#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:13:55 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178426 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/47/4024733.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_4024733
loop_
_publ_author_name
'Krishnan Damodaran'
'Simon D. Nielsen'
'Steven J. Geib'
'Wei Zhang'
'Yimin Lu'
'Dennis P. Curran'
_publ_section_title
;
Aryl-Csp3 Bond Rotation Barriers of 2-Aryl
Perhydropyrrolo[3,4-c]pyrrole-1,3-diones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5481
_journal_page_last               5485
_journal_paper_doi               10.1021/jo901123c
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C23 H29 N3 O5'
_chemical_formula_weight         427.49
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.030(2)
_cell_angle_beta                 106.955(2)
_cell_angle_gamma                114.730(2)
_cell_formula_units_Z            2
_cell_length_a                   10.4794(11)
_cell_length_b                   10.5119(12)
_cell_length_c                   11.4317(12)
_cell_measurement_reflns_used    1018
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      20.41
_cell_measurement_theta_min      2.27
_cell_volume                     1076.0(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0666
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10606
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9806
_exptl_absorpt_correction_T_min  0.9733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.885
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         4926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.885
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0552
_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)+(0.0780P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1430
_reflns_number_gt                3106
_reflns_number_total             4926
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901123c_si_003.cif
_cod_data_source_block           simon1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4024733
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.63325(16) 0.11092(15) -0.08091(13) 0.0323(4) Uani 1 1 d . . .
N1 N 0.71843(18) 0.35261(17) -0.03784(15) 0.0262(4) Uani 1 1 d . . .
C1 C 0.6381(2) 0.2142(2) -0.02542(18) 0.0265(4) Uani 1 1 d . . .
O2 O 1.09804(16) 0.05922(15) 0.16217(14) 0.0372(4) Uani 1 1 d . . .
N2 N 0.69795(18) 0.34913(18) 0.27410(15) 0.0278(4) Uani 1 1 d . . .
C2 C 0.5623(2) 0.2182(2) 0.06790(18) 0.0257(4) Uani 1 1 d . . .
H2 H 0.464(2) 0.143(2) 0.0405(19) 0.032(6) Uiso 1 1 d . . .
O3 O 0.82288(18) 0.31230(17) 0.45813(14) 0.0430(4) Uani 1 1 d . . .
N3 N 0.77394(19) 0.62225(18) 0.37409(16) 0.0322(4) Uani 1 1 d . . .
C3 C 0.6508(2) 0.2089(2) 0.20237(19) 0.0273(5) Uani 1 1 d . . .
H3 H 0.580(2) 0.135(2) 0.2338(18) 0.024(5) Uiso 1 1 d . . .
O4 O 0.61811(17) 0.64529(15) 0.20018(13) 0.0367(4) Uani 1 1 d . . .
C4 C 0.7756(2) 0.3863(2) 0.39763(19) 0.0330(5) Uani 1 1 d . . .
O5 O 0.76260(17) 0.57783(15) 0.03404(14) 0.0399(4) Uani 1 1 d . . .
C5 C 0.8049(3) 0.5293(3) 0.4580(2) 0.0372(5) Uani 1 1 d . . .
H5A H 0.742(2) 0.513(2) 0.513(2) 0.039(6) Uiso 1 1 d . . .
H5B H 0.907(3) 0.577(3) 0.503(2) 0.059(8) Uiso 1 1 d . . .
C6 C 0.6672(2) 0.5717(2) 0.26108(19) 0.0279(5) Uani 1 1 d . . .
C7 C 0.5998(2) 0.4133(2) 0.21464(18) 0.0255(4) Uani 1 1 d . . .
C8 C 0.5717(2) 0.3678(2) 0.07751(19) 0.0261(4) Uani 1 1 d . . .
H8 H 0.485(2) 0.3683(18) 0.0291(17) 0.016(5) Uiso 1 1 d . . .
C9 C 0.6966(2) 0.4516(2) 0.02671(18) 0.0276(5) Uani 1 1 d . . .
C10 C 0.8133(2) 0.3886(2) -0.1158(2) 0.0318(5) Uani 1 1 d . . .
H10A H 0.881(2) 0.494(2) -0.0877(18) 0.025(5) Uiso 1 1 d . . .
