#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/76/7207667.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_7207667
loop_
_publ_author_name
'Ghosh, Soumyajit'
'Malla Reddy, C.'
_publ_section_title
;
 Co-crystals of caffeine with substituted nitroanilines and nitrobenzoic
 acids: Structure--mechanical property and thermal studies
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              2444
_journal_paper_doi               10.1039/c2ce06754d
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C8 H10 N4 O2, C6 H5 F N2 O2'
_chemical_formula_sum            'C14 H15 F N6 O4'
_chemical_formula_weight         350.32
_chemical_melting_point          413.59
_chemical_name_common            Caffeine:2-fluoro-5nitroaniline
_chemical_name_systematic
;
?
;
_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                 92.806(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8784(5)
_cell_length_b                   33.258(3)
_cell_length_c                   8.0008(7)
_cell_measurement_reflns_used    7710
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      32.25
_cell_measurement_theta_min      3.14
_cell_volume                     1562.3(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'BRUKER KAPPA APEX II DUO'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12814
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.62
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'multi-scan absorption correction'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3384
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0588
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0452P)²+1.1664P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1458
_reflns_number_gt                2911
_reflns_number_total             3384
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce06754d.txt
_cod_data_source_block           cmr_sg_085_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      'P2(1)/c '
_cod_database_code               7207667
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
F1 F 0.3833(3) 0.67307(4) 0.5535(2) 0.0662(5) Uani 1 1 d .
O1 O 0.0771(3) 0.74468(5) 0.9870(3) 0.0581(5) Uani 1 1 d .
O2 O 0.5960(3) 0.64717(5) 1.1414(2) 0.0549(5) Uani 1 1 d .
O3 O 0.2051(5) 0.49609(6) 0.3448(4) 0.1031(10) Uani 1 1 d .
N6 N -0.0143(4) 0.66972(7) 0.3683(3) 0.0586(6) Uani 1 1 d .
N1 N 0.3350(3) 0.69561(5) 1.0624(2) 0.0401(4) Uani 1 1 d .
N2 N 0.2850(3) 0.58894(5) 0.9381(2) 0.0428(4) Uani 1 1 d .
N3 N -0.0388(3) 0.61178(6) 0.8100(3) 0.0490(5) Uani 1 1 d .
N4 N 0.0080(3) 0.68180(5) 0.8897(2) 0.0406(4) Uani 1 1 d .
C10 C 0.3141(4) 0.63639(7) 0.4953(3) 0.0439(5) Uani 1 1 d .
C9 C 0.1078(4) 0.63559(6) 0.4009(3) 0.0394(5) Uani 1 1 d .
C1 C 0.1349(4) 0.70935(6) 0.9795(3) 0.0405(5) Uani 1 1 d .
C2 C 0.4180(4) 0.65606(6) 1.0640(3) 0.0377(5) Uani 1 1 d .
C3 C 0.2739(4) 0.62982(6) 0.9675(3) 0.0363(5) Uani 1 1 d .
C4 C 0.4688(5) 0.56127(8) 0.9866(4) 0.0623(7) Uani 1 1 d .
H4A H 0.4272 0.5345 0.9519 0.093 Uiso 1 1 calc R
H4B H 0.4952 0.5619 1.1059 0.093 Uiso 1 1 calc R
H4C H 0.6050 0.5692 0.9339 0.093 Uiso 1 1 calc R
C5 C 0.4655(5) 0.72558(7) 1.1625(4) 0.0574(7) Uani 1 1 d .
H5A H 0.4703 0.7178 1.2782 0.086 Uiso 1 1 calc R
H5B H 0.3936 0.7514 1.1498 0.086 Uiso 1 1 calc R
H5C H 0.6178 0.7271 1.1247 0.086 Uiso 1 1 calc R
C6 C 0.0949(4) 0.58021(7) 0.8443(3) 0.0502(6) Uani 1 1 d .
C7 C 0.0753(4) 0.64211(6) 0.8877(3) 0.0369(5) Uani 1 1 d .
C8 C -0.1924(4) 0.69518(8) 0.7893(3) 0.0555(6) Uani 1 1 d .
H8A H -0.2871 0.7113 0.8572 0.083 Uiso 1 1 calc R
H8B H -0.2766 0.6722 0.7484 0.083 Uiso 1 1 calc R
H8C H -0.1449 0.7108 0.6965 0.083 Uiso 1 1 calc R
C11 C 0.4467(4) 0.60360(8) 0.5303(3) 0.0502(6) Uani 1 1 d .
