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

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

data_dan79_jkt2
_database_code_depnum_ccdc_archive 'CCDC 1521456'
_audit_update_record             
;
2016-12-08 deposited with the CCDC.
2017-10-16 downloaded from the CCDC.
;

_audit_creation_date             2016-11-14T15:52:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H27 N5 O'
_chemical_formula_moiety         'C18 H27 N5 O'
_chemical_formula_weight         329.44

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
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                   25.2277(15)
_cell_length_b                   8.2188(4)
_cell_length_c                   17.5148(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.025(5)
_cell_angle_gamma                90
_cell_volume                     3586.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2750
_cell_measurement_theta_min      2.9096
_cell_measurement_theta_max      28.5525

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.22
_exptl_crystal_F_000             1424

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.65055
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.992

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_ub_11      -0.0254963
_diffrn_orient_matrix_ub_12      0.002232
_diffrn_orient_matrix_ub_13      0.0122675
_diffrn_orient_matrix_ub_21      0.0126351
_diffrn_orient_matrix_ub_22      0.0122253
_diffrn_orient_matrix_ub_23      0.0386831
_diffrn_orient_matrix_ub_31      -0.001143
_diffrn_orient_matrix_ub_32      0.0853725
_diffrn_orient_matrix_ub_33      -0.0058552
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0745
_diffrn_reflns_av_unetI/netI     0.1118
_diffrn_reflns_number            14233
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.915
_diffrn_reflns_theta_max         28.615
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.924
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.924
_reflns_Friedel_coverage         0
_reflns_number_total             4248
_reflns_number_gt                2662
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0353P)²+0.5740P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4248
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.109
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1273
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_restrained_S_all      1.07
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.27
_refine_diff_density_rms         0.052

