#------------------------------------------------------------------------------
#$Date: 2015-08-31 11:59:54 +0300 (Mon, 31 Aug 2015) $
#$Revision: 153828 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/77/7117715.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_7117715
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            'C15 H16 Cl3 N O3'
_chemical_formula_weight         364.64
_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                67.611(2)
_cell_angle_beta                 89.839(2)
_cell_angle_gamma                85.877(2)
_cell_formula_units_Z            2
_cell_length_a                   6.0347(2)
_cell_length_b                   11.3911(4)
_cell_length_c                   13.0283(4)
_cell_measurement_reflns_used    2871
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.2
_cell_measurement_theta_min      1.691
_cell_volume                     825.64(5)
_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 0.959
_diffrn_measured_fraction_theta_max 0.987
_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  0.0155
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_laue_measured_fraction_full 0.959
_diffrn_reflns_laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11909
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         1.691
_exptl_absorpt_coefficient_mu    0.565
_exptl_absorpt_correction_T_max  0.8823
_exptl_absorpt_correction_T_min  0.8012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2871
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0368
_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)+(0.0317P)²+0.5977P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0901
_reflns_Friedel_coverage         0.000
_reflns_friedel_fraction_full    .
_reflns_friedel_fraction_max     .
_reflns_number_gt                2550
_reflns_number_total             2871
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc05459a2.cif
_cod_data_source_block           ram139
_cod_database_code               7117715
_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   0.872
_shelx_estimated_absorpt_t_max   0.946
_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 0.3022(4) 0.4772(2) 0.15300(19) 0.0491(5) Uani 1 1 d . . . . .
H1 H 0.1923 0.4576 0.1135 0.059 Uiso 1 1 calc R U . . .
C2 C 0.2673(5) 0.5813(2) 0.1821(2) 0.0606(6) Uani 1 1 d . . . . .
H2 H 0.1352 0.6326 0.1609 0.073 Uiso 1 1 calc R U . . .
C3 C 0.4268(5) 0.6096(2) 0.2425(2) 0.0618(7) Uani 1 1 d . . . . .
H3 H 0.4021 0.6794 0.2627 0.074 Uiso 1 1 calc R U . . .
C4 C 0.6225(5) 0.5345(3) 0.2729(2) 0.0608(7) Uani 1 1 d . . . . .
H4 H 0.7298 0.5530 0.3144 0.073 Uiso 1 1 calc R U . . .
C5 C 0.6606(4) 0.4326(2) 0.24234(19) 0.0508(6) Uani 1 1 d . . . . .
H5 H 0.7951 0.3835 0.2620 0.061 Uiso 1 1 calc R U . . .
C6 C 0.5006(3) 0.4016(2) 0.18238(16) 0.0388(5) Uani 1 1 d . . . . .
C7 C 0.5529(3) 0.2881(2) 0.15337(16) 0.0396(5) Uani 1 1 d . . . . .
C8 C 0.3676(3) 0.20653(19) 0.14441(15) 0.0346(4) Uani 1 1 d . . . . .
C9 C 0.4554(4) 0.0748(2) 0.1489(2) 0.0515(6) Uani 1 1 d . . . . .
H9A H 0.5927 0.0798 0.1091 0.062 Uiso 1 1 calc R U . . .
H9B H 0.4811 0.0153 0.2250 0.062 Uiso 1 1 calc R U . . .
C10 C 0.2712(5) 0.0355(3) 0.0929(2) 0.0627(7) Uani 1 1 d . . . . .
H10A H 0.3266 -0.0300 0.0669 0.075 Uiso 1 1 calc R U . . .
H10B H 0.1513 0.0038 0.1435 0.075 Uiso 1 1 calc R U . . .
C11 C 0.1942(5) 0.1558(3) -0.0027(2) 0.0725(8) Uani 1 1 d . . . . .
H11A H 0.0360 0.1578 -0.0168 0.087 Uiso 1 1 calc R U . . .
H11B H 0.2720 0.1609 -0.0693 0.087 Uiso 1 1 calc R U . . .
C12 C 0.2447(3) 0.2660(2) 0.02953(16) 0.0416(5) Uani 1 1 d . . . . .
