#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:35:37 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179068 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/30/4303062.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_4303062
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, C6 H2 N3 O7 -1'
_chemical_formula_sum            'C10 H11 N13 O7'
_chemical_formula_weight         425.32
_chemical_name_systematic
; 
 1,3-diazido-2-(azidomethyl)propan-2-aminium 2,4,6-trinitrophenolate 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_creation_date             2009-02-12
_audit_creation_method
'from SHELXTL CIF, local template and enCIFer'
_cell_angle_alpha                113.0670(10)
_cell_angle_beta                 96.2560(10)
_cell_angle_gamma                101.730(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4766(8)
_cell_length_b                   10.7765(11)
_cell_length_c                   12.0355(12)
_cell_measurement_temperature    93(2)
_cell_volume                     854.19(15)
_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      93(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0157
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9054
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2004/1 (Bruker, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0497P)²+0.2530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0900
_reflns_number_gt                3686
_reflns_number_total             4188
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic901019p_si_003_3.cif
_cod_data_source_block           compound10
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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               4303062
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
C1 C 0.72852(14) 0.42969(11) 1.19175(9) 0.0111(2) Uani 1 1 d . . .
N2 N 0.75415(12) 0.49301(9) 1.10155(8) 0.01089(18) Uani 1 1 d . . .
H2A H 0.8781 0.5304 1.1096 0.016 Uiso 1 1 calc R . .
H2B H 0.6939 0.5615 1.1170 0.016 Uiso 1 1 calc R . .
H2C H 0.7060 0.4256 1.0233 0.016 Uiso 1 1 calc R . .
C3 C 0.81726(15) 0.30742(11) 1.15730(10) 0.0136(2) Uani 1 1 d . . .
H3A H 0.9518 0.3407 1.1599 0.016 Uiso 1 1 calc R . .
H3B H 0.8046 0.2649 1.2165 0.016 Uiso 1 1 calc R . .
N4 N 0.72018(14) 0.20315(10) 1.03143(9) 0.0178(2) Uani 1 1 d . . .
N5 N 0.72892(14) 0.08245(10) 1.00645(9) 0.0167(2) Uani 1 1 d . . .
N6 N 0.72493(19) -0.03185(12) 0.97247(10) 0.0300(3) Uani 1 1 d . . .
C7 C 0.51731(14) 0.38325(12) 1.18207(10) 0.0129(2) Uani 1 1 d . . .
H7A H 0.4650 0.4651 1.2051 0.015 Uiso 1 1 calc R . .
H7B H 0.4545 0.3159 1.0964 0.015 Uiso 1 1 calc R . .
N8 N 0.48775(13) 0.31644(11) 1.26771(9) 0.0175(2) Uani 1 1 d . . .
N9 N 0.33770(15) 0.31697(13) 1.30085(10) 0.0242(2) Uani 1 1 d . . .
N10 N 0.20473(19) 0.3109(2) 1.33721(15) 0.0487(4) Uani 1 1 d . . .
C11 C 0.82855(15) 0.54080(11) 1.32081(10) 0.0128(2) Uani 1 1 d . . .
H11A H 0.8051 0.5052 1.3837 0.015 Uiso 1 1 calc R . .
H11B H 0.9649 0.5681 1.3260 0.015 Uiso 1 1 calc R . .
N12 N 0.75041(14) 0.66093(11) 1.34009(9) 0.0179(2) Uani 1 1 d . . .
N13 N 0.82370(13) 0.76969(10) 1.43431(8) 0.01352(19) Uani 1 1 d . . .
N14 N 0.87460(14) 0.87639(11) 1.51520(9) 0.0197(2) Uani 1 1 d . . .
C15 C 0.44695(14) 0.21255(11) 0.81580(9) 0.0109(2) Uani 1 1 d . . .
C16 C 0.27331(14) 0.10754(11) 0.79030(10) 0.0118(2) Uani 1 1 d . . .
C17 C 0.23712(15) -0.03047(11) 0.70758(10) 0.0124(2) Uani 1 1 d . . .
H17 H 0.1208 -0.0948 0.6948 0.015 Uiso 1 1 calc R . .
