#------------------------------------------------------------------------------
#$Date: 2019-11-23 19:10:06 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234588 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/63/4036348.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_4036348
loop_
_publ_author_name
'Mercalli, Valentina'
'Massarotti, Alberto'
'Varese, Monica'
'Giustiniano, Mariateresa'
'Meneghetti, Fiorella'
'Novellino, Ettore'
'Tron, Gian Cesare'
_publ_section_title
;
 Multicomponent Reaction of Z-Chlorooximes, Isocyanides, and
 Hydroxylamines as Hypernucleophilic Traps. A One-Pot Route to
 Aminodioximes and Their Transformation into 5-Amino-1,2,4-oxadiazoles by
 Mitsunobu-Beckmann Rearrangement.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9652
_journal_page_last               9661
_journal_paper_doi               10.1021/acs.joc.5b01676
_journal_volume                  80
_journal_year                    2015
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C12 H17 N3 O2'
_chemical_formula_sum            'C12 H17 N3 O2'
_chemical_formula_weight         235.29
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_date             2014-12-04T15:56:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 105.522(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.625(3)
_cell_length_b                   6.3084(14)
_cell_length_c                   14.588(3)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_measurement_wavelength     0.71073
_cell_volume                     1296.8(5)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2307
_diffrn_reflns_theta_full        25.11
_diffrn_reflns_theta_max         25.11
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2307
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0897P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1611
_reflns_number_gt                1528
_reflns_number_total             2307
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01676_si_002.cif
_cod_data_source_block           vm29
_cod_original_cell_volume        1296.7(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4036348
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
C1 C 0.29787(17) 1.1981(4) 0.14704(15) 0.0505(6) Uani 1 1 d
C2 C 0.3157(2) 0.9980(5) 0.11609(19) 0.0594(7) Uani 1 1 d
C3 C 0.4021(2) 0.9516(6) 0.0999(2) 0.0738(9) Uani 1 1 d
C4 C 0.4720(3) 1.1039(7) 0.1155(2) 0.0833(10) Uani 1 1 d
C5 C 0.4556(2) 1.3005(7) 0.1474(3) 0.0887(11) Uani 1 1 d
C6 C 0.3698(2) 1.3479(5) 0.1630(2) 0.0710(8) Uani 1 1 d
C9 C 0.19798(17) 1.0096(4) 0.34773(17) 0.0514(6) Uani 1 1 d
C10 C 0.2207(4) 1.2364(6) 0.3783(3) 0.0889(12) Uani 1 1 d
C12 C 0.2864(3) 0.8836(10) 0.3479(3) 0.0953(13) Uani 1 1 d
C11 C 0.1485(3) 0.9022(7) 0.4147(2) 0.0762(9) Uani 1 1 d
N2 N 0.07924(14) 1.0322(3) 0.08718(14) 0.0490(5) Uani 1 1 d
C7 C 0.20399(16) 1.2522(4) 0.15993(15) 0.0460(6) Uani 1 1 d
N1 N 0.18055(15) 1.4489(3) 0.15471(15) 0.0569(6) Uani 1 1 d
C8 C 0.13502(16) 1.0822(3) 0.16872(16) 0.0433(6) Uani 1 1 d
N3 N 0.13102(17) 0.9983(3) 0.25240(15) 0.0556(6) Uani 1 1 d
O1 O 0.01424(12) 0.8691(2) 0.09773(13) 0.0555(5) Uani 1 1 d
O2 O 0.09106(14) 1.4798(3) 0.16902(16) 0.0683(6) Uani 1 1 d
H6 H 0.360(2) 1.490(5) 0.188(2) 0.084(10) Uiso 1 1 d
H3 H 0.4111(18) 0.810(5) 0.0802(19) 0.070(8) Uiso 1 1 d
H2 H 0.270(2) 0.896(5) 0.1036(19) 0.068(8) Uiso 1 1 d
H5 H 0.505(3) 1.399(6) 0.160(2) 0.101(11) Uiso 1 1 d
H4 H 0.530(2) 1.066(5) 0.105(2) 0.080(9) Uiso 1 1 d
H31 H 0.081(2) 0.920(5) 0.244(2) 0.071(9) Uiso 1 1 d
H21 H 0.072(3) 1.606(6) 0.145(3) 0.118(14) Uiso 1 1 d
H12 H -0.024(3) 0.870(6) 0.041(3) 0.111(13) Uiso 1 1 d
H123 H 0.325(3) 0.885(6) 0.410(3) 0.114(13) Uiso 1 1 d
H111 H 0.195(2) 0.896(4) 0.480(2) 0.078(8) Uiso 1 1 d
H121 H 0.329(3) 0.983(7) 0.315(3) 0.135(15) Uiso 1 1 d
H103 H 0.259(3) 1.237(6) 0.444(3) 0.125(13) Uiso 1 1 d
H102 H 0.269(3) 1.295(7) 0.343(3) 0.130(15) Uiso 1 1 d
H113 H 0.087(3) 0.968(5) 0.416(2) 0.096(11) Uiso 1 1 d
H112 H 0.135(3) 0.758(7) 0.394(3) 0.113(13) Uiso 1 1 d
H101 H 0.162(3) 1.297(6) 0.367(3) 0.100(14) Uiso 1 1 d
H122 H 0.280(5) 0.734(13) 0.327(5) 0.24(3) Uiso 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 0 '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 0.006 '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
C6 C1 C2 118.3(3)
C6 C1 C7 120.7(3)
C2 C1 C7 120.9(2)
C3 C2 C1 120.6(3)
C4 C3 C2 119.9(3)
C5 C4 C3 119.9(3)
C6 C5 C4 120.5(3)
C5 C6 C1 120.8(3)
N3 C9 C10 111.3(2)
N3 C9 C12 109.1(2)
C10 C9 C12 112.1(4)
N3 C9 C11 106.0(2)
C10 C9 C11 109.7(3)
C12 C9 C11 108.5(3)
C8 N2 O1 110.47(18)
N1 C7 C1 117.3(2)
N1 C7 C8 121.4(2)
C1 C7 C8 121.0(2)
C7 N1 O2 111.90(19)
N2 C8 N3 124.8(2)
N2 C8 C7 111.70(19)
N3 C8 C7 123.5(2)
C8 N3 C9 131.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.386(4)
C1 C2 1.389(4)
C1 C7 1.475(3)
C2 C3 1.378(4)
C3 C4 1.377(5)
C4 C5 1.369(5)
C5 C6 1.367(5)
C9 N3 1.473(3)
C9 C10 1.509(4)
C9 C12 1.518(4)
C9 C11 1.522(4)
N2 C8 1.289(3)
N2 O1 1.437(2)
C7 N1 1.284(3)
C7 C8 1.501(3)
N1 O2 1.393(3)
C8 N3 1.346(3)
