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

data_1554299
_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 N3 Ni O7, Cl O4, O'
_chemical_formula_sum            'C26 H39 Cl2 N3 Ni O12'
_chemical_formula_weight         715.21
_chemical_name_systematic        ZHY7163
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-31
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-06-01 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                   10.3907(9)
_cell_length_b                   11.9429(11)
_cell_length_c                   26.537(3)
_cell_measurement_reflns_used    2543
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3128
_cell_measurement_theta_min      2.8598
_cell_volume                     3293.1(6)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
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)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -38.00   42.00   0.5000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.3121   38.0000 -150.0000 160

  2 omega  -48.00   34.00   0.5000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.3121    0.0000 -180.0000 164
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0317832000
_diffrn_orient_matrix_UB_12      0.0139577000
_diffrn_orient_matrix_UB_13      0.0227903000
_diffrn_orient_matrix_UB_21      -0.0085822000
_diffrn_orient_matrix_UB_22      0.0577360000
_diffrn_orient_matrix_UB_23      -0.0053147000
_diffrn_orient_matrix_UB_31      -0.0597852000
_diffrn_orient_matrix_UB_32      -0.0008226000
_diffrn_orient_matrix_UB_33      0.0129103000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0799
_diffrn_reflns_av_unetI/netI     0.1212
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            12444
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.866
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.814
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95385
_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            yellow-green
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       plate
_exptl_crystal_F_000             1496
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ether'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 960 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         6003
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1280
_refine_ls_R_factor_gt           0.0735
_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^)+(0.0758P)^2^+0.9217P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.1907
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3722
_reflns_number_total             6003
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00279g2.cif
_cod_data_source_block           20170530_zhy7163
_cod_original_cell_volume        3293.1(5)
_cod_database_code               1554299
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C20 H20 N8 O20 Ni1'
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.867
_reflns_odcompleteness_completeness 99.50
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Rotating group:
 O6(H6A,H6B), O7(H7A,H7B)
2.b Ternary CH refined with riding coordinates:
 C14(H14), C17(H17), C22(H22)
2.c Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
2.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12)
2.e Idealised Me refined as rotating group:
 C7(H7C,H7D,H7E), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,
 H18C), C19(H19A,H19B,H19C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,
 H26B,H26C)
;
_shelx_res_checksum              74987
_shelx_hkl_checksum              2502
_olex2_submission_special_instructions 'No special instructions were received'