#------------------------------------------------------------------------------ #$Date: 2015-12-12 22:44:01 +0000 (Sat, 12 Dec 2015) $ #$Revision: 171462 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/13/2011320.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_2011320 loop_ _publ_author_name 'Lah, Nina' 'Leban, Ivan' 'Majcen-Le Mar\'echal, Alenka' 'Le Grel, Philippe' 'Robert, Albert' 'Sieler, Joachim' 'Giester, Gerald' _publ_section_title ; From \a-carbamoyl-\a-cyanooxiranes to 3-halogenopyruvamides ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1164 _journal_page_last 1167 _journal_paper_doi 10.1107/S0108270100008623 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C10 H7 Cl N2 O2' _chemical_formula_sum 'C10 H7 Cl N2 O2' _chemical_formula_weight 222.63 _chemical_name_systematic ; 3-(4-chlorophenyl)-2-cyano-2,3-epoxypropanamide ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _audit_creation_method SHELX-97 _cell_angle_alpha 90.00 _cell_angle_beta 93.540(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.9992(8) _cell_length_b 12.694(3) _cell_length_c 16.442(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 15 _cell_measurement_theta_min 10 _cell_volume 1041.4(4) _computing_cell_refinement DIF4 _computing_data_collection 'DIF4 (Stoe, 1992)' _computing_data_reduction 'REDU4 (Stoe, 1992)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device_type STADI4(STOE) _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0251 _diffrn_reflns_av_sigmaI/netI .0203 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 3492 _diffrn_reflns_theta_full 29.15 _diffrn_reflns_theta_max 28.0 _diffrn_reflns_theta_min 2.03 _diffrn_standards_decay_% .8 _diffrn_standards_interval_count 300 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .346 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 456 _exptl_crystal_size_max .30 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .25 _refine_diff_density_max .288 _refine_diff_density_min -.337 _refine_ls_extinction_coef .061(6) _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 147 _refine_ls_number_reflns 2533 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.032 _refine_ls_R_factor_all .0683 _refine_ls_R_factor_gt .0478 _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^)+(0.0811P)^2^+0.2445P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1515 _reflns_number_gt 1852 _reflns_number_total 2533 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file gd1105.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_geom_hbond_publ_flag' value 'Y' changed to 'y' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (2 times). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0811P)^2^+0.2445P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0811P)^2^+0.2445P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_database_code 2011320 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' 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 N1 .7265(3) .03484(16) -.41529(10) .0612(5) Uani d . 1 . . N H1 .7222 .0306 -.4676 .068(7) Uiso calc R 1 . . H H2 .8713 .0541 -.3884 .083(8) Uiso calc R 1 . . H C1 .5113(3) .01177(14) -.37641(11) .0460(4) Uani d . 1 . . C O1 .2951(2) -.01638(12) -.40846(8) .0591(4) Uani d . 1 . . O C2 .5379(3) .02381(14) -.28500(10) .0458(4) Uani d . 1 . . C C10 .3935(4) -.05536(15) -.24065(11) .0534(4) Uani d . 1 . . C N2 .2806(5) -.11797(15) -.20777(13) .0795(6) Uani d . 