#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/16/7101605.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_7101605
loop_
_publ_author_name
'W. Jones'
'Jonathan C. Burley'
'Laszlo Fabian'
'Tomislav Friscic'
'W. D. Sam Motherwell'
_publ_section_title
;
Exploring cocrystal-cocrystal reactivity via
liquid-assisted grinding: assembling of racemic and dismantling of
enantiomeric cocrystals
;
_journal_issue                   48
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/b613073a
_journal_year                    2006
_chemical_formula_moiety         'C8 H10 N4 O2, C4 H6 O6'
_chemical_formula_sum            'C12 H16 N4 O8'
_chemical_formula_weight         344.29
_chemical_name_common            'Caffeine-D-tartaric acid 1/1'
_chemical_name_systematic
;
Caffeine-D-tartaric acid 1/1
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8024(1)
_cell_length_b                   10.0260(1)
_cell_length_c                   25.3674(4)
_cell_measurement_reflns_used    12291
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1475.74(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            13886
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.60
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3327
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0275
_refine_ls_shift/su_max          0.045
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0310P)²+0.3929P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0696
_reflns_number_gt                3218
_reflns_number_total             3327
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b613073a.txt
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7101605
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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 0.51177(19) -0.06706(10) 0.56310(4) 0.0261(2) Uani 1 1 d .
O2 O 0.99714(19) 0.19981(10) 0.46738(4) 0.0286(2) Uani 1 1 d .
O3 O 0.98751(17) -0.11976(9) 0.36203(3) 0.0195(2) Uani 1 1 d .
H3 H 1.1060 -0.0738 0.3677 0.029 Uiso 1 1 calc R
O4 O 1.07451(19) -0.07808(11) 0.27811(4) 0.0312(3) Uani 1 1 d .
O5 O 0.72203(17) -0.24103(9) 0.24410(3) 0.0197(2) Uani 1 1 d .
H5 H 0.6779 -0.1723 0.2281 0.030 Uiso 1 1 calc R
O6 O 0.92862(15) -0.42909(9) 0.31255(4) 0.01544(18) Uani 1 1 d .
H6 H 0.8961 -0.4677 0.2841 0.023 Uiso 1 1 calc R
O7 O 0.34186(15) -0.34709(10) 0.33913(4) 0.0213(2) Uani 1 1 d .
H7 H 0.2172 -0.3872 0.3334 0.032 Uiso 1 1 calc R
O8 O 0.49499(17) -0.51954(10) 0.29488(4) 0.0258(2) Uani 1 1 d .
N1 N 0.37218(19) 0.00898(11) 0.38341(4) 0.0180(2) Uani 1 1 d .
N2 N 0.43682(19) -0.04726(10) 0.47559(4) 0.0175(2) Uani 1 1 d .
N3 N 0.7594(2) 0.05964(11) 0.51394(4) 0.0184(2) Uani 1 1 d .
N4 N 0.67172(19) 0.14647(11) 0.37346(4) 0.0170(2) Uani 1 1 d .
C1 C 0.4889(2) 0.08884(12) 0.35055(5) 0.0189(2) Uani 1 1 d .
H1 H 0.4465 0.1031 0.3148 0.023 Uiso 1 1 calc R
C2 C 0.4905(2) 0.01748(11) 0.42940(5) 0.0154(2) Uani 1 1 d .
C3 C 0.5637(2) -0.02025(12) 0.52031(5) 0.0177(2) Uani 1 1 d .
C4 C 0.8265(2) 0.12810(12) 0.46802(5) 0.0182(3) Uani 1 1 d .
C5 C 0.6754(2) 0.10050(12) 0.42505(5) 0.0154(2) Uani 1 1 d .
C6 C 0.8381(3) 0.23542(14) 0.34823(6) 0.0254(3) Uani 1 1 d .
