Enantioselective one-pot synthesis of 4H-chromene derivatives catalyzed by a chiral Ni(ii) complex
Yu, Xuan; Lan, Wenjie; Li, Jiaqi; Bai, Hui; Qin, Zhaohai; Fu, Bin; RSC Advances 10 (2020) 44437–44441; doi:10.1039/D0RA08906K

data_7241893
_publ_section_title
;
 Enantioselective one-pot synthesis of 4H-chromene derivatives catalyzed
 by a chiral Ni(ii) complex
;
_journal_issue                   72
_journal_name_full               'RSC Advances'
_journal_page_first              44437
_journal_page_last               44441
_journal_paper_doi               10.1039/D0RA08906K
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C22 H22 O6'
_chemical_formula_sum            'C22 H22 O6'
_chemical_formula_weight         382.39
_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
_audit_creation_date             2019-06-19
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2019-07-19 deposited with the CCDC.	2020-11-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.562(3)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   21.7453(6)
_cell_length_b                   10.7363(2)
_cell_length_c                   25.2540(7)
_cell_measurement_reflns_used    21322
_cell_measurement_temperature    110.1(3)
_cell_measurement_theta_max      71.1770
_cell_measurement_theta_min      3.1420
_cell_volume                     5651.3(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.1(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9883
_diffrn_measurement_details
;
  1 omega   28.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000   60.0000 76

  2 omega   60.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000  -30.0000 42

  3 omega   66.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000  -30.0000 43

  4 omega  112.00  170.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 58

  5 omega   46.00   72.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 26

  6 omega   44.00   97.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 53

  7 omega   45.00   91.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 46

  8 omega   43.00   91.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 48

  9 omega   43.00   90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 47

 10 omega   64.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 25

 11 omega   87.00  113.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -150.0000 26

 12 omega   59.00  105.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 46

 13 omega   57.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 32

 14 omega   46.00   81.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -150.0000 35

 15 omega   39.00   87.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 48

 16 omega   33.00   60.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000 -120.0000 27

 17 omega   16.00   42.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000  -30.0000 26

 18 omega  -30.00   16.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -57.0000  150.0000 46

 19 omega  -16.00   63.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000  120.0000 79

 20 omega    1.00   71.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -99.0000   30.0000 70

 21 omega   24.00   50.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   57.0000  -60.0000 26

 22 omega  -30.00   -5.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017  -57.0000 -150.0000 25

 23 omega   69.00   95.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   19.0000   30.0000 26

 24 omega   10.00   36.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   77.0000 -180.0000 26

 25 omega   45.00   85.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   19.0000  -60.0000 40

 26 omega   19.00   55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   57.0000    0.0000 36

 27 omega   10.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   77.0000  -90.0000 87

 28 omega   35.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   57.0000  -30.0000 34

 29 omega   27.00   79.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   77.0000 -150.0000 52

 30 omega   38.00   64.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   77.0000 -180.0000 26

 31 omega   76.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017  178.0000  -90.0000 31

 32 omega   12.00   37.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   77.0000 -120.0000 25

 33 omega   27.00   52.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   57.0000  -90.0000 25

 34 omega   10.00   39.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   19.0000   30.0000 29

 35 omega   29.00   55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   37.0000   30.0000 26

 36 omega   27.00   55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   37.0000  -90.0000 28

 37 omega   81.00  106.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 25

 38 omega   90.00  115.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 25

 39 omega  135.00  161.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 26

 40 omega  123.00  149.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 26

 41 omega   87.00  113.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 26

 42 omega   81.00  107.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 26

 43 omega   81.00  106.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 25

 44 omega   73.00  101.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -120.0000 28

 45 omega   81.00  106.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -78.4545 25

 46 omega   91.00  117.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 26

 47 omega   91.00  116.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 25

 48 omega   90.00  116.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 26

 49 omega   87.00  112.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -150.0000 25

 50 omega   87.00  112.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -60.0000 25

 51 omega   90.00  116.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 26

 52 omega   87.00  113.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -120.0000 26

 53 omega   81.00  106.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 25

 54 omega   88.00  114.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -90.0000 26

 55 omega   91.00  117.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 26

 56 omega   90.00  116.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -120.0000 26

 57 omega   91.00  116.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 25

 58 omega  125.00  166.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 41

 59 omega   70.00  101.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -90.0000 31

 60 omega   90.00  116.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 26

 61 omega   90.00  116.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 26

 62 omega   81.00  106.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 25

 63 omega   87.00  113.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -150.0000 26

 64 omega   86.00  112.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   68.0000  -59.2651 26

 65 omega   71.00  142.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -60.0000 71

 66 omega   73.00   99.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 26

 67 omega   72.00  108.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000    0.0000 36

 68 omega   87.00  113.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   32.0000  -77.1747 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0595928000
_diffrn_orient_matrix_UB_12      -0.0130474000
_diffrn_orient_matrix_UB_13      0.0210175000
_diffrn_orient_matrix_UB_21      0.0426386000
_diffrn_orient_matrix_UB_22      -0.0484819000
_diffrn_orient_matrix_UB_23      0.0557988000
_diffrn_orient_matrix_UB_31      0.0095579000
_diffrn_orient_matrix_UB_32      0.1345197000
_diffrn_orient_matrix_UB_33      0.0221508000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            62103
_diffrn_reflns_point_group_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.275
_diffrn_reflns_theta_min         3.663
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.810
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             2424
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 7082 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1537
_refine_ls_number_reflns         19967
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0615
_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^)+(0.0898P)^2^+4.2700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1652
_refine_ls_wR_factor_ref         0.1688
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_full    0.850
_reflns_Friedel_fraction_max     0.823
_reflns_number_gt                18684
_reflns_number_total             19967
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra08906k2.cif
_cod_data_source_block           exp_6007
_cod_database_code               7241893
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.765
_shelx_res_checksum              62582
_shelx_shelxl_version_number     2014/7