Pd-Catalyzed intermolecular asymmetric allylic dearomatization of 1-nitro-2-naphthols with MBH adducts.
Zhang, Qing-Xia; Xie, Jia-Hao; Gu, Qing; You, Shu-Li; Chemical communications (Cambridge, England) 59 (2023) 3590–3593; doi:10.1039/d3cc00568b

data_7131356
_publ_section_title
;
 Pd-Catalyzed intermolecular asymmetric allylic dearomatization of
 1-nitro-2-naphthols with MBH adducts.
;
_journal_issue                   24
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3590
_journal_page_last               3593
_journal_paper_doi               10.1039/d3cc00568b
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C22 H19 N O5'
_chemical_formula_sum            'C22 H19 N O5'
_chemical_formula_weight         377.38
_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     dual
_audit_creation_date             2022-08-15
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-01-04 deposited with the CCDC.	2023-03-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.3800(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.01130(10)
_cell_length_b                   13.9038(2)
_cell_length_c                   8.5163(2)
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    213
_cell_measurement_theta_max      54.931
_cell_measurement_theta_min      4.519
_cell_volume                     948.59(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      213
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20296
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.939
_diffrn_reflns_theta_min         4.517
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.494
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1264 before and 0.0547 after correction.
The Ratio of minimum to maximum transmission is 0.7971.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.109
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
;
 Flack x determined using 1537 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3537
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0297
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0391P)^2^+0.1112P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0753
_reflns_Friedel_coverage         0.910
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                3419
_reflns_number_total             3537
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00568b2.cif
_cod_data_source_block           mj22278_0m
_cod_depositor_comments          'Adding full bibliography for 7131356.cif.'
_cod_database_code               7131356
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.966
_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 Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C17(H17), C18(H18), C19(H19),
 C20(H20)
2.c X=CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              51265
_shelx_hkl_checksum              16570
_olex2_submission_special_instructions 'No special instructions were received'