Visible-light-induced oxidant/additive-free atom-economic synthesis of multifunctionalized cyclopropanes <i>via</i> energy transfer.
Gore, Babasaheb Sopan; Wang, Jeh-Jeng; Chemical communications (Cambridge, England) 59 (2023) 5878–5881; doi:10.1039/d3cc01021j

data_7131593
_publ_section_title
;
 Visible-light-induced oxidant/additive-free atom-economic synthesis of
 multifunctionalized cyclopropanes <i>via</i> energy transfer.
;
_journal_issue                   39
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5878
_journal_page_last               5881
_journal_paper_doi               10.1039/d3cc01021j
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C23 H18 O'
_chemical_formula_sum            'C23 H18 O'
_chemical_formula_weight         310.37
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-26
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-12-14 deposited with the CCDC.	2023-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.338(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1546(3)
_cell_length_b                   5.92860(10)
_cell_length_c                   16.4487(3)
_cell_measurement_reflns_used    16828
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9240
_cell_measurement_theta_min      2.4720
_cell_volume                     1570.85(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_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      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -79.00  38.00   0.50   11.03    --   10.60 -82.00 -94.00  234
  2  \w    -17.00 100.00   0.50   11.03    --   10.60  82.00  27.00  234
  3  \w    -38.00  78.00   0.50   11.03    --  -10.90  82.00  27.00  232
  4  \w   -100.00  16.00   0.50   11.03    --  -10.90 -82.00 -94.00  232
  5  \w    -79.00  48.00   0.50   11.03    --   10.60 -38.00 -60.00  254
  6  \w    -79.00  41.00   0.50   11.03    --   10.60 -57.00  60.00  240
  7  \w    -79.00  38.00   0.50   11.03    --   10.60 -82.00-180.00  234
  8  \w    -15.00 100.00   0.50   11.03    --   10.60  77.00 -90.00  230
  9  \w    -15.00  72.00   0.50   11.03    --   10.60  77.00-180.00  174
 10  \w    -15.00 100.00   0.50   11.03    --   10.60  77.00 150.00  230
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0212841000
_diffrn_orient_matrix_UB_12      -0.0514697000
_diffrn_orient_matrix_UB_13      0.0312936000
_diffrn_orient_matrix_UB_21      -0.0385637000
_diffrn_orient_matrix_UB_22      0.0295785000
_diffrn_orient_matrix_UB_23      -0.0206831000
_diffrn_orient_matrix_UB_31      -0.0004451000
_diffrn_orient_matrix_UB_32      -0.1039763000
_diffrn_orient_matrix_UB_33      -0.0214124000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27269
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.484
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2759
_refine_ls_number_restraints     684
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0362
_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/[\s^2^(Fo^2^)+(0.0468P)^2^+0.4433P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0929
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2497
_reflns_number_total             2759
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01021j2.cif
_cod_data_source_block           k11008-jjw-o(nc-en-18)
_cod_depositor_comments
'Adding full bibliography for 7131590--7131593.cif.'
_cod_database_code               7131593
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C23 H18 N1 O1'
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.984
_diffrn_oxdiff_digest_frames
;
01877b3f76c6044d93a986a1ba4eb9c474000255359
;
_diffrn_oxdiff_digest_hkl
;
018b73adcdf211fece8f96464f5a9d99a74b0c
;
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim O1: within
3.8A with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1), C8(H8), C17(H17)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_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 1.916
_oxdiff_exptl_absorpt_empirical_full_min 0.479