#------------------------------------------------------------------------------ #$Date: 2014-07-15 22:48:18 +0300 (Tue, 15 Jul 2014) $ #$Revision: 120443 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/03/7150363.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7150363 loop_ _publ_author_name 'Reisinger, Ales' 'Koch, Rainer' 'Bernhardt, Paul V.' 'Wentrup, Curt' _publ_section_title ; 1H-1,3-diazepines, 5H-1,3-diazepines, 1,3-diazepinones, and 2,4-diazabicyclo[3.2.0]heptenes. ; _journal_issue 8 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 1227 _journal_page_last 1238 _journal_volume 2 _journal_year 2004 _chemical_compound_source 'synthesis as described' _chemical_formula_moiety 'C8 H6 F6 N2 O1' _chemical_formula_structural 'C8 H6 N2 F6 O' _chemical_formula_sum 'C8 H6 F6 N2 O' _chemical_formula_weight 260.15 _chemical_name_common 5,6-Bis(trifluoromethyl)-2-methoxy-1H-1,3-diazepine _chemical_name_systematic ; 5,6-Bis(trifluoromethyl)-2-methoxy-1H-1,3-diazepine ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_creation_date 2003-12-04T13:45:15-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 91.89(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.642(7) _cell_length_b 10.277(7) _cell_length_c 10.081(7) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 14.35 _cell_measurement_theta_min 10.11 _cell_measurement_wavelength 0.71073 _cell_volume 998.4(12) _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius TurboCAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_UB_11 -0.100852 _diffrn_orient_matrix_UB_12 -0.22196E-1 _diffrn_orient_matrix_UB_13 0.1608E-2 _diffrn_orient_matrix_UB_21 0.23993E-1 _diffrn_orient_matrix_UB_22 -0.88742E-1 _diffrn_orient_matrix_UB_23 0.34445E-1 _diffrn_orient_matrix_UB_31 -0.3344E-2 _diffrn_orient_matrix_UB_32 0.33249E-1 _diffrn_orient_matrix_UB_33 0.93055E-1 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_unetI/netI 0.0162 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 1854 _diffrn_reflns_theta_full 24.98 _diffrn_reflns_theta_max 24.98 _diffrn_reflns_theta_min 2.11 _diffrn_source 'Enraf Nonius FR590' _diffrn_standards_decay_% 16 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.191 _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.731 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 520 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.5 _refine_diff_density_max 0.427 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.111 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.1 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 155 _refine_ls_number_reflns 1746 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.1 _refine_ls_R_factor_all 0.0653 _refine_ls_R_factor_gt 0.0494 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0952P)^2^+0.4063P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.149 _refine_ls_wR_factor_ref 0.1637 _reflns_number_gt 1331 _reflns_number_total 1746 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file b317099c.txt _[local]_cod_data_source_block 965reis4 _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 7150363 _diffrn_standards_decay_corr_max 1.233 _diffrn_standards_decay_corr_min 1 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_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2 C 0.6697(2) 0.2410(2) 0.2761(2) 0.0351(5) Uani 1 1 d . . . C4 C 0.6834(3) 0.0649(3) 0.4172(2) 0.0437(6) Uani 1 1 d . . . H4 H 0.6261 0.0332 0.4822 0.052 Uiso 1 1 calc R . . C5 C 0.7610(3) -0.0240(2) 0.3599(2) 0.0440(6) Uani 1 1 d . . . C6 C 0.8534(3) 0.0096(2) 0.2498(2) 0.0429(6) Uani 