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_1555334
_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         'C34 H20 F4 N2 O4'
_chemical_formula_sum            'C34 H20 F4 N2 O4'
_chemical_formula_weight         596.52
_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     direct
_audit_creation_date             2015-06-18
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.347(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.755(5)
_cell_length_b                   9.629(3)
_cell_length_c                   15.724(6)
_cell_measurement_reflns_used    8990
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4785
_cell_measurement_theta_min      1.1623
_cell_volume                     2652.5(15)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.1021
	          2theta: -19.7903
scan:
	Number of images: 270
	           Slice: -76.2500 - 58.7500
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.1021
	          2theta: -19.7903
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0643
_diffrn_orient_matrix_UB_12      0.0037
_diffrn_orient_matrix_UB_13      0.0033
_diffrn_orient_matrix_UB_21      0.0080
_diffrn_orient_matrix_UB_22      -0.0741
_diffrn_orient_matrix_UB_23      -0.0723
_diffrn_orient_matrix_UB_31      0.0090
_diffrn_orient_matrix_UB_32      0.0398
_diffrn_orient_matrix_UB_33      -0.0399
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18412
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_min         2.325
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_description       rod
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         6036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0526
_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^)+(0.0412P)^2^+1.4348P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1180
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5351
_reflns_number_total             6036
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02487_si_005.cif
_cod_data_source_block           a
_cod_original_cell_volume        2652.7(14)
_cod_database_code               1555334
_diffrn_number_total             6403
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C14(H14), C21(H21), C24(H24), C25(H25), C26(H26)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C19(H19), C20(H20), C22(H22),
 C23(H23), C31(H31), C32(H32), C33(H33)
;
_shelx_res_checksum              14649
_shelx_hkl_checksum              82691
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'