# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_nh12
_database_code_depnum_ccdc_archive 'CCDC 1868741'
_audit_update_record             
;
2019-01-20 deposited with the CCDC.
2019-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C53 H40 N3 O6 Tb'
_chemical_formula_sum            'C53 H40 N3 O6 Tb'
_chemical_formula_weight         973.80

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.1862(7)
_cell_length_b                   22.5030(14)
_cell_length_c                   16.0608(10)
_cell_angle_alpha                90
_cell_angle_beta                 109.979(2)
_cell_angle_gamma                90
_cell_volume                     4478.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9988
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      24.65

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             1968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.633
_shelx_estimated_absorpt_T_min   0.736
_shelx_estimated_absorpt_T_max   0.792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6977
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'


_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            66284
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.258
_diffrn_reflns_theta_max         26.563
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9324
_reflns_number_gt                6943
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
It is noted that there is one high electron density peak near the
atom C27 which is not in a chemically meaningful position. The possible 
reasons for its presence are a)inefficient absoroption correction 
in this heavy atom structure b)due to impurity
in the crystal or c) due to hidden twinning.But it is not giving 
any singificant alert in IUCR CIF-CHECK

;

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0165P)²+3.0362P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9324
_refine_ls_number_parameters     572
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0605
_refine_ls_wR_factor_gt          0.0525
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.4684(3) 0.23440(16) 1.0754(2) 0.0551(9) Uani 1 1 d . . . . .
H1 H 0.5212 0.2343 1.0491 0.066 Uiso 1 1 calc R U . . .
C2 C 0.4771(3) 0.20666(16) 1.1520(2) 0.0618(10) Uani 1 1 d . . . . .
H2 H 0.5352 0.1844 1.1877 0.074 Uiso 1 1 calc R U . . .
C3 C 0.3200(2) 0.25196(13) 1.09790(17) 0.0369(7) Uani 1 1 d . . . . .
C4 C 0.2123(2) 0.27468(13) 1.08325(19) 0.0398(7) Uani 1 1 d . . . . .
C5 C 0.1574(3) 0.26736(16) 1.1416(2) 0.0584(9) Uani 1 1 d . . . . .
H5 H 0.1887 0.2466 1.1943 0.070 Uiso 1 1 calc R U . . .
C6 C 0.0568(3) 0.29081(18) 1.1214(3) 0.0751(12) Uani 1 1 d . . . . .
H6 H 0.0192 0.2869 1.1607 0.090 Uiso 1 1 calc R U . . .
C7 C 0.0120(3) 0.31990(18) 1.0435(3) 0.0708(11) Uani 1 1 d . . . . .
H7 H -0.0573 0.3355 1.0279 0.085 Uiso 1 1 calc R U . . .
C8 C 0.0701(3) 0.32587(16) 0.9886(2) 0.0568(9) Uani 1 1 d . . . . .
H8 H 0.0391 0.3462 0.9355 0.068 Uiso 1 1 calc R U . . .
C9 C 0.6729(3) 0.35956(16) 1.0776(2) 0.0583(9) Uani 1 1 d . . . . .
H9 H 0.6363 0.3252 1.0518 0.070 Uiso 1 1 calc R U . . .
C10 C 0.7837(3) 0.35888(18) 1.1131(3) 0.0669(10) Uani 1 1 d . . . . .
H10 H 0.8213 0.3242 1.1113 0.080 Uiso 1 1 calc R U . . .
C11 C 0.8389(3) 0.40927(19) 1.1513(3) 0.0701(11) Uani 1 1 d . . . . .
H11 H 0.9138 0.4088 1.1757 0.084 Uiso 1 1 calc R U . . .
C12 C 0.7828(3) 0.46039(18) 1.1531(2) 0.0643(10) Uani 1 1 d . . . . .
H12 H 0.8199 0.4948 1.1777 0.077 Uiso 1 1 calc R U . . .
C13 C 0.6714(3) 0.46075(15) 1.1183(2) 0.0532(8) Uani 1 1 d . . . . .
H13 H 0.6339 0.4953 1.1209 0.064 Uiso 1 1 calc R U . . .
C14 C 0.6151(2) 0.41028(14) 1.07971(19) 0.0436(7) Uani 1 1 d . . . . .
C15 C 0.4943(2) 0.40803(14) 1.03985(19) 0.0424(7) Uani 1 1 d . . . . .
C16 C 0.4323(2) 0.44699(15) 1.0706(2) 0.0502(8) Uani 1 1 d . . . . .
H16 H 0.4684 0.4737 1.1151 0.060 Uiso 1 1 calc R U . . .
C17 C 0.3205(3) 0.44839(14) 1.0389(2) 0.0447(8) Uani 1 1 d . . . . .
C18 C 0.2625(3) 0.49292(15) 1.0761(2) 0.0502(8) Uani 1 1 d . . . . .
C19 C 0.3060(3) 0.54732(17) 1.1080(2) 0.0684(11) Uani 1 1 d . . . . .
H19 H 0.3731 0.5581 1.1056 0.082 Uiso 1 1 calc R U . . .
C20 C 0.2501(4) 0.5861(2) 1.1435(3) 0.0901(14) Uani 1 1 d . . . . .
H20 H 0.2803 0.6227 1.1655 0.108 Uiso 1 1 calc R U . . .
C21 C 0.1512(4) 0.5711(2) 1.1466(3) 0.0941(16) Uani 1 1 d . . . . .
H21 H 0.1149 0.5971 1.1717 0.113 Uiso 1 1 calc R U . . .
C22 C 0.1060(4) 0.5183(2) 1.1132(3) 0.0967(15) Uani 1 1 d . . . . .
H22 H 0.0378 0.5085 1.1141 0.116 Uiso 1 1 calc R U . . .
C23 C 0.1614(3) 0.47876(19) 1.0774(3) 0.0760(12) Uani 1 1 d . . . . .
H23 H 0.1300 0.4426 1.0544 0.091 Uiso 1 1 calc R U . . .
C24 C 0.4225(3) 0.44549(17) 0.7139(2) 0.0653(10) Uani 1 1 d . . . . .
H24 H 0.4545 0.4322 0.7718 0.078 Uiso 1 1 calc R U . . .
C25 C 0.4840(3) 0.4759(2) 0.6746(3) 0.0891(14) Uani 1 1 d . . . . .
H25 H 0.5564 0.4834 0.7059 0.107 Uiso 1 1 calc R U . . .
C26 C 0.4389(4) 0.4951(2) 0.5896(3) 0.1048(17) Uani 1 1 d . . . . .
H26 H 0.4801 0.5160 0.5627 0.126 Uiso 1 1 calc R U . . .
C27 C 0.3331(4) 0.4835(2) 0.5442(3) 0.1095(18) Uani 1 1 d . . . . .
H27 H 0.3025 0.4961 0.4858 0.131 Uiso 1 1 calc R U . . .
C28 C 0.2705(3) 0.4531(2) 0.5840(2) 0.0850(14) Uani 1 1 d . . . . .
H28 H 0.1982 0.4456 0.5522 0.102 Uiso 1 1 calc R U . . .
C29 C 0.3149(3) 0.43392(14) 0.6703(2) 0.0484(8) Uani 1 1 d . . . . .
C30 C 0.2534(2) 0.40166(13) 0.71875(19) 0.0427(7) Uani 1 1 d . . . . .
C31 C 0.1429(2) 0.39196(14) 0.68192(19) 0.0477(8) Uani 1 1 d . . . . .
H31 H 0.1084 0.4035 0.6234 0.057 Uiso 1 1 calc R U . . .
C32 C 0.0800(2) 0.36605(13) 0.7267(2) 0.0420(7) Uani 1 1 d . . . . .
