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

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

data_an128
_database_code_depnum_ccdc_archive 'CCDC 1545664'
_audit_update_record             
;
2017-04-24 deposited with the CCDC.
2017-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
2-(Diethylamino)-6-phenylpyridine-3,4-dicarbonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H16 N4'
_chemical_formula_sum            'C17 H16 N4'
_chemical_formula_weight         276.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.3536(4)
_cell_length_b                   15.7200(10)
_cell_length_c                   13.2630(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.680(4)
_cell_angle_gamma                90
_cell_volume                     1519.43(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    684
_cell_measurement_theta_min      5
_cell_measurement_theta_max      56

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .18
_exptl_crystal_size_mid          .13
_exptl_crystal_size_min          .11
_exptl_absorpt_coefficient_mu    0.587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.488
_exptl_absorpt_correction_T_max  0.657
_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  'stadivari pilatus100k'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            10290
_diffrn_reflns_av_unetI/netI     0.1592
_diffrn_reflns_av_R_equivalents  0.1160
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.385
_diffrn_reflns_theta_max         66.470
_diffrn_reflns_theta_full        66.470
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2666
_reflns_number_gt                911
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_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)+(0.0316P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00142(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2666
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1597
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.0967
_refine_ls_wR_factor_gt          0.0726
_refine_ls_goodness_of_fit_ref   0.655
_refine_ls_restrained_S_all      0.655
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3043(3) 0.51881(13) 0.60390(16) 0.0453(6) Uani 1 1 d . . . . .
N2 N 0.3908(3) 0.53737(14) 0.77363(16) 0.0554(7) Uani 1 1 d . . . . .
N19 N 0.5131(5) 0.77978(18) 0.7814(2) 0.1127(12) Uani 1 1 d . . . . .
N12 N 0.4047(4) 0.84241(19) 0.5066(2) 0.0964(10) Uani 1 1 d . . . . .
C2 C 0.3675(4) 0.57382(17) 0.6796(2) 0.0453(7) Uani 1 1 d . . . . .
C3 C 0.3998(4) 0.65946(17) 0.6581(2) 0.0462(7) Uani 1 1 d . . . . .
C4 C 0.3599(4) 0.68607(17) 0.5561(2) 0.0475(7) Uani 1 1 d . . . . .
C5 C 0.2932(4) 0.62929(17) 0.4816(2) 0.0496(8) Uani 1 1 d . . . . .
H5 H 0.2652 0.6468 0.4143 0.060 Uiso 1 1 calc R U . . .
C6 C 0.2687(3) 0.54553(17) 0.5084(2) 0.0433(7) Uani 1 1 d . . . . .
C7 C 0.3247(4) 0.45134(18) 0.7880(2) 0.0641(9) Uani 1 1 d . . . . .
H7A H 0.2136 0.4420 0.7411 0.077 Uiso 1 1 calc R U . . .
H7B H 0.2934 0.4464 0.8565 0.077 Uiso 1 1 calc R U . . .
C8 C 0.4621(5) 0.38288(19) 0.7718(2) 0.0826(11) Uani 1 1 d . . . . .
H8A H 0.4825 0.3827 0.7018 0.124 Uiso 1 1 calc R U . . .
H8B H 0.4154 0.3285 0.7889 0.124 Uiso 1 1 calc R U . . .
H8C H 0.5758 0.3939 0.8144 0.124 Uiso 1 1 calc R U . . .
C9 C 0.4875(5) 0.57833(19) 0.8649(2) 0.0715(10) Uani 1 1 d . . . . .
H9A H 0.5715 0.6205 0.8443 0.086 Uiso 1 1 calc R U . . .
H9B H 0.5597 0.5359 0.9055 0.086 Uiso 1 1 calc R U . . .
C10 C 0.3596(6) 0.6208(2) 0.9293(2) 0.1078(14) Uani 1 1 d . . . . .
H10A H 0.2913 0.6645 0.8904 0.162 Uiso 1 1 calc R U . . .
H10B H 0.4297 0.6455 0.9883 0.162 Uiso 1 1 calc R U . . .
H10C H 0.2764 0.5793 0.9502 0.162 Uiso 1 1 calc R U . . .
C11 C 0.4637(4) 0.7240(2) 0.7294(2) 0.0667(10) Uani 1 1 d . . . . .
C12 C 0.3860(4) 0.7730(2) 0.5301(2) 0.0628(9) Uani 1 1 d . . . . .
C13 C 0.2031(4) 0.47921(17) 0.4320(2) 0.0443(7) Uani 1 1 d . . . . .
C14 C 0.1602(4) 0.49956(18) 0.3292(2) 0.0560(8) Uani 1 1 d . . . . .
H14 H 0.1693 0.5556 0.3078 0.067 Uiso 1 1 calc R U . . .
C15 C 0.1040(4) 0.4364(2) 0.2587(2) 0.0647(9) Uani 1 1 d . . . . .
H15 H 0.0769 0.4501 0.1901 0.078 Uiso 1 1 calc R U . . .
C16 C 0.0884(4) 0.3543(2) 0.2897(3) 0.0688(10) Uani 1 1 d . . . . .
H16 H 0.0510 0.3122 0.2421 0.083 Uiso 1 1 calc R U . . .
C17 C 0.1278(4) 0.33360(19) 0.3907(3) 0.0705(10) Uani 1 1 d . . . . .
H17 H 0.1163 0.2776 0.4116 0.085 Uiso 1 1 calc R U . . .
C18 C 0.1846(4) 0.39624(19) 0.4616(2) 0.0583(9) Uani 1 1 d . . . . .
H18 H 0.2104 0.3819 0.5300 0.070 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.327(3) . ?
N1 C2 1.359(3) . ?
N2 C2 1.362(3) . ?
N2 C7 1.458(3) . ?
N2 C9 1.468(3) . ?
N19 C11 1.144(3) . ?
N12 C12 1.148(3) . ?
C2 C3 1.403(3) . ?
C3 C4 1.409(3) . ?
C3 C11 1.423(4) . ?
C4 C5 1.373(3) . ?
C4 C12 1.428(4) . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 C13 1.489(3) . ?
C7 C8 1.511(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.509(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C13 C18 1.374(3) . ?
C13 C14 1.395(3) . ?
C14 C15 1.388(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.364(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.387(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

