# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_methyl
_database_code_depnum_ccdc_archive 'CCDC 1034365'
_audit_update_record             
;
2014-11-16 deposited with the CCDC.
2015-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 N4 O2'
_chemical_formula_sum            'C16 H16 N4 O2'
_chemical_formula_weight         296.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3985(5)
_cell_length_b                   7.5160(5)
_cell_length_c                   13.5827(9)
_cell_angle_alpha                100.7370(10)
_cell_angle_beta                 93.4910(10)
_cell_angle_gamma                103.1710(10)
_cell_volume                     718.32(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    1695
_cell_measurement_theta_min      2.844
_cell_measurement_theta_max      27.473

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9907
_exptl_absorpt_correction_T_max  0.9907
_exptl_absorpt_process_details   'SADABS, Bruker(2000)'

_exptl_special_details           
; 
The structure was solved by direct methods (Bruker, 2000) and
successive difference Fourier syntheses.
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4062
_diffrn_reflns_av_R_equivalents  0.0107
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2501
_reflns_number_gt                2119
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (BRUKER 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_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)+(0.0777P)²+0.1083P] 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         2501
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1384
_refine_ls_wR_factor_gt          0.1327
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0516(2) 0.2349(2) -0.00150(11) 0.0347(3) Uani 1 1 d . . .
C2 C 0.0756(2) 0.2120(2) -0.07238(11) 0.0361(4) Uani 1 1 d . . .
C3 C 0.0100(2) 0.0848(2) -0.16400(11) 0.0403(4) Uani 1 1 d . . .
C4 C -0.1770(2) -0.0108(2) -0.18236(12) 0.0479(4) Uani 1 1 d . . .
H4 H -0.2200 -0.0957 -0.2429 0.058 Uiso 1 1 calc R . .
C5 C -0.2997(2) 0.0183(2) -0.11217(12) 0.0494(4) Uani 1 1 d . . .
H5 H -0.4248 -0.0451 -0.1264 0.059 Uiso 1 1 calc R . .
C6 C -0.2386(2) 0.1403(2) -0.02119(12) 0.0428(4) Uani 1 1 d . . .
H6 H -0.3213 0.1591 0.0264 0.051 Uiso 1 1 calc R . .
C7 C 0.2771(2) 0.3205(2) -0.04995(13) 0.0477(4) Uani 1 1 d . . .
H7A H 0.2840 0.4514 -0.0430 0.072 Uiso 1 1 calc R . .
H7B H 0.3458 0.2809 -0.1042 0.072 Uiso 1 1 calc R . .
H7C H 0.3298 0.2981 0.0116 0.072 Uiso 1 1 calc R . .
C8 C 0.1399(3) 0.0482(3) -0.24212(13) 0.0563(5) Uani 1 1 d . . .
H8A H 0.0710 -0.0406 -0.2999 0.085 Uiso 1 1 calc R . .
H8B H 0.2360 -0.0008 -0.2144 0.085 Uiso 1 1 calc R . .
H8C H 0.1956 0.1628 -0.2619 0.085 Uiso 1 1 calc R . .
C9 C -0.0146(2) 0.4950(2) 0.25073(10) 0.0343(3) Uani 1 1 d . . .
C10 C 0.1804(2) 0.6025(2) 0.26873(11) 0.0377(4) Uani 1 1 d . . .
C11 C 0.1244(2) 0.7480(2) 0.43696(11) 0.0433(4) Uani 1 1 d . . .
C12 C -0.0680(2) 0.6337(2) 0.41725(11) 0.0386(4) Uani 1 1 d . . .
C13 C -0.1378(2) 0.5120(2) 0.32825(11) 0.0366(4) Uani 1 1 d . . .
C14 C 0.4281(2) 0.8444(3) 0.37643(13) 0.0611(5) Uani 1 1 d . . .
H14A H 0.5009 0.7968 0.4215 0.092 Uiso 1 1 calc R . .
H14B H 0.4280 0.9708 0.4059 0.092 Uiso 1 1 calc R . .
H14C H 0.4814 0.8411 0.3136 0.092 Uiso 1 1 calc R . .
C15 C -0.1777(2) 0.6571(2) 0.49966(11) 0.0447(4) Uani 1 1 d . . .
C16 C -0.3350(2) 0.3987(2) 0.31045(12) 0.0488(4) Uani 1 1 d . . .
