#------------------------------------------------------------------------------
#$Date: 2022-01-11 00:51:05 +0200 (Tue, 11 Jan 2022) $
#$Revision: 271974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/95/7129529.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_7129529
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 H9 N O3'
_chemical_formula_sum            'C9 H9 N O3'
_chemical_formula_weight         179.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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                 92.654(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.61652(15)
_cell_length_b                   8.2450(3)
_cell_length_c                   9.0227(3)
_cell_measurement_reflns_used    6319
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.9200
_cell_measurement_theta_min      7.2380
_cell_volume                     417.38(2)
_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      99.99(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 0.973
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     92.00 177.00   0.50    0.05    --  104.75  45.00 166.00  170
  2  ω     34.00 119.00   0.50    0.05    --   46.95  45.00 166.00  170
  3  ω     24.00 119.00   0.50    0.05    --   46.95  77.00 -90.00  190
  4  ω    -25.00  53.00   0.50    0.05    --   46.95 -45.00  15.00  156
  5  ω     32.00  73.00   0.50    0.05    --  104.75 -61.00-150.00   82
  6  ω     32.00  73.00   0.50    0.05    --  104.75 -61.00-120.00   82
  7  ω     32.00  73.00   0.50    0.05    --  104.75 -61.00 -60.00   82
  8  ω     32.00  73.00   0.50    0.05    --  104.75 -61.00   0.00   82
  9  ω    -24.00  29.00   0.50    0.05    --  -46.95  19.00 150.00  106
 10  ω    -49.00  25.00   0.50    0.05    --  -46.95  45.00 166.00  148
 11  ω     15.00  95.00   0.50    0.05    --   46.95-125.00-120.00  160
 12  ω     32.00 117.00   0.50    0.05    --  104.75-125.00-180.00  170
 13  ω    -24.00  29.00   0.50    0.05    --  -46.95  19.00 -30.00  106
 14  ω    -69.00 -29.00   0.50    0.05    -- -102.00  61.00   0.00   80
 15  ω    -69.00 -29.00   0.50    0.05    -- -102.00  61.00-150.00   80
 16  ω    -69.00 -29.00   0.50    0.05    -- -102.00  61.00 -60.00   80
 17  ω    -69.00 -29.00   0.50    0.05    -- -102.00  61.00 -30.00   80
 18  ω    -69.00 -29.00   0.50    0.05    -- -102.00  61.00  30.00   80
 19  ω   -119.00 -34.00   0.50    0.05    --  -46.95 -45.00  15.00  170
 20  ω   -119.00 -24.00   0.50    0.05    --  -46.95 -77.00 120.00  190
 21  ω   -119.00 -68.00   0.50    0.05    --  -46.95 -77.00   0.00  102
 22  ω   -119.00 -30.00   0.50    0.05    --  -46.95 -61.00 -81.58  178
 23  ω   -119.00 -24.00   0.50    0.05    --  -46.95 -77.00-150.00  190
 24  ω   -175.00 -78.00   0.50    0.05    -- -102.00 -79.00 -47.82  194
 25  ω   -175.00 -79.00   0.50    0.05    -- -102.00 -77.00 -60.00  192
 26  ω   -175.00 -79.00   0.50    0.05    -- -102.00 -77.00-120.00  192
 27  ω   -175.00 -85.00   0.50    0.05    -- -102.00 -61.00-120.00  180
 28  ω   -175.00 -79.00   0.50    0.05    -- -102.00 -77.00 -90.00  192
 29  ω   -174.00 -89.00   0.50    0.05    -- -102.00 -45.00-120.00  170
 30  ω   -174.00 -88.00   0.50    0.05    -- -102.00 -50.00 -37.48  172
 31  ω   -174.00 -89.00   0.50    0.05    -- -102.00 -45.00  15.00  170
 32  ω   -175.00 -79.00   0.50    0.05    -- -102.00 -77.00 120.00  192
 33  ω   -175.00 -89.00   0.50    0.05    -- -102.00 -30.00  90.00  172
 34  ω   -174.00 -89.00   0.50    0.05    -- -102.00 -45.00 -30.00  170
 35  ω   -175.00 -79.00   0.50    0.05    -- -102.00 -77.00 -30.00  192
 36  ω   -175.00 -76.00   0.50    0.05    -- -102.00 -83.00 -59.57  198
 37  ω   -119.00 -71.00   0.50    0.05    --  -46.95-125.00-180.00   96
;
_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      0.0230476000
_diffrn_orient_matrix_UB_12      -0.0009359000
_diffrn_orient_matrix_UB_13      -0.1694759000
_diffrn_orient_matrix_UB_21      0.2273730000
_diffrn_orient_matrix_UB_22      0.1039461000
_diffrn_orient_matrix_UB_23      0.0179600000
_diffrn_orient_matrix_UB_31      0.1521247000
_diffrn_orient_matrix_UB_32      -0.1553075000
_diffrn_orient_matrix_UB_33      0.0129810000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7648
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.884
_diffrn_reflns_theta_min         4.907
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.910
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47352
_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    1.426
_exptl_crystal_description       plate
_exptl_crystal_F_000             188
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 710 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.14(16)
_refine_ls_extinction_coef       0.019(4)
_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   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1631
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0315
_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)+(0.0521P)²+0.1073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0906
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_full    0.957
_reflns_Friedel_fraction_max     0.893
_reflns_number_gt                1615
_reflns_number_total             1631
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc06529g2.cif
_cod_data_source_block           20210717c
_cod_database_code               7129529
_shelx_shelxl_version_number     2018/3
_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
;
01eadae72a9e5f4d4c49880376dadc746f00142653c
;
_diffrn_oxdiff_digest_hkl
;
01da570ffeccb6717f292d8d0c6033dc6f665f
;
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
1.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C5(H5), C3(H3), C4(H4)
;
_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 2.261
_oxdiff_exptl_absorpt_empirical_full_min 0.551
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
O11 O 0.2173(3) 0.3378(2) 0.41104(17) 0.0241(4) Uani 1 1 d . . . . .
