#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2204488.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_2204488 loop_ _publ_author_name 'Charette, Andr\'e B.' 'Legault, Claude' 'B\'elanger-Gari\'epy, Francine' _publ_section_title ; 3,3-Pentamethylenediaziridine ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1921 _journal_page_last o1922 _journal_volume 60 _journal_year 2004 _chemical_formula_analytical 'C6 H12 N2' _chemical_formula_iupac 'C6 H12 N2' _chemical_formula_moiety 'C6 H12 N2' _chemical_formula_structural 'C6 H12 N2' _chemical_formula_sum 'C6 H12 N2' _chemical_formula_weight 112.176 _chemical_melting_point 107 _chemical_name_common 3,3-Pentamethylenediaziridine _chemical_name_systematic ; 3,3-Pentamethylenediaziridine ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method 'SHELXL96 (Sheldrick, 1996)' _cell_angle_alpha 90.00 _cell_angle_beta 98.86(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.373(3) _cell_length_b 8.037(3) _cell_length_c 8.077(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.00 _cell_measurement_theta_min 20.00 _cell_volume 665.3(4) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf--Nonius, 1989)' _computing_data_reduction 'NRC-2 and NRC-2A (Ahmed et al, 1973)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997) and PLATON (Spek, 1995)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Enraf--Nonius CAD-4' _diffrn_measurement_method '\w scan' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'normal-focus xray tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.070 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _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 19833 _diffrn_reflns_theta_full 69.87 _diffrn_reflns_theta_max 69.87 _diffrn_reflns_theta_min 4.31 _diffrn_standards_decay_% 2.1 _diffrn_standards_interval_time 60 _diffrn_standards_number 5 _exptl_absorpt_coefficient_mu 0.537 _exptl_absorpt_correction_T_max 0.8979 _exptl_absorpt_correction_T_min 0.8189 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details '(ABSORP in NRCVAX; Gabe et al, 1989)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.1199 _exptl_crystal_density_method none _exptl_crystal_description block _exptl_crystal_F_000 248.0 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.23 _refine_diff_density_max 0.120 _refine_diff_density_min -0.107 _refine_ls_extinction_coef 0.072(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_all 0.896 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 130 _refine_ls_number_reflns 1253 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.896 _refine_ls_restrained_S_obs 1.051 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0342 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0551P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0919 _refine_ls_wR_factor_ref 0.0878 _reflns_number_gt 872 _reflns_number_total 1253 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file dn6163.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2204488 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 N11 0.53841(11) 0.94402(18) 0.68680(19) 0.0725(4) Uani d . 1 N H11A 0.519(4) 0.836(6) 0.706(5) 0.141(15) Uiso d P 0.50 H H11B 0.521(4) 0.967(5) 0.580(4) 0.114(14) Uiso d P 0.50 H N12 0.52104(10) 1.06808(16) 0.82174(16) 0.0682(4) Uani d . 1 N H12A 0.483(3) 1.157(4) 0.756(4) 0.080(8) Uiso d P 0.50 H H12B 0.508(3) 1.015(4) 0.923(3) 0.075(8) Uiso d P 0.50 H C1 0.64843(11) 1.02759(14) 0.78250(13) 0.0541(3) Uani d . 1 C C2 0.73685(13) 0.92490(19) 0.90762(17) 0.0681(4) Uani d . 1 C H2A 0.6801(15) 0.8388(19) 0.9542(17) 0.092(4) Uiso d . 