# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_gli451
_database_code_depnum_ccdc_archive 'CCDC 1552505'
_audit_update_record             
;
2017-05-26 deposited with the CCDC.
2017-06-29 downloaded from the CCDC.
;
_audit_creation_date             2017-05-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H26 N2 O'
_chemical_formula_sum            'C22 H26 N2 O'
_chemical_formula_weight         334.45
_chemical_absolute_configuration rm
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.665(2)
_cell_length_b                   15.178(3)
_cell_length_c                   11.980(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.270(8)
_cell_angle_gamma                90
_cell_volume                     1939.2(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7250
_cell_measurement_temperature    173.0(1)
_cell_measurement_theta_max      26.15
_cell_measurement_theta_min      2.17
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0570 before and 0.0428 after correction. The Ratio of minimum to maximum transmission is 0.8986. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17023
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.431
_diffrn_reflns_theta_min         1.700
_diffrn_ambient_temperature      173.0(1)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.910
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                6780
_reflns_number_total             7850
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker Apex'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    ?
_refine_diff_density_max         0.799
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 2800 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         7850
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0520
_refine_ls_restrained_S_all      1.035
_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)+(0.0582P)²+1.1242P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1369
_refine_special_details          ?
_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 Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C8(H8), C23(H23), C25(H25), C26(H26), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C6(H6A,H6B), C24(H24A,H24B), C27(H27A,H27B),
 C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20),
 C34(H34), C35(H35), C37(H37), C38(H38), C40(H40), C41(H41), C42(H42)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C29(H29A,H29B,H29C),
 C31(H31A,H31B,H31C), C32(H32A,H32B,H32C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O1 O 0.3143(3) 0.74725(17) 0.1200(2) 0.0335(6) Uani 1 1 d . . . . .
O2 O 1.1329(2) 0.50622(16) -0.3509(2) 0.0305(6) Uani 1 1 d . . . . .
N1 N 0.2912(3) 0.80340(18) -0.0590(2) 0.0265(6) Uani 1 1 d . . . . .
N2 N 0.3186(3) 0.7903(2) -0.2870(2) 0.0315(7) Uani 1 1 d . . . . .
N3 N 0.9262(3) 0.54549(18) -0.3206(2) 0.0233(6) Uani 1 1 d . . . . .
N4 N 0.6732(3) 0.5080(2) -0.3322(3) 0.0317(7) Uani 1 1 d . . . . .
C1 C 0.2962(5) 0.5181(3) -0.0069(3) 0.0447(11) Uani 1 1 d . . . . .
H1 H 0.3447 0.5282 -0.0769 0.054 Uiso 1 1 calc R . . . .
C2 C 0.2528(4) 0.6075(2) 0.0371(3) 0.0342(8) Uani 1 1 d . . . . .
H2A H 0.2055 0.6385 -0.0224 0.041 Uiso 1 1 calc R . . . .
H2B H 0.1953 0.5982 0.1006 0.041 Uiso 1 1 calc R . . . .
C3 C 0.3620(4) 0.6650(2) 0.0750(3) 0.0316(8) Uani 1 1 d . . . . .
H3 H 0.4173 0.6778 0.0098 0.038 Uiso 1 1 calc R . . . .
C4 C 0.4384(4) 0.6193(3) 0.1661(3) 0.0400(9) Uani 1 1 d . . . . .
H4 H 0.3791 0.6036 0.2274 0.048 Uiso 1 1 calc R . . . .
C5 C 0.4878(4) 0.5334(3) 0.1180(4) 0.0561(13) Uani 1 1 d . . . . .
H5A H 0.5374 0.5022 0.1759 0.067 Uiso 1 1 calc R . . . .
H5B H 0.5443 0.5466 0.0549 0.067 Uiso 1 1 calc R . . . .
C6 C 0.3824(5) 0.4733(3) 0.0775(4) 0.0503(12) Uani 1 1 d . . . . .
H6A H 0.4194 0.4201 0.0430 0.060 Uiso 1 1 calc R . . . .
H6B H 0.3323 0.4541 0.1425 0.060 Uiso 1 1 calc R . . . .
C7 C 0.1844(7) 0.4603(3) -0.0348(4) 0.0736(18) Uani 1 1 d . . . . .
H7A H 0.1320 0.4897 -0.0910 0.110 Uiso 1 1 calc GR . . . .
H7B H 0.1351 0.4500 0.0328 0.110 Uiso 1 1 calc GR . . . .
H7C H 0.2139 0.4038 -0.0644 0.110 Uiso 1 1 calc GR . . . .
C8 C 0.5450(5) 0.6729(4) 0.2186(5) 0.0648(15) Uani 1 1 d . . . . .
H8 H 0.6027 0.6282 0.2524 0.078 Uiso 1 1 calc R . . . .
C9 C 0.5069(6) 0.7273(5) 0.3093(6) 0.0838(19) Uani 1 1 d . . . . .
H9A H 0.4363 0.7644 0.2857 0.126 Uiso 1 1 calc GR . . . .
