# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

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

data_compound_3
_database_code_depnum_ccdc_archive 'CCDC 1439077'

_audit_update_record             
;
2015-11-26 deposited with the CCDC.
2016-03-30 downloaded from the CCDC.
;
_publcif_datablock.id            {451c73e0-8e5c-420d-ac83-76e818dd3e8d}

# publcif _publ_body_element loop start

# publcif _publ_body_element loop end
_audit_creation_date             2015-11-20
_audit_creation_method           
;
Olex2 1.2
(compiled Sep 16 2015 11:44:03 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H35 N5'
_chemical_formula_sum            'C27 H35 N5'
_chemical_formula_weight         429.60
_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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8082(4)
_cell_length_b                   11.1431(5)
_cell_length_c                   13.3105(7)
_cell_angle_alpha                75.168(3)
_cell_angle_beta                 85.508(2)
_cell_angle_gamma                72.535(2)
_cell_volume                     1204.68(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4964
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.071
_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    1.184
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9711
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.626
_diffrn_reflns_theta_min         1.976
_diffrn_ambient_temperature      115
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius Kappa Apex II'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_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                4140
_reflns_number_total             5483
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5483
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0726
_refine_ls_restrained_S_all      1.119
_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)+(0.0082P)²+1.7328P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1428
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a 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), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C31(H31A,H31B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C33(H33), C34(H34),
 C35(H35), C36(H36), C37(H37), C41(H41)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6018(3) 0.0363(2) 0.30355(19) 0.0234(5) Uani 1 1 d . . . . .
H1A H 0.6235 -0.0535 0.3472 0.028 Uiso 1 1 calc R . . . .
H1B H 0.6592 0.0821 0.3343 0.028 Uiso 1 1 calc R . . . .
C2 C 0.6655(3) 0.0320(2) 0.1946(2) 0.0245(5) Uani 1 1 d . . . . .
H2A H 0.7832 -0.0002 0.1976 0.029 Uiso 1 1 calc R . . . .
H2B H 0.6272 -0.0308 0.1705 0.029 Uiso 1 1 calc R . . . .
C3 C 0.6881(3) 0.1463(3) 0.0156(2) 0.0273(6) Uani 1 1 d . . . . .
H3A H 0.6935 0.0596 0.0067 0.033 Uiso 1 1 calc R . . . .
H3B H 0.7983 0.1523 0.0132 0.033 Uiso 1 1 calc R . . . .
C4 C 0.5935(3) 0.2501(3) -0.07440(19) 0.0248(5) Uani 1 1 d . . . . .
H4A H 0.6444 0.2354 -0.1409 0.030 Uiso 1 1 calc R . . . .
H4B H 0.5962 0.3365 -0.0692 0.030 Uiso 1 1 calc R . . . .
C5 C 0.4190(3) 0.2491(2) -0.07463(19) 0.0208(5) Uani 1 1 d . . . . .
H5A H 0.4011 0.2218 -0.1368 0.025 Uiso 1 1 calc R . . . .
H5B H 0.4004 0.1839 -0.0126 0.025 Uiso 1 1 calc R . . . .
C6 C 0.3188(3) 0.4258(2) 0.01381(18) 0.0196(5) Uani 1 1 d . . . . .
H6A H 0.2427 0.5137 0.0042 0.024 Uiso 1 1 calc R . . . .
H6B H 0.4273 0.4354 0.0119 0.024 Uiso 1 1 calc R . . . .
C7 C 0.2914(3) 0.3453(2) 0.12278(17) 0.0167(4) Uani 1 1 d . . . . .
H7A H 0.1762 0.3665 0.1391 0.020 Uiso 1 1 calc R . . . .
H7B H 0.3317 0.2516 0.1251 0.020 Uiso 1 1 calc R . . . .
C8 C 0.2879(3) 0.4044(2) 0.29202(18) 0.0217(5) Uani 1 1 d . . . . .
H8A H 0.1905 0.4775 0.2706 0.026 Uiso 1 1 calc R . . . .
H8B H 0.3540 0.4323 0.3332 0.026 Uiso 1 1 calc R . . . .
C9 C 0.2405(3) 0.2877(2) 0.36102(19) 0.0256(5) Uani 1 1 d . . . . .
H9A H 0.1898 0.3115 0.4250 0.031 Uiso 1 1 calc R . . . .
H9B H 0.1599 0.2699 0.3237 0.031 Uiso 1 1 calc R . . . .
C10 C 0.3777(3) 0.1633(2) 0.39212(18) 0.0236(5) Uani 1 1 d . . . . .
H10A H 0.4681 0.1839 0.4165 0.028 Uiso 1 1 calc R . . . .
H10B H 0.3433 0.1019 0.4505 0.028 Uiso 1 1 calc R . . . .
C11 C 0.3280(3) 0.0294(2) 0.28339(19) 0.0228(5) Uani 1 1 d . . . . .
H11A H 0.3638 0.0036 0.2176 0.027 Uiso 1 1 calc R . . . .
H11B H 0.2183 0.0885 0.2723 0.027 Uiso 1 1 calc R . . . .
C12 C 0.3234(3) -0.0916(2) 0.36716(18) 0.0206(5) Uani 1 1 d . . . . .
C13 C 0.2095(3) -0.0848(3) 0.4462(2) 0.0260(5) Uani 1 1 d . . . . .
H13 H 0.1328 -0.0042 0.4468 0.031 Uiso 1 1 calc R . . . .
C14 C 0.2070(3) -0.1946(3) 0.5243(2) 0.0276(6) Uani 1 1 d . . . . .
H14 H 0.1293 -0.1887 0.5779 0.033 Uiso 1 1 calc R . . . .
C15 C 0.3174(3) -0.3119(3) 0.5234(2) 0.0283(6) Uani 1 1 d . . . . .
H15 H 0.3158 -0.3869 0.5766 0.034 Uiso 1 1 calc R . . . .
C16 C 0.4309(3) -0.3207(3) 0.4452(2) 0.0295(6) Uani 1 1 d . . . . .
H16 H 0.5071 -0.4016 0.4448 0.035 Uiso 1 1 calc R . . . .
C17 C 0.4329(3) -0.2110(2) 0.3676(2) 0.0257(5) Uani 1 1 d . . . . .
H17 H 0.5103 -0.2177 0.3139 0.031 Uiso 1 1 calc R . . . .
C31 C 0.1399(3) 0.3685(3) -0.08069(18) 0.0221(5) Uani 1 1 d . . . . .
H31A H 0.0640 0.4497 -0.0693 0.027 Uiso 1 1 calc R . . . .
H31B H 0.1239 0.2958 -0.0243 0.027 Uiso 1 1 calc R . . . .
C32 C 0.1035(3) 0.3497(2) -0.18389(18) 0.0194(5) Uani 1 1 d . . . . .
C33 C 0.1529(3) 0.4185(3) -0.27636(19) 0.0256(6) Uani 1 1 d . . . . .
H33 H 0.2132 0.4758 -0.2748 0.031 Uiso 1 1 calc R . . . .
C34 C 0.1150(3) 0.4043(3) -0.3712(2) 0.0296(6) Uani 1 1 d . . . . .
H34 H 0.1508 0.4509 -0.4340 0.036 Uiso 1 1 calc R . . . .
C35 C 0.0247(3) 0.3222(3) -0.3745(2) 0.0274(6) Uani 1 1 d . . . . .
H35 H -0.0017 0.3126 -0.4393 0.033 Uiso 1 1 calc R . . . .
C36 C -0.0261(3) 0.2546(2) -0.2826(2) 0.0272(6) Uani 1 1 d . . . . .
H36 H -0.0887 0.1990 -0.2843 0.033 Uiso 1 1 calc R . . . .
C37 C 0.0139(3) 0.2675(2) -0.1881(2) 0.0243(5) Uani 1 1 d . . . . .
H37 H -0.0204 0.2196 -0.1253 0.029 Uiso 1 1 calc R . . . .
C41 C 0.5371(3) 0.3435(2) 0.20099(18) 0.0203(5) Uani 1 1 d . . . . .
H41 H 0.5789 0.3867 0.2401 0.024 Uiso 1 1 calc R . . . .
C42 C 0.6487(3) 0.2590(2) 0.15602(18) 0.0201(5) Uani 1 1 d . . . . .
C43 C 0.8116(3) 0.2539(2) 0.1665(2) 0.0262(6) Uani 1 1 d . . . . .
N1 N 0.4310(2) 0.10115(19) 0.30544(15) 0.0199(4) Uani 1 1 d . . . . .
N2 N 0.6182(2) 0.15888(19) 0.11787(15) 0.0195(4) Uani 1 1 d . . . . .
N3 N 0.3025(2) 0.37504(19) -0.07472(15) 0.0183(4) Uani 1 1 d . . . . .
N4 N 0.3764(2) 0.37607(18) 0.19902(15) 0.0184(4) Uani 1 1 d . . . . .
N5 N 0.9440(3) 0.2458(3) 0.1745(2) 0.0407(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.520(3) . ?
C1 N1 1.462(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 N2 1.480(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.528(3) . ?
C3 N2 1.473(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.541(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 N3 1.468(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.541(3) . ?
C6 N3 1.465(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 N4 1.469(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.538(3) . ?
C8 N4 1.463(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.527(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 N1 1.470(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.523(3) . ?
C11 N1 1.465(3) . ?
C12 C13 1.396(3) . ?
C12 C17 1.388(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.393(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.377(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.388(3) . ?
C17 H17 0.9500 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.514(3) . ?
C31 N3 1.465(3) . ?
C32 C33 1.388(3) . ?
C32 C37 1.389(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.389(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.391(4) . ?
C35 H35 0.9500 . ?
C35 C36 1.381(4) . ?
C36 H36 0.9500 . ?
C36 C37 1.386(3) . ?
C37 H37 0.9500 . ?
C41 H41 0.9500 . ?
C41 C42 1.361(3) . ?
C41 N4 1.353(3) . ?
C42 C43 1.436(3) . ?
C42 N2 1.437(3) . ?
C43 N5 1.154(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
H1A C1 H1B 107.8 . . ?
C2 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
N1 C1 H1A 109.0 . . ?
N1 C1 H1B 109.0 . . ?
N1 C1 C2 113.0(2) . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
N2 C2 C1 114.0(2) . . ?
N2 C2 H2A 108.8 . . ?
N2 C2 H2B 108.8 . . ?
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 112.9(2) . . ?
C3 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
C3 C4 C5 112.2(2) . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
N3 C5 C4 113.89(19) . . ?
N3 C5 H5A 108.8 . . ?
N3 C5 H5B 108.8 . . ?
H6A C6 H6B 107.3 . . ?
C7 C6 H6A 108.1 . . ?
C7 C6 H6B 108.1 . . ?
N3 C6 H6A 108.1 . . ?
N3 C6 H6B 108.1 . . ?
N3 C6 C7 116.88(18) . . ?
C6 C7 H7A 110.0 . . ?
C6 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
N4 C7 C6 108.48(17) . . ?
N4 C7 H7A 110.0 . . ?
N4 C7 H7B 110.0 . . ?
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 113.06(19) . . ?
C8 C9 H9A 108.5 . . ?
C8 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C10 C9 C8 114.9(2) . . ?
C10 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
N1 C10 C9 112.12(19) . . ?
N1 C10 H10A 109.2 . . ?
N1 C10 H10B 109.2 . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
N1 C11 H11A 108.4 . . ?
N1 C11 H11B 108.4 . . ?
N1 C11 C12 115.46(19) . . ?
C13 C12 C11 120.6(2) . . ?
C17 C12 C11 121.0(2) . . ?
C17 C12 C13 118.3(2) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.9(2) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.8(2) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.1(2) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.9(3) . . ?
C17 C16 H16 120.1 . . ?
C12 C17 C16 121.0(2) . . ?
C12 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
H31A C31 H31B 107.8 . . ?
C32 C31 H31A 109.0 . . ?
C32 C31 H31B 109.0 . . ?
N3 C31 H31A 109.0 . . ?
N3 C31 H31B 109.0 . . ?
N3 C31 C32 113.02(19) . . ?
C33 C32 C31 120.6(2) . . ?
C33 C32 C37 118.7(2) . . ?
C37 C32 C31 120.6(2) . . ?
C32 C33 H33 119.7 . . ?
C32 C33 C34 120.6(2) . . ?
C34 C33 H33 119.7 . . ?
C33 C34 H34 119.9 . . ?
C33 C34 C35 120.2(2) . . ?
C35 C34 H34 119.9 . . ?
C34 C35 H35 120.3 . . ?
C36 C35 C34 119.4(2) . . ?
C36 C35 H35 120.3 . . ?
C35 C36 H36 119.9 . . ?
C35 C36 C37 120.3(2) . . ?
C37 C36 H36 119.9 . . ?
C32 C37 H37 119.6 . . ?
C36 C37 C32 120.8(2) . . ?
C36 C37 H37 119.6 . . ?
C42 C41 H41 114.8 . . ?
N4 C41 H41 114.8 . . ?
N4 C41 C42 130.5(2) . . ?
C41 C42 C43 116.6(2) . . ?
C41 C42 N2 124.4(2) . . ?
C43 C42 N2 117.8(2) . . ?
N5 C43 C42 177.8(3) . . ?
C1 N1 C10 114.83(19) . . ?
C1 N1 C11 115.35(19) . . ?
C11 N1 C10 114.78(19) . . ?
C3 N2 C2 110.25(19) . . ?
C42 N2 C2 111.35(18) . . ?
C42 N2 C3 115.13(19) . . ?
C6 N3 C5 113.57(18) . . ?
C6 N3 C31 110.54(18) . . ?
C31 N3 C5 110.82(18) . . ?
C8 N4 C7 116.92(19) . . ?
C41 N4 C7 121.84(19) . . ?
C41 N4 C8 118.48(19) . . ?

