# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Joel Bernstein' _publ_contact_author_email YOEL@BGU.AC.IL _publ_section_title ; The study of polymorphic system of 2-chloro-4-nitrobenzoic acid ; loop_ _publ_author_name 'Joel Bernstein' 'Inna Barsky' 'Peter W Stephens' 'Kevin H. Stone' #============================================================================== # Additional structures (sections 5-10 and associated data_? identifiers) # may be added at this point. #============================================================================== # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set. # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ #============================================================================== # Attachment 'mod1.cif' data_2c4nf21 _database_code_depnum_ccdc_archive 'CCDC 698967' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H4 Cl N O4' _chemical_formula_weight 201.56 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 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 10.833(3) _cell_length_b 5.8573(14) _cell_length_c 13.497(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.734(4) _cell_angle_gamma 90.00 _cell_volume 824.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prizm _exptl_crystal_colour 'pale yello' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.624 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.442 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4950 _diffrn_reflns_av_R_equivalents 0.0152 _diffrn_reflns_av_sigmaI/netI 0.0139 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 28.30 _reflns_number_total 1902 _reflns_number_gt 1558 _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^)+(0.0658P)^2^+0.3377P] 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 1902 _refine_ls_number_parameters 122 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0556 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1408 _refine_ls_wR_factor_gt 0.1321 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.000 _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 0.88711(7) 0.15940(12) 0.27789(5) 0.0776(3) Uani 1 1 d . . . N1 N 0.56585(19) 0.8231(3) 0.18466(16) 0.0596(5) Uani 1 1 d . . . C1 C 0.80413(19) 0.3522(3) 0.08864(15) 0.0483(5) Uani 1 1 d . . . C2 C 0.79916(19) 0.3554(3) 0.19081(15) 0.0479(4) Uani 1 1 d . . . C3 C 0.72099(19) 0.5091(4) 0.22292(14) 0.0490(5) Uani 1 1 d . . . H3 H 0.7176 0.5127 0.2910 0.059 Uiso 1 1 calc . . . C4 C 0.64840(19) 0.6567(3) 0.15082(15) 0.0486(5) Uani 1 1 d . . . C5 C 0.6482(2) 0.6550(4) 0.04862(17) 0.0630(6) Uani 1 1 d . . . H5 H 0.5963 0.7542 0.0014 0.076 Uiso 1 1 calc . . . C6 C 0.7282(2) 0.5003(5) 0.01854(16) 0.0633(6) Uani 1 1 d . . . H6 H 0.7305 0.4965 -0.0498 0.076 Uiso 1 1 calc . . . C7 C 0.89119(19) 0.1926(4) 0.05196(15) 0.0502(5) Uani 1 1 d . . . O1 O 0.84301(16) 0.0366(4) -0.00729(16) 0.0827(6) Uani 1 1 d . . . O2 O 1.00851(17) 0.2340(4) 0.0796(2) 0.1024(9) Uani 1 1 d . . . O3 O 0.4766(2) 0.9056(5) 0.11826(16) 0.1000(8) Uani 1 1 d . . . O4 O 0.58769(19) 0.8645(3) 0.27604(14) 0.0734(5) Uani 1 1 d . . . H4 H 1.068(6) 0.115(11) 0.054(5) 0.23(3) 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 0.0854(5) 0.0862(5) 0.0670(4) 0.0271(3) 0.0307(3) 0.0384(3) N1 0.0614(11) 0.0592(11) 0.0619(11) 0.0031(8) 0.0230(9) 0.0142(9) C1 0.0476(10) 0.0530(11) 0.0457(10) -0.0039(8) 0.0152(8) 0.0025(8) C2 0.0470(10) 0.0518(11) 0.0464(10) 0.0060(8) 0.0153(8) 0.0056(8) C3 0.0491(10) 0.0579(12) 0.0430(10) 0.0023(8) 0.0177(8) 0.0048(9) C4 0.0477(10) 0.0512(11) 0.0496(10) -0.0003(8) 0.0179(8) 0.0053(8) C5 0.0697(14) 0.0722(15) 0.0481(11) 0.0116(10) 0.0173(10) 0.0222(11) C6 0.0705(14) 0.0810(16) 0.0400(10) 0.0023(10) 0.0181(9) 0.0189(12) C7 0.0493(10) 0.0579(11) 0.0446(10) -0.0063(8) 0.0147(8) 0.0020(9) O1 0.0582(10) 0.0825(13) 0.1093(16) -0.0441(11) 0.0257(10) -0.0061(9) O2 0.0503(9) 0.1108(17) 0.145(2) -0.0757(16) 0.0236(11) -0.0047(10) O3 0.1037(15) 0.1203(17) 0.0777(13) 0.0159(12) 0.0275(11) 0.0654(14) O4 0.0812(12) 0.0795(12) 0.0634(10) -0.0149(9) 0.0260(9) 0.0144(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 Cl1 C2 1.732(2) . ? N1 O4 1.216(3) . ? N1 O3 1.226(3) . ? N1 C4 1.477(3) . ? C1 C6 1.379(3) . ? C1 C2 1.395(3) . ? C1 C7 1.504(3) . ? C2 C3 1.384(3) . ? C3 C4 1.378(3) . ? C4 C5 1.379(3) . ? C5 C6 1.388(3) . ? C7 O1 1.233(3) . ? C7 O2 1.247(3) . ? 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 O4 N1 O3 124.1(2) . . ? O4 N1 C4 118.54(18) . . ? O3 N1 C4 117.3(2) . . ? C6 C1 C2 119.60(18) . . ? C6 C1 C7 118.42(18) . . ? C2 C1 C7 121.97(18) . . ? C3 C2 C1 120.62(18) . . ? C3 C2 Cl1 119.31(15) . . ? C1 C2 Cl1 120.04(15) . . ? C4 C3 C2 117.88(17) . . ? C3 C4 C5 123.23(18) . . ? C3 C4 N1 118.25(18) . . ? C5 C4 N1 118.51(18) . . ? C4 C5 C6 117.74(19) . . ? C1 C6 C5 120.90(19) . . ? O1 C7 O2 123.8(2) . . ? O1 C7 C1 118.77(18) . . ? O2 C7 C1 117.35(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.5(3) . . . . ? C7 C1 C2 C3 177.99(19) . . . . ? C6 C1 C2 Cl1 176.30(19) . . . . ? C7 C1 C2 Cl1 -4.2(3) . . . . ? C1 C2 C3 C4 0.3(3) . . . . ? Cl1 C2 C3 C4 -177.46(16) . . . . ? C2 C3 C4 C5 1.3(3) . . . . ? C2 C3 C4 N1 -179.30(19) . . . . ? O4 N1 C4 C3 18.3(3) . . . . ? O3 N1 C4 C3 -159.5(2) . . . . ? O4 N1 C4 C5 -162.3(2) . . . . ? O3 N1 C4 C5 19.9(3) . . . . ? C3 C4 C5 C6 -1.8(4) . . . . ? N1 C4 C5 C6 178.8(2) . . . . ? C2 C1 C6 C5 1.0(4) . . . . ? C7 C1 C6 C5 -178.5(2) . . . . ? C4 C5 C6 C1 0.6(4) . . . . ? C6 C1 C7 O1 -68.9(3) . . . . ? C2 C1 C7 O1 111.6(3) . . . . ? C6 C1 C7 O2 107.5(3) . . . . ? C2 C1 C7 O2 -72.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.931 _refine_diff_density_max 0.379 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.045 # Attachment 'mod2.cif' data_2c4nm11 _database_code_depnum_ccdc_archive 'CCDC 698968' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H4 Cl N O4' _chemical_formula_weight 201.56 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 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 14.209(10) _cell_length_b 29.43(2) _cell_length_c 7.735(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.619(12) _cell_angle_gamma 90.00 _cell_volume 3228(4) _cell_formula_units_Z 16 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour 'pale yello' _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.659 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1632 _exptl_absorpt_coefficient_mu 0.451 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20196 _diffrn_reflns_av_R_equivalents 0.0635 _diffrn_reflns_av_sigmaI/netI 0.1548 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 28.38 _reflns_number_total 7495 _reflns_number_gt 2464 _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^)+(0.0517P)^2^+0.0000P] 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 7495 _refine_ls_number_parameters 476 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1707 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1226 _refine_ls_wR_factor_gt 0.1004 _refine_ls_goodness_of_fit_ref 0.758 _refine_ls_restrained_S_all 0.758 _refine_ls_shift/su_max 0.000 _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 Cl1A Cl 0.02662(7) 0.16501(3) 0.06300(15) 0.0779(4) Uani 1 1 d . . . Cl1B Cl 0.81603(7) 0.27079(3) 0.76745(14) 0.0736(3) Uani 1 1 d . . . Cl1D Cl 1.14712(6) 0.46488(3) 0.87661(14) 0.0725(3) Uani 1 1 d . . . Cl1C Cl 0.39441(7) 0.57540(3) 0.11325(14) 0.0725(3) Uani 1 1 d . . . O2C O 0.66457(17) 0.56632(8) 0.3961(3) 0.0588(7) Uani 1 1 d . . . O1D O 1.08525(16) 0.59673(7) 0.6496(3) 0.0601(7) Uani 1 1 d . . . O1A O 0.22430(16) 0.13770(8) 0.1106(3) 0.0669(8) Uani 1 1 d . . . O4D O 0.82387(17) 0.38926(8) 0.7231(3) 0.0756(9) Uani 1 1 d . . . O2D O 1.15019(19) 0.56384(8) 0.8870(4) 0.0791(9) Uani 1 1 d . . . H4D H 1.1882 0.5847 0.8810 0.119 Uiso 1 1 calc R . . O2A O 0.29880(19) 0.17056(8) 0.3423(3) 0.0749(8) Uani 1 1 d . . . H4A H 0.3342 0.1486 0.3373 0.112 Uiso 1 1 calc R . . O3D O 0.74110(18) 0.43534(8) 0.5586(4) 0.0840(9) Uani 1 1 d . . . C1C C 0.5407(2) 0.52461(10) 0.2565(4) 0.0416(9) Uani 1 1 d . . . N1C N 0.3753(3) 0.40512(11) 0.2217(4) 0.0603(9) Uani 1 1 d . . . O1B O 0.73686(18) 0.13621(9) 0.6036(4) 0.0899(10) Uani 1 1 d . . . N1D N 0.8106(2) 0.42571(11) 0.6553(4) 0.0585(9) Uani 1 1 d . . . C3B C 0.6379(3) 0.28751(11) 0.6575(5) 0.0548(10) Uani 1 1 d . . . H3B H 0.6535 0.3180 0.6718 0.066 Uiso 1 1 calc . . . C5C C 0.5245(2) 0.44391(11) 0.3074(5) 0.0554(10) Uani 1 1 d . . . H5C H 0.5497 0.4163 0.3458 0.067 Uiso 1 1 calc R . . C7D C 1.0891(2) 0.56570(11) 0.7547(5) 0.0486(10) Uani 1 1 d . . . O3C O 0.4162(2) 0.36906(9) 