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 N1 C2 120.5(2) . . ?
C2 N2 C7 120.4(2) . . ?
C2 N2 C9 123.9(2) . . ?
C7 N2 C9 115.6(2) . . ?
N1 C2 N2 113.4(2) . . ?
N1 C2 C3 120.7(2) . . ?
N2 C2 C3 125.8(2) . . ?
C4 C3 C2 117.4(2) . . ?
C4 C3 C11 115.7(3) . . ?
C2 C3 C11 126.8(2) . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 C12 119.6(2) . . ?
C3 C4 C12 119.9(2) . . ?
C4 C5 C6 118.7(2) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
N1 C6 C5 122.1(2) . . ?
N1 C6 C13 115.7(2) . . ?
C5 C6 C13 122.2(2) . . ?
N2 C7 C8 113.6(3) . . ?
N2 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
N2 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C10 113.0(3) . . ?
N2 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
N2 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N19 C11 C3 175.3(3) . . ?
N12 C12 C4 178.2(3) . . ?
C18 C13 C14 118.6(2) . . ?
C18 C13 C6 120.4(2) . . ?
C14 C13 C6 121.0(2) . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.2(3) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C18 120.0(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 120.8(3) . . ?
C13 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?

_refine_diff_density_max         0.206
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_AN1
_database_code_depnum_ccdc_archive 'CCDC 1545662'
_audit_update_record             
;
2017-04-24 deposited with the CCDC.
2017-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
2-(Diethylamino)-5-methyl-6-phenylpyridine-3,4-dicarbonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 N4'
_chemical_formula_sum            'C18 H18 N4'
_chemical_formula_weight         290.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.5477(2)
_cell_length_b                   7.8499(2)
_cell_length_c                   21.8199(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.249(3)
_cell_angle_gamma                90
_cell_volume                     1598.14(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    765
_cell_measurement_theta_min      3
_cell_measurement_theta_max      64

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .23
_exptl_crystal_size_mid          .15
_exptl_crystal_size_min          .12
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.488
_exptl_absorpt_correction_T_max  0.657
_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  'stadivari pilatus100k'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'

