Crystal structure and absolute configuration of (3<i>S</i>,4a<i>S</i>,8a<i>S</i>)-<i>N</i>-<i>tert</i>-butyl-2-[(<i>S</i>)-3-(2-chloro-4-nitrobenzamido)-2-hydroxypropyl]decahydroisoquinoline-3-carboxamide and (3<i>S</i>,4a<i>S</i>,8a<i>S</i>)-<i>N</i>-<i>tert</i>-butyl-2-{(<i>S</i>)-2-[(<i>S</i>)-1-(2-chloro-4-nitrobenzoyl)pyrrolidin-2-yl]-2-hydroxyethyl}decahydroisoquinoline-3-carboxamide
Maxson, Tucker; Bertke, Jeffery A.; Gray, Danielle L.; Mitchell, Douglas A.; Acta Crystallographica Section E 71 (2015) 1401–1407; doi:10.1107/S2056989015020046

data_2241261
_publ_contact_author
;
Jeffery A. Bertke
University of Illinois
School of Chemical Sciences, Box 59-1
505 South Mathews Avenue
Urbana, Illinois  61801
USA
;
_publ_section_title
;
 Crystal structure and absolute configuration of
 (3<i>S</i>,4a<i>S</i>,8a<i>S</i>)-<i>N</i>-<i>tert</i>-butyl-2-[(<i>S</i>)-3-(2-chloro-4-nitrobenzamido)-2-hydroxypropyl]decahydroisoquinoline-3-carboxamide
 and
 (3<i>S</i>,4a<i>S</i>,8a<i>S</i>)-<i>N</i>-<i>tert</i>-butyl-2-{(<i>S</i>)-2-[(<i>S</i>)-1-(2-chloro-4-nitrobenzoyl)pyrrolidin-2-yl]-2-hydroxyethyl}decahydroisoquinoline-3-carboxamide
;
_journal_coeditor_code           PK2566
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1401
_journal_page_last               1407
_journal_paper_doi               10.1107/S2056989015020046
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C24 H35 Cl N4 O5'
_chemical_formula_moiety         'C24 H35 Cl N4 O5'
_chemical_formula_sum            'C24 H35 Cl N4 O5'
_chemical_formula_weight         495.01
_chemical_name_systematic
(3<i>S</i>,4a<i>S</i>,8a<i>S</i>)-<i>N</i>-<i>tert</i>-Butyl-2-[(<i>S</i>)-3-(2-chloro-4-nitrobenzamido)-2-hydroxypropyl]decahydroisoquinoline-3-carboxamide
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.8408(7)
_cell_length_b                   20.2263(8)
_cell_length_c                   6.7923(3)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      24.52
_cell_measurement_theta_min      2.29
_cell_volume                     2588.41(18)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014), XPREP (Bruker, 2014), and SADABS (Bruker,
2014)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and CrystalMaker (CrystalMaker, 1994)
;
_computing_publication_material
;
XCIF (Bruker, 2014) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS2014 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Siemens Platform/APEXII CCD'
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            30342
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.279
_diffrn_reflns_theta_min         1.477
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.9604
_exptl_absorpt_correction_T_min  0.9526
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(SHELXTL/XPREP; Bruker, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.368
_exptl_crystal_size_mid          0.356
_exptl_crystal_size_min          0.286
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.434
_refine_ls_abs_structure_details
;
Flack (1983); Hooft <i>et al.</i> (2008); 2720 Friedels
;
_refine_ls_abs_structure_Flack   -0.008(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         5243
_refine_ls_number_restraints     53
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0355P)^2^+0.5785P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0854
_reflns_number_gt                4694
_reflns_number_total             5243
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            pk2566sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P2(1)2(1)2 '
_cod_database_code               2241261
_cod_database_fobs_code          2241261
_shelx_estimated_absorpt_t_min   0.934
_shelx_estimated_absorpt_t_max   0.948
_shelx_hkl_checksum              34970
_shelx_res_checksum              42945
_shelxl_version_number           2014/6