# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2016

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1479516'
_audit_update_record             
;
2016-05-12 deposited with the CCDC.
2016-12-08 downloaded from the CCDC.
;

_audit_creation_date             2015-07-13T13:24:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H18 N4 O2'
_chemical_formula_sum            'C18 H18 N4 O2'
_chemical_formula_weight         322.36
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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                   5.8457(6)
_cell_length_b                   13.5935(14)
_cell_length_c                   9.8497(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.476(9)
_cell_angle_gamma                90
_cell_volume                     774.14(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    3395
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      27.88
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none

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

_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_detector                 'image plate ( 34 cm diameter )'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'sealed X-ray tube, 12 x 0.4 mm fine focus'
_diffrn_source_voltage           50
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'planar graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    '0.5 mm, multiple pinhole'
_diffrn_ambient_temperature      180
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 169 frames, detector distance = 115 mm
;
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_number            4612
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.572
_diffrn_reflns_theta_max         27.332
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_reflns_number_total             1717
_reflns_number_gt                1194
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   difmap

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0662P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.084(15)
_refine_ls_number_reflns         1717
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1034
_refine_ls_wR_factor_gt          0.0964
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_restrained_S_all      0.962
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.03

#----------------------------------------------------------------------------#
#                   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_disorder_assembly
_atom_site_disorder_group
C1 C 0.3540(3) 0.66544(13) 0.22865(16) 0.0528(4) Uani 1 d . .
C9 C 0.0690(2) 0.73248(10) 0.36360(13) 0.0445(3) Uani 1 d . .
C8 C 0.0911(2) 0.82850(11) 0.31660(15) 0.0519(4) Uani 1 d . .
C7 C -0.0429(3) 0.90276(12) 0.35847(17) 0.0570(4) Uani 1 d . .
C6 C -0.2029(3) 0.88390(12) 0.44652(17) 0.0572(4) Uani 1 d . .
C5 C -0.2304(2) 0.78949(11) 0.49114(15) 0.0519(4) Uani 1 d . .
C4 C -0.0961(2) 0.71305(11) 0.45184(14) 0.0445(3) Uani 1 d . .
C3 C 0.0181(2) 0.55075(10) 0.47949(12) 0.0421(3) Uani 1 d . .
C2 C 0.2414(2) 0.57735(11) 0.42835(14) 0.0438(3) Uani 1 d . .
N1 N 0.19427(19) 0.65334(9) 0.32773(12) 0.0476(3) Uani 1 d . .