H16A H -0.3972 0.4275 0.3692 0.073 Uiso 1 1 calc R . .
H16B H -0.3365 0.2684 0.2969 0.073 Uiso 1 1 calc R . .
H16C H -0.3981 0.4274 0.2538 0.073 Uiso 1 1 calc R . .
N1 N 0.01746(18) 0.35746(17) 0.09150(9) 0.0361(3) Uani 1 1 d . . .
N2 N -0.08778(17) 0.37807(16) 0.16408(9) 0.0359(3) Uani 1 1 d . . .
N3 N 0.23635(17) 0.72923(18) 0.35861(9) 0.0423(3) Uani 1 1 d . . .
N4 N -0.2623(2) 0.6751(2) 0.56665(11) 0.0660(5) Uani 1 1 d . . .
O1 O 0.29254(15) 0.58442(17) 0.20624(8) 0.0484(3) Uani 1 1 d . . .
O2 O 0.18616(18) 0.85469(19) 0.51685(9) 0.0633(4) Uani 1 1 d . . .
H1 H 0.138(3) 0.428(3) 0.1085(18) 0.093(8) Uiso 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 C6 1.388(2) . ?
C1 C2 1.401(2) . ?
C1 N1 1.4067(19) . ?
C2 C3 1.403(2) . ?
C2 C7 1.510(2) . ?
C3 C4 1.390(2) . ?
C3 C8 1.503(2) . ?
C4 C5 1.378(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 N2 1.3307(18) . ?
C9 C13 1.4404(19) . ?
C9 C10 1.465(2) . ?
C10 O1 1.2334(18) . ?
C10 N3 1.3765(19) . ?
C11 O2 1.2157(19) . ?
C11 N3 1.3939(19) . ?
C11 C12 1.465(2) . ?
C12 C13 1.364(2) . ?
C12 C15 1.430(2) . ?
C13 C16 1.492(2) . ?
C14 N3 1.463(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N4 1.140(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1 N2 1.3014(17) . ?
N1 H1 0.92(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
C6 C1 C2 121.81(14) . . ?
C6 C1 N1 120.74(13) . . ?
C2 C1 N1 117.45(13) . . ?
C1 C2 C3 118.03(14) . . ?
C1 C2 C7 120.65(14) . . ?
C3 C2 C7 121.31(14) . . ?
C4 C3 C2 119.62(14) . . ?
C4 C3 C8 119.42(15) . . ?
C2 C3 C8 120.95(15) . . ?
C5 C4 C3 120.99(15) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C6 C5 C4 120.57(15) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 118.95(14) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C13 116.50(13) . . ?
N2 C9 C10 122.99(13) . . ?
C13 C9 C10 120.51(13) . . ?
O1 C10 N3 119.96(14) . . ?
O1 C10 C9 122.39(14) . . ?
N3 C10 C9 117.63(13) . . ?
O2 C11 N3 120.64(15) . . ?
O2 C11 C12 122.81(14) . . ?
N3 C11 C12 116.55(13) . . ?
C13 C12 C15 122.11(14) . . ?
C13 C12 C11 123.20(13) . . ?
C15 C12 C11 114.68(13) . . ?
C12 C13 C9 117.90(14) . . ?
C12 C13 C16 121.79(13) . . ?
C9 C13 C16 120.30(13) . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N4 C15 C12 178.57(18) . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 N1 C1 121.61(13) . . ?
N2 N1 H1 113.1(15) . . ?
C1 N1 H1 125.3(15) . . ?
N1 N2 C9 119.01(13) . . ?
C10 N3 C11 123.92(13) . . ?
C10 N3 C14 118.67(13) . . ?
C11 N3 C14 117.30(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -2.0(2) . . . . ?
N1 C1 C2 C3 177.65(12) . . . . ?
C6 C1 C2 C7 178.39(13) . . . . ?
N1 C1 C2 C7 -1.9(2) . . . . ?
C1 C2 C3 C4 1.2(2) . . . . ?
C7 C2 C3 C4 -179.23(13) . . . . ?
C1 C2 C3 C8 -177.91(13) . . . . ?
C7 C2 C3 C8 1.7(2) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C8 C3 C4 C5 179.56(15) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C2 C1 C6 C5 1.2(2) . . . . ?
N1 C1 C6 C5 -178.48(14) . . . . ?
