#------------------------------------------------------------------------------
#$Date: 2025-07-30 07:51:54 +0200 (Wed 30 de Jul de 2025) $
#$Revision: 301408 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/92/4519248.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_4519248
loop_
_publ_author_name
'Xu, Xian'
'Zheng, Xizhou'
'Xu, Xin'
_publ_section_title
;
 Synthesis of Tetrahydroquinolines by Scandium-Catalyzed [3 + 3]
 Annulation of Anilines with Allenes and Dienes
;
_journal_issue                   24
_journal_name_full               'ACS Catalysis'
_journal_page_first              14995
_journal_page_last               15003
_journal_paper_doi               10.1021/acscatal.1c04657
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C24 H25 N'
_chemical_formula_sum            'C24 H25 N'
_chemical_formula_weight         327.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                92.736(2)
_cell_angle_beta                 93.818(2)
_cell_angle_gamma                93.332(2)
_cell_formula_units_Z            4
_cell_length_a                   10.1618(5)
_cell_length_b                   13.2018(6)
_cell_length_c                   13.7980(6)
_cell_measurement_reflns_used    6775
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      108.042
_cell_measurement_theta_min      5.592
_cell_volume                     1841.35(15)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            54395
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.021
_diffrn_reflns_theta_min         2.796
_diffrn_source_current           3.57
_diffrn_source_power             0.2494716
_diffrn_source_voltage           69.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.325
_exptl_absorpt_correction_T_max  0.7506
_exptl_absorpt_correction_T_min  0.6355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1026 before and 0.0724 after correction.
The Ratio of minimum to maximum transmission is 0.8467.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     468
_refine_ls_number_reflns         6775
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0555
_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)+(0.0834P)²+0.2145P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1518
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4604
_reflns_number_total             6775
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c04657_si_002.cif
_cod_data_source_block           ga210511i_0m
_cod_depositor_comments
;

2025-07-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C48 H50 N2'
_cod_original_formula_weight         654.90
_cod_original_formula_moiety         '2(C24 H25 N)'
_cod_original_formula_units_Z            2
_cod_database_code               4519248
_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_max   0.909
_shelx_estimated_absorpt_t_min   0.881
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C39(H39A,H39B), C40(H40A,H40B)
2.b Aromatic/amide H refined with riding coordinates:
 C35(H35), C14(H14), C34(H34), C28(H28), C38(H38), C24(H24), C11(H11),
 C44(H44), C6(H6), C4(H4), C27(H27), C30(H30), C48(H48), C22(H22), C31(H31),
 C20(H20), C3(H3), C10(H10), C23(H23), C47(H47), C7(H7), C21(H21), C45(H45),
 C46(H46)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C32(H32A,H32B,H32C), C41(H41A,H41B,H41C), C8(H8A,H8B,
 H8C), C25(H25A,H25B,H25C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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
N2 N 0.63780(14) 0.06641(11) 0.85354(11) 0.0291(4) Uani 1 1 d . . . . .
N1 N 0.85452(15) 0.55987(11) 0.65585(10) 0.0289(4) Uani 1 1 d . . . . .
C36 C 0.57376(17) -0.03045(13) 0.84938(12) 0.0273(4) Uani 1 1 d . . . . .
C29 C 0.57345(17) 0.14920(13) 0.81113(13) 0.0281(4) Uani 1 1 d . . . . .
C33 C 0.44357(18) -0.22737(13) 0.83763(13) 0.0306(4) Uani 1 1 d . . . . .
C19 C 0.85861(17) 0.56768(13) 0.83688(13) 0.0284(4) Uani 1 1 d . . . . .
C12 C 0.84009(17) 0.46277(13) 0.61000(12) 0.0286(4) Uani 1 1 d . . . . .
C35 C 0.44701(18) -0.04941(14) 0.80245(13) 0.0300(4) Uani 1 1 d . . . . .
H35 H 0.403889 0.004696 0.773456 0.036 Uiso 1 1 calc R U . . .