_diffrn_reflns_number            9704
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.147
_diffrn_reflns_theta_max         72.131
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3075
_reflns_number_gt                2050
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1162P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0141(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3075
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1643
_refine_ls_wR_factor_gt          0.1513
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_restrained_S_all      0.929
_refine_ls_shift/su_max          0.007
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.72413(15) 0.70876(17) 0.32827(6) 0.0433(4) Uani 1 1 d . . . . .
N2 N 0.76478(15) 0.7559(2) 0.43415(6) 0.0488(4) Uani 1 1 d . . . . .
N3 N 0.3916(2) 0.6858(3) 0.46669(9) 0.0775(6) Uani 1 1 d . . . . .
N4 N 0.2014(2) 0.4592(3) 0.31684(11) 0.0902(7) Uani 1 1 d . . . . .
C2 C 0.67274(18) 0.7045(2) 0.38153(8) 0.0418(4) Uani 1 1 d . . . . .
C3 C 0.52977(18) 0.6532(2) 0.37832(8) 0.0448(4) Uani 1 1 d . . . . .
C4 C 0.45301(18) 0.5856(2) 0.32122(8) 0.0474(4) Uani 1 1 d . . . . .
C5 C 0.50978(19) 0.5807(2) 0.26746(8) 0.0487(4) Uani 1 1 d . . . . .
C6 C 0.64660(18) 0.6535(2) 0.27416(8) 0.0432(4) Uani 1 1 d . . . . .
C7 C 0.7187(2) 0.6711(2) 0.22011(8) 0.0471(4) Uani 1 1 d . . . . .
C8 C 0.6502(2) 0.7479(3) 0.16413(9) 0.0595(5) Uani 1 1 d . . . . .
H8 H 0.5567 0.7873 0.1594 0.071 Uiso 1 1 calc R U . . .
C9 C 0.7221(3) 0.7653(3) 0.11555(10) 0.0731(7) Uani 1 1 d . . . . .
H9 H 0.6766 0.8177 0.0784 0.088 Uiso 1 1 calc R U . . .
C10 C 0.8582(3) 0.7069(3) 0.12151(11) 0.0761(7) Uani 1 1 d . . . . .
H10 H 0.9047 0.7175 0.0883 0.091 Uiso 1 1 calc R U . . .
C11 C 0.9274(3) 0.6319(3) 0.17668(11) 0.0697(6) Uani 1 1 d . . . . .
H11 H 1.0205 0.5916 0.1808 0.084 Uiso 1 1 calc R U . . .
C12 C 0.8581(2) 0.6165(2) 0.22603(9) 0.0560(5) Uani 1 1 d . . . . .
H12 H 0.9061 0.5687 0.2636 0.067 Uiso 1 1 calc R U . . .
C13 C 0.4295(3) 0.4973(3) 0.20867(10) 0.0685(6) Uani 1 1 d . . . . .
H13A H 0.3619 0.4173 0.2189 0.103 Uiso 1 1 calc R U . . .
H13B H 0.4957 0.4387 0.1886 0.103 Uiso 1 1 calc R U . . .
H13C H 0.3793 0.5825 0.1808 0.103 Uiso 1 1 calc R U . . .
C14 C 0.3123(2) 0.5172(3) 0.31910(9) 0.0601(5) Uani 1 1 d . . . . .
C15 C 0.45629(19) 0.6708(3) 0.42850(9) 0.0532(5) Uani 1 1 d . . . . .
C16 C 0.7505(2) 0.7117(3) 0.49801(9) 0.0627(6) Uani 1 1 d . . . . .
H16A H 0.8404 0.6643 0.5207 0.075 Uiso 1 1 calc R U . . .
H16B H 0.6774 0.6246 0.4956 0.075 Uiso 1 1 calc R U . . .
C17 C 0.9037(2) 0.8274(3) 0.42951(9) 0.0558(5) Uani 1 1 d . . . . .
H17A H 0.9374 0.9009 0.4654 0.067 Uiso 1 1 calc R U . . .
H17B H 0.8911 0.8973 0.3921 0.067 Uiso 1 1 calc R U . . .
C18 C 0.7115(3) 0.8608(4) 0.53363(12) 0.0989(10) Uani 1 1 d . . . . .
H18A H 0.7893 0.9408 0.5413 0.148 Uiso 1 1 calc R U . . .
H18B H 0.6928 0.8225 0.5729 0.148 Uiso 1 1 calc R U . . .
H18C H 0.6273 0.9148 0.5096 0.148 Uiso 1 1 calc R U . . .
C19 C 1.0157(2) 0.6957(3) 0.42705(12) 0.0746(7) Uani 1 1 d . . . . .
H19A H 1.0220 0.6186 0.4617 0.112 Uiso 1 1 calc R U . . .
H19B H 1.1067 0.7504 0.4295 0.112 Uiso 1 1 calc R U . . .
H19C H 0.9903 0.6335 0.3884 0.112 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.326(2) . ?
N1 C2 1.354(2) . ?
N2 C2 1.351(2) . ?
N2 C17 1.463(2) . ?
N2 C16 1.470(2) . ?
N3 C15 1.144(2) . ?
N4 C14 1.144(3) . ?
C2 C3 1.410(2) . ?
C3 C4 1.408(3) . ?
C3 C15 1.427(2) . ?
C4 C5 1.393(2) . ?
C4 C14 1.439(3) . ?
C5 C6 1.405(3) . ?
C5 C13 1.498(3) . ?
C6 C7 1.493(2) . ?
C7 C12 1.378(3) . ?
C7 C8 1.394(3) . ?
C8 C9 1.387(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.358(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.376(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C16 C18 1.495(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C19 1.497(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C2 121.36(14) . . ?
C2 N2 C17 119.44(14) . . ?
C2 N2 C16 124.08(15) . . ?
C17 N2 C16 115.09(15) . . ?
N1 C2 N2 115.66(14) . . ?
N1 C2 C3 119.17(15) . . ?
N2 C2 C3 125.14(15) . . ?
C2 C3 C4 117.89(15) . . ?
C2 C3 C15 124.24(16) . . ?
C4 C3 C15 117.84(15) . . ?
C5 C4 C3 122.21(16) . . ?
C5 C4 C14 119.35(16) . . ?
C3 C4 C14 118.44(15) . . ?
C4 C5 C6 114.86(15) . . ?
C4 C5 C13 120.88(17) . . ?
C6 C5 C13 124.23(16) . . ?
N1 C6 C5 123.83(15) . . ?
N1 C6 C7 114.15(15) . . ?
C5 C6 C7 122.01(15) . . ?
C12 C7 C8 118.74(17) . . ?
C12 C7 C6 119.69(16) . . ?
C8 C7 C6 121.52(17) . . ?
C9 C8 C7 119.7(2) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 120.0(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 119.9(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C11 120.77(19) . . ?
C7 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 C4 178.3(2) . . ?
N3 C15 C3 176.8(2) . . ?
N2 C16 C18 113.05(19) . . ?
N2 C16 H16A 109.0 . . ?
C18 C16 H16A 109.0 . . ?
N2 C16 H16B 109.0 . . ?
C18 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
N2 C17 C19 113.71(17) . . ?
N2 C17 H17A 108.8 . . ?
C19 C17 H17A 108.8 . . ?
N2 C17 H17B 108.8 . . ?
C19 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_refine_diff_density_max         0.470
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.081

####################################################################### 
# 
# 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_an65
_database_code_depnum_ccdc_archive 'CCDC 1545663'
_audit_update_record             
;
2017-04-24 deposited with the CCDC.
2017-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
2-(Diethylamino)-6-(3,4-dimethoxyphenyl)pyridine-3,4-dicarbonitrile  
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 N4 O2'
_chemical_formula_sum            'C19 H20 N4 O2'
_chemical_formula_weight         336.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   15.5322(8)
_cell_length_b                   15.6186(8)
_cell_length_c                   15.7678(8)
_cell_angle_alpha                90
_cell_angle_beta                 111.743(4)
_cell_angle_gamma                90
_cell_volume                     3553.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3652
_cell_measurement_theta_min      4
_cell_measurement_theta_max      65

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .18
_exptl_crystal_size_mid          .12
_exptl_crystal_size_min          .12
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.488
_exptl_absorpt_correction_T_max  0.657
_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  'stadivari pilatus100k'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'


_exptl_special_details           
;
 ?
;

