#------------------------------------------------------------------------------
#$Date: 2022-05-19 00:56:21 +0300 (Thu, 19 May 2022) $
#$Revision: 275522 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/01/7130113.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_7130113
loop_
_publ_author_name
'Puerta Lombardi, Braulio M.'
'Pezoulas, Ethan R.'
'Suvinen, Roope A.'
'Harrison, Alexander'
'Dubrawski, Zachary S.'
'Gelfand, Benjamin S.'
'Tuononen, Heikki M.'
'Roesler, Roland'
_publ_section_title
;
 Bis[cyclic (alkyl)(amino)carbene] isomers: Stable trans-bis(CAAC) versus
 facile olefin formation for cis-bis(CAAC)
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01476A
_journal_year                    2022
_chemical_formula_moiety         '2(C44 H64 N4), C2 H3 N'
_chemical_formula_sum            'C90 H131 N9'
_chemical_formula_weight         1339.03
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-12-27 deposited with the CCDC.	2022-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                96.8960(10)
_cell_angle_beta                 101.8520(10)
_cell_angle_gamma                100.5620(10)
_cell_formula_units_Z            1
_cell_length_a                   10.1013(11)
_cell_length_b                   14.1448(16)
_cell_length_c                   14.8032(17)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      28.290
_cell_measurement_theta_min      2.253
_cell_volume                     2007.4(4)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 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      173.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0411
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31614
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.339
_diffrn_reflns_theta_min         1.425
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0430 before and 0.0348 after correction.
The Ratio of minimum to maximum transmission is 0.9619.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.108
_exptl_crystal_description       needle
_exptl_crystal_F_000             734
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         9983
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0493
_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)+(0.0540P)²+0.3127P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1237
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6898
_reflns_number_total             9983
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc01476a2.cif
_cod_data_source_block           cisdicaach2(ch2cn)2
_cod_database_code               7130113
_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.
;
_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. Others
 Fixed Sof: C1S(0.5) C2S(0.5) H2SA(0.5) H2SB(0.5) H2SC(0.5) N1S(0.5)
3.a Ternary CH refined with riding coordinates:
 C24(H24), C12(H12), C7(H7), C27(H27), C39(H39), C36(H36)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C2(H2A,H2B), C8(H8A,H8B), C6(H6A,H6B), C41(H41A,
 H41B), C13(H13A,H13B), C43(H43A,H43B)
3.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C21(H21), C33(H33), C31(H31), C32(H32)
3.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C10(H10A,H10B,H10C), C15(H15A,H15B,
 H15C), C28(H28A,H28B,H28C), C11(H11A,H11B,H11C), C26(H26A,H26B,H26C), C16(H16A,
 H16B,H16C), C40(H40A,H40B,H40C), C38(H38A,H38B,H38C), C37(H37A,H37B,H37C),
 C35(H35A,H35B,H35C), C2S(H2SA,H2SB,H2SC)
;
_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
N1 N 0.10283(11) 0.76431(7) 0.43125(7) 0.0177(2) Uani 1 1 d . . . . .
N2 N 0.61019(11) 0.64969(8) 0.82346(7) 0.0196(2) Uani 1 1 d . . . . .
N3 N 0.36289(15) 0.92649(10) 0.74017(9) 0.0385(3) Uani 1 1 d . . . . .
C17 C 0.05963(13) 0.83224(9) 0.37319(9) 0.0168(3) Uani 1 1 d . . . . .
C18 C -0.07047(13) 0.85604(9) 0.37112(9) 0.0177(3) Uani 1 1 d . . . . .
C19 C -0.11376(14) 0.92011(10) 0.31246(9) 0.0220(3) Uani 1 1 d . . . . .
H19 H -0.202591 0.934672 0.309282 0.026 Uiso 1 1 calc R U . . .
C22 C 0.14598(13) 0.87616(10) 0.31854(9) 0.0197(3) Uani 1 1 d . . . . .
C1 C 0.28561(13) 0.70912(9) 0.53086(9) 0.0184(3) Uani 1 1 d . . . . .
C4 C 0.50668(13) 0.62958(9) 0.65917(9) 0.0183(3) Uani 1 1 d . . . . .
