Copper-catalyzed synthesis of glycosyl carboxamides from glycosyl carboxylic acids and isocyanates.
Fan, Guo-Zhao; Hu, Xiang-Guo; Liu, Shuai; Organic & biomolecular chemistry 23 (2025) 10067–10071; doi:10.1039/d5ob01490e

data_7160833
_publ_section_title
;
 Copper-catalyzed synthesis of glycosyl carboxamides from glycosyl
 carboxylic acids and isocyanates.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10067
_journal_page_last               10071
_journal_paper_doi               10.1039/d5ob01490e
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration rm
_chemical_formula_moiety         '4(C16 H21 N O5)'
_chemical_formula_sum            'C64 H84 N4 O20'
_chemical_formula_weight         1229.3823
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_Int_Tables_number      5
_audit_creation_date             2025-09-11
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.06.29 svn.r12e2184c for OlexSys, GUI svn.r6374)
;
_audit_update_record
;
2025-09-11 deposited with the CCDC.	2025-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.607(9)
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   19.1760(15)
_cell_length_b                   5.7616(6)
_cell_length_c                   14.2746(16)
_cell_measurement_reflns_used    1967
_cell_measurement_temperature    293
_cell_measurement_theta_max      24.0720
_cell_measurement_theta_min      3.9760
_cell_volume                     1575.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-beta (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0353
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9962
_diffrn_measured_fraction_theta_max 0.8903
_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    -35.00  53.00   1.00    7.46    --  -15.92  37.00  90.00   88
  2  \w    -85.00  53.00   1.00    7.46    --  -15.92   0.00-120.00  138
  3  \w    -10.00  42.00   1.00    7.46    --   16.85  77.00 -30.00   52
  4  \w    -45.00  -3.00   1.00    7.46    --  -15.92  19.00 -30.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0129579000
_diffrn_orient_matrix_UB_12      -0.0505102000
_diffrn_orient_matrix_UB_13      0.0410509000
_diffrn_orient_matrix_UB_21      -0.0346939000
_diffrn_orient_matrix_UB_22      0.0199593000
_diffrn_orient_matrix_UB_23      -0.0175096000
_diffrn_orient_matrix_UB_31      -0.0003968000
_diffrn_orient_matrix_UB_32      -0.1102084000
_diffrn_orient_matrix_UB_33      -0.0221634000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.9962
_diffrn_reflns_Laue_measured_fraction_max 0.8903
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5433
_diffrn_reflns_point_group_measured_fraction_full 0.9081
_diffrn_reflns_point_group_measured_fraction_max 0.7654
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.88
_diffrn_reflns_theta_min         3.48
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38443
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light gray'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    gray
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             164.097
_refine_diff_density_max         0.3600
_refine_diff_density_min         -0.3642
_refine_diff_density_rms         0.0852
_refine_ls_abs_structure_details
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   2.4(10)
_refine_ls_d_res_high            0.7357
_refine_ls_d_res_low             5.8481
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0549
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3184
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0549
_refine_ls_R_factor_all          0.1042
_refine_ls_R_factor_gt           0.0824
_refine_ls_shift/su_max          -0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1294P)^2^+0.4063P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2072
_refine_ls_wR_factor_ref         0.2351
_reflns_Friedel_coverage         0.614
_reflns_limit_h_max              24
_reflns_limit_h_min              -25
_reflns_limit_k_max              7
_reflns_limit_k_min              -7
_reflns_limit_l_max              19
_reflns_limit_l_min              -18
_reflns_number_gt                2359
_reflns_number_total             3184
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ob01490e2.cif
_cod_data_source_block           FGZ-1_auto
_cod_depositor_comments          'Adding full bibliography for 7160833.cif.'
_cod_original_sg_symbol_Hall     ' C 2y'
_cod_database_code               7160833
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18), C21(H21), C19(H19), C20(H20)
2.b Aromatic/amide H refined with riding coordinates:
 N5(H5), C13(H13), C11(H11), C10(H10), C14(H14)
2.c Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c), C00K(H00a,H00b,H00c), C00L(H00d,H00e,H00f), C00M(H00g,
 H00h,H00i)
;
_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 2.184
_oxdiff_exptl_absorpt_empirical_full_min 0.571