# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Bushmarinov, Ivan' 'Nabiev, Orudzh' 'Kostyanovsky, Remir' 'Antipin, Mikhail' 'Lyssenko, Konstantin' _publ_contact_author_name 'Lyssenko, Konstantin' _publ_contact_author_email kostya@xray.ineos.ac.ru _publ_section_title ; The azide anion as a building block in crystal engineering from charge density point of view ; # Attachment '- DCDA.cif' data_DCDA _database_code_depnum_ccdc_archive 'CCDC 801422' #TrackingRef '- DCDA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H28 N2 O4, 2(N3)' _chemical_formula_sum 'C12 H28 N8 O4' _chemical_formula_weight 348.42 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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 7.60360(10) _cell_length_b 8.54800(10) _cell_length_c 13.8275(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.3164(7) _cell_angle_gamma 90.00 _cell_volume 898.71(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 394 _cell_measurement_theta_min 3 _cell_measurement_theta_max 55 _exptl_crystal_description prizm _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.973 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type "Bruker APEX II CCD area detector'" _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 75866 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_sigmaI/netI 0.0268 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 55.73 _reflns_number_total 11838 _reflns_number_gt 7780 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0606P)^2^+0.0335P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary direct _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11838 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0740 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1222 _refine_ls_wR_factor_gt 0.1021 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 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 O1 O 0.31963(4) -0.31889(4) 1.00989(2) 0.01617(4) Uani 1 1 d . . . O2 O 0.26702(4) -0.08387(3) 1.16192(2) 0.01601(4) Uani 1 1 d . . . N1 N 0.57709(4) -0.21303(4) 0.88934(2) 0.01370(4) Uani 1 1 d . . . H2N H 0.5029(12) -0.1363(11) 0.8729(6) 0.025(2) Uiso 1 1 d . . . H1N H 0.6016(13) -0.2053(11) 0.9528(7) 0.029(2) Uiso 1 1 d . . . N2 N 0.30236(5) -0.00334(4) 0.83374(3) 0.01854(5) Uani 1 1 d . . . N3 N 0.28833(4) 0.11346(4) 0.87837(2) 0.01362(4) Uani 1 1 d . . . N4 N 0.27126(6) 0.23159(5) 0.92141(3) 0.02207(6) Uani 1 1 d . . . C1 C 0.48924(5) -0.36689(4) 0.87039(3) 0.01595(5) Uani 1 1 d . . . H1B H 0.5585(11) -0.4485(9) 0.9026(6) 0.0187(17) Uiso 1 1 d . . . H1A H 0.4878(12) -0.3842(10) 0.8004(6) 0.0222(19) Uiso 1 1 d . . . C2 C 0.30547(5) -0.36514(4) 0.91125(3) 0.01621(5) Uani 1 1 d . . . H2B H 0.2532(11) -0.4681(10) 0.9053(6) 0.0218(19) Uiso 1 1 d . . . H2A H 0.2332(11) -0.2894(10) 0.8773(6) 0.0200(18) Uiso 1 1 d . . . C3 C 0.15350(5) -0.28859(5) 1.05163(3) 0.01708(5) Uani 1 1 d . . . H3B H 0.0881(12) -0.2123(10) 1.0124(6) 0.0216(19) Uiso 1 1 d . . . H3A H 0.0829(13) -0.3839(11) 1.0559(7) 0.028(2) Uiso 1 1 d . . . C4 C 0.17961(5) -0.23113(5) 1.15413(3) 0.01699(5) Uani 1 1 d . . . H4B H 0.2536(12) -0.3052(10) 1.1890(6) 0.024(2) Uiso 1 1 d . . . H4A H 0.0634(12) -0.2267(10) 1.1846(6) 0.0224(19) Uiso 1 1 d . . . C5 C 0.16048(5) 0.04500(5) 1.13465(3) 0.01917(6) Uani 1 1 d . . . H5B H 0.0452(12) 0.0369(11) 1.1666(7) 0.028(2) Uiso 1 1 d . . . H5A H 0.1369(12) 0.0421(11) 1.0636(7) 0.028(2) Uiso 1 1 d . . . C6 C 0.25481(5) 0.19353(5) 1.16411(3) 0.01921(6) Uani 1 1 d . . . H6B H 0.1804(12) 0.2823(11) 1.1503(7) 0.026(2) Uiso 1 1 d . . . H6A H 0.2844(13) 0.1932(11) 1.2343(7) 0.028(2) 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 O1 0.01547(9) 