# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2004 data_global _publ_contact_author_email WENTRUP@UQ.EDU.AU _publ_contact_author_name 'Prof Curt Wentrup' _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_address ; Chemistry University of Queensland School of Molecular and Microbial S Coopers Road Brisbane Qld 4072 AUSTRALIA ; _publ_section_title ; 1H-1,3-Diazepines, 5H-1,3-diazepines, 1,3-diazepinones, and 2,4-diazabicyclo[3.2.0]heptenes ; _publ_requested_category FO _publ_author_name 'Curt Wentrup' # compound 4k data_965reis4 _database_code_depnum_ccdc_archive 'CCDC 225886' _chemical_name_common 5,6-Bis(trifluoromethyl)-2-methoxy-1H-1,3-diazepine _audit_creation_date 2003-12-04T13:45:15-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 5,6-Bis(trifluoromethyl)-2-methoxy-1H-1,3-diazepine ; _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_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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' _cell_length_a 9.642(7) _cell_length_b 10.277(7) _cell_length_c 10.081(7) _cell_angle_alpha 90 _cell_angle_beta 91.89(3) _cell_angle_gamma 90 _cell_volume 998.4(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.11 _cell_measurement_theta_max 14.35 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.5 _exptl_crystal_density_diffrn 1.731 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.191 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _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_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius TurboCAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 16 _diffrn_standards_decay_corr_max 1.233 _diffrn_standards_decay_corr_min 1 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 _diffrn_reflns_number 1854 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_unetI/netI 0.0162 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 24.98 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 1746 _reflns_number_gt 1331 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0952P)^2^+0.4063P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1746 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0653 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1637 _refine_ls_wR_factor_gt 0.149 _refine_ls_goodness_of_fit_ref 1.1 _refine_ls_restrained_S_all 1.1 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.427 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.111 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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_ _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) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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) . ? 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) . . ? #===END # Compound 26 # CIF produced by WinGX routine CIF_UPDATE # Created on 2003-12-04 at 13:39:26 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.1 # Request file : c:\wingx\files\archive.dat # CIF files read : 1071al5 dreduc struct data_1071al5 _database_code_depnum_ccdc_archive 'CCDC 225887' _chemical_name_common 6,7-Bis(trifluoromethyl)-2,4-diazabicyclo(3.2.0)heptan-3-one _audit_creation_date 2003-12-04T13:39:26-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 6,7-Bis(trifluoromethyl)-2,4-diazabicyclo[3.2.0]heptan-3-one ; _chemical_formula_moiety 'C7 H6 F6 N2 O1' _chemical_formula_structural 'C7 H6 F6 N2 O1' _chemical_formula_sum 'C7 H6 F6 N2 O' _chemical_formula_weight 248.14 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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' _cell_length_a 13.243(3) _cell_length_b 5.6585(5) _cell_length_c 13.304(3) _cell_angle_alpha 90 _cell_angle_beta 116.610(10) _cell_angle_gamma 90 _cell_volume 891.