#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2200239.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_2200239 loop_ _publ_author_name 'Tu, Shu-Jiang' 'Deng, Xu' 'Fang, Ya-Yin' 'Guo, Ya-Mei' 'Du, Miao' 'Liu, Xiao-Hong' _publ_section_title ; 2-Amino-7,7-dimethyl-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o358 _journal_page_last o359 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C18 H18 N2 O2' _chemical_formula_moiety 'C18 H18 N2 O2' _chemical_formula_sum 'C18 H18 N2 O2' _chemical_formula_weight 294.34 _chemical_name_systematic ;2-Amino-7,7-dimethyl-4-benzyl-5-oxo-4,5,6,8-tetrahydro-7H-chromene -3-carbornitrile ; _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' _cell_angle_alpha 90.00 _cell_angle_beta 99.340(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.3070(10) _cell_length_b 9.4750(10) _cell_length_c 14.919(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 15.05 _cell_measurement_theta_min 3.27 _cell_volume 1577.1(3) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker SMART 1000' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0134 _diffrn_reflns_av_sigmaI/netI .0303 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 3252 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 1.83 _diffrn_standards_decay_% 2.67 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .082 _exptl_absorpt_correction_type none _exptl_absorpt_process_details 'SAINT (Bruker 1998) and SADABS (Sheldrick, 1997)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 624 _exptl_crystal_size_max .56 _exptl_crystal_size_mid .50 _exptl_crystal_size_min .40 _refine_diff_density_max .186 _refine_diff_density_min -.135 _refine_ls_extinction_coef .044(3) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 208 _refine_ls_number_reflns 2783 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.021 _refine_ls_R_factor_all .0581 _refine_ls_R_factor_gt .0381 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0561P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1023 _reflns_number_gt 1942 _reflns_number_total 2783 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file wn6009.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: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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 2200239 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_type_symbol O1 .38594(9) .19829(12) .53586(7) .0478(3) Uani d . 1 O O2 .39678(10) .42950(13) .81702(8) .0578(4) Uani d . 1 O N1 -.00294(13) .07976(16) .59525(10) .0590(4) Uani d . 1 N N2 .24217(15) .06252(18) .46297(11) .0604(5) Uani d . 1 N C1 .09420(14) .48169(19) .69650(12) .0554(5) Uani d . 1 C H1 .0781 .4273 .7450 .067 Uiso calc R 1 H C2 .03121(17) .6051(2) .67480(15) .0680(6) Uani d . 1 C H2 -.0275 .6321 .7084 .082 Uiso calc R 1 H C3 .05366(18) .6873(2) .60535(13) .0681(6) Uani d . 1 C H3 .0103 .7699 .5908 .082 Uiso calc R 1 H C4 .1409(2) .6476(2) .55686(15) .0919(8) Uani d . 1 C H4 .1587 .7043 .5100 .110 Uiso calc R 1 H C5 .2025(2) .5232(2) .57764(13) .0809(7) Uani d . 1 C H5 .2606 .4962 .5435 .097 Uiso calc R 1 H C6 .18021(13) .43816(17) .64756(10) .0411(4) Uani d . 1 C C7 .24657(13) .29886(15) .66897(10) .0385(4) Uani d . 1 C H7 .2291 .2648 .7275 .046 Uiso calc R 1 H C8 .20547(13) .18659(16) .59795(10) .0397(4) Uani d . 1 C C9 .27108(13) .14927(17) .53365(10) .0425(4) Uani d . 1 C C10 .44066(13) .26733(15) .61272(10) .0386(4) Uani d . 1 C C11 .38057(13) .31358(15) .67676(10) .0371(4) Uani d . 1 C C12 .44793(15) .38037(16) .75796(10) .0434(4) Uani d . 1 C C13 .58247(14) .3810(2) .76731(11) .0563(5) Uani d . 1 C H13A .6132 .2940 .7965 .068 Uiso calc R 1 H H13B .6136 .4585 .8067 .068 Uiso calc R 1 H C14 .62930(14) .39550(18) .67704(11) .0473(4) Uani d . 