C24 C -0.16600(13) 0.81448(10) 0.43054(9) 0.0210(3) Uani 1 1 d . . . . .
H24 H -0.116962 0.773535 0.470645 0.025 Uiso 1 1 calc R U . . .
C12 C 0.56499(13) 0.70566(9) 0.75078(9) 0.0182(3) Uani 1 1 d . . . . .
H12 H 0.487186 0.734117 0.766254 0.022 Uiso 1 1 calc R U . . .
C29 C 0.61392(14) 0.68679(10) 0.91953(9) 0.0217(3) Uani 1 1 d . . . . .
C42 C 0.27487(15) 0.89039(10) 0.67728(10) 0.0251(3) Uani 1 1 d . . . . .
C3 C 0.34904(13) 0.58940(9) 0.64068(9) 0.0203(3) Uani 1 1 d . . . . .
H3A H 0.321507 0.534505 0.587716 0.024 Uiso 1 1 calc R U . . .
H3B H 0.328152 0.563420 0.696556 0.024 Uiso 1 1 calc R U . . .
C20 C -0.03024(15) 0.96291(10) 0.25885(10) 0.0255(3) Uani 1 1 d . . . . .
H20 H -0.061306 1.006706 0.219605 0.031 Uiso 1 1 calc R U . . .
C5 C 0.52838(14) 0.66838(10) 0.56926(9) 0.0210(3) Uani 1 1 d . . . . .
H5A H 0.627750 0.697836 0.577534 0.025 Uiso 1 1 calc R U . . .
H5B H 0.502902 0.613031 0.516811 0.025 Uiso 1 1 calc R U . . .
C7 C 0.21528(13) 0.79763(9) 0.51393(9) 0.0185(3) Uani 1 1 d . . . . .
H7 H 0.284761 0.849959 0.499141 0.022 Uiso 1 1 calc R U . . .
C2 C 0.26211(13) 0.66508(9) 0.61821(9) 0.0195(3) Uani 1 1 d . . . . .
H2A H 0.285281 0.718175 0.672599 0.023 Uiso 1 1 calc R U . . .
H2B H 0.162905 0.634088 0.608014 0.023 Uiso 1 1 calc R U . . .
C21 C 0.09875(15) 0.94155(10) 0.26273(10) 0.0249(3) Uani 1 1 d . . . . .
H21 H 0.156512 0.972019 0.226650 0.030 Uiso 1 1 calc R U . . .
C8 C 0.21894(14) 0.63510(10) 0.43960(9) 0.0223(3) Uani 1 1 d . . . . .
H8A H 0.279305 0.641193 0.394778 0.027 Uiso 1 1 calc R U . . .
H8B H 0.205855 0.567682 0.453391 0.027 Uiso 1 1 calc R U . . .
C9 C 0.07848(14) 0.65825(10) 0.39800(10) 0.0223(3) Uani 1 1 d . . . . .
C6 C 0.44314(13) 0.74436(10) 0.54376(9) 0.0201(3) Uani 1 1 d . . . . .
H6A H 0.460964 0.764982 0.485004 0.024 Uiso 1 1 calc R U . . .
H6B H 0.475677 0.802343 0.593531 0.024 Uiso 1 1 calc R U . . .
C34 C 0.48938(15) 0.68713(11) 0.94978(10) 0.0258(3) Uani 1 1 d . . . . .
C41 C 0.16222(14) 0.84286(10) 0.59632(9) 0.0234(3) Uani 1 1 d . . . . .
H41A H 0.108690 0.891369 0.575058 0.028 Uiso 1 1 calc R U . . .
H41B H 0.098931 0.791028 0.615535 0.028 Uiso 1 1 calc R U . . .
C13 C 0.58580(15) 0.54851(10) 0.68051(9) 0.0241(3) Uani 1 1 d . . . . .
H13A H 0.674493 0.561132 0.660854 0.029 Uiso 1 1 calc R U . . .
H13B H 0.530104 0.484577 0.645958 0.029 Uiso 1 1 calc R U . . .
