#------------------------------------------------------------------------------
#$Date: 2020-09-23 00:57:31 +0300 (Wed, 23 Sep 2020) $
#$Revision: 256625 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/80/4518071.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_4518071
loop_
_publ_author_name
'Cole, Bren E.'
'Cheisson, Thibault'
'Nelson, Joshua J. M.'
'Higgins, Robert F.'
'Gau, Michael R.'
'Carroll, Patrick J.'
'Schelter, Eric J.'
_publ_section_title
;
 Understanding Molecular Factors That Determine Performance in the Rare
 Earth (TriNOx) Separations System
;
_journal_name_full               'ACS Sustainable Chemistry & Engineering'
_journal_paper_doi               10.1021/acssuschemeng.0c03974
_journal_year                    2020
_chemical_formula_moiety         'C45 H72 N4 O3'
_chemical_formula_sum            'C45 H72 N4 O3'
_chemical_formula_weight         717.06
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-08-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.321(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.470(2)
_cell_length_b                   7.2574(7)
_cell_length_c                   24.738(2)
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.48
_cell_volume                     4366.5(7)
_computing_cell_refinement       'Bruker SAINT v8.34A'
_computing_data_collection       'Bruker APEX2 v2014.11-0'
_computing_data_reduction        'Bruker SAINT v8.34A'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'CCD area detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            61842
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.395
_diffrn_reflns_theta_min         1.111
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/4'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.091
_exptl_crystal_description       block
_exptl_crystal_F_000             1576
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.721
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     490
_refine_ls_number_reflns         8015
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0623
_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)+(0.0964P)²+4.3352P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1706
_refine_ls_wR_factor_ref         0.1847
_reflns_number_gt                6217
_reflns_number_total             8015
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sc0c03974_si_002.cif
_cod_data_source_block           40285
_cod_database_code               4518071
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.58022(9) 0.6341(3) 0.23279(10) 0.0270(5) Uani 1 1 d . . . . .
H1a H 0.599921 0.612637 0.269380 0.036 Uiso 1 1 calc R . . . .
H1b H 0.577309 0.768884 0.227016 0.036 Uiso 1 1 calc R . . . .
C2 C 0.61307(9) 0.5508(3) 0.19031(10) 0.0252(5) Uani 1 1 d . . . . .
C3 C 0.62677(10) 0.6650(4) 0.14783(11) 0.0342(6) Uani 1 1 d . . . . .
H3 H 0.617341 0.791846 0.148601 0.046 Uiso 1 1 calc R . . . .
C4 C 0.65333(10) 0.6008(4) 0.10501(11) 0.0383(7) Uani 1 1 d . . . . .
H4 H 0.663040 0.685193 0.078303 0.051 Uiso 1 1 calc R . . . .
C5 C 0.66613(10) 0.4149(4) 0.10027(11) 0.0343(6) Uani 1 1 d . . . . .
C6 C 0.65402(9) 0.3022(4) 0.14281(10) 0.0291(5) Uani 1 1 d . . . . .
H6 H 0.663223 0.175234 0.141374 0.039 Uiso 1 1 calc R . . . .
C7 C 0.62901(9) 0.3651(3) 0.18769(10) 0.0239(5) Uani 1 1 d . . . . .
C8 C 0.66626(9) 0.2062(3) 0.27428(10) 0.0243(5) Uani 1 1 d . . . . .
C9 C 0.65413(11) 0.0331(4) 0.30550(12) 0.0399(7) Uani 1 1 d . . . . .
H9a H 0.620399 0.051085 0.322849 0.060 Uiso 1 1 calc GR . . . .
H9b H 0.684835 0.008097 0.333416 0.060 Uiso 1 1 calc GR . . . .
H9c H 0.649321 -0.071405 0.280336 0.060 Uiso 1 1 calc GR . . . .
C10 C 0.72086(9) 0.1779(4) 0.25059(11) 0.0304(6) Uani 1 1 d . . . . .
H10a H 0.717720 0.072168 0.225788 0.046 Uiso 1 1 calc GR . . . .
H10b H 0.750093 0.154598 0.280178 0.046 Uiso 1 1 calc GR . . . .
H10c H 0.729731 0.288634 0.230653 0.046 Uiso 1 1 calc GR . . . .
C11 C 0.67033(10) 0.3726(4) 0.31216(10) 0.0321(6) Uani 1 1 d . . . . .
H11a H 0.679242 0.482534 0.291875 0.048 Uiso 1 1 calc GR . . . .