1 C C15 .57150(13) .28023(17) .61307(11) .0465(4) Uani d . 1 C H15A .5853 .3008 .5519 .056 Uiso calc R 1 H H15B .6096 .1907 .6312 .056 Uiso calc R 1 H C16 .09006(14) .12739(17) .59504(10) .0428(4) Uani d . 1 C C17 .59603(18) .5406(2) .63562(14) .0682(6) Uani d . 1 C H17A .5105 .5515 .6259 .102 Uiso calc R 1 H H17B .6246 .5487 .5787 .102 Uiso calc R 1 H H17C .6321 .6128 .6763 .102 Uiso calc R 1 H C18 .76479(16) .3782(3) .69277(15) .0805(7) Uani d . 1 C H18A .7855 .2872 .7189 .121 Uiso calc R 1 H H18B .8007 .4504 .7334 .121 Uiso calc R 1 H H18C .7936 .3860 .6359 .121 Uiso calc R 1 H H2A .2899(17) .056(2) .4222(13) .068(6) Uiso d . 1 H H2B .1700(16) .0265(18) .4520(11) .054(5) Uiso d . 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 O1 .0410(6) .0565(7) .0487(6) -.0109(5) .0161(5) -.0157(6) O2 .0618(8) .0685(8) .0462(7) -.0064(6) .0177(6) -.0128(6) N1 .0507(9) .0708(11) .0583(9) -.0157(8) .0175(7) -.0097(8) N2 .0487(10) .0773(12) .0588(10) -.0214(9) .0198(8) -.0297(9) C1 .0545(11) .0535(11) .0642(11) .0079(9) .0271(9) .0057(9) C2 .0611(12) .0657(13) .0834(14) .0199(10) .0302(11) .0015(11) C3 .0761(14) .0589(12) .0682(13) .0283(11) .0089(11) .0016(10) C4 .130(2) .0824(16) .0735(15) .0496(15) .0457(14) .0345(13) C5 .1047(17) .0796(15) .0706(14) .0456(13) .0508(13) .0277(12) C6 .0407(9) .0445(9) .0386(8) .0023(7) .0079(7) -.0027(7) C7 .0398(8) .0409(9) .0366(8) .0006(7) .0120(6) .0015(7) C8 .0358(8) .0403(8) .0442(9) -.0028(7) .0104(7) -.0014(7) C9 .0407(9) .0420(9) .0457(9) -.0049(7) .0099(7) -.0019(8) C10 .0396(8) .0340(8) .0424(9) -.0020(7) .0072(7) -.0020(7) C11 .0382(8) .0351(8) .0385(9) .0007(7) .0081(7) .0000(7) C12 .0496(10) .0427(9) .0388(9) -.0028(8) .0103(7) .0007(7) C13 .0488(10) .0706(12) .0486(10) -.0096(9) .0052(8) -.0046(9) C14 .0399(9) .0521(10) .0502(10) -.0083(8) .0086(7) -.0060(8) C15 .0393(9) .0456(10) .0563(10) .0002(7) .0129(8) -.0036(8) C16 .0449(10) .0452(9) .0396(9) -.0012(8) .0102(7) -.0025(7) C17 .0838(15) .0507(11) .0750(13) -.0181(10) .0276(11) -.0065(10) C18 .0438(11) .1192(19) .0783(14) -.0144(12) .0095(10) -.0203(14) 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 C9 O1 C10 118.41(11) yes C6 C1 C2 120.91(17) no C3 C2 C1 120.92(18) no C2 C3 C4 119.17(18) no C3 C4 C5 119.9(2) no C6 C5 C4 121.61(18) no C1 C6 C5 117.49(16) no C1 C6 C7 121.05(14) no C5 C6 C7 121.45(14) no C11 C7 C8 107.96(12) no C11 C7 C6 112.96(12) no C8 C7 C6 112.03(12) no C9 C8 C16 118.97(14) no C9 C8 C7 122.48(13) no C16 C8 C7 118.36(13) no N2 C9 C8 129.01(15) yes N2 C9 O1 109.64(14) yes C8 C9 O1 121.32(14) no C11 C10 O1 122.73(13) no C11 C10 C15 126.46(14) no O1 C10 C15 110.81(12) no C10 C11 C12 118.51(14) no C10 C11 C7 122.50(14) no C12 C11 C7 118.99(13) no O2 C12 C11 121.14(15) yes O2 C12 C13 121.42(15) yes C11 C12 C13 117.40(14) no C12 C13 C14 114.05(14) no C18 C14 C15 109.75(14) no C18 C14 C17 109.57(16) no C15 C14 C17 109.79(14) no C18 C14 C13 109.76(15) no C15 C14 C13 108.16(13) no C17 C14 C13 109.79(15) no C10 C15 C14 112.76(13) no N1 C16 C8 178.11(17) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C9 1.3746(17) yes O1 C10 1.3767(17) yes O2 C12 1.2219(18) yes N1 C16 1.1448(19) yes N2 C9 1.335(2) yes C1 C6 1.371(2) no C1 C2 1.380(2) no C2 C3 1.353(3) no C3 C4 1.368(3) no C4 C5 1.378(3) no C5 C6 1.373(2) no C6 C7 1.526(2) no C7 C11 1.5071(19) no C7 C8 1.520(2) no C8 C9 1.351(2) yes C8 C16 1.415(2) no C10 C11 1.333(2) yes C10 C15 1.4835(19) no C11 C12 1.466(2) no C12 C13 1.505(2) no C13 C14 1.531(2) no C14 C18 1.521(2) no C14 C15 1.526(2) no C14 C17 1.529(2) 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 N2 H2B N1 3_556 .875(17) 2.156(18) 3.021(2) 169.8(15) yes N2 H2A O2 4_565 .88(2) 2.13(2) 3.006(2) 171.6(18) yes