#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/81/4038139.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_4038139
loop_
_publ_author_name
'Chang, Meng-Yang'
'Tsai, Yu-Lin'
_publ_section_title
;
 One-Pot Amberlyst 15-Controlled Cyclocondensation of Piperidines and
 Arylaldehydes. Synthesis of 3,5-Diarylmethyl Pyridines.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03315
_journal_year                    2020
_chemical_absolute_configuration rm
_chemical_formula_sum            'C29 H27 N3'
_chemical_formula_weight         417.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 94.557(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2091(7)
_cell_length_b                   11.4310(14)
_cell_length_c                   31.863(4)
_cell_measurement_reflns_used    6358
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.9409
_cell_measurement_theta_min      2.1952
_cell_volume                     2254.4(5)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            23467
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.397
_diffrn_reflns_theta_min         1.282
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lump
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.239
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0(4)
_refine_ls_extinction_coef       0.046(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     579
_refine_ls_number_reflns         9068
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0471
_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)+(0.0618P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1236
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                7153
_reflns_number_total             9068
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03315_si_001.cif
_cod_data_source_block           mo_180935lt_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P n'
_cod_database_code               4038139
_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.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, 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
C1 C 0.5173(6) 0.5655(3) 0.35540(12) 0.0189(8) Uani 1 1 d . . . . .
C2 C 0.4089(6) 0.6681(4) 0.35902(13) 0.0223(9) Uani 1 1 d . . . . .
H2 H 0.4548 0.7320 0.3765 0.027 Uiso 1 1 calc R U . . .
C3 C 0.2161(7) 0.6631(4) 0.33220(13) 0.0254(9) Uani 1 1 d . . . . .
H3 H 0.1105 0.7230 0.3281 0.030 Uiso 1 1 calc R U . . .
C4 C 0.2111(7) 0.5559(4) 0.31336(14) 0.0247(9) Uani 1 1 d . . . . .
H4 H 0.0995 0.5274 0.2939 0.030 Uiso 1 1 calc R U . . .
C5 C 0.4537(7) 0.3793(3) 0.31362(13) 0.0223(9) Uani 1 1 d . . . . .
H5A H 0.3229 0.3406 0.3003 0.027 Uiso 1 1 calc R U . . .
H5B H 0.5042 0.3329 0.3387 0.027 Uiso 1 1 calc R U . . .
C6 C 0.6262(7) 0.3775(4) 0.28308(16) 0.0198(11) Uani 1 1 d . . . . .
C7 C 0.6441(7) 0.4668(5) 0.25357(16) 0.0212(11) Uani 1 1 d . . . . .
H7 H 0.5471 0.5311 0.2530 0.025 Uiso 1 1 calc R U . . .
C8 C 0.8008(8) 0.4626(5) 0.22530(17) 0.0243(12) Uani 1 1 d . . . . .
H8 H 0.8118 0.5244 0.2056 0.029 Uiso 1 1 calc R U . . .
C9 C 0.9417(8) 0.3693(4) 0.22533(17) 0.0240(12) Uani 1 1 d . . . . .
H9 H 1.0488 0.3662 0.2057 0.029 Uiso 1 1 calc R U . . .
C10 C 0.9254(8) 0.2798(5) 0.25446(17) 0.0241(12) Uani 1 1 d . . . . .
H10 H 1.0218 0.2152 0.2547 0.029 Uiso 1 1 calc R U . . .
C11 C 0.7690(8) 0.2846(5) 0.28320(17) 0.0249(12) Uani 1 1 d . . . . .
H11 H 0.7599 0.2234 0.3032 0.030 Uiso 1 1 calc R U . . .
C12 C 0.7305(7) 0.5267(4) 0.37564(14) 0.0203(10) Uani 1 1 d . . . . .
H12A H 0.8011 0.5946 0.3903 0.024 Uiso 1 1 calc R U . . .
