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_4133191
_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         '0.2(C11 H14 O4)'
_chemical_formula_sum            'C2.2 H2.8 O0.8'
_chemical_formula_weight         42.04
_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     dual
_audit_creation_date             2018-05-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_cell_angle_alpha                96.927(4)
_cell_angle_beta                 104.549(4)
_cell_angle_gamma                116.762(3)
_cell_formula_units_Z            30
_cell_length_a                   10.7657(7)
_cell_length_b                   11.8832(9)
_cell_length_c                   14.3028(10)
_cell_measurement_reflns_used    3503
_cell_measurement_temperature    150(2)
_cell_volume                     1522.5(2)
_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      150.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0324
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19303
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         2.248
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6903
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     412
_refine_ls_number_reflns         5959
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1555
_refine_ls_R_factor_gt           0.0745
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0320P)^2^+4.1110P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1727
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2283
_reflns_number_total             5959
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b08781_si_005.cif
_cod_data_source_block           mo_hu109_0m
_cod_original_cell_volume        1522.46(19)
_cod_original_formula_sum        'C2.20 H2.80 O0.80'
_cod_database_code               4133191
_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. Uiso/Uaniso restraints and constraints
Uanis(C017) \\sim Ueq: with sigma of 0.0001 and sigma for terminal atoms of
0.0002
3.a Ternary CH refined with riding coordinates:
 C00F(H00F), C00H(H00U), C00J(H00J), C00M(H00M), C00O(H00O), C00Y(H00Y)
3.b Secondary CH2 refined with riding coordinates:
 C00L(H00I,H00K), C00N(H00A,H00B), C00S(H00L,H00N), C00T(H00V,H00W), C00X(H00G,
 H00H), C00Z(H00S,H00T), C010(H01A,H01B), C018(H01O,H01P), C019(H01Q,H01R)
3.c Idealised Me refined as rotating group:
 C00U(H00P,H00Q,H00R), C00W(H00C,H00D,H00E), C012(H01C,H01D,H01E), C014(H01I,
 H01J,H01K), C015(H01L,H01M,H01N), C016(H01F,H01G,H01H)
;
_olex2_submission_special_instructions 'No special instructions were received'