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 178.6(2) . . . . ?
C1 C2 N2 C42 49.6(3) . . . . ?
C2 C1 N1 C10 -151.9(2) . . . . ?
C2 C1 N1 C11 71.2(3) . . . . ?
C3 C4 C5 N3 125.2(2) . . . . ?
C4 C3 N2 C2 155.2(2) . . . . ?
C4 C3 N2 C42 -77.9(3) . . . . ?
C4 C5 N3 C6 -58.0(3) . . . . ?
C4 C5 N3 C31 176.90(19) . . . . ?
C6 C7 N4 C8 132.3(2) . . . . ?
C6 C7 N4 C41 -66.8(3) . . . . ?
C7 C6 N3 C5 -62.9(3) . . . . ?
C7 C6 N3 C31 62.4(3) . . . . ?
C8 C9 C10 N1 -74.2(3) . . . . ?
C9 C8 N4 C7 64.5(3) . . . . ?
C9 C8 N4 C41 -97.1(2) . . . . ?
C9 C10 N1 C1 145.5(2) . . . . ?
C9 C10 N1 C11 -77.3(2) . . . . ?
C11 C12 C13 C14 -178.6(2) . . . . ?
C11 C12 C17 C16 178.6(2) . . . . ?
C12 C11 N1 C1 69.7(3) . . . . ?
C12 C11 N1 C10 -67.2(3) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C13 C12 C17 C16 -0.8(4) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C14 C15 C16 C17 -0.1(4) . . . . ?
C15 C16 C17 C12 0.5(4) . . . . ?
C17 C12 C13 C14 0.8(4) . . . . ?
C31 C32 C33 C34 -177.9(2) . . . . ?
C31 C32 C37 C36 176.9(2) . . . . ?
C32 C31 N3 C5 -67.7(3) . . . . ?
C32 C31 N3 C6 165.51(19) . . . . ?
C32 C33 C34 C35 1.0(4) . . . . ?
C33 C32 C37 C36 -0.2(4) . . . . ?
C33 C34 C35 C36 -0.3(4) . . . . ?
C34 C35 C36 C37 -0.7(4) . . . . ?
C35 C36 C37 C32 0.9(4) . . . . ?
C37 C32 C33 C34 -0.7(4) . . . . ?
C41 C42 N2 C2 -97.8(3) . . . . ?
C41 C42 N2 C3 135.8(2) . . . . ?
C42 C41 N4 C7 -15.7(4) . . . . ?
C42 C41 N4 C8 144.9(3) . . . . ?
C43 C42 N2 C2 69.3(3) . . . . ?
C43 C42 N2 C3 -57.1(3) . . . . ?
N1 C1 C2 N2 49.6(3) . . . . ?
N1 C11 C12 C13 91.4(3) . . . . ?
N1 C11 C12 C17 -88.0(3) . . . . ?
N2 C3 C4 C5 -57.4(3) . . . . ?
N3 C6 C7 N4 155.85(19) . . . . ?
N3 C31 C32 C33 -42.8(3) . . . . ?
N3 C31 C32 C37 140.1(2) . . . . ?
N4 C8 C9 C10 53.4(3) . . . . ?
N4 C41 C42 C43 175.3(2) . . . . ?
N4 C41 C42 N2 -17.5(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder 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_4
_database_code_depnum_ccdc_archive 'CCDC 1439078'

_audit_update_record             
;
2015-11-26 deposited with the CCDC.
2016-03-30 downloaded from the CCDC.
;
_publcif_datablock.id            {46137393-b90a-47c3-8acd-9511e03bacc4}

# publcif _publ_body_element loop start

# publcif _publ_body_element loop end
_audit_creation_date             2015-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled Sep 16 2015 11:44:03 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H27 N5'
_chemical_formula_sum            'C15 H27 N5'
_chemical_formula_weight         277.41
_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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8695(3)
_cell_length_b                   12.1158(3)
_cell_length_c                   14.4185(5)
_cell_angle_alpha                78.653(2)
_cell_angle_beta                 80.2470(10)
_cell_angle_gamma                73.002(2)
_cell_volume                     1605.02(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6734
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.072
_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    1.148
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_special_details           ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13714
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_min         1.451
_diffrn_ambient_temperature      115
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean 9
_diffrn_detector_type            CCD
_diffrn_measured_fraction_theta_full 0.995
_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                5760
_reflns_number_total             7301
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         7301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0558
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0165P)²+1.2470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1153
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C1B(H1BA,H1BB), C2A(H2AA,H2AB), C2B(H2BA,H2BB), C3A(H3AA,
 H3AB), C3B(H3BA,H3BB), C4A(H4AA,H4AB), C4B(H4BA,H4BB), C5A(H5AA,H5AB),
 C5B(H5BA,H5BB), C6A(H6AA,H6AB), C6B(H6BA,H6BB), C7A(H7AA,H7AB), C7B(H7BA,H7BB),
  C8A(H8AA,H8AB), C8B(H8BA,H8BB), C9A(H9AA,H9AB), C9B(H9BA,H9BB), C10A(H10A,
 H10B), C10B(H10C,H10D)
2.b Aromatic/amide H refined with riding coordinates:
 C11A(H11A), C11B(H11B)
2.c Idealised Me refined as rotating group:
 C21A(H21A,H21B,H21C), C21B(H21D,H21E,H21F), C41A(H41A,H41B,H41C), C41B(H41D,
 H41E,H41F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.23313(18) 0.06821(15) -0.06781(12) 0.0209(3) Uani 1 1 d . . . . .
H1AA H 0.2377 0.0663 -0.1366 0.025 Uiso 1 1 calc R . . . .
H1AB H 0.2540 -0.0135 -0.0344 0.025 Uiso 1 1 calc R . . . .
C1B C 0.55173(18) 0.26482(14) 0.41112(12) 0.0206(3) Uani 1 1 d . . . . .
H1BA H 0.5008 0.2113 0.4538 0.025 Uiso 1 1 calc R . . . .
H1BB H 0.6362 0.2168 0.3759 0.025 Uiso 1 1 calc R . . . .
C2A C 0.34780(18) 0.12389(15) -0.05297(12) 0.0229(4) Uani 1 1 d . . . . .
H2AA H 0.4431 0.0705 -0.0679 0.027 Uiso 1 1 calc R . . . .
H2AB H 0.3410 0.1976 -0.0984 0.027 Uiso 1 1 calc R . . . .
C2B C 0.45341(18) 0.34607(15) 0.34062(12) 0.0230(4) Uani 1 1 d . . . . .
H2BA H 0.5017 0.4038 0.3018 0.028 Uiso 1 1 calc R . . . .
H2BB H 0.4348 0.2998 0.2971 0.028 Uiso 1 1 calc R . . . .
C3A C 0.33516(18) 0.15025(15) 0.04845(12) 0.0223(4) Uani 1 1 d . . . . .
H3AA H 0.3218 0.0811 0.0948 0.027 Uiso 1 1 calc R . . . .
H3AB H 0.4250 0.1650 0.0579 0.027 Uiso 1 1 calc R . . . .
C3B C 0.22247(19) 0.33180(16) 0.42901(13) 0.0256(4) Uani 1 1 d . . . . .
H3BA H 0.2784 0.2492 0.4300 0.031 Uiso 1 1 calc R . . . .
H3BB H 0.1469 0.3474 0.3872 0.031 Uiso 1 1 calc R . . . .
C4A C 0.15322(19) 0.24774(16) 0.16632(12) 0.0247(4) Uani 1 1 d . . . . .
H4AA H 0.2044 0.2839 0.2001 0.030 Uiso 1 1 calc R . . . .
H4AB H 0.1665 0.1652 0.1967 0.030 Uiso 1 1 calc R . . . .
C4B C 0.1524(2) 0.34991(16) 0.53041(13) 0.0280(4) Uani 1 1 d . . . . .
H4BA H 0.1622 0.4244 0.5431 0.034 Uiso 1 1 calc R . . . .
H4BB H 0.0492 0.3566 0.5344 0.034 Uiso 1 1 calc R . . . .
C5A C -0.00541(19) 0.31096(16) 0.17758(13) 0.0263(4) Uani 1 1 d . . . . .
H5AA H -0.0437 0.2976 0.2457 0.032 Uiso 1 1 calc R . . . .
H5AB H -0.0170 0.3960 0.1583 0.032 Uiso 1 1 calc R . . . .
C5B C 0.2165(2) 0.25166(16) 0.60704(13) 0.0277(4) Uani 1 1 d . . . . .
H5BA H 0.1740 0.2729 0.6706 0.033 Uiso 1 1 calc R . . . .
H5BB H 0.1921 0.1797 0.6015 0.033 Uiso 1 1 calc R . . . .
C6A C -0.24306(19) 0.32518(16) 0.14437(13) 0.0273(4) Uani 1 1 d . . . . .
H6AA H -0.2603 0.4105 0.1409 0.033 Uiso 1 1 calc R . . . .
H6AB H -0.2729 0.2929 0.2107 0.033 Uiso 1 1 calc R . . . .
C6B C 0.4340(2) 0.11986(15) 0.66305(13) 0.0286(4) Uani 1 1 d . . . . .
H6BA H 0.4241 0.0524 0.6382 0.034 Uiso 1 1 calc R . . . .
H6BB H 0.3784 0.1218 0.7269 0.034 Uiso 1 1 calc R . . . .
C7A C -0.33445(19) 0.30311(17) 0.07837(14) 0.0292(4) Uani 1 1 d . . . . .
H7AA H -0.4349 0.3468 0.0942 0.035 Uiso 1 1 calc R . . . .
H7AB H -0.3300 0.2189 0.0901 0.035 Uiso 1 1 calc R . . . .
C7B C 0.5906(2) 0.10107(16) 0.67323(13) 0.0303(4) Uani 1 1 d . . . . .
H7BA H 0.5990 0.1625 0.7065 0.036 Uiso 1 1 calc R . . . .
H7BB H 0.6251 0.0247 0.7134 0.036 Uiso 1 1 calc R . . . .
C8A C -0.28807(19) 0.33930(15) -0.02794(13) 0.0278(4) Uani 1 1 d . . . . .
H8AA H -0.3735 0.3845 -0.0596 0.033 Uiso 1 1 calc R . . . .
H8AB H -0.2246 0.3909 -0.0342 0.033 Uiso 1 1 calc R . . . .
C8B C 0.8056(2) 0.14912(17) 0.58000(14) 0.0324(4) Uani 1 1 d . . . . .
H8BA H 0.8870 0.0840 0.6013 0.039 Uiso 1 1 calc R . . . .
H8BB H 0.7816 0.2061 0.6249 0.039 Uiso 1 1 calc R . . . .
C9A C -0.08527(18) 0.25542(15) -0.13958(12) 0.0229(4) Uani 1 1 d . . . . .
H9AA H -0.1095 0.3325 -0.1806 0.028 Uiso 1 1 calc R . . . .
H9AB H -0.0525 0.1946 -0.1814 0.028 Uiso 1 1 calc R . . . .
C9B C 0.8495(2) 0.20847(16) 0.48015(14) 0.0307(4) Uani 1 1 d . . . . .
H9BA H 0.8527 0.1574 0.4336 0.037 Uiso 1 1 calc R . . . .
H9BB H 0.9471 0.2166 0.4776 0.037 Uiso 1 1 calc R . . . .
C10A C 0.03477(18) 0.24935(14) -0.08369(12) 0.0210(3) Uani 1 1 d . . . . .
H10A H 0.1134 0.2729 -0.1279 0.025 Uiso 1 1 calc R . . . .
H10B H -0.0006 0.3048 -0.0373 0.025 Uiso 1 1 calc R . . . .
C10B C 0.74944(19) 0.32963(16) 0.45013(14) 0.0269(4) Uani 1 1 d . . . . .
H10C H 0.7654 0.3864 0.4852 0.032 Uiso 1 1 calc R . . . .
H10D H 0.7738 0.3551 0.3813 0.032 Uiso 1 1 calc R . . . .
C11A C 0.03691(17) 0.09094(14) 0.05664(11) 0.0174(3) Uani 1 1 d . . . . .
H11A H 0.0670 0.0085 0.0745 0.021 Uiso 1 1 calc R . . . .
C11B C 0.52742(19) 0.36205(14) 0.55227(12) 0.0214(3) Uani 1 1 d . . . . .
H11B H 0.5578 0.4187 0.5745 0.026 Uiso 1 1 calc R . . . .
C12A C -0.05112(18) 0.14887(14) 0.12502(12) 0.0198(3) Uani 1 1 d . . . . .
C12B C 0.41979(19) 0.32537(14) 0.61010(12) 0.0222(4) Uani 1 1 d . . . . .
C13A C -0.09623(19) 0.08052(15) 0.21185(12) 0.0241(4) Uani 1 1 d . . . . .
C13B C 0.3610(2) 0.37811(15) 0.69391(13) 0.0281(4) Uani 1 1 d . . . . .
C21A C 0.2483(2) 0.36232(16) 0.02748(15) 0.0306(4) Uani 1 1 d . . . . .
H21A H 0.3198 0.3727 0.0621 0.046 Uiso 1 1 calc GR . . . .
H21B H 0.1611 0.4263 0.0337 0.046 Uiso 1 1 calc GR . . . .
H21C H 0.2856 0.3626 -0.0400 0.046 Uiso 1 1 calc GR . . . .
C21B C 0.2445(2) 0.50850(16) 0.32414(14) 0.0318(4) Uani 1 1 d . . . . .
H21D H 0.3056 0.5616 0.3019 0.048 Uiso 1 1 calc GR . . . .
H21E H 0.1548 0.5496 0.3578 0.048 Uiso 1 1 calc GR . . . .
H21F H 0.2244 0.4817 0.2694 0.048 Uiso 1 1 calc GR . . . .
C41A C -0.3099(2) 0.20833(17) -0.12720(14) 0.0304(4) Uani 1 1 d . . . . .
H41A H -0.3914 0.1934 -0.0823 0.046 Uiso 1 1 calc GR . . . .
H41B H -0.2597 0.1381 -0.1557 0.046 Uiso 1 1 calc GR . . . .
H41C H -0.3439 0.2733 -0.1774 0.046 Uiso 1 1 calc GR . . . .
C41B C 0.7234(2) -0.00839(16) 0.54822(15) 0.0346(5) Uani 1 1 d . . . . .
H41D H 0.7843 -0.0672 0.5915 0.052 Uiso 1 1 calc GR . . . .
H41E H 0.7760 -0.0008 0.4843 0.052 Uiso 1 1 calc GR . . . .
H41F H 0.6377 -0.0325 0.5459 0.052 Uiso 1 1 calc GR . . . .
N1A N 0.08903(14) 0.13113(11) -0.03284(9) 0.0182(3) Uani 1 1 d . . . . .
N1B N 0.59849(15) 0.33120(12) 0.46826(10) 0.0211(3) Uani 1 1 d . . . . .
N2A N 0.21608(15) 0.25140(12) 0.06696(10) 0.0206(3) Uani 1 1 d . . . . .
N2B N 0.31735(16) 0.40802(12) 0.38865(10) 0.0230(3) Uani 1 1 d . . . . .
N3A N -0.08992(15) 0.27294(12) 0.12076(10) 0.0214(3) Uani 1 1 d . . . . .
N3B N 0.37217(16) 0.22822(12) 0.59947(10) 0.0224(3) Uani 1 1 d . . . . .
N4A N -0.21289(15) 0.23831(12) -0.07682(10) 0.0226(3) Uani 1 1 d . . . . .
N4B N 0.68222(17) 0.10362(12) 0.58230(11) 0.0261(3) Uani 1 1 d . . . . .
N5A N -0.13631(19) 0.03211(15) 0.28366(11) 0.0361(4) Uani 1 1 d . . . . .
N5B N 0.3088(2) 0.41374(15) 0.76397(12) 0.0434(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
C1A C2A 1.538(2) . ?
C1A N1A 1.460(2) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
C1B C2B 1.525(2) . ?
C1B N1B 1.465(2) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C2A C3A 1.535(2) . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
C2B N2B 1.465(2) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C3A N2A 1.461(2) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C3B C4B 1.536(2) . ?
C3B N2B 1.476(2) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C4A C5A 1.525(2) . ?
C4A N2A 1.459(2) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C4B C5B 1.522(3) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C5A N3A 1.478(2) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C5B N3B 1.468(2) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C6A C7A 1.524(3) . ?
C6A N3A 1.467(2) . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C6B C7B 1.524(3) . ?
C6B N3B 1.478(2) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C7A C8A 1.538(3) . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C7B N4B 1.461(2) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C8A N4A 1.475(2) . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C8B C9B 1.530(3) . ?
C8B N4B 1.469(2) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C9A C10A 1.519(2) . ?
C9A N4A 1.463(2) . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C9B C10B 1.538(3) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C10A N1A 1.465(2) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C10B N1B 1.463(2) . ?
C11A H11A 0.9500 . ?
C11A C12A 1.358(2) . ?
C11A N1A 1.357(2) . ?
C11B H11B 0.9500 . ?
C11B C12B 1.361(2) . ?
C11B N1B 1.355(2) . ?
C12A C13A 1.439(2) . ?
C12A N3A 1.430(2) . ?
C12B C13B 1.433(2) . ?
C12B N3B 1.431(2) . ?
C13A N5A 1.153(2) . ?
C13B N5B 1.156(2) . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C21A H21C 0.9800 . ?
C21A N2A 1.455(2) . ?
C21B H21D 0.9800 . ?
C21B H21E 0.9800 . ?
C21B H21F 0.9800 . ?
C21B N2B 1.461(2) . ?
C41A H41A 0.9800 . ?
C41A H41B 0.9800 . ?
C41A H41C 0.9800 . ?
C41A N4A 1.456(2) . ?
C41B H41D 0.9800 . ?
C41B H41E 0.9800 . ?
C41B H41F 0.9800 . ?
C41B N4B 1.456(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
H1AA C1A H1AB 107.8 . . ?
C2A C1A H1AA 109.0 . . ?
C2A C1A H1AB 109.0 . . ?
N1A C1A H1AA 109.0 . . ?
N1A C1A H1AB 109.0 . . ?
N1A C1A C2A 112.83(13) . . ?
H1BA C1B H1BB 108.0 . . ?
C2B C1B H1BA 109.4 . . ?
C2B C1B H1BB 109.4 . . ?
N1B C1B H1BA 109.4 . . ?
N1B C1B H1BB 109.4 . . ?
N1B C1B C2B 111.13(13) . . ?
C1A C2A H2AA 108.8 . . ?
C1A C2A H2AB 108.8 . . ?
H2AA C2A H2AB 107.7 . . ?
C3A C2A C1A 113.77(14) . . ?
C3A C2A H2AA 108.8 . . ?
C3A C2A H2AB 108.8 . . ?
C1B C2B H2BA 109.2 . . ?
C1B C2B H2BB 109.2 . . ?
H2BA C2B H2BB 107.9 . . ?
N2B C2B C1B 112.08(13) . . ?
N2B C2B H2BA 109.2 . . ?
N2B C2B H2BB 109.2 . . ?
C2A C3A H3AA 109.2 . . ?
C2A C3A H3AB 109.2 . . ?
H3AA C3A H3AB 107.9 . . ?
N2A C3A C2A 112.18(14) . . ?
N2A C3A H3AA 109.2 . . ?
N2A C3A H3AB 109.2 . . ?
H3BA C3B H3BB 107.8 . . ?
C4B C3B H3BA 109.0 . . ?
C4B C3B H3BB 109.0 . . ?
N2B C3B H3BA 109.0 . . ?
N2B C3B H3BB 109.0 . . ?
N2B C3B C4B 112.90(15) . . ?
H4AA C4A H4AB 107.8 . . ?
C5A C4A H4AA 109.0 . . ?
C5A C4A H4AB 109.0 . . ?
N2A C4A H4AA 109.0 . . ?
N2A C4A H4AB 109.0 . . ?
N2A C4A C5A 112.98(14) . . ?
C3B C4B H4BA 108.9 . . ?
C3B C4B H4BB 108.9 . . ?
H4BA C4B H4BB 107.7 . . ?
C5B C4B C3B 113.45(15) . . ?
C5B C4B H4BA 108.9 . . ?
C5B C4B H4BB 108.9 . . ?
C4A C5A H5AA 108.9 . . ?
C4A C5A H5AB 108.9 . . ?
H5AA C5A H5AB 107.7 . . ?
N3A C5A C4A 113.54(14) . . ?
N3A C5A H5AA 108.9 . . ?
N3A C5A H5AB 108.9 . . ?
C4B C5B H5BA 109.2 . . ?
C4B C5B H5BB 109.2 . . ?
H5BA C5B H5BB 107.9 . . ?
N3B C5B C4B 112.13(14) . . ?
N3B C5B H5BA 109.2 . . ?
N3B C5B H5BB 109.2 . . ?
H6AA C6A H6AB 107.8 . . ?
C7A C6A H6AA 109.0 . . ?
C7A C6A H6AB 109.0 . . ?
N3A C6A H6AA 109.0 . . ?
N3A C6A H6AB 109.0 . . ?
N3A C6A C7A 113.09(14) . . ?
H6BA C6B H6BB 107.6 . . ?
C7B C6B H6BA 108.7 . . ?
C7B C6B H6BB 108.7 . . ?
N3B C6B H6BA 108.7 . . ?
N3B C6B H6BB 108.7 . . ?
N3B C6B C7B 114.08(15) . . ?
C6A C7A H7AA 108.9 . . ?
C6A C7A H7AB 108.9 . . ?
C6A C7A C8A 113.53(15) . . ?
H7AA C7A H7AB 107.7 . . ?
C8A C7A H7AA 108.9 . . ?
C8A C7A H7AB 108.9 . . ?
C6B C7B H7BA 108.9 . . ?
C6B C7B H7BB 108.9 . . ?
H7BA C7B H7BB 107.7 . . ?
N4B C7B C6B 113.57(15) . . ?
N4B C7B H7BA 108.9 . . ?
N4B C7B H7BB 108.9 . . ?
C7A C8A H8AA 109.1 . . ?
C7A C8A H8AB 109.1 . . ?
H8AA C8A H8AB 107.8 . . ?
N4A C8A C7A 112.70(14) . . ?
N4A C8A H8AA 109.1 . . ?
N4A C8A H8AB 109.1 . . ?
H8BA C8B H8BB 107.9 . . ?
C9B C8B H8BA 109.2 . . ?
C9B C8B H8BB 109.2 . . ?
N4B C8B H8BA 109.2 . . ?
N4B C8B H8BB 109.2 . . ?
N4B C8B C9B 111.88(15) . . ?
H9AA C9A H9AB 107.9 . . ?
C10A C9A H9AA 109.2 . . ?
C10A C9A H9AB 109.2 . . ?
N4A C9A H9AA 109.2 . . ?
N4A C9A H9AB 109.2 . . ?
N4A C9A C10A 111.89(14) . . ?
C8B C9B H9BA 108.7 . . ?
C8B C9B H9BB 108.7 . . ?
C8B C9B C10B 114.11(16) . . ?
H9BA C9B H9BB 107.6 . . ?
C10B C9B H9BA 108.7 . . ?
C10B C9B H9BB 108.7 . . ?
C9A C10A H10A 109.4 . . ?
C9A C10A H10B 109.4 . . ?
H10A C10A H10B 108.0 . . ?
N1A C10A C9A 111.21(14) . . ?
N1A C10A H10A 109.4 . . ?
N1A C10A H10B 109.4 . . ?
C9B C10B H10C 109.0 . . ?
C9B C10B H10D 109.0 . . ?
H10C C10B H10D 107.8 . . ?
N1B C10B C9B 113.03(14) . . ?
N1B C10B H10C 109.0 . . ?
N1B C10B H10D 109.0 . . ?
C12A C11A H11A 114.6 . . ?
N1A C11A H11A 114.6 . . ?
N1A C11A C12A 130.77(15) . . ?
C12B C11B H11B 114.6 . . ?
N1B C11B H11B 114.6 . . ?
N1B C11B C12B 130.70(16) . . ?
C11A C12A C13A 117.83(15) . . ?
C11A C12A N3A 124.31(15) . . ?
N3A C12A C13A 117.51(15) . . ?
C11B C12B C13B 118.04(16) . . ?
C11B C12B N3B 124.48(15) . . ?
N3B C12B C13B 117.05(15) . . ?
N5A C13A C12A 175.8(2) . . ?
N5B C13B C12B 174.8(2) . . ?
H21A C21A H21B 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
N2A C21A H21A 109.5 . . ?
N2A C21A H21B 109.5 . . ?
N2A C21A H21C 109.5 . . ?
H21D C21B H21E 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
N2B C21B H21D 109.5 . . ?
N2B C21B H21E 109.5 . . ?
N2B C21B H21F 109.5 . . ?
H41A C41A H41B 109.5 . . ?
H41A C41A H41C 109.5 . . ?
H41B C41A H41C 109.5 . . ?
N4A C41A H41A 109.5 . . ?
N4A C41A H41B 109.5 . . ?
N4A C41A H41C 109.5 . . ?
H41D C41B H41E 109.5 . . ?
H41D C41B H41F 109.5 . . ?
H41E C41B H41F 109.5 . . ?
N4B C41B H41D 109.5 . . ?
N4B C41B H41E 109.5 . . ?
N4B C41B H41F 109.5 . . ?
C1A N1A C10A 115.82(13) . . ?
C11A N1A C1A 116.67(13) . . ?
C11A N1A C10A 124.51(14) . . ?
C10B N1B C1B 116.24(14) . . ?
C11B N1B C1B 123.99(14) . . ?
C11B N1B C10B 116.64(15) . . ?
C4A N2A C3A 114.37(13) . . ?
C21A N2A C3A 113.12(14) . . ?
C21A N2A C4A 112.11(14) . . ?
C2B N2B C3B 112.93(13) . . ?
C21B N2B C2B 110.66(14) . . ?
C21B N2B C3B 110.27(15) . . ?
C6A N3A C5A 110.75(13) . . ?
C12A N3A C5A 112.61(14) . . ?
C12A N3A C6A 114.23(14) . . ?
C5B N3B C6B 110.91(14) . . ?
C12B N3B C5B 114.12(14) . . ?
C12B N3B C6B 113.02(14) . . ?
C9A N4A C8A 112.85(14) . . ?
C41A N4A C8A 110.67(14) . . ?
C41A N4A C9A 111.74(14) . . ?
C7B N4B C8B 114.77(15) . . ?
C41B N4B C7B 111.98(15) . . ?
C41B N4B C8B 112.03(16) . . ?

