Synthesis of tri-substituted allyl alcohols via a copper/iron co-catalyzed cascade perfluoroalkylation/rearrangement of aryl propynyl ethers
He, Wei; Yu, Jipan; Wang, Dawei; Ran, Guoxia; Xia, Xiao-Feng; Organic Chemistry Frontiers 6 (2019) 3575–; doi:10.1039/C9QO00848A

data_1555085
_publ_section_title
;
 Synthesis of tri-substituted allyl alcohols via a copper/iron
 co-catalyzed cascade perfluoroalkylation/rearrangement of aryl propynyl
 ethers
;
_journal_issue                   20
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3575
_journal_paper_doi               10.1039/C9QO00848A
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C19 H12 Cl F9 O'
_chemical_formula_sum            'C19 H12 Cl F9 O'
_chemical_formula_weight         462.74
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-03-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-06 deposited with the CCDC.	2019-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.543(5)
_cell_length_b                   10.400(2)
_cell_length_c                   32.618(6)
_cell_measurement_reflns_used    8162
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      68.37
_cell_measurement_theta_min      5.05
_cell_volume                     3916(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      300.09
_diffrn_measured_fraction_theta_full 0.997
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            18092
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.285
_diffrn_reflns_theta_min         4.251
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.603
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1269 before and 0.0577 after correction.
The Ratio of minimum to maximum transmission is 0.7606.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_description       block
_exptl_crystal_F_000             1848
_refine_diff_density_max         0.789
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 2092 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.052(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         6902
_refine_ls_number_restraints     475
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0712
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1560P)^2^+0.9071P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2132
_refine_ls_wR_factor_ref         0.2395
_reflns_Friedel_coverage         0.889
_reflns_Friedel_fraction_full    0.925
_reflns_Friedel_fraction_max     0.922
_reflns_number_gt                5377
_reflns_number_total             6902
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00848a2.cif
_cod_data_source_block           2019032701_0m_a
_cod_depositor_comments
;

2025-06-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         82.08
_cod_original_formula_moiety      '0.09(C19 H9 Cl F9 O), 0.09(C19 H11 Cl F9 O)'
_cod_original_formula_units_Z            45
_cod_original_cell_volume        3915.8(19)
_cod_original_formula_sum        'C3.38 H1.96 Cl0.18 F1.60 N0 O0.18'
_cod_database_code               1555085
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
3.b Aromatic/amide H refined with riding coordinates:
 C4AA(H4AA), C19(H19), C15(H15), C16(H16), C1(H1), C00S(H00S), C4(H4), C2(H2),
 C3(H3), C6AA(H6AA), C00Z(H00Z), C14(H14), C17(H17), C18(H18), C5(H5), C20(H20),
  C5AA(H5AA), C01F(H01F)
;
_shelx_res_checksum              3749
_shelx_hkl_checksum              1960
_olex2_submission_special_instructions 'No special instructions were received'