#------------------------------------------------------------------------------
#$Date: 2026-04-03 02:42:21 +0200 (Fri 03 de Apr de 2026) $
#$Revision: 305257 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/10/7161096.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_7161096
loop_
_publ_author_name
'Ballanki, Trinadh'
'Subramanian, Anjali Devi'
'Chinnappa, Pravin'
'Suresh Kumar, Vaishnu'
'Garg, Mohit'
'Jebiti, Haribabu'
'Moraga, Daniel'
'Viswambharan, Baby'
_publ_section_title
;
 Potassium Hydrogen Sulfate Promoted One-pot Synthesis of
 Bis(indolyl)alkane Esters from α-Keto Carboxylic Acids: In Silico and In
 Vitro Anticancer Studies
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D6OB00318D
_journal_year                    2025
_chemical_formula_moiety         'C25 H24 N2 O2'
_chemical_formula_sum            'C25 H24 N2 O2'
_chemical_formula_weight         384.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2m7vlb
_audit_creation_date             2024-12-08
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-01-30 deposited with the CCDC.	2026-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.097(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.933(2)
_cell_length_b                   12.500(2)
_cell_length_c                   15.856(3)
_cell_measurement_reflns_used    9756
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      2.56
_cell_volume                     2047.7(6)
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            57573
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         2.558
_diffrn_source                   'i-mu-s microfocus source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (BRUKER)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.185
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         5061
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0607
_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/[σ²(Fo²)+(0.0635P)²+0.8114P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1464
_refine_ls_wR_factor_ref         0.1576
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4063
_reflns_number_total             5061
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6ob00318d2.cif
_cod_data_source_block           cp_111_96_181024_0m_a
_cod_original_cell_volume        2047.7(7)
_cod_database_code               7161096
_shelx_shelxl_version_number     2019/3
_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_max   0.985
_shelx_estimated_absorpt_t_min   0.971
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-C4 \\sim N1-C4A
 with sigma of 0.02
 C4-C17 \\sim C4A-C17A
 with sigma of 0.02
 C17-C18 \\sim C17A-C18A
 with sigma of 0.02
 N1-C17 \\sim N1-C17A
 with sigma of 0.04
 C4-C18 \\sim C4A-C18A
 with sigma of 0.04
3. Rigid bond restraints
 C17, C18
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
C17 \\sim C18A: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
N1 \\sim C4A: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
C20 \\sim C21B: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
C21A \\sim C22A: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
C21B \\sim C22B: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
5. Others
 Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18C)=
 Sof(H18D)=1-FVAR(1)
 Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18A)=Sof(H18B)=
 FVAR(1)
 Sof(H20C)=Sof(H20D)=Sof(C21B)=Sof(H21B)=Sof(C22B)=Sof(H22C)=Sof(H22D)=1-FVAR(2)
 Sof(H20A)=Sof(H20B)=Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22A)=Sof(H22B)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C12(H12)
6.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C4A(H4AA,H4AB), C20(H20C,H20D), C20(H20A,H20B)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C17(H17),
 C17A(H17A), C21A(H21A), C21B(H21B), C23(H23), C24(H24), C25(H25)
6.d X=CH2 refined with riding coordinates:
 C18(H18A,H18B), C18A(H18C,H18D), C22A(H22A,H22B), C22B(H22C,H22D)
6.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.16152(13) 0.53460(12) 0.57180(9) 0.0645(4) Uani 1 1 d . . . . .
O2 O 0.34943(13) 0.57379(11) 0.55372(10) 0.0647(4) Uani 1 1 d . . . . .
N1 N 0.46713(15) 0.23054(13) 0.57134(11) 0.0591(4) Uani 1 1 d D U . . .
N2 N 0.29706(15) 0.51287(13) 0.26170(10) 0.0546(4) Uani 1 1 d . . . . .
C1 C 0.1247(2) 0.64642(15) 0.18251(12) 0.0578(5) Uani 1 1 d . . . . .
