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

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

data_compound_5
_database_code_depnum_ccdc_archive 'CCDC 1476682'
#Added by publCIF



_audit_update_record             
;
2016-04-26 deposited with the CCDC.
2017-05-23 downloaded from the CCDC.
;
_publcif_datablock.id            {9af17915-6190-4092-a302-a37855ef3ff5}


_refine_ls_number_constraints    0

# publcif _publ_body_element loop start

# publcif _publ_body_element loop end
_audit_creation_date             2016-04-01
_audit_creation_method           
;
Olex2 1.2
(compiled Feb 16 2016 13:09:46 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H51 N11, H2 O'
_chemical_formula_sum            'C27 H53 N11 O'
_chemical_formula_weight         547.80
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.4773(5)
_cell_length_b                   14.9989(4)
_cell_length_c                   21.0082(7)
_cell_angle_alpha                90
_cell_angle_beta                 123.022(2)
_cell_angle_gamma                90
_cell_volume                     3032.29(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6421
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1200
_exptl_crystal_recrystallization_method 
'The material was recrystallised from ether by slow evaporation'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_exptl_special_details           ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10062
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.783
_diffrn_ambient_temperature      115(2)
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean 9
_diffrn_detector_type            CCD
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_orient_matrix_type       'Nonius Collect from scalepack cell'
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4136
_reflns_number_total             5308
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR97 (Burla et al., 2007)'
_refine_diff_density_max         0.988
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5308
_refine_ls_number_restraints     39
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0828
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0659P)²+7.6741P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1885
_refine_ls_wR_factor_ref         0.2062
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Riding coordinates:
 N1(H1), N2(H2), N3(H3), N5(H5), N7(H7A), N9(H9), N10(H10), N11(H11A)
3.b Free rotating group:
 O1(H1C,H1D)
3.c Ternary CH refined with riding coordinates:
 C7(H7), C11(H11), C17(H17), C19(H19)
3.d Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C18(H18A,H18B), C20(H20A,H20B),
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B),
  C26(H26A,H26B), C27(H27A,H27B)
3.e Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4099(4) 0.0935(2) 0.6962(2) 0.0416(9) Uani 1 1 d . U . . .
H1A H 0.3686 0.0740 0.7247 0.050 Uiso 1 1 calc R . . . .
H1B H 0.5105 0.0796 0.7272 0.050 Uiso 1 1 calc R . . . .
C2 C 0.3418(5) 0.0432(3) 0.6213(2) 0.0481(10) Uani 1 1 d . U . . .
H2A H 0.3805 -0.0179 0.6314 0.058 Uiso 1 1 calc R . . . .
H2B H 0.3667 0.0730 0.5883 0.058 Uiso 1 1 calc R . . . .
C3 C 0.1841(5) 0.0371(3) 0.5787(2) 0.0478(10) Uani 1 1 d . U . . .
H3A H 0.1493 0.0022 0.5317 0.057 Uiso 1 1 calc R . . . .
H3B H 0.1591 0.0043 0.6106 0.057 Uiso 1 1 calc R . . . .
C4 C 0.1158(4) 0.1682(3) 0.4977(2) 0.0422(9) Uani 1 1 d . U . . .
H4A H 0.0820 0.1269 0.4543 0.051 Uiso 1 1 calc R . . . .
H4B H 0.2120 0.1859 0.5155 0.051 Uiso 1 1 calc R . . . .
C5 C 0.0259(4) 0.2481(3) 0.4731(2) 0.0439(10) Uani 1 1 d . U . . .
H5A H -0.0706 0.2283 0.4523 0.053 Uiso 1 1 calc R . . . .
H5B H 0.0277 0.2764 0.4310 0.053 Uiso 1 1 calc R . . . .
C6 C 0.1812(4) 0.3698(3) 0.5485(2) 0.0398(9) Uani 1 1 d . U . . .
H6A H 0.1547 0.4096 0.5050 0.048 Uiso 1 1 calc R . . . .
H6B H 0.2551 0.3292 0.5552 0.048 Uiso 1 1 calc R . . . .
C7 C 0.2350(5) 0.4243(2) 0.6190(2) 0.0443(10) Uani 1 1 d . U . . .
H7 H 0.3112 0.4644 0.6265 0.053 Uiso 1 1 calc R . . . .
C8 C 0.4344(4) 0.3412(3) 0.7310(2) 0.0401(9) Uani 1 1 d . U . . .
H8A H 0.4838 0.3775 0.7779 0.048 Uiso 1 1 calc R . . . .
H8B H 0.4744 0.3556 0.7007 0.048 Uiso 1 1 calc R . . . .
C9 C 0.4586(4) 0.2429(3) 0.7523(2) 0.0367(9) Uani 1 1 d . U . . .
H9A H 0.5595 0.2301 0.7829 0.044 Uiso 1 1 calc R . . . .
H9B H 0.4198 0.2277 0.7831 0.044 Uiso 1 1 calc R . . . .
C10 C 0.1173(4) 0.4818(2) 0.6178(2) 0.0366(9) Uani 1 1 d . U . . .
H10A H 0.1447 0.5454 0.6281 0.044 Uiso 1 1 calc R . . . .
H10B H 0.0285 0.4771 0.5678 0.044 Uiso 1 1 calc R . . . .
C11 C 0.2381(3) 0.4062(2) 0.73198(18) 0.0255(7) Uani 1 1 d . U . . .
H11 H 0.3030 0.4553 0.7636 0.031 Uiso 1 1 calc R . . . .
C12 C 0.2309(3) 0.3395(2) 0.78377(18) 0.0226(7) Uani 1 1 d . U . . .
C13 C 0.3128(3) 0.3489(2) 0.86236(18) 0.0286(7) Uani 1 1 d . U . . .
H13 H 0.3719 0.3991 0.8850 0.034 Uiso 1 1 calc R . . . .
C14 C 0.3064(4) 0.2839(2) 0.90674(19) 0.0303(8) Uani 1 1 d . U . . .
H14 H 0.3616 0.2882 0.9605 0.036 Uiso 1 1 calc R . . . .
C15 C 0.2184(4) 0.2125(2) 0.87151(19) 0.0298(7) Uani 1 1 d . U . . .
H15 H 0.2134 0.1664 0.9010 0.036 Uiso 1 1 calc R . . . .
C16 C 0.1371(3) 0.2083(2) 0.79274(18) 0.0252(7) Uani 1 1 d . U . . .
C17 C 0.0393(4) 0.1309(2) 0.75114(19) 0.0299(7) Uani 1 1 d . U . . .
H17 H 0.0476 0.0874 0.7895 0.036 Uiso 1 1 calc R . . . .
C18 C -0.0481(4) 0.0321(2) 0.6520(2) 0.0391(9) Uani 1 1 d . U . . .
H18A H -0.0397 -0.0280 0.6736 0.047 Uiso 1 1 calc R . . . .
H18B H -0.0601 0.0256 0.6018 0.047 Uiso 1 1 calc R . . . .
C19 C -0.1760(4) 0.0841(2) 0.6439(2) 0.0425(9) Uani 1 1 d . U . . .
H19 H -0.2276 0.0440 0.6583 0.051 Uiso 1 1 calc R . . . .
C20 C -0.2729(5) 0.1196(3) 0.5662(2) 0.0495(10) Uani 1 1 d . U . . .
H20A H -0.3213 0.0694 0.5307 0.059 Uiso 1 1 calc R . . . .
H20B H -0.3438 0.1575 0.5659 0.059 Uiso 1 1 calc R . . . .
C21 C -0.2993(4) 0.2299(3) 0.4721(2) 0.0487(10) Uani 1 1 d . U . . .
H21A H -0.2522 0.2457 0.4457 0.058 Uiso 1 1 calc R . . . .
H21B H -0.3820 0.1939 0.4364 0.058 Uiso 1 1 calc R . . . .
C22 C -0.3471(4) 0.3132(3) 0.4884(2) 0.0494(10) Uani 1 1 d . U . . .
H22A H -0.4067 0.3469 0.4407 0.059 Uiso 1 1 calc R . . . .
H22B H -0.4030 0.2987 0.5099 0.059 Uiso 1 1 calc R . . . .
C23 C -0.2721(4) 0.4567(3) 0.5518(3) 0.0491(10) Uani 1 1 d . U . . .
H23A H -0.3361 0.4837 0.5013 0.059 Uiso 1 1 calc R . . . .
H23B H -0.1883 0.4949 0.5791 0.059 Uiso 1 1 calc R . . . .
C24 C -0.3425(4) 0.4563(3) 0.5955(3) 0.0488(10) Uani 1 1 d . U . . .
H24A H -0.3684 0.5184 0.5986 0.059 Uiso 1 1 calc R . . . .
H24B H -0.4296 0.4215 0.5661 0.059 Uiso 1 1 calc R . . . .
C25 C -0.2588(5) 0.4191(3) 0.6737(3) 0.0479(10) Uani 1 1 d . U . . .
H25A H -0.1630 0.4429 0.6998 0.057 Uiso 1 1 calc R . . . .
H25B H -0.2995 0.4385 0.7026 0.057 Uiso 1 1 calc R . . . .
C26 C -0.1739(4) 0.2821(3) 0.7497(2) 0.0377(9) Uani 1 1 d . U . . .
H26A H -0.2174 0.2974 0.7780 0.045 Uiso 1 1 calc R . . . .
H26B H -0.0778 0.3056 0.7783 0.045 Uiso 1 1 calc R . . . .
C27 C -0.1714(4) 0.1826(3) 0.7422(2) 0.0387(9) Uani 1 1 d . U . . .
H27A H -0.1194 0.1553 0.7933 0.046 Uiso 1 1 calc R . . . .
H27B H -0.2676 0.1594 0.7146 0.046 Uiso 1 1 calc R . . . .
N1 N 0.3908(3) 0.18930(18) 0.68302(15) 0.0278(6) Uani 1 1 d . U . . .
H1 H 0.3018 0.1995 0.6571 0.033 Uiso 1 1 d R . . . .
N2 N 0.1144(3) 0.1236(2) 0.55859(17) 0.0385(7) Uani 1 1 d . U . . .
H2 H 0.0278 0.1174 0.5438 0.046 Uiso 1 1 d R . . . .
N3 N 0.0624(3) 0.3184(2) 0.53286(17) 0.0339(7) Uani 1 1 d . U . . .
H3 H 0.0857 0.2930 0.5755 0.041 Uiso 1 1 d R . . . .
N4 N 0.2884(3) 0.36511(18) 0.68782(16) 0.0281(6) Uani 1 1 d . U . . .
N5 N 0.1033(3) 0.44426(18) 0.67776(15) 0.0277(6) Uani 1 1 d . U . . .
H5 H 0.0446 0.4003 0.6584 0.033 Uiso 1 1 d R . . . .
N6 N 0.1437(3) 0.27113(17) 0.74895(14) 0.0229(6) Uani 1 1 d . U . . .
N7 N 0.0753(3) 0.08584(19) 0.70301(16) 0.0318(7) Uani 1 1 d . U . . .
H7A H 0.0879 0.1289 0.6797 0.038 Uiso 1 1 d R . . . .
N8 N -0.1068(3) 0.15785(19) 0.70174(16) 0.0304(7) Uani 1 1 d . U . . .
N9 N -0.2540(3) 0.32248(19) 0.67329(17) 0.0331(7) Uani 1 1 d . U . . .
H9 H -0.2108 0.3100 0.6509 0.040 Uiso 1 1 d R . . . .
N10 N -0.2304(3) 0.3669(2) 0.54118(18) 0.0449(8) Uani 1 1 d . U . . .
H10 H -0.1759 0.3684 0.5244 0.054 Uiso 1 1 d R . . . .
N11 N -0.1994(3) 0.1709(2) 0.54139(18) 0.0408(8) Uani 1 1 d . U . . .
H11A H -0.1481 0.2072 0.5788 0.049 Uiso 1 1 d R . . . .
O1 O 0.5200(3) 0.7566(2) 0.41265(14) 0.0456(7) Uani 1 1 d . U . . .
H1C H 0.5476 0.7732 0.3832 0.068 Uiso 1 1 d G . . . .
H1D H 0.4369 0.7340 0.3852 0.068 Uiso 1 1 d G . . . .


