Towards the enantioselective synthesis of (-)-euonyminol‒preparation of a fully functionalised lower-rim model.
Webber, Matthew J; Warren, Sarah A; Grainger, Damian M; Weston, Matthew; Clark, Stacy; Woodhead, Steven J; Powell, Lyn; Stokes, Stephen; Alanine, Alexander; Stonehouse, Jeffrey P; Frampton, Christopher S; White, Andrew J P; Spivey, Alan C; Organic & biomolecular chemistry 11 (2013) 2514–2533; doi:10.1039/c3ob27187k

data_7152856
_publ_section_title
;
 Towards the enantioselective synthesis of (-)-euonyminol--preparation of
 a fully functionalised lower-rim model.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2514
_journal_page_last               2533
_journal_paper_doi               10.1039/c3ob27187k
_journal_volume                  11
_journal_year                    2013
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C17 H23 N O4, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C19 H27 N O5'
_chemical_formula_weight         349.42
_chemical_name_systematic
;
?
;
_space_group_IT_number           78
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4cw'
_symmetry_space_group_name_H-M   'P 43'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.17422(15)
_cell_length_b                   16.17422(15)
_cell_length_c                   7.32793(11)
_cell_measurement_reflns_used    9356
_cell_measurement_temperature    173
_cell_measurement_theta_max      71.3444
_cell_measurement_theta_min      2.7297
_cell_volume                     1917.03(4)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.2556
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'OD Xcalibur PX Ultra'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            28203
_diffrn_reflns_theta_full        71.49
_diffrn_reflns_theta_max         71.49
_diffrn_reflns_theta_min         2.73
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_platon_squeeze_details
;
SQUEEZE suggested 102 e/cell = 25.5 e/asu
The solvents used were thf (C4H8O, 40e) in the preparation, and ethyl
acetate (C4H8O2, 48e) and hexane (C6H14, 60e) in the recrystallisation.
Before SQUEEZE, the solvent looked like ethyl acetate
0.5EtOAc = 24e, so this was used as the solvent present.
So, the atom list is low by 0.5(C4 H8 O2) = C2 H4 O, and the UNIT is
low by C8 H16 O4, i.e. C68 H92 N4 O16
;
_refine_diff_density_max         0.109
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 1390 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.13(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3400
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0616P)^2^+0.0234P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0987
_reflns_number_gt                3022
_reflns_number_total             3400
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob27187k.txt
_cod_data_source_block           28a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

 Adding full bibliography for 7152853--7152857.cif.
;
_cod_original_cell_volume        1917.03(5)
_cod_original_sg_symbol_H-M      P4(3)
_cod_database_code               7152856