# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_c
_database_code_depnum_ccdc_archive 'CCDC 1061273'
_audit_update_record             
;
2015-04-23 deposited with the CCDC.
2016-09-27 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         ?
_chemical_formula_sum            'C60 H66 N9 O13 Sm'
_chemical_formula_weight         1271.56

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   12.4150(18)
_cell_length_b                   15.719(2)
_cell_length_c                   16.661(2)
_cell_angle_alpha                97.375(2)
_cell_angle_beta                 103.260(2)
_cell_angle_gamma                105.382(2)
_cell_volume                     2988.8(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_F_000             1310
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.053
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15826
_diffrn_reflns_av_unetI/netI     0.1191
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.282
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             10670
_reflns_number_gt                6278
_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0853P)²] 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         10670
_refine_ls_number_parameters     778
_refine_ls_number_restraints     92
_refine_ls_R_factor_all          0.1195
_refine_ls_R_factor_gt           0.0709
_refine_ls_wR_factor_ref         0.1923
_refine_ls_wR_factor_gt          0.1617
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.071
_refine_ls_shift/su_mean         0.001

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 0.6302(3) 0.4632(2) 0.3061(2) 0.0591(12) Uani 1 1 d . . . . .
H1 H 0.6180 0.4469 0.2483 0.071 Uiso 1 1 calc R U . . .
C2 C 0.6780(3) 0.5516(2) 0.3424(2) 0.0720(14) Uani 1 1 d . . . . .
H2 H 0.6973 0.5947 0.3105 0.086 Uiso 1 1 calc R U . . .
C3 C 0.6970(3) 0.5756(2) 0.4279(2) 0.0850(16) Uani 1 1 d . . . . .
H3 H 0.7306 0.6357 0.4550 0.102 Uiso 1 1 calc R U . . .
C4 C 0.6668(3) 0.5115(2) 0.4723(2) 0.0741(14) Uani 1 1 d . . . . .
H4 H 0.6783 0.5272 0.5301 0.089 Uiso 1 1 calc R U . . .
C5 C 0.6184(2) 0.42221(19) 0.43108(19) 0.0491(10) Uani 1 1 d . . . . .
C6 C 0.5850(2) 0.3488(2) 0.47719(18) 0.0513(11) Uani 1 1 d . . . . .
H6 H 0.5781 0.3746 0.5319 0.062 Uiso 1 1 calc R U . . .
C7 C 0.4065(3) 0.24796(19) 0.46937(18) 0.0505(10) Uani 1 1 d . . . . .
H7 H 0.4328 0.2684 0.5274 0.061 Uiso 1 1 calc R U . . .
C8 C 0.2937(3) 0.1787(2) 0.43768(18) 0.0508(10) Uani 1 1 d . . . . .
C9 C 0.2360(3) 0.1489(2) 0.4969(2) 0.0673(13) Uani 1 1 d . . . . .
H9 H 0.2717 0.1731 0.5538 0.081 Uiso 1 1 calc R U . . .
C10 C 0.1306(3) 0.0863(3) 0.4740(2) 0.0783(14) Uani 1 1 d . . . . .
H10 H 0.0960 0.0646 0.5143 0.094 Uiso 1 1 calc R U . . .
C11 C 0.0753(3) 0.0554(3) 0.3888(2) 0.0791(14) Uani 1 1 d . . . . .
H11 H 0.0017 0.0134 0.3720 0.095 Uiso 1 1 calc R U . . .
C12 C 0.1265(3) 0.0851(2) 0.3284(2) 0.0660(13) Uani 1 1 d . . . . .
C13 C 0.2420(2) 0.14470(18) 0.35064(18) 0.0448(9) Uani 1 1 d . . . . .
C14 C -0.0529(4) 0.0302(3) 0.2173(3) 0.107(2) Uani 1 1 d . . . . .
H14A H -0.0783 -0.0320 0.2234 0.129 Uiso 1 1 calc R U . . .
H14B H -0.0839 0.0655 0.2529 0.129 Uiso 1 1 calc R U . . .
C15 C -0.0946(4) 0.0362(3) 0.1316(3) 0.138(3) Uani 1 1 d . . . . .
H15A H -0.0917 0.0973 0.1285 0.207 Uiso 1 1 calc R U . . .
H15B H -0.1734 -0.0023 0.1090 0.207 Uiso 1 1 calc R U . . .
H15C H -0.0468 0.0175 0.0995 0.207 Uiso 1 1 calc R U . . .
C16 C 0.4096(3) 0.0118(2) 0.3318(2) 0.0713(14) Uani 1 1 d . . . . .
H16 H 0.3385 0.0126 0.2988 0.086 Uiso 1 1 calc R U . . .
C17 C 0.4141(4) -0.0652(3) 0.3592(3) 0.1009(19) Uani 1 1 d . . . . .
H17 H 0.3491 -0.1156 0.3468 0.121 Uiso 1 1 calc R U . . .
C18 C 0.5218(4) -0.0636(3) 0.4067(3) 0.140(2) Uani 1 1 d . . . . .
H18 H 0.5293 -0.1151 0.4264 0.168 Uiso 1 1 calc R U . . .
C19 C 0.6178(4) 0.0102(2) 0.4262(3) 0.1113(19) Uani 1 1 d . . . . .
H19 H 0.6896 0.0098 0.4582 0.134 Uiso 1 1 calc R U . . .
C20 C 0.6033(3) 0.0847(2) 0.3964(2) 0.0626(12) Uani 1 1 d . . . . .
C21 C 0.7063(3) 0.1668(2) 0.4074(2) 0.0774(14) Uani 1 1 d . . . . .
H21A H 0.7636 0.1730 0.4601 0.093 Uiso 1 1 calc R U . . .
H21B H 0.7419 0.1586 0.3621 0.093 Uiso 1 1 calc R U . . .
C22 C 0.6714(3) 0.29006(19) 0.49105(19) 0.0545(11) Uani 1 1 d . . . . .
H22 H 0.6381 0.2416 0.5181 0.065 Uiso 1 1 calc R U . . .
C23 C 0.7886(3) 0.3453(2) 0.5497(2) 0.0580(11) Uani 1 1 d . . . . .
C24 C 0.8806(3) 0.3896(3) 0.5204(2) 0.0953(18) Uani 1 1 d . . . . .
H24 H 0.8699 0.3855 0.4628 0.114 Uiso 1 1 calc R U . . .
C25 C 0.9881(4) 0.4399(3) 0.5755(3) 0.109(2) Uani 1 1 d . . . . .
H25 H 1.0490 0.4689 0.5554 0.130 Uiso 1 1 calc R U . . .
C26 C 1.0018(3) 0.4456(3) 0.6625(3) 0.0960(17) Uani 1 1 d . . . . .
H26 H 1.0725 0.4797 0.7003 0.115 Uiso 1 1 calc R U . . .
C27 C 0.9130(3) 0.4019(2) 0.6924(2) 0.0683(12) Uani 1 1 d . . . . .
C28 C 0.8074(3) 0.3521(2) 0.6349(2) 0.0572(11) Uani 1 1 d . . . . .
C29 C 1.0363(4) 0.4383(3) 0.8343(2) 0.118(2) Uani 1 1 d . . . . .
