#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/73/2017314.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_2017314
loop_
_publ_author_name
'Zhang, Zhi-Hui'
'Tan, Xue'
'Chen, Sheng-Chun'
_publ_section_title
;
 4,4'-Methylenediphenol--4,4'-bipyridine (2/3): decarboxylation of
 5,5'-methylenedisalicylic acid under hydrothermal conditions
;
_journal_coeditor_code           SQ3200
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o457
_journal_page_last               o459
_journal_paper_doi               10.1107/S0108270109030832
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '2 C13 H12 O2 , 3 C10 H8 N2'
_chemical_formula_moiety         '2 C13 H12 O2 , 3 C10 H8 N2'
_chemical_formula_sum            'C56 H48 N6 O4'
_chemical_formula_weight         869.00
_chemical_name_systematic
;
4,4'-Methylenediphenol--4,4'-bipyridine (2/3)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 127.755(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   19.606(2)
_cell_length_b                   5.7354(6)
_cell_length_c                   25.4316(18)
_cell_measurement_reflns_used    1921
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      21.53
_cell_measurement_theta_min      2.63
_cell_volume                     2261.0(4)
_computing_cell_refinement
'APEX2 (Bruker, 2003) and SAINT (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005)
;
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0548
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11614
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.988000
_exptl_absorpt_correction_T_min  0.981191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             916
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.146
_refine_ls_extinction_coef       0.0044(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0414
_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)+(0.0340P)²+0.4007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1195
_reflns_number_gt                2727
_reflns_number_total             3976
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sq3200.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               2017314
_cod_database_fobs_code          2017314
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_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 0.11056(11) 0.8519(3) 0.86394(9) 0.0727(5) Uani d . 1 . .
O O1 0.16109(8) 0.4496(2) 0.84099(7) 0.0749(4) Uani d . 1 . .
H H1 0.1541 0.5759 0.8522 0.112 Uiso d R 1 . .
O O2 0.27022(8) 0.9862(3) 0.55323(7) 0.0886(5) Uani d . 1 . .
H H2 0.3015 1.0933 0.5583 0.133 Uiso d R 1 . .
C C1 0.34478(11) 0.4928(3) 0.80898(9) 0.0580(5) Uani d . 1 . .
C C2 0.29339(12) 0.2992(3) 0.79159(9) 0.0636(5) Uani d . 1 . .
H H2A 0.3001 0.1728 0.7722 0.076 Uiso calc R 1 . .
C C3 0.23241(13) 0.2872(3) 0.80200(9) 0.0635(5) Uani d . 1 . .
H H3 0.1984 0.1545 0.7893 0.076 Uiso calc R 1 . .
C C4 0.22140(11) 0.4711(3) 0.83116(9) 0.0559(5) Uani d . 1 . .
C C5 0.27270(12) 0.6659(3) 0.84973(9) 0.0608(5) Uani d . 1 . .
H H5 0.2666 0.7908 0.8698 0.073 Uiso calc R 1 . .
C C6 0.33302(12) 0.6755(3) 0.83850(9) 0.0634(5) Uani d . 1 . .
H H6 0.3669 0.8085 0.8511 0.076 Uiso calc R 1 . .
C C7 0.40905(12) 0.5113(4) 0.79462(10) 0.0729(6) Uani d . 1 . .
H H7A 0.4603 0.5911 0.8313 0.087 Uiso calc R 1 . .
H H7B 0.4260 0.3556 0.7919 0.087 Uiso calc R 1 . .
C C8 0.37374(11) 0.6403(3) 0.73083(9) 0.0579(5) Uani d . 1 . .
C C9 0.41147(11) 0.8411(4) 0.72991(9) 0.0624(5) Uani d . 1 . .
H H9 0.4606 0.8983 0.7697 0.075 Uiso calc R 1 . .
C C10 0.37854(11) 0.9602(3) 0.67170(9) 0.0608(5) Uani d . 1 . .
H H10 0.4051 1.0962 0.6726 0.073 Uiso calc R 1 . .
C C11 0.30667(11) 0.8778(4) 0.61251(9) 0.0598(5) Uani d . 1 . .
C C12 0.26806(13) 0.6763(4) 0.61194(10) 0.0719(6) Uani d . 1 . .
H H12 0.2195 0.6183 0.5720 0.086 Uiso calc R 1 . .
C C13 0.30136(12) 0.5608(4) 0.67043(10) 0.0689(5) Uani d . 1 . .
