#------------------------------------------------------------------------------
#$Date: 2025-11-29 22:58:17 +0100 (Sat 29 de Nov de 2025) $
#$Revision: 303898 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/08/7160833.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7160833
loop_
_publ_author_name
'Fan, Guo-Zhao'
'Hu, Xiang-Guo'
'Liu, Shuai'
_publ_section_title
;
 Copper-catalyzed synthesis of glycosyl carboxamides from glycosyl
 carboxylic acids and isocyanates.
;
_journal_issue                   44
_journal_name_full               'Organic & 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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -35.00  53.00   1.00    7.46    --  -15.92  37.00  90.00   88
  2  ω    -85.00  53.00   1.00    7.46    --  -15.92   0.00-120.00  138
  3  ω    -10.00  42.00   1.00    7.46    --   16.85  77.00 -30.00   52
  4  ω    -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       'ω 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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.1294P)²+0.4063P] where P=(Fo²+2Fc²)/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
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z
3 x+1/2,y+1/2,z
4 -x+1/2,y+1/2,-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
O001 O -0.51290(14) -0.2645(5) -0.7719(2) 0.0553(8) Uani 1.000000 .
O8 O -0.62048(14) -0.6418(6) -0.8080(2) 0.0597(9) Uani 1.000000 .
N5 N -0.44586(17) -0.3095(7) -0.5966(2) 0.0498(9) Uani 1.000000 .
H5 H -0.46070(17) -0.1802(7) -0.6202(2) 0.0597(11) Uiso 1.000000 R
O9 O -0.40497(15) -0.4122(7) -0.8156(2) 0.0738(11) Uani 1.000000 .
O6 O -0.4596(2) -0.6997(6) -0.6130(3) 0.0769(11) Uani 1.000000 .
C17 C -0.4741(2) -0.5045(8) -0.6352(3) 0.0476(10) Uani 1.000000 .
O7 O -0.56260(16) -0.5695(9) -0.9360(2) 0.0866(14) Uani 1.000000 .
C22 C -0.6234(2) -0.6815(8) -0.9041(3) 0.0520(11) Uani 1.000000 .
C12 C -0.39460(18) -0.2928(8) -0.5217(3) 0.0436(9) Uani 1.000000 .
C15 C -0.2956(2) -0.2432(8) -0.3729(3) 0.0527(11) Uani 1.000000 .
C13 C -0.3470(2) -0.4714(8) -0.5006(3) 0.0518(11) Uani 1.000000 .
H13 H -0.3480(2) -0.6088(8) -0.5348(3) 0.0622(13) Uiso 1.000000 R
C11 C -0.3923(2) -0.0926(7) -0.4693(3) 0.0513(11) Uani 1.000000 .
H11 H -0.4237(2) 0.0267(7) -0.4835(3) 0.0616(13) Uiso 1.000000 R
C18 C -0.53212(19) -0.4512(8) -0.7116(3) 0.0495(11) Uani 1.000000 .
H18 H -0.57474(19) -0.4074(8) -0.6806(3) 0.0594(13) Uiso 1.000000 R
C10 C -0.3430(2) -0.0670(8) -0.3946(3) 0.0581(12) Uani 1.000000 .
H10 H -0.3420(2) 0.0688(8) -0.3594(3) 0.0697(14) Uiso 1.000000 R
C14 C -0.2984(2) -0.4377(9) -0.4272(3) 0.0579(12) Uani 1.000000 .
H14 H -0.2658(2) -0.5543(9) -0.4143(3) 0.0695(15) Uiso 1.000000 R
C21 C -0.5484(2) -0.6497(8) -0.7756(3) 0.0543(11) Uani 1.000000 .
H21 H -0.5352(2) -0.7996(8) -0.7477(3) 0.0651(14) Uiso 1.000000 R
C19 C -0.4759(2) -0.3659(10) -0.8438(3) 0.0616(14) Uani 1.000000 .
H19 H -0.4784(2) -0.2677(10) -0.8999(3) 0.0740(17) Uiso 1.000000 R
C20 C -0.5094(2) -0.5970(10) -0.8641(3) 0.0613(13) Uani 1.000000 .
H20 H -0.4755(2) -0.7176(10) -0.8785(3) 0.0735(15) Uiso 1.000000 R
C16 C -0.2442(3) -0.2181(12) -0.2906(4) 0.0843(18) Uani 1.000000 .
H16a H -0.2572(15) -0.320(6) -0.2411(14) 0.126(3) Uiso 1.000000 GR
H16b H -0.1983(5) -0.258(8) -0.3095(10) 0.126(3) Uiso 1.000000 GR
H16c H -0.2444(19) -0.060(2) -0.269(2) 0.126(3) Uiso 1.000000 GR
C00K C -0.6860(2) -0.5553(10) -0.9491(4) 0.0732(15) Uani 1.000000 .
H00a H -0.6862(12) -0.397(2) -0.928(2) 0.110(2) Uiso 1.000000 GR
H00b H -0.6832(12) -0.558(6) -1.0160(4) 0.110(2) Uiso 1.000000 GR
H00c H -0.7282(3) -0.631(5) -0.932(2) 0.110(2) Uiso 1.000000 GR
C00L C -0.3669(3) -0.1993(13) -0.7989(5) 0.097(2) Uani 1.000000 .
