#------------------------------------------------------------------------------
#$Date: 2022-11-07 07:19:46 +0200 (Mon, 07 Nov 2022) $
#$Revision: 278978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/75/1567538.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_1567538
loop_
_publ_author_name
'Balanna, Kuruva'
'Barik, Soumen'
'Shee, Sayan'
'Gonnade, Rajesh G.'
'Biju, Akkattu T.'
_publ_section_title
;
 Dynamic kinetic resolution of γ,γ-disubstituted indole
 2-carboxaldehydes via NHC-Lewis acid cooperative catalysis for the
 synthesis of tetracyclic ε-lactones.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              11513
_journal_page_last               11518
_journal_paper_doi               10.1039/d2sc03745a
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H33 N O3, CH3 CH2 OH'
_chemical_formula_sum            'C33 H39 N O4'
_chemical_formula_weight         513.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-01-01 deposited with the CCDC.	2022-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.351(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2800(10)
_cell_length_b                   17.0143(19)
_cell_length_c                   10.0461(10)
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.20
_cell_measurement_theta_min      2.60
_cell_volume                     1433.5(3)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            28158
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.240
_diffrn_reflns_theta_min         4.871
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (BRUKER, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       0.0121(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         5575
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0433
_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/[σ²(Fo²)+(0.0408P)²+0.6926P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1073
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                5497
_reflns_number_total             5575
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc03745a2.cif
_cod_data_source_block           dh_hme_050821
_cod_depositor_comments          'Adding full bibliography for 1567538.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1567538
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.919
_shelx_estimated_absorpt_t_max   0.970
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7816(2) 0.39864(13) 0.2864(2) 0.0310(5) Uani 1 1 d . . . . .
O2 O 0.9906(4) 0.33747(19) 0.2830(3) 0.0597(9) Uani 1 1 d . . . . .
O3 O 0.9869(3) 0.76357(15) 0.4616(3) 0.0448(6) Uani 1 1 d . . . . .
H3A H 0.927952 0.802666 0.451764 0.067 Uiso 1 1 d R U . . .
N1 N 0.9014(3) 0.37499(13) -0.0136(2) 0.0212(5) Uani 1 1 d . . . . .
H1A H 0.967366 0.334765 0.011952 0.025 Uiso 1 1 d R U . . .
C1 C 0.6454(3) 0.52412(15) 0.0514(3) 0.0179(5) Uani 1 1 d . . . . .
H1 H 0.565571 0.551945 -0.037129 0.021 Uiso 1 1 calc R U . . .
C2 C 0.5505(3) 0.47544(15) 0.1132(3) 0.0205(5) Uani 1 1 d . . . . .
C3 C 0.3873(3) 0.49010(17) 0.0655(3) 0.0252(6) Uani 1 1 d . . . . .
H3 H 0.338025 0.529966 -0.005899 0.030 Uiso 1 1 calc R U . . .
C4 C 0.2958(4) 0.44826(19) 0.1193(3) 0.0321(6) Uani 1 1 d . . . . .
H4 H 0.185518 0.459634 0.085365 0.038 Uiso 1 1 calc R U . . .
C5 C 0.3657(4) 0.38970(19) 0.2228(4) 0.0373(7) Uani 1 1 d . . . . .
H5 H 0.303409 0.360739 0.259996 0.045 Uiso 1 1 calc R U . . .
C6 C 0.5268(4) 0.37336(19) 0.2721(3) 0.0350(7) Uani 1 1 d . . . . .
H6 H 0.575198 0.333147 0.342907 0.042 Uiso 1 1 calc R U . . .
C7 C 0.6168(3) 0.41629(17) 0.2170(3) 0.0261(6) Uani 1 1 d . . . . .
C8 C 0.8733(4) 0.37792(19) 0.2162(3) 0.0327(7) Uani 1 1 d . . . . .
C9 C 0.8325(3) 0.40830(16) 0.0703(3) 0.0212(5) Uani 1 1 d . . . . .