H29A H 1.0895 0.4087 0.8180 0.142 Uiso 1 1 calc R U . . .
H29B H 1.0661 0.5020 0.8348 0.142 Uiso 1 1 calc R U . . .
C30 C 1.0266(5) 0.4255(3) 0.9151(3) 0.165(3) Uani 1 1 d . . . . .
H30A H 0.9864 0.4644 0.9353 0.247 Uiso 1 1 calc R U . . .
H30B H 1.1028 0.4396 0.9530 0.247 Uiso 1 1 calc R U . . .
H30C H 0.9839 0.3639 0.9118 0.247 Uiso 1 1 calc R U . . .
C31 C 0.3195(3) 0.3826(2) 0.2842(2) 0.0604(11) Uani 1 1 d . . . . .
H31 H 0.3335 0.3731 0.3391 0.072 Uiso 1 1 calc R U . . .
C32 C 0.2627(3) 0.4435(2) 0.2646(2) 0.0883(14) Uani 1 1 d . . . . .
H32 H 0.2401 0.4753 0.3054 0.106 Uiso 1 1 calc R U . . .
C33 C 0.2397(4) 0.4568(2) 0.1846(3) 0.0963(16) Uani 1 1 d . . . . .
H33 H 0.2001 0.4974 0.1691 0.116 Uiso 1 1 calc R U . . .
C34 C 0.2774(3) 0.4076(2) 0.1246(2) 0.0754(14) Uani 1 1 d . . . . .
H34 H 0.2630 0.4153 0.0691 0.090 Uiso 1 1 calc R U . . .
C35 C 0.3347(3) 0.34949(19) 0.15028(18) 0.0509(10) Uani 1 1 d . . . . .
C36 C 0.3776(3) 0.2955(2) 0.09081(19) 0.0555(11) Uani 1 1 d . . . . .
H36 H 0.3848 0.3243 0.0427 0.067 Uiso 1 1 calc R U . . .
C37 C 0.5672(3) 0.3034(2) 0.09398(19) 0.0588(12) Uani 1 1 d . . . . .
H37 H 0.5439 0.3168 0.0412 0.071 Uiso 1 1 calc R U . . .
C38 C 0.6851(3) 0.3005(2) 0.12010(19) 0.0611(12) Uani 1 1 d . . . . .
C39 C 0.7570(3) 0.3220(2) 0.0656(2) 0.0861(15) Uani 1 1 d . . . . .
H39 H 0.7271 0.3363 0.0143 0.103 Uiso 1 1 calc R U . . .
C40 C 0.8706(3) 0.3216(3) 0.0884(3) 0.1169(18) Uani 1 1 d . . . . .
H40 H 0.9169 0.3343 0.0522 0.140 Uiso 1 1 calc R U . . .
C41 C 0.9160(3) 0.3022(3) 0.1661(3) 0.1032(17) Uani 1 1 d . . . . .
H41 H 0.9932 0.3029 0.1815 0.124 Uiso 1 1 calc R U . . .
C42 C 0.8490(3) 0.2820(2) 0.2203(3) 0.0831(15) Uani 1 1 d . . . . .
C43 C 0.7277(3) 0.2773(2) 0.1965(2) 0.0580(11) Uani 1 1 d . . . . .
C44 C 1.0092(3) 0.2803(3) 0.3272(3) 0.141(2) Uani 1 1 d . . . . .
H44A H 1.0329 0.2360 0.2952 0.170 Uiso 1 1 calc R U . . .
H44B H 1.0501 0.3395 0.3203 0.170 Uiso 1 1 calc R U . . .
C45 C 1.0374(4) 0.2758(4) 0.4082(4) 0.254(3) Uani 1 1 d . . . . .
H45A H 1.0184 0.3220 0.4404 0.381 Uiso 1 1 calc R U . . .
H45B H 1.1193 0.2841 0.4274 0.381 Uiso 1 1 calc R U . . .
H45C H 0.9950 0.2178 0.4153 0.381 Uiso 1 1 calc R U . . .
C46 C 0.5582(3) 0.0444(2) 0.1663(2) 0.0808(15) Uani 1 1 d . . . . .
H46 H 0.6293 0.0798 0.2028 0.097 Uiso 1 1 calc R U . . .
C47 C 0.5560(3) -0.0346(3) 0.1204(3) 0.0975(17) Uani 1 1 d . . . . .
H47 H 0.6228 -0.0522 0.1254 0.117 Uiso 1 1 calc R U . . .
C48 C 0.4550(4) -0.0854(3) 0.0684(3) 0.1195(19) Uani 1 1 d . . . . .
H48 H 0.4490 -0.1412 0.0380 0.143 Uiso 1 1 calc R U . . .
C49 C 0.3558(3) -0.0549(2) 0.0588(2) 0.0849(15) Uani 1 1 d . . . . .
H49 H 0.2860 -0.0876 0.0193 0.102 Uiso 1 1 calc R U . . .
C50 C 0.3663(3) 0.0252(2) 0.11022(19) 0.0558(11) Uani 1 1 d . . . . .
C51 C 0.2625(2) 0.0563(2) 0.1109(2) 0.0543(11) Uani 1 1 d . . . . .
H51A H 0.2066 0.0348 0.0559 0.065 Uiso 1 1 calc R U . . .
H51B H 0.2258 0.0309 0.1516 0.065 Uiso 1 1 calc R U . . .
C52 C 0.2985(3) 0.1962(2) 0.05937(17) 0.0510(10) Uani 1 1 d . . . . .
H52 H 0.3370 0.1651 0.0256 0.061 Uiso 1 1 calc R U . . .
C53 C 0.1822(3) 0.1913(2) 0.00141(17) 0.0508(11) Uani 1 1 d . . . . .
C54 C 0.0831(3) 0.1788(2) 0.0273(2) 0.0625(12) Uani 1 1 d . . . . .
H54 H 0.0847 0.1727 0.0823 0.075 Uiso 1 1 calc R U . . .
C55 C -0.0203(3) 0.1755(3) -0.0299(3) 0.0861(16) Uani 1 1 d . . . . .
H55 H -0.0870 0.1693 -0.0117 0.103 Uiso 1 1 calc R U . . .
C56 C -0.0265(3) 0.1813(2) -0.1123(2) 0.0744(14) Uani 1 1 d . . . . .
H56 H -0.0971 0.1761 -0.1498 0.089 Uiso 1 1 calc R U . . .
C57 C 0.0708(3) 0.1946(2) -0.1384(2) 0.0626(12) Uani 1 1 d . . . . .
C58 C 0.1763(3) 0.1994(2) -0.0797(2) 0.0589(11) Uani 1 1 d . . . . .
C59 C -0.0255(3) 0.1898(3) -0.2816(2) 0.0992(16) Uani 1 1 d . . . . .
H59A H -0.0649 0.2322 -0.2658 0.119 Uiso 1 1 calc R U . . .
H59B H -0.0771 0.1292 -0.2891 0.119 Uiso 1 1 calc R U . . .
C60 C 0.0058(4) 0.2037(3) -0.3603(2) 0.135(2) Uani 1 1 d . . . . .
H60A H 0.0568 0.2638 -0.3521 0.203 Uiso 1 1 calc R U . . .
