#------------------------------------------------------------------------------ #$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $ #$Revision: 176432 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/06/2010641.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_2010641 loop_ _publ_author_name 'Foces-Foces, C.' 'Jagerovic, N.' 'Elguero, J.' _publ_section_title ; Weak C--H···O and C--H···N interactions in nitropyrazoles ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 215 _journal_page_last 218 _journal_paper_doi 10.1107/S0108270199013876 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C4 H5 N3 O2' _chemical_formula_sum 'C4 H5 N3 O2' _chemical_formula_weight 127.1 _chemical_name_systematic 1-methyl-3-nitro-pyrazole _space_group_IT_number 62 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2c 2n' _symmetry_space_group_name_H-M 'P n a m' _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_formula_units_Z 4 _cell_length_a 10.5062(5) _cell_length_b 8.5940(4) _cell_length_c 6.3562(3) _cell_measurement_reflns_used 69 _cell_measurement_temperature 293 _cell_measurement_theta_max 45 _cell_measurement_theta_min 2 _cell_volume 573.90(5) _computing_cell_refinement 'LSUCRE (Appleman, 1984)' _computing_data_collection 'Philips PW1100 (Hornstra & Vossers, 1973)' _computing_data_reduction 'Xtal3.2 (Hall et al., 1992)' _computing_molecular_graphics Xtal3.2 _computing_publication_material Xtal3.2 _computing_structure_refinement Xtal3.2 _computing_structure_solution Xtal3.2? _diffrn_ambient_temperature 293 _diffrn_measurement_device_type 'Philips PW1100 four-circle' _diffrn_measurement_method '\w/2\q scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents .044 _diffrn_reflns_av_sigmaI/netI .024 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1164 _diffrn_reflns_reduction_process 'perpendicular monochr Lp' _diffrn_reflns_theta_max 67.46 _diffrn_reflns_theta_min 6.65 _diffrn_standards_decay_% none _diffrn_standards_interval_time 90 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 1.038 _exptl_absorpt_correction_T_max .788 _exptl_absorpt_correction_T_min .518 _exptl_absorpt_correction_type \y-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_meas ? _exptl_crystal_description 'rectangular prism' _exptl_crystal_F_000 264 _exptl_crystal_size_max .60 _exptl_crystal_size_mid .50 _exptl_crystal_size_min .23 _refine_diff_density_max .215 _refine_diff_density_min -.188 _refine_ls_extinction_coef 16(6) _refine_ls_extinction_method '(Zachariasen, 1967)' _refine_ls_goodness_of_fit_all 1.016 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 56 _refine_ls_number_reflns 571 _refine_ls_number_restraints 0 _refine_ls_R_factor_all .043 _refine_ls_R_factor_gt .043 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = k/[(A+B Fo)^2^(C+D(sin\q)/\l)]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .045 _refine_ls_wR_factor_ref .045 _reflns_number_gt 571 _reflns_number_total 571 _reflns_threshold_expression I>0 _cod_data_source_file na1434.