H1 H 0.155990 0.661177 0.135803 0.069 Uiso 1 1 calc R U . . .
C2 C 0.25190(14) 0.52238(12) 0.53337(10) 0.0405(3) Uani 1 1 d . . . . .
C3 C 0.42836(16) 0.32563(15) 0.52762(12) 0.0526(4) Uani 1 1 d . . . . .
H3 H 0.483469 0.375435 0.515378 0.063 Uiso 1 1 calc R U . . .
C4 C 0.6048(2) 0.1998(2) 0.61323(16) 0.0649(7) Uani 0.873(4) 1 d D . P A 1
H4A H 0.656060 0.263440 0.635184 0.078 Uiso 0.873(4) 1 calc R U P A 1
H4B H 0.612943 0.153314 0.663776 0.078 Uiso 0.873(4) 1 calc R U P A 1
C4A C 0.5726(13) 0.1481(12) 0.5785(13) 0.0590(14) Uani 0.127(4) 1 d D U P A 2
H4AA H 0.587508 0.103689 0.631035 0.071 Uiso 0.127(4) 1 calc R U P A 2
H4AB H 0.550497 0.102805 0.525963 0.071 Uiso 0.127(4) 1 calc R U P A 2
C5 C 0.25085(16) 0.24339(12) 0.53710(10) 0.0433(4) Uani 1 1 d . . . . .
C6 C 0.36014(18) 0.17840(14) 0.57781(11) 0.0506(4) Uani 1 1 d . . . . .
C7 C 0.3497(2) 0.08064(16) 0.61787(14) 0.0671(6) Uani 1 1 d . . . . .
H7 H 0.421939 0.038124 0.644157 0.080 Uiso 1 1 calc R U . . .
C8 C 0.2292(3) 0.04996(17) 0.61690(16) 0.0780(7) Uani 1 1 d . . . . .
H8 H 0.219845 -0.014689 0.643179 0.094 Uiso 1 1 calc R U . . .
C9 C 0.1205(2) 0.11247(18) 0.57785(17) 0.0750(6) Uani 1 1 d . . . . .
H9 H 0.040050 0.088800 0.578343 0.090 Uiso 1 1 calc R U . . .
C10 C 0.12960(19) 0.20942(15) 0.53819(13) 0.0567(4) Uani 1 1 d . . . . .
H10 H 0.056400 0.251206 0.512733 0.068 Uiso 1 1 calc R U . . .
C11 C 0.29740(15) 0.33670(12) 0.50464(10) 0.0414(3) Uani 1 1 d . . . . .
C12 C 0.21654(14) 0.43318(12) 0.46348(10) 0.0394(3) Uani 1 1 d . . . . .
H12 H 0.125589 0.414530 0.452544 0.047 Uiso 1 1 calc R U . . .
C13 C 0.22812(15) 0.47450(12) 0.37720(10) 0.0413(3) Uani 1 1 d . . . . .
C14 C 0.32054(17) 0.45502(15) 0.33922(12) 0.0519(4) Uani 1 1 d . . . . .
H14 H 0.390220 0.408883 0.362413 0.062 Uiso 1 1 calc R U . . .
C15 C 0.18733(16) 0.57371(13) 0.24939(11) 0.0454(4) Uani 1 1 d . . . . .
C16 C 0.14085(14) 0.55086(12) 0.32056(10) 0.0400(3) Uani 1 1 d . . . . .