H60B H -0.0633 0.1951 -0.4046 0.203 Uiso 1 1 calc R U . . .
H60C H 0.0444 0.1611 -0.3754 0.203 Uiso 1 1 calc R U . . .
N1 N 0.59921(19) 0.39755(15) 0.34794(14) 0.0486(8) Uani 1 1 d . . . . .
N2 N 0.4721(2) 0.28301(15) 0.42783(14) 0.0459(8) Uani 1 1 d . . . . .
N3 N 0.4998(2) 0.08648(16) 0.34882(16) 0.0599(10) Uani 1 1 d . . . . .
N4 N 0.6722(2) 0.24843(15) 0.40752(15) 0.0528(9) Uani 1 1 d . . . . .
H4B H 0.7362 0.2914 0.3949 0.063 Uiso 1 1 calc R U . . .
N5 N 0.3563(2) 0.33572(16) 0.22967(15) 0.0502(8) Uani 1 1 d . . . . .
N6 N 0.4904(2) 0.28958(16) 0.13546(14) 0.0496(8) Uani 1 1 d . . . . .
N7 N 0.4675(2) 0.07598(17) 0.16354(16) 0.0596(9) Uani 1 1 d . . . . .
N8 N 0.2950(2) 0.15417(15) 0.13235(13) 0.0446(8) Uani 1 1 d . . . . .
H8A H 0.2297 0.1663 0.1502 0.054 Uiso 1 1 calc R U . . .
Sm1 Sm 0.48152(2) 0.22589(2) 0.27254(2) 0.04809(5) Uani 1 1 d . . . . .
O2 O 0.29442(16) 0.16476(13) 0.29451(11) 0.0506(7) Uani 1 1 d . . . . .
O1 O 0.0732(2) 0.06402(18) 0.24251(15) 0.0859(10) Uani 1 1 d . . . . .
O4 O 0.7205(2) 0.30857(17) 0.66168(14) 0.0869(11) Uani 1 1 d . . . . .
H4A H 0.7402 0.3178 0.7133 0.130 Uiso 1 1 calc R U . . .
O3 O 0.9216(2) 0.40024(17) 0.77482(15) 0.0941(11) Uani 1 1 d . . . . .
O6 O 0.66719(17) 0.25345(14) 0.24756(13) 0.0586(8) Uani 1 1 d . . . . .
O5 O 0.8868(2) 0.26386(19) 0.29553(19) 0.1028(12) Uani 1 1 d . . . . .
O8 O 0.27389(19) 0.20683(17) -0.10628(14) 0.0773(9) Uani 1 1 d . . . . .
H8 H 0.2751 0.2390 -0.1413 0.116 Uiso 1 1 calc R U . . .
O7 O 0.0797(2) 0.20330(17) -0.21801(14) 0.0868(10) Uani 1 1 d . . . . .
N9 N 0.4342(4) 0.2737(5) 0.7727(3) 0.3493(12) Uani 1 1 d D U . . .
O9 O 0.4754(4) 0.2741(4) 0.7079(2) 0.352(2) Uani 1 1 d D U . . .
O10 O 0.5122(7) 0.3177(9) 0.8425(4) 0.3518(18) Uani 0.5 1 d D U P A 1
O11' O 0.3201(5) 0.2418(8) 0.7469(6) 0.3341(18) Uani 0.5 1 d D U P A 1
O10' O 0.4813(8) 0.3454(5) 0.8327(4) 0.3550(18) Uani 0.5 1 d D U P A 2
O11 O 0.3265(4) 0.2629(9) 0.7566(6) 0.3350(18) Uani 0.5 1 d D U P A 2
O1W O 0.6937(4) 0.2903(4) 0.8190(2) 0.251(3) Uani 1 1 d . . . . .
H1WA H 0.6656 0.3272 0.8423 0.376 Uiso 1 1 d R U . . .
H1WB H 0.7618 0.3192 0.8185 0.376 Uiso 1 1 d R U . . .
O2W O 0.4027(3) 0.4541(3) 0.9128(3) 0.330(5) Uani 1 1 d D . . . .
H2WA H 0.4508(3) 0.4313(5) 0.8968(6) 0.496 Uiso 1 1 d D U . . .
H2WB H 0.3396(4) 0.4459(9) 0.8757(5) 0.496 Uiso 1 1 d D U . . .


_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 N1 1.340(4) . ?
C1 C2 1.353(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.350(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(4) . ?
C4 H4 0.9300 . ?
C5 N1 1.337(4) . ?
C5 C6 1.488(4) . ?
C6 N2 1.482(3) . ?
C6 C22 1.588(5) . ?
C6 H6 0.9800 . ?
C7 N2 1.250(4) . ?
C7 C8 1.459(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.403(5) . ?
C8 C13 1.412(4) . ?
C9 C10 1.348(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.386(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(5) . ?
C11 H11 0.9300 . ?
C12 O1 1.386(4) . ?
C12 C13 1.423(4) . ?
C13 O2 1.282(4) . ?
C14 C15 1.428(6) . ?
C14 O1 1.453(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N3 1.336(4) . ?
C16 C17 1.357(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.381(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.365(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(5) . ?
C19 H19 0.9300 . ?
C20 N3 1.356(4) . ?
C20 C21 1.512(4) . ?
C21 N4 1.454(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 N4 1.464(4) . ?
C22 C23 1.512(4) . ?
C22 H22 0.9800 . ?
C23 C28 1.371(5) . ?
C23 C24 1.395(5) . ?
C24 C25 1.393(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.408(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.368(6) . ?
C26 H26 0.9300 . ?
C27 O3 1.357(4) . ?
C27 C28 1.391(4) . ?
C28 O4 1.319(4) . ?
C29 C30 1.413(6) . ?
C29 O3 1.454(5) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 N5 1.332(4) . ?
C31 C32 1.361(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.353(6) . ?
C32 H32 0.9300 . ?
C33 C34 1.423(6) . ?
C33 H33 0.9300 . ?
C34 C35 1.353(5) . ?
C34 H34 0.9300 . ?
C35 N5 1.345(4) . ?
C35 C36 1.500(5) . ?
C36 N6 1.461(4) . ?
C36 C52 1.555(4) . ?
C36 H36 0.9800 . ?
C37 N6 1.290(4) . ?
C37 C38 1.443(5) . ?
C37 H37 0.9300 . ?
C38 C43 1.396(5) . ?
C38 C39 1.424(5) . ?
C39 C40 1.375(6) . ?
C39 H39 0.9300 . ?
C40 C41 1.395(6) . ?
C40 H40 0.9300 . ?
C41 C42 1.374(6) . ?
C41 H41 0.9300 . ?
C42 O5 1.328(5) . ?
C42 C43 1.445(5) . ?
C43 O6 1.286(4) . ?
C44 C45 1.331(9) . ?
C44 O5 1.429(4) . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C46 N7 1.340(5) . ?
C46 C47 1.363(5) . ?
C46 H46 0.9300 . ?
C47 C48 1.325(5) . ?
C47 H47 0.9300 . ?
C48 C49 1.419(6) . ?
C48 H48 0.9300 . ?
C49 C50 1.385(5) . ?
C49 H49 0.9300 . ?
C50 N7 1.334(3) . ?
C50 C51 1.497(5) . ?