N2 C9 C10 O1 -3.7(2) . . . . ?
C13 C9 C10 O1 176.11(13) . . . . ?
N2 C9 C10 N3 175.29(13) . . . . ?
C13 C9 C10 N3 -4.9(2) . . . . ?
O2 C11 C12 C13 -179.21(15) . . . . ?
N3 C11 C12 C13 0.9(2) . . . . ?
O2 C11 C12 C15 -0.2(2) . . . . ?
N3 C11 C12 C15 179.90(13) . . . . ?
C15 C12 C13 C9 -178.42(13) . . . . ?
C11 C12 C13 C9 0.5(2) . . . . ?
C15 C12 C13 C16 1.5(2) . . . . ?
C11 C12 C13 C16 -179.56(14) . . . . ?
N2 C9 C13 C12 -178.68(13) . . . . ?
C10 C9 C13 C12 1.5(2) . . . . ?
N2 C9 C13 C16 1.4(2) . . . . ?
C10 C9 C13 C16 -178.46(13) . . . . ?
C6 C1 N1 N2 4.2(2) . . . . ?
C2 C1 N1 N2 -175.52(12) . . . . ?
C1 N1 N2 C9 179.52(12) . . . . ?
C13 C9 N2 N1 -179.99(12) . . . . ?
C10 C9 N2 N1 -0.1(2) . . . . ?
O1 C10 N3 C11 -174.35(14) . . . . ?
C9 C10 N3 C11 6.6(2) . . . . ?
O1 C10 N3 C14 1.8(2) . . . . ?
C9 C10 N3 C14 -177.22(14) . . . . ?
O2 C11 N3 C10 175.42(15) . . . . ?
C12 C11 N3 C10 -4.7(2) . . . . ?
O2 C11 N3 C14 -0.8(2) . . . . ?
C12 C11 N3 C14 179.10(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_ethyl
_database_code_depnum_ccdc_archive 'CCDC 1034366'
_audit_update_record             
;
2014-11-16 deposited with the CCDC.
2015-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H18 N4 O2'
_chemical_formula_sum            'C17 H18 N4 O2'
_chemical_formula_weight         310.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0716(9)
_cell_length_b                   9.9236(12)
_cell_length_c                   11.1322(13)
_cell_angle_alpha                65.8720(10)
_cell_angle_beta                 80.149(2)
_cell_angle_gamma                74.023(2)
_cell_volume                     780.60(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    2294
_cell_measurement_theta_min      2.310
_cell_measurement_theta_max      27.359

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9905
_exptl_absorpt_correction_T_max  0.9941
_exptl_absorpt_process_details   'SADABS, Bruker(2000)'

_exptl_special_details           
; 
The structure was solved by direct methods (Bruker, 2000) and
successive difference Fourier syntheses.
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5679
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_sigmaI/netI    0.0722
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2699
_reflns_number_gt                2241
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (BRUKER 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_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)+(0.0963P)²+0.0544P] 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         2699
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1754
_refine_ls_wR_factor_gt          0.1665
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.11605(19) 1.12408(17) 0.83740(15) 0.0329(4) Uani 1 1 d . . .
C2 C 0.10281(19) 1.11196(17) 0.71832(15) 0.0342(4) Uani 1 1 d . . .
C3 C -0.0011(2) 1.23355(18) 0.62492(15) 0.0381(4) Uani 1 1 d . . .
C4 C -0.0893(2) 1.35987(18) 0.65307(16) 0.0418(4) Uani 1 1 d . . .
H4 H -0.1583 1.4406 0.5908 0.050 Uiso 1 1 calc R . .
C5 C -0.0762(2) 1.36749(18) 0.77229(16) 0.0435(4) Uani 1 1 d . . .
H5 H -0.1373 1.4524 0.7898 0.052 Uiso 1 1 calc R . .
C6 C 0.0268(2) 1.25011(18) 0.86510(15) 0.0387(4) Uani 1 1 d . . .
H6 H 0.0364 1.2552 0.9451 0.046 Uiso 1 1 calc R . .
C7 C 0.1976(2) 0.97132(19) 0.69305(17) 0.0465(5) Uani 1 1 d . . .
H7A H 0.3142 0.9427 0.7179 0.070 Uiso 1 1 calc R . .
H7B H 0.1983 0.9913 0.6010 0.070 Uiso 1 1 calc R . .
