# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_kw21
_database_code_depnum_ccdc_archive 'CCDC 1851001'
_audit_update_record             
;
2018-06-22 deposited with the CCDC.
2018-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H42 N3, C2 N3'
_chemical_formula_sum            'C23 H42 N6'
_chemical_formula_weight         402.63

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'

_symmetry_cell_setting           monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'

loop_
_symmetry_equiv_pos_as_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                   21.8840(7)
_cell_length_b                   9.4228(3)
_cell_length_c                   27.0076(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.472(2)
_cell_angle_gamma                90.00
_cell_volume                     5108.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.38
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.047
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1776
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            55815
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         27.50
_reflns_number_total             5876
_reflns_number_gt                4258
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5876
_refine_ls_number_parameters     297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1665
_refine_ls_wR_factor_gt          0.1369
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_restrained_S_all      1.160
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.003

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.26687(6) 0.01274(12) 0.05246(5) 0.0257(3) Uani 1 1 d . . .
N2 N 0.23505(6) 0.13837(12) 0.16920(4) 0.0266(3) Uani 1 1 d . . .
C11B C 0.25780(7) 0.07583(14) -0.03998(6) 0.0264(3) Uani 1 1 d . . .
H11ba H 0.2377 0.1664 -0.0383 0.032 Uiso 1 1 calc R . .
H11bb H 0.3056 0.0894 -0.0263 0.032 Uiso 1 1 calc R . .
C2 C 0.21393(6) 0.11453(13) 0.11651(5) 0.0223(3) Uani 1 1 d . . .
C11C C 0.23230(8) 0.02684(15) -0.09831(6) 0.0307(3) Uani 1 1 d . . .
H11ca H 0.2425 0.0973 -0.1196 0.046 Uiso 1 1 calc R . .
H11cc H 0.1849 0.0134 -0.1120 0.046 Uiso 1 1 calc R . .
H11cb H 0.2534 -0.0612 -0.1003 0.046 Uiso 1 1 calc R . .
C1 C 0.22573(7) 0.06754(13) 0.07272(5) 0.0231(3) Uani 1 1 d . . .
C12A C 0.33541(6) -0.02442(13) 0.08798(6) 0.0246(3) Uani 1 1 d . . .
H12ab H 0.3516 0.0433 0.1174 0.029 Uiso 1 1 calc R . .
H12aa H 0.3633 -0.0164 0.0678 0.029 Uiso 1 1 calc R . .
C11A C 0.24199(7) -0.03053(13) -0.00449(5) 0.0240(3) Uani 1 1 d . . .
H11aa H 0.1941 -0.0430 -0.0181 0.029 Uiso 1 1 calc R . .
H11ab H 0.2615 -0.1214 -0.0069 0.029 Uiso 1 1 calc R . .
C21A C 0.30048(7) 0.08730(16) 0.20669(6) 0.0305(3) Uani 1 1 d . . .
H21aa H 0.3133 0.0066 0.1907 0.037 Uiso 1 1 calc R . .
H21ab H 0.2971 0.0552 0.2397 0.037 Uiso 1 1 calc R . .
C22A C 0.19081(8) 0.20080(16) 0.19209(6) 0.0310(3) Uani 1 1 d . . .
H22aa H 0.1599 0.2646 0.1658 0.037 Uiso 1 1 calc R . .
H22ab H 0.2171 0.2562 0.2237 0.037 Uiso 1 1 calc R . .
C31B C 0.07648(7) 0.39678(15) 0.06347(6) 0.0317(3) Uani 1 1 d . . .
H31bb H 0.1232 0.4101 0.0864 0.038 Uiso 1 1 calc R . .
H31ba H 0.0679 0.4413 0.0290 0.038 Uiso 1 1 calc R . .
C3 C 0.16511(7) 0.12566(14) 0.06525(6) 0.0259(3) Uani 1 1 d . A .
N3 N 0.10426(7) 0.16589(15) 0.03255(5) 0.0386(3) Uani 1 1 d . . .
C31A C 0.06145(7) 0.23903(15) 0.05511(6) 0.0308(3) Uani 1 1 d . A .
H31aa H 0.0677 0.1960 0.0894 0.037 Uiso 1 1 calc R . .
H31ab H 0.0152 0.2263 0.0309 0.037 Uiso 1 1 calc R . .
C12B C 0.34243(7) -0.17314(14) 0.11135(6) 0.0275(3) Uani 1 1 d . . .