H11b H 0.699267 0.351253 0.342160 0.048 Uiso 1 1 calc GR . . . .
H11c H 0.635099 0.390810 0.326783 0.048 Uiso 1 1 calc GR . . . .
C12 C 0.69126(11) 0.3401(4) 0.05010(11) 0.0395(7) Uani 1 1 d . . . . .
C13 C 0.69749(14) 0.1270(5) 0.05136(14) 0.0537(8) Uani 1 1 d . . . . .
H13a H 0.711655 0.085290 0.017889 0.081 Uiso 1 1 calc GR . . . .
H13b H 0.661582 0.070155 0.054169 0.081 Uiso 1 1 calc GR . . . .
H13c H 0.723168 0.091079 0.082813 0.081 Uiso 1 1 calc GR . . . .
C14 C 0.74715(13) 0.4234(6) 0.04649(14) 0.0630(10) Uani 1 1 d . . . . .
H14a H 0.744055 0.557996 0.045469 0.094 Uiso 1 1 calc GR . . . .
H14b H 0.761567 0.379911 0.013332 0.094 Uiso 1 1 calc GR . . . .
H14c H 0.772170 0.386392 0.078304 0.094 Uiso 1 1 calc GR . . . .
C15 C 0.65251(14) 0.3847(5) -0.00140(14) 0.0599(9) Uani 1 1 d . . . . .
H15a H 0.649354 0.518595 -0.005721 0.090 Uiso 1 1 calc GR . . . .
H15b H 0.616127 0.332125 0.001850 0.090 Uiso 1 1 calc GR . . . .
H15c H 0.667351 0.331687 -0.033176 0.090 Uiso 1 1 calc GR . . . .
C16 C 0.49278(9) 0.6078(3) 0.17766(9) 0.0226(5) Uani 1 1 d . . . . .
H16a H 0.513454 0.567273 0.147551 0.030 Uiso 1 1 calc R . . . .
H16b H 0.489801 0.743717 0.175962 0.030 Uiso 1 1 calc R . . . .
C17 C 0.43576(9) 0.5257(3) 0.16961(9) 0.0207(5) Uani 1 1 d . . . . .
C18 C 0.38971(9) 0.6337(3) 0.17734(9) 0.0248(5) Uani 1 1 d . . . . .
H18 H 0.394608 0.760575 0.185946 0.033 Uiso 1 1 calc R . . . .
C19 C 0.33753(9) 0.5597(3) 0.17272(9) 0.0264(5) Uani 1 1 d . . . . .
H19 H 0.307030 0.637384 0.176916 0.035 Uiso 1 1 calc R . . . .
C20 C 0.32871(9) 0.3720(3) 0.16196(9) 0.0242(5) Uani 1 1 d . . . . .
C21 C 0.37413(9) 0.2658(3) 0.15329(9) 0.0215(5) Uani 1 1 d . . . . .
H21 H 0.369208 0.138243 0.145639 0.029 Uiso 1 1 calc R . . . .
C22 C 0.42707(9) 0.3414(3) 0.15550(8) 0.0196(5) Uani 1 1 d . . . . .
C23 C 0.47676(9) 0.1692(3) 0.08802(9) 0.0253(5) Uani 1 1 d . . . . .
C24 C 0.52893(11) 0.0533(4) 0.08849(10) 0.0334(6) Uani 1 1 d . . . . .
H24a H 0.559805 0.118850 0.108533 0.050 Uiso 1 1 calc GR . . . .
H24b H 0.536894 0.031800 0.051034 0.050 Uiso 1 1 calc GR . . . .
H24c H 0.523566 -0.065124 0.106193 0.050 Uiso 1 1 calc GR . . . .
C25 C 0.42771(11) 0.0497(5) 0.06522(11) 0.0423(7) Uani 1 1 d . . . . .
H25a H 0.421317 -0.046550 0.091604 0.063 Uiso 1 1 calc GR . . . .
H25b H 0.435712 -0.007600 0.031091 0.063 Uiso 1 1 calc GR . . . .
H25c H 0.394815 0.126899 0.058439 0.063 Uiso 1 1 calc GR . . . .
C26 C 0.48165(13) 0.3389(4) 0.05351(11) 0.0436(7) Uani 1 1 d . . . . .
H26a H 0.449898 0.419311 0.056261 0.065 Uiso 1 1 calc GR . . . .
H26b H 0.482728 0.302318 0.015506 0.065 Uiso 1 1 calc GR . . . .
H26c H 0.515494 0.405198 0.066364 0.065 Uiso 1 1 calc GR . . . .
