#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/46/1514629.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_1514629
loop_
_publ_author_name
'Bučar, Dejan-Krešimir'
'Day, Graeme M.'
'Halasz, Ivan'
'Zhang, Geoff G. Z.'
'Sander, John R. G.'
'Reid, David G.'
'MacGillivray, Leonard R.'
'Duer, Melinda J.'
'Jones, William'
_publ_section_title
;
 The curious case of (caffeine)·(benzoic acid): how heteronuclear
 seeding allowed the formation of an elusive cocrystal
;
_journal_issue                   12
_journal_name_full               'Chemical Science'
_journal_page_first              4417
_journal_paper_doi               10.1039/c3sc51419f
_journal_volume                  4
_journal_year                    2013
_chemical_formula_moiety         'C8 H10 N4 O2, C7 H6 O2'
_chemical_formula_sum            'C15 H16 N4 O4'
_chemical_formula_weight         316.32
_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'
_cell_angle_alpha                90
_cell_angle_beta                 104.5787(42)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2358(13)
_cell_length_b                   9.1056(10)
_cell_length_c                   15.9131(18)
_cell_measurement_temperature    293
_cell_volume                     1575.6(3)
_computing_cell_refinement       'TOPAS (Bruker 2009)'
_computing_data_collection       'X'Pert Data Collector (Panalytical)'
_computing_structure_refinement  'TOPAS (Bruker 2009)'
_computing_structure_solution    'TOPAS (Bruker 2009)'
_diffrn_ambient_temperature      293
_diffrn_detector_type            'X'Celerator RTMS'
_diffrn_measurement_device_type  'Panalytical X'pert PRO'
_diffrn_radiation_monochromator  none
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Cu
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       'microcrystaline powder'
_pd_char_colour                  white
_pd_meas_2theta_range_inc        0.033
_pd_meas_2theta_range_max        60
_pd_meas_2theta_range_min        3
_pd_meas_number_of_points        1726
_pd_meas_scan_method             cont
_pd_prep_temperature             293
_pd_proc_ls_background_function  'Chebyshev polynomial'
_pd_proc_ls_pref_orient_corr     'Spherical harmonics, 4th order'
_pd_proc_ls_profile_function     'Fundamental parameters'
_pd_proc_ls_prof_R_factor        0.062
_pd_proc_ls_prof_wR_expected     2.61
_pd_proc_ls_prof_wR_factor       0.081
_pd_spec_mounting                'packed powder pellet'
_pd_spec_mount_mode              reflection
_pd_spec_shape                   flat_sheet
_pd_spec_size_axial              14
_pd_spec_size_equat              10
_pd_spec_size_thick              0.5
_refine_ls_goodness_of_fit_all   3.11
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_R_Fsqd_factor         0.016
_refine_ls_shift/su_max          <0.01
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      calc
_cod_data_source_file            c3sc51419f.txt
_cod_data_source_block           caf-BA
_cod_original_cell_volume        1575.64(31)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1514629
loop_
_symmetry_equiv_pos_as_xyz
'-x, -y, -z'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
'x, y, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
C1 C 4 -0.02886(29) 0.21531(40) 0.46825(23) 1 7.30(32)
C2 C 4 -0.12020(30) 0.14561(50) 0.50163(17) 1 7.30(32)
C3 C 4 -0.19998(30) 0.03061(48) 0.45348(22) 1 7.30(32)
N1 N 4 -0.17584(35) -0.00446(42) 0.37351(22) 1 7.30(32)
C4 C 4 -0.08310(37) 0.06494(47) 0.34195(17) 1 7.30(32)
N2 N 4 -0.00833(33) 0.17502(46) 0.39234(21) 1 7.30(32)
N3 N 4 0.03428(41) 0.31756(57) 0.52724(30) 1 7.30(32)
C5 C 4 -0.02173(30) 0.31299(48) 0.59289(19) 1 7.30(32)
N4 N 4 -0.11554(33) 0.21161(41) 0.58120(19) 1 7.30(32)
