Strategies, Setbacks, and Successes in the Synthesis of (-)-Spiroleucettadine.
Lamb, Richard A.; Lucas, Nigel T.; Lessene, Guillaume; Hawkins, Bill C.; The Journal of organic chemistry 83 (2018) 10120–10133; doi:10.1021/acs.joc.8b01404

data_4035088
_publ_section_title
;
 Strategies, Setbacks, and Successes in the Synthesis of
 (-)-Spiroleucettadine.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10120
_journal_page_last               10133
_journal_paper_doi               10.1021/acs.joc.8b01404
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C30 H34 N2 O5'
_chemical_formula_sum            'C30 H34 N2 O5'
_chemical_formula_weight         502.59
_chemical_name_systematic
;
t-Butyl 2-benzyl-5-{[4-(benzyloxy)phenyl]methyl}-2-hydroxy-3-methyl-
4-oxoimidazolidine-1-carboxylate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_block_code                ntl1606_bch_RAL_1_408
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                97.047(2)
_cell_angle_beta                 91.529(2)
_cell_angle_gamma                101.080(2)
_cell_formula_units_Z            4
_cell_length_a                   9.1299(2)
_cell_length_b                   13.1630(3)
_cell_length_c                   23.1982(4)
_cell_measurement_reflns_used    20095
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      74.759
_cell_measurement_theta_min      3.425
_cell_volume                     2711.64(10)
_computing_cell_refinement       'CrysAlisPro 1.171.37.33 (Rigaku OD, 2014)'
_computing_data_collection       'CrysAlisPro 1.171.37.33 (Rigaku OD, 2014)'
_computing_data_reduction        'CrysAlisPro 1.171.37.33 (Rigaku OD, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.9 (CCDC, 2016)'
_computing_publication_material  'enCIFer 1.6 (CCDC, 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0(1)
_diffrn_crystal_treatment
; 
Crystal was attached with Paratone N oil to a 0.3 mm CryoLoop supported 
in a copper mounting pin, then quenched in a cold nitrogen gas stream
from an Oxford Cryosystems Cryostream.
;
_diffrn_detector_area_resol_mean 5.1725
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            45735
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         74.903
_diffrn_reflns_theta_min         3.451
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.37.33 (Rigaku Oxford Diffraction, 2014)
Numerical absorption correction based on gaussian integration 
over a multifaceted crystal model. 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       plate
_exptl_crystal_F_000             1072
_exptl_crystal_preparation
;
Crystals were grown by evaporation of an ethyl acetate solution at RT.
;
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     677
_refine_ls_number_reflns         10848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0486
_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^)+(0.0670P)^2^+0.8995P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1320
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9152
_reflns_number_total             10848
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01404_si_002.cif
_cod_data_source_block           45
_cod_original_cell_volume        2711.63(10)
_cod_database_code               4035088
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.793
_shelx_estimated_absorpt_t_max   0.980
_shelx_res_checksum              87835
_shelx_hkl_checksum              53166