#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/61/7106185.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_7106185
loop_
_publ_author_name
'Gautam R. Desiraju'
'Arijit Mukherjee'
_publ_section_title
;
 Synthon polymorphism and pseudopolymorphism in co-crystals. The
 4,4?-bipyridine–4-hydroxybenzoic acid structural landscape
;
_journal_name_full               Chem.Commun.
_journal_page_first              4090
_journal_paper_doi               10.1039/c0cc05857b
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         '2(C11 H9 N), C7 H6 O3'
_chemical_formula_sum            'C29 H24 N2 O3'
_chemical_formula_weight         448.50
_chemical_name_common
;
4phenylpyridine:4-hydroxybenzoicacid
;
_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                66.060(5)
_cell_angle_beta                 84.424(6)
_cell_angle_gamma                83.795(6)
_cell_formula_units_Z            4
_cell_length_a                   7.5084(7)
_cell_length_b                   18.0404(16)
_cell_length_c                   19.0238(17)
_cell_measurement_reflns_used    18780
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.0
_cell_volume                     2337.3(4)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-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  0.0611
_diffrn_reflns_av_sigmaI/netI    0.0830
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25067
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_correction_T_min  0.9755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     805
_refine_ls_number_reflns         10707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1188
_refine_ls_R_factor_gt           0.0610
_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)+(0.0537P)²+0.3916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1402
_reflns_number_gt                6382
_reflns_number_total             10707
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c0cc05857b.txt
_cod_data_source_block           datam4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               7106185
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
H4 H 0.370(3) 0.8941(12) 0.4401(13) 0.020(6) Uiso 1 1 d . . .
H52 H 0.352(3) 0.0611(14) 0.4308(13) 0.029(6) Uiso 1 1 d . . .
H54 H 0.417(3) 0.1632(15) 0.1737(13) 0.035(7) Uiso 1 1 d . . .
H49 H 0.387(3) 0.3364(14) 0.2807(13) 0.033(7) Uiso 1 1 d . . .
H47 H -0.425(3) 1.3159(14) -0.1235(13) 0.034(7) Uiso 1 1 d . . .
H7 H 0.575(3) 1.0196(12) 0.1778(12) 0.020(5) Uiso 1 1 d . . .
H15 H 1.362(3) 0.5579(14) -0.0996(13) 0.032(6) Uiso 1 1 d . . .
H30 H 0.719(3) 0.2846(13) 0.5445(12) 0.030(6) Uiso 1 1 d . . .
H58 H 0.194(3) 0.3733(15) 0.1835(14) 0.042(7) Uiso 1 1 d . . .
H21 H 1.075(3) 0.6846(15) -0.3173(13) 0.035(7) Uiso 1 1 d . . .
H10 H 1.207(3) 0.4613(13) 0.3196(13) 0.025(6) Uiso 1 1 d . . .
H3 H 0.154(3) 0.9397(13) 0.3411(13) 0.033(6) Uiso 1 1 d . . .
H51 H 0.317(3) 0.1109(14) 0.2982(13) 0.034(7) Uiso 1 1 d . . .
H13 H 1.062(3) 0.5810(13) 0.0599(13) 0.024(6) Uiso 1 1 d . . .
H48 H 0.421(3) 0.2835(15) 0.4140(14) 0.042(7) Uiso 1 1 d . . .
H29 H 0.445(3) 0.2422(15) 0.6214(15) 0.042(7) Uiso 1 1 d . . .
H6 H 0.775(3) 0.9776(14) 0.2748(13) 0.036(7) Uiso 1 1 d . . .
H16 H 1.283(3) 0.6263(15) -0.2276(15) 0.044(7) Uiso 1 1 d . . .
H36 H 0.028(3) 0.4331(16) 0.5969(14) 0.040(7) Uiso 1 1 d . . .
H46 H -0.663(3) 1.3680(15) -0.2050(14) 0.041(7) Uiso 1 1 d . . .
H43 H -0.492(3) 1.0874(15) -0.1156(13) 0.037(7) Uiso 1 1 d . . .
H11 H 1.437(3) 0.5078(13) 0.2210(13) 0.030(6) Uiso 1 1 d . . .
H45 H -0.815(3) 1.2820(15) -0.2435(14) 0.043(7) Uiso 1 1 d . . .
H32 H 0.159(3) 0.1967(14) 0.6293(13) 0.033(6) Uiso 1 1 d . . .
H40 H -0.118(3) 1.2544(14) -0.1243(14) 0.034(7) Uiso 1 1 d . . .