N2 N -0.13542(17) 0.61693(8) 0.49363(11) 0.0434(3) Uani 1 d . .
O1 O 0.39651(16) 0.60633(8) 0.54675(10) 0.0497(3) Uani 1 d . .
H1A H 0.485(3) 0.7068(13) 0.2667(18) 0.060(4) Uiso 1 d . .
H1B H 0.272(3) 0.6928(13) 0.1425(19) 0.060(4) Uiso 1 d . .
H1C H 0.413(3) 0.6004(14) 0.2126(18) 0.059(5) Uiso 1 d . .
H8 H 0.206(3) 0.8438(13) 0.2523(17) 0.060(4) Uiso 1 d . .
H7 H -0.024(3) 0.9709(14) 0.3284(18) 0.064(5) Uiso 1 d . .
H6 H -0.291(3) 0.9368(15) 0.4733(19) 0.070(5) Uiso 1 d . .
H5 H -0.347(3) 0.7700(13) 0.5510(18) 0.058(4) Uiso 1 d . .
H2 H 0.302(2) 0.5222(11) 0.3845(14) 0.039(3) Uiso 1 d . .
H9 H 0.541(4) 0.6015(15) 0.524(2) 0.083(6) 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
C1 N1 1.4560(16) . ?
C1 H1A 0.979(19) . ?
C1 H1B 0.983(19) . ?
C1 H1C 0.971(19) . ?
C9 N1 1.3764(18) . ?
C9 C8 1.397(2) . ?
C9 C4 1.4157(17) . ?
C8 C7 1.378(2) . ?
C8 H8 1.008(17) . ?
C7 C6 1.390(2) . ?
C7 H7 0.984(19) . ?
C6 C5 1.374(2) . ?
C6 H6 0.95(2) . ?
C5 C4 1.391(2) . ?
C5 H5 1.001(17) . ?
C4 N2 1.3991(18) . ?
C3 N2 1.2926(17) . ?
C3 C3 1.462(3) 3_566 ?
C3 C2 1.5111(16) . ?
C2 O1 1.4232(17) . ?
C2 N1 1.4299(19) . ?
C2 H2 0.958(14) . ?
O1 H9 0.91(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
N1 C1 H1A 110.6(10) . . ?
N1 C1 H1B 110.1(10) . . ?
H1A C1 H1B 111.5(15) . . ?
N1 C1 H1C 106.6(10) . . ?
H1A C1 H1C 107.9(14) . . ?
H1B C1 H1C 110.1(15) . . ?
N1 C9 C8 124.51(12) . . ?
N1 C9 C4 116.64(12) . . ?
C8 C9 C4 118.84(13) . . ?
C7 C8 C9 120.06(13) . . ?
C7 C8 H8 119.8(10) . . ?
C9 C8 H8 120.2(10) . . ?
C8 C7 C6 121.08(15) . . ?
C8 C7 H7 120.4(10) . . ?
C6 C7 H7 118.5(9) . . ?
C5 C6 C7 119.56(14) . . ?
C5 C6 H6 121.8(11) . . ?
C7 C6 H6 118.7(11) . . ?
C6 C5 C4 120.75(13) . . ?
C6 C5 H5 123.9(10) . . ?
C4 C5 H5 115.3(10) . . ?
C5 C4 N2 119.46(11) . . ?
C5 C4 C9 119.68(13) . . ?
N2 C4 C9 120.75(12) . . ?
N2 C3 C3 119.75(12) . 3_566 ?
N2 C3 C2 121.13(12) . . ?
C3 C3 C2 119.03(13) 3_566 . ?
O1 C2 N1 113.73(12) . . ?
O1 C2 C3 105.69(10) . . ?
N1 C2 C3 108.43(11) . . ?
O1 C2 H2 110.7(8) . . ?
N1 C2 H2 107.4(8) . . ?
C3 C2 H2 110.9(8) . . ?
C9 N1 C2 116.25(10) . . ?
C9 N1 C1 120.11(12) . . ?
C2 N1 C1 117.96(11) . . ?
C3 N2 C4 118.13(10) . . ?
C2 O1 H9 106.6(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C9 C8 C7 179.88(13) . . . . ?
C4 C9 C8 C7 1.4(2) . . . . ?
C9 C8 C7 C6 -0.6(2) . . . . ?
C8 C7 C6 C5 -0.9(2) . . . . ?
C7 C6 C5 C4 1.6(2) . . . . ?
C6 C5 C4 N2 -177.02(14) . . . . ?
C6 C5 C4 C9 -0.7(2) . . . . ?
N1 C9 C4 C5 -179.37(13) . . . . ?
C8 C9 C4 C5 -0.8(2) . . . . ?
N1 C9 C4 N2 -3.12(19) . . . . ?
C8 C9 C4 N2 175.49(13) . . . . ?
N2 C3 C2 O1 86.36(15) . . . . ?
C3 C3 C2 O1 -90.29(17) 3_566 . . . ?
N2 C3 C2 N1 -35.93(17) . . . . ?
C3 C3 C2 N1 147.43(15) 3_566 . . . ?
C8 C9 N1 C2 149.39(14) . . . . ?
C4 C9 N1 C2 -32.08(17) . . . . ?
C8 C9 N1 C1 -3.5(2) . . . . ?
C4 C9 N1 C1 175.00(13) . . . . ?
O1 C2 N1 C9 -68.11(14) . . . . ?
C3 C2 N1 C9 49.13(16) . . . . ?
O1 C2 N1 C1 85.41(15) . . . . ?
C3 C2 N1 C1 -157.35(12) . . . . ?
C3 C3 N2 C4 -179.30(14) 3_566 . . . ?
C2 C3 N2 C4 4.07(18) . . . . ?
C5 C4 N2 C3 -166.65(13) . . . . ?
C9 C4 N2 C3 17.10(19) . . . . ?


# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1479517'
_audit_update_record             
;
2016-05-12 deposited with the CCDC.
2016-12-08 downloaded from the CCDC.
;

_audit_creation_date             2015-07-13T13:37:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H22 N4 O2'
_chemical_formula_sum            'C20 H22 N4 O2'
_chemical_formula_weight         350.41
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a b'
_symmetry_space_group_name_Hall  '-P 2bc 2ac'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'x+1/2, -y, -z+1/2'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x-1/2, y, z-1/2'
'x-1/2, -y-1/2, z'

_cell_length_a                   10.2451(8)
_cell_length_b                   11.0740(7)
_cell_length_c                   15.3632(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1743.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    4729
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      27.95
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.222
_exptl_crystal_size_min          0.194
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none

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

_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_voltage           50
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_ambient_temperature      180
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 149 frames, detector distance = 115 mm
;
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_number            8828
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.016
_diffrn_reflns_theta_max         27.37
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.984
_reflns_number_total             1941
_reflns_number_gt                1339
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   difmap

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0824P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.066(6)
_refine_ls_number_reflns         1941
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1326
_refine_ls_wR_factor_gt          0.1214
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.05

#----------------------------------------------------------------------------#
#                   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_disorder_assembly
_atom_site_disorder_group
C1 C 0.5921(2) 0.30156(17) 0.34335(13) 0.0397(4) Uani 1 d . .
C9 C 0.43667(16) 0.14135(15) 0.30415(10) 0.0308(4) Uani 1 d . .
C8 C 0.41520(18) 0.18819(17) 0.22071(11) 0.0362(4) Uani 1 d . .
C7 C 0.3286(2) 0.13168(18) 0.16494(11) 0.0397(4) Uani 1 d . .
C6 C 0.26313(19) 0.02662(17) 0.18926(11) 0.0388(4) Uani 1 d . .
C5 C 0.28986(18) -0.02445(16) 0.26932(10) 0.0347(4) Uani 1 d . .
C4 C 0.37706(16) 0.03080(15) 0.32692(10) 0.0306(4) Uani 1 d . .
C3 C 0.47441(16) 0.03137(15) 0.46179(9) 0.0295(4) Uani 1 d . .
C2 C 0.49185(17) 0.16612(15) 0.45473(10) 0.0312(4) Uani 1 d . .
C10 C 0.3809(2) 0.34257(17) 0.50447(15) 0.0443(5) Uani 1 d . .
N1 N 0.51617(14) 0.19528(13) 0.36516(9) 0.0320(4) Uani 1 d . .
N2 N 0.41211(14) -0.02948(12) 0.40321(9) 0.0309(3) Uani 1 d . .
O1 O 0.37415(12) 0.21612(10) 0.48927(8) 0.0362(3) Uani 1 d . .
H1A H 0.533(2) 0.377(2) 0.3332(13) 0.052(6) Uiso 1 d . .
H1B H 0.649(2) 0.325(2) 0.3917(15) 0.051(6) Uiso 1 d . .