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
C1A C2A C3A N2A -74.19(18) . . . . ?
C1B C2B N2B C3B -72.85(18) . . . . ?
C1B C2B N2B C21B 162.99(15) . . . . ?
C2A C1A N1A C10A 66.18(18) . . . . ?
C2A C1A N1A C11A -95.14(17) . . . . ?
C2A C3A N2A C4A 150.66(14) . . . . ?
C2A C3A N2A C21A -79.34(18) . . . . ?
C2B C1B N1B C10B -111.00(16) . . . . ?
C2B C1B N1B C11B 89.74(18) . . . . ?
C3B C4B C5B N3B 52.7(2) . . . . ?
C4A C5A N3A C6A 172.44(15) . . . . ?
C4A C5A N3A C12A 43.1(2) . . . . ?
C4B C3B N2B C2B 135.39(15) . . . . ?
C4B C3B N2B C21B -100.23(17) . . . . ?
C4B C5B N3B C6B -169.93(15) . . . . ?
C4B C5B N3B C12B 61.05(19) . . . . ?
C5A C4A N2A C3A -149.82(15) . . . . ?
C5A C4A N2A C21A 79.69(18) . . . . ?
C6A C7A C8A N4A 105.28(18) . . . . ?
C6B C7B N4B C8B 148.23(15) . . . . ?
C6B C7B N4B C41B -82.60(19) . . . . ?
C7A C6A N3A C5A 171.87(15) . . . . ?
C7A C6A N3A C12A -59.7(2) . . . . ?
C7A C8A N4A C9A -135.66(15) . . . . ?
C7A C8A N4A C41A 98.29(17) . . . . ?
C7B C6B N3B C5B -169.35(15) . . . . ?
C7B C6B N3B C12B -39.8(2) . . . . ?
C8B C9B C10B N1B -47.8(2) . . . . ?
C9A C10A N1A C1A 111.09(16) . . . . ?
C9A C10A N1A C11A -89.23(19) . . . . ?
C9B C8B N4B C7B -150.23(15) . . . . ?
C9B C8B N4B C41B 80.63(19) . . . . ?
C9B C10B N1B C1B -67.2(2) . . . . ?
C9B C10B N1B C11B 93.66(18) . . . . ?
C10A C9A N4A C8A 72.16(18) . . . . ?
C10A C9A N4A C41A -162.37(14) . . . . ?
C11A C12A N3A C5A -99.28(19) . . . . ?
C11A C12A N3A C6A 133.25(18) . . . . ?
C11B C12B N3B C5B -134.18(18) . . . . ?
C11B C12B N3B C6B 97.9(2) . . . . ?
C12A C11A N1A C1A 145.53(18) . . . . ?
C12A C11A N1A C10A -14.0(3) . . . . ?
C12B C11B N1B C1B 13.1(3) . . . . ?
C12B C11B N1B C10B -146.14(19) . . . . ?
C13A C12A N3A C5A 73.87(19) . . . . ?
C13A C12A N3A C6A -53.6(2) . . . . ?
C13B C12B N3B C5B 53.5(2) . . . . ?
C13B C12B N3B C6B -74.4(2) . . . . ?
N1A C1A C2A C3A 49.16(19) . . . . ?
N1A C11A C12A C13A 175.68(17) . . . . ?
N1A C11A C12A N3A -11.2(3) . . . . ?
N1B C1B C2B N2B -66.87(18) . . . . ?
N1B C11B C12B C13B -177.43(17) . . . . ?
N1B C11B C12B N3B 10.3(3) . . . . ?
N2A C4A C5A N3A 52.2(2) . . . . ?
N2B C3B C4B C5B -105.50(18) . . . . ?
N3A C6A C7A C8A -53.2(2) . . . . ?
N3B C6B C7B N4B -55.0(2) . . . . ?
N4A C9A C10A N1A 67.46(18) . . . . ?
N4B C8B C9B C10B 74.9(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'
####################################################################### 
# 
# 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_4Cu
_database_code_depnum_ccdc_archive 'CCDC 1439079'
_audit_update_record             
;
2015-11-26 deposited with the CCDC.
2016-03-30 downloaded from the CCDC.
;
_publcif_datablock.id            {6a986e8d-1050-4315-9b51-56b24bcd4825}

