# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email soumyajitghosh89@gmail.com _publ_contact_author_name 'Soumyajit Ghosh' loop_ _publ_author_name 'Soumyajit Ghosh' 'C. Malla Reddy' data_cmr_043_sg_1 _database_code_depnum_ccdc_archive 'CCDC 860122' #TrackingRef 'ALL CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Caffeine:2-iodo-4nitroaniline _chemical_melting_point 430.08 _chemical_formula_moiety 'C8 H10 N4 O2, C6 H5 I N2 O2' _chemical_formula_sum 'C14 H15 I N6 O4' _chemical_formula_weight 458.22 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' _symmetry_space_group_name_Hall -P2yn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.1283(5) _cell_length_b 13.8659(7) _cell_length_c 14.9447(8) _cell_angle_alpha 90.00 _cell_angle_beta 97.473(3) _cell_angle_gamma 90.00 _cell_volume 1670.05(16) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9892 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 26.88 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.822 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 1.952 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.308 _exptl_absorpt_correction_T_max 0.872 _exptl_absorpt_process_details 'multi-scan absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER KAPPA APEX II DUO' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 41560 _diffrn_reflns_av_R_equivalents 0.0626 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 26.99 _reflns_number_total 3644 _reflns_number_gt 2992 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0324P)^2^+5.3100P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3644 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0608 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1111 _refine_ls_wR_factor_gt 0.1015 _refine_ls_goodness_of_fit_ref 1.208 _refine_ls_restrained_S_all 1.208 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.85086(5) 0.05052(3) 0.88676(2) 0.04591(13) Uani 1 1 d . . . O1 O 0.0730(5) 0.7673(3) 0.6891(3) 0.0534(10) Uani 1 1 d . . . O2 O 0.2646(5) 0.9841(3) 0.4968(3) 0.0531(10) Uani 1 1 d . . . N5 N 0.7816(7) 0.2720(6) 0.9517(3) 0.0528(13) Uani 1 1 d . . . O4 O 1.1403(7) 0.3577(4) 0.6149(3) 0.0789(15) Uani 1 1 d . . . N2 N 0.1635(5) 0.8743(3) 0.5896(3) 0.0396(10) Uani 1 1 d . . . C3 C 0.2909(6) 0.8169(3) 0.4692(3) 0.0333(10) Uani 1 1 d . . . N3 N 0.3764(5) 0.8073(3) 0.3960(3) 0.0350(9) Uani 1 1 d . . . N4 N 0.3140(6) 0.6584(3) 0.4401(3) 0.0447(10) Uani 1 1 d . . . C9 C 0.8555(6) 0.2713(4) 0.8759(3) 0.0342(10) Uani 1 1 d . . . O3 O 1.1388(7) 0.2024(4) 0.6133(3) 0.0798(16) Uani 1 1 d . . . C1 C 0.1339(6) 0.7811(4) 0.6203(3) 0.0382(11) Uani 1 1 d . . . C2 C 0.2428(6) 0.9004(4) 0.5152(3) 0.0380(11) Uani 1 1 d . . . C6 C 0.4479(7) 0.8823(4) 0.3451(4) 0.0428(12) Uani 1 1 d . . . H6A H 0.5087 0.8532 0.3013 0.064 Uiso 1 1 calc R . . H6B H 0.5214 0.9214 0.3855 0.064 Uiso 1 1 calc R . . H6C H 0.3608 0.9218 0.3150 0.064 Uiso 1 1 calc R . . C4 C 0.3873(7) 0.7116(4) 0.3817(4) 0.0403(12) Uani 1 1 d . . . C5 C 0.2569(6) 0.7254(4) 0.4939(3) 0.0349(10) Uani 1 1 d . . . N1 N 0.1781(5) 0.7054(3) 0.5682(3) 0.0379(9) Uani 1 1 d . . . C7 C 0.1476(8) 0.6060(4) 0.5936(4) 0.0554(15) Uani 1 1 d . . . H7A H 0.2203 0.5896 0.6473 0.083 Uiso 1 1 calc R . . H7B H 0.1678 0.5635 0.5456 0.083 Uiso 1 1 calc R . . H7C H 0.0344 0.5995 0.6048 0.083 Uiso 1 1 calc R . . C8 C 0.1087(9) 0.9532(4) 0.6454(5) 0.0605(16) Uani 1 1 d . . . H8A H 0.1424 1.0140 0.6230 0.091 Uiso 1 1 calc R . . H8B H 0.1580 0.9451 0.7068 0.091 Uiso 1 1 calc R . . H8C H -0.0100 0.9517 0.6424 0.091 Uiso 1 1 calc R . . C10 C 0.8996(6) 0.1863(3) 0.8342(3) 0.0315(10) Uani 1 1 d . . . C11 C 0.9797(6) 0.1901(3) 0.7594(3) 0.0350(10) Uani 1 1 d . . . H10 H 1.0094 0.1335 0.7323 0.042 Uiso 1 1 calc R . . C12 C 1.0168(6) 0.2789(4) 0.7239(3) 0.0361(11) Uani 1 1 d . . . N6 N 1.1033(6) 0.2802(4) 0.6455(3) 0.0494(12) Uani 1 1 d . . . C14 C 0.8913(7) 0.3597(4) 0.8369(4) 0.0429(12) Uani 1 1 d . . . H14 H 0.8600 0.4167 0.8628 0.051 Uiso 1 1 calc R . . C13 C 0.9711(7) 0.3642(3) 0.7619(4) 0.0412(12) Uani 1 1 d . . . H13 H 0.9941 0.4234 0.7369 0.049 Uiso 1 1 calc R . . H5A H 0.775(11) 0.222(7) 0.968(6) 0.09(3) Uiso 1 1 d . . . H5B H 0.756(9) 0.325(6) 0.969(5) 0.07(2) Uiso 1 1 d . . . H4 H 0.454(6) 0.687(4) 0.338(4) 0.039(14) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0513(2) 0.0428(2) 0.0442(2) 0.01275(15) 0.00846(15) -0.00566(16) O1 0.055(2) 0.067(3) 0.043(2) 0.0046(19) 0.0222(18) 0.000(2) O2 0.075(3) 0.0336(19) 0.055(2) -0.0012(17) 0.025(2) -0.0004(18) N5 0.061(3) 0.065(4) 0.037(3) -0.009(3) 0.023(2) 0.001(3) O4 0.099(4) 0.072(3) 0.075(3) 0.028(3) 0.048(3) -0.005(3) N2 0.041(2) 0.041(2) 0.039(2) -0.0068(18) 0.0128(19) 0.0020(18) C3 0.031(2) 0.037(3) 0.031(2) -0.0012(19) 0.0013(19) 0.0025(19) N3 0.040(2) 0.035(2) 0.030(2) 0.0018(16) 0.0038(17) -0.0009(17) N4 0.052(3) 0.038(2) 0.044(3) -0.0009(19) 0.010(2) 0.001(2) C9 0.027(2) 0.049(3) 0.027(2) -0.001(2) 0.0041(18) -0.001(2) O3 0.112(4) 0.077(3) 0.064(3) -0.004(2) 0.063(3) 0.007(3) C1 0.034(3) 0.047(3) 0.034(3) -0.002(2) 0.008(2) -0.002(2) C2 0.043(3) 0.037(3) 0.035(3) -0.004(2) 0.007(2) -0.001(2) C6 0.047(3) 0.040(3) 0.042(3) 0.001(2) 0.009(2) -0.004(2) C4 0.043(3) 0.041(3) 0.039(3) -0.008(2) 0.010(2) 0.002(2) C5 0.034(3) 0.041(3) 0.028(2) -0.0002(19) 0.0003(19) 0.002(2) N1 0.039(2) 0.036(2) 0.041(2) 0.0056(18) 0.0122(18) -0.0018(17) C7 0.058(4) 0.043(3) 0.067(4) 0.016(3) 0.018(3) -0.009(3) C8 0.071(4) 0.055(4) 0.061(4) -0.013(3) 0.030(3) 0.007(3) C10 0.032(2) 0.034(2) 0.027(2) 0.0032(18) 0.0026(18) -0.0017(18) C11 0.039(3) 0.034(2) 0.032(2) -0.0028(19) 0.007(2) 0.002(2) C12 0.035(3) 0.043(3) 0.032(2) 0.004(2) 0.011(2) 0.001(2) N6 0.053(3) 0.062(3) 0.038(2) 0.010(2) 0.020(2) -0.001(2) C14 0.048(3) 0.035(3) 0.046(3) -0.005(2) 0.009(2) 0.006(2) C13 0.050(3) 0.028(2) 0.046(3) 0.007(2) 0.009(2) 0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C10 2.098(5) . ? O1 C1 1.213(6) . ? O2 C2 1.211(6) . ? N5 C9 1.349(6) . ? N5 H5A 0.74(9) . ? N5 H5B 0.82(8) . ? O4 N6 1.222(6) . ? N2 C1 1.402(7) . ? N2 C2 1.403(6) . ? N2 C8 1.479(7) . ? C3 C5 1.361(7) . ? C3 N3 1.377(6) . ? C3 C2 1.427(7) . ? N3 C4 1.349(6) . ? N3 C6 1.453(6) . ? N4 C4 1.340(7) . ? N4 C5 1.349(6) . ? C9 C10 1.401(7) . ? C9 C14 1.404(7) . ? O3 N6 1.230(7) . ? C1 N1 1.381(6) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C4 H4 0.97(5) . ? C5 N1 1.381(6) . ? N1 C7 1.459(7) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C10 C11 1.367(6) . ? C11 C12 1.388(7) . ? C11 H10 0.9300 . ? C12 C13 1.384(7) . ? C12 N6 1.443(6) . ? C14 C13 1.368(7) . ? C14 H14 0.9300 . ? C13 H13 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N5 H5A 109(7) . . ? C9 N5 H5B 116(5) . . ? H5A N5 H5B 136(8) . . ? C1 N2 C2 127.8(4) . . ? C1 N2 C8 114.9(4) . . ? C2 N2 C8 117.3(4) . . ? C5 C3 N3 105.4(4) . . ? C5 C3 C2 123.3(4) . . ? N3 C3 C2 131.3(4) . . ? C4 N3 C3 105.8(4) . . ? C4 N3 C6 125.6(4) . . ? C3 N3 C6 128.6(4) . . ? C4 N4 C5 103.0(4) . . ? N5 C9 C10 123.2(5) . . ? N5 C9 C14 118.7(5) . . ? C10 C9 C14 118.1(4) . . ? O1 C1 N1 121.5(5) . . ? O1 C1 N2 121.9(5) . . ? N1 C1 N2 116.6(4) . . ? O2 C2 N2 121.6(5) . . ? O2 C2 C3 127.6(5) . . ? N2 C2 C3 110.8(4) . . ? N3 C6 H6A 109.5 . . ? N3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N4 C4 N3 113.2(4) . . ? N4 C4 H4 126(3) . . ? N3 C4 H4 121(3) . . ? N4 C5 C3 112.5(4) . . ? N4 C5 N1 125.0(5) . . ? C3 C5 N1 122.5(4) . . ? C5 N1 C1 118.9(4) . . ? C5 N1 C7 120.7(4) . . ? C1 N1 C7 120.4(4) . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C11 C10 C9 120.5(4) . . ? C11 C10 I1 118.3(3) . . ? C9 C10 I1 121.1(3) . . ? C10 C11 C12 119.8(4) . . ? C10 C11 H10 120.1 . . ? C12 C11 H10 120.1 . . ? C13 C12 C11 121.2(4) . . ? C13 C12 N6 120.5(5) . . ? C11 C12 N6 118.3(4) . . ? O4 N6 O3 122.9(5) . . ? O4 N6 C12 119.0(5) . . ? O3 N6 C12 118.1(5) . . ? C13 C14 C9 121.8(5) . . ? C13 C14 H14 119.1 . . ? C9 C14 H14 119.1 . . ? C14 C13 C12 118.6(5) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.908 _refine_diff_density_min -0.717 _refine_diff_density_rms 0.102 #END# data_cmr_sg_068_1 _database_code_depnum_ccdc_archive 'CCDC 860123' #TrackingRef 'ALL CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Caffeine:4-iodo-3nitroaniline _chemical_melting_point 438 _chemical_formula_moiety 'C8 H10 N4 O2, C6 H5 I N2 O2' _chemical_formula_sum 'C14 H15 I N6 O4' _chemical_formula_weight 458.22 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _symmetry_space_group_name_Hall -P2ybc 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' _cell_length_a 8.0323(5) _cell_length_b 13.7265(8) _cell_length_c 15.3774(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.5480(10) _cell_angle_gamma 90.00 _cell_volume 1692.19(18) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 8701 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 31.37 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.799 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 1.926 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.831 _exptl_absorpt_correction_T_max 0.944 _exptl_absorpt_process_details 'multi-scan absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER KAPPA APEX II DUO' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13862 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3697 _reflns_number_gt 3227 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0297P)^2^+1.2141P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3697 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0312 _refine_ls_R_factor_gt 0.0256 _refine_ls_wR_factor_ref 0.0687 _refine_ls_wR_factor_gt 0.0649 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.53677(2) 0.932209(13) 0.175771(11) 0.05072(8) Uani 1 1 d . . . O1 O 1.0197(3) 0.22442(18) 0.76587(14) 0.0684(6) Uani 1 1 d . . . C7 C 0.9545(5) 0.4142(3) 0.7984(2) 0.0684(9) Uani 1 1 d . . . H7A H 1.0112 0.3878 