#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:23:26 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179628 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/92/4509296.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_4509296
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         'C7 H6 O4, C8 H10 O2 N4, O1 H2'
_chemical_formula_sum            'C15 H18 N4 O7'
_chemical_formula_weight         366.33
_chemical_name_systematic
; 
 ? 
;
_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                77.832(9)
_cell_angle_beta                 83.426(9)
_cell_angle_gamma                71.568(9)
_cell_formula_units_Z            2
_cell_length_a                   6.657(4)
_cell_length_b                   8.796(5)
_cell_length_c                   15.670(9)
_cell_measurement_reflns_used    889
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.897
_cell_measurement_theta_min      2.663
_cell_volume                     849.8(9)
_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 0.961
_diffrn_measured_fraction_theta_max 0.961
_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  0.0476
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9762
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         1.33
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.835
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.253
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4038
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.253
_refine_ls_R_factor_all          0.1302
_refine_ls_R_factor_gt           0.1064
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3082
_refine_ls_wR_factor_ref         0.3303
_reflns_number_gt                2841
_reflns_number_total             4038
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cg801178msup1.cif
_cod_data_source_block           5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        849.8(8)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4509296
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
O1 O -0.0279(4) 0.9151(3) 0.21300(15) 0.0500(7) Uani 1 1 d .
H1 H 0.0133 0.8151 0.2243 0.075 Uiso 1 1 calc R
O2 O -0.0672(4) 0.8819(3) 0.35870(15) 0.0494(7) Uani 1 1 d .
O3 O -0.1876(4) 1.1290(3) 0.43343(14) 0.0450(6) Uani 1 1 d .
H3 H -0.1436 1.0319 0.4305 0.068 Uiso 1 1 calc R
O4 O -0.3218(4) 1.4461(3) 0.42112(15) 0.0488(7) Uani 1 1 d .
H4 H -0.3650 1.5461 0.4108 0.073 Uiso 1 1 calc R
C1 C -0.0821(5) 0.9719(4) 0.2858(2) 0.0398(7) Uani 1 1 d .
C2 C -0.1610(5) 1.1518(3) 0.2756(2) 0.0350(7) Uani 1 1 d .
C3 C -0.2097(5) 1.2200(4) 0.35115(19) 0.0348(7) Uani 1 1 d .
C4 C -0.2832(5) 1.3897(4) 0.3449(2) 0.0359(7) Uani 1 1 d .
C5 C -0.3101(5) 1.4899(4) 0.2621(2) 0.0383(7) Uani 1 1 d .
H5 H -0.3601 1.6026 0.2572 0.046 Uiso 1 1 calc R
C6 C -0.2623(5) 1.4213(4) 0.1871(2) 0.0372(7) Uani 1 1 d .
H6 H -0.2808 1.4886 0.1323 0.045 Uiso 1 1 calc R
C7 C -0.1879(5) 1.2544(4) 0.1933(2) 0.0364(7) Uani 1 1 d .
H7 H -0.1555 1.2097 0.1428 0.044 Uiso 1 1 calc R
O5 O 0.3893(4) 0.0314(3) 0.29696(19) 0.0585(8) Uani 1 1 d .
O6 O 0.3281(5) 0.3188(4) 0.01695(16) 0.0572(7) Uani 1 1 d .
N1 N 0.2244(4) 0.3593(3) 0.35587(17) 0.0408(7) Uani 1 1 d .
N2 N 0.3572(4) 0.1772(3) 0.15710(18) 0.0391(7) Uani 1 1 d .
N3 N 0.2321(4) 0.4648(3) 0.12612(17) 0.0373(6) Uani 1 1 d .
N4 N 0.1414(4) 0.5934(3) 0.2543(2) 0.0433(7) Uani 1 1 d .
C8 C 0.2449(7) 0.2559(5) 0.4405(2) 0.0580(10) Uani 1 1 d .
H8A H 0.2444 0.3184 0.4839 0.087 Uiso 1 1 calc R
H8B H 0.3757 0.1689 0.4410 0.087 Uiso 1 1 calc R
H8C H 0.1283 0.2111 0.4531 0.087 Uiso 1 1 calc R
C9 C 0.2608(5) 0.3205(4) 0.27343(19) 0.0332(7) Uani 1 1 d .