C27 C 0.28915(14) 0.85677(11) 0.31947(9) 0.0244(3) Uani 1 1 d . . . . .
H27 H 0.301897 0.803211 0.356637 0.029 Uiso 1 1 calc R U . . .
C14 C 0.61344(15) 0.54770(10) 0.78716(9) 0.0241(3) Uani 1 1 d . . . . .
C23 C -0.19976(16) 0.89526(11) 0.49543(10) 0.0302(3) Uani 1 1 d . . . . .
H23A H -0.113555 0.935779 0.535369 0.045 Uiso 1 1 calc R U . . .
H23B H -0.257653 0.865810 0.534630 0.045 Uiso 1 1 calc R U . . .
H23C H -0.249604 0.935747 0.457704 0.045 Uiso 1 1 calc R U . . .
C25 C -0.29964(14) 0.74896(11) 0.36934(10) 0.0279(3) Uani 1 1 d . . . . .
H25A H -0.355885 0.788974 0.335693 0.042 Uiso 1 1 calc R U . . .
H25B H -0.351784 0.714374 0.408881 0.042 Uiso 1 1 calc R U . . .
H25C H -0.276894 0.701566 0.324216 0.042 Uiso 1 1 calc R U . . .
C30 C 0.74174(15) 0.72874(11) 0.98342(10) 0.0287(3) Uani 1 1 d . . . . .
C39 C 0.34596(15) 0.64816(11) 0.88677(10) 0.0289(3) Uani 1 1 d . . . . .
H39 H 0.357404 0.621121 0.823924 0.035 Uiso 1 1 calc R U . . .
N4 N 0.90066(16) 0.73785(14) 0.70367(11) 0.0558(5) Uani 1 1 d . . . . .
C43 C 0.68511(15) 0.79072(11) 0.74873(10) 0.0280(3) Uani 1 1 d . . . . .
H43A H 0.649342 0.831105 0.703162 0.034 Uiso 1 1 calc R U . . .
H43B H 0.714934 0.832241 0.811157 0.034 Uiso 1 1 calc R U . . .
C10 C 0.03905(17) 0.63336(11) 0.29144(10) 0.0324(4) Uani 1 1 d . . . . .
H10A H -0.047256 0.653863 0.267466 0.049 Uiso 1 1 calc R U . . .
H10B H 0.026057 0.562851 0.272489 0.049 Uiso 1 1 calc R U . . .
H10C H 0.113026 0.667392 0.265931 0.049 Uiso 1 1 calc R U . . .
C44 C 0.80659(16) 0.76102(13) 0.72416(11) 0.0359(4) Uani 1 1 d . . . . .
C33 C 0.49629(17) 0.72773(13) 1.04151(10) 0.0362(4) Uani 1 1 d . . . . .
H33 H 0.412861 0.728171 1.061556 0.043 Uiso 1 1 calc R U . . .
C15 C 0.50680(17) 0.47194(11) 0.81485(11) 0.0331(4) Uani 1 1 d . . . . .
H15A H 0.521262 0.481690 0.883132 0.050 Uiso 1 1 calc R U . . .
H15B H 0.517513 0.406352 0.792415 0.050 Uiso 1 1 calc R U . . .
H15C H 0.413303 0.479259 0.786760 0.050 Uiso 1 1 calc R U . . .
C28 C 0.40121(15) 0.94709(12) 0.36774(11) 0.0347(4) Uani 1 1 d . . . . .
H28A H 0.395565 0.999251 0.330031 0.052 Uiso 1 1 calc R U . . .
H28B H 0.492613 0.930900 0.374309 0.052 Uiso 1 1 calc R U . . .
H28C H 0.387199 0.968956 0.429780 0.052 Uiso 1 1 calc R U . . .
C11 C -0.03873(15) 0.60177(11) 0.43521(12) 0.0326(4) Uani 1 1 d . . . . .
H11A H -0.022103 0.623000 0.502824 0.049 Uiso 1 1 calc R U . . .
H11B H -0.041184 0.531782 0.422533 0.049 Uiso 1 1 calc R U . . .
H11C H -0.127515 0.614585 0.403969 0.049 Uiso 1 1 calc R U . . .