H9B H 0.5771 0.7648 0.3326 0.126 Uiso 1 1 calc GR . . . .
H9C H 0.4810 0.6902 0.3720 0.126 Uiso 1 1 calc GR . . . .
C10 C 0.6246(5) 0.7242(4) 0.1384(6) 0.083(2) Uani 1 1 d . . . . .
H10A H 0.6965 0.7494 0.1784 0.125 Uiso 1 1 calc GR . . . .
H10B H 0.5746 0.7716 0.1051 0.125 Uiso 1 1 calc GR . . . .
H10C H 0.6546 0.6848 0.0794 0.125 Uiso 1 1 calc GR . . . .
C11 C 0.2798(3) 0.8125(2) 0.0488(3) 0.0278(7) Uani 1 1 d . . . . .
C12 C 0.2312(4) 0.8887(3) 0.1025(3) 0.0354(8) Uani 1 1 d . . . . .
H12 H 0.2279 0.8926 0.1816 0.043 Uiso 1 1 calc R . . . .
C13 C 0.1901(4) 0.9552(3) 0.0374(3) 0.0375(9) Uani 1 1 d . . . . .
H13 H 0.1557 1.0066 0.0705 0.045 Uiso 1 1 calc R . . . .
C14 C 0.1981(3) 0.9488(2) -0.0804(3) 0.0305(8) Uani 1 1 d . . . . .
C15 C 0.1555(4) 1.0170(3) -0.1526(4) 0.0400(9) Uani 1 1 d . . . . .
H15 H 0.1182 1.0682 -0.1215 0.048 Uiso 1 1 calc R . . . .
C16 C 0.1670(4) 1.0103(3) -0.2649(4) 0.0374(9) Uani 1 1 d . . . . .
H16 H 0.1380 1.0568 -0.3113 0.045 Uiso 1 1 calc R . . . .
C17 C 0.2220(3) 0.9344(3) -0.3141(3) 0.0323(8) Uani 1 1 d . . . . .
C18 C 0.2351(3) 0.9248(3) -0.4299(3) 0.0378(9) Uani 1 1 d . . . . .
H18 H 0.2077 0.9702 -0.4787 0.045 Uiso 1 1 calc R . . . .
C19 C 0.2872(4) 0.8502(3) -0.4718(3) 0.0392(9) Uani 1 1 d . . . . .
H19 H 0.2956 0.8423 -0.5501 0.047 Uiso 1 1 calc R . . . .
C20 C 0.3287(4) 0.7847(3) -0.3964(3) 0.0381(9) Uani 1 1 d . . . . .
H20 H 0.3663 0.7332 -0.4265 0.046 Uiso 1 1 calc R . . . .
C21 C 0.2653(3) 0.8644(2) -0.2446(3) 0.0264(7) Uani 1 1 d . . . . .
C22 C 0.2524(3) 0.8716(2) -0.1244(3) 0.0258(7) Uani 1 1 d . . . . .
C23 C 1.0079(4) 0.2724(3) -0.3625(5) 0.0485(11) Uani 1 1 d . . . . .
H23 H 0.9343 0.2831 -0.4127 0.058 Uiso 1 1 calc R . . . .
C24 C 1.0488(4) 0.3607(2) -0.3133(3) 0.0368(9) Uani 1 1 d . . . . .
H24A H 0.9780 0.3867 -0.2714 0.044 Uiso 1 1 calc R . . . .
H24B H 1.1187 0.3509 -0.2601 0.044 Uiso 1 1 calc R . . . .
C25 C 1.0903(3) 0.4246(2) -0.4021(3) 0.0271(7) Uani 1 1 d . . . . .
H25 H 1.0187 0.4372 -0.4539 0.032 Uiso 1 1 calc R . . . .
C26 C 1.2007(3) 0.3879(2) -0.4685(3) 0.0302(8) Uani 1 1 d . . . . .
H26 H 1.2691 0.3747 -0.4136 0.044(12) Uiso 1 1 calc R . . . .
C27 C 1.1603(4) 0.2996(3) -0.5202(3) 0.0402(9) Uani 1 1 d . . . . .
H27A H 1.0927 0.3103 -0.5754 0.048 Uiso 1 1 calc R . . . .
H27B H 1.2323 0.2735 -0.5602 0.048 Uiso 1 1 calc R . . . .
C28 C 1.1139(4) 0.2343(3) -0.4327(4) 0.0454(10) Uani 1 1 d . . . . .
H28A H 1.1846 0.2177 -0.3831 0.054 Uiso 1 1 calc R . . . .
H28B H 1.0840 0.1802 -0.4706 0.054 Uiso 1 1 calc R . . . .
C29 C 0.9667(6) 0.2103(3) -0.2698(7) 0.091(3) Uani 1 1 d . . . . .
H29A H 0.8924 0.2344 -0.2330 0.137 Uiso 1 1 calc GR . . . .
H29B H 1.0348 0.2039 -0.2151 0.137 Uiso 1 1 calc GR . . . .
H29C H 0.9466 0.1525 -0.3017 0.137 Uiso 1 1 calc GR . . . .