_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 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.521(6) . ?
C1 N1 1.457(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.523(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 N2 1.461(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.478(6) . ?
C4 N2 1.451(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 N3 1.514(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.500(5) . ?
C6 N3 1.440(5) . ?
C7 H7 1.0000 . ?
C7 C10 1.591(5) . ?
C7 N4 1.513(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.522(6) . ?
C8 N4 1.450(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 N1 1.461(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 N5 1.466(4) . ?
C11 H11 1.0000 . ?
C11 C12 1.513(4) . ?
C11 N4 1.469(4) . ?
C11 N5 1.447(4) . ?
C12 C13 1.392(4) . ?
C12 N6 1.338(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.379(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.378(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(5) . ?
C16 C17 1.516(5) . ?
C16 N6 1.348(4) . ?
C17 H17 1.0000 . ?
C17 N7 1.451(4) . ?
C17 N8 1.468(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.588(6) . ?
C18 N7 1.467(5) . ?
C19 H19 1.0000 . ?
C19 C20 1.485(6) . ?
C19 N8 1.509(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 N11 1.433(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.478(6) . ?
C21 N11 1.549(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 N10 1.433(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.518(6) . ?
C23 N10 1.487(6) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.489(6) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 N9 1.450(5) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.502(6) . ?
C26 N9 1.477(5) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 N8 1.448(4) . ?
N1 H1 0.8700 . ?
N2 H2 0.8700 . ?
N3 H3 0.8701 . ?
N5 H5 0.8700 . ?
N7 H7A 0.8700 . ?
N9 H9 0.8699 . ?
N10 H10 0.8698 . ?
N11 H11A 0.8700 . ?
O1 H1C 0.8707 . ?
O1 H1D 0.8700 . ?