H H13 0.2745 0.4254 0.6694 0.083 Uiso calc R 1 . .
N N2 -0.09001(18) 1.7374(4) 0.92117(14) 0.1026(7) Uani d . 1 . .
C C14 0.03104(11) 1.2046(3) 0.88543(9) 0.0568(5) Uani d . 1 . .
C C15 0.11644(11) 1.1427(4) 0.93340(10) 0.0666(5) Uani d . 1 . .
H H15 0.1493 1.2187 0.9743 0.080 Uiso calc R 1 . .
C C16 0.15242(13) 0.9692(4) 0.92056(11) 0.0730(6) Uani d . 1 . .
H H16 0.2099 0.9314 0.9537 0.088 Uiso calc R 1 . .
C C17 0.02891(14) 0.9140(4) 0.81768(11) 0.0789(6) Uani d . 1 . .
H H17 -0.0021 0.8364 0.7771 0.095 Uiso calc R 1 . .
C C18 -0.01223(13) 1.0849(4) 0.82604(10) 0.0729(6) Uani d . 1 . .
H H18 -0.0695 1.1205 0.7916 0.087 Uiso calc R 1 . .
C C19 -0.01131(12) 1.3883(4) 0.89741(10) 0.0622(5) Uani d . 1 . .
C C20 -0.09922(14) 1.3839(4) 0.86562(11) 0.0823(7) Uani d . 1 . .
H H20 -0.1336 1.2650 0.8360 0.099 Uiso calc R 1 . .
C C21 -0.13467(18) 1.5614(6) 0.87907(15) 0.0993(9) Uani d . 1 . .
H H21 -0.1938 1.5575 0.8572 0.119 Uiso calc R 1 . .
C C22 -0.00638(19) 1.7353(4) 0.95122(14) 0.0910(7) Uani d . 1 . .
H H22 0.0268 1.8549 0.9810 0.109 Uiso calc R 1 . .
C C23 0.03511(15) 1.5685(4) 0.94149(11) 0.0728(6) Uani d . 1 . .
H H23 0.0945 1.5770 0.9646 0.087 Uiso calc R 1 . .
C C24 0.47205(10) 1.4604(3) 0.50883(8) 0.0510(4) Uani d . 1 . .
N N3 0.36938(10) 1.3029(3) 0.54424(8) 0.0697(5) Uani d . 1 . .
C C25 0.42120(13) 1.2642(4) 0.48076(10) 0.0734(6) Uani d . 1 . .
H H25 0.4200 1.1794 0.4491 0.088 Uiso calc R 1 . .
C C26 0.37212(14) 1.1942(4) 0.49982(11) 0.0822(7) Uani d . 1 . .
H H26 0.3385 1.0609 0.4800 0.099 Uiso calc R 1 . .
C C27 0.41740(13) 1.4927(4) 0.57059(10) 0.0715(6) Uani d . 1 . .
H H27 0.4166 1.5749 0.6017 0.086 Uiso calc R 1 . .
C C28 0.46844(12) 1.5757(4) 0.55469(10) 0.0656(5) Uani d . 1 . .
H H28 0.5008 1.7104 0.5750 0.079 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
C16 N1 C17 . . 115.79(18) ?
C4 O1 H1 . . 109.5 ?
C11 O2 H2 . . 109.5 ?
C2 C1 C6 . . 116.81(17) ?
C2 C1 C7 . . 122.11(19) ?
C6 C1 C7 . . 121.05(18) ?
C3 C2 C1 . . 121.97(18) ?
C3 C2 H2A . . 119.0 ?
C1 C2 H2A . . 119.0 ?
C2 C3 C4 . . 120.36(18) ?
C2 C3 H3 . . 119.8 ?
C4 C3 H3 . . 119.8 ?
O1 C4 C5 . . 123.13(17) ?
O1 C4 C3 . . 118.05(17) ?
C5 C4 C3 . . 118.81(17) ?
C6 C5 C4 . . 120.03(18) ?
C6 C5 H5 . . 120.0 ?
C4 C5 H5 . . 120.0 ?
C5 C6 C1 . . 122.00(18) ?
C5 C6 H6 . . 119.0 ?
C1 C6 H6 . . 119.0 ?
C8 C7 C1 . . 113.02(15) ?
C8 C7 H7A . . 109.0 ?
C1 C7 H7A . . 109.0 ?