_audit_creation_date             2015-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled Sep 16 2015 11:44:03 for OlexSys, GUI svn.r5103)
;
# publcif _publ_body_element loop start


_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H31 Cu N5 O2, 2(N O3)'
_chemical_formula_sum            'C15 H31 Cu N7 O8'
_chemical_formula_weight         501.01
_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'
Cu Cu 0.3201 1.2651 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.103(5)
_cell_length_b                   14.421(5)
_cell_length_c                   18.511(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4299(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5139
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.074
_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 blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2104
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_special_details           ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9161
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.192
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean 9
_diffrn_detector_type            CCD
_diffrn_measured_fraction_theta_full 0.997
_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                3820
_reflns_number_total             4897
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.232
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4897
_refine_ls_number_restraints     279
_refine_ls_R_factor_all          0.1309
_refine_ls_R_factor_gt           0.1076
_refine_ls_restrained_S_all      1.147
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0935P)²+31.0231P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2621
_refine_ls_wR_factor_ref         0.2768
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Rigid body (RIGU) restrains
 O4, C2, O3, C10, O5, N5, O2, C14, Cu1, C7, C15, C8, N4, C1, O1, O8, C5, C3,
 N3, C9, N1, O7, N7, C13, O6, C4, C12, N6, N2, C6, C11
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Rotating group:
 O2(H2A,H2B), O1(H1A,H1B)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1C,H1D), C9(H9A,H9B), C6(H6A,H6B), C2(H2C,H2D), C10(H10A,H10B), C5(H5A,
 H5B), C8(H8A,H8B), C4(H4A,H4B), C7(H7A,H7B), C3(H3A,H3B)
3.c Aromatic/amide H refined with riding coordinates:
 C11(H11)
3.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.38190(5) 0.73517(6) 0.64742(4) 0.0362(3) Uani 1 1 d . U . . .
O2 O 0.2562(3) 0.6582(4) 0.6675(3) 0.0493(12) Uani 1 1 d . U . . .
H2A H 0.2147 0.6921 0.6529 0.074 Uiso 1 1 d GR . . . .
H2B H 0.2499 0.6471 0.7133 0.074 Uiso 1 1 d GR . . . .
O1 O 0.4141(4) 0.6802(5) 0.7419(3) 0.0666(16) Uani 1 1 d . U . . .
H1A H 0.4672 0.6844 0.7478 0.100 Uiso 1 1 d GR . . . .
H1B H 0.4004 0.6224 0.7433 0.100 Uiso 1 1 d GR . . . .
N3 N 0.5059(4) 0.7943(5) 0.6144(4) 0.0495(14) Uani 1 1 d . U . . .
N1 N 0.3417(4) 0.7969(5) 0.5536(3) 0.0518(14) Uani 1 1 d . U . . .
N7 N 0.2416(6) 0.4221(5) 0.3503(4) 0.0662(19) Uani 1 1 d . U . . .
C12 C 0.4867(4) 0.8387(5) 0.5479(4) 0.0396(13) Uani 1 1 d . U . . .
N2 N 0.3511(5) 0.8635(5) 0.6948(4) 0.0593(16) Uani 1 1 d . U . . .
N6 N 0.4421(4) 0.2484(6) 0.6388(4) 0.0620(18) Uani 1 1 d . U . . .
O8 O 0.2728(6) 0.4561(6) 0.4048(4) 0.098(3) Uani 1 1 d . U . . .
N4 N 0.4229(5) 0.6158(5) 0.5896(4) 0.0623(17) Uani 1 1 d . U . . .
C13 C 0.5522(5) 0.8880(5) 0.5098(4) 0.0497(17) Uani 1 1 d . U . . .
N5 N 0.6081(5) 0.9237(6) 0.4840(5) 0.071(2) Uani 1 1 d . U . . .
O5 O 0.4250(5) 0.1981(7) 0.6914(4) 0.101(3) Uani 1 1 d . U . . .
C11 C 0.4125(5) 0.8377(5) 0.5188(4) 0.0464(16) Uani 1 1 d . U . . .
H11 H 0.4053 0.8647 0.4736 0.056 Uiso 1 1 calc R . . . .
O4 O 0.3921(5) 0.2747(7) 0.5965(5) 0.105(3) Uani 1 1 d . U . . .
O3 O 0.5140(5) 0.2704(8) 0.6317(4) 0.118(4) Uani 1 1 d . U . . .
C1 C 0.2815(6) 0.8794(6) 0.5795(5) 0.063(2) Uani 1 1 d . U . . .
H1C H 0.2703 0.9210 0.5395 0.076 Uiso 1 1 calc R . . . .
H1D H 0.2292 0.8542 0.5965 0.076 Uiso 1 1 calc R . . . .
O7 O 0.2845(7) 0.4043(9) 0.3000(5) 0.150(5) Uani 1 1 d . U . . .
O6 O 0.1706(7) 0.4042(12) 0.3461(6) 0.184(7) Uani 1 1 d . U . . .
C9 C 0.3364(7) 0.6621(7) 0.4781(6) 0.075(2) Uani 1 1 d . U . . .
H9A H 0.3034 0.6325 0.4408 0.090 Uiso 1 1 calc R . . . .
H9B H 0.3867 0.6844 0.4552 0.090 Uiso 1 1 calc R . . . .
C6 C 0.5581(7) 0.7043(8) 0.5973(6) 0.081(3) Uani 1 1 d . U . . .
H6A H 0.6077 0.7203 0.5702 0.097 Uiso 1 1 calc R . . . .
H6B H 0.5748 0.6741 0.6418 0.097 Uiso 1 1 calc R . . . .
C2 C 0.3239(7) 0.9304(7) 0.6390(5) 0.072(2) Uani 1 1 d . U . . .
H2C H 0.3716 0.9635 0.6200 0.086 Uiso 1 1 calc R . . . .
H2D H 0.2861 0.9752 0.6600 0.086 Uiso 1 1 calc R . . . .
C10 C 0.2888(6) 0.7454(7) 0.5043(5) 0.068(2) Uani 1 1 d . U . . .
H10A H 0.2733 0.7843 0.4637 0.081 Uiso 1 1 calc R . . . .
H10B H 0.2386 0.7258 0.5288 0.081 Uiso 1 1 calc R . . . .
C5 C 0.5532(7) 0.8502(8) 0.6637(5) 0.079(3) Uani 1 1 d . U . . .
H5A H 0.6029 0.8729 0.6400 0.095 Uiso 1 1 calc R . . . .
H5B H 0.5699 0.8132 0.7050 0.095 Uiso 1 1 calc R . . . .
C8 C 0.3603(8) 0.5908(7) 0.5297(6) 0.084(3) Uani 1 1 d . U . . .
H8A H 0.3831 0.5392 0.5027 0.101 Uiso 1 1 calc R . . . .
H8B H 0.3101 0.5687 0.5530 0.101 Uiso 1 1 calc R . . . .
C15 C 0.4278(8) 0.5370(7) 0.6356(6) 0.090(3) Uani 1 1 d . U . . .
H15A H 0.4627 0.5510 0.6762 0.135 Uiso 1 1 calc GR . . . .
H15B H 0.4509 0.4857 0.6093 0.135 Uiso 1 1 calc GR . . . .
H15C H 0.3732 0.5210 0.6523 0.135 Uiso 1 1 calc GR . . . .
C14 C 0.2905(8) 0.8481(7) 0.7522(6) 0.091(3) Uani 1 1 d . U . . .
H14A H 0.2406 0.8227 0.7320 0.136 Uiso 1 1 calc GR . . . .
H14B H 0.2781 0.9060 0.7755 0.136 Uiso 1 1 calc GR . . . .
H14C H 0.3130 0.8056 0.7870 0.136 Uiso 1 1 calc GR . . . .
C4 C 0.5007(7) 0.9308(9) 0.6884(6) 0.088(3) Uani 1 1 d . U . . .
H4A H 0.4820 0.9639 0.6458 0.106 Uiso 1 1 calc R . . . .
H4B H 0.5362 0.9727 0.7154 0.106 Uiso 1 1 calc R . . . .
C7 C 0.5009(7) 0.6382(7) 0.5515(7) 0.083(3) Uani 1 1 d . U . . .
H7A H 0.4880 0.6678 0.5058 0.099 Uiso 1 1 calc R . . . .
H7B H 0.5308 0.5813 0.5412 0.099 Uiso 1 1 calc R . . . .
C3 C 0.4253(7) 0.9103(9) 0.7344(6) 0.089(3) Uani 1 1 d . U . . .
H3A H 0.4059 0.9680 0.7554 0.107 Uiso 1 1 calc R . . . .
H3B H 0.4422 0.8703 0.7739 0.107 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
Cu1 O2 2.339(5) . ?
Cu1 O1 1.989(5) . ?
Cu1 N3 2.255(6) . ?
Cu1 N1 2.056(6) . ?
Cu1 N2 2.107(7) . ?
Cu1 N4 2.133(7) . ?
O2 H2A 0.8706 . ?
O2 H2B 0.8700 . ?
O1 H1A 0.8634 . ?
O1 H1B 0.8630 . ?
N3 C12 1.423(9) . ?
N3 C6 1.578(13) . ?
N3 C5 1.436(11) . ?
N1 C11 1.436(9) . ?
N1 C1 1.607(11) . ?
N1 C10 1.452(11) . ?
N7 O8 1.230(10) . ?
N7 O7 1.187(11) . ?
N7 O6 1.175(12) . ?
C12 C13 1.454(10) . ?
C12 C11 1.311(10) . ?
N2 C2 1.480(13) . ?
N2 C14 1.460(11) . ?
N2 C3 1.556(13) . ?
N6 O5 1.244(11) . ?
N6 O4 1.187(10) . ?
N6 O3 1.207(10) . ?
N4 C8 1.540(14) . ?
N4 C15 1.422(12) . ?
N4 C7 1.477(12) . ?
C13 N5 1.142(10) . ?
C11 H11 0.9300 . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C1 C2 1.490(14) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.505(14) . ?
C9 C8 1.455(15) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.573(16) . ?
C2 H2C 0.9700 . ?
C2 H2D 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.509(16) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.513(15) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?

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 Cu1 O2 84.1(2) . . ?
O1 Cu1 N3 99.1(2) . . ?
O1 Cu1 N1 175.8(3) . . ?
O1 Cu1 N2 92.6(3) . . ?
O1 Cu1 N4 92.2(3) . . ?
N3 Cu1 O2 171.4(2) . . ?
N1 Cu1 O2 93.8(2) . . ?
N1 Cu1 N3 83.5(2) . . ?
N1 Cu1 N2 84.1(3) . . ?
N1 Cu1 N4 91.3(3) . . ?
N2 Cu1 O2 98.5(2) . . ?
N2 Cu1 N3 89.4(3) . . ?
N2 Cu1 N4 172.3(3) . . ?
N4 Cu1 O2 87.9(2) . . ?
N4 Cu1 N3 84.0(3) . . ?
Cu1 O2 H2A 110.4 . . ?
Cu1 O2 H2B 110.1 . . ?
H2A O2 H2B 108.4 . . ?
Cu1 O1 H1A 110.0 . . ?
Cu1 O1 H1B 110.1 . . ?
H1A O1 H1B 108.6 . . ?
C12 N3 Cu1 102.3(4) . . ?
C12 N3 C6 108.2(7) . . ?
C12 N3 C5 114.3(7) . . ?
C6 N3 Cu1 102.4(5) . . ?
C5 N3 Cu1 120.7(6) . . ?
C5 N3 C6 107.8(8) . . ?
C11 N1 Cu1 107.8(5) . . ?
C11 N1 C1 108.0(6) . . ?
C11 N1 C10 113.1(7) . . ?
C1 N1 Cu1 105.0(5) . . ?
C10 N1 Cu1 119.6(6) . . ?
C10 N1 C1 102.3(7) . . ?
O7 N7 O8 119.5(11) . . ?
O6 N7 O8 122.6(9) . . ?
O6 N7 O7 117.9(9) . . ?
N3 C12 C13 118.9(6) . . ?
C11 C12 N3 123.3(6) . . ?
C11 C12 C13 117.9(7) . . ?
C2 N2 Cu1 110.6(5) . . ?
C2 N2 C3 105.9(8) . . ?
C14 N2 Cu1 109.1(6) . . ?
C14 N2 C2 114.2(8) . . ?
C14 N2 C3 103.6(8) . . ?
C3 N2 Cu1 113.4(6) . . ?
O4 N6 O5 123.5(9) . . ?
O4 N6 O3 119.6(10) . . ?
O3 N6 O5 116.9(8) . . ?
C8 N4 Cu1 110.3(6) . . ?
C15 N4 Cu1 111.2(6) . . ?
C15 N4 C8 106.3(8) . . ?
C15 N4 C7 114.4(8) . . ?
C7 N4 Cu1 109.0(6) . . ?
C7 N4 C8 105.4(9) . . ?
N5 C13 C12 174.3(9) . . ?
N1 C11 H11 118.5 . . ?
C12 C11 N1 123.0(6) . . ?
C12 C11 H11 118.5 . . ?
N1 C1 H1C 110.1 . . ?
N1 C1 H1D 110.1 . . ?
H1C C1 H1D 108.4 . . ?
C2 C1 N1 108.0(7) . . ?
C2 C1 H1C 110.1 . . ?
C2 C1 H1D 110.1 . . ?
H9A C9 H9B 107.0 . . ?
C10 C9 H9A 107.5 . . ?
C10 C9 H9B 107.5 . . ?
C8 C9 H9A 107.5 . . ?
C8 C9 H9B 107.5 . . ?
C8 C9 C10 119.1(10) . . ?
N3 C6 H6A 110.3 . . ?
N3 C6 H6B 110.3 . . ?
H6A C6 H6B 108.5 . . ?
C7 C6 N3 107.1(8) . . ?
C7 C6 H6A 110.3 . . ?
C7 C6 H6B 110.3 . . ?
N2 C2 C1 109.3(8) . . ?
N2 C2 H2C 109.8 . . ?
N2 C2 H2D 109.8 . . ?
C1 C2 H2C 109.8 . . ?
C1 C2 H2D 109.8 . . ?
H2C C2 H2D 108.3 . . ?
N1 C10 C9 108.2(8) . . ?
N1 C10 H10A 110.1 . . ?
N1 C10 H10B 110.1 . . ?
C9 C10 H10A 110.1 . . ?
C9 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
N3 C5 H5A 109.8 . . ?
N3 C5 H5B 109.8 . . ?
N3 C5 C4 109.2(9) . . ?
H5A C5 H5B 108.3 . . ?
C4 C5 H5A 109.8 . . ?
C4 C5 H5B 109.8 . . ?
N4 C8 H8A 107.6 . . ?
N4 C8 H8B 107.6 . . ?
C9 C8 N4 118.7(8) . . ?
C9 C8 H8A 107.6 . . ?
C9 C8 H8B 107.6 . . ?
H8A C8 H8B 107.1 . . ?
N4 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
N4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C4 H4A 107.8 . . ?
C5 C4 H4B 107.8 . . ?
C5 C4 C3 118.0(10) . . ?
H4A C4 H4B 107.1 . . ?
C3 C4 H4A 107.8 . . ?
C3 C4 H4B 107.8 . . ?
N4 C7 C6 112.0(9) . . ?
N4 C7 H7A 109.2 . . ?
N4 C7 H7B 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N2 C3 H3A 108.3 . . ?
N2 C3 H3B 108.3 . . ?
C4 C3 N2 115.8(8) . . ?
C4 C3 H3A 108.3 . . ?
C4 C3 H3B 108.3 . . ?
H3A C3 H3B 107.4 . . ?

