#------------------------------------------------------------------------------
#$Date: 2022-01-11 00:51:05 +0200 (Tue, 11 Jan 2022) $
#$Revision: 271974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/95/7129526.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_7129526
loop_
_publ_author_name
'Cao, Haoying'
'Ma, Shanshan'
'Feng, Yanhong'
'Guo, Yawen'
'Jiao, Peng'
_publ_section_title
;
 Synthesis of β-Nitro Ketone from Geminal Bromonitroalkane and Silyl Enol
 Ether by Visible Light Photoredox Catalysis
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06529G
_journal_year                    2022
_chemical_formula_moiety         'C9 H13 N O3'
_chemical_formula_sum            'C9 H13 N O3'
_chemical_formula_weight         183.20
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-09-01
_audit_creation_method
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_audit_update_record
;
2021-09-05 deposited with the CCDC.	2022-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.274(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.94438(17)
_cell_length_b                   15.3656(5)
_cell_length_c                   9.9491(4)
_cell_measurement_reflns_used    7781
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.6740
_cell_measurement_theta_min      5.3130
_cell_volume                     903.30(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00 120.00   0.50    0.05    --   46.70  37.00  30.00  172
  2  ω     32.00  69.00   0.50    0.05    --   46.70  57.00 150.00   74
  3  ω     92.00 178.00   0.50    0.16    --  104.75  30.00  30.00  172
  4  ω     92.00 178.00   0.50    0.16    --  104.75  30.00 -90.00  172
  5  ω     32.00 109.00   0.50    0.16    --  104.75 -94.00-120.00  154
  6  ω     35.00 121.00   0.50    0.05    --   46.70-165.00-128.00  172
  7  ω     35.00 145.00   0.50    0.16    --  104.75-165.00-128.00  220
  8  ω     32.00 117.00   0.50    0.16    --  104.75-125.00 -60.00  170
  9  ω     32.00 109.00   0.50    0.16    --  104.75 -94.00-150.00  154
 10  ω      9.00  90.00   0.50    0.05    --   46.70-116.00  18.00  162
 11  ω     32.00 112.00   0.50    0.16    --  104.75-116.00  18.00  160
 12  ω     32.00 108.00   0.50    0.16    --  104.75 -77.00   0.00  152
 13  ω     32.00  73.00   0.50    0.16    --  104.75 -61.00  60.00   82
 14  ω     32.00  73.00   0.50    0.16    --  104.75 -61.00 150.00   82
 15  ω     81.00 178.00   0.50    0.16    --  104.75 116.00 107.00  194
 16  ω     76.00 178.00   0.50    0.16    --  104.75 125.00  60.00  204
 17  ω     50.00 119.00   0.50    0.05    --   46.70 165.00-105.00  138
 18  ω     50.00 159.00   0.50    0.16    --  104.75 165.00-105.00  218
 19  ω     76.00 178.00   0.50    0.16    --  104.75 125.00-180.00  204
 20  ω   -121.00 -31.00   0.50    0.05    --  -46.70 165.00-105.00  180
 21  ω   -144.00 -31.00   0.50    0.16    -- -102.00 165.00-105.00  226
 22  ω    -90.00  -4.00   0.50    0.05    --  -46.70 116.00 107.00  172
 23  ω   -112.00 -29.00   0.50    0.16    -- -102.00 116.00 107.00  166
 24  ω    -69.00 -29.00   0.50    0.16    -- -102.00  61.00  60.00   80
 25  ω    -24.00  29.00   0.50    0.05    --  -46.70  19.00-180.00  106
 26  ω    -24.00  29.00   0.50    0.05    --  -46.70  19.00 120.00  106
 27  ω    -69.00 -29.00   0.50    0.16    -- -102.00  61.00 150.00   80
 28  ω    -69.00 -29.00   0.50    0.16    -- -102.00  61.00 120.00   80
 29  ω    -69.00 -29.00   0.50    0.16    -- -102.00  61.00  90.00   80
 30  ω   -175.00 -88.00   0.50    0.16    -- -102.00 -15.00  90.00  174
