#------------------------------------------------------------------------------
#$Date: 2017-02-04 16:14:03 +0200 (Sat, 04 Feb 2017) $
#$Revision: 191740 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/54/7155412.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7155412
loop_
_publ_author_name
'Kubyshkin, Vladimir'
'Budisa, Nediljko'
_publ_section_title
;
 Construction of a polyproline structure with hydrophobic exterior using
 octahydroindole-2-carboxylic acid.
;
_journal_issue                   3
_journal_name_full               'Organic & 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       'ω 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/[σ²(Fo²)+(0.0352P)²+0.7846P] where P=(Fo²+2Fc²)/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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.21920(19) 0.88316(16) 0.15847(3) 0.0251(3) Uani 1 1 d .
N2 N 0.48362(19) 0.54085(16) 0.09155(3) 0.0261(3) Uani 1 1 d .
O1 O 0.03424(19) 0.75049(14) 0.21523(3) 0.0373(3) Uani 1 1 d .
O2 O 0.09629(19) 0.51423(14) 0.19304(3) 0.0394(3) Uani 1 1 d .
O3 O -0.03312(18) 0.77628(15) 0.13333(3) 0.0367(3) Uani 1 1 d .
O4 O 0.3555(2) 0.35170(16) 0.03705(3) 0.0428(3) Uani 1 1 d .
O5 O 0.06291(18) 0.36450(16) 0.05909(3) 0.0391(3) Uani 1 1 d .
O6 O 0.4352(2) 0.30752(15) 0.11619(3) 0.0444(3) Uani 1 1 d .
C1 C 0.2723(2) 0.73074(19) 0.17282(4) 0.0266(3) Uani 1 1 d .
H1A H 0.2969 0.6517 0.1551 0.032 Uiso 1 1 calc R
C2 C 0.4582(2) 0.7672(2) 0.19146(4) 0.0316(4) Uani 1 1 d .
H2A H 0.4327 0.7871 0.2150 0.038 Uiso 1 1 calc R
H2B H 0.5494 0.6785 0.1895 0.038 Uiso 1 1 calc R
C3 C 0.5349(2) 0.9158(2) 0.17472(4) 0.0289(4) Uani 1 1 d .
H3A H 0.5935 0.8831 0.1534 0.035 Uiso 1 1 calc R
C4 C 0.3546(2) 1.0098(2) 0.16699(4) 0.0261(3) Uani 1 1 d .
H4A H 0.3764 1.0799 0.1476 0.031 Uiso 1 1 calc R
C5 C 0.2824(3) 1.1072(2) 0.19599(4) 0.0329(4) Uani 1 1 d .
H5A H 0.1785 1.1773 0.1885 0.040 Uiso 1 1 calc R
H5B H 0.2296 1.0349 0.2128 0.040 Uiso 1 1 calc R
C6 C 0.4386(3) 1.2073(2) 0.21141(5) 0.0388(4) Uani 1 1 d .
H6A H 0.3867 1.2664 0.2304 0.047 Uiso 1 1 calc R
H6B H 0.4863 1.2849 0.1952 0.047 Uiso 1 1 calc R
C7 C 0.6013(3) 1.1015(2) 0.22273(4) 0.0365(4) Uani 1 1 d .
H7A H 0.7020 1.1672 0.2329 0.044 Uiso 1 1 calc R
H7B H 0.5542 1.0264 0.2395 0.044 Uiso 1 1 calc R
C8 C 0.6840(2) 1.0098(2) 0.19398(4) 0.0359(4) Uani 1 1 d .
H8A H 0.7818 0.9357 0.2023 0.043 Uiso 1 1 calc R
H8B H 0.7476 1.0849 0.1789 0.043 Uiso 1 1 calc R
C9 C 0.1188(2) 0.6699(2) 0.19584(4) 0.0273(3) Uani 1 1 d .
C10 C -0.0394(3) 0.4460(2) 0.21571(6) 0.0531(6) Uani 1 1 d .
H10A H -0.0578 0.3339 0.2105 0.080 Uiso 1 1 calc R
H10B H -0.1611 0.5019 0.2138 0.080 Uiso 1 1 calc R
H10C H 0.0088 0.4562 0.2382 0.080 Uiso 1 1 calc R
C11 C 0.0676(2) 0.8930(2) 0.13842(4) 0.0273(3) Uani 1 1 d .
C12 C 0.0283(3) 1.0494(2) 0.12211(4) 0.0348(4) Uani 1 1 d .
H12A H -0.1034 1.0515 0.1143 0.052 Uiso 1 1 calc R
H12B H 0.1149 1.0634 0.1035 0.052 Uiso 1 1 calc R
H12C H 0.0478 1.1352 0.1379 0.052 Uiso 1 1 calc R
C13 C 0.2871(2) 0.5419(2) 0.07989(4) 0.0266(3) Uani 1 1 d .
H13A H 0.1981 0.5361 0.0990 0.032 Uiso 1 1 calc R
C14 C 0.2673(2) 0.7033(2) 0.06285(4) 0.0291(4) Uani 1 1 d .
H14A H 0.2893 0.6939 0.0389 0.035 Uiso 1 1 calc R
H14B H 0.1397 0.7492 0.0666 0.035 Uiso 1 1 calc R
C15 C 0.4220(2) 0.80375(19) 0.07909(4) 0.0266(3) Uani 1 1 d .
