LiCl-promoted amination of β-methoxy amides (γ-lactones)
Zhao, Ru; Zeng, Bing-Lin; Jia, Wen-Qiang; Zhao, Hong-Yi; Shen, Long-Ying; Wang, Xiao-Jian; Pan, Xian-Dao; RSC Advances 10 (2020) 34938–34942; doi:10.1039/D0RA07170F

data_7241284
_publ_section_title
;
 LiCl-promoted amination of \b-methoxy amides (\g-lactones)
;
_journal_issue                   57
_journal_name_full               'RSC Advances'
_journal_page_first              34938
_journal_page_last               34942
_journal_paper_doi               10.1039/D0RA07170F
_journal_volume                  10
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H29 N O3'
_chemical_formula_sum            'C19 H29 N O3'
_chemical_formula_weight         319.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-29 deposited with the CCDC.	2020-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.02107(3)
_cell_length_b                   12.63736(6)
_cell_length_c                   23.03193(10)
_cell_measurement_reflns_used    31182
_cell_measurement_temperature    170.00(12)
_cell_measurement_theta_max      75.4120
_cell_measurement_theta_min      3.4900
_cell_volume                     1752.509(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 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_environment      N~2~
_diffrn_ambient_temperature      170.00(12)
_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 0.990
_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   -120.00 -59.00   0.50    0.05    --  -47.20-147.00 -19.00  122
  2  \w    -94.00 -12.00   0.50    0.05    --  -47.20 124.00-135.00  164
  3  \w   -107.00 -25.00   0.50    0.05    --  -47.20 147.00  29.00  164
  4  \w     31.00 107.00   0.50    0.05    --   47.20-147.00 -19.00  152
  5  \w     65.00 120.00   0.50    0.05    --   47.20 147.00  29.00  110
  6  \w     19.00  94.00   0.50    0.05    --   47.20-124.00 145.00  150
  7  \w   -127.00 -26.00   0.50    0.05    --  -99.00 147.00  29.00  202
  8  \w   -168.00 -59.00   0.50    0.05    --  -99.00-147.00 -19.00  218
  9  \w   -168.00 -75.00   0.50    0.05    --  -99.00-124.00 145.00  186
 10  \w   -111.00 -26.00   0.50    0.05    --  -99.00 124.00-135.00  170
 11  \w     81.00 169.00   0.50    0.05    --  103.25 124.00-135.00  176
 12  \w     31.00 127.00   0.50    0.05    --  103.25-147.00 -19.00  192
 13  \w     31.00 110.00   0.50    0.05    --  103.25-124.00 145.00  158
 14  \w    -23.00  28.00   0.50    0.05    --  -47.20  19.00-120.00  102
 15  \w    -23.00  28.00   0.50    0.05    --  -47.20  19.00  60.00  102
 16  \w   -120.00 -74.00   0.50    0.05    --  -47.20-125.00  30.00   92
 17  \w    -23.00  28.00   0.50    0.05    --  -47.20  19.00-180.00  102
 18  \w    -23.00  28.00   0.50    0.05    --  -47.20  19.00 -90.00  102
 19  \w   -120.00 -74.00   0.50    0.05    --  -47.20-125.00-180.00   92
 20  \w    -23.00  28.00   0.50    0.05    --  -47.20  19.00 120.00  102
 21  \w    -27.00  30.00   0.50    0.05    --   47.20 -19.00-120.00  114
 22  \w   -168.00 -86.00   0.50    0.05    --  -99.00 -45.00   0.00  164
 23  \w   -112.00 -26.00   0.50    0.05    --  -99.00 125.00 -30.00  172
 24  \w   -168.00 -84.00   0.50    0.05    --  -99.00 -94.00 -90.00  168
 25  \w   -168.00 -85.00   0.50    0.05    --  -99.00 -15.00  30.00  166
 26  \w   -112.00 -26.00   0.50    0.05    --  -99.00 125.00 150.00  172
 27  \w   -112.00 -26.00   0.50    0.05    --  -99.00 125.00-180.00  172
 28  \w    -64.00 -29.00   0.50    0.05    --  -99.00  61.00  30.00   70
 29  \w     91.00 164.00   0.50    0.05    --  103.25  45.00  60.00  146
 30  \w     33.00 102.00   0.50    0.05    --  103.25 -94.00   0.00  138
 31  \w     41.00  74.00   0.50    0.05    --  103.25 -61.00-180.00   66
 32  \w     31.00  78.00   0.50    0.05    --  103.25 -94.00 150.00   94
 33  \w     54.00  80.00   0.50    0.05    --  103.25 -77.00 -60.00   52
 34  \w     32.00  75.00   0.50    0.05    --  103.25 -61.00 150.00   86
 35  \w     31.00  69.00   0.50    0.05    --  103.25 -61.00 120.00   76
 36  \w    132.00 169.00   0.50    0.05    --  103.25  77.00-150.00   74
 37  \w     37.00  72.00   0.50    0.05    --  103.25 -61.00   0.00   70
 38  \w     93.00 124.00   0.50    0.05    --  103.25  77.00-150.00   62
 39  \w     34.00  74.00   0.50    0.05    --  103.25 -61.00-150.00   80
 40  \w     33.00  95.00   0.50    0.05    --  103.25 -94.00 -60.00  124
 41  \w     32.00  82.00   0.50    0.05    --  103.25 -77.00   0.00  100
 42  \w     91.00 154.00   0.50    0.05    --  103.25  30.00 -30.00  126
 43  \w     82.00 162.00   0.50    0.05    --  103.25  77.00 120.00  160
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0301400000
_diffrn_orient_matrix_UB_12      0.1210206000
_diffrn_orient_matrix_UB_13      0.0017510000
_diffrn_orient_matrix_UB_21      0.2193853000
_diffrn_orient_matrix_UB_22      0.0107324000
_diffrn_orient_matrix_UB_23      0.0339061000
_diffrn_orient_matrix_UB_31      0.1281462000
_diffrn_orient_matrix_UB_32      0.0100155000
_diffrn_orient_matrix_UB_33      -0.0576328000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0088
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            33825
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.512
_diffrn_reflns_theta_min         3.838
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.642
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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    1.211
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM MeOH'
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1465 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3578
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0299
_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^)+(0.0481P)^2^+0.2095P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0774
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                3550
_reflns_number_total             3578
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra07170f2.cif
_cod_data_source_block           tx2212
_cod_depositor_comments          'Adding full bibliography for 7241284.cif.'
_cod_original_cell_volume        1752.508(14)
_cod_database_code               7241284
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNOSCl
_reflns_odcompleteness_completeness 99.79
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3A), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C10(H10A,H10B), C11(H11A,H11B), C15(H15A,H15B),
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              82138
_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 1.318
_oxdiff_exptl_absorpt_empirical_full_min 0.767