H12ba H 0.3165 -0.1802 0.1332 0.033 Uiso 1 1 calc R . .
H12bb H 0.3246 -0.2411 0.0821 0.033 Uiso 1 1 calc R . .
C31C C 0.03400(8) 0.46728(16) 0.08926(7) 0.0380(4) Uani 1 1 d . . .
H31ca H -0.0122 0.4509 0.0673 0.057 Uiso 1 1 calc R . .
H31cc H 0.0426 0.5675 0.0922 0.057 Uiso 1 1 calc R . .
H31cb H 0.0448 0.4280 0.1246 0.057 Uiso 1 1 calc R . .
C12C C 0.41422(8) -0.20994(18) 0.14555(7) 0.0408(4) Uani 1 1 d . . .
H12cc H 0.4397 -0.2070 0.1237 0.061 Uiso 1 1 calc R . .
H12cb H 0.4165 -0.3035 0.1602 0.061 Uiso 1 1 calc R . .
H12ca H 0.4321 -0.1427 0.1745 0.061 Uiso 1 1 calc R . .
C21B C 0.35405(8) 0.19989(18) 0.22053(7) 0.0416(4) Uani 1 1 d . . .
H21bb H 0.3401 0.2835 0.2343 0.050 Uiso 1 1 calc R . .
H21ba H 0.3602 0.2269 0.1881 0.050 Uiso 1 1 calc R . .
C32d C 0.08910(10) 0.1822(2) -0.02628(10) 0.0256(6) Uani 0.719(5) 1 d P A 2
H32da H 0.1302 0.1786 -0.0319 0.031 Uiso 0.719(5) 1 calc PR A 2
H32db H 0.0685 0.2738 -0.0387 0.031 Uiso 0.719(5) 1 calc PR A 2
C22B C 0.15193(9) 0.09013(18) 0.20792(7) 0.0428(4) Uani 1 1 d . . .
H22bb H 0.1827 0.0242 0.2333 0.051 Uiso 1 1 calc R . .
H22ba H 0.1241 0.0370 0.1762 0.051 Uiso 1 1 calc R . .
C32e C 0.04275(11) 0.0654(2) -0.05862(11) 0.0332(7) Uani 0.719(5) 1 d P A 2
H32eB H 0.0646 -0.0258 -0.0479 0.040 Uiso 0.719(5) 1 calc PR A 2
H32eA H 0.0030 0.0649 -0.0511 0.040 Uiso 0.719(5) 1 calc PR A 2
C22C C 0.10816(11) 0.1582(3) 0.23355(9) 0.0630(6) Uani 1 1 d . . .
H22ca H 0.0767 0.2210 0.2080 0.095 Uiso 1 1 calc R . .
H22cc H 0.1356 0.2109 0.2650 0.095 Uiso 1 1 calc R . .
H22cb H 0.0847 0.0854 0.2437 0.095 Uiso 1 1 calc R . .
C32f C 0.02364(19) 0.0875(4) -0.11823(15) 0.0472(9) Uani 0.719(5) 1 d P A 2
H32fA H -0.0018 0.0076 -0.1378 0.071 Uiso 0.719(5) 1 calc PR A 2
H32fC H 0.0632 0.0966 -0.1252 0.071 Uiso 0.719(5) 1 calc PR A 2
H32fB H -0.0026 0.1722 -0.1296 0.071 Uiso 0.719(5) 1 calc PR A 2
C21C C 0.41954(10) 0.1462(3) 0.26250(9) 0.0678(6) Uani 1 1 d . . .
H21ca H 0.4335 0.0639 0.2488 0.102 Uiso 1 1 calc R . .
H21cb H 0.4138 0.1217 0.2949 0.102 Uiso 1 1 calc R . .
H21cc H 0.4527 0.2191 0.2703 0.102 Uiso 1 1 calc R . .
C5 C 0.12489(7) 0.75638(14) 0.04446(6) 0.0285(3) Uani 1 1 d . . .
N6 N 0.12143(7) 0.72419(15) 0.00217(5) 0.0400(3) Uani 1 1 d . . .
N4 N 0.12249(7) 0.80173(15) 0.08955(6) 0.0427(3) Uani 1 1 d . . .
C4 C 0.17011(9) 0.76659(17) 0.13544(7) 0.0377(4) Uani 1 1 d . . .
N5 N 0.20997(10) 0.7445(2) 0.17752(7) 0.0751(6) Uani 1 1 d . . .