H00d H -0.3859(17) -0.118(4) -0.747(2) 0.145(3) Uiso 1.000000 GR
H00e H -0.3186(6) -0.2343(14) -0.784(4) 0.145(3) Uiso 1.000000 GR
H00f H -0.371(2) -0.104(4) -0.8540(14) 0.145(3) Uiso 1.000000 GR
C00M C -0.6256(4) -0.9344(12) -0.9266(6) 0.112(3) Uani 1.000000 .
H00g H -0.6662(16) -1.003(2) -0.901(3) 0.168(4) Uiso 1.000000 GR
H00h H -0.627(3) -0.9548(12) -0.9935(6) 0.168(4) Uiso 1.000000 GR
H00i H -0.5844(14) -1.008(2) -0.900(3) 0.168(4) Uiso 1.000000 GR
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O001 C18 106.2(3) . . ?
C21 O8 C22 107.8(3) . . ?
C12 N5 C17 127.7(4) . . ?
C00L O9 C19 110.9(4) . . ?
O6 C17 N5 126.1(4) . . ?
C18 C17 N5 112.5(4) . . ?
C18 C17 O6 121.4(4) . . ?
C20 O7 C22 106.8(3) . . ?
O7 C22 O8 104.1(3) . . ?
C00K C22 O8 109.5(4) . . ?
C00K C22 O7 106.9(4) . . ?
C00M C22 O8 111.9(5) . . ?
C00M C22 O7 112.9(5) . . ?
C00M C22 C00K 111.3(4) . . ?
C13 C12 N5 122.3(4) . . ?
C11 C12 N5 118.0(4) . . ?
C11 C12 C13 119.7(4) . . ?
C14 C15 C10 117.7(4) . . ?
C16 C15 C10 120.2(5) . . ?
C16 C15 C14 122.1(5) . . ?
C14 C13 C12 118.1(4) . . ?
C10 C11 C12 120.4(4) . . ?
C17 C18 O001 111.9(3) . . ?
C21 C18 O001 105.0(3) . . ?
C21 C18 C17 113.8(4) . . ?
C11 C10 C15 120.4(4) . . ?
C13 C14 C15 123.7(4) . . ?
C18 C21 O8 110.1(4) . . ?
C20 C21 O8 103.2(3) . . ?
C20 C21 C18 105.0(4) . . ?
O9 C19 O001 112.3(4) . . ?
C20 C19 O001 106.5(4) . . ?
C20 C19 O9 106.4(4) . . ?
C21 C20 O7 104.9(3) . . ?
C19 C20 O7 109.1(4) . . ?
C19 C20 C21 103.8(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C18 1.437(5) . ?
O001 C19 1.401(6) . ?
O8 C22 1.391(5) . ?
O8 C21 1.439(5) . ?
N5 C17 1.353(6) . ?
N5 C12 1.422(5) . ?
O9 C19 1.426(5) . ?
O9 C00L 1.442(8) . ?
O6 C17 1.198(6) . ?
C17 C18 1.553(5) . ?
O7 C22 1.425(5) . ?
O7 C20 1.423(5) . ?
C22 C00K 1.521(6) . ?
C22 C00M 1.492(8) . ?
C12 C13 1.399(6) . ?
C12 C11 1.375(6) . ?
C15 C10 1.389(7) . ?
C15 C14 1.363(7) . ?
C15 C16 1.505(6) . ?
C13 C14 1.383(6) . ?
C11 C10 1.400(6) . ?
C18 C21 1.488(7) . ?
C21 C20 1.526(7) . ?
C19 C20 1.501(7) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C18 C17 N5 42.8(4) . . . . ?
O001 C18 C17 O6 -139.8(4) . . . . ?
O001 C18 C21 O8 -87.7(3) . . . . ?
O001 C18 C21 C20 22.7(3) . . . . ?
O001 C19 O9 C00L -66.7(5) . . . . ?
O001 C19 C20 O7 91.2(3) . . . . ?
O001 C19 C20 C21 -20.2(3) . . . . ?
O8 C22 O7 C20 35.0(4) . . . . ?
O8 C21 C18 C17 149.6(3) . . . . ?
O8 C21 C20 O7 -1.0(4) . . . . ?
O8 C21 C20 C19 113.4(3) . . . . ?
N5 C17 C18 C21 161.6(4) . . . . ?
N5 C12 C13 C14 179.1(4) . . . . ?
N5 C12 C11 C10 179.9(4) . . . . ?
O9 C19 C20 O7 -148.8(3) . . . . ?
O9 C19 C20 C21 99.8(3) . . . . ?
O6 C17 C18 C21 -20.9(5) . . . . ?
C17 C18 C21 C20 -100.0(4) . . . . ?
O7 C20 C21 C18 -116.4(4) . . . . ?
C12 C13 C14 C15 1.9(5) . . . . ?
C12 C11 C10 C15 0.3(5) . . . . ?
C18 C21 C20 C19 -1.9(3) . . . . ?
