#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/92/4509293.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_4509293
loop_
_publ_author_name
'Bučar, Dejan-Krešimir'
'Henry, Rodger F.'
'Lou, Xiaochun'
'Duerst, Richard W.'
'MacGillivray, Leonard R.'
'Zhang, Geoff G. Z.'
_publ_section_title
;
 Cocrystals of Caffeine and Hydroxybenzoic Acids Composed of Multiple
 Supramolecular Heterosynthons: Screening via Solution-Mediated Phase
 Transformation and Structural Characterization
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1932
_journal_paper_doi               10.1021/cg801178m
_journal_volume                  9
_journal_year                    2009
_chemical_formula_moiety         'C8 H10 N4 O2, C7 H6 O3'
_chemical_formula_sum            'C15 H16 N4 O5'
_chemical_formula_weight         332.32
_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'
_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                 95.029(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.687(3)
_cell_length_b                   6.948(3)
_cell_length_c                   28.098(11)
_cell_measurement_reflns_used    952
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.0325
_cell_measurement_theta_min      2.911
_cell_volume                     1494.9(10)
_computing_cell_refinement       'Bruker saintplus (Bruker 1999)'
_computing_data_collection       'Bruker SMART (Bruker 2001)'
_computing_data_reduction        'Bruker saintplus (Bruker 1999)'
_computing_molecular_graphics    'ORTEP (Johnson 1976), Accelrys (2004)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2000)'
_computing_structure_solution    'SHELXL (Sheldrick, 2000)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'omega scan'
_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  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            16724
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.46
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       paralellapiped
_exptl_crystal_F_000             696
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .1
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3647
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.200
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0636
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0489P)²+1.2460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1464
_reflns_number_gt                3364
_reflns_number_total             3647
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cg801178msup1.cif
_cod_data_source_block           2
_cod_original_cell_volume        1494.8(10)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4509293
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 -0.0094(2) -0.1832(2) 0.34293(5) 0.0362(4) Uani 1 1 d .
O2 O 0.2197(2) -0.0363(2) 0.49532(5) 0.0388(4) Uani 1 1 d .
N1 N 0.1472(2) 0.2054(2) 0.31378(6) 0.0272(4) Uani 1 1 d .
N2 N 0.0963(2) -0.1014(2) 0.41964(6) 0.0286(4) Uani 1 1 d .
N3 N 0.2609(2) 0.1826(2) 0.43768(6) 0.0277(4) Uani 1 1 d .
N4 N 0.2878(2) 0.3949(2) 0.36916(6) 0.0295(4) Uani 1 1 d .
C1 C 0.0771(3) 0.1332(3) 0.26706(7) 0.0347(5) Uani 1 1 d .
H1A H -0.0482 0.1328 0.2654 0.052 Uiso 1 1 calc R
H1B H 0.1184 0.0045 0.2627 0.052 Uiso 1 1 calc R
H1C H 0.1150 0.2148 0.2424 0.052 Uiso 1 1 calc R
C2 C 0.1451(2) 0.1120(3) 0.35729(6) 0.0262(4) Uani 1 1 d .
C3 C 0.0697(2) -0.0676(3) 0.36966(7) 0.0269(4) Uani 1 1 d .
C4 C 0.0199(3) -0.2805(3) 0.43690(8) 0.0383(5) Uani 1 1 d .
H4A H 0.0892 -0.3884 0.4286 0.057 Uiso 1 1 calc R
H4B H -0.0970 -0.2950 0.4223 0.057 Uiso 1 1 calc R
H4C H 0.0178 -0.2745 0.4710 0.057 Uiso 1 1 calc R
C5 C 0.1940(3) 0.0118(3) 0.45311(7) 0.0281(4) Uani 1 1 d .
C6 C 0.3673(3) 0.3032(3) 0.47200(7) 0.0357(5) Uani 1 1 d .
H6A H 0.4285 0.3979 0.4550 0.054 Uiso 1 1 calc R
H6B H 0.4501 0.2239 0.4906 0.054 Uiso 1 1 calc R
H6C H 0.2929 0.3664 0.4928 0.054 Uiso 1 1 calc R
C7 C 0.2332(2) 0.2312(3) 0.39003(7) 0.0258(4) Uani 1 1 d .
