A one-pot regiospecific synthesis of highly functionalized 1,4-benzodioxin derivatives from an electrochemically induced Diels-Alder reaction.
Xu, Daiwang; Chiaroni, Angèle; Largeron, Martine; Organic letters 7 (2005) 5273–5276; doi:10.1021/ol052146e

data_1506751
_publ_section_title
;
 A one-pot regiospecific synthesis of highly functionalized
 1,4-benzodioxin derivatives from an electrochemically induced Diels-Alder
 reaction.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5273
_journal_page_last               5276
_journal_paper_doi               10.1021/ol052146e
_journal_volume                  7
_journal_year                    2005
_chemical_formula_moiety         'C19 H25 N O6'
_chemical_formula_sum            'C19 H25 N O6'
_chemical_formula_weight         363.40
_chemical_melting_point          468(2)
_chemical_name_common            Fly051
_chemical_name_systematic
; 
 ((R,S)-5-hydroxy-2-morpholino-3-spiro-1'-cyclohexyl-2,3-
 dihydro-1,4-benzodioxin-6-yl)carboxylic methyl ester :[3h]
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
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_cell_angle_beta                 80.61(2)
_cell_angle_gamma                89.87(2)
_cell_formula_units_Z            4
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_cell_length_b                   12.662(4)
_cell_length_c                   13.310(4)
_cell_measurement_reflns_used    7821
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1850.7(10)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'R3M (Riche, 1983) ORTEP (Johnson, 1965)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius Kappa-CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            28529/13476
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.80
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
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_refine_diff_density_min         -0.161
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_refine_ls_extinction_coef       0.014(2)
_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   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     478
_refine_ls_number_reflns         8462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0490P)^2^+0.2869P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1156
_reflns_number_gt                5713
_reflns_number_total             8462
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol052146esi20050907_015621.cif
_cod_data_source_block           fleu
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1850.7(9)
_cod_database_code               1506751