C17 C 0.6550(2) 0.1443(2) 0.54938(17) 0.0657(7) Uani 0.873(4) 1 d D U P A 1
H17 H 0.608480 0.085967 0.518654 0.079 Uiso 0.873(4) 1 calc R U P A 1
C17A C 0.6854(12) 0.2146(11) 0.5852(10) 0.054(4) Uani 0.127(4) 1 d D . P A 2
H17A H 0.700187 0.272615 0.623940 0.065 Uiso 0.127(4) 1 calc R U P A 2
C18 C 0.7590(5) 0.1711(3) 0.5333(4) 0.0847(12) Uani 0.873(4) 1 d D U P A 1
H18A H 0.807713 0.229028 0.562865 0.102 Uiso 0.873(4) 1 calc R U P A 1
H18B H 0.785249 0.132538 0.492071 0.102 Uiso 0.873(4) 1 calc R U P A 1
C18A C 0.765(3) 0.201(2) 0.543(2) 0.068(3) Uani 0.127(4) 1 d D U P A 2
H18C H 0.754722 0.143627 0.503712 0.082 Uiso 0.127(4) 1 calc R U P A 2
H18D H 0.834650 0.247411 0.551978 0.082 Uiso 0.127(4) 1 calc R U P A 2
C19 C 0.1886(3) 0.6136(2) 0.64207(17) 0.0847(7) Uani 1 1 d . . . . .
H19A H 0.120241 0.613526 0.667635 0.127 Uiso 1 1 calc R U . . .
H19B H 0.194551 0.683049 0.617865 0.127 Uiso 1 1 calc R U . . .
H19C H 0.269099 0.596677 0.687401 0.127 Uiso 1 1 calc R U . . .
C20 C 0.3853(2) 0.5198(2) 0.20968(14) 0.0691(6) Uani 1 1 d . U . . .
H20C H 0.414936 0.448788 0.201057 0.083 Uiso 0.271(8) 1 calc R U P B 2
H20D H 0.340333 0.550152 0.151454 0.083 Uiso 0.271(8) 1 calc R U P B 2
H20A H 0.335245 0.532111 0.147551 0.083 Uiso 0.729(8) 1 calc R U P B 1
H20B H 0.429861 0.451989 0.213369 0.083 Uiso 0.729(8) 1 calc R U P B 1
C21A C 0.4839(9) 0.6073(7) 0.2409(6) 0.119(2) Uani 0.729(8) 1 d . U P B 1
H21A H 0.534322 0.601023 0.300568 0.143 Uiso 0.729(8) 1 calc R U P B 1
C21B C 0.4893(16) 0.5828(12) 0.2536(10) 0.0647(13) Uani 0.271(8) 1 d . U P B 2
H21B H 0.491825 0.586142 0.312758 0.078 Uiso 0.271(8) 1 calc R U P B 2
C22A C 0.5079(8) 0.6747(6) 0.2090(4) 0.133(2) Uani 0.729(8) 1 d . U P B 1
H22A H 0.462933 0.688134 0.149153 0.160 Uiso 0.729(8) 1 calc R U P B 1
H22B H 0.573859 0.720507 0.240846 0.160 Uiso 0.729(8) 1 calc R U P B 1
C22B C 0.5849(11) 0.6391(9) 0.2483(8) 0.075(2) Uani 0.271(8) 1 d . U P B 2
H22C H 0.599403 0.646006 0.193995 0.090 Uiso 0.271(8) 1 calc R U P B 2
H22D H 0.639448 0.673054 0.298866 0.090 Uiso 0.271(8) 1 calc R U P B 2
C23 C 0.0156(2) 0.69529(15) 0.18812(13) 0.0634(5) Uani 1 1 d . . . . .
H23 H -0.027776 0.744058 0.144240 0.076 Uiso 1 1 calc R U . . .
C24 C -0.03214(19) 0.67403(15) 0.25765(14) 0.0602(5) Uani 1 1 d . . . . .
H24 H -0.106499 0.708791 0.259358 0.072 Uiso 1 1 calc R U . . .
C25 C 0.02921(16) 0.60207(13) 0.32423(12) 0.0477(4) Uani 1 1 d . . . . .
H25 H -0.003201 0.588041 0.370504 0.057 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 0.0033 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
C2 O1 C19 115.88(15) . . ?
C3 N1 C4 123.47(19) . . ?
C3 N1 C4A 136.5(6) . . ?