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
O2 H2A O5 0.87 2.36 3.007(10) 131.2 8_665
O2 H2B O7 0.87 1.85 2.694(10) 162.6 2_565
O1 H1A O5 0.86 2.08 2.881(11) 154.4 3_656
O1 H1B O6 0.86 2.25 2.657(11) 108.6 2_565

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
Cu1 N3 C12 C13 178.5(5) . . . . ?
Cu1 N3 C12 C11 -1.3(8) . . . . ?
Cu1 N3 C6 C7 44.6(8) . . . . ?
Cu1 N3 C5 C4 -56.0(10) . . . . ?
Cu1 N1 C11 C12 -4.6(10) . . . . ?
Cu1 N1 C1 C2 46.3(7) . . . . ?
Cu1 N1 C10 C9 -62.0(9) . . . . ?
Cu1 N2 C2 C1 32.0(9) . . . . ?
Cu1 N2 C3 C4 59.1(12) . . . . ?
Cu1 N4 C8 C9 53.5(12) . . . . ?
Cu1 N4 C7 C6 36.9(10) . . . . ?
N3 C12 C11 N1 4.2(12) . . . . ?
N3 C6 C7 N4 -57.2(10) . . . . ?
N3 C5 C4 C3 66.5(12) . . . . ?
N1 C1 C2 N2 -51.8(9) . . . . ?
C12 N3 C6 C7 -63.0(9) . . . . ?
C12 N3 C5 C4 66.6(10) . . . . ?
C13 C12 C11 N1 -175.6(7) . . . . ?
C11 N1 C1 C2 -68.6(8) . . . . ?
C11 N1 C10 C9 66.8(10) . . . . ?
C1 N1 C11 C12 108.4(9) . . . . ?
C1 N1 C10 C9 -177.3(7) . . . . ?
C6 N3 C12 C13 -73.8(9) . . . . ?
C6 N3 C12 C11 106.4(9) . . . . ?
C6 N3 C5 C4 -173.0(8) . . . . ?
C2 N2 C3 C4 -62.3(12) . . . . ?
C10 N1 C11 C12 -139.2(8) . . . . ?
C10 N1 C1 C2 171.9(7) . . . . ?
C10 C9 C8 N4 -65.4(14) . . . . ?
C5 N3 C12 C13 46.3(10) . . . . ?
C5 N3 C12 C11 -133.5(9) . . . . ?
C5 N3 C6 C7 172.9(8) . . . . ?
C5 C4 C3 N2 -71.5(14) . . . . ?
C8 N4 C7 C6 155.4(8) . . . . ?
C8 C9 C10 N1 64.4(11) . . . . ?
C15 N4 C8 C9 174.2(10) . . . . ?
C15 N4 C7 C6 -88.2(11) . . . . ?
C14 N2 C2 C1 -91.5(9) . . . . ?
C14 N2 C3 C4 177.3(10) . . . . ?
C7 N4 C8 C9 -64.0(12) . . . . ?
C3 N2 C2 C1 155.2(8) . . . . ?

_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 superglue'
_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_5a
_database_code_depnum_ccdc_archive 'CCDC 1439080'

_audit_update_record             
;
2015-11-26 deposited with the CCDC.
2016-03-30 downloaded from the CCDC.
;
_publcif_datablock.id            {e2766dd4-be0c-4ff4-9bcd-1aa657219e8f}

# publcif _publ_body_element loop start

# publcif _publ_body_element loop end
_audit_creation_date             2015-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled Sep 16 2015 11:44:03 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H36 N6'
_chemical_formula_sum            'C28 H36 N6'
_chemical_formula_weight         456.63
_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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.5335(5)
_cell_length_b                   7.6860(2)
_cell_length_c                   21.3414(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.0610(10)
_cell_angle_gamma                90
_cell_volume                     2547.52(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3096
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.073
_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    1.191
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_special_details           ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            5583
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.511
_diffrn_reflns_theta_min         1.909
_diffrn_ambient_temperature      115
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius Kappa Apex II'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_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                2510
_reflns_number_total             2920
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2920
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.095
_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)+(0.0292P)²+3.1423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1060
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 C6, C7
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Ternary CH refined with riding coordinates:
 C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.62895(9) 0.60994(18) 0.29064(6) 0.0190(3) Uani 1 1 d . . . . .
H1A H 0.6590 0.7126 0.3085 0.023 Uiso 1 1 calc R . . . .
H1B H 0.5748 0.6512 0.2705 0.023 Uiso 1 1 calc R . . . .
C2 C 0.68552(8) 0.52898(18) 0.24058(6) 0.0194(3) Uani 1 1 d . . . . .
H2A H 0.6894 0.6104 0.2048 0.023 Uiso 1 1 calc R . . . .
H2B H 0.7443 0.5122 0.2582 0.023 Uiso 1 1 calc R . . . .
C3 C 0.65122(8) 0.35482(18) 0.21690(6) 0.0174(3) Uani 1 1 d . . . . .
H3A H 0.6859 0.3162 0.1810 0.021 Uiso 1 1 calc R . . . .
H3B H 0.6578 0.2669 0.2506 0.021 Uiso 1 1 calc R . . . .
C4 C 0.54458(8) 0.41721(18) 0.13181(6) 0.0182(3) Uani 1 1 d . . . . .
H4A H 0.5307 0.3130 0.1063 0.022 Uiso 1 1 calc R . . . .
H4B H 0.5977 0.4698 0.1152 0.022 Uiso 1 1 calc R . . . .
C5 C 0.47087(8) 0.54774(18) 0.12564(6) 0.0187(3) Uani 1 1 d . . . . .
H5A H 0.4900 0.6609 0.1431 0.022 Uiso 1 1 calc R . . . .
H5B H 0.4567 0.5653 0.0807 0.022 Uiso 1 1 calc R . . . .
C6 C 0.50967(8) 0.21441(17) 0.21438(6) 0.0158(3) Uani 1 1 d . U . . .
H6 H 0.4534 0.2211 0.1910 0.019 Uiso 1 1 calc R . . . .
C7 C 0.55243(8) 0.04775(18) 0.19665(6) 0.0175(3) Uani 1 1 d . U . . .
C8 C 0.68052(9) 0.45636(18) 0.38498(6) 0.0200(3) Uani 1 1 d . . . . .
H8A H 0.6915 0.5602 0.4114 0.024 Uiso 1 1 calc R . . . .
H8B H 0.7329 0.4334 0.3606 0.024 Uiso 1 1 calc R . . . .
C9 C 0.66227(8) 0.30195(19) 0.42638(6) 0.0193(3) Uani 1 1 d . . . . .
C10 C 0.66393(9) 0.13398(19) 0.40221(7) 0.0241(3) Uani 1 1 d . . . . .
H10 H 0.6791 0.1164 0.3598 0.029 Uiso 1 1 calc R . . . .
C11 C 0.64374(11) -0.0083(2) 0.43916(8) 0.0335(4) Uani 1 1 d . . . . .
H11 H 0.6445 -0.1222 0.4219 0.040 Uiso 1 1 calc R . . . .
C12 C 0.62241(11) 0.0164(2) 0.50146(8) 0.0366(4) Uani 1 1 d . . . . .
H12 H 0.6083 -0.0806 0.5269 0.044 Uiso 1 1 calc R . . . .
C13 C 0.62172(11) 0.1820(2) 0.52633(8) 0.0348(4) Uani 1 1 d . . . . .
H13 H 0.6076 0.1991 0.5690 0.042 Uiso 1 1 calc R . . . .
C14 C 0.64153(10) 0.3234(2) 0.48907(7) 0.0266(3) Uani 1 1 d . . . . .
H14 H 0.6409 0.4371 0.5066 0.032 Uiso 1 1 calc R . . . .
N1 N 0.60761(7) 0.49097(15) 0.34179(5) 0.0167(2) Uani 1 1 d . . . . .
N2 N 0.56017(7) 0.36438(15) 0.19719(5) 0.0157(2) Uani 1 1 d . . . . .
N3 N 0.59021(8) -0.07338(16) 0.18238(6) 0.0249(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.5282(19) . ?
C1 N1 1.4668(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5235(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 N2 1.4699(16) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5263(19) . ?
C4 N2 1.4690(16) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 N1 1.4801(17) 2_655 ?
C6 C6 1.555(2) 2_655 ?
C6 H6 1.0000 . ?
C6 C7 1.4948(18) . ?
C6 N2 1.4454(16) . ?
C7 N3 1.1447(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5096(19) . ?
C8 N1 1.4711(16) . ?
C9 C10 1.391(2) . ?
C9 C14 1.392(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(2) . ?
C14 H14 0.9500 . ?
N1 C5 1.4801(17) 2_655 ?

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 107.6 . . ?
C2 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
N1 C1 H1A 108.7 . . ?
N1 C1 H1B 108.7 . . ?
N1 C1 C2 114.03(11) . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 C1 112.80(11) . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
N2 C3 C2 112.32(11) . . ?
N2 C3 H3A 109.1 . . ?
N2 C3 H3B 109.1 . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
N2 C4 H4A 109.2 . . ?
N2 C4 H4B 109.2 . . ?
N2 C4 C5 111.95(11) . . ?
C4 C5 H5A 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
N1 C5 C4 112.88(11) 2_655 . ?
N1 C5 H5A 109.0 2_655 . ?
N1 C5 H5B 109.0 2_655 . ?
C6 C6 H6 107.8 2_655 . ?
C7 C6 C6 110.01(8) . 2_655 ?
C7 C6 H6 107.8 . . ?
N2 C6 C6 111.32(9) . 2_655 ?
N2 C6 H6 107.8 . . ?
N2 C6 C7 111.93(10) . . ?
N3 C7 C6 175.29(14) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
N1 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
N1 C8 C9 110.99(11) . . ?
C10 C9 C8 120.51(12) . . ?
C10 C9 C14 118.23(14) . . ?
C14 C9 C8 121.24(13) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 120.98(14) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.81(16) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.85(15) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.00(15) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 H14 119.4 . . ?
C13 C14 C9 121.12(15) . . ?
C13 C14 H14 119.4 . . ?
C1 N1 C5 111.42(10) . 2_655 ?
C1 N1 C8 113.40(10) . . ?
C8 N1 C5 112.98(10) . 2_655 ?
C4 N2 C3 115.24(10) . . ?
C6 N2 C3 114.29(10) . . ?
C6 N2 C4 112.38(10) . . ?

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 51.56(15) . . . . ?
C2 C1 N1 C5 -158.08(11) . . . 2_655 ?
C2 C1 N1 C8 73.12(14) . . . . ?
C2 C3 N2 C4 87.31(14) . . . . ?
C2 C3 N2 C6 -140.26(11) . . . . ?
C5 C4 N2 C3 -137.09(12) . . . . ?
C5 C4 N2 C6 89.60(13) . . . . ?
C6 C6 N2 C3 74.49(14) 2_655 . . . ?
C6 C6 N2 C4 -151.74(12) 2_655 . . . ?
C7 C6 N2 C3 -49.09(14) . . . . ?
C7 C6 N2 C4 84.68(13) . . . . ?
C8 C9 C10 C11 -177.28(13) . . . . ?
C8 C9 C14 C13 177.59(13) . . . . ?
C9 C8 N1 C1 -165.89(11) . . . . ?
C9 C8 N1 C5 66.11(15) . . . 2_655 ?
C9 C10 C11 C12 -0.7(2) . . . . ?
C10 C9 C14 C13 -1.0(2) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C13 C14 C9 0.1(2) . . . . ?
C14 C9 C10 C11 1.3(2) . . . . ?
N1 C1 C2 C3 50.00(15) . . . . ?
N1 C8 C9 C10 73.61(16) . . . . ?
N1 C8 C9 C14 -104.93(15) . . . . ?
N2 C4 C5 N1 -49.93(15) . . . 2_655 ?

