Enantioselective total synthesis and structural reassignment of (+)-alsmaphorazine E via a traceless chirality transfer strategy.
Yu, Kuan; Gao, Beiling; Liu, Zhaobo; Ding, Hanfeng; Chemical communications (Cambridge, England) 52 (2016) 4485–4488; doi:10.1039/c6cc00930a

data_7118807
_publ_section_title
;
 Enantioselective total synthesis and structural reassignment of
 (+)-alsmaphorazine E via a traceless chirality transfer strategy.
;
_journal_issue                   24
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4485
_journal_page_last               4488
_journal_paper_doi               10.1039/c6cc00930a
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C30 H34 N2 O9'
_chemical_formula_sum            'C30 H34 N2 O9'
_chemical_formula_weight         566.59
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-12-15
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2016-01-02 deposited with the CCDC.
2016-02-25 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                   9.09127(13)
_cell_length_b                   10.54359(15)
_cell_length_c                   30.6974(5)
_cell_measurement_reflns_used    9178
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.3693
_cell_measurement_theta_min      4.1896
_cell_volume                     2942.49(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0152282000
_diffrn_orient_matrix_UB_12      -0.0499083000
_diffrn_orient_matrix_UB_13      -0.0469465000
_diffrn_orient_matrix_UB_21      0.1215284000
_diffrn_orient_matrix_UB_22      -0.0919631000
_diffrn_orient_matrix_UB_23      0.0149897000
_diffrn_orient_matrix_UB_31      -0.1171289000
_diffrn_orient_matrix_UB_32      -0.1019861000
_diffrn_orient_matrix_UB_33      0.0094638000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            19424
_diffrn_reflns_theta_full        67.48
_diffrn_reflns_theta_max         67.48
_diffrn_reflns_theta_min         4.43
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.789
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack (1983), 2238 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.05(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         5252
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0318
_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^)+(0.0438P)^2^+0.2142P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0803
_reflns_number_gt                4859
_reflns_number_total             5252
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc00930a2.cif
_cod_data_source_block           151214_yk_3_139
_cod_depositor_comments
'Adding full bibliography for 7118807--7118808.cif.'
_cod_database_code               7118807
_chemical_oxdiff_formula         'c10 h10 n2 o8'
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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:
 C12(H12), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C14(H14A,H14B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;