H56 H 0.252(3) 0.3473(14) -0.0248(14) 0.040(7) Uiso 1 1 d . . .
H35 H -0.241(3) 0.3936(15) 0.6749(14) 0.044(7) Uiso 1 1 d . . .
H14 H 0.829(3) 0.5363(14) 0.1570(13) 0.034(6) Uiso 1 1 d . . .
H34 H -0.298(3) 0.2576(14) 0.7327(14) 0.040(7) Uiso 1 1 d . . .
H22 H 1.012(3) 0.7579(15) -0.4513(15) 0.045(8) Uiso 1 1 d . . .
H55 H 0.374(3) 0.2139(14) 0.0397(14) 0.039(7) Uiso 1 1 d . . .
H38 H -0.384(3) 1.0597(14) 0.0159(14) 0.040(7) Uiso 1 1 d . . .
H44 H -0.725(4) 1.1438(16) -0.1999(16) 0.056(9) Uiso 1 1 d . . .
H27 H 0.188(4) 0.4531(15) 0.4752(14) 0.046(7) Uiso 1 1 d . . .
H25 H 1.208(3) 0.8947(14) -0.3081(14) 0.037(7) Uiso 1 1 d . . .
H33 H -0.097(4) 0.1562(17) 0.7125(15) 0.054(8) Uiso 1 1 d . . .
H41 H 0.133(3) 1.2013(15) -0.0477(14) 0.043(7) Uiso 1 1 d . . .
H37 H -0.129(3) 1.0105(16) 0.0899(15) 0.051(8) Uiso 1 1 d . . .
H57 H 0.162(3) 0.4280(16) 0.0470(14) 0.048(8) Uiso 1 1 d . . .
H18 H 1.114(3) 0.8249(16) -0.1805(14) 0.043(7) Uiso 1 1 d . . .
H19 H 1.193(3) 0.7503(15) -0.0543(15) 0.046(8) Uiso 1 1 d . . .
H26 H 0.471(4) 0.4839(17) 0.4046(16) 0.056(8) Uiso 1 1 d . . .
H6O H 1.362(4) 0.6022(19) 0.0238(19) 0.076(10) Uiso 1 1 d . . .
H24 H 1.149(4) 0.9656(18) -0.4367(17) 0.066(9) Uiso 1 1 d . . .
H4O H 0.791(4) 0.4148(18) 0.4150(18) 0.077(10) Uiso 1 1 d . . .
H23 H 1.047(4) 0.8993(18) -0.5096(18) 0.067(9) Uiso 1 1 d . . .
H1O H 0.188(5) 1.066(2) 0.083(2) 0.109(13) Uiso 1 1 d . . .
H3O H 0.669(4) 0.8765(19) 0.4750(19) 0.080(11) Uiso 1 1 d . . .
O3 O 0.7146(2) 0.90767(10) 0.41998(9) 0.0337(4) Uani 1 1 d . . .
O1 O 0.2851(2) 1.04158(10) 0.11920(9) 0.0310(4) Uani 1 1 d . . .
C42 C -0.4369(3) 1.19555(13) -0.11106(12) 0.0244(5) Uani 1 1 d . . .
O2 O 0.0559(2) 1.00399(13) 0.20593(10) 0.0535(6) Uani 1 1 d . . .
C5 C 0.5913(3) 0.93169(13) 0.36602(12) 0.0246(5) Uani 1 1 d . . .
C3 C 0.2896(3) 0.94668(13) 0.32773(13) 0.0262(5) Uani 1 1 d . . .
N3 N 0.0200(3) 1.10120(13) 0.02602(11) 0.0354(5) Uani 1 1 d . . .
C2 C 0.3492(3) 0.98280(13) 0.25044(12) 0.0238(5) Uani 1 1 d . . .
C41 C 0.0193(3) 1.17251(16) -0.03517(13) 0.0341(6) Uani 1 1 d . . .
C1 C 0.2161(3) 1.00993(14) 0.19082(13) 0.0292(5) Uani 1 1 d . . .
C45 C -0.7183(3) 1.26038(16) -0.20878(14) 0.0336(6) Uani 1 1 d . . .
C4 C 0.4095(3) 0.92091(13) 0.38533(13) 0.0260(5) Uani 1 1 d . . .
C43 C -0.5271(3) 1.14566(15) -0.13317(13) 0.0301(5) Uani 1 1 d . . .
C6 C 0.6517(3) 0.96859(14) 0.28907(13) 0.0262(5) Uani 1 1 d . . .