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O9 O 0.30718(5) 0.36974(15) 0.08079(7) 0.0265(3) Uani 1 1 d . . . . .
N7 N 0.39177(6) 0.33305(18) 0.03679(9) 0.0201(4) Uani 1 1 d . . . . .
C6 C 0.37241(7) 0.4235(2) -0.03421(10) 0.0197(4) Uani 1 1 d . . . . .
H6 H 0.3552 0.3415 -0.0725 0.024 Uiso 1 1 calc R U . . .
C14 C 0.36874(8) 0.1718(2) 0.14483(11) 0.0251(5) Uani 1 1 d . . . . .
H14 H 0.338 0.1094 0.16 0.03 Uiso 1 1 calc R U . . .
N4 N 0.42956(7) 0.64004(18) -0.08534(9) 0.0265(4) Uani 1 1 d . . . . .
N2 N 0.49729(6) 0.4926(2) -0.10944(9) 0.0300(4) Uani 1 1 d . . . . .
N1 N 0.46190(6) 0.39561(18) -0.08032(9) 0.0232(4) Uani 1 1 d . . . . .
C8 C 0.34871(7) 0.2564(2) 0.06863(11) 0.0218(4) Uani 1 1 d . . . . .
H8 H 0.3322 0.1722 0.031 0.026 Uiso 1 1 calc R U . . .
C11 C 0.32830(8) 0.5483(2) -0.02434(11) 0.0219(4) Uani 1 1 d . . . . .
C5 C 0.42028(7) 0.4881(2) -0.06606(10) 0.0210(4) Uani 1 1 d . . . . .
N3 N 0.47741(7) 0.6386(2) -0.11209(9) 0.0326(4) Uani 1 1 d . . . . .
C10 C 0.28597(8) 0.4485(2) 0.01012(11) 0.0264(5) Uani 1 1 d . . . . .
H10A H 0.2564 0.5217 0.0193 0.032 Uiso 1 1 calc R U . . .
H10B H 0.2707 0.3652 -0.0279 0.032 Uiso 1 1 calc R U . . .
C19 C 0.39551(8) 0.1461(2) -0.17748(11) 0.0246(4) Uani 1 1 d . . . . .
C24 C 0.35928(8) 0.0460(2) -0.14786(12) 0.0283(5) Uani 1 1 d . . . . .
H24 H 0.3723 -0.039 -0.1132 0.034 Uiso 1 1 calc R U . . .
C12 C 0.30110(8) 0.6143(2) -0.10212(11) 0.0281(5) Uani 1 1 d . . . . .
H12A H 0.2707 0.6831 -0.0943 0.042 Uiso 1 1 calc R U . . .
H12B H 0.2883 0.5235 -0.1363 0.042 Uiso 1 1 calc R U . . .
H12C H 0.3269 0.6789 -0.1257 0.042 Uiso 1 1 calc R U . . .
C16 C 0.38849(9) 0.2895(2) 0.21010(12) 0.0340(5) Uani 1 1 d . . . . .
H16A H 0.4198 0.3488 0.1979 0.051 Uiso 1 1 calc R U . . .
H16B H 0.3985 0.2287 0.2583 0.051 Uiso 1 1 calc R U . . .
H16C H 0.3599 0.3669 0.2161 0.051 Uiso 1 1 calc R U . . .
C18 C 0.45480(8) 0.1305(2) -0.14953(12) 0.0304(5) Uani 1 1 d . . . . .
H18A H 0.4747 0.175 -0.1893 0.037 Uiso 1 1 calc R U . . .
H18B H 0.4642 0.0139 -0.1425 0.037 Uiso 1 1 calc R U . . .
C21 C 0.32060(9) 0.2888(2) -0.25093(12) 0.0324(5) Uani 1 1 d . . . . .
H21 H 0.3075 0.3711 -0.2871 0.039 Uiso 1 1 calc R U . . .
C22 C 0.28506(9) 0.1909(2) -0.21940(12) 0.0332(5) Uani 1 1 d . . . . .
H22 H 0.2475 0.2077 -0.2328 0.04 Uiso 1 1 calc R U . . .
C20 C 0.37553(8) 0.2666(2) -0.22965(11) 0.0277(5) Uani 1 1 d . . . . .
H20 H 0.3998 0.3349 -0.2511 0.033 Uiso 1 1 calc R U . . .
C17 C 0.47221(8) 0.2203(2) -0.07325(11) 0.0270(5) Uani 1 1 d . . . . .
H17A H 0.4526 0.1749 -0.0333 0.032 Uiso 1 1 calc R U . . .
H17B H 0.511 0.202 -0.056 0.032 Uiso 1 1 calc R U . . .
C15 C 0.41269(8) 0.0498(2) 0.13435(12) 0.0316(5) Uani 1 1 d . . . . .
H15A H 0.4003 -0.0203 0.0899 0.047 Uiso 1 1 calc R U . . .
H15B H 0.421 -0.0171 0.181 0.047 Uiso 1 1 calc R U . . .
H15C H 0.445 0.1085 0.1255 0.047 Uiso 1 1 calc R U . . .
C13 C 0.34903(8) 0.6865(2) 0.03046(12) 0.0297(5) Uani 1 1 d . . . . .
H13A H 0.3745 0.7526 0.0071 0.045 Uiso 1 1 calc R U . . .
H13B H 0.367 0.641 0.0795 0.045 Uiso 1 1 calc R U . . .
H13C H 0.3188 0.7545 0.04 0.045 Uiso 1 1 calc R U . . .
C23 C 0.30434(9) 0.0683(2) -0.16818(12) 0.0333(5) Uani 1 1 d . . . . .
H23 H 0.28 -0.0003 -0.147 0.04 Uiso 1 1 calc R U . . .