C26 C 0.30950(17) 0.82418(14) 0.22142(11) 0.0410(4) Uani 1 1 d . . . . .
H26A H 0.237445 0.766641 0.190159 0.062 Uiso 1 1 calc R U . . .
H26B H 0.400780 0.808002 0.226822 0.062 Uiso 1 1 calc R U . . .
H26C H 0.303264 0.877100 0.184719 0.062 Uiso 1 1 calc R U . . .
C36 C 0.88270(15) 0.73769(13) 0.95971(11) 0.0349(4) Uani 1 1 d . . . . .
H36 H 0.868144 0.707405 0.892847 0.042 Uiso 1 1 calc R U . . .
C16 C 0.75479(17) 0.52321(13) 0.82150(11) 0.0361(4) Uani 1 1 d . . . . .
H16A H 0.826334 0.569142 0.803742 0.054 Uiso 1 1 calc R U . . .
H16B H 0.753268 0.456681 0.792991 0.054 Uiso 1 1 calc R U . . .
H16C H 0.775287 0.528111 0.889748 0.054 Uiso 1 1 calc R U . . .
C31 C 0.74174(17) 0.76685(14) 1.07500(11) 0.0413(4) Uani 1 1 d . . . . .
H31 H 0.827707 0.793265 1.118541 0.050 Uiso 1 1 calc R U . . .
C32 C 0.62101(18) 0.76719(14) 1.10380(11) 0.0442(4) Uani 1 1 d . . . . .
H32 H 0.623607 0.794431 1.166168 0.053 Uiso 1 1 calc R U . . .
C40 C 0.26265(17) 0.56511(13) 0.92354(12) 0.0429(4) Uani 1 1 d . . . . .
H40A H 0.314026 0.512941 0.930147 0.064 Uiso 1 1 calc R U . . .
H40B H 0.172899 0.539421 0.879346 0.064 Uiso 1 1 calc R U . . .
H40C H 0.247913 0.590040 0.984558 0.064 Uiso 1 1 calc R U . . .
C38 C 0.26612(17) 0.72988(14) 0.87383(12) 0.0407(4) Uani 1 1 d . . . . .
H38A H 0.250577 0.756235 0.934160 0.061 Uiso 1 1 calc R U . . .
H38B H 0.176773 0.703726 0.829318 0.061 Uiso 1 1 calc R U . . .
H38C H 0.320037 0.781872 0.849744 0.061 Uiso 1 1 calc R U . . .
C37 C 0.97412(18) 0.68282(17) 1.02096(13) 0.0523(5) Uani 1 1 d . . . . .
H37A H 0.993674 0.713574 1.086593 0.078 Uiso 1 1 calc R U . . .
H37B H 1.061313 0.685154 1.001167 0.078 Uiso 1 1 calc R U . . .
H37C H 0.925615 0.614762 1.014153 0.078 Uiso 1 1 calc R U . . .
C35 C 0.95756(19) 0.84434(15) 0.97111(13) 0.0509(5) Uani 1 1 d . . . . .
H35A H 0.896732 0.880207 0.935340 0.076 Uiso 1 1 calc R U . . .
H35B H 1.042133 0.847611 0.947875 0.076 Uiso 1 1 calc R U . . .
H35C H 0.981711 0.873470 1.037418 0.076 Uiso 1 1 calc R U . . .
C1S C 0.3931(6) 1.0102(3) 1.0414(3) 0.0636(12) Uani 0.5 1 d . . P A -1
C2S C 0.503(4) 0.997(3) 0.997(3) 0.086(3) Uani 0.5 1 d . . P A -1
H2SA H 0.466513 0.980195 0.928716 0.129 Uiso 0.5 1 calc R U P A -1
H2SB H 0.543936 0.943751 1.019370 0.129 Uiso 0.5 1 calc R U P A -1
H2SC H 0.574596 1.057074 1.011097 0.129 Uiso 0.5 1 calc R U P A -1
N1S N 0.3050(5) 1.0160(3) 1.0767(3) 0.0851(13) Uani 0.5 1 d . . P A -1
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'
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
C17 N1 C7 120.03(10) . . ?