O13 O 0.7035(3) 0.4852(2) 0.40524(17) 0.0252(4) Uani 1 1 d . . . . .
O12 O 0.1637(3) 0.3853(2) 0.64259(18) 0.0324(5) Uani 1 1 d . . . . .
N10 N 0.2158(3) 0.4287(2) 0.5182(2) 0.0207(4) Uani 1 1 d . . . . .
C7 C 0.5864(4) 0.5580(3) 0.3098(2) 0.0205(5) Uani 1 1 d . . . . .
C6 C 0.8562(4) 0.4717(3) 0.1125(2) 0.0223(5) Uani 1 1 d . . . . .
H6 H 0.937616 0.408010 0.183221 0.027 Uiso 1 1 calc R . . . .
C1 C 0.6608(4) 0.5647(3) 0.1529(2) 0.0204(5) Uani 1 1 d . . . . .
C2 C 0.5405(4) 0.6592(3) 0.0456(2) 0.0246(5) Uani 1 1 d . . . . .
H2 H 0.410442 0.721479 0.070994 0.030 Uiso 1 1 calc R . . . .
C8 C 0.3560(4) 0.6419(3) 0.3463(2) 0.0215(5) Uani 1 1 d . . . . .
H8A H 0.376416 0.758142 0.336712 0.026 Uiso 1 1 calc R . . . .
H8B H 0.231007 0.608541 0.274987 0.026 Uiso 1 1 calc R . . . .
C5 C 0.9289(4) 0.4740(3) -0.0321(2) 0.0257(5) Uani 1 1 d . . . . .
H5 H 1.058637 0.411895 -0.058275 0.031 Uiso 1 1 calc R . . . .
C3 C 0.6142(5) 0.6607(3) -0.0990(2) 0.0275(5) Uani 1 1 d . . . . .
H3 H 0.532962 0.723842 -0.170252 0.033 Uiso 1 1 calc R . . . .
C4 C 0.8080(4) 0.5689(3) -0.1380(2) 0.0270(5) Uani 1 1 d . . . . .
H4 H 0.857154 0.570848 -0.235055 0.032 Uiso 1 1 calc R . . . .
C9 C 0.2793(4) 0.6043(3) 0.5006(2) 0.0233(5) Uani 1 1 d . . . . .
H9A H 0.407442 0.631929 0.571919 0.028 Uiso 1 1 calc R . . . .
H9B H 0.142400 0.670699 0.521804 0.028 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
O11 N10 O12 123.7(2) . . ?
O11 N10 C9 119.80(18) . . ?
O12 N10 C9 116.52(19) . . ?
O13 C7 C1 121.49(19) . . ?
O13 C7 C8 120.62(19) . . ?
C1 C7 C8 117.87(18) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C1 120.4(2) . . ?
C6 C1 C7 118.84(19) . . ?
C2 C1 C7 122.05(19) . . ?
C2 C1 C6 119.11(19) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 119.9 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 C7 112.96(18) . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 120.0(2) . . ?
C4 C5 H5 120.0 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C5 C4 H4 120.1 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4 120.1 . . ?
N10 C9 C8 112.02(18) . . ?
N10 C9 H9A 109.2 . . ?
N10 C9 H9B 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
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
O11 N10 1.224(2) . ?
O13 C7 1.217(3) . ?
O12 N10 1.226(2) . ?
N10 C9 1.501(3) . ?
C7 C1 1.496(3) . ?
C7 C8 1.517(3) . ?
C6 H6 0.9300 . ?
C6 C1 1.401(3) . ?
C6 C5 1.385(3) . ?
C1 C2 1.393(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.508(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.388(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(4) . ?
C4 H4 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
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
O11 N10 C9 C8 -4.1(3) . . . . ?
O13 C7 C1 C6 6.4(3) . . . . ?
O13 C7 C1 C2 -174.2(2) . . . . ?
O13 C7 C8 C9 -7.9(3) . . . . ?
O12 N10 C9 C8 176.17(18) . . . . ?
C7 C1 C2 C3 -179.4(2) . . . . ?
C7 C8 C9 N10 -65.5(2) . . . . ?
C6 C1 C2 C3 0.0(4) . . . . ?
C6 C5 C4 C3 -0.3(4) . . . . ?
C1 C7 C8 C9 170.65(19) . . . . ?
C1 C6 C5 C4 0.0(4) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C8 C7 C1 C6 -172.1(2) . . . . ?
C8 C7 C1 C2 7.2(3) . . . . ?
C5 C6 C1 C7 179.5(2) . . . . ?
C5 C6 C1 C2 0.1(3) . . . . ?