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
H1A C1 H1B 108.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 C2 110.7(3) . . ?
C1 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
C1 C2 C3 114.4(3) . . ?
H2A C2 H2B 107.6 . . ?
C3 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
C2 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
N2 C3 C2 113.9(3) . . ?
N2 C3 H3A 108.8 . . ?
N2 C3 H3B 108.8 . . ?
H4A C4 H4B 108.2 . . ?
C5 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
N2 C4 H4A 109.7 . . ?
N2 C4 H4B 109.7 . . ?
N2 C4 C5 110.0(3) . . ?
C4 C5 H5A 108.1 . . ?
C4 C5 H5B 108.1 . . ?
C4 C5 N3 116.7(3) . . ?
H5A C5 H5B 107.3 . . ?
N3 C5 H5A 108.1 . . ?
N3 C5 H5B 108.1 . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
N3 C6 H6A 109.6 . . ?
N3 C6 H6B 109.6 . . ?
N3 C6 C7 110.2(3) . . ?
C6 C7 H7 109.8 . . ?
C6 C7 C10 113.0(4) . . ?
C6 C7 N4 111.0(3) . . ?
C10 C7 H7 109.8 . . ?
N4 C7 H7 109.8 . . ?
N4 C7 C10 103.4(3) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
N4 C8 H8A 109.0 . . ?
N4 C8 H8B 109.0 . . ?
N4 C8 C9 112.8(3) . . ?
C8 C9 H9A 109.9 . . ?
C8 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
N1 C9 C8 109.1(3) . . ?
N1 C9 H9A 109.9 . . ?
N1 C9 H9B 109.9 . . ?
C7 C10 H10A 110.6 . . ?
C7 C10 H10B 110.6 . . ?
H10A C10 H10B 108.8 . . ?
N5 C10 C7 105.5(3) . . ?
N5 C10 H10A 110.6 . . ?
N5 C10 H10B 110.6 . . ?
C12 C11 H11 108.8 . . ?
N4 C11 H11 108.8 . . ?
N4 C11 C12 111.8(3) . . ?
N5 C11 H11 108.8 . . ?
N5 C11 C12 111.9(3) . . ?
N5 C11 N4 106.7(3) . . ?
C13 C12 C11 121.3(3) . . ?
N6 C12 C11 115.5(3) . . ?
N6 C12 C13 123.2(3) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 C12 118.7(3) . . ?
C14 C13 H13 120.7 . . ?
C13 C14 H14 120.7 . . ?
C15 C14 C13 118.7(3) . . ?
C15 C14 H14 120.7 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.7(3) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 121.8(3) . . ?
N6 C16 C15 122.0(3) . . ?
N6 C16 C17 116.2(3) . . ?
C16 C17 H17 108.6 . . ?
N7 C17 C16 110.9(3) . . ?
N7 C17 H17 108.6 . . ?
N7 C17 N8 106.5(3) . . ?
N8 C17 C16 113.5(3) . . ?
N8 C17 H17 108.6 . . ?
H18A C18 H18B 108.7 . . ?
C19 C18 H18A 110.5 . . ?
C19 C18 H18B 110.5 . . ?
N7 C18 H18A 110.5 . . ?
N7 C18 H18B 110.5 . . ?
N7 C18 C19 106.0(3) . . ?
C18 C19 H19 109.7 . . ?
C20 C19 C18 112.8(3) . . ?
C20 C19 H19 109.7 . . ?
C20 C19 N8 111.9(3) . . ?
N8 C19 C18 102.9(3) . . ?
N8 C19 H19 109.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
N11 C20 C19 110.8(4) . . ?
N11 C20 H20A 109.5 . . ?
N11 C20 H20B 109.5 . . ?
H21A C21 H21B 107.4 . . ?
C22 C21 H21A 108.2 . . ?
C22 C21 H21B 108.2 . . ?
C22 C21 N11 116.3(3) . . ?
N11 C21 H21A 108.2 . . ?
N11 C21 H21B 108.2 . . ?
C21 C22 H22A 109.6 . . ?
C21 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
N10 C22 C21 110.2(4) . . ?
N10 C22 H22A 109.6 . . ?
N10 C22 H22B 109.6 . . ?
H23A C23 H23B 107.6 . . ?
C24 C23 H23A 108.7 . . ?
C24 C23 H23B 108.7 . . ?
N10 C23 H23A 108.7 . . ?
N10 C23 H23B 108.7 . . ?
N10 C23 C24 114.1(3) . . ?
C23 C24 H24A 108.4 . . ?
C23 C24 H24B 108.4 . . ?
H24A C24 H24B 107.4 . . ?
C25 C24 C23 115.6(4) . . ?
C25 C24 H24A 108.4 . . ?
C25 C24 H24B 108.4 . . ?
C24 C25 H25A 109.3 . . ?
C24 C25 H25B 109.3 . . ?
H25A C25 H25B 107.9 . . ?
N9 C25 C24 111.8(4) . . ?
N9 C25 H25A 109.3 . . ?
N9 C25 H25B 109.3 . . ?
H26A C26 H26B 108.3 . . ?
C27 C26 H26A 109.8 . . ?
C27 C26 H26B 109.8 . . ?
N9 C26 H26A 109.8 . . ?
N9 C26 H26B 109.8 . . ?
N9 C26 C27 109.2(3) . . ?
C26 C27 H27A 109.4 . . ?
C26 C27 H27B 109.4 . . ?
H27A C27 H27B 108.0 . . ?
N8 C27 C26 111.3(3) . . ?
N8 C27 H27A 109.4 . . ?
N8 C27 H27B 109.4 . . ?
C1 N1 C9 114.2(3) . . ?
C1 N1 H1 107.2 . . ?
C9 N1 H1 109.5 . . ?
C3 N2 H2 110.3 . . ?
C4 N2 C3 113.4(3) . . ?
C4 N2 H2 107.1 . . ?
C5 N3 H3 109.8 . . ?
C6 N3 C5 111.1(3) . . ?
C6 N3 H3 106.1 . . ?
C8 N4 C7 118.1(3) . . ?
C8 N4 C11 115.3(3) . . ?
C11 N4 C7 105.2(3) . . ?
C10 N5 H5 108.1 . . ?
C11 N5 C10 104.9(3) . . ?
C11 N5 H5 107.0 . . ?
C12 N6 C16 117.8(3) . . ?
C17 N7 C18 103.8(3) . . ?
C17 N7 H7A 104.2 . . ?
C18 N7 H7A 112.8 . . ?
C17 N8 C19 105.4(3) . . ?
C27 N8 C17 114.1(3) . . ?
C27 N8 C19 116.6(3) . . ?
C25 N9 C26 114.0(3) . . ?
C25 N9 H9 104.7 . . ?
C26 N9 H9 107.5 . . ?
C22 N10 C23 112.6(3) . . ?
C22 N10 H10 106.0 . . ?
C23 N10 H10 113.5 . . ?
C20 N11 C21 111.6(3) . . ?
C20 N11 H11A 104.5 . . ?
C21 N11 H11A 106.3 . . ?
H1C O1 H1D 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N2 0.87 2.31 2.972(4) 132.6 .
N9 H9 N10 0.87 2.35 3.007(4) 132.4 .
O1 H1C N1 0.87 1.96 2.826(4) 179.9 3_666
O1 H1D N9 0.87 1.96 2.825(4) 176.9 3_566

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 N2 60.0(5) . . . . ?
C2 C1 N1 C9 -177.4(3) . . . . ?
C2 C3 N2 C4 72.6(4) . . . . ?
C4 C5 N3 C6 76.0(4) . . . . ?
C5 C4 N2 C3 171.6(3) . . . . ?
C6 C7 C10 N5 113.6(3) . . . . ?
C6 C7 N4 C8 91.9(4) . . . . ?
C6 C7 N4 C11 -137.7(3) . . . . ?
C7 C6 N3 C5 -167.3(3) . . . . ?
C7 C10 N5 C11 27.1(4) . . . . ?
C8 C9 N1 C1 178.4(3) . . . . ?
C9 C8 N4 C7 -135.7(3) . . . . ?
C9 C8 N4 C11 98.8(3) . . . . ?
C10 C7 N4 C8 -146.6(3) . . . . ?
C10 C7 N4 C11 -16.3(4) . . . . ?
C11 C12 C13 C14 -177.1(3) . . . . ?
C11 C12 N6 C16 177.8(3) . . . . ?
C12 C11 N4 C7 157.1(3) . . . . ?
C12 C11 N4 C8 -70.9(4) . . . . ?
C12 C11 N5 C10 -161.5(3) . . . . ?
C12 C13 C14 C15 -0.5(5) . . . . ?
C13 C12 N6 C16 -0.8(4) . . . . ?
C13 C14 C15 C16 -1.0(5) . . . . ?
C14 C15 C16 C17 179.6(3) . . . . ?
C14 C15 C16 N6 1.7(5) . . . . ?
C15 C16 C17 N7 -120.4(3) . . . . ?
C15 C16 C17 N8 119.7(3) . . . . ?
C15 C16 N6 C12 -0.8(4) . . . . ?
C16 C17 N7 C18 -164.3(3) . . . . ?
C16 C17 N8 C19 157.7(3) . . . . ?
C16 C17 N8 C27 -73.2(4) . . . . ?
C17 C16 N6 C12 -178.7(3) . . . . ?
C18 C19 C20 N11 -52.2(4) . . . . ?
C18 C19 N8 C17 -16.0(3) . . . . ?
C18 C19 N8 C27 -143.7(3) . . . . ?
C19 C18 N7 C17 28.8(4) . . . . ?
C19 C20 N11 C21 -163.8(3) . . . . ?
C20 C19 N8 C17 -137.5(3) . . . . ?
C20 C19 N8 C27 94.9(4) . . . . ?
C21 C22 N10 C23 172.3(3) . . . . ?
C22 C21 N11 C20 78.9(4) . . . . ?
C23 C24 C25 N9 -76.5(5) . . . . ?
C24 C23 N10 C22 71.1(5) . . . . ?
C24 C25 N9 C26 -179.0(3) . . . . ?
C26 C27 N8 C17 98.8(4) . . . . ?
C26 C27 N8 C19 -137.9(3) . . . . ?
C27 C26 N9 C25 -177.8(3) . . . . ?
N1 C1 C2 C3 -76.0(4) . . . . ?
N2 C4 C5 N3 58.9(4) . . . . ?
N3 C6 C7 C10 -51.3(4) . . . . ?
N3 C6 C7 N4 64.3(4) . . . . ?
N4 C7 C10 N5 -6.4(4) . . . . ?
N4 C8 C9 N1 61.2(4) . . . . ?
N4 C11 C12 C13 116.6(3) . . . . ?
N4 C11 C12 N6 -62.1(4) . . . . ?
N4 C11 N5 C10 -38.9(3) . . . . ?
N5 C11 C12 C13 -123.8(3) . . . . ?
N5 C11 C12 N6 57.5(4) . . . . ?
N5 C11 N4 C7 34.4(3) . . . . ?
N5 C11 N4 C8 166.4(3) . . . . ?
N6 C12 C13 C14 1.5(5) . . . . ?
N6 C16 C17 N7 57.6(4) . . . . ?
N6 C16 C17 N8 -62.3(4) . . . . ?
N7 C17 N8 C19 35.4(3) . . . . ?
N7 C17 N8 C27 164.6(3) . . . . ?
N7 C18 C19 C20 113.0(3) . . . . ?
N7 C18 C19 N8 -7.8(4) . . . . ?
N8 C17 N7 C18 -40.4(3) . . . . ?
N8 C19 C20 N11 63.3(4) . . . . ?
N9 C26 C27 N8 60.2(4) . . . . ?
N10 C23 C24 C25 59.5(5) . . . . ?
N11 C21 C22 N10 56.8(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a glass fibre oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_compound_12
_database_code_depnum_ccdc_archive 'CCDC 1476683'
#Added by publCIF



