#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:29:03 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178901 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/30/4113021.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_4113021
loop_
_publ_author_name
'Joseph E. Saavedra'
'D. Scott Bohle'
'Kamilah N. Smith'
'Clifford George'
'Jeffrey R. Deschamps'
'Damon Parrish'
'Joseph Ivanic'
'Yan-Ni Wang'
'Michael L. Citro'
'Larry K. Keefer'
_publ_section_title
;
 Chemistry of the Diazeniumdiolates. O- versus N-Alkylation of the
 RNH[N(O)NO]- Ion
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12880
_journal_page_last               12887
_journal_paper_doi               10.1021/ja031538i
_journal_volume                  126
_journal_year                    2004
_chemical_formula_moiety         'C7 H15 N3 O2'
_chemical_formula_sum            'C7 H15 N3 O2'
_chemical_formula_weight         173.22
_chemical_name_systematic
; 
 ? 
;
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.738(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.517(5)
_cell_length_b                   6.0509(16)
_cell_length_c                   9.311(3)
_cell_measurement_reflns_used    1879
_cell_measurement_temperature    93(1)
_cell_measurement_theta_max      26.15
_cell_measurement_theta_min      2.48
_cell_volume                     927.4(5)
_computing_cell_refinement       'Bruker SMART v5.059 (Bruker, 1999)'
_computing_data_collection       'Bruker SMART v5.059 (Bruker, 1999)'
_computing_data_reduction
;
Bruker SAINT v6.02A (Bruker, 2000a), Bruker XPREP v5.1 (Bruker, 1997)
;
_computing_molecular_graphics    'Bruker Shelxtl v6.10 (Bruker, 2000b)'
_computing_publication_material  'Bruker Shelxtl v6.10 (Bruker, 2000b)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      93(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0843
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5868
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         1.24
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  variable
_diffrn_standards_number         41
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.894331
_exptl_absorpt_correction_T_min  0.614872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.01 (Bruker, 2000c)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       rod
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1898
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.921
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0425
_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)+(0.0661P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.1317
_reflns_number_gt                1106
_reflns_number_total             1898
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja031538isi20031124_103744.cif
_cod_data_source_block           nci50c
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4113021
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
N2 N 0.88264(11) 0.3796(3) 0.07144(19) 0.0204(5) Uani 1 1 d .
N1 N 0.84208(11) 0.2073(3) 0.0979(2) 0.0184(5) Uani 1 1 d .
N3 N 0.82369(12) 0.0672(3) -0.0196(2) 0.0192(5) Uani 1 1 d .
H3 H 0.8344(14) 0.142(4) -0.092(3) 0.023 Uiso 1 1 d .
O1 O 0.82063(10) 0.1464(3) 0.21849(16) 0.0239(5) Uani 1 1 d .
O2 O 0.90166(9) 0.4838(3) 0.20201(16) 0.0224(4) Uani 1 1 d .
C7 C 0.94956(15) 0.6753(4) 0.1769(3) 0.0287(6) Uani 1 1 d .
H7A H 0.9630 0.7506 0.2665 0.043 Uiso 1 1 calc R
H7B H 0.9192 0.7725 0.1112 0.043 Uiso 1 1 calc R
H7C H 0.9986 0.6309 0.1363 0.043 Uiso 1 1 calc R
C1 C 0.73721(13) 0.0050(4) -0.0331(2) 0.0184(5) Uani 1 1 d .
H1A H 0.7254 -0.0719 0.0554 0.022 Uiso 1 1 calc R
C2 C 0.72334(15) -0.1562(4) -0.1574(2) 0.0234(6) Uani 1 1 d .
H2A H 0.7579 -0.2845 -0.1394 0.028 Uiso 1 1 calc R
H2B H 0.7379 -0.0866 -0.2455 0.028 Uiso 1 1 calc R
C3 C 0.63509(14) -0.2285(4) -0.1755(3) 0.0277(6) Uani 1 1 d .
H3A H 0.6224 -0.3120 -0.0913 0.033 Uiso 1 1 calc R
H3B H 0.6269 -0.3246 -0.2588 0.033 Uiso 1 1 calc R
C4 C 0.57801(15) -0.0322(4) -0.1949(3) 0.0259(6) Uani 1 1 d .
H4A H 0.5222 -0.0835 -0.2006 0.031 Uiso 1 1 calc R
H4B H 0.5867 0.0430 -0.2843 0.031 Uiso 1 1 calc R
C5 C 0.59237(14) 0.1284(4) -0.0696(2) 0.0236(6) Uani 1 1 d .
H5A H 0.5575 0.2563 -0.0864 0.028 Uiso 1 1 calc R
H5B H 0.5784 0.0575 0.0185 0.028 Uiso 1 1 calc R
C6 C 0.68051(14) 0.2026(4) -0.0521(3) 0.0209(6) Uani 1 1 d .