H7C H 0.1406 0.8903 0.7441 0.070 Uiso 1 1 calc R . .
C8 C -0.0179(3) 1.2312(2) 0.49308(16) 0.0541(5) Uani 1 1 d . . .
H8A H -0.0931 1.3240 0.4421 0.081 Uiso 1 1 calc R . .
H8B H -0.0651 1.1470 0.5062 0.081 Uiso 1 1 calc R . .
H8C H 0.0939 1.2211 0.4470 0.081 Uiso 1 1 calc R . .
C9 C 0.35857(19) 0.88816(17) 1.12023(14) 0.0332(4) Uani 1 1 d . . .
C10 C 0.4375(2) 0.74883(18) 1.09669(15) 0.0352(4) Uani 1 1 d . . .
C11 C 0.5678(2) 0.63592(18) 1.30879(15) 0.0377(4) Uani 1 1 d . . .
C12 C 0.4887(2) 0.77843(18) 1.32762(14) 0.0352(4) Uani 1 1 d . . .
C13 C 0.38772(19) 0.89949(17) 1.23936(14) 0.0339(4) Uani 1 1 d . . .
C14 C 0.6033(2) 0.48554(18) 1.17180(16) 0.0434(4) Uani 1 1 d . . .
H14A H 0.5216 0.4714 1.1258 0.052 Uiso 1 1 calc R . .
H14B H 0.6163 0.4019 1.2569 0.052 Uiso 1 1 calc R . .
C15 C 0.7746(3) 0.4823(2) 1.0939(2) 0.0634(6) Uani 1 1 d . . .
H15A H 0.7648 0.5696 1.0126 0.095 Uiso 1 1 calc R . .
H15B H 0.8089 0.3919 1.0751 0.095 Uiso 1 1 calc R . .
H15C H 0.8595 0.4832 1.1441 0.095 Uiso 1 1 calc R . .
C16 C 0.5246(2) 0.77948(19) 1.44921(15) 0.0416(4) Uani 1 1 d . . .
C17 C 0.3077(2) 1.04324(19) 1.26175(16) 0.0442(4) Uani 1 1 d . . .
H17A H 0.3420 1.0342 1.3437 0.066 Uiso 1 1 calc R . .
H17B H 0.1842 1.0613 1.2651 0.066 Uiso 1 1 calc R . .
H17C H 0.3457 1.1263 1.1908 0.066 Uiso 1 1 calc R . .
N1 N 0.22527(17) 1.00207(15) 0.92833(12) 0.0357(4) Uani 1 1 d . . .
N2 N 0.25670(16) 1.00771(14) 1.03726(12) 0.0346(4) Uani 1 1 d . . .
N3 N 0.53322(17) 0.62966(14) 1.19227(12) 0.0368(4) Uani 1 1 d . . .
N4 N 0.5545(2) 0.78227(19) 1.54457(14) 0.0580(5) Uani 1 1 d . . .
O1 O 0.65771(17) 0.52893(14) 1.38772(12) 0.0560(4) Uani 1 1 d . . .
O2 O 0.42073(16) 0.73605(13) 0.99353(11) 0.0462(4) Uani 1 1 d . . .
H1 H 0.285(3) 0.911(2) 0.9154(19) 0.057(6) Uiso 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 C6 1.386(2) . ?
C1 C2 1.403(2) . ?
C1 N1 1.408(2) . ?
C2 C3 1.399(2) . ?
C2 C7 1.507(2) . ?
C3 C4 1.389(2) . ?
C3 C8 1.507(2) . ?
C4 C5 1.383(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 N2 1.328(2) . ?
C9 C13 1.439(2) . ?
C9 C10 1.463(2) . ?
C10 O2 1.2391(19) . ?
C10 N3 1.370(2) . ?
C11 O1 1.2074(19) . ?
C11 N3 1.401(2) . ?
C11 C12 1.467(2) . ?
C12 C13 1.357(2) . ?
C12 C16 1.436(2) . ?
C13 C17 1.497(2) . ?
C14 N3 1.4814(19) . ?
C14 C15 1.501(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N4 1.141(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N1 N2 1.3063(18) . ?
N1 H1 0.95(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
C6 C1 C2 121.99(14) . . ?
C6 C1 N1 121.05(14) . . ?
C2 C1 N1 116.96(14) . . ?