H12B H 0.8229 0.5025 0.3532 0.024 Uiso 1 1 calc R U . . .
C13 C 0.5581(7) 0.4172(4) 0.43400(13) 0.0225(9) Uani 1 1 d . . . . .
H13 H 0.4484 0.4753 0.4323 0.027 Uiso 1 1 calc R U . . .
C14 C 0.7218(7) 0.4270(4) 0.40685(13) 0.0190(9) Uani 1 1 d . . . . .
C15 C 0.8809(7) 0.3419(4) 0.40993(13) 0.0189(10) Uani 1 1 d . . . . .
H15 H 0.9960 0.3453 0.3920 0.023 Uiso 1 1 calc R U . . .
C16 C 0.8738(6) 0.2507(3) 0.43921(12) 0.0194(9) Uani 1 1 d . . . . .
C17 C 0.7014(8) 0.2510(5) 0.46431(19) 0.0227(13) Uani 1 1 d . . . . .
H17 H 0.6940 0.1898 0.4843 0.027 Uiso 1 1 calc R U . . .
C18 C 1.0467(6) 0.1573(4) 0.44325(13) 0.0213(9) Uani 1 1 d . . . . .
H18A H 1.1759 0.1891 0.4596 0.026 Uiso 1 1 calc R U . . .
H18B H 0.9933 0.0902 0.4591 0.026 Uiso 1 1 calc R U . . .
C19 C 1.1095(6) 0.1155(3) 0.40176(12) 0.0210(9) Uani 1 1 d . . . . .
C20 C 1.2837(7) 0.1432(3) 0.37989(13) 0.0225(9) Uani 1 1 d . . . . .
H20 H 1.4013 0.1919 0.3896 0.027 Uiso 1 1 calc R U . . .
C21 C 1.2578(7) 0.0866(4) 0.34032(14) 0.0251(10) Uani 1 1 d . . . . .
H21 H 1.3548 0.0902 0.3188 0.030 Uiso 1 1 calc R U . . .
C22 C 1.0709(7) 0.0268(4) 0.33875(13) 0.0253(9) Uani 1 1 d . . . . .
H22 H 1.0133 -0.0198 0.3158 0.030 Uiso 1 1 calc R U . . .
C23 C 0.7785(7) -0.0094(4) 0.38749(16) 0.0256(11) Uani 1 1 d . . . . .
H23A H 0.6974 -0.0393 0.3617 0.031 Uiso 1 1 calc R U . . .
H23B H 0.6883 0.0512 0.3997 0.031 Uiso 1 1 calc R U . . .
C24 C 0.8131(7) -0.1090(4) 0.41874(15) 0.0227(11) Uani 1 1 d . . . . .
C25 C 0.9995(8) -0.1745(4) 0.42186(14) 0.0280(10) Uani 1 1 d . . . . .
H25 H 1.1154 -0.1542 0.4055 0.034 Uiso 1 1 calc R U . . .
C26 C 1.0191(9) -0.2697(4) 0.44870(15) 0.0365(12) Uani 1 1 d . . . . .
H26 H 1.1480 -0.3147 0.4504 0.044 Uiso 1 1 calc R U . . .
C27 C 0.8551(10) -0.2998(4) 0.47291(14) 0.0433(14) Uani 1 1 d . . . . .
H27 H 0.8690 -0.3655 0.4912 0.052 Uiso 1 1 calc R U . . .
C28 C 0.6695(11) -0.2333(7) 0.4703(2) 0.0435(18) Uani 1 1 d . . . . .
H28 H 0.5551 -0.2534 0.4870 0.052 Uiso 1 1 calc R U . . .
C29 C 0.6465(8) -0.1372(5) 0.44353(15) 0.0330(11) Uani 1 1 d . . . . .
H29 H 0.5184 -0.0914 0.4422 0.040 Uiso 1 1 calc R U . . .
