Total Synthesis of the Proposed Structure of Marineosin A.
Xu, Bing; Li, Guang; Li, Jing; Shi, Yian; Organic letters 18 (2016) 2028–2031; doi:10.1021/acs.orglett.6b00632

data_1555528
_publ_section_title
;
 Total Synthesis of the Proposed Structure of Marineosin A.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2028
_journal_page_last               2031
_journal_paper_doi               10.1021/acs.orglett.6b00632
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H31 N O5'
_chemical_formula_sum            'C18 H31 N O5'
_chemical_formula_weight         341.44
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-04-05
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.71375(6)
_cell_length_b                   8.88494(9)
_cell_length_c                   28.0459(2)
_cell_measurement_reflns_used    25721
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      73.7960
_cell_measurement_theta_min      4.6930
_cell_volume                     1922.16(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -77.00    4.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7306  -19.0000 -180.0000 81

  2 omega  -50.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7306   38.0000   30.0000 83

  3 omega   62.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7306  178.0000 -180.0000 41

  4 omega   36.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -30.0000 -150.0000 43

  5 omega   34.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -45.0000  -90.0000 57

  6 omega   59.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -30.0000  120.0000 26

  7 omega   99.00  169.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  125.0000 -180.0000 70

  8 omega   41.00  138.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -61.0000   60.0000 97

  9 omega   82.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   45.0000 -120.0000 95

 10 omega -115.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7306  -57.0000   30.0000 104

 11 omega   57.00  131.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7306  178.0000  -30.0000 74

 12 omega   46.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   15.0000   30.0000 132

 13 omega   32.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775 -125.0000  -60.0000 90

 14 omega   77.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   61.0000  -90.0000 101

 15 omega   46.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   15.0000 -180.0000 132

 16 omega -119.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7306  -77.0000  150.0000 112

 17 omega   11.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7306   57.0000  -30.0000 104

 18 omega   77.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   61.0000   60.0000 101

 19 omega   23.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -94.0000   30.0000 86

 20 omega   74.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   77.0000    0.0000 104

 21 omega   80.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   45.0000 -150.0000 98

 22 omega -119.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7306  -77.0000    0.0000 112

 23 omega   57.00  131.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7306  178.0000 -150.0000 74

 24 omega   94.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  125.0000  -60.0000 84

 25 omega   77.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   61.0000 -120.0000 101

 26 omega   74.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   77.0000  -60.0000 104

 27 omega   74.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   77.0000  150.0000 104

 28 omega -115.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7306  -57.0000 -180.0000 104

 29 omega  -50.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7306   38.0000  -60.0000 85

 30 omega   74.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   77.0000  120.0000 104

 31 omega   80.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   45.0000    0.0000 98

 32 omega   77.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   61.0000   30.0000 101

 33 omega   77.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   61.0000   90.0000 101

 34 omega -119.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7306  -77.0000  -60.0000 112

 35 omega -119.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7306  -77.0000   90.0000 112

 36 omega   23.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -94.0000  -60.0000 86

 37 omega   77.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   61.0000  120.0000 101

 38 omega   77.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   61.0000 -150.0000 101

 39 omega   77.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   61.0000  -60.0000 101

 40 omega -115.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7306  -57.0000 -120.0000 104

 41 omega  -50.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7306   38.0000 -180.0000 85

 42 omega   74.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3775   77.0000 -120.0000 28
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1290226000
_diffrn_orient_matrix_UB_12      0.0186875000
_diffrn_orient_matrix_UB_13      0.0415136000
_diffrn_orient_matrix_UB_21      0.1451433000
_diffrn_orient_matrix_UB_22      0.0675161000
_diffrn_orient_matrix_UB_23      0.0310719000
_diffrn_orient_matrix_UB_31      -0.0465626000
_diffrn_orient_matrix_UB_32      0.1586169000
_diffrn_orient_matrix_UB_33      -0.0181267000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            41233
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_min         5.222
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_description
;
;
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1373 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3390
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0649P)^2^+0.4755P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1042
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3337
_reflns_number_total             3390
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00632_si_003.cif
_cod_data_source_block           exp_5061
_cod_database_code               1555528
_shelxl_version_number           2013-3
_chemical_oxdiff_formula         C18H31N1O5
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.903
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C7(H7A,H7B), C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C15(H15)
2.d X=CH2 refined with riding coordinates:
 C12(H12A,H12B), C16(H16A,H16B)
2.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C17(H17A,H17B,H17C), C24(H24A,H24B,H24C)
2.f Idealised tetrahedral OH refined as rotating group:
 O3(H3A)
;
_olex2_submission_special_instructions 'No special instructions were received'