C32A C 0.0653(3) 0.0960(5) -0.0226(2) 0.0263(16) Uani 0.281(5) 1 d P A 1
H32ab H 0.0826 0.0021 -0.0244 0.032 Uiso 0.281(5) 1 calc PR A 1
H32aa H 0.0183 0.0887 -0.0299 0.032 Uiso 0.281(5) 1 calc PR A 1
C32B C 0.0770(3) 0.1966(6) -0.0614(3) 0.0356(17) Uani 0.281(5) 1 d P A 1
H32bb H 0.1245 0.2061 -0.0518 0.043 Uiso 0.281(5) 1 calc PR A 1
H32ba H 0.0595 0.2895 -0.0586 0.043 Uiso 0.281(5) 1 calc PR A 1
C32C C 0.0426(5) 0.1423(12) -0.1203(4) 0.052(3) Uani 0.281(5) 1 d P A 1
H32cb H 0.0594 0.0497 -0.1230 0.078 Uiso 0.281(5) 1 calc PR A 1
H32cc H 0.0519 0.2064 -0.1441 0.078 Uiso 0.281(5) 1 calc PR A 1
H32ca H -0.0046 0.1372 -0.1304 0.078 Uiso 0.281(5) 1 calc PR A 1


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.3301(17) . ?
N1 C12A 1.4649(17) . ?
N1 C11A 1.4703(17) . ?
N2 C2 1.3286(17) . ?
N2 C22A 1.4635(18) . ?
N2 C21A 1.4669(18) . ?
C11B C11C 1.5187(19) . ?
C11B C11A 1.5188(18) . ?
C2 C3 1.3752(19) . ?
C2 C1 1.3801(18) . ?
C1 C3 1.3738(19) . ?
C12A C12B 1.5194(18) . ?
C21A C21B 1.514(2) . ?
C22A C22B 1.511(2) . ?
C31B C31C 1.519(2) . ?
C31B C31A 1.520(2) . ?
C3 N3 1.3266(18) . ?
N3 C31A 1.4760(18) . ?
N3 C32d 1.496(3) . ?
N3 C32A 1.538(6) . ?
C12B C12C 1.512(2) . ?
C21B C21C 1.517(3) . ?
C32d C32e 1.515(3) . ?
C22B C22C 1.528(2) . ?
C32e C32f 1.508(5) . ?
C5 N6 1.1546(19) . ?
C5 N4 1.311(2) . ?
N4 C4 1.305(2) . ?
C4 N5 1.143(2) . ?
C32A C32B 1.508(9) . ?
C32B C32C 1.551(13) . ?

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
C1 N1 C12A 120.51(11) . . ?
C1 N1 C11A 120.57(11) . . ?
C12A N1 C11A 118.35(10) . . ?
C2 N2 C22A 120.93(12) . . ?
C2 N2 C21A 120.75(11) . . ?
C22A N2 C21A 117.93(11) . . ?
C11C C11B C11A 111.85(11) . . ?
N2 C2 C3 149.86(13) . . ?
N2 C2 C1 150.25(13) . . ?
C3 C2 C1 59.81(10) . . ?
N1 C1 C3 150.07(13) . . ?
N1 C1 C2 149.92(13) . . ?
C3 C1 C2 59.92(10) . . ?
N1 C12A C12B 113.59(11) . . ?
N1 C11A C11B 113.25(11) . . ?
N2 C21A C21B 112.80(13) . . ?
N2 C22A C22B 112.57(12) . . ?
C31C C31B C31A 111.11(12) . . ?
N3 C3 C1 150.02(14) . . ?
N3 C3 C2 149.69(13) . . ?
C1 C3 C2 60.27(9) . . ?
C3 N3 C31A 119.51(12) . . ?
C3 N3 C32d 118.39(13) . . ?
C31A N3 C32d 118.80(12) . . ?
C3 N3 C32A 123.0(2) . . ?
C31A N3 C32A 113.7(2) . . ?
N3 C31A C31B 112.50(12) . . ?
C12C C12B C12A 111.96(12) . . ?
C21A C21B C21C 111.05(15) . . ?
N3 C32d C32e 110.60(19) . . ?
C22A C22B C22C 111.32(15) . . ?
C32f C32e C32d 110.7(2) . . ?
N6 C5 N4 173.29(16) . . ?
C4 N4 C5 119.16(13) . . ?