H7 H 0.4097(8) 0.399(2) 0.0711(12) 0.030(6) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O9 C10 1.424(2) . ?
O9 C8 1.442(2) . ?
N7 C8 1.441(2) . ?
N7 C6 1.465(2) . ?
C6 C5 1.504(2) . ?
C6 C11 1.543(2) . ?
C14 C8 1.519(3) . ?
C14 C16 1.521(3) . ?
C14 C15 1.527(3) . ?
N4 C5 1.324(2) . ?
N4 N3 1.362(2) . ?
N2 N3 1.299(2) . ?
N2 N1 1.355(2) . ?
N1 C5 1.351(2) . ?
N1 C17 1.466(2) . ?
C11 C13 1.526(2) . ?
C11 C12 1.526(3) . ?
C11 C10 1.543(2) . ?
C19 C20 1.388(3) . ?
C19 C24 1.389(3) . ?
C19 C18 1.505(3) . ?
C24 C23 1.388(3) . ?
C18 C17 1.529(3) . ?
C21 C22 1.382(3) . ?
C21 C20 1.390(3) . ?
C22 C23 1.386(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
C10 O9 C8 110.33(14) . . ?
C8 N7 C6 112.27(15) . . ?
N7 C6 C5 108.29(15) . . ?
N7 C6 C11 113.10(15) . . ?
C5 C6 C11 116.22(15) . . ?
C8 C14 C16 113.17(15) . . ?
C8 C14 C15 110.03(16) . . ?
C16 C14 C15 110.46(17) . . ?
C5 N4 N3 106.36(15) . . ?
N3 N2 N1 106.47(16) . . ?
C5 N1 N2 108.39(15) . . ?
C5 N1 C17 132.08(16) . . ?
N2 N1 C17 119.45(16) . . ?
N7 C8 O9 112.58(14) . . ?
N7 C8 C14 111.90(16) . . ?
O9 C8 C14 108.36(15) . . ?
C13 C11 C12 111.01(15) . . ?
C13 C11 C10 109.85(15) . . ?
C12 C11 C10 107.26(16) . . ?
C13 C11 C6 112.54(16) . . ?
C12 C11 C6 111.58(15) . . ?
C10 C11 C6 104.25(14) . . ?
N4 C5 N1 108.05(16) . . ?
N4 C5 C6 127.75(16) . . ?
N1 C5 C6 124.20(16) . . ?
N2 N3 N4 110.72(15) . . ?
O9 C10 C11 113.14(15) . . ?
C20 C19 C24 118.43(19) . . ?
C20 C19 C18 120.98(18) . . ?
C24 C19 C18 120.47(18) . . ?
C23 C24 C19 121.02(19) . . ?
C19 C18 C17 112.22(16) . . ?
C22 C21 C20 119.9(2) . . ?
C21 C22 C23 119.9(2) . . ?
C19 C20 C21 120.95(19) . . ?
N1 C17 C18 112.18(16) . . ?
C22 C23 C24 119.80(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
C8 N7 C6 C5 -175.85(14) . . . . ?
C8 N7 C6 C11 53.8(2) . . . . ?
N3 N2 N1 C5 0.27(19) . . . . ?
N3 N2 N1 C17 177.46(16) . . . . ?
C6 N7 C8 O9 -54.1(2) . . . . ?
C6 N7 C8 C14 -176.45(14) . . . . ?
C10 O9 C8 N7 57.52(19) . . . . ?
C10 O9 C8 C14 -178.18(14) . . . . ?
C16 C14 C8 N7 68.5(2) . . . . ?
C15 C14 C8 N7 -55.6(2) . . . . ?
C16 C14 C8 O9 -56.2(2) . . . . ?
C15 C14 C8 O9 179.72(15) . . . . ?
N7 C6 C11 C13 66.2(2) . . . . ?
C5 C6 C11 C13 -60.0(2) . . . . ?
N7 C6 C11 C12 -168.22(15) . . . . ?
C5 C6 C11 C12 65.6(2) . . . . ?
N7 C6 C11 C10 -52.77(19) . . . . ?
C5 C6 C11 C10 -178.95(15) . . . . ?
N3 N4 C5 N1 0.4(2) . . . . ?
N3 N4 C5 C6 -179.25(17) . . . . ?
N2 N1 C5 N4 -0.4(2) . . . . ?
C17 N1 C5 N4 -177.12(18) . . . . ?
N2 N1 C5 C6 179.23(16) . . . . ?
C17 N1 C5 C6 2.5(3) . . . . ?
N7 C6 C5 N4 -127.21(19) . . . . ?
C11 C6 C5 N4 1.4(3) . . . . ?
N7 C6 C5 N1 53.2(2) . . . . ?
C11 C6 C5 N1 -178.22(17) . . . . ?
N1 N2 N3 N4 0.0(2) . . . . ?
C5 N4 N3 N2 -0.2(2) . . . . ?
C8 O9 C10 C11 -61.28(19) . . . . ?
C13 C11 C10 O9 -63.4(2) . . . . ?
C12 C11 C10 O9 175.83(15) . . . . ?
C6 C11 C10 O9 57.38(19) . . . . ?
C20 C19 C24 C23 -1.7(3) . . . . ?
C18 C19 C24 C23 174.42(18) . . . . ?
C20 C19 C18 C17 94.4(2) . . . . ?
C24 C19 C18 C17 -81.6(2) . . . . ?
C20 C21 C22 C23 -1.6(3) . . . . ?
C24 C19 C20 C21 1.0(3) . . . . ?
C18 C19 C20 C21 -175.04(18) . . . . ?
C22 C21 C20 C19 0.6(3) . . . . ?
C5 N1 C17 C18 94.6(2) . . . . ?
N2 N1 C17 C18 -81.8(2) . . . . ?
C19 C18 C17 N1 -61.6(2) . . . . ?
C21 C22 C23 C24 1.0(3) . . . . ?
C19 C24 C23 C22 0.7(3) . . . . ?

