Atropselective syntheses of (-) and (+) rugulotrosin A utilizing point-to-axial chirality transfer
Tian Qin; Sarah L. Skraba-Joiner; Zeinab G. Khalil; Richard P. Johnson; Robert J. Capon; John A. Porco Jr; Nature Chemistry 7 (2015) 234–240; doi:10.1038/nchem.2173

data_1551961
_publ_section_title
;
 Atropselective syntheses of (-) and (+) rugulotrosin A utilizing
 point-to-axial chirality transfer
;
_journal_name_full               'Nature Chemistry'
_journal_page_first              234
_journal_page_last               240
_journal_paper_doi               10.1038/nchem.2173
_journal_volume                  7
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C40 H42 O16'
_chemical_formula_sum            'C40 H42 O16'
_chemical_formula_weight         778.73
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 111.0750(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.3036(4)
_cell_length_b                   15.8950(5)
_cell_length_c                   11.5465(4)
_cell_measurement_reflns_used    9861
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.111
_cell_measurement_theta_min      4.103
_cell_volume                     1935.80(11)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.98
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Proteum-R'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            48580
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.144
_diffrn_reflns_theta_max         67.144
_diffrn_reflns_theta_min         4.103
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    0.877
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0977 before and 0.0417 after correction.
The Ratio of minimum to maximum transmission is 0.8632.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       prism
_exptl_crystal_F_000             820
_exptl_crystal_size_max          0.367
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.092
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 3263 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     529
_refine_ls_number_reflns         6886
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0270
_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^)+(0.0477P)^2^+0.2798P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0741
_reflns_Friedel_coverage         0.916
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                6839
_reflns_number_total             6886
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            nchem.2173-s3.cif
_cod_data_source_block           tian10a_0m
_cod_database_code               1551961
_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 O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C3A) = Uanis(C3A)
Uanis(O9B) = Uanis(O9A)
Uanis(C2B) = Uanis(C2A)
Uanis(C1A) = Uanis(C1A)
Uanis(C1B) = Uanis(C1A)
Uanis(C3B) = Uanis(C3A)
3. Others
 Sof(O9B)=Sof(C3B)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=
 Sof(H1BC)=1-FVAR(1)
 Sof(O9A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=
 Sof(C3A)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C4(H4A), C16(H16)
4.b Secondary CH2 refined with riding coordinates:
 C2A(H2AA,H2AB), C18(H18A,H18B), C23(H23A,H23B), C24(H24A,H24B), C36(H36A,
 H36B), C37(H37A,H37B), C2B(H2BA,H2BB)
4.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C30(H30)
4.d Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C), C1A(H1AA,H1AB,H1AC), C19(H19A,H19B,H19C), C26(H26A,H26B,
 H26C), C28(H28A,H28B,H28C), C31(H31A,H31B,H31C), C35(H35A,H35B,H35C), C39(H39A,
 H39B,H39C), C1B(H1BA,H1BB,H1BC)
4.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5)
;
_shelx_res_checksum              7210
_shelx_hkl_checksum              10187
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'