#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:35:37 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179068 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/30/4303060.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_4303060
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         'C5 H8 N12 O3'
_chemical_formula_sum            'C5 H8 N12 O3'
_chemical_formula_weight         284.23
_chemical_name_systematic
; 
 1-(1,3-diazido-2-(azidomethyl)propan-2-yl)-3-nitrourea
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2009-02-11
_audit_creation_method
'from SHELXTL CIF, local template and enCIFer'
_cell_angle_alpha                90.00
_cell_angle_beta                 92.481(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.6078(18)
_cell_length_b                   6.2557(7)
_cell_length_c                   24.224(3)
_cell_measurement_temperature    93(2)
_cell_volume                     2363.0(5)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            11919
_diffrn_reflns_theta_full        28.43
_diffrn_reflns_theta_max         28.43
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2004/1 (Bruker, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.042
_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     181
_refine_ls_number_reflns         2981
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0306
_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)+(0.0403P)²+1.8141P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0822
_reflns_number_gt                2693
_reflns_number_total             2981
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic901019p_si_003_1.cif
_cod_data_source_block           compound20
_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        2362.9(5)
_cod_database_code               4303060
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.16264(6) 0.84685(15) 0.39165(4) 0.01300(18) Uani 1 1 d . . .
N2 N 0.16835(5) 0.86212(14) 0.33128(3) 0.01405(17) Uani 1 1 d . . .
H2 H 0.2145 0.8121 0.3161 0.017 Uiso 1 1 calc R . .
C3 C 0.10677(6) 0.94824(15) 0.29861(4) 0.01367(19) Uani 1 1 d . . .
O4 O 0.03929(4) 1.02462(12) 0.31436(3) 0.01662(16) Uani 1 1 d . . .
N5 N 0.11660(5) 0.95152(14) 0.24105(3) 0.01537(18) Uani 1 1 d . . .
H5 H 0.0773 1.0228 0.2215 0.018 Uiso 1 1 calc R . .
N6 N 0.17954(5) 0.85796(14) 0.21170(3) 0.01598(17) Uani 1 1 d . . .
O7 O 0.16623(5) 0.85558(14) 0.16152(3) 0.02222(18) Uani 1 1 d . . .
O8 O 0.24409(5) 0.78746(14) 0.23630(3) 0.02232(18) Uani 1 1 d . . .
C9 C 0.07827(6) 0.74129(16) 0.40815(4) 0.0163(2) Uani 1 1 d . . .
H9A H 0.0794 0.7208 0.4487 0.020 Uiso 1 1 calc R . .
H9B H 0.0294 0.8360 0.3977 0.020 Uiso 1 1 calc R . .
N10 N 0.06659(6) 0.53211(15) 0.38029(4) 0.0216(2) Uani 1 1 d . . .
N11 N 0.00961(6) 0.52642(14) 0.34311(4) 0.01907(19) Uani 1 1 d . . .
N12 N -0.04083(7) 0.49776(18) 0.30908(5) 0.0311(2) Uani 1 1 d . . .
C13 C 0.17114(6) 1.07409(16) 0.41512(4) 0.01515(19) Uani 1 1 d . . .
H13A H 0.2254 1.1392 0.4037 0.018 Uiso 1 1 calc R . .
H13B H 0.1230 1.1636 0.4005 0.018 Uiso 1 1 calc R . .
N14 N 0.17028(6) 1.06488(15) 0.47644(4) 0.01964(19) Uani 1 1 d . . .
N15 N 0.13477(5) 1.21924(15) 0.49784(4) 0.01803(18) Uani 1 1 d . . .
N16 N 0.10451(7) 1.35115(17) 0.52233(4) 0.0273(2) Uani 1 1 d . . .
C17 C 0.23680(6) 0.70457(16) 0.41229(4) 0.01492(19) Uani 1 1 d . . .
H17A H 0.2395 0.6998 0.4532 0.018 Uiso 1 1 calc R . .
H17B H 0.2285 0.5571 0.3982 0.018 Uiso 1 1 calc R . .
N18 N 0.31726(5) 0.79565(15) 0.39198(4) 0.01945(19) Uani 1 1 d . . .
N19 N 0.38340(5) 0.72243(14) 0.41463(3) 0.01621(18) Uani 1 1 d . . .
N20 N 0.44791(6) 0.66968(16) 0.43280(4) 0.0214(2) 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 C17 106.58(8) . . ?
