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_1513452
_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         'C30 H35 N4 O11, C H4 O'
_chemical_formula_sum            'C31 H36 D4 N4 O12'
_chemical_formula_weight         664.69
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_cell_angle_alpha                87.895(5)
_cell_angle_beta                 83.248(5)
_cell_angle_gamma                88.205(5)
_cell_formula_units_Z            2
_cell_length_a                   8.2246(5)
_cell_length_b                   10.2692(6)
_cell_length_c                   19.3753(13)
_cell_measurement_reflns_used    3372
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.8780
_cell_measurement_theta_min      4.2980
_cell_volume                     1623.39(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_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 10.6296
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1673827000
_diffrn_orient_matrix_UB_12      0.0649555000
_diffrn_orient_matrix_UB_13      -0.0043518000
_diffrn_orient_matrix_UB_21      -0.0142697000
_diffrn_orient_matrix_UB_22      0.0006537000
_diffrn_orient_matrix_UB_23      0.0799833000
_diffrn_orient_matrix_UB_31      0.0859269000
_diffrn_orient_matrix_UB_32      -0.1353991000
_diffrn_orient_matrix_UB_33      0.0012565000
_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  0.0459
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11682
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.714
_diffrn_reflns_theta_min         4.310
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    0.881
_exptl_absorpt_correction_T_max  1.264
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
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    1.360
_exptl_crystal_description       needle
_exptl_crystal_F_000             700
_exptl_crystal_recrystallization_method
'crystallised by the slow evaporation of a CD3OD solution'
_exptl_crystal_size_max          0.3765
_exptl_crystal_size_mid          0.0743
_exptl_crystal_size_min          0.0303
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     465
_refine_ls_number_reflns         6380
_refine_ls_number_restraints     75
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0712
_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^)+(0.0760P)^2^+1.0119P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1803
_refine_ls_wR_factor_ref         0.1941
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4890
_reflns_number_total             6380
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol403598k_si_002.cif
_cod_data_source_block           ajcjmc_sq_s
_cod_original_cell_volume        1623.38(17)
_cod_database_code               1513452
_nottingham_internal_coll_name   AJCJMC
_nottingham_internal_coll_number 12857
_nottingham_internal_coll_client AJ/CJM
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_time '4, 16'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_user   WL
_nottingham_internal_coll_date   30/9/2013
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_user WL
_nottingham_internal_process_date 30/9/2013
_nottingham_internal_solution_user wl
_nottingham_internal_solution_date 30/9/2013
_nottingham_internal_refinement_user wl
_nottingham_internal_refinement_date 2/10/2013
_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         'C31 H40 N4 O12'
_chemical_oxdiff_usercomment
'AJCJMC #12857 IN FOMBLIN FIML ON MICROMOUNT FOR AJ/CJM'
_reflns_odcompleteness_completeness 99.50
_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, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Shared sites
{C32, C32A}
3. Uiso/Uaniso restraints and constraints
N33A \\sim N33 \\sim C32: within 2A with sigma of 0.005 and sigma for terminal
atoms of 0.01
Uanis(C32) = Uanis(C32A)
4. Rigid body (RIGU) restrains
 N34, N33, N33A, O37, O36, O36A, C41, C39, C40, C39A, C41A, C40A, C38
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C32A)=Sof(N33A)=Sof(H33C)=Sof(H33D)=Sof(O36A)=Sof(C39A)=Sof(H39D)=
 Sof(H39E)=Sof(H39F)=Sof(C40A)=Sof(H40D)=Sof(H40E)=Sof(H40F)=Sof(C41A)=
 Sof(H41D)=Sof(H41E)=Sof(H41F)=1-FVAR(1)
 Sof(C32)=Sof(N33)=Sof(H33A)=Sof(H33B)=Sof(O36)=Sof(C39)=Sof(H39A)=Sof(H39B)=
 Sof(H39C)=Sof(C40)=Sof(H40A)=Sof(H40B)=Sof(H40C)=Sof(C41)=Sof(H41A)=Sof(H41B)=
 Sof(H41C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C12(H12)
6.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C16(H16A,H16B), C22(H22A,H22B), C23(H23A,H23B)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8)
6.d X=CH2 refined with riding coordinates:
 N33(H33A,H33B), N33A(H33C,H33D)
6.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,
 H31C), C39(H39A,H39B,H39C), C39A(H39D,H39E,H39F), C40(H40A,H40B,H40C),
 C40A(H40D,H40E,H40F), C41(H41A,H41B,H41C), C41A(H41D,H41E,H41F)
;
_shelx_res_checksum              25526
_shelx_hkl_checksum              50255
_shelx_fab_checksum              72834