_audit_update_record             
;
2016-04-26 deposited with the CCDC.
2017-05-23 downloaded from the CCDC.
;
_publcif_datablock.id            {2dce831f-99e8-4974-ad19-540f259f3a8c}


_refine_ls_number_constraints    0

# publcif _publ_body_element loop start

# publcif _publ_body_element loop end
_audit_creation_date             2016-03-31
_audit_creation_method           
;
Olex2 1.2
(compiled Feb 16 2016 13:09:46 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H27 N5 O'
_chemical_formula_sum            'C18 H27 N5 O'
_chemical_formula_weight         329.44
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.2517(5)
_cell_length_b                   12.3383(4)
_cell_length_c                   12.0306(4)
_cell_angle_alpha                90
_cell_angle_beta                 114.6840(10)
_cell_angle_gamma                90
_cell_volume                     1787.31(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    28874
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_recrystallization_method 
'The material was recrystallised from hexane by slow evaporation'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14520
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.562
_diffrn_reflns_theta_min         2.363
_diffrn_ambient_temperature      115(2)
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean 9
_diffrn_detector_type            CCD
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_orient_matrix_type       'Nonius Collect from scalepack cell'
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2485
_reflns_number_total             4104
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR97 (Burla et al., 2007)'
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4104
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0412P)²+0.4008P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1180
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Fixed occupancy and ADP/Uiso:
 H2, H3, H4
3.b Ternary CH refined with riding coordinates:
 C8(H8), C11(H11)
3.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B)
3.d Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.24544(13) -0.19615(14) 0.27041(15) 0.0347(4) Uani 1 1 d . U . . .
H1A H 0.2762 -0.1733 0.2119 0.042 Uiso 1 1 calc R . . . .
H1B H 0.1846 -0.2483 0.2278 0.042 Uiso 1 1 calc R . . . .
C2 C 0.33567(13) -0.25263(14) 0.37776(15) 0.0356(4) Uani 1 1 d . U . . .
H2A H 0.3027 -0.2855 0.4300 0.043 Uiso 1 1 calc R . . . .
H2B H 0.3677 -0.3117 0.3470 0.043 Uiso 1 1 calc R . . . .
C3 C 0.50639(14) -0.23293(15) 0.55777(17) 0.0442(5) Uani 1 1 d . U . . .
H3A H 0.5508 -0.2822 0.5309 0.053 Uiso 1 1 calc R . . . .
H3B H 0.4679 -0.2776 0.5966 0.053 Uiso 1 1 calc R . . . .
C4 C 0.58375(14) -0.15444(16) 0.65150(16) 0.0445(5) Uani 1 1 d . U . . .
H4A H 0.6161 -0.1049 0.6103 0.053 Uiso 1 1 calc R . . . .
H4B H 0.6455 -0.1958 0.7138 0.053 Uiso 1 1 calc R . . . .
C5 C 0.52786(15) -0.08731(16) 0.71558(16) 0.0450(5) Uani 1 1 d . U . . .
H5A H 0.4818 -0.1354 0.7415 0.054 Uiso 1 1 calc R . . . .
H5B H 0.5855 -0.0542 0.7900 0.054 Uiso 1 1 calc R . . . .
C6 C 0.39212(15) 0.05754(16) 0.68919(16) 0.0425(5) Uani 1 1 d . U . . .
H6A H 0.3916 0.1357 0.6703 0.051 Uiso 1 1 calc R . . . .
H6B H 0.4269 0.0491 0.7792 0.051 Uiso 1 1 calc R . . . .
C7 C 0.27387(15) 0.01578(16) 0.63890(15) 0.0413(5) Uani 1 1 d . U . . .
H7A H 0.2743 -0.0639 0.6487 0.050 Uiso 1 1 calc R . . . .
H7B H 0.2347 0.0481 0.6852 0.050 Uiso 1 1 calc R . . . .
C8 C 0.11985(14) -0.02498(17) 0.44110(17) 0.0449(5) Uani 1 1 d . U . . .
H8 H 0.0846 -0.0461 0.4970 0.054 Uiso 1 1 calc R . . . .
C9 C 0.15215(14) -0.12854(15) 0.39452(16) 0.0410(5) Uani 1 1 d . U . . .
H9A H 0.2075 -0.1693 0.4641 0.049 Uiso 1 1 calc R . . . .
H9B H 0.0859 -0.1750 0.3542 0.049 Uiso 1 1 calc R . . . .
C10 C 0.03461(16) 0.0371(2) 0.33415(17) 0.0634(7) Uani 1 1 d . U . . .
H10A H -0.0374 -0.0016 0.3022 0.076 Uiso 1 1 calc R . . . .
H10B H 0.0234 0.1101 0.3614 0.076 Uiso 1 1 calc R . . . .
C11 C 0.11218(13) -0.04933(15) 0.19832(15) 0.0346(4) Uani 1 1 d . U . . .
H11 H 0.0492 -0.1008 0.1571 0.042 Uiso 1 1 calc R . . . .
C12 C 0.09736(15) 0.14096(19) 0.19585(17) 0.0518(6) Uani 1 1 d . U . . .
C13 C 0.14449(14) 0.10962(15) 0.10866(16) 0.0397(5) Uani 1 1 d . U . . .
C14 C 0.15065(12) -0.00207(14) 0.10657(14) 0.0310(4) Uani 1 1 d . U . . .
C15 C 0.18349(13) -0.05141(14) 0.02331(15) 0.0350(4) Uani 1 1 d . U . . .
H15 H 0.1847 -0.1282 0.0177 0.042 Uiso 1 1 calc R . . . .
C16 C 0.21446(15) 0.01329(16) -0.05146(16) 0.0429(5) Uani 1 1 d . U . . .
H16 H 0.2384 -0.0200 -0.1075 0.051 Uiso 1 1 calc R . . . .
C17 C 0.21125(15) 0.12414(17) -0.04641(18) 0.0493(5) Uani 1 1 d . U . . .
H17 H 0.2341 0.1665 -0.0977 0.059 Uiso 1 1 calc R . . . .
C18 C 0.17496(15) 0.17496(16) 0.03281(18) 0.0496(5) Uani 1 1 d . U . . .
H18 H 0.1709 0.2517 0.0355 0.060 Uiso 1 1 calc R . . . .
N1 N 0.19956(10) -0.10086(11) 0.30627(12) 0.0291(3) Uani 1 1 d . U . . .
N2 N 0.42339(11) -0.17844(12) 0.45062(13) 0.0330(3) Uani 1 1 d . U . . .
H2 H 0.3980(14) -0.1230(14) 0.4774(16) 0.040 Uiso 1 1 d . . . . .
N3 N 0.45738(12) -0.00112(13) 0.63660(12) 0.0366(4) Uani 1 1 d . U . . .
H3 H 0.4984(15) 0.0468(14) 0.6172(16) 0.044 Uiso 1 1 d . . . . .
N4 N 0.21586(12) 0.04381(12) 0.50981(13) 0.0374(4) Uani 1 1 d . U . . .
H4 H 0.2644(15) 0.0328(14) 0.4758(16) 0.045 Uiso 1 1 d . . . . .
N5 N 0.07388(12) 0.04679(15) 0.23912(13) 0.0463(4) Uani 1 1 d . U . . .
O1 O 0.07985(12) 0.23325(12) 0.22274(13) 0.0754(5) Uani 1 1 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 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.514(2) . ?
C1 N1 1.469(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 N2 1.451(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.515(3) . ?
