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

data_1554301
_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         'C26 H39 Cl Fe N3 O7, Cl O4, H2 O'
_chemical_formula_sum            'C26 H41 Cl2 Fe N3 O12'
_chemical_formula_weight         714.37
_chemical_name_systematic        zhy8105
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc1pd9yb
_audit_creation_date             2017-07-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-07-08 deposited with the CCDC.
2018-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3081(3)
_cell_length_b                   11.9800(2)
_cell_length_c                   26.1548(5)
_cell_measurement_reflns_used    6800
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      67.9420
_cell_measurement_theta_min      3.3250
_cell_volume                     3229.88(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 Hypix-6000HE
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -83.00 -57.00   0.50    0.50    --  -47.40 -31.00  35.00   52
  2  \w      8.00  40.00   0.50    0.50    --  -47.40  31.00-164.00   64
  3  \w    -45.00 -20.00   0.50    0.50    --  -47.40  31.00-164.00   50
  4  \w    -81.00 -56.00   0.50    1.00    -- -105.60  31.00-164.00   50
  5  \w   -156.00-130.00   0.50    1.00    -- -105.60 -31.00  35.00   52
  6  \w    -49.00 -22.00   0.50    0.50    --    5.00 -31.00  35.00   54
  7  \w     43.00  94.00   0.50    0.50    --    5.00  57.00 -90.00  102
  8  \w    -77.00  41.00   0.50    0.50    --  -47.40  57.00 -90.00  236
  9  \w    -90.00 -65.00   0.50    1.00    -- -105.60  57.00-150.00   50
 10  \w    -53.00 -16.00   0.50    1.00    -- -105.60  57.00 -60.00   74
 11  \w   -137.00 -16.00   0.50    1.00    -- -105.60  57.00-180.00  242
 12  \w    -58.00 -17.00   0.50    1.00    -- -105.60  57.00-150.00   82
 13  \w   -126.00 -24.00   0.50    1.00    -- -105.60  75.00 -60.00  204
 14  \w   -132.00-107.00   0.50    1.00    -- -105.60  57.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0268020000
_diffrn_orient_matrix_UB_12      -0.0152240000
_diffrn_orient_matrix_UB_13      -0.0575447000
_diffrn_orient_matrix_UB_21      0.0538056000
_diffrn_orient_matrix_UB_22      -0.1197697000
_diffrn_orient_matrix_UB_23      0.0028021000
_diffrn_orient_matrix_UB_31      -0.1367500000
_diffrn_orient_matrix_UB_32      -0.0442218000
_diffrn_orient_matrix_UB_33      0.0124303000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13721
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.237
_diffrn_reflns_theta_min         3.380
_diffrn_source                   'Rotating Anode X-ray tube'
_diffrn_source_type              'MM007(Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.822
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_description       block
_exptl_crystal_F_000             1496
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: ether'
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.804
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 1928 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         5690
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0491
_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^)+(0.0701P)^2^+1.9500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1266
_refine_ls_wR_factor_ref         0.1292
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_full    0.917
_reflns_Friedel_fraction_max     0.912
_reflns_number_gt                5219
_reflns_number_total             5690
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00279g2.cif
_cod_data_source_block           zhy8105_2
_cod_database_code               1554301
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H O N Cl Fe'
_diffrn_oxdiff_ac3_digest_frames
;
01b68c997098c8854c18f6b160c8c7ca6001362646f
;
_diffrn_oxdiff_ac3_digest_hkl
;
01ab9cb492dede85f8022d28a2911ab2d19093
;
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H,H) groups
2.a Free rotating group:
 O12(H12A,H12B)
2.b Rotating group:
 O6(H6A,H6B), O7(H7A,H7B)
2.c Ternary CH refined with riding coordinates:
 C14(H14), C16(H16), C19(H19)
2.d Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.e Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11)
2.f Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,
 H26B,H26C)
;
_shelx_res_checksum              73279
_shelx_hkl_checksum              429
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.491
_oxdiff_exptl_absorpt_empirical_full_min 0.773