Total synthesis of (±)-distomadines a and B.
Jolibois, Alexandre E. R.; Lewis, William; Moody, Christopher J.; Organic letters 16 (2014) 1064–1067; doi:10.1021/ol403598k

data_1513451
_publ_section_title
;
 Total synthesis of (+-)-distomadines a and B.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              1064
_journal_page_last               1067
_journal_paper_doi               10.1021/ol403598k
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C18 H15 N O7'
_chemical_formula_sum            'C18 H15 N O7'
_chemical_formula_weight         357.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-12-02
_audit_creation_method
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Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   30.1051(6)
_cell_length_b                   30.0687(6)
_cell_length_c                   7.05381(16)
_cell_measurement_reflns_used    13278
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.45
_cell_measurement_theta_min      3.28
_cell_volume                     6385.3(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3613
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova Cu'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0442190000
_diffrn_orient_matrix_UB_12      0.0228667000
_diffrn_orient_matrix_UB_13      -0.0509416000
_diffrn_orient_matrix_UB_21      -0.0257564000
_diffrn_orient_matrix_UB_22      0.0395417000
_diffrn_orient_matrix_UB_23      -0.0848195000
_diffrn_orient_matrix_UB_31      0.0003377000
_diffrn_orient_matrix_UB_32      0.0232076000
_diffrn_orient_matrix_UB_33      0.1946953000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            38876
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.618
_diffrn_reflns_theta_min         4.156
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.985
_exptl_absorpt_correction_T_max  2.041
_exptl_absorpt_correction_T_min  1.086
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2976
_exptl_crystal_size_max          0.4988
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.0355
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         6465
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0499P)^2^+1.9782P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0933
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5423
_reflns_number_total             6465
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol403598k_si_002.cif
_cod_data_source_block           ajcjma
_cod_database_code               1513451
_nottingham_internal_coll_name   AJCJMA
_nottingham_internal_coll_number 11660
_nottingham_internal_coll_client AJ/CJM
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_time '20.0000 and 80.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_user   WL
_nottingham_internal_coll_date   12/7/2012
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_user WL
_nottingham_internal_process_date 17/07/2012
_nottingham_internal_solution_user wl
_nottingham_internal_solution_date 24/7/2012
_nottingham_internal_refinement_user wl
_nottingham_internal_refinement_date 24/7/2012
_nottingham_internal_validation_user wl
_nottingham_internal_validation_date 5/12/2013
_nottingham_internal_archive_date 5/12/2013
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C18 H15 N O7'
_chemical_oxdiff_usercomment
'AJCJMA #11660 IN FOMBLIN FILM ON MICROMOUNT FOR AJ/CJM'
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 C(H,H,H,H,H,H) groups
2. Others
 Sof(H51D)=Sof(H51E)=Sof(H51F)=1-FVAR(1)
 Sof(H51A)=Sof(H51B)=Sof(H51C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B), C16(H16A,H16B), C42(H42A,H42B), C44(H44A,
 H44B), C46(H46A,H46B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C33(H33), C37(H37), C38(H38)
3.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C21(H21A,H21B,H21C), C47(H47A,H47B,H47C), C51(H51A,H51B,
 H51C), C51(H51D,H51E,H51F)
;