C3 N2 1.463(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.519(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 N3 1.471(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.515(2) . ?
C6 N3 1.459(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 N4 1.458(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.526(3) . ?
C8 C10 1.518(3) . ?
C8 N4 1.464(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 N1 1.482(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 N5 1.445(2) . ?
C11 H11 1.0000 . ?
C11 C14 1.513(2) . ?
C11 N1 1.475(2) . ?
C11 N5 1.454(2) . ?
C12 C13 1.479(3) . ?
C12 N5 1.361(3) . ?
C12 O1 1.232(2) . ?
C13 C14 1.381(2) . ?
C13 C18 1.398(3) . ?
C14 C15 1.388(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.370(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.384(3) . ?
C18 H18 0.9500 . ?
N2 H2 0.880(18) . ?
N3 H3 0.898(18) . ?
N4 H4 0.905(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
H1A C1 H1B 107.7 . . ?
C2 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
N1 C1 H1A 108.9 . . ?
N1 C1 H1B 108.9 . . ?
N1 C1 C2 113.21(13) . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
N2 C2 C1 111.89(14) . . ?
N2 C2 H2A 109.2 . . ?
N2 C2 H2B 109.2 . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
N2 C3 H3A 109.0 . . ?
N2 C3 H3B 109.0 . . ?
N2 C3 C4 112.85(15) . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C3 C4 C5 113.87(14) . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
N3 C5 C4 112.27(15) . . ?
N3 C5 H5A 109.1 . . ?
N3 C5 H5B 109.1 . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
N3 C6 H6A 109.4 . . ?
N3 C6 H6B 109.4 . . ?
N3 C6 C7 111.08(14) . . ?
C6 C7 H7A 109.7 . . ?
C6 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
N4 C7 C6 110.00(15) . . ?
N4 C7 H7A 109.7 . . ?
N4 C7 H7B 109.7 . . ?
C9 C8 H8 108.1 . . ?
C10 C8 H8 108.1 . . ?
C10 C8 C9 109.56(15) . . ?
N4 C8 H8 108.1 . . ?
N4 C8 C9 112.44(14) . . ?
N4 C8 C10 110.45(17) . . ?
C8 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
N1 C9 C8 109.75(15) . . ?
N1 C9 H9A 109.7 . . ?
N1 C9 H9B 109.7 . . ?
C8 C10 H10A 109.9 . . ?
C8 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
N5 C10 C8 109.02(14) . . ?
N5 C10 H10A 109.9 . . ?
N5 C10 H10B 109.9 . . ?
C14 C11 H11 110.4 . . ?
N1 C11 H11 110.4 . . ?
N1 C11 C14 115.39(12) . . ?
N5 C11 H11 110.4 . . ?
N5 C11 C14 101.75(15) . . ?
N5 C11 N1 108.10(13) . . ?
N5 C12 C13 106.25(16) . . ?
O1 C12 C13 127.6(2) . . ?
O1 C12 N5 126.2(2) . . ?
C14 C13 C12 108.63(18) . . ?
C14 C13 C18 121.89(18) . . ?
C18 C13 C12 129.42(18) . . ?
C13 C14 C11 109.32(15) . . ?
C13 C14 C15 119.29(17) . . ?
C15 C14 C11 131.31(16) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 C14 118.84(17) . . ?
C16 C15 H15 120.6 . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.51(18) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.59(19) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 H18 121.1 . . ?
C17 C18 C13 117.80(18) . . ?
C17 C18 H18 121.1 . . ?
C1 N1 C9 112.17(13) . . ?
C1 N1 C11 110.82(12) . . ?
C11 N1 C9 108.56(12) . . ?
C2 N2 C3 111.12(14) . . ?
C2 N2 H2 112.2(11) . . ?
C3 N2 H2 107.2(11) . . ?
C5 N3 H3 110.7(11) . . ?
C6 N3 C5 114.20(14) . . ?
C6 N3 H3 108.6(12) . . ?
C7 N4 C8 114.28(15) . . ?
C7 N4 H4 106.7(11) . . ?
C8 N4 H4 105.8(11) . . ?
C10 N5 C11 119.45(18) . . ?
C12 N5 C10 126.04(17) . . ?
C12 N5 C11 113.54(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 N3 0.880(18) 2.300(18) 3.026(2) 139.7(15) .
N3 H3 N2 0.898(18) 2.255(19) 3.145(2) 171.3(16) 3_656
N4 H4 N1 0.905(19) 2.481(18) 2.9643(19) 113.8(14) .
N4 H4 N3 0.905(19) 2.515(18) 2.966(2) 111.3(13) .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 N2 C3 176.66(14) . . . . ?
C2 C1 N1 C9 -58.42(17) . . . . ?
C2 C1 N1 C11 -179.93(13) . . . . ?
C3 C4 C5 N3 -74.80(19) . . . . ?
C4 C3 N2 C2 -166.31(15) . . . . ?
C4 C5 N3 C6 173.36(14) . . . . ?
C6 C7 N4 C8 157.60(15) . . . . ?
C7 C6 N3 C5 -99.23(17) . . . . ?
C8 C9 N1 C1 172.59(13) . . . . ?
C8 C9 N1 C11 -64.62(16) . . . . ?
C8 C10 N5 C11 50.2(2) . . . . ?
C8 C10 N5 C12 -117.7(2) . . . . ?
C9 C8 C10 N5 -49.4(2) . . . . ?
C9 C8 N4 C7 -85.34(18) . . . . ?
C10 C8 C9 N1 59.61(18) . . . . ?
C10 C8 N4 C7 151.93(15) . . . . ?
C11 C14 C15 C16 179.56(15) . . . . ?
C12 C13 C14 C11 -2.68(17) . . . . ?
C12 C13 C14 C15 174.48(14) . . . . ?
C12 C13 C18 C17 -176.16(16) . . . . ?
C13 C12 N5 C10 174.73(14) . . . . ?
C13 C12 N5 C11 6.22(18) . . . . ?
C13 C14 C15 C16 3.1(2) . . . . ?
C14 C11 N1 C1 -64.38(18) . . . . ?
C14 C11 N1 C9 172.01(14) . . . . ?
C14 C11 N5 C10 -176.87(14) . . . . ?
C14 C11 N5 C12 -7.53(17) . . . . ?
C14 C13 C18 C17 0.5(2) . . . . ?
C14 C15 C16 C17 -1.3(3) . . . . ?
C15 C16 C17 C18 -1.1(3) . . . . ?
C16 C17 C18 C13 1.4(3) . . . . ?
C18 C13 C14 C11 -179.95(14) . . . . ?
C18 C13 C14 C15 -2.8(2) . . . . ?
N1 C1 C2 N2 -53.79(18) . . . . ?
N1 C11 C14 C13 -110.80(15) . . . . ?
N1 C11 C14 C15 72.5(2) . . . . ?
N1 C11 N5 C10 -54.96(19) . . . . ?
N1 C11 N5 C12 114.38(15) . . . . ?
N2 C3 C4 C5 68.6(2) . . . . ?
N3 C6 C7 N4 -68.4(2) . . . . ?
N4 C8 C9 N1 -63.62(19) . . . . ?
N4 C8 C10 N5 74.9(2) . . . . ?
N5 C11 C14 C13 5.94(16) . . . . ?
N5 C11 C14 C15 -170.76(16) . . . . ?
N5 C11 N1 C1 -177.47(14) . . . . ?
N5 C11 N1 C9 58.92(17) . . . . ?
N5 C12 C13 C14 -1.99(18) . . . . ?
N5 C12 C13 C18 175.01(16) . . . . ?
O1 C12 C13 C14 179.59(17) . . . . ?
O1 C12 C13 C18 -3.4(3) . . . . ?
O1 C12 N5 C10 -6.8(3) . . . . ?
O1 C12 N5 C11 -175.34(16) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a glass fibre oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound_3
_database_code_depnum_ccdc_archive 'CCDC 1476681'
#Added by publCIF



_audit_update_record             
;
2016-04-26 deposited with the CCDC.
2017-05-23 downloaded from the CCDC.
;
_publcif_datablock.id            {64343868-cd66-4bf2-8930-ef488cc57d34}