0.2253(4) 0.0827(9) Uani 1 1 d . . . C1A C 0.1828(2) 0.21270(10) 0.1850(4) 0.0413(9) Uani 1 1 d . . . C1D C 1.0203(2) 0.52752(10) 0.7367(4) 0.0429(9) Uani 1 1 d . . . O2B O 0.8075(2) 0.17173(9) 0.8275(4) 0.0867(9) Uani 1 1 d . . . H4B H 0.8431 0.1498 0.8261 0.130 Uiso 1 1 calc R . . C4A C 0.0923(2) 0.29414(10) 0.1185(4) 0.0462(9) Uani 1 1 d . . . C4C C 0.4330(2) 0.44692(11) 0.2381(4) 0.0464(9) Uani 1 1 d . . . O1C O 0.60217(17) 0.59319(8) 0.1437(3) 0.0681(8) Uani 1 1 d . . . C5A C 0.1826(2) 0.29492(11) 0.1918(4) 0.0503(10) Uani 1 1 d . . . H5A H 0.2131 0.3223 0.2177 0.060 Uiso 1 1 calc R . . C2C C 0.4482(2) 0.52604(10) 0.1872(4) 0.0430(9) Uani 1 1 d . . . C2D C 1.0386(2) 0.48263(11) 0.7899(4) 0.0464(9) Uani 1 1 d . . . C5D C 0.8626(2) 0.50530(11) 0.6333(4) 0.0525(10) Uani 1 1 d . . . H5D H 0.8037 0.5127 0.5819 0.063 Uiso 1 1 calc R . . C7C C 0.6046(2) 0.56538(12) 0.2599(5) 0.0489(10) Uani 1 1 d . . . C3D C 0.9688(2) 0.44960(10) 0.7646(4) 0.0497(10) Uani 1 1 d . . . H3D H 0.9800 0.4198 0.8002 0.060 Uiso 1 1 calc R . . C6A C 0.2266(2) 0.25405(11) 0.2257(4) 0.0496(10) Uani 1 1 d . . . H6A H 0.2875 0.2540 0.2774 0.059 Uiso 1 1 calc R . . O3A O 0.0844(2) 0.37194(9) 0.1009(4) 0.1026(11) Uani 1 1 d . . . N1A N 0.0430(2) 0.33711(10) 0.0766(4) 0.0641(9) Uani 1 1 d . . . C4D C 0.8829(2) 0.46192(11) 0.6857(4) 0.0467(9) Uani 1 1 d . . . C2A C 0.0900(2) 0.21381(10) 0.1123(4) 0.0429(9) Uani 1 1 d . . . C3A C 0.0444(2) 0.25448(11) 0.0803(4) 0.0464(9) Uani 1 1 d . . . H3A H -0.0175 0.2551 0.0336 0.056 Uiso 1 1 calc R . . O4C O 0.2909(2) 0.40958(9) 0.2014(4) 0.0860(10) Uani 1 1 d . . . C6C C 0.5774(2) 0.48313(11) 0.3178(5) 0.0561(10) Uani 1 1 d . . . H6C H 0.6388 0.4820 0.3668 0.067 Uiso 1 1 calc R . . C3C C 0.3937(2) 0.48707(11) 0.1810(4) 0.0480(9) Uani 1 1 d . . . H3C H 0.3310 0.4881 0.1386 0.058 Uiso 1 1 calc R . . C7A C 0.2365(2) 0.16965(12) 0.2103(5) 0.0516(10) Uani 1 1 d . . . N1B N 0.4770(3) 0.31047(13) 0.5641(5) 0.0766(11) Uani 1 1 d . . . C6D C 0.9318(2) 0.53782(11) 0.6588(4) 0.0511(10) Uani 1 1 d . . . H6D H 0.9192 0.5675 0.6229 0.061 Uiso 1 1 calc R . . O4A O -0.0390(2) 0.33542(9) 0.0228(4) 0.1042(11) Uani 1 1 d . . . C2B C 0.7048(2) 0.25365(11) 0.6952(4) 0.0494(9) Uani 1 1 d . . . C1B C 0.6803(2) 0.20820(11) 0.6692(4) 0.0475(9) Uani 1 1 d . . . C7B C 0.7453(2) 0.16889(12) 0.6995(5) 0.0557(10) Uani 1 1 d . . . O4B O 0.5016(2) 0.34895(11) 0.5881(4) 0.1171(13) Uani 1 1 d . . . C5B C 0.5216(2) 0.23077(14) 0.5746(5) 0.0627(11) Uani 1 1 d . . . H5B H 0.4601 0.2234 0.5364 0.075 Uiso 1 1 calc R . . C4B C 0.5488(3) 0.27475(13) 0.5987(5) 0.0560(10) Uani 1 1 d . . . C6B C 0.5881(2) 0.19774(12) 0.6088(5) 0.0599(11) Uani 1 1 d . . . H6B H 0.5715 0.1675 0.5912 0.072 Uiso 1 1 calc R . . O3B O 0.3982(2) 0.29865(10) 0.5085(4) 0.1039(11) Uani 1 1 d . . . H4C H 0.700(3) 0.5912(13) 0.393(5) 0.098(16) 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 Cl1A 0.0579(6) 0.0464(6) 0.1269(10) -0.0026(6) -0.0123(6) -0.0061(5) Cl1B 0.0589(6) 0.0631(6) 0.0964(9) -0.0017(6) -0.0123(6) -0.0064(5) Cl1D 0.0603(6) 0.0569(6) 0.0981(9) 0.0089(6) -0.0128(6) 0.0058(5) Cl1C 0.0678(7) 0.0564(6) 0.0920(8) 0.0072(6) -0.0057(6) 0.0062(5) O2C 0.0559(17) 0.0558(17) 0.0629(19) 0.0109(14) -0.0113(15) -0.0204(13) O1D 0.0752(18) 0.0434(14) 0.0605(18) 0.0130(13) -0.0060(14) -0.0106(12) O1A 0.0549(16) 0.0507(15) 0.093(2) -0.0158(15) -0.0125(15) 0.0156(13) O4D 0.080(2) 0.0500(17) 0.096(2) 0.0155(16) -0.0035(17) -0.0093(15) O2D 0.089(2) 0.0611(18) 0.083(2) 0.0205(15) -0.0269(18) -0.0255(14) O2A 0.090(2) 0.0695(19) 0.0622(18) -0.0054(15) -0.0181(17) 0.0350(15) O3D 0.0554(18) 0.078(2) 0.116(3) 0.0162(17) -0.0163(18) -0.0094(14) C1C 0.042(2) 0.042(2) 0.041(2) -0.0028(17) 0.0044(18) -0.0078(16) N1C 0.071(2) 0.059(2) 0.050(2) -0.0049(17) -0.001(2) -0.017(2) O1B 0.0736(19) 0.0595(17) 0.131(3) -0.0338(18) -0.0360(19) 0.0173(14) N1D 0.054(2) 0.053(2) 0.069(3) 0.0023(19) 0.0030(18) -0.0031(18) C3B 0.068(3) 0.043(2) 0.053(3) 0.0003(18) 0.002(2) 0.006(2) C5C 0.062(3) 0.043(2) 0.061(3) 0.0070(18) -0.004(2) -0.0066(19) C7D 0.054(2) 0.040(2) 0.051(3) -0.0008(19) 0.003(2) -0.0021(18) O3C 0.106(2) 0.0487(17) 0.091(2) 0.0066(16) -0.0104(18) -0.0137(16) C1A 0.039(2) 0.041(2) 0.044(2) -0.0001(17) 0.0016(18) 0.0044(17) C1D 0.055(2) 0.0330(19) 0.041(2) 0.0010(16) 0.0066(19) -0.0017(17) O2B 0.096(2) 0.0637(19) 0.095(2) -0.0163(16) -0.0372(19) 0.0306(15) C4A 0.053(2) 0.034(2) 0.052(2) 0.0013(17) 0.003(2) 0.0074(17) C4C 0.052(2) 0.047(2) 0.041(2) -0.0068(17) 0.0056(19) -0.0138(19) O1C 0.090(2) 0.0639(17) 0.0486(18) 0.0126(14) -0.0104(15) -0.0348(14) C5A 0.048(2) 0.040(2) 0.063(3) -0.0050(18) 0.002(2) -0.0041(18) C2C 0.048(2) 0.044(2) 0.037(2) -0.0019(16) 0.0035(18) -0.0015(17) C2D 0.050(2) 0.048(2) 0.041(2) 0.0022(17) 0.0015(18) 0.0002(18) C5D 0.050(2) 0.051(2) 0.055(3) -0.0008(19) -0.004(2) 0.0060(19) C7C 0.048(2) 0.052(2) 0.047(3) -0.011(2) 0.001(2) -0.0069(18) C3D 0.064(3) 0.0330(19) 0.052(3) 0.0060(17) 0.008(2) 0.0007(18) C6A 0.040(2) 0.051(2) 0.056(3) -0.0043(19) -0.0045(19) 0.0025(18) O3A 0.088(2) 0.0455(17) 0.172(3) 0.0110(19) -0.006(2) -0.0017(16) N1A 0.069(2) 0.042(2) 0.080(3) 0.0032(18) -0.006(2) 0.0061(19) C4D 0.050(2) 0.043(2) 0.048(2) 0.0011(18) 0.0051(19) -0.0026(18) C2A 0.036(2) 0.040(2) 0.052(2) -0.0018(17) 0.0071(18) -0.0028(16) C3A 0.042(2) 0.046(2) 0.051(2) -0.0005(18) -0.0015(18) 0.0040(17) O4C 0.0643(19) 0.083(2) 0.110(3) -0.0096(17) -0.0004(19) -0.0284(17) C6C 0.047(2) 0.057(2) 0.063(3) 0.000(2) -0.004(2) -0.005(2) C3C 0.039(2) 0.058(2) 0.046(2) -0.0053(19) -0.0023(18) -0.0017(18) C7A 0.047(2) 0.048(2) 0.060(3) 0.000(2) 0.003(2) 0.0087(19) N1B 0.080(3) 0.079(3) 0.069(3) -0.006(2) -0.013(2) 0.021(2) C6D 0.054(2) 0.040(2) 0.059(3) -0.0009(18) 0.000(2) 0.0046(18) O4A 0.090(2) 0.0643(19) 0.151(3) -0.0035(18) -0.044(2) 0.0230(17) C2B 0.052(2) 0.050(2) 0.045(2) -0.0023(18) 0.0000(19) 0.0023(18) C1B 0.054(2) 0.042(2) 0.046(2) 0.0004(18) 0.0042(19) 0.0071(18) C7B 0.051(2) 0.050(2) 0.065(3) -0.005(2) -0.008(2) 0.000(2) O4B 0.131(3) 0.083(2) 0.130(3) -0.032(2) -0.049(2) 0.046(2) C5B 0.051(2) 0.068(3) 0.069(3) 0.002(2) -0.003(2) 0.011(2) C4B 0.061(3) 0.060(3) 0.046(3) 0.002(2) 0.001(2) 0.023(2) C6B 0.052(2) 0.058(2) 0.068(3) -0.003(2) -0.004(2) -0.006(2) O3B 0.073(2) 0.114(3) 0.124(3) 0.022(2) -0.005(2) 0.0289(19) _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 Cl1A C2A 1.725(3) . ? Cl1B C2B 1.719(3) . ? Cl1D C2D 1.724(3) . ? Cl1C C2C 1.722(3) . ? O2C C7C 1.312(4) . ? O1D C7D 1.222(4) . ? O1A C7A 1.221(4) . ? O4D N1D 1.204(3) . ? O2D C7D 1.300(4) . ? O2A C7A 1.309(4) . ? O3D N1D 1.234(3) . ? C1C C2C 1.389(4) . ? C1C C6C 1.398(4) . ? C1C C7C 1.504(4) . ? N1C O4C 1.207(4) . ? N1C O3C 1.209(4) . ? N1C C4C 1.479(4) . ? O1B C7B 1.216(4) . ? N1D C4D 1.488(4) . ? C3B C4B 1.370(4) . ? C3B C2B 1.395(4) . ? C5C C4C 1.377(4) . ? C5C C6C 1.377(4) . ? C7D C1D 1.490(4) . ? C1A C6A 1.394(4) . ? C1A C2A 1.401(4) . ? C1A C7A 1.486(4) . ? C1D C6D 1.392(4) . ? C1D C2D 1.403(4) . ? O2B C7B 1.287(4) . ? C4A C5A 1.370(4) . ? C4A C3A 1.373(4) . ? C4A N1A 1.471(4) . ? C4C C3C 1.368(4) . ? O1C C7C 1.215(4) . ? C5A C6A 1.374(4) . ? C2C C3C 1.383(4) . ? C2D C3D 1.394(4) . ? C5D C4D 1.365(4) . ? C5D C6D 1.378(4) . ? C3D C4D 1.378(4) . ? O3A N1A 1.191(3) . ? N1A O4A 1.214(3) . ? C2A C3A 1.376(4) . ? N1B O4B 1.196(4) . ? N1B O3B 1.224(4) . ? N1B C4B 1.478(5) . ? C2B C1B 1.394(4) . ? C1B C6B 1.397(4) . ? C1B C7B 1.490(5) . ? C5B C4B 1.360(5) . ? C5B C6B 1.370(4) . ? 