C3 N1 C6 108.63(14) . . ?
C6 N1 C4 127.48(18) . . ?
C6 N1 C4A 108.5(6) . . ?
C14 N2 C15 108.40(14) . . ?
C14 N2 C20 124.77(17) . . ?
C15 N2 C20 126.24(17) . . ?
C15 C1 H1 121.2 . . ?
C23 C1 H1 121.2 . . ?
C23 C1 C15 117.57(17) . . ?
O1 C2 C12 111.49(13) . . ?
O2 C2 O1 123.09(15) . . ?
O2 C2 C12 125.39(15) . . ?
N1 C3 H3 124.9 . . ?
C11 C3 N1 110.29(16) . . ?
C11 C3 H3 124.9 . . ?
N1 C4 H4A 109.3 . . ?
N1 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C17 C4 N1 111.45(19) . . ?
C17 C4 H4A 109.3 . . ?
C17 C4 H4B 109.3 . . ?
N1 C4A H4AA 111.2 . . ?
N1 C4A H4AB 111.2 . . ?
H4AA C4A H4AB 109.1 . . ?
C17A C4A N1 102.8(11) . . ?
C17A C4A H4AA 111.2 . . ?
C17A C4A H4AB 111.2 . . ?
C6 C5 C11 106.56(15) . . ?
C10 C5 C6 118.89(16) . . ?
C10 C5 C11 134.52(15) . . ?
N1 C6 C5 107.86(15) . . ?
N1 C6 C7 130.34(17) . . ?
C7 C6 C5 121.78(18) . . ?
C6 C7 H7 121.3 . . ?
C8 C7 C6 117.49(19) . . ?
C8 C7 H7 121.3 . . ?
C7 C8 H8 119.0 . . ?
C7 C8 C9 121.9(2) . . ?
C9 C8 H8 119.0 . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.1(2) . . ?
C10 C9 H9 119.4 . . ?
C5 C10 H10 120.6 . . ?
C9 C10 C5 118.79(19) . . ?
C9 C10 H10 120.6 . . ?
C3 C11 C5 106.65(14) . . ?
C3 C11 C12 127.65(15) . . ?
C5 C11 C12 125.31(14) . . ?
C2 C12 H12 107.6 . . ?
C11 C12 C2 107.17(12) . . ?
C11 C12 H12 107.6 . . ?
C13 C12 C2 109.37(12) . . ?
C13 C12 C11 117.06(13) . . ?
C13 C12 H12 107.6 . . ?
C14 C13 C12 129.63(15) . . ?
C14 C13 C16 106.27(14) . . ?
C16 C13 C12 124.01(14) . . ?
N2 C14 H14 124.6 . . ?
C13 C14 N2 110.72(15) . . ?
C13 C14 H14 124.6 . . ?
N2 C15 C1 130.90(17) . . ?
N2 C15 C16 107.43(14) . . ?
C1 C15 C16 121.67(17) . . ?
C15 C16 C13 107.17(14) . . ?
C25 C16 C13 133.54(15) . . ?
C25 C16 C15 119.29(15) . . ?
C4 C17 H17 117.8 . . ?
C18 C17 C4 124.4(3) . . ?
C18 C17 H17 117.8 . . ?
C4A C17A H17A 116.9 . . ?
C18A C17A C4A 126.3(18) . . ?
C18A C17A H17A 116.9 . . ?
C17 C18 H18A 120.0 . . ?
C17 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?
C17A C18A H18C 120.0 . . ?
C17A C18A H18D 120.0 . . ?
H18C C18A H18D 120.0 . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 H20C 109.7 . . ?
N2 C20 H20D 109.7 . . ?
N2 C20 H20A 109.0 . . ?
N2 C20 H20B 109.0 . . ?
N2 C20 C21A 113.1(3) . . ?
H20C C20 H20D 108.2 . . ?
H20A C20 H20B 107.8 . . ?
