Lewis Acid Catalyzed Formal Intramolecular [3 + 3] Cross-Cycloaddition of Cyclopropane 1,1-Diesters for Construction of Benzobicyclo[2.2.2]octane Skeletons.
Ma, Weiwei; Fang, Jie; Ren, Jun; Wang, Zhongwen; Organic letters 17 (2015) 4180–4183; doi:10.1021/acs.orglett.5b01927

data_1555163
_publ_section_title
;
 Lewis Acid Catalyzed Formal Intramolecular [3 + 3] Cross-Cycloaddition of
 Cyclopropane 1,1-Diesters for Construction of Benzobicyclo[2.2.2]octane
 Skeletons.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4180
_journal_page_last               4183
_journal_paper_doi               10.1021/acs.orglett.5b01927
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C16.5 H16 Cl1.5 N2 O3'
_chemical_formula_sum            'C16.5 H16 Cl1.5 N2 O3'
_chemical_formula_weight         343.49
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-08-13
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.99(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.298(3)
_cell_length_b                   11.852(2)
_cell_length_c                   9.939(2)
_cell_measurement_reflns_used    3299
_cell_measurement_temperature    293.1500
_cell_measurement_theta_max      25.0122
_cell_measurement_theta_min      2.1247
_cell_volume                     1919.6(6)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_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
;
????
;
_diffrn_ambient_temperature      293.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device
;
Saturn70 (4x4 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0195
_diffrn_orient_matrix_UB_12      0.0987
_diffrn_orient_matrix_UB_13      0.0024
_diffrn_orient_matrix_UB_21      0.0798
_diffrn_orient_matrix_UB_22      0.0163
_diffrn_orient_matrix_UB_23      -0.0219
_diffrn_orient_matrix_UB_31      -0.0161
_diffrn_orient_matrix_UB_32      -0.0007
_diffrn_orient_matrix_UB_33      -0.0592
_diffrn_radiation_detector       CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1005
_diffrn_reflns_av_unetI/netI     0.0846
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14543
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.25
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           16.0000
_diffrn_source_power             0.8000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5137
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             714
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.839
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       0.093(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3377
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.1439
_refine_ls_R_factor_gt           0.1147
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3265
_refine_ls_wR_factor_ref         0.3439
_reflns_number_gt                1822
_reflns_number_total             3377
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b01927_si_004.cif
_cod_data_source_block           r131106b1
_cod_original_cell_volume        1919.7(7)
_cod_database_code               1555163
_diffrn_number_total             3591
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2
 0.9 with sigma of 0.01
 C17-Cl1 = C17-Cl2 = C17-Cl3 = C17-Cl1' = C17-Cl2' = C17-Cl3'
 1.78 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C17) \\sim Ueq, Uanis(Cl1) \\sim Ueq, Uanis(Cl2) \\sim Ueq, Uanis(Cl3)
\\sim Ueq, Uanis(Cl1') \\sim Ueq, Uanis(Cl2') \\sim Ueq, Uanis(Cl3') \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: Cl1(0.25) Cl2(0.25) Cl3(0.25) Cl1'(0.25) Cl2'(0.25) Cl3'(0.25)
 C17(0.5)
5.a Ternary CH refined with riding coordinates:
 C2(H2A), C4(H4), C11(H11)
5.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C13(H13A,H13B)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C8(H8), C9(H9)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;