C7 C 0.5306(3) 0.99341(13) 0.23206(13) 0.0235(5) Uani 1 1 d . . .
C39 C -0.2800(3) 1.16267(13) -0.06282(12) 0.0262(5) Uani 1 1 d . . .
C46 C -0.6314(3) 1.30990(16) -0.18687(14) 0.0346(6) Uani 1 1 d . . .
C47 C -0.4908(3) 1.27828(14) -0.13801(13) 0.0294(5) Uani 1 1 d . . .
C38 C -0.2792(4) 1.08869(16) 0.00068(14) 0.0366(6) Uani 1 1 d . . .
C40 C -0.1264(3) 1.20452(15) -0.08038(14) 0.0311(6) Uani 1 1 d . . .
C37 C -0.1282(3) 1.06122(17) 0.04298(15) 0.0399(7) Uani 1 1 d . . .
C44 C -0.6671(3) 1.17796(16) -0.18200(14) 0.0333(6) Uani 1 1 d . . .
O4 O 0.9005(2) 0.43729(10) 0.37952(9) 0.0312(4) Uani 1 1 d . . .
O6 O 1.4047(2) 0.57229(10) 0.07645(10) 0.0328(4) Uani 1 1 d . . .
O5 O 0.6932(2) 0.47856(10) 0.29219(9) 0.0369(4) Uani 1 1 d . . .
C10 C 1.1773(3) 0.48768(13) 0.26537(13) 0.0252(5) Uani 1 1 d . . .
C8 C 0.8499(3) 0.47046(13) 0.30751(12) 0.0252(5) Uani 1 1 d . . .
C9 C 0.9985(3) 0.49610(13) 0.24770(12) 0.0230(5) Uani 1 1 d . . .
C11 C 1.3115(3) 0.51349(14) 0.20786(13) 0.0269(5) Uani 1 1 d . . .
C14 C 0.9571(3) 0.53072(14) 0.17034(13) 0.0264(5) Uani 1 1 d . . .
N1 N 1.2828(3) 0.64811(13) -0.06569(11) 0.0358(5) Uani 1 1 d . . .
C17 C 1.1910(3) 0.73522(14) -0.21864(13) 0.0266(5) Uani 1 1 d . . .
C12 C 1.2689(3) 0.54830(13) 0.13091(12) 0.0240(5) Uani 1 1 d . . .
C18 C 1.1640(3) 0.77010(16) -0.16505(14) 0.0331(6) Uani 1 1 d . . .
C16 C 1.2625(3) 0.65511(15) -0.19286(14) 0.0298(5) Uani 1 1 d . . .
C13 C 1.0902(3) 0.55679(14) 0.11252(13) 0.0267(5) Uani 1 1 d . . .
C20 C 1.1487(3) 0.78194(14) -0.30052(13) 0.0288(5) Uani 1 1 d . . .
C15 C 1.3066(3) 0.61437(16) -0.11715(14) 0.0325(6) Uani 1 1 d . . .
C21 C 1.0945(3) 0.74326(17) -0.34383(14) 0.0336(6) Uani 1 1 d . . .
C22 C 1.0574(3) 0.78583(19) -0.42032(15) 0.0414(7) Uani 1 1 d . . .
C25 C 1.1662(3) 0.86565(16) -0.33636(16) 0.0377(6) Uani 1 1 d . . .
C23 C 1.0737(3) 0.86857(19) -0.45471(16) 0.0449(7) Uani 1 1 d . . .
C19 C 1.2112(3) 0.72478(17) -0.09049(15) 0.0377(6) Uani 1 1 d . . .
C24 C 1.1293(4) 0.90825(19) -0.41326(17) 0.0474(7) Uani 1 1 d . . .
N4 N 0.3932(3) 0.16654(12) 0.43252(11) 0.0315(5) Uani 1 1 d . . .
C50 C 0.3423(3) 0.22977(13) 0.27362(12) 0.0226(5) Uani 1 1 d . . .
C53 C 0.3130(3) 0.26315(13) 0.19015(12) 0.0232(5) Uani 1 1 d . . .
C58 C 0.2347(3) 0.34174(14) 0.15207(13) 0.0274(5) Uani 1 1 d . . .
C54 C 0.3620(3) 0.21596(15) 0.14771(13) 0.0287(5) Uani 1 1 d . . .
C48 C 0.4011(3) 0.24573(15) 0.38850(14) 0.0309(5) Uani 1 1 d . . .