C5 C 0.78913(18) 0.64190(13) 0.61343(13) 0.0291(4) Uani 1 1 d . . . . .
C37 C 0.63529(18) -0.11266(14) 0.89020(13) 0.0295(4) Uani 1 1 d . . . . .
C14 C 0.88731(18) 0.28567(14) 0.60074(13) 0.0315(5) Uani 1 1 d . . . . .
H14 H 0.931902 0.231216 0.627800 0.038 Uiso 1 1 calc R U . . .
C34 C 0.38409(18) -0.14521(14) 0.79775(13) 0.0316(4) Uani 1 1 d . . . . .
H34 H 0.297876 -0.155285 0.766440 0.038 Uiso 1 1 calc R U . . .
C13 C 0.90616(18) 0.38105(14) 0.64793(13) 0.0297(4) Uani 1 1 d . . . . .
C43 C 0.87686(17) 0.07101(13) 0.82177(13) 0.0288(4) Uani 1 1 d . . . . .
C17 C 0.93858(18) 0.58207(13) 0.74739(13) 0.0299(4) Uani 1 1 d . . . . .
C28 C 0.46935(18) 0.19118(14) 0.85524(14) 0.0323(5) Uani 1 1 d . . . . .
H28 H 0.438034 0.162956 0.912074 0.039 Uiso 1 1 calc R U . . .
C38 C 0.56931(18) -0.20841(14) 0.88305(13) 0.0317(5) Uani 1 1 d . . . . .
H38 H 0.612316 -0.263377 0.910543 0.038 Uiso 1 1 calc R U . . .
C24 C 0.74274(18) 0.50518(13) 0.83219(13) 0.0322(5) Uani 1 1 d . . . . .
H24 H 0.709770 0.473356 0.771514 0.039 Uiso 1 1 calc R U . . .
C9 C 0.80645(19) 0.26563(14) 0.51579(13) 0.0338(5) Uani 1 1 d . . . . .
C11 C 0.75615(19) 0.44289(14) 0.52524(13) 0.0328(5) Uani 1 1 d . . . . .
H11 H 0.708839 0.496362 0.498873 0.039 Uiso 1 1 calc R U . . .
C42 C 0.77435(17) 0.08674(14) 0.89754(13) 0.0310(4) Uani 1 1 d . . . . .
C15 C 0.99743(18) 0.39845(14) 0.73849(14) 0.0338(5) Uani 1 1 d . . . . .
H15A H 1.071972 0.353666 0.734809 0.041 Uiso 1 1 calc R U . . .
H15B H 0.949113 0.381298 0.796088 0.041 Uiso 1 1 calc R U . . .
C44 C 1.00387(18) 0.11817(14) 0.83520(14) 0.0348(5) Uani 1 1 d . . . . .
H44 H 1.025563 0.163604 0.890165 0.042 Uiso 1 1 calc R U . . .
C6 C 0.68462(18) 0.68461(14) 0.65635(14) 0.0339(5) Uani 1 1 d . . . . .
H6 H 0.651542 0.656565 0.712704 0.041 Uiso 1 1 calc R U . . .
C4 C 0.83377(19) 0.68277(14) 0.53022(13) 0.0333(5) Uani 1 1 d . . . . .
H4 H 0.905308 0.654235 0.499911 0.040 Uiso 1 1 calc R U . . .
C27 C 0.41069(19) 0.27383(14) 0.81716(14) 0.0349(5) Uani 1 1 d . . . . .
H27 H 0.338227 0.300751 0.847626 0.042 Uiso 1 1 calc R U . . .
C30 C 0.61746(18) 0.19140(14) 0.72829(14) 0.0331(5) Uani 1 1 d . . . . .
H30 H 0.687635 0.162780 0.696366 0.040 Uiso 1 1 calc R U . . .
C26 C 0.45543(18) 0.31831(13) 0.73536(14) 0.0337(5) Uani 1 1 d . . . . .
