#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:35:37 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179068 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/30/4303064.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_4303064
loop_
_publ_author_name
'Young-Hyuk Joo'
'Jean'ne M. Shreeve'
_publ_contact_author_address
;
Laboratory for the Structure of Matter
Naval Research Laboratory
Washington, DC 20375
;
_publ_contact_author_email       damon.parrish@nrl.navy.mil
_publ_contact_author_fax         202-767-6874
_publ_contact_author_name        'Dr Damon A. Parrish'
_publ_contact_author_phone       202-404-2141
_publ_section_title
;
1,3-Diazido-2-(azidomethyl)-2-propylammonium Salts
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              8431
_journal_page_last               8438
_journal_paper_doi               10.1021/ic901019p
_journal_volume                  48
_journal_year                    2009
_chemical_formula_moiety         'C4 H9 N10 +1, C2 N3 -1'
_chemical_formula_sum            'C6 H9 N13'
_chemical_formula_weight         263.26
_chemical_name_systematic
; 
 1,3-diazido-2-(azidomethyl)propan-2-aminium dicyanoimide 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2009-05-07
_audit_creation_method
'from SHELXTL CIF, local template and enCIFer'
_cell_angle_alpha                90.00
_cell_angle_beta                 95.3950(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4871(5)
_cell_length_b                   8.5229(3)
_cell_length_c                   12.8121(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1248.79(9)
_computing_cell_refinement       'Bruker APEX2 v2009.3-0 (Bruker, 2006)'
_computing_data_collection       'Bruker APEX2 v2009.3-0 (Bruker, 2006)'
_computing_data_reduction
;
Bruker SAINT v7.60A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008)
;
_computing_molecular_graphics    'Bruker SHELXTL v6.12 (Bruker, 2000b)'
_computing_publication_material  'Bruker SHELXTL v6.12 (Bruker, 2000b)'
_computing_structure_refinement  'Bruker SHELXTL v6.12 (Bruker, 2000b)'
_computing_structure_solution    'Bruker SHELXTL v6.12 (Bruker, 2000b)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14520
_diffrn_reflns_theta_full        29.72
_diffrn_reflns_theta_max         29.72
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.85
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0638P)²+0.2691P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1371
_reflns_number_gt                2789
_reflns_number_total             3484
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic901019p_si_003_5.cif
_cod_data_source_block           compound18
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4303064
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C 0.74572(9) 0.16082(13) 0.01787(9) 0.0332(2) Uani 1 1 d . . .
N2 N 0.80667(9) 0.00860(11) 0.00263(8) 0.0378(2) Uani 1 1 d . . .
H2A H 0.8419 0.0126 -0.0563 0.057 Uiso 1 1 calc R . .
H2B H 0.7547 -0.0691 -0.0016 0.057 Uiso 1 1 calc R . .
H2C H 0.8597 -0.0083 0.0567 0.057 Uiso 1 1 calc R . .
C3 C 0.65069(11) 0.18548(16) -0.07244(10) 0.0425(3) Uani 1 1 d . . .
H3A H 0.5923 0.1033 -0.0720 0.051 Uiso 1 1 calc R . .
H3B H 0.6124 0.2856 -0.0646 0.051 Uiso 1 1 calc R . .
N4 N 0.70524(12) 0.18209(19) -0.17190(10) 0.0621(4) Uani 1 1 d . . .
N5 N 0.64693(14) 0.1238(2) -0.24606(11) 0.0710(4) Uani 1 1 d . . .
N6 N 0.6013(2) 0.0740(4) -0.32025(16) 0.1227(9) Uani 1 1 d . . .
C7 C 0.83934(10) 0.28824(13) 0.02083(10) 0.0365(3) Uani 1 1 d . . .
H7A H 0.9030 0.2641 0.0736 0.044 Uiso 1 1 calc R . .
H7B H 0.8705 0.2968 -0.0467 0.044 Uiso 1 1 calc R . .
N8 N 0.78174(11) 0.43548(14) 0.04680(13) 0.0597(4) Uani 1 1 d . . .
N9 N 0.84256(11) 0.55053(14) 0.05970(11) 0.0523(3) Uani 1 1 d . . .
N10 N 0.88718(16) 0.66632(18) 0.07506(19) 0.0909(6) Uani 1 1 d . . .
C11 C 0.68580(11) 0.15151(16) 0.11972(10) 0.0418(3) Uani 1 1 d . . .
H11A H 0.6563 0.2545 0.1359 0.050 Uiso 1 1 calc R . .
H11B H 0.6197 0.0806 0.1097 0.050 Uiso 1 1 calc R . .
