#------------------------------------------------------------------------------
#$Date: 2022-02-12 23:53:43 +0100 (Sat 12 de Feb de 2022) $
#$Revision: 272945 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/97/7129707.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_7129707
loop_
_publ_author_name
'Huang, Shuai'
'Zhang, Gao-Peng'
'Jiang, Yang-Jie'
'Yu, Fei-Le'
'Ding, Chang-Hua'
'Hou, Xuelong'
_publ_section_title
;
 Pd-Catalyzed Umpolung Asymmetric Allylic Alkylation of Hydrazones to
 Vicinal Tertiary and Quaternary Chiral Carbon Centers
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC07074F
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H21 N'
_chemical_formula_weight         239.35
_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-2013
_audit_update_record
;
2020-03-24 deposited with the CCDC.	2022-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.5730(10)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   6.06320(10)
_cell_length_b                   31.1441(6)
_cell_length_c                   11.8320(2)
_cell_measurement_reflns_used    9826
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      140.179
_cell_measurement_theta_min      5.675
_cell_volume                     2171.87(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            34262
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.985
_diffrn_reflns_theta_min         2.838
_exptl_absorpt_coefficient_mu    0.474
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.105
_refine_diff_density_min         -0.098
_refine_diff_density_rms         0.020
_refine_ls_abs_structure_details
; 
 Flack x determined using 3321 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.13(17)
_refine_ls_extinction_coef       0.0110(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     518
_refine_ls_number_reflns         7552
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0348
_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)+(0.0488P)²+0.1304P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0915
_reflns_Friedel_coverage         0.956
_reflns_Friedel_fraction_full    0.959
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                7176
_reflns_number_total             7552
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc07074f2.cif
_cod_data_source_block           cu_d8v19809_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7129707
_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   0.915
_shelx_estimated_absorpt_t_max   0.941
_shelxl_version_number           2013-4
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
N1 N 0.8625(4) 0.31226(8) 0.5142(2) 0.0624(5) Uani 1 1 d . . . . .
C1 C 0.6552(4) 0.29727(7) 0.54701(19) 0.0525(5) Uani 1 1 d . . . . .
C2 C 0.4435(5) 0.31194(10) 0.4569(2) 0.0703(7) Uani 1 1 d . . . . .
H2A H 0.4467 0.3426 0.4486 0.106 Uiso 1 1 calc R U . . .
H2B H 0.3101 0.3038 0.4822 0.106 Uiso 1 1 calc R U . . .
H2C H 0.4411 0.2986 0.3834 0.106 Uiso 1 1 calc R U . . .
C3 C 0.6618(4) 0.31559(7) 0.67141(19) 0.0502(5) Uani 1 1 d . . . . .
H3 H 0.7994 0.3039 0.7228 0.060 Uiso 1 1 calc R U . . .
C4 C 0.4637(4) 0.30027(8) 0.7208(2) 0.0595(6) Uani 1 1 d . . . . .
H4A H 0.3248 0.3132 0.6764 0.071 Uiso 1 1 calc R U . . .
H4B H 0.4489 0.2694 0.7111 0.071 Uiso 1 1 calc R U . . .
C5 C 0.4902(7) 0.31101(10) 0.8477(3) 0.0845(9) Uani 1 1 d . . . . .
H5A H 0.4889 0.3416 0.8571 0.127 Uiso 1 1 calc R U . . .
H5B H 0.6314 0.2997 0.8919 0.127 Uiso 1 1 calc R U . . .
H5C H 0.3671 0.2986 0.8748 0.127 Uiso 1 1 calc R U . . .
C6 C 0.6887(4) 0.36423(7) 0.67711(19) 0.0510(5) Uani 1 1 d . . . . .
C7 C 0.5073(4) 0.39208(8) 0.6395(2) 0.0601(6) Uani 1 1 d . . . . .
H7 H 0.3625 0.3809 0.6111 0.072 Uiso 1 1 calc R U . . .
C8 C 0.5383(5) 0.43600(8) 0.6435(3) 0.0697(7) Uani 1 1 d . . . . .
H8 H 0.4148 0.4540 0.6168 0.084 Uiso 1 1 calc R U . . .
C9 C 0.7495(5) 0.45338(8) 0.6866(2) 0.0706(7) Uani 1 1 d . . . . .