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
C17 H17A N7 0.99 2.48 3.149(3) 124.7 .
N7 H7 N2 0.88(2) 2.50(2) 3.223(2) 139.6(17) 5_665
C17 H17A N7 0.99 2.48 3.149(3) 124.7 .
N7 H7 N2 0.88(2) 2.50(2) 3.223(2) 139.6(17) 5_665

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_dan_81_1
_database_code_depnum_ccdc_archive 'CCDC 1521499'
_audit_update_record             
;
2016-12-08 deposited with the CCDC.
2017-10-16 downloaded from the CCDC.
;

_audit_creation_date             2016-11-21T15:39:37-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C18 H35 N5 O'
_chemical_formula_moiety         'C18 H35 N5 O'
_chemical_formula_weight         337.51

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_space_group_name_H-M_alt 'P 1 21/c 1'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_space_group_IT_number           14
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.4795(8)
_cell_length_b                   15.9839(7)
_cell_length_c                   10.6108(8)
_cell_angle_alpha                90
_cell_angle_beta                 112.921(8)
_cell_angle_gamma                90
_cell_volume                     1949.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    129.6(8)
_cell_measurement_reflns_used    6618
_cell_measurement_theta_min      3.7740
_cell_measurement_theta_max      28.2730
_cell_oxdiff_length_a            12.4677(9)
_cell_oxdiff_length_b            15.9984(9)
_cell_oxdiff_length_c            10.6019(10)
_cell_oxdiff_angle_alpha         89.969(6)
_cell_oxdiff_angle_beta          112.801(8)
_cell_oxdiff_angle_gamma         90.066(5)
_cell_oxdiff_volume              1949.4(3)

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_crystal_density_diffrn    1.15
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_min  0.64204
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.714
_oxdiff_exptl_absorpt_empirical_full_max 1.397
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      129.6(8)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.3756
_diffrn_reflns_number            15428
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.1046
_diffrn_reflns_theta_max         28.5238
_diffrn_measured_fraction_theta_max 0.9211
_diffrn_reflns_theta_full        26.3154
_diffrn_measured_fraction_theta_full 0.9981
_reflns_number_total             4568
_reflns_number_gt                3611
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0156(13)
_refine_ls_number_reflns         4568
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1108
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.042