C27 C 0.27073(9) 0.2891(4) 0.16046(10) 0.0293(6) Uani 1 1 d . . . . .
C28 C 0.27022(11) 0.0828(4) 0.14747(13) 0.0415(7) Uani 1 1 d . . . . .
H28a H 0.295185 0.018149 0.174825 0.062 Uiso 1 1 calc GR . . . .
H28b H 0.282276 0.063665 0.111406 0.062 Uiso 1 1 calc GR . . . .
H28c H 0.232856 0.034586 0.147874 0.062 Uiso 1 1 calc GR . . . .
C29 C 0.23152(11) 0.3906(5) 0.11738(12) 0.0455(7) Uani 1 1 d . . . . .
H29a H 0.194424 0.339184 0.116810 0.068 Uiso 1 1 calc GR . . . .
H29b H 0.244406 0.375182 0.081527 0.068 Uiso 1 1 calc GR . . . .
H29c H 0.230771 0.521988 0.126414 0.068 Uiso 1 1 calc GR . . . .
C30 C 0.25022(10) 0.3141(4) 0.21652(11) 0.0343(6) Uani 1 1 d . . . . .
H30a H 0.275624 0.253022 0.244265 0.051 Uiso 1 1 calc GR . . . .
H30b H 0.213545 0.259562 0.216145 0.051 Uiso 1 1 calc GR . . . .
H30c H 0.248396 0.445835 0.224908 0.051 Uiso 1 1 calc GR . . . .
C31 C 0.49539(9) 0.6227(3) 0.27629(9) 0.0238(5) Uani 1 1 d . . . . .
H31a H 0.456601 0.581565 0.270739 0.032 Uiso 1 1 calc R . . . .
H31b H 0.495504 0.759055 0.275740 0.032 Uiso 1 1 calc R . . . .
C32 C 0.52074(9) 0.5576(3) 0.33177(9) 0.0228(5) Uani 1 1 d . . . . .
C33 C 0.55368(10) 0.6773(3) 0.36565(10) 0.0280(5) Uani 1 1 d . . . . .
H33 H 0.557753 0.801256 0.354383 0.037 Uiso 1 1 calc R . . . .
C34 C 0.58059(10) 0.6207(4) 0.41519(10) 0.0289(5) Uani 1 1 d . . . . .
H34 H 0.602341 0.706497 0.437155 0.038 Uiso 1 1 calc R . . . .
C35 C 0.57621(9) 0.4415(4) 0.43303(9) 0.0265(5) Uani 1 1 d . . . . .
C36 C 0.54202(9) 0.3236(3) 0.40043(9) 0.0240(5) Uani 1 1 d . . . . .
H36 H 0.537822 0.200329 0.412221 0.032 Uiso 1 1 calc R . . . .
C37 C 0.51366(9) 0.3790(3) 0.35120(9) 0.0209(5) Uani 1 1 d . . . . .
C38 C 0.42416(9) 0.2085(3) 0.33462(9) 0.0248(5) Uani 1 1 d . . . . .
C39 C 0.39670(10) 0.0693(4) 0.29423(10) 0.0326(6) Uani 1 1 d . . . . .
H39a H 0.400121 0.110991 0.257073 0.049 Uiso 1 1 calc GR . . . .
H39b H 0.357706 0.058311 0.299434 0.049 Uiso 1 1 calc GR . . . .
H39c H 0.414611 -0.050851 0.300216 0.049 Uiso 1 1 calc GR . . . .
C40 C 0.42709(10) 0.1299(4) 0.39267(10) 0.0307(6) Uani 1 1 d . . . . .
H40a H 0.451503 0.022440 0.395765 0.046 Uiso 1 1 calc GR . . . .
H40b H 0.390217 0.092905 0.400368 0.046 Uiso 1 1 calc GR . . . .
H40c H 0.441434 0.224200 0.418823 0.046 Uiso 1 1 calc GR . . . .
C41 C 0.39083(10) 0.3868(4) 0.33109(11) 0.0344(6) Uani 1 1 d . . . . .
H41a H 0.410714 0.481562 0.353629 0.052 Uiso 1 1 calc GR . . . .
H41b H 0.355023 0.364693 0.344153 0.052 Uiso 1 1 calc GR . . . .
H41c H 0.385366 0.428734 0.293217 0.052 Uiso 1 1 calc GR . . . .
C42 C 0.60612(10) 0.3686(4) 0.48697(10) 0.0335(6) Uani 1 1 d . . . . .