H11 H 0.5837 0.6062 0.5926 0.060 Uiso 1 1 calc R
C12 C 0.3749(4) 0.56623(8) 0.4719(3) 0.0529(6) Uani 1 1 d .
H12 H 0.4605 0.5432 0.4939 0.063 Uiso 1 1 calc R
C13 C 0.1703(4) 0.56483(7) 0.3794(3) 0.0466(5) Uani 1 1 d .
N5 N 0.0906(4) 0.52585(6) 0.3141(3) 0.0638(6) Uani 1 1 d .
O4 O -0.0884(5) 0.52426(6) 0.2311(4) 0.1012(10) Uani 1 1 d .
C14 C 0.0367(4) 0.59807(7) 0.3430(3) 0.0428(5) Uani 1 1 d .
H14 H -0.0997 0.5954 0.2801 0.051 Uiso 1 1 calc R
H6A H 0.033(5) 0.6913(9) 0.407(3) 0.051(7) Uiso 1 1 d .
H6B H -0.147(5) 0.6674(8) 0.304(4) 0.059(8) Uiso 1 1 d .
H6 H 0.068(5) 0.5516(9) 0.807(3) 0.059(8) 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'
F F 0.0171 0.0103 '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
C9 N6 H6A 119(2)
C9 N6 H6B 117.6(18)
H6A N6 H6B 123(3)
C1 N1 C2 126.53(18)
C1 N1 C5 116.15(19)
C2 N1 C5 117.28(19)
C6 N2 C3 105.20(19)
C6 N2 C4 126.6(2)
C3 N2 C4 128.1(2)
C6 N3 C7 102.69(19)
C1 N4 C7 119.99(18)
C1 N4 C8 119.35(19)
C7 N4 C8 120.59(19)
F1 C10 C11 119.3(2)
F1 C10 C9 116.0(2)
C11 C10 C9 124.7(2)
N6 C9 C14 122.5(2)
N6 C9 C10 121.6(2)
C14 C9 C10 115.9(2)
O1 C1 N4 121.6(2)
O1 C1 N1 121.3(2)
N4 C1 N1 117.12(18)
O2 C2 N1 121.3(2)
O2 C2 C3 126.8(2)
N1 C2 C3 111.94(18)
C7 C3 N2 105.15(18)
C7 C3 C2 122.99(19)
N2 C3 C2 131.8(2)
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
N1 C5 H5A 109.5
N1 C5 H5B 109.5
H5A C5 H5B 109.5
N1 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
N3 C6 N2 114.2(2)
N3 C6 H6 126.9(16)
N2 C6 H6 118.9(16)
N3 C7 C3 112.76(19)
N3 C7 N4 125.9(2)
C3 C7 N4 121.36(19)
N4 C8 H8A 109.5
N4 C8 H8B 109.5
H8A C8 H8B 109.5
N4 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C10 C11 C12 119.1(2)
C10 C11 H11 120.4
C12 C11 H11 120.4
C13 C12 C11 117.0(2)
C13 C12 H12 121.5
C11 C12 H12 121.5
C14 C13 C12 123.9(2)
C14 C13 N5 117.7(2)
C12 C13 N5 118.4(2)
O3 N5 O4 122.0(2)
O3 N5 C13 118.9(2)
O4 N5 C13 119.0(2)
C13 C14 C9 119.4(2)
C13 C14 H14 120.3
C9 C14 H14 120.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C10 1.361(3)
O1 C1 1.226(3)
O2 C2 1.226(3)
O3 N5 1.215(3)
N6 C9 1.362(3)
N6 H6A 0.82(3)
N6 H6B 0.91(3)
N1 C1 1.398(3)
N1 C2 1.403(3)
N1 C5 1.471(3)
N2 C6 1.347(3)
N2 C3 1.382(3)
N2 C4 1.457(3)
N3 C6 1.332(3)
N3 C7 1.347(3)
N4 C1 1.364(3)
N4 C7 1.378(3)
N4 C8 1.462(3)
C10 C11 1.362(3)
C10 C9 1.397(3)
C9 C14 1.389(3)
C2 C3 1.418(3)
C3 C7 1.366(3)
C4 H4A 0.9600
C4 H4B 0.9600
C4 H4C 0.9600
C5 H5A 0.9600
C5 H5B 0.9600
C5 H5C 0.9600
C6 H6 1.01(3)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C11 C12 1.387(3)
C11 H11 0.9300
C12 C13 1.382(3)
C12 H12 0.9300
C13 C14 1.379(3)
C13 N5 1.466(3)
N5 O4 1.217(3)
C14 H14 0.9300