C8 C 0.2325(3) 0.3715(3) 0.32279(7) 0.0305(4) Uani 1 1 d .
H8 H 0.2516 0.4616 0.2993 0.037 Uiso 1 1 calc R
O3 O 0.4215(2) 0.7553(2) 0.30626(5) 0.0447(4) Uani 1 1 d .
O4 O 0.4741(2) 0.7284(2) 0.38575(5) 0.0360(4) Uani 1 1 d .
H1 H 0.414(4) 0.617(5) 0.3803(11) 0.063(9) Uiso 1 1 d .
O5 O 0.8276(2) 1.3118(2) 0.43792(6) 0.0408(4) Uani 1 1 d .
C9 C 0.4851(3) 0.8184(3) 0.34421(7) 0.0299(4) Uani 1 1 d .
C10 C 0.6586(2) 1.0691(3) 0.39270(7) 0.0268(4) Uani 1 1 d .
H10 H 0.6532 0.9935 0.4198 0.032 Uiso 1 1 calc R
C11 C 0.5798(2) 1.0068(3) 0.34877(7) 0.0265(4) Uani 1 1 d .
C12 C 0.6713(3) 1.2970(3) 0.31166(7) 0.0320(4) Uani 1 1 d .
H12 H 0.6740 1.3741 0.2847 0.038 Uiso 1 1 calc R
C13 C 0.5866(3) 1.1199(3) 0.30798(7) 0.0294(4) Uani 1 1 d .
H13 H 0.5350 1.0776 0.2787 0.035 Uiso 1 1 calc R
C14 C 0.7519(3) 1.3603(3) 0.35501(7) 0.0319(4) Uani 1 1 d .
H14 H 0.8095 1.4781 0.3570 0.038 Uiso 1 1 calc R
C15 C 0.7455(3) 1.2453(3) 0.39563(7) 0.0293(4) Uani 1 1 d .
H2 H 0.817(4) 1.226(5) 0.4602(12) 0.069(10) 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
C8 N1 C2 106.25(16)
C8 N1 C1 126.90(17)
C2 N1 C1 126.80(17)
C5 N2 C3 126.57(17)
C5 N2 C4 117.42(16)
C3 N2 C4 115.93(16)
C5 N3 C7 119.07(16)
C5 N3 C6 119.07(16)
C7 N3 C6 121.79(17)
C8 N4 C7 103.51(16)
C8 N4 H1 112.6(10)
C7 N4 H1 143.8(10)
N1 C1 H1A 109.5
N1 C1 H1B 109.5
H1A C1 H1B 109.5
N1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C7 C2 N1 105.43(17)
C7 C2 C3 123.36(17)
N1 C2 C3 131.21(17)
O1 C3 N2 121.22(18)
O1 C3 C2 127.80(18)
N2 C3 C2 110.98(16)
N2 C4 H4A 109.5
N2 C4 H4B 109.5
H4A C4 H4B 109.5
N2 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
O2 C5 N3 120.26(18)
O2 C5 N2 121.87(18)
N3 C5 N2 117.87(17)
N3 C6 H6A 109.5
N3 C6 H6B 109.5
H6A C6 H6B 109.5
N3 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
N4 C7 C2 111.57(17)
N4 C7 N3 126.51(17)
C2 C7 N3 121.92(18)
N1 C8 N4 113.24(17)
N1 C8 H8 123.4
N4 C8 H8 123.4
C9 O4 H1 108.8(19)
C15 O5 H2 109(2)
O3 C9 O4 123.22(19)
O3 C9 C11 123.04(18)
O4 C9 C11 113.73(17)
C15 C10 C11 119.57(18)
C15 C10 H10 120.2
C11 C10 H10 120.2
C13 C11 C10 120.51(18)
C13 C11 C9 118.37(17)
C10 C11 C9 121.11(17)
C14 C12 C13 121.01(18)
C14 C12 H12 119.5
C13 C12 H12 119.5
C12 C13 C11 119.21(18)
C12 C13 H13 120.4
