#------------------------------------------------------------------------------
#$Date: 2023-07-06 03:45:00 +0300 (Thu, 06 Jul 2023) $
#$Revision: 285011 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/94/7159450.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_7159450
loop_
_publ_author_name
'Qi, Rui'
'Bai, Tianwen'
'Tang, Shuwang'
'Hou, Ming'
'Zhang, Zhide'
'Xie, Wenlin'
'Deng, Yangling'
'Zhou, Hongwei'
'Qiu, Guanyinsheng'
_publ_section_title
;
 Solvent-promoted photochemical carbonylation of benzylic C-H bonds under
 iron catalysis.
;
_journal_issue                   26
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5382
_journal_page_last               5386
_journal_paper_doi               10.1039/d3ob00328k
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C14 H9 O'
_chemical_formula_sum            'C14 H9 O'
_chemical_formula_weight         193.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2022-12-09 deposited with the CCDC.	2023-06-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.970(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.8930(10)
_cell_length_b                   7.7491(4)
_cell_length_c                   13.6613(7)
_cell_measurement_reflns_used    1294
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.2400
_cell_measurement_theta_min      4.0480
_cell_volume                     1893.93(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     79.00 109.00   1.00    1.00    --   36.33 178.00  30.00   30
  2  ω     43.00  69.00   1.00    1.00    --   36.33 -99.00 -30.00   26
  3  ω     12.00  41.00   1.00    1.00    --   36.33  77.00 150.00   29
  4  ω     -1.00  25.00   1.00    1.00    --   36.33 -99.00 -30.00   26
  5  ω     54.00 103.00   1.00    1.00    --   36.33  77.00-150.00   49
  6  ω     12.00  49.00   1.00    1.00    --   36.33  77.00-150.00   37
  7  ω     58.00 109.00   1.00    1.00    --   36.33 178.00  90.00   51
  8  ω     63.00  89.00   1.00    1.00    --   36.33-178.00-150.00   26
  9  ω     65.00 100.00   1.00    1.00    --   36.33  77.00 150.00   35
 10  ω     62.00 113.00   1.00    2.38    --  108.00-111.00 -30.00   51
 11  ω     49.00 124.00   1.00    2.38    --  108.00 -61.00-180.00   75
 12  ω     45.00  88.00   1.00    2.38    --  108.00 -77.00  90.00   43
 13  ω     83.00 123.00   1.00    2.38    --  108.00 -45.00  30.00   40
 14  ω     43.00  68.00   1.00    2.38    --  108.00 -45.00  30.00   25
 15  ω     44.00 107.00   1.00    2.38    --  108.00 -95.00-180.00   63
 16  ω     94.00 165.00   1.00    2.38    --  108.00  45.00   0.00   71
 17  ω     94.00 136.00   1.00    2.38    --  108.00  61.00 -60.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0840837000
_diffrn_orient_matrix_UB_12      -0.0059262000
_diffrn_orient_matrix_UB_13      0.0262532000
_diffrn_orient_matrix_UB_21      -0.0168607000
_diffrn_orient_matrix_UB_22      -0.1122538000
_diffrn_orient_matrix_UB_23      0.0900515000
_diffrn_orient_matrix_UB_31      0.0085461000
_diffrn_orient_matrix_UB_32      -0.1637907000
_diffrn_orient_matrix_UB_33      -0.0626065000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3062
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.830
_diffrn_reflns_theta_min         4.944
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.680
_refine_diff_density_rms         0.203
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1819
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0670
_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)+(0.1063P)²+0.1837P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1604
_refine_ls_wR_factor_ref         0.1731
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1511
_reflns_number_total             1819
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00328k2.cif
_cod_data_source_block           20220623-1
_cod_database_code               7159450
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H O N'
_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.
;
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C002(H002)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D),
 C00E(H00E), C00F(H00F)
;
_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 2.975
_oxdiff_exptl_absorpt_empirical_full_min 0.643
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.61696(10) -0.00674(19) 0.31860(15) 0.0821(6) Uani 1 1 d . . . . .
C002 C 0.74856(8) 0.38370(18) 0.44117(9) 0.0351(4) Uani 1 1 d . . . . .
H002 H 0.779138 0.480546 0.418921 0.042 Uiso 1 1 calc R . . . .
C003 C 0.78278(9) 0.22046(19) 0.40233(10) 0.0363(4) Uani 1 1 d . . . . .
C004 C 0.66947(9) 0.41589(19) 0.40633(10) 0.0384(4) Uani 1 1 d . . . . .
C005 C 0.62528(9) 0.2851(2) 0.36548(11) 0.0419(4) Uani 1 1 d . . . . .
C006 C 0.73784(10) 0.0872(2) 0.36498(11) 0.0415(4) Uani 1 1 d . . . . .
C007 C 0.85987(9) 0.1940(2) 0.40781(11) 0.0451(4) Uani 1 1 d . . . . .
H007 H 0.890866 0.282927 0.429561 0.054 Uiso 1 1 calc R . . . .
