##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Diisopropylammonium nitrite
;
_chemical_name_common     ?
_chemical_formula_moiety     'C6 H16 N +, N O2 -'
_chemical_formula_sum     'C6 H16 N2 O2'
_chemical_formula_iupac     'C6 H16 N +, N O2 -'
_chemical_formula_weight     148.21
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
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'
_cell_length_a     8.2314(16)
_cell_length_b     7.7466(15)
_cell_length_c     14.583(3)
_cell_angle_alpha     90.00
_cell_angle_beta     94.16(3)
_cell_angle_gamma     90.00
_cell_volume     927.5(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2127
_cell_measurement_theta_min     3.62
_cell_measurement_theta_max     27.48
_cell_measurement_temperature     298(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.10
_exptl_crystal_size_mid     0.03
_exptl_crystal_size_min     0.03
_exptl_crystal_density_diffrn     1.061
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     328
_exptl_absorpt_coefficient_mu     0.079
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrystalClear; Rigaku, 2005)'
_exptl_absorpt_correction_T_min     0.910
_exptl_absorpt_correction_T_max     1.000
_exptl_special_details     ?
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku Mercury2 CCD'
_diffrn_measurement_method     'CCD profile fitting'
_diffrn_detector_area_resol_mean     13.6612
_diffrn_reflns_number     9189
_diffrn_reflns_av_R_equivalents     0.0745
_diffrn_reflns_av_sigmaI/netI     0.0673
_diffrn_reflns_theta_min     3.62
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2127
_reflns_number_gt     1130
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1382
_refine_ls_R_factor_gt     0.0843
_refine_ls_wR_factor_gt     0.2450
_refine_ls_wR_factor_ref     0.2848
_refine_ls_goodness_of_fit_ref     1.069
_refine_ls_restrained_S_all     1.199
_refine_ls_number_reflns     2127
_refine_ls_number_parameters     95
_refine_ls_number_restraints     15
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.1379P)²+0.0979P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.501
_refine_diff_density_min     -0.317
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement     'CrystalClear (Rigaku, 2005)'
_computing_data_reduction     'CrystalClear (Rigaku, 2005)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.6713(3) 0.1958(3) 0.35567(15) 0.0543(7) Uani d . 1 1 . .
    H H1D 0.6950 0.0825 0.3543 0.065 Uiso calc R 1 1 . .
    H H1E 0.6890 0.2393 0.3000 0.065 Uiso calc R 1 1 . .
    C C2 0.4930(4) 0.2132(4) 0.3690(2) 0.0624(9) Uani d . 1 1 . .
    H H2A 0.4733 0.1702 0.4304 0.075 Uiso calc R 1 1 . .
    O O1 0.7263(3) 0.3533(3) 0.18791(17) 0.0931(9) Uani d U 1 1 . .
    C C5 0.7889(4) 0.2792(4) 0.4247(2) 0.0686(9) Uani d . 1 1 . .
    H H5A 0.7676 0.4037 0.4255 0.082 Uiso calc R 1 1 . .
    N N2 0.7438(4) 0.2425(4) 0.1320(2) 0.0925(9) Uani d U 1 1 . .
    O O2 0.8050(4) 0.2847(5) 0.0648(2) 0.1177(10) Uani d U 1 1 . .
    C C6 0.7724(5) 0.2066(6) 0.5196(2) 0.0918(12) Uani d . 1 1 . .
    H H6A 0.6642 0.2277 0.5376 0.138 Uiso calc R 1 1 . .
    H H6B 0.8500 0.2614 0.5626 0.138 Uiso calc R 1 1 . .
    H H6C 0.7925 0.0846 0.5192 0.138 Uiso calc R 1 1 . .
    C C3 0.3999(4) 0.1012(6) 0.2986(3) 0.0909(12) Uani d . 1 1 . .
    H H3A 0.4409 -0.0148 0.3032 0.136 Uiso calc R 1 1 . .
    H H3B 0.4133 0.1453 0.2381 0.136 Uiso calc R 1 1 . .
    H H3C 0.2865 0.1017 0.3099 0.136 Uiso calc R 1 1 . .