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O9 O 0.76970(8) 0.31591(5) 0.87254(9) 0.0242(2) Uani 1 d . . .
N1 N 0.87385(8) 0.53377(6) 1.28582(10) 0.0174(2) Uani 1 d . . .
N7 N 0.79892(9) 0.45772(6) 0.95610(10) 0.0180(2) Uani 1 d . . .
N2 N 0.96337(9) 0.58475(7) 1.35959(11) 0.0223(2) Uani 1 d . . .
N4 N 1.01360(9) 0.51460(6) 1.21383(11) 0.0213(2) Uani 1 d . . .
N3 N 1.04547(9) 0.57290(7) 1.31562(12) 0.0240(3) Uani 1 d . . .
C5 C 0.90745(10) 0.49043(7) 1.19708(12) 0.0171(3) Uani 1 d . . .
C14 C 0.68601(11) 0.42464(8) 0.71220(13) 0.0218(3) Uani 1 d . . .
H14 H 0.7553 0.4219 0.6903 0.026 Uiso 1 calc R . .
C17 C 0.76058(10) 0.53927(7) 1.30554(13) 0.0184(3) Uani 1 d . . .
C11 C 0.89895(11) 0.33836(7) 1.11365(13) 0.0202(3) Uani 1 d . . .
C22 C 0.65273(11) 0.65174(8) 1.10119(14) 0.0224(3) Uani 1 d . . .
C21 C 0.66108(10) 0.56506(8) 1.16983(13) 0.0191(3) Uani 1 d . . .
H21A H 0.5893 0.5578 1.1836 0.023 Uiso 1 calc R . .
H21B H 0.6601 0.5238 1.1023 0.023 Uiso 1 calc R . .
C8 C 0.72092(11) 0.39827(8) 0.86096(13) 0.0199(3) Uani 1 d . . .
H8 H 0.6502 0.3945 0.8798 0.024 Uiso 1 calc R . .
C16 C 0.59577(12) 0.36400(9) 0.61794(14) 0.0284(3) Uani 1 d . . .
H16A H 0.525 0.3686 0.6331 0.043 Uiso 1 calc R . .
H16B H 0.6249 0.3078 0.6371 0.043 Uiso 1 calc R . .
H16C H 0.5807 0.3774 0.5244 0.043 Uiso 1 calc R . .
C6 C 0.83871(10) 0.42513(7) 1.09644(12) 0.0171(3) Uani 1 d . . .
H6 H 0.7682 0.416 1.1142 0.021 Uiso 1 calc R . .
C24 C 0.61886(15) 0.72228(9) 1.17693(16) 0.0365(4) Uani 1 d . . .
H24A H 0.551 0.7061 1.1925 0.055 Uiso 1 calc R . .
H24B H 0.6025 0.7723 1.1225 0.055 Uiso 1 calc R . .
H24C H 0.6819 0.7326 1.2631 0.055 Uiso 1 calc R . .
C13 C 0.92465(13) 0.30320(8) 1.25647(14) 0.0263(3) Uani 1 d . . .
H13A H 0.9557 0.2477 1.2629 0.04 Uiso 1 calc R . .
H13B H 0.8541 0.3015 1.2725 0.04 Uiso 1 calc R . .
H13C H 0.9803 0.3384 1.3237 0.04 Uiso 1 calc R . .
C12 C 1.01003(12) 0.33907(8) 1.08412(15) 0.0261(3) Uani 1 d . . .
H12A H 0.9931 0.3626 0.9952 0.039 Uiso 1 calc R . .
H12B H 1.0379 0.2829 1.0867 0.039 Uiso 1 calc R . .
H12C H 1.0685 0.3722 1.152 0.039 Uiso 1 calc R . .
C10 C 0.80652(12) 0.28358(8) 1.00804(14) 0.0244(3) Uani 1 d . . .
H10A H 0.8378 0.2278 1.0103 0.029 Uiso 1 calc R . .
H10B H 0.7397 0.2791 1.0328 0.029 Uiso 1 calc R . .
C18 C 0.73248(11) 0.45288(8) 1.34898(14) 0.0230(3) Uani 1 d . . .
H18A H 0.7991 0.4322 1.4243 0.035 Uiso 1 calc R . .
H18B H 0.7128 0.4147 1.2734 0.035 Uiso 1 calc R . .
H18C H 0.668 0.4578 1.3764 0.035 Uiso 1 calc R . .
C23 C 0.76412(13) 0.67547(9) 1.08106(17) 0.0350(4) Uani 1 d . . .
H23A H 0.7508 0.7255 1.027 0.053 Uiso 1 calc R . .
H23B H 0.7855 0.6308 1.035 0.053 Uiso 1 calc R . .