1 1 d . . . C7 C 0.8175(3) 0.0991(3) 0.1601(2) 0.0424(6) Uani 1 1 d . . . H7 H 0.8777 0.1148 0.0917 0.051 Uiso 1 1 calc R . . C8 C 0.5865(3) 0.4447(3) 0.3507(3) 0.0586(8) Uani 1 1 d . . . H8A H 0.5126 0.4015 0.3947 0.088 Uiso 1 1 calc R . . H8B H 0.553 0.5254 0.3139 0.088 Uiso 1 1 calc R . . H8C H 0.6613 0.4617 0.4135 0.088 Uiso 1 1 calc R . . C9 C 0.7460(4) -0.1623(3) 0.4001(3) 0.0680(9) Uani 1 1 d . . . C10 C 0.9928(4) -0.0513(4) 0.2414(3) 0.0656(9) Uani 1 1 d . . . N1 N 0.6949(2) 0.1712(2) 0.16221(18) 0.0404(5) Uani 1 1 d . . . H1 H 0.6825 0.2142 0.0972 0.048 Uiso 1 1 d R . . N3 N 0.6744(2) 0.1987(2) 0.39498(18) 0.0396(5) Uani 1 1 d . . . O2 O 0.63525(19) 0.36271(17) 0.24566(17) 0.0459(5) Uani 1 1 d . . . F1 F 0.6465(3) -0.1801(2) 0.4868(3) 0.1103(9) Uani 1 1 d . . . F2 F 0.8597(3) -0.2135(2) 0.4559(3) 0.1049(9) Uani 1 1 d . . . F3 F 0.7130(3) -0.2382(2) 0.2970(2) 0.1057(9) Uani 1 1 d . . . F4 F 1.0662(2) -0.0436(3) 0.3536(2) 0.1084(10) Uani 1 1 d . . . F5 F 0.9893(3) -0.1760(2) 0.2105(3) 0.1016(8) Uani 1 1 d . . . F6 F 1.0682(2) 0.0022(3) 0.1472(3) 0.0997(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0369(12) 0.0368(12) 0.0317(12) -0.0017(9) 0.0011(9) -0.0016(10) C4 0.0553(15) 0.0461(15) 0.0299(12) 0.0035(10) 0.0023(10) -0.0011(12) C5 0.0577(15) 0.0395(14) 0.0343(12) 0.0007(10) -0.0063(11) 0.0020(11) C6 0.0509(15) 0.0435(14) 0.0341(13) -0.0075(10) -0.0017(10) 0.0045(11) C7 0.0517(14) 0.0454(14) 0.0305(12) -0.0087(10) 0.0058(10) -0.0011(11) C8 0.0713(19) 0.0482(16) 0.0563(17) -0.0071(13) 0.0001(14) 0.0200(14) C9 0.094(2) 0.0462(17) 0.0640(19) 0.0100(15) 0.0002(18) 0.0070(16) C10 0.0654(19) 0.076(2) 0.0553(18) -0.0132(16) 0.0009(15) 0.0217(16) N1 0.0561(13) 0.0408(11) 0.0241(9) 0.0026(8) -0.0015(8) 0.0028(9) N3 0.0492(12) 0.0400(12) 0.0298(11) -0.0022(8) 0.0033(8) 0.0020(9) O2 0.0586(11) 0.0384(10) 0.0405(10) 0.0020(7) 0.0002(8) 0.0072(8) F1 0.148(2) 0.0653(14) 0.120(2) 0.0400(13) 0.0487(18) 0.0027(14) F2 0.136(2) 0.0759(16) 0.1013(17) 0.0286(12) -0.0167(15) 0.0394(14) F3 0.172(2) 0.0449(11) 0.0992(17) -0.0075(11) -0.0106(16) -0.0147(13) F4 0.0716(13) 0.173(3) 0.0787(15) -0.0346(15) -0.0283(11) 0.0443(15) F5 0.1167(19) 0.0740(14) 0.1136(18) -0.0234(13) -0.0043(15) 0.0475(13) F6 0.0709(14) 0.128(2) 0.1019(18) 0.0058(14) 0.0322(13) 0.0321(13) 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 Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables 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 -5 -3 1 3 -3 4 -1 1 6 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 C2 O2 122.7(2) . . ? N3 C2 N1 127.0(2) . . ? O2 C2 N1 110.30(19) . . ? C5 C4 N3 130.0(2) . . ? C4 C5 C9 118.6(3) . . ? C4 C5 C6 121.7(2) . . ? C9 C5 C6 119.4(3) . . ? C7 C6 C5 121.3(2) . . ? C7 C6 C10 118.0(3) . . ? C5 C6 C10 120.7(2) . . ? C6 C7 N1 124.0(2) . . ? F2 C9 F3 105.8(3) . . ? F2 C9 F1 105.7(3) . . ? F3 C9 F1 105.8(3) . . ? F2 C9 C5 114.2(3) . . ? F3 C9 C5 111.8(3) . . ? F1 C9 C5 112.9(3) . . ? F4 C10 F5 105.7(3) . . ? F4 C10 F6 107.3(3) . . ? F5 C10 F6 104.1(3) . . ? F4 C10 C6 112.7(2) . . ? F5 C10 C6 113.9(3) . . ? F6 C10 C6 112.5(3) . . ? C2 N1 C7 117.42(19) . . ? C2 N3 C4 119.2(2) . . ? C2 O2 C8 117.7(2) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 N3 1.275(3) . ? C2 O2 1.327(3) . ? C2 N1 1.382(3) . ? C4 C5 1.325(4) . ? C4 N3 1.396(3) . ? C5 C9 1.486(4) . ? C5 C6 1.487(4) . ? C6 C7 1.328(4) . ? C6 C10 1.488(4) . ? C7 N1 1.395(3) . ? C8 O2 1.444(3) . ? C9 F2 1.325(4) . ? C9 F3 1.330(4) . ? C9 F1 1.332(4) . ? C10 F4 1.317(4) . ? C10 F5 1.320(4) . ? C10 F6 1.333(4) . ? _journal_paper_doi 10.1039/b317099c