#------------------------------------------------------------------------------
#$Date: 2022-03-16 04:16:28 +0200 (Wed, 16 Mar 2022) $
#$Revision: 273717 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/46/7244614.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_7244614
loop_
_publ_author_name
'Ziemniak, Marcin'
'Pawlędzio, Sylwia'
'Zawadzka-Kaźmierczuk, Anna'
'Dominiak, Paulina M.'
'Trzybiński, Damian'
'Koźmiński, Wiktor'
'Zieliński, Rafał'
'Fokt, Izabela'
'Priebe, Waldemar'
'Woźniak, Krzysztof'
'Pająk, Beata'
_publ_section_title
;
 X-ray wavefunction refinement and comprehensive structural studies on
 bromo-substituted analogues of 2-deoxy-d-glucose in solid state and
 solution
;
_journal_issue                   14
_journal_name_full               'RSC Advances'
_journal_page_first              8345
_journal_page_last               8360
_journal_paper_doi               10.1039/D1RA08312K
_journal_volume                  12
_journal_year                    2022
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C12 H22 O11'
_chemical_formula_sum            'C12 H22 O11'
_chemical_formula_weight         342.302
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_Int_Tables_number      4
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-08-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-11-09 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.983(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7727(9)
_cell_length_b                   8.7216(11)
_cell_length_c                   10.8637(11)
_cell_measurement_reflns_used    4334
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.8820
_cell_measurement_theta_min      2.0180
_cell_volume                     717.63(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9971
_diffrn_measured_fraction_theta_max 0.9588
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 109.00   1.00    3.27    --   20.00  54.00   6.06  183
  2  ω     65.00 110.00   1.00    3.27    --   20.00  54.00-180.00   45
  3  ω    -74.00 109.00   1.00    3.27    --   20.00  54.00 -60.00  183
  4  ω    -74.00 109.00   1.00    3.27    --   20.00  54.00-150.00  183
  5  ω    -74.00 109.00   1.00    3.27    --   20.00  54.00-150.00  183
  6  ω    -74.00 109.00   1.00    3.27    --   20.00  54.00-180.00  183
  7  ω    -74.00 109.00   1.00    3.27    --   20.00  54.00-180.00  183
  8  ω    -74.00  69.00   1.00    3.27    --   20.00  54.00-120.00  143
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0067778000
_diffrn_orient_matrix_UB_12      0.0437926000
_diffrn_orient_matrix_UB_13      -0.0557807000
_diffrn_orient_matrix_UB_21      -0.0263053000
_diffrn_orient_matrix_UB_22      -0.0666037000
_diffrn_orient_matrix_UB_23      -0.0370776000
_diffrn_orient_matrix_UB_31      -0.0895987000
_diffrn_orient_matrix_UB_32      0.0162712000
_diffrn_orient_matrix_UB_33      -0.0005508000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.9971
_diffrn_reflns_Laue_measured_fraction_max 0.9588
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13618
_diffrn_reflns_point_group_measured_fraction_full 0.9228
_diffrn_reflns_point_group_measured_fraction_max 0.8545
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         29.21
_diffrn_reflns_theta_min         2.69
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95459
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.12b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_description       prism
_exptl_crystal_F_000             364.302
_refine_diff_density_max         0.1220
_refine_diff_density_min         -0.1424
_refine_diff_density_rms         0.0311
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.1(8)
_refine_ls_d_res_high            0.7283
_refine_ls_d_res_low             7.5740
_refine_ls_goodness_of_fit_ref   1.0926
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    1
_refine_ls_number_parameters     400
_refine_ls_number_reflns         3318
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0926
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0238
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0118P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0395
_refine_ls_wR_factor_ref         0.0410
_reflns_Friedel_coverage         0.736
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              9
_reflns_limit_k_min              -11
_reflns_limit_l_max              14
_reflns_limit_l_min              -14
_reflns_number_gt                3002
_reflns_number_total             3318
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1ra08312k2.cif
_cod_data_source_block           sucrose
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7244614
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All H(H) groups
;
_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 1.075
_oxdiff_exptl_absorpt_empirical_full_min 0.948
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,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
O1 O 0.13146(10) -0.93498(10) -0.87713(7) 0.0211(2) Uani 1.000000 .
O2 O 0.21415(14) -0.78925(14) -1.08140(9) 0.0344(3) Uani 1.000000 .
H2 H 0.218(3) -0.906(3) -1.100(3) 0.106(12) Uani 1.000000 .
O3 O 0.14314(16) -0.51956(14) -0.84868(12) 0.0426(3) Uani 1.000000 .
H3 H 0.068(3) -0.436(4) -0.830(3) 0.111(12) Uani 1.000000 .
O4 O -0.20277(15) -0.58615(13) -0.80825(9) 0.0361(3) Uani 1.000000 .