H6A H 0.7835 0.2589 0.3129 0.038 Uiso 1 1 calc R
H6B H 0.9875 0.1903 0.3455 0.038 Uiso 1 1 calc R
H6C H 0.8550 0.3167 0.3694 0.038 Uiso 1 1 calc R
C7 C 0.2482(2) -0.14344(14) 0.47729(6) 0.0245(3) Uani 1 1 d .
H7A H 0.2498 -0.1899 0.5113 0.037 Uiso 1 1 calc R
H7B H 0.2671 -0.2083 0.4487 0.037 Uiso 1 1 calc R
H7C H 0.1011 -0.0966 0.4730 0.037 Uiso 1 1 calc R
C8 C 0.8921(3) 0.08786(16) 0.56184(6) 0.0289(3) Uani 1 1 d .
H8A H 1.0523 0.1073 0.5524 0.043 Uiso 1 1 calc R
H8B H 0.8874 0.0101 0.5852 0.043 Uiso 1 1 calc R
H8C H 0.8252 0.1650 0.5800 0.043 Uiso 1 1 calc R
C9 C 0.9544(2) -0.13049(12) 0.31098(5) 0.0166(2) Uani 1 1 d .
C10 C 0.7409(2) -0.21325(12) 0.29834(5) 0.0144(2) Uani 1 1 d .
H10 H 0.6015 -0.1618 0.3095 0.017 Uiso 1 1 calc R
C11 C 0.7426(2) -0.34650(12) 0.32781(5) 0.0133(2) Uani 1 1 d .
H11 H 0.7575 -0.3276 0.3664 0.016 Uiso 1 1 calc R
C12 C 0.5128(2) -0.41510(12) 0.31855(5) 0.0154(2) 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 N1 C2 104.00(11)
C2 N2 C3 119.15(11)
C2 N2 C7 120.46(11)
C3 N2 C7 120.38(11)
C3 N3 C4 126.85(11)
C3 N3 C8 116.16(11)
C4 N3 C8 116.53(11)
C1 N4 C5 106.13(11)
C1 N4 C6 126.58(11)
C5 N4 C6 127.25(11)
N1 C1 N4 112.82(11)
N1 C2 C5 111.55(11)
N1 C2 N2 126.05(11)
C5 C2 N2 122.40(11)
O1 C3 N2 121.61(12)
O1 C3 N3 121.57(12)
N2 C3 N3 116.78(11)
O2 C4 N3 121.43(12)
O2 C4 C5 126.97(12)
N3 C4 C5 111.59(11)
C2 C5 N4 105.50(11)
C2 C5 C4 122.74(12)
N4 C5 C4 131.75(12)
O4 C9 O3 124.12(12)
O4 C9 C10 124.10(12)
O3 C9 C10 111.75(11)
O5 C10 C9 112.09(10)
O5 C10 C11 107.76(10)
C9 C10 C11 111.51(10)
O6 C11 C12 111.25(9)
O6 C11 C10 112.48(10)
C12 C11 C10 108.29(10)
O8 C12 O7 125.58(12)
O8 C12 C11 122.89(11)
O7 C12 C11 111.52(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.2203(16)
O2 C4 1.2238(16)
O3 C9 1.3136(15)
O4 C9 1.2071(17)
O5 C10 1.4082(14)
O6 C11 1.4143(14)
O7 C12 1.3120(15)
O8 C12 1.2115(16)
N1 C1 1.3395(17)
N1 C2 1.3564(16)
N2 C2 1.3752(16)
N2 C3 1.3794(17)
N2 C7 1.4591(17)
N3 C3 1.3988(17)
N3 C4 1.4071(17)
N3 C8 1.4662(17)
N4 C1 1.3407(17)
N4 C5 1.3877(16)
N4 C6 1.4620(17)
C2 C5 1.3623(18)
C4 C5 1.4259(18)
C9 C10 1.5252(17)
C10 C11 1.5309(16)
C11 C12 1.5187(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21198159