_diffrn_reflns_number            14553
_diffrn_reflns_av_unetI/netI     0.0768
_diffrn_reflns_av_R_equivalents  0.1284
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.138
_diffrn_reflns_theta_max         72.307
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             6856
_reflns_number_gt                3636
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1590P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0042(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6856
_refine_ls_number_parameters     460
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1254
_refine_ls_R_factor_gt           0.0826
_refine_ls_wR_factor_ref         0.2413
_refine_ls_wR_factor_gt          0.2140
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_restrained_S_all      0.909
_refine_ls_shift/su_max          0.015
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.80060(14) 0.71328(13) 0.38919(17) 0.0654(6) Uani 1 1 d . . . . .
O2A O 0.65072(16) 0.79283(12) 0.37530(19) 0.0728(7) Uani 1 1 d . . . . .
N1 N 0.58372(14) 0.59911(13) 0.14970(15) 0.0405(5) Uani 1 1 d . . . . .
N2 N 0.72956(16) 0.58364(14) 0.14811(17) 0.0495(6) Uani 1 1 d . . . . .
N3 N 0.8153(2) 0.81308(18) 0.1684(2) 0.0793(9) Uani 1 1 d . . . . .
N4 N 0.5853(2) 0.93864(17) 0.1253(3) 0.0863(11) Uani 1 1 d . . . . .
C2 C 0.66033(18) 0.63697(16) 0.14662(18) 0.0403(6) Uani 1 1 d . . . . .
C3 C 0.66603(19) 0.72824(17) 0.14457(19) 0.0436(7) Uani 1 1 d . . . . .
C4 C 0.58624(19) 0.77433(16) 0.13718(19) 0.0448(7) Uani 1 1 d . . . . .
C5 C 0.50732(19) 0.73379(17) 0.1362(2) 0.0469(7) Uani 1 1 d . . . . .
H5 H 0.4543 0.7648 0.1301 0.056 Uiso 1 1 calc R U . . .
C6 C 0.50903(17) 0.64464(16) 0.14447(17) 0.0381(6) Uani 1 1 d . . . . .
C7 C 0.42847(18) 0.59531(15) 0.14515(18) 0.0377(6) Uani 1 1 d . . . . .
C8 C 0.34519(19) 0.63352(17) 0.13514(19) 0.0450(7) Uani 1 1 d . . . . .
H8 H 0.3400 0.6928 0.1313 0.054 Uiso 1 1 calc R U . . .
C9 C 0.26942(19) 0.58485(17) 0.1308(2) 0.0464(7) Uani 1 1 d . . . . .
H9 H 0.2139 0.6116 0.1244 0.056 Uiso 1 1 calc R U . . .
C10 C 0.27570(17) 0.49688(17) 0.13587(18) 0.0415(6) Uani 1 1 d . . . . .
C11 C 0.35994(18) 0.45730(15) 0.14685(19) 0.0414(6) Uani 1 1 d . . . . .
C12 C 0.43491(18) 0.50571(15) 0.15167(18) 0.0400(6) Uani 1 1 d . . . . .
H12 H 0.4908 0.4790 0.1594 0.048 Uiso 1 1 calc R U . . .
C13 C 0.1144(2) 0.4796(3) 0.1026(4) 0.0916(14) Uani 1 1 d . . . . .
H13A H 0.1133 0.5220 0.1463 0.137 Uiso 1 1 calc R U . . .
H13B H 0.0703 0.4354 0.0992 0.137 Uiso 1 1 calc R U . . .
H13C H 0.0986 0.5059 0.0437 0.137 Uiso 1 1 calc R U . . .
C14 C 0.4394(3) 0.32761(19) 0.1480(3) 0.0819(12) Uani 1 1 d . . . . .
H14A H 0.4491 0.3442 0.0937 0.123 Uiso 1 1 calc R U . . .
H14B H 0.4308 0.2667 0.1479 0.123 Uiso 1 1 calc R U . . .
H14C H 0.4923 0.3436 0.2006 0.123 Uiso 1 1 calc R U . . .
C15 C 0.5870(2) 0.86646(18) 0.1314(2) 0.0585(8) Uani 1 1 d . . . . .
C16 C 0.7487(2) 0.77415(18) 0.1567(2) 0.0555(8) Uani 1 1 d . . . . .
C17 C 0.7923(2) 0.6035(2) 0.0998(3) 0.0657(9) Uani 1 1 d . . . . .
H17A H 0.7733 0.6576 0.0681 0.079 Uiso 1 1 calc R U . . .
H17B H 0.7848 0.5598 0.0540 0.079 Uiso 1 1 calc R U . . .
C18 C 0.7233(2) 0.49188(18) 0.1692(2) 0.0543(8) Uani 1 1 d . . . . .
H18A H 0.6963 0.4874 0.2155 0.065 Uiso 1 1 calc R U . . .
H18B H 0.7855 0.4684 0.1947 0.065 Uiso 1 1 calc R U . . .
C19 C 0.8919(3) 0.6094(3) 0.1582(3) 0.0933(13) Uani 1 1 d . . . . .
