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_1555526
_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 rm
_chemical_formula_moiety         'C25 H35 N3 O2, H2 O'
_chemical_formula_sum            'C25 H37 N3 O3'
_chemical_formula_weight         427.57
_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     direct
_audit_creation_date             2015-04-23
_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                   8.174(3)
_cell_length_b                   12.797(5)
_cell_length_c                   21.823(8)
_cell_measurement_reflns_used    6166
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4830
_cell_measurement_theta_min      1.5913
_cell_volume                     2282.7(15)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
scan:
	Number of images: 330
	           Slice: -110.0000 - 55.0000
	     Image width: 0.5000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 45.0771
	          2theta: -19.8243
scan:
	Number of images: 240
	           Slice: -80.0000 - 40.0000
	     Image width: 0.5000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.0771
	          2theta: -19.8243
;
_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      -0.0013
_diffrn_orient_matrix_UB_12      -0.1029
_diffrn_orient_matrix_UB_13      -0.0661
_diffrn_orient_matrix_UB_21      0.0455
_diffrn_orient_matrix_UB_22      0.0339
_diffrn_orient_matrix_UB_23      -0.0537
_diffrn_orient_matrix_UB_31      0.0373
_diffrn_orient_matrix_UB_32      -0.0147
_diffrn_orient_matrix_UB_33      0.0222
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            14336
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.957
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       rod
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1446 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         5203
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0595
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0305P)^2^+0.7119P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1086
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                4672
_reflns_number_total             5203
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00632_si_006.cif
_cod_data_source_block           sa4069
_cod_database_code               1555526
_diffrn_number_total             3002
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Riding coordinates:
 O3(H3C,H3D)
2.b Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C18(H18)
2.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B),
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C19(H19A,H19B)
2.d Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C7(H7), C8(H8), C22(H22), C23(H23), C24(H24)
2.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              13508
_shelx_hkl_checksum              11042
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'