C30 C 1.2546(4) 0.4531(3) -0.5535(4) 0.0407(10) Uani 1 1 d . . . . .
H30 H 1.2746 0.5088 -0.5127 0.027(10) Uiso 1 1 calc R . . . .
C31 C 1.1589(5) 0.4758(5) -0.6459(5) 0.083(2) Uani 1 1 d . . . . .
H31A H 1.1475 0.4248 -0.6950 0.124 Uiso 1 1 calc GR . . . .
H31B H 1.1898 0.5258 -0.6896 0.124 Uiso 1 1 calc GR . . . .
H31C H 1.0784 0.4913 -0.6119 0.124 Uiso 1 1 calc GR . . . .
C32 C 1.3755(4) 0.4195(3) -0.6042(3) 0.0438(10) Uani 1 1 d . . . . .
H32A H 1.3566 0.3722 -0.6574 0.066 Uiso 1 1 calc GR . . . .
H32B H 1.4303 0.3968 -0.5450 0.066 Uiso 1 1 calc GR . . . .
H32C H 1.4178 0.4678 -0.6431 0.066 Uiso 1 1 calc GR . . . .
C33 C 1.0449(3) 0.5624(2) -0.3099(3) 0.0264(7) Uani 1 1 d . . . . .
C34 C 1.0956(4) 0.6387(2) -0.2571(3) 0.0348(9) Uani 1 1 d . . . . .
H34 H 1.1835 0.6487 -0.2533 0.042 Uiso 1 1 calc R . . . .
C35 C 1.0125(4) 0.6966(2) -0.2125(3) 0.0370(9) Uani 1 1 d . . . . .
H35 H 1.0423 0.7484 -0.1765 0.044 Uiso 1 1 calc R . . . .
C36 C 0.8824(4) 0.6805(2) -0.2190(3) 0.0289(7) Uani 1 1 d . . . . .
C37 C 0.7911(4) 0.7390(2) -0.1715(3) 0.0390(9) Uani 1 1 d . . . . .
H37 H 0.8185 0.7906 -0.1337 0.047 Uiso 1 1 calc R . . . .
C38 C 0.6678(4) 0.7220(3) -0.1796(3) 0.0389(9) Uani 1 1 d . . . . .
H38 H 0.6092 0.7623 -0.1489 0.047 Uiso 1 1 calc R . . . .
C39 C 0.6234(4) 0.6438(2) -0.2342(3) 0.0298(8) Uani 1 1 d . . . . .
C40 C 0.4949(4) 0.6225(3) -0.2419(3) 0.0369(9) Uani 1 1 d . . . . .
H40 H 0.4337 0.6610 -0.2114 0.044 Uiso 1 1 calc R . . . .
C41 C 0.4591(4) 0.5465(3) -0.2933(3) 0.0415(10) Uani 1 1 d . . . . .
H41 H 0.3729 0.5316 -0.3001 0.050 Uiso 1 1 calc R . . . .
C42 C 0.5516(4) 0.4910(3) -0.3360(3) 0.0397(9) Uani 1 1 d . . . . .
H42 H 0.5254 0.4375 -0.3700 0.048 Uiso 1 1 calc R . . . .
C43 C 0.7100(3) 0.5842(2) -0.2819(3) 0.0248(7) Uani 1 1 d . . . . .
C44 C 0.8432(3) 0.6035(2) -0.2748(3) 0.0232(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O1 C3 1.452(4) . ?
O1 C11 1.357(4) . ?
O2 C25 1.454(4) . ?
O2 C33 1.361(4) . ?
N1 C11 1.306(4) . ?
N1 C22 1.361(4) . ?
N2 C20 1.318(5) . ?
N2 C21 1.359(5) . ?
N3 C33 1.298(4) . ?
N3 C44 1.366(4) . ?
N4 C42 1.323(5) . ?
N4 C43 1.361(5) . ?
C1 C2 1.527(5) . ?
C1 C6 1.524(6) . ?
C1 C7 1.516(7) . ?
C2 C3 1.523(5) . ?
C3 C4 1.527(5) . ?
C4 C5 1.521(7) . ?
C4 C8 1.530(6) . ?
C5 C6 1.525(7) . ?
C8 C9 1.426(9) . ?
C8 C10 1.503(7) . ?
C11 C12 1.422(5) . ?
C12 C13 1.348(6) . ?
C13 C14 1.417(5) . ?
C14 C15 1.421(5) . ?
C14 C22 1.411(5) . ?
C15 C16 1.356(6) . ?
C16 C17 1.421(6) . ?
C17 C18 1.402(5) . ?
C17 C21 1.426(5) . ?
C18 C19 1.358(6) . ?
C19 C20 1.414(6) . ?
C21 C22 1.451(5) . ?
C23 C24 1.528(6) . ?
C23 C28 1.526(6) . ?
C23 C29 1.522(7) . ?
C24 C25 1.507(5) . ?
C25 C26 1.529(5) . ?
C26 C27 1.538(6) . ?