C10 C 0.3390(5) 0.1653(4) 0.2481(2) 0.0385(7) Uani 1 1 d .
C11 C 0.4349(7) 0.0248(5) 0.1228(3) 0.0584(10) Uani 1 1 d .
H11A H 0.3433 0.0277 0.0790 0.088 Uiso 1 1 calc R
H11B H 0.4362 -0.0657 0.1695 0.088 Uiso 1 1 calc R
H11C H 0.5760 0.0128 0.0974 0.088 Uiso 1 1 calc R
C12 C 0.3063(5) 0.3209(4) 0.0950(2) 0.0395(7) Uani 1 1 d .
C13 C 0.1769(7) 0.6212(5) 0.0635(3) 0.0544(10) Uani 1 1 d .
H13A H 0.0353 0.6455 0.0456 0.082 Uiso 1 1 calc R
H13B H 0.2743 0.6132 0.0133 0.082 Uiso 1 1 calc R
H13C H 0.1854 0.7067 0.0910 0.082 Uiso 1 1 calc R
C14 C 0.2111(5) 0.4631(4) 0.2150(2) 0.0347(7) Uani 1 1 d .
C15 C 0.1519(6) 0.5261(4) 0.3406(3) 0.0486(9) Uani 1 1 d .
H15 H 0.1136 0.5872 0.3848 0.058 Uiso 1 1 calc R
O7 O -0.4255(5) 1.2579(3) 0.59022(17) 0.0600(8) 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
C1 O1 H1 109.5
C3 O3 O7 122.29(18)
C3 O3 H3 109.5
O7 O3 H3 124.0
C4 O4 H4 109.5
O2 C1 O1 122.5(3)
O2 C1 C2 121.9(3)
O1 C1 C2 115.6(3)
C3 C2 C7 119.6(3)
C3 C2 C1 118.2(3)
C7 C2 C1 122.3(3)
O3 C3 C2 123.2(3)
O3 C3 C4 116.4(3)
C2 C3 C4 120.3(3)
O4 C4 C3 116.7(3)
O4 C4 C5 124.1(3)
C3 C4 C5 119.2(3)
C6 C5 C4 120.3(3)
C6 C5 H5 119.9
C4 C5 H5 119.9
C7 C6 C5 120.5(3)
C7 C6 H6 119.7
C5 C6 H6 119.7
C6 C7 C2 120.2(3)
C6 C7 H7 119.9
C2 C7 H7 119.9
C15 N1 C9 104.1(3)
C15 N1 C8 125.4(3)
C9 N1 C8 130.4(3)
C12 N2 C10 126.2(3)
C12 N2 C11 116.1(3)
C10 N2 C11 117.6(3)
C12 N3 C14 120.3(3)
C12 N3 C13 119.4(3)
C14 N3 C13 120.3(3)
C14 N4 C15 103.3(3)
C14 N4 H1 138.2
C15 N4 H1 117.8
N1 C8 H8A 109.5
N1 C8 H8B 109.5
H8A C8 H8B 109.5
N1 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C14 C9 N1 107.2(3)
C14 C9 C10 123.0(3)
N1 C9 C10 129.8(3)
O5 C10 N2 120.8(3)
O5 C10 C9 126.7(3)
N2 C10 C9 112.5(3)
N2 C11 H11A 109.5
N2 C11 H11B 109.5
H11A C11 H11B 109.5
N2 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O6 C12 N3 121.7(3)
O6 C12 N2 121.4(3)
N3 C12 N2 116.9(3)
N3 C13 H13A 109.5
N3 C13 H13B 109.5
H13A C13 H13B 109.5
N3 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
N4 C14 C9 112.2(3)
N4 C14 N3 126.7(3)
C9 C14 N3 121.1(3)
N4 C15 N1 113.2(3)
N4 C15 H15 123.4
N1 C15 H15 123.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.309(4)
O1 H1 0.8200
O2 C1 1.240(4)
O3 C3 1.363(4)
O3 O7 2.996(4)
O3 H3 0.8200
O4 C4 1.355(4)
O4 H4 0.8200
C1 C2 1.480(4)
C2 C3 1.398(4)
C2 C7 1.404(4)
C3 C4 1.401(4)
C4 C5 1.402(4)
C5 C6 1.393(4)
C5 H5 0.9300
C6 C7 1.378(4)
C6 H6 0.9300
C7 H7 0.9300
O5 C10 1.231(4)
O6 C12 1.219(4)
N1 C15 1.369(5)
N1 C9 1.381(4)
N1 C8 1.434(4)
N2 C12 1.395(4)
N2 C10 1.401(4)
N2 C11 1.468(4)
N3 C12 1.376(4)
N3 C14 1.381(4)
N3 C13 1.478(4)
N4 C14 1.343(4)
N4 C15 1.356(5)
N4 H1 1.8459
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 C14 1.358(4)
C9 C10 1.422(4)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C15 H15 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
O1 H1 N4 0.82 1.85 2.660(4) 171.7 .