H23C H 0.8258 0.685 1.1686 0.053 Uiso 1 calc R . .
C15 C 0.64009(13) 0.51409(9) 0.68819(15) 0.0301(3) Uani 1 d . . .
H15A H 0.7 0.5518 0.743 0.045 Uiso 1 calc R . .
H15B H 0.5742 0.5188 0.7132 0.045 Uiso 1 calc R . .
H15C H 0.6171 0.5281 0.5933 0.045 Uiso 1 calc R . .
C19 C 0.77818(12) 0.59968(9) 1.42348(13) 0.0247(3) Uani 1 d . . .
H19A H 0.8078 0.6519 1.4059 0.037 Uiso 1 calc R . .
H19B H 0.8327 0.5761 1.5071 0.037 Uiso 1 calc R . .
H19C H 0.7052 0.609 1.4316 0.037 Uiso 1 calc R . .
C25 C 0.55376(13) 0.64365(9) 0.95966(14) 0.0301(3) Uani 1 d . . .
H25A H 0.5724 0.6004 0.9087 0.045 Uiso 1 calc R . .
H25B H 0.5441 0.6958 0.9116 0.045 Uiso 1 calc R . .
H25C H 0.4829 0.6296 0.9701 0.045 Uiso 1 calc R . .
H7 H 0.8589(14) 0.4674(10) 0.9361(17) 0.032(4) Uiso 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O9 C10 1.4250(16) . ?
O9 C8 1.4354(15) . ?
N1 N2 1.3578(14) . ?
N1 C5 1.3601(16) . ?
N1 C17 1.5099(15) . ?
N7 C8 1.4507(16) . ?
N7 C6 1.4695(15) . ?
N7 H7 0.868(17) . ?
N2 N3 1.2944(15) . ?
N4 C5 1.3237(16) . ?
N4 N3 1.3633(15) . ?
C5 C6 1.5008(17) . ?
C14 C8 1.5243(18) . ?
C14 C15 1.5244(19) . ?
C14 C16 1.5267(18) . ?
C14 H14 0.98 . ?
C17 C19 1.5273(17) . ?
C17 C18 1.5388(17) . ?
C17 C21 1.5469(17) . ?
C11 C13 1.5286(18) . ?
C11 C10 1.5317(18) . ?
C11 C12 1.5358(18) . ?
C11 C6 1.5539(16) . ?
C22 C25 1.5339(19) . ?
C22 C23 1.5340(19) . ?
C22 C24 1.5363(19) . ?
C22 C21 1.5498(17) . ?
C21 H21A 0.97 . ?
C21 H21B 0.97 . ?
C8 H8 0.98 . ?
C16 H16A 0.96 . ?
C16 H16B 0.96 . ?
C16 H16C 0.96 . ?
C6 H6 0.98 . ?
C24 H24A 0.96 . ?
C24 H24B 0.96 . ?
C24 H24C 0.96 . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C23 H23A 0.96 . ?
C23 H23B 0.96 . ?
C23 H23C 0.96 . ?
C15 H15A 0.96 . ?
C15 H15B 0.96 . ?
C15 H15C 0.96 . ?
C19 H19A 0.96 . ?
C19 H19B 0.96 . ?
C19 H19C 0.96 . ?
C25 H25A 0.96 . ?
C25 H25B 0.96 . ?
C25 H25C 0.96 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O9 C8 112.23(9) . . ?
N2 N1 C5 107.36(10) . . ?
N2 N1 C17 119.32(9) . . ?
C5 N1 C17 133.10(10) . . ?
C8 N7 C6 110.08(10) . . ?
C8 N7 H7 110.8(11) . . ?
C6 N7 H7 109.1(11) . . ?
N3 N2 N1 107.06(10) . . ?
C5 N4 N3 105.88(10) . . ?
N2 N3 N4 110.97(10) . . ?
N4 C5 N1 108.71(11) . . ?
N4 C5 C6 124.28(11) . . ?
N1 C5 C6 127.01(11) . . ?
C8 C14 C15 111.69(11) . . ?
C8 C14 C16 110.07(11) . . ?
C15 C14 C16 110.65(11) . . ?
C8 C14 H14 108.1 . . ?
C15 C14 H14 108.1 . . ?
C16 C14 H14 108.1 . . ?
N1 C17 C19 107.86(10) . . ?
N1 C17 C18 108.91(9) . . ?
C19 C17 C18 107.38(10) . . ?
N1 C17 C21 109.99(9) . . ?
C19 C17 C21 113.67(10) . . ?
C18 C17 C21 108.91(10) . . ?
C13 C11 C10 108.82(10) . . ?
C13 C11 C12 110.33(11) . . ?