C26 C30 1.533(5) . ?
C27 C28 1.526(6) . ?
C30 C31 1.542(6) . ?
C30 C32 1.516(5) . ?
C33 C34 1.425(5) . ?
C34 C35 1.360(6) . ?
C35 C36 1.410(5) . ?
C36 C37 1.436(5) . ?
C36 C44 1.409(5) . ?
C37 C38 1.344(6) . ?
C38 C39 1.434(6) . ?
C39 C40 1.410(6) . ?
C39 C43 1.415(5) . ?
C40 C41 1.361(6) . ?
C41 C42 1.396(6) . ?
C43 C44 1.453(5) . ?

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
C11 O1 C3 119.2(3) . . ?
C33 O2 C25 118.1(2) . . ?
C11 N1 C22 117.3(3) . . ?
C20 N2 C21 117.5(3) . . ?
C33 N3 C44 117.8(3) . . ?
C42 N4 C43 117.5(3) . . ?
C6 C1 C2 110.5(3) . . ?
C7 C1 C2 110.6(4) . . ?
C7 C1 C6 111.1(4) . . ?
C3 C2 C1 112.3(3) . . ?
O1 C3 C2 109.6(3) . . ?
O1 C3 C4 108.1(3) . . ?
C2 C3 C4 110.9(3) . . ?
C3 C4 C8 116.4(4) . . ?
C5 C4 C3 107.7(3) . . ?
C5 C4 C8 110.7(4) . . ?
C4 C5 C6 112.2(4) . . ?
C1 C6 C5 112.7(4) . . ?
C9 C8 C4 114.0(5) . . ?
C9 C8 C10 110.6(6) . . ?
C10 C8 C4 115.7(5) . . ?
O1 C11 C12 114.1(3) . . ?
N1 C11 O1 121.2(3) . . ?
N1 C11 C12 124.7(3) . . ?
C13 C12 C11 117.7(3) . . ?
C12 C13 C14 120.3(4) . . ?
C13 C14 C15 122.4(4) . . ?
C22 C14 C13 117.1(3) . . ?
C22 C14 C15 120.5(3) . . ?
C16 C15 C14 121.3(4) . . ?
C15 C16 C17 120.8(3) . . ?
C16 C17 C21 119.6(3) . . ?
C18 C17 C16 122.5(3) . . ?
C18 C17 C21 117.8(4) . . ?
C19 C18 C17 119.7(4) . . ?
C18 C19 C20 118.5(4) . . ?
N2 C20 C19 124.3(4) . . ?
N2 C21 C17 122.2(3) . . ?
N2 C21 C22 118.3(3) . . ?
C17 C21 C22 119.5(3) . . ?
N1 C22 C14 122.8(3) . . ?
N1 C22 C21 118.9(3) . . ?
C14 C22 C21 118.3(3) . . ?
C28 C23 C24 109.5(3) . . ?
C29 C23 C24 110.2(5) . . ?
C29 C23 C28 112.6(4) . . ?
C25 C24 C23 112.1(3) . . ?
O2 C25 C24 110.0(3) . . ?
O2 C25 C26 106.8(3) . . ?
C24 C25 C26 111.3(3) . . ?
C25 C26 C27 108.2(3) . . ?
C25 C26 C30 113.8(3) . . ?
C30 C26 C27 113.5(3) . . ?
C28 C27 C26 112.4(3) . . ?
C27 C28 C23 112.1(3) . . ?
C26 C30 C31 111.9(4) . . ?
C32 C30 C26 111.8(3) . . ?
C32 C30 C31 110.5(4) . . ?
O2 C33 C34 114.1(3) . . ?
N3 C33 O2 120.9(3) . . ?
N3 C33 C34 124.9(3) . . ?
C35 C34 C33 116.9(3) . . ?
C34 C35 C36 120.6(3) . . ?
C35 C36 C37 122.7(3) . . ?
C44 C36 C35 117.3(3) . . ?
C44 C36 C37 120.0(3) . . ?
C38 C37 C36 121.2(3) . . ?
C37 C38 C39 120.9(3) . . ?
C40 C39 C38 122.5(3) . . ?
C40 C39 C43 117.6(3) . . ?
C43 C39 C38 119.9(3) . . ?
C41 C40 C39 119.6(3) . . ?
C40 C41 C42 118.7(4) . . ?
N4 C42 C41 124.3(4) . . ?
N4 C43 C39 122.3(3) . . ?
N4 C43 C44 118.5(3) . . ?
C39 C43 C44 119.1(3) . . ?
N3 C44 C36 122.3(3) . . ?
N3 C44 C43 118.8(3) . . ?
C36 C44 C43 118.9(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_gli453
_database_code_depnum_ccdc_archive 'CCDC 1552506'
_audit_update_record             
;
2017-05-26 deposited with the CCDC.
2017-06-29 downloaded from the CCDC.
