Enantioselective gold(i)-catalyzed rearrangement of cyclopropyl-substituted 1,6-enynes into 2-oxocyclobutyl-cyclopentanes
Wu, Zhiyong; Lebœuf, David; Retailleau, Pascal; Gandon, Vincent; Marinetti, Angela; Voituriez, Arnaud; Chem. Commun.  (2017) –; doi:10.1039/C7CC03234J

data_7120276
_publ_section_title
;
 Enantioselective gold(i)-catalyzed rearrangement of
 cyclopropyl-substituted 1,6-enynes into 2-oxocyclobutyl-cyclopentanes
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC03234J
_journal_year                    2017
_chemical_formula_moiety         'C20 H22 N4 O8'
_chemical_formula_sum            'C20 H22 N4 O8'
_chemical_formula_weight         446.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-12-01
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.24 svn.r3368 for OlexSys, GUI svn.r5267)
;
_audit_update_record
;
2016-12-01 deposited with the CCDC.
2017-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                105.992(7)
_cell_angle_beta                 97.837(7)
_cell_angle_gamma                111.220(8)
_cell_formula_units_Z            4
_cell_length_a                   10.5093(3)
_cell_length_b                   13.2957(4)
_cell_length_c                   17.9828(12)
_cell_measurement_reflns_used    11427
_cell_measurement_temperature    293
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      6.7
_cell_volume                     2172.2(3)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'RAPID2 curved IP'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details
;
scan:
    Number of images: 36
               Slice: 20.0000 - 200.0000
         Image width: 5.0000
            Exp time: 180.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 0.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 36
               Slice: 20.0000 - 200.0000
         Image width: 5.0000
            Exp time: 180.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 30.0000
                 Phi: 180.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 36
               Slice: 20.0000 - 200.0000
         Image width: 5.0000
            Exp time: 180.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 0.0000
                 Phi: 0.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 33
               Slice: 20.0000 - 185.0000
         Image width: 5.0000
            Exp time: 180.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 270.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 24
               Slice: 20.0000 - 140.0000
         Image width: 5.0000
            Exp time: 180.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 180.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 21
               Slice: 20.0000 - 125.0000
         Image width: 5.0000
            Exp time: 180.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 30.0000
                 Phi: 0.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 15
               Slice: 39.0000 - 114.0000
         Image width: 5.0000
            Exp time: 180.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 90.0000
                 XTD: 127.4000
              2theta: 0.0000
;
_diffrn_measurement_device
;
Crystal Goniometer
;
_diffrn_measurement_device_type
;
Rigaku RAXIS conversion
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       FS_PROCESS
_diffrn_orient_matrix_UB_11      -0.021463
_diffrn_orient_matrix_UB_12      -0.066395
_diffrn_orient_matrix_UB_13      -0.049920
_diffrn_orient_matrix_UB_21      -0.010189
_diffrn_orient_matrix_UB_22      -0.051874
_diffrn_orient_matrix_UB_23      0.031989
_diffrn_orient_matrix_UB_31      -0.103111
_diffrn_orient_matrix_UB_32      -0.018160
_diffrn_orient_matrix_UB_33      -0.008981
_diffrn_radiation_monochromator  'OSMIC Confocal CMF mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24719
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.205
_diffrn_reflns_theta_min         6.699
_diffrn_source                   'Rigaku mm007HF Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    0.909
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Higashi, Reqab, FS_PROCESS, 1998'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       stick
_exptl_crystal_F_000             936
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane/dichloromethane'
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     642
_refine_ls_number_reflns         7638
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0946
_refine_ls_R_factor_gt           0.0676
_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^)+(0.0815P)^2^+1.1867P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1812
_refine_ls_wR_factor_ref         0.2033
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5246
_reflns_number_total             7638
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc03234j2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        2172.2(2)
_cod_database_code               7120276
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H) groups
2. Shared sites
{N4B, N4B2}
3. Restrained distances
 N2B-H2B = N2A-H2A
 0.87 with sigma of 0.02
 O7B-N4B \\sim O7B2-N4B2 \\sim O8B-N4B \\sim O8B2-N4B2
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(N4B) = Uanis(N4B2)
5. Rigid body (RIGU) restrains
 O7B, N4B, O8B, O7B2, N4B2, O8B2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(O7B2)=Sof(N4B2)=Sof(O8B2)=Sof(H6BC)=Sof(H6BD)=Sof(H6AC)=Sof(H6AD)=
 Sof(C4B')=Sof(H4B')=Sof(C5B')=Sof(H5B')=Sof(C4A')=Sof(H4A')=Sof(C5A')=
 Sof(H5A')=Sof(H3BC)=Sof(H3BD)=Sof(H3AC)=Sof(H3AD)=1-FVAR(1)
 Sof(O7B)=Sof(N4B)=Sof(O8B)=Sof(H6BA)=Sof(H6BB)=Sof(H6AA)=Sof(H6AB)=Sof(C4B)=
 Sof(H4B)=Sof(C5B)=Sof(H5B)=Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(H5A)=Sof(H3BA)=
 Sof(H3BB)=Sof(H3AA)=Sof(H3AB)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C4B(H4B), C5B(H5B), C4B'(H4B'), C5B'(H5B'), C4A(H4A), C5A(H5A), C4A'(H4A'),
 C5A'(H5A')
7.b Secondary CH2 refined with riding coordinates:
 C8A(H8AA,H8AB), C8B(H8BA,H8BB), C6B(H6BA,H6BB), C6B(H6BC,H6BD), C6A(H6AA,
 H6AB), C6A(H6AC,H6AD), C3B(H3BA,H3BB), C3B(H3BC,H3BD), C3A(H3AA,H3AB),
 C3A(H3AC,H3AD), C2B(H2BA,H2BB), C2A(H2AA,H2AB)
7.c Aromatic/amide H refined with riding coordinates:
 C19A(H19A), C17B(H17B), C17A(H17A), C16B(H16B), C16A(H16A), C19B(H19B)
7.d X=CH2 refined with riding coordinates:
 C10B(H10A,H10B), C10A(H10C,H10D)
7.e Idealised Me refined as rotating group:
 C14B(H14A,H14B,H14C), C14A(H14D,H14E,H14F), C12B(H12A,H12B,H12C), C12A(H12D,
 H12E,H12F)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'