C51 N8 1.457(4) . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
C52 N8 1.460(4) . ?
C52 C53 1.519(4) . ?
C52 H52 0.9800 . ?
C53 C58 1.361(4) . ?
C53 C54 1.369(5) . ?
C54 C55 1.397(5) . ?
C54 H54 0.9300 . ?
C55 C56 1.373(6) . ?
C55 H55 0.9300 . ?
C56 C57 1.349(5) . ?
C56 H56 0.9300 . ?
C57 O7 1.377(4) . ?
C57 C58 1.420(4) . ?
C58 O8 1.364(4) . ?
C59 O7 1.426(4) . ?
C59 C60 1.477(6) . ?
C59 H59A 0.9700 . ?
C59 H59B 0.9700 . ?
C60 H60A 0.9600 . ?
C60 H60B 0.9600 . ?
C60 H60C 0.9600 . ?
N1 Sm1 2.681(2) . ?
N2 Sm1 2.667(2) . ?
N3 Sm1 2.705(3) . ?
N4 Sm1 2.774(2) . ?
N4 H4B 0.9800 . ?
N5 Sm1 2.672(3) . ?
N6 Sm1 2.622(3) . ?
N7 Sm1 2.724(3) . ?
N8 Sm1 2.7470(19) . ?
N8 H8A 0.9800 . ?
Sm1 O6 2.373(2) . ?
Sm1 O2 2.398(2) . ?
O4 H4A 0.8200 . ?
O8 H8 0.8200 . ?
N9 O11 1.262(7) . ?
N9 O9 1.296(7) . ?
N9 O10 1.300(7) . ?
N9 O10' 1.306(8) . ?
N9 O11' 1.316(7) . ?
O1W H1WA 0.8482 . ?
O1W H1WB 0.8500 . ?
O2W H2WA 0.847(7) . ?
O2W H2WB 0.846(6) . ?

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
N1 C1 C2 124.3(3) . . ?
N1 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?
C1 C2 C3 117.9(3) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 119.4(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 121.8(3) . . ?
N1 C5 C6 116.6(2) . . ?
C4 C5 C6 121.6(3) . . ?
N2 C6 C5 109.9(2) . . ?
N2 C6 C22 104.2(2) . . ?
C5 C6 C22 114.6(3) . . ?
N2 C6 H6 109.3 . . ?
C5 C6 H6 109.3 . . ?
C22 C6 H6 109.3 . . ?
N2 C7 C8 127.8(3) . . ?
N2 C7 H7 116.1 . . ?
C8 C7 H7 116.1 . . ?
C9 C8 C13 120.8(2) . . ?
C9 C8 C7 117.6(3) . . ?
C13 C8 C7 121.6(3) . . ?
C10 C9 C8 122.2(3) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C9 C10 C11 118.1(4) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
C12 C11 C10 121.8(3) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 O1 125.3(3) . . ?
C11 C12 C13 121.2(3) . . ?
O1 C12 C13 113.4(3) . . ?
O2 C13 C8 123.1(2) . . ?
O2 C13 C12 121.4(2) . . ?
C8 C13 C12 115.5(3) . . ?
C15 C14 O1 108.9(4) . . ?
C15 C14 H14A 109.9 . . ?
O1 C14 H14A 109.9 . . ?
C15 C14 H14B 109.9 . . ?
O1 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C17 124.7(3) . . ?
N3 C16 H16 117.7 . . ?
C17 C16 H16 117.7 . . ?
C16 C17 C18 115.5(4) . . ?
C16 C17 H17 122.2 . . ?
C18 C17 H17 122.2 . . ?
C19 C18 C17 122.9(4) . . ?
C19 C18 H18 118.5 . . ?
C17 C18 H18 118.5 . . ?
C18 C19 C20 116.9(4) . . ?
C18 C19 H19 121.6 . . ?
C20 C19 H19 121.6 . . ?
N3 C20 C19 122.6(3) . . ?
N3 C20 C21 116.2(3) . . ?
C19 C20 C21 120.9(3) . . ?
N4 C21 C20 111.6(3) . . ?
N4 C21 H21A 109.3 . . ?
C20 C21 H21A 109.3 . . ?
N4 C21 H21B 109.3 . . ?
C20 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
N4 C22 C23 115.8(3) . . ?
N4 C22 C6 107.0(2) . . ?
C23 C22 C6 111.2(2) . . ?
N4 C22 H22 107.5 . . ?
C23 C22 H22 107.5 . . ?
C6 C22 H22 107.5 . . ?
C28 C23 C24 117.8(3) . . ?
C28 C23 C22 119.7(3) . . ?
C24 C23 C22 122.5(3) . . ?
C25 C24 C23 121.5(4) . . ?
C25 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?
C24 C25 C26 118.1(4) . . ?
C24 C25 H25 120.9 . . ?
C26 C25 H25 120.9 . . ?
C27 C26 C25 121.2(3) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
O3 C27 C26 124.6(3) . . ?
O3 C27 C28 116.8(3) . . ?
C26 C27 C28 118.6(3) . . ?
O4 C28 C23 117.2(2) . . ?
O4 C28 C27 120.1(3) . . ?
C23 C28 C27 122.7(3) . . ?
C30 C29 O3 108.4(4) . . ?
C30 C29 H29A 110.0 . . ?
O3 C29 H29A 110.0 . . ?
C30 C29 H29B 110.0 . . ?
O3 C29 H29B 110.0 . . ?
H29A C29 H29B 108.4 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N5 C31 C32 124.1(3) . . ?
N5 C31 H31 117.9 . . ?
C32 C31 H31 117.9 . . ?
C33 C32 C31 118.7(4) . . ?
C33 C32 H32 120.6 . . ?
C31 C32 H32 120.6 . . ?
C32 C33 C34 118.7(4) . . ?
C32 C33 H33 120.7 . . ?
C34 C33 H33 120.7 . . ?
C35 C34 C33 118.4(3) . . ?
C35 C34 H34 120.8 . . ?
C33 C34 H34 120.8 . . ?
N5 C35 C34 122.8(3) . . ?
N5 C35 C36 115.7(3) . . ?
C34 C35 C36 121.5(3) . . ?
N6 C36 C35 109.0(2) . . ?
N6 C36 C52 104.9(3) . . ?
C35 C36 C52 112.9(3) . . ?
N6 C36 H36 110.0 . . ?
C35 C36 H36 110.0 . . ?
C52 C36 H36 110.0 . . ?
N6 C37 C38 127.5(3) . . ?
N6 C37 H37 116.3 . . ?
C38 C37 H37 116.3 . . ?
C43 C38 C39 120.8(3) . . ?
C43 C38 C37 121.1(3) . . ?
C39 C38 C37 118.1(3) . . ?
C40 C39 C38 120.2(4) . . ?
C40 C39 H39 119.9 . . ?
C38 C39 H39 119.9 . . ?
C39 C40 C41 119.8(4) . . ?
C39 C40 H40 120.1 . . ?
C41 C40 H40 120.1 . . ?
C42 C41 C40 121.3(4) . . ?
C42 C41 H41 119.3 . . ?
C40 C41 H41 119.3 . . ?
O5 C42 C41 124.5(3) . . ?
O5 C42 C43 115.1(4) . . ?