H19A H 0.9009 0.6541 0.2024 0.140 Uiso 1 1 calc R U . . .
H19B H 0.9272 0.6220 0.1210 0.140 Uiso 1 1 calc R U . . .
H19C H 0.9123 0.5559 0.1891 0.140 Uiso 1 1 calc R U . . .
C20 C 0.6673(3) 0.4392(2) 0.0888(2) 0.0672(9) Uani 1 1 d . . . . .
H20A H 0.6052 0.4613 0.0637 0.101 Uiso 1 1 calc R U . . .
H20B H 0.6659 0.3809 0.1076 0.101 Uiso 1 1 calc R U . . .
H20C H 0.6947 0.4416 0.0433 0.101 Uiso 1 1 calc R U . . .
O1 O 0.20445(13) 0.44346(13) 0.12992(16) 0.0604(6) Uani 1 1 d . . . . .
O2 O 0.35947(14) 0.36938(11) 0.15083(17) 0.0614(6) Uani 1 1 d . . . . .
N1A N 0.41620(15) 0.56936(13) 0.37299(15) 0.0419(5) Uani 1 1 d . . . . .
N2A N 0.26846(17) 0.58838(15) 0.3665(2) 0.0582(7) Uani 1 1 d . . . . .
N3A N 0.1793(2) 0.3586(2) 0.3479(3) 0.0981(12) Uani 1 1 d . . . . .
N4A N 0.4049(2) 0.22929(17) 0.3799(2) 0.0793(9) Uani 1 1 d . . . . .
C2A C 0.33669(19) 0.53288(17) 0.37013(19) 0.0441(6) Uani 1 1 d . . . . .
C3A C 0.32854(19) 0.44229(17) 0.37063(19) 0.0444(7) Uani 1 1 d . . . . .
C4A C 0.40724(19) 0.39452(16) 0.37762(18) 0.0432(7) Uani 1 1 d . . . . .
C5A C 0.48808(19) 0.43300(16) 0.38252(19) 0.0440(7) Uani 1 1 d . . . . .
H5A H 0.5403 0.4008 0.3883 0.053 Uiso 1 1 calc R U . . .
C6A C 0.48955(17) 0.52209(15) 0.37855(17) 0.0376(6) Uani 1 1 d . . . . .
C7A C 0.57262(17) 0.56994(15) 0.38093(17) 0.0376(6) Uani 1 1 d . . . . .
C8A C 0.65279(18) 0.52870(16) 0.38502(19) 0.0423(6) Uani 1 1 d . . . . .
H8A H 0.6548 0.4692 0.3856 0.051 Uiso 1 1 calc R U . . .
C9A C 0.73019(19) 0.57461(17) 0.38823(19) 0.0448(7) Uani 1 1 d . . . . .
H9A H 0.7838 0.5456 0.3920 0.054 Uiso 1 1 calc R U . . .
C10A C 0.72873(18) 0.66259(17) 0.3859(2) 0.0447(7) Uani 1 1 d . . . . .
C11A C 0.64655(19) 0.70569(16) 0.3795(2) 0.0465(7) Uani 1 1 d . . . . .
C12A C 0.57110(19) 0.65967(16) 0.3777(2) 0.0443(7) Uani 1 1 d . . . . .
H12A H 0.5175 0.6885 0.3743 0.053 Uiso 1 1 calc R U . . .
C13A C 0.8861(2) 0.6726(2) 0.4035(3) 0.0790(11) Uani 1 1 d . . . . .
H13D H 0.9057 0.6414 0.4599 0.118 Uiso 1 1 calc R U . . .
H13E H 0.9318 0.7150 0.4062 0.118 Uiso 1 1 calc R U . . .
H13F H 0.8788 0.6338 0.3541 0.118 Uiso 1 1 calc R U . . .
C14A C 0.5726(3) 0.83901(19) 0.3744(3) 0.0773(11) Uani 1 1 d . . . . .
H14D H 0.5191 0.8208 0.3234 0.116 Uiso 1 1 calc R U . . .
H14E H 0.5827 0.8991 0.3689 0.116 Uiso 1 1 calc R U . . .
H14F H 0.5627 0.8286 0.4301 0.116 Uiso 1 1 calc R U . . .
C15A C 0.4037(2) 0.30202(18) 0.3783(2) 0.0559(8) Uani 1 1 d . . . . .
C16A C 0.2449(2) 0.3976(2) 0.3585(3) 0.0620(9) Uani 1 1 d . . . . .
C17A C 0.1934(4) 0.5679(3) 0.3974(5) 0.138(3) Uani 1 1 d . . . . .
H17C H 0.2081 0.5114 0.4244 0.166 Uiso 1 1 calc R U . . .
H17D H 0.2015 0.6068 0.4478 0.166 Uiso 1 1 calc R U . . .
C18A C 0.2817(2) 0.6809(2) 0.3544(3) 0.0678(10) Uani 1 1 d . . . . .
H18C H 0.3123 0.6875 0.3111 0.081 Uiso 1 1 calc R U . . .
H18D H 0.2213 0.7080 0.3282 0.081 Uiso 1 1 calc R U . . .
C19A C 0.1081(4) 0.5665(4) 0.3531(6) 0.179(4) Uani 1 1 d . . . . .
H19D H 0.0916 0.6130 0.3102 0.268 Uiso 1 1 calc R U . . .
H19E H 0.0757 0.5723 0.3941 0.268 Uiso 1 1 calc R U . . .
H19F H 0.0915 0.5132 0.3208 0.268 Uiso 1 1 calc R U . . .
C20A C 0.3361(3) 0.7254(2) 0.4388(3) 0.0814(11) Uani 1 1 d . . . . .
H20D H 0.3080 0.7171 0.4832 0.122 Uiso 1 1 calc R U . . .
H20E H 0.3380 0.7855 0.4267 0.122 Uiso 1 1 calc R U . . .
H20F H 0.3980 0.7029 0.4621 0.122 Uiso 1 1 calc R U . . .


