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_4133194
_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         '0.13(C18 H20 O6.01)'
_chemical_formula_sum            'C2.25 H2.5 O0.75'
_chemical_formula_weight         41.55
_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                77.958(4)
_cell_angle_beta                 87.753(4)
_cell_angle_gamma                61.189(4)
_cell_formula_units_Z            2
_cell_length_a                   8.1399(7)
_cell_length_b                   8.1896(6)
_cell_length_c                   14.1026(11)
_cell_measurement_reflns_used    2383
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.576
_cell_measurement_theta_min      2.864
_cell_volume                     803.55(12)
_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 1.000
_diffrn_measured_fraction_theta_max 0.997
_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  0.0787
_diffrn_reflns_av_unetI/netI     0.0666
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13371
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.413
_diffrn_reflns_theta_min         2.863
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6810
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3289
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.0596
_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^)+(0.0570P)^2^+0.7390P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1524
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2019
_reflns_number_total             3289
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b08781_si_004.cif
_cod_data_source_block           mo_hu106a_0m
_cod_original_cell_volume        803.55(11)
_cod_original_formula_sum        'C2.25 H2.50 O0.75'
_cod_database_code               4133194
_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. Shared sites
{C6, O1A}
{C6A, O1}
3. Uiso/Uaniso restraints and constraints
Uanis(O2A) \\sim Ueq: with sigma of 0.0001 and sigma for terminal atoms of
0.0002
4. Others
 Sof(H5B)=Sof(H10A)=Sof(O2A)=Sof(O1A)=Sof(C6A)=1-FVAR(1)
 Sof(O1)=Sof(C6)=Sof(H5A)=Sof(H10)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C5(H5A), C5(H5B), C10(H10), C10(H10A)
5.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C2(H2A,H2B), C9(H9A,H9B), C8(H8A,H8B)
5.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C13(H13), C15(H15), C12(H12)
5.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'