O1 O 4 -0.06747(65) 0.02984(90) 0.27098(54) 1 7.30(32)
O2 O 4 -0.28117(88) -0.03497(84) 0.47912(42) 1 7.30(32)
C6 C 4 0.08526(22) 0.24746(30) 0.36178(16) 1 7.30(32)
C7 C 4 -0.24931(23) -0.11571(28) 0.32191(16) 1 7.30(32)
C8 C 4 -0.19079(20) 0.17824(26) 0.63969(15) 1 7.30(32)
H1 H 4 0.0012(10) 0.3720(14) 0.64344(64) 1 7.30(32)
H2 H 4 0.0877(11) 0.2058(17) 0.30599(64) 1 7.30(32)
H3 H 4 0.0661(11) 0.3515(14) 0.35540(66) 1 7.30(32)
H4 H 4 0.16440(91) 0.2328(13) 0.40384(65) 1 7.30(32)
H5 H 4 -0.22240(91) -0.1290(13) 0.26882(68) 1 7.30(32)
H6 H 4 -0.2394(10) -0.2076(14) 0.35507(73) 1 7.30(32)
H7 H 4 -0.33507(95) -0.0845(14) 0.30789(76) 1 7.30(32)
H8 H 4 -0.2494(10) 0.1019(12) 0.61384(70) 1 7.30(32)
H9 H 4 -0.1376(10) 0.1433(15) 0.69494(75) 1 7.30(32)
H10 H 4 -0.2350(10) 0.2671(14) 0.64937(73) 1 7.30(32)
C11 C 4 0.40707(29) 0.73887(47) 0.70116(18) 1 7.30(32)
C12 C 4 0.50580(28) 0.83308(47) 0.71020(19) 1 7.30(32)
C13 C 4 0.57098(31) 0.83875(45) 0.64547(18) 1 7.30(32)
C14 C 4 0.53394(30) 0.75050(45) 0.56986(18) 1 7.30(32)
C15 C 4 0.43524(27) 0.65562(47) 0.56059(19) 1 7.30(32)
C16 C 4 0.36918(30) 0.65240(42) 0.62547(18) 1 7.30(32)
C17 C 4 0.26541(28) 0.55435(40) 0.61414(19) 1 7.30(32)
O11 O 4 0.19748(71) 0.53245(64) 0.66256(36) 1 7.30(32)
O12 O 4 0.23877(37) 0.47258(63) 0.53874(26) 1 7.30(32)
H16 H 4 0.3626(10) 0.7327(16) 0.74616(70) 1 7.30(32)
H11 H 4 0.5334(11) 0.8909(16) 0.76339(83) 1 7.30(32)
H12 H 4 0.64133(94) 0.9036(14) 0.65246(64) 1 7.30(32)
H13 H 4 0.5781(10) 0.7557(12) 0.52454(84) 1 7.30(32)
H14 H 4 0.4062(10) 0.5967(14) 0.50725(80) 1 7.30(32)
H15 H 4 0.16804(92) 0.4107(13) 0.53768(72) 1 7.30(32)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C17 O12 H15 108.9(8)
C3 N1 C4 123.3(3)
C4 N1 C7 118.9(3)
C3 N1 C7 117.8(3)
C1 N2 C4 119.4(3)
C1 N2 C6 119.4(3)
C4 N2 C6 121.2(3)
C1 N3 C5 104.1(4)
C2 N4 C5 105.4(3)
C5 N4 C8 127.5(3)
C2 N4 C8 127.2(3)
N2 C1 C2 121.4(3)
N3 C1 C2 110.1(3)
N2 C1 N3 128.4(4)
N4 C2 C3 131.6(3)
C1 C2 C3 122.0(3)
N4 C2 C1 106.4(3)
O2 C3 C2 125.2(4)
N1 C3 C2 113.9(3)
O2 C3 N1 120.9(4)
O1 C4 N1 119.9(5)
N1 C4 N2 120.0(3)
O1 C4 N2 120.1(5)
N3 C5 N4 114.0(4)
N4 C5 H1 122.0(8)
N3 C5 H1 124.0(8)
N2 C6 H3 108.9(8)
N2 C6 H4 109.0(7)
C16 C11 H16 119.7(8)
C11 C12 H11 119.7(8)
C13 C12 H11 120.2(8)
C12 C13 H12 119.8(7)
C14 C13 H12 120.0(6)
H2 C6 H3 110.0(11)
H2 C6 H4 110.0(10)
H3 C6 H4 110.2(10)
N2 C6 H2 108.8(9)
N1 C7 H5 109.0(7)
N1 C7 H7 108.7(8)
H5 C7 H6 110.1(10)
H5 C7 H7 110.0(10)
H6 C7 H7 110.1(10)
N1 C7 H6 108.9(7)
N4 C8 H8 108.8(7)
N4 C8 H9 108.8(7)
H8 C8 H9 110.0(10)
H8 C8 H10 109.9(10)
H9 C8 H10 110.1(10)
N4 C8 H10 109.3(7)
C12 C11 C16 119.8(3)
C11 C12 C13 120.0(3)
C12 C13 C14 120.2(3)
C13 C14 C15 120.0(3)
C14 C15 C16 119.2(3)
C11 C16 C17 120.8(3)
C15 C16 C17 118.5(3)
C11 C16 C15 120.7(3)
O11 C17 C16 129.1(4)
O12 C17 C16 115.7(3)
O11 C17 O12 115.2(4)
C12 C11 H16 120.5(8)
C13 C14 H13 120.3(8)
C15 C14 H13 119.7(7)
C14 C15 H14 120.9(8)
C16 C15 H14 119.7(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.228(8)
O2 C3 1.242(10)
O11 C17 1.230(8)
O12 C17 1.380(6)
O12 H15 0.972(12)
N1 C3 1.404(5)
N1 C4 1.414(6)
N1 C7 1.428(4)
N2 C4 1.419(6)
N2 C1 1.339(5)
N2 C6 1.427(4)
N3 C1 1.384(6)
N3 C5 1.350(6)
N4 C8 1.439(4)
N4 C5 1.378(5)
N4 C2 1.391(4)
C1 C2 1.418(5)
C2 C3 1.463(6)
C5 H1 0.947(11)
C6 H2 0.972(11)
C6 H3 0.971(13)
C6 H4 0.978(11)
C7 H7 0.976(12)
C7 H6 0.981(13)
C7 H5 0.974(11)
C8 H8 0.974(11)
C8 H9 0.983(13)
C8 H10 0.982(13)
C11 C16 1.412(5)
C11 C12 1.381(6)
C12 C13 1.407(4)
C13 C14 1.420(4)
C14 C15 1.384(5)
C15 C16 1.415(4)
C16 C17 1.443(5)
C11 H16 0.973(12)
C12 H11 0.979(14)
C13 H12 0.970(12)
C14 H13 0.975(12)
C15 H14 0.987(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 64120