C10 C 0.7392(3) 0.47167(14) -0.0027(3) 0.0171(5) Uani 1 1 d . . . . .
C11 C 0.7481(3) 0.47666(14) -0.1409(2) 0.0155(5) Uani 1 1 d . . . . .
C12 C 0.8496(3) 0.41528(14) -0.1431(3) 0.0180(5) Uani 1 1 d . . . . .
C13 C 0.8844(3) 0.40253(16) -0.2638(3) 0.0212(5) Uani 1 1 d . . . . .
H13 H 0.951663 0.360664 -0.264787 0.025 Uiso 1 1 calc R U . . .
C14 C 0.8172(3) 0.45305(17) -0.3805(3) 0.0256(6) Uani 1 1 d . . . . .
H14 H 0.840609 0.446205 -0.463049 0.031 Uiso 1 1 calc R U . . .
C15 C 0.7137(3) 0.51542(16) -0.3831(3) 0.0234(5) Uani 1 1 d . . . . .
C16 C 0.6786(3) 0.52650(15) -0.2645(3) 0.0195(5) Uani 1 1 d . . . . .
H16 H 0.608164 0.567330 -0.265868 0.023 Uiso 1 1 calc R U . . .
C17 C 0.6443(4) 0.5672(2) -0.5168(3) 0.0357(7) Uani 1 1 d . . . . .
H17D H 0.597534 0.614098 -0.494151 0.054 Uiso 1 1 calc R U . . .
H17E H 0.561398 0.538361 -0.597959 0.054 Uiso 1 1 calc R U . . .
H17F H 0.728541 0.583022 -0.545514 0.054 Uiso 1 1 calc R U . . .
C18 C 0.7414(3) 0.58831(15) 0.1611(3) 0.0184(5) Uani 1 1 d . . . . .
C19 C 0.9010(3) 0.57954(16) 0.2582(3) 0.0210(5) Uani 1 1 d . . . . .
H19 H 0.955814 0.533365 0.252863 0.025 Uiso 1 1 calc R U . . .
C20 C 0.9833(3) 0.63666(17) 0.3636(3) 0.0244(6) Uani 1 1 d . . . . .
C21 C 0.9000(3) 0.70545(16) 0.3663(3) 0.0237(6) Uani 1 1 d . . . . .
C22 C 0.7375(3) 0.71608(16) 0.2709(3) 0.0211(5) Uani 1 1 d . . . . .
C23 C 0.6634(3) 0.65602(15) 0.1698(3) 0.0188(5) Uani 1 1 d . . . . .
H23 H 0.554104 0.661957 0.103816 0.023 Uiso 1 1 calc R U . . .
C24 C 1.1588(3) 0.6227(2) 0.4732(3) 0.0328(7) Uani 1 1 d . . . . .
C25 C 1.2196(4) 0.5421(2) 0.4503(4) 0.0388(8) Uani 1 1 d . . . . .
H25D H 1.329533 0.534501 0.524369 0.058 Uiso 1 1 calc R U . . .
H25E H 1.216471 0.539758 0.351633 0.058 Uiso 1 1 calc R U . . .
H25F H 1.151688 0.500609 0.460380 0.058 Uiso 1 1 calc R U . . .
C26 C 1.2669(4) 0.6858(2) 0.4543(4) 0.0421(8) Uani 1 1 d . . . . .
H26D H 1.377092 0.677311 0.526977 0.063 Uiso 1 1 calc R U . . .
H26E H 1.231227 0.737955 0.469074 0.063 Uiso 1 1 calc R U . . .
H26F H 1.261342 0.682459 0.354850 0.063 Uiso 1 1 calc R U . . .
C27 C 1.1731(4) 0.6234(3) 0.6316(3) 0.0491(9) Uani 1 1 d . . . . .
H27D H 1.283012 0.610999 0.700729 0.074 Uiso 1 1 calc R U . . .
H27E H 1.100797 0.584008 0.640866 0.074 Uiso 1 1 calc R U . . .
