# Electronic Supplementary Material (ESI) for Dalton Transactions.
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#                                CCDC 
# 
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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_mo_molan011_0m

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C56 H66 K2 N8 O4'
_chemical_formula_weight         993.36

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
K K 0.2009 0.2494 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.4184(5)
_cell_length_b                   16.0507(10)
_cell_length_c                   17.5178(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.646(2)
_cell_angle_gamma                90
_cell_volume                     2639.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9865
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.40

_exptl_crystal_description       platelet
_exptl_crystal_colour            violet
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_max          0.45
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.233
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6364
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            106038
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_av_R_equivalents  0.1112
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.379
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6073
_reflns_number_gt                4342
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury 3.3'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0458P)²+2.4506P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6073
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1198
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
K1 K 0.12670(5) 0.10768(3) 0.90698(2) 0.02020(12) Uani 1 1 d . . . . .
O1 O 0.33671(18) 0.15075(11) 0.81684(10) 0.0402(4) Uani 1 1 d . . . . .
O2 O 0.02680(16) 0.25723(9) 0.85188(8) 0.0266(3) Uani 1 1 d . . . . .
N1 N 0.10035(18) 0.21277(11) 1.10795(9) 0.0217(4) Uani 1 1 d . . . . .
N2 N 0.15033(18) 0.15297(10) 1.06937(9) 0.0204(4) Uani 1 1 d . . . . .
N3 N 0.18530(17) 0.01825(10) 1.04804(9) 0.0186(4) Uani 1 1 d . . . . .
N4 N 0.16368(17) -0.06068(10) 1.06109(9) 0.0184(4) Uani 1 1 d . . . . .
C1 C 0.1378(2) 0.29181(13) 1.07957(11) 0.0219(4) Uani 1 1 d . . . . .
C2 C 0.2537(2) 0.30556(13) 1.03670(12) 0.0251(5) Uani 1 1 d . . . . .
H2 H 0.3103 0.2599 1.0227 0.030 Uiso 1 1 calc R U . . .
C3 C 0.2875(2) 0.38675(14) 1.01411(12) 0.0282(5) Uani 1 1 d . . . . .
H3 H 0.3675 0.3960 0.9855 0.034 Uiso 1 1 calc R U . . .
C4 C 0.2041(2) 0.45291(13) 1.03355(12) 0.0269(5) Uani 1 1 d . . . . .
H4 H 0.2266 0.5080 1.0187 0.032 Uiso 1 1 calc R U . . .
C5 C 0.0871(2) 0.43827(14) 1.07512(12) 0.0275(5) Uani 1 1 d . . . . .
H5 H 0.0283 0.4836 1.0875 0.033 Uiso 1 1 calc R U . . .
C6 C 0.0550(2) 0.35902(13) 1.09864(11) 0.0245(5) Uani 1 1 d . . . . .
H6 H -0.0242 0.3504 1.1280 0.029 Uiso 1 1 calc R U . . .
C7 C 0.1284(2) 0.07423(12) 1.09410(11) 0.0174(4) Uani 1 1 d . . . . .
C8 C 0.0534(2) 0.05119(12) 1.16254(10) 0.0170(4) Uani 1 1 d . . . . .
C9 C -0.0852(2) 0.07786(12) 1.17181(11) 0.0195(4) Uani 1 1 d . . . . .
H9 H -0.1230 0.1277 1.1425 0.023 Uiso 1 1 calc R U . . .
C10 C -0.1571(2) 0.04927(13) 1.23249(11) 0.0223(4) Uani 1 1 d . . . . .
H10 H -0.2520 0.0673 1.2373 0.027 Uiso 1 1 calc R U . . .
C11 C -0.0932(2) -0.00534(13) 1.28677(11) 0.0227(4) Uani 1 1 d . . . . .
C12 C 0.0472(2) -0.02875(12) 1.27931(11) 0.0215(4) Uani 1 1 d . . . . .
H12 H 0.0947 -0.0636 1.3170 0.026 Uiso 1 1 calc R U . . .
C13 C 0.1186(2) -0.00202(12) 1.21785(11) 0.0194(4) Uani 1 1 d . . . . .
H13 H 0.2135 -0.0202 1.2132 0.023 Uiso 1 1 calc R U . . .
C14 C -0.1745(3) -0.04051(15) 1.35027(13) 0.0325(5) Uani 1 1 d . . . . .
H14A H -0.1084 -0.0516 1.3952 0.049 Uiso 1 1 calc R U . . .
H14B H -0.2212 -0.0925 1.3330 0.049 Uiso 1 1 calc R U . . .
H14C H -0.2465 -0.0002 1.3638 0.049 Uiso 1 1 calc R U . . .
C15 C 0.2422(2) -0.11226(13) 1.01513(10) 0.0184(4) Uani 1 1 d . . . . .
C16 C 0.3613(2) -0.08597(14) 0.97851(12) 0.0240(5) Uani 1 1 d . . . . .
H16 H 0.3910 -0.0295 0.9824 0.029 Uiso 1 1 calc R U . . .
C17 C 0.4357(2) -0.14181(16) 0.93680(12) 0.0303(5) Uani 1 1 d . . . . .
H17 H 0.5168 -0.1234 0.9126 0.036 Uiso 1 1 calc R U . . .
C18 C 0.3933(2) -0.22434(15) 0.93001(12) 0.0296(5) Uani 1 1 d . . . . .
H18 H 0.4437 -0.2621 0.9004 0.036 Uiso 1 1 calc R U . . .
C19 C 0.2771(2) -0.25118(14) 0.96671(12) 0.0257(5) Uani 1 1 d . . . . .
H19 H 0.2480 -0.3078 0.9626 0.031 Uiso 1 1 calc R U . . .
C20 C 0.2027(2) -0.19607(13) 1.00938(11) 0.0210(4) Uani 1 1 d . . . . .
H20 H 0.1240 -0.2155 1.0350 0.025 Uiso 1 1 calc R U . . .
C21 C -0.0008(2) 0.34141(13) 0.87326(12) 0.0258(5) Uani 1 1 d . . . . .
H21A H 0.0771 0.3787 0.8600 0.031 Uiso 1 1 calc R U . . .
H21B H -0.0109 0.3456 0.9289 0.031 Uiso 1 1 calc R U . . .
C22 C -0.1376(3) 0.36354(16) 0.82830(14) 0.0397(6) Uani 1 1 d . . . . .
H22A H -0.1481 0.4246 0.8223 0.048 Uiso 1 1 calc R U . . .
H22B H -0.2209 0.3411 0.8526 0.048 Uiso 1 1 calc R U . . .
C23 C -0.1192(3) 0.32135(16) 0.75220(13) 0.0405(6) Uani 1 1 d . . . . .
H23A H -0.2126 0.3080 0.7248 0.049 Uiso 1 1 calc R U . . .
H23B H -0.0640 0.3568 0.7190 0.049 Uiso 1 1 calc R U . . .
C24 C -0.0385(3) 0.24321(16) 0.77580(14) 0.0370(6) Uani 1 1 d . . . . .
H24A H -0.1041 0.1950 0.7755 0.044 Uiso 1 1 calc R U . . .
H24B H 0.0352 0.2316 0.7400 0.044 Uiso 1 1 calc R U . . .
C25 C 0.3560(3) 0.23665(16) 0.79644(17) 0.0422(6) Uani 1 1 d . . . . .
H25A H 0.2889 0.2729 0.8217 0.051 Uiso 1 1 calc R U . . .
H25B H 0.3405 0.2444 0.7403 0.051 Uiso 1 1 calc R U . . .
C26 C 0.5072(3) 0.25630(17) 0.82418(17) 0.0418(6) Uani 1 1 d . . . . .
H26A H 0.5166 0.2679 0.8799 0.050 Uiso 1 1 calc R U . . .
H26B H 0.5439 0.3044 0.7964 0.050 Uiso 1 1 calc R U . . .
C27 C 0.5830(2) 0.17617(16) 0.80550(13) 0.0335(6) Uani 1 1 d . . . . .
H27A H 0.6687 0.1673 0.8412 0.040 Uiso 1 1 calc R U . . .
H27B H 0.6115 0.1770 0.7523 0.040 Uiso 1 1 calc R U . . .
C28 C 0.4716(3) 0.10903(16) 0.81550(15) 0.0375(6) Uani 1 1 d . . . . .
H28A H 0.4689 0.0689 0.7725 0.045 Uiso 1 1 calc R U . . .
H28B H 0.4943 0.0783 0.8640 0.045 Uiso 1 1 calc R 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
K1 O1 2.7185(17) . ?
K1 O2 2.7262(15) . ?
K1 N3 2.8723(16) . ?
K1 N2 2.9270(17) . ?
K1 N4 2.9342(17) 3_557 ?
K1 C8 3.2448(19) 3_557 ?
K1 C9 3.292(2) 3_557 ?
K1 C7 3.3202(19) . ?
K1 C24 3.443(3) . ?
K1 C13 3.4895(19) 3_557 ?
K1 C10 3.537(2) 3_557 ?
O1 C28 1.438(3) . ?
O1 C25 1.439(3) . ?
O2 C21 1.431(2) . ?
O2 C24 1.439(3) . ?
N1 N2 1.285(2) . ?
N1 C1 1.418(3) . ?
N2 C7 1.357(3) . ?
N3 N4 1.306(2) . ?
N3 C7 1.347(3) . ?
N4 C15 1.406(3) . ?
N4 K1 2.9343(17) 3_557 ?
C1 C6 1.388(3) . ?
C1 C2 1.392(3) . ?
C2 C3 1.406(3) . ?
C3 C4 1.380(3) . ?
C4 C5 1.389(3) . ?
C5 C6 1.378(3) . ?
C7 C8 1.487(3) . ?
C8 C9 1.396(3) . ?
C8 C13 1.396(3) . ?
C8 K1 3.2448(19) 3_557 ?
C9 C10 1.384(3) . ?
C9 K1 3.292(2) 3_557 ?
C10 C11 1.393(3) . ?
C10 K1 3.537(2) 3_557 ?
C11 C12 1.391(3) . ?
C11 C14 1.510(3) . ?
C12 C13 1.383(3) . ?
C13 K1 3.4894(19) 3_557 ?
C15 C20 1.397(3) . ?
C15 C16 1.401(3) . ?
C16 C17 1.383(3) . ?
C17 C18 1.386(3) . ?
C18 C19 1.382(3) . ?
C19 C20 1.384(3) . ?
C21 C22 1.497(3) . ?
C22 C23 1.518(3) . ?
C23 C24 1.507(4) . ?
C25 C26 1.501(3) . ?
C26 C27 1.519(4) . ?
C27 C28 1.524(3) . ?

