Construction of the Erythrinane Core Skeleton via Asymmetric Catalytic Cascade Reaction of Tertiary Enamides.
Zhen, Li; Tong, Shuo; Zhu, Jieping; Wang, Mei-Xiang; The Journal of organic chemistry 85 (2020) 13211–13219; doi:10.1021/acs.joc.0c01992

data_4038876
_publ_section_title
;
 Construction of the Erythrinane Core Skeleton via Asymmetric Catalytic
 Cascade Reaction of Tertiary Enamides.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13211
_journal_page_last               13219
_journal_paper_doi               10.1021/acs.joc.0c01992
_journal_volume                  85
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H27 N O4'
_chemical_formula_sum            'C24 H27 N O4'
_chemical_formula_weight         393.46
_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             2020-07-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.06370(10)
_cell_length_b                   16.8612(2)
_cell_length_c                   19.9302(2)
_cell_measurement_reflns_used    13380
_cell_measurement_temperature    169.99(11)
_cell_measurement_theta_max      75.3260
_cell_measurement_theta_min      3.4090
_cell_volume                     2037.69(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_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      169.99(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_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    -24.00  62.00   0.50    0.05    --   47.20 -58.00-137.00  172
  2  \w     32.00 120.00   0.50    0.05    --   47.20  58.00   3.00  176
  3  \w   -114.00 -26.00   0.50    0.12    --  -99.00  58.00   3.00  176
  4  \w   -168.00 -84.00   0.50    0.12    --  -99.00 -58.00-137.00  168
  5  \w     88.00 169.00   0.50    0.12    --  103.25  58.00   3.00  162
  6  \w     31.00 119.00   0.50    0.12    --  103.25 -58.00-137.00  176
  7  \w    -62.00  25.00   0.50    0.05    --  -47.20  58.00   3.00  174
  8  \w   -120.00 -71.00   0.50    0.05    --  -47.20-125.00  30.00   98
  9  \w   -120.00 -71.00   0.50    0.05    --  -47.20-125.00   0.00   98
 10  \w   -168.00 -86.00   0.50    0.12    --  -99.00 -45.00 -60.00  164
 11  \w   -112.00 -27.00   0.50    0.12    --  -99.00  45.00-150.00  170
 12  \w     77.00 169.00   0.50    0.12    --  103.25 125.00 -90.00  184
 13  \w     90.00 169.00   0.50    0.12    --  103.25  15.00  90.00  158
 14  \w     91.00 169.00   0.50    0.12    --  103.25  45.00 -60.00  156
 15  \w     91.00 169.00   0.50    0.12    --  103.25  30.00 150.00  156
 16  \w     31.00 109.00   0.50    0.12    --  103.25 -94.00-180.00  156
 17  \w     25.00  50.00   0.50    0.05    --   47.20  77.00-120.00   50
;
_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      0.0988307000
_diffrn_orient_matrix_UB_12      0.0803974000
_diffrn_orient_matrix_UB_13      -0.0210487000
_diffrn_orient_matrix_UB_21      -0.1562881000
_diffrn_orient_matrix_UB_22      0.0427795000
_diffrn_orient_matrix_UB_23      0.0490604000
_diffrn_orient_matrix_UB_31      0.1741940000
_diffrn_orient_matrix_UB_32      -0.0072159000
_diffrn_orient_matrix_UB_33      0.0559247000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19298
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.506
_diffrn_reflns_theta_min         3.433
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.700
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.005
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1564 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4100
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0655P)^2^+0.3076P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1116
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                3894
_reflns_number_total             4100
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01992_si_002.cif
_cod_data_source_block           tx1109
_cod_depositor_comments
'Adding full bibliography for 4038875--4038876.cif.'
_cod_database_code               4038876
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         CHNO
_reflns_odcompleteness_completeness 100.00
_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 Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C7(H7A,H7B), C4(H4A,H4B), C6(H6A,H6B), C17(H17A,H17B), C5(H5A,
 H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C15(H15), C23(H23), C22(H22), C14(H14), C11(H11), C13(H13), C12(H12)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C27(H27A,H27B,H27C)
2.d Idealised tetrahedral OH refined as rotating group:
 O29(H29)
;
_shelx_res_checksum              49547
_shelx_hkl_checksum              2489
_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 2.457
_oxdiff_exptl_absorpt_empirical_full_min 0.253