#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:18:41 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180499 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/68/7216868.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_7216868
loop_
_publ_author_name
'Kopylovich, Maximilian N.'
'Kukushkin, Vadim Yu.'
'Guedes da Silva, M. Fátima C.'
'Haukka, Matti'
'Fraústo da Silva, João J. R.'
'Pombeiro, Armando J. L.'
_publ_section_title
;
 Conversion of alkanenitriles to amidines and carboxylic acids mediated by
 a cobalt(II)--ketoxime system 
;
_journal_issue                   13
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              1569
_journal_paper_doi               10.1039/b101337h
_journal_year                    2001
_chemical_formula_sum            'C3 H9 N3 O3'
_chemical_formula_weight         135.13
_chemical_name_common            '[CH3CH2C(NH2)2][NO3]'
_chemical_name_systematic
; 
 ? 
;
_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_method           SHELXL-97
_cell_angle_alpha                72.830(2)
_cell_angle_beta                 87.467(2)
_cell_angle_gamma                82.367(2)
_cell_formula_units_Z            2
_cell_length_a                   6.5627(2)
_cell_length_b                   6.6924(2)
_cell_length_c                   8.2274(3)
_cell_measurement_temperature    120(2)
_cell_volume                     342.18(2)
_computing_cell_refinement       'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius, 1999)'
_computing_data_reduction        'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP in SHELXTL v.5.1 (Bruker Axs, 1998)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       phi/omega-scan
_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  0.0127
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2183
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         4.06
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.9664
_exptl_absorpt_correction_T_min  0.9664
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             144
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     99
_refine_ls_number_reflns         1240
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0338
_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)+(0.0360P)²+0.1199P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0892
_reflns_number_gt                1165
_reflns_number_total             1240
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b101337h.txt
_cod_data_source_block           structure1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        342.181(19)
_cod_database_code               7216868
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
N1 N 1.15836(16) 0.25976(18) 0.31694(14) 0.0259(3) Uani 1 1 d .
N2 N 0.89862(17) 0.52802(16) 0.29828(13) 0.0237(3) Uani 1 1 d .
C1 C 0.96308(17) 0.33401(18) 0.30018(14) 0.0197(3) Uani 1 1 d .
C2 C 0.81161(18) 0.19619(18) 0.27568(15) 0.0221(3) Uani 1 1 d .
H2A H 0.6800 0.2276 0.3322 0.026 Uiso 1 1 calc R
H2B H 0.8649 0.0464 0.3288 0.026 Uiso 1 1 calc R
C3 C 0.7751(4) 0.2331(4) 0.0880(2) 0.0663(6) Uani 1 1 d .
H3A H 0.7199 0.3808 0.0361 0.099 Uiso 1 1 calc R
H3B H 0.6766 0.1415 0.0741 0.099 Uiso 1 1 calc R
H3C H 0.9053 0.2009 0.0324 0.099 Uiso 1 1 calc R
N3 N 0.61687(15) 0.25402(15) 0.68172(12) 0.0209(3) Uani 1 1 d .
O1 O 0.80612(12) 0.19179(13) 0.67588(11) 0.0253(2) Uani 1 1 d .
O2 O 0.55834(13) 0.43344(13) 0.69731(12) 0.0274(3) Uani 1 1 d .
O3 O 0.48885(14) 0.13804(15) 0.67157(14) 0.0373(3) Uani 1 1 d .
H22 H 0.988(2) 0.610(2) 0.3053(18) 0.027(4) Uiso 1 1 d .
H21 H 0.770(3) 0.570(2) 0.2933(19) 0.029(4) Uiso 1 1 d .
H12 H 1.249(2) 0.342(3) 0.3234(19) 0.031(4) Uiso 1 1 d .
H11 H 1.195(2) 0.130(3) 0.3170(19) 0.035(4) Uiso 1 1 d .
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
N1 0.0192(5) 0.0197(5) 0.0417(6) -0.0128(5) -0.0009(4) -0.0036(4)
N2 0.0172(6) 0.0200(5) 0.0352(6) -0.0093(4) -0.0003(4) -0.0041(4)
C1 0.0204(6) 0.0196(6) 0.0195(5) -0.0053(4) 0.0012(4) -0.0051(4)
C2 0.0207(6) 0.0203(6) 0.0266(6) -0.0072(5) 0.0006(4) -0.0069(5)
C3 0.0967(15) 0.0877(14) 0.0287(8) -0.0133(8) -0.0025(8) -0.0696(12)
N3 0.0199(5) 0.0195(5) 0.0243(5) -0.0068(4) 0.0008(4) -0.0051(4)
O1 0.0173(4) 0.0231(4) 0.0382(5) -0.0132(4) 0.0011(3) -0.0019(3)
O2 0.0222(5) 0.0200(4) 0.0432(6) -0.0150(4) -0.0020(4) -0.0007(3)
O3 0.0244(5) 0.0280(5) 0.0661(7) -0.0200(5) 0.0028(4) -0.0135(4)
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
C1 N1 H12 120.1(10)
C1 N1 H11 118.6(10)
H12 N1 H11 121.2(15)
C1 N2 H22 119.1(10)
C1 N2 H21 119.1(10)
H22 N2 H21 121.8(14)
N2 C1 N1 121.30(11)
N2 C1 C2 119.39(11)
N1 C1 C2 119.27(10)
C1 C2 C3 110.45(10)
C1 C2 H2A 109.6
C3 C2 H2A 109.6
C1 C2 H2B 109.6
C3 C2 H2B 109.6
H2A C2 H2B 108.1
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
O3 N3 O2 120.04(10)
O3 N3 O1 119.97(9)
O2 N3 O1 119.98(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.3093(16)
N1 H12 0.875(17)
N1 H11 0.869(18)
N2 C1 1.3068(15)
N2 H22 0.873(17)
N2 H21 0.854(17)
C1 C2 1.5002(15)
C2 C3 1.5149(19)
C2 H2A 0.9900
C2 H2B 0.9900
C3 H3A 0.9800
C3 H3B 0.9800
C3 H3C 0.9800
N3 O3 1.2381(13)
N3 O2 1.2529(13)
N3 O1 1.2599(13)
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
N2 C1 C2 C3 84.09(16)
N1 C1 C2 C3 -93.47(16)