H4 H -0.243(3) -0.568(3) -0.731(2) 0.072(9) Uani 1.000000 .
O5 O -0.24740(13) -0.89823(14) -0.72945(9) 0.0264(2) Uani 1.000000 .
H5 H -0.342(3) -0.965(3) -0.771(2) 0.061(7) Uani 1.000000 .
O6 O 0.18430(9) -1.23913(11) -0.71193(7) 0.0212(2) Uani 1.000000 .
O7 O 0.45919(13) -1.09608(14) -0.82656(9) 0.0329(2) Uani 1.000000 .
H7 H 0.330(3) -1.056(4) -0.852(2) 0.080(10) Uani 1.000000 .
O8 O 0.58917(12) -1.23596(14) -0.47860(9) 0.0283(2) Uani 1.000000 .
H8 H 0.694(3) -1.182(3) -0.4837(17) 0.053(7) Uani 1.000000 .
O9 O 0.29549(13) -1.01621(13) -0.42617(9) 0.0245(2) Uani 1.000000 .
H9 H 0.323(3) -0.931(3) -0.4655(19) 0.055(7) Uani 1.000000 .
O10 O -0.12103(14) -1.09834(14) -0.53026(10) 0.0286(3) Uani 1.000000 .
H10 H -0.154(3) -1.013(3) -0.5832(19) 0.063(8) Uani 1.000000 .
O11 O 0.10832(9) -0.98735(10) -0.67146(6) 0.01790(19) Uani 1.000000 .
C1 C 0.20471(16) -0.78258(16) -0.85891(11) 0.0216(3) Uani 1.000000 .
H1 H 0.2937(18) -0.7688(19) -0.7613(11) 0.038(5) Uani 1.000000 .
C2 C 0.31586(19) -0.7636(2) -0.95703(12) 0.0284(3) Uani 1.000000 .
H2A H 0.433(2) -0.850(2) -0.9350(14) 0.042(5) Uani 1.000000 .
H2B H 0.364(2) -0.646(2) -0.9507(19) 0.067(6) Uani 1.000000 .
C3 C 0.05780(17) -0.66283(16) -0.87416(12) 0.0235(3) Uani 1.000000 .
H3B H -0.0224(19) -0.666(2) -0.9722(12) 0.050(5) Uani 1.000000 .
C4 C -0.06423(17) -0.69748(16) -0.78530(11) 0.0224(3) Uani 1.000000 .
H4B H 0.0119(18) -0.685(2) -0.6868(13) 0.046(5) Uani 1.000000 .
C5 C -0.13604(16) -0.85951(16) -0.81241(11) 0.0195(3) Uani 1.000000 .
H5B H -0.2103(18) -0.8634(19) -0.9122(13) 0.041(5) Uani 1.000000 .
C6 C 0.01492(15) -0.97612(17) -0.79973(10) 0.0178(3) Uani 1.000000 .
H6 H -0.0344(19) -1.088(2) -0.8340(13) 0.038(4) Uani 1.000000 .
C7 C 0.13094(14) -1.14137(14) -0.62433(9) 0.0162(2) Uani 1.000000 .
C8 C -0.04395(16) -1.20287(18) -0.60301(12) 0.0227(3) Uani 1.000000 .
H8A H -0.0219(19) -1.313(2) -0.5539(13) 0.038(2) Uani 1.000000 .
H8B H -0.1312(19) -1.222(2) -0.6929(14) 0.056(4) Uiso 1.000000 .
C9 C 0.28561(15) -1.14278(16) -0.50720(10) 0.0172(3) Uani 1.000000 .
H9B H 0.2697(17) -1.243(2) -0.4535(12) 0.036(4) Uani 1.000000 .
C10 C 0.44512(15) -1.16733(17) -0.56483(11) 0.0190(3) Uani 1.000000 .
H10B H 0.4844(19) -1.058(2) -0.5996(14) 0.043(5) Uani 1.000000 .
C11 C 0.37135(16) -1.27262(17) -0.67630(11) 0.0199(3) Uani 1.000000 .
H11 H 0.384(2) -1.393(2) -0.6480(14) 0.047(5) Uani 1.000000 .
C12 C 0.45341(19) -1.25206(18) -0.78939(13) 0.0279(3) Uani 1.000000 .
H12A H 0.379(2) -1.322(3) -0.8690(14) 0.074(7) Uani 1.000000 .
H12B H 0.5929(19) -1.292(2) -0.7612(15) 0.055(6) Uani 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'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
C6 O1 C1 116.00(9) . . ?
C11 O6 C7 111.85(8) . . ?
C7 O11 C6 114.13(9) . . ?
C2 C1 O1 105.79(11) . . ?
C3 C1 O1 110.64(10) . . ?
C3 C1 C2 112.15(11) . . ?
C1 C2 O2 111.48(11) . . ?
C1 C3 O3 106.06(11) . . ?