N5 C4 N4 174.36(19) . . ?
C32B C32A N3 102.8(4) . . ?
C32A C32B C32C 111.0(6) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.148
####################################################################### 
# 
# 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_mry2767a
_database_code_depnum_ccdc_archive 'CCDC 1851002'
_audit_update_record             
;
2018-06-22 deposited with the CCDC.
2018-08-01 downloaded from the CCDC.
;
_audit_creation_date             2018-05-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
matthew.polson@canterbury.ac.nz
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'H2 O, C9 H18 N3, C2 N3'
_chemical_formula_sum            'C11 H20 N6 O'
_chemical_formula_weight         252.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         C11H20N6O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   23.2120(4)
_cell_length_b                   9.00560(10)
_cell_length_c                   13.5409(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.386(2)
_cell_angle_gamma                90
_cell_volume                     2741.81(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    15377
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.6250
_cell_measurement_theta_min      3.8980
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.818
_exptl_absorpt_coefficient_mu    0.684
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1088
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0649
1 0 -1 0.0198
0 1 0 0.1209
0 -1 0 0.1856
-5 0 4 0.0781
-1 0 0 0.1088
-5 2 4 0.0632
3 -2 -5 0.0799

_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.098
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0013 -0.0004 0.9989 -0.0668 0.0592 -0.0763
0.9992 0.0003 -0.9995 0.0291 -0.1075 0.0456
-0.0009 1.0004 0.0007 -0.1209 0.0182 0.1198
0.0009 -1.0004 -0.0007 0.1209 -0.0182 -0.1198
-4.9975 -0.0009 3.9986 -0.0787 0.4782 -0.1516
-1.0005 0.0001 0.0006 0.0377 0.0483 0.0307
-4.9993 1.9999 4.0000 -0.3205 0.5147 0.0879
2.9969 -1.9993 -4.9976 0.4626 -0.4773 0.0498

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0097
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29797
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.824
_diffrn_reflns_theta_min         3.932
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6501
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     63.00 115.00   1.00    4.00    --  111.00-125.00 120.00   52
  2  ω     47.00  79.00   1.00    4.00    --  111.00 -94.00   0.00   32
  3  ω     44.00  73.00   1.00    4.00    --  111.00 -94.00  60.00   29
  4  ω     44.00  81.00   1.00    4.00    --  111.00 -94.00 120.00   37
  5  ω     44.00 119.00   1.00    4.00    --  111.00-125.00  60.00   75
  6  ω     84.00 109.00   1.00    4.00    --  111.00 -94.00 -60.00   25
  7  ω     68.00 118.00   1.00    4.00    --  111.00-125.00 -60.00   50
  8  ω    101.00 141.00   1.00    4.00    --  111.00 -77.00-150.00   40
  9  ω     70.00  99.00   1.00    4.00    --  111.00-125.00-180.00   29
 10  ω     56.00  96.00   1.00    4.00    --  111.00 -94.00-180.00   40
 11  ω     47.00  83.00   1.00    4.00    --  111.00 -77.00-150.00   36
 12  ω     31.00  66.00   1.00    4.00    --  111.00 -94.00 -60.00   35
 13  ω     24.00  94.00   1.00    1.00    --   42.50-125.00-120.00   70
 14  ω     23.00  89.00   1.00    1.00    --   42.50-125.00 120.00   66
 15  ω     64.00 121.00   1.00    4.00    --   86.00  64.00 -89.72   57
 16  ω    128.00 153.00   1.00    4.00    --   86.00  64.00 -89.72   25
 17  ω    141.00 167.00   1.00    4.00    --  111.00  61.00-141.98   26
 18  ω    120.00 174.00   1.00    4.00    --  111.00  77.00 -60.00   54