H15A H 0.3767 0.8323 0.1016 0.032 Uiso 1 1 calc R
C16 C 0.5863(2) 0.68625(19) 0.08292(4) 0.0243(3) Uani 1 1 d .
H16A H 0.6703 0.7192 0.1015 0.029 Uiso 1 1 calc R
C17 C 0.7036(2) 0.6678(2) 0.05161(4) 0.0279(4) Uani 1 1 d .
H17A H 0.8162 0.6009 0.0561 0.034 Uiso 1 1 calc R
H17B H 0.6261 0.6146 0.0346 0.034 Uiso 1 1 calc R
C18 C 0.7680(2) 0.8295(2) 0.03912(4) 0.0327(4) Uani 1 1 d .
H18A H 0.8463 0.8823 0.0561 0.039 Uiso 1 1 calc R
H18B H 0.8473 0.8158 0.0193 0.039 Uiso 1 1 calc R
C19 C 0.5971(3) 0.9320(2) 0.03104(4) 0.0356(4) Uani 1 1 d .
H19A H 0.5201 0.8801 0.0138 0.043 Uiso 1 1 calc R
H19B H 0.6408 1.0354 0.0225 0.043 Uiso 1 1 calc R
C20 C 0.4754(3) 0.9577(2) 0.06143(5) 0.0353(4) Uani 1 1 d .
H20A H 0.3574 1.0135 0.0550 0.042 Uiso 1 1 calc R
H20B H 0.5453 1.0269 0.0769 0.042 Uiso 1 1 calc R
C21 C 0.2470(2) 0.4071(2) 0.05639(4) 0.0296(4) Uani 1 1 d .
C22 C -0.0072(3) 0.2490(2) 0.03602(5) 0.0485(5) Uani 1 1 d .
H22A H -0.1419 0.2282 0.0404 0.073 Uiso 1 1 calc R
H22B H 0.0653 0.1506 0.0383 0.073 Uiso 1 1 calc R
H22C H 0.0074 0.2897 0.0136 0.073 Uiso 1 1 calc R
C23 C 0.5424(3) 0.41956(19) 0.11074(4) 0.0305(4) Uani 1 1 d .
C24 C 0.7404(3) 0.4276(2) 0.12467(5) 0.0391(4) Uani 1 1 d .
H24A H 0.7559 0.3452 0.1414 0.059 Uiso 1 1 calc R
H24B H 0.7610 0.5317 0.1346 0.059 Uiso 1 1 calc R
H24C H 0.8332 0.4110 0.1071 0.059 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C11 N1 C1 119.96(13)
C11 N1 C4 127.57(14)
C1 N1 C4 112.35(12)
C23 N2 C13 118.79(14)
C23 N2 C16 128.44(14)
C13 N2 C16 112.45(13)
C9 O2 C10 114.68(14)
C21 O5 C22 117.12(15)
N1 C1 C9 111.32(13)
N1 C1 C2 103.71(13)
C9 C1 C2 111.42(13)
C3 C2 C1 104.08(13)
C2 C3 C4 103.07(13)
C2 C3 C8 116.02(14)
C4 C3 C8 113.83(14)
N1 C4 C5 111.05(14)
N1 C4 C3 101.96(13)
C5 C4 C3 113.34(13)
C6 C5 C4 112.30(15)
C5 C6 C7 109.92(15)
C8 C7 C6 110.67(15)
C7 C8 C3 113.41(14)
O1 C9 O2 123.95(16)
O1 C9 C1 124.48(15)
O2 C9 C1 111.50(14)
O3 C11 N1 120.51(15)
O3 C11 C12 121.56(15)
N1 C11 C12 117.92(15)
N2 C13 C21 112.17(14)
N2 C13 C14 103.78(13)
C21 C13 C14 111.39(13)
C15 C14 C13 103.44(13)
C14 C15 C16 102.75(12)
C14 C15 C20 116.21(14)
C16 C15 C20 114.42(13)
N2 C16 C17 112.35(13)
N2 C16 C15 101.31(12)
C17 C16 C15 112.85(13)
C18 C17 C16 110.33(14)
C19 C18 C17 110.37(14)
C18 C19 C20 110.50(14)
C19 C20 C15 113.48(14)
O4 C21 O5 124.29(16)
O4 C21 C13 126.41(16)
O5 C21 C13 109.17(14)
O6 C23 N2 119.97(16)
O6 C23 C24 122.22(16)
N2 C23 C24 117.80(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C11 1.346(2)
N1 C1 1.463(2)
N1 C4 1.474(2)
N2 C23 1.354(2)
N2 C13 1.461(2)
N2 C16 1.468(2)
O1 C9 1.201(2)
O2 C9 1.330(2)
O2 C10 1.448(2)
O3 C11 1.232(2)
O4 C21 1.193(2)
O5 C21 1.348(2)
O5 C22 1.442(2)
O6 C23 1.231(2)
C1 C9 1.520(2)
C1 C2 1.543(2)
C2 C3 1.527(2)
C3 C4 1.529(2)
C3 C8 1.532(2)
C4 C5 1.527(2)
C5 C6 1.522(2)
C6 C7 1.524(3)
C7 C8 1.520(3)
C11 C12 1.505(2)
C13 C21 1.515(2)
C13 C14 1.536(2)
C14 C15 1.530(2)
C15 C16 1.531(2)
C15 C20 1.534(2)
C16 C17 1.527(2)
C17 C18 1.527(2)
C18 C19 1.517(2)
C19 C20 1.521(3)
C23 C24 1.505(3)
