Synthesis of Psychrophilin E.
Ngen, Sarah T. Y.; Kaur, Harveen; Hume, Paul A.; Furkert, Daniel P.; Brimble, Margaret A.; The Journal of organic chemistry 81 (2016) 7635–7643; doi:10.1021/acs.joc.6b01369

data_4037053
_publ_section_title
;
 Synthesis of Psychrophilin E.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7635
_journal_page_last               7643
_journal_paper_doi               10.1021/acs.joc.6b01369
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C25 H24 N4 O4'
_chemical_formula_sum            'C25 H24 N4 O4'
_chemical_formula_weight         444.48
_chemical_name_common            'Psychrophilin E'
_chemical_name_systematic
;
N-(2,10,16-trioxo-1,9,15-triazapentacyclo[17.6.1.03,8.011,15.020,25]hexacosa-3,5,7,19(26),20,22,24-heptaen-17-yl)acetamide
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3522(3)
_cell_length_b                   12.7928(4)
_cell_length_c                   13.7288(5)
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.337
_cell_measurement_theta_min      3.110
_cell_volume                     2169.41(12)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2008)'
_computing_data_collection       '<i>APEX2</i> (Bruker, 2008)'
_computing_data_reduction        '<i>SAINT</i> (Bruker, 2008)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_av_unetI/netI     0.0863
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16207
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.953
_diffrn_reflns_theta_min         2.176
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9123
_exptl_absorpt_correction_T_min  0.8897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(<i>SADABS</i>; Bruker, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       plate
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1268 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5159
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0501
_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^)+(0.0441P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1084
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                3731
_reflns_number_total             5159
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01369_si_001.cif
_cod_data_source_block           pc0621_0m
_cod_database_code               4037053
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2013-2
_shelx_res_checksum              32759
_shelx_hkl_checksum              4911