Enantioselective Dearomative Mizoroki–Heck Reaction of Naphthalenes
Han, Xiao-Qing; Wang, Lei; Yang, Ping; Liu, Jing-Yuan; Xu, Wei-Yan; Zheng, Chao; Liang, Ren-Xiao; You, Shu-Li; Zhang, Junliang; Jia, Yi-Xia; ACS Catalysis  (2021) 655–661; doi:10.1021/acscatal.1c05008

data_4519242
_publ_section_title
;
 Enantioselective Dearomative Mizoroki--Heck Reaction of Naphthalenes
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              655
_journal_page_last               661
_journal_paper_doi               10.1021/acscatal.1c05008
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H19 N O'
_chemical_formula_sum            'C19 H19 N O'
_chemical_formula_weight         277.35
_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             2020-10-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.807(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8561(10)
_cell_length_b                   10.1465(8)
_cell_length_c                   12.2213(11)
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      68.33
_cell_measurement_theta_min      3.62
_cell_volume                     1469.5(2)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_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_temperature      170.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21445
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.458
_diffrn_reflns_theta_min         3.618
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1069 before and 0.0345 after correction.
The Ratio of minimum to maximum transmission is 0.8971.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 2467 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         5358
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0283
_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^)+(0.0456P)^2^+0.1900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0722
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                5338
_reflns_number_total             5358
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c05008_si_004.cif
_cod_data_source_block           cu_201028_hxq_t1_0m
_cod_database_code               4519242
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.870
_shelx_estimated_absorpt_t_min   0.770
_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:
 C11(H11), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C28(H28A,H28B), C29(H29A,H29B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C14(H14), C15(H15), C16(H16), C17(H17),
 C20(H20), C21(H21), C22(H22), C23(H23), C33(H33), C34(H34), C35(H35), C36(H36)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C37(H37A,H37B,H37C), C38(H38A,H38B,
 H38C)
;
_shelx_res_checksum              27060
_shelx_hkl_checksum              64316
_olex2_submission_special_instructions 'No special instructions were received'