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.34 _cell_measurement_theta_max 13.17 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.849 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.209 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.72867E-1 _diffrn_orient_matrix_ub_12 -0.745E-3 _diffrn_orient_matrix_ub_13 0.5576E-2 _diffrn_orient_matrix_ub_21 0.41342E-1 _diffrn_orient_matrix_ub_22 -0.44207E-1 _diffrn_orient_matrix_ub_23 0.81145E-1 _diffrn_orient_matrix_ub_31 0.01048 _diffrn_orient_matrix_ub_32 0.170974 _diffrn_orient_matrix_ub_33 0.21087E-1 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius TurboCAD4' _diffrn_measurement_method 'non-profiled omega scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% -3 _diffrn_standards_decay_corr_max 1.01 _diffrn_standards_decay_corr_min 0.949 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 8 0 -2 -2 0 8 3 3 2 _diffrn_reflns_number 1668 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_unetI/netI 0.0479 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 1561 _reflns_number_gt 928 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0595P)^2^+0.0859P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1561 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0909 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1223 _refine_ls_wR_factor_gt 0.101 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.192 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.052 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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_ _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 C1 C 0.8434(2) -0.0656(6) 1.0585(3) 0.0392(8) Uani 1 1 d . . . H1 H 0.862 -0.234 1.0711 0.047 Uiso 1 1 calc R . . C3 C 0.9517(2) 0.2703(6) 1.0881(2) 0.0344(7) Uani 1 1 d . . . C5 C 0.8309(2) 0.0265(5) 0.9436(2) 0.0352(7) Uani 1 1 d . . . H5 H 0.8545 -0.0844 0.9016 0.042 Uiso 1 1 calc R . . C6 C 0.7021(2) 0.0476(6) 0.9014(2) 0.0354(7) Uani 1 1 d . . . H6 H 0.6739 0.2081 0.8772 0.042 Uiso 1 1 calc R . . C7 C 0.7166(3) -0.0103(6) 1.0209(3) 0.0383(8) Uani 1 1 d . . . H7 H 0.6755 -0.155 1.0199 0.046 Uiso 1 1 calc R . . C8 C 0.6355(3) -0.1355(6) 0.8174(3) 0.0431(8) Uani 1 1 d . . . C9 C 0.6876(3) 0.1828(6) 1.0795(3) 0.0482(9) Uani 1 1 d . . . N2 N 0.9277(2) 0.0858(5) 1.1382(2) 0.0446(7) Uani 1 1 d . . . H2 H 0.9531 0.078 1.2058 0.053 Uiso 1 1 d R . . N4 N 0.8941(2) 0.2439(5) 0.9761(2) 0.0392(7) Uani 1 1 d . . . H4 H 0.9112 0.3245 0.9364 0.047 Uiso 1 1 d R . . O3 O 1.01646(18) 0.4339(4) 1.13708(17) 0.0427(6) Uani 1 1 d . . . F1 F 0.67721(17) -0.3521(3) 0.85242(17) 0.0565(6) Uani 1 1 d . . . F2 F 0.63592(19) -0.1049(4) 0.71885(16) 0.0710(7) Uani 1 1 d . . . F3 F 0.52817(16) -0.1408(4) 0.79908(19) 0.0669(7) Uani 1 1 d . . . F4 F 0.7216(2) 0.1358(4) 1.18764(19) 0.0752(7) Uani 1 1 d . . . F5 F 0.73298(17) 0.3917(3) 1.07500(17) 0.0575(6) Uani 1 1 d . . . F6 F 0.57668(18) 0.2200(5) 1.0332(2) 0.0803(8) 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 C1 0.0426(18) 0.0307(17) 0.0387(17) 0.0041(15) 0.0131(14) 0.0023(15) C3 0.0320(16) 0.0409(19) 0.0299(17) -0.0001(15) 0.0136(13) 0.0002(15) C5 0.0420(18) 0.0300(17) 0.0363(17) -0.0049(14) 0.0200(14) -0.0017(14) C6 0.0378(17) 0.0245(16) 0.0431(18) 0.0004(14) 0.0174(14) -0.0006(14) C7 0.0446(18) 0.0308(17) 0.0435(18) 0.0039(15) 0.0233(15) -0.0024(14) C8 0.047(2) 0.037(2) 0.0390(18) 0.0027(16) 0.0134(15) -0.0011(16) C9 0.059(2) 0.040(2) 0.057(2) -0.0015(17) 0.0356(19) -0.0018(17) N2 0.0498(16) 0.0480(17) 0.0288(13) 0.0059(13) 0.0113(12) -0.0065(14) N4 0.0471(15) 0.0413(16) 0.0313(14) -0.0008(13) 0.0195(12) -0.0154(13) O3 0.0474(13) 0.0464(14) 0.0341(11) -0.0058(11) 