 31  ω   -174.00 -89.00   0.50    0.16    -- -102.00 -45.00  60.00  170
 32  ω   -175.00 -89.00   0.50    0.16    -- -102.00 -30.00-150.00  172
 33  ω   -175.00 -85.00   0.50    0.16    -- -102.00 -61.00 -60.00  180
 34  ω   -175.00 -77.00   0.50    0.16    -- -102.00-116.00  18.00  196
 35  ω   -118.00 -71.00   0.50    0.05    --  -46.70-125.00  90.00   94
 36  ω   -118.00 -71.00   0.50    0.05    --  -46.70-125.00  60.00   94
 37  ω   -118.00 -71.00   0.50    0.05    --  -46.70-125.00 -90.00   94
 38  ω   -118.00 -45.00   0.50    0.05    --  -46.70-165.00-128.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1256122000
_diffrn_orient_matrix_UB_12      0.0454845000
_diffrn_orient_matrix_UB_13      -0.1243558000
_diffrn_orient_matrix_UB_21      0.1020241000
_diffrn_orient_matrix_UB_22      0.0879533000
_diffrn_orient_matrix_UB_23      0.0497269000
_diffrn_orient_matrix_UB_31      0.2042406000
_diffrn_orient_matrix_UB_32      -0.0159222000
_diffrn_orient_matrix_UB_33      -0.0796306000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16839
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.990
_diffrn_reflns_theta_min         5.319
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.843
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0032(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0428
_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)+(0.0738P)²+0.2199P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1233
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1685
_reflns_number_total             1860
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc06529g2.cif
_cod_data_source_block           20210716f
_cod_database_code               7129526
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C1H1N1O1
_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.
;
_diffrn_oxdiff_digest_frames
;
0104b6f008d6c2b3862f21288451aaea0000103556b
;
_diffrn_oxdiff_digest_hkl
;
01e9779195c9e8bffaccc8525cd868af8995ce
;
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C1(H1)
1.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C5(H5A,H5B)
1.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
1.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.426
_oxdiff_exptl_absorpt_empirical_full_min 0.620
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O13 O 0.27171(15) 0.73695(6) 0.69172(10) 0.0305(3) Uani 1 1 d . . . . .
O9 O 0.63042(16) 0.86181(6) 0.81462(9) 0.0325(3) Uani 1 1 d . . . . .
O10 O 0.39387(17) 0.94006(7) 0.68575(11) 0.0377(3) Uani 1 1 d . . . . .
N8 N 0.53437(18) 0.88151(7) 0.70332(11) 0.0273(3) Uani 1 1 d . . . . .
C2 C 0.4361(2) 0.69518(8) 0.66418(12) 0.0249(3) Uani 1 1 d . . . . .
C7 C 0.61074(19) 0.83485(8) 0.57892(12) 0.0239(3) Uani 1 1 d . . . . .
C1 C 0.6453(2) 0.73836(8) 0.61706(12) 0.0240(3) Uani 1 1 d . . . . .
H1 H 0.763900 0.736315 0.693616 0.029 Uiso 1 1 calc R . . . .
C3 C 0.4471(2) 0.60013(9) 0.67913(13) 0.0285(3) Uani 1 1 d . . . . .
H3 H 0.336089 0.571763 0.721577 0.034 Uiso 1 1 calc R . . . .
C6 C 0.7287(2) 0.68263(8) 0.50423(13) 0.0291(3) Uani 1 1 d . . . . .
H6A H 0.610553 0.678183 0.429204 0.035 Uiso 1 1 calc R . . . .
H6B H 0.859430 0.709998 0.471597 0.035 Uiso 1 1 calc R . . . .
C11 C 0.8356(2) 0.87951(9) 0.55949(14) 0.0287(3) Uani 1 1 d . . . . .
H11A H 0.812035 0.941125 0.550305 0.043 Uiso 1 1 calc GR . . . .
H11B H 0.892019 0.857226 0.479490 0.043 Uiso 1 1 calc GR . . . .
H11C H 0.943470 0.868128 0.636507 0.043 Uiso 1 1 calc GR . . . .
C5 C 0.7923(2) 0.59189(9) 0.55821(15) 0.0313(3) Uani 1 1 d . . . . .
H5A H 0.817967 0.554169 0.483203 0.038 Uiso 1 1 calc R . . . .