_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
O1A C10A 1.354(3) . ?
O1A C13A 1.413(4) . ?
O2A C11A 1.365(3) . ?
O2A C14A 1.407(4) . ?
N1 C6 1.337(3) . ?
N1 C2 1.346(3) . ?
N2 C2 1.353(3) . ?
N2 C17 1.475(4) . ?
N2 C18 1.483(4) . ?
N3 C16 1.154(4) . ?
N4 C15 1.131(4) . ?
C2 C3 1.429(3) . ?
C3 C4 1.400(4) . ?
C3 C16 1.421(4) . ?
C4 C5 1.374(4) . ?
C4 C15 1.442(4) . ?
C5 C6 1.398(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.473(3) . ?
C7 C8 1.379(4) . ?
C7 C12 1.404(3) . ?
C8 C9 1.381(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(4) . ?
C9 H9 0.9300 . ?
C10 O1 1.361(3) . ?
C10 C11 1.399(4) . ?
C11 C12 1.367(4) . ?
C11 O2 1.375(3) . ?
C12 H12 0.9300 . ?
C13 O1 1.420(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O2 1.417(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C17 C19 1.482(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C20 1.492(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N1A C6A 1.333(3) . ?
N1A C2A 1.346(3) . ?
N2A C2A 1.354(4) . ?
N2A C17A 1.457(5) . ?
N2A C18A 1.482(4) . ?
N3A C16A 1.144(4) . ?
N4A C15A 1.136(4) . ?
C2A C3A 1.421(4) . ?
C3A C4A 1.401(4) . ?
C3A C16A 1.425(4) . ?
C4A C5A 1.368(4) . ?
C4A C15A 1.446(4) . ?
C5A C6A 1.393(3) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.480(4) . ?
C7A C8A 1.382(4) . ?
C7A C12A 1.402(3) . ?
C8A C9A 1.385(4) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.375(4) . ?
C9A H9A 0.9300 . ?
C10A C11A 1.413(4) . ?
C11A C12A 1.366(4) . ?
C12A H12A 0.9300 . ?
C13A H13D 0.9600 . ?
C13A H13E 0.9600 . ?
C13A H13F 0.9600 . ?
C14A H14D 0.9600 . ?
C14A H14E 0.9600 . ?
C14A H14F 0.9600 . ?
C17A C19A 1.248(7) . ?
C17A H17C 0.9700 . ?
C17A H17D 0.9700 . ?
C18A C20A 1.462(5) . ?
C18A H18C 0.9700 . ?
C18A H18D 0.9700 . ?
C19A H19D 0.9600 . ?
C19A H19E 0.9600 . ?
C19A H19F 0.9600 . ?
C20A H20D 0.9600 . ?
C20A H20E 0.9600 . ?
C20A H20F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10A O1A C13A 117.1(2) . . ?
C11A O2A C14A 117.1(2) . . ?
C6 N1 C2 121.5(2) . . ?
C2 N2 C17 122.3(2) . . ?
C2 N2 C18 118.8(2) . . ?
C17 N2 C18 115.5(2) . . ?
N1 C2 N2 115.9(2) . . ?
N1 C2 C3 120.1(2) . . ?
N2 C2 C3 124.0(2) . . ?
C4 C3 C16 118.7(2) . . ?
C4 C3 C2 117.0(2) . . ?
C16 C3 C2 124.1(3) . . ?
C5 C4 C3 121.5(2) . . ?
C5 C4 C15 119.2(3) . . ?
C3 C4 C15 119.4(2) . . ?
C4 C5 C6 118.2(3) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
N1 C6 C5 121.4(2) . . ?
N1 C6 C7 116.2(2) . . ?
C5 C6 C7 122.3(2) . . ?
C8 C7 C12 118.6(2) . . ?
C8 C7 C6 122.4(2) . . ?
C12 C7 C6 119.0(2) . . ?
C7 C8 C9 120.9(2) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
O1 C10 C9 124.7(2) . . ?
O1 C10 C11 115.9(2) . . ?
C9 C10 C11 119.4(2) . . ?
C12 C11 O2 124.7(2) . . ?
C12 C11 C10 120.1(2) . . ?
O2 C11 C10 115.2(2) . . ?
C11 C12 C7 120.7(2) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N4 C15 C4 178.2(4) . . ?
N3 C16 C3 177.9(4) . . ?
N2 C17 C19 115.4(3) . . ?
N2 C17 H17A 108.4 . . ?
C19 C17 H17A 108.4 . . ?
N2 C17 H17B 108.4 . . ?
C19 C17 H17B 108.4 . . ?
H17A C17 H17B 107.5 . . ?
N2 C18 C20 114.1(3) . . ?
N2 C18 H18A 108.7 . . ?
C20 C18 H18A 108.7 . . ?
N2 C18 H18B 108.7 . . ?
C20 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10 O1 C13 117.5(2) . . ?
C11 O2 C14 116.0(2) . . ?
C6A N1A C2A 121.3(2) . . ?
C2A N2A C17A 123.8(3) . . ?
C2A N2A C18A 119.1(2) . . ?
C17A N2A C18A 115.1(3) . . ?
N1A C2A N2A 115.1(2) . . ?
N1A C2A C3A 120.3(2) . . ?
N2A C2A C3A 124.6(3) . . ?
C4A C3A C2A 117.0(2) . . ?
C4A C3A C16A 118.4(2) . . ?
C2A C3A C16A 124.5(3) . . ?
C5A C4A C3A 121.7(2) . . ?
C5A C4A C15A 118.4(3) . . ?
C3A C4A C15A 119.9(3) . . ?
C4A C5A C6A 117.8(3) . . ?
C4A C5A H5A 121.1 . . ?
C6A C5A H5A 121.1 . . ?
N1A C6A C5A 121.9(2) . . ?
N1A C6A C7A 116.0(2) . . ?
C5A C6A C7A 122.1(2) . . ?
C8A C7A C12A 118.1(2) . . ?
C8A C7A C6A 121.9(2) . . ?
C12A C7A C6A 120.1(2) . . ?
C7A C8A C9A 121.0(2) . . ?
C7A C8A H8A 119.5 . . ?
C9A C8A H8A 119.5 . . ?
C10A C9A C8A 120.7(2) . . ?
C10A C9A H9A 119.6 . . ?
C8A C9A H9A 119.6 . . ?
O1A C10A C9A 125.3(2) . . ?
O1A C10A C11A 115.8(2) . . ?
C9A C10A C11A 118.9(2) . . ?
O2A C11A C12A 125.4(2) . . ?
O2A C11A C10A 114.8(2) . . ?
C12A C11A C10A 119.7(2) . . ?
C11A C12A C7A 121.5(2) . . ?
C11A C12A H12A 119.3 . . ?
C7A C12A H12A 119.3 . . ?
O1A C13A H13D 109.5 . . ?
O1A C13A H13E 109.5 . . ?
H13D C13A H13E 109.5 . . ?
O1A C13A H13F 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
O2A C14A H14D 109.5 . . ?
O2A C14A H14E 109.5 . . ?
H14D C14A H14E 109.5 . . ?
O2A C14A H14F 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
N4A C15A C4A 177.0(3) . . ?
N3A C16A C3A 177.1(4) . . ?
C19A C17A N2A 129.1(7) . . ?
C19A C17A H17C 105.0 . . ?
N2A C17A H17C 105.0 . . ?
C19A C17A H17D 105.0 . . ?
N2A C17A H17D 105.0 . . ?
H17C C17A H17D 105.9 . . ?
C20A C18A N2A 114.0(3) . . ?
C20A C18A H18C 108.7 . . ?
N2A C18A H18C 108.7 . . ?
C20A C18A H18D 108.7 . . ?
N2A C18A H18D 108.7 . . ?
H18C C18A H18D 107.6 . . ?
C17A C19A H19D 109.5 . . ?
C17A C19A H19E 109.5 . . ?
H19D C19A H19E 109.5 . . ?
C17A C19A H19F 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
C18A C20A H20D 109.5 . . ?
C18A C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
C18A C20A H20F 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?