C4 C3 O3 112.46(11) . . ?
C4 C3 C1 110.55(11) . . ?
C3 C4 O4 107.80(11) . . ?
C5 C4 O4 111.55(11) . . ?
C5 C4 C3 108.29(10) . . ?
C4 C5 O5 110.25(10) . . ?
C6 C5 O5 110.32(10) . . ?
C6 C5 C4 110.95(10) . . ?
O11 C6 O1 110.24(9) . . ?
C5 C6 O1 110.94(10) . . ?
C5 C6 O11 110.18(9) . . ?
O11 C7 O6 110.92(8) . . ?
C8 C7 O6 107.30(10) . . ?
C8 C7 O11 109.96(10) . . ?
C9 C7 O6 105.04(9) . . ?
C9 C7 O11 108.20(10) . . ?
C9 C7 C8 115.32(9) . . ?
C7 C8 O10 111.06(12) . . ?
C7 C9 O9 115.73(11) . . ?
C10 C9 O9 115.67(11) . . ?
C10 C9 C7 102.56(9) . . ?
C9 C10 O8 112.44(10) . . ?
C11 C10 O8 111.71(12) . . ?
C11 C10 C9 102.43(10) . . ?
C10 C11 O6 105.46(10) . . ?
C12 C11 O6 109.84(10) . . ?
C12 C11 C10 114.86(11) . . ?
C11 C12 O7 112.88(12) . . ?
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
O1 C1 1.4420(16) . ?
O1 C6 1.4137(13) . ?
O2 C2 1.4215(18) . ?
O3 C3 1.4126(17) . ?
O4 C4 1.4296(16) . ?
O5 C5 1.4233(15) . ?
O6 C7 1.4078(13) . ?
O6 C11 1.4478(14) . ?
O7 C12 1.423(2) . ?
O8 C10 1.4206(15) . ?
O9 C9 1.4032(16) . ?
O10 C8 1.4239(18) . ?
O11 C6 1.4226(13) . ?
O11 C7 1.4343(15) . ?
C1 C2 1.5243(17) . ?
C1 C3 1.5287(18) . ?
C3 C4 1.5279(16) . ?
C4 C5 1.5236(19) . ?
C5 C6 1.5354(17) . ?
C7 C8 1.5267(15) . ?
C7 C9 1.5418(15) . ?
C9 C10 1.5244(16) . ?
C10 C11 1.5253(18) . ?
C11 C12 1.5168(16) . ?
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
O1 C1 C2 O2 56.59(11) . . . . ?
O1 C1 C3 O3 177.27(10) . . . . ?
O1 C1 C3 C4 55.10(10) . . . . ?
O1 C6 O11 C7 -108.04(11) . . . . ?
O1 C6 C5 O5 -177.17(10) . . . . ?
O1 C6 C5 C4 -54.69(10) . . . . ?
O2 C2 C1 C3 -64.12(15) . . . . ?
O3 C3 C1 C2 -64.87(12) . . . . ?
O3 C3 C4 O4 64.32(12) . . . . ?
O3 C3 C4 C5 -174.85(11) . . . . ?
O4 C4 C3 C1 -177.34(10) . . . . ?
O4 C4 C5 O5 -62.94(10) . . . . ?
O4 C4 C5 C6 174.54(9) . . . . ?
O5 C5 C4 C3 178.59(10) . . . . ?
O5 C5 C6 O11 -54.81(11) . . . . ?
O6 C7 O11 C6 44.94(10) . . . . ?
O6 C7 C8 O10 -171.28(9) . . . . ?
O6 C7 C9 O9 157.70(9) . . . . ?
O6 C7 C9 C10 30.83(10) . . . . ?
O6 C11 C10 O8 147.84(9) . . . . ?
O6 C11 C10 C9 27.28(10) . . . . ?
O6 C11 C12 O7 69.26(12) . . . . ?
O7 C12 C11 C10 -49.40(13) . . . . ?
O8 C10 C9 O9 78.12(13) . . . . ?
O8 C10 C9 C7 -154.97(12) . . . . ?
O8 C10 C11 C12 -91.08(11) . . . . ?
O9 C9 C7 O11 39.17(10) . . . . ?
O9 C9 C7 C8 -84.41(12) . . . . ?
O9 C9 C10 C11 -161.83(12) . . . . ?
O10 C8 C7 O11 -50.56(11) . . . . ?
O10 C8 C7 C9 72.09(12) . . . . ?
O11 C6 C5 C4 67.67(11) . . . . ?
O11 C7 C9 C10 -87.70(10) . . . . ?
C1 C3 C4 C5 -56.51(11) . . . . ?
C3 C4 C5 C6 56.07(10) . . . . ?
C7 C9 C10 C11 -34.92(11) . . . . ?
C9 C10 C11 C12 148.36(11) . . . . ?