H1C H 0.646(2) 0.2839(18) 0.2915(15) 0.045(5) Uiso 1 d . .
H8 H 0.456(2) 0.2645(19) 0.2022(13) 0.040(5) Uiso 1 d . .
H7 H 0.310(2) 0.1695(19) 0.1059(14) 0.045(5) Uiso 1 d . .
H6 H 0.198(2) -0.0156(19) 0.1494(12) 0.040(5) Uiso 1 d . .
H5 H 0.242(2) -0.103(2) 0.2905(14) 0.047(6) Uiso 1 d . .
H2 H 0.571(2) 0.1964(15) 0.4895(11) 0.030(4) Uiso 1 d . .
H10A H 0.388(3) 0.393(2) 0.4491(16) 0.063(7) Uiso 1 d . .
H10B H 0.301(3) 0.368(2) 0.5382(18) 0.078(8) Uiso 1 d . .
H10C H 0.461(3) 0.366(2) 0.5382(16) 0.068(8) 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
C1 N1 1.450(2) . ?
C1 H1A 1.04(3) . ?
C1 H1B 0.98(2) . ?
C1 H1C 0.99(2) . ?
C9 N1 1.378(2) . ?
C9 C8 1.400(2) . ?
C9 C4 1.412(2) . ?
C8 C7 1.383(3) . ?
C8 H8 0.99(2) . ?
C7 C6 1.394(3) . ?
C7 H7 1.02(2) . ?
C6 C5 1.381(2) . ?
C6 H6 1.02(2) . ?
C5 C4 1.398(2) . ?
C5 H5 1.05(2) . ?
C4 N2 1.396(2) . ?
C3 N2 1.293(2) . ?
C3 C3 1.462(3) 5_656 ?
C3 C2 1.507(2) . ?
C2 O1 1.429(2) . ?
C2 N1 1.435(2) . ?
C2 H2 1.03(2) . ?
C10 O1 1.421(2) . ?
C10 H10A 1.02(3) . ?
C10 H10B 1.01(3) . ?
C10 H10C 1.00(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
N1 C1 H1A 111.8(14) . . ?
N1 C1 H1B 111.1(13) . . ?
H1A C1 H1B 104.1(18) . . ?
N1 C1 H1C 109.1(12) . . ?
H1A C1 H1C 111.5(17) . . ?
H1B C1 H1C 109(2) . . ?
N1 C9 C8 123.72(16) . . ?
N1 C9 C4 117.57(14) . . ?
C8 C9 C4 118.68(16) . . ?
C7 C8 C9 120.03(18) . . ?
C7 C8 H8 118.9(12) . . ?
C9 C8 H8 120.9(12) . . ?
C8 C7 C6 121.35(17) . . ?
C8 C7 H7 119.0(12) . . ?
C6 C7 H7 119.6(12) . . ?
C5 C6 C7 119.01(17) . . ?
C5 C6 H6 118.5(11) . . ?
C7 C6 H6 122.5(11) . . ?
C6 C5 C4 120.73(17) . . ?
C6 C5 H5 121.3(12) . . ?
C4 C5 H5 117.8(12) . . ?
N2 C4 C5 119.11(15) . . ?
N2 C4 C9 120.75(15) . . ?
C5 C4 C9 119.93(15) . . ?
N2 C3 C3 119.25(19) . 5_656 ?
N2 C3 C2 121.65(14) . . ?
C3 C3 C2 119.07(18) 5_656 . ?
O1 C2 N1 114.54(14) . . ?
O1 C2 C3 104.89(13) . . ?
N1 C2 C3 108.20(13) . . ?
O1 C2 H2 110.3(10) . . ?
N1 C2 H2 106.7(10) . . ?
C3 C2 H2 112.3(10) . . ?
O1 C10 H10A 114.0(13) . . ?
O1 C10 H10B 108.4(16) . . ?
H10A C10 H10B 110(2) . . ?
O1 C10 H10C 112.2(16) . . ?
H10A C10 H10C 103(2) . . ?
H10B C10 H10C 109(2) . . ?
C9 N1 C2 116.88(14) . . ?
C9 N1 C1 120.77(14) . . ?
C2 N1 C1 119.82(14) . . ?
C3 N2 C4 117.54(15) . . ?
C10 O1 C2 113.67(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C9 C8 C7 -176.69(16) . . . . ?
C4 C9 C8 C7 5.3(3) . . . . ?
C9 C8 C7 C6 -1.2(3) . . . . ?
C8 C7 C6 C5 -2.8(3) . . . . ?
C7 C6 C5 C4 2.7(3) . . . . ?
C6 C5 C4 N2 -173.39(15) . . . . ?
C6 C5 C4 C9 1.4(3) . . . . ?
N1 C9 C4 N2 -8.8(2) . . . . ?
C8 C9 C4 N2 169.32(15) . . . . ?
N1 C9 C4 C5 176.50(15) . . . . ?
C8 C9 C4 C5 -5.3(2) . . . . ?
N2 C3 C2 O1 83.65(18) . . . . ?
C3 C3 C2 O1 -94.3(2) 5_656 . . . ?
N2 C3 C2 N1 -39.0(2) . . . . ?
C3 C3 C2 N1 143.00(19) 5_656 . . . ?
C8 C9 N1 C2 156.98(16) . . . . ?
C4 C9 N1 C2 -25.0(2) . . . . ?
C8 C9 N1 C1 -5.0(3) . . . . ?
C4 C9 N1 C1 173.11(16) . . . . ?
O1 C2 N1 C9 -70.86(19) . . . . ?
C3 C2 N1 C9 45.72(19) . . . . ?
O1 C2 N1 C1 91.26(19) . . . . ?
C3 C2 N1 C1 -152.17(16) . . . . ?
C3 C3 N2 C4 -173.25(17) 5_656 . . . ?
C2 C3 N2 C4 8.8(2) . . . . ?
C5 C4 N2 C3 -168.46(16) . . . . ?
C9 C4 N2 C3 16.8(2) . . . . ?
N1 C2 O1 C10 -73.30(19) . . . . ?
C3 C2 O1 C10 168.23(15) . . . . ?


# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1479519'
_audit_update_record             
;
2016-05-12 deposited with the CCDC.
2016-12-08 downloaded from the CCDC.
;

_audit_creation_date             2015-07-13T14:06:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C26 H34 N4 O4'
_chemical_formula_sum            'C26 H34 N4 O4'
_chemical_formula_weight         466.57
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/a '
_symmetry_space_group_name_Hall  ' -P2yab'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'

_cell_length_a                   8.6751(8)
_cell_length_b                   11.2503(10)
_cell_length_c                   13.3424(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.681(7)
_cell_angle_gamma                90
_cell_volume                     1297.84(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    2399
_cell_measurement_theta_min      1.53
_cell_measurement_theta_max      21.46
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             500
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none

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

_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_detector                 'image plate ( 34 cm diameter )'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'sealed X-ray tube, 12 x 0.4 mm fine focus'
_diffrn_source_voltage           50
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'planar graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    '0.5 mm, multiple pinhole'
_diffrn_ambient_temperature      180
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 194 frames, detector distance = 115 mm
;
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_number            7771
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.371
_diffrn_reflns_theta_max         27.453
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.971
_reflns_number_total             2890
_reflns_number_gt                1622
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0937P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.193(18)
_refine_ls_number_reflns         2890
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.146
_refine_ls_wR_factor_gt          0.1279
_refine_ls_goodness_of_fit_ref   0.878
_refine_ls_restrained_S_all      0.878
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.036

#----------------------------------------------------------------------------#
#                   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_disorder_assembly
_atom_site_disorder_group
C1 C 0.4216(2) 0.63008(15) 1.02619(15) 0.0690(5) Uani 1 d . .
H1A H 0.4572 0.5909 1.0877 0.103 Uiso 1 calc . .
H1B H 0.5004 0.6263 0.9798 0.103 Uiso 1 calc . .
H1C H 0.3297 0.5914 0.9974 0.103 Uiso 1 calc . .
C9 C 0.31075(19) 0.78472(15) 1.12912(12) 0.0605(4) Uani 1 d . .
C8 C 0.2334(2) 0.70298(17) 1.18626(13) 0.0676(5) Uani 1 d . .
H8 H 0.231 0.623 1.1686 0.081 Uiso 1 calc . .
C7 C 0.1612(2) 0.7407(2) 1.26811(14) 0.0751(5) Uani 1 d . .
H7 H 0.1078 0.686 1.3044 0.09 Uiso 1 calc . .
C6 C 0.1660(2) 0.85876(19) 1.29814(14) 0.0754(5) Uani 1 d . .
H6 H 0.1163 0.8828 1.3539 0.091 Uiso 1 calc . .
C5 C 0.2450(2) 0.93989(18) 1.24463(13) 0.0688(5) Uani 1 d . .
H5 H 0.2505 1.0189 1.2652 0.083 Uiso 1 calc . .
C4 C 0.31673(19) 0.90483(15) 1.16006(12) 0.0600(4) Uani 1 d . .
C3 C 0.45228(18) 0.95789(14) 1.02557(11) 0.0561(4) Uani 1 d . .
C2 C 0.41397(19) 0.84215(14) 0.97412(12) 0.0578(4) Uani 1 d . .
H2 H 0.5008 0.8177 0.9362 0.069 Uiso 1 calc . .
C10 C 0.2673(2) 0.79322(17) 0.81959(12) 0.0684(5) Uani 1 d . .
H10A H 0.2306 0.7154 0.838 0.082 Uiso 1 calc . .
H10B H 0.3668 0.7837 0.7923 0.082 Uiso 1 calc . .
C11 C 0.1545(2) 0.84919(18) 0.74310(13) 0.0729(5) Uani 1 d . .
H11A H 0.0632 0.8754 0.7743 0.088 Uiso 1 calc . .
H11B H 0.2009 0.9175 0.7129 0.088 Uiso 1 calc . .
C12 C 0.0117(3) 0.8028(3) 0.58955(15) 0.1012(8) Uani 1 d . .
H12A H 0.0603 0.8649 0.5527 0.121 Uiso 1 calc . .
H12B H -0.0806 0.8353 0.6156 0.121 Uiso 1 calc . .
C13 C -0.0300(4) 0.7014(4) 0.52193(19) 0.1328(12) Uani 1 d . .
H13A H 0.0625 0.6649 0.5016 0.199 Uiso 1 calc . .
H13B H -0.0915 0.7294 0.4636 0.199 Uiso 1 calc . .
H13C H -0.088 0.6442 0.5567 0.199 Uiso 1 calc . .
N1 N 0.38725(17) 0.75354(12) 1.04690(10) 0.0610(4) Uani 1 d . .
N2 N 0.40235(16) 0.98832(12) 1.11059(10) 0.0593(4) Uani 1 d . .
O1 O 0.28217(13) 0.86801(10) 0.90501(8) 0.0615(3) Uani 1 d . .
O2 O 0.11481(17) 0.76225(14) 0.66964(9) 0.0846(5) Uani 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
C1 N1 1.452(2) . ?
C9 N1 1.373(2) . ?
C9 C8 1.400(2) . ?
C9 C4 1.413(2) . ?
C8 C7 1.370(3) . ?
C7 C6 1.386(3) . ?
C6 C5 1.376(3) . ?
C5 C4 1.389(2) . ?
C4 N2 1.396(2) . ?
C3 N2 1.293(2) . ?
C3 C3 1.463(3) 3_677 ?
C3 C2 1.497(2) . ?
C2 N1 1.424(2) . ?
C2 O1 1.439(2) . ?
C10 O1 1.4140(19) . ?
C10 C11 1.494(3) . ?
C11 O2 1.408(2) . ?
C12 O2 1.412(3) . ?
C12 C13 1.481(4) . ?

