Copper-catalyzed one-pot amine-alkylation of quinones with amines and alkanes.
Yang, Jian; Wang, Bei; Zhang, Yuankang; Zhang, Shuqing; He, Shuai; Shi, Zhi-Chuan; Wang, Ji-Yu; Organic & biomolecular chemistry 19 (2021) 988–992; doi:10.1039/d0ob02514c

data_7157835
_publ_section_title
;
 Copper-catalyzed one-pot amine-alkylation of quinones with amines and
 alkanes.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              988
_journal_page_last               992
_journal_paper_doi               10.1039/d0ob02514c
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H30 N2 O4'
_chemical_formula_sum            'C30 H30 N2 O4'
_chemical_formula_weight         482.56
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-08
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.04.02 svn.r1fbe7b6f for OlexSys, GUI svn.r6076)
;
_audit_update_record
;
2020-07-08 deposited with the CCDC.	2021-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.1583(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.14946(15)
_cell_length_b                   6.86531(7)
_cell_length_c                   15.15149(18)
_cell_measurement_reflns_used    9367
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4200
_cell_measurement_theta_min      3.0100
_cell_volume                     1200.85(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -69.00  32.00   1.00    1.00    --  -40.98  57.00  90.00  101
  2  \w   -129.00  47.00   1.00    1.00    --  -40.98   0.00  60.00  176
  3  \w     17.00 115.00   1.00    1.00    --   40.98  37.00-150.00   98
  4  \w     23.00  97.00   1.00    1.00    --   40.98-125.00-150.00   74
  5  \w     23.00  97.00   1.00    1.00    --   40.98-125.00 -30.00   74
  6  \w     24.00 109.00   1.00    1.00    --  106.95 -94.00-120.00   85
  7  \w     24.00 109.00   1.00    1.00    --  106.95 -94.00  90.00   85
  8  \w     31.00 135.00   1.00    1.00    --  106.95 -30.00  60.00  104
  9  \w     79.00 178.00   1.00    1.00    --  106.95  30.00  30.00   99
 10  \w     81.00 178.00   1.00    1.00    --  106.95  45.00 150.00   97
 11  \w     74.00 178.00   1.00    1.00    --  106.95  77.00 150.00  104
 12  \w     35.00 136.00   1.00    1.00    --  106.95 -61.00 -60.00  101
 13  \w     34.00 133.00   1.00    1.00    --  106.95 -45.00-120.00   99
 14  \w     77.00 174.00   1.00    1.00    --  106.95  77.00  90.00   97
 15  \w     91.00 169.00   1.00    1.00    --  106.95  45.00-150.00   78
 16  \w     75.00 101.00   1.00    1.00    --  106.95  77.00-180.00   26
 17  \w    129.00 156.00   1.00    1.00    --  106.95  77.00-180.00   27
 18  \w     48.00 109.00   1.00    1.00    --  106.95 -94.00 -30.00   61
 19  \w     99.00 125.00   1.00    1.00    --  106.95  30.00-150.00   26
 20  \w   -117.00 -64.00   1.00    1.00    --  -41.23 -77.00  60.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0701845000
_diffrn_orient_matrix_UB_12      -0.1657781000
_diffrn_orient_matrix_UB_13      0.0253044000
_diffrn_orient_matrix_UB_21      0.1106666000
_diffrn_orient_matrix_UB_22      -0.0752764000
_diffrn_orient_matrix_UB_23      0.0731325000
_diffrn_orient_matrix_UB_31      -0.0252153000
_diffrn_orient_matrix_UB_32      0.1312291000
_diffrn_orient_matrix_UB_33      0.0738918000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11875
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.548
_diffrn_reflns_theta_min         3.070
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 2030 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4737
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0311
_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^)+(0.0580P)^2^+0.1239P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0849
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.953
_reflns_number_gt                4644
_reflns_number_total             4737
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02514c3.cif
_cod_data_source_block           yj-2
_cod_depositor_comments
'Adding full bibliography for 7157835--7157836.cif.'
_cod_original_cell_volume        1200.84(3)
_cod_database_code               7157835
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.91
_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
2.a Ternary CH refined with riding coordinates:
 C25(H25), C11(H11), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C12(H12A,H12B), C27(H27A,H27B), C15(H15A,H15B), C29(H29A,
 H29B), C28(H28A,H28B), C26(H26A,H26B), C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C21(H21), C3(H3), C4(H4), C5(H5), C2(H2), C23(H23), C22(H22)
;
_shelx_res_checksum              56228
_shelx_hkl_checksum              72592
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.352
_oxdiff_exptl_absorpt_empirical_full_min 0.759