H27F H 1.144536 0.675532 0.654199 0.074 Uiso 1 1 calc R U . . .
C28 C 0.6426(3) 0.78953(16) 0.2761(3) 0.0247(6) Uani 1 1 d . . . . .
C29 C 0.7160(5) 0.86463(18) 0.2461(5) 0.0422(8) Uani 1 1 d . . . . .
H29D H 0.648648 0.909820 0.241668 0.063 Uiso 1 1 calc R U . . .
H29E H 0.723386 0.859422 0.152071 0.063 Uiso 1 1 calc R U . . .
H29F H 0.822900 0.872507 0.325534 0.063 Uiso 1 1 calc R U . . .
C30 C 0.6341(3) 0.79609(19) 0.4252(3) 0.0301(6) Uani 1 1 d . . . . .
H30D H 0.572654 0.842902 0.425376 0.045 Uiso 1 1 calc R U . . .
H30E H 0.742199 0.800308 0.504274 0.045 Uiso 1 1 calc R U . . .
H30F H 0.581976 0.749220 0.440971 0.045 Uiso 1 1 calc R U . . .
C31 C 0.4698(4) 0.78558(18) 0.1593(3) 0.0345(7) Uani 1 1 d . . . . .
H31A H 0.411914 0.832217 0.167192 0.052 Uiso 1 1 calc R U . . .
H31B H 0.418733 0.738267 0.174947 0.052 Uiso 1 1 calc R U . . .
H31C H 0.467975 0.783717 0.061152 0.052 Uiso 1 1 calc R U . . .
O4 O 1.0789(3) 0.24260(15) -0.0208(3) 0.0480(7) Uani 1 1 d . . . . .
H4A H 1.090(7) 0.223(4) -0.090(6) 0.078(17) Uiso 1 1 d . . . . .
C32 C 1.1025(5) 0.1825(2) 0.0834(4) 0.0491(9) Uani 1 1 d . . . . .
H32A H 1.131925 0.206275 0.181516 0.059 Uiso 1 1 calc R U . . .
H32B H 1.191786 0.148487 0.089717 0.059 Uiso 1 1 calc R U . . .
C33 C 0.9565(5) 0.1337(3) 0.0430(5) 0.0567(10) Uani 1 1 d . . . . .
H33A H 0.980795 0.088762 0.110281 0.085 Uiso 1 1 calc R U . . .
H33B H 0.920544 0.114588 -0.058232 0.085 Uiso 1 1 calc R U . . .
H33C H 0.872272 0.165481 0.050438 0.085 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C7 125.6(2) . . ?
C21 O3 H3A 109.3 . . ?
C12 N1 C9 108.1(2) . . ?
C12 N1 H1A 125.9 . . ?
C9 N1 H1A 126.0 . . ?
C10 C1 C2 110.5(2) . . ?
C10 C1 C18 115.7(2) . . ?
C2 C1 C18 110.72(19) . . ?
C10 C1 H1 106.4 . . ?
C2 C1 H1 106.4 . . ?
C18 C1 H1 106.4 . . ?
C7 C2 C3 116.9(2) . . ?
C7 C2 C1 123.6(2) . . ?
C3 C2 C1 119.6(2) . . ?
C4 C3 C2 121.9(3) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C7 119.5(3) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C2 C7 C6 122.0(3) . . ?
C2 C7 O1 124.2(2) . . ?
C6 C7 O1 113.5(2) . . ?
O2 C8 O1 118.0(3) . . ?
O2 C8 C9 123.1(3) . . ?
O1 C8 C9 118.8(2) . . ?
N1 C9 C10 110.2(2) . . ?
N1 C9 C8 119.0(2) . . ?
C10 C9 C8 130.6(2) . . ?
C9 C10 C11 106.1(2) . . ?
C9 C10 C1 126.9(2) . . ?
C11 C10 C1 126.9(2) . . ?
C16 C11 C12 119.2(2) . . ?
C16 C11 C10 134.1(2) . . ?