H10B H 0.876(2) 0.338(2) -0.0940(19) 0.035(6) Uiso 1 1 d . . .
C11 C 0.7227(3) 0.3543(3) -0.2527(2) 0.0411(6) Uani 1 1 d . . .
H11C H 0.668(3) 0.411(2) -0.271(2) 0.041(6) Uiso 1 1 d . . .
H11A H 0.650(3) 0.251(3) -0.281(2) 0.057(8) Uiso 1 1 d . . .
H11B H 0.792(3) 0.379(3) -0.303(2) 0.058(7) Uiso 1 1 d . . .
C12 C 0.9164(2) 0.2739(2) 0.20873(19) 0.0293(5) Uani 1 1 d . . .
H12 H 0.937(2) 0.378(2) 0.2215(19) 0.031(6) Uiso 1 1 d . . .
C13 C 1.0220(2) 0.2329(2) 0.1961(2) 0.0307(5) Uani 1 1 d . . .
H13 H 1.118(3) 0.301(2) 0.197(2) 0.042(6) Uiso 1 1 d . . .
C14 C 0.9888(2) 0.0894(2) 0.17877(18) 0.0278(5) Uani 1 1 d . . .
C15 C 0.8524(2) -0.0119(2) 0.17901(18) 0.0289(5) Uani 1 1 d . . .
H15 H 0.829(2) -0.111(2) 0.1663(18) 0.024(5) Uiso 1 1 d . . .
C16 C 0.7491(2) 0.0315(2) 0.19471(18) 0.0284(5) Uani 1 1 d . . .
H16 H 0.653(3) -0.041(2) 0.194(2) 0.038(6) Uiso 1 1 d . . .
C17 C 0.7773(2) 0.1727(2) 0.20648(17) 0.0258(4) Uani 1 1 d . . .
C18 C 1.0623(3) -0.0886(3) 0.1345(3) 0.0394(6) Uani 1 1 d . . .
H18B H 1.048(2) -0.136(2) 0.207(2) 0.041(6) Uiso 1 1 d . . .
H18C H 1.146(3) -0.091(2) 0.116(2) 0.049(7) Uiso 1 1 d . . .
H18A H 0.972(3) -0.136(3) 0.062(2) 0.051(7) Uiso 1 1 d . . .
C19 C 0.8288(3) 0.7704(2) 0.4315(2) 0.0381(5) Uani 1 1 d . . .
H19A H 0.929(3) 0.797(2) 0.493(2) 0.039(6) Uiso 1 1 d . . .
H19B H 0.845(3) 0.830(3) 0.366(2) 0.052(7) Uiso 1 1 d . . .
C20 C 0.7254(3) 0.7936(3) 0.4873(2) 0.0406(6) Uani 1 1 d . . .
H20B H 0.715(2) 0.747(2) 0.562(2) 0.038(6) Uiso 1 1 d . . .
H20A H 0.618(3) 0.746(3) 0.425(3) 0.074(9) Uiso 1 1 d . . .
C21 C 0.7715(4) 0.9504(3) 0.5252(3) 0.0523(7) Uani 1 1 d . . .
H21B H 0.784(3) 0.998(3) 0.457(3) 0.074(9) Uiso 1 1 d . . .
H21A H 0.874(3) 0.994(2) 0.593(2) 0.044(7) Uiso 1 1 d . . .
C22 C 0.6628(4) 0.9757(4) 0.5733(4) 0.0786(12) Uani 1 1 d . . .
H22A H 0.696(3) 1.080(4) 0.589(3) 0.091(11) Uiso 1 1 d . . .
H22B H 0.562(5) 0.921(4) 0.524(4) 0.108(13) Uiso 1 1 d . . .
H22C H 0.662(4) 0.940(4) 0.655(4) 0.113(15) Uiso 1 1 d . . .
C23 C 0.4510(3) 0.3448(3) 0.2395(2) 0.0348(5) Uani 1 1 d . . .
H23B H 0.388(2) 0.388(2) 0.1984(19) 0.031(6) Uiso 1 1 d . . .
H23C H 0.394(3) 0.237(3) 0.209(2) 0.042(6) Uiso 1 1 d . . .
H23A H 0.466(3) 0.362(2) 0.327(2) 0.046(7) Uiso 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C9 113.60(17) . . ?
