Stereoselective synthesis of medicinally relevant furo[2,3-d]pyrimidine framework by thermal rearrangement of spirocyclic barbiturates
Vereshchagin, Anatoly N.; Elinson, Michail N.; Dorofeeva, Evgeniya O.; Sokolova, Olga O.; Bushmarinov, Ivan S.; Egorov, Michail N.; RSC Adv.  (2015) –; doi:10.1039/C5RA19169F

data_7222970
_publ_section_title
;
 Stereoselective synthesis of medicinally relevant furo[2,3-d]pyrimidine
 framework by thermal rearrangement of spirocyclic barbiturates
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA19169F
_journal_year                    2015
_chemical_formula_moiety         'C17 H15 N3 O5'
_chemical_formula_sum            'C17 H15 N3 O5'
_chemical_formula_weight         341.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-09-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-09-09 deposited with the CCDC.
2015-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   26.589(4)
_cell_length_b                   32.239(5)
_cell_length_c                   7.3315(12)
_cell_measurement_reflns_used    1794
_cell_measurement_temperature    100
_cell_measurement_theta_max      22.345
_cell_measurement_theta_min      2.526
_cell_volume                     6284.6(17)
_computing_data_collection       'SMART v5.054 (Bruker, 2001)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17890
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.068
_diffrn_reflns_theta_min         1.986
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.8032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1159 before and 0.0524 after correction.
The Ratio of minimum to maximum transmission is 0.9316.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       needle
_exptl_crystal_F_000             2848
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details
;
 Flack x determined using 1058 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4565
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.1161
_refine_ls_R_factor_gt           0.0725
_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^)+(0.0822P)^2^+6.0441P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1516
_refine_ls_wR_factor_ref         0.1737
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                3077
_reflns_number_total             4565
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra19169f2.cif
_cod_data_source_block           x6
_cod_original_cell_volume        6284.5(17)
_cod_database_code               7222970
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C15(H15), C19(H19), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C20(H20A,H20B,H20C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              14548
_shelx_hkl_checksum              67449
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'