C21A C20 H20A 109.0 . . ?
C21A C20 H20B 109.0 . . ?
C21B C20 N2 109.8(6) . . ?
C21B C20 H20C 109.7 . . ?
C21B C20 H20D 109.7 . . ?
C20 C21A H21A 113.3 . . ?
C22A C21A C20 133.3(8) . . ?
C22A C21A H21A 113.3 . . ?
C20 C21B H21B 106.5 . . ?
C22B C21B C20 147.0(14) . . ?
C22B C21B H21B 106.5 . . ?
C21A C22A H22A 120.0 . . ?
C21A C22A H22B 120.0 . . ?
H22A C22A H22B 120.0 . . ?
C21B C22B H22C 120.0 . . ?
C21B C22B H22D 120.0 . . ?
H22C C22B H22D 120.0 . . ?
C1 C23 H23 119.1 . . ?
C1 C23 C24 121.83(17) . . ?
C24 C23 H23 119.1 . . ?
C23 C24 H24 119.5 . . ?
C25 C24 C23 121.02(18) . . ?
C25 C24 H24 119.5 . . ?
C16 C25 H25 120.7 . . ?
C24 C25 C16 118.62(17) . . ?
C24 C25 H25 120.7 . . ?
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 C2 1.329(2) . ?
O1 C19 1.445(2) . ?
O2 C2 1.1953(19) . ?
N1 C3 1.371(2) . ?
N1 C4 1.483(2) . ?
N1 C4A 1.522(12) . ?
N1 C6 1.372(2) . ?
N2 C14 1.376(2) . ?
N2 C15 1.379(2) . ?
N2 C20 1.463(2) . ?
C1 H1 0.9300 . ?
C1 C15 1.394(2) . ?
C1 C23 1.369(3) . ?
C2 C12 1.530(2) . ?
C3 H3 0.9300 . ?
C3 C11 1.364(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C17 1.474(4) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C4A C17A 1.462(15) . ?
C5 C6 1.414(2) . ?
C5 C10 1.397(2) . ?
C5 C11 1.434(2) . ?
C6 C7 1.399(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.367(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.388(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.384(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.511(2) . ?
C12 H12 0.9800 . ?
C12 C13 1.506(2) . ?
C13 C14 1.357(2) . ?
C13 C16 1.438(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.410(2) . ?
C16 C25 1.396(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.289(4) . ?
C17A H17A 0.9300 . ?
C17A C18A 1.274(17) . ?
C18 H18A 0.9300 . ?
C18 H18B 0.9300 . ?
C18A H18C 0.9300 . ?
C18A H18D 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20C 0.9700 . ?
C20 H20D 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21A 1.501(7) . ?
C20 C21B 1.371(17) . ?
C21A H21A 0.9300 . ?
C21A C22A 1.058(7) . ?
C21B H21B 0.9300 . ?
C21B C22B 1.285(19) . ?
C22A H22A 0.9300 . ?
C22A H22B 0.9300 . ?
C22B H22C 0.9300 . ?
C22B H22D 0.9300 . ?
C23 H23 0.9300 . ?
C23 C24 1.391(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.382(2) . ?
C25 H25 0.9300 . ?
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
C3 H3 O2 0.93 2.50 3.346(2) 151.4 3_666 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
O1 C2 C12 C11 -103.21(15) . . . . ?
O1 C2 C12 C13 128.96(14) . . . . ?
O2 C2 C12 C11 74.9(2) . . . . ?
O2 C2 C12 C13 -52.9(2) . . . . ?
N1 C3 C11 C5 0.9(2) . . . . ?
N1 C3 C11 C12 173.89(15) . . . . ?
N1 C4 C17 C18 127.6(4) . . . . ?
N1 C4A C17A C18A -135(3) . . . . ?
N1 C6 C7 C8 177.6(2) . . . . ?
N2 C15 C16 C13 0.72(17) . . . . ?
N2 C15 C16 C25 -179.83(14) . . . . ?