H9 H 0.7695 0.4830 0.6892 0.085 Uiso 1 1 calc R U . . .
C10 C 0.9308(5) 0.42645(9) 0.7257(2) 0.0694(7) Uani 1 1 d . . . . .
H10 H 1.0745 0.4379 0.7553 0.083 Uiso 1 1 calc R U . . .
C11 C 0.9008(4) 0.38242(8) 0.7214(2) 0.0601(6) Uani 1 1 d . . . . .
H11 H 1.0250 0.3646 0.7487 0.072 Uiso 1 1 calc R U . . .
C12 C 0.6726(4) 0.24818(8) 0.5564(2) 0.0572(6) Uani 1 1 d . . . . .
C13 C 0.8791(5) 0.22913(8) 0.6052(3) 0.0711(7) Uani 1 1 d . . . . .
H13 H 1.0059 0.2464 0.6312 0.085 Uiso 1 1 calc R U . . .
C14 C 0.9019(6) 0.18508(10) 0.6162(3) 0.0902(9) Uani 1 1 d . . . . .
H14 H 1.0433 0.1731 0.6484 0.108 Uiso 1 1 calc R U . . .
C15 C 0.7181(8) 0.15910(11) 0.5801(3) 0.0965(11) Uani 1 1 d . . . . .
H15 H 0.7330 0.1295 0.5877 0.116 Uiso 1 1 calc R U . . .
C16 C 0.5130(7) 0.17694(12) 0.5327(3) 0.0949(11) Uani 1 1 d . . . . .
H16 H 0.3873 0.1592 0.5080 0.114 Uiso 1 1 calc R U . . .
C17 C 0.4873(5) 0.22126(10) 0.5204(3) 0.0743(7) Uani 1 1 d . . . . .
H17 H 0.3452 0.2328 0.4878 0.089 Uiso 1 1 calc R U . . .
N2 N 0.3562(3) 0.54151(8) 0.25526(18) 0.0611(5) Uani 1 1 d . . . . .
C18 C 0.5972(3) 0.53582(7) 0.31599(17) 0.0465(4) Uani 1 1 d . . . . .
C19 C 0.7506(5) 0.56257(8) 0.2574(2) 0.0624(6) Uani 1 1 d . . . . .
H19A H 0.7138 0.5568 0.1754 0.094 Uiso 1 1 calc R U . . .
H19B H 0.9063 0.5552 0.2899 0.094 Uiso 1 1 calc R U . . .
H19C H 0.7278 0.5925 0.2701 0.094 Uiso 1 1 calc R U . . .
C20 C 0.6471(3) 0.48644(6) 0.31437(17) 0.0451(4) Uani 1 1 d . . . . .
H20 H 0.5404 0.4725 0.3534 0.054 Uiso 1 1 calc R U . . .
C21 C 0.8852(4) 0.47388(7) 0.38364(19) 0.0535(5) Uani 1 1 d . . . . .
H21A H 0.9967 0.4850 0.3443 0.064 Uiso 1 1 calc R U . . .
H21B H 0.9133 0.4870 0.4600 0.064 Uiso 1 1 calc R U . . .
C22 C 0.9148(6) 0.42556(9) 0.3975(3) 0.0803(8) Uani 1 1 d . . . . .
H22A H 0.8926 0.4125 0.3222 0.120 Uiso 1 1 calc R U . . .
H22B H 0.8053 0.4144 0.4368 0.120 Uiso 1 1 calc R U . . .
H22C H 1.0650 0.4193 0.4423 0.120 Uiso 1 1 calc R U . . .
C23 C 0.5982(4) 0.46796(6) 0.19188(17) 0.0469(5) Uani 1 1 d . . . . .
C24 C 0.4001(4) 0.44489(8) 0.1478(2) 0.0587(6) Uani 1 1 d . . . . .
H24 H 0.2962 0.4410 0.1936 0.070 Uiso 1 1 calc R U . . .
C25 C 0.3552(5) 0.42770(9) 0.0369(2) 0.0716(7) Uani 1 1 d . . . . .
H25 H 0.2224 0.4122 0.0090 0.086 Uiso 1 1 calc R U . . .
C26 C 0.5068(5) 0.43343(9) -0.0326(2) 0.0704(7) Uani 1 1 d . . . . .
H26 H 0.4757 0.4222 -0.1075 0.084 Uiso 1 1 calc R U . . .
