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_1560603
_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_formula_moiety         'C15 H15 F O2'
_chemical_formula_sum            'C15 H15 F O2'
_chemical_formula_weight         246.27
_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             2020-08-20
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_audit_update_record
;
2020-08-20 deposited with the CCDC.	2021-02-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.972(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3867(2)
_cell_length_b                   19.0785(5)
_cell_length_c                   9.3357(2)
_cell_measurement_reflns_used    6160
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.7310
_cell_measurement_theta_min      2.4110
_cell_volume                     1220.09(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 n/a (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.951
_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    -78.00  26.00   0.50    0.11    --  -46.62  93.00-110.00  208
  2  \w    -13.00  78.00   0.50    0.11    --   46.62 -93.00 137.00  182
  3  \w    -80.00 -15.00   0.50    0.44    --  -88.50  93.00-110.00  130
  4  \w     34.00 105.00   0.50    0.44    --  106.69 -93.00 137.00  142
  5  \w    104.00 178.00   0.50    0.44    --  106.69  93.00-110.00  148
  6  \w   -119.00 -87.00   0.50    0.11    --  -46.62-125.00 -60.00   64
  7  \w   -119.00 -83.00   0.50    0.11    --  -46.62 -57.00-180.00   72
  8  \w   -119.00 -83.00   0.50    0.11    --  -46.62 -57.00-120.00   72
  9  \w   -119.00 -83.00   0.50    0.11    --  -46.62 -57.00 150.00   72
 10  \w   -119.00 -87.00   0.50    0.11    --  -46.62-125.00-150.00   64
 11  \w     83.00 120.00   0.50    0.11    --   46.62  57.00  30.00   74
 12  \w    -51.00 -16.00   0.50    0.44    --  -88.50  45.00-180.00   70
 13  \w    -71.00 -15.00   0.50    0.44    --  -88.50  61.00  30.00  112
 14  \w    -51.00 -16.00   0.50    0.44    --  -88.50  45.00-120.00   70
 15  \w    -51.00 -16.00   0.50    0.44    --  -88.50  45.00 -60.00   70
 16  \w   -160.00-101.00   0.50    0.44    --  -88.50 -77.00 -90.00  118
 17  \w    -51.00 -16.00   0.50    0.44    --  -88.50  45.00  90.00   70
 18  \w   -160.00 -83.00   0.50    0.44    --  -88.50 -93.00 137.00  154
 19  \w     34.00 101.00   0.50    0.44    --  106.69 -77.00-180.00  134
 20  \w     34.00  71.00   0.50    0.44    --  106.69 -61.00 -90.00   74
 21  \w     34.00  71.00   0.50    0.44    --  106.69 -61.00-180.00   74
 22  \w    101.00 178.00   0.50    0.44    --  106.69  77.00 -60.00  154
 23  \w     34.00  71.00   0.50    0.44    --  106.69 -61.00-150.00   74
 24  \w     34.00  71.00   0.50    0.44    --  106.69 -61.00 -30.00   74
 25  \w     34.00 105.00   0.50    0.44    --  106.69 -94.00  30.00  142
 26  \w   -120.00 -32.00   0.50    0.11    --  -46.62 -37.00 -90.00  176
 27  \w   -120.00 -32.00   0.50    0.11    --  -46.62 -37.00-180.00  176
 28  \w   -120.00 -32.00   0.50    0.11    --  -46.62 -37.00  90.00  176
 29  \w   -120.00 -32.00   0.50    0.11    --  -46.62 -37.00   0.00  176
 30  \w   -120.00 -52.00   0.50    0.11    --  -46.62 -37.00-150.00  136
 31  \w     83.00 120.00   0.50    0.11    --   46.62  57.00 -90.00   74
;
_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      0.0838337000
_diffrn_orient_matrix_UB_12      0.0726802000
_diffrn_orient_matrix_UB_13      -0.0122402000
_diffrn_orient_matrix_UB_21      -0.1863442000
_diffrn_orient_matrix_UB_22      0.0173456000
_diffrn_orient_matrix_UB_23      -0.1405486000
_diffrn_orient_matrix_UB_31      -0.0939081000
_diffrn_orient_matrix_UB_32      0.0305977000
_diffrn_orient_matrix_UB_33      0.1084869000
_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  0.0414
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13853
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.263
_diffrn_reflns_theta_min         4.635
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.600
_exptl_absorpt_correction_type   gaussian
_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    1.341
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0550P)^2^+0.3500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1096
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2122
_reflns_number_total             2429
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc00158b2.cif
_cod_data_source_block           hpd207
_cod_depositor_comments
'Adding full bibliography for 1560602--1560604.cif.'
_cod_database_code               1560603
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O F Si'
_chemical_oxdiff_usercomment     HF_08_17
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.872
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C3(H3), C8(H8), C15(H15)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              16168
_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 1.376
_oxdiff_exptl_absorpt_empirical_full_min 0.789