C51 C 0.3369(3) 0.14732(14) 0.31944(13) 0.0286(5) Uani 1 1 d . . .
C55 C 0.3376(3) 0.24650(15) 0.06978(14) 0.0308(5) Uani 1 1 d . . .
C49 C 0.3763(3) 0.27929(15) 0.31037(13) 0.0275(5) Uani 1 1 d . . .
C57 C 0.2101(3) 0.37207(15) 0.07389(14) 0.0324(6) Uani 1 1 d . . .
C56 C 0.2625(3) 0.32462(16) 0.03222(14) 0.0329(6) Uani 1 1 d . . .
C52 C 0.3624(3) 0.11899(15) 0.39695(13) 0.0302(5) Uani 1 1 d . . .
N2 N 0.6120(3) 0.38795(13) 0.47112(11) 0.0348(5) Uani 1 1 d . . .
C31 C 0.1169(3) 0.31898(13) 0.60438(12) 0.0262(5) Uani 1 1 d . . .
C28 C 0.2865(3) 0.34286(14) 0.55727(13) 0.0274(5) Uani 1 1 d . . .
C33 C -0.0744(3) 0.21490(16) 0.68729(14) 0.0352(6) Uani 1 1 d . . .
C32 C 0.0777(3) 0.23801(14) 0.63882(14) 0.0306(5) Uani 1 1 d . . .
C36 C -0.0028(3) 0.37689(15) 0.61839(14) 0.0325(6) Uani 1 1 d . . .
C30 C 0.6019(3) 0.31772(16) 0.53260(14) 0.0337(6) Uani 1 1 d . . .
C35 C -0.1565(3) 0.35360(17) 0.66625(15) 0.0371(6) Uani 1 1 d . . .
C29 C 0.4448(3) 0.29320(15) 0.57622(14) 0.0314(6) Uani 1 1 d . . .
C34 C -0.1919(3) 0.27235(17) 0.70057(14) 0.0360(6) Uani 1 1 d . . .
C27 C 0.2974(3) 0.41538(16) 0.49268(14) 0.0392(6) Uani 1 1 d . . .
C26 C 0.4597(4) 0.43532(17) 0.45202(16) 0.0444(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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O3 H3O 116.2(18) . . ?
C1 O1 H1O 110(2) . . ?
C43 C42 C47 119.0(2) . . ?
C43 C42 C39 121.0(2) . . ?
C47 C42 C39 119.9(2) . . ?
O3 C5 C4 122.3(2) . . ?
O3 C5 C6 117.7(2) . . ?
C4 C5 C6 120.0(2) . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 120.8(13) . . ?
C2 C3 H3 118.6(13) . . ?
C37 N3 C41 117.2(2) . . ?
C7 C2 C3 119.0(2) . . ?
C7 C2 C1 122.2(2) . . ?
C3 C2 C1 118.8(2) . . ?
N3 C41 C40 122.7(2) . . ?
N3 C41 H41 116.2(14) . . ?
C40 C41 H41 121.2(14) . . ?
O2 C1 O1 122.2(2) . . ?
O2 C1 C2 123.1(2) . . ?
O1 C1 C2 114.6(2) . . ?
C46 C45 C44 120.1(2) . . ?
C46 C45 H45 121.1(15) . . ?
C44 C45 H45 118.7(15) . . ?
C3 C4 C5 119.7(2) . . ?
C3 C4 H4 121.5(12) . . ?
C5 C4 H4 118.8(12) . . ?
C44 C43 C42 120.5(2) . . ?
C44 C43 H43 118.6(14) . . ?
C42 C43 H43 120.9(14) . . ?
C7 C6 C5 119.6(2) . . ?
C7 C6 H6 119.0(14) . . ?
C5 C6 H6 121.3(14) . . ?
C6 C7 C2 121.0(2) . . ?
C6 C7 H7 118.8(12) . . ?
C2 C7 H7 120.2(12) . . ?
C40 C39 C38 117.3(2) . . ?
C40 C39 C42 120.8(2) . . ?
C38 C39 C42 121.9(2) . . ?
C45 C46 C47 120.6(2) . . ?
C45 C46 H46 122.3(15) . . ?
C47 C46 H46 117.1(15) . . ?
C46 C47 C42 119.9(2) . . ?
C46 C47 H47 119.7(13) . . ?
C42 C47 H47 120.3(13) . . ?
C37 C38 C39 119.0(3) . . ?
C37 C38 H38 121.3(15) . . ?
C39 C38 H38 119.6(15) . . ?