C17 N1 C9 123.61(10) . . ?
C7 N1 C9 112.75(10) . . ?
C12 N2 C14 114.03(10) . . ?
C29 N2 C12 118.89(11) . . ?
C29 N2 C14 125.18(10) . . ?
C18 C17 N1 119.20(11) . . ?
C18 C17 C22 119.79(12) . . ?
C22 C17 N1 121.01(11) . . ?
C17 C18 C24 122.55(11) . . ?
C19 C18 C17 118.98(12) . . ?
C19 C18 C24 118.47(12) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 C18 121.45(13) . . ?
C20 C19 H19 119.3 . . ?
C17 C22 C27 122.87(12) . . ?
C21 C22 C17 118.78(12) . . ?
C21 C22 C27 118.34(12) . . ?
C2 C1 C7 114.35(10) . . ?
C2 C1 C8 111.65(11) . . ?
C8 C1 C7 102.73(10) . . ?
C6 C1 C7 108.26(10) . . ?
C6 C1 C2 107.46(10) . . ?
C6 C1 C8 112.42(11) . . ?
C3 C4 C12 112.99(11) . . ?
C5 C4 C12 114.74(11) . . ?
C5 C4 C3 104.84(10) . . ?
C5 C4 C13 112.52(11) . . ?
C13 C4 C12 101.61(10) . . ?
C13 C4 C3 110.34(11) . . ?
C18 C24 H24 107.9 . . ?
C18 C24 C23 111.77(11) . . ?
C18 C24 C25 111.14(11) . . ?
C23 C24 H24 107.9 . . ?
C25 C24 H24 107.9 . . ?
C25 C24 C23 110.17(11) . . ?
N2 C12 C4 105.40(10) . . ?
N2 C12 H12 108.2 . . ?
N2 C12 C43 110.13(10) . . ?
C4 C12 H12 108.2 . . ?
C43 C12 C4 116.30(11) . . ?
C43 C12 H12 108.2 . . ?
C34 C29 N2 120.69(12) . . ?
C30 C29 N2 120.32(12) . . ?
C30 C29 C34 118.88(12) . . ?
N3 C42 C41 179.32(16) . . ?
C4 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C2 C3 C4 113.89(11) . . ?
C2 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.55(13) . . ?
C21 C20 H20 120.2 . . ?
C4 C5 H5A 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 C4 113.11(11) . . ?
C6 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
N1 C7 C1 106.73(10) . . ?
N1 C7 H7 107.7 . . ?
N1 C7 C41 110.50(11) . . ?
C1 C7 H7 107.7 . . ?
C41 C7 C1 116.14(10) . . ?
C41 C7 H7 107.7 . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 C1 112.85(11) . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C22 C21 H21 119.3 . . ?
C20 C21 C22 121.41(13) . . ?
C20 C21 H21 119.3 . . ?
C1 C8 H8A 110.2 . . ?
C1 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
C9 C8 C1 107.34(11) . . ?
C9 C8 H8A 110.2 . . ?
C9 C8 H8B 110.2 . . ?
N1 C9 C8 102.20(10) . . ?
N1 C9 C10 112.17(11) . . ?
N1 C9 C11 111.01(11) . . ?
C8 C9 C11 111.65(11) . . ?
C10 C9 C8 112.04(12) . . ?
C10 C9 C11 107.78(12) . . ?
C1 C6 H6A 108.6 . . ?
C1 C6 H6B 108.6 . . ?
C5 C6 C1 114.70(11) . . ?
C5 C6 H6A 108.6 . . ?
C5 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C29 C34 C39 123.81(12) . . ?
C33 C34 C29 119.33(13) . . ?
C33 C34 C39 116.83(13) . . ?
C42 C41 C7 112.59(12) . . ?
C42 C41 H41A 109.1 . . ?
C42 C41 H41B 109.1 . . ?
C7 C41 H41A 109.1 . . ?
C7 C41 H41B 109.1 . . ?
H41A C41 H41B 107.8 . . ?
C4 C13 H13A 110.1 . . ?
C4 C13 H13B 110.1 . . ?