    C C4 0.9579(5) 0.2488(7) 0.3938(3) 0.1037(14) Uani d . 1 1 . .
    H H4A 0.9700 0.3099 0.3374 0.156 Uiso calc R 1 1 . .
    H H4B 0.9736 0.1275 0.3841 0.156 Uiso calc R 1 1 . .
    H H4C 1.0374 0.2895 0.4402 0.156 Uiso calc R 1 1 . .
    C C1 0.4425(5) 0.3998(5) 0.3631(3) 0.0941(13) Uani d . 1 1 . .
    H H1A 0.5025 0.4643 0.4104 0.141 Uiso calc R 1 1 . .
    H H1B 0.3280 0.4089 0.3710 0.141 Uiso calc R 1 1 . .
    H H1C 0.4646 0.4452 0.3040 0.141 Uiso calc R 1 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    N1 0.0532(15) 0.0552(13) 0.0547(13) 0.0026(10) 0.0053(10) 0.0051(10)
    C2 0.0558(19) 0.0711(19) 0.0611(17) 0.0005(14) 0.0101(14) 0.0032(14)
    O1 0.1178(19) 0.0879(17) 0.0762(14) 0.0013(13) 0.0258(13) 0.0032(11)
    C5 0.063(2) 0.0582(17) 0.082(2) -0.0024(14) -0.0121(16) 0.0038(15)
    N2 0.116(2) 0.0955(18) 0.0689(15) 0.0076(14) 0.0293(14) -0.0001(13)
    O2 0.145(2) 0.126(2) 0.0854(16) 0.0130(16) 0.0308(15) 0.0006(14)
    C6 0.102(3) 0.110(3) 0.061(2) 0.003(2) -0.0109(18) -0.005(2)
    C3 0.061(2) 0.114(3) 0.097(3) -0.0143(19) 0.0022(19) -0.014(2)
    C4 0.056(2) 0.142(4) 0.111(3) -0.011(2) -0.003(2) 0.025(3)
    C1 0.068(2) 0.089(3) 0.125(3) 0.0240(19) 0.006(2) 0.003(2)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N1 C5 . 1.492(4) ?
    N1 C2 . 1.500(4) ?
    N1 H1D . 0.9000 ?
    N1 H1E . 0.9000 ?
    C2 C1 . 1.505(5) ?
    C2 C3 . 1.509(5) ?
    C2 H2A . 0.9800 ?
    O1 N2 . 1.200(4) ?
    C5 C6 . 1.510(5) ?
    C5 C4 . 1.512(5) ?
    C5 H5A . 0.9800 ?
    N2 O2 . 1.181(4) ?
    C6 H6A . 0.9600 ?
    C6 H6B . 0.9600 ?
    C6 H6C . 0.9600 ?
    C3 H3A . 0.9600 ?
    C3 H3B . 0.9600 ?
    C3 H3C . 0.9600 ?
    C4 H4A . 0.9600 ?
    C4 H4B . 0.9600 ?
    C4 H4C . 0.9600 ?
    C1 H1A . 0.9600 ?
    C1 H1B . 0.9600 ?
    C1 H1C . 0.9600 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C5 N1 C2 . . 117.8(2) ?
    C5 N1 H1D . . 107.9 ?
    C2 N1 H1D . . 107.9 ?
    C5 N1 H1E . . 107.9 ?
    C2 N1 H1E . . 107.9 ?
    H1D N1 H1E . . 107.2 ?
    N1 C2 C1 . . 110.4(3) ?
    N1 C2 C3 . . 108.2(2) ?
    C1 C2 C3 . . 112.9(3) ?
    N1 C2 H2A . . 108.4 ?
    C1 C2 H2A . . 108.4 ?
    C3 C2 H2A . . 108.4 ?
    N1 C5 C6 . . 111.1(3) ?
    N1 C5 C4 . . 107.3(3) ?
    C6 C5 C4 . . 111.2(3) ?
    N1 C5 H5A . . 109.1 ?
    C6 C5 H5A . . 109.1 ?
    C4 C5 H5A . . 109.1 ?
    O2 N2 O1 . . 116.4(4) ?
