New synthesis of tetraoxaspirododecane-diamines and tetraoxazaspirobicycloalkanes
Makhmudiyarova, Nataliya N.; Shangaraev, Kamil R.; Dzhemileva, Lilya U.; Tyumkina, Tatyana V.; Mescheryakova, Ekaterina S.; D'yakonov, Vladimir A.; Ibragimov, Askhat G.; Dzhemilev, Usein M.; RSC Advances 9 (2019) 29949–; doi:10.1039/C9RA06372B

data_7234164
_publ_section_title
;
 New synthesis of tetraoxaspirododecane-diamines and
 tetraoxazaspirobicycloalkanes
;
_journal_issue                   51
_journal_name_full               'RSC Advances'
_journal_page_first              29949
_journal_paper_doi               10.1039/C9RA06372B
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C17 H22 F N O4'
_chemical_formula_sum            'C17 H22 F N O4'
_chemical_formula_weight         323.36
_chemical_name_systematic
11-(2-fluorophenyl)-2,3,5,6-tetraoxa-11-azaspiro[bicyclo[5.3.1]undecane-4,1'-cyclohexane]
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-25 deposited with the CCDC.    2019-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                75.029(7)
_cell_angle_beta                 80.670(6)
_cell_angle_gamma                88.090(6)
_cell_formula_units_Z            2
_cell_length_a                   6.4738(3)
_cell_length_b                   10.2056(9)
_cell_length_c                   12.4931(10)
_cell_measurement_reflns_used    1778
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1290
_cell_measurement_theta_min      3.0190
_cell_volume                     786.81(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1709
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -39.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1042  -57.0000   30.0000 68

  2 omega   -3.00   23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.4011  -99.0000   30.0000 26

  3 omega  -15.00   17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.4011  -99.0000  -60.0000 32

  4 omega   35.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1042 -156.0000 -114.0000 54

  5 omega   33.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1042 -178.0000    0.0000 56

  6 omega  -45.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1042    0.0000   60.0000 131
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0122143000
_diffrn_orient_matrix_UB_12      0.0708934000
_diffrn_orient_matrix_UB_13      -0.0069965000
_diffrn_orient_matrix_UB_21      0.0047298000
_diffrn_orient_matrix_UB_22      0.0092013000
_diffrn_orient_matrix_UB_23      -0.0585988000
_diffrn_orient_matrix_UB_31      -0.1102624000
_diffrn_orient_matrix_UB_32      -0.0081079000
_diffrn_orient_matrix_UB_33      0.0077923000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6506
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.279
_diffrn_reflns_theta_min         2.319
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'XCalibur E'
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       prizm
_exptl_crystal_F_000             344.0
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3611
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0548P)^2^+0.0778P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1303
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2526
_reflns_number_total             3611
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra06372b2.cif
_cod_data_source_block           skr-135-3
_cod_original_cell_volume        786.81(11)
_cod_database_code               7234164
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C008(H008), C010(H010)
2.b Secondary CH2 refined with riding coordinates:
 C013(H01A,H01B), C014(H01C,H01D), C016(H01E,H01F), C017(H01G,H01H), C018(H01I,
 H01J), C020(H02A,H02B), C021(H02C,H02D), C023(H02E,H02F)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C015(H015), C019(H019), C022(H022)
;