#------------------------------------------------------------------------------
#$Date: 2015-08-31 11:59:54 +0300 (Mon, 31 Aug 2015) $
#$Revision: 153828 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/77/7117713.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_7117713
loop_
_publ_author_name
'Isai Ramakrishna'
'Gowri Sankar Grandhi'
'Harekrishna Sahoo'
'Mahiuddin Baidya'
_publ_section_title
;
 The Mukaiyama aldol reaction of in situ generated nitrosocarbonyl
 compounds: selective C-N bond formation and N-O bond cleavage in one-pot
 for alpha-amination of ketones
;
_journal_name_full               Chem.Commun.
_journal_page_first              13976
_journal_paper_doi               10.1039/C5cc05459A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C17 H17 N O3'
_chemical_formula_weight         283.31
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2012
_audit_update_record
;
2015-06-22 deposited with the CCDC.
2015-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                100.410(4)
_cell_angle_beta                 96.485(4)
_cell_angle_gamma                93.141(4)
_cell_formula_units_Z            2
_cell_length_a                   6.0589(4)
_cell_length_b                   8.0710(5)
_cell_length_c                   15.6647(10)
_cell_measurement_reflns_used    2516
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.34
_cell_volume                     746.38(8)
_computing_cell_refinement       'APEXII/SAINT (Bruker, 2012)'
_computing_data_collection       'APEXII (Bruker, 2012)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2012)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997) '
_computing_publication_material  'SHELXL-97 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Bruker kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1788
_diffrn_reflns_av_unetI/netI     0.1043
_diffrn_reflns_laue_measured_fraction_full 0.927
_diffrn_reflns_laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9021
_diffrn_reflns_point_group_measured_fraction_full 0.927
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.332
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9710
_exptl_absorpt_correction_T_min  0.9216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.049(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0663
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0671P)²+0.3494P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1884
_refine_ls_wR_factor_ref         0.1986
_reflns_Friedel_coverage         0.000
_reflns_friedel_fraction_full    .
_reflns_friedel_fraction_max     .
_reflns_number_gt                2008
_reflns_number_total             2516
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc05459a2.cif
_cod_data_source_block           ram114
_cod_database_code               7117713
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.974
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2012-9
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6185(6) 0.8025(4) 0.81716(17) 0.0508(8) Uani 1 1 d . . . . .
H1 H 0.7146 0.8669 0.7915 0.061 Uiso 1 1 calc R U . . .
C2 C 0.6190(7) 0.8345(4) 0.90702(18) 0.0622(9) Uani 1 1 d . . . . .
H2 H 0.7156 0.9205 0.9415 0.075 Uiso 1 1 calc R U . . .
C3 C 0.4794(7) 0.7413(5) 0.94518(19) 0.0681(10) Uani 1 1 d . . . . .
H3 H 0.4820 0.7627 1.0057 0.082 Uiso 1 1 calc R U . . .
C4 C 0.3347(7) 0.6157(5) 0.89456(19) 0.0653(10) Uani 1 1 d . . . . .
H4 H 0.2374 0.5535 0.9207 0.078 Uiso 1 1 calc R U . . .
C5 C 0.3329(5) 0.5812(4) 0.80487(18) 0.0500(8) Uani 1 1 d . . . . .
H5 H 0.2359 0.4948 0.7710 0.060 Uiso 1 1 calc R U . . .
C6 C 0.4745(4) 0.6745(3) 0.76521(15) 0.0370(6) Uani 1 1 d . . . . .
C7 C 0.4706(4) 0.6318(3) 0.66746(15) 0.0350(6) Uani 1 1 d . . . . .
C8 C 0.6290(4) 0.7314(3) 0.62399(15) 0.0367(6) Uani 1 1 d . . . . .
H8 H 0.6437 0.8495 0.6544 0.044 Uiso 1 1 calc R U . . .
C9 C 0.3697(5) 0.8068(3) 0.51222(15) 0.0353(6) Uani 1 1 d . . . . .
C10 C 0.1084(5) 0.8495(4) 0.39672(16) 0.0435(7) Uani 1 1 d . . . . .
H10A H 0.1203 0.9689 0.4224 0.052 Uiso 1 1 calc R U . . .
