Regio- and diastereoselective dearomatizations of N-alkyl activated azaarenes: the maximization of the reactive sites
Miao, Hong-Jie; Wang, Le-Le; Han, Hua-Bin; Zhao, Yong-De; Wang, Qi-Lin; Bu, Zhan-Wei; Chemical Science 11 (2020) 1418–1424; doi:10.1039/C9SC04880D

data_1556631
_publ_section_title
;
 Regio- and diastereoselective dearomatizations of N-alkyl activated
 azaarenes: the maximization of the reactive sites
;
_journal_issue                   5
_journal_name_full               'Chemical Science'
_journal_page_first              1418
_journal_page_last               1424
_journal_paper_doi               10.1039/C9SC04880D
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C29 H27 Cl N2 O'
_chemical_formula_sum            'C29 H27 Cl N2 O'
_chemical_formula_weight         454.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-17 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.0100(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8554(2)
_cell_length_b                   18.2505(2)
_cell_length_c                   12.2873(2)
_cell_measurement_reflns_used    6504
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8490
_cell_measurement_theta_min      4.4320
_cell_volume                     2351.26(6)
_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    '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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -68.00  -42.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -120.0000 52

  2 omega -108.00  -75.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -120.0000 66

  3 omega  -77.00  -51.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   60.0000 52

  4 omega -100.00  -66.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000  -60.0000 68

  5 omega   50.00   77.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   30.0000 54

  6 omega   58.00   83.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 50

  7 omega  -33.00   57.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000 -150.0000 180

  8 omega  -33.00    3.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000  150.0000 72

  9 omega   19.00   55.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -120.0000 72

 10 omega  -33.00   55.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -180.0000 176

 11 omega    8.00   37.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -150.0000 58

 12 omega   -3.00   25.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   30.0000 56

 13 omega  -31.00   26.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000   60.0000 114

 14 omega   58.00  108.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 100

 15 omega   76.00  102.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -90.0000 52

 16 omega   59.00  101.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -150.0000 84

 17 omega   40.00   65.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000   60.0000 50

 18 omega   23.00   68.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   30.0000 90

 19 omega   -1.00   52.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000 -180.0000 106

 20 omega   38.00   85.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 94

 21 omega   40.00   67.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 54

 22 omega   65.00   99.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 68

 23 omega   70.00  109.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 78

 24 omega  107.00  144.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  120.0000 74

 25 omega   61.00   97.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  120.0000 72

 26 omega   45.00  153.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000    0.0000 216

 27 omega   55.00  111.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 112

 28 omega   49.00   95.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 92

 29 omega   49.00  115.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 132

 30 omega   44.00  131.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -30.0000 174

 31 omega   41.00  124.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   60.0000 166

 32 omega   96.00  137.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 82

 33 omega   43.00   91.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 96

 34 omega   37.00   87.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 100

 35 omega   43.00  151.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  120.0000 216

 36 omega   79.00  137.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 116
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0226261000
_diffrn_orient_matrix_UB_12      -0.0808169000
_diffrn_orient_matrix_UB_13      -0.0252511000
_diffrn_orient_matrix_UB_21      0.0588653000
_diffrn_orient_matrix_UB_22      -0.0138223000
_diffrn_orient_matrix_UB_23      0.1264910000
_diffrn_orient_matrix_UB_31      -0.1327522000
_diffrn_orient_matrix_UB_32      -0.0199418000
_diffrn_orient_matrix_UB_33      0.0146024000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17116
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.066
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         4.217
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.619
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92914
_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_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       prism
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4192
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0779P)^2^+0.3819P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1396
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3540
_reflns_number_total             4192
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc04880d2.cif
_cod_data_source_block           201809377
_cod_depositor_comments
;Adding full bibliography for 1556630--1556636.cif.

 Adding full bibliography for 1556630--1556636.cif.
;
_cod_database_code               1556631
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N2
_shelx_estimated_absorpt_t_max   0.855
_shelx_estimated_absorpt_t_min   0.793
_reflns_odcompleteness_completeness 99.98
_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
2.a Ternary CH refined with riding coordinates:
 C20(H20), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C21(H21A,H21B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C16(H16), C17(H17), C25(H25),
 C26(H26), C27(H27), C28(H28), C29(H29)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_olex2_submission_special_instructions 'No special instructions were received'