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
O1 K1 O2 79.45(5) . . ?
O1 K1 N3 121.92(5) . . ?
O2 K1 N3 141.39(5) . . ?
O1 K1 N2 119.99(5) . . ?
O2 K1 N2 97.03(5) . . ?
N3 K1 N2 45.08(5) . . ?
O1 K1 N4 155.42(5) . 3_557 ?
O2 K1 N4 89.63(5) . 3_557 ?
N3 K1 N4 79.90(5) . 3_557 ?
N2 K1 N4 82.95(5) . 3_557 ?
O1 K1 C8 111.38(5) . 3_557 ?
O2 K1 C8 113.84(5) . 3_557 ?
N3 K1 C8 89.33(5) . 3_557 ?
N2 K1 C8 123.80(5) . 3_557 ?
N4 K1 C8 53.31(5) 3_557 3_557 ?
O1 K1 C9 93.08(5) . 3_557 ?
O2 K1 C9 128.48(5) . 3_557 ?
N3 K1 C9 85.22(5) . 3_557 ?
N2 K1 C9 128.99(5) . 3_557 ?
N4 K1 C9 76.50(5) 3_557 3_557 ?
C8 K1 C9 24.65(5) 3_557 3_557 ?
O1 K1 C7 131.99(5) . . ?
O2 K1 C7 117.77(5) . . ?
N3 K1 C7 23.74(5) . . ?
N2 K1 C7 24.05(5) . . ?
N4 K1 C7 72.57(5) 3_557 . ?
C8 K1 C7 101.78(5) 3_557 . ?
C9 K1 C7 104.98(5) 3_557 . ?
O1 K1 C24 76.25(6) . . ?
O2 K1 C24 23.51(5) . . ?
N3 K1 C24 159.22(6) . . ?
N2 K1 C24 119.11(5) . . ?
N4 K1 C24 84.95(6) 3_557 . ?
C8 K1 C24 92.97(5) 3_557 . ?
C9 K1 C24 105.06(5) 3_557 . ?
C7 K1 C24 136.63(5) . . ?
O1 K1 C13 103.62(5) . 3_557 ?
O2 K1 C13 90.80(5) . 3_557 ?
N3 K1 C13 111.57(5) . 3_557 ?
N2 K1 C13 136.39(5) . 3_557 ?
N4 K1 C13 54.16(5) 3_557 3_557 ?
C8 K1 C13 23.57(5) 3_557 3_557 ?
C9 K1 C13 41.20(5) 3_557 3_557 ?
C7 K1 C13 119.35(5) . 3_557 ?
C24 K1 C13 69.41(5) . 3_557 ?
O1 K1 C10 71.13(5) . 3_557 ?
O2 K1 C10 115.30(5) . 3_557 ?
N3 K1 C10 102.57(5) . 3_557 ?
N2 K1 C10 147.58(5) . 3_557 ?
N4 K1 C10 94.43(5) 3_557 3_557 ?
C8 K1 C10 41.41(5) 3_557 3_557 ?
C9 K1 C10 23.02(5) 3_557 3_557 ?
C7 K1 C10 124.93(5) . 3_557 ?
C24 K1 C10 92.66(5) . 3_557 ?
C13 K1 C10 46.16(5) 3_557 3_557 ?
C28 O1 C25 108.24(18) . . ?
C28 O1 K1 125.19(14) . . ?
C25 O1 K1 119.99(15) . . ?
C21 O2 C24 108.47(16) . . ?
C21 O2 K1 143.44(12) . . ?
C24 O2 K1 107.42(13) . . ?
N2 N1 C1 111.84(17) . . ?
N1 N2 C7 117.15(17) . . ?
N1 N2 K1 133.98(12) . . ?
C7 N2 K1 94.43(11) . . ?
N4 N3 C7 117.84(16) . . ?
N4 N3 K1 127.84(11) . . ?
C7 N3 K1 97.11(11) . . ?
N3 N4 C15 111.98(16) . . ?
N3 N4 K1 116.34(12) . 3_557 ?
C15 N4 K1 119.95(12) . 3_557 ?
C6 C1 C2 119.2(2) . . ?
C6 C1 N1 116.78(19) . . ?
C2 C1 N1 124.01(19) . . ?
C1 C2 C3 120.3(2) . . ?
C4 C3 C2 119.9(2) . . ?
C3 C4 C5 119.4(2) . . ?
C6 C5 C4 121.0(2) . . ?
C5 C6 C1 120.3(2) . . ?
N3 C7 N2 110.61(17) . . ?
N3 C7 C8 123.71(17) . . ?
N2 C7 C8 125.68(18) . . ?
N3 C7 K1 59.14(10) . . ?
N2 C7 K1 61.52(10) . . ?
C8 C7 K1 150.64(12) . . ?
C9 C8 C13 118.02(18) . . ?
C9 C8 C7 121.85(17) . . ?
C13 C8 C7 120.05(18) . . ?
C9 C8 K1 79.58(11) . 3_557 ?
C13 C8 K1 88.10(12) . 3_557 ?
C7 C8 K1 99.26(11) . 3_557 ?
C10 C9 C8 120.51(19) . . ?
C10 C9 K1 88.48(12) . 3_557 ?
C8 C9 K1 75.77(11) . 3_557 ?
C9 C10 C11 121.5(2) . . ?
C9 C10 K1 68.50(11) . 3_557 ?
C11 C10 K1 88.21(12) . 3_557 ?
C12 C11 C10 117.83(19) . . ?
C12 C11 C14 120.70(19) . . ?
C10 C11 C14 121.4(2) . . ?
C13 C12 C11 121.01(19) . . ?
C12 C13 C8 121.05(19) . . ?
C12 C13 K1 89.89(12) . 3_557 ?
C8 C13 K1 68.34(11) . 3_557 ?
C20 C15 C16 118.37(19) . . ?
C20 C15 N4 117.32(18) . . ?
C16 C15 N4 124.21(18) . . ?
C17 C16 C15 120.4(2) . . ?
C16 C17 C18 120.6(2) . . ?
C19 C18 C17 119.5(2) . . ?
C18 C19 C20 120.4(2) . . ?
C19 C20 C15 120.7(2) . . ?
O2 C21 C22 104.67(17) . . ?
C21 C22 C23 101.6(2) . . ?
C24 C23 C22 102.78(19) . . ?
O2 C24 C23 106.97(18) . . ?
O2 C24 K1 49.07(10) . . ?
C23 C24 K1 154.10(15) . . ?
O1 C25 C26 104.8(2) . . ?
C25 C26 C27 101.7(2) . . ?
C26 C27 C28 103.53(19) . . ?
O1 C28 C27 106.9(2) . . ?

