Me2(CH2=CH)SiCN: a bifunctional ethylene equivalent for Diels-Alder reaction based controllable tandem synthesis
Wu, Wen-Biao; Mu, Bo-Shuai; Yu, Jin-Sheng; Zhou, Jian; Chemical Science  (2022) –; doi:10.1039/D2SC00147K

data_1566412
_publ_section_title
;
 Me2(CH2=CH)SiCN: a bifunctional ethylene equivalent for Diels-Alder
 reaction based controllable tandem synthesis
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00147K
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H32 O2'
_chemical_formula_sum            'C25 H32 O2'
_chemical_formula_weight         364.50
_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             2019-07-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-09 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.530(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.1960(5)
_cell_length_b                   6.2725(2)
_cell_length_c                   13.2067(7)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1720
_cell_measurement_theta_min      4.5940
_cell_volume                     1001.59(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.969
_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     94.00 125.00   1.00    1.00    --   95.80   4.00   5.00   31
  2  \w    156.00 182.00   1.00    1.00    --   95.80   4.00   5.00   26
  3  \w      7.00  32.00   1.00    1.00    --   95.80  -4.00-171.00   25
  4  \w     29.00  55.00   1.00    1.00    --   95.80   4.00   5.00   26
  5  \w     19.00  60.00   1.00    1.00    --    0.00  57.00  30.00   41
  6  \w    -23.00  15.00   1.00    1.00    --    0.00  57.00  30.00   38
  7  \w    -11.00  28.00   1.00    1.00    --    0.00   4.00   5.00   39
  8  \w    -77.00 -32.00   1.00    1.00    --    0.00  -4.00-171.00   45
  9  \w     21.00  70.00   1.00    1.00    --    0.00  38.00-120.00   49
 10  \w      5.00  84.00   1.00    1.00    --    0.00  57.00 120.00   79
 11  \w     35.00  75.00   1.00    1.00    --    0.00  57.00 150.00   40
 12  \w    -23.00  89.00   1.00    1.00    --    0.00  57.00-120.00  112
 13  \w      2.00  29.00   1.00    1.00    --    0.00  77.00 -90.00   27
 14  \w    -16.00  13.00   1.00    1.00    --    0.00  -4.00-171.00   29
 15  \w     37.00  87.00   1.00    1.00    --    0.00  77.00 -90.00   50
 16  \w     54.00  88.00   1.00    1.00    --    0.00  38.00  90.00   34
 17  \w    -83.00 -56.00   1.00    1.00    --    0.00   4.00   5.00   27
 18  \w    -19.00  41.00   1.00    1.00    --    0.00  38.00  90.00   60
 19  \w     66.00 104.00   1.00    1.00    --   95.80  82.00  30.00   38
 20  \w    145.00 171.00   1.00    1.00    --   95.80  73.00-155.52   26
 21  \w      7.00  38.00   1.00    1.00    --   95.80 -82.00  60.00   31
 22  \w     67.00  93.00   1.00    1.00    --   95.80  73.00-155.52   26
 23  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 24  \w     72.00 184.00   1.00    1.00    --   95.80  61.00 150.00  112
 25  \w    110.00 182.00   1.00    1.00    --   95.80  77.00  60.00   72
 26  \w    126.00 152.00   1.00    1.00    --   95.80  77.00-180.00   26
 27  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 28  \w      6.00 125.00   1.00    1.00    --   95.80 -77.00   0.00  119
 29  \w      6.00 126.00   1.00    1.00    --   95.80 -77.00-180.00  120
 30  \w     75.00 159.00   1.00    1.00    --   95.80  45.00 -90.00   84
 31  \w     71.00 102.00   1.00    1.00    --   95.80  61.00  90.00   31
 32  \w    147.00 178.00   1.00    1.00    --   95.80  61.00  90.00   31
 33  \w     65.00  93.00   1.00    1.00    --   95.80  77.00 120.00   28
 34  \w     71.00  97.00   1.00    1.00    --   95.80  61.00 -90.00   26
 35  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  60.00   26
 36  \w    110.00 153.00   1.00    1.00    --   95.80  77.00   0.00   43
 37  \w     38.00  71.00   1.00    1.00    --   95.80 -82.00 -30.00   33
 38  \w     65.00 104.00   1.00    1.00    --   95.80  77.00   0.00   39
 39  \w     64.00  89.00   1.00    1.00    --   95.80  82.00 120.00   25
 40  \w    139.00 183.00   1.00    1.00    --   95.80  77.00-120.00   44