C27 C 0.7028(5) 0.45574(8) 0.0094(2) 0.0668(7) Uani 1 1 d . . . . .
H27 H 0.8056 0.4595 -0.0371 0.080 Uiso 1 1 calc R U . . .
C28 C 0.7498(4) 0.47279(8) 0.1205(2) 0.0563(5) Uani 1 1 d . . . . .
H28 H 0.8846 0.4877 0.1479 0.068 Uiso 1 1 calc R U . . .
C29 C 0.6199(3) 0.54993(6) 0.44234(18) 0.0445(4) Uani 1 1 d . . . . .
C30 C 0.8154(4) 0.56911(8) 0.5077(2) 0.0568(5) Uani 1 1 d . . . . .
H30 H 0.9366 0.5743 0.4738 0.068 Uiso 1 1 calc R U . . .
C31 C 0.8327(5) 0.58058(8) 0.6228(2) 0.0668(7) Uani 1 1 d . . . . .
H31 H 0.9665 0.5926 0.6659 0.080 Uiso 1 1 calc R U . . .
C32 C 0.6547(5) 0.57426(8) 0.6733(2) 0.0660(7) Uani 1 1 d . . . . .
H32 H 0.6650 0.5829 0.7496 0.079 Uiso 1 1 calc R U . . .
C33 C 0.4606(5) 0.55517(8) 0.6107(2) 0.0620(6) Uani 1 1 d . . . . .
H33 H 0.3397 0.5504 0.6451 0.074 Uiso 1 1 calc R U . . .
C34 C 0.4437(4) 0.54295(7) 0.49691(19) 0.0515(5) Uani 1 1 d . . . . .
H34 H 0.3114 0.5298 0.4559 0.062 Uiso 1 1 calc R U . . .
N3 N -0.1423(4) 0.68733(8) 0.7885(2) 0.0647(5) Uani 1 1 d . . . . .
C35 C 0.0953(4) 0.70267(7) 0.8246(2) 0.0521(5) Uani 1 1 d . . . . .
C36 C 0.2266(5) 0.69015(9) 0.7344(2) 0.0670(6) Uani 1 1 d . . . . .
H36A H 0.2171 0.6597 0.7224 0.101 Uiso 1 1 calc R U . . .
H36B H 0.3827 0.6984 0.7616 0.101 Uiso 1 1 calc R U . . .
H36C H 0.1627 0.7045 0.6624 0.101 Uiso 1 1 calc R U . . .
C37 C 0.2009(4) 0.68241(7) 0.94661(19) 0.0524(5) Uani 1 1 d . . . . .
H37 H 0.1062 0.6922 0.9982 0.063 Uiso 1 1 calc R U . . .
C38 C 0.4414(4) 0.69841(8) 1.0011(2) 0.0637(6) Uani 1 1 d . . . . .
H38A H 0.5441 0.6873 0.9563 0.076 Uiso 1 1 calc R U . . .
H38B H 0.4435 0.7295 0.9962 0.076 Uiso 1 1 calc R U . . .
C39 C 0.5266(7) 0.68521(13) 1.1265(3) 0.1022(11) Uani 1 1 d . . . . .
H39A H 0.5366 0.6545 1.1314 0.153 Uiso 1 1 calc R U . . .
H39B H 0.4235 0.6953 1.1710 0.153 Uiso 1 1 calc R U . . .
H39C H 0.6740 0.6974 1.1568 0.153 Uiso 1 1 calc R U . . .
C40 C 0.1870(4) 0.63358(7) 0.94585(18) 0.0492(5) Uani 1 1 d . . . . .
C41 C 0.3453(4) 0.60773(8) 0.9104(2) 0.0584(5) Uani 1 1 d . . . . .
H41 H 0.4655 0.6205 0.8866 0.070 Uiso 1 1 calc R U . . .
C42 C 0.3277(5) 0.56347(8) 0.9098(2) 0.0636(6) Uani 1 1 d . . . . .
H42 H 0.4369 0.5468 0.8868 0.076 Uiso 1 1 calc R U . . .
C43 C 0.1493(5) 0.54389(8) 0.9432(2) 0.0652(6) Uani 1 1 d . . . . .
H43 H 0.1358 0.5141 0.9412 0.078 Uiso 1 1 calc R U . . .