_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'
####################################################################### 
# 
# 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_5b
_database_code_depnum_ccdc_archive 'CCDC 1439081'

_audit_update_record             
;
2015-11-26 deposited with the CCDC.
2016-03-30 downloaded from the CCDC.
;
# publcif _publ_body_element loop end
_audit_creation_date             2015-11-19
_audit_creation_method           
;
Olex2 1.2
(compiled Sep 16 2015 11:44:03 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H36 N6'
_chemical_formula_sum            'C28 H36 N6'
_chemical_formula_weight         456.63
_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'

_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                   9.3978(4)
_cell_length_b                   7.9771(3)
_cell_length_c                   33.7475(14)
_cell_angle_alpha                90
_cell_angle_beta                 96.7820(10)
_cell_angle_gamma                90
_cell_volume                     2512.25(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5133
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.074
_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    1.207
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_special_details           ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            10092
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.452
_diffrn_reflns_theta_min         2.182
_diffrn_ambient_temperature      115
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius Kappa Apex II'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_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                4480
_reflns_number_total             5662
_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       'APEX3 (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5662
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0627
_refine_ls_restrained_S_all      1.096
_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)+(0.0177P)²+2.9590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1296
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C13(H13)
2.b 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), C9(H9A,H9B), C10(H10A,H10B), C15(H15A,H15B),
 C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C24(H24), C25(H25),
 C26(H26), C27(H27), C28(H28)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9371(2) 0.8602(3) 0.94883(6) 0.0232(4) Uani 1 1 d . . . . .
H1A H 0.8758 0.9592 0.9518 0.028 Uiso 1 1 calc R . . . .
H1B H 1.0214 0.8685 0.9693 0.028 Uiso 1 1 calc R . . . .
C2 C 0.8531(2) 0.7022(3) 0.95669(6) 0.0239(4) Uani 1 1 d . . . . .
H2A H 0.9077 0.6024 0.9498 0.029 Uiso 1 1 calc R . . . .
H2B H 0.8418 0.6958 0.9854 0.029 Uiso 1 1 calc R . . . .
C3 C 0.7115(2) 0.6244(3) 0.89380(6) 0.0222(4) Uani 1 1 d . . . . .
H3A H 0.6975 0.5019 0.8960 0.027 Uiso 1 1 calc R . . . .
H3B H 0.8062 0.6431 0.8845 0.027 Uiso 1 1 calc R . . . .
C4 C 0.5955(2) 0.6949(3) 0.86299(6) 0.0245(5) Uani 1 1 d . . . . .
H4A H 0.5003 0.6654 0.8708 0.029 Uiso 1 1 calc R . . . .
H4B H 0.6038 0.6421 0.8368 0.029 Uiso 1 1 calc R . . . .
C5 C 0.6053(2) 0.8847(3) 0.85879(6) 0.0223(4) Uani 1 1 d . . . . .
H5A H 0.5312 0.9230 0.8374 0.027 Uiso 1 1 calc R . . . .
H5B H 0.5856 0.9383 0.8840 0.027 Uiso 1 1 calc R . . . .
C6 C 0.7773(2) 0.9108(3) 0.80834(6) 0.0201(4) Uani 1 1 d . . . . .
H6A H 0.8010 1.0201 0.7968 0.024 Uiso 1 1 calc R . . . .
H6B H 0.6894 0.8683 0.7925 0.024 Uiso 1 1 calc R . . . .
C7 C 0.8993(2) 0.7888(3) 0.80397(6) 0.0215(4) Uani 1 1 d . . . . .
H7A H 0.8895 0.6905 0.8213 0.026 Uiso 1 1 calc R . . . .
H7B H 0.8912 0.7486 0.7760 0.026 Uiso 1 1 calc R . . . .
C8 C 1.1508(2) 0.7410(3) 0.83051(6) 0.0249(5) Uani 1 1 d . . . . .
H8A H 1.2458 0.7962 0.8337 0.030 Uiso 1 1 calc R . . . .
H8B H 1.1540 0.6501 0.8107 0.030 Uiso 1 1 calc R . . . .
C9 C 1.1258(2) 0.6627(3) 0.87042(6) 0.0250(5) Uani 1 1 d . . . . .
H9A H 1.2015 0.5777 0.8773 0.030 Uiso 1 1 calc R . . . .
H9B H 1.0331 0.6023 0.8665 0.030 Uiso 1 1 calc R . . . .
C10 C 1.1233(2) 0.7781(3) 0.90653(6) 0.0248(4) Uani 1 1 d . . . . .
H10A H 1.1465 0.7107 0.9311 0.030 Uiso 1 1 calc R . . . .
H10B H 1.1998 0.8631 0.9059 0.030 Uiso 1 1 calc R . . . .
C11 C 1.0370(2) 1.1689(3) 0.91501(6) 0.0237(4) Uani 1 1 d . . . . .
C12 C 0.9757(2) 1.0260(3) 0.88958(6) 0.0193(4) Uani 1 1 d . . . . .
H12 H 1.0319 1.0187 0.8663 0.023 Uiso 1 1 calc R . . . .
C13 C 0.8170(2) 1.0708(3) 0.87256(6) 0.0197(4) Uani 1 1 d . . . . .
H13 H 0.7620 1.0933 0.8956 0.024 Uiso 1 1 calc R . . . .
C14 C 0.8232(2) 1.2298(3) 0.84927(6) 0.0213(4) Uani 1 1 d . . . . .
C15 C 1.0869(2) 0.9468(3) 0.77894(6) 0.0235(4) Uani 1 1 d . . . . .
H15A H 1.0061 1.0156 0.7664 0.028 Uiso 1 1 calc R . . . .
H15B H 1.1070 0.8597 0.7595 0.028 Uiso 1 1 calc R . . . .
C16 C 1.2176(2) 1.0577(3) 0.78732(6) 0.0222(4) Uani 1 1 d . . . . .
C17 C 1.2208(2) 1.1901(3) 0.81436(6) 0.0272(5) Uani 1 1 d . . . . .
H17 H 1.1410 1.2087 0.8287 0.033 Uiso 1 1 calc R . . . .
C18 C 1.3389(2) 1.2948(3) 0.82066(7) 0.0311(5) Uani 1 1 d . . . . .
H18 H 1.3404 1.3832 0.8396 0.037 Uiso 1 1 calc R . . . .
C19 C 1.4553(2) 1.2709(3) 0.79936(7) 0.0290(5) Uani 1 1 d . . . . .
H19 H 1.5363 1.3427 0.8037 0.035 Uiso 1 1 calc R . . . .
C20 C 1.4524(2) 1.1424(3) 0.77198(7) 0.0281(5) Uani 1 1 d . . . . .
H20 H 1.5309 1.1267 0.7570 0.034 Uiso 1 1 calc R . . . .
C21 C 1.3344(2) 1.0354(3) 0.76621(6) 0.0249(5) Uani 1 1 d . . . . .
H21 H 1.3339 0.9460 0.7476 0.030 Uiso 1 1 calc R . . . .
C22 C 0.5946(2) 0.6393(3) 0.95488(6) 0.0218(4) Uani 1 1 d . . . . .
H22A H 0.5029 0.6842 0.9416 0.026 Uiso 1 1 calc R . . . .
H22B H 0.6085 0.6859 0.9823 0.026 Uiso 1 1 calc R . . . .
C23 C 0.5811(2) 0.4501(3) 0.95785(6) 0.0194(4) Uani 1 1 d . . . . .
C24 C 0.6806(2) 0.3546(3) 0.98220(6) 0.0228(4) Uani 1 1 d . . . . .
H24 H 0.7570 0.4087 0.9982 0.027 Uiso 1 1 calc R . . . .
C25 C 0.6689(2) 0.1814(3) 0.98327(7) 0.0267(5) Uani 1 1 d . . . . .
H25 H 0.7368 0.1180 1.0002 0.032 Uiso 1 1 calc R . . . .
C26 C 0.5591(2) 0.1003(3) 0.95988(7) 0.0279(5) Uani 1 1 d . . . . .
H26 H 0.5525 -0.0185 0.9603 0.033 Uiso 1 1 calc R . . . .
C27 C 0.4591(2) 0.1930(3) 0.93589(7) 0.0299(5) Uani 1 1 d . . . . .
H27 H 0.3830 0.1383 0.9199 0.036 Uiso 1 1 calc R . . . .
C28 C 0.4701(2) 0.3670(3) 0.93519(6) 0.0252(5) Uani 1 1 d . . . . .
H28 H 0.4001 0.4300 0.9189 0.030 Uiso 1 1 calc R . . . .
N1 N 0.98672(17) 0.8657(2) 0.90908(5) 0.0191(3) Uani 1 1 d . . . . .
N2 N 0.71105(18) 0.7007(2) 0.93327(5) 0.0205(4) Uani 1 1 d . . . . .
N3 N 0.74674(17) 0.9382(2) 0.84930(5) 0.0192(3) Uani 1 1 d . . . . .
N4 N 1.04301(17) 0.8643(2) 0.81451(5) 0.0194(3) Uani 1 1 d . . . . .
N5 N 1.0841(2) 1.2761(3) 0.93473(6) 0.0359(5) Uani 1 1 d . . . . .
N6 N 0.8314(2) 1.3445(2) 0.82922(6) 0.0300(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.527(3) . ?
C1 N1 1.472(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 N2 1.469(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.523(3) . ?
C3 N2 1.465(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.525(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 N3 1.467(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.524(3) . ?
C6 N3 1.461(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 N4 1.483(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.528(3) . ?
C8 N4 1.468(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.530(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 N1 1.472(3) . ?
C11 C12 1.500(3) . ?
C11 N5 1.141(3) . ?
C12 H12 1.0000 . ?
C12 C13 1.575(3) . ?
C12 N1 1.437(3) . ?
C13 H13 1.0000 . ?
C13 C14 1.497(3) . ?
C13 N3 1.431(2) . ?
C14 N6 1.146(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.513(3) . ?
C15 N4 1.470(2) . ?
C16 C17 1.393(3) . ?
C16 C21 1.389(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.391(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.378(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.394(3) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.519(3) . ?
C22 N2 1.469(2) . ?
C23 C24 1.396(3) . ?
C23 C28 1.388(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.387(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.384(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.380(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.391(3) . ?
C28 H28 0.9500 . ?

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 107.6 . . ?
C2 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
N1 C1 H1A 108.7 . . ?
N1 C1 H1B 108.7 . . ?
N1 C1 C2 114.10(17) . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
N2 C2 C1 111.65(17) . . ?
N2 C2 H2A 109.3 . . ?
N2 C2 H2B 109.3 . . ?
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 112.87(17) . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C3 C4 C5 112.57(17) . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N3 C5 C4 112.06(17) . . ?
N3 C5 H5A 109.2 . . ?
N3 C5 H5B 109.2 . . ?
H6A C6 H6B 107.5 . . ?
C7 C6 H6A 108.5 . . ?
C7 C6 H6B 108.5 . . ?
N3 C6 H6A 108.5 . . ?
N3 C6 H6B 108.5 . . ?
N3 C6 C7 114.93(16) . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
N4 C7 C6 113.05(16) . . ?
N4 C7 H7A 109.0 . . ?
N4 C7 H7B 109.0 . . ?
H8A C8 H8B 107.5 . . ?
C9 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
N4 C8 H8A 108.5 . . ?
N4 C8 H8B 108.5 . . ?
N4 C8 C9 115.27(17) . . ?
C8 C9 H9A 107.7 . . ?
C8 C9 H9B 107.7 . . ?
C8 C9 C10 118.29(19) . . ?
H9A C9 H9B 107.1 . . ?
C10 C9 H9A 107.7 . . ?
C10 C9 H9B 107.7 . . ?
C9 C10 H10A 108.4 . . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
N1 C10 C9 115.32(16) . . ?
N1 C10 H10A 108.4 . . ?
N1 C10 H10B 108.4 . . ?
N5 C11 C12 179.1(2) . . ?
C11 C12 H12 107.0 . . ?
C11 C12 C13 108.63(16) . . ?
C13 C12 H12 107.0 . . ?
N1 C12 C11 114.35(16) . . ?
N1 C12 H12 107.0 . . ?
N1 C12 C13 112.49(16) . . ?
C12 C13 H13 108.2 . . ?
C14 C13 C12 106.83(16) . . ?
C14 C13 H13 108.2 . . ?
N3 C13 C12 112.86(16) . . ?
N3 C13 H13 108.2 . . ?
N3 C13 C14 112.46(16) . . ?
N6 C14 C13 174.9(2) . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
N4 C15 H15A 108.7 . . ?
N4 C15 H15B 108.7 . . ?
N4 C15 C16 114.15(16) . . ?
C17 C16 C15 121.30(19) . . ?
C21 C16 C15 120.15(19) . . ?
C21 C16 C17 118.4(2) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.8(2) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.6(2) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.1(2) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C20 120.9(2) . . ?
C16 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
H22A C22 H22B 107.4 . . ?
C23 C22 H22A 108.3 . . ?
C23 C22 H22B 108.3 . . ?
N2 C22 H22A 108.3 . . ?
N2 C22 H22B 108.3 . . ?
N2 C22 C23 115.90(17) . . ?
C24 C23 C22 121.73(19) . . ?
C28 C23 C22 120.13(18) . . ?
C28 C23 C24 118.12(19) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 C23 120.6(2) . . ?
C25 C24 H24 119.7 . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.5(2) . . ?
C26 C25 H25 119.8 . . ?
C25 C26 H26 120.2 . . ?
C27 C26 C25 119.6(2) . . ?
C27 C26 H26 120.2 . . ?
C26 C27 H27 120.1 . . ?
C26 C27 C28 119.9(2) . . ?
C28 C27 H27 120.1 . . ?
C23 C28 C27 121.3(2) . . ?
C23 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
C1 N1 C10 114.29(16) . . ?
C12 N1 C1 115.51(16) . . ?
C12 N1 C10 114.29(16) . . ?
C3 N2 C2 113.10(16) . . ?
C3 N2 C22 113.28(16) . . ?
C22 N2 C2 114.75(16) . . ?
C6 N3 C5 116.60(15) . . ?
C13 N3 C5 117.80(16) . . ?
C13 N3 C6 119.99(16) . . ?
C8 N4 C7 112.68(17) . . ?
C8 N4 C15 110.62(16) . . ?
C15 N4 C7 108.75(15) . . ?