 41  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-120.00   26
 42  \w     65.00 100.00   1.00    1.00    --   95.80  82.00  90.00   35
 43  \w      8.00 114.00   1.00    1.00    --   95.80 -82.00 150.00  106
 44  \w     76.00 114.00   1.00    1.00    --   95.80 -82.00 -30.00   38
 45  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  90.00   26
 46  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -90.00   26
 47  \w    154.00 181.00   1.00    1.00    --   95.80  82.00 -90.00   27
 48  \w     75.00 116.00   1.00    1.00    --   95.80  45.00   0.00   41
 49  \w     75.00 158.00   1.00    1.00    --   95.80  45.00  90.00   83
 50  \w     72.00 165.00   1.00    1.00    --   95.80  61.00-150.00   93
 51  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 150.00   26
 52  \w     51.00 121.00   1.00    1.00    --   95.80 -82.00-120.00   70
 53  \w     63.00  89.00   1.00    1.00    --   95.80  82.00   0.00   26
 54  \w    150.00 175.00   1.00    1.00    --   95.80  82.00   0.00   25
 55  \w     65.00  92.00   1.00    1.00    --   95.80  77.00-150.00   27
 56  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -30.00   26
 57  \w     65.00  97.00   1.00    1.00    --   95.80  77.00 -60.00   32
 58  \w     76.00 103.00   1.00    1.00    --   95.80  45.00  60.00   27
 59  \w    119.00 153.00   1.00    1.00    --   95.80  45.00  60.00   34
 60  \w     78.00 109.00   1.00    1.00    --   95.80  61.00-180.00   31
 61  \w     74.00 184.00   1.00    1.00    --   95.80  61.00   0.00  110
 62  \w     65.00 101.00   1.00    1.00    --   95.80  82.00-150.00   36
 63  \w     64.00  89.00   1.00    1.00    --   95.80  82.00 -60.00   25
 64  \w     74.00 146.00   1.00    1.00    --   95.80  50.00 -57.10   72
 65  \w     67.00  93.00   1.00    1.00    --   95.80  71.00 153.66   26
 66  \w     71.00  96.00   1.00    1.00    --   95.80  63.00 -12.30   25
 67  \w    146.00 171.00   1.00    1.00    --   95.80  82.00  30.00   25
 68  \w     49.00 110.00   1.00    1.00    --   95.80 -82.00  60.00   61
 69  \w    160.00 185.00   1.00    1.00    --   95.80  -4.00-171.00   25
 70  \w     83.00 118.00   1.00    1.00    --   95.80  -4.00-171.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0070652000
_diffrn_orient_matrix_UB_12      0.2451783000
_diffrn_orient_matrix_UB_13      0.0010518000
_diffrn_orient_matrix_UB_21      0.1249777000
_diffrn_orient_matrix_UB_22      0.0139515000
_diffrn_orient_matrix_UB_23      -0.0067954000
_diffrn_orient_matrix_UB_31      -0.0241168000
_diffrn_orient_matrix_UB_32      0.0010427000
_diffrn_orient_matrix_UB_33      -0.1174306000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21715
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.386
_diffrn_reflns_theta_min         4.642
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.574
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details
;
 Flack x determined using 1494 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3981
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0858
_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^)+(0.1657P)^2^+0.9415P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2572
_refine_ls_wR_factor_ref         0.2587
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                3786
_reflns_number_total             3981
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00147k2.cif
_cod_data_source_block           exp_947
_cod_database_code               1566412
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.34
_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:
 C1(H1), C6(H6), C10(H10), C19(H19), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C8(H8A,H8B), C9(H9A,H9B), C17(H17A,H17B), C18(H18A,
 H18B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C12(H12), C13(H13), C15(H15)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              97896
_shelx_hkl_checksum              79503
_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 3.013
_oxdiff_exptl_absorpt_empirical_full_min 0.413