C3 C2 C1 118.00(14) . . ?
C3 C2 C7 121.40(14) . . ?
C1 C2 C7 120.60(14) . . ?
C4 C3 C2 119.66(15) . . ?
C4 C3 C8 119.13(14) . . ?
C2 C3 C8 121.21(15) . . ?
C5 C4 C3 121.04(15) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C6 C5 C4 120.38(15) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 118.91(15) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C13 116.63(14) . . ?
N2 C9 C10 123.43(14) . . ?
C13 C9 C10 119.93(14) . . ?
O2 C10 N3 119.51(14) . . ?
O2 C10 C9 122.07(14) . . ?
N3 C10 C9 118.42(13) . . ?
O1 C11 N3 120.93(15) . . ?
O1 C11 C12 123.01(15) . . ?
N3 C11 C12 116.06(13) . . ?
C13 C12 C16 122.12(15) . . ?
C13 C12 C11 123.47(14) . . ?
C16 C12 C11 114.41(14) . . ?
C12 C13 C9 118.28(14) . . ?
C12 C13 C17 122.25(14) . . ?
C9 C13 C17 119.46(14) . . ?
N3 C14 C15 112.45(14) . . ?
N3 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
N3 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
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 . . ?
N4 C16 C12 178.83(18) . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 N1 C1 121.53(14) . . ?
N2 N1 H1 114.5(12) . . ?
C1 N1 H1 124.0(12) . . ?
N1 N2 C9 118.80(13) . . ?
C10 N3 C11 123.76(13) . . ?
C10 N3 C14 118.18(13) . . ?
C11 N3 C14 118.06(13) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.071
####################################################################### 
# 
# 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_Cocrystal
_database_code_depnum_ccdc_archive 'CCDC 1034367'
_audit_update_record             
;
2014-11-16 deposited with the CCDC.
2015-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H18 N4 O2, C16 H16 N4 O2'
_chemical_formula_sum            'C33 H34 N8 O4'
_chemical_formula_weight         606.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.811(2)
_cell_length_b                   12.550(4)
_cell_length_c                   16.146(5)
_cell_angle_alpha                94.579(5)
_cell_angle_beta                 91.539(4)
_cell_angle_gamma                98.774(5)
_cell_volume                     1558.0(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    2052
_cell_measurement_theta_min      2.162
_cell_measurement_theta_max      25.678

_exptl_crystal_description       rod
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9895
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_process_details   'SADABS, Bruker(2000)'

_exptl_special_details           
; 
The structure was solved by direct methods (Bruker, 2000) and
successive difference Fourier syntheses.
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8747
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.27
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5458
_reflns_number_gt                3513
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (BRUKER 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_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)+(0.0929P)²+1.4880P] 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         5454
_refine_ls_number_parameters     421
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0645
_refine_ls_wR_factor_ref         0.1986
_refine_ls_wR_factor_gt          0.1692
_refine_ls_goodness_of_fit_ref   0.903
_refine_ls_restrained_S_all      0.904
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1602(3) 1.1114(2) 0.07075(17) 0.0445(6) Uani 1 1 d . . .
C2 C 0.1259(3) 1.1360(2) 0.15448(17) 0.0457(6) Uani 1 1 d . . .
C3 C 0.0647(4) 1.2336(2) 0.17594(19) 0.0517(7) Uani 1 1 d . . .
C4 C 0.0408(4) 1.3011(2) 0.1141(2) 0.0622(8) Uani 1 1 d . . .
H4 H 0.0009 1.3660 0.1281 0.075 Uiso 1 1 calc R . .
C5 C 0.0748(4) 1.2742(2) 0.0322(2) 0.0636(9) Uani 1 1 d . . .
H5 H 0.0563 1.3207 -0.0080 0.076 Uiso 1 1 calc R . .
C6 C 0.1358(4) 1.1794(2) 0.00949(19) 0.0547(7) Uani 1 1 d . . .
H6 H 0.1601 1.1614 -0.0455 0.066 Uiso 1 1 calc R . .
C7 C 0.1526(4) 1.0590(2) 0.21885(19) 0.0591(8) Uani 1 1 d . . .
H7A H 0.1209 1.0880 0.2721 0.089 Uiso 1 1 calc R . .
H7B H 0.2723 1.0498 0.2216 0.089 Uiso 1 1 calc R . .
