Double cyclization of O-acylated hydroxyamides generates 1,6-dioxa-3,9-diazaspiro[4.4]nonanes a new class of oxy-oxazolidinones
Nazarian, Zohreh; Forsyth, Craig; RSC Advances 6 (2016) 55534–; doi:10.1039/C6RA11604C

data_7236238
_publ_section_title
;
 Double cyclization of O-acylated hydroxyamides generates
 1,6-dioxa-3,9-diazaspiro[4.4]nonanes a new class of oxy-oxazolidinones
;
_journal_issue                   60
_journal_name_full               'RSC Advances'
_journal_page_first              55534
_journal_paper_doi               10.1039/C6RA11604C
_journal_volume                  6
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H24 N2 O4'
_chemical_formula_sum            'C22 H24 N2 O4'
_chemical_formula_weight         380.43
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
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_audit_update_record
;
2016-04-29 deposited with the CCDC.
2016-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0291(1)
_cell_length_b                   14.3287(3)
_cell_length_c                   14.8824(3)
_cell_measurement_reflns_used    7898
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      66.3886
_cell_measurement_theta_min      2.9668
_cell_volume                     1925.41(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_molecular_graphics    X-Seed
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_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.3389
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0125
_diffrn_reflns_av_sigmaI/netI    0.0129
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10532
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         66.50
_diffrn_reflns_theta_min         4.28
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(12)
_refine_ls_extinction_coef       0.0052(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0226
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0328P)^2^+0.3184P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0589
_refine_ls_wR_factor_ref         0.0595
_reflns_number_gt                3344
_reflns_number_total             3387
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra11604c2.cif
_cod_data_source_block           108_11a
_cod_database_code               7236238