C2 C 0.67166(19) 0.80940(14) 0.53434(14) 0.0352(5) Uani 1 1 d . . . . .
C48 C 0.84939(19) 0.00549(14) 0.73978(14) 0.0346(5) Uani 1 1 d . . . . .
H48 H 0.763454 -0.026867 0.727998 0.041 Uiso 1 1 calc R U . . .
C22 C 0.7200(2) 0.53566(14) 1.00270(14) 0.0374(5) Uani 1 1 d . . . . .
H22 H 0.672502 0.525517 1.058821 0.045 Uiso 1 1 calc R U . . .
C31 C 0.55913(19) 0.27554(14) 0.69181(14) 0.0363(5) Uani 1 1 d . . . . .
H31 H 0.591276 0.304423 0.635538 0.044 Uiso 1 1 calc R U . . .
C16 C 1.05022(18) 0.50867(14) 0.74912(14) 0.0337(5) Uani 1 1 d . . . . .
H16A H 1.107488 0.523004 0.695484 0.040 Uiso 1 1 calc R U . . .
H16B H 1.104913 0.520089 0.811206 0.040 Uiso 1 1 calc R U . . .
C18 C 1.00147(19) 0.69081(14) 0.74703(15) 0.0368(5) Uani 1 1 d . . . . .
H18A H 1.067283 0.702665 0.802224 0.055 Uiso 1 1 calc R U . . .
H18B H 0.932778 0.739499 0.752412 0.055 Uiso 1 1 calc R U . . .
H18C H 1.044441 0.699587 0.686212 0.055 Uiso 1 1 calc R U . . .
C20 C 0.90361(19) 0.61234(14) 0.92727(13) 0.0350(5) Uani 1 1 d . . . . .
H20 H 0.983498 0.653942 0.932988 0.042 Uiso 1 1 calc R U . . .
C39 C 0.77045(19) -0.09718(14) 0.94208(14) 0.0356(5) Uani 1 1 d . . . . .
H39A H 0.838237 -0.115330 0.897044 0.043 Uiso 1 1 calc R U . . .
H39B H 0.776799 -0.141990 0.997510 0.043 Uiso 1 1 calc R U . . .
C3 C 0.77509(19) 0.76479(14) 0.49085(14) 0.0364(5) Uani 1 1 d . . . . .
H3 H 0.805976 0.791142 0.433065 0.044 Uiso 1 1 calc R U . . .
C10 C 0.74108(19) 0.34684(14) 0.47942(13) 0.0353(5) Uani 1 1 d . . . . .
H10 H 0.684636 0.336200 0.421678 0.042 Uiso 1 1 calc R U . . .
C23 C 0.6749(2) 0.48862(14) 0.91408(14) 0.0361(5) Uani 1 1 d . . . . .
H23 H 0.596985 0.444752 0.909458 0.043 Uiso 1 1 calc R U . . .
C47 C 0.94436(19) -0.01341(14) 0.67532(15) 0.0381(5) Uani 1 1 d . . . . .
H47 H 0.923655 -0.059376 0.620616 0.046 Uiso 1 1 calc R U . . .
C7 C 0.62813(19) 0.76796(15) 0.61756(15) 0.0375(5) Uani 1 1 d . . . . .
H7 H 0.557914 0.797349 0.648784 0.045 Uiso 1 1 calc R U . . .
C40 C 0.79553(19) 0.01261(14) 0.97875(13) 0.0361(5) Uani 1 1 d . . . . .
H40A H 0.887410 0.023158 1.007645 0.043 Uiso 1 1 calc R U . . .
H40B H 0.735409 0.027405 1.030508 0.043 Uiso 1 1 calc R U . . .
C21 C 0.8348(2) 0.59754(15) 1.00875(14) 0.0395(5) Uani 1 1 d . . . . .
H21 H 0.866526 0.630115 1.069375 0.047 Uiso 1 1 calc R U . . .
