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_7157836
_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_formula_moiety         'C22 H21 N O2'
_chemical_formula_sum            'C22 H21 N O2'
_chemical_formula_weight         331.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-18
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.10.31 svn.r3677 for OlexSys, GUI svn.r5972)
;
_audit_update_record
;
2020-07-08 deposited with the CCDC.	2021-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.577(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9597(10)
_cell_length_b                   15.0950(12)
_cell_length_c                   12.0193(12)
_cell_measurement_reflns_used    2988
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.0400
_cell_measurement_theta_min      2.5480
_cell_volume                     1712.9(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 2018/2 (Sheldrick, 2018)'
_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 0.999
_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    -53.00  42.00   1.00    2.50    --   11.74 -77.00 -60.00   95
  2  \w     -3.00  83.00   1.00    2.50    --   11.74  57.00  60.00   86
;
_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      0.0128761000
_diffrn_orient_matrix_UB_12      0.0396903000
_diffrn_orient_matrix_UB_13      -0.0265760000
_diffrn_orient_matrix_UB_21      0.0310138000
_diffrn_orient_matrix_UB_22      -0.0248736000
_diffrn_orient_matrix_UB_23      -0.0354742000
_diffrn_orient_matrix_UB_31      -0.0673201000
_diffrn_orient_matrix_UB_32      -0.0039001000
_diffrn_orient_matrix_UB_33      -0.0435901000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6760
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.240
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.06173
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3018
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0486
_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^)+(0.0515P)^2^+0.4352P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1210
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2392
_reflns_number_total             3018
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02514c2.cif
_cod_data_source_block           yj-1
_cod_depositor_comments
'Adding full bibliography for 7157835--7157836.cif.'
_cod_original_cell_volume        1712.8(3)
_cod_database_code               7157836
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.989
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C12(H12A,H12B), C15(H15A,H15B), C14(H14A,H14B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C5(H5), C18(H18), C3(H3), C19(H19), C4(H4), C22(H22),
 C21(H21), C20(H20)
;
_shelx_res_checksum              31406
_shelx_hkl_checksum              29648
_olex2_date_sample_data_collection 2019-11-11
_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 12.072
_oxdiff_exptl_absorpt_empirical_full_min 0.526