C41 C40 C39 120.0(2) . . ?
C41 C40 H40 119.4(14) . . ?
C39 C40 H40 120.6(14) . . ?
N3 C37 C38 123.8(2) . . ?
N3 C37 H37 116.5(16) . . ?
C38 C37 H37 119.6(16) . . ?
C45 C44 C43 119.8(2) . . ?
C45 C44 H44 119.7(16) . . ?
C43 C44 H44 120.4(16) . . ?
C8 O4 H4O 107.9(17) . . ?
C12 O6 H6O 112.7(18) . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H10 120.2(13) . . ?
C9 C10 H10 118.9(13) . . ?
O5 C8 O4 122.4(2) . . ?
O5 C8 C9 122.84(19) . . ?
O4 C8 C9 114.80(19) . . ?
C10 C9 C14 118.8(2) . . ?
C10 C9 C8 122.73(19) . . ?
C14 C9 C8 118.48(19) . . ?
C10 C11 C12 119.9(2) . . ?
C10 C11 H11 120.2(13) . . ?
C12 C11 H11 119.9(13) . . ?
C13 C14 C9 120.7(2) . . ?
C13 C14 H14 119.9(13) . . ?
C9 C14 H14 119.4(13) . . ?
C19 N1 C15 116.8(2) . . ?
C16 C17 C18 117.1(2) . . ?
C16 C17 C20 121.2(2) . . ?
C18 C17 C20 121.6(2) . . ?
O6 C12 C11 118.0(2) . . ?
O6 C12 C13 122.4(2) . . ?
C11 C12 C13 119.7(2) . . ?
C19 C18 C17 119.2(2) . . ?
C19 C18 H18 121.3(15) . . ?
C17 C18 H18 119.5(15) . . ?
C15 C16 C17 119.8(2) . . ?
C15 C16 H16 118.8(15) . . ?
C17 C16 H16 121.3(15) . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H13 120.9(13) . . ?
C12 C13 H13 119.1(13) . . ?
C21 C20 C25 118.2(2) . . ?
C21 C20 C17 120.8(2) . . ?
C25 C20 C17 120.9(2) . . ?
N1 C15 C16 123.2(2) . . ?
N1 C15 H15 117.3(13) . . ?
C16 C15 H15 119.4(13) . . ?
C22 C21 C20 121.4(3) . . ?
C22 C21 H21 120.6(14) . . ?
C20 C21 H21 117.9(14) . . ?
C23 C22 C21 119.7(3) . . ?
C23 C22 H22 118.9(14) . . ?
C21 C22 H22 121.3(14) . . ?
C24 C25 C20 120.3(3) . . ?
C24 C25 H25 119.2(14) . . ?
C20 C25 H25 120.5(14) . . ?
C24 C23 C22 120.0(3) . . ?
C24 C23 H23 120.1(17) . . ?
C22 C23 H23 119.8(17) . . ?
N1 C19 C18 123.9(2) . . ?
N1 C19 H19 118.0(15) . . ?
C18 C19 H19 118.0(15) . . ?
C23 C24 C25 120.3(3) . . ?
C23 C24 H24 121.8(18) . . ?
C25 C24 H24 117.8(18) . . ?
C48 N4 C52 116.6(2) . . ?
C51 C50 C49 116.4(2) . . ?
C51 C50 C53 121.6(2) . . ?
C49 C50 C53 121.9(2) . . ?
C54 C53 C58 118.3(2) . . ?
C54 C53 C50 120.4(2) . . ?
C58 C53 C50 121.4(2) . . ?
C57 C58 C53 120.5(2) . . ?
C57 C58 H58 122.2(15) . . ?
C53 C58 H58 117.3(14) . . ?
C55 C54 C53 121.1(2) . . ?
C55 C54 H54 121.1(14) . . ?
C53 C54 H54 117.8(14) . . ?
N4 C48 C49 123.3(2) . . ?
N4 C48 H48 118.4(14) . . ?
C49 C48 H48 118.3(14) . . ?
C52 C51 C50 119.8(2) . . ?
C52 C51 H51 119.6(15) . . ?
C50 C51 H51 120.6(15) . . ?
C54 C55 C56 120.4(2) . . ?
C54 C55 H55 121.2(14) . . ?
C56 C55 H55 118.4(14) . . ?
C48 C49 C50 120.0(2) . . ?
C48 C49 H49 120.3(14) . . ?
C50 C49 H49 119.6(14) . . ?
C58 C57 C56 120.5(2) . . ?
C58 C57 H57 120.1(15) . . ?