C1 N1 C10 122.34(17) . . ?
C9 N1 C10 124.02(17) . . ?
O1 C1 N1 124.11(19) . . ?
O1 C1 C2 128.07(18) . . ?
N1 C1 C2 107.81(16) . . ?
C14 O2 C18 116.89(17) . . ?
C4 N2 C3 122.56(16) . . ?
C4 N2 C7 121.12(17) . . ?
C3 N2 C7 111.18(15) . . ?
C1 C2 C8 104.04(15) . . ?
C1 C2 C3 112.66(16) . . ?
C8 C2 C3 105.84(16) . . ?
C1 C2 H2 109.6(13) . . ?
C8 C2 H2 114.9(13) . . ?
C3 C2 H2 109.8(13) . . ?
C6 N3 C5 122.63(18) . . ?
C6 N3 C19 118.74(18) . . ?
C5 N3 C19 115.90(18) . . ?
N2 C3 C17 114.45(16) . . ?
N2 C3 C2 102.50(15) . . ?
C17 C3 C2 113.56(16) . . ?
N2 C3 H3 108.8(11) . . ?
C17 C3 H3 108.9(11) . . ?
C2 C3 H3 108.3(11) . . ?
O3 C4 N2 123.8(2) . . ?
O3 C4 C5 120.6(2) . . ?
N2 C4 C5 115.56(18) . . ?
N3 C5 C4 116.11(18) . . ?
N3 C5 H5A 108.4(12) . . ?
C4 C5 H5A 107.7(12) . . ?
N3 C5 H5B 106.2(16) . . ?
C4 C5 H5B 106.4(15) . . ?
H5A C5 H5B 112(2) . . ?
O4 C6 N3 123.47(19) . . ?
O4 C6 C7 120.19(18) . . ?
N3 C6 C7 116.19(17) . . ?
N2 C7 C6 113.21(16) . . ?
N2 C7 C8 100.75(15) . . ?
C6 C7 C8 116.22(16) . . ?
N2 C7 C23 110.80(16) . . ?
C6 C7 C23 106.76(17) . . ?
C8 C7 C23 109.03(17) . . ?
C7 C8 C9 117.00(16) . . ?
C7 C8 C2 104.77(15) . . ?
C9 C8 C2 103.69(16) . . ?
C7 C8 H8 110.0(11) . . ?
C9 C8 H8 108.9(12) . . ?
C2 C8 H8 112.2(11) . . ?
O5 C9 N1 124.00(19) . . ?
O5 C9 C8 128.96(19) . . ?
N1 C9 C8 106.98(16) . . ?
N1 C10 C11 112.00(19) . . ?
N1 C10 H10A 105.2(11) . . ?
C11 C10 H10A 111.3(11) . . ?
N1 C10 H10B 107.0(12) . . ?
C11 C10 H10B 113.3(12) . . ?
H10A C10 H10B 107.7(17) . . ?
C10 C11 H11C 110.3(13) . . ?
C10 C11 H11A 112.5(15) . . ?
H11C C11 H11A 109(2) . . ?
C10 C11 H11B 109.5(15) . . ?
H11C C11 H11B 107.8(19) . . ?
H11A C11 H11B 108(2) . . ?
C13 C12 C17 120.6(2) . . ?
C13 C12 H12 121.9(11) . . ?
C17 C12 H12 117.5(11) . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13 121.8(13) . . ?
C14 C13 H13 118.1(13) . . ?
O2 C14 C15 124.34(19) . . ?
O2 C14 C13 115.78(18) . . ?
C15 C14 C13 119.88(19) . . ?
C14 C15 C16 119.2(2) . . ?
C14 C15 H15 120.2(11) . . ?
C16 C15 H15 120.6(11) . . ?
C17 C16 C15 121.9(2) . . ?
C17 C16 H16 119.4(13) . . ?
C15 C16 H16 118.7(13) . . ?
C16 C17 C12 118.27(19) . . ?
C16 C17 C3 118.60(17) . . ?
C12 C17 C3 122.79(18) . . ?
O2 C18 H18B 110.6(13) . . ?
O2 C18 H18C 106.3(14) . . ?
H18B C18 H18C 110.5(19) . . ?