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 C2C C1C C6C 118.7(3) . . ? C2C C1C C7C 122.6(3) . . ? C6C C1C C7C 118.6(3) . . ? O4C N1C O3C 124.8(3) . . ? O4C N1C C4C 117.5(3) . . ? O3C N1C C4C 117.7(3) . . ? O4D N1D O3D 124.5(3) . . ? O4D N1D C4D 118.8(3) . . ? O3D N1D C4D 116.7(3) . . ? C4B C3B C2B 118.4(3) . . ? C4C C5C C6C 117.8(3) . . ? O1D C7D O2D 123.7(3) . . ? O1D C7D C1D 120.0(3) . . ? O2D C7D C1D 116.3(3) . . ? C6A C1A C2A 117.8(3) . . ? C6A C1A C7A 119.7(3) . . ? C2A C1A C7A 122.4(3) . . ? C6D C1D C2D 118.5(3) . . ? C6D C1D C7D 116.4(3) . . ? C2D C1D C7D 125.0(3) . . ? C5A C4A C3A 122.8(3) . . ? C5A C4A N1A 119.8(3) . . ? C3A C4A N1A 117.5(3) . . ? C3C C4C C5C 122.5(3) . . ? C3C C4C N1C 118.5(3) . . ? C5C C4C N1C 119.0(3) . . ? C4A C5A C6A 117.9(3) . . ? C3C C2C C1C 120.2(3) . . ? C3C C2C Cl1C 116.9(3) . . ? C1C C2C Cl1C 122.9(2) . . ? C3D C2D C1D 119.9(3) . . ? C3D C2D Cl1D 117.0(3) . . ? C1D C2D Cl1D 123.0(3) . . ? C4D C5D C6D 118.2(3) . . ? O1C C7C O2C 124.6(3) . . ? O1C C7C C1C 122.3(3) . . ? O2C C7C C1C 113.0(3) . . ? C4D C3D C2D 118.8(3) . . ? C5A C6A C1A 122.0(3) . . ? O3A N1A O4A 122.9(3) . . ? O3A N1A C4A 118.8(3) . . ? O4A N1A C4A 118.2(3) . . ? C5D C4D C3D 122.8(3) . . ? C5D C4D N1D 119.5(3) . . ? C3D C4D N1D 117.7(3) . . ? C3A C2A C1A 120.8(3) . . ? C3A C2A Cl1A 116.9(2) . . ? C1A C2A Cl1A 122.3(2) . . ? C4A C3A C2A 118.7(3) . . ? C5C C6C C1C 121.4(3) . . ? C4C C3C C2C 119.3(3) . . ? O1A C7A O2A 124.8(3) . . ? O1A C7A C1A 121.5(3) . . ? O2A C7A C1A 113.7(3) . . ? O4B N1B O3B 125.2(4) . . ? O4B N1B C4B 117.0(4) . . ? O3B N1B C4B 117.8(4) . . ? C5D C6D C1D 121.8(3) . . ? C1B C2B C3B 119.7(3) . . ? C1B C2B Cl1B 123.0(3) . . ? C3B C2B Cl1B 117.3(3) . . ? C2B C1B C6B 118.7(3) . . ? C2B C1B C7B 125.2(3) . . ? C6B C1B C7B 116.1(3) . . ? O1B C7B O2B 123.8(3) . . ? O1B C7B C1B 118.8(3) . . ? O2B C7B C1B 117.3(3) . . ? C4B C5B C6B 117.5(3) . . ? C5B C4B C3B 123.7(3) . . ? C5B C4B N1B 117.7(4) . . ? C3B C4B N1B 118.6(4) . . ? C5B C6B C1B 121.9(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1D C7D C1D C6D -29.5(5) . . . . ? O2D C7D C1D C6D 149.5(3) . . . . ? O1D C7D C1D C2D 149.6(3) . . . . ? O2D C7D C1D C2D -31.3(5) . . . . ? C6C C5C C4C C3C -0.3(6) . . . . ? C6C C5C C4C N1C 178.6(3) . . . . ? O4C N1C C4C C3C -18.7(5) . . . . ? O3C N1C C4C C3C 159.6(3) . . . . ? O4C N1C C4C C5C 162.4(3) . . . . ? O3C N1C C4C C5C -19.3(5) . . . . ? C3A C4A C5A C6A 0.8(5) . . . . ? N1A C4A C5A C6A -178.8(3) . . . . ? C6C C1C C2C C3C 0.5(5) . . . . ? C7C C1C C2C C3C 177.4(3) . . . . ? C6C C1C C2C Cl1C 178.1(3) . . . . ? C7C C1C C2C Cl1C -5.0(5) . . . . ? C6D C1D C2D C3D -0.2(5) . . . . ? C7D C1D C2D C3D -179.3(3) . . . . ? C6D C1D C2D Cl1D 176.2(3) . . . . ? C7D C1D C2D Cl1D -2.9(5) . . . . ? C2C C1C C7C O1C -35.9(5) . . . . ? C6C C1C C7C O1C 141.0(4) . . . . ? C2C C1C C7C O2C 146.8(3) . . . . ? C6C C1C C7C O2C -36.4(4) . . . . ? C1D C2D C3D C4D 0.5(5) . . . . ? Cl1D C2D C3D C4D -176.1(3) . . . . ? C4A C5A C6A C1A 1.2(5) . . . . ? C2A C1A C6A C5A -2.0(5) . . . . ? C7A C1A C6A C5A 174.7(3) . . . . ? C5A C4A N1A O3A 3.1(5) . . . . ? C3A C4A N1A O3A -176.5(4) . . . . ? C5A C4A N1A O4A -175.1(4) . . . . ? C3A C4A N1A O4A 5.3(5) . . . . ? C6D C5D C4D C3D 0.9(5) . . . . ? C6D C5D C4D N1D -178.2(3) . . . . ? C2D C3D C4D C5D -0.9(5) . . . . ? C2D C3D C4D N1D 178.2(3) . . . . ? O4D N1D C4D C5D -169.6(3) . . . . ? O3D N1D C4D C5D 11.5(5) . . . . ? O4D N1D C4D C3D 11.3(5) . . . . ? O3D N1D C4D C3D -167.6(3) . . . . ? C6A C1A C2A C3A 0.9(5) . . . . ? C7A C1A C2A C3A -175.7(3) . . . . ? C6A C1A C2A Cl1A -177.8(3) . . . . ? C7A C1A C2A Cl1A 5.7(5) . . . . ? C5A C4A C3A C2A -1.9(5) . . . . ? N1A C4A C3A C2A 177.7(3) . . . . ? C1A C2A C3A C4A 1.0(5) . . . . ? Cl1A C2A C3A C4A 179.7(3) . . . . ? C4C C5C C6C C1C -1.6(6) . . . . ? C2C C1C C6C C5C 1.5(5) . . . . ? C7C C1C C6C C5C -175.5(3) . . . . ? C5C C4C C3C C2C 2.2(5) . . . . ? N1C C4C C3C C2C -176.7(3) . . . . ? C1C C2C C3C C4C -2.3(5) . . . . ? Cl1C C2C C3C C4C 179.9(3) . . . . ? C6A C1A C7A O1A -144.0(4) . . . . ? C2A C1A C7A O1A 32.5(5) . . . . ? C6A C1A C7A O2A 33.4(5) . . . . ? C2A C1A C7A O2A -150.1(3) . . . . ? C4D C5D C6D C1D -0.5(5) . . . . ? C2D C1D C6D C5D 0.1(5) . . . . ? C7D C1D C6D C5D 179.3(3) . . . . ? C4B C3B C2B C1B 1.3(5) . . . . ? C4B C3B C2B Cl1B 179.7(3) . . . . ? C3B C2B C1B C6B -1.2(5) . . . . ? Cl1B C2B C1B C6B -179.5(3) . . . . ? C3B C2B C1B C7B 178.2(3) . . . . ? Cl1B C2B C1B C7B 0.0(5) . . . . ? C2B C1B C7B O1B -144.6(4) . . . . ? C6B C1B C7B O1B 34.9(5) . . . . ? C2B C1B C7B O2B 35.5(6) . . . . ? C6B C1B C7B O2B -145.0(4) . . . . ? C6B C5B C4B C3B -1.1(6) . . . . ? C6B C5B C4B N1B -179.3(3) . . . . ? C2B C3B C4B C5B -0.1(6) . . . . ? C2B C3B C4B N1B 178.0(3) . . . . ? O4B N1B C4B C5B 179.0(4) . . . . ? O3B N1B C4B C5B -3.1(6) . . . . ? O4B N1B C4B C3B 0.7(6) . . . . ? O3B N1B C4B C3B 178.6(4) . . . . ? C4B C5B C6B C1B 1.2(6) . . . . ? C2B C1B C6B C5B 0.0(6) . . . . ? C7B C1B C6B C5B -179.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.926 _diffrn_reflns_theta_full 28.38 _diffrn_measured_fraction_theta_full 0.926 _refine_diff_density_max 0.599 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.057 # Attachment '104C Full.cif' ############################################################################## ### CIF submission form for results of Rietveld refinements (IUCr journals)### ### Version 10 February 2005 ### ############################################################################## # This is an electronic "form" for submitting the results of a Rietveld # refinement of a model against powder diffraction data to an # IUCr journal as a Crystallographic Information File (CIF). Full details # of the CIF format are given in the paper "The Crystallographic Information # File (CIF): a New Standard Archive File for Crystallography" by S. R. Hall, # F. H. Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # The current version of the powder CIF dictionary, which contains definitions # of the terms staring _pd_, may be obtained from # http://www.iucr.org/iucr-top/cif/pd/index.html. Other terms are defined in # the core CIF dictionary at http://www.iucr.org/iucr-top/cif/core/index.html. # # Note that all fields should be numeric or character type EXCEPT those which # are flagged as 'text' - free-form text of any length may be included in # these latter fields provided the text block begins and ends with a semicolon # as the first character of a new line. Note also that the query marks # '?' are significant as placeholders, and should not be deleted where a data # item is not given, UNLESS the accompanying data name is also deleted. # Lines should not exceed 80 characters in length. The comments following # a hash symbol '#' may be deleted if wished. #============================================================================= data_104C_Full.cif _database_code_depnum_ccdc_archive 'CCDC 700780' _chemical_name_systematic ; ??? ; _chemical_name_common '2-chloro-4-nitrobenzoic acid' _chemical_formula_moiety 'C7 O4 N Cl H4' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum ? _chemical_formula_weight 201.562 _chemical_melting_point ? _chemical_compound_source ? # for minerals and # natural products loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source _atom_type_scat_length_neutron # include if applicable ? ? ? ? ? ? #============================================================================== # 6. POWDER SPECIMEN AND CRYSTAL DATA _space_group_crystal_system Monoclinic _space_group_name_H-M_alt P21/c _space_group_name_Hall P21/c loop_ _symmetry_equiv_pos_as_xyz '-x, -y, -z' '-x, y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' 'x, y, z' _cell_length_a 10.36698 _cell_length_b 6.20725 _cell_length_c 13.54374 _cell_angle_alpha 90 _cell_angle_beta 109.0579 _cell_angle_gamma 90 _cell_volume 823.7755 _cell_formula_units_Z 4 # The next three fields give the specimen dimensions in mm. The equatorial # plane contains the incident and diffracted beam. _pd_spec_size_axial 8 # perpendicular to # equatorial plane _pd_spec_size_equat ? # parallel to # scattering vector # in transmission _pd_spec_size_thick 1.5 # parallel to # scattering vector # in reflection # The next five fields are character fields that describe the specimen. _pd_spec_mounting # This field should be # used to give details of the # container. ; capillary ; _pd_spec_mount_mode transmission # options are 'reflection' # or 'transmission' _pd_spec_shape cylinder # options are 'cylinder' # 'flat_sheet' or 'irregular' _pd_char_particle_morphology ? _pd_char_colour ? # use ICDD colour descriptions # The following three fields describe the preparation of the specimen. # The cooling rate is in K/min. The pressure at which the sample was # prepared is in kPa. The temperature of preparation is in K. _pd_prep_cool_rate ? _pd_prep_pressure ? _pd_prep_temperature ? # The next four fields are normally only needed for transmission experiments. _exptl_absorpt_coefficient_mu ? _exptl_absorpt_correction_type none # include if applicable _exptl_absorpt_process_details ? # include if applicable _exptl_absorpt_correction_T_min ? # include if applicable _exptl_absorpt_correction_T_max ? # include if applicable #============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; # The following item is used to identify the equipment used to record # the powder pattern when the diffractogram was measured at a laboratory # other than the authors' home institution, e.g. when neutron or synchrotron # radiation is used. _pd_instr_location ; X16C, National Synchrotron Light Source, Brookhaven National Laboratory ; _pd_calibration_special_details # description of the method used # to calibrate the instrument ; NIST standard reference material 1976(sintered plate of Al2O3). 