_refine_diff_density_max         0.590
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.064

_shelxl_version_number           2013-4



_database_code_depnum_ccdc_archive 'CCDC 1020937'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mo_molan040_0m

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H38 N5 Na O2'
_chemical_formula_weight         499.62

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 2yc'

_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+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   13.1681(6)
_cell_length_b                   15.7367(7)
_cell_length_c                   13.2976(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.788(2)
_cell_angle_gamma                90
_cell_volume                     2754.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9965
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      32.95

_exptl_crystal_description       octagonal
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.11
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_max          0.28
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7224
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            134350
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.009
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6845
_reflns_number_gt                5804
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury 3.3'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0569P)²+1.2485P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6845
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1136
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
Na2 Na 0.5000 0.32900(4) 0.7500 0.01659(14) Uani 1 2 d S T P . .
Na1 Na 0.5000 0.82927(4) 0.7500 0.01810(14) Uani 1 2 d S T P . .
O13 O 0.33554(7) 0.82134(6) 0.66971(7) 0.0253(2) Uani 1 1 d . . . . .
O14 O 0.62965(7) 0.32087(5) 0.63385(7) 0.0244(2) Uani 1 1 d . . . . .
N11 N 0.63073(8) 1.00750(6) 0.64429(7) 0.0182(2) Uani 1 1 d . . . . .
N12 N 0.35022(7) 0.51105(6) 0.66490(7) 0.01474(18) Uani 1 1 d . . . . .
N21 N 0.56391(7) 0.96741(6) 0.69373(7) 0.0167(2) Uani 1 1 d . . . . .
N22 N 0.42520(7) 0.46895(6) 0.70315(7) 0.01325(18) Uani 1 1 d . . . . .
N31 N 0.5000 1.17819(9) 0.7500 0.0210(3) Uani 1 2 d S T P . .
N32 N 0.5000 0.67922(9) 0.7500 0.0206(3) Uani 1 2 d S T P . .
C11 C 0.69042(9) 0.95402(7) 0.58304(9) 0.0175(2) Uani 1 1 d . . . . .
C12 C 0.27634(8) 0.46012(7) 0.61292(8) 0.0139(2) Uani 1 1 d . . . . .
C13 C 0.27813(10) 0.88780(8) 0.62038(10) 0.0269(3) Uani 1 1 d . . . . .
H13A H 0.3038 0.8987 0.5524 0.032 Uiso 1 1 calc R U . . .
H13B H 0.2824 0.9411 0.6599 0.032 Uiso 1 1 calc R U . . .
C14 C 0.70640(10) 0.25670(9) 0.64288(12) 0.0306(3) Uani 1 1 d . . . . .
H14A H 0.6988 0.2146 0.5879 0.037 Uiso 1 1 calc R U . . .
H14B H 0.7028 0.2268 0.7082 0.037 Uiso 1 1 calc R U . . .
C21 C 0.79491(9) 0.97295(7) 0.58255(9) 0.0201(2) Uani 1 1 d . . . . .
C22 C 0.17468(8) 0.47476(7) 0.63764(8) 0.0164(2) Uani 1 1 d . . . . .
C23 C 0.16942(11) 0.85533(10) 0.61373(11) 0.0327(3) Uani 1 1 d . . . . .
H23A H 0.1577 0.8192 0.5536 0.039 Uiso 1 1 calc R U . . .
H23B H 0.1201 0.9028 0.6120 0.039 Uiso 1 1 calc R U . . .
C24 C 0.80559(10) 0.30454(9) 0.63588(11) 0.0291(3) Uani 1 1 d . . . . .
H24A H 0.8612 0.2667 0.6150 0.035 Uiso 1 1 calc R U . . .
H24B H 0.8252 0.3320 0.7006 0.035 Uiso 1 1 calc R U . . .
C31 C 0.85714(9) 0.92816(8) 0.51848(9) 0.0223(2) Uani 1 1 d . . . . .
H31 H 0.9278 0.9403 0.5195 0.027 Uiso 1 1 calc R U . . .
C32 C 0.09725(8) 0.43466(8) 0.58200(9) 0.0186(2) Uani 1 1 d . . . . .
H32 H 0.0287 0.4439 0.5994 0.022 Uiso 1 1 calc R U . . .
C33 C 0.16236(11) 0.80393(10) 0.71027(11) 0.0332(3) Uani 1 1 d . . . . .
H33A H 0.1427 0.8404 0.7671 0.040 Uiso 1 1 calc R U . . .
H33B H 0.1125 0.7572 0.7021 0.040 Uiso 1 1 calc R U . . .
C34 C 0.77878(9) 0.37023(9) 0.55501(10) 0.0257(3) Uani 1 1 d . . . . .
H34A H 0.8211 0.4219 0.5633 0.031 Uiso 1 1 calc R U . . .
H34B H 0.7876 0.3467 0.4868 0.031 Uiso 1 1 calc R U . . .
C41 C 0.81902(10) 0.86616(8) 0.45295(9) 0.0222(2) Uani 1 1 d . . . . .
C42 C 0.11775(9) 0.38141(7) 0.50161(9) 0.0182(2) Uani 1 1 d . . . . .
C43 C 0.26899(11) 0.76965(10) 0.72660(12) 0.0376(4) Uani 1 1 d . . . . .
H43A H 0.2890 0.7718 0.7989 0.045 Uiso 1 1 calc R U . . .
H43B H 0.2724 0.7098 0.7038 0.045 Uiso 1 1 calc R U . . .
C44 C 0.66749(10) 0.38947(9) 0.57312(11) 0.0280(3) Uani 1 1 d . . . . .
H44A H 0.6609 0.4444 0.6087 0.034 Uiso 1 1 calc R U . . .
H44B H 0.6286 0.3928 0.5083 0.034 Uiso 1 1 calc R U . . .
C51 C 0.71568(10) 0.84850(8) 0.45490(9) 0.0221(2) Uani 1 1 d . . . . .
H51 H 0.6886 0.8061 0.4109 0.027 Uiso 1 1 calc R U . . .
C52 C 0.21870(9) 0.36754(7) 0.47907(8) 0.0178(2) Uani 1 1 d . . . . .
H52 H 0.2336 0.3310 0.4246 0.021 Uiso 1 1 calc R U . . .
C61 C 0.64987(9) 0.89035(7) 0.51870(8) 0.0188(2) Uani 1 1 d . . . . .
C62 C 0.29912(8) 0.40531(7) 0.53339(8) 0.0157(2) Uani 1 1 d . . . . .
C71 C 0.83939(10) 1.03949(8) 0.65212(11) 0.0279(3) Uani 1 1 d . . . . .
H71A H 0.9128 1.0435 0.6428 0.042 Uiso 1 1 calc R U . . .
H71B H 0.8268 1.0238 0.7220 0.042 Uiso 1 1 calc R U . . .
H71C H 0.8076 1.0945 0.6370 0.042 Uiso 1 1 calc R U . . .
C72 C 0.15141(9) 0.53288(8) 0.72398(10) 0.0231(2) Uani 1 1 d . . . . .
H72A H 0.0783 0.5318 0.7356 0.035 Uiso 1 1 calc R U . . .
H72B H 0.1721 0.5910 0.7077 0.035 Uiso 1 1 calc R U . . .
H72C H 0.1887 0.5137 0.7848 0.035 Uiso 1 1 calc R U . . .
C81 C 0.88669(11) 0.82119(9) 0.38042(10) 0.0286(3) Uani 1 1 d . . . . .
H81A H 0.8668 0.7613 0.3753 0.043 Uiso 1 1 calc R U . . .
H81B H 0.9575 0.8252 0.4048 0.043 Uiso 1 1 calc R U . . .
H81C H 0.8796 0.8479 0.3140 0.043 Uiso 1 1 calc R U . . .
C82 C 0.03400(10) 0.33911(9) 0.43983(10) 0.0250(3) Uani 1 1 d . . . . .
H82A H 0.0462 0.3472 0.3681 0.037 Uiso 1 1 calc R U . . .
H82B H -0.0315 0.3645 0.4560 0.037 Uiso 1 1 calc R U . . .
H82C H 0.0329 0.2782 0.4552 0.037 Uiso 1 1 calc R U . . .
C91 C 0.53868(10) 0.86734(9) 0.51251(9) 0.0249(3) Uani 1 1 d . . . . .
H91A H 0.5212 0.8456 0.4451 0.037 Uiso 1 1 calc R U . . .
H91B H 0.4978 0.9179 0.5258 0.037 Uiso 1 1 calc R U . . .
H91C H 0.5248 0.8235 0.5626 0.037 Uiso 1 1 calc R U . . .
C92 C 0.40590(9) 0.38857(8) 0.50138(9) 0.0210(2) Uani 1 1 d . . . . .
H92A H 0.4047 0.3710 0.4306 0.031 Uiso 1 1 calc R U . . .
H92B H 0.4361 0.3433 0.5431 0.031 Uiso 1 1 calc R U . . .
H92C H 0.4464 0.4405 0.5095 0.031 Uiso 1 1 calc R U . . .
C101 C 0.5000 1.01458(10) 0.7500 0.0169(3) Uani 1 2 d S T P . .
C102 C 0.5000 0.51558(9) 0.7500 0.0132(3) Uani 1 2 d S T P . .
C111 C 0.5000 1.10525(10) 0.7500 0.0172(3) Uani 1 2 d S T P . .
C112 C 0.5000 0.60622(10) 0.7500 0.0147(3) Uani 1 2 d S T P . .


