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_1560604
_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         'C28 H20 F N O4'
_chemical_formula_sum            'C28 H20 F N O4'
_chemical_formula_weight         453.45
_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             2020-08-10
_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                 99.0372(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.28538(14)
_cell_length_b                   20.3181(2)
_cell_length_c                   8.91344(10)
_cell_measurement_reflns_used    11498
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.0240
_cell_measurement_theta_min      3.6450
_cell_volume                     2197.31(4)
_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      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 0.970
_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     31.00 120.00   0.50    0.05    --   46.87  58.00 -18.00  178
  2  \w     90.00 178.00   0.50    0.14    --  106.69  58.00 -18.00  176
  3  \w    101.00 178.00   0.50    0.14    --  106.69  77.00  30.00  154
  4  \w     95.00 178.00   0.50    0.14    --  106.69 125.00 150.00  166
  5  \w     96.00 177.00   0.50    0.14    --  106.69  61.00  60.00  162
  6  \w     56.00  87.00   0.50    0.14    --  106.69 -77.00-180.00   62
  7  \w     34.00  67.00   0.50    0.14    --  106.69 -58.00-159.00   66
  8  \w     40.00  65.00   0.50    0.14    --  106.69 -61.00 -90.00   50
  9  \w     34.00  71.00   0.50    0.14    --  106.69 -61.00 -30.00   74
 10  \w     46.00  95.00   0.50    0.14    --  106.69 -94.00   0.00   98
 11  \w     43.00  71.00   0.50    0.14    --  106.69 -61.00  60.00   56
 12  \w     45.00  71.00   0.50    0.14    --  106.69 -61.00  90.00   52
 13  \w     34.00  71.00   0.50    0.14    --  106.69 -61.00  30.00   74
 14  \w     35.00  62.00   0.50    0.14    --  106.69 -61.00   0.00   54
 15  \w     34.00 105.00   0.50    0.14    --  106.69 -94.00 -60.00  142
 16  \w    -25.00  63.00   0.50    0.05    --   46.87 -58.00-159.00  176
 17  \w    -63.00  26.00   0.50    0.05    --  -46.87  58.00 -18.00  178
 18  \w    -51.00 -16.00   0.50    0.14    --  -88.50  45.00 150.00   70
 19  \w    -51.00 -16.00   0.50    0.14    --  -88.50  45.00 120.00   70
 20  \w    -67.00 -15.00   0.50    0.14    --  -88.50  58.00 -18.00  104
 21  \w    -51.00 -16.00   0.50    0.14    --  -88.50  45.00 -90.00   70
 22  \w    -51.00 -16.00   0.50    0.14    --  -88.50  45.00-180.00   70
 23  \w   -120.00 -30.00   0.50    0.05    --  -46.87 -58.00-159.00  180
 24  \w   -120.00 -87.00   0.50    0.05    --  -46.87-125.00  30.00   66
 25  \w   -120.00 -87.00   0.50    0.05    --  -46.87-125.00 -30.00   66
 26  \w   -160.00 -72.00   0.50    0.14    --  -88.50 -58.00-159.00  176
;
_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      0.1150120000
_diffrn_orient_matrix_UB_12      0.0009997000
_diffrn_orient_matrix_UB_13      -0.0483264000
_diffrn_orient_matrix_UB_21      0.0398951000
_diffrn_orient_matrix_UB_22      -0.0522985000
_diffrn_orient_matrix_UB_23      0.1215419000
_diffrn_orient_matrix_UB_31      -0.0360271000
_diffrn_orient_matrix_UB_32      -0.0548960000
_diffrn_orient_matrix_UB_33      -0.1162831000
_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  0.0402
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            21382
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.713
_diffrn_reflns_theta_min         3.643
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.804
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.437
_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    1.371
_exptl_crystal_description       plank
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.369
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0467P)^2^+0.6233P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0947
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4040
_reflns_number_total             4485
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc00158b2.cif
_cod_data_source_block           hpd195
_cod_depositor_comments
'Adding full bibliography for 1560602--1560604.cif.'
_cod_database_code               1560604
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N F'
_chemical_oxdiff_usercomment     hf-08-07
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.756
_reflns_odcompleteness_completeness 100.00
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C12(H12), C24(H24), C5(H5), C25(H25), C16(H16), C13(H13),
 C19(H19), C26(H26), C27(H27), C28(H28), C11(H11), C18(H18)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              8355
_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 1.242
_oxdiff_exptl_absorpt_empirical_full_min 0.852