C8 C7 H7B . . 109.0 ?
C1 C7 H7B . . 109.0 ?
H7A C7 H7B . . 107.8 ?
C9 C8 C13 . . 116.98(17) ?
C9 C8 C7 . . 122.02(18) ?
C13 C8 C7 . . 121.00(18) ?
C8 C9 C10 . . 121.92(18) ?
C8 C9 H9 . . 119.0 ?
C10 C9 H9 . . 119.0 ?
C11 C10 C9 . . 119.93(18) ?
C11 C10 H10 . . 120.0 ?
C9 C10 H10 . . 120.0 ?
O2 C11 C10 . . 123.29(18) ?
O2 C11 C12 . . 117.37(17) ?
C10 C11 C12 . . 119.33(17) ?
C13 C12 C11 . . 119.96(19) ?
C13 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
C12 C13 C8 . . 121.87(19) ?
C12 C13 H13 . . 119.1 ?
C8 C13 H13 . . 119.1 ?
C22 N2 C21 . . 115.5(2) ?
C18 C14 C15 . . 115.99(18) ?
C18 C14 C19 . . 122.13(17) ?
C15 C14 C19 . . 121.88(18) ?
C16 C15 C14 . . 119.86(19) ?
C16 C15 H15 . . 120.1 ?
C14 C15 H15 . . 120.1 ?
N1 C16 C15 . . 124.17(19) ?
N1 C16 H16 . . 117.9 ?
C15 C16 H16 . . 117.9 ?
N1 C17 C18 . . 124.1(2) ?
N1 C17 H17 . . 118.0 ?
C18 C17 H17 . . 118.0 ?
C17 C18 C14 . . 120.10(19) ?
C17 C18 H18 . . 120.0 ?
C14 C18 H18 . . 120.0 ?
C23 C19 C20 . . 117.0(2) ?
C23 C19 C14 . . 121.67(18) ?
C20 C19 C14 . . 121.3(2) ?
C19 C20 C21 . . 118.3(3) ?
C19 C20 H20 . . 120.8 ?
C21 C20 H20 . . 120.8 ?
N2 C21 C20 . . 124.8(3) ?
N2 C21 H21 . . 117.6 ?
C20 C21 H21 . . 117.6 ?
N2 C22 C23 . . 124.5(3) ?
N2 C22 H22 . . 117.8 ?
C23 C22 H22 . . 117.8 ?
C22 C23 C19 . . 120.0(2) ?
C22 C23 H23 . . 120.0 ?
C19 C23 H23 . . 120.0 ?
C25 C24 C28 . . 115.72(17) ?
C25 C24 C24 . 3_686 121.8(2) ?
C28 C24 C24 . 3_686 122.5(2) ?
C26 N3 C27 . . 115.68(17) ?
C26 C25 C24 . . 119.75(19) ?
C26 C25 H25 . . 120.1 ?
C24 C25 H25 . . 120.1 ?
N3 C26 C25 . . 124.6(2) ?
N3 C26 H26 . . 117.7 ?
C25 C26 H26 . . 117.7 ?
N3 C27 C28 . . 123.85(19) ?
N3 C27 H27 . . 118.1 ?
C28 C27 H27 . . 118.1 ?
C27 C28 C24 . . 120.43(19) ?
C27 C28 H28 . . 119.8 ?
C24 C28 H28 . . 119.8 ?
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 C16 . 1.324(3) ?
N1 C17 . 1.330(3) ?
O1 C4 . 1.356(2) ?
O1 H1 . 0.8200 ?
O2 C11 . 1.360(2) ?
O2 H2 . 0.8199 ?
C1 C2 . 1.378(3) ?
C1 C6 . 1.388(3) ?
C1 C7 . 1.515(3) ?
C2 C3 . 1.376(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.380(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.379(3) ?
C5 C6 . 1.377(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.511(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.377(3) ?
C8 C13 . 1.383(3) ?
C9 C10 . 1.380(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.370(2) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.377(3) ?
C12 C13 . 1.374(3) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
N2 C22 . 1.318(3) ?
N2 C21 . 1.336(4) ?
C14 C18 . 1.380(3) ?
C14 C15 . 1.384(2) ?
C14 C19 . 1.484(3) ?
C15 C16 . 1.370(3) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C17 C18 . 1.366(3) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
C19 C23 . 1.380(3) ?
C19 C20 . 1.385(3) ?