7 reflections were used to calibrate wavelength and detector zero. ; _diffrn_ambient_temperature 377 _diffrn_source synchrotron _diffrn_source_target ? _diffrn_source_type ? _diffrn_radiation_type ? _diffrn_measurement_device_type 'Huber diffractometer' _diffrn_detector 'NaI scintillation counter' _diffrn_detector_type ? # make or model of detector _pd_meas_scan_method step # options are 'step', 'cont', # 'tof', 'fixed' or # 'disp' (= dispersive) _pd_meas_special_details ; ? ; # The following six items are used for angular dispersive measurements only. _diffrn_radiation_wavelength 0.69865 _diffrn_radiation_monochromator 'double Si(111)' # The following four items give details of the measured (not processed) # powder pattern. Angles are in degrees. _pd_meas_number_of_points 6000 _pd_meas_2theta_range_min 2 _pd_meas_2theta_range_max 32 _pd_meas_2theta_range_inc 0.005 # The following three items are used for time-of-flight measurements only. _pd_instr_dist_src/spec ? _pd_instr_dist_spec/detc ? _pd_meas_2theta_fixed ? #============================================================================== # 8. REFINEMENT DATA # Use the next field to give any special details about the fitting of the # powder pattern. _pd_proc_ls_special_details ; ? ; # The next three items are given as text. _pd_proc_ls_profile_function ; Simple_Axial_Model(7.66523) function with Rp=9999,Rs=300 in TOPAS-Academic ; _pd_proc_ls_background_function ; Chebyshev polynomial with 5 coeffecients and a psuedo-Voight function at an angle of 2.54 degrees and a width of 0.46 degrees. ; _pd_proc_ls_pref_orient_corr ; none ; _pd_proc_ls_prof_R_factor ? _pd_proc_ls_prof_wR_factor ? _pd_proc_ls_prof_wR_expected ? _refine_ls_R_I_factor ? _refine_ls_R_Fsqd_factor ? _refine_ls_R_factor_all ? _refine_special_details ; The molecule was treated as a rigid body. All aromatic bond lengths were refined as a single parameter. Other bond lengths refined were the C-COOH distance, C-Cl distance, C-N distance, and N-O distance, both of which were refined as a single parameter. The Hydrogen atoms were tethered to their respective atoms at a distance of 0.9 angstroms. The torsions around C-COOH and C-NO2 bonds were also refined. ; _refine_ls_matrix_type ? _refine_ls_weighting_scheme sigma # options are 'sigma'(based on measured su's) # or 'calc' (calculated weights) _refine_ls_weighting_details 1/(sigma*sigma) _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method ? _refine_ls_extinction_coef ? _refine_ls_number_parameters 42 _refine_ls_number_restraints ? _refine_ls_number_constraints ? # The following item is the same as CHI, the square root of 'CHI squared' _refine_ls_goodness_of_fit_all 1.433 _refine_ls_restrained_S_all ? _refine_ls_shift/su_max ? _refine_ls_shift/su_mean ? # The following four items apply to angular dispersive measurements. # 2theta minimum, maximum and increment (in degrees) are for the # intensities used in the refinement. _pd_proc_2theta_range_min 2 _pd_proc_2theta_range_max 32 _pd_proc_2theta_range_inc 0.005 _pd_proc_wavelength 0.69865 _pd_block_diffractogram_id 2c4n-acid_104K_profile # The id used for the block containing # the powder pattern profile (section 11) # Give appropriate details in the next two text fields. _pd_proc_info_excluded_regions ? _pd_proc_info_data_reduction ? # The following items are used to identify the programs used. _computing_data_collection EPICS _computing_cell_refinement 'TOPAS Academic' _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'TOPAS Academic' _computing_molecular_graphics ? _computing_publication_material ? # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_symmetry_multiplicity _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_B_iso_or_equiv Cl1 Cl 4 0.883083 0.1408767 0.2706554 1 8.0691 N1 N 4 0.5656692 0.8085354 0.1770861 1 8.0691 C1 C 4 0.80744 0.3512 0.08502 1 8.0691 O4 O 4 0.4940635 0.9163594 0.1135692 1 8.0691 C3 C 4 0.718372 0.4901208 0.2132168 1 8.0691 C2 C 4 0.7967681 0.3418263 0.1833637 1 8.0691 C4 C 4 0.6506479 0.6477891 0.1447263 1 8.0691 O1 O 4 0.8388259 0.04474383 0.002444181 1 8.0691 C7 C 4 0.8932801 0.1888242 0.05233217 1 8.0691 C6 C 4 0.7397159 0.5088683 0.01652949 1 8.0691 C5 C 4 0.6613198 0.6571628 0.04638263 1 8.0691 O3 O 4 0.5756453 0.8172905 0.2640714 1 8.0691 O2 O 4 1.009456 0.2161511 0.07871653 1 8.0691 H1 H 4 0.7467099 0.5150114 -0.04792106 1 8.0691 H2 H 4 0.6169361 0.7604924 0.001496656 1 8.0691 H3 H 4 0.711378 0.4839777 0.2776673 1 8.0691 H4 H 4 1.069436 0.1111738 0.05830041 1 8.0691 #============================================================================== # Additional structures (sections 5-10 and associated data_? identifiers) # may be added at this point. #============================================================================== # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set. # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ #============================================================================== # Attachment '129C Full.cif' ############################################################################## ### CIF submission form for results of Rietveld refinements (IUCr journals)### ### Version 10 February 2005 ### ############################################################################## # This is an electronic "form" for submitting the results of a Rietveld # refinement of a model against powder diffraction data to an # IUCr journal as a Crystallographic Information File (CIF). Full details # of the CIF format are given in the paper "The Crystallographic Information # File (CIF): a New Standard Archive File for Crystallography" by S. R. Hall, # F. H. Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # The current version of the powder CIF dictionary, which contains definitions # of the terms staring _pd_, may be obtained from # http://www.iucr.org/iucr-top/cif/pd/index.html. Other terms are defined in # the core CIF dictionary at http://www.iucr.org/iucr-top/cif/core/index.html. # # Note that all fields should be numeric or character type EXCEPT those which # are flagged as 'text' - free-form text of any length may be included in # these latter fields provided the text block begins and ends with a semicolon # as the first character of a new line. Note also that the query marks # '?' are significant as placeholders, and should not be deleted where a data # item is not given, UNLESS the accompanying data name is also deleted. # Lines should not exceed 80 characters in length. The comments following # a hash symbol '#' may be deleted if wished. #============================================================================= data_129C_Full.cif _database_code_depnum_ccdc_archive 'CCDC 700781' _chemical_name_systematic ; ??? ; _chemical_name_common '2-chloro-4-nitrobenzoic acid' _chemical_formula_moiety 'C7 O4 N Cl H4' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum ? _chemical_formula_weight 201.562 _chemical_melting_point ? _chemical_compound_source ? # for minerals and # natural products loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source _atom_type_scat_length_neutron # include if applicable ? ? ? ? ? ? #============================================================================== # 6. POWDER SPECIMEN AND CRYSTAL DATA _space_group_crystal_system Monoclinic _space_group_name_H-M_alt P21/c _space_group_name_Hall P21/c loop_ _symmetry_equiv_pos_as_xyz '-x, -y, -z' '-x, y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' 'x, y, z' _cell_length_a 10.29897 _cell_length_b 6.2928 _cell_length_c 13.61244 _cell_angle_alpha 90 _cell_angle_beta 110.0103 _cell_angle_gamma 90 _cell_volume 828.9555 _cell_formula_units_Z 4 # The next three fields give the specimen dimensions in mm. The equatorial # plane contains the incident and diffracted beam. _pd_spec_size_axial 8 # perpendicular to # equatorial plane _pd_spec_size_equat ? # parallel to # scattering vector # in transmission _pd_spec_size_thick 1.5 # parallel to # scattering vector # in reflection # The next five fields are character fields that describe the specimen. _pd_spec_mounting # This field should be # used to give details of the # container. ; capillary ; _pd_spec_mount_mode transmission # options are 'reflection' # or 'transmission' _pd_spec_shape cylinder # options are 'cylinder' # 'flat_sheet' or 'irregular' _pd_char_particle_morphology ? _pd_char_colour ? # use ICDD colour descriptions # The following three fields describe the preparation of the specimen. # The cooling rate is in K/min. The pressure at which the sample was # prepared is in kPa. The temperature of preparation is in K. _pd_prep_cool_rate ? _pd_prep_pressure ? _pd_prep_temperature ? # The next four fields are normally only needed for transmission experiments. _exptl_absorpt_coefficient_mu ? _exptl_absorpt_correction_type none # include if applicable _exptl_absorpt_process_details ? # include if applicable _exptl_absorpt_correction_T_min ? # include if applicable _exptl_absorpt_correction_T_max ? # include if applicable #============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; # The following item is used to identify the equipment used to record # the powder pattern when the diffractogram was measured at a laboratory # other than the authors' home institution, e.g. when neutron or synchrotron # radiation is used. _pd_instr_location ; X16C, National Synchrotron Light Source, Brookhaven National Laboratory ; _pd_calibration_special_details # description of the method used # to calibrate the instrument ; NIST standard reference material 1976(sintered plate of Al2O3). 