Diastereoselective construction of anti-4,5-disubstituted-1,3-dioxolanes via a bismuth-mediated two-component hemiacetal oxa-conjugate addition of gamma-hydroxy-alpha,beta-unsaturated ketones with paraformaldehyde
Aleksandr Grisin; Samuel Oliver; Michael D. Ganton; John Bacsa; P. Andrew Evans; Chem.Commun. 51 (2015) 15681–; doi:10.1039/C5cc01949D

data_7117972
_publ_section_title
;
 Diastereoselective construction of anti-4,5-disubstituted-1,3-dioxolanes
 via a bismuth-mediated two-component hemiacetal oxa-conjugate addition of
 gamma-hydroxy-alpha,beta-unsaturated ketones with paraformaldehyde
;
_journal_name_full               Chem.Commun.
_journal_page_first              15681
_journal_paper_doi               10.1039/C5cc01949D
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C20 H22 N4 O6'
_chemical_formula_sum            'C20 H22 N4 O6'
_chemical_formula_weight         414.41
_chemical_name_common            'hydrazone 5'
_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_cell_setting           monoclinic
_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     direct
_audit_creation_date             2014-11-21
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.11.18 svn.r3084 for OlexSys, GUI svn.r4945)
;
_audit_update_record
;
2015-08-06 deposited with the CCDC.
2015-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.760(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.938(6)
_cell_length_b                   5.2580(17)
_cell_length_c                   20.517(7)
_cell_measurement_reflns_used    2544
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.587
_cell_measurement_theta_min      2.265
_cell_volume                     1934.5(11)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v.5.632 (Bruker, 2005)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  apex
_diffrn_measurement_method       '\w scans with a narrow frame width'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0825
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9510
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         1.274
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008-1 (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3543
_refine_ls_number_restraints     114
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0510
_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^)+(0.0549P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1268
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2158
_reflns_number_total             3543
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc01949d2.cif.txt
_cod_data_source_block           1012071m
_cod_original_cell_volume        1934.4(11)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7117972
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.948
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C4, C2, C3, C12
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
 O1, C2, C3, C4
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
 O1, C1, O2
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
 O2, C3, C12
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
 C12, C13, C20, N1
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C19, C14, C15
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N3, O3
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 O4, N3
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N3, C15
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C15, C16, C17
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N4, C17, C18, C16
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N4, O5, O6
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N1, N2
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N2, C14
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3.a Ternary CH refined with riding coordinates:
 C2(H2A), C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C4(H4A,H4B), C5(H5A,H5B), C1(H1A,H1B)
3.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C18(H18), C19(H19), C16(H16), C11(H11), C7(H7), C10(H10), C9(H9),
 C8(H8)
3.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_original_sample_id 1012071M
_olex2_submission_special_instructions 'No special instructions were received'