#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/96/4509629.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4509629
loop_
_publ_author_name
'Basu, Tannistha'
'Sparkes, Hazel A.'
'Mondal, Raju'
_publ_section_title
;
 Construction of Extended Molecular Networks with Heterosynthons in
 Cocrystals of Pyrazole and Acids
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5164
_journal_paper_doi               10.1021/cg900559q
_journal_volume                  9
_journal_year                    2009
_chemical_formula_moiety         'C11 H16 N4, 0.5(C8 H6 O4)'
_chemical_formula_sum            'C15 H19 N4 O2'
_chemical_formula_weight         287.34
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.467(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3836(4)
_cell_length_b                   8.2281(3)
_cell_length_c                   16.0591(6)
_cell_measurement_reflns_used    3875
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.272
_cell_measurement_theta_min      2.478
_cell_volume                     1483.70(9)
_computing_cell_refinement       'SAINT version 6.45A (Bruker, 2003)'
_computing_data_collection       'SMART version 5.054 (Bruker, 1999)'
_computing_data_reduction        'SAINT version 6.45A (Bruker, 2003)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 6K CCD Detector'
_diffrn_measurement_method       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    0.0290
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11372
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (G. Sheldrick, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0454
_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)+(0.0700P)²+0.3758P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1348
_reflns_number_gt                2884
_reflns_number_total             3678
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg900559qsup1.cif
_cod_data_source_block           08has017
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4509629
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
O1 O 0.53188(9) 0.63751(14) 0.22065(6) 0.0336(3) Uani 1 1 d .
O2 O 0.68638(10) 0.47769(14) 0.20592(6) 0.0349(3) Uani 1 1 d .
H2 H 0.7006 0.4839 0.2588 0.042 Uiso 1 1 calc R
N1 N 0.75829(11) 0.47917(15) 0.36758(7) 0.0267(3) Uani 1 1 d .
N2 N 0.81245(10) 0.34441(15) 0.40396(7) 0.0265(3) Uani 1 1 d .
H2A H 0.8193 0.2526 0.3770 0.032 Uiso 1 1 calc R
N3 N 0.81015(11) 0.40602(15) 0.78651(7) 0.0287(3) Uani 1 1 d .
N4 N 0.69832(11) 0.41973(15) 0.74222(7) 0.0289(3) Uani 1 1 d .
H4 H 0.6342 0.3850 0.7607 0.035 Uiso 1 1 calc R
C1 C 0.76613(12) 0.59091(17) 0.42867(8) 0.0261(3) Uani 1 1 d .
C2 C 0.82679(12) 0.52649(17) 0.50516(8) 0.0252(3) Uani 1 1 d .
C3 C 0.85472(12) 0.36820(17) 0.48678(8) 0.0254(3) Uani 1 1 d .
C4 C 0.71499(15) 0.75650(19) 0.41057(9) 0.0348(3) Uani 1 1 d .
H4A H 0.6660 0.7577 0.3544 0.052 Uiso 1 1 calc R
H4B H 0.7797 0.8356 0.4124 0.052 Uiso 1 1 calc R
H4C H 0.6657 0.7850 0.4530 0.052 Uiso 1 1 calc R
C5 C 0.91965(14) 0.23798(18) 0.54040(9) 0.0322(3) Uani 1 1 d .
H5A H 0.9187 0.1376 0.5075 0.048 Uiso 1 1 calc R
H5B H 0.8807 0.2189 0.5896 0.048 Uiso 1 1 calc R
H5C H 1.0022 0.2720 0.5594 0.048 Uiso 1 1 calc R
C6 C 0.85697(14) 0.61317(18) 0.58874(8) 0.0297(3) Uani 1 1 d .
H6A H 0.9446 0.6243 0.6028 0.036 Uiso 1 1 calc R
H6B H 0.8227 0.7240 0.5827 0.036 Uiso 1 1 calc R
C7 C 0.69642(13) 0.49241(16) 0.66686(8) 0.0267(3) Uani 1 1 d .
C8 C 0.81253(13) 0.52929(16) 0.66088(8) 0.0255(3) Uani 1 1 d .
C9 C 0.88056(13) 0.47255(17) 0.73665(8) 0.0258(3) Uani 1 1 d .
C10 C 0.58312(14) 0.51711(19) 0.60704(10) 0.0340(3) Uani 1 1 d .
H10A H 0.5187 0.5405 0.6389 0.051 Uiso 1 1 calc R
H10B H 0.5640 0.4185 0.5733 0.051 Uiso 1 1 calc R
H10C H 0.5922 0.6086 0.5695 0.051 Uiso 1 1 calc R
C11 C 1.01270(14) 0.4768(2) 0.76375(9) 0.0336(3) Uani 1 1 d .