C44 C -0.0078(5) 0.56860(9) 0.9792(2) 0.0651(6) Uani 1 1 d . . . . .
H44 H -0.1285 0.5556 1.0019 0.078 Uiso 1 1 calc R U . . .
C45 C 0.0120(4) 0.61298(8) 0.9821(2) 0.0573(5) Uani 1 1 d . . . . .
H45 H -0.0939 0.6293 1.0087 0.069 Uiso 1 1 calc R U . . .
C46 C 0.0843(4) 0.75154(8) 0.8385(2) 0.0547(5) Uani 1 1 d . . . . .
C47 C -0.0797(5) 0.76977(9) 0.8874(3) 0.0705(7) Uani 1 1 d . . . . .
H47 H -0.1833 0.7520 0.9113 0.085 Uiso 1 1 calc R U . . .
C48 C -0.0938(6) 0.81353(10) 0.9018(3) 0.0856(9) Uani 1 1 d . . . . .
H48 H -0.2068 0.8249 0.9341 0.103 Uiso 1 1 calc R U . . .
C49 C 0.0599(6) 0.84038(10) 0.8681(3) 0.0844(9) Uani 1 1 d . . . . .
H49 H 0.0510 0.8699 0.8774 0.101 Uiso 1 1 calc R U . . .
C50 C 0.2241(6) 0.82333(10) 0.8214(3) 0.0826(8) Uani 1 1 d . . . . .
H50 H 0.3285 0.8413 0.7989 0.099 Uiso 1 1 calc R U . . .
C51 C 0.2379(5) 0.77935(9) 0.8068(2) 0.0694(7) Uani 1 1 d . . . . .
H51 H 0.3525 0.7683 0.7751 0.083 Uiso 1 1 calc R U . . .
H1A H 0.871(5) 0.3406(12) 0.511(3) 0.082(9) Uiso 1 1 d . . . . .
H2D H 0.340(5) 0.5331(10) 0.179(3) 0.076(8) Uiso 1 1 d . . . . .
H1B H 0.866(5) 0.3002(11) 0.445(3) 0.088(10) Uiso 1 1 d . . . . .
H3A H -0.131(6) 0.6571(12) 0.770(3) 0.093(10) Uiso 1 1 d . . . . .
H3B H -0.214(7) 0.7019(13) 0.713(4) 0.119(13) Uiso 1 1 d . . . . .
H2E H 0.325(6) 0.5705(12) 0.251(3) 0.089(10) 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 0.0181 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'
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 H1A 113(2) . . ?
C1 N1 H1B 108(2) . . ?
H1A N1 H1B 111(3) . . ?
N1 C1 C2 110.4(2) . . ?
N1 C1 C12 106.61(19) . . ?
C2 C1 C12 112.3(2) . . ?
N1 C1 C3 107.18(19) . . ?
C2 C1 C3 112.13(19) . . ?
C12 C1 C3 107.93(18) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C6 C3 C4 112.24(18) . . ?
C6 C3 C1 112.45(18) . . ?
C4 C3 C1 113.25(18) . . ?
C6 C3 H3 106.1 . . ?
C4 C3 H3 106.1 . . ?
C1 C3 H3 106.1 . . ?
C5 C4 C3 113.6(2) . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C11 117.3(2) . . ?
C7 C6 C3 122.6(2) . . ?
C11 C6 C3 120.1(2) . . ?
C8 C7 C6 121.1(2) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 119.1(2) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C6 121.3(2) . . ?
C10 C11 H11 119.3 . . ?
C6 C11 H11 119.3 . . ?
C13 C12 C17 117.2(3) . . ?
C13 C12 C1 119.9(2) . . ?
C17 C12 C1 122.9(2) . . ?
C14 C13 C12 121.8(3) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 119.3(3) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 121.2(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C12 C17 C16 120.3(3) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C18 N2 H2D 107.7(19) . . ?
C18 N2 H2E 108(2) . . ?
H2D N2 H2E 105(3) . . ?
N2 C18 C19 110.51(19) . . ?
N2 C18 C29 106.95(17) . . ?
C19 C18 C29 111.13(19) . . ?
N2 C18 C20 106.43(18) . . ?
C19 C18 C20 112.89(17) . . ?
C29 C18 C20 108.64(15) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C23 C20 C21 111.16(17) . . ?