0.7505 0.103 Uiso 1 1 calc R . . H7B H 1.0246 0.4615 0.8286 0.103 Uiso 1 1 calc R . . H7C H 0.8527 0.4447 0.7768 0.103 Uiso 1 1 calc R . . O2 O 0.8034(4) 0.44856(15) 0.94770(17) 0.0770(7) Uani 1 1 d . . . O4 O 0.4531(4) 0.71486(19) 0.20817(17) 0.0835(8) Uani 1 1 d . . . N2 N 0.9163(3) 0.33541(16) 0.85855(14) 0.0456(5) Uani 1 1 d . . . N3 N 0.7316(3) 0.27721(17) 1.06556(14) 0.0474(5) Uani 1 1 d . . . N1 N 0.9172(3) 0.16700(15) 0.89016(14) 0.0430(5) Uani 1 1 d . . . C12 C 0.6161(3) 0.83162(18) 0.08447(15) 0.0392(5) Uani 1 1 d . . . N5 N 0.5657(3) 0.67945(18) 0.17006(14) 0.0512(6) Uani 1 1 d . . . O3 O 0.6245(5) 0.6008(2) 0.1897(2) 0.1028(10) Uani 1 1 d . . . C1 C 0.9547(3) 0.2405(2) 0.83428(16) 0.0462(6) Uani 1 1 d . . . C2 C 0.8375(3) 0.3626(2) 0.93371(17) 0.0463(6) Uani 1 1 d . . . C3 C 0.8051(3) 0.28215(18) 0.98710(15) 0.0399(5) Uani 1 1 d . . . C8 C 0.6760(5) 0.3568(3) 1.1192(2) 0.0679(9) Uani 1 1 d . . . H8A H 0.6099 0.3313 1.1638 0.102 Uiso 1 1 calc R . . H8B H 0.6101 0.4015 1.0835 0.102 Uiso 1 1 calc R . . H8C H 0.7712 0.3902 1.1456 0.102 Uiso 1 1 calc R . . C4 C 0.7302(4) 0.1817(2) 1.0855(2) 0.0581(7) Uani 1 1 d . . . N4 N 0.7970(3) 0.12407(17) 1.02640(16) 0.0553(6) Uani 1 1 d . . . C5 C 0.8420(3) 0.18853(18) 0.96595(16) 0.0395(5) Uani 1 1 d . . . C6 C 0.9537(4) 0.0660(2) 0.8677(2) 0.0599(8) Uani 1 1 d . . . H6A H 0.9745 0.0288 0.9201 0.090 Uiso 1 1 calc R . . H6B H 1.0505 0.0641 0.8341 0.090 Uiso 1 1 calc R . . H6C H 0.8602 0.0388 0.8342 0.090 Uiso 1 1 calc R . . C13 C 0.6754(3) 0.87050(19) 0.00839(17) 0.0463(6) Uani 1 1 d . . . H9 H 0.6711 0.9375 -0.0002 0.056 Uiso 1 1 calc R . . C14 C 0.7399(4) 0.8125(2) -0.05420(17) 0.0480(6) Uani 1 1 d . . . H10 H 0.7761 0.8412 -0.1045 0.058 Uiso 1 1 calc R . . C9 C 0.7523(3) 0.71191(19) -0.04412(16) 0.0429(5) Uani 1 1 d . . . N6 N 0.8180(4) 0.6542(2) -0.10524(18) 0.0640(8) Uani 1 1 d . . . C10 C 0.6934(3) 0.67134(19) 0.03190(16) 0.0438(6) Uani 1 1 d . . . H13 H 0.6995 0.6044 0.0409 0.053 Uiso 1 1 calc R . . C11 C 0.6262(3) 0.73055(18) 0.09352(15) 0.0394(5) Uani 1 1 d . . . H4 H 0.683(4) 0.156(2) 1.141(2) 0.064(9) Uiso 1 1 d . . . H4B H 0.852(4) 0.683(3) -0.149(2) 0.068(10) Uiso 1 1 d . . . H4A H 0.817(4) 0.598(3) -0.096(2) 0.061(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.05873(12) 0.04843(12) 0.04659(11) -0.00457(7) 0.01590(8) 0.00043(8) O1 0.0802(14) 0.0809(16) 0.0473(11) -0.0036(11) 0.0285(10) 0.0132(12) C7 0.083(2) 0.061(2) 0.0638(19) 0.0241(16) 0.0240(17) 0.0023(16) O2 0.118(2) 0.0366(11) 0.0807(16) 0.0036(10) 0.0377(15) 0.0102(12) O4 0.1055(19) 0.0736(16) 0.0774(16) 0.0088(13) 0.0542(15) -0.0022(14) N2 0.0521(12) 0.0429(11) 0.0432(11) 0.0082(9) 0.0134(10) 0.0024(10) N3 0.0563(13) 0.0495(13) 0.0379(11) -0.0059(9) 0.0145(9) -0.0021(10) N1 0.0493(11) 0.0362(10) 0.0447(11) -0.0048(9) 0.0110(9) 0.0058(9) C12 0.0419(12) 0.0399(12) 0.0363(12) 0.0008(10) 0.0056(10) -0.0012(10) N5 0.0649(14) 0.0493(14) 0.0409(11) 0.0078(10) 0.0164(11) -0.0047(11) O3 0.145(3) 0.0747(17) 0.095(2) 0.0470(16) 0.0586(19) 0.0276(19) C1 0.0442(13) 0.0545(16) 0.0408(13) -0.0011(11) 0.0087(11) 0.0051(11) C2 0.0531(14) 0.0403(13) 0.0467(14) 0.0006(11) 0.0112(11) 0.0025(11) C3 0.0457(13) 0.0376(12) 0.0373(12) -0.0014(10) 0.0103(10) 0.0004(10) C8 0.085(2) 0.069(2) 0.0520(17) -0.0179(15) 0.0222(16) 0.0007(17) C4 0.0737(19) 0.0545(17) 0.0480(15) 0.0071(13) 0.0179(14) -0.0045(15) N4 0.0704(15) 0.0414(12) 0.0554(14) 0.0101(11) 0.0136(12) -0.0015(11) C5 0.0413(12) 0.0386(12) 0.0391(12) -0.0009(10) 0.0054(10) 0.0006(10) C6 0.0645(18) 0.0446(16) 0.072(2) -0.0154(14) 0.0139(15) 0.0114(13) C13 0.0621(16) 0.0351(12) 0.0426(13) 0.0061(10) 0.0102(12) 0.0000(11) C14 0.0631(16) 0.0448(14) 0.0376(12) 0.0080(10) 0.0145(12) -0.0036(12) C9 0.0508(13) 0.0421(13) 0.0366(12) 0.0004(10) 0.0098(10) -0.0027(11) N6 0.102(2) 0.0448(15) 0.0486(14) -0.0015(12) 0.0323(14) -0.0008(15) C10 0.0564(14) 0.0354(12) 0.0405(12) 0.0042(10) 0.0098(11) -0.0019(11) C11 0.0418(12) 0.0429(13) 0.0340(11) 0.0075(10) 0.0062(10) -0.0037(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C12 2.096(2) . ? O1 C1 1.223(3) . ? C7 N2 1.467(3) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? O2 C2 1.234(3) . ? O4 N5 1.210(3) . ? N2 C1 1.395(4) . ? N2 C2 1.402(3) . ? N3 C4 1.347(4) . ? N3 C3 1.377(3) . ? N3 C8 1.456(4) . ? N1 C1 1.371(3) . ? N1 C5 1.377(3) . ? N1 C6 1.463(3) . ? C12 C13 1.396(3) . ? C12 C11 1.396(3) . ? N5 O3 1.209(4) . ? N5 C11 1.478(3) . ? C2 C3 1.409(4) . ? C3 C5 1.363(3) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C4 N4 1.341(4) . ? C4 H4 1.02(3) . ? N4 C5 1.349(3) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C13 C14 1.375(4) . ? C13 H9 0.9300 . ? C14 C9 1.392(4) . ? C14 H10 0.9300 . ? C9 N6 1.360(4) . ? C9 C10 1.403(3) . ? N6 H4B 0.84(4) . ? N6 H4A 0.79(4) . ? C10 C11 1.383(4) . ? C10 H13 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C7 H7A 109.5 . . ? N2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C1 N2 C2 126.0(2) . . ? C1 N2 C7 117.5(2) . . ? C2 N2 C7 116.5(2) . . ? C4 N3 C3 104.9(2) . . ? C4 N3 C8 126.5(2) . . ? C3 N3 C8 128.5(2) . . ? C1 N1 C5 119.8(2) . . ? C1 N1 C6 119.7(2) . . ? C5 N1 C6 120.5(2) . . ? C13 C12 C11 116.3(2) . . ? C13 C12 I1 116.29(18) . . ? C11 C12 I1 127.29(18) . . ? O3 N5 O4 122.0(3) . . ? O3 N5 C11 118.7(2) . . ? O4 N5 C11 119.2(2) . . ? O1 C1 N1 121.9(3) . . ? O1 C1 N2 120.8(3) . . ? N1 C1 N2 117.3(2) . . ? O2 C2 N2 121.0(2) . . ? O2 C2 C3 126.6(3) . . ? N2 C2 C3 112.4(2) . . ? C5 C3 N3 105.9(2) . . ? C5 C3 C2 123.3(2) . . ? N3 C3 C2 130.8(2) . . ? N3 C8 H8A 109.5 . . ? N3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N4 C4 N3 114.2(2) . . ? N4 C4 H4 123.3(19) . . ? N3 C4 H4 122.4(19) . . ? C4 N4 C5 102.5(2) . . ? N4 C5 C3 112.5(2) . . ? N4 C5 N1 126.3(2) . . ? C3 C5 N1 121.2(2) . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C14 C13 C12 121.9(2) . . ? C14 C13 H9 119.1 . . ? C12 C13 H9 119.1 . . ? C13 C14 C9 121.6(2) . . ? C13 C14 H10 119.2 . . ? C9 C14 H10 119.2 . . ? N6 C9 C14 121.9(2) . . ? N6 C9 C10 120.6(3) . . ? C14 C9 C10 117.4(2) . . ? C9 N6 H4B 116(2) . . ? C9 N6 H4A 116(3) . . ? H4B N6 H4A 128(4) . . ? C11 C10 C9 120.2(2) . . ? C11 C10 H13 119.9 . . ? C9 C10 H13 119.9 . . ? C10 C11 C12 122.6(2) . . ? C10 C11 N5 115.3(2) . . ? C12 C11 N5 122.1(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.765 _refine_diff_density_min -0.453 _refine_diff_density_rms 0.058 #END# data_cmr_sg_069_1 _database_code_depnum_ccdc_archive 'CCDC 860124' #TrackingRef 'ALL CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Caffeine:4-chloro-3nitroaniline _chemical_melting_point 420.53 _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 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _symmetry_space_group_name_Hall -P2ybc 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' _cell_length_a 7.7950(6) _cell_length_b 13.5627(9) _cell_length_c 14.9920(10) _cell_angle_alpha 90.00 _cell_angle_beta 95.6570(10) _cell_angle_gamma 90.00 _cell_volume 1577.25(19) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9981 _cell_measurement_theta_min 3.03 _cell_measurement_theta_max 32.48 _exptl_crystal_description needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.545 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.278 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.977 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details 'multi-scan absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER KAPPA APEX II DUO' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13582 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 26.98 _reflns_number_total 3420 _reflns_number_gt 3181 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0538P)^2^+0.7563P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3420 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0969 _refine_ls_wR_factor_gt 0.0936 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group 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_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0358(2) 0.0290(2) 0.0292(2) 0.00938(13) 0.00964(14) -0.00144(13) O1 0.0360(6) 0.0444(6) 0.0293(5) 0.0005(5) 0.0178(4) 0.0005(5) O2 0.0571(8) 0.0380(6) 0.0333(6) -0.0141(5) 0.0167(5) -0.0112(5) O3 0.0384(6) 0.0319(5) 0.0242(5) 0.0024(4) 0.0146(4) -0.0041(4) O4 0.0543(7) 0.0191(5) 0.0359(6) -0.0004(4) 0.0201(5) -0.0050(5) N1 0.0288(6) 0.0294(6) 0.0185(5) 0.0013(4) 0.0058(4) 0.0036(5) N2 0.0245(5) 0.0181(5) 0.0199(5) 0.0020(4) 0.0055(4) -0.0026(4) N3 0.0252(5) 0.0258(6) 0.0178(5) 0.0027(4) 0.0065(4) 0.0014(4) N4 0.0312(6) 0.0219(6) 0.0238(6) -0.0043(4) 0.0045(4) 0.0023(4) N5 0.0252(5) 0.0191(5) 0.0204(5) -0.0021(4) 0.0087(4) -0.0007(4) C6 0.0401(8) 0.0242(7) 0.0277(7) -0.0060(5) 0.0157(6) -0.0004(6) C1 0.0284(7) 0.0239(7) 0.0214(6) -0.0029(5) 0.0063(5) 0.0035(5) C2 0.0226(6) 0.0226(6) 0.0202(6) 0.0008(5) 0.0049(5) 0.0021(5) C3 0.0238(6) 0.0199(6) 0.0205(6) -0.0002(5) 0.0048(5) 0.0015(5) C4 0.0203(6) 0.0241(6) 0.0178(6) -0.0009(5) 0.0030(4) 0.0021(5) C5 0.0209(6) 0.0228(6) 0.0220(6) 0.0042(5) 0.0030(5) -0.0004(5) C7 0.0268(6) 0.0197(6) 0.0272(7) -0.0005(5) 0.0029(5) 0.0003(5) N6 0.0492(8) 0.0219(6) 0.0261(6) 0.0003(5) 0.0196(5) 0.0021(5) C8 0.0210(6) 0.0227(6) 0.0210(6) 0.0011(5) 0.0049(5) -0.0011(5) C9 0.0200(6) 0.0202(6) 0.0182(6) 0.0003(4) 0.0029(4) 0.0004(4) C10 0.0214(6) 0.0200(6) 0.0172(6) 0.0005(4) 0.0061(4) 0.0002(5) C11 0.0369(8) 0.0282(7) 0.0244(7) 0.0063(5) 0.0106(6) 0.0013(6) C12 0.0324(7) 0.0183(6) 0.0281(7) 0.0048(5) 0.0056(5) -0.0033(5) C13 0.0316(7) 0.0253(7) 0.0216(6) -0.0025(5) 0.0064(5) 0.0023(5) C14 0.0239(6) 0.0210(6) 0.0214(6) -0.0005(5) 0.0073(5) -0.0005(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag 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) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag 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) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.98 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.452 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.046 #END# data_cmr_sg_070a_1 _database_code_depnum_ccdc_archive 'CCDC 860125' #TrackingRef 'ALL CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Caffeine:4-fluoro-3nitroaniline _chemical_melting_point 401.5 _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 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pna2(1) ' _symmetry_space_group_name_Hall P2c-2n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 15.8624(19) _cell_length_b 13.5643(15) _cell_length_c 7.3360(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1578.