C18 C 0.37179(15) -0.07499(11) 0.64293(10) 0.0123(2) Uani 1 1 d . . .
C19 C 0.54330(15) 0.01703(11) 0.66055(10) 0.0124(2) Uani 1 1 d . . .
H19 H 0.6346 -0.0143 0.6157 0.015 Uiso 1 1 calc R . .
C20 C 0.57825(14) 0.15449(11) 0.74431(10) 0.0116(2) Uani 1 1 d . . .
O21 O 0.48054(10) 0.33965(8) 0.88877(7) 0.01278(16) Uani 1 1 d . . .
N22 N 0.12265(13) 0.14368(10) 0.85490(9) 0.01341(19) Uani 1 1 d . . .
O23 O 0.15024(12) 0.26010(8) 0.93996(8) 0.01835(18) Uani 1 1 d . . .
O24 O -0.02691(12) 0.05371(10) 0.82137(9) 0.0273(2) Uani 1 1 d . . .
N25 N 0.33126(13) -0.22083(10) 0.55503(8) 0.01358(19) Uani 1 1 d . . .
O26 O 0.18081(11) -0.30051(8) 0.54580(8) 0.01703(17) Uani 1 1 d . . .
O27 O 0.44815(12) -0.25746(9) 0.49377(8) 0.01959(18) Uani 1 1 d . . .
N28 N 0.76001(12) 0.24543(10) 0.75620(8) 0.01208(18) Uani 1 1 d . . .
O29 O 0.84535(12) 0.20520(9) 0.67300(8) 0.01990(18) Uani 1 1 d . . .
O30 O 0.82389(11) 0.35862(9) 0.84849(7) 0.01725(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 C11 108.48(8) . . ?
N2 C1 C3 108.43(8) . . ?
C11 C1 C3 109.24(8) . . ?
N2 C1 C7 106.28(8) . . ?
C11 C1 C7 111.67(9) . . ?
C3 C1 C7 112.58(9) . . ?
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 107.98(8) . . ?
N4 C3 H3A 110.1 . . ?
C1 C3 H3A 110.1 . . ?
N4 C3 H3B 110.1 . . ?
C1 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
N5 N4 C3 115.22(9) . . ?
N6 N5 N4 172.96(12) . . ?
N8 C7 C1 107.40(8) . . ?
N8 C7 H7A 110.2 . . ?
C1 C7 H7A 110.2 . . ?
N8 C7 H7B 110.2 . . ?
C1 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
N9 N8 C7 113.81(9) . . ?
N10 N9 N8 173.63(13) . . ?
N12 C11 C1 105.52(8) . . ?
N12 C11 H11A 110.6 . . ?
C1 C11 H11A 110.6 . . ?
N12 C11 H11B 110.6 . . ?
C1 C11 H11B 110.6 . . ?
H11A C11 H11B 108.8 . . ?
N13 N12 C11 117.23(9) . . ?
N14 N13 N12 171.11(11) . . ?
O21 C15 C16 124.76(9) . . ?
O21 C15 C20 123.27(10) . . ?
C16 C15 C20 111.96(9) . . ?
C17 C16 C15 123.95(9) . . ?
C17 C16 N22 115.25(9) . . ?
C15 C16 N22 120.79(9) . . ?
C16 C17 C18 119.49(10) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C19 121.25(10) . . ?
C17 C18 N25 118.96(10) . . ?
C19 C18 N25 119.79(9) . . ?
C20 C19 C18 118.66(10) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C19 C20 C15 124.69(10) . . ?
C19 C20 N28 115.53(9) . . ?
C15 C20 N28 119.76(9) . . ?
O23 N22 O24 122.65(9) . . ?
O23 N22 C16 119.69(9) . . ?
O24 N22 C16 117.65(9) . . ?
O27 N25 O26 123.82(9) . . ?
O27 N25 C18 118.32(9) . . ?
O26 N25 C18 117.86(9) . . ?
O29 N28 O30 122.16(9) . . ?
O29 N28 C20 117.86(9) . . ?
O30 N28 C20 119.98(9) . . ?
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 1.5012(13) . ?
C1 C11 1.5268(14) . ?
C1 C3 1.5283(14) . ?
