.30293(16) 0.35988(5) 0.0200(3) Uani 1 1 d . . .
O2 O -0.18815(10) 0.57924(15) 0.61540(4) 0.0263(3) Uani 1 1 d . . .
C9 C 0.38612(13) 0.30514(18) 0.54988(6) 0.0168(3) Uani 1 1 d . . .
N2 N 0.61683(11) 0.18780(15) 0.49341(5) 0.0175(2) Uani 1 1 d . . .
O1 O -0.12524(10) 0.53577(15) 0.71116(4) 0.0283(3) Uani 1 1 d . . .
C5 C 0.72583(13) 0.12767(18) 0.58751(6) 0.0182(3) Uani 1 1 d . . .
C19 C 0.02817(13) 0.48591(19) 0.63197(6) 0.0184(3) Uani 1 1 d . . .
N1 N 0.71374(12) 0.12098(18) 0.64703(5) 0.0250(3) Uani 1 1 d . . .
C16 C 0.26372(13) 0.36938(18) 0.57936(6) 0.0172(3) Uani 1 1 d . . .
C6 C 0.60841(13) 0.19228(18) 0.55320(6) 0.0171(3) Uani 1 1 d . . .
C7 C 0.51137(13) 0.24110(17) 0.46120(6) 0.0168(3) Uani 1 1 d . . .
C10 C 0.49647(13) 0.25286(18) 0.58288(6) 0.0181(3) Uani 1 1 d . . .
C18 C 0.05804(13) 0.53743(19) 0.57356(6) 0.0197(3) Uani 1 1 d . . .
C13 C 0.66282(15) 0.1817(2) 0.30934(7) 0.0256(3) Uani 1 1 d . . .
C21 C 0.23437(13) 0.32132(19) 0.63841(6) 0.0198(3) Uani 1 1 d . . .
C8 C 0.39451(13) 0.29631(19) 0.48765(6) 0.0180(3) Uani 1 1 d . . .
C4 C 0.84094(14) 0.0764(2) 0.55886(7) 0.0245(3) Uani 1 1 d . . .
C11 C 0.52844(13) 0.23877(18) 0.39493(6) 0.0172(3) Uani 1 1 d . . .
C22 C -0.10211(13) 0.53621(19) 0.65793(6) 0.0199(3) Uani 1 1 d . . .
C12 C 0.64618(14) 0.1752(2) 0.37046(6) 0.0217(3) Uani 1 1 d . . .
C20 C 0.11784(14) 0.3796(2) 0.66468(6) 0.0198(3) Uani 1 1 d . . .
C15 C 0.44785(15) 0.3064(2) 0.30057(6) 0.0248(3) Uani 1 1 d . . .
C17 C 0.17451(13) 0.48153(19) 0.54775(6) 0.0193(3) Uani 1 1 d . . .
C3 C 0.94702(15) 0.0168(2) 0.59318(7) 0.0288(3) Uani 1 1 d . . .
C14 C 0.56277(16) 0.2500(2) 0.27335(6) 0.0272(3) Uani 1 1 d . . .
C2 C 0.93514(15) 0.0074(2) 0.65446(7) 0.0275(3) Uani 1 1 d . . .
C1 C 0.81695(16) 0.0614(2) 0.67920(7) 0.0284(3) Uani 1 1 d . . .
H10A H 0.4990(14) 0.256(2) 0.6269(6) 0.023(4) Uiso 1 1 d . . .
H20A H 0.0978(16) 0.338(2) 0.7050(7) 0.025(4) Uiso 1 1 d . . .
H8A H 0.3183(16) 0.329(2) 0.4626(7) 0.024(4) Uiso 1 1 d . . .
H2A H 1.0075(18) -0.028(2) 0.6785(7) 0.032(4) Uiso 1 1 d . . .
H17A H 0.1935(16) 0.521(2) 0.5069(7) 0.032(4) Uiso 1 1 d . . .
H12A H 0.7168(17) 0.125(2) 0.3979(7) 0.031(5) Uiso 1 1 d . . .
H13A H 0.7406(18) 0.137(2) 0.2921(7) 0.034(5) Uiso 1 1 d . . .
H21A H 0.2976(16) 0.244(2) 0.6618(7) 0.028(4) Uiso 1 1 d . . .
H18A H -0.0042(15) 0.611(2) 0.5501(7) 0.022(4) Uiso 1 1 d . . .
H4A H 0.8432(18) 0.086(2) 0.5163(8) 0.038(5) Uiso 1 1 d . . .
H15A H 0.3782(17) 0.353(2) 0.2760(7) 0.029(4) Uiso 1 1 d . . .
H14A H 0.5683(17) 0.256(3) 0.2303(8) 0.038(5) Uiso 1 1 d . . .
H2B H -0.275(3) 0.619(3) 0.6295(10) 0.075(7) Uiso 1 1 d . . .
H1A H 0.8054(18) 0.059(2) 0.7241(8) 0.043(5) Uiso 1 1 d . . .