H12A H 0.1082 0.3139 0.0343 0.050 Uiso 1 1 calc R U . . .
H12B H 0.3378 0.3229 -0.0251 0.050 Uiso 1 1 calc R U . . .
C13 C 0.2844(3) 0.15492(18) 0.33797(16) 0.0362(4) Uani 1 1 d . . . . .
C14 C 0.1700(4) 0.1183(2) 0.52096(17) 0.0472(5) Uani 1 1 d . . . . .
H14A H 0.3305 0.1110 0.5306 0.057 Uiso 1 1 calc R U . . .
H14B H 0.1140 0.0384 0.5688 0.057 Uiso 1 1 calc R U . . .
C15 C 0.0700(3) 0.2257(2) 0.55119(16) 0.0411(5) Uani 1 1 d . . . . .
Cl1 Cl -0.22004(11) 0.24284(11) 0.53487(7) 0.0963(3) Uani 1 1 d . . . . .
Cl2 Cl 0.14028(12) 0.18860(6) 0.69296(5) 0.06045(19) Uani 1 1 d . . . . .
Cl3 Cl 0.18185(13) 0.36941(6) 0.46865(6) 0.0669(2) Uani 1 1 d . . . . .
N1 N 0.2097(3) 0.19328(17) 0.23261(13) 0.0355(4) Uani 1 1 d . . . . .
O1 O 0.7435(2) 0.26013(19) 0.13531(15) 0.0614(5) Uani 1 1 d . . . . .
O2 O 0.4770(3) 0.13246(15) 0.36830(12) 0.0493(4) Uani 1 1 d . . . . .
O3 O 0.1109(2) 0.14492(15) 0.40756(11) 0.0457(4) Uani 1 1 d . . . . .
H1N H 0.084(4) 0.207(2) 0.2190(19) 0.039(6) 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'
Cl Cl 0.1484 0.1585 '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 120.2(2) . .
C2 C1 H1 119.9 . .
C6 C1 H1 119.9 . .
C3 C2 C1 120.3(2) . .
C3 C2 H2 119.8 . .
C1 C2 H2 119.8 . .
C4 C3 C2 119.8(2) . .
C4 C3 H3 120.1 . .
C2 C3 H3 120.1 . .
C5 C4 C3 120.3(2) . .
C5 C4 H4 119.8 . .
C3 C4 H4 119.8 . .
C4 C5 C6 120.8(2) . .
C4 C5 H5 119.6 . .
C6 C5 H5 119.6 . .
C1 C6 C5 118.5(2) . .
C1 C6 C7 123.75(19) . .
C5 C6 C7 117.73(19) . .
O1 C7 C6 120.04(19) . .
O1 C7 C8 119.35(19) . .
C6 C7 C8 120.61(17) . .
N1 C8 C9 110.17(17) . .
N1 C8 C7 109.37(15) . .
C9 C8 C7 113.10(17) . .
N1 C8 C12 109.84(15) . .
C9 C8 C12 102.69(16) . .
C7 C8 C12 111.50(16) . .
C10 C9 C8 103.67(19) . .
C10 C9 H9A 111.0 . .
C8 C9 H9A 111.0 . .
C10 C9 H9B 111.0 . .
C8 C9 H9B 111.0 . .
H9A C9 H9B 109.0 . .
C11 C10 C9 104.1(2) . .
C11 C10 H10A 110.9 . .
C9 C10 H10A 110.9 . .
C11 C10 H10B 110.9 . .
C9 C10 H10B 110.9 . .
H10A C10 H10B 109.0 . .
C10 C11 C12 107.0(2) . .
C10 C11 H11A 110.3 . .
C12 C11 H11A 110.3 . .
C10 C11 H11B 110.3 . .
C12 C11 H11B 110.3 . .
H11A C11 H11B 108.6 . .
C11 C12 C8 106.39(19) . .
C11 C12 H12A 110.5 . .
C8 C12 H12A 110.5 . .
C11 C12 H12B 110.5 . .
C8 C12 H12B 110.5 . .
H12A C12 H12B 108.6 . .
O2 C13 N1 125.47(19) . .
O2 C13 O3 124.10(18) . .
N1 C13 O3 110.43(18) . .
O3 C14 C15 108.37(18) . .