H6B H 0.6888 0.2986 0.0312 0.025 Uiso 1 1 calc R
H6C H 0.6930 0.2860 -0.1364 0.025 Uiso 1 1 calc R
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
N2 0.0217(12) 0.0220(12) 0.0175(11) -0.0032(9) 0.0014(8) -0.0037(9)
N1 0.0190(11) 0.0217(12) 0.0146(10) -0.0006(8) 0.0018(8) 0.0013(9)
N3 0.0242(12) 0.0227(12) 0.0108(10) -0.0015(8) 0.0017(8) -0.0008(9)
O1 0.0339(11) 0.0279(10) 0.0108(8) 0.0021(7) 0.0064(7) -0.0046(8)
O2 0.0255(10) 0.0234(10) 0.0181(9) -0.0052(7) 0.0012(7) -0.0053(8)
C7 0.0315(16) 0.0214(15) 0.0329(15) -0.0010(12) 0.0012(12) -0.0052(12)
C1 0.0198(13) 0.0208(13) 0.0145(12) 0.0010(10) 0.0018(10) -0.0002(10)
C2 0.0277(15) 0.0213(15) 0.0212(14) -0.0036(11) 0.0033(11) 0.0020(11)
C3 0.0296(16) 0.0280(16) 0.0258(14) -0.0071(12) 0.0039(11) -0.0060(13)
C4 0.0211(14) 0.0348(16) 0.0216(14) -0.0016(11) -0.0005(10) -0.0057(12)
C5 0.0201(14) 0.0262(15) 0.0244(14) 0.0009(11) 0.0011(10) 0.0014(11)
C6 0.0240(14) 0.0182(13) 0.0205(13) -0.0023(10) 0.0020(10) 0.0005(11)
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
N1 N2 O2 106.76(16)
O1 N1 N2 127.02(19)
O1 N1 N3 117.48(18)
N2 N1 N3 115.41(17)
N1 N3 C1 111.64(17)
N1 N3 H3 105.0(17)
C1 N3 H3 109.4(16)
N2 O2 C7 108.29(16)
O2 C7 H7A 109.5
O2 C7 H7B 109.5
H7A C7 H7B 109.5
O2 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
N3 C1 C2 108.31(17)
N3 C1 C6 113.15(19)
C2 C1 C6 111.37(19)
N3 C1 H1A 107.9
C2 C1 H1A 107.9
C6 C1 H1A 107.9
C1 C2 C3 110.69(19)
C1 C2 H2A 109.5
C3 C2 H2A 109.5
C1 C2 H2B 109.5
C3 C2 H2B 109.5
H2A C2 H2B 108.1
C2 C3 C4 111.6(2)
C2 C3 H3A 109.3
C4 C3 H3A 109.3
C2 C3 H3B 109.3
C4 C3 H3B 109.3
H3A C3 H3B 108.0
C3 C4 C5 110.7(2)
C3 C4 H4A 109.5
C5 C4 H4A 109.5
C3 C4 H4B 109.5
C5 C4 H4B 109.5
H4A C4 H4B 108.1
C6 C5 C4 110.98(19)
C6 C5 H5A 109.4
C4 C5 H5A 109.4
C6 C5 H5B 109.4
C4 C5 H5B 109.4
H5A C5 H5B 108.0
C5 C6 C1 110.86(19)
C5 C6 H6B 109.5
C1 C6 H6B 109.5
C5 C6 H6C 109.5
C1 C6 H6C 109.5
H6B C6 H6C 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N2 N1 1.274(2)
N2 O2 1.382(2)
N1 O1 1.260(2)
N1 N3 1.397(3)
N3 C1 1.472(3)
N3 H3 0.84(2)
O2 C7 1.433(3)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C1 C2 1.516(3)
C1 C6 1.520(3)
C1 H1A 0.9800
C2 C3 1.518(3)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.518(3)
C3 H3A 0.9700
C3 H3B 0.9700
C4 C5 1.521(3)
C4 H4A 0.9700
C4 H4B 0.9700
C5 C6 1.519(3)
C5 H5A 0.9700
C5 H5B 0.9700
C6 H6B 0.9700
C6 H6C 0.9700
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
O2 N2 N1 O1 2.3(3)
O2 N2 N1 N3 -174.09(17)
O1 N1 N3 C1 51.7(3)
N2 N1 N3 C1 -131.5(2)
N1 N2 O2 C7 178.24(18)
N1 N3 C1 C2 -176.92(18)
N1 N3 C1 C6 59.1(2)
N3 C1 C2 C3 179.33(19)
C6 C1 C2 C3 -55.6(3)
C1 C2 C3 C4 55.7(3)
C2 C3 C4 C5 -56.0(3)
C3 C4 C5 C6 56.0(3)
C4 C5 C6 C1 -56.2(3)
N3 C1 C6 C5 178.45(18)
C2 C1 C6 C5 56.2(2)