C12 C11 C10 106.7(2) . . ?
N1 C12 C13 129.1(2) . . ?
N1 C12 C11 108.8(2) . . ?
C13 C12 C11 122.1(2) . . ?
C14 C13 C12 117.1(2) . . ?
C14 C13 H13 121.5 . . ?
C12 C13 H13 121.5 . . ?
C13 C14 C15 122.7(2) . . ?
C13 C14 H14 118.7 . . ?
C15 C14 H14 118.7 . . ?
C16 C15 C14 119.6(2) . . ?
C16 C15 C17 121.6(2) . . ?
C14 C15 C17 118.8(2) . . ?
C15 C16 C11 119.4(2) . . ?
C15 C16 H16 120.3 . . ?
C11 C16 H16 120.3 . . ?
C15 C17 H17D 109.5 . . ?
C15 C17 H17E 109.5 . . ?
H17D C17 H17E 109.5 . . ?
C15 C17 H17F 109.5 . . ?
H17D C17 H17F 109.5 . . ?
H17E C17 H17F 109.5 . . ?
C23 C18 C19 118.3(2) . . ?
C23 C18 C1 118.6(2) . . ?
C19 C18 C1 122.9(2) . . ?
C18 C19 C20 122.0(2) . . ?
C18 C19 H19 119.0 . . ?
C20 C19 H19 119.0 . . ?
C19 C20 C21 117.7(2) . . ?
C19 C20 C24 120.0(2) . . ?
C21 C20 C24 122.2(2) . . ?
O3 C21 C20 116.6(2) . . ?
O3 C21 C22 121.3(2) . . ?
C20 C21 C22 122.0(2) . . ?
C23 C22 C21 116.8(2) . . ?
C23 C22 C28 120.5(2) . . ?
C21 C22 C28 122.8(2) . . ?
C18 C23 C22 123.2(2) . . ?
C18 C23 H23 118.4 . . ?
C22 C23 H23 118.4 . . ?
C26 C24 C25 107.7(3) . . ?
C26 C24 C27 110.6(3) . . ?
C25 C24 C27 106.6(3) . . ?
C26 C24 C20 110.5(3) . . ?
C25 C24 C20 111.9(2) . . ?
C27 C24 C20 109.5(2) . . ?
C24 C25 H25D 109.5 . . ?
C24 C25 H25E 109.5 . . ?
H25D C25 H25E 109.5 . . ?
C24 C25 H25F 109.5 . . ?
H25D C25 H25F 109.5 . . ?
H25E C25 H25F 109.5 . . ?
C24 C26 H26D 109.5 . . ?
C24 C26 H26E 109.5 . . ?
H26D C26 H26E 109.5 . . ?
C24 C26 H26F 109.5 . . ?
H26D C26 H26F 109.5 . . ?
H26E C26 H26F 109.5 . . ?
C24 C27 H27D 109.5 . . ?
C24 C27 H27E 109.5 . . ?
H27D C27 H27E 109.5 . . ?
C24 C27 H27F 109.5 . . ?
H27D C27 H27F 109.5 . . ?
H27E C27 H27F 109.5 . . ?
C31 C28 C29 107.1(3) . . ?
C31 C28 C30 106.0(2) . . ?
C29 C28 C30 110.0(2) . . ?
C31 C28 C22 111.4(2) . . ?
C29 C28 C22 111.1(2) . . ?
C30 C28 C22 111.1(2) . . ?
C28 C29 H29D 109.5 . . ?
C28 C29 H29E 109.5 . . ?
H29D C29 H29E 109.5 . . ?
C28 C29 H29F 109.5 . . ?
H29D C29 H29F 109.5 . . ?
H29E C29 H29F 109.5 . . ?
C28 C30 H30D 109.5 . . ?
C28 C30 H30E 109.5 . . ?
H30D C30 H30E 109.5 . . ?
C28 C30 H30F 109.5 . . ?
H30D C30 H30F 109.5 . . ?
