#------------------------------------------------------------------------------
#$Date: 2019-10-11 09:30:19 +0300 (Fri, 11 Oct 2019) $
#$Revision: 219271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/67/4106738.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_4106738
loop_
_publ_author_name
'Baidya, Mahiuddin'
'Yamamoto, Hisashi'
_publ_section_title
;
 Metal Nitrite: A Powerful Oxidizing Reagent
;
_journal_coden_ASTM              JACSAT
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13880
_journal_page_last               13882
_journal_paper_doi               10.1021/ja206736q
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C12 H21 N O2'
_chemical_formula_weight         211.30
_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                96.069(12)
_cell_angle_beta                 100.109(11)
_cell_angle_gamma                104.700(11)
_cell_formula_units_Z            2
_cell_length_a                   5.492(4)
_cell_length_b                   8.188(6)
_cell_length_c                   13.970(10)
_cell_measurement_temperature    100(2)
_cell_volume                     590.7(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_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  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6822
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9905
_exptl_absorpt_correction_T_min  0.9780
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0527
_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)+(0.0876P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1373
_refine_ls_wR_factor_ref         0.1436
_reflns_number_gt                2226
_reflns_number_total             2816
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja206736q_si_003.cif
_cod_data_source_block           baid04s
_cod_depositor_comments
;
 Updated bibliographic information.

 Antanas Vaitkus,
 2019-10-11
;
_cod_original_cell_volume        590.6(7)
_cod_database_code               4106738
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
C1 C 0.7846(3) 0.80643(18) 0.41510(10) 0.0201(3) Uani 1 1 d .
C2 C 0.7902(3) 0.62742(18) 0.42660(10) 0.0228(3) Uani 1 1 d .
H2A H 0.6998 0.5907 0.4794 0.027 Uiso 1 1 calc R
H2B H 0.9711 0.6247 0.4465 0.027 Uiso 1 1 calc R
C3 C 0.6616(3) 0.50249(18) 0.33055(11) 0.0246(3) Uani 1 1 d .
H3A H 0.7515 0.5405 0.2779 0.030 Uiso 1 1 calc R
H3B H 0.6811 0.3879 0.3397 0.030 Uiso 1 1 calc R
C4 C 0.3753(3) 0.48864(19) 0.29769(10) 0.0246(3) Uani 1 1 d .
H4A H 0.3514 0.6047 0.3062 0.030 Uiso 1 1 calc R
H4B H 0.2787 0.4218 0.3409 0.030 Uiso 1 1 calc R
C5 C 0.2617(3) 0.40376(19) 0.19029(11) 0.0266(3) Uani 1 1 d .
H5A H 0.3053 0.2940 0.1797 0.032 Uiso 1 1 calc R
H5B H 0.0718 0.3777 0.1785 0.032 Uiso 1 1 calc R
C6 C 0.3581(3) 0.51351(19) 0.11539(11) 0.0276(4) Uani 1 1 d .
H6A H 0.3062 0.4423 0.0494 0.033 Uiso 1 1 calc R
H6B H 0.5486 0.5521 0.1325 0.033 Uiso 1 1 calc R
C7 C 0.2554(3) 0.6707(2) 0.11044(11) 0.0280(4) Uani 1 1 d .
H7A H 0.0804 0.6349 0.0681 0.034 Uiso 1 1 calc R
H7B H 0.2402 0.7141 0.1774 0.034 Uiso 1 1 calc R
C8 C 0.4219(3) 0.8165(2) 0.07073(11) 0.0295(4) Uani 1 1 d .
H8A H 0.3268 0.9028 0.0590 0.035 Uiso 1 1 calc R
H8B H 0.4517 0.7709 0.0066 0.035 Uiso 1 1 calc R
C9 C 0.6828(3) 0.9043(2) 0.13990(11) 0.0279(4) Uani 1 1 d .
H9A H 0.7675 0.8161 0.1594 0.033 Uiso 1 1 calc R
H9B H 0.7938 0.9790 0.1040 0.033 Uiso 1 1 calc R
C10 C 0.6603(3) 1.01161(19) 0.23276(11) 0.0253(3) Uani 1 1 d .
H10A H 0.5123 0.9476 0.2578 0.030 Uiso 1 1 calc R
H10B H 0.6244 1.1185 0.2153 0.030 Uiso 1 1 calc R
C11 C 0.9032(3) 1.05735(18) 0.31495(11) 0.0234(3) Uani 1 1 d .
H11A H 1.0536 1.1171 0.2897 0.028 Uiso 1 1 calc R
H11B H 0.8833 1.1359 0.3701 0.028 Uiso 1 1 calc R
C12 C 0.9500(3) 0.89868(18) 0.35181(10) 0.0216(3) Uani 1 1 d .
N1 N 0.6571(2) 0.89502(15) 0.45599(8) 0.0207(3) Uani 1 1 d .
O1 O 1.11564(19) 0.83726(13) 0.32854(7) 0.0261(3) Uani 1 1 d .
O2 O 0.5142(2) 0.80916(13) 0.51819(8) 0.0251(3) Uani 1 1 d .
H2 H 0.4418 0.8745 0.5452 0.038 Uiso 1 1 calc R
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 C1 C2 127.23(13)
N1 C1 C12 114.61(13)
C2 C1 C12 118.13(12)
C1 C2 C3 111.53(12)
C4 C3 C2 113.09(12)
C3 C4 C5 113.53(12)
C6 C5 C4 113.68(13)
C5 C6 C7 113.61(13)
C8 C7 C6 114.52(13)
C7 C8 C9 113.58(13)
C10 C9 C8 113.05(13)
C9 C10 C11 113.36(13)
C12 C11 C10 110.91(12)
O1 C12 C1 117.57(14)
O1 C12 C11 121.67(13)
C1 C12 C11 120.71(12)
C1 N1 O2 113.50(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.2862(18)
C1 C2 1.499(2)
C1 C12 1.500(2)
C2 C3 1.535(2)
C3 C4 1.530(2)
C4 C5 1.534(2)
C5 C6 1.528(2)
C6 C7 1.534(2)
C7 C8 1.527(2)
C8 C9 1.532(2)
C9 C10 1.530(2)
C10 C11 1.535(2)
C11 C12 1.511(2)
C12 O1 1.2198(18)
N1 O2 1.3976(15)
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
N1 C1 C2 C3 112.39(17)
C12 C1 C2 C3 -69.62(16)
C1 C2 C3 C4 -62.97(16)
C2 C3 C4 C5 164.68(12)
C3 C4 C5 C6 -70.06(17)
C4 C5 C6 C7 -70.16(17)
C5 C6 C7 C8 156.54(12)
C6 C7 C8 C9 -68.54(17)
C7 C8 C9 C10 -70.78(17)
C8 C9 C10 C11 163.49(12)
C9 C10 C11 C12 -64.70(16)
N1 C1 C12 O1 164.50(12)
C2 C1 C12 O1 -13.75(19)
N1 C1 C12 C11 -18.18(19)
C2 C1 C12 C11 163.58(12)
C10 C11 C12 O1 103.67(16)
C10 C11 C12 C1 -73.54(17)
C2 C1 N1 O2 0.9(2)
C12 C1 N1 O2 -177.13(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4911461