C10 C11 C12 109.71(11) . . ?
C13 C11 C6 110.47(10) . . ?
C10 C11 C6 103.43(10) . . ?
C12 C11 C6 113.78(10) . . ?
C25 C22 C23 108.20(12) . . ?
C25 C22 C24 107.06(11) . . ?
C23 C22 C24 109.89(12) . . ?
C25 C22 C21 105.41(11) . . ?
C23 C22 C21 112.82(10) . . ?
C24 C22 C21 113.09(11) . . ?
C17 C21 C22 123.95(10) . . ?
C17 C21 H21A 106.3 . . ?
C22 C21 H21A 106.3 . . ?
C17 C21 H21B 106.3 . . ?
C22 C21 H21B 106.3 . . ?
H21A C21 H21B 106.4 . . ?
O9 C8 N7 113.20(10) . . ?
O9 C8 C14 106.43(10) . . ?
N7 C8 C14 112.53(10) . . ?
O9 C8 H8 108.2 . . ?
N7 C8 H8 108.2 . . ?
C14 C8 H8 108.2 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N7 C6 C5 110.39(9) . . ?
N7 C6 C11 113.12(10) . . ?
C5 C6 C11 114.89(10) . . ?
N7 C6 H6 105.9 . . ?
C5 C6 H6 105.9 . . ?
C11 C6 H6 105.9 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O9 C10 C11 112.70(10) . . ?
O9 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
O9 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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
C5 N1 N2 N3 0.69(13) . . . . ?
C17 N1 N2 N3 -174.62(10) . . . . ?
N1 N2 N3 N4 -0.26(13) . . . . ?
C5 N4 N3 N2 -0.28(13) . . . . ?
N3 N4 C5 N1 0.71(13) . . . . ?
N3 N4 C5 C6 -178.78(11) . . . . ?
N2 N1 C5 N4 -0.88(13) . . . . ?
C17 N1 C5 N4 173.52(11) . . . . ?
N2 N1 C5 C6 178.59(11) . . . . ?
C17 N1 C5 C6 -7.0(2) . . . . ?
N2 N1 C17 C19 -5.95(14) . . . . ?
C5 N1 C17 C19 -179.82(12) . . . . ?
N2 N1 C17 C18 -122.19(11) . . . . ?
C5 N1 C17 C18 63.94(16) . . . . ?
N2 N1 C17 C21 118.52(11) . . . . ?
C5 N1 C17 C21 -55.34(16) . . . . ?
N1 C17 C21 C22 -66.67(14) . . . . ?
C19 C17 C21 C22 54.38(16) . . . . ?
C18 C17 C21 C22 174.05(11) . . . . ?
C25 C22 C21 C17 170.57(11) . . . . ?
C23 C22 C21 C17 52.70(17) . . . . ?
C24 C22 C21 C17 -72.79(16) . . . . ?
C10 O9 C8 N7 55.74(13) . . . . ?
C10 O9 C8 C14 179.87(10) . . . . ?
C6 N7 C8 O9 -53.64(13) . . . . ?
C6 N7 C8 C14 -174.37(10) . . . . ?
C15 C14 C8 O9 -176.15(10) . . . . ?
C16 C14 C8 O9 60.53(13) . . . . ?
C15 C14 C8 N7 -51.61(14) . . . . ?
C16 C14 C8 N7 -174.93(10) . . . . ?
C8 N7 C6 C5 -173.04(10) . . . . ?
C8 N7 C6 C11 56.65(13) . . . . ?
N4 C5 C6 N7 -72.10(14) . . . . ?
N1 C5 C6 N7 108.51(13) . . . . ?
N4 C5 C6 C11 57.26(16) . . . . ?
N1 C5 C6 C11 -122.13(13) . . . . ?
C13 C11 C6 N7 -173.03(10) . . . . ?
C10 C11 C6 N7 -56.72(13) . . . . ?
C12 C11 C6 N7 62.24(14) . . . . ?
C13 C11 C6 C5 58.97(14) . . . . ?
C10 C11 C6 C5 175.28(10) . . . . ?
C12 C11 C6 C5 -65.76(14) . . . . ?
C8 O9 C10 C11 -59.44(14) . . . . ?
C13 C11 C10 O9 174.91(10) . . . . ?
C12 C11 C10 O9 -64.29(13) . . . . ?
C6 C11 C10 O9 57.44(13) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