C33 C -0.0378(3) 0.35488(14) 0.6800(2) 0.0465(8) Uani 1 1 d . . . . .
C34 C -0.0973(3) 0.38309(18) 0.6025(2) 0.0699(11) Uani 1 1 d . . . . .
H34 H -0.0637 0.4104 0.5769 0.084 Uiso 1 1 calc R U . . .
C35 C -0.2057(3) 0.3715(2) 0.5622(3) 0.0998(16) Uani 1 1 d . . . . .
H35 H -0.2446 0.3908 0.5099 0.120 Uiso 1 1 calc R U . . .
C36 C -0.2554(4) 0.3321(3) 0.5987(4) 0.1124(19) Uani 1 1 d . . . . .
H36 H -0.3288 0.3249 0.5715 0.135 Uiso 1 1 calc R U . . .
C37 C -0.1995(4) 0.3028(2) 0.6747(3) 0.0887(14) Uani 1 1 d . . . . .
H37 H -0.2343 0.2754 0.6990 0.106 Uiso 1 1 calc R U . . .
C38 C -0.0907(3) 0.31412(16) 0.7156(2) 0.0630(10) Uani 1 1 d . . . . .
H38 H -0.0525 0.2942 0.7676 0.076 Uiso 1 1 calc R U . . .
C39 C 0.0779(3) 0.14664(19) 0.8960(3) 0.0740(11) Uani 1 1 d . . . . .
H39 H 0.0730 0.1843 0.9183 0.089 Uiso 1 1 calc R U . . .
C40 C 0.0058(3) 0.1028(3) 0.8994(3) 0.0910(14) Uani 1 1 d . . . . .
H40 H -0.0466 0.1110 0.9244 0.109 Uiso 1 1 calc R U . . .
C41 C 0.0114(4) 0.0476(3) 0.8662(3) 0.1042(17) Uani 1 1 d . . . . .
H41 H -0.0367 0.0181 0.8692 0.125 Uiso 1 1 calc R U . . .
C42 C 0.0872(5) 0.0359(2) 0.8289(3) 0.0976(15) Uani 1 1 d . . . . .
H42 H 0.0898 -0.0015 0.8051 0.117 Uiso 1 1 calc R U . . .
C43 C 0.1610(4) 0.07887(18) 0.8255(3) 0.0781(12) Uani 1 1 d . . . . .
H43 H 0.2131 0.0700 0.8003 0.094 Uiso 1 1 calc R U . . .
C44 C 0.1572(3) 0.13497(17) 0.8597(2) 0.0623(10) Uani 1 1 d . . . . .
C45 C 0.2340(3) 0.18375(17) 0.8585(2) 0.0589(9) Uani 1 1 d . . . . .
C46 C 0.3369(3) 0.17058(16) 0.8552(2) 0.0626(9) Uani 1 1 d . . . . .
H46 H 0.3565 0.1309 0.8554 0.075 Uiso 1 1 calc R U . . .
C47 C 0.4104(3) 0.21351(17) 0.8515(2) 0.0537(9) Uani 1 1 d . . . . .
C48 C 0.5162(3) 0.19707(18) 0.8437(2) 0.0622(10) Uani 1 1 d . . . . .
C49 C 0.5997(3) 0.2373(2) 0.8708(2) 0.0740(11) Uani 1 1 d . . . . .
H49 H 0.5887 0.2734 0.8947 0.089 Uiso 1 1 calc R U . . .
C50 C 0.6995(4) 0.2258(3) 0.8636(3) 0.0958(15) Uani 1 1 d . . . . .
H50 H 0.7554 0.2532 0.8834 0.115 Uiso 1 1 calc R U . . .
C51 C 0.7139(5) 0.1727(3) 0.8262(4) 0.110(2) Uani 1 1 d . . . . .
H51 H 0.7797 0.1647 0.8193 0.133 Uiso 1 1 calc R U . . .
C52 C 0.6336(5) 0.1321(3) 0.7994(3) 0.1109(19) Uani 1 1 d . . . . .
H52 H 0.6451 0.0962 0.7755 0.133 Uiso 1 1 calc R U . . .
C53 C 0.5341(4) 0.1440(2) 0.8077(3) 0.0840(13) Uani 1 1 d . . . . .
H53 H 0.4790 0.1160 0.7888 0.101 Uiso 1 1 calc R U . . .
N1 N 0.37112(19) 0.26261(11) 1.04183(15) 0.0442(6) Uani 1 1 d . . . . .
N2 N 0.16862(19) 0.30424(11) 1.00667(16) 0.0436(6) Uani 1 1 d . . . . .
N3 N 0.3815(2) 0.21823(13) 1.16629(19) 0.0548(8) Uani 1 1 d . . . . .
O1 O 0.45556(15) 0.36917(10) 0.98099(14) 0.0498(5) Uani 1 1 d . . . . .
O2 O 0.26121(16) 0.41336(9) 0.98040(14) 0.0477(5) Uani 1 1 d . . . . .
O3 O 0.39366(18) 0.26915(10) 0.85378(14) 0.0565(6) Uani 1 1 d . . . . .
O4 O 0.20048(17) 0.23578(10) 0.86183(14) 0.0562(6) Uani 1 1 d . . . . .
O5 O 0.30871(16) 0.38362(11) 0.79473(14) 0.0624(7) Uani 1 1 d . . . . .
O6 O 0.11623(16) 0.35010(10) 0.80655(14) 0.0554(6) Uani 1 1 d . . . . .
Tb1 Tb 0.28641(2) 0.32824(2) 0.90944(2) 0.03855(5) Uani 1 1 d . . . . .
H3 H 0.362(3) 0.2123(15) 1.208(2) 0.064(12) Uiso 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
C1 C2 1.350(4) . ?
C1 N1 1.366(4) . ?
C1 H1 0.9300 . ?
C2 N3 1.381(4) . ?
C2 H2 0.9300 . ?
C3 N1 1.319(3) . ?
C3 N3 1.353(4) . ?
C3 C4 1.450(4) . ?
C4 N2 1.343(4) . ?
C4 C5 1.377(4) . ?
C5 C6 1.359(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.356(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.359(4) . ?
C7 H7 0.9300 . ?
C8 N2 1.323(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.375(4) . ?
C9 C14 1.379(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.373(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.502(4) . ?
C15 O1 1.261(3) . ?
C15 C16 1.399(4) . ?
C16 C17 1.386(4) . ?
C16 H16 0.9300 . ?
C17 O2 1.270(4) . ?
C17 C18 1.502(4) . ?
C18 C19 1.374(5) . ?
C18 C23 1.379(5) . ?
C19 C20 1.385(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.365(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.355(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.394(5) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.368(5) . ?
C24 C29 1.376(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.359(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.360(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.385(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.377(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.490(4) . ?
C30 O5 1.256(3) . ?
C30 C31 1.390(4) . ?
C31 C32 1.397(4) . ?
C31 H31 0.9300 . ?
C32 O6 1.258(3) . ?
C32 C33 1.498(4) . ?
C33 C34 1.379(5) . ?
C33 C38 1.388(4) . ?
C34 C35 1.378(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.348(6) . ?
C35 H35 0.9300 . ?
C36 C37 1.362(6) . ?
C36 H36 0.9300 . ?
C37 C38 1.382(5) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 C40 1.384(5) . ?
C39 C44 1.386(5) . ?
C39 H39 0.9300 . ?
C40 C41 1.363(7) . ?
C40 H40 0.9300 . ?
C41 C42 1.357(7) . ?
C41 H41 0.9300 . ?
C42 C43 1.386(6) . ?
C42 H42 0.9300 . ?
C43 C44 1.384(5) . ?
C43 H43 0.9300 . ?
C44 C45 1.498(5) . ?
C45 O4 1.259(4) . ?
C45 C46 1.407(5) . ?
C46 C47 1.385(5) . ?
C46 H46 0.9300 . ?
C47 O3 1.274(4) . ?
C47 C48 1.489(5) . ?
C48 C49 1.377(5) . ?
C48 C53 1.382(5) . ?
C49 C50 1.384(5) . ?
C49 H49 0.9300 . ?
C50 C51 1.380(7) . ?
C50 H50 0.9300 . ?
C51 C52 1.352(7) . ?
C51 H51 0.9300 . ?
C52 C53 1.390(6) . ?
C52 H52 0.9300 . ?
C53 H53 0.9300 . ?
N1 Tb1 2.515(2) . ?
N2 Tb1 2.608(2) . ?
N3 H3 0.81(3) . ?
O1 Tb1 2.322(2) . ?
O2 Tb1 2.310(2) . ?
O3 Tb1 2.330(2) . ?
O4 Tb1 2.368(2) . ?
O5 Tb1 2.325(2) . ?
O6 Tb1 2.340(2) . ?