C56 C57 H57 119.3(15) . . ?
C55 C56 C57 119.3(2) . . ?
C55 C56 H56 119.8(14) . . ?
C57 C56 H56 120.8(14) . . ?
N4 C52 C51 123.9(2) . . ?
N4 C52 H52 115.4(13) . . ?
C51 C52 H52 120.6(13) . . ?
C30 N2 C26 116.9(2) . . ?
C32 C31 C36 118.4(2) . . ?
C32 C31 C28 120.8(2) . . ?
C36 C31 C28 120.7(2) . . ?
C27 C28 C29 116.4(2) . . ?
C27 C28 C31 122.5(2) . . ?
C29 C28 C31 121.2(2) . . ?
C34 C33 C32 120.3(2) . . ?
C34 C33 H33 120.6(16) . . ?
C32 C33 H33 119.2(16) . . ?
C33 C32 C31 120.9(2) . . ?
C33 C32 H32 119.4(14) . . ?
C31 C32 H32 119.7(14) . . ?
C35 C36 C31 120.5(2) . . ?
C35 C36 H36 120.8(15) . . ?
C31 C36 H36 118.6(15) . . ?
N2 C30 C29 123.3(2) . . ?
N2 C30 H30 113.8(13) . . ?
C29 C30 H30 122.9(13) . . ?
C34 C35 C36 120.0(2) . . ?
C34 C35 H35 119.2(15) . . ?
C36 C35 H35 120.7(15) . . ?
C30 C29 C28 120.1(2) . . ?
C30 C29 H29 120.1(15) . . ?
C28 C29 H29 119.8(15) . . ?
C33 C34 C35 119.9(2) . . ?
C33 C34 H34 121.2(15) . . ?
C35 C34 H34 118.9(15) . . ?
C26 C27 C28 120.0(2) . . ?
C26 C27 H27 119.6(15) . . ?
C28 C27 H27 120.5(15) . . ?
N2 C26 C27 123.4(2) . . ?
N2 C26 H26 114.1(17) . . ?
C27 C26 H26 122.4(17) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C5 1.355(3) . ?
O3 H3O 1.01(3) . ?
O1 C1 1.321(3) . ?
O1 H1O 1.00(4) . ?
C42 C43 1.392(3) . ?
C42 C47 1.394(3) . ?
C42 C39 1.483(3) . ?
O2 C1 1.216(3) . ?
C5 C4 1.392(3) . ?
C5 C6 1.392(3) . ?
C3 C4 1.384(3) . ?
C3 C2 1.394(3) . ?
C3 H3 1.03(2) . ?
N3 C37 1.333(3) . ?
N3 C41 1.340(3) . ?
C2 C7 1.387(3) . ?
C2 C1 1.479(3) . ?
C41 C40 1.383(3) . ?
C41 H41 1.01(3) . ?
C45 C46 1.370(3) . ?
C45 C44 1.385(3) . ?
C45 H45 0.97(3) . ?
C4 H4 0.99(2) . ?
C43 C44 1.388(3) . ?
C43 H43 0.98(2) . ?
C6 C7 1.383(3) . ?
C6 H6 0.95(2) . ?
C7 H7 0.99(2) . ?
C39 C40 1.386(3) . ?
C39 C38 1.390(3) . ?
C46 C47 1.391(3) . ?
C46 H46 0.97(2) . ?
C47 H47 1.01(2) . ?
C38 C37 1.382(3) . ?
C38 H38 0.95(3) . ?
C40 H40 0.95(2) . ?
C37 H37 0.98(3) . ?
C44 H44 0.97(3) . ?
O4 C8 1.329(3) . ?
O4 H4O 1.02(3) . ?
O6 C12 1.351(3) . ?
O6 H6O 0.99(3) . ?
O5 C8 1.219(3) . ?
C10 C11 1.379(3) . ?
C10 C9 1.393(3) . ?
C10 H10 0.98(2) . ?
C8 C9 1.480(3) . ?
C9 C14 1.398(3) . ?
C11 C12 1.393(3) . ?
C11 H11 0.98(2) . ?
C14 C13 1.378(3) . ?
C14 H14 1.00(2) . ?
N1 C19 1.336(3) . ?
N1 C15 1.337(3) . ?
C17 C16 1.388(3) . ?
C17 C18 1.389(3) . ?
C17 C20 1.487(3) . ?
C12 C13 1.396(3) . ?
C18 C19 1.378(4) . ?
C18 H18 0.96(3) . ?
