Crystal structure of (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-((1-acetyl-5-bromo-4-chloro-1H-indol-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate hemihydrate C24H25BrClNO11
Liu, Yucong; Wang, Pingqiao; Ding, Haixin; Zeitschrift für Kristallographie - New Crystal Structures 237 (2022) 755–757; doi:10.1515/ncrs-2022-0132

data_8107207
_publ_section_title
;
 Crystal structure of
 (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-((1-acetyl-5-bromo-4-chloro-1H-indol-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl
 triacetate hemihydrate C24H25BrClNO11
;
_journal_issue                   4
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              755
_journal_page_last               757
_journal_paper_doi               10.1515/ncrs-2022-0132
_journal_volume                  237
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C24 H25 Br Cl N O11, 0.5(H2 O)'
_chemical_formula_sum            'C24 H26 Br Cl N O11.5'
_chemical_formula_weight         627.82
_chemical_name_systematic
;
(N-acetyl-5-bromo-4-chloro-3-indoxyl)-2,3,4,6-tetra-O-acetyl-\b-D-galactopyranoside
;
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 114.867(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.914(5)
_cell_length_b                   7.9349(14)
_cell_length_c                   13.062(2)
_cell_measurement_reflns_used    3114
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.49
_cell_measurement_theta_min      2.68
_cell_volume                     2719.0(8)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker Smart APEX-II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8181
_diffrn_reflns_point_group_measured_fraction_full 0.909
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.591
_diffrn_reflns_theta_min         2.759
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.672
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4779
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1093 before and 0.0555 after correction.
The Ratio of minimum to maximum transmission is 0.6410.
The \l/2 correction factor is 0.00150.
;
_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    1.534
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             1284
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1365 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.033(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         5436
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0147P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0804
_reflns_Friedel_coverage         0.647
_reflns_Friedel_fraction_full    0.809
_reflns_Friedel_fraction_max     0.733
_reflns_number_gt                4033
_reflns_number_total             5436
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0132_suppl.cif
_cod_data_source_block           1
_cod_original_cell_volume        2718.9(8)
_cod_original_formula_sum        'C24 H26 Br Cl N O11.50'
_cod_database_code               8107207
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.952
_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, All O(H,H) groups
2. Others
 Fixed Sof: H12D(0.5) H12E(0.5)
3.a Free rotating group:
 O12(H12D,H12E)
3.b Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C1(H1), C4(H4)
3.c Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
3.d Aromatic/amide H refined with riding coordinates:
 C22(H22), C20(H20), C19(H19)
3.e Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C12(H12A,H12B,H12C), C8(H8A,H8B,H8C), C10(H10A,H10B,
 H10C), C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'