_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
Na2 O14 2.3412(8) . ?
Na2 O14 2.3412(8) 2_656 ?
Na2 N31 2.3732(15) 1_545 ?
Na2 N22 2.4840(10) . ?
Na2 N22 2.4841(10) 2_656 ?
Na2 C102 2.9362(16) . ?
Na1 N32 2.3612(15) . ?
Na1 O13 2.3878(9) . ?
Na1 O13 2.3878(9) 2_656 ?
Na1 N21 2.4562(11) 2_656 ?
Na1 N21 2.4563(11) . ?
Na1 C101 2.9162(16) . ?
O13 C43 1.4294(16) . ?
O13 C13 1.4369(15) . ?
O14 C14 1.4311(15) . ?
O14 C44 1.4460(14) . ?
N11 N21 1.2809(14) . ?
N11 C11 1.4246(15) . ?
N12 N22 1.2810(13) . ?
N12 C12 1.4228(14) . ?
N21 C101 1.3632(12) . ?
N22 C102 1.3633(12) . ?
N31 C111 1.148(2) . ?
N31 Na2 2.3732(15) 1_565 ?
N32 C112 1.149(2) . ?
C11 C21 1.4081(16) . ?
C11 C61 1.4115(16) . ?
C12 C62 1.4044(15) . ?
C12 C22 1.4073(15) . ?
C13 C23 1.5199(19) . ?
C14 C24 1.5130(19) . ?
C21 C31 1.3920(17) . ?
C21 C71 1.5038(17) . ?
C22 C32 1.3921(16) . ?
C22 C72 1.5069(16) . ?
C23 C33 1.523(2) . ?
C24 C34 1.5251(18) . ?
C31 C41 1.3913(18) . ?
C32 C42 1.3913(17) . ?
C33 C43 1.514(2) . ?
C34 C44 1.5230(17) . ?
C41 C51 1.3899(18) . ?
C41 C81 1.5096(17) . ?
C42 C52 1.3891(16) . ?
C42 C82 1.5092(16) . ?
C51 C61 1.3966(17) . ?
C52 C62 1.3959(16) . ?
C61 C91 1.5080(17) . ?
C62 C92 1.5050(15) . ?
C101 N21 1.3632(12) 2_656 ?
C101 C111 1.427(2) . ?
C102 N22 1.3633(12) 2_656 ?
C102 C112 1.426(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
O14 Na2 O14 173.73(5) . 2_656 ?
O14 Na2 N31 86.87(3) . 1_545 ?
O14 Na2 N31 86.87(3) 2_656 1_545 ?
O14 Na2 N22 100.06(3) . . ?
O14 Na2 N22 85.54(3) 2_656 . ?
N31 Na2 N22 152.45(2) 1_545 . ?
O14 Na2 N22 85.54(3) . 2_656 ?
O14 Na2 N22 100.06(3) 2_656 2_656 ?
N31 Na2 N22 152.45(2) 1_545 2_656 ?
N22 Na2 N22 55.10(4) . 2_656 ?
O14 Na2 C102 93.13(3) . . ?
O14 Na2 C102 93.13(3) 2_656 . ?
N31 Na2 C102 180.0 1_545 . ?
N22 Na2 C102 27.55(2) . . ?
N22 Na2 C102 27.55(2) 2_656 . ?
N32 Na1 O13 87.01(3) . . ?
N32 Na1 O13 87.01(3) . 2_656 ?
O13 Na1 O13 174.01(5) . 2_656 ?
N32 Na1 N21 152.26(2) . 2_656 ?
O13 Na1 N21 82.41(3) . 2_656 ?
O13 Na1 N21 102.98(3) 2_656 2_656 ?
N32 Na1 N21 152.26(2) . . ?
O13 Na1 N21 102.98(3) . . ?
O13 Na1 N21 82.41(3) 2_656 . ?
N21 Na1 N21 55.49(5) 2_656 . ?
N32 Na1 C101 180.0 . . ?
O13 Na1 C101 92.99(3) . . ?
O13 Na1 C101 92.99(3) 2_656 . ?
N21 Na1 C101 27.74(2) 2_656 . ?
N21 Na1 C101 27.74(2) . . ?
C43 O13 C13 109.47(10) . . ?
C43 O13 Na1 110.83(8) . . ?
C13 O13 Na1 128.54(7) . . ?
C14 O14 C44 108.60(9) . . ?
C14 O14 Na2 120.72(7) . . ?
C44 O14 Na2 126.78(7) . . ?
N21 N11 C11 113.74(9) . . ?
N22 N12 C12 114.11(9) . . ?
N11 N21 C101 117.34(10) . . ?
N11 N21 Na1 147.10(8) . . ?
C101 N21 Na1 95.25(7) . . ?
N12 N22 C102 116.10(9) . . ?
N12 N22 Na2 148.51(7) . . ?
C102 N22 Na2 95.02(7) . . ?
C111 N31 Na2 180.0 . 1_565 ?
C112 N32 Na1 180.0 . . ?
C21 C11 C61 119.91(11) . . ?
C21 C11 N11 115.74(10) . . ?
C61 C11 N11 124.11(11) . . ?
C62 C12 C22 120.23(10) . . ?
C62 C12 N12 123.57(10) . . ?
C22 C12 N12 115.81(10) . . ?
O13 C13 C23 105.25(10) . . ?
O14 C14 C24 104.62(10) . . ?
C31 C21 C11 119.31(11) . . ?
C31 C21 C71 120.25(11) . . ?
C11 C21 C71 120.43(11) . . ?
C32 C22 C12 119.21(10) . . ?
C32 C22 C72 121.13(10) . . ?
C12 C22 C72 119.66(10) . . ?
C13 C23 C33 102.22(11) . . ?
C14 C24 C34 101.50(11) . . ?
C41 C31 C21 122.05(12) . . ?
C42 C32 C22 121.66(10) . . ?
C43 C33 C23 103.27(12) . . ?
C44 C34 C24 103.06(10) . . ?
C51 C41 C31 117.57(11) . . ?
C51 C41 C81 121.06(12) . . ?
C31 C41 C81 121.35(12) . . ?
C52 C42 C32 118.05(10) . . ?
C52 C42 C82 120.08(11) . . ?
C32 C42 C82 121.87(11) . . ?
O13 C43 C33 107.61(11) . . ?
O14 C44 C34 106.85(10) . . ?
C41 C51 C61 122.92(12) . . ?
C42 C52 C62 122.49(11) . . ?
C51 C61 C11 118.21(11) . . ?
C51 C61 C91 118.26(11) . . ?
C11 C61 C91 123.49(11) . . ?
C52 C62 C12 118.34(10) . . ?
C52 C62 C92 118.65(10) . . ?
C12 C62 C92 122.95(10) . . ?
N21 C101 N21 114.02(13) 2_656 . ?
N21 C101 C111 122.99(7) 2_656 . ?
N21 C101 C111 122.99(7) . . ?
N21 C101 Na1 57.01(7) 2_656 . ?
N21 C101 Na1 57.01(7) . . ?
C111 C101 Na1 180.0 . . ?
N22 C102 N22 114.87(13) . 2_656 ?
N22 C102 C112 122.57(6) . . ?
N22 C102 C112 122.57(6) 2_656 . ?
N22 C102 Na2 57.43(6) . . ?
N22 C102 Na2 57.43(6) 2_656 . ?
C112 C102 Na2 180.0 . . ?
N31 C111 C101 180.0 . . ?
N32 C112 C102 180.0 . . ?

_refine_diff_density_max         0.389
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-4



_database_code_depnum_ccdc_archive 'CCDC 1020938'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mo_molan042_0m

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C102 H114 N24 Na6'
_chemical_formula_weight         1814.11

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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   16.7609(8)
_cell_length_b                   16.7609(8)
_cell_length_c                   30.0579(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7312.8(8)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9894
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      28.31

