Cerium-Catalyzed Formal Cycloaddition of Cycloalkanols with Alkenes through Dual Photoexcitation.
Hu, Anhua; Chen, Yilin; Guo, Jing-Jing; Yu, Na; An, Qing; Zuo, Zhiwei; Journal of the American Chemical Society 140 (2018) 13580–13585; doi:10.1021/jacs.8b08781

data_4133192
_publ_section_title
;
 Cerium-Catalyzed Formal Cycloaddition of Cycloalkanols with Alkenes
 through Dual Photoexcitation.
;
_journal_issue                   42
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13580
_journal_page_last               13585
_journal_paper_doi               10.1021/jacs.8b08781
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C17 H17 F O6'
_chemical_formula_sum            'C17 H17 F O6'
_chemical_formula_weight         336.30
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_cell_angle_alpha                98.618(8)
_cell_angle_beta                 93.721(7)
_cell_angle_gamma                96.898(7)
_cell_formula_units_Z            2
_cell_length_a                   8.5820(10)
_cell_length_b                   9.1420(12)
_cell_length_c                   10.6911(14)
_cell_measurement_reflns_used    1661
_cell_measurement_temperature    166(2)
_cell_measurement_theta_max      21.79
_cell_measurement_theta_min      2.40
_cell_volume                     820.37(18)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      166.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1263
_diffrn_reflns_av_unetI/netI     0.0980
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14666
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         2.273
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6568
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3233
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1591
_refine_ls_R_factor_gt           0.0648
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.1320P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1390
_refine_ls_wR_factor_ref         0.1780
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1565
_reflns_number_total             3233
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b08781_si_007.cif
_cod_data_source_block           mo_0928_6_0m
_cod_database_code               4133192
_shelx_shelxl_version_number     2014/7
_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. Restrained distances
 C2-C1A
 1.5 with sigma of 0.02
 C2-C1
 1.5 with sigma of 0.02
 H2-C2
 1 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C1A: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
C1A \\sim C1: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
4. Others
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=1-FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C00B(H00B), C00D(H00D)
5.b Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00C)
5.c Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00I(H00I), C00M(H00M)
5.d Idealised Me refined as rotating group:
 C00J(H00E,H00F,H00G), C00L(H00J,H00K,H00L), C1A(H1AA,H1AB,H1AC), C1(H1A,H1B,
 H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'