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
N1 C9 C8 123.47(16) . . ?
N1 C9 C4 117.98(15) . . ?
C8 C9 C4 118.48(16) . . ?
C7 C8 C9 120.05(18) . . ?
C8 C7 C6 121.50(19) . . ?
C5 C6 C7 119.33(18) . . ?
C6 C5 C4 120.55(19) . . ?
C5 C4 N2 118.92(16) . . ?
C5 C4 C9 120.05(16) . . ?
N2 C4 C9 120.90(15) . . ?
N2 C3 C3 118.72(18) . 3_677 ?
N2 C3 C2 123.71(15) . . ?
C3 C3 C2 117.54(17) 3_677 . ?
N1 C2 O1 114.42(13) . . ?
N1 C2 C3 109.80(13) . . ?
O1 C2 C3 104.66(13) . . ?
O1 C10 C11 108.14(15) . . ?
O2 C11 C10 106.99(16) . . ?
O2 C12 C13 108.7(2) . . ?
C9 N1 C2 118.83(14) . . ?
C9 N1 C1 121.09(14) . . ?
C2 N1 C1 119.52(13) . . ?
C3 N2 C4 117.76(14) . . ?
C10 O1 C2 114.31(13) . . ?
C11 O2 C12 113.99(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C9 C8 C7 179.20(16) . . . . ?
C4 C9 C8 C7 2.2(3) . . . . ?
C9 C8 C7 C6 -1.8(3) . . . . ?
C8 C7 C6 C5 0.0(3) . . . . ?
C7 C6 C5 C4 1.3(3) . . . . ?
C6 C5 C4 N2 -176.83(16) . . . . ?
C6 C5 C4 C9 -0.9(3) . . . . ?
N1 C9 C4 C5 -178.06(15) . . . . ?
C8 C9 C4 C5 -0.9(2) . . . . ?
N1 C9 C4 N2 -2.2(2) . . . . ?
C8 C9 C4 N2 174.99(15) . . . . ?
N2 C3 C2 N1 -28.8(2) . . . . ?
C3 C3 C2 N1 153.19(17) 3_677 . . . ?
N2 C3 C2 O1 94.46(17) . . . . ?
C3 C3 C2 O1 -83.5(2) 3_677 . . . ?
O1 C10 C11 O2 -166.81(14) . . . . ?
C8 C9 N1 C2 157.90(16) . . . . ?
C4 C9 N1 C2 -25.1(2) . . . . ?
C8 C9 N1 C1 -13.5(3) . . . . ?
C4 C9 N1 C1 163.56(15) . . . . ?
O1 C2 N1 C9 -79.18(18) . . . . ?
C3 C2 N1 C9 38.1(2) . . . . ?
O1 C2 N1 C1 92.33(18) . . . . ?
C3 C2 N1 C1 -150.34(15) . . . . ?
C3 C3 N2 C4 -177.47(17) 3_677 . . . ?
C2 C3 N2 C4 4.5(2) . . . . ?
C5 C4 N2 C3 -171.83(15) . . . . ?
C9 C4 N2 C3 12.3(2) . . . . ?
C11 C10 O1 C2 -165.02(15) . . . . ?
N1 C2 O1 C10 -86.79(17) . . . . ?
C3 C2 O1 C10 152.98(13) . . . . ?
C10 C11 O2 C12 -178.10(17) . . . . ?
C13 C12 O2 C11 -175.76(19) . . . . ?


# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1479518'
_audit_update_record             
;
2016-05-12 deposited with the CCDC.
2016-12-08 downloaded from the CCDC.
;

_audit_creation_date             2015-07-13T13:48:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H26 N4 O2'
_chemical_formula_sum            'C22 H26 N4 O2'
_chemical_formula_weight         378.47
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/a'
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'

_cell_length_a                   8.8290(11)
_cell_length_b                   11.3130(16)
_cell_length_c                   10.4030(13)
_cell_angle_alpha                90
_cell_angle_beta                 107.834(9)
_cell_angle_gamma                90
_cell_volume                     989.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    3628
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      27.97
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.378
_exptl_crystal_size_mid          0.353
_exptl_crystal_size_min          0.156
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.987

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

_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_detector                 'image plate ( 34 cm diameter )'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'sealed X-ray tube, 12 x 0.4 mm fine focus'
_diffrn_source_voltage           50
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'planar graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    '0.5 mm, multiple pinhole'
_diffrn_ambient_temperature      180(2)
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 190 frames, detector distance = 115 mm
;
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_number            4943
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.734
_diffrn_reflns_theta_max         27.402
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.98
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.98
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.98
_reflns_number_total             2205
_reflns_number_gt                1399
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   difmap

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0687P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.094(10)
_refine_ls_number_reflns         2205
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1075
_refine_ls_wR_factor_gt          0.0968
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_restrained_S_all      0.927
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.031