O3 C14 H14A 110.0 . .
C15 C14 H14A 110.0 . .
O3 C14 H14B 110.0 . .
C15 C14 H14B 110.0 . .
H14A C14 H14B 108.4 . .
C14 C15 Cl1 111.69(16) . .
C14 C15 Cl3 109.96(15) . .
Cl1 C15 Cl3 109.65(12) . .
C14 C15 Cl2 107.47(15) . .
Cl1 C15 Cl2 108.67(11) . .
Cl3 C15 Cl2 109.34(11) . .
C13 N1 C8 119.60(17) . .
C13 N1 H1N 120.0(17) . .
C8 N1 H1N 120.4(17) . .
C13 O3 C14 115.73(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.379(3) .
C1 C6 1.388(3) .
C1 H1 0.9300 .
C2 C3 1.375(4) .
C2 H2 0.9300 .
C3 C4 1.372(4) .
C3 H3 0.9300 .
C4 C5 1.368(4) .
C4 H4 0.9300 .
C5 C6 1.389(3) .
C5 H5 0.9300 .
C6 C7 1.493(3) .
C7 O1 1.217(2) .
C7 C8 1.536(3) .
C8 N1 1.460(2) .
C8 C9 1.534(3) .
C8 C12 1.553(3) .
C9 C10 1.514(3) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 C11 1.503(4) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C12 1.517(3) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 O2 1.206(2) .
C13 N1 1.340(3) .
C13 O3 1.365(2) .
C14 O3 1.431(2) .
C14 C15 1.509(3) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 Cl1 1.752(2) .
C15 Cl3 1.762(2) .
C15 Cl2 1.776(2) .
N1 H1N 0.77(2) .
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
C12 H12A O1 0.97 2.55 3.315(2) 135.5 1_455
C14 H14B O3 0.97 2.49 3.365(3) 149.6 2_556
N1 H1N O1 0.77(2) 2.26(2) 3.014(2) 166(2) 1_455
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 -1.3(4) . . . .
C1 C2 C3 C4 0.6(4) . . . .
C2 C3 C4 C5 0.7(4) . . . .
C3 C4 C5 C6 -1.4(4) . . . .
C2 C1 C6 C5 0.7(3) . . . .
C2 C1 C6 C7 -179.4(2) . . . .
C4 C5 C6 C1 0.7(3) . . . .
C4 C5 C6 C7 -179.2(2) . . . .
C1 C6 C7 O1 147.4(2) . . . .
C5 C6 C7 O1 -32.7(3) . . . .
C1 C6 C7 C8 -31.8(3) . . . .
C5 C6 C7 C8 148.1(2) . . . .
O1 C7 C8 N1 141.3(2) . . . .
C6 C7 C8 N1 -39.5(2) . . . .
O1 C7 C8 C9 18.1(3) . . . .
C6 C7 C8 C9 -162.73(18) . . . .
O1 C7 C8 C12 -97.0(2) . . . .
C6 C7 C8 C12 82.1(2) . . . .
N1 C8 C9 C10 79.8(2) . . . .
C7 C8 C9 C10 -157.42(18) . . . .
C12 C8 C9 C10 -37.1(2) . . . .
C8 C9 C10 C11 40.0(3) . . . .
C9 C10 C11 C12 -26.8(3) . . . .
C10 C11 C12 C8 3.5(3) . . . .
N1 C8 C12 C11 -96.5(2) . . . .
C9 C8 C12 C11 20.7(2) . . . .
C7 C8 C12 C11 142.1(2) . . . .
O3 C14 C15 Cl1 59.6(2) . . . .
O3 C14 C15 Cl3 -62.4(2) . . . .
O3 C14 C15 Cl2 178.67(14) . . . .
O2 C13 N1 C8 2.1(3) . . . .
O3 C13 N1 C8 -178.11(16) . . . .
C9 C8 N1 C13 73.8(2) . . . .
C7 C8 N1 C13 -51.1(2) . . . .
C12 C8 N1 C13 -173.75(17) . . . .
O2 C13 O3 C14 6.4(3) . . . .
N1 C13 O3 C14 -173.37(17) . . . .
C15 C14 O3 C13 120.1(2) . . . .