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
C2 C1 N1 110.5(3) . . ?
C2 C1 H1 124.7 . . ?
N1 C1 H1 124.7 . . ?
C1 C2 N3 105.4(3) . . ?
C1 C2 H2 127.3 . . ?
N3 C2 H2 127.3 . . ?
N1 C3 N3 110.6(3) . . ?
N1 C3 C4 121.7(3) . . ?
N3 C3 C4 127.7(3) . . ?
N2 C4 C5 121.5(3) . . ?
N2 C4 C3 114.4(2) . . ?
C5 C4 C3 124.1(3) . . ?
C6 C5 C4 119.2(3) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C7 C6 C5 119.3(3) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C8 118.8(3) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
N2 C8 C7 123.4(3) . . ?
N2 C8 H8 118.3 . . ?
C7 C8 H8 118.3 . . ?
C10 C9 C14 121.1(3) . . ?
C10 C9 H9 119.5 . . ?
C14 C9 H9 119.5 . . ?
C11 C10 C9 120.1(4) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.1(4) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C14 120.7(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C9 C14 C13 118.3(3) . . ?
C9 C14 C15 118.4(3) . . ?
C13 C14 C15 123.2(3) . . ?
O1 C15 C16 124.3(3) . . ?
O1 C15 C14 116.2(3) . . ?
C16 C15 C14 119.4(3) . . ?
C17 C16 C15 124.2(3) . . ?
C17 C16 H16 117.9 . . ?
C15 C16 H16 117.9 . . ?
O2 C17 C16 124.4(3) . . ?
O2 C17 C18 116.1(3) . . ?
C16 C17 C18 119.4(3) . . ?
C19 C18 C23 118.8(3) . . ?
C19 C18 C17 122.6(3) . . ?
C23 C18 C17 118.6(3) . . ?
C18 C19 C20 120.2(4) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 120.6(4) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C20 119.9(4) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.1(4) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C18 C23 C22 120.3(4) . . ?
C18 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C29 122.1(4) . . ?
C25 C24 H24 119.0 . . ?
C29 C24 H24 119.0 . . ?
C26 C25 C24 119.7(4) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C27 119.7(4) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C26 C27 C28 120.7(4) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C29 C28 C27 120.2(4) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C24 C29 C28 117.6(3) . . ?
C24 C29 C30 118.5(3) . . ?
C28 C29 C30 123.9(3) . . ?
O5 C30 C31 122.6(3) . . ?
O5 C30 C29 115.2(3) . . ?
C31 C30 C29 122.2(3) . . ?
C30 C31 C32 124.5(3) . . ?
C30 C31 H31 117.7 . . ?
C32 C31 H31 117.7 . . ?
O6 C32 C31 123.9(3) . . ?
O6 C32 C33 115.5(3) . . ?
C31 C32 C33 120.6(3) . . ?
C34 C33 C38 117.8(3) . . ?
C34 C33 C32 123.2(3) . . ?
C38 C33 C32 119.1(3) . . ?
C35 C34 C33 121.0(4) . . ?
C35 C34 H34 119.5 . . ?
C33 C34 H34 119.5 . . ?
C36 C35 C34 120.1(5) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C35 C36 C37 120.8(4) . . ?
C35 C36 H36 119.6 . . ?
C37 C36 H36 119.6 . . ?
C36 C37 C38 119.6(4) . . ?
C36 C37 H37 120.2 . . ?
C38 C37 H37 120.2 . . ?
C37 C38 C33 120.8(4) . . ?
C37 C38 H38 119.6 . . ?
C33 C38 H38 119.6 . . ?
C40 C39 C44 120.6(4) . . ?
C40 C39 H39 119.7 . . ?
C44 C39 H39 119.7 . . ?
C41 C40 C39 120.4(5) . . ?
C41 C40 H40 119.8 . . ?
C39 C40 H40 119.8 . . ?
C42 C41 C40 119.7(5) . . ?
C42 C41 H41 120.2 . . ?
C40 C41 H41 120.2 . . ?
C41 C42 C43 121.0(5) . . ?
C41 C42 H42 119.5 . . ?
C43 C42 H42 119.5 . . ?
C44 C43 C42 120.0(4) . . ?
C44 C43 H43 120.0 . . ?
C42 C43 H43 120.0 . . ?
C43 C44 C39 118.3(4) . . ?
C43 C44 C45 123.2(4) . . ?
C39 C44 C45 118.5(4) . . ?
O4 C45 C46 123.7(3) . . ?
O4 C45 C44 115.6(3) . . ?
C46 C45 C44 120.7(3) . . ?
C47 C46 C45 123.6(3) . . ?
C47 C46 H46 118.2 . . ?
C45 C46 H46 118.2 . . ?
O3 C47 C46 123.6(3) . . ?
O3 C47 C48 115.1(3) . . ?
C46 C47 C48 121.3(3) . . ?
C49 C48 C53 117.9(4) . . ?
C49 C48 C47 118.7(3) . . ?
C53 C48 C47 123.3(4) . . ?
C48 C49 C50 122.1(4) . . ?
C48 C49 H49 119.0 . . ?
C50 C49 H49 119.0 . . ?
C51 C50 C49 118.3(5) . . ?
C51 C50 H50 120.8 . . ?
C49 C50 H50 120.8 . . ?
C52 C51 C50 121.0(5) . . ?
C52 C51 H51 119.5 . . ?
C50 C51 H51 119.5 . . ?
C51 C52 C53 120.2(5) . . ?
C51 C52 H52 119.9 . . ?
C53 C52 H52 119.9 . . ?
C48 C53 C52 120.5(5) . . ?
C48 C53 H53 119.7 . . ?
C52 C53 H53 119.7 . . ?
C3 N1 C1 106.1(2) . . ?
C3 N1 Tb1 120.06(19) . . ?
C1 N1 Tb1 133.8(2) . . ?
C8 N2 C4 117.7(3) . . ?
C8 N2 Tb1 122.2(2) . . ?
C4 N2 Tb1 119.61(19) . . ?
C3 N3 C2 107.4(3) . . ?
C3 N3 H3 119(3) . . ?
C2 N3 H3 133(3) . . ?
C15 O1 Tb1 136.10(19) . . ?
C17 O2 Tb1 136.36(19) . . ?
C47 O3 Tb1 134.9(2) . . ?
C45 O4 Tb1 134.0(2) . . ?
C30 O5 Tb1 139.0(2) . . ?
C32 O6 Tb1 135.92(19) . . ?
O2 Tb1 O1 72.71(7) . . ?
O2 Tb1 O5 91.43(8) . . ?
O1 Tb1 O5 79.59(8) . . ?
O2 Tb1 O3 150.54(8) . . ?
O1 Tb1 O3 79.05(8) . . ?
O5 Tb1 O3 75.18(8) . . ?
O2 Tb1 O6 84.79(8) . . ?
O1 Tb1 O6 142.50(8) . . ?
O5 Tb1 O6 71.22(7) . . ?
O3 Tb1 O6 114.23(8) . . ?
O2 Tb1 O4 138.96(7) . . ?
O1 Tb1 O4 141.37(7) . . ?
O5 Tb1 O4 113.04(8) . . ?
O3 Tb1 O4 70.18(8) . . ?
O6 Tb1 O4 73.68(8) . . ?
O2 Tb1 N1 99.61(8) . . ?
O1 Tb1 N1 74.96(8) . . ?
O5 Tb1 N1 147.66(7) . . ?
O3 Tb1 N1 80.61(8) . . ?
O6 Tb1 N1 139.66(8) . . ?
O4 Tb1 N1 77.43(8) . . ?
O2 Tb1 N2 70.17(8) . . ?
O1 Tb1 N2 116.98(7) . . ?
O5 Tb1 N2 148.00(8) . . ?
O3 Tb1 N2 132.47(8) . . ?
O6 Tb1 N2 80.95(7) . . ?
O4 Tb1 N2 72.19(8) . . ?
N1 Tb1 N2 63.61(8) . . ?