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2763 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 26.48 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.991 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_process_details 'multi-scan absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER KAPPA APEX II DUO' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7079 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 2 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2053 _reflns_number_gt 1704 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0629P)^2^+0.6271P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.8(16) _refine_ls_number_reflns 2053 _refine_ls_number_parameters 241 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0568 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1212 _refine_ls_wR_factor_gt 0.1106 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.035 _refine_ls_shift/su_mean 0.002 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 _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.16268(18) 0.60845(17) -0.0087(4) 0.0709(8) Uani 1 1 d . . . O1 O 0.24481(15) 0.22947(19) -0.0831(4) 0.0490(7) Uani 1 1 d . . . O2 O 0.44095(13) 0.46039(15) 0.0813(4) 0.0373(6) Uani 1 1 d . . . O3 O 0.2345(2) 0.7711(3) -0.1072(6) 0.0870(13) Uani 1 1 d . . . O4 O 0.18675(18) 0.9090(2) -0.0209(7) 0.0851(14) Uani 1 1 d . . . N1 N 0.34219(14) 0.34266(18) 0.0078(4) 0.0287(6) Uani 1 1 d . . . N2 N 0.55443(16) 0.28690(18) 0.1863(4) 0.0264(6) Uani 1 1 d . . . N3 N 0.50896(18) 0.12988(19) 0.1475(4) 0.0326(6) Uani 1 1 d . . . N4 N 0.36984(15) 0.17146(18) 0.0262(4) 0.0298(6) Uani 1 1 d . . . N5 N -0.0941(2) 0.8470(3) 0.2431(5) 0.0424(8) Uani 1 1 d . . . N6 N 0.18211(17) 0.8209(2) -0.0295(5) 0.0427(7) Uani 1 1 d . . . C1 C 0.31545(19) 0.2455(2) -0.0198(5) 0.0327(7) Uani 1 1 d . . . C2 C 0.42209(18) 0.3723(2) 0.0707(5) 0.0277(7) Uani 1 1 d . . . C3 C 0.47338(18) 0.2909(2) 0.1162(4) 0.0228(6) Uani 1 1 d . . . C4 C 0.6091(2) 0.3701(2) 0.2311(5) 0.0322(8) Uani 1 1 d . . . H4A H 0.6610 0.3460 0.2818 0.048 Uiso 1 1 calc R . . H4B H 0.5814 0.4117 0.3184 0.048 Uiso 1 1 calc R . . H4C H 0.6208 0.4072 0.1226 0.048 Uiso 1 1 calc R . . C5 C 0.5726(2) 0.1897(2) 0.2021(5) 0.0323(7) Uani 1 1 d . . . C6 C 0.44878(18) 0.1939(2) 0.0957(4) 0.0252(6) Uani 1 1 d . . . C7 C 0.3446(2) 0.0679(2) 0.0063(6) 0.0474(10) Uani 1 1 d . . . H7A H 0.3263 0.0428 0.1221 0.071 Uiso 1 1 calc R . . H7B H 0.3916 0.0299 -0.0364 0.071 Uiso 1 1 calc R . . H7C H 0.2992 0.0632 -0.0798 0.071 Uiso 1 1 calc R . . C8 C 0.2811(2) 0.4216(3) -0.0344(6) 0.0427(9) Uani 1 1 d . . . H8A H 0.2790 0.4317 -0.1639 0.064 Uiso 1 1 calc R . . H8B H 0.2983 0.4815 0.0244 0.064 Uiso 1 1 calc R . . H8C H 0.2263 0.4029 0.0088 0.064 Uiso 1 1 calc R . . C9 C -0.0306(2) 0.7887(2) 0.1778(5) 0.0306(7) Uani 1 1 d . . . C10 C 0.04277(18) 0.8305(2) 0.1066(5) 0.0269(6) Uani 1 1 d . . . H10 H 0.0480 0.8988 0.1011 0.032 Uiso 1 1 calc R . . C11 C 0.1077(2) 0.7715(2) 0.0444(5) 0.0329(7) Uani 1 1 d . . . C12 C 0.1005(2) 0.6689(3) 0.0524(5) 0.0424(9) Uani 1 1 d . . . C13 C 0.0294(3) 0.6268(3) 0.1221(6) 0.0508(11) Uani 1 1 d . . . H13 H 0.0248 0.5585 0.1272 0.061 Uiso 1 1 calc R . . C14 C -0.0359(2) 0.6852(3) 0.1850(5) 0.0392(9) Uani 1 1 d . . . H14 H -0.0840 0.6557 0.2327 0.047 Uiso 1 1 calc R . . H5 H 0.624(2) 0.163(3) 0.257(6) 0.041(10) Uiso 1 1 d . . . H6A H -0.143(3) 0.820(3) 0.275(7) 0.058(13) Uiso 1 1 d . . . H6B H -0.097(2) 0.907(3) 0.214(5) 0.032(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0958(18) 0.0528(13) 0.0642(17) -0.0202(14) -0.0134(16) 0.0459(13) O1 0.0284(13) 0.0610(16) 0.0575(18) -0.0046(16) -0.0077(12) -0.0180(11) O2 0.0292(11) 0.0229(11) 0.0597(16) 0.0016(12) 0.0006(12) -0.0019(9) O3 0.076(2) 0.096(3) 0.088(3) 0.027(2) 0.052(2) 0.049(2) O4 0.0514(17) 0.0560(18) 0.148(4) -0.037(2) 0.053(2) -0.0199(14) N1 0.0202(11) 0.0324(13) 0.0335(15) 0.0035(13) -0.0029(11) -0.0025(10) N2 0.0281(13) 0.0216(13) 0.0294(14) -0.0012(12) -0.0048(12) -0.0015(10) N3 0.0444(15) 0.0252(13) 0.0282(14) 0.0005(12) 0.0026(12) 0.0023(12) N4 0.0300(13) 0.0272(13) 0.0321(16) -0.0005(12) 0.0012(12) -0.0111(11) N5 0.0318(16) 0.0382(18) 0.057(2) 0.0150(17) 0.0146(15) -0.0056(15) N6 0.0330(15) 0.060(2) 0.0355(17) -0.0040(17) 0.0042(13) 0.0126(14) C1 0.0283(16) 0.0400(18) 0.0299(17) 0.0009(16) 0.0029(14) -0.0125(13) C2 0.0225(13) 0.0306(16) 0.0301(17) 0.0020(15) 0.0021(13) -0.0014(12) C3 0.0245(14) 0.0198(14) 0.0241(15) -0.0018(13) 0.0005(12) -0.0013(11) C4 0.0271(16) 0.0305(17) 0.0392(19) -0.0076(16) -0.0071(14) -0.0031(13) C5 0.0379(18) 0.0287(16) 0.0304(18) 0.0031(15) -0.0035(15) 0.0062(14) C6 0.0295(15) 0.0247(14) 0.0216(15) -0.0001(13) 0.0022(13) 0.0002(12) C7 0.054(2) 0.0314(17) 0.056(3) -0.010(2) 0.011(2) -0.0219(16) C8 0.0226(14) 0.046(2) 0.060(2) 0.018(2) -0.0058(17) 0.0013(14) C9 0.0354(17) 0.0273(16) 0.0291(16) 0.0059(15) -0.0048(14) -0.0063(13) C10 0.0311(15) 0.0195(13) 0.0300(16) -0.0027(14) -0.0015(13) 0.0017(12) C11 0.0387(16) 0.0339(17) 0.0261(16) -0.0026(14) -0.0041(13) 0.0078(13) C12 0.062(2) 0.0311(18) 0.0339(19) -0.0074(16) -0.0127(18) 0.0207(17) C13 0.088(3) 0.0218(15) 0.042(2) -0.0001(17) -0.031(2) -0.0006(19) C14 0.055(2) 0.0275(17) 0.0353(19) 0.0097(16) -0.0148(17) -0.0123(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C12 1.358(4) . ? O1 C1 1.232(4) . ? O2 C2 1.234(4) . ? O3 N6 1.214(4) . ? O4 N6 1.198(4) . ? N1 C1 1.399(4) . ? N1 C2 1.407(4) . ? N1 C8 1.477(4) . ? N2 C5 1.355(4) . ? N2 C3 1.386(4) . ? N2 C4 1.460(4) . ? N3 C6 1.345(4) . ? N3 C5 1.356(4) . ? N4 C1 1.366(4) . ? N4 C6 1.386(4) . ? N4 C7 1.468(4) . ? N5 C9 1.367(5) . ? N5 H6A 0.88(5) . ? N5 H6B 0.84(4) . ? N6 C11 1.462(4) . ? C2 C3 1.412(4) . ? C3 C6 1.380(4) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5 0.98(4) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.396(4) . ? C9 C14 1.407(4) . ? C10 C11 1.382(4) . ? C10 H10 0.9300 . ? C11 C12 1.397(5) . ? C12 C13 1.364(6) . ? C13 C14 1.384(6) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 126.1(2) . . ? C1 N1 C8 117.0(3) . . ? C2 N1 C8 116.9(3) . . ? C5 N2 C3 105.5(2) . . ? C5 N2 C4 127.3(3) . . ? C3 N2 C4 127.2(3) . . ? C6 N3 C5 103.0(3) . . ? C1 N4 C6 120.0(2) . . ? C1 N4 C7 120.4(3) . . ? C6 N4 C7 119.6(3) . . ? C9 N5 H6A 120(3) . . ? C9 N5 H6B 121(3) . . ? H6A N5 H6B 115(4) . . ? O4 N6 O3 122.5(3) . . ? O4 N6 C11 119.2(3) . . ? O3 N6 C11 118.2(3) . . ? O1 C1 N4 122.5(3) . . ? O1 C1 N1 119.8(3) . . ? N4 C1 N1 117.7(3) . . ? O2 C2 N1 121.0(3) . . ? O2 C2 C3 127.1(3) . . ? N1 C2 C3 111.9(3) . . ? C6 C3 N2 105.4(2) . . ? C6 C3 C2 123.8(3) . . ? N2 C3 C2 130.7(3) . . ? 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 . . ? N2 C5 N3 113.5(3) . . ? N2 C5 H5 125(2) . . ? N3 C5 H5 121(2) . . ? N3 C6 C3 112.6(3) . . ? N3 C6 N4 127.1(3) . . ? C3 C6 N4 120.3(3) . . ? N4 C7 H7A 109.5 . . ? N4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? 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 . . ? N5 C9 C10 120.7(3) . . ? N5 C9 C14 121.3(3) . . ? C10 C9 C14 118.0(3) . . ? C11 C10 C9 120.6(3) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 120.2(3) . . ? C10 C11 N6 117.3(3) . . ? C12 C11 N6 122.5(3) . . ? F1 C12 C13 118.1(3) . . ? F1 C12 C11 121.9(4) . . ? C13 C12 C11 120.0(3) . . ? C12 C13 C14 120.3(3) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C13 C14 C9 120.9(3) . . ? C13 C14 H14 119.5 . . ? C9 C14 H14 119.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.417 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.046 #END# data_cmr_sg_073_1 _database_code_depnum_ccdc_archive 'CCDC 860126' #TrackingRef 'ALL CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Caffeine:2-chloro-5nitroaniline _chemical_melting_point 379.5 _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 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _symmetry_space_group_name_Hall -P2ybc 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' _cell_length_a 13.5850(6) _cell_length_b 13.9085(6) _cell_length_c 17.5266(8) _cell_angle_alpha 90.00 _cell_angle_beta 104.8920(10) _cell_angle_gamma 90.00 _cell_volume 3200.4(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9614 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 32.04 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.522 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 0.274 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.877 _exptl_absorpt_correction_T_max 0.947 _exptl_absorpt_process_details 'multi-scan absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER KAPPA APEX II DUO' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 26368 _diffrn_reflns_av_R_equivalents 0.0206 _diffrn_reflns_av_sigmaI/netI 0.0172 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 27.00 _reflns_number_total 6933 _reflns_number_gt 6332 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0429P)^2^+1.2507P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6933 _refine_ls_number_parameters 473 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.0834 _refine_ls_wR_factor_gt 0.0805 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.16666(2) 0.39648(2) 