_exptl_crystal_description       block
_exptl_crystal_colour            'dark purple'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_F_000             2880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7058
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44691
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.887
_diffrn_reflns_theta_max         27.087
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             3461
_reflns_number_gt                2906
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury 3.3'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0382P)²+9.4286P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3461
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.003
_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
Na1 Na 0.35557(4) 0.34002(3) 1.01519(2) 0.01891(13) Uani 1 1 d . . . . .
C1 C 0.49948(8) 0.46124(8) 0.92682(4) 0.0157(2) Uani 1 1 d . . . . .
N2 N 0.35723(7) 0.44399(7) 0.92475(3) 0.0141(2) Uani 1 1 d . . . . .
C2 C 0.51745(9) 0.48993(9) 0.88223(4) 0.0193(3) Uani 1 1 d . . . . .
H2 H 0.4702 0.4886 0.8643 0.023 Uiso 1 1 calc R U . . .
N3 N 0.24281(7) 0.36650(7) 0.97807(3) 0.0136(2) Uani 1 1 d . . . . .
C3 C 0.60421(9) 0.52020(10) 0.86453(4) 0.0244(3) Uani 1 1 d . . . . .
H3 H 0.6162 0.5404 0.8345 0.029 Uiso 1 1 calc R U . . .
N1 N 0.41402(7) 0.42996(7) 0.94859(3) 0.0152(2) Uani 1 1 d . . . . .
C7 C 0.27162(8) 0.41674(8) 0.94047(4) 0.0135(2) Uani 1 1 d . . . . .
C6 C 0.57015(9) 0.46284(9) 0.95230(4) 0.0212(3) Uani 1 1 d . . . . .
H6 H 0.5589 0.4434 0.9825 0.025 Uiso 1 1 calc R U . . .
C5 C 0.65648(9) 0.49252(11) 0.93393(5) 0.0278(3) Uani 1 1 d . . . . .
H5 H 0.7039 0.4930 0.9515 0.033 Uiso 1 1 calc R U . . .
C8 C 0.21447(8) 0.44666(8) 0.91284(4) 0.0154(2) Uani 1 1 d . . . . .
C10 C 0.12379(9) 0.36130(9) 0.89817(4) 0.0207(3) Uani 1 1 d . . . . .
H10A H 0.0833 0.3810 0.8846 0.031 Uiso 1 1 calc R U . . .
H10B H 0.0932 0.3226 0.9241 0.031 Uiso 1 1 calc R U . . .
H10C H 0.1372 0.3260 0.8765 0.031 Uiso 1 1 calc R U . . .
C9 C 0.26561(9) 0.49708(9) 0.87030(4) 0.0205(3) Uani 1 1 d . . . . .
H9A H 0.2267 0.5138 0.8529 0.031 Uiso 1 1 calc R U . . .
H9B H 0.2797 0.4566 0.8526 0.031 Uiso 1 1 calc R U . . .
H9C H 0.3231 0.5530 0.8783 0.031 Uiso 1 1 calc R U . . .
C11 C 0.19667(9) 0.51364(9) 0.94026(4) 0.0192(3) Uani 1 1 d . . . . .
H11A H 0.1525 0.5256 0.9245 0.029 Uiso 1 1 calc R U . . .
H11B H 0.2547 0.5717 0.9443 0.029 Uiso 1 1 calc R U . . .
H11C H 0.1715 0.4864 0.9694 0.029 Uiso 1 1 calc R U . . .
N4 N 0.16426(7) 0.34873(7) 0.99642(3) 0.0143(2) Uani 1 1 d . . . . .
C4 C 0.67367(9) 0.52143(11) 0.88998(5) 0.0298(3) Uani 1 1 d . . . . .
H4 H 0.7328 0.5420 0.8774 0.036 Uiso 1 1 calc R U . . .
C12 C 0.14092(8) 0.28607(8) 1.03224(4) 0.0138(2) Uani 1 1 d . . . . .
C17 C 0.15348(8) 0.20968(8) 1.03013(4) 0.0163(2) Uani 1 1 d . . . . .
H17 H 0.1818 0.2007 1.0047 0.020 Uiso 1 1 calc R U . . .
C13 C 0.09722(8) 0.29702(9) 1.06946(4) 0.0173(3) Uani 1 1 d . . . . .
H13 H 0.0871 0.3479 1.0711 0.021 Uiso 1 1 calc R U . . .
C15 C 0.08312(9) 0.15894(9) 1.10212(4) 0.0204(3) Uani 1 1 d . . . . .
H15 H 0.0645 0.1164 1.1261 0.025 Uiso 1 1 calc R U . . .
C14 C 0.06864(9) 0.23370(9) 1.10407(4) 0.0202(3) Uani 1 1 d . . . . .
H14 H 0.0390 0.2415 1.1293 0.024 Uiso 1 1 calc R U . . .
C16 C 0.12489(9) 0.14695(9) 1.06489(4) 0.0195(3) Uani 1 1 d . . . . .
H16 H 0.1340 0.0954 1.0632 0.023 Uiso 1 1 calc R 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
Na1 N1 2.4006(11) . ?
Na1 N3 2.4192(11) . ?
Na1 N4 2.5754(11) 11_557 ?
Na1 C17 3.0080(13) . ?
Na1 C6 3.0511(14) 10_667 ?
C1 C6 1.3996(18) . ?
C1 C2 1.4046(17) . ?
C1 N1 1.4155(15) . ?
N2 N1 1.3033(14) . ?
N2 C7 1.3549(15) . ?
C2 C3 1.3848(18) . ?
N3 N4 1.3170(14) . ?
N3 C7 1.3465(15) . ?
C3 C4 1.385(2) . ?
C7 C8 1.5293(16) . ?
C6 C5 1.3878(19) . ?
C6 Na1 3.0511(14) 10_667 ?
C5 C4 1.387(2) . ?
C8 C9 1.5361(16) . ?
C8 C11 1.5374(17) . ?
C8 C10 1.5417(17) . ?
N4 C12 1.4157(15) . ?
N4 Na1 2.5754(11) 12_557 ?
C12 C13 1.3989(17) . ?
C12 C17 1.3989(17) . ?
C17 C16 1.3867(17) . ?
C13 C14 1.3890(18) . ?
C15 C16 1.3869(19) . ?
C15 C14 1.3916(19) . ?

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 Na1 N3 67.12(4) . . ?
N1 Na1 N4 108.68(4) . 11_557 ?
N3 Na1 N4 118.67(4) . 11_557 ?
N1 Na1 C17 122.57(4) . . ?
N3 Na1 C17 60.18(4) . . ?
N4 Na1 C17 79.69(3) 11_557 . ?
N1 Na1 C6 76.68(4) . 10_667 ?
N3 Na1 C6 83.24(4) . 10_667 ?
N4 Na1 C6 158.00(4) 11_557 10_667 ?
C17 Na1 C6 116.12(4) . 10_667 ?
C6 C1 C2 118.75(11) . . ?
C6 C1 N1 116.37(11) . . ?
C2 C1 N1 124.88(11) . . ?
N1 N2 C7 119.56(10) . . ?
C3 C2 C1 119.88(12) . . ?
N4 N3 C7 119.88(10) . . ?
N4 N3 Na1 123.35(7) . . ?
C7 N3 Na1 115.67(8) . . ?
C4 C3 C2 120.95(13) . . ?
N2 N1 C1 111.97(10) . . ?
N2 N1 Na1 117.79(7) . . ?
C1 N1 Na1 129.62(8) . . ?
N3 C7 N2 119.45(10) . . ?
N3 C7 C8 124.99(10) . . ?
N2 C7 C8 115.56(10) . . ?
C5 C6 C1 120.66(12) . . ?
C5 C6 Na1 87.22(9) . 10_667 ?
C1 C6 Na1 94.54(8) . 10_667 ?
C4 C5 C6 120.09(13) . . ?
C7 C8 C9 111.33(10) . . ?
C7 C8 C11 109.29(10) . . ?
C9 C8 C11 107.65(10) . . ?
C7 C8 C10 109.85(10) . . ?
C9 C8 C10 107.01(10) . . ?
C11 C8 C10 111.70(10) . . ?
N3 N4 C12 111.12(9) . . ?
N3 N4 Na1 144.44(8) . 12_557 ?
C12 N4 Na1 102.80(7) . 12_557 ?
C3 C4 C5 119.66(12) . . ?
C13 C12 C17 118.98(11) . . ?
C13 C12 N4 118.65(10) . . ?
C17 C12 N4 122.17(10) . . ?
C16 C17 C12 120.45(11) . . ?
C16 C17 Na1 119.99(8) . . ?
C12 C17 Na1 88.41(7) . . ?
C14 C13 C12 120.12(11) . . ?
C16 C15 C14 119.50(11) . . ?
C13 C14 C15 120.51(12) . . ?
C17 C16 C15 120.40(12) . . ?