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 88.9(2) . . . . ?
C1 C2 N2 C22 -139.06(18) . . . . ?
C2 C1 N1 C10 -84.7(2) . . . . ?
C2 C1 N1 C12 139.66(17) . . . . ?
C3 C4 C5 N3 55.7(2) . . . . ?
C4 C3 N2 C2 -151.38(17) . . . . ?
C4 C3 N2 C22 75.9(2) . . . . ?
C4 C5 N3 C6 75.5(2) . . . . ?
C4 C5 N3 C13 -130.90(19) . . . . ?
C6 C7 N4 C8 149.99(17) . . . . ?
C6 C7 N4 C15 -87.0(2) . . . . ?
C7 C6 N3 C5 -116.20(19) . . . . ?
C7 C6 N3 C13 90.8(2) . . . . ?
C8 C9 C10 N1 81.4(2) . . . . ?
C9 C8 N4 C7 -65.2(2) . . . . ?
C9 C8 N4 C15 172.82(18) . . . . ?
C9 C10 N1 C1 133.62(19) . . . . ?
C9 C10 N1 C12 -90.2(2) . . . . ?
C11 C12 C13 C14 58.6(2) . . . . ?
C11 C12 C13 N3 -177.26(16) . . . . ?
C11 C12 N1 C1 49.4(2) . . . . ?
C11 C12 N1 C10 -86.3(2) . . . . ?
C12 C13 N3 C5 129.38(18) . . . . ?
C12 C13 N3 C6 -77.9(2) . . . . ?
C13 C12 N1 C1 -75.1(2) . . . . ?
C13 C12 N1 C10 149.19(17) . . . . ?
C14 C13 N3 C5 -109.67(19) . . . . ?
C14 C13 N3 C6 43.0(2) . . . . ?
C15 C16 C17 C18 -177.5(2) . . . . ?
C15 C16 C21 C20 176.41(19) . . . . ?
C16 C15 N4 C7 168.54(17) . . . . ?
C16 C15 N4 C8 -67.2(2) . . . . ?
C16 C17 C18 C19 1.2(3) . . . . ?
C17 C16 C21 C20 0.2(3) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C18 C19 C20 C21 -1.1(3) . . . . ?
C19 C20 C21 C16 1.0(3) . . . . ?
C21 C16 C17 C18 -1.3(3) . . . . ?
C22 C23 C24 C25 -177.6(2) . . . . ?
C22 C23 C28 C27 176.9(2) . . . . ?
C23 C22 N2 C2 -80.7(2) . . . . ?
C23 C22 N2 C3 51.3(2) . . . . ?
C23 C24 C25 C26 0.6(3) . . . . ?
C24 C23 C28 C27 -1.4(3) . . . . ?
C24 C25 C26 C27 -1.2(3) . . . . ?
C25 C26 C27 C28 0.5(3) . . . . ?
C26 C27 C28 C23 0.9(4) . . . . ?
C28 C23 C24 C25 0.6(3) . . . . ?
N1 C1 C2 N2 -71.1(2) . . . . ?
N1 C12 C13 C14 -173.73(16) . . . . ?
N1 C12 C13 N3 -49.6(2) . . . . ?
N2 C3 C4 C5 56.4(2) . . . . ?
N2 C22 C23 C24 71.6(3) . . . . ?
N2 C22 C23 C28 -106.6(2) . . . . ?
N3 C6 C7 N4 -77.7(2) . . . . ?
N4 C8 C9 C10 -60.9(3) . . . . ?
N4 C15 C16 C17 -57.3(3) . . . . ?
N4 C15 C16 C21 126.6(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 mylar loop 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_5Cu
_database_code_depnum_ccdc_archive 'CCDC 1439082'
_audit_update_record             
;
2015-11-26 deposited with the CCDC.
2016-03-30 downloaded from the CCDC.
;
_publcif_datablock.id            {8da8e4cd-e166-413b-839e-6753b836c24b}

_audit_creation_date             2015-11-20
_audit_creation_method           
;
Olex2 1.2
(compiled Sep 16 2015 11:44:03 for OlexSys, GUI svn.r5103)
;
# publcif _publ_body_element loop start


_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H36 Cu N7 O3, C H4 O, N O3'
_chemical_formula_sum            'C29 H40 Cu N8 O7'
_chemical_formula_weight         676.23
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.0052(3)
_cell_length_b                   14.4455(4)
_cell_length_c                   23.8253(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3099.30(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3978
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.862
_exptl_absorpt_coefficient_mu    0.764
_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 blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1420
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_special_details           ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_number            7065
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         1.649
_diffrn_ambient_temperature      115
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius Kappa Apex II'
_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  graphite
_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         0.780
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                5738
_reflns_number_total             7065
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.106
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         7065
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.0778
_refine_ls_restrained_S_all      1.224
_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)+13.6087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1621
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.96(3) 0.04(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(O1A) = Uanis(O2A) = Uanis(O3A) = Uanis(O1B) = Uanis(O2B) = Uanis(O3B)
4. Others
 Fixed Sof: O1A(0.58) O2A(0.58) O3A(0.58) O1B(0.42) O2B(0.42) O3B(0.42)
5.a Ternary CH refined with riding coordinates:
 C42(H42), C43(H43)
5.b 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), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C31(H31A,H31B)
5.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C33(H33), C34(H34),
 C35(H35), C36(H36), C37(H37)
5.d Idealised Me refined as rotating group:
 C45(H45A,H45B,H45C)
5.e Idealised tetrahedral OH refined as rotating group:
 O7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8027(9) 0.7451(6) 0.6688(3) 0.0249(18) Uani 1 1 d . . . . .
H1A H 0.8134 0.7746 0.7060 0.030 Uiso 1 1 calc R . . . .
H1B H 0.7809 0.6786 0.6746 0.030 Uiso 1 1 calc R . . . .
C2 C 0.9437(9) 0.7554(5) 0.6364(4) 0.0242(17) Uani 1 1 d . . . . .
H2A H 0.9348 0.7222 0.6002 0.029 Uiso 1 1 calc R . . . .
H2B H 1.0263 0.7271 0.6578 0.029 Uiso 1 1 calc R . . . .
C3 C 1.0860(10) 0.8621(6) 0.5781(4) 0.031(2) Uani 1 1 d . . . . .
H3A H 1.0511 0.8213 0.5474 0.037 Uiso 1 1 calc R . . . .
H3B H 1.1830 0.8380 0.5911 0.037 Uiso 1 1 calc R . . . .
C4 C 1.1089(9) 0.9590(6) 0.5546(4) 0.0287(19) Uani 1 1 d . . . . .
H4A H 1.1470 0.9984 0.5854 0.034 Uiso 1 1 calc R . . . .
H4B H 1.1883 0.9554 0.5259 0.034 Uiso 1 1 calc R . . . .
C5 C 0.9782(10) 1.0087(6) 0.5284(4) 0.0297(19) Uani 1 1 d . . . . .
H5A H 1.0147 1.0671 0.5116 0.036 Uiso 1 1 calc R . . . .
H5B H 0.9396 0.9699 0.4975 0.036 Uiso 1 1 calc R . . . .
C6 C 0.9031(10) 1.0906(6) 0.6151(3) 0.0303(19) Uani 1 1 d . . . . .
H6A H 0.9110 1.1559 0.6030 0.036 Uiso 1 1 calc R . . . .
H6B H 1.0024 1.0697 0.6276 0.036 Uiso 1 1 calc R . . . .
C7 C 0.7938(10) 1.0825(6) 0.6628(3) 0.0295(19) Uani 1 1 d . . . . .
H7A H 0.8307 1.1179 0.6955 0.035 Uiso 1 1 calc R . . . .
H7B H 0.6972 1.1093 0.6513 0.035 Uiso 1 1 calc R . . . .
C8 C 0.6292(10) 0.9732(6) 0.7102(4) 0.028(2) Uani 1 1 d . . . . .
H8A H 0.5499 1.0031 0.6878 0.034 Uiso 1 1 calc R . . . .
H8B H 0.6378 1.0081 0.7458 0.034 Uiso 1 1 calc R . . . .
C9 C 0.5798(9) 0.8756(6) 0.7240(3) 0.0270(18) Uani 1 1 d . . . . .
H9A H 0.4880 0.8795 0.7467 0.032 Uiso 1 1 calc R . . . .
H9B H 0.6571 0.8467 0.7478 0.032 Uiso 1 1 calc R . . . .
C10 C 0.5497(9) 0.8108(6) 0.6745(3) 0.0251(17) Uani 1 1 d . . . . .
H10A H 0.5108 0.7517 0.6896 0.030 Uiso 1 1 calc R . . . .
H10B H 0.4703 0.8387 0.6513 0.030 Uiso 1 1 calc R . . . .
C11 C 0.6261(10) 0.7253(5) 0.5904(3) 0.0268(18) Uani 1 1 d . . . . .
H11A H 0.5473 0.7573 0.5689 0.032 Uiso 1 1 calc R . . . .
H11B H 0.7104 0.7148 0.5645 0.032 Uiso 1 1 calc R . . . .
C12 C 0.5670(10) 0.6319(6) 0.6091(4) 0.0304(19) Uani 1 1 d . . . . .
C13 C 0.4142(11) 0.6196(7) 0.6166(4) 0.040(2) Uani 1 1 d . . . . .
H13 H 0.3486 0.6700 0.6102 0.048 Uiso 1 1 calc R . . . .
C14 C 0.3574(13) 0.5346(9) 0.6333(4) 0.054(3) Uani 1 1 d . . . . .
H14 H 0.2532 0.5263 0.6371 0.065 Uiso 1 1 calc R . . . .
C15 C 0.4526(16) 0.4624(8) 0.6442(4) 0.054(3) Uani 1 1 d . . . . .
H15 H 0.4145 0.4048 0.6570 0.065 Uiso 1 1 calc R . . . .
C16 C 0.6006(15) 0.4732(7) 0.6368(4) 0.049(3) Uani 1 1 d . . . . .
H16 H 0.6649 0.4225 0.6443 0.058 Uiso 1 1 calc R . . . .
C17 C 0.6611(12) 0.5568(6) 0.6185(4) 0.037(2) Uani 1 1 d . . . . .
H17 H 0.7650 0.5624 0.6124 0.044 Uiso 1 1 calc R . . . .
C31 C 0.7320(10) 1.0833(6) 0.5345(3) 0.0278(17) Uani 1 1 d . . . . .
H31A H 0.6443 1.0908 0.5591 0.033 Uiso 1 1 calc R . . . .
H31B H 0.7012 1.0445 0.5022 0.033 Uiso 1 1 calc R . . . .
C32 C 0.7754(10) 1.1781(5) 0.5123(3) 0.0282(18) Uani 1 1 d . . . . .
C33 C 0.7496(12) 1.2590(5) 0.5436(3) 0.0326(18) Uani 1 1 d . . . . .
H33 H 0.7070 1.2552 0.5800 0.039 Uiso 1 1 calc R . . . .
C34 C 0.7870(11) 1.3449(6) 0.5210(4) 0.038(2) Uani 1 1 d . . . . .
H34 H 0.7707 1.3994 0.5424 0.045 Uiso 1 1 calc R . . . .
C35 C 0.8470(10) 1.3521(7) 0.4682(5) 0.040(2) Uani 1 1 d . . . . .
H35 H 0.8733 1.4109 0.4534 0.048 Uiso 1 1 calc R . . . .
C36 C 0.8685(12) 1.2731(7) 0.4369(5) 0.046(3) Uani 1 1 d . . . . .
H36 H 0.9085 1.2771 0.4000 0.055 Uiso 1 1 calc R . . . .
C37 C 0.8314(11) 1.1867(7) 0.4595(4) 0.037(2) Uani 1 1 d . . . . .
H37 H 0.8457 1.1327 0.4374 0.045 Uiso 1 1 calc R . . . .
C41 C 0.9558(9) 1.0106(6) 0.7551(4) 0.0271(18) Uani 1 1 d . . . . .
C42 C 0.8996(10) 0.9450(6) 0.7128(4) 0.0267(19) Uani 1 1 d . . . . .
H42 H 0.8592 0.8908 0.7339 0.032 Uiso 1 1 calc R . . . .
C43 C 1.0305(8) 0.9073(6) 0.6758(3) 0.0248(16) Uani 1 1 d . . . . .
H43 H 1.0885 0.9620 0.6624 0.030 Uiso 1 1 calc R . . . .
C44 C 1.1292(10) 0.8524(7) 0.7121(4) 0.032(2) Uani 1 1 d . . . . .
C45 C 0.9689(11) 0.8485(8) 0.8646(4) 0.043(2) Uani 1 1 d . . . . .
H45A H 0.9802 0.9142 0.8738 0.065 Uiso 1 1 calc GR . . . .
H45B H 1.0631 0.8244 0.8500 0.065 Uiso 1 1 calc GR . . . .
H45C H 0.9413 0.8141 0.8985 0.065 Uiso 1 1 calc GR . . . .
N1 N 0.6780(8) 0.7895(5) 0.6373(3) 0.0233(15) Uani 1 1 d . . . . .
N2 N 0.9781(8) 0.8564(5) 0.6255(3) 0.0252(15) Uani 1 1 d . . . . .
N3 N 0.8510(8) 1.0317(5) 0.5669(3) 0.0261(16) Uani 1 1 d . . . . .
N4 N 0.7729(8) 0.9833(4) 0.6788(3) 0.0251(14) Uani 1 1 d . . . . .
N5 N 0.9967(10) 1.0577(6) 0.7903(3) 0.040(2) Uani 1 1 d . . . . .
N6 N 1.2040(9) 0.8084(6) 0.7402(3) 0.042(2) Uani 1 1 d . . . . .
N7 N 0.5647(10) 0.8960(5) 0.5147(3) 0.0377(19) Uani 1 1 d . . . . .
N8 N 0.7092(10) 0.6185(6) 0.8123(4) 0.045(2) Uani 1 1 d . . . . .
O1A O 0.7048(13) 0.8784(8) 0.5241(5) 0.0367(14) Uani 0.58 1 d . . P A 1
O2A O 0.4937(13) 0.9291(9) 0.5575(5) 0.0367(14) Uani 0.58 1 d . . P A 1
O3A O 0.5046(13) 0.8830(9) 0.4706(5) 0.0367(14) Uani 0.58 1 d . . P A 1
O1B O 0.6869(18) 0.8653(12) 0.4945(7) 0.0367(14) Uani 0.42 1 d . . P A 2
O2B O 0.5609(18) 0.9238(13) 0.5620(7) 0.0367(14) Uani 0.42 1 d . . P A 2
O3B O 0.4467(19) 0.8933(12) 0.4847(7) 0.0367(14) Uani 0.42 1 d . . P A 2
O4 O 0.8348(8) 0.6523(6) 0.8125(4) 0.058(2) Uani 1 1 d . . . . .
O5 O 0.6022(9) 0.6642(5) 0.7957(4) 0.061(2) Uani 1 1 d . . . . .
O6 O 0.6931(9) 0.5382(5) 0.8307(4) 0.069(3) Uani 1 1 d . . . . .
O7 O 0.8568(8) 0.8378(5) 0.8236(3) 0.0458(18) Uani 1 1 d . . . . .
H7 H 0.8502 0.7817 0.8145 0.069 Uiso 1 1 calc GR . . . .
Cu Cu 0.76164(11) 0.91166(6) 0.60126(4) 0.0228(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.492(11) . ?
C1 N1 1.495(10) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 N2 1.515(10) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.522(12) . ?
C3 N2 1.492(10) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.513(12) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 N3 1.504(11) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.508(11) . ?
C6 N3 1.504(10) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 N4 1.495(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.516(12) . ?
C8 N4 1.502(11) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.528(11) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 N1 1.489(10) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.518(11) . ?
C11 N1 1.526(10) . ?
C12 C13 1.399(13) . ?
C12 C17 1.395(13) . ?
C13 H13 0.9500 . ?
C13 C14 1.389(15) . ?
C14 H14 0.9500 . ?
C14 C15 1.376(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.353(17) . ?
C16 H16 0.9500 . ?
C16 C17 1.395(13) . ?
C17 H17 0.9500 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.519(11) . ?
C31 N3 1.518(10) . ?
C32 C33 1.405(11) . ?
C32 C37 1.361(13) . ?
C33 H33 0.9500 . ?
C33 C34 1.394(11) . ?
C34 H34 0.9500 . ?
C34 C35 1.373(14) . ?
C35 H35 0.9500 . ?
C35 C36 1.378(15) . ?
C36 H36 0.9500 . ?
C36 C37 1.399(13) . ?
C37 H37 0.9500 . ?
C41 C42 1.474(11) . ?
C41 N5 1.141(11) . ?
C42 H42 1.0000 . ?
C42 C43 1.569(12) . ?
C42 N4 1.504(11) . ?
C43 H43 1.0000 . ?
C43 C44 1.471(12) . ?
C43 N2 1.484(10) . ?
C44 N6 1.143(11) . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C45 O7 1.414(11) . ?
N1 Cu 2.102(7) . ?
N2 Cu 2.184(7) . ?
N3 Cu 2.079(7) . ?
N4 Cu 2.120(6) . ?
N7 O1A 1.307(14) . ?
N7 O2A 1.294(15) . ?
N7 O3A 1.197(14) . ?
N7 O1B 1.281(18) . ?
N7 O2B 1.198(19) . ?
N7 O3B 1.281(18) . ?
N8 O4 1.232(11) . ?
N8 O5 1.233(11) . ?
N8 O6 1.248(11) . ?
O1A Cu 1.968(11) . ?
O2A Cu 2.641(12) . ?
O1B Cu 2.715(16) . ?
O2B Cu 2.042(16) . ?
O7 H7 0.8400 . ?

