Glycosylation with 3,5-Dimethyl-4-(2'-phenylethynylphenyl)phenyl (EPP) Glycosides via a Dearomative Activation Mechanism.
Hu, Zhifei; Tang, Yu; Yu, Biao; Journal of the American Chemical Society 141 (2019) 4806–4810; doi:10.1021/jacs.9b00210

data_4129035
_publ_section_title
;
 Glycosylation with 3,5-Dimethyl-4-(2'-phenylethynylphenyl)phenyl (EPP)
 Glycosides via a Dearomative Activation Mechanism.
;
_journal_issue                   12
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4806
_journal_page_last               4810
_journal_paper_doi               10.1021/jacs.9b00210
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C36 H36 O10'
_chemical_formula_sum            'C36 H36 O10'
_chemical_formula_weight         628.65
_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     dual
_audit_creation_date             2019-02-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.0850(10)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   10.7002(4)
_cell_length_b                   23.8506(8)
_cell_length_c                   22.5203(8)
_cell_measurement_reflns_used    9874
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.803
_cell_measurement_theta_min      3.63
_cell_volume                     5690.2(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            69176
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.906
_diffrn_reflns_theta_min         3.224
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.426
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1385 before and 0.0831 after correction. The Ratio of minimum to maximum transmission is 0.7577. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.101
_exptl_crystal_description       block
_exptl_crystal_F_000             1992
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.785
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details
;
 Flack x determined using 5025 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.30(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1261
_refine_ls_number_reflns         21429
_refine_ls_number_restraints     110
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.1336
_refine_ls_R_factor_gt           0.1020
_refine_ls_shift/su_max          0.046
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2625
_refine_ls_wR_factor_ref         0.2990
_reflns_Friedel_coverage         0.941
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                13882
_reflns_number_total             21429
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b00210_si_003.cif
_cod_data_source_block           mjl18376_0m
_cod_database_code               4129035
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.939
_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
2. Rigid bond restraints
 C26B, C27B
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
C31 \\sim C32 \\sim C33 \\sim C34 \\sim C35 \\sim C36: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
C31A \\sim C32A \\sim C33A \\sim C34A \\sim C35A \\sim C36A: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
C31B \\sim C32B \\sim C33B \\sim C34B \\sim C35B \\sim C36B: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C1A(H1A), C2A(H2A), C3A(H3A),
 C4A(H4A), C5A(H5A), C1B(H1B), C2B(H2B), C3B(H3B), C4B(H4B), C5B(H5B)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C6A(H6AA,H6AB), C6B(H6BA,H6BB)
4.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C20(H20), C24(H24), C25(H25), C26(H26), C27(H27), C32(H32),
 C33(H33), C34(H34), C35(H35), C36(H36), C16A(H16A), C20A(H20A), C24A(H24A),
 C25A(H25A), C26A(H26A), C27A(H27A), C32A(H32A), C33A(H33A), C34A(H34A),
 C35A(H35A), C36A(H36A), C16B(H16B), C20B(H20B), C24B(H24B), C25B(H25B),
 C26B(H26B), C27B(H27B), C32B(H32B), C33B(H33B), C34B(H34B), C35B(H35B),
 C36B(H36B)
4.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C14(H14A,H14B,
 H14C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C8A(H8AA,H8AB,H8AC),
 C10A(H10D,H10E,H10F), C12A(H12D,H12E,H12F), C14A(H14D,H14E,H14F), C21A(H21D,
 H21E,H21F), C22A(H22D,H22E,H22F), C8B(H8BA,H8BB,H8BC), C10B(H10G,H10H,H10I),
 C12B(H12G,H12H,H12I), C14B(H14G,H14H,H14I), C21B(H21G,H21H,H21I), C22B(H22G,
 H22H,H22I)
;
_shelx_res_checksum              36797
_shelx_hkl_checksum              638
_shelx_fab_checksum              56106
_olex2_submission_special_instructions 'No special instructions were received'