C16 C15 1.380(3) . ?
C16 H16 0.99(3) . ?
C13 H13 0.95(2) . ?
C20 C21 1.387(3) . ?
C20 C25 1.397(3) . ?
C15 H15 0.99(2) . ?
C21 C22 1.382(4) . ?
C21 H21 0.99(2) . ?
C22 C23 1.379(4) . ?
C22 H22 1.02(3) . ?
C25 C24 1.388(4) . ?
C25 H25 0.98(2) . ?
C23 C24 1.377(4) . ?
C23 H23 0.99(3) . ?
C19 H19 0.96(3) . ?
C24 H24 0.97(3) . ?
N4 C48 1.336(3) . ?
N4 C52 1.339(3) . ?
C50 C51 1.388(3) . ?
C50 C49 1.394(3) . ?
C50 C53 1.482(3) . ?
C53 C54 1.394(3) . ?
C53 C58 1.396(3) . ?
C58 C57 1.384(3) . ?
C58 H58 0.99(3) . ?
C54 C55 1.380(3) . ?
C54 H54 0.94(2) . ?
C48 C49 1.382(3) . ?
C48 H48 1.01(3) . ?
C51 C52 1.376(3) . ?
C51 H51 0.93(2) . ?
C55 C56 1.380(3) . ?
C55 H55 0.98(2) . ?
C49 H49 0.96(2) . ?
C57 C56 1.390(4) . ?
C57 H57 0.97(3) . ?
C56 H56 1.00(2) . ?
C52 H52 0.99(2) . ?
N2 C30 1.334(3) . ?
N2 C26 1.337(3) . ?
C31 C32 1.389(3) . ?
C31 C36 1.395(3) . ?
C31 C28 1.481(3) . ?
C28 C27 1.388(3) . ?
C28 C29 1.391(3) . ?
C33 C34 1.374(4) . ?
C33 C32 1.384(3) . ?
C33 H33 1.00(3) . ?
C32 H32 0.97(2) . ?
C36 C35 1.388(4) . ?
C36 H36 0.97(2) . ?
C30 C29 1.378(3) . ?
C30 H30 1.00(2) . ?
C35 C34 1.385(4) . ?
C35 H35 0.96(3) . ?
C29 H29 0.97(2) . ?
C34 H34 0.95(3) . ?
C27 C26 1.378(4) . ?
C27 H27 1.00(3) . ?
C26 H26 0.97(3) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C3 C2 C7 -0.7(3) . . . . ?
C4 C3 C2 C1 -179.6(2) . . . . ?
C37 N3 C41 C40 -0.6(4) . . . . ?
C7 C2 C1 O2 -177.1(2) . . . . ?
C3 C2 C1 O2 1.7(4) . . . . ?
C7 C2 C1 O1 2.8(3) . . . . ?
C3 C2 C1 O1 -178.4(2) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
O3 C5 C4 C3 180.0(2) . . . . ?
C6 C5 C4 C3 0.3(3) . . . . ?
C47 C42 C43 C44 0.7(3) . . . . ?
C39 C42 C43 C44 -176.2(2) . . . . ?
O3 C5 C6 C7 179.4(2) . . . . ?
C4 C5 C6 C7 -0.9(3) . . . . ?
C5 C6 C7 C2 0.6(3) . . . . ?
C3 C2 C7 C6 0.1(3) . . . . ?
C1 C2 C7 C6 179.0(2) . . . . ?
C43 C42 C39 C40 135.3(2) . . . . ?
C47 C42 C39 C40 -41.6(3) . . . . ?
C43 C42 C39 C38 -43.7(3) . . . . ?
C47 C42 C39 C38 139.4(2) . . . . ?
C44 C45 C46 C47 0.3(4) . . . . ?
C45 C46 C47 C42 0.2(4) . . . . ?
C43 C42 C47 C46 -0.7(3) . . . . ?
C39 C42 C47 C46 176.3(2) . . . . ?
C40 C39 C38 C37 0.6(4) . . . . ?
C42 C39 C38 C37 179.6(2) . . . . ?
N3 C41 C40 C39 0.3(4) . . . . ?
C38 C39 C40 C41 -0.3(4) . . . . ?
C42 C39 C40 C41 -179.4(2) . . . . ?
C41 N3 C37 C38 0.9(4) . . . . ?
C39 C38 C37 N3 -0.9(4) . . . . ?
C46 C45 C44 C43 -0.3(4) . . . . ?
C42 C43 C44 C45 -0.3(4) . . . . ?