H7C H 0.0817 0.9904 0.2039 0.089 Uiso 1 1 calc R . .
C8 C 0.0265(5) 1.2672(3) 0.2644(2) 0.0699(9) Uani 1 1 d . . .
H8A H -0.0556 1.2117 0.2852 0.105 Uiso 1 1 calc R . .
H8B H -0.0209 1.3335 0.2662 0.105 Uiso 1 1 calc R . .
H8C H 0.1317 1.2778 0.2982 0.105 Uiso 1 1 calc R . .
C9 C 0.3272(3) 0.8968(2) -0.04412(17) 0.0449(6) Uani 1 1 d . . .
C10 C 0.3518(4) 0.8200(2) 0.01682(18) 0.0505(7) Uani 1 1 d . . .
C11 C 0.4418(4) 0.6994(3) -0.09447(19) 0.0581(8) Uani 1 1 d . . .
C12 C 0.4219(4) 0.7794(2) -0.15218(17) 0.0502(7) Uani 1 1 d . . .
C13 C 0.3683(3) 0.8752(2) -0.12961(17) 0.0472(7) Uani 1 1 d . . .
C14 C 0.4387(6) 0.6485(3) 0.0489(2) 0.0793(10) Uani 1 1 d U . .
H14A H 0.5297 0.6086 0.0304 0.095 Uiso 1 1 calc R . .
H14B H 0.4759 0.6870 0.1024 0.095 Uiso 1 1 calc R . .
C15 C 0.2805(7) 0.5733(4) 0.0578(3) 0.1247(18) Uani 1 1 d U . .
H15A H 0.1945 0.6118 0.0821 0.187 Uiso 1 1 calc R . .
H15B H 0.3042 0.5188 0.0931 0.187 Uiso 1 1 calc R . .
H15C H 0.2383 0.5397 0.0042 0.187 Uiso 1 1 calc R . .
C16 C 0.4617(4) 0.7501(3) -0.2365(2) 0.0597(8) Uani 1 1 d . . .
C17 C 0.3481(4) 0.9571(3) -0.18980(18) 0.0591(8) Uani 1 1 d . . .
H17A H 0.3719 0.9291 -0.2446 0.089 Uiso 1 1 calc R . .
H17B H 0.4279 1.0222 -0.1741 0.089 Uiso 1 1 calc R . .
H17C H 0.2317 0.9729 -0.1893 0.089 Uiso 1 1 calc R . .
C18 C 0.3014(4) 0.5705(2) 0.43246(18) 0.0550(7) Uani 1 1 d . . .
C19 C 0.2863(4) 0.6803(2) 0.43896(19) 0.0578(8) Uani 1 1 d . . .
C20 C 0.3315(5) 0.7388(3) 0.3701(2) 0.0703(9) Uani 1 1 d . . .
C21 C 0.3888(6) 0.6864(4) 0.2997(2) 0.0854(11) Uani 1 1 d . . .
H21 H 0.4191 0.7255 0.2544 0.102 Uiso 1 1 calc R . .
C22 C 0.4022(6) 0.5777(3) 0.2951(2) 0.0843(11) Uani 1 1 d . . .
H22 H 0.4400 0.5444 0.2469 0.101 Uiso 1 1 calc R . .
C23 C 0.3595(5) 0.5187(3) 0.3617(2) 0.0689(9) Uani 1 1 d . . .
H23 H 0.3692 0.4456 0.3596 0.083 Uiso 1 1 calc R . .
C24 C 0.2247(5) 0.7322(3) 0.5166(2) 0.0751(10) Uani 1 1 d . . .
H24A H 0.1206 0.6891 0.5328 0.113 Uiso 1 1 calc R . .
H24B H 0.2014 0.8032 0.5069 0.113 Uiso 1 1 calc R . .
H24C H 0.3125 0.7378 0.5602 0.113 Uiso 1 1 calc R . .
C25 C 0.3226(6) 0.8588(3) 0.3719(3) 0.1024(14) Uani 1 1 d . . .
H25A H 0.3482 0.8834 0.3181 0.154 Uiso 1 1 calc R . .
H25B H 0.4056 0.8976 0.4127 0.154 Uiso 1 1 calc R . .
H25C H 0.2082 0.8713 0.3860 0.154 Uiso 1 1 calc R . .
C26 C 0.2159(4) 0.3546(2) 0.56499(19) 0.0550(7) Uani 1 1 d . . .