O3 H3 O2 0.82 1.83 2.549(3) 146.0 .
O4 H4 O7 0.82 1.84 2.597(3) 152.5 2_486
C15 H15 O2 0.93 2.45 3.065(5) 123.2 .
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
O2 C1 C2 C3 3.1(5)
O1 C1 C2 C3 -176.3(3)
O2 C1 C2 C7 -176.9(3)
O1 C1 C2 C7 3.7(5)
O7 O3 C3 C2 -158.0(2)
O7 O3 C3 C4 22.6(4)
C7 C2 C3 O3 -179.9(3)
C1 C2 C3 O3 0.1(5)
C7 C2 C3 C4 -0.5(5)
C1 C2 C3 C4 179.5(3)
O3 C3 C4 O4 1.0(4)
C2 C3 C4 O4 -178.4(3)
O3 C3 C4 C5 -179.7(3)
C2 C3 C4 C5 0.9(5)
O4 C4 C5 C6 178.7(3)
C3 C4 C5 C6 -0.6(4)
C4 C5 C6 C7 -0.1(5)
C5 C6 C7 C2 0.4(5)
C3 C2 C7 C6 -0.1(5)
C1 C2 C7 C6 179.8(3)
C15 N1 C9 C14 0.6(3)
C8 N1 C9 C14 178.0(3)
C15 N1 C9 C10 179.4(3)
C8 N1 C9 C10 -3.2(6)
C12 N2 C10 O5 -179.8(3)
C11 N2 C10 O5 0.9(5)
C12 N2 C10 C9 -0.2(4)
C11 N2 C10 C9 -179.6(3)
C14 C9 C10 O5 179.2(3)
N1 C9 C10 O5 0.6(6)
C14 C9 C10 N2 -0.3(4)
N1 C9 C10 N2 -178.9(3)
C14 N3 C12 O6 -179.4(3)
C13 N3 C12 O6 0.1(5)
C14 N3 C12 N2 0.1(4)
C13 N3 C12 N2 179.6(3)
C10 N2 C12 O6 179.8(3)
C11 N2 C12 O6 -0.8(5)
C10 N2 C12 N3 0.3(5)
C11 N2 C12 N3 179.7(3)
C15 N4 C14 C9 0.7(4)
H1 N4 C14 C9 -169.1
C15 N4 C14 N3 -179.9(3)
H1 N4 C14 N3 10.4
N1 C9 C14 N4 -0.9(4)
C10 C9 C14 N4 -179.7(3)
N1 C9 C14 N3 179.7(3)
C10 C9 C14 N3 0.8(5)
C12 N3 C14 N4 179.9(3)
C13 N3 C14 N4 0.5(5)
C12 N3 C14 C9 -0.7(4)
C13 N3 C14 C9 179.9(3)
C14 N4 C15 N1 -0.3(4)
H1 N4 C15 N1 172.0
C9 N1 C15 N4 -0.2(4)
C8 N1 C15 N4 -177.8(3)