    C5 C6 H6A . . 109.5 ?
    C5 C6 H6B . . 109.5 ?
    H6A C6 H6B . . 109.5 ?
    C5 C6 H6C . . 109.5 ?
    H6A C6 H6C . . 109.5 ?
    H6B C6 H6C . . 109.5 ?
    C2 C3 H3A . . 109.5 ?
    C2 C3 H3B . . 109.5 ?
    H3A C3 H3B . . 109.5 ?
    C2 C3 H3C . . 109.5 ?
    H3A C3 H3C . . 109.5 ?
    H3B C3 H3C . . 109.5 ?
    C5 C4 H4A . . 109.5 ?
    C5 C4 H4B . . 109.5 ?
    H4A C4 H4B . . 109.5 ?
    C5 C4 H4C . . 109.5 ?
    H4A C4 H4C . . 109.5 ?
    H4B C4 H4C . . 109.5 ?
    C2 C1 H1A . . 109.5 ?
    C2 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    C2 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C5 N1 C2 C1 . . . . 63.0(3) ?
    C5 N1 C2 C3 . . . . -173.0(3) ?
    C2 N1 C5 C6 . . . . 60.4(3) ?
    C2 N1 C5 C4 . . . . -177.8(3) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N1 H1E O1 . 0.90 1.90 2.800(3) 174
    N1 H1D O1 2_645 0.90 2.00 2.869(3) 161
_iucr_refine_instructions_details
;
TITL 1 in P2(1)/n
CELL 0.71073   8.2314   7.7466  14.5834  90.000  94.162  90.000
ZERR  4.00   0.0016   0.0015   0.0029   0.000   0.030   0.000
LATT  1
SYMM 0.5-X, 0.5+Y, 0.5-Z
SFAC C H N O
UNIT 24 64 8 8
L.S. 14
BOND $H
FMAP 2
PLAN 20
ACTA
SIMU 0.09 0.002 O1 O2 N2
DELU 0.09 0.002 O1 O2 N2
CONF
EQIV $1 -x+3/2, y-1/2, -z+1/2
HTAB N1 O1_$1
HTAB N1 O1
WGHT    0.137900    0.097900
FVAR       0.31328
N1    3    0.671272    0.195799    0.355667    11.00000    0.05315    0.05516 =
         0.05467    0.00514    0.00535    0.00262
AFIX  23
H1D   2    0.694982    0.082455    0.354279    11.00000   -1.20000
H1E   2    0.688957    0.239265    0.300031    11.00000   -1.20000
AFIX   0
C2    1    0.492964    0.213249    0.368965    11.00000    0.05576    0.07110 =
         0.06114    0.00320    0.01009    0.00050
AFIX  13
H2A   2    0.473264    0.170198    0.430367    11.00000   -1.20000
AFIX   0
O1    4    0.726321    0.353323    0.187911    11.00000    0.11783    0.08786 =
         0.07625    0.00323    0.02584    0.00134
C5    1    0.788887    0.279218    0.424677    11.00000    0.06307    0.05821 =
         0.08210    0.00384   -0.01212   -0.00243
AFIX  13
H5A   2    0.767593    0.403654    0.425526    11.00000   -1.20000
AFIX   0
N2    3    0.743774    0.242476    0.132033    11.00000    0.11639    0.09553 =
         0.06886   -0.00012    0.02928    0.00760
O2    4    0.805009    0.284729    0.064784    11.00000    0.14510    0.12575 =
         0.08545    0.00056    0.03077    0.01300
C6    1    0.772380    0.206627    0.519645    11.00000    0.10181    0.10975 =
         0.06128   -0.00528   -0.01089    0.00252
AFIX 137
H6A   2    0.664215    0.227733    0.537573    11.00000   -1.50000
H6B   2    0.849957    0.261427    0.562557    11.00000   -1.50000
H6C   2    0.792473    0.084568    0.519182    11.00000   -1.50000
AFIX   0
C3    1    0.399932    0.101169    0.298634    11.00000    0.06097    0.11420 =
         0.09698   -0.01414    0.00223   -0.01433
AFIX 137
H3A   2    0.440856   -0.014795    0.303163    11.00000   -1.50000
H3B   2    0.413314    0.145296    0.238131    11.00000   -1.50000
H3C   2    0.286456    0.101721    0.309876    11.00000   -1.50000
