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_1566410
_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_formula_moiety         'C16 H18 O'
_chemical_formula_sum            'C16 H18 O'
_chemical_formula_weight         226.30
_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             2019-06-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-10 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.1790(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.27630(10)
_cell_length_b                   13.18790(10)
_cell_length_c                   12.60950(10)
_cell_measurement_reflns_used    17005
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.0780
_cell_measurement_theta_min      4.8500
_cell_volume                     1206.78(2)
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.989
_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     44.00  70.00   1.00    1.00    --    0.00  57.00  90.00   26
  2  \w    -17.00  62.00   1.00    1.00    --    0.00  38.00  60.00   79
  3  \w     64.00  89.00   1.00    1.00    --    0.00  57.00-180.00   25
  4  \w    -18.00  89.00   1.00    1.00    --    0.00  38.00 -90.00  107
  5  \w    -19.00  32.00   1.00    1.00    --    0.00  38.00 -30.00   51
  6  \w    -89.00 -37.00   1.00    1.00    --    0.00 -57.00 150.00   52
  7  \w     57.00  82.00   1.00    1.00    --    0.00  77.00  90.00   25
  8  \w      8.00  47.00   1.00    1.00    --    0.00  77.00  90.00   39
  9  \w     10.00  37.00   1.00    1.00    --    0.00  57.00  90.00   27
 10  \w    -29.00  23.00   1.00    1.00    --    0.00 -57.00 150.00   52
 11  \w    -23.00  24.00   1.00    1.00    --    0.00  57.00-180.00   47
 12  \w     29.00  57.00   1.00    1.00    --    0.00  57.00-180.00   28
 13  \w     41.00  83.00   1.00    1.00    --    0.00  38.00 -30.00   42
 14  \w     49.00 118.00   1.00    1.00    --   95.80 -82.00  60.00   69
 15  \w     71.00 181.00   1.00    1.00    --   95.80  61.00   0.00  110
 16  \w     71.00 164.00   1.00    1.00    --   95.80  61.00  30.00   93
 17  \w    116.00 184.00   1.00    1.00    --   95.80  45.00 120.00   68
 18  \w     75.00 112.00   1.00    1.00    --   95.80  45.00 120.00   37
 19  \w     63.00 185.00   1.00    1.00    --   95.80  82.00-150.00  122
 20  \w     68.00 148.00   1.00    1.00    --   95.80  68.00  63.11   80
 21  \w     75.00 103.00   1.00    1.00    --   95.80  45.00   0.00   28
 22  \w     71.00 156.00   1.00    1.00    --   95.80  61.00 -90.00   85
 23  \w    108.00 134.00   1.00    1.00    --   95.80  45.00   0.00   26
 24  \w     65.00  92.00   1.00    1.00    --   95.80  77.00 150.00   27
 25  \w     65.00 100.00   1.00    1.00    --   95.80  77.00 -90.00   35
 26  \w    143.00 174.00   1.00    1.00    --   95.80  45.00-150.00   31
 27  \w     60.00  86.00   1.00    1.00    --   95.80 -77.00-150.00   26
 28  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 120.00   25
 29  \w     99.00 125.00   1.00    1.00    --   95.80  82.00  30.00   26
 30  \w     65.00  90.00   1.00    1.00    --   95.80  77.00   0.00   25
 31  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  30.00   26
 32  \w      7.00  46.00   1.00    1.00    --   95.80 -77.00-150.00   39
 33  \w     63.00  98.00   1.00    1.00    --   95.80  82.00 -60.00   35
 34  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -30.00   26
 35  \w    118.00 177.00   1.00    1.00    --   95.80  82.00-180.00   59
 36  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-180.00   25
 37  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-180.00   25
 38  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  30.00   25
 39  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  60.00   25
 40  \w     97.00 122.00   1.00    1.00    --   95.80  82.00  60.00   25
 41  \w    122.00 147.00   1.00    1.00    --   95.80  77.00-120.00   25
 42  \w     64.00  91.00   1.00    1.00    --   95.80  82.00  90.00   27
 43  \w     75.00 160.00   1.00    1.00    --   95.80  45.00-180.00   85
 44  \w     11.00 107.00   1.00    1.00    --   95.80 -61.00 -90.00   96
 45  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-150.00   26
 46  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  90.00   25
 47  \w     57.00 123.00   1.00    1.00    --   95.80 -77.00  90.00   66
 48  \w     74.00 101.00   1.00    1.00    --   95.80  61.00-150.00   27
 49  \w     75.00 158.00   1.00    1.00    --   95.80  45.00 150.00   83
 50  \w      9.00 128.00   1.00    1.00    --   95.80 -82.00 -90.00  119
 51  \w      6.00 115.00   1.00    1.00    --   95.80 -82.00 150.00  109
 52  \w     75.00 100.00   1.00    1.00    --   95.80  45.00-150.00   25
 53  \w     65.00  97.00   1.00    1.00    --   95.80  77.00-120.00   32
 54  \w     64.00  90.00   1.00    1.00    --   95.80  82.00 150.00   26
 55  \w     67.00 179.00   1.00    1.00    --   95.80  72.00 -65.32  112
 56  \w    148.00 185.00   1.00    1.00    --   95.80  53.00 153.40   37
 57  \w     93.00 119.00   1.00    1.00    --   95.80 -82.00 -30.00   26
 58  \w     73.00  99.00   1.00    1.00    --   95.80  53.00 153.40   26
;
_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      0.0557865000
_diffrn_orient_matrix_UB_12      0.1124506000
_diffrn_orient_matrix_UB_13      -0.0045678000
_diffrn_orient_matrix_UB_21      0.1257746000
_diffrn_orient_matrix_UB_22      -0.0134281000
_diffrn_orient_matrix_UB_23      0.1026535000
_diffrn_orient_matrix_UB_31      0.1618132000
_diffrn_orient_matrix_UB_32      -0.0284542000
_diffrn_orient_matrix_UB_33      -0.0666460000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25070
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.434
_diffrn_reflns_theta_min         4.859
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27564
_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    1.246
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2436
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0514P)^2^+0.6685P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1109
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2371
_reflns_number_total             2436
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00147k2.cif
_cod_data_source_block           exp_879
_cod_database_code               1566410
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.883
_shelx_estimated_absorpt_t_min   0.836
_reflns_odcompleteness_completeness 99.91
_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:
 C9(H9), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              65756
_shelx_hkl_checksum              30473
_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 2.707
_oxdiff_exptl_absorpt_empirical_full_min 0.396