C4 C13 C14 107.98(11) . . ?
H13A C13 H13B 108.4 . . ?
C14 C13 H13A 110.1 . . ?
C14 C13 H13B 110.1 . . ?
C22 C27 H27 107.8 . . ?
C22 C27 C28 110.68(12) . . ?
C22 C27 C26 113.23(12) . . ?
C28 C27 H27 107.8 . . ?
C28 C27 C26 109.29(12) . . ?
C26 C27 H27 107.8 . . ?
N2 C14 C13 101.43(10) . . ?
N2 C14 C15 113.10(12) . . ?
N2 C14 C16 112.56(12) . . ?
C15 C14 C13 113.42(12) . . ?
C15 C14 C16 106.67(12) . . ?
C16 C14 C13 109.74(12) . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C29 C30 C36 124.69(13) . . ?
C31 C30 C29 119.00(13) . . ?
C31 C30 C36 116.31(13) . . ?
C34 C39 H39 107.7 . . ?
C34 C39 C40 111.82(13) . . ?
C34 C39 C38 111.17(13) . . ?
C40 C39 H39 107.7 . . ?
C38 C39 H39 107.7 . . ?
C38 C39 C40 110.45(13) . . ?
C12 C43 H43A 108.5 . . ?
C12 C43 H43B 108.5 . . ?
H43A C43 H43B 107.5 . . ?
C44 C43 C12 115.13(13) . . ?
C44 C43 H43A 108.5 . . ?
C44 C43 H43B 108.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N4 C44 C43 179.03(17) . . ?
C34 C33 H33 119.2 . . ?
C32 C33 C34 121.56(15) . . ?
C32 C33 H33 119.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C27 C26 H26A 109.5 . . ?
C27 C26 H26B 109.5 . . ?
C27 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C30 C36 H36 108.2 . . ?
C30 C36 C37 110.88(13) . . ?
C30 C36 C35 111.74(15) . . ?
C37 C36 H36 108.2 . . ?
C35 C36 H36 108.2 . . ?
C35 C36 C37 109.57(14) . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C30 C31 H31 119.1 . . ?
C32 C31 C30 121.85(15) . . ?
C32 C31 H31 119.1 . . ?
C33 C32 H32 120.3 . . ?
C31 C32 C33 119.36(14) . . ?
C31 C32 H32 120.3 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C39 C38 H38A 109.5 . . ?
C39 C38 H38B 109.5 . . ?
C39 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C35 H35A 109.5 . . ?
C36 C35 H35B 109.5 . . ?
C36 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N1S C1S C2S 176.6(19) . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C17 1.4319(16) . ?
N1 C7 1.4507(16) . ?
N1 C9 1.4802(17) . ?
N2 C12 1.4587(16) . ?
N2 C29 1.4460(16) . ?
N2 C14 1.4865(17) . ?
N3 C42 1.1390(19) . ?
C17 C18 1.4105(18) . ?
C17 C22 1.4189(17) . ?
C18 C19 1.3946(18) . ?
C18 C24 1.5217(18) . ?
C19 H19 0.9500 . ?
C19 C20 1.3825(19) . ?
C22 C21 1.3961(18) . ?
C22 C27 1.5183(19) . ?
C1 C7 1.5694(18) . ?
C1 C2 1.5433(18) . ?
C1 C8 1.5501(18) . ?
C1 C6 1.5423(18) . ?
C4 C12 1.5598(18) . ?
C4 C3 1.5444(18) . ?
C4 C5 1.5401(18) . ?
C4 C13 1.5405(18) . ?
C24 H24 1.0000 . ?
C24 C23 1.5358(19) . ?
C24 C25 1.5295(19) . ?
C12 H12 1.0000 . ?
C12 C43 1.5523(18) . ?
C29 C34 1.4200(19) . ?
C29 C30 1.413(2) . ?
C42 C41 1.466(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.5289(18) . ?
C20 H20 0.9500 . ?
C20 C21 1.382(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5303(18) . ?
C7 H7 1.0000 . ?
C7 C41 1.5463(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C21 H21 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5360(19) . ?
C9 C10 1.526(2) . ?
