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_7234165
_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         'C20 H22 Cl2 N2 O4'
_chemical_formula_sum            'C20 H22 Cl2 N2 O4'
_chemical_formula_weight         425.30
_chemical_name_systematic
9-N,10-N-bis(4-chlorophenyl)-7,8,11,12-tetraoxaspiro[5.6]dodecane-9,10-diamine
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_audit_update_record
;
2019-03-25 deposited with the CCDC.    2019-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.462(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5362(9)
_cell_length_b                   9.4705(6)
_cell_length_c                   20.3165(17)
_cell_measurement_reflns_used    3198
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.7810
_cell_measurement_theta_min      2.3840
_cell_volume                     1999.7(3)
_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   -1.00   76.00   1.0000   25.1900
omega____ theta____ kappa____ phi______ frames
    -       16.8699   38.0000  -30.0000 77

  2 omega   24.00   86.00   1.0000   25.1900
omega____ theta____ kappa____ phi______ frames
    -       16.8699    0.0000 -150.0000 62

  3 omega  -14.00   22.00   1.0000   25.1900
omega____ theta____ kappa____ phi______ frames
    -      -16.0886  -99.0000  -60.0000 36

  4 omega  -41.00  -14.00   1.0000   25.1900
omega____ theta____ kappa____ phi______ frames
    -       16.8699    0.0000 -150.0000 27

  5 omega  -43.00   50.00   1.0000   25.1900
omega____ theta____ kappa____ phi______ frames
    -      -16.0886   77.0000 -180.0000 93

  6 omega  -84.00  -69.00   1.0000   25.1900
omega____ theta____ kappa____ phi______ frames
    -      -16.0886  -77.0000   60.0000 15
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0662341000
_diffrn_orient_matrix_UB_12      -0.0158695000
_diffrn_orient_matrix_UB_13      -0.0096882000
_diffrn_orient_matrix_UB_21      -0.0063124000
_diffrn_orient_matrix_UB_22      -0.0087330000
_diffrn_orient_matrix_UB_23      0.0339996000
_diffrn_orient_matrix_UB_31      -0.0152781000
_diffrn_orient_matrix_UB_32      0.0726195000
_diffrn_orient_matrix_UB_33      0.0019778000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13245
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.281
_diffrn_reflns_theta_min         2.032
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'XCalibur E'
_exptl_absorpt_coefficient_mu    0.354
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64675
_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            colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       prizm
_exptl_crystal_F_000             888.0
_exptl_crystal_recrystallization_method hexane/Et2O
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4644
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0608
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1582
_refine_ls_wR_factor_ref         0.1916
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2780
_reflns_number_total             4644
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra06372b2.cif
_cod_data_source_block           iir-303-7
_cod_database_code               7234165
_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, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C3(H3A,H3B), C6(H6A,H6B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 N20(H20), N13(H13), C22(H22), C15(H15), C19(H19), C16(H16), C23(H23),
 C18(H18), C26(H26), C25(H25)
;