Formal [4 + 4]-, [4 + 3]-, and [4 + 2]-cycloaddition reactions of donor–acceptor cyclobutenes, cyclopropenes and siloxyalkynes induced by Brønsted acid catalysis
Zheng, Haifeng; Wang, Rui; Wang, Kan; Wherritt, Daniel; Arman, Hadi; Doyle, Michael P.; Chemical Science 12 (2021) 4819–4824; doi:10.1039/D1SC00158B

data_1560602
_publ_section_title
;
 Formal [4 + 4]-, [4 + 3]-, and [4 + 2]-cycloaddition reactions of
 donor--acceptor cyclobutenes, cyclopropenes and siloxyalkynes induced by
 Br\/onsted acid catalysis
;
_journal_issue                   13
_journal_name_full               'Chemical Science'
_journal_page_first              4819
_journal_page_last               4824
_journal_paper_doi               10.1039/D1SC00158B
_journal_volume                  12
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H23 F O5'
_chemical_formula_sum            'C29 H23 F O5'
_chemical_formula_weight         470.47
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-15
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_audit_update_record
;
2020-06-16 deposited with the CCDC.	2021-02-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.001(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.9631(3)
_cell_length_b                   9.1494(2)
_cell_length_c                   13.3605(4)
_cell_measurement_reflns_used    6038
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      75.3640
_cell_measurement_theta_min      4.5230
_cell_volume                     1191.28(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (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      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 0.999
_diffrn_measured_fraction_theta_max 0.978
_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    -81.00  -1.00   0.50    0.38    --  -46.62 109.00 122.00  160
  2  \w    -51.00 -16.00   0.50    1.52    --  -88.50  45.00  60.00   70
  3  \w    -51.00 -16.00   0.50    1.52    --  -88.50  45.00  90.00   70
  4  \w    -82.00 -15.00   0.50    1.52    --  -88.50 109.00 122.00  134
  5  \w    -51.00 -16.00   0.50    1.52    --  -88.50  45.00 -30.00   70
  6  \w    -51.00 -16.00   0.50    1.52    --  -88.50  45.00 -60.00   70
  7  \w   -119.00 -83.00   0.50    0.38    --  -46.62 -57.00-150.00   72
  8  \w   -120.00 -48.00   0.50    0.38    --  -46.62 -37.00-120.00  144
  9  \w   -119.00 -87.00   0.50    0.38    --  -46.62-125.00-120.00   64
 10  \w   -119.00 -83.00   0.50    0.38    --  -46.62 -57.00   0.00   72
 11  \w   -120.00 -32.00   0.50    0.38    --  -46.62 -37.00   0.00  176
 12  \w     22.00  87.00   0.50    0.38    --   46.62-109.00  26.00  130
 13  \w     34.00 108.00   0.50    1.52    --  106.69-109.00  26.00  148
 14  \w     34.00 111.00   0.50    1.52    --  106.69-125.00   0.00  154
 15  \w     34.00 101.00   0.50    1.52    --  106.69 -77.00   0.00  134
 16  \w     34.00  71.00   0.50    1.52    --  106.69 -61.00 120.00   74
 17  \w     34.00 101.00   0.50    1.52    --  106.69 -77.00  60.00  134
 18  \w     34.00  71.00   0.50    1.52    --  106.69 -61.00   0.00   74
 19  \w     83.00 120.00   0.50    0.38    --   46.62  57.00-150.00   74
 20  \w     83.00 120.00   0.50    0.38    --   46.62  57.00-180.00   74
 21  \w     83.00 120.00   0.50    0.38    --   46.62  57.00 -90.00   74
 22  \w     95.00 178.00   0.50    1.52    --  106.69 125.00-150.00  166
 23  \w    104.00 178.00   0.50    1.52    --  106.69 109.00 122.00  148
 24  \w     34.00 101.00   0.50    1.52    --  106.69 -77.00-180.00  134
 25  \w     34.00  71.00   0.50    1.52    --  106.69 -61.00-180.00   74
 26  \w   -119.00 -87.00   0.50    0.38    --  -46.62-125.00  60.00   64
 27  \w   -120.00 -32.00   0.50    0.38    --  -46.62 -37.00  90.00  176
 28  \w   -160.00 -82.00   0.50    1.52    --  -88.50-109.00  26.00  156
 29  \w   -160.00-100.00   0.50    1.52    --  -88.50 -94.00  60.00  120
 30  \w   -160.00-101.00   0.50    1.52    --  -88.50 -77.00  90.00  118
 31  \w   -160.00-101.00   0.50    1.52    --  -88.50 -77.00  60.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1513375000
_diffrn_orient_matrix_UB_12      -0.0430721000
_diffrn_orient_matrix_UB_13      0.0388238000
_diffrn_orient_matrix_UB_21      -0.0343531000
_diffrn_orient_matrix_UB_22      -0.1585794000
_diffrn_orient_matrix_UB_23      -0.0352750000
_diffrn_orient_matrix_UB_31      0.0303977000
_diffrn_orient_matrix_UB_32      0.0366671000
_diffrn_orient_matrix_UB_33      -0.1055404000
_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  0.0406
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14112
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.406
_diffrn_reflns_theta_min         3.382
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.63a (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    1.312
_exptl_crystal_description       plate
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.141
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         4208
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0475
_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^)+(0.0500P)^2^+0.9000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1168
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    0.838
_reflns_Friedel_fraction_max     0.792
_reflns_number_gt                3887
_reflns_number_total             4208
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc00158b2.cif
_cod_data_source_block           hpd119b
_cod_depositor_comments
'Adding full bibliography for 1560602--1560604.cif.'
_cod_database_code               1560602
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O F'
_chemical_oxdiff_usercomment     HF-0610
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7(3)
 0.3(3)
2. 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, All O(H) groups
3.a Ternary CH refined with riding coordinates:
 C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
3.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C28(H28), C5(H5), C27(H27), C15(H15), C19(H19), C8(H8), C25(H25),
 C7(H7), C24(H24), C17(H17), C16(H16), C18(H18)
3.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C29(H29A,H29B,H29C)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.654
_oxdiff_exptl_absorpt_empirical_full_min 0.732