H3A H 1.0308(19) -0.019(3) 0.5745(8) 0.045(5) Uiso 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_1
_geom_angle_site_symmetry_3
C15 N3 C11 118.30(12) . .
C22 O2 H2B 115.5(13) . .
C10 C9 C8 117.34(12) . .
C10 C9 C16 121.70(11) . .
C8 C9 C16 120.96(12) . .
C6 N2 C7 117.95(11) . .
N1 C5 C4 122.30(13) . .
N1 C5 C6 116.21(12) . .
C4 C5 C6 121.50(12) . .
C20 C19 C18 119.23(12) . .
C20 C19 C22 120.55(12) . .
C18 C19 C22 120.14(12) . .
C5 N1 C1 117.77(13) . .
C21 C16 C17 118.24(12) . .
C21 C16 C9 121.96(12) . .
C17 C16 C9 119.80(12) . .
N2 C6 C10 122.83(12) . .
N2 C6 C5 116.55(11) . .
C10 C6 C5 120.62(12) . .
N2 C7 C8 122.47(12) . .
N2 C7 C11 115.33(12) . .
C8 C7 C11 122.20(12) . .
C9 C10 C6 119.54(12) . .
C9 C10 H10A 122.5(9) . .
C6 C10 H10A 117.9(9) . .
C17 C18 C19 120.69(13) . .
C17 C18 H18A 119.3(9) . .
C19 C18 H18A 120.0(9) . .
C12 C13 C14 119.39(14) . .
C12 C13 H13A 120.4(10) . .
C14 C13 H13A 120.2(10) . .
C20 C21 C16 120.98(13) . .
C20 C21 H21A 119.7(9) . .
C16 C21 H21A 119.3(9) . .
C7 C8 C9 119.79(12) . .
C7 C8 H8A 120.0(9) . .
C9 C8 H8A 120.2(9) . .
C3 C4 C5 118.90(13) . .
C3 C4 H4A 123.2(11) . .
C5 C4 H4A 117.9(11) . .
N3 C11 C12 121.35(12) . .
N3 C11 C7 118.65(12) . .
C12 C11 C7 119.98(12) . .
O1 C22 O2 124.75(13) . .
O1 C22 C19 124.04(13) . .
O2 C22 C19 111.21(11) . .
C13 C12 C11 119.37(14) . .
C13 C12 H12A 121.4(9) . .
C11 C12 H12A 119.2(9) . .
C19 C20 C21 120.05(12) . .
C19 C20 H20A 120.7(10) . .
C21 C20 H20A 119.2(10) . .
N3 C15 C14 123.52(14) . .
N3 C15 H15A 117.9(10) . .
C14 C15 H15A 118.5(10) . .
C18 C17 C16 120.76(12) . .
C18 C17 H17A 119.1(10) . .
C16 C17 H17A 120.1(10) . .
C2 C3 C4 119.27(14) . .
C2 C3 H3A 119.4(11) . .
C4 C3 H3A 121.3(11) . .
C13 C14 C15 118.05(13) . .
C13 C14 H14A 123.0(11) . .
C15 C14 H14A 118.9(11) . .
C3 C2 C1 117.92(14) . .
C3 C2 H2A 120.2(10) . .
C1 C2 H2A 121.8(10) . .
N1 C1 C2 123.83(14) . .
N1 C1 H1A 116.1(11) . .
C2 C1 H1A 120.1(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N3 C15 1.3392(17) .
N3 C11 1.3469(17) .
O2 C22 1.3230(17) .
O2 H2B 0.99(3) .
C9 C10 1.3901(18) .
C9 C8 1.3950(17) .
C9 C16 1.4891(18) .
N2 C6 1.3398(16) .
N2 C7 1.3429(17) .
O1 C22 1.2146(16) .
C5 N1 1.3373(17) .
C5 C4 1.3913(19) .
C5 C6 1.4884(19) .
C19 C20 1.3906(19) .
C19 C18 1.3924(18) .
C19 C22 1.4981(18) .
N1 C1 1.3381(19) .
C16 C21 1.3985(18) .
C16 C17 1.3986(19) .
C6 C10 1.3943(18) .
C7 C8 1.3920(18) .
C7 C11 1.4925(17) .
C10 H10A 0.985(14) .
C18 C17 1.3838(18) .
C18 H18A 0.974(15) .
C13 C12 1.3785(19) .
C13 C14 1.382(2) .
C13 H13A 0.940(18) .
C21 C20 1.3938(19) .
C21 H21A 0.993(16) .
C8 H8A 0.981(16) .
C4 C3 1.387(2) .
C4 H4A 0.953(18) .
C11 C12 1.3993(18) .
C12 H12A 1.006(17) .
C20 H20A 0.971(16) .
C15 C14 1.385(2) .
C15 H15A 0.953(17) .
C17 H17A 0.975(17) .
C3 C2 1.377(2) .
C3 H3A 0.988(19) .
C14 H14A 0.965(17) .
C2 C1 1.385(2) .
C2 H2A 0.943(18) .
C1 H1A 1.011(18) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2B N3 0.99(3) 1.69(3) 2.6685(16) 169(2) 3_566
