Co-Crystals of Caffeine and Hydroxy-2-naphthoic Acids: Unusual Formation of the Carboxylic Acid Dimer in the Presence of a Heterosynthon
Bučar, Dejan-Krešimir; Henry, Rodger F.; Lou, Xiaochun; Duerst, Richard W.; Borchardt, Thomas B.; MacGillivray, Leonard R.; Zhang, Geoff G. Z.; Molecular Pharmaceutics 4 (2007) 339–; doi:10.1021/mp070004b

data_1505183
_publ_section_title
;
 Co-Crystals of Caffeine and Hydroxy-2-naphthoic Acids:&#x00A0; Unusual
 Formation of the Carboxylic Acid Dimer in the Presence of a Heterosynthon
;
_journal_issue                   3
_journal_name_full               'Molecular Pharmaceutics'
_journal_page_first              339
_journal_paper_doi               10.1021/mp070004b
_journal_volume                  4
_journal_year                    2007
_chemical_formula_moiety         'C8 H10 N4 O2, C11 H8 O3'
_chemical_formula_sum            'C19 H18 N4 O5'
_chemical_formula_weight         382.37
_chemical_name_common            'caffeine 3-hydroxy-2-naphthoic acid'
_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                 117.015(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.040(9)
_cell_length_b                   24.42(2)
_cell_length_c                   8.654(8)
_cell_measurement_reflns_used    883
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.1825
_cell_measurement_theta_min      2.663
_cell_volume                     1702(3)
_computing_cell_refinement       'Bruker saintplus (Bruker 1999)'
_computing_data_collection       'Bruker SMART (Bruker 2001)'
_computing_data_reduction        'Bruker saintplus (Bruker 1999)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2000)'
_computing_structure_solution    'SHELXL (Sheldrick, 2000)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.1024
_diffrn_reflns_av_sigmaI/netI    0.0689
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19094
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         1.67
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.559
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4167
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.559
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0631
_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/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1011
_reflns_number_gt                2538
_reflns_number_total             4167
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            mp070004bsi20070105_112232.cif
_cod_data_source_block           crystal_B
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1505183