Stereodivergent and enantioselective total syntheses of isochaetominines A–C and four pairs of isochaetominine C enantiomers: a six-step approach
Mao, Zhong-Yi; Geng, Hui; Zhang, Tian-Tian; Ruan, Yuan-Ping; Ye, Jian-Liang; Huang, Pei-Qiang; Organic Chemistry Frontiers 3 (2016) 24–; doi:10.1039/C5QO00298B

data_1553195
_publ_section_title
;
 Stereodivergent and enantioselective total syntheses of isochaetominines
 A--C and four pairs of isochaetominine C enantiomers: a six-step approach
;
_journal_issue                   1
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              24
_journal_paper_doi               10.1039/C5QO00298B
_journal_volume                  3
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C24 H22 N4 O4'
_chemical_formula_sum            'C24 H22 N4 O4'
_chemical_formula_weight         430.46
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-09-07
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-09-24 deposited with the CCDC.
2015-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6889(2)
_cell_length_b                   15.5382(5)
_cell_length_c                   16.4272(6)
_cell_measurement_reflns_used    1932
_cell_measurement_temperature    99.8(5)
_cell_measurement_theta_max      69.0010
_cell_measurement_theta_min      5.6740
_cell_volume                     1962.58(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.8(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4741
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
  1 omega   32.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0610  -94.0000 -120.0000 77

  2 omega   45.00   84.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0610  -30.0000   30.0000 39

  3 omega   56.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0610  -30.0000  120.0000 35

  4 omega   21.00   85.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0610  -30.0000   90.0000 64

  5 omega   21.00   69.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0610  -30.0000 -120.0000 48

  6 omega -103.00   32.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6297    0.0000   90.0000 135
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0997282000
_diffrn_orient_matrix_UB_12      0.0362368000
_diffrn_orient_matrix_UB_13      0.0738339000
_diffrn_orient_matrix_UB_21      -0.0689895000
_diffrn_orient_matrix_UB_22      -0.0743453000
_diffrn_orient_matrix_UB_23      0.0529421000
_diffrn_orient_matrix_UB_31      0.1595100000
_diffrn_orient_matrix_UB_32      -0.0546079000
_diffrn_orient_matrix_UB_33      -0.0233828000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4748
_diffrn_reflns_theta_full        68.84
_diffrn_reflns_theta_max         68.84
_diffrn_reflns_theta_min         3.92
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.832
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       pillar
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0495P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1021
_reflns_number_gt                2925
_reflns_number_total             3186
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5qo00298b2.cif
_cod_data_source_block           exp_7070
_cod_database_code               1553195
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     63.60
_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:
 C7(H7), C11(H11), C12(H12), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C1A(H1AA,H1AB,H1AC)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'