C9 C11 1.540(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C34 C39 1.517(2) . ?
C34 C33 1.392(2) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5475(19) . ?
C27 H27 1.0000 . ?
C27 C28 1.530(2) . ?
C27 C26 1.536(2) . ?
C14 C15 1.530(2) . ?
C14 C16 1.531(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C30 C36 1.522(2) . ?
C30 C31 1.397(2) . ?
C39 H39 1.0000 . ?
C39 C40 1.537(2) . ?
C39 C38 1.534(2) . ?
N4 C44 1.145(2) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C43 C44 1.466(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C33 H33 0.9500 . ?
C33 C32 1.375(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C36 H36 1.0000 . ?
C36 C37 1.538(2) . ?
C36 C35 1.531(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C31 H31 0.9500 . ?
C31 C32 1.373(2) . ?
C32 H32 0.9500 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C1S C2S 1.44(4) . ?
C1S N1S 1.131(6) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?
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 C17 C18 C19 -178.21(11) . . . . ?
N1 C17 C18 C24 1.80(18) . . . . ?
N1 C17 C22 C21 179.68(12) . . . . ?
N1 C17 C22 C27 -1.59(19) . . . . ?
N1 C7 C41 C42 -171.64(11) . . . . ?
N2 C12 C43 C44 63.55(15) . . . . ?
N2 C29 C34 C39 1.2(2) . . . . ?
N2 C29 C34 C33 -176.84(13) . . . . ?
N2 C29 C30 C36 -0.9(2) . . . . ?
N2 C29 C30 C31 177.92(14) . . . . ?
C17 N1 C7 C1 -151.66(11) . . . . ?
C17 N1 C7 C41 81.22(14) . . . . ?
C17 N1 C9 C8 135.68(12) . . . . ?
C17 N1 C9 C10 15.50(18) . . . . ?
C17 N1 C9 C11 -105.15(14) . . . . ?
C17 C18 C19 C20 -2.1(2) . . . . ?
C17 C18 C24 C23 121.65(13) . . . . ?
C17 C18 C24 C25 -114.81(14) . . . . ?
C17 C22 C21 C20 -0.9(2) . . . . ?
C17 C22 C27 C28 -110.03(15) . . . . ?
C17 C22 C27 C26 126.86(15) . . . . ?
C18 C17 C22 C21 -0.76(19) . . . . ?
C18 C17 C22 C27 177.97(12) . . . . ?
C18 C19 C20 C21 0.4(2) . . . . ?
C19 C18 C24 C23 -58.34(16) . . . . ?
C19 C18 C24 C25 65.20(16) . . . . ?
C19 C20 C21 C22 1.1(2) . . . . ?
C22 C17 C18 C19 2.22(18) . . . . ?
C22 C17 C18 C24 -177.77(12) . . . . ?
C1 C7 C41 C42 66.63(15) . . . . ?
C1 C8 C9 N1 29.02(13) . . . . ?
C1 C8 C9 C10 149.29(12) . . . . ?
C1 C8 C9 C11 -89.69(13) . . . . ?
C4 C12 C43 C44 -56.22(16) . . . . ?
C4 C3 C2 C1 59.36(14) . . . . ?
C4 C5 C6 C1 -57.34(15) . . . . ?
C4 C13 C14 N2 -24.92(14) . . . . ?
C4 C13 C14 C15 96.66(14) . . . . ?
C4 C13 C14 C16 -144.16(12) . . . . ?
C24 C18 C19 C20 177.93(12) . . . . ?
C12 N2 C29 C34 70.83(16) . . . . ?
C12 N2 C29 C30 -105.32(15) . . . . ?
C12 N2 C14 C13 8.17(14) . . . . ?
C12 N2 C14 C15 -113.63(13) . . . . ?
C12 N2 C14 C16 125.38(12) . . . . ?
C12 C4 C3 C2 67.39(14) . . . . ?
C12 C4 C5 C6 -68.14(15) . . . . ?
C12 C4 C13 C14 31.47(14) . . . . ?
C29 N2 C12 C4 -153.94(11) . . . . ?
C29 N2 C12 C43 79.87(14) . . . . ?