C008 C 0.63722(10) 0.5778(2) 0.42028(13) 0.0476(4) Uani 1 1 d . . . . .
H008 H 0.665870 0.666698 0.447025 0.057 Uiso 1 1 calc R . . . .
C009 C 0.65667(10) 0.1114(2) 0.34828(12) 0.0489(5) Uani 1 1 d . . . . .
C00A C 0.55043(10) 0.3174(3) 0.34015(13) 0.0525(5) Uani 1 1 d . . . . .
H00A H 0.521298 0.229718 0.312969 0.063 Uiso 1 1 calc R . . . .
C00B C 0.56322(11) 0.6077(3) 0.39488(14) 0.0570(5) Uani 1 1 d . . . . .
H00B H 0.542589 0.716416 0.404659 0.068 Uiso 1 1 calc R . . . .
C00C C 0.89087(11) 0.0380(3) 0.38147(13) 0.0561(5) Uani 1 1 d . . . . .
H00C H 0.942353 0.022599 0.386272 0.067 Uiso 1 1 calc R . . . .
C00D C 0.77000(12) -0.0698(2) 0.33859(13) 0.0537(5) Uani 1 1 d . . . . .
H00D H 0.739740 -0.158046 0.314340 0.064 Uiso 1 1 calc R . . . .
C00E C 0.51966(11) 0.4771(3) 0.35502(14) 0.0583(5) Uani 1 1 d . . . . .
H00E H 0.469820 0.497483 0.338409 0.070 Uiso 1 1 calc R . . . .
C00F C 0.84602(12) -0.0957(3) 0.34800(14) 0.0596(5) Uani 1 1 d . . . . .
H00F H 0.866874 -0.201769 0.332036 0.071 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'
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
C002 C002 H002 107.6 2_656 . ?
C003 C002 C002 110.25(9) . 2_656 ?
C003 C002 H002 107.6 . . ?
C003 C002 C004 114.41(12) . . ?
C004 C002 C002 109.26(14) . 2_656 ?
C004 C002 H002 107.6 . . ?
C006 C003 C002 120.91(14) . . ?
C007 C003 C002 120.79(14) . . ?
C007 C003 C006 118.20(15) . . ?
C005 C004 C002 121.92(14) . . ?
C008 C004 C002 119.63(14) . . ?
C008 C004 C005 118.33(15) . . ?
C004 C005 C009 120.68(15) . . ?
C004 C005 C00A 120.10(16) . . ?
C00A C005 C009 119.22(15) . . ?
C003 C006 C009 121.30(15) . . ?
C00D C006 C003 120.02(16) . . ?
C00D C006 C009 118.61(16) . . ?
C003 C007 H007 119.5 . . ?
C00C C007 C003 121.05(16) . . ?
C00C C007 H007 119.5 . . ?
C004 C008 H008 119.6 . . ?
C00B C008 C004 120.88(17) . . ?
C00B C008 H008 119.6 . . ?
O001 C009 C005 120.91(18) . . ?
O001 C009 C006 121.30(17) . . ?
C005 C009 C006 117.76(14) . . ?
C005 C00A H00A 119.7 . . ?
C00E C00A C005 120.66(17) . . ?
C00E C00A H00A 119.7 . . ?
C008 C00B H00B 119.8 . . ?
C008 C00B C00E 120.43(17) . . ?
C00E C00B H00B 119.8 . . ?
C007 C00C H00C 119.7 . . ?
C007 C00C C00F 120.57(18) . . ?
C00F C00C H00C 119.7 . . ?
C006 C00D H00D 119.6 . . ?
C00F C00D C006 120.89(18) . . ?
C00F C00D H00D 119.6 . . ?
C00A C00E C00B 119.59(17) . . ?
C00A C00E H00E 120.2 . . ?
C00B C00E H00E 120.2 . . ?
C00C C00F H00F 120.4 . . ?
C00D C00F C00C 119.17(17) . . ?
C00D C00F H00F 120.4 . . ?
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
O001 C009 1.224(2) . ?
C002 C002 1.607(3) 2_656 ?
C002 H002 0.9800 . ?
C002 C003 1.506(2) . ?
C002 C004 1.506(2) . ?
C003 C006 1.400(2) . ?
C003 C007 1.395(2) . ?
C004 C005 1.396(2) . ?
C004 C008 1.395(2) . ?
C005 C009 1.478(2) . ?
C005 C00A 1.400(2) . ?
C006 C009 1.478(2) . ?
C006 C00D 1.396(2) . ?
C007 H007 0.9300 . ?
C007 C00C 1.381(2) . ?
C008 H008 0.9300 . ?
C008 C00B 1.383(3) . ?
C00A H00A 0.9300 . ?
C00A C00E 1.371(3) . ?
C00B H00B 0.9300 . ?
C00B C00E 1.384(3) . ?
C00C H00C 0.9300 . ?
C00C C00F 1.384(3) . ?
C00D H00D 0.9300 . ?
C00D C00F 1.379(3) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