C32 C 0.3763(2) -0.33214(14) 0.83193(15) 0.0397(5) Uani 1 1 d . . . . .
H32A H 0.311545 -0.336380 0.881345 0.060 Uiso 1 1 calc R U . . .
H32B H 0.442304 -0.382262 0.843491 0.060 Uiso 1 1 calc R U . . .
H32C H 0.331255 -0.346080 0.767240 0.060 Uiso 1 1 calc R U . . .
C45 C 1.09867(19) 0.10007(15) 0.77014(15) 0.0400(5) Uani 1 1 d . . . . .
H45 H 1.184317 0.133166 0.780755 0.048 Uiso 1 1 calc R U . . .
C46 C 1.06959(19) 0.03424(14) 0.68993(15) 0.0407(5) Uani 1 1 d . . . . .
H46 H 1.134705 0.021746 0.645244 0.049 Uiso 1 1 calc R U . . .
C41 C 0.7877(2) 0.19487(14) 0.94501(15) 0.0405(5) Uani 1 1 d . . . . .
H41A H 0.787323 0.244336 0.894260 0.061 Uiso 1 1 calc R U . . .
H41B H 0.870814 0.204208 0.985560 0.061 Uiso 1 1 calc R U . . .
H41C H 0.713386 0.205017 0.985479 0.061 Uiso 1 1 calc R U . . .
C8 C 0.7936(2) 0.16211(14) 0.46541(15) 0.0451(5) Uani 1 1 d . . . . .
H8A H 0.703698 0.149078 0.435414 0.068 Uiso 1 1 calc R U . . .
H8B H 0.811759 0.110875 0.512839 0.068 Uiso 1 1 calc R U . . .
H8C H 0.857008 0.158652 0.415023 0.068 Uiso 1 1 calc R U . . .
C25 C 0.3944(2) 0.41043(15) 0.69518(16) 0.0465(6) Uani 1 1 d . . . . .
H25A H 0.337846 0.389924 0.636411 0.070 Uiso 1 1 calc R U . . .
H25B H 0.464520 0.459682 0.679068 0.070 Uiso 1 1 calc R U . . .
H25C H 0.341338 0.441513 0.743963 0.070 Uiso 1 1 calc R U . . .
C1 C 0.6096(3) 0.90034(18) 0.4938(2) 0.0492(6) Uani 1 1 d . . . . .
H1A H 0.517(3) 0.887(2) 0.477(2) 0.103(11) Uiso 1 1 d . . . . .
H1B H 0.615(3) 0.953(2) 0.538(2) 0.109(12) Uiso 1 1 d . . . . .
H1C H 0.636(3) 0.914(2) 0.429(3) 0.123(13) 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 0.0137 0.0067 '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 0.0241 0.0134 '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
C36 N2 C29 120.13(14) . . ?
C36 N2 C42 122.04(14) . . ?
C29 N2 C42 117.79(14) . . ?
C12 N1 C5 119.90(14) . . ?
C12 N1 C17 122.01(14) . . ?
C5 N1 C17 118.08(13) . . ?
N2 C36 C35 121.17(16) . . ?
N2 C36 C37 121.01(16) . . ?
C37 C36 C35 117.81(16) . . ?
C28 C29 N2 120.17(16) . . ?
C30 C29 N2 120.93(16) . . ?
C30 C29 C28 118.83(17) . . ?
C34 C33 C32 122.08(17) . . ?
C38 C33 C34 116.82(16) . . ?
C38 C33 C32 121.10(17) . . ?
C24 C19 C17 121.64(16) . . ?
C20 C19 C17 120.86(16) . . ?
C20 C19 C24 117.41(17) . . ?
N1 C12 C13 121.48(16) . . ?
N1 C12 C11 120.89(16) . . ?
C11 C12 C13 117.61(16) . . ?
C36 C35 H35 119.4 . . ?
C34 C35 C36 121.19(17) . . ?
