Catalyst-free, scalable heterocyclic flow photocyclopropanation
Klöpfer, Viktor; Eckl, Robert; Floß, Johannes; Roth, Philippe M. C.; Reiser, Oliver; Barham, Joshua P.; Green Chemistry 23 (2021) 6366–6372; doi:10.1039/D1GC01624E

data_7243124
_publ_section_title
;
 Catalyst-free, scalable heterocyclic flow photocyclopropanation
;
_journal_issue                   17
_journal_name_full               'Green Chemistry'
_journal_page_first              6366
_journal_page_last               6372
_journal_paper_doi               10.1039/D1GC01624E
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C17 H14 O2 S'
_chemical_formula_sum            'C17 H14 O2 S'
_chemical_formula_weight         282.34
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-08
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-06-24 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.790(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6106(3)
_cell_length_b                   16.0508(3)
_cell_length_c                   7.5624(2)
_cell_measurement_reflns_used    9542
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      72.5480
_cell_measurement_theta_min      3.9090
_cell_volume                     1362.63(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.964
_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     39.00  64.00   0.50    0.30    --   34.00  74.00 -97.14   50
  2  \w     40.00  65.00   0.50    0.30    --   34.00  73.00-111.59   50
  3  \w     57.00  82.00   0.50    0.30    --   50.00  70.00-109.44   50
  4  \w     58.00  83.00   0.50    0.30    --   50.00  68.00-121.14   50
  5  \w     53.00  78.00   0.50    0.30    --   46.00  70.00-157.79   50
  6  \w     40.00  65.00   0.50    0.30    --   34.00  73.00-169.22   50
  7  \w     38.00  63.00   0.50    0.30    --   30.00  69.00-133.63   50
  8  \w      7.00  33.00   0.50    0.30    --   14.00  93.00-154.07   52
  9  \w     29.00  71.00   0.50    0.30    --   62.57 -95.00 -90.00   84
 10  \w     32.00 102.00   0.50    0.30    --   75.21-125.00 -90.00  140
 11  \w     43.00  93.00   0.50    0.30    --   75.21-125.00  30.00  100
 12  \w     22.00  89.00   0.50    0.30    --   62.57-125.00  30.00  134
 13  \w     50.00  84.00   0.50    0.30    --   75.21 -95.00  90.00   68
 14  \w     26.00  59.00   0.50    0.30    --   62.57 -95.00 150.00   66
 15  \w     40.00  80.00   0.50    0.30    --   75.21 -95.00 150.00   80
 16  \w     30.00  67.00   0.50    0.30    --   62.57 -95.00  90.00   74
 17  \w    -86.00 -53.00   0.50    0.30    --  -64.16 -24.00 -23.00   66
 18  \w   -115.00 -80.00   0.50    0.30    --  -70.24 -24.00 -23.00   70
 19  \w   -101.00 -76.00   0.50    0.30    --  -70.00 -72.00 -55.57   50
 20  \w   -105.00 -80.00   0.50    0.30    --  -75.50 -79.00-156.93   50
 21  \w    -99.00 -69.00   0.50    0.30    --  -62.00 -71.00-174.80   60
 22  \w   -106.00 -80.00   0.50    0.30    --  -75.50 -83.00 -91.22   52
 23  \w    -67.00 -38.00   0.50    0.30    --  -34.00 -75.00  13.13   58
 24  \w    -97.00 -60.00   0.50    0.30    --  -70.24 125.00 -90.00   74
 25  \w    -54.00 -26.00   0.50    0.30    --  -70.24 125.00 -90.00   56
 26  \w     77.00 105.00   0.50    0.30    --   62.57  15.00-150.00   56
 27  \w     60.00  88.00   0.50    0.30    --   54.00  72.00 -69.88   56
 28  \w     75.00 103.00   0.50    0.30    --   70.00  75.00 -68.78   56
 29  \w     63.00  88.00   0.50    0.30    --   54.00  61.00 -83.63   50
 30  \w     68.00  93.00   0.50    0.30    --   62.00  72.00 -97.67   50
 31  \w     76.00 101.00   0.50    0.30    --   70.00  73.00-133.02   50
 32  \w     61.00  86.00   0.50    0.30    --   54.00  71.00-151.65   50
 33  \w     87.00 124.00   0.50    0.30    --   76.92  25.00 -66.72   74
 34  \w     74.00 124.00   0.50    0.30    --   76.92  25.00 -13.29  100
 35  \w     66.00  93.00   0.50    0.30    --   75.21  24.00 140.00   54
 36  \w     90.00 117.00   0.50    0.30    --   72.44  24.00 140.00   54
 37  \w     85.00 110.00   0.50    0.30    --   62.57  24.00 140.00   50
 38  \w     51.00  80.00   0.50    0.30    --   62.57  24.00 140.00   58
 39  \w     75.00 102.00   0.50    0.30    --   62.57  15.00  90.00   54
 40  \w     56.00 118.00   0.50    0.30    --   75.21  15.00  90.00  124
 41  \w     44.00 117.00   0.50    0.30    --   75.21  15.00 -90.00  146
 42  \w     33.00  72.00   0.50    0.30    --   62.57  15.00-150.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1291162000
_diffrn_orient_matrix_UB_12      0.0160238000
_diffrn_orient_matrix_UB_13      -0.1107666000
_diffrn_orient_matrix_UB_21      0.0457080000
_diffrn_orient_matrix_UB_22      0.0262811000
_diffrn_orient_matrix_UB_23      -0.1659814000
_diffrn_orient_matrix_UB_31      -0.0095977000
_diffrn_orient_matrix_UB_32      -0.0908764000
_diffrn_orient_matrix_UB_33      -0.0673764000
_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  0.0250
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15601
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.823
_diffrn_reflns_theta_min         3.938
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.089
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.729
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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_density_diffrn    1.376
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.677
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2655
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0461
_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/[\s^2^(Fo^2^)+(0.0641P)^2^+1.1676P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1274
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2453
_reflns_number_total             2655
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc01624e2.cif
_cod_data_source_block           u070
_cod_depositor_comments          'Adding full bibliography for 7243124.cif.'
_cod_database_code               7243124
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C17 H14 O2 S'
_shelx_estimated_absorpt_t_max   0.803
_shelx_estimated_absorpt_t_min   0.759
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C13(H13), C7(H7), C9(H9), C8(H8), C15(H15), C14(H14), C16(H16)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              93906
_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 1.822
_oxdiff_exptl_absorpt_empirical_full_min 0.677