H30E C30 H30F 109.5 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C32 O4 H4A 108(4) . . ?
O4 C32 C33 111.6(3) . . ?
O4 C32 H32A 109.3 . . ?
C33 C32 H32A 109.3 . . ?
O4 C32 H32B 109.3 . . ?
C33 C32 H32B 109.3 . . ?
H32A C32 H32B 108.0 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
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 C8 1.364(3) . ?
O1 C7 1.415(3) . ?
O2 C8 1.218(4) . ?
O3 C21 1.373(3) . ?
O3 H3A 0.8395 . ?
N1 C12 1.363(3) . ?
N1 C9 1.379(3) . ?
N1 H1A 0.8801 . ?
C1 C10 1.501(3) . ?
C1 C2 1.521(3) . ?
C1 C18 1.536(3) . ?
C1 H1 1.0000 . ?
C2 C7 1.389(4) . ?
C2 C3 1.402(4) . ?
C3 C4 1.383(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.391(4) . ?
C6 H6 0.9500 . ?
C8 C9 1.444(4) . ?
C9 C10 1.381(4) . ?
C10 C11 1.429(3) . ?
C11 C16 1.411(3) . ?
C11 C12 1.412(3) . ?
C12 C13 1.399(3) . ?
C13 C14 1.370(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.424(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(3) . ?
C15 C17 1.501(4) . ?
C16 H16 0.9500 . ?
C17 H17D 0.9800 . ?
C17 H17E 0.9800 . ?
C17 H17F 0.9800 . ?
C18 C23 1.383(4) . ?
C18 C19 1.389(4) . ?
C19 C20 1.399(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.409(4) . ?
C20 C24 1.544(4) . ?
C21 C22 1.410(4) . ?
C22 C23 1.396(4) . ?
C22 C28 1.542(4) . ?
C23 H23 0.9500 . ?
C24 C26 1.535(5) . ?
C24 C25 1.538(5) . ?
C24 C27 1.540(4) . ?
C25 H25D 0.9800 . ?
C25 H25E 0.9800 . ?
C25 H25F 0.9800 . ?
C26 H26D 0.9800 . ?
C26 H26E 0.9800 . ?
C26 H26F 0.9800 . ?
C27 H27D 0.9800 . ?
C27 H27E 0.9800 . ?
C27 H27F 0.9800 . ?
C28 C31 1.530(4) . ?
C28 C29 1.537(4) . ?
C28 C30 1.538(4) . ?
C29 H29D 0.9800 . ?
C29 H29E 0.9800 . ?
C29 H29F 0.9800 . ?
C30 H30D 0.9800 . ?
C30 H30E 0.9800 . ?
C30 H30F 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
O4 C32 1.412(4) . ?
O4 H4A 0.82(6) . ?
C32 C33 1.489(6) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O4 0.88 1.98 2.810(3) 156.1 . yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C7 51.0(3) . . . . ?
C18 C1 C2 C7 -78.6(3) . . . . ?
C10 C1 C2 C3 -129.5(2) . . . . ?
C18 C1 C2 C3 100.9(3) . . . . ?
C7 C2 C3 C4 0.3(4) . . . . ?
C1 C2 C3 C4 -179.2(2) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C4 C5 C6 C7 0.2(5) . . . . ?
C3 C2 C7 C6 -0.1(4) . . . . ?
C1 C2 C7 C6 179.4(3) . . . . ?
C3 C2 C7 O1 -174.1(2) . . . . ?
C1 C2 C7 O1 5.4(4) . . . . ?
C5 C6 C7 C2 -0.1(4) . . . . ?
C5 C6 C7 O1 174.5(3) . . . . ?
C8 O1 C7 C2 -58.2(4) . . . . ?
C8 O1 C7 C6 127.3(3) . . . . ?
C7 O1 C8 O2 -153.2(3) . . . . ?
C7 O1 C8 C9 30.2(4) . . . . ?
C12 N1 C9 C10 -1.7(3) . . . . ?
