Smart and concise entry to chiral spiro[cyclopentane-indolizidine]-tetraol diastereomers as a new aza-spirocyclic framework
Fraňová, Paula; Marchalín, Štefan; Šafář, Peter; Cvečko, Matej; Moncol, Ján; Žídeková, Ivana; Othman, Mohamed; Daïch, Adam; New Journal of Chemistry 45 (2021) 15956–15967; doi:10.1039/D1NJ02180J

data_7060866
_publ_section_title
;
 Smart and concise entry to chiral
 spiro[cyclopentane-indolizidine]-tetraol diastereomers as a new
 aza-spirocyclic framework
;
_journal_issue                   35
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15956
_journal_page_last               15967
_journal_paper_doi               10.1039/D1NJ02180J
_journal_volume                  45
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H29 N O6'
_chemical_formula_sum            'C20 H29 N O6'
_chemical_formula_weight         379.44
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-03-13 deposited with the CCDC.	2021-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.638(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.5826(2)
_cell_length_b                   9.04830(10)
_cell_length_c                   16.3477(4)
_cell_measurement_reflns_used    117336
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.60
_cell_measurement_theta_min      4.89
_cell_volume                     962.65(4)
_computing_cell_refinement
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection
;
X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)
;
_computing_data_reduction
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area LANA 1.73.2.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.84, Darmstadt 2018
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Pilatus3R 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe StadiVari'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            36055
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.914
_diffrn_reflns_theta_min         5.474
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_T_max  0.8075
_exptl_absorpt_correction_T_min  0.1634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE LANA, J. Koziskova, F. Hahn, J. Richter, J. Kozisek, 
Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.798
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.146
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3471
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.165
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0893
_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^)+(0.1779P)^2^+0.6477P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2453
_refine_ls_wR_factor_ref         0.2477
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    0.880
_reflns_Friedel_fraction_max     0.836
_reflns_number_gt                3399
_reflns_number_total             3471
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj02180j2.cif
_cod_data_source_block           10b
_cod_depositor_comments
'Adding full bibliography for 7060865--7060866.cif.'
_cod_database_code               7060866
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.827
_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:
 C4(H4), C7(H7), C9(H9), C15(H15), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C8(H8A,H8B), C10(H10A,H10B), C14(H14A,H14B),
 C17(H17A,H17B)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
;
_shelx_res_checksum              85507
_olex2_submission_special_instructions 'No special instructions were received'