Synthesis of Sialidase-Resistant Oligosaccharide and Antibody Glycoform Containing α2,6-Linked 3F<sup>ax</sup>-Neu5Ac.
Lo, Hong-Jay; Krasnova, Larissa; Dey, Supriya; Cheng, Ting; Liu, Haitian; Tsai, Tsung-I; Wu, Kevin Binchia; Wu, Chung-Yi; Wong, Chi-Huey; Journal of the American Chemical Society 141 (2019) 6484–6488; doi:10.1021/jacs.9b01991

data_4128251
_publ_section_title
;
 Synthesis of Sialidase-Resistant Oligosaccharide and Antibody Glycoform
 Containing \a2,6-Linked 3F<sup>ax</sup>-Neu5Ac.
;
_journal_issue                   16
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6484
_journal_page_last               6488
_journal_paper_doi               10.1021/jacs.9b01991
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C54 H58 F N O19 S'
_chemical_formula_sum            'C54 H58 F N O19 S'
_chemical_formula_weight         1076.07
_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_Hall           'P 61'
_space_group_name_H-M_alt        'P 61'
_symmetry_space_group_name_Hall  'P 61'
_symmetry_space_group_name_H-M   'P 61'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-05-01
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   21.1703(5)
_cell_length_b                   21.1703(5)
_cell_length_c                   22.7806(6)
_cell_measurement_reflns_used    9773
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      67.653
_cell_measurement_theta_min      3.094
_cell_volume                     8842.0(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_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      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II Cu'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            88061
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         68.329
_diffrn_reflns_theta_min         2.410
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker Microstar FR-592'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.107
_exptl_absorpt_correction_T_max  0.3201
_exptl_absorpt_correction_T_min  0.2175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0966 before and 0.0608 after correction. The Ratio of minimum to maximum transmission is 0.6795. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       Rod
_exptl_crystal_F_000             3396
_exptl_crystal_size_max          0.457
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.091
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 4263 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     786
_refine_ls_number_reflns         10475
_refine_ls_number_restraints     181
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0641P)^2^+0.6903P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0970
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_full    0.948
_reflns_Friedel_fraction_max     0.944
_reflns_number_gt                9561
_reflns_number_total             10475
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b01991_si_002.cif
_cod_data_source_block           Wong_Jay144
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        8842.0(5)
_cod_database_code               4128251
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.906
_shelx_estimated_absorpt_t_min   0.632
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O3B) = Uanis(O3)
Uanis(O18) = Uanis(O18B)
Uanis(C51B) = Uanis(C51)
Uanis(C52B) = Uanis(C52)
Uanis(O11B) = Uanis(O11)
Uanis(C37) = Uanis(C37B)
3. Rigid body (RIGU) restrains
 O3, O3B, O14, O14B, C3, C30, C30B, C31, C31B, C32, C32B, C33, C33B, C34, C34B,
  C35, C35B, C36, C36B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 O11, O11B, O18, O18B, C14, C51, C51B, C52, C52B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4. Others
 Sof(O3B)=Sof(O14B)=Sof(H3B)=Sof(C30B)=Sof(C31B)=Sof(C32B)=Sof(H32B)=Sof(C33B)=
 Sof(H33B)=Sof(C34B)=Sof(H34B)=Sof(C35B)=Sof(H35B)=Sof(C36B)=Sof(H36B)=1-FVAR(1)
 Sof(O3)=Sof(O14)=Sof(H3A)=Sof(C30)=Sof(C31)=Sof(C32)=Sof(H32)=Sof(C33)=
 Sof(H33)=Sof(C34)=Sof(H34)=Sof(C35)=Sof(H35)=Sof(C36)=Sof(H36)=FVAR(1)
 Sof(O11B)=Sof(O18B)=Sof(H14A)=Sof(C51B)=Sof(C52B)=Sof(H52D)=Sof(H52E)=
 Sof(H52F)=1-FVAR(2)
 Sof(O11)=Sof(O18)=Sof(H14)=Sof(C51)=Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(H52C)=
 FVAR(2)
 Sof(C37B)=Sof(H37C)=Sof(H37D)=1-FVAR(3)
 Sof(C37)=Sof(H37A)=Sof(H37B)=FVAR(3)
5.a Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3A), C3(H3B), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11),
  C12(H12), C13(H13), C14(H14), C14(H14A)
5.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C15(H15A,H15B), C37(H37A,H37B), C37B(H37C,H37D)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C17(H17), C18(H18), C20(H20), C21(H21), C25(H25), C26(H26), C27(H27),
 C28(H28), C29(H29), C32(H32), C32B(H32B), C33(H33), C33B(H33B), C34(H34),
 C34B(H34B), C35(H35), C35B(H35B), C36(H36), C36B(H36B), C39(H39), C40(H40),
 C41(H41), C42(H42), C43(H43)
5.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C44(H44A,H44B,H44C), C46(H46A,H46B,H46C), C48(H48A,H48B,
 H48C), C50(H50A,H50B,H50C), C52(H52A,H52B,H52C), C52B(H52D,H52E,H52F),
 C54(H54A,H54B,H54C)
;
_shelx_res_checksum              97558
_shelx_hkl_checksum              34541
_shelx_fab_checksum              55596
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'