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 C2 N3 0.0(4) . . . . ?
N1 C3 C4 N2 3.2(4) . . . . ?
N3 C3 C4 N2 -176.4(3) . . . . ?
N1 C3 C4 C5 -176.7(3) . . . . ?
N3 C3 C4 C5 3.6(5) . . . . ?
N2 C4 C5 C6 -0.3(5) . . . . ?
C3 C4 C5 C6 179.7(3) . . . . ?
C4 C5 C6 C7 1.3(6) . . . . ?
C5 C6 C7 C8 -1.4(6) . . . . ?
C6 C7 C8 N2 0.6(6) . . . . ?
C14 C9 C10 C11 -0.2(6) . . . . ?
C9 C10 C11 C12 -0.5(6) . . . . ?
C10 C11 C12 C13 1.3(6) . . . . ?
C11 C12 C13 C14 -1.4(5) . . . . ?
C10 C9 C14 C13 0.1(5) . . . . ?
C10 C9 C14 C15 -179.9(3) . . . . ?
C12 C13 C14 C9 0.7(5) . . . . ?
C12 C13 C14 C15 -179.3(3) . . . . ?
C9 C14 C15 O1 -24.6(4) . . . . ?
C13 C14 C15 O1 155.3(3) . . . . ?
C9 C14 C15 C16 153.9(3) . . . . ?
C13 C14 C15 C16 -26.2(4) . . . . ?
O1 C15 C16 C17 -1.2(5) . . . . ?
C14 C15 C16 C17 -179.5(3) . . . . ?
C15 C16 C17 O2 2.3(5) . . . . ?
C15 C16 C17 C18 -179.1(3) . . . . ?
O2 C17 C18 C19 -151.4(3) . . . . ?
C16 C17 C18 C19 29.8(5) . . . . ?
O2 C17 C18 C23 28.0(4) . . . . ?
C16 C17 C18 C23 -150.8(3) . . . . ?
C23 C18 C19 C20 2.2(5) . . . . ?
C17 C18 C19 C20 -178.4(3) . . . . ?
C18 C19 C20 C21 -0.6(6) . . . . ?
C19 C20 C21 C22 -1.3(7) . . . . ?
C20 C21 C22 C23 1.5(7) . . . . ?
C19 C18 C23 C22 -2.0(6) . . . . ?
C17 C18 C23 C22 178.6(4) . . . . ?
C21 C22 C23 C18 0.2(7) . . . . ?
C29 C24 C25 C26 -0.6(7) . . . . ?
C24 C25 C26 C27 -0.5(8) . . . . ?
C25 C26 C27 C28 0.9(9) . . . . ?
C26 C27 C28 C29 -0.2(8) . . . . ?
C25 C24 C29 C28 1.3(6) . . . . ?
C25 C24 C29 C30 -178.7(4) . . . . ?
C27 C28 C29 C24 -0.8(6) . . . . ?
C27 C28 C29 C30 179.2(4) . . . . ?
C24 C29 C30 O5 -5.2(5) . . . . ?
C28 C29 C30 O5 174.8(4) . . . . ?
C24 C29 C30 C31 175.3(3) . . . . ?
C28 C29 C30 C31 -4.7(5) . . . . ?
O5 C30 C31 C32 5.5(5) . . . . ?
C29 C30 C31 C32 -174.9(3) . . . . ?
C30 C31 C32 O6 2.1(5) . . . . ?
C30 C31 C32 C33 -177.2(3) . . . . ?
O6 C32 C33 C34 161.7(3) . . . . ?
C31 C32 C33 C34 -19.0(5) . . . . ?
O6 C32 C33 C38 -18.5(4) . . . . ?
C31 C32 C33 C38 160.8(3) . . . . ?
C38 C33 C34 C35 0.5(6) . . . . ?
C32 C33 C34 C35 -179.7(4) . . . . ?
C33 C34 C35 C36 0.2(7) . . . . ?
C34 C35 C36 C37 -0.8(8) . . . . ?
C35 C36 C37 C38 0.8(8) . . . . ?
C36 C37 C38 C33 -0.1(6) . . . . ?
C34 C33 C38 C37 -0.5(5) . . . . ?
C32 C33 C38 C37 179.7(3) . . . . ?
C44 C39 C40 C41 -0.6(6) . . . . ?
C39 C40 C41 C42 -0.7(7) . . . . ?
C40 C41 C42 C43 1.4(8) . . . . ?
C41 C42 C43 C44 -0.8(7) . . . . ?
C42 C43 C44 C39 -0.5(6) . . . . ?
C42 C43 C44 C45 180.0(4) . . . . ?
C40 C39 C44 C43 1.2(6) . . . . ?
C40 C39 C44 C45 -179.3(3) . . . . ?
C43 C44 C45 O4 155.9(3) . . . . ?
C39 C44 C45 O4 -23.5(5) . . . . ?
C43 C44 C45 C46 -24.9(5) . . . . ?
C39 C44 C45 C46 155.7(3) . . . . ?
O4 C45 C46 C47 -2.7(6) . . . . ?
C44 C45 C46 C47 178.1(3) . . . . ?
C45 C46 C47 O3 2.4(5) . . . . ?
C45 C46 C47 C48 -177.0(3) . . . . ?
O3 C47 C48 C49 23.0(5) . . . . ?
C46 C47 C48 C49 -157.5(3) . . . . ?
O3 C47 C48 C53 -154.8(3) . . . . ?
C46 C47 C48 C53 24.7(5) . . . . ?
C53 C48 C49 C50 -0.5(6) . . . . ?
C47 C48 C49 C50 -178.4(3) . . . . ?
C48 C49 C50 C51 1.4(6) . . . . ?
C49 C50 C51 C52 -1.8(8) . . . . ?
C50 C51 C52 C53 1.3(8) . . . . ?
C49 C48 C53 C52 0.0(6) . . . . ?
C47 C48 C53 C52 177.8(4) . . . . ?
C51 C52 C53 C48 -0.4(7) . . . . ?
N3 C3 N1 C1 0.4(4) . . . . ?
C4 C3 N1 C1 -179.4(3) . . . . ?
N3 C3 N1 Tb1 -177.01(19) . . . . ?
C4 C3 N1 Tb1 3.3(4) . . . . ?
C2 C1 N1 C3 -0.2(4) . . . . ?
C2 C1 N1 Tb1 176.6(2) . . . . ?
C7 C8 N2 C4 0.4(5) . . . . ?
C7 C8 N2 Tb1 -172.0(3) . . . . ?
C5 C4 N2 C8 -0.5(5) . . . . ?
C3 C4 N2 C8 179.5(3) . . . . ?
C5 C4 N2 Tb1 172.1(2) . . . . ?
C3 C4 N2 Tb1 -7.9(3) . . . . ?
N1 C3 N3 C2 -0.4(4) . . . . ?
C4 C3 N3 C2 179.3(3) . . . . ?
C1 C2 N3 C3 0.2(4) . . . . ?
C16 C15 O1 Tb1 -11.4(5) . . . . ?
C14 C15 O1 Tb1 166.95(19) . . . . ?
C16 C17 O2 Tb1 9.3(5) . . . . ?
C18 C17 O2 Tb1 -169.4(2) . . . . ?
C46 C47 O3 Tb1 25.0(5) . . . . ?
C48 C47 O3 Tb1 -155.5(2) . . . . ?
C46 C45 O4 Tb1 -23.6(5) . . . . ?
C44 C45 O4 Tb1 155.6(2) . . . . ?
C31 C30 O5 Tb1 3.5(5) . . . . ?
C29 C30 O5 Tb1 -176.0(2) . . . . ?
C31 C32 O6 Tb1 -19.4(5) . . . . ?
C33 C32 O6 Tb1 159.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 O6 0.93 2.60 3.229(4) 125.2 .
N3 H3 O3 0.81(3) 2.27(3) 2.974(4) 146(3) 4_566

_refine_diff_density_max         1.140
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_NH11
_database_code_depnum_ccdc_archive 'CCDC 1868742'
_audit_update_record             
;
2019-01-20 deposited with the CCDC.
2019-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C53 H40 N3 O6 Sm'
_chemical_formula_sum            'C53 H40 N3 O6 Sm'
_chemical_formula_weight         965.23

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'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.1514(18)
_cell_length_b                   22.502(3)
_cell_length_c                   16.201(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.849(4)
_cell_angle_gamma                90
_cell_volume                     4509.6(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9890
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      24.16

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_F_000             1956
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.356
_shelx_estimated_absorpt_T_min   0.822
_shelx_estimated_absorpt_T_max   0.822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6429
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'


_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            56265
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.250
_diffrn_reflns_theta_max         26.799
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9582
_reflns_number_gt                6692
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.