_refine_diff_density_max         0.511
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.193

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mv185
_database_code_depnum_ccdc_archive 'CCDC 1545665'
_audit_update_record             
;
2017-04-24 deposited with the CCDC.
2017-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
2-(Diethylamino)-5,6,7,8,9,10-hexahydrocycloocta[b]
pyridine-3,4-dicarbonitrile     
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H22 N4'
_chemical_formula_sum            'C17 H22 N4'
_chemical_formula_weight         282.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   4.9799(3)
_cell_length_b                   14.1541(7)
_cell_length_c                   22.8964(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.652(2)
_cell_angle_gamma                90
_cell_volume                     1612.15(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1549
_cell_measurement_theta_min      4
_cell_measurement_theta_max      65

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .17
_exptl_crystal_size_mid          .13
_exptl_crystal_size_min          .12
_exptl_absorpt_coefficient_mu    0.554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.361
_exptl_absorpt_correction_T_max  0.553
_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  'stadivari pilatus100k'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            10788
_diffrn_reflns_av_unetI/netI     0.0734
_diffrn_reflns_av_R_equivalents  0.1044
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.672
_diffrn_reflns_theta_max         70.587
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             2931
_reflns_number_gt                1699
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1903P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2931
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1289
_refine_ls_R_factor_gt           0.0957
_refine_ls_wR_factor_ref         0.2923
_refine_ls_wR_factor_gt          0.2673
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8313(6) 0.36097(18) 0.62043(11) 0.0563(8) Uani 1 1 d . . . . .
N2 N 0.5674(7) 0.3939(2) 0.69650(13) 0.0756(10) Uani 1 1 d . . . . .
N3 N 0.2478(11) 0.1454(3) 0.72054(18) 0.1163(16) Uani 1 1 d . . . . .
N4 N 0.6010(10) -0.0046(3) 0.61604(19) 0.1077(15) Uani 1 1 d . . . . .
C2 C 0.6588(7) 0.3287(2) 0.65928(13) 0.0570(9) Uani 1 1 d . . . . .
C3 C 0.5870(8) 0.2310(2) 0.65840(14) 0.0610(9) Uani 1 1 d . . . . .
C4 C 0.7150(7) 0.1733(2) 0.61865(14) 0.0591(9) Uani 1 1 d . . . . .
C5 C 0.8976(7) 0.2061(2) 0.57993(14) 0.0562(9) Uani 1 1 d . . . . .
C6 C 1.0273(8) 0.1433(2) 0.53653(17) 0.0703(10) Uani 1 1 d . . . . .
H6A H 1.0608 0.0819 0.5542 0.084 Uiso 1 1 calc R U . . .
H6B H 1.1995 0.1701 0.5273 0.084 Uiso 1 1 calc R U . . .
C7 C 0.8574(9) 0.1305(3) 0.48027(17) 0.0768(12) Uani 1 1 d . . . . .
H7A H 0.9622 0.0960 0.4527 0.092 Uiso 1 1 calc R U . . .
H7B H 0.7028 0.0919 0.4886 0.092 Uiso 1 1 calc R U . . .
C8 C 0.7584(8) 0.2208(3) 0.45148(16) 0.0698(10) Uani 1 1 d . . . . .
H8A H 0.6322 0.2506 0.4768 0.084 Uiso 1 1 calc R U . . .
H8B H 0.6605 0.2047 0.4152 0.084 Uiso 1 1 calc R U . . .
C9 C 0.9735(8) 0.2926(3) 0.43791(15) 0.0692(10) Uani 1 1 d . . . . .
H9A H 0.9299 0.3191 0.3996 0.083 Uiso 1 1 calc R U . . .
H9B H 1.1434 0.2595 0.4357 0.083 Uiso 1 1 calc R U . . .
C10 C 1.0121(9) 0.3737(2) 0.48116(15) 0.0709(11) Uani 1 1 d . . . . .
H10A H 0.8381 0.4031 0.4855 0.085 Uiso 1 1 calc R U . . .
H10B H 1.1261 0.4204 0.4636 0.085 Uiso 1 1 calc R U . . .
C11 C 1.1320(8) 0.3524(2) 0.54252(14) 0.0618(9) Uani 1 1 d . . . . .
H11A H 1.2893 0.3128 0.5388 0.074 Uiso 1 1 calc R U . . .
