#------------------------------------------------------------------------------
#$Date: 2016-03-05 09:39:21 +0200 (Sat, 05 Mar 2016) $
#$Revision: 177656 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/84/7118498.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_7118498
loop_
_publ_author_name
'Ramakrishna, Isai'
'Sahoo, Harekrishna'
'Baidya, Mahiuddin'
_publ_section_title
;
 Brønsted acid mediated N-O bond cleavage for α-amination of ketones
 through the aromatic nitroso aldol reaction.
;
_journal_issue                   15
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3215
_journal_page_last               3218
_journal_paper_doi               10.1039/c5cc10102f
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C15 H15 N O'
_chemical_formula_sum            'C15 H15 N O'
_chemical_formula_weight         225.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-12-05 deposited with the CCDC.
2016-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.037(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9551(4)
_cell_length_b                   9.4163(6)
_cell_length_c                   14.8711(9)
_cell_measurement_reflns_used    2967
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.26
_cell_measurement_theta_min      2.56
_cell_volume                     1249.15(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9305
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.560
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0394
_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)+(0.0554P)²+0.0318P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1100
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1498
_reflns_number_total             2188
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc10102f2.cif
_cod_data_source_block           131
_cod_depositor_comments
'Adding full bibliography for 7118495--7118498.cif.'
_cod_database_code               7118498
_shelx_shelxl_version_number     2014/7
_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   0.982
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.27417(18) 0.03509(17) 0.53655(11) 0.0646(5) Uani 1 1 d . .
H1 H 0.3551 0.0250 0.5019 0.078 Uiso 1 1 calc R U
C2 C 0.2008(2) -0.08353(19) 0.56376(13) 0.0823(6) Uani 1 1 d . .
H2 H 0.2318 -0.1733 0.5472 0.099 Uiso 1 1 calc R U
C3 C 0.0817(2) -0.0698(2) 0.61538(12) 0.0791(6) Uani 1 1 d . .
H3 H 0.0327 -0.1504 0.6339 0.095 Uiso 1 1 calc R U
C4 C 0.03510(19) 0.0612(2) 0.63962(12) 0.0702(5) Uani 1 1 d . .
H4 H -0.0455 0.0700 0.6746 0.084 Uiso 1 1 calc R U
C5 C 0.10741(16) 0.18105(16) 0.61230(10) 0.0572(4) Uani 1 1 d . .
H5 H 0.0748 0.2703 0.6288 0.069 Uiso 1 1 calc R U
C6 C 0.22846(14) 0.16960(15) 0.56030(9) 0.0473(4) Uani 1 1 d . .
C7 C 0.30965(14) 0.29510(15) 0.52863(9) 0.0490(4) Uani 1 1 d . .
C8 C 0.25644(15) 0.44443(15) 0.54934(9) 0.0497(4) Uani 1 1 d . .
H8 H 0.1477 0.4419 0.5527 0.060 Uiso 1 1 calc R U
C9 C 0.22114(14) 0.54937(15) 0.39600(10) 0.0489(4) Uani 1 1 d . .
C10 C 0.26217(16) 0.65257(17) 0.33543(11) 0.0643(5) Uani 1 1 d . .
H10 H 0.3374 0.7172 0.3535 0.077 Uiso 1 1 calc R U
C11 C 0.1930(2) 0.6599(2) 0.24964(13) 0.0809(6) Uani 1 1 d . .
H11 H 0.2222 0.7293 0.2103 0.097 Uiso 1 1 calc R U
C12 C 0.0813(2) 0.5665(2) 0.22085(12) 0.0825(6) Uani 1 1 d . .
H12 H 0.0346 0.5722 0.1626 0.099 Uiso 1 1 calc R U
C13 C 0.03975(18) 0.46456(19) 0.27958(11) 0.0685(5) Uani 1 1 d . .
H13 H -0.0358 0.4006 0.2608 0.082 Uiso 1 1 calc R U
C14 C 0.10866(16) 0.45538(16) 0.36652(10) 0.0559(4) Uani 1 1 d . .
H14 H 0.0790 0.3854 0.4054 0.067 Uiso 1 1 calc R U
C15 C 0.33025(18) 0.48861(18) 0.64115(10) 0.0662(5) Uani 1 1 d . .
H15A H 0.4369 0.4936 0.6386 0.099 Uiso 1 1 calc R U
H15B H 0.3074 0.4201 0.6857 0.099 Uiso 1 1 calc R U
H15C H 0.2931 0.5800 0.6570 0.099 Uiso 1 1 calc R U
N1 N 0.28951(15) 0.54810(14) 0.48301(9) 0.0581(4) Uani 1 1 d . .