C41 C42 C43 120.4(4) . . ?
O6 C43 C38 124.6(3) . . ?
O6 C43 C42 118.0(3) . . ?
C38 C43 C42 117.4(3) . . ?
C45 C44 O5 110.9(4) . . ?
C45 C44 H44A 109.5 . . ?
O5 C44 H44A 109.5 . . ?
C45 C44 H44B 109.5 . . ?
O5 C44 H44B 109.5 . . ?
H44A C44 H44B 108.0 . . ?
C44 C45 H45A 109.5 . . ?
C44 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C44 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
N7 C46 C47 126.0(3) . . ?
N7 C46 H46 117.0 . . ?
C47 C46 H46 117.0 . . ?
C48 C47 C46 117.3(4) . . ?
C48 C47 H47 121.4 . . ?
C46 C47 H47 121.4 . . ?
C47 C48 C49 120.2(4) . . ?
C47 C48 H48 119.9 . . ?
C49 C48 H48 119.9 . . ?
C50 C49 C48 117.9(3) . . ?
C50 C49 H49 121.0 . . ?
C48 C49 H49 121.0 . . ?
N7 C50 C49 122.0(3) . . ?
N7 C50 C51 117.0(3) . . ?
C49 C50 C51 121.0(3) . . ?
N8 C51 C50 111.2(2) . . ?
N8 C51 H51A 109.4 . . ?
C50 C51 H51A 109.4 . . ?
N8 C51 H51B 109.4 . . ?
C50 C51 H51B 109.4 . . ?
H51A C51 H51B 108.0 . . ?
N8 C52 C53 116.6(3) . . ?
N8 C52 C36 108.3(2) . . ?
C53 C52 C36 110.7(3) . . ?
N8 C52 H52 106.9 . . ?
C53 C52 H52 106.9 . . ?
C36 C52 H52 106.9 . . ?
C58 C53 C54 118.8(3) . . ?
C58 C53 C52 118.5(3) . . ?
C54 C53 C52 122.7(3) . . ?
C53 C54 C55 119.1(3) . . ?
C53 C54 H54 120.4 . . ?
C55 C54 H54 120.4 . . ?
C56 C55 C54 121.9(4) . . ?
C56 C55 H55 119.1 . . ?
C54 C55 H55 119.1 . . ?
C57 C56 C55 119.5(3) . . ?
C57 C56 H56 120.2 . . ?
C55 C56 H56 120.2 . . ?
C56 C57 O7 126.6(3) . . ?
C56 C57 C58 118.5(3) . . ?
O7 C57 C58 114.9(3) . . ?
C53 C58 O8 118.4(3) . . ?
C53 C58 C57 122.2(3) . . ?
O8 C58 C57 119.3(3) . . ?
O7 C59 C60 107.3(3) . . ?
O7 C59 H59A 110.2 . . ?
C60 C59 H59A 110.2 . . ?
O7 C59 H59B 110.2 . . ?
C60 C59 H59B 110.2 . . ?
H59A C59 H59B 108.5 . . ?
C59 C60 H60A 109.5 . . ?
C59 C60 H60B 109.5 . . ?
H60A C60 H60B 109.5 . . ?
C59 C60 H60C 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
C5 N1 C1 116.9(2) . . ?
C5 N1 Sm1 119.00(19) . . ?
C1 N1 Sm1 123.70(18) . . ?
C7 N2 C6 116.2(2) . . ?
C7 N2 Sm1 130.67(17) . . ?
C6 N2 Sm1 109.85(18) . . ?
C16 N3 C20 117.4(3) . . ?
C16 N3 Sm1 120.5(2) . . ?
C20 N3 Sm1 121.6(2) . . ?
C21 N4 C22 112.9(3) . . ?
C21 N4 Sm1 111.26(16) . . ?
C22 N4 Sm1 118.30(19) . . ?
C21 N4 H4B 104.2 . . ?
C22 N4 H4B 104.2 . . ?
Sm1 N4 H4B 104.2 . . ?
C31 N5 C35 117.4(3) . . ?
C31 N5 Sm1 123.5(2) . . ?
C35 N5 Sm1 119.0(2) . . ?
C37 N6 C36 114.3(3) . . ?
C37 N6 Sm1 133.1(2) . . ?
C36 N6 Sm1 111.66(19) . . ?
C50 N7 C46 116.4(3) . . ?
C50 N7 Sm1 121.1(2) . . ?
C46 N7 Sm1 122.12(18) . . ?
C51 N8 C52 113.0(2) . . ?
C51 N8 Sm1 112.31(17) . . ?
C52 N8 Sm1 116.89(15) . . ?
C51 N8 H8A 104.3 . . ?
C52 N8 H8A 104.3 . . ?
Sm1 N8 H8A 104.3 . . ?
O6 Sm1 O2 167.53(8) . . ?
O6 Sm1 N6 67.18(8) . . ?
O2 Sm1 N6 118.14(7) . . ?
O6 Sm1 N2 117.98(7) . . ?
O2 Sm1 N2 66.54(6) . . ?
N6 Sm1 N2 138.22(8) . . ?
O6 Sm1 N5 118.80(8) . . ?
O2 Sm1 N5 72.38(7) . . ?
N6 Sm1 N5 61.42(8) . . ?
N2 Sm1 N5 84.19(8) . . ?
O6 Sm1 N1 74.08(8) . . ?
O2 Sm1 N1 116.98(7) . . ?
N6 Sm1 N1 82.73(7) . . ?
N2 Sm1 N1 61.95(7) . . ?
N5 Sm1 N1 68.81(7) . . ?
O6 Sm1 N3 94.29(8) . . ?
O2 Sm1 N3 75.07(8) . . ?
N6 Sm1 N3 144.69(8) . . ?
N2 Sm1 N3 76.75(8) . . ?
N5 Sm1 N3 146.74(8) . . ?
N1 Sm1 N3 122.31(7) . . ?
O6 Sm1 N7 74.63(7) . . ?
O2 Sm1 N7 94.91(7) . . ?
N6 Sm1 N7 78.84(8) . . ?
N2 Sm1 N7 142.71(8) . . ?
N5 Sm1 N7 122.24(7) . . ?
N1 Sm1 N7 147.92(8) . . ?
N3 Sm1 N7 67.03(8) . . ?
O6 Sm1 N8 115.57(7) . . ?
O2 Sm1 N8 62.55(7) . . ?
N6 Sm1 N8 61.71(7) . . ?
N2 Sm1 N8 126.06(7) . . ?
N5 Sm1 N8 64.85(7) . . ?
N1 Sm1 N8 130.92(7) . . ?
N3 Sm1 N8 105.43(7) . . ?
N7 Sm1 N8 59.70(8) . . ?
O6 Sm1 N4 61.74(8) . . ?
O2 Sm1 N4 116.18(7) . . ?
N6 Sm1 N4 124.89(7) . . ?
N2 Sm1 N4 61.02(8) . . ?
N5 Sm1 N4 131.28(7) . . ?
N1 Sm1 N4 65.06(7) . . ?
N3 Sm1 N4 60.09(7) . . ?
N7 Sm1 N4 105.32(8) . . ?
N8 Sm1 N4 163.69(7) . . ?
C13 O2 Sm1 143.80(15) . . ?