1 . . N C3 .5770(4) .13093(15) -.24897(12) .0521(4) Uani d . 1 . . C H3 .5857 .1889 -.2882 .065(6) Uiso calc R 1 . . H O2 .7912(2) .05587(13) -.24926(8) .0618(4) Uani d . 1 . . O C4 .4738(4) .15929(14) -.16894(11) .0508(4) Uani d . 1 . . C C5 .2670(4) .23174(16) -.16634(13) .0577(5) Uani d . 1 . . C H5 .1976 .2631 -.2142 .054(5) Uiso calc R 1 . . H C6 .1631(4) .25776(17) -.09257(15) .0644(5) Uani d . 1 . . C H6 .0219 .3052 -.0907 .092(8) Uiso calc R 1 . . H C7 .2730(4) .21197(17) -.02199(13) .0607(5) Uani d . 1 . . C C8 .4810(5) .14142(18) -.02315(12) .0642(5) Uani d . 1 . . C H8 .5532 .1118 .0251 .081(7) Uiso calc R 1 . . H C9 .5820(4) .11482(17) -.09691(12) .0601(5) Uani d . 1 . . C H9 .7226 .0670 -.0983 .075(7) Uiso calc R 1 . . H Cl .13798(15) .24047(7) .07086(4) .0936(3) Uani d . 1 . . Cl 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 .0338(7) .0949(13) .0556(9) -.0122(7) .0080(6) -.0042(8) C1 .0327(7) .0515(9) .0544(9) .0011(6) .0065(6) -.0012(7) O1 .0327(6) .0863(10) .0589(7) -.0083(6) .0072(5) -.0086(7) C2 .0344(7) .0494(9) .0537(9) .0004(6) .0045(6) .0023(7) C10 .0597(10) .0432(9) .0586(10) .0059(8) .0140(8) .0004(8) N2 .1039(15) .0507(10) .0877(13) -.0041(10) .0376(11) .0039(9) C3 .0487(9) .0516(10) .0560(10) -.0070(7) .0028(7) .0024(8) O2 .0366(6) .0857(10) .0626(7) .0000(6) -.0006(5) -.0085(7) C4 .0502(9) .0456(9) .0567(10) -.0089(7) .0044(7) -.0022(7) C5 .0561(10) .0504(10) .0665(11) -.0034(8) .0026(8) .0027(9) C6 .0577(11) .0549(11) .0815(14) .0004(9) .0117(9) -.0070(10) C7 .0627(11) .0571(11) .0635(11) -.0100(9) .0119(9) -.0127(9) C8 .0729(13) .0637(12) .0555(11) -.0009(10) .0009(9) -.0017(9) C9 .0600(10) .0581(11) .0618(11) .0051(9) .0017(8) -.0028(9) Cl .0949(5) .1114(6) .0768(4) .0013(4) .0235(3) -.0278(4) 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' Cl Cl .1484 .1585 '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 C1 N1 H1 120.0 ? C1 N1 H2 120.0 ? H1 N1 H2 120.0 ? O1 C1 N1 125.49(17) yes O1 C1 C2 118.63(14) yes N1 C1 C2 115.87(15) yes O2 C2 C10 116.49(15) yes O2 C2 C3 58.89(11) yes C10 C2 C3 119.11(15) yes O2 C2 C1 117.53(13) yes C10 C2 C1 114.35(15) yes C3 C2 C1 119.31(15) yes N2 C10 C2 178.5(2) yes O2 C3 C4 117.63(16) yes O2 C3 C2 58.15(11) yes C4 C3 C2 121.88(16) yes O2 C3 H3 115.7 ? C4 C3 H3 115.7 ? C2 C3 H3 115.7 ? C2 O2 C3 62.96(11) yes C5 C4 C9 119.63(18) yes C5 C4 C3 119.20(17) yes C9 C4 C3 121.16(18) yes C4 C5 C6 120.31(19) yes C4 C5 H5 119.8 ? C6 C5 H5 119.8 ? C7 C6 C5 118.9(2) yes C7 C6 H6 120.6 ? C5 C6 H6 120.6 ? C8 C7 C6 121.66(19) yes C8 C7 Cl 118.78(17) yes C6 C7 Cl 119.51(17) yes C7 C8 C9 119.3(2) yes C7 C8 H8 120.4 ? C9 C8 H8 120.4 ? C8 C9 C4 120.2(2) yes C8 C9 H9 119.9 ? C4 C9 H9 119.9 ? 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 N1 C1 . 1.318(2) yes N1 H1 . .8600 ? N1 H2 . .8600 ? C1 O1 . 1.226(2) yes C1 C2 . 1.508(2) yes C2 O2 . 1.422(2) yes C2 C10 . 1.459(2) yes C2 C3 . 1.491(3) yes C10 N2 . 1.132(3) yes C3 O2 . 1.434(2) yes C3 C4 . 1.487(3) yes C3 H3 . .9800 ? C4 C5 . 1.386(3) yes C4 C9 . 1.391(3) yes C5 C6 . 1.389(3) yes C5 H5 . .9300 ? C6 C7 . 1.381(3) yes C6 H6 . .9300 ? C7 C8 . 1.373(3) yes C7 Cl . 1.745(2) yes C8 C9 . 1.384(3) yes C8 H8 . .9300 ? C9 H9 . .9300 ? 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 H2 O2 . .86 2.35 2.742(2) 108.4 ? N1 H2 O1 1_655 .86 2.34 2.911(2) 124.0 y N1 H1 O1 3_654 .86 2.04 2.903(2) 178.2 y