N2 C1 C13 107.45(8) . . ?
C17 C1 C13 111.49(8) . . ?
N2 C1 C9 112.01(8) . . ?
C17 C1 C9 108.02(8) . . ?
C13 C1 C9 111.22(8) . . ?
C3 N2 C1 122.90(8) . . ?
C3 N2 H2 118.5 . . ?
C1 N2 H2 118.5 . . ?
O4 C3 N2 125.27(9) . . ?
O4 C3 N5 115.58(8) . . ?
N2 C3 N5 119.14(9) . . ?
N6 N5 C3 128.24(8) . . ?
N6 N5 H5 115.9 . . ?
C3 N5 H5 115.9 . . ?
O7 N6 O8 125.24(9) . . ?
O7 N6 N5 115.22(8) . . ?
O8 N6 N5 119.52(8) . . ?
N10 C9 C1 110.51(8) . . ?
N10 C9 H9A 109.5 . . ?
C1 C9 H9A 109.5 . . ?
N10 C9 H9B 109.5 . . ?
C1 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N11 N10 C9 115.30(9) . . ?
N12 N11 N10 172.44(11) . . ?
N14 C13 C1 109.25(8) . . ?
N14 C13 H13A 109.8 . . ?
C1 C13 H13A 109.8 . . ?
N14 C13 H13B 109.8 . . ?
C1 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?
N15 N14 C13 114.30(8) . . ?
N16 N15 N14 173.13(11) . . ?
N18 C17 C1 107.96(8) . . ?
N18 C17 H17A 110.1 . . ?
C1 C17 H17A 110.1 . . ?
N18 C17 H17B 110.1 . . ?
C1 C17 H17B 110.1 . . ?
H17A C17 H17B 108.4 . . ?
N19 N18 C17 114.43(8) . . ?
N20 N19 N18 173.60(11) . . ?
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 1.4720(12) . ?
C1 C17 1.5271(13) . ?
C1 C13 1.5347(14) . ?
C1 C9 1.5411(13) . ?
N2 C3 1.3321(12) . ?
N2 H2 0.8800 . ?
C3 O4 1.2320(12) . ?
C3 N5 1.4093(12) . ?
N5 N6 1.3689(12) . ?
N5 H5 0.8800 . ?
N6 O7 1.2242(11) . ?
N6 O8 1.2300(11) . ?
C9 N10 1.4800(14) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N10 N11 1.2386(13) . ?
N11 N12 1.1293(14) . ?
C13 N14 1.4872(12) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
N14 N15 1.2382(13) . ?
N15 N16 1.1315(13) . ?
C17 N18 1.4823(13) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
N18 N19 1.2360(12) . ?
N19 N20 1.1305(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 H2 O8 0.88 2.01 2.6728(11) 130.9 .
N5 H5 O4 0.88 1.98 2.7655(11) 147.6 2
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
C17 C1 N2 C3 169.98(9) . . . . ?
C13 C1 N2 C3 -70.39(11) . . . . ?
C9 C1 N2 C3 52.05(12) . . . . ?
C1 N2 C3 O4 0.30(16) . . . . ?
C1 N2 C3 N5 -178.43(9) . . . . ?
O4 C3 N5 N6 -172.14(9) . . . . ?
N2 C3 N5 N6 6.71(15) . . . . ?
C3 N5 N6 O7 168.85(9) . . . . ?
C3 N5 N6 O8 -12.32(15) . . . . ?
N2 C1 C9 N10 53.60(10) . . . . ?
C17 C1 C9 N10 -63.48(10) . . . . ?
C13 C1 C9 N10 173.86(8) . . . . ?
C1 C9 N10 N11 -108.49(10) . . . . ?
C9 N10 N11 N12 -172.3(8) . . . . ?
N2 C1 C13 N14 -177.07(7) . . . . ?
C17 C1 C13 N14 -60.62(10) . . . . ?
C9 C1 C13 N14 60.01(10) . . . . ?
C1 C13 N14 N15 -145.45(9) . . . . ?
C13 N14 N15 N16 -178(80) . . . . ?
N2 C1 C17 N18 54.35(10) . . . . ?
C13 C1 C17 N18 -62.62(10) . . . . ?
C9 C1 C17 N18 174.89(8) . . . . ?
C1 C17 N18 N19 166.05(9) . . . . ?
C17 N18 N19 N20 -172.0(9) . . . . ?