C30 C 0.7871(7) 1.3036(4) 0.68767(14) 0.0239(9) Uani 1 1 d . . . . .
H30 H 0.8960 1.2746 0.7076 0.029 Uiso 1 1 calc R U . . .
C31 C 0.7852(7) 1.4107(4) 0.66890(13) 0.0254(9) Uani 1 1 d . . . . .
H31 H 0.8926 1.4696 0.6732 0.031 Uiso 1 1 calc R U . . .
C32 C 0.5939(6) 1.4182(4) 0.64174(12) 0.0214(9) Uani 1 1 d . . . . .
H32 H 0.5502 1.4831 0.6245 0.026 Uiso 1 1 calc R U . . .
C33 C 0.4831(6) 1.3156(3) 0.64470(12) 0.0184(8) Uani 1 1 d . . . . .
C34 C 0.5422(7) 1.1289(3) 0.68615(13) 0.0226(9) Uani 1 1 d . . . . .
H34A H 0.6722 1.0889 0.6992 0.027 Uiso 1 1 calc R U . . .
H34B H 0.4896 1.0834 0.6610 0.027 Uiso 1 1 calc R U . . .
C35 C 0.3702(7) 1.1277(4) 0.71700(16) 0.0184(11) Uani 1 1 d . . . . .
C36 C 0.2254(7) 1.0349(5) 0.71683(17) 0.0230(12) Uani 1 1 d . . . . .
H36 H 0.2326 0.9740 0.6967 0.028 Uiso 1 1 calc R U . . .
C37 C 0.0712(8) 1.0305(5) 0.74571(18) 0.0277(12) Uani 1 1 d . . . . .
H37 H -0.0253 0.9660 0.7456 0.033 Uiso 1 1 calc R U . . .
C38 C 0.0561(8) 1.1194(4) 0.77483(16) 0.0244(12) Uani 1 1 d . . . . .
H38 H -0.0522 1.1169 0.7943 0.029 Uiso 1 1 calc R U . . .
C39 C 0.1998(8) 1.2117(5) 0.77544(16) 0.0220(12) Uani 1 1 d . . . . .
H39 H 0.1915 1.2726 0.7955 0.026 Uiso 1 1 calc R U . . .
C40 C 0.3563(7) 1.2157(5) 0.74674(16) 0.0203(11) Uani 1 1 d . . . . .
H40 H 0.4550 1.2793 0.7474 0.024 Uiso 1 1 calc R U . . .
C41 C 0.2716(7) 1.2784(4) 0.62347(15) 0.0222(10) Uani 1 1 d . . . . .
H41A H 0.2052 1.3466 0.6083 0.027 Uiso 1 1 calc R U . . .
H41B H 0.1753 1.2558 0.6454 0.027 Uiso 1 1 calc R U . . .
C42 C 0.4416(7) 1.1696(4) 0.56506(13) 0.0223(9) Uani 1 1 d . . . . .
H42 H 0.5503 1.2283 0.5663 0.027 Uiso 1 1 calc R U . . .
C43 C 0.2787(7) 1.1780(4) 0.59259(13) 0.0187(9) Uani 1 1 d . . . . .
C44 C 0.1218(7) 1.0920(4) 0.59025(13) 0.0197(10) Uani 1 1 d . . . . .
H44 H 0.0091 1.0947 0.6087 0.024 Uiso 1 1 calc R U . . .
C45 C 0.1274(6) 1.0021(3) 0.56131(12) 0.0190(9) Uani 1 1 d . . . . .
C46 C 0.2968(8) 1.0012(5) 0.53552(18) 0.0220(12) Uani 1 1 d . . . . .
H46 H 0.3028 0.9394 0.5157 0.026 Uiso 1 1 calc R U . . .
C47 C -0.0474(6) 0.9081(4) 0.55759(13) 0.0213(9) Uani 1 1 d . . . . .
