Intramolecular etherification of five-membered cyclic carbonates bearing hydroxyalkyl groups
Tomczyk, Karolina M.; Guńka, Piotr A.; Parzuchowski, Paweł G.; Zachara, Janusz; Rokicki, Gabriel; Green Chemistry 14 (2012) 1749–; doi:10.1039/c2gc35265f

data_7208025
_publ_section_title
;
 Intramolecular etherification of five-membered cyclic carbonates bearing
 hydroxyalkyl groups
;
_journal_issue                   6
_journal_name_full               'Green Chemistry'
_journal_page_first              1749
_journal_paper_doi               10.1039/c2gc35265f
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C8 H8 O7'
_chemical_formula_sum            'C8 H8 O7'
_chemical_formula_weight         216.14
_chemical_name_systematic
;
6-(1,3-dioxolan-2-one-4-yl)-2,4,7-trioxa-3-oxy-bicyclo[3.3.0]octane
;
_space_group_crystal_system      orthorhombic
_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_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-01-19
_audit_creation_method
;
Olex2 1.1
(compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9412(2)
_cell_length_b                   10.0129(3)
_cell_length_c                   10.8310(3)
_cell_measurement_reflns_used    4403
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.4573
_cell_measurement_theta_min      3.2676
_cell_volume                     861.22(4)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10.3347
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details
;
1 omega -15.00 68.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -11.4008 19.0000 90.0000 83

2 omega -15.00 40.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 11.7133 19.0000 30.0000 55

3 omega -31.00 24.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 11.7133 100.0000 96.0000 55

4 omega -64.00 38.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 11.7133 -38.0000 150.0000 102

5 omega -62.00 38.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 11.7133 -60.0000 -4.0000 100

6 omega -62.00 41.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 11.7133 -57.0000 -90.0000 103
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0267267000
_diffrn_orient_matrix_UB_12      -0.0473596000
_diffrn_orient_matrix_UB_13      -0.0445899000
_diffrn_orient_matrix_UB_21      0.0570905000
_diffrn_orient_matrix_UB_22      -0.0275689000
_diffrn_orient_matrix_UB_23      0.0434380000
_diffrn_orient_matrix_UB_31      -0.0632783000
_diffrn_orient_matrix_UB_32      -0.0448838000
_diffrn_orient_matrix_UB_33      0.0203510000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11362
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         29.52
_diffrn_reflns_theta_min         3.27
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86045
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
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    1.667
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
The absolute configuration was assigned to agree with that
of its precursor. All Friedel pairs were merged.
;
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_coef       0.042(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   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         1321
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0276
_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^)+(0.0296P)^2^+0.24P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0632
_reflns_number_gt                1224
_reflns_number_total             1321
_reflns_threshold_expression     I>2u(I)
_cod_data_source_file            c2gc35265f.txt
_cod_data_source_block           comp20
_cod_database_code               7208025