Tandem Cyclization/Hydroarylation of α,ω-Dienes Triggered by Scandium-Catalyzed C–H Activation
Tang, Bin; Hu, Xiaoyan; Liu, Chunli; Jiang, Tao; Alam, Fakhre; Chen, Yanhui; ACS Catalysis 9 (2018) 599–; doi:10.1021/acscatal.8b04713

data_4515478
_publ_section_title
;
 Tandem Cyclization/Hydroarylation of \a,\w-Dienes Triggered by
 Scandium-Catalyzed C--H Activation
;
_journal_issue                   1
_journal_name_full               'ACS Catalysis'
_journal_page_first              599
_journal_paper_doi               10.1021/acscatal.8b04713
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H24 N, F6 P'
_chemical_formula_sum            'C15 H24 F6 N P'
_chemical_formula_weight         363.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-11-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
????
;
_cell_angle_alpha                90
_cell_angle_beta                 96.73(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.003(4)
_cell_length_b                   10.452(2)
_cell_length_c                   8.8763(18)
_cell_measurement_reflns_used    2481
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      27.8904
_cell_measurement_theta_min      2.2275
_cell_volume                     1750.9(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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      113.15
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2797
_diffrn_reflns_point_group_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        25.020
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_min         2.227
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.7471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear(Rigaku,2008)
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.840
_refine_diff_density_min         -0.916
_refine_diff_density_rms         0.116
_refine_ls_abs_structure_details
;
 Flack x determined using 674 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         2797
_refine_ls_number_restraints     278
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.1036
_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^)+(0.1904P)^2^+2.6997P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2987
_refine_ls_wR_factor_ref         0.3075
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_full    0.824
_reflns_Friedel_fraction_max     0.824
_reflns_number_gt                2414
_reflns_number_total             2797
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b04713_si_003.cif
_cod_data_source_block           shelxl_tw
_cod_original_cell_volume        1750.8(6)
_cod_database_code               4515478
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.959
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.595
 0.405
2. 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
3. Restrained distances
 C10'-C11' = C11'-C12' = C12'-C13' = C13'-C14' = C14'-C10' = C13'-C15'
 1.54 with sigma of 0.01
 C10-C11 = C11-C12 = C12-C13 = C13-C14 = C14-C10 = C13-C15
 1.54 with sigma of 0.01
 C6-C10 = C6-C10'
 1.54 with sigma of 0.01
 C6-C11 = C6-C14 = C6-C11' = C6-C14'
 2.58 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C10' \\sim C11' \\sim C12'
\\sim C13' \\sim C14' \\sim C15 \\sim C15': within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C10) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C10') \\sim Ueq, Uanis(C11') \\sim Ueq,
Uanis(C12') \\sim Ueq, Uanis(C13') \\sim Ueq, Uanis(C14') \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C15') \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
5. Others
 Fixed Sof: C10(0.5) H10(0.5) C11(0.5) H11A(0.5) H11B(0.5) C12(0.5) H12A(0.5)
 H12B(0.5) C13(0.5) H13(0.5) C14(0.5) H14A(0.5) H14B(0.5) C15(0.5) H15A(0.5)
 H15B(0.5) H15C(0.5) C10'(0.5) H10'(0.5) C11'(0.5) H11C(0.5) H11D(0.5)
 C12'(0.5) H12C(0.5) H12D(0.5) C13'(0.5) H13'(0.5) C14'(0.5) H14C(0.5)
 H14D(0.5) C15'(0.5) H15D(0.5) H15E(0.5) H15F(0.5)
6.a Ternary CH refined with riding coordinates:
 N1(H1), C10(H10), C13(H13), C10'(H10'), C13'(H13')
6.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B), C11'(H11C,H11D), C12'(H12C,
 H12D), C14'(H14C,H14D)
6.c Me refined with riding coordinates:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C15(H15A,H15B,H15C),
 C15'(H15D,H15E,H15F)
6.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7)
;
_shelx_res_checksum              97826
_shelx_hkl_checksum              21437
_olex2_submission_special_instructions 'No special instructions were received'