C23 C20 C18 112.78(16) . . ?
C21 C20 C18 113.79(16) . . ?
C23 C20 H20 106.1 . . ?
C21 C20 H20 106.1 . . ?
C18 C20 H20 106.1 . . ?
C22 C21 C20 112.5(2) . . ?
C22 C21 H21A 109.1 . . ?
C20 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
C20 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C28 117.5(2) . . ?
C24 C23 C20 120.68(19) . . ?
C28 C23 C20 121.80(19) . . ?
C25 C24 C23 121.0(2) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C26 C25 C24 120.3(3) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C27 C26 C25 119.5(2) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C26 C27 C28 120.6(2) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C27 C28 C23 121.0(2) . . ?
C27 C28 H28 119.5 . . ?
C23 C28 H28 119.5 . . ?
C30 C29 C34 117.2(2) . . ?
C30 C29 C18 122.38(19) . . ?
C34 C29 C18 120.36(19) . . ?
C31 C30 C29 121.0(2) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
C32 C31 C30 120.4(2) . . ?
C32 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C31 C32 C33 119.6(2) . . ?
C31 C32 H32 120.2 . . ?
C33 C32 H32 120.2 . . ?
C32 C33 C34 120.3(2) . . ?
C32 C33 H33 119.8 . . ?
C34 C33 H33 119.8 . . ?
C33 C34 C29 121.4(2) . . ?
C33 C34 H34 119.3 . . ?
C29 C34 H34 119.3 . . ?
C35 N3 H3A 105(2) . . ?
C35 N3 H3B 107(2) . . ?
H3A N3 H3B 106(3) . . ?
N3 C35 C36 110.4(2) . . ?
N3 C35 C46 106.67(19) . . ?
C36 C35 C46 111.85(19) . . ?
N3 C35 C37 107.14(18) . . ?
C36 C35 C37 111.98(19) . . ?
C46 C35 C37 108.58(18) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C40 C37 C38 111.92(19) . . ?
C40 C37 C35 112.71(18) . . ?
C38 C37 C35 113.50(19) . . ?
C40 C37 H37 106.0 . . ?
C38 C37 H37 106.0 . . ?
C35 C37 H37 106.0 . . ?
C39 C38 C37 113.4(3) . . ?
C39 C38 H38A 108.9 . . ?
C37 C38 H38A 108.9 . . ?
C39 C38 H38B 108.9 . . ?
C37 C38 H38B 108.9 . . ?
H38A C38 H38B 107.7 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C45 C40 C41 117.1(2) . . ?
C45 C40 C37 120.3(2) . . ?
C41 C40 C37 122.6(2) . . ?
C42 C41 C40 121.4(2) . . ?
C42 C41 H41 119.3 . . ?
C40 C41 H41 119.3 . . ?
C43 C42 C41 120.3(2) . . ?
C43 C42 H42 119.8 . . ?
C41 C42 H42 119.8 . . ?
C44 C43 C42 119.4(2) . . ?
C44 C43 H43 120.3 . . ?
C42 C43 H43 120.3 . . ?
C43 C44 C45 120.4(2) . . ?
C43 C44 H44 119.8 . . ?
C45 C44 H44 119.8 . . ?
C44 C45 C40 121.3(2) . . ?
C44 C45 H45 119.3 . . ?
C40 C45 H45 119.3 . . ?
C47 C46 C51 116.8(2) . . ?
C47 C46 C35 120.4(2) . . ?
C51 C46 C35 122.8(2) . . ?
C48 C47 C46 121.9(3) . . ?
C48 C47 H47 119.1 . . ?
C46 C47 H47 119.1 . . ?
C47 C48 C49 119.9(3) . . ?
C47 C48 H48 120.0 . . ?
C49 C48 H48 120.0 . . ?
C50 C49 C48 119.4(3) . . ?
C50 C49 H49 120.3 . . ?
C48 C49 H49 120.3 . . ?
C49 C50 C51 120.7(3) . . ?
C49 C50 H50 119.7 . . ?
C51 C50 H50 119.7 . . ?
C50 C51 C46 121.3(3) . . ?
C50 C51 H51 119.3 . . ?
C46 C51 H51 119.3 . . ?
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
N1 C1 1.476(3) . ?
N1 H1A 0.89(4) . ?
N1 H1B 0.91(4) . ?
