Construction of a polyproline structure with hydrophobic exterior using octahydroindole-2-carboxylic acid.
Kubyshkin, Vladimir; Budisa, Nediljko; Organic & biomolecular chemistry 15 (2017) 619–627; doi:10.1039/c6ob02306a

data_7155412
_publ_section_title
;
 Construction of a polyproline structure with hydrophobic exterior using
 octahydroindole-2-carboxylic acid.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              619
_journal_page_last               627
_journal_paper_doi               10.1039/c6ob02306a
_journal_volume                  15
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C12 H19 N O3'
_chemical_formula_weight         225.28
_chemical_melting_point          343
_chemical_name_common
'N-acetyl octahydroindole-2-carboxylic acid methyl ester'
_chemical_name_systematic
'methyl (2S,3aS,7aS)-1-acetyloctahydro-1H-indole-2-carboxylate'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_audit_update_record
;
2016-10-17 deposited with the CCDC.
2016-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.03210(18)
_cell_length_b                   8.4501(2)
_cell_length_c                   40.7561(11)
_cell_measurement_reflns_used    8794
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.5070
_cell_measurement_theta_min      3.2210
_cell_volume                     2421.81(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5435
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            15629
_diffrn_reflns_theta_full        67.49
_diffrn_reflns_theta_max         67.49
_diffrn_reflns_theta_min         4.34
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.719
_exptl_absorpt_correction_T_max  0.9521
_exptl_absorpt_correction_T_min  0.7619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             976
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.12(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4373
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0333
_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^)+(0.0352P)^2^+0.7846P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0840
_reflns_number_gt                4266
_reflns_number_total             4373
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob02306a2.cif
_cod_data_source_block           cu-1834
_cod_depositor_comments
'Adding full bibliography for 7155412--7155413.cif.'
_cod_original_cell_volume        2421.79(11)
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7155412