Nickel-catalyzed enantioselective sequential Nazarov cyclization/decarboxylation
Zhang, Heyi; Lu, Zhan; Organic Chemistry Frontiers 5 (2018) 1763–; doi:10.1039/C8QO00279G

data_1554300
_publ_section_title
;
 Nickel-catalyzed enantioselective sequential Nazarov
 cyclization/decarboxylation
;
_journal_issue                   11
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1763
_journal_paper_doi               10.1039/C8QO00279G
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C22 H18 O'
_chemical_formula_sum            'C22 H18 O'
_chemical_formula_weight         298.36
_chemical_name_systematic        ZHY8126
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-07-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-07-19 deposited with the CCDC.
2018-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.2266(16)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.96436(13)
_cell_length_b                   7.91974(13)
_cell_length_c                   15.2392(3)
_cell_measurement_reflns_used    9206
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.7881
_cell_measurement_theta_min      5.5815
_cell_volume                     839.90(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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;
  1 omega  -96.00  -18.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega   15.00  112.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega   27.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6938   38.0000   90.0000 79

  4 omega   19.00   73.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  120.0000 54

  5 omega  122.00  163.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000   60.0000 41

  6 omega   73.00  103.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  -60.0000 30

  7 omega   73.00  119.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000   60.0000 46

  8 omega   11.00  121.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -85.0000  116.0000 110

  9 omega   93.00  163.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000  120.0000 70

 10 omega   75.00  107.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000   60.0000 32

 11 omega  140.00  165.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000   60.0000 25

 12 omega   61.00   99.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -60.0000 38

 13 omega   74.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  -90.0000 35

 14 omega  113.00  167.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  -90.0000 54

 15 omega  122.00  167.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  -60.0000 45

 16 omega   51.00   77.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  -90.0000 26

 17 omega   19.00   76.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000    0.0000 57

 18 omega   71.00  165.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000    0.0000 94

 19 omega   13.00  116.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6938   52.0000  134.0000 103

 20 omega    8.00  120.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6938   77.0000  -90.0000 112

 21 omega    8.00  120.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6938   77.0000 -180.0000 112

 22 omega  -32.00   70.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6938  -52.0000   45.0000 102

 23 omega -159.00  -51.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -69.0000  -28.0000 108

 24 omega -162.00  -49.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -90.0000 113

 25 omega -162.00  -49.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   30.0000 113

 26 omega -121.00  -18.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  125.0000  -90.0000 103

 27 omega -162.00  -49.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   90.0000 113

 28 omega   60.00  172.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -150.0000 112

 29 omega    8.00  131.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -88.0000   -9.0000 123

 30 omega   60.00  172.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  120.0000 112

 31 omega   19.00   77.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000 -150.0000 58

 32 omega    8.00  132.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -91.0000 -133.0000 124

 33 omega   66.00  168.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000 -180.0000 102

 34 omega   60.00  132.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -180.0000 72
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
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_diffrn_orient_matrix_UB_12      0.0581705000
_diffrn_orient_matrix_UB_13      0.0962470000
_diffrn_orient_matrix_UB_21      0.1770549000
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_diffrn_orient_matrix_UB_31      0.1326544000
_diffrn_orient_matrix_UB_32      0.1498600000
_diffrn_orient_matrix_UB_33      -0.0196285000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
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_diffrn_reflns_point_group_measured_fraction_full 0.984
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_diffrn_reflns_theta_full        66.899
_diffrn_reflns_theta_max         66.899
_diffrn_reflns_theta_min         5.811
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.546
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: ether'
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.097
_refine_diff_density_min         -0.183
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_refine_ls_abs_structure_details
;
 Flack x determined using 1243 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2962
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0738P)^2^+0.0319P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1077
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                2829
_reflns_number_total             2962
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00279g2.cif
_cod_data_source_block           170718_zhy8126
_cod_database_code               1554300
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c h o'
_shelx_estimated_absorpt_t_max   0.828
_shelx_estimated_absorpt_t_min   0.776
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_shelx_res_checksum              70567
_shelx_hkl_checksum              54391
_olex2_submission_special_instructions 'No special instructions were received'