_refine_ls_number_constraints    0

# publcif _publ_body_element loop start

# publcif _publ_body_element loop end
_audit_creation_date             2016-04-01
_audit_creation_method           
;
Olex2 1.2
(compiled Feb 16 2016 13:09:46 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H52 N10, H2 O '
_chemical_formula_sum            'C28 H54 N10 O'
_chemical_formula_weight         546.81
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   11.4792(3)
_cell_length_b                   15.0992(4)
_cell_length_c                   17.6024(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.3720(10)
_cell_angle_gamma                90
_cell_volume                     3050.90(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    28874
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1200
_exptl_crystal_recrystallization_method 
'The material was recrystallised from diethyl ether by slow evaporation'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.2
_exptl_special_details           ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12417
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_min         1.777
_diffrn_ambient_temperature      115(2)
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean 9
_diffrn_detector_type            CCD
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_orient_matrix_type       'Nonius Collect from scalepack cell'
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4919
_reflns_number_total             6959
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR97 (Burla et al., 2007)'
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         6959
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0713
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0923P)²+2.7095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1799
_refine_ls_wR_factor_ref         0.1991
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Riding coordinates:
 N10(H2), N3(H3), N4(H4), N5(H5), N7(H7), N8(H8), N9(H9), N9(H10)
2.b Free rotating group:
 O1(H1C,H1D)
2.c Ternary CH refined with riding coordinates:
 C9(H9A), C11(H11), C18(H18), C20(H20)
2.d Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C8(H8A,H8B), C10(H10A,H10B), C19(H19A,H19B), C21(H21A,H21B),
 C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B),
  C27(H27A,H27B), C28(H28A,H28B)
2.e Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C17(H17)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.10854(16) 0.24259(15) 0.41370(10) 0.0429(5) Uani 1 1 d . . . . .
H1C H 0.0506 0.2634 0.3872 0.064 Uiso 1 1 d G . . . .
H1D H 0.1614 0.2219 0.3834 0.064 Uiso 1 1 d G . . . .
N1 N 0.80829(18) 0.15313(13) 0.30017(11) 0.0302(5) Uani 1 1 d . . . . .
N2 N 0.92546(18) 0.31866(14) 0.32855(12) 0.0327(5) Uani 1 1 d . . . . .
N10 N 0.56455(17) 0.45578(12) 0.32144(11) 0.0283(4) Uani 1 1 d . . . . .
H2 H 0.8614 0.3023 0.3514 0.034 Uiso 1 1 d R . . . .
N3 N 0.7689(2) 0.35954(16) 0.46109(13) 0.0427(6) Uani 1 1 d . . . . .
H3 H 0.6989 0.3615 0.4796 0.051 Uiso 1 1 d R . . . .
N4 N 0.74472(18) 0.16396(16) 0.46055(12) 0.0381(5) Uani 1 1 d . . . . .
H4 H 0.7286 0.1995 0.4231 0.046 Uiso 1 1 d R . . . .
N5 N 0.63151(18) 0.07734(13) 0.29588(12) 0.0332(5) Uani 1 1 d . . . . .
H5 H 0.5951 0.1166 0.3230 0.040 Uiso 1 1 d R . . . .
N6 N 0.39540(16) 0.37021(12) 0.31287(10) 0.0247(4) Uani 1 1 d . . . . .
N7 N 0.29383(18) 0.19292(13) 0.31757(10) 0.0284(4) Uani 1 1 d . . . . .
H7 H 0.3560 0.2026 0.3448 0.034 Uiso 1 1 d R . . . .
N8 N 0.44937(18) 0.13150(13) 0.44370(11) 0.0313(5) Uani 1 1 d . . . . .
H8 H 0.5217 0.1277 0.4585 0.038 Uiso 1 1 d R . . . .
N9 N 0.46570(17) 0.32623(14) 0.46811(11) 0.0291(4) Uani 1 1 d . . . . .
H9 H 0.4797 0.2995 0.4254 0.035 Uiso 1 1 d R . . . .
H10 H 0.6075 0.4148 0.3426 0.035 Uiso 1 1 d R . . . .
C1 C 0.9139(2) 0.17971(18) 0.26028(14) 0.0340(6) Uani 1 1 d . . . . .
H1A H 0.9142 0.1526 0.2091 0.041 Uiso 1 1 calc R . . . .
H1B H 0.9830 0.1575 0.2884 0.041 Uiso 1 1 calc R . . . .
C2 C 0.9221(2) 0.27907(17) 0.25272(13) 0.0336(6) Uani 1 1 d . . . . .
H2A H 0.9934 0.2951 0.2246 0.040 Uiso 1 1 calc R . . . .
H2B H 0.8539 0.3018 0.2240 0.040 Uiso 1 1 calc R . . . .
C3 C 0.9272(3) 0.41511(17) 0.32868(16) 0.0411(6) Uani 1 1 d . . . . .
H3A H 0.8563 0.4376 0.3028 0.049 Uiso 1 1 calc R . . . .
H3B H 0.9957 0.4362 0.3000 0.049 Uiso 1 1 calc R . . . .
C4 C 0.9324(2) 0.45146(18) 0.40825(17) 0.0422(6) Uani 1 1 d . . . . .
H4A H 0.9599 0.5135 0.4057 0.051 Uiso 1 1 calc R . . . .
H4B H 0.9913 0.4173 0.4373 0.051 Uiso 1 1 calc R . . . .
C5 C 0.8194(3) 0.44971(19) 0.45180(16) 0.0440(7) Uani 1 1 d . . . . .
H5A H 0.8331 0.4756 0.5027 0.053 Uiso 1 1 calc R . . . .
H5B H 0.7619 0.4876 0.4251 0.053 Uiso 1 1 calc R . . . .
C6 C 0.8352(3) 0.3052(2) 0.51371(16) 0.0441(7) Uani 1 1 d . . . . .
H6A H 0.8472 0.3381 0.5618 0.053 Uiso 1 1 calc R . . . .
H6B H 0.9127 0.2924 0.4919 0.053 Uiso 1 1 calc R . . . .
C7 C 0.7734(2) 0.2199(2) 0.52981(14) 0.0432(7) Uani 1 1 d . . . . .
H7A H 0.7000 0.2336 0.5565 0.052 Uiso 1 1 calc R . . . .
