#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/76/7207662.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_7207662
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 Cl N2 O2'
_chemical_formula_sum            'C14 H15 Cl N6 O4'
_chemical_formula_weight         366.77
_chemical_melting_point          420.53
_chemical_name_common            Caffeine:4-chloro-3nitroaniline
_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                 95.6570(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7950(6)
_cell_length_b                   13.5627(9)
_cell_length_c                   14.9920(10)
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.48
_cell_measurement_theta_min      3.03
_cell_volume                     1577.25(19)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13582
_diffrn_reflns_theta_full        26.98
_diffrn_reflns_theta_max         26.98
_diffrn_reflns_theta_min         2.63
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'multi-scan absorption correction'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3420
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0538P)²+0.7563P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0969
_reflns_number_gt                3181
_reflns_number_total             3420
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce06754d.txt
_cod_data_source_block           cmr_sg_069_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               7207662
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
Cl1 Cl 0.55310(5) 0.08202(3) 0.16396(2) 0.03091(12) Uani 1 1 d .
O1 O 0.45854(14) 0.28213(9) 0.20898(7) 0.0356(3) Uani 1 1 d .
O2 O 0.65519(17) 0.39219(9) 0.19657(8) 0.0420(3) Uani 1 1 d .
O3 O 1.00243(14) 0.76888(8) 0.76540(7) 0.0307(2) Uani 1 1 d .
O4 O 0.78721(16) 0.54189(8) 0.95179(8) 0.0354(3) Uani 1 1 d .
N1 N 0.57984(15) 0.31569(9) 0.17229(7) 0.0254(3) Uani 1 1 d .
N2 N 0.90461(14) 0.82693(8) 0.89308(7) 0.0206(2) Uani 1 1 d .
N3 N 0.71918(15) 0.71678(9) 1.07297(7) 0.0227(2) Uani 1 1 d .
N4 N 0.78741(15) 0.87180(9) 1.03243(8) 0.0255(3) Uani 1 1 d .
N5 N 0.90121(14) 0.65610(8) 0.86116(7) 0.0212(2) Uani 1 1 d .
C6 C 0.9331(2) 0.57582(11) 0.79942(10) 0.0299(3) Uani 1 1 d .
H6A H 0.9824 0.6022 0.7483 0.045 Uiso 1 1 calc R
H6B H 0.8262 0.5435 0.7801 0.045 Uiso 1 1 calc R
H6C H 1.0114 0.5292 0.8294 0.045 Uiso 1 1 calc R
C1 C 0.73951(17) 0.17793(10) -0.05876(9) 0.0243(3) Uani 1 1 d .
H1 H 0.7732 0.1484 -0.1102 0.029 Uiso 1 1 calc R
C2 C 0.75365(17) 0.28096(10) -0.04873(9) 0.0216(3) Uani 1 1 d .
C3 C 0.70082(16) 0.32272(10) 0.02984(8) 0.0212(3) Uani 1 1 d .
H3 H 0.7100 0.3904 0.0390 0.025 Uiso 1 1 calc R
C4 C 0.63507(16) 0.26361(10) 0.09393(8) 0.0207(3) Uani 1 1 d .
C5 C 0.62181(16) 0.16146(10) 0.08388(9) 0.0219(3) Uani 1 1 d .
C7 C 0.67662(17) 0.12007(10) 0.00633(9) 0.0245(3) Uani 1 1 d .
H6 H 0.6706 0.0521 -0.0016 0.029 Uiso 1 1 calc R
N6 N 0.81391(19) 0.33910(10) -0.11288(9) 0.0313(3) Uani 1 1 d .
C8 C 0.93998(16) 0.75230(10) 0.83570(8) 0.0214(3) Uani 1 1 d .
C9 C 0.83107(16) 0.80587(9) 0.97090(8) 0.0194(2) Uani 1 1 d .
C10 C 0.79235(16) 0.71070(9) 0.99289(8) 0.0193(3) Uani 1 1 d .
C11 C 0.6625(2) 0.63580(11) 1.12665(10) 0.0293(3) Uani 1 1 d .
H11A H 0.7612 0.6027 1.1560 0.044 Uiso 1 1 calc R
H11B H 0.5958 0.5901 1.0885 0.044 Uiso 1 1 calc R
H11C H 0.5929 0.6612 1.1708 0.044 Uiso 1 1 calc R
C12 C 0.93758(19) 0.92914(10) 0.86839(10) 0.0261(3) Uani 1 1 d .