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 108.2 . . ?
C2 C1 H1A 109.7 . . ?
C2 C1 H1B 109.7 . . ?
C2 C1 N1 109.7(6) . . ?
N1 C1 H1A 109.7 . . ?
N1 C1 H1B 109.7 . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C1 C2 N2 111.0(6) . . ?
H2A C2 H2B 108.0 . . ?
N2 C2 H2A 109.4 . . ?
N2 C2 H2B 109.4 . . ?
H3A C3 H3B 107.6 . . ?
C4 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
N2 C3 H3A 108.6 . . ?
N2 C3 H3B 108.6 . . ?
N2 C3 C4 114.7(7) . . ?
C3 C4 H4A 107.6 . . ?
C3 C4 H4B 107.6 . . ?
H4A C4 H4B 107.0 . . ?
C5 C4 C3 118.8(8) . . ?
C5 C4 H4A 107.6 . . ?
C5 C4 H4B 107.6 . . ?
C4 C5 H5A 108.2 . . ?
C4 C5 H5B 108.2 . . ?
H5A C5 H5B 107.3 . . ?
N3 C5 C4 116.5(7) . . ?
N3 C5 H5A 108.2 . . ?
N3 C5 H5B 108.2 . . ?
H6A C6 H6B 108.3 . . ?
C7 C6 H6A 109.8 . . ?
C7 C6 H6B 109.8 . . ?
N3 C6 H6A 109.8 . . ?
N3 C6 H6B 109.8 . . ?
N3 C6 C7 109.2(7) . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
N4 C7 C6 110.4(7) . . ?
N4 C7 H7A 109.6 . . ?
N4 C7 H7B 109.6 . . ?
H8A C8 H8B 107.3 . . ?
C9 C8 H8A 108.1 . . ?
C9 C8 H8B 108.1 . . ?
N4 C8 H8A 108.1 . . ?
N4 C8 H8B 108.1 . . ?
N4 C8 C9 116.8(7) . . ?
C8 C9 H9A 108.0 . . ?
C8 C9 H9B 108.0 . . ?
C8 C9 C10 117.1(7) . . ?
H9A C9 H9B 107.3 . . ?
C10 C9 H9A 108.0 . . ?
C10 C9 H9B 108.0 . . ?
C9 C10 H10A 108.1 . . ?
C9 C10 H10B 108.1 . . ?
H10A C10 H10B 107.3 . . ?
N1 C10 C9 116.6(7) . . ?
N1 C10 H10A 108.1 . . ?
N1 C10 H10B 108.1 . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C12 C11 N1 115.6(7) . . ?
N1 C11 H11A 108.4 . . ?
N1 C11 H11B 108.4 . . ?
C13 C12 C11 119.7(9) . . ?
C17 C12 C11 121.8(8) . . ?
C17 C12 C13 118.5(9) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(10) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.7(10) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.1(10) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.2 . . ?
C15 C16 C17 121.7(11) . . ?
C17 C16 H16 119.2 . . ?
C12 C17 H17 120.4 . . ?
C16 C17 C12 119.1(10) . . ?
C16 C17 H17 120.4 . . ?
H31A C31 H31B 107.4 . . ?
C32 C31 H31A 108.3 . . ?
C32 C31 H31B 108.3 . . ?
N3 C31 H31A 108.3 . . ?
N3 C31 H31B 108.3 . . ?
N3 C31 C32 116.0(7) . . ?
C33 C32 C31 121.5(8) . . ?
C37 C32 C31 119.9(8) . . ?
C37 C32 C33 118.4(8) . . ?
C32 C33 H33 120.2 . . ?
C34 C33 C32 119.7(8) . . ?
C34 C33 H33 120.2 . . ?
C33 C34 H34 119.5 . . ?
C35 C34 C33 121.1(9) . . ?
C35 C34 H34 119.5 . . ?
C34 C35 H35 120.4 . . ?
C34 C35 C36 119.3(9) . . ?
C36 C35 H35 120.4 . . ?
C35 C36 H36 120.1 . . ?
C35 C36 C37 119.7(10) . . ?
C37 C36 H36 120.1 . . ?
C32 C37 C36 121.8(9) . . ?
C32 C37 H37 119.1 . . ?
C36 C37 H37 119.1 . . ?
N5 C41 C42 175.9(9) . . ?
C41 C42 H42 106.5 . . ?
C41 C42 C43 110.4(7) . . ?
C41 C42 N4 113.1(7) . . ?
C43 C42 H42 106.5 . . ?
N4 C42 H42 106.5 . . ?
N4 C42 C43 113.3(7) . . ?
C42 C43 H43 107.4 . . ?
C44 C43 C42 108.2(7) . . ?
C44 C43 H43 107.4 . . ?
C44 C43 N2 113.5(7) . . ?
N2 C43 C42 112.7(6) . . ?
N2 C43 H43 107.4 . . ?
N6 C44 C43 178.7(10) . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
O7 C45 H45A 109.5 . . ?
O7 C45 H45B 109.5 . . ?
O7 C45 H45C 109.5 . . ?
C1 N1 C11 109.7(6) . . ?
C1 N1 Cu 107.2(5) . . ?
C10 N1 C1 112.0(6) . . ?
C10 N1 C11 108.9(6) . . ?
C10 N1 Cu 110.3(5) . . ?
C11 N1 Cu 108.7(5) . . ?
C2 N2 Cu 102.4(5) . . ?
C3 N2 C2 108.4(6) . . ?
C3 N2 Cu 111.2(5) . . ?
C43 N2 C2 113.8(6) . . ?
C43 N2 C3 112.2(7) . . ?
C43 N2 Cu 108.4(5) . . ?
C5 N3 C6 110.6(7) . . ?
C5 N3 C31 109.6(6) . . ?
C5 N3 Cu 110.5(5) . . ?
C6 N3 C31 109.3(6) . . ?
C6 N3 Cu 107.0(5) . . ?
C31 N3 Cu 109.7(5) . . ?
C7 N4 C8 109.2(6) . . ?
C7 N4 C42 113.3(6) . . ?
C7 N4 Cu 104.6(4) . . ?
C8 N4 C42 110.5(6) . . ?
C8 N4 Cu 110.2(5) . . ?
C42 N4 Cu 109.0(5) . . ?
O2A N7 O1A 114.5(9) . . ?
O3A N7 O1A 123.8(11) . . ?
O3A N7 O2A 121.7(11) . . ?
O1B N7 O3B 119.5(12) . . ?
O2B N7 O1B 119.7(12) . . ?
O2B N7 O3B 120.8(13) . . ?
O4 N8 O5 120.5(9) . . ?
O4 N8 O6 118.3(9) . . ?
O5 N8 O6 121.2(10) . . ?
N7 O1A Cu 111.3(8) . . ?
N7 O2A Cu 79.9(7) . . ?
N7 O1B Cu 77.0(8) . . ?
N7 O2B Cu 112.1(12) . . ?
C45 O7 H7 109.5 . . ?
N1 Cu N2 84.5(3) . . ?
N1 Cu N4 94.1(2) . . ?
N1 Cu O2A 85.1(3) . . ?
N1 Cu O1B 95.0(4) . . ?
N2 Cu O2A 162.7(3) . . ?
N2 Cu O1B 112.3(4) . . ?
N3 Cu N1 178.1(3) . . ?
N3 Cu N2 93.6(3) . . ?
N3 Cu N4 85.3(3) . . ?
N3 Cu O2A 96.8(3) . . ?
N3 Cu O1B 86.1(4) . . ?
N4 Cu N2 84.6(3) . . ?
N4 Cu O2A 110.0(4) . . ?
N4 Cu O1B 161.6(4) . . ?
O1A Cu N1 94.8(4) . . ?
O1A Cu N2 112.9(4) . . ?
O1A Cu N3 86.3(4) . . ?
O1A Cu N4 161.0(4) . . ?
O1A Cu O2A 54.3(4) . . ?
O2B Cu N1 86.7(6) . . ?
O2B Cu N2 160.5(5) . . ?
O2B Cu N3 95.2(6) . . ?
O2B Cu N4 113.5(6) . . ?
O2B Cu O1B 51.2(6) . . ?

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
O7 H7 O4 0.84 1.88 2.699(12) 166.6 .

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
C1 C2 N2 C3 -160.9(7) . . . . ?
C1 C2 N2 C43 73.5(9) . . . . ?
C1 C2 N2 Cu -43.3(7) . . . . ?
C2 C1 N1 C10 -160.1(6) . . . . ?
C2 C1 N1 C11 78.9(8) . . . . ?
C2 C1 N1 Cu -38.9(7) . . . . ?
C3 C4 C5 N3 64.3(11) . . . . ?
C4 C3 N2 C2 168.7(7) . . . . ?
C4 C3 N2 C43 -64.7(9) . . . . ?
C4 C3 N2 Cu 56.9(9) . . . . ?
C4 C5 N3 C6 57.8(9) . . . . ?
C4 C5 N3 C31 178.4(7) . . . . ?
C4 C5 N3 Cu -60.5(8) . . . . ?
C6 C7 N4 C8 -159.8(7) . . . . ?
C6 C7 N4 C42 76.7(8) . . . . ?
C6 C7 N4 Cu -41.9(7) . . . . ?
C7 C6 N3 C5 -158.7(7) . . . . ?
C7 C6 N3 C31 80.4(8) . . . . ?
C7 C6 N3 Cu -38.3(8) . . . . ?
C8 C9 C10 N1 62.5(10) . . . . ?
C9 C8 N4 C7 173.0(7) . . . . ?
C9 C8 N4 C42 -61.9(9) . . . . ?
C9 C8 N4 Cu 58.7(8) . . . . ?
C9 C10 N1 C1 59.2(9) . . . . ?
C9 C10 N1 C11 -179.3(7) . . . . ?
C9 C10 N1 Cu -60.1(8) . . . . ?
C11 C12 C13 C14 179.4(8) . . . . ?
C11 C12 C17 C16 178.7(8) . . . . ?
C12 C11 N1 C1 61.1(9) . . . . ?
C12 C11 N1 C10 -61.8(9) . . . . ?
C12 C11 N1 Cu 178.0(6) . . . . ?
C12 C13 C14 C15 2.0(15) . . . . ?
C13 C12 C17 C16 -2.3(13) . . . . ?
C13 C14 C15 C16 -2.4(15) . . . . ?
C14 C15 C16 C17 0.5(16) . . . . ?
C15 C16 C17 C12 1.9(15) . . . . ?
C17 C12 C13 C14 0.3(13) . . . . ?
C31 C32 C33 C34 -178.0(9) . . . . ?
C31 C32 C37 C36 178.0(9) . . . . ?
C32 C31 N3 C5 -65.1(9) . . . . ?
C32 C31 N3 C6 56.3(9) . . . . ?
C32 C31 N3 Cu 173.3(5) . . . . ?
C32 C33 C34 C35 0.8(15) . . . . ?
C33 C32 C37 C36 2.4(15) . . . . ?
C33 C34 C35 C36 0.9(15) . . . . ?
C34 C35 C36 C37 -1.0(15) . . . . ?
C35 C36 C37 C32 -0.7(16) . . . . ?
C37 C32 C33 C34 -2.4(14) . . . . ?
C41 C42 C43 C44 65.4(9) . . . . ?
C41 C42 C43 N2 -168.3(7) . . . . ?
C41 C42 N4 C7 40.8(10) . . . . ?
C41 C42 N4 C8 -82.0(9) . . . . ?
C41 C42 N4 Cu 156.8(6) . . . . ?
C42 C43 N2 C2 -85.1(8) . . . . ?
C42 C43 N2 C3 151.3(7) . . . . ?
C42 C43 N2 Cu 28.1(8) . . . . ?
C43 C42 N4 C7 -85.8(8) . . . . ?
C43 C42 N4 C8 151.4(7) . . . . ?
C43 C42 N4 Cu 30.1(8) . . . . ?
C44 C43 N2 C2 38.3(9) . . . . ?
C44 C43 N2 C3 -85.2(8) . . . . ?
C44 C43 N2 Cu 151.6(6) . . . . ?
N1 C1 C2 N2 57.9(9) . . . . ?
N1 C11 C12 C13 95.2(10) . . . . ?
N1 C11 C12 C17 -85.7(10) . . . . ?
N2 C3 C4 C5 -62.3(11) . . . . ?
N3 C6 C7 N4 55.6(9) . . . . ?
N3 C31 C32 C33 -91.9(10) . . . . ?
N3 C31 C32 C37 92.6(10) . . . . ?
N4 C8 C9 C10 -61.7(10) . . . . ?
N4 C42 C43 C44 -166.6(7) . . . . ?
N4 C42 C43 N2 -40.2(9) . . . . ?
O1A N7 O2A Cu 0.9(8) . . . . ?
O2A N7 O1A Cu -1.3(12) . . . . ?
O3A N7 O1A Cu 178.8(10) . . . . ?
O3A N7 O2A Cu -179.2(10) . . . . ?
O1B N7 O2B Cu -1.4(19) . . . . ?
O2B N7 O1B Cu 1.0(13) . . . . ?
O3B N7 O1B Cu -176.4(12) . . . . ?
O3B N7 O2B Cu 176.0(12) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a mylar loop oil'
_olex2_submission_special_instructions 'No special instructions were received'

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.96(3)
2 0.04(3)
