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_1551960
_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         'C34 H34 O14, 0.48(C H2 Cl2)'
_chemical_formula_sum            'C34.48 H34.96 Cl0.96 O14'
_chemical_formula_weight         707.21
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8002(8)
_cell_length_b                   11.4061(10)
_cell_length_c                   30.952(3)
_cell_measurement_reflns_used    9192
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.629
_cell_measurement_theta_min      2.856
_cell_volume                     3459.9(5)
_computing_cell_refinement       'SAINT v8.34A (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  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker Proteum-R'
_diffrn_measurement_method       '\w & \f scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            37641
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        66.624
_diffrn_reflns_theta_max         66.624
_diffrn_reflns_theta_min         2.855
_diffrn_source                   'rotating anode'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.543
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1138 before and 0.0516 after correction.
The Ratio of minimum to maximum transmission is 0.9220.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       block
_exptl_crystal_F_000             1480.3
_exptl_crystal_size_max          0.172
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.123
_refine_ls_abs_structure_details
;
 Flack x determined using 1277 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.039(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.217
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         2986
_refine_ls_number_restraints     244
_refine_ls_restrained_S_all      1.174
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0628P)^2^+4.8498P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1259
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    0.948
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                2960
_reflns_number_total             2986
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            nchem.2173-s2.cif
_cod_data_source_block           tian11a_0m
_cod_database_code               1551960
_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. Restrained distances
 C2-C1A
 1.54 with sigma of 0.02
 C2-C1B
 1.54 with sigma of 0.02
 C1S-Cl2S
 1.65 with sigma of 0.02
 C1S-Cl1S
 1.65 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(C1A) = Uanis(C1B)
Uanis(Cl1S) = Uanis(Cl2S)
Uanis(C1S) = Uanis(Cl2S)
5. Others
 Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=1-FVAR(1)
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=FVAR(1)
 Sof(Cl1S)=Sof(C1S)=Sof(H1SA)=Sof(H1SB)=Sof(Cl2S)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C14(H14)
6.b Secondary CH2 refined with riding coordinates:
 C1S(H1SA,H1SB), C12(H12A,H12B), C13(H13A,H13B)
6.c Aromatic/amide H refined with riding coordinates:
 C7(H7A)
6.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,
 H1BC)
6.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O7(H7)
;
_shelx_res_checksum              39310
_shelx_hkl_checksum              74790
_olex2_submission_special_instructions 'No special instructions were received'