#----------------------------------------------------------------------------#
#                   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_disorder_assembly
_atom_site_disorder_group
C1 C 0.0793(2) 0.13445(12) 0.4605(2) 0.0633(4) Uani 1 d . .
C9 C 0.14510(14) 0.29242(12) 0.32287(15) 0.0521(3) Uani 1 d . .
C8 C 0.20661(16) 0.21441(15) 0.24648(17) 0.0617(4) Uani 1 d . .
C7 C 0.24686(18) 0.25563(17) 0.13669(18) 0.0715(5) Uani 1 d . .
C6 C 0.2249(2) 0.37243(18) 0.09755(19) 0.0731(5) Uani 1 d . .
C5 C 0.16094(18) 0.45052(15) 0.16907(17) 0.0628(4) Uani 1 d . .
C4 C 0.12286(14) 0.41216(12) 0.28261(14) 0.0520(3) Uani 1 d . .
C3 C 0.03811(13) 0.45955(11) 0.46427(14) 0.0465(3) Uani 1 d . .
C2 C 0.10123(15) 0.34495(11) 0.53218(15) 0.0489(3) Uani 1 d . .
C10 C 0.3075(2) 0.30802(16) 0.74179(17) 0.0653(4) Uani 1 d . .
C11 C 0.4522(2) 0.36535(19) 0.83390(19) 0.0709(5) Uani 1 d . .
N1 N 0.10014(13) 0.25810(10) 0.43250(12) 0.0525(3) Uani 1 d . .
N2 N 0.05322(12) 0.49212(9) 0.34977(12) 0.0491(3) Uani 1 d . .
O1 O 0.25732(10) 0.37296(8) 0.61961(9) 0.0529(3) Uani 1 d . .
H1A H 0.020(2) 0.0891(16) 0.368(2) 0.079(5) Uiso 1 d . .
H1B H 0.179(2) 0.0926(16) 0.504(2) 0.083(5) Uiso 1 d . .
H1C H 0.006(3) 0.1310(18) 0.526(2) 0.100(6) Uiso 1 d . .
H8 H 0.221(2) 0.1265(16) 0.2741(18) 0.074(5) Uiso 1 d . .
H7 H 0.294(2) 0.1975(16) 0.082(2) 0.088(6) Uiso 1 d . .
H6 H 0.248(2) 0.4011(16) 0.022(2) 0.086(6) Uiso 1 d . .
H5 H 0.1383(19) 0.5353(16) 0.1444(18) 0.067(4) Uiso 1 d . .
H2 H 0.0338(16) 0.3139(11) 0.5899(15) 0.050(4) Uiso 1 d . .
H10A H 0.329(2) 0.223(2) 0.719(2) 0.094(6) Uiso 1 d . .
H10B H 0.214(2) 0.3061(15) 0.7854(19) 0.082(5) Uiso 1 d . .
H11A H 0.534(2) 0.3706(16) 0.791(2) 0.089(6) Uiso 1 d . .
H11B H 0.488(2) 0.3234(18) 0.919(2) 0.094(6) Uiso 1 d . .
H11C H 0.428(2) 0.4521(19) 0.859(2) 0.092(6) 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
C1 N1 1.4522(18) . ?
C9 N1 1.3735(19) . ?
C9 C8 1.403(2) . ?
C9 C4 1.414(2) . ?
C8 C7 1.377(3) . ?
C7 C6 1.379(3) . ?
C6 C5 1.382(2) . ?
C5 C4 1.393(2) . ?
C4 N2 1.3955(17) . ?
C3 N2 1.2922(18) . ?
C3 C3 1.466(3) 3_566 ?
C3 C2 1.4997(18) . ?
C2 N1 1.4264(18) . ?
C2 O1 1.4350(16) . ?
C10 O1 1.4166(18) . ?
C10 C11 1.491(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
N1 C9 C8 123.56(14) . . ?
N1 C9 C4 117.88(11) . . ?
C8 C9 C4 118.52(14) . . ?
C7 C8 C9 119.97(16) . . ?
C8 C7 C6 121.38(15) . . ?
C7 C6 C5 119.82(18) . . ?
C6 C5 C4 120.13(17) . . ?
C5 C4 N2 118.71(14) . . ?
C5 C4 C9 120.14(13) . . ?
N2 C4 C9 121.02(12) . . ?
N2 C3 C3 118.84(14) . 3_566 ?
N2 C3 C2 123.52(11) . . ?
C3 C3 C2 117.58(15) 3_566 . ?
N1 C2 O1 113.85(10) . . ?
N1 C2 C3 109.53(12) . . ?
O1 C2 C3 104.71(10) . . ?
O1 C10 C11 108.78(14) . . ?
C9 N1 C2 118.01(11) . . ?
C9 N1 C1 121.72(12) . . ?
C2 N1 C1 119.38(13) . . ?
C3 N2 C4 117.54(11) . . ?
C10 O1 C2 115.45(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C9 C8 C7 179.09(13) . . . . ?
C4 C9 C8 C7 1.3(2) . . . . ?
C9 C8 C7 C6 -1.4(2) . . . . ?
C8 C7 C6 C5 -0.1(2) . . . . ?
C7 C6 C5 C4 1.8(2) . . . . ?
C6 C5 C4 N2 -177.74(13) . . . . ?
C6 C5 C4 C9 -1.9(2) . . . . ?
N1 C9 C4 C5 -177.59(12) . . . . ?
C8 C9 C4 C5 0.31(19) . . . . ?
N1 C9 C4 N2 -1.81(18) . . . . ?
C8 C9 C4 N2 176.09(12) . . . . ?
N2 C3 C2 N1 -30.26(16) . . . . ?
C3 C3 C2 N1 152.63(13) 3_566 . . . ?
N2 C3 C2 O1 92.19(14) . . . . ?
C3 C3 C2 O1 -84.92(15) 3_566 . . . ?
C8 C9 N1 C2 155.14(12) . . . . ?
C4 C9 N1 C2 -27.07(17) . . . . ?
C8 C9 N1 C1 -14.0(2) . . . . ?
C4 C9 N1 C1 163.80(13) . . . . ?
O1 C2 N1 C9 -76.27(15) . . . . ?
C3 C2 N1 C9 40.56(14) . . . . ?
O1 C2 N1 C1 93.12(14) . . . . ?
C3 C2 N1 C1 -150.06(12) . . . . ?
C3 C3 N2 C4 -178.53(13) 3_566 . . . ?
C2 C3 N2 C4 4.39(18) . . . . ?
C5 C4 N2 C3 -171.14(12) . . . . ?
C9 C4 N2 C3 13.02(18) . . . . ?
C11 C10 O1 C2 -167.02(13) . . . . ?
N1 C2 O1 C10 -93.61(15) . . . . ?
C3 C2 O1 C10 146.80(13) . . . . ?


# END of CIF
