#------------------------------------------------------------------------------
#$Date: 2025-08-20 21:19:29 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301836 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/30/4303061.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_4303061
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, N1 O3 -1'
_chemical_formula_sum            'C4 H9 N11 O3'
_chemical_formula_weight         259.22
_chemical_name_systematic
; 
 1,3-diazido-2-(azidomethyl)propan-2-aminium nitrate 
;
_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_date             2009-01-23
_audit_creation_method           'from SHELXTL CIF, local template and enCIFer'
_cell_angle_alpha                90.00
_cell_angle_beta                 93.330(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7297(16)
_cell_length_b                   9.0361(17)
_cell_length_c                   13.415(3)
_cell_measurement_temperature    173(2)
_cell_volume                     1056.4(4)
_computing_cell_refinement       'Bruker APEX2 v2.1-0 (Bruker, 2006)'
_computing_data_collection       'Bruker APEX2 v2.1-0 (Bruker, 2006)'
_computing_data_reduction
;
Bruker SAINT v7.34A (Bruker, 2005), Bruker XPREP v2005/2 (Bruker, 2004)
;
_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      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10611
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2004/1 (Bruker, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'large prism'
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.89
_exptl_crystal_size_mid          0.83
_exptl_crystal_size_min          0.79
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0324
_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)+(0.0508P)²+0.2371P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0886
_reflns_number_gt                2414
_reflns_number_total             2606
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic901019p_si_003_2.cif
_cod_data_source_block           compound8
_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_original_cell_volume        1056.4(3)
_cod_database_code               4303061
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_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 -0.24237(10) 0.20733(10) 0.63008(6) 0.01476(18) Uani 1 1 d . . .
N2 N -0.08082(9) 0.14929(9) 0.64071(6) 0.01581(16) Uani 1 1 d . . .
H2A H -0.0353 0.1605 0.5818 0.024 Uiso 1 1 calc R . .
H2B H -0.0825 0.0517 0.6573 0.024 Uiso 1 1 calc R . .
H2C H -0.0269 0.2006 0.6894 0.024 Uiso 1 1 calc R . .
C3 C -0.31667(11) 0.18794(10) 0.73031(7) 0.01872(19) Uani 1 1 d . . .
H3A H -0.2466 0.2264 0.7850 0.022 Uiso 1 1 calc R . .
H3B H -0.4131 0.2456 0.7297 0.022 Uiso 1 1 calc R . .
N4 N -0.34992(10) 0.03024(10) 0.74857(6) 0.02404(19) Uani 1 1 d . . .
N5 N -0.28354(10) -0.02533(10) 0.82324(6) 0.02277(19) Uani 1 1 d . . .
N6 N -0.23229(13) -0.09096(12) 0.88864(7) 0.0363(2) Uani 1 1 d . . .
C7 C -0.33572(10) 0.12008(10) 0.55017(6) 0.01720(18) Uani 1 1 d . . .
H7A H -0.3361 0.0139 0.5683 0.021 Uiso 1 1 calc R . .
H7B H -0.4431 0.1557 0.5460 0.021 Uiso 1 1 calc R . .
N8 N -0.26834(10) 0.13883(9) 0.45235(6) 0.02144(18) Uani 1 1 d . . .
N9 N -0.27788(9) 0.02959(10) 0.39703(6) 0.02023(18) Uani 1 1 d . . .
N10 N -0.27825(12) -0.06032(12) 0.33844(7) 0.0330(2) Uani 1 1 d . . .
C11 C -0.22480(10) 0.37138(10) 0.60430(7) 0.01737(19) Uani 1 1 d . . .
H11A H -0.1660 0.4229 0.6593 0.021 Uiso 1 1 calc R . .
H11B H -0.1683 0.3818 0.5428 0.021 Uiso 1 1 calc R . .
N12 N -0.37901(10) 0.43746(9) 0.58916(7) 0.02368(19) Uani 1 1 d . . .
