Improved synthesis and application of conjugation-amenable polyols from d-mannose
Mattsson, Ida; Sitdikov, Ruzal; Gunell, Andreas C. M.; Lahtinen, Manu; Saloranta-Simell, Tiina; Leino, Reko; RSC Advances 10 (2020) 3960–3966; doi:10.1039/C9RA10378C

data_7239831
_publ_section_title
;
 Improved synthesis and application of conjugation-amenable polyols from
 d-mannose
;
_journal_issue                   7
_journal_name_full               'RSC Advances'
_journal_page_first              3960
_journal_page_last               3966
_journal_paper_doi               10.1039/C9RA10378C
_journal_volume                  10
_journal_year                    2020
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C16 H23 N3 O6'
_chemical_formula_sum            'C16 H23 N3 O6'
_chemical_formula_weight         353.37
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-28 deposited with the CCDC.	2020-01-14 downloaded from the CCDC.
;
_cell_angle_alpha                83.212(8)
_cell_angle_beta                 87.407(7)
_cell_angle_gamma                85.031(8)
_cell_formula_units_Z            1
_cell_length_a                   4.7849(5)
_cell_length_b                   5.3125(5)
_cell_length_c                   17.3017(15)
_cell_measurement_reflns_used    2259
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.0420
_cell_measurement_theta_min      2.5250
_cell_volume                     434.81(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.974
_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    -66.00  32.00   2.00   25.00    --  -41.40  37.00  60.00   49
  2  \w    -66.00  32.00   2.00   25.00    --  -41.40  37.00 -30.00   49
  3  \w    -95.00  -3.00   2.00   25.00    --  -41.40 125.00 150.00   46
  4  \w     13.00 115.00   2.00   25.00    --   41.40  57.00  90.00   51
  5  \w     17.00 115.00   2.00   25.00    --   41.40  37.00-180.00   49
  6  \w     36.00 144.00   2.00  100.00    --  112.00 -77.00-120.00   54
  7  \w     79.00 177.00   2.00  100.00    --  112.00  77.00   0.00   49
  8  \w     29.00 109.00   2.00  100.00    --  112.00 -94.00 150.00   40
  9  \w     86.00 178.00   2.00  100.00    --  112.00  45.00 -60.00   46
 10  \w     36.00 116.00   2.00  100.00    --  112.00-111.00-150.00   40
 11  \w     57.00 151.00   2.00  100.00    --  112.00 178.00 150.00   47
 12  \w     40.00 140.00   2.00  100.00    --  112.00 -61.00-180.00   50
 13  \w     36.00 116.00   2.00  100.00    --  112.00-111.00  30.00   40
 14  \w     83.00 177.00   2.00  100.00    --  112.00  61.00 -30.00   47
 15  \w     36.00 116.00   2.00  100.00    --  112.00-111.00 120.00   40
 16  \w     79.00 177.00   2.00  100.00    --  112.00  77.00-120.00   49
 17  \w     13.00 115.00   2.00   25.00    --   41.40  57.00  30.00   51
 18  \w     13.00 115.00   2.00   25.00    --   41.40  57.00-120.00   51
 19  \w      4.00  82.00   2.00   25.00    --   41.40-101.00 142.00   39
 20  \w      9.00 117.00   2.00   25.00    --   41.40  77.00 150.00   54
 21  \w      9.00 117.00   2.00   25.00    --   41.40  77.00 -90.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0985380000
_diffrn_orient_matrix_UB_12      -0.1005984000
_diffrn_orient_matrix_UB_13      0.0830481000
_diffrn_orient_matrix_UB_21      0.3069466000
_diffrn_orient_matrix_UB_22      -0.0794325000
_diffrn_orient_matrix_UB_23      0.0211095000
_diffrn_orient_matrix_UB_31      0.0254487000
_diffrn_orient_matrix_UB_32      0.2634959000
_diffrn_orient_matrix_UB_33      0.0266128000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4839
_diffrn_reflns_point_group_measured_fraction_full 0.734
_diffrn_reflns_point_group_measured_fraction_max 0.695
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.592
_diffrn_reflns_theta_min         2.573
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.873
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       plate
_exptl_crystal_F_000             188
_exptl_crystal_size_max          0.096
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.029
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 606 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         2541
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0460P)^2^+0.0194P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0922
_reflns_Friedel_coverage         0.426
_reflns_Friedel_fraction_full    0.470
_reflns_Friedel_fraction_max     0.415
_reflns_number_gt                2219
_reflns_number_total             2541
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra10378c2.cif
_cod_data_source_block           im-ii-100_1_r4-halfcell-absclark
_cod_depositor_comments          'Adding full bibliography for 7239831.cif.'
_cod_database_code               7239831
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C16 H18 O6 N3'
_reflns_odcompleteness_completeness 98.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 O(H) groups
2. Others
 Fixed Sof: C15A(0.5) H15A(0.5) C15B(0.5) H15B(0.5) C16A(0.5) H16A(0.5)
 C16B(0.5) H16B(0.5) H17A(0.5) H17(0.5) C18A(0.5) H18A(0.5) C18B(0.5) H18B(0.5)
 C19A(0.5) H19A(0.5) C19B(0.5) H19B(0.5)
3.a Ternary CH refined with riding coordinates:
 C2(H2A), C3(H3A), C4(H4A), C5(H5A), C6(H6A)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C7(H7A,H7B), C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C15A(H15A), C15B(H15B), C16A(H16A), C16B(H16B), C17(H17A), C17(H17),
  C18A(H18A), C18B(H18B), C19A(H19A), C19B(H19B)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3), O4(H4), O5(H5), O6(H6)
;
_shelx_res_checksum              14779
_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 1.241
_oxdiff_exptl_absorpt_empirical_full_min 0.862