C34 C35 H35 119.4 . . ?
C6 C5 N1 121.24(16) . . ?
C4 C5 N1 119.93(16) . . ?
C4 C5 C6 118.77(17) . . ?
C36 C37 C39 120.38(16) . . ?
C38 C37 C36 119.34(17) . . ?
C38 C37 C39 120.27(17) . . ?
C13 C14 H14 118.3 . . ?
C13 C14 C9 123.37(18) . . ?
C9 C14 H14 118.3 . . ?
C33 C34 H34 119.1 . . ?
C35 C34 C33 121.74(17) . . ?
C35 C34 H34 119.1 . . ?
C12 C13 C15 119.66(16) . . ?
C14 C13 C12 119.47(17) . . ?
C14 C13 C15 120.87(16) . . ?
C44 C43 C42 121.04(16) . . ?
C48 C43 C42 121.62(16) . . ?
C48 C43 C44 117.26(17) . . ?
N1 C17 C19 111.23(14) . . ?
N1 C17 C16 108.04(14) . . ?
N1 C17 C18 108.87(14) . . ?
C19 C17 C18 111.38(15) . . ?
C16 C17 C19 109.24(15) . . ?
C16 C17 C18 107.96(15) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 C29 120.49(18) . . ?
C27 C28 H28 119.8 . . ?
C33 C38 C37 123.10(17) . . ?
C33 C38 H38 118.5 . . ?
C37 C38 H38 118.5 . . ?
C19 C24 H24 119.4 . . ?
C23 C24 C19 121.30(17) . . ?
C23 C24 H24 119.4 . . ?
C14 C9 C8 121.29(18) . . ?
C10 C9 C14 116.59(17) . . ?
C10 C9 C8 122.10(18) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 C12 121.28(17) . . ?
C10 C11 H11 119.4 . . ?
N2 C42 C43 111.32(14) . . ?
N2 C42 C40 107.76(14) . . ?
N2 C42 C41 108.85(14) . . ?
C40 C42 C43 109.33(15) . . ?
C40 C42 C41 107.50(15) . . ?
C41 C42 C43 111.92(15) . . ?
C13 C15 H15A 109.6 . . ?
C13 C15 H15B 109.6 . . ?
C13 C15 C16 110.14(15) . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
C43 C44 H44 119.3 . . ?
C45 C44 C43 121.36(18) . . ?
C45 C44 H44 119.3 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.33(18) . . ?
C7 C6 H6 119.8 . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.52(17) . . ?
C3 C4 H4 119.7 . . ?
C28 C27 H27 119.3 . . ?
C28 C27 C26 121.37(18) . . ?
C26 C27 H27 119.3 . . ?
C29 C30 H30 120.0 . . ?
C29 C30 C31 120.06(17) . . ?
C31 C30 H30 120.0 . . ?
C27 C26 C25 121.63(18) . . ?
C31 C26 C27 117.59(18) . . ?
C31 C26 C25 120.78(18) . . ?
C3 C2 C1 121.7(2) . . ?
C7 C2 C3 117.72(18) . . ?
C7 C2 C1 120.6(2) . . ?
C43 C48 H48 119.3 . . ?
C47 C48 C43 121.42(18) . . ?
C47 C48 H48 119.3 . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C21 C22 C23 119.26(18) . . ?
C30 C31 H31 119.2 . . ?
C26 C31 C30 121.63(18) . . ?
C26 C31 H31 119.2 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C15 C16 C17 111.95(15) . . ?
C15 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C19 C20 H20 119.3 . . ?
C21 C20 C19 121.43(18) . . ?
C21 C20 H20 119.3 . . ?
C37 C39 H39A 109.7 . . ?
C37 C39 H39B 109.7 . . ?
C37 C39 C40 109.95(16) . . ?
H39A C39 H39B 108.2 . . ?
C40 C39 H39A 109.7 . . ?
C40 C39 H39B 109.7 . . ?