7 reflections were used to calibrate wavelength and detector zero. ; _diffrn_ambient_temperature 402 _diffrn_source synchrotron _diffrn_source_target ? _diffrn_source_type ? _diffrn_radiation_type ? _diffrn_measurement_device_type 'Huber diffractometer' _diffrn_detector 'NaI scintillation counter' _diffrn_detector_type ? # make or model of detector _pd_meas_scan_method step # options are 'step', 'cont', # 'tof', 'fixed' or # 'disp' (= dispersive) _pd_meas_special_details ; ? ; # The following six items are used for angular dispersive measurements only. _diffrn_radiation_wavelength 0.69865 _diffrn_radiation_monochromator 'double Si(111)' # The following four items give details of the measured (not processed) # powder pattern. Angles are in degrees. _pd_meas_number_of_points 6000 _pd_meas_2theta_range_min 2 _pd_meas_2theta_range_max 32 _pd_meas_2theta_range_inc 0.005 # The following three items are used for time-of-flight measurements only. _pd_instr_dist_src/spec ? _pd_instr_dist_spec/detc ? _pd_meas_2theta_fixed ? #============================================================================== # 8. REFINEMENT DATA # Use the next field to give any special details about the fitting of the # powder pattern. _pd_proc_ls_special_details ; ? ; # The next three items are given as text. _pd_proc_ls_profile_function ; Simple_Axial_Model(7.82445) function with Rp=9999,Rs=300 in TOPAS-Academic ; _pd_proc_ls_background_function ; Chebyshev polynomial with 5 coeffecients and a psuedo-Voight function at an angle of 2.57 degrees and a width of 0.34 degrees. ; _pd_proc_ls_pref_orient_corr ; none ; _pd_proc_ls_prof_R_factor ? _pd_proc_ls_prof_wR_factor ? _pd_proc_ls_prof_wR_expected ? _refine_ls_R_I_factor ? _refine_ls_R_Fsqd_factor ? _refine_ls_R_factor_all ? _refine_special_details ; The molecule was treated as a rigid body. All aromatic bond lengths were refined as a single parameter. Other bond lengths refined were the C-COOH distance, C-Cl distance, C-N distance, and N-O distance, both of which were refined as a single parameter. The Hydrogen atoms were tethered to their respective atoms at a distance of 0.9 angstroms. The torsions around C-COOH and C-NO2 bonds were also refined. ; _refine_ls_matrix_type ? _refine_ls_weighting_scheme sigma # options are 'sigma'(based on measured su's) # or 'calc' (calculated weights) _refine_ls_weighting_details 1/(sigma*sigma) _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method ? _refine_ls_extinction_coef ? _refine_ls_number_parameters 41 _refine_ls_number_restraints ? _refine_ls_number_constraints ? # The following item is the same as CHI, the square root of 'CHI squared' _refine_ls_goodness_of_fit_all 4.581 _refine_ls_restrained_S_all ? _refine_ls_shift/su_max ? _refine_ls_shift/su_mean ? # The following four items apply to angular dispersive measurements. # 2theta minimum, maximum and increment (in degrees) are for the # intensities used in the refinement. _pd_proc_2theta_range_min 2 _pd_proc_2theta_range_max 32 _pd_proc_2theta_range_inc 0.005 _pd_proc_wavelength 0.69865 _pd_block_diffractogram_id 2c4n-acid_129K_profile # The id used for the block containing # the powder pattern profile (section 11) # Give appropriate details in the next two text fields. _pd_proc_info_excluded_regions ? _pd_proc_info_data_reduction ? # The following items are used to identify the programs used. _computing_data_collection EPICS _computing_cell_refinement 'TOPAS Academic' _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'TOPAS Academic' _computing_molecular_graphics ? _computing_publication_material ? # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_symmetry_multiplicity _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_B_iso_or_equiv Cl1 Cl 4 0.8809557 0.1376301 0.2670541 1 7.9833 N1 N 4 0.5702336 0.7940404 0.1804122 1 7.9833 C1 C 4 0.80673 0.3484 0.08489 1 7.9833 O4 O 4 0.492318 0.9117609 0.1132256 1 7.9833 C3 C 4 0.7185517 0.4825469 0.2162841 1 7.9833 C2 C 4 0.797136 0.3344672 0.1845435 1 7.9833 C4 C 4 0.6495614 0.6445595 0.1483713 1 7.9833 O1 O 4 0.8351148 0.04462835 0.001282732 1 7.9833 C7 C 4 0.8917865 0.1881244 0.05053521 1 7.9833 C6 C 4 0.7377397 0.5104126 0.01697717 1 7.9833 C5 C 4 0.6591554 0.6584924 0.04871781 1 7.9833 O3 O 4 0.5828463 0.7993731 0.2739751 1 7.9833 O2 O 4 1.009583 0.2164404 0.07509904 1 7.9833 H1 H 4 0.7439241 0.5193939 -0.04726059 1 7.9833 H2 H 4 0.6146835 0.7629275 0.004940425 1 7.9833 H3 H 4 0.7123673 0.4735657 0.2805219 1 7.9833 H4 H 4 1.068815 0.1133808 0.05364044 1 7.9833 #============================================================================== # Additional structures (sections 5-10 and associated data_? identifiers) # may be added at this point. #============================================================================== # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set. # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ #============================================================================== # Attachment '83C Full.cif' ############################################################################## ### CIF submission form for results of Rietveld refinements (IUCr journals)### ### Version 10 February 2005 ### ############################################################################## # This is an electronic "form" for submitting the results of a Rietveld # refinement of a model against powder diffraction data to an # IUCr journal as a Crystallographic Information File (CIF). Full details # of the CIF format are given in the paper "The Crystallographic Information # File (CIF): a New Standard Archive File for Crystallography" by S. R. Hall, # F. H. Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # The current version of the powder CIF dictionary, which contains definitions # of the terms staring _pd_, may be obtained from # http://www.iucr.org/iucr-top/cif/pd/index.html. Other terms are defined in # the core CIF dictionary at http://www.iucr.org/iucr-top/cif/core/index.html. # # Note that all fields should be numeric or character type EXCEPT those which # are flagged as 'text' - free-form text of any length may be included in # these latter fields provided the text block begins and ends with a semicolon # as the first character of a new line. Note also that the query marks # '?' are significant as placeholders, and should not be deleted where a data # item is not given, UNLESS the accompanying data name is also deleted. # Lines should not exceed 80 characters in length. The comments following # a hash symbol '#' may be deleted if wished. data_83C_Full.cif _database_code_depnum_ccdc_archive 'CCDC 700782' _chemical_name_systematic ; ??? ; _chemical_name_common '2-chloro-4-nitrobenzoic acid' _chemical_formula_moiety 'C7 O4 N Cl H4' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum ? _chemical_formula_weight 201.562 _chemical_melting_point ? _chemical_compound_source ? # for minerals and # natural products loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source _atom_type_scat_length_neutron # include if applicable ? ? ? ? ? ? #============================================================================== # 6. POWDER SPECIMEN AND CRYSTAL DATA _space_group_crystal_system Monoclinic _space_group_name_H-M_alt P21/c _space_group_name_Hall P21/c loop_ _symmetry_equiv_pos_as_xyz '-x, -y, -z' '-x, y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' 'x, y, z' _cell_length_a 