Catalyst- and additive-free [3 + 3] cyclization–aromatization of β,γ-dioxobutanoate with amines for synthesis of p-aminophenols
Qian, Hang; Wang, Cui-Cui; Shen, Zi-Chen; Sun, Ming-Xue; Zhang, Hong-Chao; Fan, Shiming; Feng, Juan; Liu, Shouxin; Zhang, Zhi-Wei; Green Chemistry 24 (2022) 9690–9696; doi:10.1039/D2GC03936B

data_7245915
_publ_section_title
;
 Catalyst- and additive-free [3 + 3] cyclization--aromatization of
 \b,\g-dioxobutanoate with amines for synthesis of p-aminophenols
;
_journal_issue                   24
_journal_name_full               'Green Chemistry'
_journal_page_first              9690
_journal_page_last               9696
_journal_paper_doi               10.1039/D2GC03936B
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C23 H26 N2 O6'
_chemical_formula_sum            'C23 H26 N2 O6'
_chemical_formula_weight         426.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-10
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-09-27 deposited with the CCDC.	2022-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                112.233(6)
_cell_angle_beta                 90.786(5)
_cell_angle_gamma                95.430(4)
_cell_formula_units_Z            2
_cell_length_a                   8.6271(4)
_cell_length_b                   11.5365(6)
_cell_length_c                   12.0186(8)
_cell_measurement_reflns_used    1934
_cell_measurement_temperature    292.8(2)
_cell_measurement_theta_max      75.1880
_cell_measurement_theta_min      3.9450
_cell_volume                     1100.68(12)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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_environment      air
_diffrn_ambient_temperature      292.8(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.941
_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    -98.00 -60.00   1.00    0.20    --  -47.57 142.00-123.00   38
  2  \w    -95.00 -29.00   1.00    0.20    --  -47.57 127.00  66.00   66
  3  \w     38.00 112.00   1.00    0.20    --   47.57  77.00  60.00   74
  4  \w     98.00 154.00   1.00    0.61    --  107.75  57.00 -30.00   56
  5  \w    127.00 171.00   1.00    0.61    --  107.75  37.00-120.00   44
  6  \w    -65.00 -28.00   1.00    0.61    -- -100.00  57.00  60.00   37
  7  \w   -102.00 -28.00   1.00    0.61    -- -100.00  77.00 -30.00   74
  8  \w     41.00  67.00   1.00    0.20    --   47.57-142.00-179.00   26
  9  \w     55.00  80.00   1.00    0.61    --  107.75-142.00-179.00   25
 10  \w     38.00 107.00   1.00    0.61    --  107.75-125.00-180.00   69
 11  \w     73.00 102.00   1.00    0.61    --  107.75 -99.00-150.00   29
 12  \w     74.00 100.00   1.00    0.61    --  107.75 -99.00-120.00   26
 13  \w     68.00  94.00   1.00    0.61    --  107.75-127.00  -9.00   26
 14  \w     39.00  65.00   1.00    0.61    --  107.75 -99.00-120.00   26
 15  \w     33.00  58.00   1.00    0.20    --   47.57-127.00  -9.00   25
 16  \w     66.00  92.00   1.00    0.61    --  107.75 -99.00   0.00   26
 17  \w     62.00  88.00   1.00    0.61    --  107.75 -77.00   0.00   26
 18  \w     35.00  60.00   1.00    0.61    --  107.75 -57.00  30.00   25
 19  \w     36.00  62.00   1.00    0.61    --  107.75 -57.00  60.00   26
 20  \w     35.00  61.00   1.00    0.61    --  107.75 -57.00 120.00   26
 21  \w    -26.00  19.00   1.00    0.20    --   47.57 -19.00  90.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0470618000
_diffrn_orient_matrix_UB_12      0.0058675000
_diffrn_orient_matrix_UB_13      -0.1217407000
_diffrn_orient_matrix_UB_21      0.0480764000
_diffrn_orient_matrix_UB_22      -0.1332692000
_diffrn_orient_matrix_UB_23      -0.0660069000
_diffrn_orient_matrix_UB_31      -0.1666048000
_diffrn_orient_matrix_UB_32      -0.0570099000
_diffrn_orient_matrix_UB_33      0.0073104000
_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  0.0315
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13568
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.434
_diffrn_reflns_theta_min         3.979
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_description       plate
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4395
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0624
_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^)+(0.0838P)^2^+0.2581P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1739
_refine_ls_wR_factor_ref         0.1903
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3095
_reflns_number_total             4395
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc03936b2.cif
_cod_data_source_block           zhzhw_1010_auto
_cod_depositor_comments          'Adding full bibliography for 7245915.cif.'
_cod_database_code               7245915
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.941
_reflns_odcompleteness_completeness 76.92
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C3(H3A), C6(H6), C17(H17), C19(H19), C20(H20), C22(H22)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C12(H12A,H12B,H12C), C23(H23A,H23B,H23C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              79165
_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 1.713
_oxdiff_exptl_absorpt_empirical_full_min 0.792