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_1555332
_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         'C24 H15 F2 N O2'
_chemical_formula_sum            'C24 H15 F2 N O2'
_chemical_formula_weight         387.37
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-05-18
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                84.646(13)
_cell_angle_beta                 78.696(12)
_cell_angle_gamma                74.768(10)
_cell_formula_units_Z            2
_cell_length_a                   8.126(3)
_cell_length_b                   9.511(3)
_cell_length_c                   12.210(4)
_cell_measurement_reflns_used    3117
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4629
_cell_measurement_theta_min      2.2215
_cell_volume                     892.0(5)
_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 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 7.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 40.1088
	          2theta: -20.1904
scan:
	Number of images: 346
	           Slice: -110.0000 - 63.0000
	     Image width: 0.5000
	        Exp time: 7.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 40.1088
	          2theta: -20.1904
scan:
	Number of images: 272
	           Slice: -81.0000 - 55.0000
	     Image width: 0.5000
	        Exp time: 7.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 40.1088
	          2theta: -20.1904
scan:
	Number of images: 200
	           Slice: -65.0000 - 35.0000
	     Image width: 0.5000
	        Exp time: 7.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 40.1088
	          2theta: -20.1904
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0468
_diffrn_orient_matrix_UB_12      0.0663
_diffrn_orient_matrix_UB_13      -0.1011
_diffrn_orient_matrix_UB_21      0.0819
_diffrn_orient_matrix_UB_22      0.0615
_diffrn_orient_matrix_UB_23      0.0374
_diffrn_orient_matrix_UB_31      0.0522
_diffrn_orient_matrix_UB_32      -0.0522
_diffrn_orient_matrix_UB_33      -0.0393
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12088
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.465
_diffrn_reflns_theta_min         2.640
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0566P)^2^+0.3449P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1251
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3870
_reflns_number_total             4047
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02487_si_003.cif
_cod_data_source_block           sa4117
_cod_database_code               1555332
_shelxl_version_number           2013-4
_diffrn_number_total             4049
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C15(H15), C16(H16), C21(H21),
 C22(H22), C23(H23)
;
_shelx_res_checksum              11867
_shelx_hkl_checksum              11602
_olex2_submission_special_instructions 'No special instructions were received'