0.362065(16) 0.01950(8) Uani 1 1 d . . . Cl2 Cl 0.34741(2) 0.60425(2) 0.309366(16) 0.02024(8) Uani 1 1 d . . . O1 O 0.13965(9) 0.30974(8) -0.01341(5) 0.0330(2) Uani 1 1 d . . . O2 O 0.12735(8) 0.16487(7) 0.02841(5) 0.0313(2) Uani 1 1 d . . . O3 O 0.10291(7) 0.78807(6) 0.45150(5) 0.02018(18) Uani 1 1 d . . . N5 N 0.09074(8) 0.67595(7) 0.19614(6) 0.0178(2) Uani 1 1 d . . . O5 O 0.10798(7) 1.00181(6) 0.25274(5) 0.02226(19) Uani 1 1 d . . . O6 O 0.58166(7) 0.70737(6) 0.08319(5) 0.02061(19) Uani 1 1 d . . . O7 O 0.63198(7) 0.50184(6) 0.29525(5) 0.02242(19) Uani 1 1 d . . . O8 O 0.34721(9) 0.82394(8) -0.02224(6) 0.0353(3) Uani 1 1 d . . . O9 O 0.33982(8) 0.67724(8) -0.06509(5) 0.0308(2) Uani 1 1 d . . . N1 N 0.13745(8) 0.25188(8) 0.03927(6) 0.0220(2) Uani 1 1 d . . . N2 N 0.16556(8) 0.19219(8) 0.31625(6) 0.0189(2) Uani 1 1 d . . . N3 N 0.10147(8) 0.89453(7) 0.35104(6) 0.0159(2) Uani 1 1 d . . . N4 N 0.09427(7) 0.82433(7) 0.14590(6) 0.0169(2) Uani 1 1 d . . . C11 C 0.10029(11) 0.90047(9) 0.09003(7) 0.0234(3) Uani 1 1 d . . . H11A H 0.1074 0.8724 0.0417 0.035 Uiso 1 1 calc R . . H11B H 0.1581 0.9406 0.1120 0.035 Uiso 1 1 calc R . . H11C H 0.0393 0.9385 0.0796 0.035 Uiso 1 1 calc R . . N6 N 0.09351(7) 0.72629(7) 0.33015(5) 0.0149(2) Uani 1 1 d . . . N7 N 0.60495(8) 0.60519(7) 0.18951(6) 0.0166(2) Uani 1 1 d . . . N8 N 0.61043(8) 0.68098(8) 0.39310(6) 0.0190(2) Uani 1 1 d . . . N9 N 0.58337(7) 0.77289(7) 0.20232(6) 0.0155(2) Uani 1 1 d . . . N10 N 0.58790(8) 0.82694(8) 0.33552(6) 0.0201(2) Uani 1 1 d . . . N11 N 0.34240(8) 0.73679(8) -0.01250(6) 0.0228(2) Uani 1 1 d . . . N14 N 0.33409(8) 0.80609(8) 0.25605(6) 0.0185(2) Uani 1 1 d . . . C1 C 0.14716(9) 0.28918(9) 0.11928(7) 0.0172(2) Uani 1 1 d . . . C2 C 0.14932(9) 0.38793(9) 0.13057(7) 0.0189(2) Uani 1 1 d . . . H2 H 0.1466 0.4302 0.0890 0.023 Uiso 1 1 calc R . . C3 C 0.15576(9) 0.42120(9) 0.20644(7) 0.0181(2) Uani 1 1 d . . . H3 H 0.1572 0.4869 0.2165 0.022 Uiso 1 1 calc R . . C4 C 0.16009(8) 0.35585(9) 0.26719(6) 0.0156(2) Uani 1 1 d . . . C5 C 0.15196(8) 0.22302(9) 0.17880(7) 0.0160(2) Uani 1 1 d . . . H5 H 0.1507 0.1575 0.1680 0.019 Uiso 1 1 calc R . . C6 C 0.15871(8) 0.25558(8) 0.25598(7) 0.0145(2) Uani 1 1 d . . . C7 C 0.09954(8) 0.80174(8) 0.38179(7) 0.0152(2) Uani 1 1 d . . . C8 C 0.10120(9) 0.91773(9) 0.27280(7) 0.0159(2) Uani 1 1 d . . . C9 C 0.09300(8) 0.83513(9) 0.22420(6) 0.0149(2) Uani 1 1 d . . . C10 C 0.09240(9) 0.72880(9) 0.13295(7) 0.0182(2) Uani 1 1 d . . . H10 H 0.0923 0.7021 0.0843 0.022 Uiso 1 1 calc R . . C11A C 0.09162(8) 0.74328(9) 0.25233(7) 0.0146(2) Uani 1 1 d . . . C12 C 0.09162(10) 0.62831(9) 0.35995(7) 0.0196(2) Uani 1 1 d . . . H12A H 0.0701 0.5848 0.3163 0.029 Uiso 1 1 calc R . . H12B H 0.0450 0.6250 0.3927 0.029 Uiso 1 1 calc R . . H12C H 0.1586 0.6108 0.3903 0.029 Uiso 1 1 calc R . . C13 C 0.10516(10) 0.97551(9) 0.40537(7) 0.0221(3) Uani 1 1 d . . . H13A H 0.1726 1.0021 0.4194 0.033 Uiso 1 1 calc R . . H13B H 0.0877 0.9534 0.4521 0.033 Uiso 1 1 calc R . . H13C H 0.0576 1.0240 0.3801 0.033 Uiso 1 1 calc R . . C14 C 0.58977(8) 0.69636(9) 0.15390(7) 0.0154(2) Uani 1 1 d . . . C15 C 0.61572(9) 0.58463(9) 0.26957(7) 0.0162(2) Uani 1 1 d . . . C16 C 0.60560(9) 0.66787(9) 0.31366(7) 0.0159(2) Uani 1 1 d . . . C17 C 0.61980(11) 0.60725(10) 0.45367(7) 0.0265(3) Uani 1 1 d . . . H17A H 0.6237 0.6373 0.5037 0.040 Uiso 1 1 calc R . . H17B H 0.6804 0.5703 0.4570 0.040 Uiso 1 1 calc R . . H17C H 0.5615 0.5657 0.4403 0.040 Uiso 1 1 calc R . . C18 C 0.56687(9) 0.86937(9) 0.16825(7) 0.0198(2) Uani 1 1 d . . . H18A H 0.5357 0.9091 0.2003 0.030 Uiso 1 1 calc R . . H18B H 0.5230 0.8656 0.1158 0.030 Uiso 1 1 calc R . . H18C H 0.6310 0.8968 0.1663 0.030 Uiso 1 1 calc R . . C19 C 0.59166(8) 0.75824(9) 0.28141(7) 0.0152(2) Uani 1 1 d . . . C20 C 0.59880(10) 0.77640(9) 0.40210(7) 0.0214(3) Uani 1 1 d . . . H20 H 0.5984 0.8044 0.4502 0.026 Uiso 1 1 calc R . . C21 C 0.61201(11) 0.52310(9) 0.13864(7) 0.0236(3) Uani 1 1 d . . . H21A H 0.6791 0.4959 0.1548 0.035 Uiso 1 1 calc R . . H21B H 0.5988 0.5443 0.0848 0.035 Uiso 1 1 calc R . . H21C H 0.5627 0.4754 0.1430 0.035 Uiso 1 1 calc R . . C22 C 0.34026(9) 0.70198(9) 0.06600(7) 0.0174(2) Uani 1 1 d . . . C23 C 0.34480(9) 0.60373(9) 0.08031(7) 0.0193(2) Uani 1 1 d . . . H23 H 0.3463 0.5598 0.0406 0.023 Uiso 1 1 calc R . . C24 C 0.34703(9) 0.57357(9) 0.15637(7) 0.0183(2) Uani 1 1 d . . . H24 H 0.3504 0.5084 0.1685 0.022 Uiso 1 1 calc R . . C25 C 0.34421(8) 0.64096(9) 0.21416(7) 0.0156(2) Uani 1 1 d . . . C26 C 0.33665(8) 0.77016(9) 0.12260(7) 0.0159(2) Uani 1 1 d . . . H26 H 0.3329 0.8352 0.1098 0.019 Uiso 1 1 calc R . . C27 C 0.33874(8) 0.74061(8) 0.19955(7) 0.0145(2) Uani 1 1 d . . . H2A H 0.1562(13) 0.2111(13) 0.3591(11) 0.036(5) Uiso 1 1 d . . . H2B H 0.1471(12) 0.1331(13) 0.3036(10) 0.028(4) Uiso 1 1 d . . . H14A H 0.3452(13) 0.8654(14) 0.2463(10) 0.037(5) Uiso 1 1 d . . . H14B H 0.3432(13) 0.7889(13) 0.3007(11) 0.034(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.02654(16) 0.01896(15) 0.01347(13) -0.00326(10) 0.00599(11) -0.00014(11) Cl2 0.02732(16) 0.01964(15) 0.01494(14) 0.00353(10) 0.00760(11) 0.00037(11) O1 0.0481(6) 0.0387(6) 0.0145(4) 0.0029(4) 0.0121(4) -0.0019(5) O2 0.0457(6) 0.0303(5) 0.0197(4) -0.0084(4) 0.0118(4) -0.0047(4) O3 0.0260(4) 0.0227(4) 0.0121(4) 0.0008(3) 0.0055(3) -0.0003(4) N5 0.0176(5) 0.0199(5) 0.0166(5) -0.0042(4) 0.0055(4) -0.0004(4) O5 0.0324(5) 0.0163(4) 0.0183(4) 0.0012(3) 0.0069(4) 0.0009(4) O6 0.0244(4) 0.0238(5) 0.0145(4) 0.0026(3) 0.0067(3) 0.0014(4) O7 0.0324(5) 0.0169(4) 0.0191(4) 0.0026(3) 0.0087(4) 0.0004(4) O8 0.0577(7) 0.0297(6) 0.0203(5) 0.0074(4) 0.0136(5) 0.0000(5) O9 0.0397(6) 0.0391(6) 0.0148(4) -0.0055(4) 0.0094(4) 0.0012(5) N1 0.0227(5) 0.0302(6) 0.0137(5) -0.0016(4) 0.0060(4) -0.0013(4) N2 0.0271(6) 0.0167(5) 0.0138(5) 0.0002(4) 0.0068(4) 0.0000(4) N3 0.0200(5) 0.0152(5) 0.0127(4) -0.0016(4) 0.0047(4) 0.0009(4) N4 0.0180(5) 0.0209(5) 0.0119(4) -0.0005(4) 0.0043(4) 0.0013(4) C11 0.0314(7) 0.0255(7) 0.0145(5) 0.0038(5) 0.0084(5) 0.0023(5) N6 0.0178(5) 0.0144(5) 0.0129(4) 0.0007(4) 0.0049(4) -0.0004(4) N7 0.0216(5) 0.0150(5) 0.0145(5) -0.0010(4) 0.0071(4) -0.0005(4) N8 0.0217(5) 0.0223(5) 0.0133(5) -0.0019(4) 0.0051(4) -0.0024(4) N9 0.0167(5) 0.0150(5) 0.0153(4) 0.0009(4) 0.0049(4) -0.0001(4) N10 0.0204(5) 0.0204(5) 0.0194(5) -0.0052(4) 0.0049(4) -0.0006(4) N11 0.0240(5) 0.0306(6) 0.0137(5) 0.0005(4) 0.0049(4) 0.0008(5) N14 0.0254(5) 0.0166(5) 0.0145(5) -0.0007(4) 0.0072(4) -0.0019(4) C1 0.0153(5) 0.0249(6) 0.0121(5) -0.0024(5) 0.0049(4) -0.0018(5) C2 0.0192(6) 0.0219(6) 0.0159(5) 0.0040(5) 0.0052(4) -0.0022(5) C3 0.0190(6) 0.0172(6) 0.0185(5) 0.0011(5) 0.0054(4) -0.0022(5) C4 0.0149(5) 0.0190(6) 0.0129(5) -0.0014(4) 0.0036(4) -0.0009(4) C5 0.0149(5) 0.0180(6) 0.0154(5) -0.0023(4) 0.0043(4) -0.0009(4) C6 0.0117(5) 0.0176(6) 0.0143(5) -0.0001(4) 0.0033(4) 0.0000(4) C7 0.0134(5) 0.0181(6) 0.0141(5) 0.0003(4) 0.0036(4) 0.0005(4) C8 0.0156(5) 0.0184(6) 0.0133(5) 0.0006(4) 0.0032(4) 0.0023(4) C9 0.0142(5) 0.0193(6) 0.0114(5) 0.0006(4) 0.0036(4) 0.0019(4) C10 0.0180(6) 0.0224(6) 0.0147(5) -0.0047(5) 0.0050(4) 0.0000(5) C11A 0.0116(5) 0.0185(6) 0.0140(5) -0.0011(4) 0.0036(4) -0.0003(4) C12 0.0260(6) 0.0149(6) 0.0181(6) 0.0018(5) 0.0060(5) -0.0013(5) C13 0.0328(7) 0.0183(6) 0.0158(5) -0.0042(5) 0.0076(5) 0.0002(5) C14 0.0135(5) 0.0178(6) 0.0154(5) 0.0012(4) 0.0047(4) -0.0010(4) C15 0.0159(5) 0.0185(6) 0.0146(5) 0.0000(4) 0.0048(4) -0.0027(4) C16 0.0154(5) 0.0192(6) 0.0132(5) -0.0009(4) 0.0039(4) -0.0025(4) C17 0.0359(7) 0.0289(7) 0.0148(6) 0.0032(5) 0.0066(5) -0.0018(6) C18 0.0212(6) 0.0152(6) 0.0236(6) 0.0035(5) 0.0070(5) 0.0010(5) C19 0.0126(5) 0.0177(6) 0.0155(5) -0.0016(4) 0.0038(4) -0.0017(4) C20 0.0236(6) 0.0235(6) 0.0173(5) -0.0065(5) 0.0053(5) -0.0013(5) C21 0.0364(7) 0.0184(6) 0.0175(5) -0.0025(5) 0.0097(5) 0.0025(5) C22 0.0157(5) 0.0243(6) 0.0120(5) 0.0010(5) 0.0031(4) -0.0006(5) C23 0.0209(6) 0.0209(6) 0.0164(5) -0.0059(5) 0.0051(5) -0.0010(5) C24 0.0193(6) 0.0157(5) 0.0203(6) -0.0015(5) 0.0056(4) -0.0015(4) C25 0.0149(5) 0.0182(6) 0.0139(5) 0.0012(4) 0.0044(4) -0.0013(4) C26 0.0151(5) 0.0171(6) 0.0154(5) 0.0013(4) 0.0038(4) -0.0004(4) C27 0.0114(5) 0.0169(6) 0.0153(5) -0.0007(4) 0.0035(4) -0.0013(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C4 1.7367(12) . ? Cl2 C25 1.7348(12) . ? O1 N1 1.2310(14) . ? O2 N1 1.2273(15) . ? O3 C7 1.2257(14) . ? N5 C10 1.3342(16) . ? N5 C11A 1.3569(15) . ? O5 C8 1.2314(15) . ? O6 C14 1.2254(14) . ? O7 C15 1.2353(15) . ? O8 N11 1.2282(15) . ? O9 N11 1.2330(14) . ? N1 C1 1.4689(15) . ? N2 C6 1.3608(15) . ? N2 H2A 0.836(19) . ? N2 H2B 0.871(18) . ? N3 C7 1.4014(15) . ? N3 C8 1.4077(14) . ? N3 C13 1.4674(15) . ? N4 C10 1.3471(16) . ? N4 C9 1.3850(14) . ? N4 C11 1.4588(15) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? N6 C7 1.3744(15) . ? N6 C11A 1.3779(14) . ? N6 C12 1.4621(15) . ? N7 C15 1.4023(14) . ? N7 C14 1.4049(15) . ? N7 C21 1.4668(15) . ? N8 C20 1.3506(16) . ? N8 C16 1.3888(14) . ? N8 C17 1.4579(16) . ? N9 C19 1.3768(15) . ? N9 C14 1.3778(15) . ? N9 C18 1.4625(15) . ? N10 C20 1.3375(17) . ? N10 C19 1.3565(15) . ? N11 C22 1.4658(15) . ? N14 C27 1.3588(15) . ? N14 H14A 0.86(2) . ? N14 H14B 0.797(18) . ? C1 C5 1.3799(17) . ? C1 C2 1.3868(17) . ? C2 C3 1.3893(17) . ? C2 H2 0.9300 . ? C3 C4 1.3897(17) . ? C3 H3 0.9300 . ? C4 C6 1.4078(16) . ? C5 C6 1.4070(15) . ? C5 H5 0.9300 . ? C8 C9 1.4174(16) . ? C9 C11A 1.3712(17) . ? C10 H10 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C15 C16 1.4182(16) . ? C16 C19 1.3712(16) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C20 H20 0.9300 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C26 1.3824(17) . ? C22 C23 1.3879(17) . ? C23 C24 1.3905(17) . ? C23 H23 0.9300 . ? C24 C25 1.3877(17) . ? C24 H24 0.9300 . ? C25 C27 1.4080(16) . ? C26 C27 1.4032(16) . ? C26 H26 