C12 O1 C14 116.2(3) . . ?
C28 O4 H4A 109.5 . . ?
C27 O3 C29 117.6(3) . . ?
C43 O6 Sm1 145.7(2) . . ?
C42 O5 C44 117.2(4) . . ?
C58 O8 H8 109.5 . . ?
C57 O7 C59 117.2(3) . . ?
O11 N9 O9 115.0(6) . . ?
O9 N9 O10 112.8(6) . . ?
O11 N9 O10' 104.5(9) . . ?
O9 N9 O10' 116.0(7) . . ?
O9 N9 O11' 109.2(6) . . ?
O10 N9 O11' 136.7(8) . . ?
H1WA O1W H1WB 107.9 . . ?
H2WA O2W H2WB 115.4(10) . . ?

_refine_diff_density_max         1.079
_refine_diff_density_min         -0.842
_refine_diff_density_rms         0.111

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1061274'
_audit_update_record             
;
2015-04-23 deposited with the CCDC.
2016-09-27 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H64 N10 O14 Sm2'
_chemical_formula_iupac          ?
_chemical_formula_weight         1329.81

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.675(4)
_cell_length_b                   11.181(4)
_cell_length_c                   13.204(4)
_cell_angle_alpha                79.820(6)
_cell_angle_beta                 81.137(6)
_cell_angle_gamma                65.029(6)
_cell_volume                     1400.6(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    298.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             670

_exptl_absorpt_coefficient_mu    2.147
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   
;
;
_exptl_absorpt_correction_T_min  0.58
_exptl_absorpt_correction_T_max  0.79

_exptl_special_details           
;
;

_diffrn_ambient_temperature      298.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            7292
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0682
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             5024
_reflns_number_gt                3890
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1112
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.040
_refine_ls_number_reflns         5024
_refine_ls_number_parameters     356
_refine_ls_number_restraints     8
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0474P)²+0.2017P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.163
_refine_diff_density_min         -0.744
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sm Sm1 1.00086(3) 0.87653(3) 0.61828(2) 0.04912(14) Uani d . . D 1 . .
C C11 0.9188(7) 0.7277(6) 0.4482(4) 0.0470(15) Uani d . . . 1 . .
C C10 0.7898(6) 0.8350(6) 0.4897(5) 0.0502(15) Uani d . . . 1 . .
H H10 0.707 0.8234 0.4788 0.06 Uiso calc U . R 1 . .
C C12 0.9136(8) 0.6473(7) 0.3816(5) 0.0576(17) Uani d . . . 1 . .
H H12 0.8292 0.6598 0.3608 0.069 Uiso calc U . R 1 . .
C C13 1.0348(8) 0.5490(7) 0.3467(5) 0.067(2) Uani d . . . 1 . .
H H13 1.0338 0.4925 0.3032 0.081 Uiso calc U . R 1 . .
C C14 1.1576(7) 0.5361(7) 0.3777(5) 0.0605(18) Uani d . . . 1 . .
H H14 1.2417 0.4731 0.3531 0.073 Uiso calc U . R 1 . .
C C7 0.7273(7) 0.7659(6) 0.7770(5) 0.0596(18) Uani d . . . 1 . .
C C9 0.7181(7) 0.7936(6) 0.6662(5) 0.0596(17) Uani d . . . 1 . .
H H9 0.6444 0.7874 0.6413 0.072 Uiso calc U . R 1 . .
C C15 1.1541(8) 0.6173(7) 0.4451(6) 0.0649(19) Uani d . . . 1 . .
H H15 1.2377 0.606 0.4669 0.078 Uiso calc U . R 1 . .
C C8 0.8403(8) 0.7595(6) 0.8232(5) 0.0600(18) Uani d . . . 1 . .
C C6 0.6230(8) 0.7365(8) 0.8394(6) 0.078(2) Uani d . . . 1 . .
H H6 0.5499 0.7386 0.8078 0.094 Uiso calc U . R 1 . .
C C5 0.6227(10) 0.7054(10) 0.9422(7) 0.099(3) Uani d . . . 1 . .
H H5 0.5513 0.6868 0.9813 0.119 Uiso calc U . R 1 . .
C C3 0.8422(9) 0.7269(8) 0.9324(5) 0.075(2) Uani d . . . 1 . .
C C4 0.7361(11) 0.7018(9) 0.9894(6) 0.097(3) Uani d . . . 1 . .
H H4 0.7377 0.6819 1.0608 0.116 Uiso calc U . R 1 . .
C C1 1.1254(13) 0.6638(12) 1.0819(8) 0.131(4) Uani d . . . 1 . .
H H1A 1.1965 0.6106 1.0347 0.196 Uiso calc U . R 1 . .
H H1B 1.1478 0.6275 1.1515 0.196 Uiso calc U . R 1 . .
H H1C 1.1191 0.7533 1.0689 0.196 Uiso calc U . R 1 . .
C C2 0.9907(12) 0.6636(10) 1.0671(6) 0.113(3) Uani d . . . 1 . .
H H2B 0.9982 0.5729 1.0752 0.136 Uiso calc U . R 1 . .
H H2A 0.9198 0.7107 1.1184 0.136 Uiso calc U . R 1 . .
C C21 0.7802(7) 0.9759(6) 0.4422(5) 0.0522(16) Uani d . . . 1 . .
H H21 0.6905 1.0408 0.468 0.063 Uiso calc U . R 1 . .
C C20 0.7846(7) 0.9935(6) 0.3238(5) 0.0519(16) Uani d . . . 1 . .
C C16 0.8789(8) 1.0632(8) 0.1688(6) 0.074(2) Uani d . . . 1 . .
H H16 0.9402 1.0984 0.1326 0.089 Uiso calc U . R 1 . .
C C19 0.6978(8) 0.9663(7) 0.2727(6) 0.071(2) Uani d . . . 1 . .
H H19 0.6336 0.9354 0.3096 0.086 Uiso calc U . R 1 . .
C C18 0.7078(9) 0.9858(8) 0.1662(6) 0.082(2) Uani d . . . 1 . .
H H18 0.6526 0.9649 0.1305 0.098 Uiso calc U . R 1 . .
C C17 0.7986(10) 1.0356(8) 0.1139(6) 0.086(3) Uani d . . . 1 . .
H H17 0.8057 1.0505 0.0421 0.103 Uiso calc U . R 1 . .
N N3 0.8817(4) 1.0006(4) 0.4748(3) 0.0308(9) Uani d . . D 1 . .
N N1 0.8023(5) 0.8255(5) 0.6003(4) 0.0525(13) Uani d . . . 1 . .
N N2 1.0386(6) 0.7112(5) 0.4813(4) 0.0559(14) Uani d . . . 1 . .
N N4 0.8747(6) 1.0423(5) 0.2731(4) 0.0590(14) Uani d . . . 1 . .
O O3 0.8059(5) 1.0738(5) 0.6803(3) 0.0727(14) Uani d . . D 1 . .
H H3A 0.749(5) 1.124(5) 0.636(2) 0.109 Uiso d U . D 1 . .
O O2 0.9458(5) 0.7815(5) 0.7712(3) 0.0688(13) Uani d . . . 1 . .