;
_audit_creation_date             2017-05-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H52 N7 O11 Tb'
_chemical_formula_sum            'C44 H52 N7 O11 Tb'
_chemical_formula_weight         1013.84
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/2, x+1/2, z+1/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+3/4'
'x+1/2, -y+1/2, -z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   12.1768(3)
_cell_length_b                   12.1768(3)
_cell_length_c                   30.2213(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4481.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2914
_cell_measurement_temperature    173.0(1)
_cell_measurement_theta_max      22.10
_cell_measurement_theta_min      2.62
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.645
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0761 before and 0.0686 after correction. The Ratio of minimum to maximum transmission is 0.8603. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2072
_exptl_crystal_size_max          0.136
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.109
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_av_unetI/netI     0.1017
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            23895
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.838
_diffrn_reflns_theta_min         1.803
_diffrn_ambient_temperature      173.0(1)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_reflns_Friedel_coverage         0.676
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.853
_reflns_number_gt                4806
_reflns_number_total             6284
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker Apex'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    ?
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.116
_refine_ls_abs_structure_details 
;
 Flack x determined using 1610 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.006(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         6284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      0.977
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0556
_refine_ls_wR_factor_ref         0.0627
_refine_special_details          ?
_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 Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Tb1 Tb 0.19704(2) 0.19704(2) 0.5000 0.01493(8) Uani 1 2 d S T P . .
O1 O 0.2366(3) 0.4768(2) 0.50832(13) 0.0216(9) Uani 1 1 d . . . . .
O2 O 0.3257(3) 0.0530(3) 0.46560(12) 0.0221(9) Uani 1 1 d . . . . .
O3 O 0.1851(3) 0.1065(3) 0.42746(12) 0.0239(9) Uani 1 1 d . . . . .
O4 O 0.2903(3) -0.0249(3) 0.40212(13) 0.0250(9) Uani 1 1 d . . . . .
O5 O 0.1257(2) 0.0068(3) 0.51143(13) 0.0206(10) Uani 1 1 d . . . . .
O6 O -0.0439(2) -0.0439(2) 0.5000 0.0279(14) Uani 1 2 d S T P . .
N1 N 0.2943(3) 0.3367(3) 0.55045(14) 0.0163(10) Uani 1 1 d . . . . .
N2 N 0.3172(4) 0.1135(3) 0.55895(14) 0.0154(10) Uani 1 1 d . . . . .
N3 N 0.2679(4) 0.0422(3) 0.43108(16) 0.0190(11) Uani 1 1 d . . . . .
N4 N 0.0271(3) 0.0271(3) 0.5000 0.0201(14) Uani 1 2 d S T P . .
C1 C 0.0441(4) 0.6996(5) 0.4694(2) 0.0343(15) Uani 1 1 d . . . . .
H1 H 0.0497 0.7506 0.4952 0.041 Uiso 1 1 calc R . . . .
C2 C 0.0865(4) 0.5865(4) 0.4837(2) 0.0273(14) Uani 1 1 d . . . . .
H2A H 0.0400 0.5584 0.5081 0.033 Uiso 1 1 calc R . . . .
H2B H 0.0803 0.5348 0.4586 0.033 Uiso 1 1 calc R . . . .
C3 C 0.2057(4) 0.5909(3) 0.4991(2) 0.0234(11) Uani 1 1 d . . . . .
H3 H 0.2113 0.6355 0.5268 0.028 Uiso 1 1 calc R . . . .
C4 C 0.2823(5) 0.6381(4) 0.4638(2) 0.0325(17) Uani 1 1 d . . . . .
H4 H 0.2796 0.5872 0.4378 0.039 Uiso 1 1 calc R . . . .
C5 C 0.2362(5) 0.7501(4) 0.4481(2) 0.0439(18) Uani 1 1 d . . . . .
H5A H 0.2411 0.8034 0.4728 0.053 Uiso 1 1 calc R . . . .
H5B H 0.2822 0.7780 0.4236 0.053 Uiso 1 1 calc R . . . .
C6 C 0.1174(5) 0.7431(4) 0.4326(2) 0.0453(19) Uani 1 1 d . . . . .
H6A H 0.0918 0.8169 0.4235 0.054 Uiso 1 1 calc R . . . .
H6B H 0.1127 0.6939 0.4066 0.054 Uiso 1 1 calc R . . . .
C7 C -0.0760(5) 0.6931(6) 0.4554(2) 0.055(2) Uani 1 1 d . . . . .
H7A H -0.1203 0.6664 0.4802 0.082 Uiso 1 1 calc GR . . . .
H7B H -0.0832 0.6424 0.4303 0.082 Uiso 1 1 calc GR . . . .
H7C H -0.1016 0.7662 0.4466 0.082 Uiso 1 1 calc GR . . . .
C8 C 0.4029(5) 0.6460(5) 0.4782(2) 0.045(2) Uani 1 1 d . . . . .
H8 H 0.4226 0.5748 0.4927 0.054 Uiso 1 1 calc R . . . .
C9 C 0.4791(5) 0.6606(5) 0.4380(3) 0.069(3) Uani 1 1 d . . . . .
H9A H 0.5558 0.6590 0.4478 0.103 Uiso 1 1 calc GR . . . .