H7B H 0.8225 0.1843 0.5648 0.052 Uiso 1 1 calc R . . . .
C8 C 0.8433(3) 0.11300(19) 0.43503(15) 0.0407(6) Uani 1 1 d . . . . .
H8A H 0.8566 0.0627 0.4701 0.049 Uiso 1 1 calc R . . . .
H8B H 0.9139 0.1507 0.4357 0.049 Uiso 1 1 calc R . . . .
C9 C 0.8227(2) 0.07841(17) 0.35599(15) 0.0374(6) Uani 1 1 d . . . . .
H9A H 0.8902 0.0407 0.3406 0.045 Uiso 1 1 calc R . . . .
C10 C 0.7078(2) 0.02480(16) 0.34609(16) 0.0379(6) Uani 1 1 d . . . . .
H10A H 0.7240 -0.0337 0.3231 0.046 Uiso 1 1 calc R . . . .
H10B H 0.6702 0.0155 0.3959 0.046 Uiso 1 1 calc R . . . .
C11 C 0.7122(2) 0.12682(16) 0.24853(13) 0.0296(5) Uani 1 1 d . . . . .
H11 H 0.7439 0.0862 0.2088 0.035 Uiso 1 1 calc R . . . .
C12 C 0.65547(19) 0.20511(16) 0.20964(12) 0.0258(5) Uani 1 1 d . . . . .
C13 C 0.6508(2) 0.21235(17) 0.13077(13) 0.0297(5) Uani 1 1 d . . . . .
H13 H 0.6838 0.1669 0.1004 0.036 Uiso 1 1 calc R . . . .
C14 C 0.5990(2) 0.28428(17) 0.09589(12) 0.0297(5) Uani 1 1 d . . . . .
H14 H 0.5979 0.2886 0.0421 0.036 Uiso 1 1 calc R . . . .
C15 C 0.5484(2) 0.35035(16) 0.13966(12) 0.0269(5) Uani 1 1 d . . . . .
H15 H 0.5129 0.3999 0.1156 0.032 Uiso 1 1 calc R . . . .
C16 C 0.54940(19) 0.34406(15) 0.21882(12) 0.0236(5) Uani 1 1 d . . . . .
C17 C 0.60413(19) 0.27187(15) 0.25267(12) 0.0248(5) Uani 1 1 d . . . . .
H17 H 0.6066 0.2679 0.3065 0.030 Uiso 1 1 calc R . . . .
C18 C 0.48783(19) 0.41154(15) 0.26719(12) 0.0245(5) Uani 1 1 d . . . . .
H18 H 0.4518 0.4572 0.2332 0.029 Uiso 1 1 calc R . . . .
C19 C 0.4844(2) 0.49102(16) 0.37907(15) 0.0365(6) Uani 1 1 d . . . . .
H19A H 0.4622 0.5527 0.3666 0.044 Uiso 1 1 calc R . . . .
H19B H 0.5221 0.4905 0.4298 0.044 Uiso 1 1 calc R . . . .
C20 C 0.3755(2) 0.43041(16) 0.37865(14) 0.0323(5) Uani 1 1 d . . . . .
H20 H 0.3042 0.4669 0.3692 0.039 Uiso 1 1 calc R . . . .
C21 C 0.3606(2) 0.37672(16) 0.45114(13) 0.0299(5) Uani 1 1 d . . . . .
H21A H 0.3435 0.4171 0.4940 0.036 Uiso 1 1 calc R . . . .
H21B H 0.2939 0.3357 0.4451 0.036 Uiso 1 1 calc R . . . .
C22 C 0.4460(2) 0.25920(17) 0.52852(13) 0.0326(6) Uani 1 1 d . . . . .
H22A H 0.4001 0.2872 0.5694 0.039 Uiso 1 1 calc R . . . .
H22B H 0.5225 0.2426 0.5505 0.039 Uiso 1 1 calc R . . . .
C23 C 0.3843(2) 0.17581(17) 0.50406(13) 0.0326(5) Uani 1 1 d . . . . .
H23A H 0.3766 0.1355 0.5481 0.039 Uiso 1 1 calc R . . . .
H23B H 0.3051 0.1906 0.4855 0.039 Uiso 1 1 calc R . . . .
C24 C 0.4015(2) 0.04363(17) 0.42404(16) 0.0386(6) Uani 1 1 d . . . . .
H24A H 0.3898 0.0095 0.4714 0.046 Uiso 1 1 calc R . . . .
H24B H 0.4592 0.0114 0.3929 0.046 Uiso 1 1 calc R . . . .
C25 C 0.2865(3) 0.04779(17) 0.38059(16) 0.0410(6) Uani 1 1 d . . . . .
H25A H 0.2279 0.0771 0.4131 0.049 Uiso 1 1 calc R . . . .
H25B H 0.2594 -0.0135 0.3710 0.049 Uiso 1 1 calc R . . . .
C26 C 0.2916(3) 0.09675(17) 0.30494(15) 0.0381(6) Uani 1 1 d . . . . .
H26A H 0.3623 0.0786 0.2771 0.046 Uiso 1 1 calc R . . . .
H26B H 0.2228 0.0810 0.2736 0.046 Uiso 1 1 calc R . . . .
C27 C 0.2921(2) 0.24557(16) 0.24835(13) 0.0301(5) Uani 1 1 d . . . . .
H27A H 0.2217 0.2313 0.2179 0.036 Uiso 1 1 calc R . . . .
H27B H 0.3615 0.2319 0.2174 0.036 Uiso 1 1 calc R . . . .
C28 C 0.2918(2) 0.34391(17) 0.26992(14) 0.0328(5) Uani 1 1 d . . . . .
H28A H 0.2867 0.3799 0.2230 0.039 Uiso 1 1 calc R . . . .
H28B H 0.2218 0.3566 0.3006 0.039 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1C 0.8692 . ?
O1 H1D 0.8684 . ?
N1 C1 1.462(3) . ?
N1 C9 1.505(3) . ?
N1 C11 1.479(3) . ?
N2 H2 0.8751 . ?
N2 C2 1.463(3) . ?
N2 C3 1.457(3) . ?
N10 H10 0.8733 . ?
N10 C18 1.457(3) . ?
N10 C19 1.473(3) . ?
N3 H3 0.8701 . ?
N3 C5 1.489(4) . ?
N3 C6 1.449(4) . ?
N4 H4 0.8700 . ?
N4 C7 1.518(4) . ?
N4 C8 1.442(3) . ?
N5 H5 0.8698 . ?
N5 C10 1.472(3) . ?
N5 C11 1.456(3) . ?
N6 C18 1.474(3) . ?
N6 C20 1.491(3) . ?
N6 C28 1.460(3) . ?
N7 H7 0.8700 . ?
N7 C26 1.469(3) . ?
N7 C27 1.455(3) . ?
N8 H8 0.8700 . ?
N8 C23 1.464(3) . ?
N8 C24 1.476(3) . ?
N9 H9 0.8700 . ?
N9 C21 1.457(3) . ?
N9 C22 1.486(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.509(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.505(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.511(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.498(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.503(4) . ?
C9 H9A 1.0000 . ?
C9 C10 1.557(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11 1.0000 . ?
C11 C12 1.511(3) . ?
C12 C13 1.393(3) . ?
C12 C17 1.394(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.390(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.397(3) . ?
C16 C17 1.390(3) . ?
C16 C18 1.507(3) . ?
C17 H17 0.9500 . ?
C18 H18 1.0000 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.549(4) . ?
C20 H20 1.0000 . ?
C20 C21 1.522(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.506(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.522(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.525(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.533(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?