N2 C20 C21A C22A -122.5(11) . . . . ?
N2 C20 C21B C22B -161(2) . . . . ?
C1 C15 C16 C13 -179.32(14) . . . . ?
C1 C15 C16 C25 0.1(2) . . . . ?
C1 C23 C24 C25 -0.1(3) . . . . ?
C2 C12 C13 C14 105.35(19) . . . . ?
C2 C12 C13 C16 -70.74(18) . . . . ?
C3 N1 C4 C17 -88.7(3) . . . . ?
C3 N1 C4A C17A 41.6(18) . . . . ?
C3 N1 C6 C5 -0.3(2) . . . . ?
C3 N1 C6 C7 -178.52(19) . . . . ?
C3 C11 C12 C2 -67.1(2) . . . . ?
C3 C11 C12 C13 56.1(2) . . . . ?
C4 N1 C3 C11 -173.44(18) . . . . ?
C4 N1 C6 C5 172.42(19) . . . . ?
C4 N1 C6 C7 -5.8(3) . . . . ?
C4A N1 C3 C11 146.8(11) . . . . ?
C4A N1 C6 C5 -157.1(8) . . . . ?
C4A N1 C6 C7 24.7(8) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C5 C11 C12 C2 104.68(17) . . . . ?
C5 C11 C12 C13 -132.12(16) . . . . ?
C6 N1 C3 C11 -0.4(2) . . . . ?
C6 N1 C4 C17 99.6(3) . . . . ?
C6 N1 C4A C17A -171.2(9) . . . . ?
C6 C5 C10 C9 -1.0(3) . . . . ?
C6 C5 C11 C3 -1.03(18) . . . . ?
C6 C5 C11 C12 -174.24(14) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C8 C9 C10 C5 0.7(3) . . . . ?
C10 C5 C6 N1 -177.49(16) . . . . ?
C10 C5 C6 C7 0.9(3) . . . . ?
C10 C5 C11 C3 176.88(19) . . . . ?
C10 C5 C11 C12 3.7(3) . . . . ?
C11 C5 C6 N1 0.81(18) . . . . ?
C11 C5 C6 C7 179.22(16) . . . . ?
C11 C5 C10 C9 -178.74(19) . . . . ?
C11 C12 C13 C14 -16.7(2) . . . . ?
C11 C12 C13 C16 167.19(13) . . . . ?
C12 C13 C14 N2 -177.34(15) . . . . ?
C12 C13 C16 C15 176.85(14) . . . . ?
C12 C13 C16 C25 -2.5(3) . . . . ?
C13 C16 C25 C24 179.13(16) . . . . ?
C14 N2 C15 C1 178.89(17) . . . . ?
C14 N2 C15 C16 -1.15(18) . . . . ?
C14 N2 C20 C21A -87.0(5) . . . . ?
C14 N2 C20 C21B -73.0(7) . . . . ?
C14 C13 C16 C15 -0.01(17) . . . . ?
C14 C13 C16 C25 -179.35(17) . . . . ?
C15 N2 C14 C13 1.2(2) . . . . ?
C15 N2 C20 C21A 83.1(5) . . . . ?
C15 N2 C20 C21B 97.1(7) . . . . ?
C15 C1 C23 C24 0.0(3) . . . . ?
C15 C16 C25 C24 -0.1(2) . . . . ?
C16 C13 C14 N2 -0.71(19) . . . . ?
C19 O1 C2 O2 -1.1(3) . . . . ?
C19 O1 C2 C12 177.12(17) . . . . ?
C20 N2 C14 C13 172.77(17) . . . . ?
C20 N2 C15 C1 7.5(3) . . . . ?
C20 N2 C15 C16 -172.58(16) . . . . ?
C23 C1 C15 N2 179.87(17) . . . . ?
C23 C1 C15 C16 -0.1(2) . . . . ?
C23 C24 C25 C16 0.1(3) . . . . ?
