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_1566411
_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         'C18 H21 N O2'
_chemical_formula_sum            'C18 H21 N O2'
_chemical_formula_weight         283.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-05 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                95.047(2)
_cell_angle_beta                 96.626(2)
_cell_angle_gamma                94.254(2)
_cell_formula_units_Z            2
_cell_length_a                   7.2466(2)
_cell_length_b                   8.3731(2)
_cell_length_c                   12.6472(3)
_cell_measurement_reflns_used    10273
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      74.0700
_cell_measurement_theta_min      3.5260
_cell_volume                     756.54(3)
_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      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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    -88.00 -33.00   1.00    1.00    --    0.00 -82.00-150.00   55
  2  \w    -35.00  -9.00   1.00    1.00    --    0.00 -38.00 120.00   26
  3  \w    -18.00  35.00   1.00    1.00    --    0.00  38.00  60.00   53
  4  \w    -19.00  30.00   1.00    1.00    --    0.00  38.00-150.00   49
  5  \w     64.00  89.00   1.00    1.00    --    0.00  38.00-150.00   25
  6  \w    -26.00  14.00   1.00    1.00    --    0.00 -82.00-150.00   40
  7  \w    -16.00  43.00   1.00    1.00    --    0.00  38.00 150.00   59
  8  \w    -74.00 -46.00   1.00    1.00    --    0.00 -38.00 120.00   28
  9  \w    -23.00  85.00   1.00    1.00    --    0.00  19.00 -60.00  108
 10  \w     44.00  69.00   1.00    1.00    --    0.00  38.00  60.00   25
 11  \w     75.00 117.00   1.00    1.00    --   95.80  45.00 -30.00   42
 12  \w     98.00 124.00   1.00    1.00    --   95.80  77.00 150.00   26
 13  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 14  \w    141.00 167.00   1.00    1.00    --   95.80  77.00  30.00   26
 15  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -60.00   25
 16  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 150.00   26
 17  \w    151.00 178.00   1.00    1.00    --   95.80  59.00  74.53   27
 18  \w     65.00 136.00   1.00    1.00    --   95.80  82.00-120.00   71
 19  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 120.00   25
 20  \w     72.00  98.00   1.00    1.00    --   95.80  61.00   0.00   26
 21  \w     65.00  91.00   1.00    1.00    --   95.80  82.00 150.00   26
 22  \w     76.00 101.00   1.00    1.00    --   95.80  45.00  30.00   25
 23  \w    123.00 185.00   1.00    1.00    --   95.80  45.00  30.00   62
 24  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  60.00   25
 25  \w    141.00 175.00   1.00    1.00    --   95.80  77.00  60.00   34
 26  \w     75.00 135.00   1.00    1.00    --   95.80  45.00   0.00   60
 27  \w    151.00 179.00   1.00    1.00    --   95.80  45.00   0.00   28
 28  \w      6.00 128.00   1.00    1.00    --   95.80 -82.00 -30.00  122
 29  \w     71.00 182.00   1.00    1.00    --   95.80  61.00 120.00  111
 30  \w     76.00 132.00   1.00    1.00    --   95.80  61.00  30.00   56
 31  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 32  \w     73.00 125.00   1.00    1.00    --   95.80 -82.00  66.66   52
 33  \w     88.00 125.00   1.00    1.00    --   95.80 -82.00-120.00   37
 34  \w     28.00  85.00   1.00    1.00    --   95.80 -82.00-120.00   57
 35  \w     66.00  92.00   1.00    1.00    --   95.80  82.00 120.00   26
 36  \w     76.00 131.00   1.00    1.00    --   95.80  61.00-180.00   55
 37  \w     72.00 136.00   1.00    1.00    --   95.80  61.00  90.00   64
 38  \w    122.00 185.00   1.00    1.00    --   95.80  77.00 -30.00   63
 39  \w     64.00 158.00   1.00    1.00    --   95.80  82.00-180.00   94
 40  \w      8.00 120.00   1.00    1.00    --   95.80 -61.00  30.00  112
 41  \w     63.00  89.00   1.00    1.00    --   95.80  82.00   0.00   26
 42  \w     63.00  96.00   1.00    1.00    --   95.80  82.00  30.00   33
 43  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-120.00   25
 44  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -30.00   25
 45  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  90.00   25
 46  \w     36.00  62.00   1.00    1.00    --   95.80 -82.00  66.66   26
 47  \w     71.00 122.00   1.00    1.00    --   95.80  59.00  74.53   51
 48  \w     75.00 101.00   1.00    1.00    --   95.80  61.00 -60.00   26
 49  \w    154.00 185.00   1.00    1.00    --   95.80  61.00 -60.00   31
 50  \w     67.00  93.00   1.00    1.00    --   95.80  77.00 -90.00   26
 51  \w    141.00 168.00   1.00    1.00    --   95.80  77.00 -90.00   27
 52  \w     77.00 160.00   1.00    1.00    --   95.80  30.00 -90.00   83
 53  \w     71.00  98.00   1.00    1.00    --   95.80  61.00-120.00   27
 54  \w     73.00  99.00   1.00    1.00    --   95.80  61.00 150.00   26
 55  \w     62.00 116.00   1.00    1.00    --   95.80 -61.00 -60.00   54
 56  \w     65.00 112.00   1.00    1.00    --   95.80  77.00-150.00   47
 57  \w     60.00 125.00   1.00    1.00    --   95.80 -82.00-180.00   65
 58  \w     71.00 180.00   1.00    1.00    --   95.80  58.00 -70.70  109
;
_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      0.0325604000
_diffrn_orient_matrix_UB_12      0.0376282000
_diffrn_orient_matrix_UB_13      0.1224832000
_diffrn_orient_matrix_UB_21      0.1076318000
_diffrn_orient_matrix_UB_22      0.1613977000
_diffrn_orient_matrix_UB_23      -0.0129325000
_diffrn_orient_matrix_UB_31      -0.1830173000
_diffrn_orient_matrix_UB_32      0.0830698000
_diffrn_orient_matrix_UB_33      -0.0035614000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14785
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.063
_diffrn_reflns_theta_max         67.063
_diffrn_reflns_theta_min         3.535
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.638
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88915
_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    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2694
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0406
_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^)+(0.0498P)^2^+0.2534P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1077
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2546
_reflns_number_total             2694
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00147k2.cif
_cod_data_source_block           exp_2169
_cod_database_code               1566411
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.56
_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), C10(H10), C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              30078
_shelx_hkl_checksum              19215
_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 1.863
_oxdiff_exptl_absorpt_empirical_full_min 0.628