 19  ω    116.00 177.00   1.00    4.00    --  111.00  77.00-150.00   61
 20  ω    122.00 174.00   1.00    4.00    --  111.00  77.00-180.00   52
 21  ω    105.00 135.00   1.00    1.00    --   66.00  76.00-167.58   30
 22  ω     99.00 125.00   1.00    1.00    --   54.00  77.00-133.48   26
 23  ω    102.00 129.00   1.00    1.00    --   70.00  76.00 -59.59   27
 24  ω     89.00 124.00   1.00    1.00    --   62.00  77.00  -4.20   35
 25  ω    109.00 135.00   1.00    1.00    --   66.00  77.00  46.04   26
 26  ω    113.00 139.00   1.00    4.00    --   82.00  68.00  60.82   26
 27  ω    112.00 159.00   1.00    4.00    --  111.00  77.00  60.00   47
 28  ω    124.00 157.00   1.00    4.00    --  111.00  61.00 120.00   33
 29  ω    143.00 169.00   1.00    4.00    --  111.00  77.00 120.00   26
 30  ω    127.00 177.00   1.00    4.00    --  111.00  77.00  90.00   50
 31  ω     85.00 115.00   1.00    4.00    --  111.00  61.00 120.00   30
 32  ω     87.00 165.00   1.00    4.00    --  111.00  61.00 150.00   78
 33  ω     86.00 136.00   1.00    4.00    --  111.00  61.00  60.00   50
 34  ω     83.00 161.00   1.00    4.00    --  111.00  72.00  80.92   78
 35  ω     85.00 134.00   1.00    4.00    --  111.00  61.00 -30.00   49
 36  ω     91.00 178.00   1.00    4.00    --  111.00  61.00-120.00   87
 37  ω     86.00 119.00   1.00    4.00    --  111.00  61.00-141.98   33
 38  ω     85.00 143.00   1.00    4.00    --  111.00  61.00-180.00   58
 39  ω     85.00 148.00   1.00    4.00    --  111.00  61.00 -90.00   63
 40  ω     81.00 115.00   1.00    4.00    --  111.00  77.00 -60.00   34
 41  ω     81.00 178.00   1.00    4.00    --  111.00  77.00   0.00   97
 42  ω     81.00 106.00   1.00    4.00    --  111.00  77.00  60.00   25
 43  ω     81.00 176.00   1.00    4.00    --  111.00  77.00  30.00   95
 44  ω     84.00 178.00   1.00    4.00    --  111.00  77.00 -90.00   94
 45  ω     81.00 177.00   1.00    4.00    --  111.00  77.00 -30.00   96
 46  ω     78.00 103.00   1.00    4.00    --  106.00  69.00 -59.77   25
 47  ω     77.00 103.00   1.00    4.00    --  106.00  71.00  -2.37   26
 48  ω     66.00  92.00   1.00    4.00    --   94.00  67.00  27.61   26
 49  ω     65.00  92.00   1.00    4.00    --   94.00  72.00  -9.00   27
 50  ω     55.00  81.00   1.00    4.00    --   82.00  68.00  60.82   26
 51  ω     60.00  92.00   1.00    4.00    --   90.00  77.00 105.51   32
 52  ω     81.00 111.00   1.00    4.00    --  111.00  77.00 120.00   30
 53  ω     82.00 108.00   1.00    4.00    --  111.00  77.00  90.00   26
 54  ω     61.00  92.00   1.00    4.00    --   90.00  73.00 156.98   31
 55  ω     57.00  83.00   1.00    4.00    --   82.00  75.00 149.36   26
 56  ω     48.00  74.00   1.00    4.00    --   78.00  76.00 100.71   26
 57  ω     44.00  70.00   1.00    1.00    --   74.00  75.00  85.66   26
 58  ω     36.00  73.00   1.00    1.00    --   66.00  77.00  46.04   37
 59  ω     48.00  74.00   1.00    4.00    --   78.00  76.00  10.82   26
 60  ω     54.00  80.00   1.00    4.00    --   82.00  67.00 -44.77   26
 61  ω     49.00  84.00   1.00    4.00    --   78.00  74.00 -96.39   35
 62  ω     65.00  91.00   1.00    4.00    --   90.00  61.00-145.44   26
 63  ω     85.00 107.00   1.00    4.00    --  111.00  77.00-150.00   22
 64  ω     81.00 107.00   1.00    4.00    --  111.00  77.00-120.00   26
 65  ω     91.00 108.00   1.00    4.00    --  111.00  77.00-180.00   17
 66  ω     48.00  63.00   1.00    4.00    --   78.00  77.00-170.82   15
 67  ω     44.00  69.00   1.00    1.00    --   74.00  75.00-126.63   25
 68  ω     38.00  82.00   1.00    1.00    --   66.00  76.00-167.58   44