_refine_diff_density_max         0.354
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.041

_shelxl_version_number           2013-4



_database_code_depnum_ccdc_archive 'CCDC 1020939'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mo_molan069_0m

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H53 N5'
_chemical_formula_weight         555.83

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.5964(5)
_cell_length_b                   19.7591(14)
_cell_length_c                   19.9085(15)
_cell_angle_alpha                90
_cell_angle_beta                 99.724(2)
_cell_angle_gamma                90
_cell_volume                     3333.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6731
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      26.62

_exptl_crystal_description       needle
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.108
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.065
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6454
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35087
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.926
_diffrn_reflns_theta_max         26.818
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7106
_reflns_number_gt                4686
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury 3.3'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0524P)²+1.1079P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7106
_refine_ls_number_parameters     375
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1284
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
N1 N 0.85461(16) 0.64872(7) 0.22305(7) 0.0237(3) Uani 1 1 d . . . . .
N2 N 0.89801(16) 0.70093(7) 0.19116(7) 0.0220(3) Uani 1 1 d . . . . .
N3 N 0.99102(15) 0.80545(7) 0.18894(7) 0.0201(3) Uani 1 1 d . . . . .
N4 N 1.05111(15) 0.86124(7) 0.21715(7) 0.0209(3) Uani 1 1 d . . . . .
N5 N 0.51117(16) 0.79932(7) 0.26211(7) 0.0232(3) Uani 1 1 d . . . . .
C1 C 0.78354(19) 0.59825(8) 0.17792(9) 0.0228(4) Uani 1 1 d . . . . .
C2 C 0.6944(2) 0.54969(8) 0.20477(10) 0.0266(4) Uani 1 1 d . . . . .
H2 H 0.6853 0.5517 0.2516 0.032 Uiso 1 1 calc R U . . .
C3 C 0.6186(2) 0.49845(9) 0.16462(10) 0.0280(4) Uani 1 1 d . . . . .
H3 H 0.5578 0.4660 0.1840 0.034 Uiso 1 1 calc R U . . .
C4 C 0.6308(2) 0.49417(9) 0.09640(10) 0.0301(4) Uani 1 1 d . . . . .
H4 H 0.5779 0.4593 0.0686 0.036 Uiso 1 1 calc R U . . .
C5 C 0.7214(2) 0.54155(9) 0.06920(10) 0.0330(5) Uani 1 1 d . . . . .
H5 H 0.7312 0.5387 0.0225 0.040 Uiso 1 1 calc R U . . .
C6 C 0.7981(2) 0.59298(9) 0.10908(10) 0.0275(4) Uani 1 1 d . . . . .
H6 H 0.8608 0.6247 0.0897 0.033 Uiso 1 1 calc R U . . .
C7 C 0.97076(18) 0.75241(8) 0.22994(9) 0.0192(4) Uani 1 1 d . . . . .
C8 C 1.02713(18) 0.74941(8) 0.30442(9) 0.0194(4) Uani 1 1 d . . . . .
C9 C 1.02484(19) 0.80541(8) 0.34740(9) 0.0214(4) Uani 1 1 d . . . . .
H9 H 0.9796 0.8467 0.3290 0.026 Uiso 1 1 calc R U . . .
C10 C 1.0872(2) 0.80186(9) 0.41629(9) 0.0259(4) Uani 1 1 d . . . . .
H10 H 1.0831 0.8407 0.4441 0.031 Uiso 1 1 calc R U . . .
C11 C 1.1554(2) 0.74301(9) 0.44541(10) 0.0299(4) Uani 1 1 d . . . . .
C12 C 1.1561(2) 0.68706(9) 0.40324(10) 0.0293(4) Uani 1 1 d . . . . .
H12 H 1.2004 0.6458 0.4221 0.035 Uiso 1 1 calc R U . . .
C13 C 1.0939(2) 0.68990(9) 0.33458(9) 0.0241(4) Uani 1 1 d . . . . .
H13 H 1.0965 0.6506 0.3073 0.029 Uiso 1 1 calc R U . . .
C14 C 1.2262(3) 0.73922(11) 0.52018(11) 0.0497(6) Uani 1 1 d . . . . .
H14A H 1.2060 0.6944 0.5379 0.074 Uiso 1 1 calc R U . . .
H14B H 1.1782 0.7740 0.5453 0.074 Uiso 1 1 calc R U . . .
H14C H 1.3403 0.7469 0.5258 0.074 Uiso 1 1 calc R U . . .
C15 C 1.08238(18) 0.90840(8) 0.16770(9) 0.0193(4) Uani 1 1 d . . . . .
C16 C 1.12595(19) 0.97349(8) 0.19046(9) 0.0236(4) Uani 1 1 d . . . . .
H16 H 1.1284 0.9847 0.2370 0.028 Uiso 1 1 calc R U . . .
C17 C 1.1657(2) 1.02199(9) 0.14626(10) 0.0276(4) Uani 1 1 d . . . . .
H17 H 1.1950 1.0661 0.1626 0.033 Uiso 1 1 calc R U . . .
C18 C 1.1628(2) 1.00661(9) 0.07872(10) 0.0334(5) Uani 1 1 d . . . . .
H18 H 1.1899 1.0399 0.0483 0.040 Uiso 1 1 calc R U . . .
C19 C 1.1201(2) 0.94216(9) 0.05558(10) 0.0345(5) Uani 1 1 d . . . . .
H19 H 1.1183 0.9314 0.0089 0.041 Uiso 1 1 calc R U . . .
