Non-classical <i>C</i>-saccharide linkage of dehydroalanine: synthesis of <i>C</i>-glycoamino acids and <i>C</i>-glycopeptides.
Wang, Mengran; Wang, Chao; Xie, Xiuling; Pan, Da; Liu, Liangyu; Chen, Qiao; Li, Zhixuan; Zhang, Qi; Xu, Zhaoqing; Chemical communications (Cambridge, England) 59 (2023) 3305–3308; doi:10.1039/d2cc06653j

data_7131300
_publ_section_title
;
 Non-classical <i>C</i>-saccharide linkage of dehydroalanine: synthesis of
 <i>C</i>-glycoamino acids and <i>C</i>-glycopeptides.
;
_journal_issue                   22
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3305
_journal_page_last               3308
_journal_paper_doi               10.1039/d2cc06653j
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C44 H41 N O10'
_chemical_formula_sum            'C44 H41 N O10'
_chemical_formula_weight         743.78
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-07
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-09-07 deposited with the CCDC.	2023-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4574(2)
_cell_length_b                   10.5099(2)
_cell_length_c                   39.2952(6)
_cell_measurement_reflns_used    10438
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      77.0520
_cell_measurement_theta_min      3.3830
_cell_volume                     3905.80(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Image Plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'Rigaku IP'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -21.00  23.00   0.50    0.05    --   47.57 -19.00 120.00   88
  2  \w     47.00  87.00   0.50    0.05    --  107.75-122.00  27.00   80
  3  \w     58.00 100.00   0.50    0.05    --  107.75 -77.00  90.00   84
  4  \w     98.00 141.00   0.50    0.05    --  107.75  37.00 -30.00   86
  5  \w     98.00 173.00   0.50    0.05    --  107.75  15.00  34.00  150
  6  \w     35.00  61.00   0.50    0.05    --  107.75 -57.00-180.00   52
  7  \w    -14.00  22.00   0.50    0.05    --   47.57 -19.00-180.00   72
  8  \w    -24.00   5.00   0.50    0.05    --  -47.57  19.00  60.00   58
  9  \w   -145.00 -50.00   0.50    0.05    -- -100.00 172.00 -14.00  190
 10  \w    -66.00 -27.00   0.50    0.05    -- -100.00  57.00 150.00   78
 11  \w    -40.00  25.00   0.50    0.05    --  -47.57  37.00 150.00  130
 12  \w   -113.00 -87.00   0.50    0.05    --  -47.57-150.00-134.00   52
 13  \w   -117.00 -92.00   0.50    0.05    --  -47.57-172.00 -26.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IP'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0591564000
_diffrn_orient_matrix_UB_12      -0.0185290000
_diffrn_orient_matrix_UB_13      0.0361655000
_diffrn_orient_matrix_UB_21      0.1509861000
_diffrn_orient_matrix_UB_22      0.0225766000
_diffrn_orient_matrix_UB_23      -0.0135025000
_diffrn_orient_matrix_UB_31      -0.0157735000
_diffrn_orient_matrix_UB_32      0.1436299000
_diffrn_orient_matrix_UB_33      0.0068165000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            14695
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.369
_diffrn_reflns_theta_min         2.249
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33015
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.8(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         7108
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0736
_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^)+(0.1037P)^2^+2.7059P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1985
_refine_ls_wR_factor_ref         0.2018
_reflns_Friedel_coverage         0.606
_reflns_Friedel_fraction_full    0.832
_reflns_Friedel_fraction_max     0.745
_reflns_number_gt                6423
_reflns_number_total             7108
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06653j2.cif
_cod_data_source_block           wangmengran-xzhq_0907-1_auto
_cod_depositor_comments          'Adding full bibliography for 7131300.cif.'
_cod_database_code               7131300
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.879
_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. Restrained distances
 O9-C34 \\sim O10-C34
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O10) \\sim Ueq, Uanis(O9) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.005
4. Others
 Fixed Sof: O9(0.5) O10(0.5)
5.a Ternary CH refined with riding coordinates:
 C2(H2A), C6(H6), C18(H18), C20(H20), C29(H29), C31(H31)
5.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C23(H23A,H23B)
5.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C15(H15), C16(H16),
 C19(H19), C21(H21), C22(H22), C24(H24), C26(H26), C27(H27), C30(H30), C32(H32),
  C33(H33), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40),
 C41(H41), C42(H42)
5.d Idealised Me refined as rotating group:
 C43(H43A,H43B,H43C), C44(H44A,H44B,H44C)
;
_shelx_res_checksum              25748
_shelx_hkl_checksum              34183
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.540
_oxdiff_exptl_absorpt_empirical_full_min 0.548