O2 C18 H18A 109.7(14) . . ?
H18B C18 H18A 110(2) . . ?
H18C C18 H18A 109(2) . . ?
N3 C19 C20 113.66(19) . . ?
N3 C19 H19A 105.6(13) . . ?
C20 C19 H19A 113.1(13) . . ?
N3 C19 H19B 107.4(14) . . ?
C20 C19 H19B 110.0(14) . . ?
H19A C19 H19B 106.6(19) . . ?
C19 C20 C21 112.2(2) . . ?
C19 C20 H20B 114.3(12) . . ?
C21 C20 H20B 107.7(12) . . ?
C19 C20 H20A 110.2(15) . . ?
C21 C20 H20A 109.0(15) . . ?
H20B C20 H20A 103(2) . . ?
C22 C21 C20 112.8(3) . . ?
C22 C21 H21B 110.6(17) . . ?
C20 C21 H21B 109.8(17) . . ?
C22 C21 H21A 109.4(13) . . ?
C20 C21 H21A 107.9(13) . . ?
H21B C21 H21A 106(2) . . ?
C21 C22 H22A 107.7(19) . . ?
C21 C22 H22B 114(2) . . ?
H22A C22 H22B 114(3) . . ?
C21 C22 H22C 111(2) . . ?
H22A C22 H22C 109(3) . . ?
H22B C22 H22C 100(3) . . ?
C7 C23 H23B 109.0(12) . . ?
C7 C23 H23C 113.0(12) . . ?
H23B C23 H23C 108.8(18) . . ?
C7 C23 H23A 111.6(14) . . ?
H23B C23 H23A 106.6(18) . . ?
H23C C23 H23A 107.7(19) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.212(2) . ?
N1 C1 1.380(2) . ?
N1 C9 1.386(2) . ?
N1 C10 1.467(3) . ?
C1 C2 1.513(3) . ?
O2 C14 1.369(2) . ?
O2 C18 1.437(3) . ?
N2 C4 1.354(3) . ?
N2 C3 1.469(3) . ?
N2 C7 1.477(2) . ?
C2 C8 1.532(3) . ?
C2 C3 1.577(3) . ?
C2 H2 0.94(2) . ?
O3 C4 1.221(2) . ?
N3 C6 1.347(3) . ?
N3 C5 1.459(3) . ?
N3 C19 1.464(3) . ?
C3 C17 1.513(3) . ?
C3 H3 0.99(2) . ?
O4 C6 1.229(2) . ?
C4 C5 1.499(3) . ?
O5 C9 1.199(2) . ?
C5 H5A 1.01(2) . ?
C5 H5B 0.93(3) . ?
C6 C7 1.512(3) . ?
C7 C8 1.527(3) . ?
C7 C23 1.538(3) . ?
C8 C9 1.530(3) . ?
C8 H8 0.918(18) . ?
C10 C11 1.512(3) . ?
C10 H10A 1.01(2) . ?
C10 H10B 0.99(2) . ?
C11 H11C 0.98(2) . ?
C11 H11A 1.00(3) . ?
C11 H11B 1.01(3) . ?
C12 C13 1.386(3) . ?
C12 C17 1.391(3) . ?
C12 H12 1.01(2) . ?
C13 C14 1.391(3) . ?
C13 H13 0.95(2) . ?
C14 C15 1.380(3) . ?
C15 C16 1.390(3) . ?
C15 H15 0.96(2) . ?
C16 C17 1.381(3) . ?
C16 H16 0.98(2) . ?
C18 H18B 1.00(2) . ?
C18 H18C 0.97(2) . ?
C18 H18A 0.97(3) . ?
C19 C20 1.501(3) . ?
C19 H19A 0.99(2) . ?
C19 H19B 1.00(3) . ?
C20 C21 1.516(3) . ?
C20 H20B 1.01(2) . ?
C20 H20A 1.03(3) . ?
C21 C22 1.510(5) . ?
C21 H21B 0.95(3) . ?
C21 H21A 1.02(2) . ?
C22 H22A 1.00(3) . ?
C22 H22B 0.94(4) . ?
C22 H22C 1.02(4) . ?
C23 H23B 0.97(2) . ?
C23 H23C 1.02(2) . ?
C23 H23A 0.97(2) . ?