 69  ω     37.00  68.00   1.00    1.00    --   66.00  77.00 -93.88   31
 70  ω     40.00  66.00   1.00    1.00    --   70.00  76.00 -59.59   26
 71  ω     44.00  70.00   1.00    1.00    --   74.00  76.00  -5.53   26
 72  ω     32.00  58.00   1.00    1.00    --   62.00  77.00  -4.20   26
 73  ω     19.00  44.00   1.00    1.00    --   50.00  81.00  21.30   25
 74  ω     19.00  44.00   1.00    1.00    --   50.00  80.00 -31.34   25
 75  ω     14.00  39.00   1.00    1.00    --   46.00  83.00 -66.37   25
 76  ω     25.00  51.00   1.00    1.00    --   54.00  77.00-133.48   26
 77  ω     -1.00  24.00   1.00    1.00    --   34.00  89.00  78.40   25
 78  ω     19.00  44.00   1.00    1.00    --   50.00  81.00  79.19   25
 79  ω     32.00  58.00   1.00    1.00    --   62.00  77.00 115.03   26
 80  ω     36.00  62.00   1.00    1.00    --   66.00  77.00 166.57   26
 81  ω     18.00  43.00   1.00    1.00    --   50.00  82.00 154.89   25
 82  ω    -64.00  29.00   1.00    1.00    --  -38.50  57.00   0.00   93
 83  ω    -54.00  -8.00   1.00    1.00    --  -38.50 -77.00 -30.00   46
 84  ω   -108.00 -19.00   1.00    1.00    --  -38.50 -37.00  30.00   89
 85  ω   -110.00 -57.00   1.00    1.00    --  -38.50 -77.00 -30.00   53
 86  ω    -99.00 -18.00   1.00    1.00    --  -38.50 -37.00-180.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0377159000
_diffrn_orient_matrix_UB_12      -0.1208544000
_diffrn_orient_matrix_UB_13      -0.0668428000
_diffrn_orient_matrix_UB_21      -0.0482207000
_diffrn_orient_matrix_UB_22      0.0181131000
_diffrn_orient_matrix_UB_23      0.0593419000
_diffrn_orient_matrix_UB_31      -0.0307108000
_diffrn_orient_matrix_UB_32      0.1197276000
_diffrn_orient_matrix_UB_33      -0.0762724000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2635
_reflns_number_total             2881
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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         0.293
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.120
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2881
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      1.078
_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)+(0.0654P)²+1.0121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1103
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H) groups
2. Restrained distances
 O1-H1B = O1-H1A
 0.86 with sigma of 0.02
3.a Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C4(H4A,H4B,H4C), C6(H6A,H6B,H6C), C9(H9A,H9B,H9C), C7(H7A,
 H7B,H7C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.67541(4) 0.89524(9) 0.59936(7) 0.0387(2) Uani 1 1 d D . . . .
N1 N 0.70567(3) 0.81408(9) 0.87539(6) 0.0238(2) Uani 1 1 d . . . . .
N2 N 0.54817(3) 0.82551(9) 0.87472(6) 0.0248(2) Uani 1 1 d . . . . .
N3 N 0.62419(4) 0.46402(10) 0.88448(7) 0.0269(2) Uani 1 1 d . . . . .
N4 N 0.64918(4) 0.59582(10) 0.65023(8) 0.0333(2) Uani 1 1 d . . . . .
N6 N 0.59619(4) 0.12457(10) 0.64823(8) 0.0347(2) Uani 1 1 d . . . . .
N5 N 0.57700(4) 0.39056(10) 0.61331(8) 0.0369(2) Uani 1 1 d . . . . .
C1 C 0.65610(4) 0.74159(10) 0.87689(7) 0.0206(2) Uani 1 1 d . . . . .
C2 C 0.59698(4) 0.74578(10) 0.87897(7) 0.0208(2) Uani 1 1 d . . . . .
C3 C 0.62557(4) 0.61083(11) 0.88128(7) 0.0212(2) Uani 1 1 d . . . . .
C11 C 0.59022(4) 0.25104(12) 0.63369(7) 0.0256(2) Uani 1 1 d . . . . .
C10 C 0.61761(4) 0.49426(11) 0.63499(7) 0.0259(2) Uani 1 1 d . . . . .
C5 C 0.70505(4) 0.97608(11) 0.87217(8) 0.0261(2) Uani 1 1 d . . . . .
H5A H 0.681153 1.008803 0.807419 0.039 Uiso 1 1 calc GR . . . .
H5B H 0.744931 1.012249 0.881305 0.039 Uiso 1 1 calc GR . . . .
H5C H 0.688651 1.013732 0.925667 0.039 Uiso 1 1 calc GR . . . .