C29 N2 C14 C13 172.22(12) . . . . ?
C29 N2 C14 C15 50.41(17) . . . . ?
C29 N2 C14 C16 -70.58(17) . . . . ?
C29 C34 C39 C40 120.55(16) . . . . ?
C29 C34 C39 C38 -115.49(16) . . . . ?
C29 C34 C33 C32 -0.3(2) . . . . ?
C29 C30 C36 C37 -120.03(17) . . . . ?
C29 C30 C36 C35 117.41(17) . . . . ?
C29 C30 C31 C32 -1.9(3) . . . . ?
C3 C4 C12 N2 92.77(12) . . . . ?
C3 C4 C12 C43 -144.93(12) . . . . ?
C3 C4 C5 C6 56.40(14) . . . . ?
C3 C4 C13 C14 -88.62(13) . . . . ?
C5 C4 C12 N2 -147.11(11) . . . . ?
C5 C4 C12 C43 -24.82(16) . . . . ?
C5 C4 C3 C2 -58.25(14) . . . . ?
C5 C4 C13 C14 154.67(11) . . . . ?
C7 N1 C17 C18 -110.40(13) . . . . ?
C7 N1 C17 C22 69.16(16) . . . . ?
C7 N1 C9 C8 -22.79(14) . . . . ?
C7 N1 C9 C10 -142.97(12) . . . . ?
C7 N1 C9 C11 96.38(13) . . . . ?
C7 C1 C2 C3 -171.51(11) . . . . ?
C7 C1 C8 C9 -24.76(13) . . . . ?
C7 C1 C6 C5 175.07(10) . . . . ?
C2 C1 C7 N1 -110.38(12) . . . . ?
C2 C1 C7 C41 13.32(16) . . . . ?
C2 C1 C8 C9 98.22(12) . . . . ?
C2 C1 C6 C5 51.09(14) . . . . ?
C21 C22 C27 C28 68.71(16) . . . . ?
C21 C22 C27 C26 -54.41(18) . . . . ?
C8 C1 C7 N1 10.78(13) . . . . ?
C8 C1 C7 C41 134.48(12) . . . . ?
C8 C1 C2 C3 72.40(14) . . . . ?
C8 C1 C6 C5 -72.16(14) . . . . ?
C9 N1 C17 C18 92.61(15) . . . . ?
C9 N1 C17 C22 -87.83(15) . . . . ?
C9 N1 C7 C1 7.67(14) . . . . ?
C9 N1 C7 C41 -119.45(12) . . . . ?
C6 C1 C7 N1 129.88(11) . . . . ?
C6 C1 C7 C41 -106.42(12) . . . . ?
C6 C1 C2 C3 -51.32(14) . . . . ?
C6 C1 C8 C9 -140.91(11) . . . . ?
C34 C29 C30 C36 -177.13(14) . . . . ?
C34 C29 C30 C31 1.7(2) . . . . ?
C34 C33 C32 C31 0.1(3) . . . . ?
C13 C4 C12 N2 -25.43(13) . . . . ?
C13 C4 C12 C43 96.87(13) . . . . ?
C13 C4 C3 C2 -179.63(11) . . . . ?
C13 C4 C5 C6 176.34(11) . . . . ?
C27 C22 C21 C20 -179.73(13) . . . . ?
C14 N2 C12 C4 11.19(14) . . . . ?
C14 N2 C12 C43 -115.00(13) . . . . ?
C14 N2 C29 C34 -92.51(17) . . . . ?
C14 N2 C29 C30 91.35(17) . . . . ?
C30 C29 C34 C39 177.40(14) . . . . ?
C30 C29 C34 C33 -0.6(2) . . . . ?
C30 C31 C32 C33 1.0(3) . . . . ?
C39 C34 C33 C32 -178.47(16) . . . . ?
C33 C34 C39 C40 -61.36(19) . . . . ?
C33 C34 C39 C38 62.60(17) . . . . ?
C36 C30 C31 C32 177.02(17) . . . . ?
C31 C30 C36 C37 61.1(2) . . . . ?
C31 C30 C36 C35 -61.45(19) . . . . ?