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_Hall '-P 2c -2n' _cod_database_code 2010641 _cod_database_fobs_code 2010641 loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -x,-y,1/2+z 1/2+x,1/2-y,1/2-z 1/2-x,1/2+y,-z -x,-y,-z +x,+y,1/2-z 1/2-x,1/2+y,1/2+z 1/2+x,1/2-y,+z 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_calc_attached_atom _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N1 .13497(16) .2825(2) 0.25 .0246(9) Uani ? ? 1 ? ? N2 .03272(16) .3748(2) 0.25 .0198(8) Uani ? ? 1 ? ? C3 .0822(2) .5158(2) 0.25 .0213(10) Uani ? ? 1 ? ? C4 .2139(2) .5173(3) 0.25 .0375(13) Uani ? ? 1 ? ? C5 .2443(2) .3637(3) 0.25 .0379(13) Uani ? ? 1 ? ? C6 .1188(3) .1150(3) 0.25 .0410(14) Uani ? ? 1 ? ? N7 -.0017(2) .6490(2) 0.25 .0300(10) Uani ? ? 1 ? ? O8 -.11584(17) .6290(2) 0.25 .0407(10) Uani ? ? 1 ? ? O9 .0478(3) .7769(2) 0.25 .0634(14) Uani ? ? 1 ? ? H4 .27059 .60650 0.25 .05900 Uiso ? ? 1 ? ? H5 .32337 .31664 0.25 .05600 Uiso ? ? 1 ? ? H61 .20302 .06790 0.25 .05900 Uiso ? ? 1 ? ? H62 .07152 .08229 0.12590 .05900 Uiso ? ? 1 ? ? 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 N1 .0228(9) .0302(10) .0208(9) .0055(7) 0 0 N2 .0166(8) .0255(9) .0173(8) .0006(7) 0 0 C3 .0257(10) .0252(10) .0132(9) -.0037(8) 0 0 C4 .0291(12) .0461(14) .0374(13) -.0145(11) 0 0 C5 .0173(10) .0569(16) .0395(13) .0031(10) 0 0 C6 .0478(15) .0274(12) .0478(15) .0118(11) 0 0 N7 .0450(12) .0246(10) .0203(9) -.0003(8) 0 0 O8 .0369(10) .0411(10) .0441(11) .0141(8) 0 0 O9 .0824(16) .0235(9) .0843(16) -.0093(10) 0 0 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C .017 .009 'INTERNATIONAL TABLES FOR X-RAY=' H 0 0 'INTERNATIONAL TABLES FOR X-RAY=' N .029 .018 'INTERNATIONAL TABLES FOR X-RAY=' O .047 .032 'INTERNATIONAL TABLES FOR X-RAY=' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 2 0 0 -2 0 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N2 N1 C5 . . 112.3(2) yes N2 N1 C6 . . 119.7(2) ? C5 N1 C6 . . 128.0(2) ? C3 N2 N1 . . 103.2(2) yes N2 C3 C4 . . 113.8(2) yes N2 C3 N7 . . 119.2(2) yes C4 C3 N7 . . 127.1(2) yes H4 C4 C5 . . 128.6(2) ? H4 C4 C3 . . 128.4(3) ? C5 C4 C3 . . 103.0(2) yes H5 C5 N1 . . 122.8(3) ? H5 C5 C4 . . 129.5(3) ? N1 C5 C4 . . 107.7(2) yes H61 C6 H62 . 6 110.12(17) ? H61 C6 H62 . . 110.12(17) ? H61 C6 N1 . . 107.8(2) ? H62 C6 H62 6 . 108.3(3) ? H62 C6 N1 6 . 110.26(16) ? H62 C6 N1 . . 110.26(16) ? O8 N7 O9 . . 123.5(2) ? O8 N7 C3 . . 119.5(2) ? O9 N7 C3 . . 