N12 N 0.76593(11) 0.09649(14) 0.20863(9) 0.0479(3) Uani 1 1 d . . .
N13 N 0.81995(11) 0.19908(15) 0.26050(9) 0.0504(3) Uani 1 1 d . . .
N14 N 0.87522(16) 0.2792(2) 0.31426(13) 0.0824(5) Uani 1 1 d . . .
N15 N 0.55144(16) -0.44276(17) -0.16056(11) 0.0711(4) Uani 1 1 d . . .
C16 C 0.54179(12) -0.46458(15) -0.26098(11) 0.0448(3) Uani 1 1 d . . .
N17 N 0.52710(12) -0.49929(16) -0.34794(10) 0.0576(3) Uani 1 1 d . . .
C18 C 0.59752(12) -0.31680(17) -0.11752(12) 0.0493(3) Uani 1 1 d . . .
N19 N 0.63367(15) -0.21154(18) -0.07046(13) 0.0714(4) Uani 1 1 d . . .
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'
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 C7 106.45(9) . . ?
N2 C1 C3 109.27(9) . . ?
C7 C1 C3 111.86(10) . . ?
N2 C1 C11 108.62(9) . . ?
C7 C1 C11 112.78(10) . . ?
C3 C1 C11 107.78(10) . . ?
C1 N2 H2A 109.5 . . ?
C1 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C1 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
N4 C3 C1 108.70(10) . . ?
N4 C3 H3A 109.9 . . ?
C1 C3 H3A 109.9 . . ?
N4 C3 H3B 109.9 . . ?
C1 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
N5 N4 C3 115.87(14) . . ?
N6 N5 N4 173.4(2) . . ?
N8 C7 C1 106.36(10) . . ?
N8 C7 H7A 110.5 . . ?
C1 C7 H7A 110.5 . . ?
N8 C7 H7B 110.5 . . ?
C1 C7 H7B 110.5 . . ?
H7A C7 H7B 108.6 . . ?
N9 N8 C7 117.22(12) . . ?
N10 N9 N8 171.54(16) . . ?
N12 C11 C1 112.14(10) . . ?
N12 C11 H11A 109.2 . . ?
C1 C11 H11A 109.2 . . ?
N12 C11 H11B 109.2 . . ?
C1 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
N13 N12 C11 116.00(12) . . ?
N14 N13 N12 172.14(16) . . ?
C16 N15 C18 122.34(14) . . ?
N17 C16 N15 172.40(15) . . ?
N19 C18 N15 172.91(18) . . ?
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 1.4957(14) . ?
C1 C7 1.5263(15) . ?
C1 C3 1.5288(16) . ?
C1 C11 1.5335(17) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
C3 N4 1.4723(19) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
N4 N5 1.2161(19) . ?
N5 N6 1.124(2) . ?
C7 N8 1.4713(16) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
N8 N9 1.2063(17) . ?
N9 N10 1.1209(19) . ?
C11 N12 1.4723(17) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
N12 N13 1.2303(17) . ?
N13 N14 1.1230(19) . ?
N15 C16 1.294(2) . ?
N15 C18 1.2968(19) . ?
C16 N17 1.1498(18) . ?
C18 N19 1.1375(19) . ?
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
N2 H2A N17 0.89 2.03 2.8793(18) 158.8 2_654
N2 H2B N19 0.89 1.99 2.8277(17) 156.7 .
N2 H2C N17 0.89 2.18 3.0285(16) 159.1 4_656
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
N2 C1 C3 N4 -57.65(13) . . . . ?
C7 C1 C3 N4 59.96(14) . . . . ?
C11 C1 C3 N4 -175.51(11) . . . . ?
C1 C3 N4 N5 144.85(15) . . . . ?
C3 N4 N5 N6 175(2) . . . . ?
N2 C1 C7 N8 -174.22(10) . . . . ?
C3 C1 C7 N8 66.48(13) . . . . ?
C11 C1 C7 N8 -55.21(13) . . . . ?
C1 C7 N8 N9 175.42(14) . . . . ?
C7 N8 N9 N10 -174.8(13) . . . . ?
N2 C1 C11 N12 50.21(13) . . . . ?
C7 C1 C11 N12 -67.54(13) . . . . ?
C3 C1 C11 N12 168.49(11) . . . . ?
C1 C11 N12 N13 90.94(14) . . . . ?
C11 N12 N13 N14 -177.6(12) . . . . ?
C18 N15 C16 N17 -177.5(12) . . . . ?
C16 N15 C18 N19 169.1(14) . . . . ?