H11B H 1.1917 0.4113 0.5604 0.074 Uiso 1 1 calc R U . . .
C12 C 0.9459(7) 0.3044(2) 0.58265(13) 0.0520(8) Uani 1 1 d . . . . .
C13 C 0.6510(9) 0.0734(3) 0.61766(18) 0.0771(12) Uani 1 1 d . . . . .
C14 C 0.3985(10) 0.1864(3) 0.69436(16) 0.0794(12) Uani 1 1 d . . . . .
C15 C 0.3677(14) 0.3773(4) 0.7398(2) 0.1131(19) Uani 1 1 d . . . . .
H15A H 0.2720 0.4357 0.7466 0.136 Uiso 1 1 calc R U . . .
H15B H 0.2383 0.3312 0.7247 0.136 Uiso 1 1 calc R U . . .
C16 C 0.484(2) 0.3443(6) 0.7933(2) 0.167(4) Uani 1 1 d . . . . .
H16A H 0.5987 0.2914 0.7861 0.250 Uiso 1 1 calc R U . . .
H16B H 0.3447 0.3251 0.8183 0.250 Uiso 1 1 calc R U . . .
H16C H 0.5880 0.3940 0.8119 0.250 Uiso 1 1 calc R U . . .
C17 C 0.6715(10) 0.4915(3) 0.69542(18) 0.0821(13) Uani 1 1 d . . . . .
H17A H 0.8583 0.4905 0.6852 0.099 Uiso 1 1 calc R U . . .
H17B H 0.6630 0.5191 0.7341 0.099 Uiso 1 1 calc R U . . .
C18 C 0.5121(11) 0.5512(4) 0.6521(2) 0.0993(15) Uani 1 1 d . . . . .
H18A H 0.5157 0.5229 0.6140 0.149 Uiso 1 1 calc R U . . .
H18B H 0.5891 0.6133 0.6509 0.149 Uiso 1 1 calc R U . . .
H18C H 0.3295 0.5555 0.6636 0.149 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C12 1.327(4) . ?
N1 C2 1.345(4) . ?
N2 C2 1.349(4) . ?
N2 C15 1.456(6) . ?
N2 C17 1.477(5) . ?
N3 C14 1.141(5) . ?
N4 C13 1.132(5) . ?
C2 C3 1.428(5) . ?
C3 C4 1.398(5) . ?
C3 C14 1.424(5) . ?
C4 C5 1.380(5) . ?
C4 C13 1.450(5) . ?
C5 C12 1.413(5) . ?
C5 C6 1.501(5) . ?
C6 C7 1.519(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.511(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.519(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.523(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.531(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.498(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C15 C16 1.410(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.502(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N1 C2 122.3(3) . . ?
C2 N2 C15 125.5(4) . . ?
C2 N2 C17 120.0(3) . . ?
C15 N2 C17 114.4(3) . . ?
N1 C2 N2 115.5(3) . . ?
N1 C2 C3 119.1(3) . . ?
N2 C2 C3 125.4(3) . . ?
C4 C3 C14 116.7(3) . . ?
C4 C3 C2 116.9(3) . . ?
C14 C3 C2 126.3(3) . . ?
C5 C4 C3 123.8(3) . . ?
C5 C4 C13 118.0(3) . . ?
C3 C4 C13 118.2(3) . . ?
C4 C5 C12 114.8(3) . . ?
C4 C5 C6 122.9(3) . . ?
C12 C5 C6 122.3(3) . . ?
C5 C6 C7 113.1(3) . . ?
C5 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C6 115.2(3) . . ?
C8 C7 H7A 108.5 . . ?
C6 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
C6 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C7 C8 C9 115.9(3) . . ?
C7 C8 H8A 108.3 . . ?
C9 C8 H8A 108.3 . . ?
C7 C8 H8B 108.3 . . ?
C9 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C8 C9 C10 116.1(3) . . ?
C8 C9 H9A 108.3 . . ?
C10 C9 H9A 108.3 . . ?
C8 C9 H9B 108.3 . . ?
C10 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
C9 C10 C11 118.7(3) . . ?
C9 C10 H10A 107.6 . . ?
C11 C10 H10A 107.6 . . ?
C9 C10 H10B 107.6 . . ?
C11 C10 H10B 107.6 . . ?
H10A C10 H10B 107.1 . . ?
C12 C11 C10 115.2(3) . . ?
C12 C11 H11A 108.5 . . ?
C10 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
C10 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
N1 C12 C5 123.0(3) . . ?
N1 C12 C11 115.1(3) . . ?
C5 C12 C11 121.9(3) . . ?
N4 C13 C4 179.0(5) . . ?
N3 C14 C3 175.2(5) . . ?
C16 C15 N2 112.3(6) . . ?
C16 C15 H15A 109.1 . . ?
N2 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
N2 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 C18 111.2(4) . . ?
N2 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
N2 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_refine_diff_density_max         0.371
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.090