H9B H 0.4637 0.7313 0.4237 0.103 Uiso 1 1 calc GR . . . .
H9C H 0.4663 0.6010 0.4168 0.103 Uiso 1 1 calc GR . . . .
C10 C 0.4259(5) 0.7380(4) 0.5117(3) 0.056(2) Uani 1 1 d . . . . .
H10A H 0.4238 0.8092 0.4965 0.083 Uiso 1 1 calc GR . . . .
H10B H 0.4987 0.7271 0.5248 0.083 Uiso 1 1 calc GR . . . .
H10C H 0.3700 0.7366 0.5350 0.083 Uiso 1 1 calc GR . . . .
C11 C 0.2867(4) 0.4461(4) 0.54579(19) 0.0190(12) Uani 1 1 d . . . . .
C12 C 0.3286(4) 0.5194(4) 0.5776(2) 0.0237(14) Uani 1 1 d . . . . .
H12 H 0.3191 0.5963 0.5741 0.028 Uiso 1 1 calc R . . . .
C13 C 0.3829(4) 0.4792(5) 0.6134(2) 0.0285(15) Uani 1 1 d . . . . .
H13 H 0.4119 0.5282 0.6350 0.034 Uiso 1 1 calc R . . . .
C14 C 0.3963(4) 0.3642(4) 0.6187(2) 0.0213(13) Uani 1 1 d . . . . .
C15 C 0.4580(4) 0.3189(5) 0.65452(19) 0.0274(14) Uani 1 1 d . . . . .
H15 H 0.4889 0.3660 0.6763 0.033 Uiso 1 1 calc R . . . .
C16 C 0.4725(4) 0.2097(5) 0.65753(19) 0.0250(13) Uani 1 1 d . . . . .
H16 H 0.5148 0.1806 0.6812 0.030 Uiso 1 1 calc R . . . .
C17 C 0.4257(4) 0.1373(4) 0.62593(19) 0.0208(13) Uani 1 1 d . . . . .
C18 C 0.4387(4) 0.0215(5) 0.6284(2) 0.0239(14) Uani 1 1 d . . . . .
H18 H 0.4799 -0.0106 0.6518 0.029 Uiso 1 1 calc R . . . .
C19 C 0.3914(4) -0.0426(4) 0.59699(19) 0.0209(13) Uani 1 1 d . . . . .
H19 H 0.3985 -0.1202 0.5984 0.025 Uiso 1 1 calc R . . . .
C20 C 0.3322(4) 0.0060(4) 0.56257(19) 0.0194(13) Uani 1 1 d . . . . .
H20 H 0.3011 -0.0404 0.5406 0.023 Uiso 1 1 calc R . . . .
C21 C 0.3634(4) 0.1794(4) 0.59012(18) 0.0167(12) Uani 1 1 d . . . . .
C22 C 0.3500(3) 0.2968(5) 0.58606(18) 0.0175(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Tb1 O2 2.571(3) 7_556 ?
Tb1 O2 2.571(3) . ?
Tb1 O3 2.458(4) . ?
Tb1 O3 2.458(4) 7_556 ?
Tb1 O5 2.497(3) . ?
Tb1 O5 2.497(3) 7_556 ?
Tb1 N1 2.573(4) . ?
Tb1 N1 2.573(4) 7_556 ?
Tb1 N2 2.519(4) 7_556 ?
Tb1 N2 2.520(4) . ?
O1 C3 1.465(5) . ?
O1 C11 1.340(6) . ?
O2 N3 1.265(5) . ?
O3 N3 1.281(5) . ?
O4 N3 1.228(5) . ?
O5 N4 1.274(4) . ?
O6 N4 1.221(6) . ?
N1 C11 1.343(6) . ?
N1 C22 1.361(6) . ?
N2 C20 1.327(6) . ?
N2 C21 1.359(6) . ?
N4 O5 1.274(4) 7_556 ?
C1 C2 1.533(7) . ?
C1 C6 1.521(8) . ?
C1 C7 1.524(7) . ?
C2 C3 1.527(7) . ?
C3 C4 1.531(7) . ?
C4 C5 1.549(7) . ?
C4 C8 1.535(8) . ?
C5 C6 1.522(8) . ?
C8 C9 1.541(9) . ?
C8 C10 1.535(8) . ?
C11 C12 1.407(7) . ?
C12 C13 1.360(8) . ?
C13 C14 1.418(7) . ?
C14 C15 1.428(7) . ?
C14 C22 1.403(7) . ?
C15 C16 1.344(8) . ?
C16 C17 1.420(7) . ?
C17 C18 1.421(7) . ?
C17 C21 1.417(7) . ?
C18 C19 1.358(7) . ?
C19 C20 1.397(7) . ?
C21 C22 1.444(7) . ?

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
O2 Tb1 O2 174.12(16) . 7_556 ?
O2 Tb1 N1 114.20(12) 7_556 7_556 ?
O2 Tb1 N1 70.82(12) 7_556 . ?
O2 Tb1 N1 114.20(12) . . ?