0.0180(10) -0.0117(12) F1 0.0696(13) 0.0312(11) 0.0598(13) -0.0035(10) 0.0211(10) -0.0016(10) F2 0.0999(17) 0.0652(15) 0.0429(12) -0.0064(11) 0.0276(11) -0.0234(13) F3 0.0406(12) 0.0623(14) 0.0828(15) -0.0096(12) 0.0143(10) -0.0103(10) F4 0.125(2) 0.0624(15) 0.0636(15) -0.0005(12) 0.0646(14) 0.0012(14) F5 0.0825(15) 0.0352(12) 0.0708(14) -0.0063(10) 0.0486(12) -0.0026(10) F6 0.0591(15) 0.0824(18) 0.114(2) -0.0186(15) 0.0517(14) 0.0047(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 N2 1.429(4) . ? C1 C5 1.551(4) . ? C1 C7 1.555(4) . ? C3 O3 1.231(4) . ? C3 N4 1.344(4) . ? C3 N2 1.351(4) . ? C5 N4 1.442(4) . ? C5 C6 1.543(4) . ? C6 C8 1.489(5) . ? C6 C7 1.549(4) . ? C7 C9 1.488(5) . ? C8 F2 1.325(4) . ? C8 F3 1.331(4) . ? C8 F1 1.339(4) . ? C9 F4 1.328(4) . ? C9 F6 1.331(4) . ? C9 F5 1.339(4) . ? 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 N2 C1 C5 103.5(2) . . ? N2 C1 C7 119.3(3) . . ? C5 C1 C7 89.5(2) . . ? O3 C3 N4 125.8(3) . . ? O3 C3 N2 125.6(3) . . ? N4 C3 N2 108.6(3) . . ? N4 C5 C6 116.2(3) . . ? N4 C5 C1 101.5(2) . . ? C6 C5 C1 89.9(2) . . ? C8 C6 C5 113.9(3) . . ? C8 C6 C7 112.5(3) . . ? C5 C6 C7 90.1(2) . . ? C9 C7 C6 116.1(3) . . ? C9 C7 C1 118.3(3) . . ? C6 C7 C1 89.5(2) . . ? F2 C8 F3 107.4(3) . . ? F2 C8 F1 106.3(3) . . ? F3 C8 F1 106.4(3) . . ? F2 C8 C6 112.9(3) . . ? F3 C8 C6 112.2(3) . . ? F1 C8 C6 111.2(3) . . ? F4 C9 F6 107.5(3) . . ? F4 C9 F5 106.5(3) . . ? F6 C9 F5 105.3(3) . . ? F4 C9 C7 112.2(3) . . ? F6 C9 C7 111.4(3) . . ? F5 C9 C7 113.5(3) . . ? C3 N2 C1 112.1(3) . . ? C3 N4 C5 113.1(3) . . ? #===END # compound 129b # CIF produced by WinGX routine CIF_UPDATE # Created on 2003-12-12 at 09:36:41 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.1 # Request file : c:\wingx\files\archive.dat # CIF files read : cw15332 dreduc struct data_cw15332 _database_code_depnum_ccdc_archive 'CCDC 226705' _chemical_name_common 4-Diethylamino-1,5-dihydro-(1,3)diazepin-2-one _audit_creation_date 2003-12-12T09:36:41-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 4-Diethylamino-1,5-dihydro-[1,3]diazepin-2-one ; _chemical_formula_moiety 'C9 H15 N3 O1' _chemical_formula_structural 'C9 H15 N3 O' _chemical_formula_sum 'C9 H15 N3 O' _chemical_formula_weight 181.24 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.607(2) _cell_length_b 8.040(2) _cell_length_c 8.369(1) _cell_angle_alpha 96.79(2) _cell_angle_beta 98.36(3) _cell_angle_gamma 104.70(2) _cell_volume 483.36(18) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.148 _cell_measurement_theta_max 14.361 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 196 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.084 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.26248E-1 _diffrn_orient_matrix_ub_12 -0.128238 _diffrn_orient_matrix_ub_13 0.286E-3 _diffrn_orient_matrix_ub_21 0.13543 _diffrn_orient_matrix_ub_22 0.10589E-1 _diffrn_orient_matrix_ub_23 0.15823E-1 _diffrn_orient_matrix_ub_31 0.7804E-2 _diffrn_orient_matrix_ub_32 0.20249E-1 _diffrn_orient_matrix_ub_33 0.121437 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 7 _diffrn_standards_decay_corr_max 1.072 _diffrn_standards_decay_corr_min 0.988 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 4 0 0 3 -5 1 -1 1 4 _diffrn_reflns_number 1839 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_unetI/netI 0.0309 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 24.98 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 1697 _reflns_number_gt 1181 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0665P)^2^+0.0725P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 1697 _refine_ls_number_parameters 124 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0727 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1244 _refine_ls_wR_factor_gt 0.1088 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.184 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.045 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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' 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 0.4908(3) 0.7457(2) 0.3857(2) 0.0406(5) Uani 1 1 d . . . C4 C 0.6050(3) 0.5089(2) 0.3018(2) 0.0378(5) Uani 1 1 d . . . C5 C 0.7865(3) 0.5839(2) 0.4152(3) 0.0483(5) Uani 1 1 d . . . H5A H 0.8589 0.5005 0.414 0.058 Uiso 1 1 calc R . . H5B H 0.7671 0.6117 0.5261 0.058 Uiso 1 1 calc R . . C6 C 0.8860(3) 0.7455(3) 0.3584(3) 0.0511(5) Uani 1 1 d . . . H6 H 0.9988 0.752 0.3253 0.061 Uiso 1 1 calc R . . C7 C 0.8150(3) 0.8783(3) 0.3549(3) 0.0484(5) Uani 1 1 d . . . H7 H 0.8832 0.9775 0.3218 0.058 Uiso 1 1 calc R . . C8 C 0.4028(3) 0.2874(3) 0.0811(3) 0.0501(5) Uani 1 1 d . . . H8A H 0.4287 0.2451 -0.0239 0.06 Uiso 1 1 calc R . . H8B H 0.3415 0.378 0.0659 0.06 Uiso 1 1 calc R . . C9 C 0.2757(3) 0.1400(3) 0.1392(3) 0.0690(7) Uani 1 1 d . . . H9A H 0.3387 0.0536 0.1614 0.104 Uiso 1 1 calc R . . H9B H 0.1679 0.0886 0.0559 0.104 Uiso 1 1 calc R . . H9C H 0.2392 0.1838 0.2372 0.104 Uiso 1 1 calc R . . C10 C 0.7144(3) 0.2636(3) 0.1870(3) 0.0502(5) Uani 1 1 d . . . H10A H 0.6518 0.1423 0.1432 0.06 Uiso 1 1 calc R . . H10B H 0.7812 0.2687 0.2962 0.06 Uiso 1 1 calc R . . C11 C 0.8502(4) 0.3348(3) 0.0802(4) 0.0742(8) Uani 1 1 d . . . H11A H 0.784 0.3374 -0.0259 0.111 Uiso 1 1 calc R . . H11B H 0.931 0.2615 0.0691 0.111 Uiso 1 1 calc R . . H11C H 0.9217 0.4507 0.1294 0.111 Uiso 1 1 calc R . . N1 N 0.6456(2) 0.8816(2) 0.3969(2) 0.0464(5) Uani 1 1 d . . . N3 N 0.4720(2) 0.58483(19) 0.30156(19) 0.0402(4) Uani 1 1 d . . . N4 N 0.5766(2) 0.36130(19) 0.1967(2) 0.0413(4) Uani 1 1 d . . . O2 O 0.3584(2) 0.77944(18) 0.44137(18) 0.0554(4) Uani 1 1 d . . . H1 H 0.638(3) 0.982(3) 0.440(3) 0.065(7) Uiso 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 0.0473(12) 0.0424(11) 0.0372(10) 0.0091(8) 0.0079(9) 0.0204(9) C4 0.0424(11) 0.0352(10) 0.0399(11) 0.0124(8) 0.0105(8) 0.0135(8) C5 0.0474(12) 0.0457(11) 0.0518(12) 0.0043(9) -0.0016(10) 0.0201(9) C6 0.0366(11) 0.0470(12) 0.0646(14) -0.0004(10) 0.0043(10) 0.0096(9) C7 0.0457(12) 0.0411(11) 0.0571(13) 0.0042(9) 0.0117(10) 0.0098(9) C8 0.0565(13) 0.0450(11) 0.0459(12) 0.0004(9) 0.0010(10) 0.0169(10) C9 0.0573(15) 0.0613(15) 0.0769(18) -0.0016(13) 0.0091(13) 0.0031(12) C10 0.0548(13) 0.0400(11) 0.0638(14) 0.0089(10) 0.0167(11) 0.0238(10) C11 0.0704(17) 0.0684(16) 0.100(2) 0.0169(14) 0.0445(15) 0.0304(13) N1 0.0530(11) 0.0350(9) 0.0539(11) 0.0031(8) 0.0151(8) 0.0161(8) N3 0.0398(9) 0.0402(8) 0.0446(9) 0.0070(7) 0.0094(7) 0.0170(7) N4 0.0451(10) 0.0352(8) 0.0472(10) 0.0070(7) 0.0093(8) 0.0169(7) O2 0.0567(9) 0.0518(9) 0.0682(10) 0.0078(7) 0.0274(8) 0.0257(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 O2 1.245(2) . ? C2 N3 1.360(2) . ? C2 N1 1.371(3) . ? C4 N3 1.307(2) . ? C4 N4 1.340(2) . ? C4 C5 1.494(3) . ? C5 C6 1.496(3) . ? C6 C7 1.315(3) . ? C7 N1 1.390(3) . ? C8 N4 1.459(3) . ? C8 C9 1.506(3) . ? C10 N4 1.466(2) . ? C10 C11 1.511(3) . ? 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 O2 C2 N3 120.35(18) . . ? O2 C2 N1 117.08(17) . . ? N3 C2 N1 122.17(17) . . ? N3 C4 N4 118.73(18) . . ? N3 C4 C5 121.41(17) . . ? N4 C4 C5 119.86(16) . . ? C4 C5 C6 107.85(16) . . ? C7 C6 C5 120.42(19) . . ? C6 C7 N1 124.84(19) . . ? N4 C8 C9 112.07(18) . . ? N4 C10 C11 111.99(17) . . ? C2 N1 C7 128.84(17) . . ? C4 N3 C2 124.50(17) . . ? C4 N4 C8 121.20(16) . . ? C4 N4 C10 123.65(17) . . ? C8 N4 C10 115.15(16) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O2 0.87(2) 2.04(2) 2.906(2) 174(2) 2_676