C20 C 1.0802(2) 0.89333(9) 0.09914(9) 0.0259(4) Uani 1 1 d . . . . .
H20 H 1.0511 0.8493 0.0824 0.031 Uiso 1 1 calc R U . . .
C21 C 0.61552(19) 0.84175(9) 0.22427(9) 0.0249(4) Uani 1 1 d . . . . .
H21A H 0.7018 0.8609 0.2582 0.030 Uiso 1 1 calc R U . . .
H21B H 0.6646 0.8112 0.1944 0.030 Uiso 1 1 calc R U . . .
C22 C 0.5373(2) 0.89934(10) 0.18108(10) 0.0315(4) Uani 1 1 d . . . . .
H22A H 0.4967 0.9333 0.2104 0.038 Uiso 1 1 calc R U . . .
H22B H 0.4474 0.8820 0.1478 0.038 Uiso 1 1 calc R U . . .
C23 C 0.6592(2) 0.93192(9) 0.14356(10) 0.0312(4) Uani 1 1 d . . . . .
H23A H 0.7484 0.9487 0.1775 0.037 Uiso 1 1 calc R U . . .
H23B H 0.7010 0.8970 0.1157 0.037 Uiso 1 1 calc R U . . .
C24 C 0.5941(3) 0.98980(13) 0.09781(13) 0.0583(7) Uani 1 1 d . . . . .
H24A H 0.6773 1.0080 0.0749 0.087 Uiso 1 1 calc R U . . .
H24B H 0.5561 1.0255 0.1252 0.087 Uiso 1 1 calc R U . . .
H24C H 0.5064 0.9735 0.0636 0.087 Uiso 1 1 calc R U . . .
C25 C 0.4313(2) 0.84249(9) 0.30984(9) 0.0267(4) Uani 1 1 d . . . . .
H25A H 0.3584 0.8744 0.2820 0.032 Uiso 1 1 calc R U . . .
H25B H 0.3668 0.8125 0.3340 0.032 Uiso 1 1 calc R U . . .
C26 C 0.5417(2) 0.88288(10) 0.36255(10) 0.0336(5) Uani 1 1 d . . . . .
H26A H 0.5979 0.9171 0.3393 0.040 Uiso 1 1 calc R U . . .
H26B H 0.6214 0.8522 0.3883 0.040 Uiso 1 1 calc R U . . .
C27 C 0.4506(2) 0.91833(10) 0.41200(10) 0.0331(5) Uani 1 1 d . . . . .
H27A H 0.3948 0.8838 0.4351 0.040 Uiso 1 1 calc R U . . .
H27B H 0.5266 0.9417 0.4474 0.040 Uiso 1 1 calc R U . . .
C28 C 0.3321(3) 0.96916(11) 0.37798(11) 0.0426(5) Uani 1 1 d . . . . .
H28A H 0.2910 0.9956 0.4128 0.064 Uiso 1 1 calc R U . . .
H28B H 0.2449 0.9454 0.3495 0.064 Uiso 1 1 calc R U . . .
H28C H 0.3832 0.9996 0.3495 0.064 Uiso 1 1 calc R U . . .
C29 C 0.61882(19) 0.74670(9) 0.30141(9) 0.0253(4) Uani 1 1 d . . . . .
H29A H 0.6773 0.7237 0.2692 0.030 Uiso 1 1 calc R U . . .
H29B H 0.6974 0.7705 0.3353 0.030 Uiso 1 1 calc R U . . .
C30 C 0.5400(2) 0.69308(10) 0.33829(11) 0.0347(5) Uani 1 1 d . . . . .
H30A H 0.4760 0.6629 0.3047 0.042 Uiso 1 1 calc R U . . .
H30B H 0.4686 0.7148 0.3660 0.042 Uiso 1 1 calc R U . . .
C31 C 0.6649(2) 0.65170(10) 0.38432(10) 0.0352(5) Uani 1 1 d . . . . .
H31A H 0.6154 0.6098 0.3980 0.042 Uiso 1 1 calc R U . . .
H31B H 0.7478 0.6383 0.3580 0.042 Uiso 1 1 calc R U . . .
C32 C 0.7413(3) 0.68879(12) 0.44775(11) 0.0491(6) Uani 1 1 d . . . . .
H32A H 0.8148 0.6584 0.4762 0.074 Uiso 1 1 calc R U . . .
H32B H 0.6598 0.7039 0.4733 0.074 Uiso 1 1 calc R U . . .
H32C H 0.7990 0.7282 0.4348 0.074 Uiso 1 1 calc R U . . .
C33 C 0.37928(19) 0.76590(9) 0.21309(9) 0.0244(4) Uani 1 1 d . . . . .
H33A H 0.3154 0.7386 0.2400 0.029 Uiso 1 1 calc R U . . .
H33B H 0.3100 0.8019 0.1900 0.029 Uiso 1 1 calc R U . . .
C34 C 0.4287(2) 0.72083(9) 0.15907(10) 0.0278(4) Uani 1 1 d . . . . .
H34A H 0.5048 0.6865 0.1808 0.033 Uiso 1 1 calc R U . . .
H34B H 0.4812 0.7483 0.1278 0.033 Uiso 1 1 calc R U . . .
C35 C 0.2840(2) 0.68573(10) 0.11893(10) 0.0344(5) Uani 1 1 d . . . . .
H35A H 0.2369 0.6558 0.1500 0.041 Uiso 1 1 calc R U . . .
H35B H 0.2045 0.7203 0.1010 0.041 Uiso 1 1 calc R U . . .
C36 C 0.3235(2) 0.64405(10) 0.06005(10) 0.0392(5) Uani 1 1 d . . . . .
H36A H 0.2275 0.6222 0.0363 0.059 Uiso 1 1 calc R U . . .
H36B H 0.4015 0.6094 0.0775 0.059 Uiso 1 1 calc R U . . .
H36C H 0.3669 0.6737 0.0283 0.059 Uiso 1 1 calc R 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
N1 N2 1.2987(19) . ?
N1 C1 1.410(2) . ?
N2 C7 1.363(2) . ?
N3 N4 1.3036(18) . ?
N3 C7 1.357(2) . ?
N4 C15 1.414(2) . ?
N5 C33 1.517(2) . ?
N5 C21 1.518(2) . ?
N5 C29 1.518(2) . ?
N5 C25 1.524(2) . ?
C1 C2 1.390(2) . ?
C1 C6 1.401(3) . ?
C2 C3 1.383(2) . ?
C3 C4 1.382(3) . ?
C4 C5 1.385(3) . ?
C5 C6 1.386(3) . ?
C7 C8 1.481(2) . ?
C8 C13 1.399(2) . ?
C8 C9 1.401(2) . ?
C9 C10 1.388(3) . ?
C10 C11 1.384(2) . ?
C11 C12 1.389(3) . ?
C11 C14 1.512(3) . ?
C12 C13 1.382(3) . ?
C15 C16 1.394(2) . ?
C15 C20 1.394(2) . ?
C16 C17 1.382(2) . ?
C17 C18 1.375(3) . ?
C18 C19 1.383(3) . ?
C19 C20 1.379(2) . ?
C21 C22 1.514(2) . ?
C22 C23 1.528(2) . ?
C23 C24 1.510(3) . ?
C25 C26 1.517(3) . ?
C26 C27 1.528(3) . ?
C27 C28 1.507(3) . ?
C29 C30 1.513(2) . ?
C30 C31 1.526(3) . ?
C31 C32 1.511(3) . ?
C33 C34 1.512(2) . ?
C34 C35 1.526(3) . ?
C35 C36 1.517(3) . ?