C27 C 0.1671(5) 0.4058(3) 0.6431(2) 0.0665(9) Uani 1 1 d . . .
C28 C 0.1451(5) 0.2324(3) 0.7041(2) 0.0742(10) Uani 1 1 d . . .
C29 C 0.1822(4) 0.1830(2) 0.6231(2) 0.0603(8) Uani 1 1 d . . .
C30 C 0.2191(4) 0.2403(2) 0.55589(19) 0.0563(8) Uani 1 1 d . . .
C31 C 0.0997(10) 0.3994(4) 0.7949(3) 0.164(3) Uani 1 1 d U . .
H31A H 0.2063 0.4391 0.8193 0.246 Uiso 1 1 calc R . .
H31B H 0.0533 0.3457 0.8309 0.246 Uiso 1 1 calc R . .
H31C H 0.0180 0.4481 0.7876 0.246 Uiso 1 1 calc R . .
C32 C 0.1776(5) 0.0690(3) 0.6183(2) 0.0737(10) Uani 1 1 d . . .
C33 C 0.2594(5) 0.1867(3) 0.4745(2) 0.0737(10) Uani 1 1 d . . .
H33A H 0.3063 0.1221 0.4836 0.111 Uiso 1 1 calc R . .
H33B H 0.3427 0.2351 0.4473 0.111 Uiso 1 1 calc R . .
H33C H 0.1553 0.1685 0.4401 0.111 Uiso 1 1 calc R . .
H1 H 0.234(4) 0.965(3) 0.092(2) 0.079(11) Uiso 1 1 d . . .
H5A H 0.222(4) 0.539(3) 0.552(2) 0.070(10) Uiso 1 1 d . . .
N1 N 0.2248(3) 1.01372(18) 0.05058(15) 0.0474(6) Uani 1 1 d . . .
N2 N 0.2688(3) 0.98921(18) -0.02519(14) 0.0464(6) Uani 1 1 d . . .
N3 N 0.4110(3) 0.7262(2) -0.01127(15) 0.0569(7) Uani 1 1 d . . .
N4 N 0.4948(4) 0.7269(3) -0.30360(19) 0.0799(9) Uani 1 1 d . . .
N5 N 0.2565(3) 0.5119(2) 0.50187(17) 0.0588(7) Uani 1 1 d . . .
N6 N 0.2564(3) 0.4082(2) 0.49856(16) 0.0571(6) Uani 1 1 d . . .
N7 N 0.1347(5) 0.3425(2) 0.70850(19) 0.0844(10) Uani 1 1 d U . .
N8 N 0.1712(6) -0.0225(3) 0.6129(2) 0.1048(13) Uani 1 1 d . . .
O1 O 0.3211(3) 0.83649(17) 0.09108(12) 0.0636(6) Uani 1 1 d . . .
O2 O 0.4825(4) 0.61104(19) -0.11593(15) 0.0832(8) Uani 1 1 d . . .
O3 O 0.1546(4) 0.50291(19) 0.65228(16) 0.0859(8) Uani 1 1 d . . .
O4 O 0.1247(5) 0.1821(2) 0.76561(17) 0.1037(10) 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 C6 1.384(4) . ?
C1 C2 1.404(4) . ?
C1 N1 1.414(3) . ?
C2 C3 1.403(4) . ?
C2 C7 1.505(4) . ?
C3 C4 1.387(4) . ?
C3 C8 1.508(4) . ?
C4 C5 1.380(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 N2 1.326(3) . ?
C9 C13 1.440(4) . ?
C9 C10 1.461(4) . ?
C10 O1 1.237(3) . ?
C10 N3 1.377(3) . ?
C11 O2 1.226(3) . ?
C11 N3 1.395(4) . ?
C11 C12 1.445(4) . ?
C12 C13 1.358(4) . ?
C12 C16 1.437(4) . ?
C13 C17 1.493(4) . ?
C14 C15 1.454(6) . ?
C14 N3 1.465(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N4 1.145(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C23 1.390(4) . ?
C18 C19 1.396(4) . ?
C18 N5 1.413(4) . ?
C19 C20 1.404(4) . ?
C19 C24 1.492(5) . ?
C20 C21 1.386(5) . ?
C20 C25 1.516(5) . ?
C21 C22 1.380(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.374(5) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 N6 1.331(4) . ?