C4 C3 C2 121.18(18) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.67(18) . . ?
C11 C10 H10 119.2 . . ?
C24 C23 C22 120.22(18) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C48 C47 H47 119.8 . . ?
C48 C47 C46 120.38(18) . . ?
C46 C47 H47 119.8 . . ?
C6 C7 H7 119.3 . . ?
C2 C7 C6 121.45(18) . . ?
C2 C7 H7 119.3 . . ?
C42 C40 H40A 109.2 . . ?
C42 C40 H40B 109.2 . . ?
C39 C40 C42 112.26(15) . . ?
C39 C40 H40A 109.2 . . ?
C39 C40 H40B 109.2 . . ?
H40A C40 H40B 107.9 . . ?
C22 C21 H21 119.8 . . ?
C20 C21 C22 120.36(18) . . ?
C20 C21 H21 119.8 . . ?
C33 C32 H32A 109.5 . . ?
C33 C32 H32B 109.5 . . ?
C33 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C44 C45 H45 119.8 . . ?
C46 C45 C44 120.37(18) . . ?
C46 C45 H45 119.8 . . ?
C47 C46 H46 120.4 . . ?
C45 C46 C47 119.20(18) . . ?
C45 C46 H46 120.4 . . ?
C42 C41 H41A 109.5 . . ?
C42 C41 H41B 109.5 . . ?
C42 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C2 C1 H1A 111.9(18) . . ?
C2 C1 H1B 111.5(19) . . ?
C2 C1 H1C 112.4(19) . . ?
H1A C1 H1B 105(3) . . ?
H1A C1 H1C 98(3) . . ?
H1B C1 H1C 117(3) . . ?
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
N2 C36 1.398(2) . ?
N2 C29 1.435(2) . ?
N2 C42 1.481(2) . ?
N1 C12 1.398(2) . ?
N1 C5 1.432(2) . ?
N1 C17 1.484(2) . ?
C36 C35 1.406(2) . ?
C36 C37 1.406(2) . ?
C29 C28 1.385(3) . ?
C29 C30 1.385(3) . ?
C33 C34 1.390(3) . ?
C33 C38 1.389(3) . ?
C33 C32 1.503(2) . ?
C19 C17 1.536(2) . ?
C19 C24 1.394(2) . ?
C19 C20 1.391(2) . ?
C12 C13 1.407(2) . ?
C12 C11 1.406(3) . ?
C35 H35 0.9500 . ?
C35 C34 1.380(2) . ?
C5 C6 1.385(2) . ?
C5 C4 1.384(3) . ?
C37 C38 1.392(2) . ?
C37 C39 1.504(3) . ?
C14 H14 0.9500 . ?
C14 C13 1.387(2) . ?
C14 C9 1.391(3) . ?
C34 H34 0.9500 . ?
C13 C15 1.506(3) . ?
C43 C42 1.540(2) . ?
C43 C44 1.397(2) . ?
C43 C48 1.394(3) . ?
C17 C16 1.534(3) . ?
C17 C18 1.538(2) . ?
C28 H28 0.9500 . ?
C28 C27 1.382(3) . ?
C38 H38 0.9500 . ?
C24 H24 0.9500 . ?
C24 C23 1.382(3) . ?
C9 C10 1.390(3) . ?
C9 C8 1.498(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.385(3) . ?
C42 C40 1.535(3) . ?
C42 C41 1.537(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.518(2) . ?
C44 H44 0.9500 . ?
C44 C45 1.383(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.384(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.382(3) . ?
C27 H27 0.9500 . ?
C27 C26 1.388(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.389(3) . ?
C26 C31 1.382(3) . ?
C26 C25 1.509(3) . ?
C2 C3 1.391(3) . ?
C2 C7 1.383(3) . ?
C2 C1 1.502(3) . ?
C48 H48 0.9500 . ?
C48 C47 1.381(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.382(3) . ?
C22 C21 1.380(3) . ?