O O4 1.2295(5) 0.6959(5) 0.6447(4) 0.0752(14) Uani d . . D 1 . .
H H4A 1.297(3) 0.696(5) 0.600(4) 0.113 Uiso d U . D 1 . .
O O1 0.9554(7) 0.7248(6) 0.9697(4) 0.103(2) Uani d . . . 1 . .
O O5 0.3723(6) 0.7363(6) 0.4561(5) 0.1007(19) Uani d . . . 1 . .
O O7 0.5533(9) 0.7593(11) 0.3922(8) 0.177(4) Uani d . . . 1 . .
O O6 0.5372(9) 0.6750(10) 0.5435(8) 0.184(4) Uani d . . . 1 . .
N N5 0.4917(8) 0.7189(7) 0.4635(7) 0.086(2) Uani d . . . 1 . .
C C22 0.7583(11) 1.1284(12) 0.7767(7) 0.123(4) Uani d . . D 1 . .
H H22A 0.8308 1.0822 0.8233 0.147 Uiso calc U . R 1 . .
H H22B 0.7449 1.221 0.7644 0.147 Uiso calc U . R 1 . .
C C23 0.6358(13) 1.1216(14) 0.8262(9) 0.176(6) Uani d . . . 1 . .
H H23A 0.5614 1.1722 0.7831 0.263 Uiso calc U . R 1 . .
H H23B 0.6148 1.1575 0.8907 0.263 Uiso calc U . R 1 . .
H H23C 0.6471 1.0306 0.8389 0.263 Uiso calc U . R 1 . .
C C24 1.2697(12) 0.5795(13) 0.7199(10) 0.172(6) Uani d . . D 1 . .
H H24A 1.1896 0.5867 0.7686 0.207 Uiso calc U . R 1 . .
H H24B 1.2925 0.5029 0.6845 0.207 Uiso calc U . R 1 . .
C C25 1.3827(16) 0.5531(19) 0.7774(13) 0.251(11) Uani d . . D 1 . .
H H25A 1.4674 0.4962 0.7428 0.377 Uiso calc U . R 1 . .
H H25B 1.3689 0.5101 0.8452 0.377 Uiso calc U . R 1 . .
H H25C 1.3881 0.6352 0.783 0.377 Uiso calc U . R 1 . .
H H3 0.919(6) 1.044(6) 0.439(5) 0.08(3) Uiso d . . D 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Sm1 O2 . 2.227(4) ?
Sm1 N3 2_776 2.314(4) ?
Sm1 N3 . 2.336(4) ?
Sm1 O4 . 2.451(5) ?
Sm1 N1 . 2.470(5) ?
Sm1 O3 . 2.471(5) ?
Sm1 N4 2_776 2.591(5) ?
Sm1 N2 . 2.680(6) ?
Sm1 Sm1 2_776 3.7823(11) ?
C11 N2 . 1.343(8) ?
C11 C12 . 1.385(9) ?
C11 C10 . 1.497(8) ?
C10 N1 . 1.468(8) ?
C10 C21 . 1.555(8) ?
C10 H10 . 0.98 ?
C12 C13 . 1.375(9) ?
C12 H12 . 0.93 ?
C13 C14 . 1.375(10) ?
C13 H13 . 0.93 ?
C14 C15 . 1.366(10) ?
C14 H14 . 0.93 ?
C7 C6 . 1.399(9) ?
C7 C8 . 1.404(10) ?
C7 C9 . 1.451(9) ?
C9 N1 . 1.269(8) ?
C9 H9 . 0.93 ?
C15 N2 . 1.325(8) ?
C15 H15 . 0.93 ?
C8 O2 . 1.317(7) ?
C8 C3 . 1.424(9) ?
C6 C5 . 1.340(11) ?
C6 H6 . 0.93 ?
C5 C4 . 1.428(12) ?
C5 H5 . 0.93 ?
C3 O1 . 1.363(10) ?
C3 C4 . 1.364(11) ?
C4 H4 . 0.93 ?
C1 C2 . 1.481(13) ?
C1 H1A . 0.96 ?
C1 H1B . 0.96 ?
C1 H1C . 0.96 ?
C2 O1 . 1.374(9) ?
C2 H2B . 0.97 ?
C2 H2A . 0.97 ?
C21 N3 . 1.369(7) ?
C21 C20 . 1.537(8) ?
C21 H21 . 0.98 ?
C20 N4 . 1.336(8) ?
C20 C19 . 1.381(9) ?
C16 N4 . 1.353(8) ?
C16 C17 . 1.360(11) ?
C16 H16 . 0.93 ?
C19 C18 . 1.379(10) ?
C19 H19 . 0.93 ?
C18 C17 . 1.356(11) ?
C18 H18 . 0.93 ?
C17 H17 . 0.93 ?
N3 Sm1 2_776 2.314(4) ?
N3 H3 . 0.803(10) ?
N4 Sm1 2_776 2.591(5) ?
O3 C22 . 1.438(9) ?
O3 H3A . 0.854(9) ?
O4 C24 . 1.439(12) ?
O4 H4A . 0.858(9) ?
O5 N5 . 1.223(8) ?
O7 N5 . 1.196(10) ?
O6 N5 . 1.169(10) ?
C22 C23 . 1.394(14) ?
C22 H22A . 0.97 ?
C22 H22B . 0.97 ?
C23 H23A . 0.96 ?
C23 H23B . 0.96 ?
C23 H23C . 0.96 ?
C24 C25 . 1.421(9) ?
C24 H24A . 0.97 ?
C24 H24B . 0.97 ?
C25 H25A . 0.96 ?
C25 H25B . 0.96 ?
C25 H25C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 Sm1 N3 . 2_776 147.85(17) ?
O2 Sm1 N3 . . 135.33(16) ?
N3 Sm1 N3 2_776 . 71.12(17) ?
O2 Sm1 O4 . . 81.98(17) ?
N3 Sm1 O4 2_776 . 86.62(16) ?
N3 Sm1 O4 . . 135.34(16) ?
O2 Sm1 N1 . . 72.34(17) ?
N3 Sm1 N1 2_776 . 138.18(15) ?
N3 Sm1 N1 . . 67.36(16) ?
O4 Sm1 N1 . . 120.14(18) ?
O2 Sm1 O3 . . 81.32(17) ?
N3 Sm1 O3 2_776 . 93.55(17) ?
N3 Sm1 O3 . . 73.24(15) ?
O4 Sm1 O3 . . 148.48(17) ?
N1 Sm1 O3 . . 79.41(17) ?
O2 Sm1 N4 . 2_776 83.36(18) ?
N3 Sm1 N4 2_776 2_776 64.53(16) ?
N3 Sm1 N4 . 2_776 125.09(16) ?
O4 Sm1 N4 . 2_776 72.91(18) ?
N1 Sm1 N4 . 2_776 149.40(17) ?
O3 Sm1 N4 . 2_776 78.75(17) ?
O2 Sm1 N2 . . 106.33(17) ?
N3 Sm1 N2 2_776 . 99.46(15) ?
N3 Sm1 N2 . . 71.45(15) ?
O4 Sm1 N2 . . 74.91(17) ?
N1 Sm1 N2 . . 62.80(16) ?
O3 Sm1 N2 . . 135.69(17) ?