H47A H -0.1765 0.9398 0.5412 0.026 Uiso 1 1 calc R U . . .
H47B H 0.0056 0.8408 0.5418 0.026 Uiso 1 1 calc R U . . .
C48 C -0.1112(6) 0.8662(3) 0.59929(12) 0.0197(8) Uani 1 1 d . . . . .
C49 C -0.2861(7) 0.8947(3) 0.62056(13) 0.0227(9) Uani 1 1 d . . . . .
H49 H -0.4022 0.9439 0.6104 0.027 Uiso 1 1 calc R U . . .
C50 C -0.2652(7) 0.8386(4) 0.66013(15) 0.0257(9) Uani 1 1 d . . . . .
H50 H -0.3632 0.8434 0.6815 0.031 Uiso 1 1 calc R U . . .
C51 C -0.0766(7) 0.7758(4) 0.66188(13) 0.0246(9) Uani 1 1 d . . . . .
H51 H -0.0214 0.7282 0.6847 0.029 Uiso 1 1 calc R U . . .
C52 C 0.2117(7) 0.7351(4) 0.61302(15) 0.0250(11) Uani 1 1 d . . . . .
H52A H 0.2926 0.7047 0.6388 0.030 Uiso 1 1 calc R U . . .
H52B H 0.3048 0.7932 0.6002 0.030 Uiso 1 1 calc R U . . .
C53 C 0.1686(8) 0.6354(4) 0.58256(15) 0.0235(11) Uani 1 1 d . . . . .
C54 C -0.0228(7) 0.5717(4) 0.58088(13) 0.0249(10) Uani 1 1 d . . . . .
H54 H -0.1329 0.5932 0.5985 0.030 Uiso 1 1 calc R U . . .
C55 C -0.0551(9) 0.4762(4) 0.55362(14) 0.0350(12) Uani 1 1 d . . . . .
H55 H -0.1866 0.4334 0.5524 0.042 Uiso 1 1 calc R U . . .
C56 C 0.1065(10) 0.4453(5) 0.52862(15) 0.0511(16) Uani 1 1 d . . . . .
H56 H 0.0864 0.3803 0.5101 0.061 Uiso 1 1 calc R U . . .
C57 C 0.2978(12) 0.5075(8) 0.5302(2) 0.048(2) Uani 1 1 d . . . . .
H57 H 0.4088 0.4847 0.5130 0.058 Uiso 1 1 calc R U . . .
C58 C 0.3278(8) 0.6022(5) 0.55638(14) 0.0352(11) Uani 1 1 d . . . . .
H58 H 0.4584 0.6456 0.5568 0.042 Uiso 1 1 calc R U . . .
N1 N 0.3948(5) 0.4961(3) 0.32728(10) 0.0197(7) Uani 1 1 d . . . . .
N2 N 0.5440(6) 0.3319(3) 0.46229(11) 0.0262(8) Uani 1 1 d . . . . .
N3 N 0.9770(5) 0.0444(3) 0.37593(11) 0.0216(8) Uani 1 1 d . . . . .
N4 N 0.6043(5) 1.2450(3) 0.67269(10) 0.0199(7) Uani 1 1 d . . . . .
N5 N 0.4526(6) 1.0827(3) 0.53686(11) 0.0243(8) Uani 1 1 d . . . . .
N6 N 0.0187(5) 0.7937(3) 0.62498(10) 0.0210(8) Uani 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'
N N 0.0061 0.0033 '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'
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 C1 N1 107.4(3) . . ?
C2 C1 C12 130.3(4) . . ?
N1 C1 C12 122.3(3) . . ?
C1 C2 C3 108.3(4) . . ?
C1 C2 H2 125.8 . . ?
C3 C2 H2 125.8 . . ?
C4 C3 C2 106.9(4) . . ?
C4 C3 H3 126.6 . . ?
C2 C3 H3 126.6 . . ?
C3 C4 N1 108.4(4) . . ?