C1 C2 1.533(3) . ?
C1 C12 1.535(3) . ?
C1 C3 1.570(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C6 1.523(3) . ?
C3 C4 1.530(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.509(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.390(3) . ?
C6 C11 1.391(3) . ?
C7 C8 1.380(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.373(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.374(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.383(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.383(4) . ?
C12 C17 1.386(3) . ?
C13 C14 1.382(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.363(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.357(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.393(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
N2 C18 1.480(3) . ?
N2 H2D 0.92(3) . ?
N2 H2E 0.92(4) . ?
C18 C19 1.530(3) . ?
C18 C29 1.533(3) . ?
C18 C20 1.568(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C23 1.522(3) . ?
C20 C21 1.534(3) . ?
C20 H20 0.9800 . ?
C21 C22 1.520(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.392(3) . ?
C23 C28 1.395(3) . ?
C24 C25 1.384(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.381(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.366(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.384(3) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 C30 1.389(3) . ?
C29 C34 1.389(3) . ?
C30 C31 1.388(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.365(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.370(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.379(3) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
N3 C35 1.482(3) . ?
N3 H3A 0.97(4) . ?
N3 H3B 1.01(4) . ?
C35 C36 1.523(3) . ?
C35 C46 1.534(3) . ?
C35 C37 1.568(3) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 C40 1.523(3) . ?
C37 C38 1.533(3) . ?
C37 H37 0.9800 . ?
C38 C39 1.509(4) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 C45 1.391(3) . ?
C40 C41 1.391(3) . ?
C41 C42 1.382(3) . ?
C41 H41 0.9300 . ?
C42 C43 1.378(4) . ?
C42 H42 0.9300 . ?
C43 C44 1.368(4) . ?
C43 H43 0.9300 . ?
C44 C45 1.387(4) . ?
C44 H44 0.9300 . ?
C45 H45 0.9300 . ?
C46 C47 1.385(4) . ?
C46 C51 1.386(3) . ?
C47 C48 1.379(4) . ?
C47 H47 0.9300 . ?
C48 C49 1.379(5) . ?
C48 H48 0.9300 . ?
C49 C50 1.356(5) . ?
C49 H49 0.9300 . ?
C50 C51 1.386(4) . ?
C50 H50 0.9300 . ?
C51 H51 0.9300 . ?
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
N1 C1 C3 C6 55.2(2) . . . . ?
C2 C1 C3 C6 -66.1(3) . . . . ?
C12 C1 C3 C6 169.64(18) . . . . ?
N1 C1 C3 C4 -176.30(19) . . . . ?
C2 C1 C3 C4 62.4(3) . . . . ?
C12 C1 C3 C4 -61.8(2) . . . . ?
C6 C3 C4 C5 -61.7(3) . . . . ?
C1 C3 C4 C5 169.6(2) . . . . ?
C4 C3 C6 C7 -48.2(3) . . . . ?
C1 C3 C6 C7 80.9(3) . . . . ?
C4 C3 C6 C11 131.7(2) . . . . ?
C1 C3 C6 C11 -99.2(2) . . . . ?
C11 C6 C7 C8 1.5(4) . . . . ?
C3 C6 C7 C8 -178.6(2) . . . . ?
C6 C7 C8 C9 -0.9(4) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
C9 C10 C11 C6 0.4(4) . . . . ?
C7 C6 C11 C10 -1.2(4) . . . . ?
C3 C6 C11 C10 178.8(2) . . . . ?
N1 C1 C12 C13 39.6(3) . . . . ?
C2 C1 C12 C13 160.6(2) . . . . ?
C3 C1 C12 C13 -75.2(3) . . . . ?
N1 C1 C12 C17 -142.0(2) . . . . ?
C2 C1 C12 C17 -21.0(3) . . . . ?
C3 C1 C12 C17 103.1(2) . . . . ?
C17 C12 C13 C14 1.0(4) . . . . ?
C1 C12 C13 C14 179.5(3) . . . . ?
C12 C13 C14 C15 -0.8(5) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
C14 C15 C16 C17 0.1(5) . . . . ?
C13 C12 C17 C16 -0.6(4) . . . . ?
C1 C12 C17 C16 -179.0(3) . . . . ?
C15 C16 C17 C12 0.1(5) . . . . ?
N2 C18 C20 C23 57.4(2) . . . . ?