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 N5 C11A 102.90(10) . . ? O2 N1 O1 123.47(11) . . ? O2 N1 C1 118.38(10) . . ? O1 N1 C1 118.15(11) . . ? C6 N2 H2A 119.9(12) . . ? C6 N2 H2B 117.2(11) . . ? H2A N2 H2B 115.1(16) . . ? C7 N3 C8 126.16(10) . . ? C7 N3 C13 117.27(9) . . ? C8 N3 C13 116.57(10) . . ? C10 N4 C9 105.62(10) . . ? C10 N4 C11 127.22(10) . . ? C9 N4 C11 127.12(10) . . ? N4 C11 H11A 109.5 . . ? N4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C7 N6 C11A 120.24(10) . . ? C7 N6 C12 118.68(9) . . ? C11A N6 C12 121.06(10) . . ? C15 N7 C14 126.46(10) . . ? C15 N7 C21 116.30(10) . . ? C14 N7 C21 117.23(10) . . ? C20 N8 C16 105.63(10) . . ? C20 N8 C17 126.65(11) . . ? C16 N8 C17 127.63(11) . . ? C19 N9 C14 120.26(10) . . ? C19 N9 C18 120.74(10) . . ? C14 N9 C18 119.00(10) . . ? C20 N10 C19 102.96(10) . . ? O8 N11 O9 123.46(11) . . ? O8 N11 C22 118.11(11) . . ? O9 N11 C22 118.43(11) . . ? C27 N14 H14A 117.0(12) . . ? C27 N14 H14B 119.4(13) . . ? H14A N14 H14B 119.3(17) . . ? C5 C1 C2 123.88(11) . . ? C5 C1 N1 117.48(11) . . ? C2 C1 N1 118.64(11) . . ? C1 C2 C3 117.40(11) . . ? C1 C2 H2 121.3 . . ? C3 C2 H2 121.3 . . ? C2 C3 C4 119.69(11) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C4 C6 122.99(11) . . ? C3 C4 Cl1 120.16(9) . . ? C6 C4 Cl1 116.85(9) . . ? C1 C5 C6 119.40(11) . . ? C1 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? N2 C6 C5 120.83(11) . . ? N2 C6 C4 122.53(11) . . ? C5 C6 C4 116.64(10) . . ? O3 C7 N6 121.24(11) . . ? O3 C7 N3 121.78(11) . . ? N6 C7 N3 116.98(10) . . ? O5 C8 N3 120.94(10) . . ? O5 C8 C9 126.74(11) . . ? N3 C8 C9 112.32(10) . . ? C11A C9 N4 105.08(10) . . ? C11A C9 C8 123.04(10) . . ? N4 C9 C8 131.63(11) . . ? N5 C10 N4 114.03(10) . . ? N5 C10 H10 123.0 . . ? N4 C10 H10 123.0 . . ? N5 C11A C9 112.36(10) . . ? N5 C11A N6 126.48(11) . . ? C9 C11A N6 121.15(10) . . ? N6 C12 H12A 109.5 . . ? N6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? 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 . . ? O6 C14 N9 121.52(11) . . ? O6 C14 N7 121.80(11) . . ? N9 C14 N7 116.68(10) . . ? O7 C15 N7 121.17(11) . . ? O7 C15 C16 126.56(11) . . ? N7 C15 C16 112.27(10) . . ? C19 C16 N8 105.00(10) . . ? C19 C16 C15 123.10(11) . . ? N8 C16 C15 131.85(11) . . ? N8 C17 H17A 109.5 . . ? N8 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N8 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N9 C18 H18A 109.5 . . ? N9 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N9 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N10 C19 C16 112.55(10) . . ? N10 C19 N9 126.28(11) . . ? C16 C19 N9 121.17(10) . . ? N10 C20 N8 113.86(11) . . ? N10 C20 H20 123.1 . . ? N8 C20 H20 123.1 . . ? N7 C21 H21A 109.5 . . ? N7 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N7 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C26 C22 C23 123.64(11) . . ? C26 C22 N11 117.38(11) . . ? C23 C22 N11 118.96(11) . . ? C22 C23 C24 117.34(11) . . ? C22 C23 H23 121.3 . . ? C24 C23 H23 121.3 . . ? C25 C24 C23 119.88(11) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C24 C25 C27 122.83(11) . . ? C24 C25 Cl2 120.31(9) . . ? C27 C25 Cl2 116.85(9) . . ? C22 C26 C27 119.55(11) . . ? C22 C26 H26 120.2 . . ? C27 C26 H26 120.2 . . ? N14 C27 C26 120.72(11) . . ? N14 C27 C25 122.51(11) . . ? C26 C27 C25 116.76(10) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.311 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.043 #END# data_cmr_sg_083_1 _database_code_depnum_ccdc_archive 'CCDC 860127' #TrackingRef 'ALL CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Caffeine:4nitroaniline _chemical_melting_point 436.7 _chemical_formula_moiety 'C8 H10 N4 O2, C6 H6 N2 O2' _chemical_formula_sum 'C14 H16 N6 O4' _chemical_formula_weight 332.33 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _symmetry_space_group_name_Hall -P2ybc 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' _cell_length_a 10.5157(7) _cell_length_b 10.7574(7) _cell_length_c 13.6464(10) _cell_angle_alpha 90.00 _cell_angle_beta 100.1790(10) _cell_angle_gamma 90.00 _cell_volume 1519.41(18) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9897 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 31.65 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.946 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details 'multi-scan absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER KAPPA APEX II DUO' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 23085 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0140 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3326 _reflns_number_gt 2798 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0704P)^2^+0.3880P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3326 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1286 _refine_ls_wR_factor_gt 0.1192 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.73726(11) 1.21451(10) 0.92028(9) 0.0526(3) Uani 1 1 d . . . O2 O 0.54755(11) 0.83960(11) 0.82693(8) 0.0522(3) Uani 1 1 d . . . O3 O 1.03169(13) 0.81675(13) 0.24350(9) 0.0658(4) Uani 1 1 d . . . O4 O 1.02065(13) 0.94861(11) 0.12417(10) 0.0640(3) Uani 1 1 d . . . N1 N 0.64524(11) 1.02620(11) 0.87511(8) 0.0385(3) Uani 1 1 d . . . N2 N 0.58904(11) 0.77852(10) 1.04982(9) 0.0396(3) Uani 1 1 d . . . N3 N 0.68807(12) 0.91719(11) 1.16248(9) 0.0428(3) Uani 1 1 d . . . N4 N 0.71932(11) 1.07801(10) 1.04402(8) 0.0366(3) Uani 1 1 d . . . C9 C 0.94320(13) 0.75072(13) 0.08561(10) 0.0391(3) Uani 1 1 d . . . N5 N 1.00204(12) 0.84395(12) 0.15522(9) 0.0452(3) Uani 1 1 d . . . C1 C 0.70349(12) 1.11268(12) 0.94589(10) 0.0369(3) Uani 1 1 d . . . C2 C 0.59831(12) 0.90840(12) 0.89464(10) 0.0355(3) Uani 1 1 d . . . C3 C 0.61706(12) 0.88277(11) 0.99831(9) 0.0321(3) Uani 1 1 d . . . C4 C 0.52815(16) 0.66373(14) 1.01053(14) 0.0529(4) Uani 1 1 d . . . H4A H 0.5170 0.6101 1.0646 0.079 Uiso 1 1 calc R . . H4B H 0.5817 0.6232 0.9701 0.079 Uiso 1 1 calc R . . H4C H 0.4454 0.6818 0.9709 0.079 Uiso 1 1 calc R . . C5 C 0.63264(19) 1.06323(18) 0.77012(12) 0.0585(4) Uani 1 1 d . . . H5A H 0.6218 1.1517 0.7646 0.088 Uiso 1 1 calc R . . H5B H 0.5589 1.0228 0.7318 0.088 Uiso 1 1 calc R . . H5C H 0.7091 1.0394 0.7454 0.088 Uiso 1 1 calc R . . C6 C 0.67703(12) 0.96353(12) 1.06915(9) 0.0328(3) Uani 1 1 d . . . C7 C 0.63322(15) 0.80476(14) 1.14652(11) 0.0457(3) Uani 1 1 d . . . C8 C 0.78456(16) 1.16162(15) 1.12186(12) 0.0505(4) Uani 1 1 d . . . H8A H 0.8219 1.2300 1.0917 0.076 Uiso 1 1 calc R . . H8B H 0.8514 1.1170 1.1647 0.076 Uiso 1 1 calc R . . H8C H 0.7231 1.1926 1.1601 0.076 Uiso 1 1 calc R . . N6 N 0.76786(16) 0.48833(15) -0.11585(13) 0.0572(4) Uani 1 1 d . . . C12 C 0.82823(13) 0.57246(13) -0.05003(11) 0.0418(3) Uani 1 1 d . . . C13 C 0.86480(15) 0.54412(14) 0.05181(12) 0.0459(3) Uani 1 1 d . . . H13 H 0.8505 0.4645 0.0740 0.055 Uiso 1 1 calc R . . C14 C 0.92103(14) 0.63159(14) 0.11889(11) 0.0442(3) Uani 1 1 d . . . H14 H 0.9441 0.6115 0.1860 0.053 Uiso 1 1 calc R . . C11 C 0.85391(14) 0.69340(14) -0.08149(11) 0.0435(3) Uani 1 1 d . . . H11 H 0.8320 0.7139 -0.1486 0.052 Uiso 1 1 calc R . . C10 C 0.91047(13) 0.78103(14) -0.01508(11) 0.0413(3) Uani 1 1 d . . . H10 H 0.9270 0.8603 -0.0370 0.050 Uiso 1 1 calc R . . H7 H 0.6259(18) 0.7441(18) 1.2005(14) 0.060(5) Uiso 1 1 d . . . H6A H 0.749(2) 0.509(2) -0.1766(18) 0.071(6) Uiso 1 1 d . . . H6B H 0.772(2) 0.411(2) -0.0964(18) 0.080(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0600(7) 0.0354(6) 0.0655(7) 0.0076(5) 0.0192(5) -0.0068(5) O2 0.0640(7) 0.0498(6) 0.0427(6) -0.0154(5) 0.0090(5) -0.0065(5) O3 0.0801(9) 0.0666(8) 0.0454(6) 0.0068(6) -0.0032(6) -0.0018(7) O4 0.0806(9) 0.0412(6) 0.0676(8) 0.0069(6) 0.0063(6) -0.0041(6) N1 0.0454(6) 0.0380(6) 0.0338(6) 0.0026(5) 0.0116(5) -0.0001(5) N2 0.0413(6) 0.0306(6) 0.0489(6) 0.0037(5) 0.0129(5) 0.0000(5) N3 0.0501(7) 0.0430(7) 0.0351(6) 0.0037(5) 0.0069(5) 0.0046(5) N4 0.0385(6) 0.0309(6) 0.0398(6) -0.0041(4) 0.0051(4) -0.0037(4) C9 0.0352(6) 0.0392(7) 0.0436(7) 0.0081(6) 0.0093(5) 0.0075(5) N5 0.0422(6) 0.0440(7) 0.0490(7) 0.0059(5) 0.0074(5) 0.0065(5) C1 0.0362(6) 0.0317(6) 0.0446(7) 0.0014(5) 0.0119(5) 0.0005(5) C2 0.0364(6) 0.0342(7) 0.0373(6) -0.0041(5) 0.0103(5) 0.0023(5) C3 0.0335(6) 0.0270(6) 0.0369(6) -0.0006(5) 0.0097(5) 0.0009(5) C4 0.0550(9) 0.0314(7) 0.0746(11) -0.0034(7) 0.0177(8) -0.0066(6) C5 0.0781(12) 0.0628(10) 0.0371(8) 0.0087(7) 0.0171(7) -0.0016(9) C6 0.0327(6) 0.0300(6) 0.0363(6) -0.0012(5) 0.0075(5) 0.0034(5) C7 0.0533(8) 0.0420(8) 0.0431(7) 0.0084(6) 0.0121(6) 0.0033(6) C8 0.0537(9) 0.0411(8) 0.0536(9) -0.0131(7) 0.0011(7) -0.0083(7) N6 0.0729(10) 0.0435(8) 0.0541(9) 0.0021(6) 0.0085(7) -0.0005(7) C12 0.0402(7) 0.0388(7) 0.0483(8) 0.0037(6) 0.0134(6) 0.0080(6) C13 0.0506(8) 0.0358(7) 0.0526(8) 0.0142(6) 0.0131(6) 0.0040(6) C14 0.0452(7) 0.0453(8) 0.0427(7) 0.0148(6) 0.0091(6) 0.0077(6) C11 0.0483(8) 0.0443(8) 0.0396(7) 0.0113(6) 0.0123(6) 0.0081(6) C10 0.0424(7) 0.0372(7) 0.0460(7) 0.0129(6) 0.0127(6) 0.0066(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2215(17) . ? O2 C2 1.2297(16) . ? O3 N5 1.2253(17) . ? O4 N5 1.2307(17) . ? N1 C2 1.4024(18) . ? N1 C1 1.4016(18) . ? N1 C5 1.4704(18) . ? N2 C7 1.3491(19) . ? N2 C3 1.3827(16) . ? N2 C4 1.4495(19) . ? N3 C7 1.341(2) . ? N3 C6 1.3534(17) . ? N4 C1 1.3715(18) . ? N4 C6 1.3734(17) . ? N4 C8 1.4664(17) . ? C9 C14 1.393(2) . ? C9 C10 1.3948(19) . ? C9 N5 1.443(2) . ? C2 C3 1.4205(18) . ? C3 C6 1.3680(17) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C7 H7 0.997(19) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? N6 C12 1.352(2) . ? N6 H6A 0.85(2) . ? N6 H6B 0.87(3) . ? C12 C13 1.408(2) . ? C12 C11 1.411(2) . ? C13 C14 1.372(2) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C11 C10 1.369(2) . ? C11 H11 0.9300 . ? C10 H10 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C1 126.47(11) . . ? C2 N1 C5 117.12(12) . . ? C1 N1 C5 116.41(12) . . ? C7 N2 C3 105.07(11) . . ? C7 N2 C4 126.39(13) . . ? C3 N2 C4 128.53(13) . . ? C7 N3 C6 102.50(12) . . ? C1 N4 C6 119.93(11) . . ? C1 N4 C8 120.07(12) . . ? C6 N4 C8 119.98(12) . . ? C14 C9 C10 120.66(14) . . ? C14 C9 N5 120.11(13) . . ? C10 C9 N5 119.23(13) . . ? O3 N5 O4 121.91(14) . . ? O3 N5 C9 119.09(13) . . ? O4 N5 C9 119.00(13) . . ? O1 C1 N4 122.14(13) . . ? O1 C1 N1 120.78(13) . . ? N4 C1 N1 117.08(11) . . ? O2 C2 N1 121.44(12) . . ? O2 C2 C3 126.66(13) . . ? N1 C2 C3 111.90(11) . . ? C6 C3 N2 105.59(11) . . ? C6 C3 C2 123.10(12) . . ? N2 C3 C2 131.24(12) . . ? 