O1 O 0.42138(11) 0.27970(12) 0.48838(8) 0.0727(4) Uani 1 1 d . .
H1N H 0.3741(17) 0.5943(17) 0.4899(9) 0.060(5) 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
C2 C1 C6 120.51(17)
C2 C1 H1 119.7
C6 C1 H1 119.7
C3 C2 C1 120.20(17)
C3 C2 H2 119.9
C1 C2 H2 119.9
C4 C3 C2 120.26(16)
C4 C3 H3 119.9
C2 C3 H3 119.9
C3 C4 C5 120.05(17)
C3 C4 H4 120.0
C5 C4 H4 120.0
C4 C5 C6 120.63(15)
C4 C5 H5 119.7
C6 C5 H5 119.7
C1 C6 C5 118.35(14)
C1 C6 C7 118.84(14)
C5 C6 C7 122.81(13)
O1 C7 C6 120.44(13)
O1 C7 C8 119.57(13)
C6 C7 C8 119.95(12)
N1 C8 C15 109.31(12)
N1 C8 C7 113.64(11)
C15 C8 C7 108.33(12)
N1 C8 H8 108.5
C15 C8 H8 108.5
C7 C8 H8 108.5
N1 C9 C14 122.80(14)
N1 C9 C10 119.34(13)
C14 C9 C10 117.82(14)
C11 C10 C9 120.83(15)
C11 C10 H10 119.6
C9 C10 H10 119.6
C10 C11 C12 121.08(16)
C10 C11 H11 119.5
C12 C11 H11 119.5
C13 C12 C11 118.77(16)
C13 C12 H12 120.6
C11 C12 H12 120.6
C12 C13 C14 120.96(16)
C12 C13 H13 119.5
C14 C13 H13 119.5
C9 C14 C13 120.54(15)
C9 C14 H14 119.7
C13 C14 H14 119.7
C8 C15 H15A 109.5
C8 C15 H15B 109.5
H15A C15 H15B 109.5
C8 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C9 N1 C8 123.19(12)
C9 N1 H1N 114.5(10)
C8 N1 H1N 119.2(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.375(2)
C1 C6 1.386(2)
C1 H1 0.9300
C2 C3 1.374(3)
C2 H2 0.9300
C3 C4 1.361(2)
C3 H3 0.9300
C4 C5 1.380(2)
C4 H4 0.9300
C5 C6 1.3899(19)
C5 H5 0.9300
C6 C7 1.486(2)
C7 O1 1.2188(16)
C7 C8 1.5248(19)
C8 N1 1.4370(18)
C8 C15 1.5217(19)
C8 H8 0.9800
C9 N1 1.3821(18)
C9 C14 1.383(2)
C9 C10 1.396(2)
C10 C11 1.370(2)
C10 H10 0.9300
C11 C12 1.371(3)
C11 H11 0.9300
C12 C13 1.371(2)
C12 H12 0.9300
C13 C14 1.386(2)
C13 H13 0.9300
C14 H14 0.9300
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
N1 H1N 0.871(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
C6 C1 C2 C3 -0.4(3)
C1 C2 C3 C4 0.3(3)
C2 C3 C4 C5 0.0(3)
C3 C4 C5 C6 -0.3(2)
C2 C1 C6 C5 0.2(2)
C2 C1 C6 C7 -179.29(13)
C4 C5 C6 C1 0.1(2)
C4 C5 C6 C7 179.61(13)
C1 C6 C7 O1 -5.5(2)
C5 C6 C7 O1 175.02(12)
C1 C6 C7 C8 176.63(12)
C5 C6 C7 C8 -2.83(19)
O1 C7 C8 N1 31.18(18)
C6 C7 C8 N1 -150.95(12)
O1 C7 C8 C15 -90.50(15)
C6 C7 C8 C15 87.36(14)
N1 C9 C10 C11 -177.74(14)
C14 C9 C10 C11 -0.1(2)
C9 C10 C11 C12 0.2(3)
C10 C11 C12 C13 -0.2(3)
C11 C12 C13 C14 0.0(3)
N1 C9 C14 C13 177.52(13)
C10 C9 C14 C13 -0.1(2)
C12 C13 C14 C9 0.1(2)
C14 C9 N1 C8 3.6(2)
C10 C9 N1 C8 -178.82(13)
C15 C8 N1 C9 -170.28(13)
C7 C8 N1 C9 68.58(17)
