Lewis Acid Assisted Diels-Alder Reaction with Regio- and Stereoselectivity: Anti-1,4-Adducts with Rigid Scaffolds and Their Application in Explosives Sensing.
Chen, Qi; Chen, Hao; Meng, Xiao; Ma, Yuguo; Organic letters 17 (2015) 5016–5019; doi:10.1021/acs.orglett.5b02487

data_1555333
_publ_section_title
;
 Lewis Acid Assisted Diels-Alder Reaction with Regio- and
 Stereoselectivity: Anti-1,4-Adducts with Rigid Scaffolds and Their
 Application in Explosives Sensing.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5016
_journal_page_last               5019
_journal_paper_doi               10.1021/acs.orglett.5b02487
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C44 H36 F4 N2 O4 Si2'
_chemical_formula_sum            'C44 H36 F4 N2 O4 Si2'
_chemical_formula_weight         788.93
_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     iterative
_audit_creation_date             2015-06-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_cell_angle_alpha                90
_cell_angle_beta                 94.257(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.2172(5)
_cell_length_b                   11.8634(10)
_cell_length_c                   29.226(2)
_cell_measurement_reflns_used    1809
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      24.5510
_cell_measurement_theta_min      3.4670
_cell_volume                     2149.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega   36.00  100.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  178.0000  -30.0000 64

  2 omega  -89.00   20.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  -77.0000   90.0000 109
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0039765000
_diffrn_orient_matrix_UB_12      -0.0583554000
_diffrn_orient_matrix_UB_13      0.0052509000
_diffrn_orient_matrix_UB_21      0.0790748000
_diffrn_orient_matrix_UB_22      0.0106452000
_diffrn_orient_matrix_UB_23      0.0182589000
_diffrn_orient_matrix_UB_31      -0.0826523000
_diffrn_orient_matrix_UB_32      0.0074150000
_diffrn_orient_matrix_UB_33      0.0151991000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0747
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            8495
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_min         3.281
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description
;
;
_exptl_crystal_F_000             820
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_platon_squeeze_details
;
;
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1105
_refine_ls_R_factor_gt           0.0625
_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^)+(0.0688P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1376
_refine_ls_wR_factor_ref         0.1568
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2576
_reflns_number_total             4212
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02487_si_004.cif
_cod_data_source_block           exp_5433-sr
_cod_database_code               1555333
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C30 H27 O4 N1 Si2 F4 N2'
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.986
_reflns_odcompleteness_completeness 99.15
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C11(H11), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'