C3 C4 H4 125.8 . . ?
N1 C4 H4 125.8 . . ?
N1 C5 C6 114.4(4) . . ?
N1 C5 H5A 108.7 . . ?
C6 C5 H5A 108.7 . . ?
N1 C5 H5B 108.7 . . ?
C6 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C11 C6 C7 118.5(5) . . ?
C11 C6 C5 119.9(4) . . ?
C7 C6 C5 121.6(4) . . ?
C8 C7 C6 120.8(5) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 120.5(5) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 119.3(5) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 120.3(5) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C6 C11 C10 120.7(5) . . ?
C6 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C1 C12 C14 115.4(3) . . ?
C1 C12 H12A 108.4 . . ?
C14 C12 H12A 108.4 . . ?
C1 C12 H12B 108.4 . . ?
C14 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
N2 C13 C14 124.7(4) . . ?
N2 C13 H13 117.6 . . ?
C14 C13 H13 117.6 . . ?
C15 C14 C13 116.9(4) . . ?
C15 C14 C12 120.8(4) . . ?
C13 C14 C12 122.3(4) . . ?
C14 C15 C16 120.6(4) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 116.7(4) . . ?
C17 C16 C18 121.9(4) . . ?
C15 C16 C18 121.5(4) . . ?
N2 C17 C16 124.5(5) . . ?
N2 C17 H17 117.8 . . ?
C16 C17 H17 117.8 . . ?
C19 C18 C16 112.7(3) . . ?
C19 C18 H18A 109.1 . . ?
C16 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
C16 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C20 C19 N3 106.8(3) . . ?
C20 C19 C18 130.7(4) . . ?
N3 C19 C18 122.2(4) . . ?
C19 C20 C21 108.0(4) . . ?
C19 C20 H20 126.0 . . ?
C21 C20 H20 126.0 . . ?
C22 C21 C20 107.6(4) . . ?
C22 C21 H21 126.2 . . ?
C20 C21 H21 126.2 . . ?
C21 C22 N3 108.5(4) . . ?
C21 C22 H22 125.8 . . ?
N3 C22 H22 125.8 . . ?
N3 C23 C24 113.9(4) . . ?
N3 C23 H23A 108.8 . . ?
C24 C23 H23A 108.8 . . ?
N3 C23 H23B 108.8 . . ?
C24 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C25 C24 C29 119.6(5) . . ?
C25 C24 C23 122.1(4) . . ?
C29 C24 C23 118.3(5) . . ?
C24 C25 C26 120.3(5) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C27 C26 C25 120.9(5) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 C28 118.8(5) . . ?
C26 C27 H27 120.6 . . ?
C28 C27 H27 120.6 . . ?
C27 C28 C29 121.2(6) . . ?
C27 C28 H28 119.4 . . ?
C29 C28 H28 119.4 . . ?
C24 C29 C28 119.1(6) . . ?
C24 C29 H29 120.4 . . ?
C28 C29 H29 120.4 . . ?
C31 C30 N4 107.9(4) . . ?
C31 C30 H30 126.0 . . ?
N4 C30 H30 126.0 . . ?
C30 C31 C32 107.5(4) . . ?
C30 C31 H31 126.2 . . ?
C32 C31 H31 126.2 . . ?
C33 C32 C31 108.0(4) . . ?
C33 C32 H32 126.0 . . ?
C31 C32 H32 126.0 . . ?
C32 C33 N4 107.1(3) . . ?
C32 C33 C41 130.1(4) . . ?
N4 C33 C41 122.8(3) . . ?
N4 C34 C35 114.7(3) . . ?
N4 C34 H34A 108.6 . . ?
C35 C34 H34A 108.6 . . ?
N4 C34 H34B 108.6 . . ?
C35 C34 H34B 108.6 . . ?
H34A C34 H34B 107.6 . . ?
C40 C35 C36 118.7(5) . . ?