10.53231 _cell_length_b 6.075168 _cell_length_c 13.50803 _cell_angle_alpha 90 _cell_angle_beta 107.5649 _cell_angle_gamma 90 _cell_volume 824.0207 _cell_formula_units_Z 4 # The next three fields give the specimen dimensions in mm. The equatorial # plane contains the incident and diffracted beam. _pd_spec_size_axial 8 # perpendicular to # equatorial plane _pd_spec_size_equat ? # parallel to # scattering vector # in transmission _pd_spec_size_thick 1.5 # parallel to # scattering vector # in reflection # The next five fields are character fields that describe the specimen. _pd_spec_mounting # This field should be # used to give details of the # container. ; capillary ; _pd_spec_mount_mode transmission # options are 'reflection' # or 'transmission' _pd_spec_shape cylinder # options are 'cylinder' # 'flat_sheet' or 'irregular' _pd_char_particle_morphology ? _pd_char_colour ? # use ICDD colour descriptions # The following three fields describe the preparation of the specimen. # The cooling rate is in K/min. The pressure at which the sample was # prepared is in kPa. The temperature of preparation is in K. _pd_prep_cool_rate ? _pd_prep_pressure ? _pd_prep_temperature ? # The next four fields are normally only needed for transmission experiments. _exptl_absorpt_coefficient_mu ? _exptl_absorpt_correction_type none # include if applicable _exptl_absorpt_process_details ? # include if applicable _exptl_absorpt_correction_T_min ? # include if applicable _exptl_absorpt_correction_T_max ? # include if applicable #============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; # The following item is used to identify the equipment used to record # the powder pattern when the diffractogram was measured at a laboratory # other than the authors' home institution, e.g. when neutron or synchrotron # radiation is used. _pd_instr_location ; X16C, National Synchrotron Light Source, Brookhaven National Laboratory ; _pd_calibration_special_details # description of the method used # to calibrate the instrument ; NIST standard reference material 1976(sintered plate of Al2O3). 7 reflections were used to calibrate wavelength and detector zero. ; _diffrn_ambient_temperature 356 _diffrn_source synchrotron _diffrn_source_target ? _diffrn_source_type ? _diffrn_radiation_type ? _diffrn_measurement_device_type 'Huber diffractometer' _diffrn_detector 'NaI scintillation counter' _diffrn_detector_type ? # make or model of detector _pd_meas_scan_method step # options are 'step', 'cont', # 'tof', 'fixed' or # 'disp' (= dispersive) _pd_meas_special_details ; ? ; # The following six items are used for angular dispersive measurements only. _diffrn_radiation_wavelength 0.69865 _diffrn_radiation_monochromator 'double Si(111)' # The following four items give details of the measured (not processed) # powder pattern. Angles are in degrees. _pd_meas_number_of_points 5800 _pd_meas_2theta_range_min 1 _pd_meas_2theta_range_max 30 _pd_meas_2theta_range_inc 0.005 # The following three items are used for time-of-flight measurements only. _pd_instr_dist_src/spec ? _pd_instr_dist_spec/detc ? _pd_meas_2theta_fixed ? #============================================================================== # 8. REFINEMENT DATA # Use the next field to give any special details about the fitting of the # powder pattern. _pd_proc_ls_special_details ; ? ; # The next three items are given as text. _pd_proc_ls_profile_function ; Simple_Axial_Model(8.47973) function with Rp=9999,Rs=300 in TOPAS-Academic ; _pd_proc_ls_background_function ; Chebyshev polynomial with 5 coeffecients and a psuedo-Voight function at an angle of 2.31 degrees and a width of 1.79 degrees. ; _pd_proc_ls_pref_orient_corr ; none ; _pd_proc_ls_prof_R_factor ? _pd_proc_ls_prof_wR_factor ? _pd_proc_ls_prof_wR_expected ? _refine_ls_R_I_factor ? _refine_ls_R_Fsqd_factor ? _refine_ls_R_factor_all ? _refine_special_details ; The molecule was treated as a rigid body. All aromatic bond lengths were refined as a single parameter. Other bond lengths refined were the C-COOH distance, C-Cl distance, C-N distance, and N-O distance, both of which were refined as a single parameter. The Hydrogen atoms were tethered to their respective atoms at a distance of 0.9 angstroms. The torsions around C-COOH and C-NO2 bonds were also refined. ; _refine_ls_matrix_type ? _refine_ls_weighting_scheme sigma # options are 'sigma'(based on measured su's) # or 'calc' (calculated weights) _refine_ls_weighting_details 1/(sigma*sigma) _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method ? _refine_ls_extinction_coef ? _refine_ls_number_parameters 41 _refine_ls_number_restraints ? _refine_ls_number_constraints ? # The following item is the same as CHI, the square root of 'CHI squared' _refine_ls_goodness_of_fit_all 2.701 _refine_ls_restrained_S_all ? _refine_ls_shift/su_max ? _refine_ls_shift/su_mean ? # The following four items apply to angular dispersive measurements. # 2theta minimum, maximum and increment (in degrees) are for the # intensities used in the refinement. _pd_proc_2theta_range_min 1 _pd_proc_2theta_range_max 30 _pd_proc_2theta_range_inc 0.005 _pd_proc_wavelength 0.69865 _pd_block_diffractogram_id 2c4n-acid_83K_profile # The id used for the block containing # the powder pattern profile (section 11) # Give appropriate details in the next two text fields. _pd_proc_info_excluded_regions ? _pd_proc_info_data_reduction ? # The following items are used to identify the programs used. _computing_data_collection EPICS _computing_cell_refinement 'TOPAS Academic' _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'TOPAS Academic' _computing_molecular_graphics ? _computing_publication_material ? # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_symmetry_multiplicity _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_B_iso_or_equiv Cl1 Cl 4 0.8862014 0.149223 0.2734701 1 7.778768 N1 N 4 0.564959 0.8219857 0.1824732 1 7.778768 C1 C 4 0.8053007 0.3526703 0.08624755 1 7.778768 O4 O 4 0.4849359 0.921426 0.1173712 1 7.778768 C3 C 4 0.720146 0.4989312 0.2170322 1 7.778768 C2 C 4 0.797579 0.3477279 0.1860303 1 7.778768 C4 C 4 0.6504348 0.6550771 0.1482512 1 7.778768 O1 O 4 0.835319 0.02782025 0.003223224 1 7.778768 C7 C 4 0.8901745 0.186937 0.05226659 1 7.778768 C6 C 4 0.7355894 0.5088161 0.01746661 1 7.778768 C5 C 4 0.6581565 0.6600195 0.04846845 1 7.778768 O3 O 4 0.5823855 0.8447779 0.2726369 1 7.778768 O2 O 4 1.009276 0.2206017 0.075588 1 7.778768 H1 H 4 0.7406439 0.5120513 -0.04784914 1 7.778768 H2 H 4 0.612525 0.7622293 0.00344586 1 7.778768 H3 H 4 0.7150916 0.495696 0.2823479 1 7.778768 H4 H 4 1.068389 0.1138328 0.0542309 1 7.778768 #============================================================================== # Additional structures (sections 5-10 and associated data_? identifiers) # may be added at this point. #============================================================================== # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set. # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ #============================================================================== # Attachment '88C Full.cif' ############################################################################## ### CIF submission form for results of Rietveld refinements (IUCr journals)### ### Version 10 February 2005 ### ############################################################################## # This is an electronic "form" for submitting the results of a Rietveld # refinement of a model against powder diffraction data to an # IUCr journal as a Crystallographic Information File (CIF). Full details # of the CIF format are given in the paper "The Crystallographic Information # File (CIF): a New Standard Archive File for Crystallography" by S. R. Hall, # F. H. Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # The current version of the powder CIF dictionary, which contains definitions # of the terms staring _pd_, may be obtained from # http://www.iucr.org/iucr-top/cif/pd/index.html. Other terms are defined in # the core CIF dictionary at http://www.iucr.org/iucr-top/cif/core/index.html. # # Note that all fields should be numeric or character type EXCEPT those which # are flagged as 'text' - free-form text of any length may be included in # these latter fields provided the text block begins and ends with a semicolon # as the first character of a new line. Note also that the query marks # '?' are significant as placeholders, and should not be deleted where a data # item is not given, UNLESS the accompanying data name is also deleted. # Lines should not exceed 80 characters in length. The comments following # a hash symbol '#' may be deleted if wished. data_88C_Full.cif _database_code_depnum_ccdc_archive 'CCDC 700783' _chemical_name_systematic ; ??? ; _chemical_name_common '2-chloro-4-nitrobenzoic acid' _chemical_formula_moiety 'C7 O4 N Cl H4' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum ? _chemical_formula_weight 201.562 _chemical_melting_point ? _chemical_compound_source ? # for minerals and # natural products loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source _atom_type_scat_length_neutron # include if applicable ? ? ? ? ? ? #============================================================================== # 6. POWDER SPECIMEN AND CRYSTAL DATA _space_group_crystal_system Monoclinic _space_group_name_H-M_alt P21/c _space_group_name_Hall P21/c loop_ _symmetry_equiv_pos_as_xyz '-x, -y, -z' '-x, y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' 'x, y, z' _cell_length_a 10.5449 _cell_length_b 6.07214 _cell_length_c 13.51418 _cell_angle_alpha 90 _cell_angle_beta 107.4945 _cell_angle_gamma 90 _cell_volume 825.29 _cell_formula_units_Z 4 # The next three fields give the specimen dimensions in mm. The equatorial # plane contains the incident and diffracted beam. _pd_spec_size_axial 8 # perpendicular to # equatorial plane _pd_spec_size_equat ? # parallel to # scattering vector # in transmission _pd_spec_size_thick 1.5 # parallel to # scattering vector # in reflection # The next five fields are character fields that describe the specimen. _pd_spec_mounting # This field should be # used to give details of the # container. ; capillary ; _pd_spec_mount_mode transmission # options are 'reflection' # or 'transmission' _pd_spec_shape cylinder # options are 'cylinder' # 'flat_sheet' or 'irregular' _pd_char_particle_morphology ? _pd_char_colour ? # use ICDD colour descriptions # The following three fields describe the preparation of the specimen. # The cooling rate is in K/min. The pressure at which the sample was # prepared is in kPa. The temperature of preparation is in K. _pd_prep_cool_rate ? _pd_prep_pressure ? _pd_prep_temperature ? # The next four fields are normally only needed for transmission experiments. _exptl_absorpt_coefficient_mu ? _exptl_absorpt_correction_type none # include if applicable _exptl_absorpt_process_details ? # include if applicable _exptl_absorpt_correction_T_min ? # include if applicable _exptl_absorpt_correction_T_max ? # include if applicable #============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; # The following item is used to identify the equipment used to record # the powder pattern when the diffractogram was measured at a laboratory # other than the authors' home institution, e.g. when neutron or synchrotron # radiation is used. _pd_instr_location ; X16C, National Synchrotron Light Source, Brookhaven National Laboratory ; _pd_calibration_special_details # description of the method used # to calibrate the instrument ; NIST standard reference material 1976(sintered plate of Al2O3). 7 reflections were used to calibrate wavelength and detector zero. ; _diffrn_ambient_temperature 361 _diffrn_source synchrotron _diffrn_source_target ? _diffrn_source_type ? _diffrn_radiation_type ? _diffrn_measurement_device_type 'Huber diffractometer' _diffrn_detector 'NaI scintillation counter' _diffrn_detector_type ? # make or model of detector _pd_meas_scan_method step # options are 'step', 'cont', # 'tof', 'fixed' or # 'disp' (= dispersive) _pd_meas_special_details ; ? ; # The following six items are used for angular dispersive measurements only. _diffrn_radiation_wavelength 0.69865 _diffrn_radiation_monochromator 'double Si(111)' # The following four items give details of the measured (not processed) # powder pattern. Angles are in degrees. _pd_meas_number_of_points 6000 _pd_meas_2theta_range_min 2 _pd_meas_2theta_range_max 32 _pd_meas_2theta_range_inc 0.005 # The following three items are used for time-of-flight measurements only. _pd_instr_dist_src/spec ? _pd_instr_dist_spec/detc ? _pd_meas_2theta_fixed ? #============================================================================== # 8. REFINEMENT DATA # Use the next field to give any special details about the fitting of the # powder pattern. _pd_proc_ls_special_details ; ? ; # The next three items are given as text. _pd_proc_ls_profile_function ; Simple_Axial_Model(7.22276) function with Rp=9999,Rs=300 in TOPAS-Academic ; _pd_proc_ls_background_function ; Chebyshev polynomial with 5 coeffecients and a psuedo-Voight function at an angle of 2.57 degrees and a width of 0.32 degrees. ; _pd_proc_ls_pref_orient_corr ; none ; _pd_proc_ls_prof_R_factor ? _pd_proc_ls_prof_wR_factor ? _pd_proc_ls_prof_wR_expected ? _refine_ls_R_I_factor ? _refine_ls_R_Fsqd_factor ? _refine_ls_R_factor_all ? _refine_special_details ; The molecule was treated as a rigid body. All aromatic bond lengths were refined as a single parameter. Other bond lengths refined were the C-COOH distance, C-Cl distance, C-N distance, and N-O distance, both of which were refined as a single parameter. The Hydrogen atoms were tethered to their respective atoms at a distance of 0.9 angstroms. The torsions around C-COOH and C-NO2 bonds were also refined. ; _refine_ls_matrix_type ? _refine_ls_weighting_scheme sigma # options are 'sigma'(based on measured su's) # or 'calc' (calculated weights) _refine_ls_weighting_details 1/(sigma*sigma) _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method ? _refine_ls_extinction_coef ? _refine_ls_number_parameters 41 _refine_ls_number_restraints ? _refine_ls_number_constraints ? # The following item is the same as CHI, the square root of 'CHI squared' _refine_ls_goodness_of_fit_all 1.985 _refine_ls_restrained_S_all ? _refine_ls_shift/su_max ? _refine_ls_shift/su_mean ? # The following four items apply to angular dispersive measurements. # 2theta minimum, maximum and increment (in degrees) are for the # intensities used in the refinement. _pd_proc_2theta_range_min 2 _pd_proc_2theta_range_max 32 _pd_proc_2theta_range_inc 0.005 _pd_proc_wavelength 0.69865 _pd_block_diffractogram_id 2c4n-acid_88K_profile # The id used for the block containing # the powder pattern profile (section 11) # Give appropriate details in the next two text fields. _pd_proc_info_excluded_regions ? _pd_proc_info_data_reduction ? # The following items are used to identify the programs used. _computing_data_collection EPICS _computing_cell_refinement 'TOPAS Academic' _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'TOPAS Academic' _computing_molecular_graphics ? _computing_publication_material ? # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_symmetry_multiplicity _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_B_iso_or_equiv Cl1 Cl 4 0.8863844 0.1501898 0.2746946 1 7.728299 N1 N 4 0.5674676 0.8185489 0.1834517 1 7.728299 C1 C 4 0.8021301 0.35526 0.08563992 1 7.728299 O4 O 4 0.4847415 0.908899 0.1204532 1 7.728299 C3 C 4 0.7183807 0.5035029 0.2195381 1 7.728299 C2 C 4 0.7959939 0.3502729 0.1871875 1 7.728299 C4 C 4 0.6469037 0.66172 0.1503412 1 7.728299 O1 O 4 0.8323224 0.03920628 -0.002355681 1 7.728299 C7 C 4 0.8870932 0.1875194 0.05022569 1 7.728299 C6 C 4 0.7306532 0.5134771 0.01644303 1 7.728299 C5 C 4 0.65304 0.6667071 0.04879369 1 7.728299 O3 O 4 0.5896497 0.8477291 0.2716861 1 7.728299 O2 O 4 1.003804 0.2135454 0.07698921 1 7.728299 H1 H 4 0.7346164 0.5166981 -0.04914297 1 7.728299 H2 H 4 0.6068755 0.768894 0.004101845 1 7.728299 H3 H 4 0.7144175 0.5002819 0.2851241 1 7.728299 H4 H 4 1.062329 0.1065593 0.05511158 1 7.728299 #============================================================================== # Additional structures (sections 5-10 and associated data_? identifiers) # may be added at this point. #============================================================================== # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set. # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ #============================================================================== # Attachment 'RT Full.cif' ############################################################################## ### CIF submission form for results of Rietveld refinements (IUCr journals)### ### Version 10 February 2005 ### ############################################################################## # This is an electronic "form" for submitting the results of a Rietveld # refinement of a model against powder diffraction data to an # IUCr journal as a Crystallographic Information File (CIF). Full details # of the CIF format are given in the paper "The Crystallographic Information # File (CIF): a New Standard Archive File for Crystallography" by S. R. Hall, # F. H. Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # The current version of the powder CIF dictionary, which contains definitions # of the terms staring _pd_, may be obtained from # http://www.iucr.org/iucr-top/cif/pd/index.html. Other terms are defined in # the core CIF dictionary at http://www.iucr.org/iucr-top/cif/core/index.html. # # Note that all fields should be numeric or character type EXCEPT those which # are flagged as 'text' - free-form text of any length may be included in # these latter fields provided the text block begins and ends with a semicolon # as the first character of a new line. Note also that the query marks # '?' are significant as placeholders, and should not be deleted where a data # item is not given, UNLESS the accompanying data name is also deleted. # Lines should not exceed 80 characters in length. The comments following # a hash symbol '#' may be deleted if wished. data_RT_Full.cif _database_code_depnum_ccdc_archive 'CCDC 700784' _chemical_name_systematic ; ??? ; _chemical_name_common '2-chloro-4-nitrobenzoic acid' _chemical_formula_moiety 'C7 O4 N Cl H4' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum ? _chemical_formula_weight 201.562 _chemical_melting_point ? _chemical_compound_source ? # for minerals and # natural products loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source _atom_type_scat_length_neutron # include if applicable ? ? ? ? ? ? #============================================================================== # 6. POWDER SPECIMEN AND CRYSTAL DATA _space_group_crystal_system Monoclinic _space_group_name_H-M_alt P21/c _space_group_name_Hall P21/c loop_ _symmetry_equiv_pos_as_xyz '-x, -y, -z' '-x, y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' 'x, y, z' _cell_length_a 10.7946 _cell_length_b 5.848105 _cell_length_c 13.45977 _cell_angle_alpha 90 _cell_angle_beta 105.8001 _cell_angle_gamma 90 _cell_volume 817.5843 _cell_formula_units_Z 4 # The next three fields give the specimen dimensions in mm. The equatorial # plane contains the incident and diffracted beam. _pd_spec_size_axial 8 # perpendicular to # equatorial plane _pd_spec_size_equat ? # parallel to # scattering vector # in transmission _pd_spec_size_thick 1.5 # parallel to # scattering vector # in reflection # The next five fields are character fields that describe the specimen. _pd_spec_mounting # This field should be # used to give details of the # container. ; capillary ; _pd_spec_mount_mode transmission # options are 'reflection' # or 'transmission' _pd_spec_shape cylinder # options are 'cylinder' # 'flat_sheet' or 'irregular' _pd_char_particle_morphology ? _pd_char_colour ? # use ICDD colour descriptions # The following three fields describe the preparation of the specimen. # The cooling rate is in K/min. The pressure at which the sample was # prepared is in kPa. The temperature of preparation is in K. _pd_prep_cool_rate ? _pd_prep_pressure ? _pd_prep_temperature ? # The next four fields are normally only needed for transmission experiments. _exptl_absorpt_coefficient_mu ? _exptl_absorpt_correction_type none # include if applicable _exptl_absorpt_process_details ? # include if applicable _exptl_absorpt_correction_T_min ? # include if applicable _exptl_absorpt_correction_T_max ? # include if applicable #============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; # The following item is used to identify the equipment used to record # the powder pattern when the diffractogram was measured at a laboratory # other than the authors' home institution, e.g. when neutron or synchrotron # radiation is used. _pd_instr_location ; X16C, National Synchrotron Light Source, Brookhaven National Laboratory ; _pd_calibration_special_details # description of the method used # to calibrate the instrument ; NIST standard reference material 1976(sintered plate of Al2O3). 7 reflections were used to calibrate wavelength and detector zero. ; _diffrn_ambient_temperature 298 _diffrn_source synchrotron _diffrn_source_target ? _diffrn_source_type ? _diffrn_radiation_type ? _diffrn_measurement_device_type 'Huber diffractometer' _diffrn_detector 'NaI scintillation counter' _diffrn_detector_type ? # make or model of detector _pd_meas_scan_method step # options are 'step', 'cont', # 'tof', 'fixed' or # 'disp' (= dispersive) _pd_meas_special_details ; ? ; # The following six items are used for angular dispersive measurements only. _diffrn_radiation_wavelength 0.69865 _diffrn_radiation_monochromator 'double Si(111)' # The following four items give details of the measured (not processed) # powder pattern. Angles are in degrees. _pd_meas_number_of_points 6000 _pd_meas_2theta_range_min 2 _pd_meas_2theta_range_max 32 _pd_meas_2theta_range_inc 0.005 # The following three items are used for time-of-flight measurements only. _pd_instr_dist_src/spec ? _pd_instr_dist_spec/detc ? _pd_meas_2theta_fixed ? #============================================================================== # 8. REFINEMENT DATA # Use the next field to give any special details about the fitting of the # powder pattern. _pd_proc_ls_special_details ; ? ; # The next three items are given as text. _pd_proc_ls_profile_function ; Simple_Axial_Model(7.52163) function with Rp=9999,Rs=300 in TOPAS-Academic ; _pd_proc_ls_background_function ; Chebyshev polynomial with 5 coeffecients ; _pd_proc_ls_pref_orient_corr ; none ; _pd_proc_ls_prof_R_factor ? _pd_proc_ls_prof_wR_factor ? _pd_proc_ls_prof_wR_expected ? _refine_ls_R_I_factor ? _refine_ls_R_Fsqd_factor ? _refine_ls_R_factor_all ? _refine_special_details ; The molecule was treated as a rigid body. All aromatic bond lengths were refined as a single parameter. Other bond lengths refined were the C-COOH distance, C-Cl distance, C-N distance, and N-O distance, both of which were refined as a single parameter. The Hydrogen atoms were tethered to their respective atoms at a distance of 0.9 angstroms. The torsions around C-COOH and C-NO2 bonds were also refined. ; _refine_ls_matrix_type ? _refine_ls_weighting_scheme sigma # options are 'sigma'(based on measured su's) # or 'calc' (calculated weights) _refine_ls_weighting_details 1/(sigma*sigma) _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method ? _refine_ls_extinction_coef ? _refine_ls_number_parameters 38 _refine_ls_number_restraints ? _refine_ls_number_constraints ? # The following item is the same as CHI, the square root of 'CHI squared' _refine_ls_goodness_of_fit_all 3.554 _refine_ls_restrained_S_all ? _refine_ls_shift/su_max ? _refine_ls_shift/su_mean ? # The following four items apply to angular dispersive measurements. # 2theta minimum, maximum and increment (in degrees) are for the # intensities used in the refinement. _pd_proc_2theta_range_min 3 _pd_proc_2theta_range_max 32 _pd_proc_2theta_range_inc 0.005 _pd_proc_wavelength 0.69865 _pd_block_diffractogram_id 2c4n-acid_RT_profile # The id used for the block containing # the powder pattern profile (section 11) # Give appropriate details in the next two text fields. _pd_proc_info_excluded_regions ? _pd_proc_info_data_reduction ? # The following items are used to identify the programs used. _computing_data_collection EPICS _computing_cell_refinement 'TOPAS Academic' _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'TOPAS Academic' _computing_molecular_graphics ? _computing_publication_material ? # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_symmetry_multiplicity _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_B_iso_or_equiv Cl1 Cl 4 0.8901489 0.1583167 0.2768649 1 5.352359 N1 N 4 0.5660981 0.8192884 0.1856601 1 5.352359 C1 C 4 0.8031114 0.3559301 0.0869346 1 5.352359 O4 O 4 0.4776656 0.9085285 0.119953 1 5.352359 C3 C 4 0.7183459 0.5093728 0.2233473 1 5.352359 C2 C 4 0.7979796 0.3536898 0.1901767 1 5.352359 C4 C 4 0.6438439 0.6672961 0.1532759 1 5.352359 O1 O 4 0.8405148 0.0370402 -0.00193157 1 5.352359 C7 C 4 0.8893547 0.1873255 0.0510108 1 5.352359 C6 C 4 0.7286094 0.5138535 0.01686313 1 5.352359 C5 C 4 0.6489757 0.6695365 0.05003377 1 5.352359 O3 O 4 0.5892567 0.8576579 0.2785565 1 5.352359 O2 O 4 1.000077 0.2166319 0.07817679 1 5.352359 H1 H 4 0.7318949 0.5152878 -0.04923436 1 5.352359 H2 H 4 0.6012782 0.7706419 0.00517273 1 5.352359 H3 H 4 0.7150604 0.5079385 0.2894448 1 5.352359 H4 H 4 1.0594 0.1090044 0.05595589 1 5.352359