C11 C13 H13 120.4
C12 C14 C15 119.36(19)
C12 C14 H14 120.3
C15 C14 H14 120.3
O5 C15 C10 121.82(18)
O5 C15 C14 117.87(18)
C10 C15 C14 120.32(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.224(2)
O2 C5 1.231(2)
N1 C8 1.341(3)
N1 C2 1.385(2)
N1 C1 1.463(2)
N2 C5 1.394(2)
N2 C3 1.421(2)
N2 C4 1.476(3)
N3 C5 1.378(3)
N3 C7 1.379(2)
N3 C6 1.471(2)
N4 C8 1.344(3)
N4 C7 1.363(3)
N4 H1 1.83(3)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C7 1.372(3)
C2 C3 1.431(3)
C4 H4A 0.9600
C4 H4B 0.9600
C4 H4C 0.9600
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C8 H8 0.9300
O3 C9 1.215(2)
O4 C9 1.333(2)
O4 H1 0.91(3)
O5 C15 1.375(2)
O5 H2 0.87(4)
C9 C11 1.498(3)
C10 C15 1.393(3)
C10 C11 1.395(3)
C10 H10 0.9300
C11 C13 1.394(3)
C12 C14 1.389(3)
C12 C13 1.391(3)
C12 H12 0.9300
C13 H13 0.9300
C14 C15 1.398(3)
C14 H14 0.9300
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
O5 H2 O2 0.87(4) 1.86(4) 2.726(2) 176(3) 3_666
O4 H1 N4 0.91(3) 1.83(3) 2.743(2) 179(3) .
C8 H8 O3 0.93 2.42 3.091(3) 128.9 .
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
C8 N1 C2 C7 -0.6(2)
C1 N1 C2 C7 176.96(18)
C8 N1 C2 C3 178.5(2)
C1 N1 C2 C3 -3.9(3)
C5 N2 C3 O1 175.19(19)
C4 N2 C3 O1 -1.3(3)
C5 N2 C3 C2 -5.1(3)
C4 N2 C3 C2 178.44(17)
C7 C2 C3 O1 -179.3(2)
N1 C2 C3 O1 1.7(4)
C7 C2 C3 N2 1.0(3)
N1 C2 C3 N2 -178.01(19)
C7 N3 C5 O2 178.72(19)
C6 N3 C5 O2 1.8(3)
C7 N3 C5 N2 -1.9(3)
C6 N3 C5 N2 -178.85(18)
C3 N2 C5 O2 -174.87(19)
C4 N2 C5 O2 1.6(3)
C3 N2 C5 N3 5.7(3)
C4 N2 C5 N3 -177.83(18)
C8 N4 C7 C2 -0.7(2)
H1 N4 C7 C2 -175.7(16)
C8 N4 C7 N3 178.56(19)
H1 N4 C7 N3 3.5(16)
N1 C2 C7 N4 0.8(2)
C3 C2 C7 N4 -178.40(17)
N1 C2 C7 N3 -178.47(17)
C3 C2 C7 N3 2.3(3)
C5 N3 C7 N4 178.98(18)
C6 N3 C7 N4 -4.1(3)
C5 N3 C7 C2 -1.9(3)
C6 N3 C7 C2 175.01(19)
C2 N1 C8 N4 0.2(2)
C1 N1 C8 N4 -177.34(18)
C7 N4 C8 N1 0.3(2)
H1 N4 C8 N1 177.1(10)
C15 C10 C11 C13 -0.4(3)
C15 C10 C11 C9 -179.93(18)
O3 C9 C11 C13 3.8(3)
O4 C9 C11 C13 -174.95(18)
O3 C9 C11 C10 -176.7(2)
O4 C9 C11 C10 4.6(3)
C14 C12 C13 C11 1.3(3)
C10 C11 C13 C12 -0.7(3)
C9 C11 C13 C12 178.86(18)
C13 C12 C14 C15 -0.9(3)
C11 C10 C15 O5 -178.98(19)
C11 C10 C15 C14 0.8(3)
C12 C14 C15 O5 179.61(19)
C12 C14 C15 C10 -0.2(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146896