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 C3 112.54(12) . . ? N3 C6 N4 125.99(12) . . ? C3 C6 N4 121.48(12) . . ? N3 C7 N2 114.30(13) . . ? N3 C7 H7 123.8(11) . . ? N2 C7 H7 121.9(11) . . ? 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 . . ? C12 N6 H6A 118.4(15) . . ? C12 N6 H6B 116.4(16) . . ? H6A N6 H6B 123(2) . . ? N6 C12 C13 121.68(14) . . ? N6 C12 C11 120.51(14) . . ? C13 C12 C11 117.79(14) . . ? C14 C13 C12 121.36(13) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C13 C14 C9 119.38(13) . . ? C13 C14 H14 120.3 . . ? C9 C14 H14 120.3 . . ? C10 C11 C12 121.18(13) . . ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? C11 C10 C9 119.60(13) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.295 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.043 #END# data_cmr_sg_084_1 _database_code_depnum_ccdc_archive 'CCDC 860128' #TrackingRef 'ALL CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Caffeine:2,4dinitrobenzoicacid _chemical_melting_point 432.27 _chemical_formula_moiety 'C7 H4 N2 O6,C8 H10 N4 O2' _chemical_formula_sum 'C15 H14 N6 O8' _chemical_formula_weight 406.32 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5624(4) _cell_length_b 11.8197(6) _cell_length_c 18.7587(10) _cell_angle_alpha 88.2690(10) _cell_angle_beta 77.0890(10) _cell_angle_gamma 72.2120(10) _cell_volume 1760.53(15) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9935 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 31.60 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.533 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.963 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details 'multi-scan absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER KAPPA APEX II DUO' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 28334 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 27.00 _reflns_number_total 7644 _reflns_number_gt 5914 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0744P)^2^+1.2155P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7644 _refine_ls_number_parameters 545 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0714 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1665 _refine_ls_wR_factor_gt 0.1464 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0132(3) 1.2593(2) 1.07235(17) 0.0973(8) Uani 1 1 d . . . O2 O -0.0386(3) 1.1055(2) 1.12300(16) 0.1125(10) Uani 1 1 d . . . O3 O 0.3391(4) 0.69955(19) 0.95179(12) 0.0864(7) Uani 1 1 d . . . O4 O 0.4693(3) 0.71518(19) 1.03267(15) 0.0900(7) Uani 1 1 d . . . O5 O 0.6429(3) 0.7522(2) 0.87669(15) 0.1095(11) Uani 1 1 d . . . O6 O -0.0569(3) 0.22832(18) 0.88091(12) 0.0782(6) Uani 1 1 d . . . O7 O 0.2771(2) 0.26745(15) 0.66139(9) 0.0596(5) Uani 1 1 d . . . N5 N -0.1001(3) 0.60527(16) 0.78665(11) 0.0514(5) Uani 1 1 d . . . O9 O -0.1319(2) 0.22978(16) 0.64053(10) 0.0652(5) Uani 1 1 d . . . O10 O 0.0820(3) -0.17405(15) 0.61102(10) 0.0652(5) Uani 1 1 d . . . O11 O 0.5052(4) 0.2645(2) 0.80135(14) 0.1089(10) Uani 1 1 d . . . O12 O 0.3748(4) 0.86972(19) 0.68961(18) 0.1222(12) Uani 1 1 d . . . O13 O 0.2830(3) 0.3720(2) 0.87292(12) 0.0831(7) Uani 1 1 d . . . O14 O 0.6127(3) 0.76237(17) 0.62551(13) 0.0872(8) Uani 1 1 d . . . O15 O 0.8392(2) 0.51986(19) 0.61926(12) 0.0694(5) Uani 1 1 d . . . O16 O 0.6471(3) 0.5226(2) 0.56336(9) 0.0687(5) Uani 1 1 d . . . C7 C 0.5885(3) 0.8572(2) 0.86247(12) 0.0513(6) Uani 1 1 d . . . N2A N 0.3926(2) 0.75545(17) 0.98692(11) 0.0482(4) Uani 1 1 d . . . O16A O 0.6515(6) 0.8962(3) 0.8120(2) 0.210(3) Uani 1 1 d . . . C16 C 0.0834(3) 0.43943(18) 0.72723(11) 0.0394(4) Uani 1 1 d . . . N4 N 0.1004(2) 0.53632(15) 0.68690(9) 0.0389(4) Uani 1 1 d . . . N3 N 0.1055(2) 0.24909(16) 0.77045(10) 0.0462(4) Uani 1 1 d . . . N7 N 0.0894(2) 0.15637(15) 0.54542(10) 0.0435(4) Uani 1 1 d . . . N8 N 0.3413(2) -0.12950(15) 0.47976(10) 0.0439(4) Uani 1 1 d . . . C20 C 0.4094(3) -0.06011(19) 0.43393(13) 0.0464(5) Uani 1 1 d . . . N10 N -0.0197(2) 0.02832(17) 0.62688(10) 0.0468(4) Uani 1 1 d . . . N11 N 0.4053(3) 0.3594(2) 0.82327(12) 0.0641(6) Uani 1 1 d . . . N12 N 0.6954(2) 0.53165(15) 0.61809(10) 0.0416(4) Uani 1 1 d . . . C1 C 0.4413(3) 0.93064(19) 0.91864(11) 0.0405(4) Uani 1 1 d . . . C2 C 0.3943(3) 1.0533(2) 0.91413(13) 0.0507(5) Uani 1 1 d . . . H2 H 0.4528 1.0868 0.8759 0.061 Uiso 1 1 calc R . . C3 C 0.2634(3) 1.1266(2) 0.96477(14) 0.0519(6) Uani 1 1 d . . . H3 H 0.2326 1.2088 0.9610 0.062 Uiso 1 1 calc R . . C4 C 0.1793(3) 1.0756(2) 1.02089(13) 0.0483(5) Uani 1 1 d . . . N1 N 0.0411(3) 1.1529(2) 1.07640(15) 0.0678(6) Uani 1 1 d . . . C6 C 0.3510(3) 0.88464(18) 0.97701(11) 0.0398(4) Uani 1 1 d . . . C5 C 0.2199(3) 0.9549(2) 1.02858(13) 0.0482(5) Uani 1 1 d . . . H5 H 0.1610 0.9222 1.0671 0.058 Uiso 1 1 calc R . . C8 C -0.0172(3) 0.2935(2) 0.83412(14) 0.0537(6) Uani 1 1 d . . . N2 N -0.0902(3) 0.41498(17) 0.84174(11) 0.0565(5) Uani 1 1 d . . . C10 C -0.0398(3) 0.48502(19) 0.78771(12) 0.0447(5) Uani 1 1 d . . . C11 C 0.2087(3) 0.5343(2) 0.61463(12) 0.0473(5) Uani 1 1 d . . . H11A H 0.1679 0.5013 0.5791 0.071 Uiso 1 1 calc R . . H11B H 0.3215 0.4863 0.6149 0.071 Uiso 1 1 calc R . . H11C H 0.2080 0.6138 0.6023 0.071 Uiso 1 1 calc R . . C12 C 0.1659(3) 0.31533(19) 0.71405(12) 0.0423(5) Uani 1 1 d . . . C13 C -0.0112(3) 0.63162(19) 0.72428(12) 0.0456(5) Uani 1 1 d . . . C14 C -0.2105(5) 0.4678(3) 0.90991(18) 0.0965(13) Uani 1 1 d . . . H14A H -0.1931 0.5404 0.9225 0.145 Uiso 1 1 calc R . . H14B H -0.1938 0.4133 0.9485 0.145 Uiso 1 1 calc R . . H14C H -0.3232 0.4842 0.9033 0.145 Uiso 1 1 calc R . . C15 C 0.1837(4) 0.1195(2) 0.76271(16) 0.0637(7) Uani 1 1 d . . . H15A H 0.2971 0.0998 0.7689 0.096 Uiso 1 1 calc R . . H15B H 0.1845 0.0921 0.7149 0.096 Uiso 1 1 calc R . . H15C H 0.1205 0.0820 0.7993 0.096 Uiso 1 1 calc R . . C16A C -0.0271(3) 0.1441(2) 0.60629(12) 0.0469(5) Uani 1 1 d . . . C17 C 0.2063(3) 0.05731(18) 0.50906(11) 0.0386(4) Uani 1 1 d . . . C18 C 0.2090(3) -0.05436(18) 0.52931(11) 0.0399(4) Uani 1 1 d . . . C19 C 0.3970(3) -0.2598(2) 0.47694(16) 0.0593(7) Uani 1 1 d . . . H19A H 0.4920 -0.2888 0.4366 0.089 Uiso 1 1 calc R . . H19B H 0.3069 -0.2879 0.4705 0.089 Uiso 1 1 calc R . . H19C H 0.4285 -0.2879 0.5218 0.089 Uiso 1 1 calc R . . N9 N 0.3309(2) 0.05545(15) 0.44932(10) 0.0450(4) Uani 1 1 d . . . C21 C 0.0918(3) -0.07734(19) 0.59046(12) 0.0453(5) Uani 1 1 d . . . C22 C -0.1401(4) 0.0147(3) 0.69375(14) 0.0667(7) Uani 1 1 d . . . H22A H -0.0799 -0.0212 0.7303 0.100 Uiso 1 1 calc R . . H22B H -0.2024 -0.0351 0.6826 0.100 Uiso 1 1 calc R . . H22C H -0.2164 0.0914 0.7119 0.100 Uiso 1 1 calc R . . C23 C 0.0879(3) 0.2749(2) 0.52028(15) 0.0563(6) Uani 1 1 d . . . H23A H 0.1910 0.2885 0.5237 0.084 Uiso 1 1 calc R . . H23B H -0.0056 0.3336 0.5503 0.084 Uiso 1 1 calc R . . H23C H 0.0772 0.2805 0.4703 0.084 Uiso 1 1 calc R . . C24 C 0.4301(3) 0.4668(2) 0.78616(12) 0.0473(5) Uani 1 1 d . . . C25 C 0.3252(3) 0.5762(2) 0.81367(12) 0.0518(6) Uani 1 1 d . . . H25 H 0.2420 0.5836 0.8562 0.062 Uiso 1 1 calc R . . C26 C 0.3454(3) 0.6754(2) 0.77699(13) 0.0507(6) Uani 1 1 d . . . H26 H 0.2755 0.7504 0.7954 0.061 Uiso 1 1 calc R . . C27 C 0.4681(3) 0.66564(18) 0.71306(11) 0.0401(4) Uani 1 1 d . . . C28 C 0.4814(3) 0.77755(19) 0.67589(13) 0.0497(5) Uani 1 1 d . . . C29 C 0.5553(3) 0.45094(19) 0.72349(12) 0.0443(5) Uani 1 1 d . . . H29 H 0.6263 0.3758 0.7061 0.053 Uiso 1 1 calc R . . C30 C 0.5700(2) 0.55185(17) 0.68798(10) 0.0362(4) Uani 1 1 d . . . H14 H 0.623(5) 0.823(4) 0.604(2) 0.109(13) Uiso 1 1 d . . . H5A H 0.730(6) 0.708(4) 0.843(2) 0.118(14) Uiso 1 1 d . . . H13 H -0.024(3) 0.709(2) 0.7074(14) 0.052(7) Uiso 1 1 d . . . H20 H 0.507(3) -0.089(2) 0.3920(15) 0.054(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0687(14) 0.0577(13) 0.138(2) -0.0341(14) 0.0143(13) -0.0029(10) O2 0.0887(17) 0.0867(18) 0.107(2) -0.0096(15) 0.0512(15) 0.0020(14) O3 0.144(2) 0.0568(12) 0.0729(13) 0.0014(10) -0.0297(14) -0.0484(14) O4 0.1073(18) 0.0582(12) 0.1187(19) 0.0337(13) -0.0604(16) -0.0237(12) O5 0.1034(18) 0.0520(12) 0.1021(18) 0.0108(11) 0.0641(15) 0.0156(12) O6 0.0883(14) 0.0515(11) 0.0771(13) 0.0216(10) 0.0160(11) -0.0226(10) O7 0.0630(10) 0.0411(9) 0.0516(9) -0.0015(7) 0.0103(8) 0.0013(8) N5 0.0549(11) 0.0337(9) 0.0496(11) -0.0008(8) 0.0124(9) -0.0077(8) O9 0.0646(11) 0.0456(10) 0.0625(11) -0.0082(8) 0.0173(9) -0.0054(8) O10 0.0821(13) 0.0393(9) 0.0653(11) 0.0108(8) 0.0094(9) -0.0251(9) O11 0.168(3) 0.0460(12) 0.0868(17) 0.0197(11) 0.0149(17) -0.0275(15) O12 0.1107(19) 0.0351(11) 0.160(3) 0.0107(13) 0.0542(18) 0.0045(11) O13 0.0853(14) 0.0979(17) 0.0748(13) 0.0440(12) -0.0119(12) -0.0488(13) O14 0.1038(16) 0.0315(9) 0.0876(15) 0.0072(9) 0.0462(13) -0.0137(10) O15 0.0401(9) 0.0760(13) 0.0830(14) -0.0044(10) 0.0041(9) -0.0169(9) O16 0.0704(12) 0.0895(15) 0.0382(9) -0.0077(9) 0.0034(8) -0.0232(10) C7 0.0565(13) 0.0460(13) 0.0401(11) 0.0017(9) 0.0081(10) -0.0129(10) N2A 0.0506(11) 0.0409(10) 0.0467(10) 0.0030(8) 0.0033(8) -0.0153(8) O16A 0.248(4) 0.085(2) 0.141(3) 0.0420(19) 0.148(3) 0.032(2) C16 0.0398(10) 0.0333(10) 0.0384(10) 0.0030(8) 0.0019(8) -0.0093(8) N4 0.0403(9) 0.0321(8) 0.0378(9) 0.0031(7) 0.0024(7) -0.0098(7) N3 0.0532(11) 0.0307(9) 0.0485(10) 0.0049(7) -0.0035(8) -0.0100(8) N7 0.0509(10) 0.0277(8) 