It is noted that there is one high electron density peak near the
atom C20 which is not in a chemically meaningful position. The possible 
reasons for its presence are a)inefficient absoroption correction 
in this heavy atom structure b)due to impurity
in the crystal or c) due to hidden twinning.But it is not giving 
any singificant alert in IUCR CIF-CHECK


;

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0196P)²+3.4065P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9582
_refine_ls_number_parameters     572
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0724
_refine_ls_wR_factor_gt          0.0605
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.4711(3) 0.23353(17) 0.5764(3) 0.0580(11) Uani 1 1 d . . . . .
H1 H 0.5243 0.2328 0.5505 0.070 Uiso 1 1 calc R U . . .
C2 C 0.4790(3) 0.20688(18) 0.6532(3) 0.0619(11) Uani 1 1 d . . . . .
H2 H 0.5372 0.1851 0.6894 0.074 Uiso 1 1 calc R U . . .
C3 C 0.3222(3) 0.25183(14) 0.5983(2) 0.0376(8) Uani 1 1 d . . . . .
C4 C 0.2140(3) 0.27440(14) 0.5839(2) 0.0400(8) Uani 1 1 d . . . . .
C5 C 0.1602(3) 0.26753(17) 0.6433(3) 0.0589(11) Uani 1 1 d . . . . .
H5 H 0.1925 0.2474 0.6958 0.071 Uiso 1 1 calc R U . . .
C6 C 0.0590(4) 0.2909(2) 0.6233(3) 0.0759(13) Uani 1 1 d . . . . .
H6 H 0.0218 0.2873 0.6626 0.091 Uiso 1 1 calc R U . . .
C7 C 0.0127(3) 0.31965(19) 0.5451(3) 0.0739(13) Uani 1 1 d . . . . .
H7 H -0.0568 0.3351 0.5299 0.089 Uiso 1 1 calc R U . . .
C8 C 0.0707(3) 0.32506(17) 0.4902(3) 0.0599(10) Uani 1 1 d . . . . .
H8 H 0.0393 0.3451 0.4375 0.072 Uiso 1 1 calc R U . . .
C9 C -0.0913(3) 0.31535(18) 0.2134(3) 0.0682(12) Uani 1 1 d . . . . .
H9 H -0.0531 0.2960 0.2654 0.082 Uiso 1 1 calc R U . . .
C10 C -0.2016(4) 0.3035(2) 0.1730(4) 0.0890(16) Uani 1 1 d . . . . .
H10 H -0.2371 0.2766 0.1973 0.107 Uiso 1 1 calc R U . . .
C11 C -0.2556(4) 0.3330(3) 0.0965(4) 0.119(2) Uani 1 1 d . . . . .
H11 H -0.3293 0.3265 0.0694 0.143 Uiso 1 1 calc R U . . .
C12 C -0.2045(4) 0.3710(3) 0.0599(4) 0.1088(19) Uani 1 1 d . . . . .
H12 H -0.2425 0.3900 0.0075 0.131 Uiso 1 1 calc R U . . .
C13 C -0.0969(3) 0.3818(2) 0.0995(3) 0.0696(12) Uani 1 1 d . . . . .
H13 H -0.0625 0.4078 0.0730 0.083 Uiso 1 1 calc R U . . .
C14 C -0.0377(3) 0.35534(16) 0.1772(3) 0.0503(9) Uani 1 1 d . . . . .
C15 C 0.0806(3) 0.36620(15) 0.2244(2) 0.0453(9) Uani 1 1 d . . . . .
C16 C 0.1440(3) 0.39238(15) 0.1803(2) 0.0498(9) Uani 1 1 d . . . . .
H16 H 0.1098 0.4043 0.1225 0.060 Uiso 1 1 calc R U . . .
C17 C 0.2547(3) 0.40180(15) 0.2173(2) 0.0451(8) Uani 1 1 d . . . . .
C18 C 0.3166(3) 0.43410(15) 0.1695(2) 0.0492(9) Uani 1 1 d . . . . .
C19 C 0.2729(4) 0.4536(2) 0.0840(3) 0.0900(16) Uani 1 1 d . . . . .
H19 H 0.2005 0.4463 0.0523 0.108 Uiso 1 1 calc R U . . .
C20 C 0.3364(5) 0.4842(3) 0.0449(3) 0.121(2) Uani 1 1 d . . . . .
H20 H 0.3065 0.4969 -0.0129 0.145 Uiso 1 1 calc R U . . .
C21 C 0.4418(5) 0.4954(3) 0.0905(4) 0.110(2) Uani 1 1 d . . . . .
H21 H 0.4832 0.5168 0.0644 0.132 Uiso 1 1 calc R U . . .
C22 C 0.4874(4) 0.4756(2) 0.1743(3) 0.0907(15) Uani 1 1 d . . . . .
H22 H 0.5602 0.4825 0.2052 0.109 Uiso 1 1 calc R U . . .
C23 C 0.4245(3) 0.44547(18) 0.2125(3) 0.0659(11) Uani 1 1 d . . . . .
H23 H 0.4560 0.4321 0.2699 0.079 Uiso 1 1 calc R U . . .
C24 C 0.0814(4) 0.1442(2) 0.3949(3) 0.0798(13) Uani 1 1 d . . . . .
H24 H 0.0757 0.1817 0.4169 0.096 Uiso 1 1 calc R U . . .
C25 C 0.0100(4) 0.0999(3) 0.3982(3) 0.0949(16) Uani 1 1 d . . . . .
H25 H -0.0430 0.1078 0.4228 0.114 Uiso 1 1 calc R U . . .
C26 C 0.0171(5) 0.0449(3) 0.3657(4) 0.110(2) Uani 1 1 d . . . . .
H26 H -0.0306 0.0151 0.3686 0.132 Uiso 1 1 calc R U . . .
C27 C 0.0936(5) 0.0334(2) 0.3290(4) 0.1045(19) Uani 1 1 d . . . . .
H27 H 0.0972 -0.0041 0.3058 0.125 Uiso 1 1 calc R U . . .
C28 C 0.1664(4) 0.07697(19) 0.3258(3) 0.0829(14) Uani 1 1 d . . . . .
H28 H 0.2191 0.0684 0.3011 0.099 Uiso 1 1 calc R U . . .
C29 C 0.1614(4) 0.13330(18) 0.3590(3) 0.0668(12) Uani 1 1 d . . . . .
C30 C 0.2377(3) 0.18228(18) 0.3583(3) 0.0601(11) Uani 1 1 d . . . . .
C31 C 0.3408(3) 0.17019(18) 0.3548(3) 0.0648(11) Uani 1 1 d . . . . .
H31 H 0.3609 0.1305 0.3550 0.078 Uiso 1 1 calc R U . . .
C32 C 0.4151(3) 0.21302(18) 0.3512(2) 0.0559(10) Uani 1 1 d . . . . .
C33 C 0.5216(4) 0.1969(2) 0.3438(3) 0.0644(11) Uani 1 1 d . . . . .
C34 C 0.5397(4) 0.1442(2) 0.3076(3) 0.0893(15) Uani 1 1 d . . . . .
H34 H 0.4846 0.1162 0.2880 0.107 Uiso 1 1 calc R U . . .
C35 C 0.6400(6) 0.1328(3) 0.3003(4) 0.115(2) Uani 1 1 d . . . . .
H35 H 0.6523 0.0969 0.2770 0.137 Uiso 1 1 calc R U . . .
C36 C 0.7199(5) 0.1735(4) 0.3268(4) 0.117(2) Uani 1 1 d . . . . .
H36 H 0.7859 0.1659 0.3196 0.140 Uiso 1 1 calc R U . . .
C37 C 0.7049(4) 0.2262(3) 0.3642(4) 0.1011(18) Uani 1 1 d . . . . .
H37 H 0.7608 0.2536 0.3842 0.121 Uiso 1 1 calc R U . . .
C38 C 0.6047(4) 0.2375(2) 0.3716(3) 0.0767(13) Uani 1 1 d . . . . .
H38 H 0.5934 0.2733 0.3959 0.092 Uiso 1 1 calc R U . . .
