#------------------------------------------------------------------------------ #$Date: 2014-07-15 22:48:18 +0300 (Tue, 15 Jul 2014) $ #$Revision: 120443 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/03/7150365.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_7150365 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 'C9 H15 N3 O1' _chemical_formula_structural 'C9 H15 N3 O' _chemical_formula_sum 'C9 H15 N3 O' _chemical_formula_weight 181.24 _chemical_name_common 4-Diethylamino-1,5-dihydro-(1,3)diazepin-2-one _chemical_name_systematic ; 4-Diethylamino-1,5-dihydro-[1,3]diazepin-2-one ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -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 2003-12-12T09:36:41-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 96.79(2) _cell_angle_beta 98.36(3) _cell_angle_gamma 104.70(2) _cell_formula_units_Z 2 _cell_length_a 7.607(2) _cell_length_b 8.040(2) _cell_length_c 8.369(1) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 14.361 _cell_measurement_theta_min 9.148 _cell_measurement_wavelength 0.71073 _cell_volume 483.4(2) _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 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega scans' _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_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_unetI/netI 0.0309 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 1839 _diffrn_reflns_theta_full 24.98 _diffrn_reflns_theta_max 24.98 _diffrn_reflns_theta_min 2.49 _diffrn_source 'Enraf Nonius FR590' _diffrn_standards_decay_% 7 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.084 _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 196 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.3 _refine_diff_density_max 0.184 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.045 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 124 _refine_ls_number_reflns 1697 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.047 _refine_ls_R_factor_all 0.0727 _refine_ls_R_factor_gt 0.0434 _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^)+(0.0665P)^2^+0.0725P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1088 _refine_ls_wR_factor_ref 0.1244 _reflns_number_gt 1181 _reflns_number_total 1697 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file b317099c.txt _[local]_cod_data_source_block cw15332 _cod_original_cell_volume 483.36(18) _cod_database_code 7150365 _diffrn_standards_decay_corr_max 1.072 _diffrn_standards_decay_corr_min 0.988 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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) 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_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 4 0 0 3 -5 1 -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_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_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_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 _journal_paper_doi 10.1039/b317099c