H5B H 0.932427 0.595326 0.617919 0.038 Uiso 1 1 calc R . . . .
C12 C 0.4387(2) 0.84963(9) 0.45745(13) 0.0294(3) Uani 1 1 d . . . . .
H12A H 0.297936 0.822756 0.472793 0.044 Uiso 1 1 calc GR . . . .
H12B H 0.492950 0.824532 0.378725 0.044 Uiso 1 1 calc GR . . . .
H12C H 0.415929 0.910984 0.443755 0.044 Uiso 1 1 calc GR . . . .
C4 C 0.6125(2) 0.55323(9) 0.63336(13) 0.0301(3) Uani 1 1 d . . . . .
H4 H 0.615526 0.493565 0.649151 0.036 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_publ_flag
O9 N8 O10 123.48(11) . . ?
O9 N8 C7 117.47(10) . . ?
O10 N8 C7 118.84(10) . . ?
O13 C2 C1 122.49(11) . . ?
O13 C2 C3 121.74(11) . . ?
C3 C2 C1 115.74(10) . . ?
C1 C7 N8 107.06(9) . . ?
C11 C7 N8 103.32(10) . . ?
C11 C7 C1 111.56(10) . . ?
C12 C7 N8 109.81(10) . . ?
C12 C7 C1 113.72(10) . . ?
C12 C7 C11 110.77(10) . . ?
C2 C1 C7 113.75(10) . . ?
C2 C1 H1 106.7 . . ?
C2 C1 C6 108.70(10) . . ?
C7 C1 H1 106.7 . . ?
C6 C1 C7 113.70(10) . . ?
C6 C1 H1 106.7 . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.82(12) . . ?
C4 C3 H3 119.1 . . ?
C1 C6 H6A 109.7 . . ?
C1 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C5 C6 C1 109.83(11) . . ?
C5 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C4 C5 C6 112.09(10) . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 C4 C5 123.29(12) . . ?
C3 C4 H4 118.4 . . ?
C5 C4 H4 118.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O13 C2 1.2252(15) . ?
O9 N8 1.2271(14) . ?
O10 N8 1.2271(15) . ?
N8 C7 1.5410(15) . ?
C2 C1 1.5277(16) . ?
C2 C3 1.4687(18) . ?
C7 C1 1.5387(17) . ?
C7 C11 1.5333(16) . ?
C7 C12 1.5126(17) . ?
C1 H1 0.9800 . ?
C1 C6 1.5365(17) . ?
C3 H3 0.9300 . ?
C3 C4 1.3382(19) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.5267(18) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.4933(19) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C4 H4 0.9300 . ?
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
_geom_torsion_publ_flag
O13 C2 C1 C7 -12.23(17) . . . . ?
O13 C2 C1 C6 -140.01(12) . . . . ?
O13 C2 C3 C4 171.41(13) . . . . ?
O9 N8 C7 C1 41.83(13) . . . . ?
O9 N8 C7 C11 -76.05(13) . . . . ?
O9 N8 C7 C12 165.73(10) . . . . ?
O10 N8 C7 C1 -143.22(11) . . . . ?
O10 N8 C7 C11 98.90(12) . . . . ?
O10 N8 C7 C12 -19.31(15) . . . . ?
N8 C7 C1 C2 56.44(13) . . . . ?
N8 C7 C1 C6 -178.41(9) . . . . ?
C2 C1 C6 C5 -60.80(13) . . . . ?
C2 C3 C4 C5 -3.0(2) . . . . ?
C7 C1 C6 C5 171.40(10) . . . . ?
C1 C2 C3 C4 -10.62(18) . . . . ?
C1 C6 C5 C4 48.50(15) . . . . ?
C3 C2 C1 C7 169.81(10) . . . . ?
C3 C2 C1 C6 42.03(14) . . . . ?
C6 C5 C4 C3 -16.81(18) . . . . ?
C11 C7 C1 C2 168.80(10) . . . . ?
C11 C7 C1 C6 -66.05(14) . . . . ?
C12 C7 C1 C2 -65.04(13) . . . . ?
C12 C7 C1 C6 60.11(13) . . . . ?