C39 C 0.1614(4) 0.4800(2) 0.5776(3) 0.0795(14) Uani 1 1 d . . . . .
H39 H 0.1301 0.4438 0.5550 0.095 Uiso 1 1 calc R U . . .
C40 C 0.1052(4) 0.5194(3) 0.6122(4) 0.0990(17) Uani 1 1 d . . . . .
H40 H 0.0367 0.5096 0.6126 0.119 Uiso 1 1 calc R U . . .
C41 C 0.1504(5) 0.5724(3) 0.6455(3) 0.0984(18) Uani 1 1 d . . . . .
H41 H 0.1137 0.5985 0.6701 0.118 Uiso 1 1 calc R U . . .
C42 C 0.2493(5) 0.5873(2) 0.6427(3) 0.0936(17) Uani 1 1 d . . . . .
H42 H 0.2795 0.6238 0.6648 0.112 Uiso 1 1 calc R U . . .
C43 C 0.3058(3) 0.54868(18) 0.6074(3) 0.0698(12) Uani 1 1 d . . . . .
H43 H 0.3726 0.5598 0.6046 0.084 Uiso 1 1 calc R U . . .
C44 C 0.2629(3) 0.49390(16) 0.5765(2) 0.0513(9) Uani 1 1 d . . . . .
C45 C 0.3204(3) 0.44935(16) 0.5397(2) 0.0462(9) Uani 1 1 d . . . . .
C46 C 0.4332(3) 0.44851(16) 0.5713(2) 0.0514(9) Uani 1 1 d . . . . .
H46 H 0.4687 0.4752 0.6155 0.062 Uiso 1 1 calc R U . . .
C47 C 0.4964(3) 0.41003(15) 0.5408(2) 0.0437(8) Uani 1 1 d . . . . .
C48 C 0.6171(3) 0.41180(16) 0.5815(2) 0.0446(8) Uani 1 1 d . . . . .
C49 C 0.6733(3) 0.46204(17) 0.6198(2) 0.0540(10) Uani 1 1 d . . . . .
H49 H 0.6360 0.4968 0.6220 0.065 Uiso 1 1 calc R U . . .
C50 C 0.7843(3) 0.4611(2) 0.6549(3) 0.0652(11) Uani 1 1 d . . . . .
H50 H 0.8217 0.4955 0.6795 0.078 Uiso 1 1 calc R U . . .
C51 C 0.8403(3) 0.4099(2) 0.6537(3) 0.0706(12) Uani 1 1 d . . . . .
H51 H 0.9153 0.4093 0.6786 0.085 Uiso 1 1 calc R U . . .
C52 C 0.7854(3) 0.3596(2) 0.6157(3) 0.0677(12) Uani 1 1 d . . . . .
H52 H 0.8229 0.3248 0.6144 0.081 Uiso 1 1 calc R U . . .
C53 C 0.6743(3) 0.36096(17) 0.5792(3) 0.0564(10) Uani 1 1 d . . . . .
H53 H 0.6373 0.3269 0.5527 0.068 Uiso 1 1 calc R U . . .
N1 N 0.3733(2) 0.26167(13) 0.54233(18) 0.0467(7) Uani 1 1 d . . . . .
N2 N 0.1695(2) 0.30331(12) 0.50777(18) 0.0438(7) Uani 1 1 d . . . . .
N3 N 0.3838(3) 0.21853(14) 0.6664(2) 0.0547(9) Uani 1 1 d . . . . .
O1 O 0.30958(19) 0.38360(13) 0.29229(17) 0.0670(8) Uani 1 1 d . . . . .
O2 O 0.11558(19) 0.35071(12) 0.30410(17) 0.0578(7) Uani 1 1 d . . . . .
O3 O 0.26199(18) 0.41441(10) 0.48177(16) 0.0488(6) Uani 1 1 d . . . . .
O4 O 0.45780(17) 0.37141(11) 0.48177(16) 0.0520(6) Uani 1 1 d . . . . .
O5 O 0.3973(2) 0.26853(11) 0.35341(17) 0.0589(7) Uani 1 1 d . . . . .
O6 O 0.2033(2) 0.23420(11) 0.36125(17) 0.0590(7) Uani 1 1 d . . . . .
Sm1 Sm 0.28780(2) 0.32857(2) 0.40899(2) 0.03909(6) Uani 1 1 d . . . . .
H3 H 0.366(3) 0.2113(16) 0.710(2) 0.058(12) Uiso 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
C1 C2 1.352(5) . ?
C1 N1 1.370(4) . ?
C1 H1 0.9300 . ?
C2 N3 1.365(5) . ?
C2 H2 0.9300 . ?
C3 N1 1.319(4) . ?
C3 N3 1.353(4) . ?
C3 C4 1.452(4) . ?
C4 N2 1.340(4) . ?
C4 C5 1.382(4) . ?
C5 C6 1.364(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.368(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.360(5) . ?
C7 H7 0.9300 . ?
C8 N2 1.326(4) . ?
C8 H8 0.9300 . ?
C9 C14 1.389(5) . ?
C9 C10 1.400(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.345(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.362(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.501(5) . ?
C15 O2 1.264(4) . ?
C15 C16 1.398(5) . ?
C16 C17 1.390(5) . ?
C16 H16 0.9300 . ?
C17 O1 1.253(4) . ?
C17 C18 1.490(5) . ?
C18 C23 1.376(5) . ?
C18 C19 1.379(5) . ?
C19 C20 1.389(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.354(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.359(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.370(5) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.383(6) . ?
C24 C29 1.384(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.361(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.357(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.383(6) . ?
C27 H27 0.9300 . ?
C28 C29 1.388(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.493(6) . ?
C30 O6 1.260(4) . ?
C30 C31 1.403(5) . ?
C31 C32 1.388(5) . ?
C31 H31 0.9300 . ?
C32 O5 1.273(4) . ?
C32 C33 1.491(5) . ?
C33 C34 1.378(6) . ?
C33 C38 1.379(6) . ?
C34 C35 1.388(7) . ?
C34 H34 0.9300 . ?
C35 C36 1.349(8) . ?
C35 H35 0.9300 . ?
C36 C37 1.376(8) . ?
C36 H36 0.9300 . ?
C37 C38 1.386(6) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 C44 1.378(5) . ?
C39 C40 1.389(6) . ?
C39 H39 0.9300 . ?
C40 C41 1.360(7) . ?
C40 H40 0.9300 . ?
C41 C42 1.358(7) . ?
C41 H41 0.9300 . ?
C42 C43 1.386(6) . ?
C42 H42 0.9300 . ?
C43 C44 1.377(5) . ?
C43 H43 0.9300 . ?
C44 C45 1.495(5) . ?
C45 O3 1.265(4) . ?
C45 C46 1.395(5) . ?
C46 C47 1.401(5) . ?
C46 H46 0.9300 . ?
C47 O4 1.264(4) . ?
C47 C48 1.499(4) . ?
C48 C53 1.376(5) . ?
C48 C49 1.378(5) . ?
C49 C50 1.375(5) . ?
C49 H49 0.9300 . ?
C50 C51 1.371(5) . ?
C50 H50 0.9300 . ?
C51 C52 1.371(5) . ?
C51 H51 0.9300 . ?
C52 C53 1.378(5) . ?
C52 H52 0.9300 . ?
C53 H53 0.9300 . ?
N1 Sm1 2.559(3) . ?
N2 Sm1 2.645(3) . ?
N3 H3 0.83(4) . ?
O1 Sm1 2.358(2) . ?
O2 Sm1 2.377(2) . ?
O3 Sm1 2.347(2) . ?
O4 Sm1 2.351(2) . ?
O5 Sm1 2.365(2) . ?
O6 Sm1 2.399(2) . ?