C31 H31 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 H20 0.9500 . ?
C20 C21 1.379(3) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C39 C40 1.514(3) . ?
C3 H3 0.9500 . ?
C10 H10 0.9500 . ?
C23 H23 0.9500 . ?
C47 H47 0.9500 . ?
C47 C46 1.384(3) . ?
C7 H7 0.9500 . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C21 H21 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C45 H45 0.9500 . ?
C45 C46 1.379(3) . ?
C46 H46 0.9500 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C1 H1A 0.96(3) . ?
C1 H1B 0.91(3) . ?
C1 H1C 0.97(4) . ?
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
N2 C36 C35 C34 179.55(16) . . . . ?
N2 C36 C37 C38 -178.83(16) . . . . ?
N2 C36 C37 C39 1.9(3) . . . . ?
N2 C29 C28 C27 177.13(16) . . . . ?
N2 C29 C30 C31 -175.98(16) . . . . ?
N2 C42 C40 C39 56.8(2) . . . . ?
N1 C12 C13 C14 179.04(16) . . . . ?
N1 C12 C13 C15 -1.6(3) . . . . ?
N1 C12 C11 C10 -179.89(16) . . . . ?
N1 C5 C6 C7 175.93(16) . . . . ?
N1 C5 C4 C3 -177.24(16) . . . . ?
N1 C17 C16 C15 -56.2(2) . . . . ?
C36 N2 C29 C28 72.4(2) . . . . ?
C36 N2 C29 C30 -110.40(19) . . . . ?
C36 N2 C42 C43 89.11(19) . . . . ?
C36 N2 C42 C40 -30.8(2) . . . . ?
C36 N2 C42 C41 -147.06(16) . . . . ?
C36 C35 C34 C33 -1.0(3) . . . . ?
C36 C37 C38 C33 -0.5(3) . . . . ?
C36 C37 C39 C40 24.1(2) . . . . ?
C29 N2 C36 C35 1.2(2) . . . . ?
C29 N2 C36 C37 179.78(15) . . . . ?
C29 N2 C42 C43 -88.50(18) . . . . ?
C29 N2 C42 C40 151.62(15) . . . . ?
C29 N2 C42 C41 35.3(2) . . . . ?
C29 C28 C27 C26 -1.3(3) . . . . ?
C29 C30 C31 C26 -1.0(3) . . . . ?
C19 C17 C16 C15 64.95(19) . . . . ?
C19 C24 C23 C22 1.1(3) . . . . ?
C19 C20 C21 C22 1.4(3) . . . . ?
C12 N1 C5 C6 110.45(19) . . . . ?
C12 N1 C5 C4 -72.3(2) . . . . ?
C12 N1 C17 C19 -90.71(19) . . . . ?
C12 N1 C17 C16 29.2(2) . . . . ?
C12 N1 C17 C18 146.19(16) . . . . ?
C12 C13 C15 C16 -25.4(2) . . . . ?
C12 C11 C10 C9 1.0(3) . . . . ?
C35 C36 C37 C38 -0.2(2) . . . . ?
C35 C36 C37 C39 -179.51(16) . . . . ?
C5 N1 C12 C13 177.98(16) . . . . ?
C5 N1 C12 C11 -3.6(2) . . . . ?
C5 N1 C17 C19 90.52(18) . . . . ?
C5 N1 C17 C16 -149.60(15) . . . . ?
C5 N1 C17 C18 -32.6(2) . . . . ?
C5 C6 C7 C2 1.5(3) . . . . ?
C5 C4 C3 C2 1.1(3) . . . . ?
C37 C36 C35 C34 0.9(3) . . . . ?
C37 C39 C40 C42 -54.0(2) . . . . ?
C14 C13 C15 C16 153.91(17) . . . . ?
C14 C9 C10 C11 0.3(3) . . . . ?
C34 C33 C38 C37 0.4(3) . . . . ?
C13 C12 C11 C10 -1.4(3) . . . . ?