117.1(2) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 N2 . . 1.335(2) yes N1 C5 . . 1.344(3) yes N1 C6 . . 1.450(3) yes N2 C3 . . 1.319(3) yes C3 C4 . . 1.383(3) yes C3 N7 . . 1.445(3) yes C4 H4 . . .971(3) ? C4 C5 . . 1.358(4) yes C5 H5 . . .924(2) ? C6 H61 . . .973(3) ? C6 H62 . 6 .9734(16) ? C6 H62 . . .9734(16) ? N7 O8 . . 1.212(3) ? N7 O9 . . 1.216(3) ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 H62 H62 1.57761(7) 6 H61 H62 1.59569(6) 6 H61 H62 1.59569(6) . N1 H61 1.9781(18) . N1 H5 2.0010(17) . N1 H62 2.0069(17) 6 N1 H62 2.0069(17) . C4 H5 2.073(3) . N1 C3 2.080(3) . C5 H4 2.105(3) . C3 H4 2.127(2) . O8 O9 2.138(3) . C3 C5 2.146(3) . N1 C4 2.182(3) . N2 C5 2.225(3) . N2 C4 2.264(3) . C3 O9 2.273(3) . C3 O8 2.297(3) . N2 N7 2.384(3) . N2 C6 2.409(3) . H5 H61 2.48363(9) . C5 C6 2.512(4) . C4 N7 2.532(3) . O8 H61 2.5468(18) '3 455' H4 H5 2.55203(11) . O8 H4 2.5670(18) '3 465' C5 H61 2.579(3) . H62 H62 2.61161(7) 5 N2 H62 2.6659(16) . N2 H62 2.6659(16) 6 N2 O8 2.685(2) . N2 H5 2.7466(17) '3 455' O9 H62 2.7519(18) '1 565' O9 H62 2.7519(18) '6 565' O9 H4 2.761(2) . C6 H5 2.761(3) . C4 O9 2.832(3) . H5 H62 2.85897(11) 3 H5 H62 2.85897(11) 8 N7 H4 2.884(2) . H4 H62 2.91611(10) 4 H4 H62 2.91611(10) 7 O9 H62 2.9571(13) '5 565' O9 H62 2.9571(13) '2 565' O9 H61 2.986(2) '1 565' C6 O9 3.000(3) '1 545' C3 H5 3.057(2) . O9 H4 3.080(3) '3 465' N2 H5 3.0942(17) . C5 H62 3.125(3) 6 C5 H62 3.125(3) . N1 H4 3.1277(18) . C6 H5 3.159(3) '3 455' N7 H4 3.184(2) '3 465' N2 H61 3.1870(17) . N2 H4 3.1955(17) . N2 N7 3.2013(4) '2 564' N2 N7 3.2013(4) '2 565' H4 H61 3.20737(15) 4 H4 H61 3.20737(15) '4 556' N1 O8 3.2739(6) '2 564' N1 O8 3.2739(6) '2 565' N2 O8 3.2961(7) '2 564' N2 O8 3.2961(7) '2 565' C4 H61 3.3243(7) '4 556' C4 H61 3.3243(7) 4 C4 H62 3.3321(17) 4 C4 H62 3.3321(17) 7 N1 H5 3.3828(17) '3 455' C6 H4 3.3848(10) '4 546' C6 H4 3.3848(10) '4 545' N7 H62 3.4028(13) '5 565' N7 H62 3.4028(13) '2 565' H5 H62 3.41755(11) . H5 H62 3.41755(11) 6 C3 O8 3.4313(10) '2 565' C3 O8 3.4313(10) '2 564' C5 O8 3.4533(11) '2 565' C5 O8 3.4533(11) '2 564' N2 O9 3.459(2) . N1 N7 3.462(3) . C3 C6 3.466(3) . O9 H5 3.4712(10) 4 O9 H5 3.4712(10) '4 556' O8 H62 3.4757(13) '5 565' O8 H62 3.4757(13) '2 565' H5 H62 3.48429(11) 4 H5 H62 3.48429(11) 7 C6 O8 3.489(3) 3 N2 H61 3.4988(17) '3 455' N1 N7 3.5224(12) '2 564' N1 N7 3.5224(12) '2 565' C4 O8 3.527(3) '3 565' N2 C3 3.5275(12) '2 564' N2 C3 3.5275(12) '2 565' N2 O9 3.5377(12) '2 564' N2 O9 3.5377(12) '2 565' C6 H62 3.547(2) 5 C6 H62 3.547(2) 2 C5 H62 3.558(2) 3 C5 H62 3.558(2) 8 C5 N7 3.562(3) . C4 O8 3.5698(14) '2 564' C4 O8 3.5698(14) '2 565' C3 N7 3.5808(13) '2 565' C3 N7 3.5808(13) '2 564' C4 O8 3.595(3) . C4 C6 3.599(4) . C5 H62 3.603(2) 7 C5 H62 3.603(2) 