O2 Tb1 N1 70.82(12) . 7_556 ?
O3 Tb1 O2 50.91(11) . . ?
O3 Tb1 O2 50.90(11) 7_556 7_556 ?
O3 Tb1 O2 126.43(12) . 7_556 ?
O3 Tb1 O2 126.42(11) 7_556 . ?
O3 Tb1 O3 137.92(17) 7_556 . ?
O3 Tb1 O5 70.49(12) . 7_556 ?
O3 Tb1 O5 70.48(12) 7_556 . ?
O3 Tb1 O5 71.75(12) . . ?
O3 Tb1 O5 71.74(12) 7_556 7_556 ?
O3 Tb1 N1 148.45(12) . . ?
O3 Tb1 N1 73.56(12) 7_556 . ?
O3 Tb1 N1 148.46(12) 7_556 7_556 ?
O3 Tb1 N1 73.56(12) . 7_556 ?
O3 Tb1 N2 66.80(12) . 7_556 ?
O3 Tb1 N2 66.80(12) 7_556 . ?
O3 Tb1 N2 118.92(12) . . ?
O3 Tb1 N2 118.92(12) 7_556 7_556 ?
O5 Tb1 O2 68.61(11) 7_556 7_556 ?
O5 Tb1 O2 105.79(11) . 7_556 ?
O5 Tb1 O2 105.79(11) 7_556 . ?
O5 Tb1 O2 68.61(11) . . ?
O5 Tb1 O5 51.27(14) 7_556 . ?
O5 Tb1 N1 137.62(12) . 7_556 ?
O5 Tb1 N1 133.71(12) . . ?
O5 Tb1 N1 133.71(12) 7_556 7_556 ?
O5 Tb1 N1 137.61(12) 7_556 . ?
O5 Tb1 N2 74.31(12) . . ?
O5 Tb1 N2 119.72(12) . 7_556 ?
O5 Tb1 N2 74.31(12) 7_556 7_556 ?
O5 Tb1 N2 119.72(12) 7_556 . ?
N1 Tb1 N1 75.09(18) 7_556 . ?
N2 Tb1 O2 69.93(12) . . ?
N2 Tb1 O2 110.86(13) 7_556 . ?
N2 Tb1 O2 69.93(12) 7_556 7_556 ?
N2 Tb1 O2 110.86(13) . 7_556 ?
N2 Tb1 N1 102.78(13) 7_556 . ?
N2 Tb1 N1 102.78(13) . 7_556 ?
N2 Tb1 N1 65.21(13) . . ?
N2 Tb1 N1 65.20(13) 7_556 7_556 ?
N2 Tb1 N2 165.65(18) 7_556 . ?
C11 O1 C3 122.8(4) . . ?
N3 O2 Tb1 93.8(3) . . ?
N3 O3 Tb1 98.7(3) . . ?
N4 O5 Tb1 96.4(3) . . ?
C11 N1 Tb1 124.2(4) . . ?
C11 N1 C22 118.1(5) . . ?
C22 N1 Tb1 117.5(3) . . ?
C20 N2 Tb1 122.5(3) . . ?
C20 N2 C21 117.9(5) . . ?
C21 N2 Tb1 119.5(3) . . ?
O2 N3 Tb1 60.8(2) . . ?
O2 N3 O3 116.4(4) . . ?
O3 N3 Tb1 55.8(2) . . ?
O4 N3 Tb1 175.7(3) . . ?
O4 N3 O2 122.3(5) . . ?
O4 N3 O3 121.3(5) . . ?
O5 N4 Tb1 58.0(3) . . ?
O5 N4 Tb1 58.0(3) 7_556 . ?
O5 N4 O5 116.0(6) 7_556 . ?
O6 N4 Tb1 180.0(4) . . ?
O6 N4 O5 122.0(3) . . ?
O6 N4 O5 122.0(3) . 7_556 ?
C6 C1 C2 108.8(5) . . ?
C6 C1 C7 112.3(5) . . ?
C7 C1 C2 110.7(5) . . ?
C3 C2 C1 112.0(4) . . ?
O1 C3 C2 105.6(3) . . ?
O1 C3 C4 109.4(4) . . ?
C2 C3 C4 112.3(5) . . ?
C3 C4 C5 108.8(5) . . ?
C3 C4 C8 114.0(5) . . ?
C8 C4 C5 112.3(5) . . ?
C6 C5 C4 112.9(5) . . ?
C1 C6 C5 110.6(5) . . ?
C4 C8 C9 111.0(6) . . ?
C10 C8 C4 114.1(5) . . ?
C10 C8 C9 109.0(5) . . ?
O1 C11 N1 113.4(5) . . ?
O1 C11 C12 124.5(5) . . ?
N1 C11 C12 122.1(5) . . ?
C13 C12 C11 119.5(5) . . ?
C12 C13 C14 120.0(6) . . ?
C13 C14 C15 121.9(5) . . ?
C22 C14 C13 116.9(6) . . ?
C22 C14 C15 121.2(5) . . ?
