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_1553196
_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_formula_moiety         'C24 H22 N4 O4, 2(H2 O)'
_chemical_formula_sum            'C24 H26 N4 O6'
_chemical_formula_weight         466.49
_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     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                95.818(5)
_cell_angle_beta                 90.490(5)
_cell_angle_gamma                111.805(6)
_cell_formula_units_Z            2
_cell_length_a                   9.3200(6)
_cell_length_b                   10.5489(6)
_cell_length_c                   12.1772(7)
_cell_measurement_reflns_used    1875
_cell_measurement_temperature    173.00(14)
_cell_measurement_theta_max      60.2190
_cell_measurement_theta_min      4.5470
_cell_volume                     1104.44(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_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_temperature      173.00(14)
_diffrn_detector_area_resol_mean 16.1903
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
  1 omega   13.00  101.20   0.7000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       32.3584   57.0000  -90.0000 126

  2 omega  -33.00   55.20   0.7000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       32.3584  -57.0000    0.0000 126

  3 omega   10.00  102.40   0.7000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       32.3584   57.0000  150.0000 132

  4 omega   77.00  110.60   0.7000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       32.3584  178.0000    0.0000 48

  5 omega -156.00 -107.00   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -75.0000  178.0000  -30.0000 70

  6 omega  -82.00  -54.70   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -75.0000  178.0000  -30.0000 39

  7 omega -130.00 -102.00   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -75.0000 -112.0000   90.0000 40

  8 omega -148.00 -114.40   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -75.0000  -92.0000 -150.0000 48

  9 omega   24.00   82.10   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -50.0000  150.0000 83

 10 omega   29.00  103.20   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -92.0000  150.0000 106

 11 omega   38.00   99.60   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -92.0000  -90.0000 88

 12 omega   32.00   65.60   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -25.0000  -90.0000 48

 13 omega   26.00   59.60   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -38.0000    0.0000 48

 14 omega   21.00   70.00   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -38.0000 -150.0000 70

 15 omega   34.00   69.70   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -50.0000  -30.0000 51

 16 omega   16.00   57.30   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -25.0000   90.0000 59

 17 omega   19.00   50.50   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -25.0000   60.0000 45

 18 omega   23.00   70.60   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -112.0000  120.0000 68

 19 omega   17.00   68.10   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -38.0000  -30.0000 73

 20 omega   28.00   63.70   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -25.0000 -120.0000 51

 21 omega   32.00  114.60   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -92.0000  -30.0000 118

 22 omega   76.00  101.20   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -92.0000   60.0000 36

 23 omega   18.00  150.30   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   12.0000  -90.0000 189
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0563498000
_diffrn_orient_matrix_UB_12      -0.1121693000
_diffrn_orient_matrix_UB_13      0.0787808000
_diffrn_orient_matrix_UB_21      -0.1416113000
_diffrn_orient_matrix_UB_22      -0.0805012000
_diffrn_orient_matrix_UB_23      -0.0792300000
_diffrn_orient_matrix_UB_31      0.0924495000
_diffrn_orient_matrix_UB_32      -0.0774408000
_diffrn_orient_matrix_UB_33      -0.0610603000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5671
_diffrn_reflns_theta_full        60.18
_diffrn_reflns_theta_max         60.18
_diffrn_reflns_theta_min         3.65
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.849
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       pillar
_exptl_crystal_F_000             492
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3246
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.960
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0339P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0932
_reflns_number_gt                2549
_reflns_number_total             3246
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5qo00298b2.cif
_cod_data_source_block           exp_10604
_cod_original_cell_volume        1104.43(11)
_cod_database_code               1553196
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_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, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B), O6(H6A,H6B)
2.b Ternary CH refined with riding coordinates:
 C3(H3), C6(H6), C10(H10), C17(H17)
2.c Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.d Aromatic/amide H refined with riding coordinates:
 C8(H8), C13(H13), C14(H14), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21),
 C22(H22)
2.e Idealised Me refined as rotating group:
 C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,H1BC)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'