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
H1C O1 H1D 109.6 . . ?
C1 N1 C9 115.5(2) . . ?
C1 N1 C11 113.35(19) . . ?
C11 N1 C9 106.17(19) . . ?
C2 N2 H2 106.6 . . ?
C3 N2 H2 107.0 . . ?
C3 N2 C2 114.2(2) . . ?
C18 N10 H10 107.0 . . ?
C18 N10 C19 103.86(18) . . ?
C19 N10 H10 108.4 . . ?
C5 N3 H3 111.8 . . ?
C6 N3 H3 105.3 . . ?
C6 N3 C5 112.6(2) . . ?
C7 N4 H4 108.0 . . ?
C8 N4 H4 104.9 . . ?
C8 N4 C7 112.4(2) . . ?
C10 N5 H5 108.8 . . ?
C11 N5 H5 106.0 . . ?
C11 N5 C10 104.01(19) . . ?
C18 N6 C20 106.26(17) . . ?
C28 N6 C18 114.80(17) . . ?
C28 N6 C20 116.08(19) . . ?
C26 N7 H7 105.3 . . ?
C27 N7 H7 112.1 . . ?
C27 N7 C26 114.41(19) . . ?
C23 N8 H8 107.6 . . ?
C23 N8 C24 112.9(2) . . ?
C24 N8 H8 111.4 . . ?
C21 N9 H9 102.9 . . ?
C21 N9 C22 111.92(18) . . ?
C22 N9 H9 109.4 . . ?
N1 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
N1 C1 C2 111.6(2) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
N2 C2 C1 109.09(19) . . ?
N2 C2 H2A 109.9 . . ?
N2 C2 H2B 109.9 . . ?
C1 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
N2 C3 H3A 109.3 . . ?
N2 C3 H3B 109.3 . . ?
N2 C3 C4 111.5(2) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C3 C4 H4A 108.3 . . ?
C3 C4 H4B 108.3 . . ?
C3 C4 C5 115.9(2) . . ?
H4A C4 H4B 107.4 . . ?
C5 C4 H4A 108.3 . . ?
C5 C4 H4B 108.3 . . ?
N3 C5 C4 114.1(2) . . ?
N3 C5 H5A 108.7 . . ?
N3 C5 H5B 108.7 . . ?
C4 C5 H5A 108.7 . . ?
C4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
N3 C6 H6A 109.4 . . ?
N3 C6 H6B 109.4 . . ?
N3 C6 C7 111.1(2) . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
N4 C7 H7A 108.5 . . ?
N4 C7 H7B 108.5 . . ?
C6 C7 N4 115.3(2) . . ?
C6 C7 H7A 108.5 . . ?
C6 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
N4 C8 H8A 109.5 . . ?
N4 C8 H8B 109.5 . . ?
N4 C8 C9 110.8(2) . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
N1 C9 H9A 109.4 . . ?
N1 C9 C10 103.1(2) . . ?
C8 C9 N1 111.1(2) . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 C10 114.3(2) . . ?
C10 C9 H9A 109.4 . . ?
N5 C10 C9 106.7(2) . . ?
N5 C10 H10A 110.4 . . ?
N5 C10 H10B 110.4 . . ?
C9 C10 H10A 110.4 . . ?
C9 C10 H10B 110.4 . . ?
H10A C10 H10B 108.6 . . ?
N1 C11 H11 108.7 . . ?
N1 C11 C12 112.68(19) . . ?
N5 C11 N1 105.11(19) . . ?
N5 C11 H11 108.7 . . ?
N5 C11 C12 112.76(19) . . ?
C12 C11 H11 108.7 . . ?
C13 C12 C11 121.8(2) . . ?
C13 C12 C17 118.1(2) . . ?
C17 C12 C11 120.1(2) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.2(2) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 119.9(2) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C18 121.1(2) . . ?
C17 C16 C15 118.8(2) . . ?
C17 C16 C18 120.02(18) . . ?
C12 C17 H17 119.2 . . ?
C16 C17 C12 121.7(2) . . ?
C16 C17 H17 119.2 . . ?
N10 C18 N6 105.71(17) . . ?
N10 C18 C16 113.37(18) . . ?
N10 C18 H18 108.8 . . ?
N6 C18 C16 111.34(18) . . ?
N6 C18 H18 108.8 . . ?
C16 C18 H18 108.8 . . ?
N10 C19 H19A 110.3 . . ?
N10 C19 H19B 110.3 . . ?
N10 C19 C20 106.90(19) . . ?
H19A C19 H19B 108.6 . . ?
C20 C19 H19A 110.3 . . ?
C20 C19 H19B 110.3 . . ?
N6 C20 C19 103.67(18) . . ?
N6 C20 H20 109.6 . . ?
N6 C20 C21 110.18(18) . . ?
C19 C20 H20 109.6 . . ?
C21 C20 C19 113.9(2) . . ?
C21 C20 H20 109.6 . . ?
N9 C21 C20 110.67(19) . . ?
N9 C21 H21A 109.5 . . ?
N9 C21 H21B 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
N9 C22 H22A 108.3 . . ?
N9 C22 H22B 108.3 . . ?
N9 C22 C23 115.99(19) . . ?
H22A C22 H22B 107.4 . . ?
C23 C22 H22A 108.3 . . ?
C23 C22 H22B 108.3 . . ?
N8 C23 C22 110.4(2) . . ?
N8 C23 H23A 109.6 . . ?
N8 C23 H23B 109.6 . . ?
C22 C23 H23A 109.6 . . ?
C22 C23 H23B 109.6 . . ?
H23A C23 H23B 108.1 . . ?
N8 C24 H24A 108.8 . . ?
N8 C24 H24B 108.8 . . ?
N8 C24 C25 113.6(2) . . ?
H24A C24 H24B 107.7 . . ?
C25 C24 H24A 108.8 . . ?
C25 C24 H24B 108.8 . . ?
C24 C25 H25A 108.5 . . ?
C24 C25 H25B 108.5 . . ?
C24 C25 C26 114.9(2) . . ?
H25A C25 H25B 107.5 . . ?
C26 C25 H25A 108.5 . . ?
C26 C25 H25B 108.5 . . ?
N7 C26 C25 110.4(2) . . ?
N7 C26 H26A 109.6 . . ?
N7 C26 H26B 109.6 . . ?
C25 C26 H26A 109.6 . . ?
C25 C26 H26B 109.6 . . ?
H26A C26 H26B 108.1 . . ?
N7 C27 H27A 109.9 . . ?
N7 C27 H27B 109.9 . . ?
N7 C27 C28 108.78(19) . . ?
H27A C27 H27B 108.3 . . ?
C28 C27 H27A 109.9 . . ?
C28 C27 H27B 109.9 . . ?
N6 C28 C27 112.9(2) . . ?
N6 C28 H28A 109.0 . . ?
N6 C28 H28B 109.0 . . ?
C27 C28 H28A 109.0 . . ?
C27 C28 H28B 109.0 . . ?
H28A C28 H28B 107.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1C N2 0.87 1.95 2.818(3) 175.9 1_455
O1 H1D N7 0.87 1.97 2.828(3) 171.0 .
N2 H2 N3 0.88 2.37 3.018(3) 130.7 .
N7 H7 N8 0.87 2.30 2.988(3) 135.6 .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 60.7(3) . . . . ?
N1 C9 C10 N5 -7.9(3) . . . . ?
N1 C11 C12 C13 121.7(2) . . . . ?
N1 C11 C12 C17 -59.5(3) . . . . ?
N2 C3 C4 C5 -77.0(3) . . . . ?
N10 C19 C20 N6 -6.8(3) . . . . ?
N10 C19 C20 C21 113.0(2) . . . . ?
N3 C6 C7 N4 56.7(3) . . . . ?
N4 C8 C9 N1 62.1(3) . . . . ?
N4 C8 C9 C10 -54.1(3) . . . . ?
N5 C11 C12 C13 -119.5(2) . . . . ?
N5 C11 C12 C17 59.3(3) . . . . ?
N6 C20 C21 N9 62.0(3) . . . . ?
N7 C27 C28 N6 61.5(3) . . . . ?
N8 C24 C25 C26 60.0(3) . . . . ?
N9 C22 C23 N8 58.4(3) . . . . ?
C1 N1 C9 C8 94.7(3) . . . . ?
C1 N1 C9 C10 -142.4(2) . . . . ?
C1 N1 C11 N5 162.50(19) . . . . ?
C1 N1 C11 C12 -74.3(2) . . . . ?
C2 N2 C3 C4 -179.1(2) . . . . ?
C3 N2 C2 C1 -176.9(2) . . . . ?
C3 C4 C5 N3 59.1(3) . . . . ?
C5 N3 C6 C7 172.2(2) . . . . ?
C6 N3 C5 C4 71.2(3) . . . . ?
C7 N4 C8 C9 -164.6(2) . . . . ?
C8 N4 C7 C6 80.6(3) . . . . ?
C8 C9 C10 N5 112.9(2) . . . . ?
C9 N1 C1 C2 -139.5(2) . . . . ?
C9 N1 C11 N5 34.6(2) . . . . ?
C9 N1 C11 C12 157.77(19) . . . . ?
C10 N5 C11 N1 -39.2(2) . . . . ?
C10 N5 C11 C12 -162.35(19) . . . . ?
C11 N1 C1 C2 97.7(2) . . . . ?
C11 N1 C9 C8 -138.7(2) . . . . ?
C11 N1 C9 C10 -15.8(2) . . . . ?
C11 N5 C10 C9 28.8(2) . . . . ?
C11 C12 C13 C14 -179.8(2) . . . . ?
C11 C12 C17 C16 -178.9(2) . . . . ?
C12 C13 C14 C15 -1.2(3) . . . . ?
C13 C12 C17 C16 0.0(3) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C14 C15 C16 C17 1.5(3) . . . . ?
C14 C15 C16 C18 -175.7(2) . . . . ?
C15 C16 C17 C12 -1.4(3) . . . . ?
C15 C16 C18 N10 -122.2(2) . . . . ?
C15 C16 C18 N6 118.7(2) . . . . ?
C17 C12 C13 C14 1.3(3) . . . . ?
C17 C16 C18 N10 60.7(3) . . . . ?
C17 C16 C18 N6 -58.4(3) . . . . ?
C18 N10 C19 C20 27.0(2) . . . . ?
C18 N6 C20 C19 -15.9(2) . . . . ?
C18 N6 C20 C21 -138.2(2) . . . . ?
C18 N6 C28 C27 97.5(2) . . . . ?
C18 C16 C17 C12 175.8(2) . . . . ?
C19 N10 C18 N6 -37.4(2) . . . . ?
C19 N10 C18 C16 -159.64(18) . . . . ?
C19 C20 C21 N9 -54.0(3) . . . . ?
C20 N6 C18 N10 33.6(2) . . . . ?
C20 N6 C18 C16 157.15(18) . . . . ?
C20 N6 C28 C27 -137.8(2) . . . . ?
C21 N9 C22 C23 78.1(3) . . . . ?
C22 N9 C21 C20 -167.97(19) . . . . ?
C23 N8 C24 C25 72.4(3) . . . . ?
C24 N8 C23 C22 172.7(2) . . . . ?
C24 C25 C26 N7 -76.7(3) . . . . ?
C26 N7 C27 C28 178.7(2) . . . . ?
C27 N7 C26 C25 -176.7(2) . . . . ?
C28 N6 C18 N10 163.37(18) . . . . ?
C28 N6 C18 C16 -73.1(2) . . . . ?
C28 N6 C20 C19 -144.9(2) . . . . ?
C28 N6 C20 C21 92.8(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a glass fibre with grease'
_olex2_submission_special_instructions 'No special instructions were received'