H11A H 1.0507 0.4059 0.7270 0.050 Uiso 1 1 calc R
H11B H 1.0325 0.4391 0.8222 0.050 Uiso 1 1 calc R
H11C H 1.0414 0.5884 0.7597 0.050 Uiso 1 1 calc R
C12 C 0.58650(12) 0.55219(18) 0.17777(8) 0.0273(3) Uani 1 1 d .
C13 C 0.44297(12) 0.60975(17) 0.04579(8) 0.0270(3) Uani 1 1 d .
H13 H 0.4040 0.6847 0.0771 0.032 Uiso 1 1 calc R
C14 C 0.54273(12) 0.52483(17) 0.08551(8) 0.0250(3) Uani 1 1 d .
C15 C 0.59959(12) 0.41487(17) 0.03936(8) 0.0264(3) Uani 1 1 d .
H15 H 0.6675 0.3568 0.0662 0.032 Uiso 1 1 calc R
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
C12 O2 H2 109.5 .
C1 N1 N2 106.02(11) .
C3 N2 N1 111.66(11) .
C3 N2 H2A 124.2 .
N1 N2 H2A 124.2 .
C9 N3 N4 104.75(11) .
C7 N4 N3 112.52(12) .
C7 N4 H4 123.7 .
N3 N4 H4 123.7 .
N1 C1 C2 110.18(12) .
N1 C1 C4 120.57(12) .
C2 C1 C4 129.26(13) .
C3 C2 C1 105.35(12) .
C3 C2 C6 127.44(13) .
C1 C2 C6 127.20(13) .
N2 C3 C2 106.79(12) .
N2 C3 C5 121.74(13) .
C2 C3 C5 131.46(12) .
C1 C4 H4A 109.5 .
C1 C4 H4B 109.5 .
H4A C4 H4B 109.5 .
C1 C4 H4C 109.5 .
H4A C4 H4C 109.5 .
H4B C4 H4C 109.5 .
C3 C5 H5A 109.5 .
C3 C5 H5B 109.5 .
H5A C5 H5B 109.5 .
C3 C5 H5C 109.5 .
H5A C5 H5C 109.5 .
H5B C5 H5C 109.5 .
C8 C6 C2 114.31(12) .
C8 C6 H6A 108.7 .
C2 C6 H6A 108.7 .
C8 C6 H6B 108.7 .
C2 C6 H6B 108.7 .
H6A C6 H6B 107.6 .
N4 C7 C8 106.69(13) .
N4 C7 C10 121.61(13) .
C8 C7 C10 131.69(13) .
C7 C8 C9 105.34(12) .
C7 C8 C6 127.11(13) .
C9 C8 C6 127.55(13) .
N3 C9 C8 110.70(12) .
N3 C9 C11 120.51(12) .
C8 C9 C11 128.78(13) .
C7 C10 H10A 109.5 .
C7 C10 H10B 109.5 .
H10A C10 H10B 109.5 .
C7 C10 H10C 109.5 .
H10A C10 H10C 109.5 .
H10B C10 H10C 109.5 .
C9 C11 H11A 109.5 .
C9 C11 H11B 109.5 .
H11A C11 H11B 109.5 .
C9 C11 H11C 109.5 .
H11A C11 H11C 109.5 .
H11B C11 H11C 109.5 .
O1 C12 O2 124.70(13) .
O1 C12 C14 121.69(13) .
O2 C12 C14 113.60(12) .
C15 C13 C14 120.21(13) 3_665
C15 C13 H13 119.9 3_665
C14 C13 H13 119.9 .
C15 C14 C13 119.73(12) .
C15 C14 C12 120.96(12) .
C13 C14 C12 119.31(12) .
C13 C15 C14 120.06(13) 3_665
C13 C15 H15 120.0 3_665
C14 C15 H15 120.0 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C12 1.2225(17) .
O2 C12 1.3053(18) .
O2 H2 0.8400 .
N1 C1 1.3367(18) .
N1 N2 1.3536(16) .
N2 C3 1.3522(17) .
N2 H2A 0.8800 .
N3 C9 1.3396(18) .
N3 N4 1.3569(17) .
N4 C7 1.3469(17) .
N4 H4 0.8800 .
C1 C2 1.4099(18) .
C1 C4 1.491(2) .
C2 C3 1.384(2) .
C2 C6 1.5087(18) .
C3 C5 1.4921(19) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 C8 1.5058(18) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.375(2) .
C7 C10 1.490(2) .
C8 C9 1.4100(19) .
C9 C11 1.496(2) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 C14 1.5003(18) .
C13 C15 1.3884(19) 3_665
C13 C14 1.3952(19) .
C13 H13 0.9500 .
C14 C15 1.3946(19) .
C15 C13 1.3884(19) 3_665
C15 H15 0.9500 .
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 H2 N1 0.84 1.76 2.5906(15) 168.4 .
N2 H2A N3 0.88 1.94 2.7907(17) 161.0 4_565
N4 H4 O1 0.88 1.97 2.8211(16) 162.1 3_666
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146973