C16 C15 C14 120.2(5) . . ?
C15 C16 C17 121.1(5) . . ?
C16 C17 C18 122.4(5) . . ?
C21 C17 C16 120.3(5) . . ?
C21 C17 C18 117.3(5) . . ?
C19 C18 C17 119.1(5) . . ?
C18 C19 C20 119.8(5) . . ?
N2 C20 C19 123.4(5) . . ?
N2 C21 C17 122.5(5) . . ?
N2 C21 C22 118.6(5) . . ?
C17 C21 C22 118.9(5) . . ?
N1 C22 C14 123.2(5) . . ?
N1 C22 C21 118.5(5) . . ?
C14 C22 C21 118.3(5) . . ?

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
Tb1 O2 N3 O3 4.7(4) . . . . ?
Tb1 O2 N3 O4 -176.4(4) . . . . ?
Tb1 O3 N3 O2 -5.0(4) . . . . ?
Tb1 O3 N3 O4 176.2(4) . . . . ?
Tb1 O5 N4 O5 -0.001(1) . . . 7_556 ?
Tb1 O5 N4 O6 180.000(0) . . . . ?
Tb1 N1 C11 O1 -9.3(6) . . . . ?
Tb1 N1 C11 C12 171.0(4) . . . . ?
Tb1 N1 C22 C14 -172.9(4) . . . . ?
Tb1 N1 C22 C21 8.0(5) . . . . ?
Tb1 N2 C20 C19 -174.8(4) . . . . ?
Tb1 N2 C21 C17 175.6(4) . . . . ?
Tb1 N2 C21 C22 -5.5(6) . . . . ?
O1 C3 C4 C5 169.6(5) . . . . ?
O1 C3 C4 C8 -64.2(6) . . . . ?
O1 C11 C12 C13 -176.7(5) . . . . ?
N1 C11 C12 C13 2.9(8) . . . . ?
N2 C21 C22 N1 -1.9(7) . . . . ?
N2 C21 C22 C14 179.0(4) . . . . ?
C1 C2 C3 O1 -175.7(5) . . . . ?
C1 C2 C3 C4 -56.6(6) . . . . ?
C2 C1 C6 C5 -58.0(7) . . . . ?
C2 C3 C4 C5 52.7(6) . . . . ?
C2 C3 C4 C8 178.9(4) . . . . ?
C3 O1 C11 N1 171.4(4) . . . . ?
C3 O1 C11 C12 -9.0(8) . . . . ?
C3 C4 C5 C6 -54.2(7) . . . . ?
C3 C4 C8 C9 163.2(5) . . . . ?
C3 C4 C8 C10 -73.3(6) . . . . ?
C4 C5 C6 C1 58.2(7) . . . . ?
C5 C4 C8 C9 -72.5(7) . . . . ?
C5 C4 C8 C10 51.1(8) . . . . ?
C6 C1 C2 C3 57.7(7) . . . . ?
C7 C1 C2 C3 -178.4(5) . . . . ?
C7 C1 C6 C5 179.1(5) . . . . ?
C8 C4 C5 C6 178.6(6) . . . . ?
C11 O1 C3 C2 -131.5(5) . . . . ?
C11 O1 C3 C4 107.5(5) . . . . ?
C11 N1 C22 C14 2.2(7) . . . . ?
C11 N1 C22 C21 -176.9(4) . . . . ?
C11 C12 C13 C14 -0.4(8) . . . . ?
C12 C13 C14 C15 176.4(5) . . . . ?
C12 C13 C14 C22 -1.0(8) . . . . ?
C13 C14 C15 C16 -177.4(5) . . . . ?
C13 C14 C22 N1 0.1(7) . . . . ?
C13 C14 C22 C21 179.2(5) . . . . ?
C14 C15 C16 C17 -1.1(8) . . . . ?
C15 C14 C22 N1 -177.3(5) . . . . ?
C15 C14 C22 C21 1.8(7) . . . . ?
C15 C16 C17 C18 -179.4(5) . . . . ?
C15 C16 C17 C21 0.7(8) . . . . ?
C16 C17 C18 C19 180.0(5) . . . . ?
C16 C17 C21 N2 179.8(5) . . . . ?
C16 C17 C21 C22 0.9(7) . . . . ?
C17 C18 C19 C20 0.8(8) . . . . ?
C17 C21 C22 N1 177.0(4) . . . . ?
C17 C21 C22 C14 -2.1(7) . . . . ?
C18 C17 C21 N2 0.0(8) . . . . ?
C18 C17 C21 C22 -178.9(5) . . . . ?
C18 C19 C20 N2 -1.3(8) . . . . ?
C20 N2 C21 C17 -0.4(7) . . . . ?
C20 N2 C21 C22 178.5(4) . . . . ?
C21 N2 C20 C19 1.0(7) . . . . ?
C21 C17 C18 C19 -0.2(8) . . . . ?
C22 N1 C11 O1 175.9(4) . . . . ?
C22 N1 C11 C12 -3.7(8) . . . . ?
C22 C14 C15 C16 -0.2(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