C43 C 0.63560(16) 0.1902(6) 0.47653(13) 0.0710(12) Uani 1 1 d . . . . .
H43a H 0.608615 0.096892 0.462845 0.106 Uiso 1 1 calc GR . . . .
H43b H 0.655911 0.146894 0.510512 0.106 Uiso 1 1 calc GR . . . .
H43c H 0.661325 0.211738 0.449500 0.106 Uiso 1 1 calc GR . . . .
C44 C 0.56420(12) 0.3318(4) 0.52705(11) 0.0413(7) Uani 1 1 d . . . . .
H44a H 0.536895 0.242639 0.511215 0.062 Uiso 1 1 calc GR . . . .
H44b H 0.545752 0.447159 0.534743 0.062 Uiso 1 1 calc GR . . . .
H44c H 0.583035 0.281818 0.560906 0.062 Uiso 1 1 calc GR . . . .
C45 C 0.64775(12) 0.5102(5) 0.51375(12) 0.0498(8) Uani 1 1 d . . . . .
H45a H 0.664636 0.461787 0.548635 0.075 Uiso 1 1 calc GR . . . .
H45b H 0.628684 0.625864 0.519848 0.075 Uiso 1 1 calc GR . . . .
H45c H 0.676351 0.532862 0.489764 0.075 Uiso 1 1 calc GR . . . .
N1 N 0.62200(7) 0.2210(3) 0.22632(8) 0.0244(4) Uani 1 1 d . . . . .
N2 N 0.47437(7) 0.2323(2) 0.14525(7) 0.0198(4) Uani 1 1 d . . . . .
N3 N 0.47969(7) 0.2515(3) 0.31717(8) 0.0221(4) Uani 1 1 d . . . . .
N4 N 0.52418(7) 0.5542(2) 0.23047(7) 0.0190(4) Uani 1 1 d . . . . .
O1 O 0.56836(6) 0.2250(2) 0.24557(7) 0.0248(4) Uani 1 1 d . . . . .
H1 H 0.554092 0.329262 0.239456 0.037 Uiso 1 1 calc GR . . . .
O2 O 0.47477(7) 0.0705(2) 0.17969(6) 0.0258(4) Uani 1 1 d . . . . .
H2 H 0.501746 0.075796 0.203779 0.039 Uiso 1 1 calc GR . . . .
O3 O 0.50872(7) 0.0779(2) 0.31965(7) 0.0275(4) Uani 1 1 d . . . . .
H3a H 0.532930 0.080297 0.298079 0.041 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 C1 C2 112.06(18) . . ?
C3 C2 C1 118.1(2) . . ?
C3 C2 C7 116.1(2) . . ?
C7 C2 C1 125.7(2) . . ?
C4 C3 C2 123.0(2) . . ?
C3 C4 C5 121.3(2) . . ?
C4 C5 C12 121.4(2) . . ?
C6 C5 C4 115.9(2) . . ?
C6 C5 C12 122.6(3) . . ?
C5 C6 C7 123.8(2) . . ?
C2 C7 N1 127.7(2) . . ?
C6 C7 C2 119.7(2) . . ?
C6 C7 N1 112.6(2) . . ?
C9 C8 C10 108.1(2) . . ?
C9 C8 C11 110.2(2) . . ?
C11 C8 C10 109.94(19) . . ?
N1 C8 C9 107.01(18) . . ?
N1 C8 C10 106.73(19) . . ?
N1 C8 C11 114.61(18) . . ?
C5 C12 C13 112.4(2) . . ?
C14 C12 C5 110.6(2) . . ?
C14 C12 C13 108.2(3) . . ?
C14 C12 C15 110.3(3) . . ?
C15 C12 C5 109.2(2) . . ?
C15 C12 C13 106.0(3) . . ?
N4 C16 C17 113.09(17) . . ?
C18 C17 C16 120.4(2) . . ?
C22 C17 C16 121.7(2) . . ?
C22 C17 C18 117.9(2) . . ?
C19 C18 C17 121.5(2) . . ?
C18 C19 C20 121.1(2) . . ?
C19 C20 C27 120.5(2) . . ?
C21 C20 C19 117.4(2) . . ?
C21 C20 C27 122.1(2) . . ?
C20 C21 C22 121.9(2) . . ?
C17 C22 C21 120.0(2) . . ?
C17 C22 N2 117.78(19) . . ?
C21 C22 N2 122.15(19) . . ?
C24 C23 C25 108.1(2) . . ?
C26 C23 C24 109.6(2) . . ?
