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_1566409
_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         'C17 H18 Br N O'
_chemical_formula_sum            'C17 H18 Br N O'
_chemical_formula_weight         332.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-06-11 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.0900(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.7377(2)
_cell_length_b                   9.57380(10)
_cell_length_c                   7.61300(10)
_cell_measurement_reflns_used    10676
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      74.0590
_cell_measurement_theta_min      4.5170
_cell_volume                     1420.52(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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.981
_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    -18.00  19.00   1.00    1.00    --    0.00 -38.00  90.00   37
  2  \w    -10.00  24.00   1.00    1.00    --    0.00 -77.00-180.00   34
  3  \w    -89.00 -32.00   1.00    1.00    --    0.00 -19.00 -30.00   57
  4  \w    -88.00 -40.00   1.00    1.00    --    0.00 -38.00  90.00   48
  5  \w    -10.00  24.00   1.00    1.00    --    0.00 -19.00 -30.00   34
  6  \w    -65.00 -40.00   1.00    1.00    --    0.00 -77.00-180.00   25
  7  \w      6.00 118.00   1.00    1.00    --   95.80 -61.00 -60.00  112
  8  \w    103.00 128.00   1.00    1.00    --   95.80 -82.00 150.00   25
  9  \w     69.00 127.00   1.00    1.00    --   95.80  15.00  60.00   58
 10  \w     77.00 126.00   1.00    1.00    --   95.80 -82.00-120.00   49
 11  \w      7.00 101.00   1.00    1.00    --   95.80 -15.00 120.00   94
 12  \w     11.00  72.00   1.00    1.00    --   95.80 -82.00-120.00   61
 13  \w     50.00  89.00   1.00    1.00    --   95.80 -82.00 150.00   39
 14  \w     26.00  60.00   1.00    1.00    --   95.80 -82.00 -60.00   34
 15  \w     80.00 156.00   1.00    1.00    --   95.80  30.00 150.00   76
 16  \w     11.00 124.00   1.00    1.00    --   95.80 -82.00  60.00  113
 17  \w      7.00 108.00   1.00    1.00    --   95.80 -61.00  60.00  101
 18  \w     73.00 119.00   1.00    1.00    --   95.80 -82.00 -60.00   46
 19  \w    110.00 183.00   1.00    1.00    --   95.80  30.00 120.00   73
 20  \w     55.00 127.00   1.00    1.00    --   95.80 -82.00-180.00   72
 21  \w     93.00 118.00   1.00    1.00    --   95.80  45.00  30.00   25
 22  \w    147.00 184.00   1.00    1.00    --   95.80  45.00  30.00   37
 23  \w     73.00  98.00   1.00    1.00    --   95.80 -82.00 -30.00   25
 24  \w    151.00 185.00   1.00    1.00    --   95.80  15.00  60.00   34
;
_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      0.0400562000
_diffrn_orient_matrix_UB_12      -0.1373319000
_diffrn_orient_matrix_UB_13      -0.0083648000
_diffrn_orient_matrix_UB_21      0.0679647000
_diffrn_orient_matrix_UB_22      0.0787265000
_diffrn_orient_matrix_UB_23      0.0572695000
_diffrn_orient_matrix_UB_31      -0.0050742000
_diffrn_orient_matrix_UB_32      -0.0287272000
_diffrn_orient_matrix_UB_33      0.1966081000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            13942
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.623
_diffrn_reflns_theta_min         4.537
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.891
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24049
_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    1.553
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.00160(16)
_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   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0386P)^2^+0.9612P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0740
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2770
_reflns_number_total             2860
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00147k2.cif
_cod_data_source_block           exp_2044
_cod_database_code               1566409
_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:
 C9(H9), C10(H10), C11(H11), 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), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              76706
_shelx_hkl_checksum              54737
_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 5.594
_oxdiff_exptl_absorpt_empirical_full_min 0.331