C11 C10 C9 C14 0.5(3) . . . . ?
C11 C10 C9 C8 -179.0(2) . . . . ?
O5 C8 C9 C10 179.2(2) . . . . ?
O4 C8 C9 C10 -1.2(3) . . . . ?
O5 C8 C9 C14 -0.3(3) . . . . ?
O4 C8 C9 C14 179.3(2) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C10 C9 C14 C13 -0.6(3) . . . . ?
C8 C9 C14 C13 178.9(2) . . . . ?
C10 C11 C12 O6 -179.6(2) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C16 C17 C18 C19 1.0(3) . . . . ?
C20 C17 C18 C19 -177.9(2) . . . . ?
C18 C17 C16 C15 -1.3(3) . . . . ?
C20 C17 C16 C15 177.6(2) . . . . ?
C9 C14 C13 C12 0.4(3) . . . . ?
O6 C12 C13 C14 179.5(2) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C16 C17 C20 C21 31.7(3) . . . . ?
C18 C17 C20 C21 -149.5(2) . . . . ?
C16 C17 C20 C25 -146.9(2) . . . . ?
C18 C17 C20 C25 31.9(3) . . . . ?
C19 N1 C15 C16 0.6(3) . . . . ?
C17 C16 C15 N1 0.5(4) . . . . ?
C25 C20 C21 C22 -0.4(4) . . . . ?
C17 C20 C21 C22 -179.0(2) . . . . ?
C20 C21 C22 C23 -0.2(4) . . . . ?
C21 C20 C25 C24 0.2(4) . . . . ?
C17 C20 C25 C24 178.8(2) . . . . ?
C21 C22 C23 C24 1.0(4) . . . . ?
C15 N1 C19 C18 -0.9(4) . . . . ?
C17 C18 C19 N1 0.1(4) . . . . ?
C22 C23 C24 C25 -1.1(4) . . . . ?
C20 C25 C24 C23 0.5(4) . . . . ?
C51 C50 C53 C54 -30.4(3) . . . . ?
C49 C50 C53 C54 149.7(2) . . . . ?
C51 C50 C53 C58 149.0(2) . . . . ?
C49 C50 C53 C58 -30.9(3) . . . . ?
C54 C53 C58 C57 -1.2(3) . . . . ?
C50 C53 C58 C57 179.4(2) . . . . ?
C58 C53 C54 C55 1.4(3) . . . . ?
C50 C53 C54 C55 -179.2(2) . . . . ?
C52 N4 C48 C49 1.1(3) . . . . ?
C49 C50 C51 C52 0.8(3) . . . . ?
C53 C50 C51 C52 -179.1(2) . . . . ?
C53 C54 C55 C56 -0.5(4) . . . . ?
N4 C48 C49 C50 -0.5(4) . . . . ?
C51 C50 C49 C48 -0.5(3) . . . . ?
C53 C50 C49 C48 179.4(2) . . . . ?
C53 C58 C57 C56 0.2(4) . . . . ?
C54 C55 C56 C57 -0.6(4) . . . . ?
C58 C57 C56 C55 0.7(4) . . . . ?
C48 N4 C52 C51 -0.8(4) . . . . ?
C50 C51 C52 N4 -0.1(4) . . . . ?
C32 C31 C28 C27 145.3(2) . . . . ?
C36 C31 C28 C27 -38.0(3) . . . . ?
C32 C31 C28 C29 -35.1(3) . . . . ?
C36 C31 C28 C29 141.6(2) . . . . ?
C34 C33 C32 C31 1.7(4) . . . . ?
C36 C31 C32 C33 -1.4(3) . . . . ?
C28 C31 C32 C33 175.4(2) . . . . ?
C32 C31 C36 C35 0.6(3) . . . . ?
C28 C31 C36 C35 -176.2(2) . . . . ?
C26 N2 C30 C29 -0.5(4) . . . . ?
C31 C36 C35 C34 0.0(4) . . . . ?
N2 C30 C29 C28 -0.5(4) . . . . ?
C27 C28 C29 C30 1.3(4) . . . . ?
C31 C28 C29 C30 -178.3(2) . . . . ?
C32 C33 C34 C35 -1.0(4) . . . . ?
C36 C35 C34 C33 0.2(4) . . . . ?
C29 C28 C27 C26 -1.1(4) . . . . ?
C31 C28 C27 C26 178.5(2) . . . . ?
C30 N2 C26 C27 0.6(4) . . . . ?
C28 C27 C26 N2 0.1(5) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139181798