H12A H 0.8381 0.9551 0.8333 0.039 Uiso 1 1 calc R
H12B H 1.0350 0.9313 0.8339 0.039 Uiso 1 1 calc R
H12C H 0.9613 0.9680 0.9217 0.039 Uiso 1 1 calc R
C13 C 0.71984(19) 0.81422(11) 1.09309(9) 0.0259(3) Uani 1 1 d .
C14 C 0.82298(17) 0.62869(10) 0.93805(9) 0.0218(3) Uani 1 1 d .
H7A H 0.819(3) 0.4006(17) -0.1038(14) 0.044(6) Uiso 1 1 d .
H7B H 0.859(2) 0.3107(14) -0.1584(13) 0.036(5) Uiso 1 1 d .
H13 H 0.671(2) 0.8380(14) 1.1456(13) 0.035(5) 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'
Cl Cl 0.1484 0.1585 '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
O2 N1 O1 123.15(12)
O2 N1 C4 118.22(11)
O1 N1 C4 118.61(12)
C8 N2 C9 120.19(11)
C8 N2 C12 119.22(11)
C9 N2 C12 120.51(11)
C13 N3 C10 104.99(11)
C13 N3 C11 127.38(12)
C10 N3 C11 127.54(12)
C13 N4 C9 102.65(11)
C8 N5 C14 126.32(11)
C8 N5 C6 117.73(11)
C14 N5 C6 115.80(11)
N5 C6 H6A 109.5
N5 C6 H6B 109.5
H6A C6 H6B 109.5
N5 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C7 C1 C2 121.23(12)
C7 C1 H1 119.4
C2 C1 H1 119.4
N6 C2 C3 120.56(12)
N6 C2 C1 121.84(12)
C3 C2 C1 117.59(12)
C4 C3 C2 120.43(12)
C4 C3 H3 119.8
C2 C3 H3 119.8
C3 C4 C5 121.80(12)
C3 C4 N1 115.64(11)
C5 C4 N1 122.56(12)
C7 C5 C4 117.61(12)
C7 C5 Cl1 117.84(10)
C4 C5 Cl1 124.44(10)
C1 C7 C5 121.33(12)
C1 C7 H6 119.3
C5 C7 H6 119.3
C2 N6 H7A 118.2(15)
C2 N6 H7B 118.8(12)
H7A N6 H7B 122.4(19)
O3 C8 N2 121.67(12)
O3 C8 N5 121.36(12)
N2 C8 N5 116.97(11)
N4 C9 C10 112.45(12)
N4 C9 N2 126.41(12)
C10 C9 N2 121.14(12)
C9 C10 N3 105.78(11)
C9 C10 C14 123.01(12)
N3 C10 C14 131.19(12)
N3 C11 H11A 109.5
N3 C11 H11B 109.5
H11A C11 H11B 109.5
N3 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
N2 C12 H12A 109.5
N2 C12 H12B 109.5
H12A C12 H12B 109.5
N2 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
N4 C13 N3 114.13(12)
N4 C13 H13 124.8(11)
N3 C13 H13 121.0(11)
O4 C14 N5 120.89(12)
O4 C14 C10 126.80(12)
N5 C14 C10 112.30(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C5 1.7365(13)
O1 N1 1.2273(16)
O2 N1 1.2295(17)
O3 C8 1.2246(16)
O4 C14 1.2319(17)
N1 C4 1.4710(16)
N2 C8 1.3738(17)
N2 C9 1.3795(16)
N2 C12 1.4641(16)
N3 C13 1.3555(18)
N3 C10 1.3814(16)
N3 C11 1.4558(17)
N4 C13 1.3449(19)
N4 C9 1.3520(16)
N5 C8 1.4008(17)
N5 C14 1.4062(16)
N5 C6 1.4660(16)
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C1 C7 1.3794(19)
C1 C2 1.4085(19)
C1 H1 0.9300
C2 N6 1.3625(18)
C2 C3 1.4049(17)
C3 C4 1.3878(18)
C3 H3 0.9300
C4 C5 1.3963(18)
C5 C7 1.3955(19)
C7 H6 0.9300
N6 H7A 0.85(2)
N6 H7B 0.88(2)
C9 C10 1.3731(18)
C10 C14 1.4174(17)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C13 H13 0.962(19)
