Organocatalytic Access to Enantioenriched Dihydropyran Phosphonates via an Inverse-Electron-Demand Hetero-Diels-Alder Reaction.
Weise, Christian F; Lauridsen, Vibeke H; Rambo, Raoní S; Iversen, Eva H; Olsen, Marie-Luise; Jørgensen, Karl Anker; The Journal of organic chemistry 79 (2014) 3537–3546; doi:10.1021/jo500347a

data_4029275
_publ_section_title
;
 Organocatalytic Access to Enantioenriched Dihydropyran Phosphonates via
 an Inverse-Electron-Demand Hetero-Diels-Alder Reaction.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3537
_journal_page_last               3546
_journal_paper_doi               10.1021/jo500347a
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C20 H22 O4'
_chemical_formula_sum            'C20 H22 O4'
_chemical_formula_weight         326.37
_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_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2013-11-20
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4709)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2585(3)
_cell_length_b                   15.9680(7)
_cell_length_c                   17.0842(8)
_cell_measurement_reflns_used    6032
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.90
_cell_measurement_theta_min      2.74
_cell_volume                     1707.32(14)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16203
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         21.074
_diffrn_reflns_theta_min         1.377
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.055
_exptl_absorpt_correction_T_max  0.7446
_exptl_absorpt_correction_T_min  0.6595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0723 before and 0.0520 after correction.
The Ratio of minimum to maximum transmission is 0.8857.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             696
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1300 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.7(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0448P)^2^+0.3367P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0924
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3337
_reflns_number_total             3726
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo500347a_si_002.cif
_cod_data_source_block           c20h22o4_0m
_cod_depositor_comments
;Adding full bibliography for
 ./tmp-cod-update-bibliographies-12971/cifs/4029275.cif.
;
_cod_database_code               4029275
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C8(H8), C17(H17), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C12(H12), C13(H13), C15(H15), C16(H16), C20(H20), C21(H21),
 C22(H22)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;