Synthesis of cyclobutane-fused chromanones <i>via</i> gold-mediated photocatalysis.
Voloshkin, Vladislav A.; Villa, Marco; Martynova, Ekaterina A.; Beliš, Marek; Van Hecke, Kristof; Ceroni, Paola; Nolan, Steven P.; Chemical science 15 (2024) 4571–4580; doi:10.1039/d3sc06675d

data_1571053
_publ_section_title
;
 Synthesis of cyclobutane-fused chromanones <i>via</i> gold-mediated
 photocatalysis.
;
_journal_issue                   12
_journal_name_full               'Chemical science'
_journal_page_first              4571
_journal_page_last               4580
_journal_paper_doi               10.1039/d3sc06675d
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C19 H22 O2'
_chemical_formula_sum            'C19 H22 O2'
_chemical_formula_weight         282.37
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-07-21 deposited with the CCDC.	2024-02-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.755(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8092(3)
_cell_length_b                   6.61169(13)
_cell_length_c                   18.3462(4)
_cell_measurement_reflns_used    7491
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.8740
_cell_measurement_theta_min      4.3350
_cell_volume                     1430.79(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_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    -87.00  -6.00   1.00    1.00    --  -41.55 125.00 150.00   81
  2  \w   -116.00 -17.00   1.00    1.00    --  -41.55 -38.00   0.00   99
  3  \w    -21.00  74.00   1.00    1.00    --   41.55 -77.00 -60.00   95
  4  \w     27.00  96.00   1.00    1.00    --   41.55-125.00-120.00   69
  5  \w     30.00 139.00   1.00    5.00    --  106.01 -77.00  30.00  109
  6  \w     34.00 135.00   1.00    5.00    --  106.01 -61.00-120.00  101
  7  \w     33.00 132.00   1.00    5.00    --  106.01 -45.00 120.00   99
  8  \w     33.00 132.00   1.00    5.00    --  106.01 -45.00   0.00   99
  9  \w     24.00 159.00   1.00    5.00    --  106.01 -15.00-120.00  135
 10  \w   -114.00 -13.00   1.00    1.00    --  -41.55 -57.00-120.00  101
 11  \w   -114.00 -13.00   1.00    1.00    --  -41.55 -57.00 120.00  101
 12  \w     53.00 178.00   1.00    5.00    --  106.01  15.00 -30.00  125
 13  \w     35.00 112.00   1.00    5.00    --  106.01-125.00 -90.00   77
 14  \w     78.00 178.00   1.00    5.00    --  106.01  30.00 150.00  100
 15  \w     78.00 178.00   1.00    5.00    --  106.01  30.00  60.00  100
 16  \w    -87.00  -6.00   1.00    1.00    --  -41.55 125.00  30.00   81
 17  \w   -114.00 -13.00   1.00    1.00    --  -41.55 -57.00 -60.00  101
 18  \w     77.00 102.00   1.00    5.00    --  106.01  61.00-150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1042665000
_diffrn_orient_matrix_UB_12      0.0043457000
_diffrn_orient_matrix_UB_13      0.0537995000
_diffrn_orient_matrix_UB_21      -0.0294207000
_diffrn_orient_matrix_UB_22      0.2180706000
_diffrn_orient_matrix_UB_23      0.0217785000
_diffrn_orient_matrix_UB_31      -0.0729133000
_diffrn_orient_matrix_UB_32      -0.0818925000
_diffrn_orient_matrix_UB_33      0.0608484000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13957
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.902
_diffrn_reflns_theta_min         4.359
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.544
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_preparation       Synthesis
_exptl_crystal_recrystallization_method 'Hexane diffusion in chloroforom'
_exptl_crystal_size_max          0.348
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0620P)^2^+0.4661P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1118
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2610
_reflns_number_total             2868
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc06675d2.cif
_cod_data_source_block           vl705bc
_cod_depositor_comments          'Adding full bibliography for 1571053.cif.'
_cod_database_code               1571053
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H19 O2'
_shelx_estimated_absorpt_t_max   0.931
_shelx_estimated_absorpt_t_min   0.805
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C10(H10), C12(H12), C14(H14), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              29213
_olex2_date_sample_data_collection 2023-04-28
_olex2_exptl_crystal_mounting_method 'Litho loop'
_olex2_submission_original_sample_id VL705BC
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.584
_oxdiff_exptl_absorpt_empirical_full_min 0.418