AFIX   0
C4    1    0.957906    0.248751    0.393766    11.00000    0.05617    0.14217 =
         0.11133    0.02539   -0.00313   -0.01084
AFIX 137
H4A   2    0.970019    0.309864    0.337402    11.00000   -1.50000
H4B   2    0.973630    0.127494    0.384102    11.00000   -1.50000
H4C   2    1.037395    0.289547    0.440165    11.00000   -1.50000
AFIX   0
C1    1    0.442456    0.399813    0.363073    11.00000    0.06803    0.08857 =
         0.12537    0.00267    0.00561    0.02396
AFIX 137
H1A   2    0.502533    0.464344    0.410417    11.00000   -1.50000
H1B   2    0.328025    0.408942    0.371039    11.00000   -1.50000
H1C   2    0.464583    0.445189    0.304002    11.00000   -1.50000
HKLF 4
REM  1 in P2(1)/n
REM R1 =  0.0843 for   1130 Fo > 4sig(Fo)  and  0.1382 for all   2127 data
REM     95 parameters refined using     15 restraints
END
WGHT      0.1383      0.0976
REM Highest difference peak  0.501,  deepest hole -0.317,  1-sigma level  0.046
Q1    1   0.6786  0.1297  0.1204  11.00000  0.05    0.24
Q2    1   0.4746  0.2753  0.3628  11.00000  0.05    0.17
Q3    1   0.4634  0.2573  0.4167  11.00000  0.05    0.14
Q4    1   0.7751  0.2586  0.4656  11.00000  0.05    0.14
Q5    1   0.9839  0.2252  0.3283  11.00000  0.05    0.12
Q6    1   0.9981  0.2973  0.4048  11.00000  0.05    0.12
Q7    1   0.9146  0.3026  0.1033  11.00000  0.05    0.12
Q8    1   0.7160  0.2070  0.5455  11.00000  0.05    0.11
Q9    1   0.9865  0.0873  0.4144  11.00000  0.05    0.11
Q10   1   0.4686  0.0842  0.2488  11.00000  0.05    0.10
Q11   1   0.2790  0.1140  0.2832  11.00000  0.05    0.10
Q12   1   0.7975  0.3804  0.3832  11.00000  0.05    0.10
Q13   1   0.2600  0.0766  0.3676  11.00000  0.05    0.09
Q14   1   0.8197  0.3235  0.2021  11.00000  0.05    0.09
Q15   1   0.5023  0.4964  0.3412  11.00000  0.05    0.09
Q16   1   0.4617  0.1442  0.3554  11.00000  0.05    0.09
Q17   1   0.5127  0.2801  0.5051  11.00000  0.05    0.09
Q18   1   0.7049  0.2779  0.3436  11.00000  0.05    0.09
Q19   1   0.7564  0.0569  0.5157  11.00000  0.05    0.08
Q20   1   0.5762  0.2010  0.3978  11.00000  0.05    0.08
;
data_global
_journal_date_recd_electronic     2012-02-25
_journal_date_accepted     2012-02-26
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      4
_journal_page_first     o986
_journal_page_last     o986
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812008574
_journal_coeditor_code     HB6657
_publ_contact_author_name     'Ying-Chun Wang'
_publ_contact_author_address
;
College of Chemistry and Chemical Engineering,
Southeast University,
Nanjing 210096,
People's Republic of China
;
_publ_contact_author_email     wangyc33@yahoo.com.cn
_publ_contact_author_fax     '862552090598'
_publ_contact_author_phone     '862552090598'
_publ_section_title
;
Diisopropylammonium nitrite
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Wang, Ying-Chun' .
;
College of Chemistry and Chemical Engineering,
Southeast University,
Nanjing 210096,
People's Republic of China
;
    'Jie, Xu' .
;
College of Chemistry and Chemical Engineering,
Southeast University,
Nanjing 210096,
People's Republic of China
;