N4 Sm1 N2 2_776 . 144.63(17) ?
O2 Sm1 Sm1 . 2_776 163.14(13) ?
N3 Sm1 Sm1 2_776 2_776 35.75(10) ?
N3 Sm1 Sm1 . 2_776 35.37(11) ?
O4 Sm1 Sm1 . 2_776 113.78(12) ?
N1 Sm1 Sm1 . 2_776 102.61(11) ?
O3 Sm1 Sm1 . 2_776 81.94(12) ?
N4 Sm1 Sm1 2_776 2_776 95.27(12) ?
N2 Sm1 Sm1 . 2_776 84.50(11) ?
N2 C11 C12 . . 122.1(6) ?
N2 C11 C10 . . 116.5(5) ?
C12 C11 C10 . . 121.4(6) ?
N1 C10 C11 . . 106.4(5) ?
N1 C10 C21 . . 105.8(5) ?
C11 C10 C21 . . 111.8(5) ?
N1 C10 H10 . . 110.9 ?
C11 C10 H10 . . 110.9 ?
C21 C10 H10 . . 110.9 ?
C13 C12 C11 . . 119.2(7) ?
C13 C12 H12 . . 120.4 ?
C11 C12 H12 . . 120.4 ?
C12 C13 C14 . . 118.4(7) ?
C12 C13 H13 . . 120.8 ?
C14 C13 H13 . . 120.8 ?
C15 C14 C13 . . 119.0(7) ?
C15 C14 H14 . . 120.5 ?
C13 C14 H14 . . 120.5 ?
C6 C7 C8 . . 118.9(7) ?
C6 C7 C9 . . 118.3(7) ?
C8 C7 C9 . . 122.7(6) ?
N1 C9 C7 . . 125.5(7) ?
N1 C9 H9 . . 117.2 ?
C7 C9 H9 . . 117.2 ?
N2 C15 C14 . . 123.7(7) ?
N2 C15 H15 . . 118.1 ?
C14 C15 H15 . . 118.1 ?
O2 C8 C7 . . 123.8(6) ?
O2 C8 C3 . . 117.7(7) ?
C7 C8 C3 . . 118.6(7) ?
C5 C6 C7 . . 123.6(9) ?
C5 C6 H6 . . 118.2 ?
C7 C6 H6 . . 118.2 ?
C6 C5 C4 . . 117.5(8) ?
C6 C5 H5 . . 121.2 ?
C4 C5 H5 . . 121.2 ?
O1 C3 C4 . . 126.1(7) ?
O1 C3 C8 . . 114.0(7) ?
C4 C3 C8 . . 119.9(9) ?
C3 C4 C5 . . 121.6(8) ?
C3 C4 H4 . . 119.2 ?
C5 C4 H4 . . 119.2 ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O1 C2 C1 . . 108.6(8) ?
O1 C2 H2B . . 110.0 ?
C1 C2 H2B . . 110.0 ?
O1 C2 H2A . . 110.0 ?
C1 C2 H2A . . 110.0 ?
H2B C2 H2A . . 108.4 ?
N3 C21 C20 . . 112.1(5) ?
N3 C21 C10 . . 110.4(5) ?
C20 C21 C10 . . 111.4(5) ?
N3 C21 H21 . . 107.6 ?
C20 C21 H21 . . 107.6 ?
C10 C21 H21 . . 107.6 ?
N4 C20 C19 . . 121.9(6) ?
N4 C20 C21 . . 115.3(5) ?
C19 C20 C21 . . 122.7(6) ?
N4 C16 C17 . . 123.6(8) ?
N4 C16 H16 . . 118.2 ?
C17 C16 H16 . . 118.2 ?
C18 C19 C20 . . 119.0(7) ?
C18 C19 H19 . . 120.5 ?
C20 C19 H19 . . 120.5 ?
C17 C18 C19 . . 119.6(7) ?
C17 C18 H18 . . 120.2 ?
C19 C18 H18 . . 120.2 ?
C18 C17 C16 . . 118.5(7) ?
C18 C17 H17 . . 120.7 ?
C16 C17 H17 . . 120.7 ?
C21 N3 Sm1 . 2_776 127.0(4) ?
C21 N3 Sm1 . . 122.4(4) ?
Sm1 N3 Sm1 2_776 . 108.88(17) ?
C21 N3 H3 . . 123.(5) ?
Sm1 N3 H3 2_776 . 4.(5) ?
Sm1 N3 H3 . . 113.(5) ?
C9 N1 C10 . . 119.5(6) ?
C9 N1 Sm1 . . 132.3(5) ?
C10 N1 Sm1 . . 108.2(4) ?
C15 N2 C11 . . 117.5(6) ?
C15 N2 Sm1 . . 129.9(5) ?
C11 N2 Sm1 . . 112.5(4) ?
C20 N4 C16 . . 117.3(6) ?
C20 N4 Sm1 . 2_776 117.4(4) ?
C16 N4 Sm1 . 2_776 124.6(5) ?
C22 O3 Sm1 . . 135.8(5) ?
C22 O3 H3A . . 108.2(15) ?
Sm1 O3 H3A . . 115.9(14) ?
C8 O2 Sm1 . . 140.0(4) ?
C24 O4 Sm1 . . 130.2(6) ?
C24 O4 H4A . . 112.3(16) ?
Sm1 O4 H4A . . 117.3(15) ?
C3 O1 C2 . . 120.7(7) ?
O6 N5 O7 . . 121.8(9) ?
O6 N5 O5 . . 118.6(10) ?
O7 N5 O5 . . 119.2(9) ?
C23 C22 O3 . . 115.9(10) ?
C23 C22 H22A . . 108.3 ?
O3 C22 H22A . . 108.3 ?
C23 C22 H22B . . 108.3 ?
O3 C22 H22B . . 108.3 ?
H22A C22 H22B . . 107.4 ?
C22 C23 H23A . . 109.5 ?
C22 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C22 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
C25 C24 O4 . . 117.6(12) ?
C25 C24 H24A . . 107.9 ?
O4 C24 H24A . . 107.9 ?
C25 C24 H24B . . 107.9 ?
O4 C24 H24B . . 107.9 ?
H24A C24 H24B . . 107.2 ?
C24 C25 H25A . . 109.5 ?
C24 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
C24 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C24 H24A O2 . 0.97 2.59 3.278(13) 127.6 ?
C23 H23A O7 2_676 0.96 2.63 3.512(16) 153.5 ?
O4 H4A N5 1_655 0.858(9) 2.602(14) 3.457(10) 175.(4) ?
O4 H4A O6 1_655 0.858(9) 2.48(3) 3.277(11) 155.(6) ?
O4 H4A O5 1_655 0.858(9) 2.00(3) 2.782(8) 151.(5) ?
O3 H3A O5 2_676 0.854(9) 1.924(17) 2.768(8) 169.(7) ?
C19 H19 O7 . 0.93 2.49 3.347(12) 154.1 ?
C21 H21 O5 2_676 0.98 2.63 3.353(9) 130.4 ?
C15 H15 O5 1_655 0.93 2.42 3.163(10) 137.2 ?
C9 H9 O6 . 0.93 2.61 3.464(12) 153.2 ?
C10 H10 O7 . 0.98 2.53 3.455(11) 158.4 ?