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
N2 N1 C1 112.30(14) . . ?
N1 N2 C7 117.26(14) . . ?
N4 N3 C7 118.40(14) . . ?
N3 N4 C15 111.44(14) . . ?
C33 N5 C21 111.19(13) . . ?
C33 N5 C29 110.97(13) . . ?
C21 N5 C29 105.91(12) . . ?
C33 N5 C25 106.16(12) . . ?
C21 N5 C25 111.51(13) . . ?
C29 N5 C25 111.20(13) . . ?
C2 C1 C6 118.11(16) . . ?
C2 C1 N1 116.78(16) . . ?
C6 C1 N1 125.10(15) . . ?
C3 C2 C1 121.30(17) . . ?
C4 C3 C2 120.40(17) . . ?
C3 C4 C5 118.93(17) . . ?
C4 C5 C6 121.07(18) . . ?
C5 C6 C1 120.15(17) . . ?
N3 C7 N2 109.19(14) . . ?
N3 C7 C8 125.40(14) . . ?
N2 C7 C8 125.32(14) . . ?
C13 C8 C9 116.67(16) . . ?
C13 C8 C7 120.31(15) . . ?
C9 C8 C7 122.94(14) . . ?
C10 C9 C8 121.38(16) . . ?
C11 C10 C9 121.46(17) . . ?
C10 C11 C12 117.40(17) . . ?
C10 C11 C14 121.69(17) . . ?
C12 C11 C14 120.91(17) . . ?
C13 C12 C11 121.67(17) . . ?
C12 C13 C8 121.39(16) . . ?
C16 C15 C20 118.29(15) . . ?
C16 C15 N4 117.00(15) . . ?
C20 C15 N4 124.63(15) . . ?
C17 C16 C15 120.96(16) . . ?
C18 C17 C16 120.26(16) . . ?
C17 C18 C19 119.31(17) . . ?
C20 C19 C18 121.00(18) . . ?
C19 C20 C15 120.18(16) . . ?
C22 C21 N5 117.01(13) . . ?
C21 C22 C23 108.60(14) . . ?
C24 C23 C22 113.52(16) . . ?
C26 C25 N5 115.52(14) . . ?
C25 C26 C27 111.00(15) . . ?
C28 C27 C26 113.38(17) . . ?
C30 C29 N5 116.46(14) . . ?
C29 C30 C31 109.83(15) . . ?
C32 C31 C30 113.86(18) . . ?
C34 C33 N5 116.42(14) . . ?
C33 C34 C35 109.77(14) . . ?
C36 C35 C34 112.49(16) . . ?

_refine_diff_density_max         0.391
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.044

_shelxl_version_number           2013-4



_database_code_depnum_ccdc_archive 'CCDC 1020940'
