#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:33:07 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301779 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/55/1545561.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_1545561
loop_
_publ_author_name
'Reddy, Mallu Kesava'
'Mallik, Sumitava'
'Ramakrishna, Isai'
'Baidya, Mahiuddin'
_publ_section_title
;
 Nitrosocarbonyl-Henry and Denitration Cascade: Synthesis of α-Ketoamides
 and α-Keto Oximes.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1694
_journal_page_last               1697
_journal_paper_doi               10.1021/acs.orglett.7b00482
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C9 H9 N O2'
_chemical_formula_weight         163.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.761(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7456(5)
_cell_length_b                   14.1679(5)
_cell_length_c                   6.2215(2)
_cell_measurement_reflns_used    1935
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.42
_cell_measurement_theta_min      2.61
_cell_volume                     822.54(6)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0213
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6232
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.182
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.012(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   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1454
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0489P)²+0.1347P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.1057
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1092
_reflns_number_total             1454
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol7b00482_si_003.cif
_cod_data_source_block           trae
_cod_depositor_comments
'Adding full bibliography for 1545561--1545562.cif.'
_cod_database_code               1545561
_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   0.980
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.6788(2) 0.59683(12) 0.4150(3) 0.0518(5) Uani 1 1 d . .
H1 H 0.7073 0.5800 0.5659 0.062 Uiso 1 1 calc R U
C2 C 0.5368(2) 0.59201(13) 0.2955(3) 0.0583(5) Uani 1 1 d . .
H2 H 0.4700 0.5706 0.3649 0.070 Uiso 1 1 calc R U
C3 C 0.4925(2) 0.61865(13) 0.0738(3) 0.0561(5) Uani 1 1 d . .
H3 H 0.3958 0.6161 -0.0058 0.067 Uiso 1 1 calc R U
C4 C 0.5914(2) 0.64913(12) -0.0304(3) 0.0523(5) Uani 1 1 d . .
H4 H 0.5612 0.6679 -0.1800 0.063 Uiso 1 1 calc R U
C5 C 0.73543(19) 0.65196(11) 0.0864(3) 0.0435(4) Uani 1 1 d . .
H5 H 0.8021 0.6707 0.0141 0.052 Uiso 1 1 calc R U
C6 C 0.78078(18) 0.62679(11) 0.3121(3) 0.0402(4) Uani 1 1 d . .
C7 C 0.9310(2) 0.63866(11) 0.4541(3) 0.0449(4) Uani 1 1 d . .
C8 C 1.05513(18) 0.62394(12) 0.3612(3) 0.0427(4) Uani 1 1 d . .
C9 C 1.1955(2) 0.66762(15) 0.4796(3) 0.0663(6) Uani 1 1 d . .
H9A H 1.2414 0.6312 0.6108 0.100 Uiso 1 1 calc R U
H9B H 1.1803 0.7309 0.5233 0.100 Uiso 1 1 calc R U
H9C H 1.2553 0.6690 0.3812 0.100 Uiso 1 1 calc R U
N1 N 1.03159(15) 0.56899(9) 0.1921(2) 0.0434(4) Uani 1 1 d . .
O1 O 0.95689(15) 0.66052(10) 0.65092(19) 0.0660(5) Uani 1 1 d . .
O2 O 1.15328(13) 0.55243(10) 0.1227(2) 0.0555(4) Uani 1 1 d . .
H1O H 1.117(3) 0.5154(17) 0.005(4) 0.087(8) 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 120.52(16)
C2 C1 H1 119.7
C6 C1 H1 119.7
C1 C2 C3 120.44(17)
C1 C2 H2 119.8
C3 C2 H2 119.8
C2 C3 C4 119.92(18)
C2 C3 H3 120.0
C4 C3 H3 120.0
C3 C4 C5 120.25(16)
C3 C4 H4 119.9
C5 C4 H4 119.9
C4 C5 C6 120.14(16)
C4 C5 H5 119.9
C6 C5 H5 119.9
C5 C6 C1 118.69(16)
C5 C6 C7 122.87(15)
C1 C6 C7 118.20(15)
O1 C7 C6 120.63(16)
O1 C7 C8 117.88(16)
C6 C7 C8 121.49(14)
N1 C8 C9 125.66(17)
N1 C8 C7 115.47(15)
C9 C8 C7 118.72(15)
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C8 N1 O2 113.05(14)
N1 O2 H1O 100.7(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.371(3)
C1 C6 1.395(2)
C1 H1 0.9300
C2 C3 1.374(3)
C2 H2 0.9300
C3 C4 1.377(3)
C3 H3 0.9300
C4 C5 1.383(2)
C4 H4 0.9300
C5 C6 1.391(2)
C5 H5 0.9300
C6 C7 1.485(2)
C7 O1 1.2171(19)
C7 C8 1.497(2)
C8 N1 1.276(2)
C8 C9 1.489(3)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
N1 O2 1.3939(17)
O2 H1O 0.89(3)
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 -1.5(3)
C1 C2 C3 C4 0.9(3)
C2 C3 C4 C5 0.8(3)
C3 C4 C5 C6 -2.0(3)
C4 C5 C6 C1 1.5(2)
C4 C5 C6 C7 -172.77(16)
C2 C1 C6 C5 0.3(2)
C2 C1 C6 C7 174.76(16)
C5 C6 C7 O1 144.31(18)
C1 C6 C7 O1 -30.0(2)
C5 C6 C7 C8 -35.9(2)
C1 C6 C7 C8 149.82(16)
O1 C7 C8 N1 154.49(16)
C6 C7 C8 N1 -25.3(2)
O1 C7 C8 C9 -21.3(2)
C6 C7 C8 C9 158.96(16)
C9 C8 N1 O2 -0.2(2)
C7 C8 N1 O2 -175.64(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 9566063