C20 C21 . 1.389(3) ?
C20 H20 . 0.9300 ?
C21 H21 . 0.9300 ?
C22 C23 . 1.373(3) ?
C22 H22 . 0.9300 ?
C23 H23 . 0.9300 ?
C24 C25 . 1.378(3) ?
C24 C28 . 1.380(2) ?
C24 C24 3_686 1.487(3) ?
N3 C26 . 1.320(3) ?
N3 C27 . 1.322(3) ?
C25 C26 . 1.376(3) ?
C25 H25 . 0.9300 ?
C26 H26 . 0.9300 ?
C27 C28 . 1.374(3) ?
C27 H27 . 0.9300 ?
C28 H28 . 0.9300 ?
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
O1 H1 N1 . 0.82 1.91 2.712(2) 166.8
O2 H2 N3 . 0.82 1.98 2.770(2) 161.0
C15 H15 O2 4_586 0.93 2.59 3.414(2) 148.6
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
C6 C1 C2 C3 . . . . 0.8(3) ?
C7 C1 C2 C3 . . . . -177.04(17) ?
C1 C2 C3 C4 . . . . -0.6(3) ?
C2 C3 C4 O1 . . . . -179.29(17) ?
C2 C3 C4 C5 . . . . -0.2(3) ?
O1 C4 C5 C6 . . . . 179.69(16) ?
C3 C4 C5 C6 . . . . 0.6(3) ?
C4 C5 C6 C1 . . . . -0.4(3) ?
C2 C1 C6 C5 . . . . -0.4(3) ?
C7 C1 C6 C5 . . . . 177.53(17) ?
C2 C1 C7 C8 . . . . 95.7(2) ?
C6 C1 C7 C8 . . . . -82.0(2) ?
C1 C7 C8 C9 . . . . 120.0(2) ?
C1 C7 C8 C13 . . . . -59.9(3) ?
C13 C8 C9 C10 . . . . 0.6(3) ?
C7 C8 C9 C10 . . . . -179.24(17) ?
C8 C9 C10 C11 . . . . -0.5(3) ?
C9 C10 C11 O2 . . . . 179.59(17) ?
C9 C10 C11 C12 . . . . 0.0(3) ?
O2 C11 C12 C13 . . . . -179.17(18) ?
C10 C11 C12 C13 . . . . 0.4(3) ?
C11 C12 C13 C8 . . . . -0.4(3) ?
C9 C8 C13 C12 . . . . -0.2(3) ?
C7 C8 C13 C12 . . . . 179.70(18) ?
C18 C14 C15 C16 . . . . -1.0(3) ?
C19 C14 C15 C16 . . . . 178.86(18) ?
C17 N1 C16 C15 . . . . 0.9(3) ?
C14 C15 C16 N1 . . . . 0.0(3) ?
C16 N1 C17 C18 . . . . -0.8(3) ?
N1 C17 C18 C14 . . . . -0.2(4) ?
C15 C14 C18 C17 . . . . 1.1(3) ?
C19 C14 C18 C17 . . . . -178.78(19) ?
C18 C14 C19 C23 . . . . -152.72(19) ?
C15 C14 C19 C23 . . . . 27.5(3) ?
C18 C14 C19 C20 . . . . 28.5(3) ?
C15 C14 C19 C20 . . . . -151.3(2) ?
C23 C19 C20 C21 . . . . 1.2(3) ?
C14 C19 C20 C21 . . . . -179.94(18) ?
C22 N2 C21 C20 . . . . -0.2(4) ?
C19 C20 C21 N2 . . . . -0.5(4) ?
C21 N2 C22 C23 . . . . 0.3(4) ?
N2 C22 C23 C19 . . . . 0.4(3) ?
C20 C19 C23 C22 . . . . -1.2(3) ?
C14 C19 C23 C22 . . . . 179.98(18) ?
C28 C24 C25 C26 . . . . -0.8(3) ?
C24 C24 C25 C26 3_686 . . . 178.4(2) ?
C27 N3 C26 C25 . . . . 0.7(3) ?
C24 C25 C26 N3 . . . . 0.1(4) ?
C26 N3 C27 C28 . . . . -0.7(3) ?
N3 C27 C28 C24 . . . . 0.0(3) ?
C25 C24 C28 C27 . . . . 0.8(3) ?
C24 C24 C28 C27 3_686 . . . -178.4(2) ?