0.0437(10) 0.0002(7) 0.0037(8) -0.0106(7) N8 0.0453(10) 0.0287(8) 0.0485(10) 0.0021(7) 0.0018(8) -0.0070(7) C20 0.0469(12) 0.0337(11) 0.0484(12) 0.0013(9) 0.0058(10) -0.0094(9) N10 0.0511(10) 0.0431(10) 0.0393(9) 0.0017(8) 0.0059(8) -0.0160(8) N11 0.0884(17) 0.0605(15) 0.0498(12) 0.0197(10) -0.0122(12) -0.0362(13) N12 0.0430(10) 0.0278(8) 0.0440(10) -0.0032(7) 0.0054(7) -0.0070(7) C1 0.0424(11) 0.0398(11) 0.0349(10) 0.0027(8) -0.0023(8) -0.0111(9) C2 0.0559(13) 0.0423(12) 0.0465(12) 0.0098(9) -0.0013(10) -0.0123(10) C3 0.0508(13) 0.0357(11) 0.0621(14) 0.0023(10) -0.0093(11) -0.0054(10) C4 0.0354(10) 0.0471(12) 0.0538(13) -0.0074(10) -0.0020(9) -0.0052(9) N1 0.0462(12) 0.0590(15) 0.0801(17) -0.0187(12) 0.0053(11) -0.0018(10) C6 0.0389(10) 0.0375(11) 0.0399(10) 0.0024(8) -0.0027(8) -0.0114(8) C5 0.0415(11) 0.0471(12) 0.0475(12) 0.0005(10) 0.0053(9) -0.0123(9) C8 0.0577(14) 0.0418(12) 0.0548(13) 0.0101(10) 0.0031(11) -0.0176(11) N2 0.0601(12) 0.0405(10) 0.0512(11) 0.0054(8) 0.0187(9) -0.0124(9) C10 0.0464(11) 0.0346(10) 0.0440(11) 0.0029(8) 0.0064(9) -0.0114(9) C11 0.0474(12) 0.0424(12) 0.0419(11) 0.0056(9) 0.0080(9) -0.0126(9) C12 0.0427(11) 0.0346(10) 0.0427(11) 0.0027(8) -0.0032(9) -0.0068(8) C13 0.0493(12) 0.0313(10) 0.0469(12) 0.0031(9) 0.0049(9) -0.0101(9) C14 0.113(3) 0.0597(18) 0.072(2) 0.0062(15) 0.0515(19) -0.0133(17) C15 0.0806(18) 0.0324(12) 0.0697(17) 0.0069(11) -0.0119(14) -0.0090(12) C16A 0.0508(12) 0.0412(12) 0.0420(11) -0.0027(9) 0.0017(9) -0.0126(10) C17 0.0428(11) 0.0315(10) 0.0379(10) 0.0014(8) -0.0010(8) -0.0122(8) C18 0.0448(11) 0.0294(10) 0.0411(10) 0.0028(8) -0.0019(8) -0.0105(8) C19 0.0619(15) 0.0287(11) 0.0721(16) 0.0027(10) 0.0039(12) -0.0056(10) N9 0.0493(10) 0.0323(9) 0.0457(10) 0.0027(7) 0.0050(8) -0.0127(8) C21 0.0523(12) 0.0370(11) 0.0437(11) 0.0052(9) -0.0012(9) -0.0166(9) C22 0.0724(17) 0.0705(18) 0.0479(14) 0.0031(12) 0.0149(12) -0.0289(14) C23 0.0668(15) 0.0283(10) 0.0618(15) 0.0015(10) 0.0054(12) -0.0113(10) C24 0.0622(14) 0.0446(12) 0.0387(11) 0.0088(9) -0.0080(10) -0.0247(11) C25 0.0571(14) 0.0565(14) 0.0373(11) -0.0014(10) 0.0074(10) -0.0232(11) C26 0.0535(13) 0.0405(12) 0.0459(12) -0.0086(9) 0.0102(10) -0.0111(10) C27 0.0438(11) 0.0303(10) 0.0403(10) -0.0029(8) 0.0014(8) -0.0101(8) C28 0.0565(13) 0.0279(10) 0.0545(13) -0.0032(9) 0.0042(10) -0.0096(9) C29 0.0539(12) 0.0309(10) 0.0425(11) 0.0020(8) -0.0043(9) -0.0098(9) C30 0.0386(10) 0.0317(10) 0.0337(9) -0.0008(7) -0.0006(8) -0.0093(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.209(3) . ? O2 N1 1.217(3) . ? O3 N2A 1.194(3) . ? O4 N2A 1.196(3) . ? O5 C7 1.229(3) . ? O5 H5A 0.89(5) . ? O6 C8 1.210(3) . ? O7 C12 1.219(3) . ? N5 C13 1.331(3) . ? N5 C10 1.357(3) . ? O9 C16A 1.212(3) . ? O10 C21 1.216(3) . ? O11 N11 1.201(3) . ? O12 C28 1.179(3) . ? O13 N11 1.209(3) . ? O14 C28 1.266(3) . ? O14 H14 0.83(4) . ? O15 N12 1.201(3) . ? O16 N12 1.209(3) . ? C7 O16A 1.138(3) . ? C7 C1 1.498(3) . ? N2A C6 1.474(3) . ? C16 C10 1.358(3) . ? C16 N4 1.380(3) . ? C16 C12 1.422(3) . ? N4 C13 1.328(3) . ? N4 C11 1.458(3) . ? N3 C8 1.395(3) . ? N3 C12 1.397(3) . ? N3 C15 1.469(3) . ? N7 C17 1.366(3) . ? N7 C16A 1.375(3) . ? N7 C23 1.462(3) . ? N8 C20 1.333(3) . ? N8 C18 1.379(3) . ? N8 C19 1.465(3) . ? C20 N9 1.333(3) . ? C20 H20 0.99(3) . ? N10 C16A 1.397(3) . ? N10 C21 1.403(3) . ? N10 C22 1.474(3) . ? N11 C24 1.479(3) . ? N12 C30 1.470(2) . ? C1 C2 1.386(3) . ? C1 C6 1.391(3) . ? C2 C3 1.375(3) . ? C2 H2 0.9300 . ? C3 C4 1.370(3) . ? C3 H3 0.9300 . ? C4 C5 1.372(3) . ? C4 N1 1.472(3) . ? C6 C5 1.371(3) . ? C5 H5 0.9300 . ? C8 N2 1.378(3) . ? N2 C10 1.368(3) . ? N2 C14 1.467(3) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C13 H13 0.94(3) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C17 C18 1.357(3) . ? C17 N9 1.359(3) . ? C18 C21 1.425(3) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C25 1.367(3) . ? C24 C29 1.376(3) . ? C25 C26 1.378(3) . ? C25 H25 0.9300 . ? C26 C27 1.388(3) . ? C26 H26 0.9300 . ? C27 C30 1.389(3) . ? C27 C28 1.500(3) . ? C29 C30 1.374(3) . ? C29 H29 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O5 H5A 115(3) . . ? C13 N5 C10 103.96(18) . . ? C28 O14 H14 116(3) . . ? O16A C7 O5 121.9(3) . . ? O16A C7 C1 122.9(3) . . ? O5 C7 C1 115.1(2) . . ? O3 N2A O4 124.5(2) . . ? O3 N2A C6 117.8(2) . . ? O4 N2A C6 117.5(2) . . ? C10 C16 N4 105.41(17) . . ? C10 C16 C12 122.72(19) . . ? N4 C16 C12 131.87(18) . . ? C13 N4 C16 106.43(17) . . ? C13 N4 C11 126.43(18) . . ? C16 N4 C11 126.94(17) . . ? C8 N3 C12 126.77(18) . . ? C8 N3 C15 116.87(19) . . ? C12 N3 C15 116.33(19) . . ? C17 N7 C16A 119.50(18) . . ? C17 N7 C23 120.54(18) . . ? C16A N7 C23 119.96(18) . . ? C20 N8 C18 106.38(17) . . ? C20 N8 C19 126.24(19) . . ? C18 N8 C19 127.39(18) . . ? N9 C20 N8 112.98(19) . . ? N9 C20 H20 122.1(15) . . ? N8 C20 H20 124.9(15) . . ? C16A N10 C21 126.59(18) . . ? C16A N10 C22 117.2(2) . . ? C21 N10 C22 116.2(2) . . ? O11 N11 O13 123.8(2) . . ? O11 N11 C24 118.3(2) . . ? O13 N11 C24 117.9(3) . . ? O15 N12 O16 124.4(2) . . ? O15 N12 C30 118.44(19) . . ? O16 N12 C30 117.07(18) . . ? C2 C1 C6 117.1(2) . . ? C2 C1 C7 118.31(19) . . ? C6 C1 C7 124.52(19) . . ? C3 C2 C1 121.6(2) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C4 C3 C2 118.3(2) . . ? C4 C3 H3 120.8 . . ? C2 C3 H3 120.8 . . ? C3 C4 C5 122.9(2) . . ? C3 C4 N1 119.0(2) . . ? C5 C4 N1 118.1(2) . . ? O1 N1 O2 124.3(2) . . ? O1 N1 C4 117.9(3) . . ? O2 N1 C4 117.8(2) . . ? C5 C6 C1 122.9(2) . . ? C5 C6 N2A 115.93(18) . . ? C1 C6 N2A 121.17(18) . . ? C6 C5 C4 117.1(2) . . ? C6 C5 H5 121.5 . . ? C4 C5 H5 121.5 . . ? O6 C8 N2 121.4(2) . . ? O6 C8 N3 121.6(2) . . ? N2 C8 N3 117.04(19) . . ? C10 N2 C8 119.24(19) . . ? C10 N2 C14 121.0(2) . . ? C8 N2 C14 119.6(2) . . ? C16 C10 N5 111.21(18) . . ? C16 C10 N2 122.4(2) . . ? N5 C10 N2 126.4(2) . . ? N4 C11 H11A 109.5 . . ? N4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O7 C12 N3 121.4(2) . . ? O7 C12 C16 126.8(2) . . ? N3 C12 C16 111.82(18) . . ? N4 C13 N5 112.99(19) . . ? N4 C13 H13 122.4(16) . . ? N5 C13 H13 124.7(16) . . ? N2 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N3 C15 H15A 109.5 . . ? N3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O9 C16A N7 121.5(2) . . ? O9 C16A N10 121.5(2) . . ? N7 C16A N10 117.02(19) . . ? C18 C17 N9 111.41(18) . . ? C18 C17 N7 122.38(18) . . ? N9 C17 N7 126.20(18) . . ? C17 C18 N8 105.50(17) . . ? C17 C18 C21 122.74(19) . . ? N8 C18 C21 131.76(19) . . ? N8 C19 H19A 109.5 . . ? N8 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N8 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C20 N9 C17 103.73(17) . . ? O10 C21 N10 121.3(2) . . ? O10 C21 C18 127.0(2) . . ? N10 C21 C18 111.68(18) . . ? N10 C22 H22A 109.5 . . ? N10 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N10 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N7 C23 H23A 109.5 . . ? N7 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N7 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C29 123.1(2) . . ? C25 C24 N11 119.1(2) . . ? C29 C24 N11 117.8(2) . . ? C24 C25 C26 118.6(2) . . ? C24 C25 H25 120.7 . . ? C26 C25 H25 120.7 . . ? C25 C26 C27 121.3(2) . . ? C25 C26 H26 119.4 . . ? C27 C26 H26 119.4 . . ? C30 C27 C26 117.18(19) . . ? C30 C27 C28 124.62(18) . . ? C26 C27 C28 118.20(19) . . ? O12 C28 O14 123.1(2) . . ? O12 C28 C27 123.0(2) . . ? O14 C28 C27 113.75(19) . . ? C30 C29 C24 116.6(2) . . ? C30 C29 H29 121.7 . . ? C24 C29 H29 121.7 . . ? C29 C30 C27 123.26(19) . . ? C29 C30 N12 115.41(17) . . ? C27 C30 N12 121.22(17) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.766 _refine_diff_density_min -0.620 _refine_diff_density_rms 0.053 #END# data_cmr_sg_085_1 _database_code_depnum_ccdc_archive 'CCDC 860129' #TrackingRef 'ALL CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Caffeine:2-fluoro-5nitroaniline _chemical_melting_point 413.59 _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 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _symmetry_space_group_name_Hall -P2ybc 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' _cell_length_a 5.8784(5) _cell_length_b 33.258(3) _cell_length_c 8.0008(7) _cell_angle_alpha 90.00 _cell_angle_beta 92.806(2) _cell_angle_gamma 90.00 _cell_volume 1562.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7710 _cell_measurement_theta_min 3.14 _cell_measurement_theta_max 32.25 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.941 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details 'multi-scan absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER KAPPA APEX II DUO' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12814 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -40 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3384 _reflns_number_gt 2911 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0452P)^2^+1.1664P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3384 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0673 _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.1458 _refine_ls_wR_factor_gt 0.1406 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.134 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group 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_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0629(10) 0.0450(8) 0.0875(11) -0.0080(7) -0.0307(8) -0.0087(7) O1 0.0649(11) 0.0305(8) 0.0783(13) -0.0007(8) -0.0019(9) 0.0080(8) O2 0.0477(10) 0.0525(10) 0.0622(11) -0.0034(8) -0.0194(8) 0.0050(8) O3 0.1026(19) 0.0397(11) 0.162(3) -0.0193(13) -0.0441(18) 0.0178(12) N6 0.0566(14) 0.0354(11) 0.0808(16) -0.0075(11) -0.0269(12) 0.0018(10) N1 0.0402(10) 0.0303(9) 0.0492(11) -0.0058(7) -0.0039(8) -0.0043(7) N2 0.0483(11) 0.0287(9) 0.0515(11) -0.0022(8) 0.0019(8) 0.0014(8) N3 0.0450(11) 0.0432(11) 0.0580(12) -0.0097(9) -0.0056(9) -0.0093(9) N4 0.0378(10) 0.0339(9) 0.0494(11) 