0.01991(11) 0.01312(8) -0.00006(8) -0.00098(7) 0.00172(8) O2 0.01507(9) 0.01586(9) 0.01707(10) 0.00016(8) -0.00323(7) 0.00037(7) N1 0.01556(9) 0.01302(9) 0.01252(9) -0.00169(7) -0.00053(7) 0.00153(7) N2 0.01902(12) 0.01498(11) 0.02158(13) -0.00241(9) -0.00226(10) 0.00142(9) N3 0.01365(9) 0.01474(10) 0.01244(8) 0.00121(7) -0.00138(7) 0.00087(7) N4 0.02691(16) 0.02035(14) 0.01888(13) -0.00543(11) -0.00564(11) 0.00626(11) C1 0.02030(13) 0.01289(11) 0.01468(11) -0.00191(9) 0.00016(9) 0.00076(9) C2 0.01929(13) 0.01458(11) 0.01475(11) -0.00052(9) -0.00142(9) -0.00183(9) C3 0.01482(11) 0.01868(13) 0.01774(12) -0.00187(10) -0.00059(9) -0.00141(9) C4 0.01882(13) 0.01713(13) 0.01504(11) 0.00172(10) 0.00108(9) -0.00160(10) C5 0.01409(11) 0.01748(13) 0.02591(16) 0.00055(12) -0.00149(11) 0.00133(9) C6 0.01825(13) 0.01657(13) 0.02286(15) -0.00338(11) 0.00494(11) 0.00142(10) _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 O1 C3 1.4156(5) . ? O1 C2 1.4235(5) . ? O2 C5 1.4172(5) . ? O2 C4 1.4273(5) . ? N1 C6 1.4894(5) 3_657 ? N1 C1 1.4976(5) . ? N1 H2N 0.893(9) . ? N1 H1N 0.899(9) . ? N2 N3 1.1789(5) . ? N3 N4 1.1797(5) . ? C1 C2 1.5102(6) . ? C1 H1B 0.980(8) . ? C1 H1A 0.978(9) . ? C2 H2B 0.969(9) . ? C2 H2A 0.969(9) . ? C3 C4 1.5121(6) . ? C3 H3B 0.981(9) . ? C3 H3A 0.978(9) . ? C4 H4B 0.973(9) . ? C4 H4A 0.981(9) . ? C5 C6 1.5130(6) . ? C5 H5B 0.987(9) . ? C5 H5A 0.998(9) . ? C6 N1 1.4894(5) 3_657 ? C6 H6B 0.964(10) . ? C6 H6A 0.995(9) . ? 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 C3 O1 C2 112.24(3) . . ? C5 O2 C4 113.59(3) . . ? C6 N1 C1 113.24(3) 3_657 . ? C6 N1 H2N 109.5(6) 3_657 . ? C1 N1 H2N 108.6(6) . . ? C6 N1 H1N 107.6(6) 3_657 . ? C1 N1 H1N 109.0(6) . . ? H2N N1 H1N 108.8(8) . . ? N2 N3 N4 178.36(4) . . ? N1 C1 C2 109.79(3) . . ? N1 C1 H1B 107.9(5) . . ? C2 C1 H1B 109.4(5) . . ? N1 C1 H1A 108.0(5) . . ? C2 C1 H1A 111.5(5) . . ? H1B C1 H1A 110.2(7) . . ? O1 C2 C1 107.22(3) . . ? O1 C2 H2B 111.3(5) . . ? C1 C2 H2B 109.8(5) . . ? O1 C2 H2A 108.6(5) . . ? C1 C2 H2A 110.4(5) . . ? H2B C2 H2A 109.5(7) . . ? O1 C3 C4 109.20(3) . . ? O1 C3 H3B 110.3(5) . . ? C4 C3 H3B 111.5(5) . . ? O1 C3 H3A 111.3(6) . . ? C4 C3 H3A 106.4(5) . . ? H3B C3 H3A 108.1(8) . . ? O2 C4 C3 114.58(3) . . ? O2 C4 H4B 105.6(5) . . ? C3 C4 H4B 109.0(5) . . ? O2 C4 H4A 110.7(5) . . ? C3 C4 H4A 107.5(5) . . ? H4B C4 H4A 109.4(7) . . ? O2 C5 C6 108.13(3) . . ? O2 C5 H5B 109.5(5) . . ? C6 C5 H5B 111.1(6) . . ? O2 C5 H5A 110.0(5) . . ? C6 C5 H5A 111.6(5) . . ? H5B C5 H5A 106.5(8) . . ? N1 C6 C5 111.54(3) 3_657 . ? N1 C6 H6B 108.5(6) 3_657 . ? C5 C6 H6B 109.3(6) . . ? N1 C6 H6A 107.1(6) 3_657 . ? C5 C6 H6A 111.4(5) . . ? H6B C6 H6A 108.9(8) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C1 C2 -169.22(3) 3_657 . . . ? C3 O1 C2 C1 170.46(3) . . . . ? N1 C1 C2 O1 -52.82(4) . . . . ? C2 O1 C3 C4 -176.68(3) . . . . ? C5 O2 C4 C3 73.60(4) . . . . ? O1 C3 C4 O2 65.16(4) . . . . ? C4 O2 C5 C6 169.29(3) . . . . ? O2 C5 C6 N1 64.11(5) . . . 3_657 ? 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 H2N N2 0.893(9) 1.975(9) 2.8548(5) 167.8(9) . N1 H1N N4 0.899(9) 1.998(9) 2.8581(5) 159.9(9) 3_657 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 55.73 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.620 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.059 _publ_section_references ; Bruker, Programs APEX II, version 2.0-1; SAINT, version 7.23A; SADABS, version 2004/1; XPREP, version 2005/2; SHELXTL, version 6.1. Bruker AXS Inc., Madison, WI, USA, 2005. G.M. Sheldrick, Programs SHELXS97 (crystal structure solution) and SHELXL97 (crystal structure refinement), University of Gottingen, Germany, 1997. ;