C19 C18 C20 C23 -64.0(2) . . . . ?
C29 C18 C20 C23 172.28(17) . . . . ?
N2 C18 C20 C21 -174.76(17) . . . . ?
C19 C18 C20 C21 63.8(2) . . . . ?
C29 C18 C20 C21 -59.9(2) . . . . ?
C23 C20 C21 C22 -61.0(3) . . . . ?
C18 C20 C21 C22 170.4(2) . . . . ?
C21 C20 C23 C24 129.1(2) . . . . ?
C18 C20 C23 C24 -101.7(2) . . . . ?
C21 C20 C23 C28 -49.9(3) . . . . ?
C18 C20 C23 C28 79.3(2) . . . . ?
C28 C23 C24 C25 -0.4(4) . . . . ?
C20 C23 C24 C25 -179.5(2) . . . . ?
C23 C24 C25 C26 -0.4(4) . . . . ?
C24 C25 C26 C27 0.8(4) . . . . ?
C25 C26 C27 C28 -0.3(4) . . . . ?
C26 C27 C28 C23 -0.5(4) . . . . ?
C24 C23 C28 C27 0.9(3) . . . . ?
C20 C23 C28 C27 179.9(2) . . . . ?
N2 C18 C29 C30 -147.2(2) . . . . ?
C19 C18 C29 C30 -26.5(3) . . . . ?
C20 C18 C29 C30 98.3(2) . . . . ?
N2 C18 C29 C34 34.2(3) . . . . ?
C19 C18 C29 C34 154.9(2) . . . . ?
C20 C18 C29 C34 -80.3(2) . . . . ?
C34 C29 C30 C31 0.2(3) . . . . ?
C18 C29 C30 C31 -178.4(2) . . . . ?
C29 C30 C31 C32 -1.8(4) . . . . ?
C30 C31 C32 C33 2.2(4) . . . . ?
C31 C32 C33 C34 -0.9(4) . . . . ?
C32 C33 C34 C29 -0.7(4) . . . . ?
C30 C29 C34 C33 1.0(3) . . . . ?
C18 C29 C34 C33 179.7(2) . . . . ?
N3 C35 C37 C40 56.5(2) . . . . ?
C36 C35 C37 C40 -64.6(2) . . . . ?
C46 C35 C37 C40 171.39(18) . . . . ?
N3 C35 C37 C38 -174.9(2) . . . . ?
C36 C35 C37 C38 63.9(3) . . . . ?
C46 C35 C37 C38 -60.1(2) . . . . ?
C40 C37 C38 C39 -61.3(3) . . . . ?
C35 C37 C38 C39 169.7(2) . . . . ?
C38 C37 C40 C45 133.5(2) . . . . ?
C35 C37 C40 C45 -97.1(2) . . . . ?
C38 C37 C40 C41 -46.1(3) . . . . ?
C35 C37 C40 C41 83.3(3) . . . . ?
C45 C40 C41 C42 0.8(3) . . . . ?
C37 C40 C41 C42 -179.6(2) . . . . ?
C40 C41 C42 C43 0.9(4) . . . . ?
C41 C42 C43 C44 -1.4(4) . . . . ?
C42 C43 C44 C45 0.1(4) . . . . ?
C43 C44 C45 C40 1.7(4) . . . . ?
C41 C40 C45 C44 -2.1(3) . . . . ?
C37 C40 C45 C44 178.2(2) . . . . ?
N3 C35 C46 C47 39.5(3) . . . . ?
C36 C35 C46 C47 160.3(2) . . . . ?
C37 C35 C46 C47 -75.6(3) . . . . ?
N3 C35 C46 C51 -142.3(2) . . . . ?
C36 C35 C46 C51 -21.5(3) . . . . ?
C37 C35 C46 C51 102.5(3) . . . . ?
C51 C46 C47 C48 1.4(4) . . . . ?
C35 C46 C47 C48 179.7(3) . . . . ?
C46 C47 C48 C49 -0.7(5) . . . . ?
C47 C48 C49 C50 -0.2(5) . . . . ?
C48 C49 C50 C51 0.3(5) . . . . ?
C49 C50 C51 C46 0.5(5) . . . . ?
C47 C46 C51 C50 -1.3(4) . . . . ?
C35 C46 C51 C50 -179.5(3) . . . . ?