C40 C35 C34 121.6(4) . . ?
C36 C35 C34 119.7(4) . . ?
C37 C36 C35 120.5(5) . . ?
C37 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C36 C37 C38 120.5(5) . . ?
C36 C37 H37 119.8 . . ?
C38 C37 H37 119.8 . . ?
C39 C38 C37 119.5(5) . . ?
C39 C38 H38 120.2 . . ?
C37 C38 H38 120.2 . . ?
C38 C39 C40 120.1(5) . . ?
C38 C39 H39 120.0 . . ?
C40 C39 H39 120.0 . . ?
C39 C40 C35 120.7(5) . . ?
C39 C40 H40 119.6 . . ?
C35 C40 H40 119.6 . . ?
C33 C41 C43 116.2(4) . . ?
C33 C41 H41A 108.2 . . ?
C43 C41 H41A 108.2 . . ?
C33 C41 H41B 108.2 . . ?
C43 C41 H41B 108.2 . . ?
H41A C41 H41B 107.4 . . ?
N5 C42 C43 123.3(4) . . ?
N5 C42 H42 118.3 . . ?
C43 C42 H42 118.3 . . ?
C44 C43 C42 117.4(4) . . ?
C44 C43 C41 121.2(4) . . ?
C42 C43 C41 121.4(4) . . ?
C43 C44 C45 120.7(4) . . ?
C43 C44 H44 119.7 . . ?
C45 C44 H44 119.7 . . ?
C44 C45 C46 117.5(4) . . ?
C44 C45 C47 121.3(4) . . ?
C46 C45 C47 121.2(4) . . ?
N5 C46 C45 123.8(5) . . ?
N5 C46 H46 118.1 . . ?
C45 C46 H46 118.1 . . ?
C48 C47 C45 113.2(3) . . ?
C48 C47 H47A 108.9 . . ?
C45 C47 H47A 108.9 . . ?
C48 C47 H47B 108.9 . . ?
C45 C47 H47B 108.9 . . ?
H47A C47 H47B 107.7 . . ?
C49 C48 N6 107.4(3) . . ?
C49 C48 C47 130.0(4) . . ?
N6 C48 C47 122.4(4) . . ?
C48 C49 C50 108.4(4) . . ?
C48 C49 H49 125.8 . . ?
C50 C49 H49 125.8 . . ?
C51 C50 C49 107.0(4) . . ?
C51 C50 H50 126.5 . . ?
C49 C50 H50 126.5 . . ?
C50 C51 N6 108.2(4) . . ?
C50 C51 H51 125.9 . . ?
N6 C51 H51 125.9 . . ?
N6 C52 C53 114.2(4) . . ?
N6 C52 H52A 108.7 . . ?
C53 C52 H52A 108.7 . . ?
N6 C52 H52B 108.7 . . ?
C53 C52 H52B 108.7 . . ?
H52A C52 H52B 107.6 . . ?
C54 C53 C58 118.5(5) . . ?
C54 C53 C52 121.9(4) . . ?
C58 C53 C52 119.5(5) . . ?
C53 C54 C55 120.8(5) . . ?
C53 C54 H54 119.6 . . ?
C55 C54 H54 119.6 . . ?
C56 C55 C54 119.0(5) . . ?
C56 C55 H55 120.5 . . ?
C54 C55 H55 120.5 . . ?
C55 C56 C57 120.8(5) . . ?
C55 C56 H56 119.6 . . ?
C57 C56 H56 119.6 . . ?
C58 C57 C56 120.2(6) . . ?
C58 C57 H57 119.9 . . ?
C56 C57 H57 119.9 . . ?
C57 C58 C53 120.7(6) . . ?
C57 C58 H58 119.6 . . ?
C53 C58 H58 119.6 . . ?
C4 N1 C1 109.0(3) . . ?
C4 N1 C5 125.5(3) . . ?
C1 N1 C5 125.5(3) . . ?