H10B H -0.0210 0.7963 0.4151 0.052 Uiso 1 1 calc R U . . .
C11 C 0.0845(5) 0.8262(3) 0.29831(16) 0.0387(6) Uani 1 1 d . . . . .
C12 C -0.0927(5) 0.8948(4) 0.25658(18) 0.0508(8) Uani 1 1 d . . . . .
H12 H -0.1918 0.9539 0.2893 0.061 Uiso 1 1 calc R U . . .
C13 C -0.1225(6) 0.8755(4) 0.16595(19) 0.0603(9) Uani 1 1 d . . . . .
H13 H -0.2402 0.9233 0.1384 0.072 Uiso 1 1 calc R U . . .
C14 C 0.0206(6) 0.7863(4) 0.11686(19) 0.0602(9) Uani 1 1 d . . . . .
H14 H -0.0004 0.7725 0.0562 0.072 Uiso 1 1 calc R U . . .
C15 C 0.1939(6) 0.7182(4) 0.15784(19) 0.0601(9) Uani 1 1 d . . . . .
H15 H 0.2905 0.6571 0.1246 0.072 Uiso 1 1 calc R U . . .
C16 C 0.2291(6) 0.7385(4) 0.24884(18) 0.0508(8) Uani 1 1 d . . . . .
H16 H 0.3497 0.6929 0.2759 0.061 Uiso 1 1 calc R U . . .
C17 C 0.8587(5) 0.6606(4) 0.63120(19) 0.0485(7) Uani 1 1 d . . . . .
H17A H 0.8479 0.5470 0.5987 0.073 Uiso 1 1 calc R U . . .
H17B H 0.9098 0.6610 0.6915 0.073 Uiso 1 1 calc R U . . .
H17C H 0.9621 0.7296 0.6079 0.073 Uiso 1 1 calc R U . . .
N1 N 0.5484(4) 0.7251(3) 0.53294(13) 0.0414(6) Uani 1 1 d . . . . .
O1 O 0.3446(3) 0.5164(2) 0.62517(11) 0.0465(6) Uani 1 1 d . . . . .
O2 O 0.2790(4) 0.8998(2) 0.56403(12) 0.0499(6) Uani 1 1 d . . . . .
O3 O 0.3053(3) 0.7736(2) 0.42514(11) 0.0435(5) Uani 1 1 d . . . . .
H1N H 0.602(5) 0.650(3) 0.4907(18) 0.042(7) 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 0.0000 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C6 120.1(3) . .
C2 C1 H1 120.0 . .
C6 C1 H1 120.0 . .
C3 C2 C1 120.5(3) . .
C3 C2 H2 119.8 . .
C1 C2 H2 119.8 . .
C2 C3 C4 120.0(3) . .
C2 C3 H3 120.0 . .
C4 C3 H3 120.0 . .
C3 C4 C5 120.3(3) . .
C3 C4 H4 119.9 . .
C5 C4 H4 119.9 . .
C4 C5 C6 120.3(3) . .
C4 C5 H5 119.8 . .
C6 C5 H5 119.8 . .
C5 C6 C1 118.8(2) . .
C5 C6 C7 118.9(2) . .
C1 C6 C7 122.3(3) . .
O1 C7 C6 119.7(2) . .
O1 C7 C8 121.2(2) . .
C6 C7 C8 119.0(2) . .
N1 C8 C7 111.5(2) . .
N1 C8 C17 109.5(2) . .
C7 C8 C17 109.6(2) . .
N1 C8 H8 108.7 . .
C7 C8 H8 108.7 . .
C17 C8 H8 108.7 . .
O2 C9 N1 124.7(2) . .
O2 C9 O3 124.0(2) . .
N1 C9 O3 111.2(2) . .
O3 C10 C11 108.3(2) . .
O3 C10 H10A 110.0 . .
C11 C10 H10A 110.0 . .
O3 C10 H10B 110.0 . .
C11 C10 H10B 110.0 . .
H10A C10 H10B 108.4 . .
C16 C11 C12 119.1(2) . .
C16 C11 C10 122.7(2) . .
C12 C11 C10 118.2(2) . .
C11 C12 C13 120.2(3) . .
