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_1566408
_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         'C15 H16 O2'
_chemical_formula_sum            'C15 H16 O2'
_chemical_formula_weight         228.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-23 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.0970(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.78830(10)
_cell_length_b                   12.6773(2)
_cell_length_c                   10.4803(2)
_cell_measurement_reflns_used    9578
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1910
_cell_measurement_theta_min      6.1580
_cell_volume                     1152.94(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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_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    -17.00  10.00   1.00    1.00    --    0.00 -57.00-120.00   27
  2  \w     55.00  89.00   1.00    1.00    --    0.00  38.00-150.00   34
  3  \w    -82.00 -56.00   1.00    1.00    --    0.00 -82.00-150.00   26
  4  \w     27.00  88.00   1.00    1.00    --    0.00  77.00-120.00   61
  5  \w    -17.00  21.00   1.00    1.00    --    0.00  38.00-150.00   38
  6  \w    -23.00  14.00   1.00    1.00    --    0.00  77.00-120.00   37
  7  \w     24.00  50.00   1.00    1.00    --    0.00  38.00-150.00   26
  8  \w    -28.00  19.00   1.00    1.00    --    0.00 -82.00-150.00   47
  9  \w    -86.00 -34.00   1.00    1.00    --    0.00 -57.00-120.00   52
 10  \w    -23.00  10.00   1.00    1.00    --    0.00  57.00 150.00   33
 11  \w    -19.00  31.00   1.00    1.00    --    0.00  38.00   0.00   50
 12  \w     56.00  81.00   1.00    1.00    --    0.00  38.00   0.00   25
 13  \w    -16.00  26.00   1.00    1.00    --    0.00  38.00  60.00   42
 14  \w     63.00  89.00   1.00    1.00    --   95.80  82.00-150.00   26
 15  \w    123.00 170.00   1.00    1.00    --   95.80  61.00 120.00   47
 16  \w      6.00  65.00   1.00    1.00    --   95.80 -82.00 150.00   59
 17  \w     72.00  97.00   1.00    1.00    --   95.80  61.00 120.00   25
 18  \w    144.00 170.00   1.00    1.00    --   95.80  45.00  30.00   26
 19  \w    127.00 175.00   1.00    1.00    --   95.80  82.00 150.00   48
 20  \w     75.00 175.00   1.00    1.00    --   95.80  57.00  46.73  100
 21  \w     65.00  95.00   1.00    1.00    --   95.80  77.00 -90.00   30
 22  \w     78.00 107.00   1.00    1.00    --   95.80  45.00 120.00   29
 23  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-120.00   25
 24  \w    138.00 185.00   1.00    1.00    --   95.80  77.00-120.00   47
 25  \w     63.00  95.00   1.00    1.00    --   95.80  82.00 -30.00   32
 26  \w    124.00 185.00   1.00    1.00    --   95.80  82.00 -30.00   61
 27  \w     45.00 123.00   1.00    1.00    --   95.80 -82.00 -90.00   78
 28  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -60.00   26
 29  \w     66.00 104.00   1.00    1.00    --   95.80  77.00 120.00   38
 30  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-150.00   25
 31  \w     76.00 131.00   1.00    1.00    --   95.80  45.00  30.00   55
 32  \w     66.00  92.00   1.00    1.00    --   95.80  77.00  60.00   26
 33  \w     74.00 100.00   1.00    1.00    --   95.80  61.00-180.00   26
 34  \w     76.00 112.00   1.00    1.00    --   95.80  45.00 -90.00   36
 35  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 150.00   26
 36  \w     67.00  93.00   1.00    1.00    --   95.80  77.00  30.00   26
 37  \w     73.00 150.00   1.00    1.00    --   95.80  61.00 -90.00   77
 38  \w     63.00  97.00   1.00    1.00    --   95.80  82.00-180.00   34
 39  \w     75.00 110.00   1.00    1.00    --   95.80  45.00 -30.00   35
 40  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  90.00   25
 41  \w     30.00 114.00   1.00    1.00    --   95.80 -77.00-150.00   84
 42  \w     75.00 160.00   1.00    1.00    --   95.80  45.00-120.00   85
 43  \w    125.00 185.00   1.00    1.00    --   95.80  82.00  60.00   60
 44  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  60.00   25
 45  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -60.00   26
 46  \w     76.00 102.00   1.00    1.00    --   95.80  61.00  90.00   26
 47  \w    125.00 181.00   1.00    1.00    --   95.80  61.00  90.00   56
 48  \w     70.00 102.00   1.00    1.00    --   95.80 -82.00 150.00   32
 49  \w     10.00 122.00   1.00    1.00    --   95.80 -82.00   0.00  112
 50  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 150.00   25
 51  \w     75.00 111.00   1.00    1.00    --   95.80  45.00-180.00   36
 52  \w     82.00 142.00   1.00    1.00    --   95.80  45.00-150.00   60
 53  \w    148.00 185.00   1.00    1.00    --   95.80  45.00-150.00   37
 54  \w     75.00 100.00   1.00    1.00    --   95.80  45.00  90.00   25
 55  \w     74.00 100.00   1.00    1.00    --   95.80  61.00  30.00   26
 56  \w     65.00  91.00   1.00    1.00    --   95.80  77.00   0.00   26
 57  \w    123.00 149.00   1.00    1.00    --   95.80  73.00 -36.75   26
 58  \w    123.00 185.00   1.00    1.00    --   95.80  82.00 -60.00   62
 59  \w     23.00  75.00   1.00    1.00    --   95.80 -82.00  60.00   52
 60  \w     95.00 120.00   1.00    1.00    --   95.80 -82.00  60.00   25
 61  \w     67.00 117.00   1.00    1.00    --   95.80  73.00 -36.75   50
;
_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      0.0486944000
_diffrn_orient_matrix_UB_12      -0.1168264000
_diffrn_orient_matrix_UB_13      0.0074676000
_diffrn_orient_matrix_UB_21      -0.1594243000
_diffrn_orient_matrix_UB_22      -0.0313668000
_diffrn_orient_matrix_UB_23      -0.0733697000
_diffrn_orient_matrix_UB_31      0.0609041000
_diffrn_orient_matrix_UB_32      0.0110309000
_diffrn_orient_matrix_UB_33      -0.1294466000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10931
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.443
_diffrn_reflns_theta_min         6.180
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32967
_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    1.315
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1006 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(12)
_refine_ls_extinction_coef       0.0041(5)
_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   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2186
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0314
_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^)+(0.0546P)^2^+0.3822P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0845
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_full    0.887
_reflns_Friedel_fraction_max     0.866
_reflns_number_gt                2184
_reflns_number_total             2186
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00147k2.cif
_cod_data_source_block           exp_847
_cod_database_code               1566408
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.82
_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), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C9(H9A,H9B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C5(H5), C3(H3), C2(H2), C4(H4)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              45456
_shelx_hkl_checksum              98823
_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 2.248
_oxdiff_exptl_absorpt_empirical_full_min 0.445