N13 N -0.38140(9) 0.57376(9) 0.59789(6) 0.02052(18) Uani 1 1 d . . .
N14 N -0.39967(11) 0.69700(10) 0.60422(8) 0.0293(2) Uani 1 1 d . . .
N15 N 0.04535(9) 0.22063(9) 0.38267(6) 0.01703(17) Uani 1 1 d . . .
O16 O 0.01327(9) 0.35315(8) 0.38545(6) 0.02830(18) Uani 1 1 d . . .
O17 O 0.08530(8) 0.14860(8) 0.45955(5) 0.02268(17) Uani 1 1 d . . .
O18 O 0.03656(9) 0.15236(8) 0.29926(5) 0.02425(17) 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'
O O 0.0106 0.0060 '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 110.23(7) . . ?
N2 C1 C11 104.67(7) . . ?
C7 C1 C11 113.41(7) . . ?
N2 C1 C3 108.57(7) . . ?
C7 C1 C3 108.68(7) . . ?
C11 C1 C3 111.15(7) . . ?
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 110.61(7) . . ?
N4 C3 H3A 109.5 . . ?
C1 C3 H3A 109.5 . . ?
N4 C3 H3B 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
N5 N4 C3 116.06(8) . . ?
N6 N5 N4 171.84(11) . . ?
N8 C7 C1 109.89(7) . . ?
N8 C7 H7A 109.7 . . ?
C1 C7 H7A 109.7 . . ?
N8 C7 H7B 109.7 . . ?
C1 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
N9 N8 C7 115.17(8) . . ?
N10 N9 N8 171.83(10) . . ?
N12 C11 C1 108.67(7) . . ?
N12 C11 H11A 110.0 . . ?
C1 C11 H11A 110.0 . . ?
N12 C11 H11B 110.0 . . ?
C1 C11 H11B 110.0 . . ?
H11A C11 H11B 108.3 . . ?
N13 N12 C11 114.20(8) . . ?
N14 N13 N12 172.82(10) . . ?
O16 N15 O17 122.27(8) . . ?
O16 N15 O18 119.65(8) . . ?
O17 N15 O18 118.08(8) . . ?
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 1.5036(11) . ?
C1 C7 1.5275(12) . ?
C1 C11 1.5319(13) . ?
C1 C3 1.5365(12) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
C3 N4 1.4776(13) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
N4 N5 1.2344(12) . ?
N5 N6 1.1296(13) . ?
C7 N8 1.4786(12) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
N8 N9 1.2348(12) . ?
N9 N10 1.1303(13) . ?
C11 N12 1.4758(12) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N12 N13 1.2375(12) . ?
N13 N14 1.1288(13) . ?
N15 O16 1.2308(11) . ?
N15 O17 1.2518(10) . ?
N15 O18 1.2762(10) . ?
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 O17 0.91 2.00 2.9015(11) 169.0 .
N2 H2B O18 0.91 1.97 2.8621(12) 167.1 3_556
N2 H2C O18 0.91 2.04 2.9212(11) 163.7 4_566
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 -72.14(9) . . . . ?
C7 C1 C3 N4 47.76(10) . . . . ?
C11 C1 C3 N4 173.24(7) . . . . ?
C1 C3 N4 N5 118.38(9) . . . . ?
C3 N4 N5 N6 177.3(7) . . . . ?
N2 C1 C7 N8 -62.11(9) . . . . ?
C11 C1 C7 N8 54.87(10) . . . . ?
C3 C1 C7 N8 179.02(7) . . . . ?
C1 C7 N8 N9 145.84(8) . . . . ?
C7 N8 N9 N10 178.6(7) . . . . ?
N2 C1 C11 N12 178.23(7) . . . . ?
C7 C1 C11 N12 58.04(10) . . . . ?
C3 C1 C11 N12 -64.75(9) . . . . ?
C1 C11 N12 N13 159.25(8) . . . . ?
C11 N12 N13 N14 -177.4(8) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139127022