1 H H2B 0.7770(15) 0.9972(18) 1.0029(17) 0.090(5) Uiso d . 1 H C3 0.84431(14) 0.8457(2) 0.8262(2) 0.0762(4) Uani d . 1 C H3A 0.9075(15) 0.7837(19) 0.9161(19) 0.097(5) Uiso d . 1 H H3B 0.8021(15) 0.7600(19) 0.741(2) 0.094(5) Uiso d . 1 H C4 0.91702(13) 0.9740(2) 0.7386(2) 0.0822(5) Uani d . 1 C H4A 0.9852(15) 0.9166(19) 0.6830(16) 0.093(5) Uiso d . 1 H H4B 0.9613(15) 1.0492(19) 0.8250(18) 0.094(5) Uiso d . 1 H C5 0.82412(13) 1.0722(2) 0.61154(18) 0.0750(4) Uani d . 1 C H5A 0.7833(14) 0.9945(17) 0.5185(16) 0.081(4) Uiso d . 1 H H5B 0.8722(14) 1.1564(19) 0.5549(18) 0.096(5) Uiso d . 1 H C6 0.71696(12) 1.15454(17) 0.69129(17) 0.0633(4) Uani d . 1 C H6A 0.7559(15) 1.2415(18) 0.7779(18) 0.088(4) Uiso d . 1 H H6B 0.6488(13) 1.2098(15) 0.6059(17) 0.076(4) 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 N11 0.0553(6) 0.0727(8) 0.0895(9) -0.0084(6) 0.0117(6) -0.0100(7) N12 0.0582(6) 0.0736(8) 0.0764(7) 0.0117(5) 0.0220(5) 0.0074(6) C1 0.0480(6) 0.0558(6) 0.0590(6) 0.0019(5) 0.0104(5) 0.0016(5) C2 0.0623(7) 0.0761(9) 0.0662(8) 0.0130(7) 0.0112(6) 0.0120(7) C3 0.0615(8) 0.0867(10) 0.0797(9) 0.0204(7) 0.0080(7) 0.0061(8) C4 0.0513(7) 0.1095(12) 0.0865(10) 0.0066(8) 0.0131(7) 0.0023(9) C5 0.0569(7) 0.0954(10) 0.0752(9) -0.0054(7) 0.0181(6) 0.0094(8) C6 0.0567(7) 0.0635(8) 0.0695(8) -0.0065(6) 0.0090(6) 0.0059(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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 N11 N12 58.50(7) y C1 N11 H11A 122(3) ? N12 N11 H11A 117(2) ? C1 N11 H11B 117(3) ? N12 N11 H11B 123(3) ? H11A N11 H11B 111(4) ? C1 N12 N11 58.45(7) y C1 N12 H12A 111.6(17) ? N11 N12 H12A 100.5(18) ? C1 N12 H12B 110.4(17) ? N11 N12 H12B 112.2(17) ? H12A N12 H12B 136(2) ? N11 C1 N12 63.05(8) y N11 C1 C6 116.70(11) y N12 C1 C6 118.28(11) y N11 C1 C2 117.09(12) y N12 C1 C2 117.45(10) y C6 C1 C2 114.68(11) ? C1 C2 C3 110.58(11) ? C1 C2 H2A 107.1(8) ? C3 C2 H2A 112.3(8) ? C1 C2 H2B 109.7(8) ? C3 C2 H2B 109.2(9) ? H2A C2 H2B 107.8(11) ? C4 C3 C2 111.62(13) ? C4 C3 H3A 110.5(9) ? C2 C3 H3A 109.1(8) ? C4 C3 H3B 109.6(9) ? C2 C3 H3B 107.9(9) ? H3A C3 H3B 108.0(12) ? C3 C4 C5 111.09(12) ? C3 C4 H4A 109.3(8) ? C5 C4 H4A 110.7(8) ? C3 C4 H4B 107.4(9) ? C5 C4 H4B 109.8(9) ? H4A C4 H4B 108.3(13) ? C4 C5 C6 111.71(11) ? C4 C5 H5A 109.2(8) ? C6 C5 H5A 109.4(8) ? C4 C5 H5B 110.7(8) ? C6 C5 H5B 110.6(8) ? H5A C5 H5B 105.0(11) ? C1 C6 C5 110.18(11) ? C1 C6 H6A 107.2(8) ? C5 C6 H6A 110.4(8) ? C1 C6 H6B 107.4(7) ? C5 C6 H6B 112.5(7) ? H6A C6 H6B 109.0(10) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N11 C1 1.4420(16) y N11 N12 1.5083(17) y N11 H11A 0.91(5) ? N11 H11B 0.87(3) ? N12 C1 1.4427(14) y N12 H12A 0.94(3) ? N12 H12B 0.95(2) ? C1 C6 1.5002(16) ? C1 C2 1.5027(17) ? C2 C3 1.5186(18) ? C2 H2A 1.017(15) ? C2 H2B 1.002(14) ? C3 C4 1.515(2) ? C3 H3A 1.029(16) ? C3 H3B 1.024(16) ? C4 C5 1.517(2) ? C4 H4A 1.006(15) ? C4 H4B 0.983(15) ? C5 C6 1.5195(18) ? C5 H5A 1.018(13) ? C5 H5B 0.993(16) ? C6 H6A 1.027(15) ? C6 H6B 1.011(13) ? 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 N11 H11A N12 2_646 0.91 2.20 3.082(2) 164 y N11 H11B N11 3_676 0.87 2.26 3.132(3) 173 y N12 H12A N11 2_656 0.94 2.37 3.082(2) 132 y N12 H12B N12 3_677 0.95 2.23 3.173(3) 171 y loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion N12 N11 C1 C6 -109.83(13) N12 N11 C1 C2 108.71(12) N11 N12 C1 C6 107.39(13) N11 N12 C1 C2 -108.15(14) N11 C1 C2 C3 89.02(15) N12 C1 C2 C3 161.08(12) C6 C1 C2 C3 -53.21(16) C1 C2 C3 C4 53.23(18) C2 C3 C4 C5 -55.61(18) C3 C4 C5 C6 56.07(19) N11 C1 C6 C5 -88.99(14) N12 C1 C6 C5 -161.20(11) C2 C1 C6 C5 53.39(14) C4 C5 C6 C1 -53.88(17)