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_1555525
_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         'C23 H39 N O3 S Si'
_chemical_formula_sum            'C23 H39 N O3 S Si'
_chemical_formula_weight         437.70
_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     direct
_audit_creation_date             2015-07-15
_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            8
_cell_length_a                   11.2183(14)
_cell_length_b                   17.958(2)
_cell_length_c                   25.733(2)
_cell_measurement_reflns_used    18009
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4778
_cell_measurement_theta_min      1.1339
_cell_volume                     5184.1(10)
_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  'CIFTAB (Sheldrick, 2013)'
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.2768
	          2theta: -20.0900
scan:
	Number of images: 240
	           Slice: -80.0000 - 40.0000
	     Image width: 0.5000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 45.2768
	          2theta: -20.0900
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0077
_diffrn_orient_matrix_UB_12      -0.0832
_diffrn_orient_matrix_UB_13      -0.0310
_diffrn_orient_matrix_UB_21      -0.0200
_diffrn_orient_matrix_UB_22      0.0165
_diffrn_orient_matrix_UB_23      -0.0493
_diffrn_orient_matrix_UB_31      0.0361
_diffrn_orient_matrix_UB_32      0.0078
_diffrn_orient_matrix_UB_33      -0.0120
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            35540
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_min         1.947
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_description       rod
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 4213 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(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     537
_refine_ls_number_reflns         11719
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0444
_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^)+(0.0454P)^2^+1.2647P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1010
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                11180
_reflns_number_total             11719
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00632_si_002.cif
_cod_data_source_block           mx3611
_cod_database_code               1555525
_diffrn_number_total             6584
_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
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C10(H10), C2A(H2A), C3A(H3A), C5A(H5A), C10A(H10A)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C19(H19A,H19B), C20(H20A,H20B), C4A(H4AA,H4AB), C19A(H19C,H19D),
 C20A(H20C,H20D)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C11(H11), C21(H21), C7A(H7A), C8A(H8A), C11A(H11A), C21A(H21A)
2.d X=CH2 refined with riding coordinates:
 C12(H12A,H12B), C22(H22A,H22B), C12A(H12C,H12D), C22A(H22C,H22D)
2.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C23(H23A,H23B,H23C), C9A(H9AA,
 H9AB,H9AC), C13A(H13D,H13E,H13F), C14A(H14D,H14E,H14F), C16A(H16D,H16E,H16F),
 C17A(H17D,H17E,H17F), C18A(H18D,H18E,H18F), C23A(H23D,H23E,H23F)
;
_shelx_res_checksum              89927
_shelx_hkl_checksum              49682
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'