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_1555527
_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 rmad
_chemical_formula_moiety         'C21 H33 N O5'
_chemical_formula_sum            'C21 H33 N O5'
_chemical_formula_weight         379.48
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-02-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4200(6)
_cell_length_b                   19.1624(10)
_cell_length_c                   9.3685(9)
_cell_measurement_reflns_used    6672
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4795
_cell_measurement_theta_min      1.7832
_cell_volume                     2050.2(2)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.0861
	          2theta: -19.4275
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 45.0861
	          2theta: -19.4275
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0025
_diffrn_orient_matrix_UB_12      0.0197
_diffrn_orient_matrix_UB_13      0.1049
_diffrn_orient_matrix_UB_21      0.0402
_diffrn_orient_matrix_UB_22      -0.0766
_diffrn_orient_matrix_UB_23      0.0135
_diffrn_orient_matrix_UB_31      0.0463
_diffrn_orient_matrix_UB_32      0.0234
_diffrn_orient_matrix_UB_33      -0.0055
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15775
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         2.126
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1768 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         4653
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.201
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0432P)^2^+0.5085P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                4594
_reflns_number_total             4653
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00632_si_005.cif
_cod_data_source_block           a
_cod_database_code               1555527
_diffrn_number_total             2682
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C17-C16 = C18-C17A = C17A-C16 = C18-C17 = C19A-C18 = C19-C18 = C20-C19 = C20-
 C19A
 1.54 with sigma of 0.01
3. Others
 Sof(H16C)=Sof(H16D)=Sof(H18C)=Sof(H18D)=Sof(H20C)=Sof(H20D)=Sof(C17A)=
 Sof(H17C)=Sof(H17D)=Sof(C19A)=Sof(H19C)=Sof(H19D)=1-FVAR(1)
 Sof(H16A)=Sof(H16B)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H18A)=Sof(H18B)=Sof(C19)=
 Sof(H19A)=Sof(H19B)=Sof(H20A)=Sof(H20B)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C2(H2), C6(H6), C7(H7), C9(H9)
4.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C8(H8A,H8B), C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B),
 C16(H16A,H16B), C16(H16C,H16D), C17(H17A,H17B), C18(H18A,H18B), C18(H18C,H18D),
  C19(H19A,H19B), C20(H20A,H20B), C20(H20C,H20D), C21(H21A,H21B), C17A(H17C,
 H17D), C19A(H19C,H19D)
4.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              68126
_shelx_hkl_checksum              88938
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'