0.0024(8) -0.0055(8) 0.0021(7) C10 0.0437(12) 0.0384(11) 0.0484(13) -0.0026(10) -0.0086(10) -0.0071(9) C9 0.0384(11) 0.0363(11) 0.0428(11) 0.0000(9) -0.0044(9) -0.0015(9) C1 0.0433(12) 0.0313(10) 0.0470(12) 0.0034(9) 0.0037(9) -0.0003(9) C2 0.0374(11) 0.0358(11) 0.0395(11) 0.0005(8) -0.0015(9) -0.0008(9) C3 0.0391(11) 0.0282(10) 0.0414(11) -0.0010(8) -0.0009(9) 0.0008(8) C4 0.0611(16) 0.0398(13) 0.086(2) 0.0029(13) 0.0022(14) 0.0142(12) C5 0.0626(16) 0.0420(13) 0.0664(17) -0.0146(12) -0.0086(13) -0.0123(12) C6 0.0503(14) 0.0361(12) 0.0639(16) -0.0100(11) 0.0002(11) -0.0095(10) C7 0.0367(11) 0.0330(10) 0.0407(11) -0.0003(8) 0.0000(8) -0.0038(8) C8 0.0456(13) 0.0568(15) 0.0627(16) 0.0091(12) -0.0118(11) 0.0098(12) C11 0.0402(12) 0.0526(14) 0.0563(14) 0.0014(11) -0.0124(10) 0.0014(10) C12 0.0499(14) 0.0450(13) 0.0629(15) 0.0005(11) -0.0077(11) 0.0111(11) C13 0.0506(13) 0.0365(12) 0.0522(13) -0.0040(10) -0.0029(10) 0.0000(10) N5 0.0715(16) 0.0366(11) 0.0815(17) -0.0080(11) -0.0143(13) 0.0020(11) O4 0.1025(18) 0.0472(12) 0.147(2) -0.0231(13) -0.0610(18) -0.0007(12) C14 0.0408(12) 0.0397(12) 0.0471(12) -0.0032(9) -0.0078(9) -0.0031(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag 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 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag 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 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.238 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.043 #END# data_cmr_sg_087_1 _database_code_depnum_ccdc_archive 'CCDC 860130' #TrackingRef 'ALL CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Caffeine:2-fluoro-5-nitrobenzoicacid _chemical_melting_point 457 _chemical_formula_moiety 'C8 H10 N4 O2, C7 H4 F N O4' _chemical_formula_sum 'C15 H14 F N5 O6' _chemical_formula_weight 379.31 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _symmetry_space_group_name_Hall -P2ybc 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' _cell_length_a 12.5652(6) _cell_length_b 8.1475(4) _cell_length_c 16.5266(8) _cell_angle_alpha 90.00 _cell_angle_beta 93.688(2) _cell_angle_gamma 90.00 _cell_volume 1688.41(14) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6615 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 27.03 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.950 _exptl_absorpt_correction_T_max 0.960 _exptl_absorpt_process_details 'multi-scan absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER KAPPA APEX II DUO' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 14412 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0208 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3678 _reflns_number_gt 2902 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0735P)^2^+0.5055P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3678 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0582 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1417 _refine_ls_wR_factor_gt 0.1274 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.001 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 _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.13483(12) 0.15032(19) -0.06283(7) 0.0851(4) Uani 1 1 d . . . O1 O 0.45069(12) 0.07193(18) 0.71639(7) 0.0637(4) Uani 1 1 d . . . N4 N 0.53736(11) 0.30441(18) 0.46956(8) 0.0483(3) Uani 1 1 d . . . O2 O 0.23297(11) -0.0058(2) 0.48794(8) 0.0694(4) Uani 1 1 d . . . O6 O 0.27617(12) -0.0412(2) 0.01339(9) 0.0697(4) Uani 1 1 d . . . O4 O -0.0030(2) 0.1722(5) 0.28933(14) 0.1566(13) Uani 1 1 d . . . O5 O 0.31170(11) 0.0248(2) 0.14215(9) 0.0759(5) Uani 1 1 d . . . N1 N 0.50174(11) 0.19122(17) 0.60134(8) 0.0434(3) Uani 1 1 d . . . N3 N 0.39288(11) 0.20731(17) 0.40063(8) 0.0465(3) Uani 1 1 d . . . C5 C 0.48232(14) 0.2946(2) 0.39801(10) 0.0497(4) Uani 1 1 d . . . N2 N 0.34102(11) 0.03971(17) 0.60241(8) 0.0464(3) Uani 1 1 d . . . O3 O -0.13663(15) 0.2873(3) 0.22830(15) 0.1120(7) Uani 1 1 d . . . C1 C 0.43258(14) 0.1002(2) 0.64451(9) 0.0455(4) Uani 1 1 d . . . C4 C 0.47765(12) 0.21831(18) 0.52018(9) 0.0391(3) Uani 1 1 d . . . C3 C 0.38797(13) 0.15656(19) 0.48042(9) 0.0405(3) Uani 1 1 d . . . C6 C 0.31413(17) 0.1761(3) 0.33315(10) 0.0644(5) Uani 1 1 d . . . H6A H 0.2754 0.2752 0.3201 0.097 Uiso 1 1 calc R . . H6B H 0.2655 0.0925 0.3484 0.097 Uiso 1 1 calc R . . H6C H 0.3499 0.1403 0.2867 0.097 Uiso 1 1 calc R . . C7 C 0.59684(16) 0.2630(3) 0.64316(12) 0.0637(5) Uani 1 1 d . . . H7A H 0.6552 0.2579 0.6085 0.096 Uiso 1 1 calc R . . H7B H 0.6147 0.2028 0.6921 0.096 Uiso 1 1 calc R . . H7C H 0.5829 0.3754 0.6563 0.096 Uiso 1 1 calc R . . C2 C 0.31315(14) 0.0582(2) 0.51934(10) 0.0456(4) Uani 1 1 d . . . C8 C 0.26796(18) -0.0566(3) 0.64993(13) 0.0670(5) Uani 1 1 d . . . H8A H 0.2929 -0.1679 0.6544 0.100 Uiso 1 1 calc R . . H8B H 0.1978 -0.0550 0.6233 0.100 Uiso 1 1 calc R . . H8C H 0.2656 -0.0098 0.7031 0.100 Uiso 1 1 calc R . . N5 N -0.04918(17) 0.2246(3) 0.22909(15) 0.0877(6) Uani 1 1 d . . . C15 C 0.00211(15) 0.2095(3) 0.15179(13) 0.0606(5) Uani 1 1 d . . . C16 C 0.10009(14) 0.1332(2) 0.15148(11) 0.0542(4) Uani 1 1 d . . . H16 H 0.1342 0.0966 0.1998 0.065 Uiso 1 1 calc R . . C11 C 0.14742(13) 0.1114(2) 0.07885(10) 0.0473(4) Uani 1 1 d . . . C10 C 0.25401(13) 0.0274(2) 0.08171(11) 0.0492(4) Uani 1 1 d . . . C12 C 0.09287(15) 0.1692(2) 0.00898(12) 0.0570(4) Uani 1 1 d . . . C13 C -0.00359(17) 0.2493(3) 0.01003(14) 0.0715(6) Uani 1 1 d . . . H13 H -0.0367 0.2897 -0.0378 0.086 Uiso 1 1 calc R . . C14 C -0.05014(16) 0.2689(3) 0.08153(15) 0.0713(6) Uani 1 1 d . . . H14 H -0.1157 0.3213 0.0831 0.086 Uiso 1 1 calc R . . H5 H 0.5072(16) 0.341(2) 0.3479(12) 0.059(5) Uiso 1 1 d . . . H6 H 0.348(3) -0.093(4) 0.0185(17) 0.111(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0905(9) 0.1097(11) 0.0551(7) 0.0147(7) 0.0057(6) 0.0195(8) O1 0.0806(9) 0.0781(9) 0.0321(6) 0.0034(6) -0.0001(6) -0.0033(7) N4 0.0465(7) 0.0538(8) 0.0451(7) 0.0026(6) 0.0075(6) -0.0013(6) O2 0.0663(8) 0.0800(9) 0.0600(8) 0.0036(7) -0.0099(7) -0.0285(7) O6 0.0594(8) 0.0866(10) 0.0624(8) -0.0174(7) -0.0020(7) 0.0218(7) O4 0.1071(17) 0.294(4) 0.0712(13) -0.0132(18) 0.0232(12) 0.059(2) O5 0.0552(8) 0.1125(12) 0.0584(8) -0.0148(8) -0.0086(6) 0.0271(8) N1 0.0460(7) 0.0502(7) 0.0337(6) -0.0050(5) -0.0005(5) -0.0003(6) N3 0.0537(8) 0.0527(8) 0.0329(7) 0.0001(5) 0.0014(6) 0.0035(6) C5 0.0535(9) 0.0557(9) 0.0408(8) 0.0048(7) 0.0100(7) 0.0030(8) N2 0.0531(8) 0.0491(7) 0.0376(7) 0.0016(5) 0.0065(6) -0.0050(6) O3 0.0713(11) 0.1287(17) 0.1413(18) -0.0026(14) 0.0482(11) 0.0225(11) C1 0.0554(9) 0.0479(8) 0.0333(8) -0.0052(6) 0.0032(6) 0.0049(7) C4 0.0413(8) 0.0411(7) 0.0350(7) -0.0035(6) 0.0040(6) 0.0034(6) C3 0.0470(8) 0.0433(8) 0.0311(7) -0.0023(6) 0.0014(6) 0.0015(6) C6 0.0718(12) 0.0823(14) 0.0372(9) 0.0021(8) -0.0104(8) -0.0037(10) C7 0.0628(11) 0.0747(13) 0.0517(10) -0.0061(9) -0.0121(8) -0.0120(10) C2 0.0489(9) 0.0458(8) 0.0414(8) -0.0023(6) -0.0007(7) -0.0029(7) C8 0.0717(13) 0.0739(13) 0.0565(11) 0.0098(9) 0.0140(9) -0.0161(10) N5 0.0625(11) 0.1184(18) 0.0839(14) -0.0131(12) 0.0185(10) 0.0105(12) C15 0.0450(9) 0.0662(11) 0.0712(12) -0.0072(9) 0.0080(8) 0.0022(8) C16 0.0448(9) 0.0624(11) 0.0548(10) -0.0017(8) -0.0015(7) 0.0041(8) C11 0.0416(8) 0.0467(8) 0.0531(9) -0.0003(7) -0.0005(7) 0.0006(7) C10 0.0441(8) 0.0520(9) 0.0514(9) -0.0028(7) 0.0023(7) 0.0015(7) C12 0.0564(10) 0.0593(10) 0.0548(10) 0.0055(8) 0.0008(8) 0.0015(8) C13 0.0604(12) 0.0770(14) 0.0753(14) 0.0181(11) -0.0095(10) 0.0119(10) C14 0.0464(10) 0.0701(13) 0.0967(17) 0.0078(11) -0.0004(10) 0.0151(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C12 1.338(2) . ? O1 C1 1.2169(19) . ? N4 C5 1.333(2) . ? N4 C4 1.355(2) . ? O2 C2 1.220(2) . ? O6 C10 1.306(2) . ? O6 H6 0.99(3) . ? O4 N5 1.198(3) . ? O5 C10 1.196(2) . ? N1 C4 1.3738(19) . ? N1 C1 1.376(2) . ? N1 C7 1.463(2) . ? N3 C5 1.333(2) . ? N3 C3 1.3872(19) . ? N3 C6 1.465(2) . ? C5 H5 0.98(2) . ? N2 C1 1.396(2) . ? N2 C2 1.403(2) . ? N2 C8 1.473(2) . ? O3 N5 1.211(3) . ? C4 C3 1.364(2) . ? C3 C2 1.420(2) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? N5 C15 1.473(3) . ? C15 C16 1.379(3) . ? C15 C14 1.384(3) . ? C16 C11 1.385(3) . ? C16 H16 0.9300 . ? C11 C12 1.387(2) . ? C11 C10 1.502(2) . ? C12 C13 1.377(3) . ? C13 C14 1.361(3) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N4 C4 103.91(14) . . ? C10 O6 H6 110.5(17) . . ? C4 N1 C1 119.07(13) . . ? C4 N1 C7 121.26(14) . . ? C1 N1 C7 119.61(14) . . ? C5 N3 C3 106.21(13) . . ? C5 N3 C6 126.69(15) . . ? C3 N3 C6 127.08(15) . . ? N3 C5 N4 113.17(15) . . ? N3 C5 H5 123.3(12) . . ? N4 C5 H5 123.4(12) . . ? C1 N2 C2 126.58(14) . . ? C1 N2 C8 116.38(14) . . ? C2 N2 C8 117.02(15) . . ? O1 C1 N1 121.55(16) . . ? O1 C1 N2 121.09(16) . . ? N1 C1 N2 117.36(13) . . ? N4 C4 C3 111.52(13) . . ? N4 C4 N1 126.17(14) . . ? C3 C4 N1 122.31(14) . . ? C4 C3 N3 105.19(14) . . ? C4 C3 C2 122.72(14) . . ? N3 C3 C2 132.06(14) . . ? N3 C6 H6A 109.5 . . ? N3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O2 C2 N2 121.17(16) . . ? O2 C2 C3 126.95(15) . . ? N2 C2 C3 111.89(13) . . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O4 N5 O3 123.3(2) . . ? O4 N5 C15 118.4(2) . . ? O3 N5 C15 118.3(2) . . ? C16 C15 C14 122.0(2) . . ? C16 C15 N5 118.78(19) . . ? C14 C15 N5 119.21(19) . . ? C15 C16 C11 119.61(17) . . ? C15 C16 H16 120.2 . . ? C11 C16 H16 120.2 . . ? C16 C11 C12 117.48(16) . . ? C16 C11 C10 117.57(15) . . ? C12 C11 C10 124.96(16) . . ? O5 C10 O6 124.27(17) . . ? O5 C10 C11 121.71(16) . . ? O6 C10 C11 114.02(15) . . ? F1 C12 C13 117.57(17) . . ? F1 C12 C11 119.84(17) . . ? C13 C12 C11 122.58(19) . . ? C14 C13 C12 119.62(19) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C13 C14 C15 118.68(18) . . ? C13 C14 H14 120.7 . . ? C15 C14 H14 120.7 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.247 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.039 #END#