C13 C14 C9 C10 -1.1(3) . . . . ?
C13 C14 C9 C8 177.52(17) . . . . ?
C13 C15 C16 C17 54.9(2) . . . . ?
C43 C42 C40 C39 -64.34(19) . . . . ?
C43 C44 C45 C46 -0.1(3) . . . . ?
C43 C48 C47 C46 -1.2(3) . . . . ?
C17 N1 C12 C13 -0.8(2) . . . . ?
C17 N1 C12 C11 177.69(16) . . . . ?
C17 N1 C5 C6 -70.7(2) . . . . ?
C17 N1 C5 C4 106.50(19) . . . . ?
C17 C19 C24 C23 176.73(17) . . . . ?
C17 C19 C20 C21 -178.04(17) . . . . ?
C28 C29 C30 C31 1.2(3) . . . . ?
C28 C27 C26 C31 1.4(3) . . . . ?
C28 C27 C26 C25 -178.17(17) . . . . ?
C38 C33 C34 C35 0.4(3) . . . . ?
C38 C37 C39 C40 -155.25(16) . . . . ?
C24 C19 C17 N1 23.3(2) . . . . ?
C24 C19 C17 C16 -95.86(19) . . . . ?
C24 C19 C17 C18 144.97(17) . . . . ?
C24 C19 C20 C21 -1.6(3) . . . . ?
C9 C14 C13 C12 0.7(3) . . . . ?
C9 C14 C13 C15 -178.61(17) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C11 C12 C13 C15 179.87(16) . . . . ?
C42 N2 C36 C35 -176.36(15) . . . . ?
C42 N2 C36 C37 2.2(2) . . . . ?
C42 N2 C29 C28 -109.90(18) . . . . ?
C42 N2 C29 C30 67.3(2) . . . . ?
C42 C43 C44 C45 176.45(17) . . . . ?
C42 C43 C48 C47 -175.77(17) . . . . ?
C44 C43 C42 N2 157.17(16) . . . . ?
C44 C43 C42 C40 -83.9(2) . . . . ?
C44 C43 C42 C41 35.1(2) . . . . ?
C44 C43 C48 C47 1.1(3) . . . . ?
C44 C45 C46 C47 0.0(3) . . . . ?
C6 C5 C4 C3 0.1(3) . . . . ?
C4 C5 C6 C7 -1.3(3) . . . . ?
C27 C26 C31 C30 -0.3(3) . . . . ?
C30 C29 C28 C27 -0.1(3) . . . . ?
C48 C43 C42 N2 -26.1(2) . . . . ?
C48 C43 C42 C40 92.81(19) . . . . ?
C48 C43 C42 C41 -148.20(17) . . . . ?
C48 C43 C44 C45 -0.4(3) . . . . ?
C48 C47 C46 C45 0.6(3) . . . . ?
C18 C17 C16 C15 -173.78(15) . . . . ?
C20 C19 C17 N1 -160.36(16) . . . . ?
C20 C19 C17 C16 80.5(2) . . . . ?
C20 C19 C17 C18 -38.7(2) . . . . ?
C20 C19 C24 C23 0.3(3) . . . . ?
C39 C37 C38 C33 178.86(17) . . . . ?
C3 C2 C7 C6 -0.3(3) . . . . ?
C23 C22 C21 C20 0.1(3) . . . . ?
C7 C2 C3 C4 -0.9(3) . . . . ?
C21 C22 C23 C24 -1.3(3) . . . . ?
C32 C33 C34 C35 -179.36(17) . . . . ?
C32 C33 C38 C37 -179.90(17) . . . . ?
C41 C42 C40 C39 173.97(15) . . . . ?
C8 C9 C10 C11 -178.37(18) . . . . ?
C25 C26 C31 C30 179.33(17) . . . . ?
C1 C2 C3 C4 178.3(2) . . . . ?
C1 C2 C7 C6 -179.57(19) . . . . ?
