#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/00/90/2009011.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_2009011 loop_ _publ_author_name 'Linden, Anthony' 'Moya Argilagos, Dally' 'Heimgartner, Heinz' 'Garc\'ia Trimi\~no, Mar\'ia I.' 'Mac\'ias Cabrera, Arturo' _publ_section_title ; `Push--pull' effects in nitroethenamines ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1692 _journal_page_last 1698 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C4 H8 N2 O2 S ' _chemical_formula_sum 'C4 H8 N2 O2 S' _chemical_formula_weight 148.18 _chemical_melting_point 384.5(5) _chemical_name_systematic ' (E)-N-methyl-1-(methylthio)-2-nitroethenylamine' _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 90.65(3) _cell_angle_beta 106.53(3) _cell_angle_gamma 105.69(3) _cell_formula_units_Z 2 _cell_length_a 7.105(3) _cell_length_b 8.690(3) _cell_length_c 5.777(2) _cell_measurement_reflns_used 21 _cell_measurement_temperature 173.0(10) _cell_measurement_theta_max 20.0 _cell_measurement_theta_min 19.5 _cell_volume 327.7(2) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1989)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 173.0(10) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Rigaku AFC-5R' _diffrn_measurement_method '\w/2\q scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rigaku rotating anode generator' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.012 _diffrn_reflns_av_sigmaI/netI 0.018 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 2044 _diffrn_reflns_theta_full 30.0 _diffrn_reflns_theta_max 30 _diffrn_reflns_theta_min 2.5 _diffrn_standards_decay_% insignificant _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.419 _exptl_absorpt_correction_type none _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 156 _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.545 _refine_diff_density_min -0.220 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.208 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 88 _refine_ls_number_reflns 1902 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.208 _refine_ls_R_factor_all 0.043 _refine_ls_R_factor_gt 0.036 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0454P)^2^+0.1545P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.108 _reflns_number_gt 1693 _reflns_number_total 1902 _reflns_threshold_expression 'I > 2\s(I)' _[local]_cod_data_source_file fg1546.cif _[local]_cod_data_source_block 1a _[local]_cod_chemical_formula_sum_orig 'C4 H8 N2 O2 S ' _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '384-385' was changed to '384.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '384-385' was changed to '384.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2009011 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-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_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol S .15312(7) .17553(5) .22936(8) .02946(14) Uani d . 1 . . S O1 .3617(2) .56934(15) .8449(2) .0321(3) Uani d . 1 . . O O2 .2706(2) .73298(14) .5802(2) .0317(3) Uani d . 1 . . O N1 .3454(2) .27745(16) .6846(3) .0251(3) Uani d . 1 . . N H1 .388(4) .347(3) .799(4) .037(6) Uiso d . 1 . . H N2 .2888(2) .59665(15) .6275(3) .0237(3) Uani d . 1 . . N C1 .3782(3) .1198(2) .7192(3) .0311(3) Uani d . 1 . . C H11 .2460 .0368 .6670 .047 Uiso calc R 1 . . H H12 .4456 .1145 .8911 .047 Uiso calc R 1 . . H H13 .4649 .1020 .6226 .047 Uiso calc R 1 . . H C2 .2254(2) .47630(18) .4436(3) .0243(3) Uani d . 1 . . C H2 .1618 .4985 .2843 .029 Uiso calc R 1 . . H C3 .2489(2) .32235(18) .4764(3) .0222(3) Uani d . 1 . . C C4 -.0038(3) .2610(2) -.0042(3) .0313(3) Uani d . 1 . . C H41 -.0666 .1846 -.1498 .047 Uiso calc R 1 . . H H42 .0810 .3605 -.0429 .047 Uiso calc R 1 . . H H43 -.1115 .2845 .0527 .047 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 S .0331(2) .0226(2) .0307(2) .00864(15) .00617(16) -.00413(14) O1 .0395(7) .0273(6) .0259(6) .0117(5) .0022(5) -.0008(4) O2 .0383(7) .0185(5) .0385(7) .0100(5) .0098(5) .0027(4) N1 .0282(6) .0193(6) .0281(7) .0076(5) .0082(5) .0011(5) N2 .0219(6) .0187(6) .0294(6) .0048(5) .0071(5) .0009(5) C1 .0392(9) .0230(7) .0353(9) .0134(7) .0130(7) .0056(6) C2 .0245(7) .0202(7) .0262(7) .0060(5) .0051(5) .0002(5) C3 .0197(6) .0199(6) .0272(7) .0040(5) .0089(5) .0000(5) C4 .0325(8) .0312(8) .0279(8) .0100(7) .0049(6) -.0028(6) 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 S C3 . 1.7505(17) yes S C4 . 1.7973(19) yes O1 N2 . 1.2667(19) ? O2 N2 . 1.2510(17) ? N1 C1 . 1.457(2) yes N1 C3 . 1.325(2) yes N1 H1 . .82(3) ? N2 C2 . 1.369(2) yes C1 H11 . .9800 ? C1 H12 . .9800 ? C1 H13 . .9800 ? C2 C3 . 1.401(2) yes C2 H2 . .9500 ? C4 H41 . .9800 ? C4 H42 . .9800 ? C4 H43 . .9800 ? 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 for Crystallography (1992). Vol.C, Tables 4.2.6.8 and 6.1.1.4 ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol.C, Tables 4.2.6.8 and 6.1.1.4 ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol.C, Tables 4.2.6.8 and 6.1.1.4 ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992). Vol.C, Tables 4.2.6.8 and 6.1.1.4 ; S S 0.1246 0.1234 ; International Tables for Crystallography (1992). Vol.C, Tables 4.2.6.8 and 6.1.1.4 ; loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 -2 0 1 -2 -1 -1 -2 -1 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 C3 S C4 104.11(8) yes C3 N1 C1 125.24(14) yes C3 N1 H1 114.3(17) ? C1 N1 H1 120.5(17) ? O2 N2 O1 120.19(14) ? O2 N2 C2 119.59(14) ? O1 N2 C2 120.20(13) ? N1 C1 H11 109.5 ? N1 C1 H12 109.5 ? H11 C1 H12 109.5 ? N1 C1 H13 109.5 ? H11 C1 H13 109.5 ? H12 C1 H13 109.5 ? N2 C2 C3 123.83(14) yes N2 C2 H2 118.1 ? C3 C2 H2 118.1 ? N1 C3 C2 124.67(14) yes N1 C3 S 115.49(12) yes C2 C3 S 119.81(12) yes S C4 H41 109.5 ? S C4 H42 109.5 ? H41 C4 H42 109.5 ? S C4 H43 109.5 ? H41 C4 H43 109.5 ? H42 C4 H43 109.5 ? 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 H1 O1 . 0.82(3) 2.01(2) 2.652(2) 135(2) yes N1 H1 O1 2_667 0.82(3) 2.26(2) 2.948(2) 142(2) yes 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 O2 N2 C2 C3 176.61(14) ? O1 N2 C2 C3 -4.8(2) yes C1 N1 C3 C2 -177.36(15) ? C1 N1 C3 S 0.8(2) ? N2 C2 C3 N1 -4.3(2) ? N2 C2 C3 S 177.58(12) ? C4 S C3 N1 170.23(12) ? C4 S C3 C2 -11.48(15) yes _cod_database_fobs_code 2009011 _journal_paper_doi 10.1107/S0108270199006861