#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/18/2011827.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2011827 loop_ _publ_author_name 'Ferguson, George' 'Glidewell, Christopher' 'Low, John N.' 'Skakle, Janet M. S.' 'Wardell, James L.' _publ_section_title ; Hydrogen bonding in C-methylated nitroanilines: the three-dimensional framework structure of 2-methyl-4-nitroaniline ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 315 _journal_page_last 316 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C7 H8 N2 O2' _chemical_formula_sum 'C7 H8 N2 O2' _chemical_formula_weight 152.15 _chemical_name_systematic ; 2-Methyl-4-nitroaniline ; _space_group_IT_number 9 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'I -2ya' _symmetry_space_group_name_H-M 'I 1 a 1' _cell_angle_alpha 90.00 _cell_angle_beta 94.050(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.6113(5) _cell_length_b 11.6304(7) _cell_length_c 8.2286(5) _cell_measurement_reflns_used 1316 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 32.54 _cell_measurement_theta_min 3.04 _cell_volume 726.60(8) _computing_cell_refinement XPREP _computing_data_collection 'XPREP (Bruker, 1997)' _computing_data_reduction XPREP _computing_molecular_graphics 'PLATON (Spek, 2000)' _computing_publication_material 'SHELXL97 and WordPerfect macro PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .032 _diffrn_reflns_av_sigmaI/netI .0255 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 4272 _diffrn_reflns_theta_full 32.54 _diffrn_reflns_theta_max 32.54 _diffrn_reflns_theta_min 3.04 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu .104 _exptl_absorpt_correction_T_max .979 _exptl_absorpt_correction_T_min .969 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 1997)' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 320 _exptl_crystal_size_max .30 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .20 _refine_diff_density_max .248 _refine_diff_density_min -.258 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref .995 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 101 _refine_ls_number_reflns 1316 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all .994 _refine_ls_R_factor_all .056 _refine_ls_R_factor_gt .043 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0735P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .113 _reflns_number_gt 1037 _reflns_number_total 1316 _reflns_threshold_expression >2\s(I) _[local]_cod_data_source_file sk1442.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'I a' _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2011827 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z' 'x+1/2, y+1/2, z+1/2' 'x+1, -y+1/2, z+1/2' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 .9082(2) .07296(16) .7383(2) .0344(4) Uani d . 1 . . C C2 .8859(2) -.04640(14) .71078(18) .0337(4) Uani d . 1 . . C C3 .8083(3) -.08360(15) .5633(2) .0360(4) Uani d . 1 . . C C4 .7538(2) -.00392(17) .44279(18) .0352(4) Uani d . 1 . . C C5 .7736(3) .11337(16) .4687(2) .0405(4) Uani d . 1 . . C C6 .8508(3) .15102(16) .6156(2) .0399(4) Uani d . 