C4 C 0.75681(4) 0.73707(11) 0.85551(8) 0.0269(2) Uani 1 1 d . . . . .
H4A H 0.753493 0.632641 0.867242 0.040 Uiso 1 1 calc GR . . . .
H4B H 0.792614 0.774637 0.900202 0.040 Uiso 1 1 calc GR . . . .
H4C H 0.758022 0.753157 0.785969 0.040 Uiso 1 1 calc GR . . . .
C6 C 0.55255(4) 0.98679(11) 0.87931(8) 0.0279(2) Uani 1 1 d . . . . .
H6A H 0.574523 1.016498 0.946156 0.042 Uiso 1 1 calc GR . . . .
H6B H 0.513371 1.028969 0.865120 0.042 Uiso 1 1 calc GR . . . .
H6C H 0.572662 1.021226 0.829674 0.042 Uiso 1 1 calc GR . . . .
C9 C 0.67681(5) 0.37396(11) 0.88880(8) 0.0286(2) Uani 1 1 d . . . . .
H9A H 0.709720 0.437393 0.886667 0.043 Uiso 1 1 calc GR . . . .
H9B H 0.669318 0.307413 0.831643 0.043 Uiso 1 1 calc GR . . . .
H9C H 0.686115 0.317662 0.950953 0.043 Uiso 1 1 calc GR . . . .
C7 C 0.49370(4) 0.75537(12) 0.88663(8) 0.0300(2) Uani 1 1 d . . . . .
H7A H 0.489957 0.658592 0.855973 0.045 Uiso 1 1 calc GR . . . .
H7B H 0.460116 0.815102 0.853922 0.045 Uiso 1 1 calc GR . . . .
H7C H 0.495152 0.746231 0.957844 0.045 Uiso 1 1 calc GR . . . .
C8 C 0.56969(5) 0.38503(11) 0.88554(9) 0.0314(2) Uani 1 1 d . . . . .
H8A H 0.540105 0.454659 0.894569 0.047 Uiso 1 1 calc GR . . . .
H8B H 0.577479 0.314871 0.940638 0.047 Uiso 1 1 calc GR . . . .
H8C H 0.555529 0.333431 0.822098 0.047 Uiso 1 1 calc GR . . . .
H1A H 0.6690(7) 0.8073(15) 0.6193(11) 0.047 Uiso 1 1 d DR . . . .
H1B H 0.6497(6) 0.9528(17) 0.6170(11) 0.047 Uiso 1 1 d DR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1A 0.862(13) . ?
O1 H1B 0.868(13) . ?
N1 C1 1.3274(12) . ?
N1 C5 1.4595(12) . ?
N1 C4 1.4566(12) . ?
N2 C2 1.3305(12) . ?
N2 C6 1.4562(13) . ?
N2 C7 1.4576(12) . ?
N3 C3 1.3235(13) . ?
N3 C9 1.4552(12) . ?
N3 C8 1.4544(12) . ?
N4 C10 1.1580(14) . ?
N6 C11 1.1583(14) . ?
N5 C11 1.3065(14) . ?
N5 C10 1.3073(14) . ?
C1 C2 1.3801(13) . ?
C1 C3 1.3833(13) . ?
C2 C3 1.3813(13) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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 O1 H1B 106.2(15) . . ?
C1 N1 C5 119.34(8) . . ?
C1 N1 C4 121.20(8) . . ?
C4 N1 C5 118.22(7) . . ?
C2 N2 C6 119.12(8) . . ?
C2 N2 C7 120.93(8) . . ?
C6 N2 C7 118.74(8) . . ?
C3 N3 C9 122.09(8) . . ?
C3 N3 C8 121.13(8) . . ?
C8 N3 C9 116.77(8) . . ?
C11 N5 C10 121.41(9) . . ?
N1 C1 C2 148.97(9) . . ?
N1 C1 C3 151.00(9) . . ?
C2 C1 C3 59.98(6) . . ?
N2 C2 C1 148.68(9) . . ?
N2 C2 C3 151.04(9) . . ?
C1 C2 C3 60.12(6) . . ?
N3 C3 C1 150.30(9) . . ?
N3 C3 C2 149.80(9) . . ?
C2 C3 C1 59.89(7) . . ?
N6 C11 N5 173.45(11) . . ?
N4 C10 N5 173.31(10) . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.880
_oxdiff_exptl_absorpt_empirical_full_min 0.711
