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_1566413
_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 unk
_chemical_formula_moiety         'C20 H17 N O'
_chemical_formula_sum            'C20 H17 N O'
_chemical_formula_weight         287.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-01-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-05-13 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.55952(19)
_cell_length_b                   7.19955(14)
_cell_length_c                   33.3740(6)
_cell_measurement_reflns_used    10042
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5650
_cell_measurement_theta_min      5.2840
_cell_volume                     1576.11(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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    -30.00  45.00   1.00    1.00    --    0.00  82.00 120.00   75
  2  \w    -88.00  -2.00   1.00    1.00    --    0.00 -57.00 120.00   86
  3  \w     -3.00  34.00   1.00    1.00    --    0.00  19.00  90.00   37
  4  \w     48.00  84.00   1.00    1.00    --    0.00  82.00 120.00   36
  5  \w    -48.00  23.00   1.00    1.00    --    0.00 -57.00   0.00   71
  6  \w     29.00  89.00   1.00    1.00    --    0.00  19.00-180.00   60
  7  \w    -19.00  20.00   1.00    1.00    --    0.00  19.00-180.00   39
  8  \w    -21.00  86.00   1.00    1.00    --    0.00  19.00 -60.00  107
  9  \w     -5.00  22.00   1.00    1.00    --    0.00  57.00 120.00   27
 10  \w     72.00 141.00   1.00    1.00    --   95.80  56.00-155.65   69
 11  \w     94.00 183.00   1.00    1.00    --   95.80  79.00-105.36   89
 12  \w     64.00  91.00   1.00    1.00    --   95.80  79.00-105.36   27
 13  \w     63.00 107.00   1.00    1.00    --   95.80  81.00  99.10   44
 14  \w    138.00 179.00   1.00    1.00    --   95.80  81.00  99.10   41
 15  \w    136.00 185.00   1.00    1.00    --   95.80  63.00 -54.19   49
 16  \w     74.00  99.00   1.00    1.00    --   95.80  54.00  -9.01   25
 17  \w    148.00 174.00   1.00    1.00    --   95.80  78.00 140.50   26
 18  \w    120.00 185.00   1.00    1.00    --   95.80  75.00-156.18   65
 19  \w     66.00  92.00   1.00    1.00    --   95.80  75.00-156.18   26
 20  \w     97.00 124.00   1.00    1.00    --   95.80  78.00 140.50   27
 21  \w     66.00  91.00   1.00    1.00    --   95.80  74.00 172.50   25
 22  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 23  \w     65.00  92.00   1.00    1.00    --   95.80  77.00 -30.00   27
 24  \w     76.00 102.00   1.00    1.00    --   95.80  45.00 -90.00   26
 25  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-120.00   26
 26  \w      7.00 128.00   1.00    1.00    --   95.80 -82.00-150.00  121
 27  \w     99.00 182.00   1.00    1.00    --   95.80  82.00 -90.00   83
 28  \w     71.00 108.00   1.00    1.00    --   95.80  61.00   0.00   37
 29  \w     34.00  59.00   1.00    1.00    --   95.80 -82.00 120.00   25
 30  \w     71.00 103.00   1.00    1.00    --   95.80 -82.00 120.00   32
 31  \w     70.00 104.00   1.00    1.00    --   95.80  63.00 -54.19   34
 32  \w    145.00 171.00   1.00    1.00    --   95.80  77.00  55.21   26
 33  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 34  \w    117.00 142.00   1.00    1.00    --   95.80  82.00-150.00   25
 35  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  55.21   26
 36  \w     65.00  95.00   1.00    1.00    --   95.80  78.00 140.50   30
 37  \w    145.00 171.00   1.00    1.00    --   95.80  77.00  30.00   26
 38  \w     63.00  90.00   1.00    1.00    --   95.80  82.00-150.00   27
 39  \w    159.00 185.00   1.00    1.00    --   95.80  77.00 120.00   26
 40  \w     63.00  89.00   1.00    1.00    --   95.80  82.00   0.00   26
 41  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 42  \w     59.00 127.00   1.00    1.00    --   95.80 -82.00 -60.00   68
 43  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 150.00   26
 44  \w    111.00 184.00   1.00    1.00    --   95.80  82.00 150.00   73
 45  \w    113.00 139.00   1.00    1.00    --   95.80  56.00  24.21   26
 46  \w     75.00 100.00   1.00    1.00    --   95.80  61.00  60.00   25
 47  \w     94.00 138.00   1.00    1.00    --   95.80  77.00 120.00   44
 48  \w     64.00  89.00   1.00    1.00    --   95.80  82.00 120.00   25
 49  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 120.00   26
 50  \w     72.00 105.00   1.00    1.00    --   95.80  56.00  24.21   33
 51  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -60.00   26
 52  \w     75.00 156.00   1.00    1.00    --   95.80  45.00-180.00   81
 53  \w     66.00 115.00   1.00    1.00    --   95.80  77.00-150.00   49
 54  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -90.00   26
 55  \w    158.00 185.00   1.00    1.00    --   95.80  56.00-155.65   27
 56  \w     76.00 171.00   1.00    1.00    --   95.80  45.00 120.00   95
 57  \w    124.00 150.00   1.00    1.00    --   95.80  54.00  -9.01   26
 58  \w    148.00 178.00   1.00    1.00    --   95.80  49.00  56.36   30
 59  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  90.00   26
 60  \w     63.00 173.00   1.00    1.00    --   95.80  82.00  60.00  110
 61  \w     71.00 149.00   1.00    1.00    --   95.80  61.00 -30.00   78
 62  \w     14.00 113.00   1.00    1.00    --   95.80 -61.00-150.00   99
 63  \w     16.00 123.00   1.00    1.00    --   95.80 -82.00  60.00  107
 64  \w     74.00 142.00   1.00    1.00    --   95.80  49.00  56.36   68
;
_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      0.0018928000
_diffrn_orient_matrix_UB_12      0.0496753000
_diffrn_orient_matrix_UB_13      0.0448899000
_diffrn_orient_matrix_UB_21      -0.0104720000
_diffrn_orient_matrix_UB_22      0.2079197000
_diffrn_orient_matrix_UB_23      -0.0107231000
_diffrn_orient_matrix_UB_31      -0.2346435000
_diffrn_orient_matrix_UB_32      -0.0088519000
_diffrn_orient_matrix_UB_33      0.0008494000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            32998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         6.697
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
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    1.211
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 985 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2806
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0558P)^2^+0.2626P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1052
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2596
_reflns_number_total             2806
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00147k2.cif
_cod_data_source_block           exp_1154
_cod_database_code               1566413
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.869
_shelx_estimated_absorpt_t_min   0.845
_reflns_odcompleteness_completeness 99.77
_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
2. Others
 Fixed Sof: C01(0.5) C02(0.5) N01(0.5) N02(0.5)
3.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b), C12(H12a,H12b)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
;
_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 1.651
_oxdiff_exptl_absorpt_empirical_full_min 0.554