C12 N1 C9 C8 -177.7(3) . . . . ?
O2 C8 C9 N1 17.5(5) . . . . ?
O1 C8 C9 N1 -166.1(3) . . . . ?
O2 C8 C9 C10 -157.6(4) . . . . ?
O1 C8 C9 C10 18.8(5) . . . . ?
N1 C9 C10 C11 1.3(3) . . . . ?
C8 C9 C10 C11 176.7(3) . . . . ?
N1 C9 C10 C1 -179.4(2) . . . . ?
C8 C9 C10 C1 -4.0(5) . . . . ?
C2 C1 C10 C9 -46.9(3) . . . . ?
C18 C1 C10 C9 79.9(3) . . . . ?
C2 C1 C10 C11 132.2(2) . . . . ?
C18 C1 C10 C11 -101.0(3) . . . . ?
C9 C10 C11 C16 178.4(3) . . . . ?
C1 C10 C11 C16 -0.8(4) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C1 C10 C11 C12 -179.8(2) . . . . ?
C9 N1 C12 C13 -178.8(3) . . . . ?
C9 N1 C12 C11 1.3(3) . . . . ?
C16 C11 C12 N1 -179.6(2) . . . . ?
C10 C11 C12 N1 -0.4(3) . . . . ?
C16 C11 C12 C13 0.5(3) . . . . ?
C10 C11 C12 C13 179.6(2) . . . . ?
N1 C12 C13 C14 -179.1(2) . . . . ?
C11 C12 C13 C14 0.8(4) . . . . ?
C12 C13 C14 C15 -1.1(4) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C13 C14 C15 C17 -179.3(3) . . . . ?
C14 C15 C16 C11 1.1(4) . . . . ?
C17 C15 C16 C11 -179.4(3) . . . . ?
C12 C11 C16 C15 -1.4(4) . . . . ?
C10 C11 C16 C15 179.7(3) . . . . ?
C10 C1 C18 C23 153.9(2) . . . . ?
C2 C1 C18 C23 -79.3(3) . . . . ?
C10 C1 C18 C19 -30.0(3) . . . . ?
C2 C1 C18 C19 96.7(3) . . . . ?
C23 C18 C19 C20 0.3(4) . . . . ?
C1 C18 C19 C20 -175.8(2) . . . . ?
C18 C19 C20 C21 -1.6(4) . . . . ?
C18 C19 C20 C24 177.5(2) . . . . ?
C19 C20 C21 O3 -174.4(2) . . . . ?
C24 C20 C21 O3 6.4(4) . . . . ?
C19 C20 C21 C22 2.5(4) . . . . ?
C24 C20 C21 C22 -176.7(2) . . . . ?
O3 C21 C22 C23 174.8(2) . . . . ?
C20 C21 C22 C23 -1.9(4) . . . . ?
O3 C21 C22 C28 -5.6(4) . . . . ?
C20 C21 C22 C28 177.7(2) . . . . ?
C19 C18 C23 C22 0.3(4) . . . . ?
C1 C18 C23 C22 176.6(2) . . . . ?
C21 C22 C23 C18 0.5(4) . . . . ?
C28 C22 C23 C18 -179.1(2) . . . . ?
C19 C20 C24 C26 118.9(3) . . . . ?
C21 C20 C24 C26 -62.0(3) . . . . ?
C19 C20 C24 C25 -1.1(4) . . . . ?
C21 C20 C24 C25 178.0(3) . . . . ?
C19 C20 C24 C27 -119.1(3) . . . . ?
C21 C20 C24 C27 60.0(4) . . . . ?
C23 C22 C28 C31 -1.0(3) . . . . ?
C21 C22 C28 C31 179.5(3) . . . . ?
C23 C22 C28 C29 -120.2(3) . . . . ?
C21 C22 C28 C29 60.2(3) . . . . ?
C23 C22 C28 C30 117.0(3) . . . . ?
C21 C22 C28 C30 -62.6(3) . . . . ?