C1 C7 1.5332(14) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
C3 N4 1.4762(14) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
N4 N5 1.2325(14) . ?
N5 N6 1.1283(15) . ?
C7 N8 1.4819(14) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
N8 N9 1.2313(14) . ?
N9 N10 1.1292(16) . ?
C11 N12 1.4741(14) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N12 N13 1.2336(14) . ?
N13 N14 1.1309(14) . ?
C15 O21 1.2569(13) . ?
C15 C16 1.4505(15) . ?
C15 C20 1.4518(14) . ?
C16 C17 1.3762(15) . ?
C16 N22 1.4686(13) . ?
C17 C18 1.3870(15) . ?
C17 H17 0.9500 . ?
C18 C19 1.3898(15) . ?
C18 N25 1.4542(14) . ?
C19 C20 1.3762(15) . ?
C19 H19 0.9500 . ?
C20 N28 1.4608(13) . ?
N22 O23 1.2275(12) . ?
N22 O24 1.2279(13) . ?
N25 O27 1.2312(12) . ?
N25 O26 1.2329(12) . ?
N28 O29 1.2285(12) . ?
N28 O30 1.2392(12) . ?
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 O30 0.91 2.20 3.1070(12) 172.8 2_767
N2 H2B O21 0.91 1.86 2.7406(12) 163.5 2_667
N2 H2C O21 0.91 1.98 2.7643(12) 143.5 .
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 -60.91(11) . . . . ?
C11 C1 C3 N4 -178.95(9) . . . . ?
C7 C1 C3 N4 56.39(11) . . . . ?
C1 C3 N4 N5 -156.41(10) . . . . ?
C3 N4 N5 N6 174.9(10) . . . . ?
N2 C1 C7 N8 178.37(8) . . . . ?
C11 C1 C7 N8 -63.51(11) . . . . ?
C3 C1 C7 N8 59.81(11) . . . . ?
C1 C7 N8 N9 156.81(10) . . . . ?
C7 N8 N9 N10 178.3(15) . . . . ?
N2 C1 C11 N12 55.26(10) . . . . ?
C3 C1 C11 N12 173.26(9) . . . . ?
C7 C1 C11 N12 -61.54(11) . . . . ?
C1 C11 N12 N13 -173.07(10) . . . . ?
C11 N12 N13 N14 179(100) . . . . ?
O21 C15 C16 C17 178.18(10) . . . . ?
C20 C15 C16 C17 -0.38(14) . . . . ?
O21 C15 C16 N22 -2.71(15) . . . . ?
C20 C15 C16 N22 178.72(9) . . . . ?
C15 C16 C17 C18 -0.23(16) . . . . ?
N22 C16 C17 C18 -179.38(9) . . . . ?
C16 C17 C18 C19 0.35(16) . . . . ?
C16 C17 C18 N25 -179.49(9) . . . . ?
C17 C18 C19 C20 0.19(16) . . . . ?
N25 C18 C19 C20 -179.97(9) . . . . ?
C18 C19 C20 C15 -0.89(16) . . . . ?
C18 C19 C20 N28 -178.94(9) . . . . ?
O21 C15 C20 C19 -177.63(10) . . . . ?
C16 C15 C20 C19 0.95(14) . . . . ?
O21 C15 C20 N28 0.34(15) . . . . ?
C16 C15 C20 N28 178.93(9) . . . . ?
C17 C16 N22 O23 171.93(9) . . . . ?
C15 C16 N22 O23 -7.25(14) . . . . ?
C17 C16 N22 O24 -7.29(14) . . . . ?
C15 C16 N22 O24 173.53(10) . . . . ?
C17 C18 N25 O27 176.43(9) . . . . ?
C19 C18 N25 O27 -3.41(15) . . . . ?
C17 C18 N25 O26 -3.17(14) . . . . ?
C19 C18 N25 O26 176.99(9) . . . . ?
C19 C20 N28 O29 17.87(14) . . . . ?
C15 C20 N28 O29 -160.29(10) . . . . ?
C19 C20 N28 O30 -161.62(10) . . . . ?
C15 C20 N28 O30 20.22(14) . . . . ?