C26 C23 C25 111.1(2) . . ?
N2 C23 C24 106.33(18) . . ?
N2 C23 C25 114.19(18) . . ?
N2 C23 C26 107.4(2) . . ?
C20 C27 C29 109.4(2) . . ?
C28 C27 C20 112.0(2) . . ?
C28 C27 C29 109.4(2) . . ?
C28 C27 C30 108.0(2) . . ?
C30 C27 C20 108.90(19) . . ?
C30 C27 C29 109.1(2) . . ?
N4 C31 C32 113.92(17) . . ?
C33 C32 C31 120.0(2) . . ?
C33 C32 C37 117.0(2) . . ?
C37 C32 C31 123.0(2) . . ?
C34 C33 C32 122.1(2) . . ?
C35 C34 C33 121.0(2) . . ?
C34 C35 C36 117.2(2) . . ?
C34 C35 C42 123.6(2) . . ?
C36 C35 C42 119.2(2) . . ?
C35 C36 C37 122.7(2) . . ?
C32 C37 N3 118.46(19) . . ?
C36 C37 C32 119.9(2) . . ?
C36 C37 N3 121.5(2) . . ?
C39 C38 C40 109.7(2) . . ?
C39 C38 C41 109.3(2) . . ?
C41 C38 C40 109.7(2) . . ?
N3 C38 C39 107.25(18) . . ?
N3 C38 C40 113.20(19) . . ?
N3 C38 C41 107.57(19) . . ?
C35 C42 C45 111.7(2) . . ?
C43 C42 C35 109.5(2) . . ?
C43 C42 C44 109.1(3) . . ?
C43 C42 C45 109.7(3) . . ?
C44 C42 C35 109.5(2) . . ?
C44 C42 C45 107.3(2) . . ?
C7 N1 C8 116.29(17) . . ?
C7 N1 O1 112.54(16) . . ?
O1 N1 C8 109.84(16) . . ?
C22 N2 C23 116.66(17) . . ?
C22 N2 O2 107.09(15) . . ?
O2 N2 C23 108.04(16) . . ?
C37 N3 C38 116.39(17) . . ?
O3 N3 C37 106.51(16) . . ?
O3 N3 C38 105.25(16) . . ?
C1 N4 C16 108.47(17) . . ?
C1 N4 C31 110.74(17) . . ?
C31 N4 C16 109.85(17) . . ?
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 1.517(4) . ?
C1 N4 1.484(3) . ?
C2 C3 1.407(3) . ?
C2 C7 1.407(3) . ?
C3 C4 1.383(4) . ?
C4 C5 1.393(4) . ?
C5 C6 1.390(4) . ?
C5 C12 1.543(4) . ?
C6 C7 1.402(3) . ?
C7 N1 1.439(3) . ?
C8 C9 1.521(3) . ?
C8 C10 1.531(3) . ?
C8 C11 1.525(3) . ?
C8 N1 1.520(3) . ?
C12 C13 1.554(5) . ?
C12 C14 1.507(4) . ?
C12 C15 1.536(4) . ?
C16 C17 1.510(3) . ?
C16 N4 1.492(3) . ?
C17 C18 1.403(3) . ?
C17 C22 1.392(3) . ?
C18 C19 1.378(3) . ?
C19 C20 1.400(3) . ?
C20 C21 1.389(3) . ?
C20 C27 1.538(3) . ?
C21 C22 1.402(3) . ?
C22 N2 1.448(3) . ?
C23 C24 1.528(3) . ?
C23 C25 1.537(3) . ?
C23 C26 1.511(4) . ?
C23 N2 1.495(3) . ?
C27 C28 1.531(4) . ?
C27 C29 1.541(4) . ?
C27 C30 1.537(3) . ?
C31 C32 1.518(3) . ?
C31 N4 1.484(3) . ?
C32 C33 1.399(3) . ?
C32 C37 1.400(3) . ?
C33 C34 1.388(3) . ?
C34 C35 1.382(4) . ?
C35 C36 1.390(3) . ?
C35 C42 1.543(3) . ?
C36 C37 1.393(3) . ?
C37 N3 1.450(3) . ?
C38 C39 1.524(3) . ?
C38 C40 1.540(3) . ?
C38 C41 1.527(3) . ?
C38 N3 1.503(3) . ?
C42 C43 1.518(4) . ?
C42 C44 1.526(4) . ?
C42 C45 1.544(4) . ?
N1 O1 1.445(2) . ?
N2 O2 1.451(2) . ?
N3 O3 1.444(2) . ?
