Base mediated green synthesis of enantiopure 2-C-spiro-glycosyl-3-nitrochromenes.
Nayak, Sabita; Panda, Pravati; Raiguru, Bishnu Prasad; Mohapatra, Seetaram; Purohit, Chandra Shekhar; Organic & biomolecular chemistry 17 (2018) 74–82; doi:10.1039/c8ob02278j

data_7156580
_publ_section_title
;
 Base mediated green synthesis of enantiopure
 2-C-spiro-glycosyl-3-nitrochromenes.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              74
_journal_page_last               82
_journal_paper_doi               10.1039/c8ob02278j
_journal_volume                  17
_journal_year                    2018
_chemical_formula_moiety         'C22 H25 O9'
_chemical_formula_sum            'C22 H25 O9'
_chemical_formula_weight         433.42
_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_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-08-18
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_audit_update_record
;
2018-09-24 deposited with the CCDC.
2018-11-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.1820(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.83620(10)
_cell_length_b                   15.7227(3)
_cell_length_c                   10.03170(10)
_cell_measurement_reflns_used    16271
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.9640
_cell_measurement_theta_min      4.3580
_cell_volume                     1073.84(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9985
_diffrn_measured_fraction_theta_max 0.9894
_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     -1.00  67.00   0.50    0.49    --    0.00  28.00 -93.00  136
  2  \w     35.00 103.00   0.50    1.95    --  102.08 -28.00 104.00  136
  3  \w    102.00 169.00   0.50    1.95    --  102.08  28.00 -93.00  134
  4  \w    -65.00   1.00   0.50    0.49    --    0.00 -37.00 -60.00  132
  5  \w    -62.00  22.00   0.50    0.49    --    0.00 -77.00-180.00  168
  6  \w    -22.00  62.00   0.50    0.49    --    0.00  77.00 -30.00  168
  7  \w    -67.00  67.00   0.50    0.49    --    0.00   0.00 -60.00  268
  8  \w    -67.00   1.00   0.50    0.49    --    0.00 -28.00 104.00  136
  9  \w    -22.00  62.00   0.50    0.49    --    0.00  77.00  30.00  168
 10  \w    -65.00   1.00   0.50    0.49    --    0.00 -37.00 -30.00  132
 11  \w     -1.00  67.00   0.50    0.49    --    0.00  19.00 -30.00  136
 12  \w     -1.00  65.00   0.50    0.49    --    0.00  37.00 -30.00  132
 13  \w     34.00 109.00   0.50    1.95    --  102.08 -94.00-180.00  150
 14  \w     80.00 164.00   0.50    1.95    --  102.08  77.00  60.00  168
 15  \w     80.00 164.00   0.50    1.95    --  102.08  77.00 -30.00  168
 16  \w     94.00 166.00   0.50    1.95    --  102.08 125.00 150.00  144
 17  \w     91.00 164.00   0.50    1.95    --  102.08  61.00  30.00  146
 18  \w    100.00 170.00   0.50    1.95    --  102.08  15.00 -30.00  140
 19  \w     80.00 164.00   0.50    1.95    --  102.08  77.00   0.00  168
 20  \w     34.00 109.00   0.50    1.95    --  102.08 -94.00 120.00  150
 21  \w     34.00 109.00   0.50    1.95    --  102.08 -94.00 -90.00  150
 22  \w    101.00 169.00   0.50    1.95    --  102.08  30.00  30.00  136
 23  \w    100.00 170.00   0.50    1.95    --  102.08  15.00  60.00  140
 24  \w     80.00 164.00   0.50    1.95    --  102.08  77.00 -90.00  168
 25  \w    100.00 170.00   0.50    1.95    --  102.08  15.00   0.00  140
 26  \w    100.00 165.00   0.50    1.95    --  102.08  45.00  30.00  130
 27  \w     98.00 165.00   0.50    1.95    --  102.08  48.00  64.50  134
 28  \w     81.00 164.00   0.50    1.95    --  102.08  75.00  -9.20  166
 29  \w     80.00 164.00   0.50    1.95    --  102.08  77.00  30.00  168
 30  \w    133.00 163.00   0.50    1.95    --  102.08  30.00 -30.00   60
 31  \w    101.00 127.00   0.50    1.95    --  102.08  30.00 -30.00   52
 32  \w    137.00 164.00   0.50    1.95    --  102.08  77.00 -60.00   54
 33  \w     91.00 130.00   0.50    1.95    --  102.08  61.00 -30.00   78
 34  \w     92.00 118.00   0.50    1.95    --  102.08  61.00  60.00   52
 35  \w     72.00  99.00   0.50    1.95    --  102.08 -61.00 -60.00   54
 36  \w     76.00 102.00   0.50    1.95    --  102.08 -30.00  30.00   52
 37  \w    100.00 139.00   0.50    1.95    --  102.08  15.00 -60.00   78
 38  \w     91.00 122.00   0.50    1.95    --  102.08  65.00 -69.39   62
 39  \w    103.00 129.00   0.50    1.95    --  102.08  45.00 -30.00   52
 40  \w     40.00 110.00   0.50    1.95    --  102.08 -61.00 150.00  140
 41  \w     92.00 118.00   0.50    1.95    --  102.08  61.00 -60.00   52
 42  \w     81.00 107.00   0.50    1.95    --  102.08  77.00 -60.00   52
 43  \w    100.00 126.00   0.50    1.95    --  102.08  15.00  30.00   52
 44  \w     40.00  69.00   0.50    1.95    --  102.08 -30.00  30.00   58
 45  \w     71.00 109.00   0.50    1.95    --  102.08 -94.00  60.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0660699000
_diffrn_orient_matrix_UB_12      -0.0331026000
_diffrn_orient_matrix_UB_13      -0.1415103000
_diffrn_orient_matrix_UB_21      0.2158887000
_diffrn_orient_matrix_UB_22      -0.0038129000
_diffrn_orient_matrix_UB_23      -0.0322627000
_diffrn_orient_matrix_UB_31      0.0148521000
_diffrn_orient_matrix_UB_32      -0.0921614000
_diffrn_orient_matrix_UB_33      0.0520377000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17863
_diffrn_reflns_point_group_measured_fraction_full 0.902
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         4.426
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.881
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull yellowish yellow'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       block
_exptl_crystal_F_000             458
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1374 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.26(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3414
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0497
_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^)+(0.1147P)^2^+0.0544P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1455
_refine_ls_wR_factor_ref         0.1466
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    0.796
_reflns_Friedel_fraction_max     0.796
_reflns_number_gt                3342
_reflns_number_total             3414
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02278j2.cif
_cod_data_source_block           csp_27072018
_cod_depositor_comments          'Adding full bibliography for 7156580.cif.'
_cod_database_code               7156580
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C40 H48 N2 O20 '
_diffrn_oxdiff_ac3_digest_frames
;
013a60a383aab3a670033a8115d55c36760004027cb
;
_diffrn_oxdiff_ac3_digest_hkl
;
0128ff4dfdfb9a42c99888609124d7f85b3120
;
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
2.a Ternary CH refined with riding coordinates:
 C2(H2), C8(H8), C4(H4), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C14(H14), C20(H20), C19(H19)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C6(H6A,H6B,H6C), C22(H22A,H22B,H22C), C12(H12A,H12B,
 H12C), C7(H7A,H7B,H7C)
;
_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 6.049
_oxdiff_exptl_absorpt_empirical_full_min 0.309