C26 C30 1.434(4) . ?
C26 C27 1.457(4) . ?
C27 O3 1.235(4) . ?
C27 N7 1.377(4) . ?
C28 O4 1.220(4) . ?
C28 N7 1.393(4) . ?
C28 C29 1.458(5) . ?
C29 C30 1.362(4) . ?
C29 C32 1.422(5) . ?
C30 C33 1.491(4) . ?
C31 N7 1.566(5) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 N8 1.137(4) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
N1 N2 1.306(3) . ?
N1 H1 0.96(3) . ?
N5 N6 1.298(3) . ?
N5 H5A 0.92(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
C6 C1 C2 122.6(2) . . ?
C6 C1 N1 120.2(2) . . ?
C2 C1 N1 117.2(2) . . ?
C3 C2 C1 118.0(3) . . ?
C3 C2 C7 121.2(3) . . ?
C1 C2 C7 120.8(2) . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 C8 119.4(3) . . ?
C2 C3 C8 121.7(3) . . ?
C5 C4 C3 121.6(3) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 118.1(3) . . ?
C5 C6 H6 120.9 . . ?
C1 C6 H6 120.9 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C13 116.3(2) . . ?
N2 C9 C10 123.3(2) . . ?
C13 C9 C10 120.5(2) . . ?
O1 C10 N3 120.1(3) . . ?
O1 C10 C9 122.4(2) . . ?
N3 C10 C9 117.4(2) . . ?
O2 C11 N3 120.1(3) . . ?
O2 C11 C12 122.9(3) . . ?
N3 C11 C12 117.0(2) . . ?
C13 C12 C16 121.7(3) . . ?
C13 C12 C11 123.2(3) . . ?
C16 C12 C11 115.0(3) . . ?
C12 C13 C9 118.0(3) . . ?
C12 C13 C17 122.8(3) . . ?
C9 C13 C17 119.2(2) . . ?
C15 C14 N3 110.8(3) . . ?
C15 C14 H14A 109.5 . . ?
N3 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
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 . . ?
N4 C16 C12 179.5(4) . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 122.8(3) . . ?
C23 C18 N5 119.9(3) . . ?
C19 C18 N5 117.4(3) . . ?
C18 C19 C20 117.4(3) . . ?
C18 C19 C24 120.6(3) . . ?
C20 C19 C24 122.0(3) . . ?
C21 C20 C19 119.4(3) . . ?
C21 C20 C25 119.3(4) . . ?
C19 C20 C25 121.3(4) . . ?
C22 C21 C20 121.8(4) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C23 C22 C21 119.9(4) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C18 118.6(3) . . ?
C22 C23 H23 120.7 . . ?
C18 C23 H23 120.7 . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C20 C25 H25A 109.5 . . ?
C20 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C20 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N6 C26 C30 116.3(3) . . ?
N6 C26 C27 123.4(3) . . ?
C30 C26 C27 120.3(3) . . ?
O3 C27 N7 119.7(3) . . ?
O3 C27 C26 122.3(3) . . ?
N7 C27 C26 118.0(3) . . ?
O4 C28 N7 120.7(3) . . ?
O4 C28 C29 123.1(3) . . ?
N7 C28 C29 116.2(3) . . ?
C30 C29 C32 121.4(3) . . ?
C30 C29 C28 123.4(3) . . ?
C32 C29 C28 115.2(3) . . ?
C29 C30 C26 118.0(3) . . ?
C29 C30 C33 121.6(3) . . ?
C26 C30 C33 120.3(3) . . ?
N7 C31 H31A 109.5 . . ?
N7 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N7 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N8 C32 C29 178.3(4) . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N2 N1 C1 120.2(2) . . ?
N2 N1 H1 120(2) . . ?
C1 N1 H1 120(2) . . ?
N1 N2 C9 120.1(2) . . ?
C10 N3 C11 123.7(2) . . ?
C10 N3 C14 118.5(2) . . ?
C11 N3 C14 117.8(2) . . ?
N6 N5 C18 120.9(3) . . ?
N6 N5 H5A 112(2) . . ?
C18 N5 H5A 127(2) . . ?
N5 N6 C26 120.0(3) . . ?
C27 N7 C28 123.8(3) . . ?
C27 N7 C31 118.1(3) . . ?
C28 N7 C31 117.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.045

#===END