1 . . C N1 .9814(3) .11329(15) .8825(2) .0478(4) Uani d . 1 . . N C7 .9475(3) -.13003(19) .8422(3) .0465(5) Uani d . 1 . . C N2 .6745(2) -.04422(15) .29017(18) .0463(4) Uani d . 1 . . N O1 .6538(3) -.14825(15) .2675(2) .0621(5) Uani d . 1 . . O O2 .6279(4) .02700(18) .1852(2) .0811(7) Uani d . 1 . . O H3 .7922 -.1618 .5440 .043 Uiso calc R 1 . . H H5 .7354 .1657 .3883 .049 Uiso calc R 1 . . H H6 .8652 .2295 .6338 .048 Uiso calc R 1 . . H H1A .9923 .1861 .8981 .057 Uiso calc R 1 . . H H1B 1.0168 .0660 .9582 .057 Uiso calc R 1 . . H H7A .9344 -.2071 .8015 .070 Uiso calc R 1 . . H H7B .8782 -.1206 .9344 .070 Uiso calc R 1 . . H H7C 1.0692 -.1157 .8747 .070 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 .0390(9) .0353(8) .0284(7) -.0033(7) -.0018(6) -.0021(6) C2 .0384(10) .0309(8) .0310(8) -.0026(6) -.0023(6) .0024(5) C3 .0448(9) .0310(7) .0312(7) -.0022(7) -.0055(6) -.0015(6) C4 .0433(9) .0355(8) .0255(6) -.0017(6) -.0063(6) -.0026(5) C5 .0518(11) .0358(9) .0327(8) .0002(7) -.0051(7) .0050(6) C6 .0557(11) .0299(8) .0330(8) -.0019(7) -.0046(7) -.0013(6) N1 .0676(12) .0397(9) .0341(8) -.0040(8) -.0107(7) -.0052(6) C7 .0579(12) .0408(9) .0387(9) -.0025(8) -.0119(8) .0097(7) N2 .0584(11) .0479(10) .0304(8) -.0021(8) -.0121(7) -.0046(6) O1 .0877(12) .0457(8) .0497(8) -.0066(8) -.0182(8) -.0136(7) O2 .132(2) .0645(12) .0408(9) -.0039(12) -.0375(10) .0062(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 . 1.415(2) y C2 C3 . 1.381(2) y C3 C4 . 1.398(2) y C3 H3 . .9300 no C4 C5 . 1.387(3) y C5 C6 . 1.377(3) y C5 H5 . .9300 no C6 C1 . 1.405(2) y C6 H6 . .9300 no C1 N1 . 1.358(2) y C4 N2 . 1.433(2) y N2 O1 . 1.233(2) y N2 O2 . 1.231(2) y C2 C7 . 1.505(2) y N1 H1A . .8600 no N1 H1B . .8600 no C7 H7A . .9600 no C7 H7B . .9600 no C7 H7C . .9600 no loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag N1 C1 C6 119.51(16) no N1 C1 C2 121.04(15) no C6 C1 C2 119.44(15) no C3 C2 C1 119.13(14) no C3 C2 C7 121.43(15) no C1 C2 C7 119.44(14) no C2 C3 C4 120.16(16) no C2 C3 H3 119.9 no C4 C3 H3 119.9 no C5 C4 C3 121.28(15) no C5 C4 N2 119.38(16) no C3 C4 N2 119.34(17) no C6 C5 C4 118.84(16) no C6 C5 H5 120.6 no C4 C5 H5 120.6 no C5 C6 C1 121.14(17) no C5 C6 H6 119.4 no C1 C6 H6 119.4 no C1 N1 H1A 120.0 no C1 N1 H1B 120.0 no H1A N1 H1B 120.0 no C2 C7 H7A 109.5 no C2 C7 H7B 109.5 no H7A C7 H7B 109.5 no C2 C7 H7C 109.5 no H7A C7 H7C 109.5 no H7B C7 H7C 109.5 no O2 N2 O1 121.80(16) no O2 N2 C4 118.53(16) no O1 N2 C4 119.67(16) no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1A O1 3 .86 2.56 3.239(3) 136 y N1 H1B O2 2_556 .86 2.27 3.117(3) 169 y 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_publ_flag N1 C1 C2 C3 178.99(18) no N1 C1 C2 C7 -1.2(3) no C6 C1 C2 C3 .1(2) no C6 C1 C2 C7 179.93(17) no N1 C1 C6 C5 -179.0(2) no C2 C1 C6 C5 -.1(3) no C1 C2 C3 C4 .4(3) no C7 C2 C3 C4 -179.40(18) no C2 C3 C4 N2 179.62(16) no C2 C3 C4 C5 -.9(3) no C3 C4 N2 O1 .7(3) no C3 C4 N2 O2 -179.8(2) no C5 C4 N2 O1 -178.79(19) no C5 C4 N2 O2 .8(3) no N2 C4 C5 C6 -179.66(18) no C3 C4 C5 C6 .9(3) no C4 C5 C6 C1 -.4(3) no _cod_database_fobs_code 2011827