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
C2 C1 N1 110.1(3) . . ?
C2 C1 H1 124.9 . . ?
N1 C1 H1 124.9 . . ?
C1 C2 N3 105.8(3) . . ?
C1 C2 H2 127.1 . . ?
N3 C2 H2 127.1 . . ?
N1 C3 N3 110.5(3) . . ?
N1 C3 C4 122.1(3) . . ?
N3 C3 C4 127.4(3) . . ?
N2 C4 C5 121.8(3) . . ?
N2 C4 C3 114.6(3) . . ?
C5 C4 C3 123.6(3) . . ?
C6 C5 C4 118.7(4) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C7 119.6(4) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 118.4(4) . . ?
C8 C7 H7 120.8 . . ?
C6 C7 H7 120.8 . . ?
N2 C8 C7 123.6(4) . . ?
N2 C8 H8 118.2 . . ?
C7 C8 H8 118.2 . . ?
C14 C9 C10 121.4(5) . . ?
C14 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C11 C10 C9 117.8(5) . . ?
C11 C10 H10 121.1 . . ?
C9 C10 H10 121.1 . . ?
C12 C11 C10 121.6(5) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 120.0(5) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 122.1(5) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C13 C14 C9 117.2(4) . . ?
C13 C14 C15 124.3(4) . . ?
C9 C14 C15 118.5(4) . . ?
O2 C15 C16 124.3(3) . . ?
O2 C15 C14 115.5(3) . . ?
C16 C15 C14 120.2(3) . . ?
C17 C16 C15 124.3(3) . . ?
C17 C16 H16 117.9 . . ?
C15 C16 H16 117.9 . . ?
O1 C17 C16 122.9(3) . . ?
O1 C17 C18 115.3(3) . . ?
C16 C17 C18 121.8(3) . . ?
C23 C18 C19 117.1(4) . . ?
C23 C18 C17 118.6(3) . . ?
C19 C18 C17 124.3(4) . . ?
C18 C19 C20 120.4(4) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C21 C20 C19 120.4(5) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 120.4(5) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C23 118.9(5) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 H22 120.5 . . ?
C22 C23 C18 122.7(4) . . ?
C22 C23 H23 118.7 . . ?
C18 C23 H23 118.7 . . ?
C25 C24 C29 120.7(5) . . ?
C25 C24 H24 119.6 . . ?
C29 C24 H24 119.6 . . ?
C26 C25 C24 120.2(6) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C27 C26 C25 120.1(6) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C28 120.4(6) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C27 C28 C29 120.6(5) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.7 . . ?
C24 C29 C28 117.9(4) . . ?
C24 C29 C30 118.7(4) . . ?
C28 C29 C30 123.4(5) . . ?
O6 C30 C31 123.1(4) . . ?
O6 C30 C29 115.7(4) . . ?
C31 C30 C29 121.2(4) . . ?
C32 C31 C30 124.8(4) . . ?
C32 C31 H31 117.6 . . ?
C30 C31 H31 117.6 . . ?
O5 C32 C31 122.8(4) . . ?
O5 C32 C33 115.3(4) . . ?
C31 C32 C33 121.9(4) . . ?
C34 C33 C38 118.5(4) . . ?
C34 C33 C32 123.2(5) . . ?
C38 C33 C32 118.3(4) . . ?
C33 C34 C35 120.1(5) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C36 C35 C34 120.5(6) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C35 C36 C37 120.8(6) . . ?
C35 C36 H36 119.6 . . ?
C37 C36 H36 119.6 . . ?
C36 C37 C38 118.6(6) . . ?
C36 C37 H37 120.7 . . ?
C38 C37 H37 120.7 . . ?
C33 C38 C37 121.4(5) . . ?
C33 C38 H38 119.3 . . ?
C37 C38 H38 119.3 . . ?
C44 C39 C40 120.7(5) . . ?
C44 C39 H39 119.6 . . ?
C40 C39 H39 119.6 . . ?
C41 C40 C39 119.9(5) . . ?
C41 C40 H40 120.0 . . ?
C39 C40 H40 120.0 . . ?
C42 C41 C40 119.8(5) . . ?
C42 C41 H41 120.1 . . ?
C40 C41 H41 120.1 . . ?
C41 C42 C43 120.9(5) . . ?
C41 C42 H42 119.5 . . ?
C43 C42 H42 119.5 . . ?
C44 C43 C42 120.0(4) . . ?
C44 C43 H43 120.0 . . ?
C42 C43 H43 120.0 . . ?
C43 C44 C39 118.5(4) . . ?
C43 C44 C45 123.1(4) . . ?
C39 C44 C45 118.4(4) . . ?
O3 C45 C46 124.4(3) . . ?
O3 C45 C44 116.8(3) . . ?
C46 C45 C44 118.7(3) . . ?
C45 C46 C47 124.3(3) . . ?
C45 C46 H46 117.9 . . ?
C47 C46 H46 117.9 . . ?
O4 C47 C46 123.9(3) . . ?
O4 C47 C48 116.3(3) . . ?
C46 C47 C48 119.7(3) . . ?
C53 C48 C49 118.6(3) . . ?
C53 C48 C47 118.2(3) . . ?
C49 C48 C47 123.1(3) . . ?
C50 C49 C48 120.4(4) . . ?
C50 C49 H49 119.8 . . ?
C48 C49 H49 119.8 . . ?
C51 C50 C49 120.4(4) . . ?
C51 C50 H50 119.8 . . ?
C49 C50 H50 119.8 . . ?
C52 C51 C50 119.8(4) . . ?
C52 C51 H51 120.1 . . ?
C50 C51 H51 120.1 . . ?
C51 C52 C53 119.7(4) . . ?
C51 C52 H52 120.2 . . ?
C53 C52 H52 120.2 . . ?
C48 C53 C52 121.1(4) . . ?
C48 C53 H53 119.5 . . ?
C52 C53 H53 119.5 . . ?
C3 N1 C1 105.9(3) . . ?
C3 N1 Sm1 119.9(2) . . ?
C1 N1 Sm1 134.1(2) . . ?
C8 N2 C4 117.8(3) . . ?
C8 N2 Sm1 121.7(2) . . ?
C4 N2 Sm1 119.9(2) . . ?
C3 N3 C2 107.8(3) . . ?
C3 N3 H3 123(3) . . ?
C2 N3 H3 129(3) . . ?
C17 O1 Sm1 139.7(2) . . ?
C15 O2 Sm1 135.7(2) . . ?
C45 O3 Sm1 136.9(2) . . ?
C47 O4 Sm1 136.9(2) . . ?
C32 O5 Sm1 135.4(2) . . ?
C30 O6 Sm1 134.5(3) . . ?
O3 Sm1 O4 71.68(8) . . ?
O3 Sm1 O1 92.77(9) . . ?
O4 Sm1 O1 80.39(9) . . ?
O3 Sm1 O5 150.72(8) . . ?
O4 Sm1 O5 80.03(8) . . ?
O1 Sm1 O5 74.88(9) . . ?
O3 Sm1 O2 85.49(9) . . ?
O4 Sm1 O2 141.76(9) . . ?
O1 Sm1 O2 70.27(8) . . ?
O5 Sm1 O2 113.78(9) . . ?
O3 Sm1 O6 139.47(8) . . ?
O4 Sm1 O6 141.43(8) . . ?
O1 Sm1 O6 112.04(10) . . ?
O5 Sm1 O6 69.32(8) . . ?
O2 Sm1 O6 74.37(9) . . ?
O3 Sm1 N1 99.04(9) . . ?
O4 Sm1 N1 75.36(9) . . ?
O1 Sm1 N1 147.97(8) . . ?
O5 Sm1 N1 80.53(9) . . ?
O2 Sm1 N1 139.97(8) . . ?
O6 Sm1 N1 76.95(9) . . ?
O3 Sm1 N2 69.99(8) . . ?
O4 Sm1 N2 116.05(8) . . ?
O1 Sm1 N2 148.73(9) . . ?
O5 Sm1 N2 131.85(8) . . ?
O2 Sm1 N2 82.19(8) . . ?
O6 Sm1 N2 72.65(9) . . ?
N1 Sm1 N2 62.81(8) . . ?