4 N7 H61 3.619(2) '3 455' O8 O9 3.625(3) '3 465' C3 C3 3.6276(14) '2 565' C3 C3 3.6276(14) '2 564' N1 H4 3.6569(9) '4 546' N1 H4 3.6569(9) '4 545' N2 C5 3.659(3) '3 455' C5 H61 3.6724(14) 4 C5 H61 3.6724(14) '4 556' C4 C6 3.728(2) 4 C4 C6 3.728(2) '4 556' C6 O9 3.745(2) '2 565' C6 O9 3.745(2) '2 564' N1 O9 3.7481(16) '2 564' N1 O9 3.7481(16) '2 565' C3 H62 3.810(2) 6 C3 H62 3.810(2) . O8 H62 3.8353(18) '3 455' O8 H62 3.8353(18) '8 455' C4 H61 3.864(3) . C6 O8 3.8655(17) '2 564' C6 O8 3.8655(17) '2 565' C5 H4 3.8744(16) '4 546' C5 H4 3.8744(16) '4 545' O8 H5 3.8823(10) '2 564' O8 H5 3.8823(10) '2 565' O8 H5 3.8830(18) '3 455' N7 H62 3.8831(18) '1 565' N7 H62 3.8831(18) '6 565' N2 N2 3.8994(14) '2 565' N2 N2 3.8994(14) '2 564' C3 H61 3.9232(12) '4 556' C3 H61 3.9232(12) 4 C5 O9 3.928(2) '4 546' C5 O9 3.928(2) '4 545' C4 O9 3.929(3) '3 565' C4 H62 3.933(2) 3 C4 H62 3.933(2) 8 C5 C6 3.939(4) 3 C3 H5 3.944(2) '3 455' N7 H5 3.9604(12) '4 556' N7 H5 3.9604(12) 4 C6 N7 3.966(2) '2 564' C6 N7 3.966(2) '2 565' N1 O8 3.976(3) . C5 N7 4.075(2) '2 564' C5 N7 4.075(2) '2 565' N7 N7 4.0819(17) '2 565' N7 N7 4.0819(17) '2 564' C5 C6 4.103(2) '4 556' C5 C6 4.103(2) 4 C5 O9 4.107(3) . C4 N7 4.137(2) '2 564' C4 N7 4.137(2) '2 565' C4 N7 4.142(3) '3 565' N7 O8 4.1635(17) '2 564' N7 O8 4.1635(17) '2 565' C6 N7 4.200(3) '1 545' N2 C4 4.204(2) '2 565' N2 C4 4.204(2) '2 564' N1 C4 4.221(2) '4 545' N1 C4 4.221(2) '4 546' C3 O9 4.277(2) '2 565' C3 O9 4.277(2) '2 564' N1 C3 4.2793(18) '2 564' N1 C3 4.2793(18) '2 565' N1 C5 4.293(3) '3 455' N1 O9 4.346(3) . N2 C6 4.350(3) '3 455' C4 C5 4.377(3) 4 C4 C5 4.377(3) '4 556' C3 O8 4.402(3) '3 565' C4 C6 4.403(4) 3 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _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 C4 H4 O8 1_555 1_555 3_565 .97 2.57 3.527(3) 170 yes C6 H61 O8 1_555 1_555 3_555 .97 2.55 3.489(3) 163 yes C5 H5 N2 1_555 1_555 3_555 .92 2.75 3.659(3) 169 no C6 H62 O9 1_555 1_555 1_545 .97 2.75 3.000(3) 95 no 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_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C5 N1 N2 C3 . -.00006 ? C6 N1 N2 C3 . 180.0000 ? N2 N1 C5 C4 . -.00006 ? N2 N1 C5 H5 . 180.0000 ? C6 N1 C5 C4 . 180.0000 ? C6 N1 C5 H5 . -.00006 ? N2 N1 C6 H61 . 180 yes N2 N1 C6 H62 . 60 yes N2 N1 C6 H62 6 -60 ? C5 N1 C6 H61 . .00006 ? C5 N1 C6 H62 . -120.26(19) ? C5 N1 C6 H62 6 120.26(19) ? N1 N2 C3 C4 . -.00006 ? N1 N2 C3 N7 . 180.0000 ? N2 C3 C4 C5 . -.00006 ? N2 C3 C4 H4 . 180.0000 ? N7 C3 C4 C5 . 180.0000 ? N7 C3 C4 H4 . -.00006 ? N2 C3 N7 O8 . .0(2) yes N2 C3 N7 O9 . 180.0000 ? C4 C3 N7 O8 . 180.0000 ? C4 C3 N7 O9 . -.00006 ? C3 C4 C5 N1 . -.00006 ? C3 C4 C5 H5 . 180.0000 ? H4 C4 C5 N1 . 180.0000 ? H4 C4 C5 H5 . -.00006 ?