C13 N2 C17 116.6(4) . . ?
C22 N3 C19 109.0(3) . . ?
C22 N3 C23 125.7(4) . . ?
C19 N3 C23 125.2(4) . . ?
C30 N4 C33 109.5(3) . . ?
C30 N4 C34 125.0(3) . . ?
C33 N4 C34 125.4(3) . . ?
C46 N5 C42 117.3(4) . . ?
C51 N6 C48 109.0(3) . . ?
C51 N6 C52 125.3(3) . . ?
C48 N6 C52 125.3(4) . . ?
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
C1 C2 1.362(6) . ?
C1 N1 1.379(5) . ?
C1 C12 1.493(6) . ?
C2 C3 1.416(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.364(6) . ?
C3 H3 0.9500 . ?
C4 N1 1.373(5) . ?
C4 H4 0.9500 . ?
C5 N1 1.460(5) . ?
C5 C6 1.503(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C11 1.383(7) . ?
C6 C7 1.398(7) . ?
C7 C8 1.378(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.380(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(8) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C14 1.517(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N2 1.335(5) . ?
C13 C14 1.390(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(6) . ?
C15 C16 1.402(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(7) . ?
C16 C18 1.512(6) . ?
C17 N2 1.343(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.487(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.369(6) . ?
C19 N3 1.381(5) . ?
C20 C21 1.415(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.344(6) . ?
C21 H21 0.9500 . ?
C22 N3 1.376(5) . ?
C22 H22 0.9500 . ?
C23 N3 1.451(6) . ?
C23 C24 1.517(7) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.375(6) . ?
C24 C29 1.389(7) . ?
C25 C26 1.384(7) . ?
C25 H25 0.9500 . ?
C26 C27 1.369(7) . ?
C26 H26 0.9500 . ?
C27 C28 1.378(9) . ?
C27 H27 0.9500 . ?
C28 C29 1.390(10) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 C31 1.362(6) . ?
C30 N4 1.370(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.415(6) . ?
C31 H31 0.9500 . ?
C32 C33 1.366(6) . ?
C32 H32 0.9500 . ?
C33 N4 1.381(5) . ?
C33 C41 1.491(6) . ?
C34 N4 1.456(5) . ?
C34 C35 1.508(7) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C40 1.389(7) . ?
C35 C36 1.391(7) . ?
C36 C37 1.381(8) . ?
C36 H36 0.9500 . ?
C37 C38 1.384(8) . ?
C37 H37 0.9500 . ?
C38 C39 1.382(7) . ?
C38 H38 0.9500 . ?
C39 C40 1.387(8) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 C43 1.514(6) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 N5 1.346(6) . ?
C42 C43 1.394(6) . ?
C42 H42 0.9500 . ?
C43 C44 1.382(6) . ?
C44 C45 1.383(6) . ?
C44 H44 0.9500 . ?
C45 C46 1.385(7) . ?
C45 C47 1.525(5) . ?
C46 N5 1.341(6) . ?
C46 H46 0.9500 . ?
C47 C48 1.495(5) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 C49 1.365(6) . ?
C48 N6 1.379(5) . ?
C49 C50 1.411(6) . ?
C49 H49 0.9500 . ?
C50 C51 1.371(6) . ?
C50 H50 0.9500 . ?
C51 N6 1.373(5) . ?
C51 H51 0.9500 . ?
C52 N6 1.450(5) . ?
C52 C53 1.507(7) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C53 C54 1.392(6) . ?
C53 C58 1.396(7) . ?
C54 C55 1.399(6) . ?
C54 H54 0.9500 . ?
C55 C56 1.376(7) . ?
C55 H55 0.9500 . ?
C56 C57 1.382(9) . ?
C56 H56 0.9500 . ?
C57 C58 1.371(10) . ?
C57 H57 0.9500 . ?
C58 H58 0.9500 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168331234