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 C2 N3 0.4(5) . . . . ?
N1 C3 C4 N2 2.9(5) . . . . ?
N3 C3 C4 N2 -176.2(3) . . . . ?
N1 C3 C4 C5 -176.6(3) . . . . ?
N3 C3 C4 C5 4.3(6) . . . . ?
N2 C4 C5 C6 0.1(6) . . . . ?
C3 C4 C5 C6 179.6(4) . . . . ?
C4 C5 C6 C7 0.9(7) . . . . ?
C5 C6 C7 C8 -1.3(7) . . . . ?
C6 C7 C8 N2 0.8(7) . . . . ?
C14 C9 C10 C11 -0.3(7) . . . . ?
C9 C10 C11 C12 1.5(9) . . . . ?
C10 C11 C12 C13 -1.0(10) . . . . ?
C11 C12 C13 C14 -0.7(9) . . . . ?
C12 C13 C14 C9 1.9(7) . . . . ?
C12 C13 C14 C15 -179.1(4) . . . . ?
C10 C9 C14 C13 -1.3(6) . . . . ?
C10 C9 C14 C15 179.6(4) . . . . ?
C13 C14 C15 O2 162.7(4) . . . . ?
C9 C14 C15 O2 -18.3(5) . . . . ?
C13 C14 C15 C16 -16.7(5) . . . . ?
C9 C14 C15 C16 162.3(3) . . . . ?
O2 C15 C16 C17 3.6(6) . . . . ?
C14 C15 C16 C17 -177.1(3) . . . . ?
C15 C16 C17 O1 5.3(6) . . . . ?
C15 C16 C17 C18 -175.2(3) . . . . ?
O1 C17 C18 C23 -5.1(5) . . . . ?
C16 C17 C18 C23 175.4(4) . . . . ?
O1 C17 C18 C19 174.9(4) . . . . ?
C16 C17 C18 C19 -4.6(6) . . . . ?
C23 C18 C19 C20 -0.9(7) . . . . ?
C17 C18 C19 C20 179.1(5) . . . . ?
C18 C19 C20 C21 -0.4(9) . . . . ?
C19 C20 C21 C22 1.8(10) . . . . ?
C20 C21 C22 C23 -1.6(9) . . . . ?
C21 C22 C23 C18 0.2(8) . . . . ?
C19 C18 C23 C22 1.0(7) . . . . ?
C17 C18 C23 C22 -179.0(4) . . . . ?
C29 C24 C25 C26 -0.4(8) . . . . ?
C24 C25 C26 C27 -0.7(9) . . . . ?
C25 C26 C27 C28 1.3(9) . . . . ?
C26 C27 C28 C29 -0.8(8) . . . . ?
C25 C24 C29 C28 0.8(7) . . . . ?
C25 C24 C29 C30 -179.0(4) . . . . ?
C27 C28 C29 C24 -0.2(7) . . . . ?
C27 C28 C29 C30 179.5(4) . . . . ?
C24 C29 C30 O6 -24.0(6) . . . . ?
C28 C29 C30 O6 156.2(4) . . . . ?
C24 C29 C30 C31 155.8(4) . . . . ?
C28 C29 C30 C31 -24.0(6) . . . . ?
O6 C30 C31 C32 -2.3(7) . . . . ?
C29 C30 C31 C32 177.9(4) . . . . ?
C30 C31 C32 O5 2.2(6) . . . . ?
C30 C31 C32 C33 -177.3(4) . . . . ?
O5 C32 C33 C34 -154.2(4) . . . . ?
C31 C32 C33 C34 25.4(6) . . . . ?
O5 C32 C33 C38 23.5(5) . . . . ?
C31 C32 C33 C38 -157.0(4) . . . . ?
C38 C33 C34 C35 0.4(7) . . . . ?
C32 C33 C34 C35 178.0(4) . . . . ?
C33 C34 C35 C36 -1.4(9) . . . . ?
C34 C35 C36 C37 2.2(10) . . . . ?
C35 C36 C37 C38 -2.1(9) . . . . ?
C34 C33 C38 C37 -0.3(7) . . . . ?
C32 C33 C38 C37 -178.0(4) . . . . ?
C36 C37 C38 C33 1.1(8) . . . . ?
C44 C39 C40 C41 0.0(8) . . . . ?
C39 C40 C41 C42 1.7(9) . . . . ?
C40 C41 C42 C43 -0.9(8) . . . . ?
C41 C42 C43 C44 -1.6(7) . . . . ?
C42 C43 C44 C39 3.2(6) . . . . ?
C42 C43 C44 C45 -178.4(4) . . . . ?
C40 C39 C44 C43 -2.4(7) . . . . ?
C40 C39 C44 C45 179.1(4) . . . . ?
C43 C44 C45 O3 -150.4(4) . . . . ?
C39 C44 C45 O3 28.0(5) . . . . ?
C43 C44 C45 C46 30.0(5) . . . . ?
C39 C44 C45 C46 -151.5(4) . . . . ?
O3 C45 C46 C47 2.1(6) . . . . ?
C44 C45 C46 C47 -178.4(3) . . . . ?
C45 C46 C47 O4 -0.7(6) . . . . ?
C45 C46 C47 C48 -178.2(3) . . . . ?
O4 C47 C48 C53 -24.4(5) . . . . ?
C46 C47 C48 C53 153.3(4) . . . . ?
O4 C47 C48 C49 154.7(3) . . . . ?
C46 C47 C48 C49 -27.6(5) . . . . ?
C53 C48 C49 C50 0.1(6) . . . . ?
C47 C48 C49 C50 -179.0(3) . . . . ?
C48 C49 C50 C51 -1.3(6) . . . . ?
C49 C50 C51 C52 1.4(7) . . . . ?
C50 C51 C52 C53 -0.3(7) . . . . ?
C49 C48 C53 C52 1.1(6) . . . . ?
C47 C48 C53 C52 -179.8(4) . . . . ?
C51 C52 C53 C48 -1.0(6) . . . . ?
N3 C3 N1 C1 0.0(4) . . . . ?
C4 C3 N1 C1 -179.3(3) . . . . ?
N3 C3 N1 Sm1 -176.2(2) . . . . ?
C4 C3 N1 Sm1 4.5(4) . . . . ?
C2 C1 N1 C3 -0.2(4) . . . . ?
C2 C1 N1 Sm1 175.2(3) . . . . ?
C7 C8 N2 C4 0.1(6) . . . . ?
C7 C8 N2 Sm1 -171.1(3) . . . . ?
C5 C4 N2 C8 -0.6(5) . . . . ?
C3 C4 N2 C8 179.9(3) . . . . ?
C5 C4 N2 Sm1 170.8(3) . . . . ?
C3 C4 N2 Sm1 -8.7(4) . . . . ?
N1 C3 N3 C2 0.3(4) . . . . ?
C4 C3 N3 C2 179.5(3) . . . . ?
C1 C2 N3 C3 -0.4(4) . . . . ?
C16 C17 O1 Sm1 2.3(6) . . . . ?
C18 C17 O1 Sm1 -177.2(3) . . . . ?
C16 C15 O2 Sm1 -20.6(5) . . . . ?
C14 C15 O2 Sm1 160.1(2) . . . . ?
C46 C45 O3 Sm1 9.2(6) . . . . ?
C44 C45 O3 Sm1 -170.3(2) . . . . ?
C46 C47 O4 Sm1 -12.2(6) . . . . ?
C48 C47 O4 Sm1 165.3(2) . . . . ?
C31 C32 O5 Sm1 25.3(6) . . . . ?
C33 C32 O5 Sm1 -155.2(3) . . . . ?
C31 C30 O6 Sm1 -24.2(6) . . . . ?
C29 C30 O6 Sm1 155.6(3) . . . . ?

_refine_diff_density_max         0.940
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.073