C11 C12 H12 119.9 . .
C13 C12 H12 119.9 . .
C14 C13 C12 120.4(3) . .
C14 C13 H13 119.8 . .
C12 C13 H13 119.8 . .
C15 C14 C13 119.3(3) . .
C15 C14 H14 120.3 . .
C13 C14 H14 120.3 . .
C14 C15 C16 121.2(3) . .
C14 C15 H15 119.4 . .
C16 C15 H15 119.4 . .
C11 C16 C15 119.7(3) . .
C11 C16 H16 120.2 . .
C15 C16 H16 120.2 . .
C8 C17 H17A 109.5 . .
C8 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C8 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C9 N1 C8 119.4(2) . .
C9 N1 H1N 119.9(18) . .
C8 N1 H1N 119.7(18) . .
C9 O3 C10 115.42(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.384(4) .
C1 C6 1.388(4) .
C1 H1 0.9300 .
C2 C3 1.359(5) .
C2 H2 0.9300 .
C3 C4 1.371(5) .
C3 H3 0.9300 .
C4 C5 1.381(4) .
C4 H4 0.9300 .
C5 C6 1.381(4) .
C5 H5 0.9300 .
C6 C7 1.505(3) .
C7 O1 1.214(3) .
C7 C8 1.514(4) .
C8 N1 1.445(3) .
C8 C17 1.533(4) .
C8 H8 0.9800 .
C9 O2 1.205(3) .
C9 N1 1.337(3) .
C9 O3 1.350(3) .
C10 O3 1.433(3) .
C10 C11 1.508(3) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C16 1.375(4) .
C11 C12 1.387(4) .
C12 C13 1.390(4) .
C12 H12 0.9300 .
C13 C14 1.371(5) .
C13 H13 0.9300 .
C14 C15 1.362(5) .
C14 H14 0.9300 .
C15 C16 1.396(4) .
C15 H15 0.9300 .
C16 H16 0.9300 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
N1 H1N 0.91(3) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C17 H17A O3 0.96 2.65 3.515(4) 150.5 2_666
C17 H17C O2 0.96 2.53 3.481(4) 171.2 1_655
N1 H1N O1 0.91(3) 2.12(3) 3.018(3) 166(3) 2_666
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 0.0(6) . . . .
C1 C2 C3 C4 -0.8(6) . . . .
C2 C3 C4 C5 1.2(6) . . . .
C3 C4 C5 C6 -0.9(6) . . . .
C4 C5 C6 C1 0.2(5) . . . .
C4 C5 C6 C7 179.1(3) . . . .
C2 C1 C6 C5 0.2(5) . . . .
C2 C1 C6 C7 -178.6(3) . . . .
C5 C6 C7 O1 -0.3(4) . . . .
C1 C6 C7 O1 178.5(3) . . . .
C5 C6 C7 C8 -178.7(2) . . . .
C1 C6 C7 C8 0.1(4) . . . .
O1 C7 C8 N1 24.9(3) . . . .
C6 C7 C8 N1 -156.7(2) . . . .
O1 C7 C8 C17 -96.5(3) . . . .
C6 C7 C8 C17 81.9(3) . . . .
O3 C10 C11 C16 2.6(4) . . . .
O3 C10 C11 C12 -178.1(2) . . . .
C16 C11 C12 C13 -0.3(5) . . . .
C10 C11 C12 C13 -179.5(3) . . . .
C11 C12 C13 C14 1.0(5) . . . .
C12 C13 C14 C15 -0.7(5) . . . .
C13 C14 C15 C16 -0.4(5) . . . .
C12 C11 C16 C15 -0.8(5) . . . .
C10 C11 C16 C15 178.4(3) . . . .
C14 C15 C16 C11 1.2(5) . . . .
O2 C9 N1 C8 7.0(4) . . . .
O3 C9 N1 C8 -173.9(2) . . . .
C7 C8 N1 C9 70.1(3) . . . .
C17 C8 N1 C9 -168.5(2) . . . .
O2 C9 O3 C10 -3.7(4) . . . .
N1 C9 O3 C10 177.3(2) . . . .
C11 C10 O3 C9 170.0(2) . . . .
