# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_compound_1_phenyl
_database_code_depnum_ccdc_archive 'CCDC 1425934'
_audit_update_record             
;
2015-09-18 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 N2 O'
_chemical_formula_sum            'C15 H16 N2 O'
_chemical_formula_weight         240.30

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '

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

_cell_length_a                   9.5732(13)
_cell_length_b                   9.6932(13)
_cell_length_c                   14.0706(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1305.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4677
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      23.03

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9808
_exptl_absorpt_correction_T_max  0.9953
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13719
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_sigmaI/netI    0.0494
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2289
_reflns_number_gt                1788
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_cell_refinement       'SAINT (APEX2, Bruker, 2006)'
_computing_data_reduction        'SAINT (APEX2, Bruker, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0829P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(3)
_refine_ls_number_reflns         2289
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0671
_refine_ls_wR_factor_ref         0.1711
_refine_ls_wR_factor_gt          0.1611
_refine_ls_goodness_of_fit_ref   1.236
_refine_ls_restrained_S_all      1.236
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0781(3) 0.4778(2) 0.27608(15) 0.0650(7) Uani 1 1 d . . .
N1 N 0.1688(3) 0.6553(3) -0.15490(18) 0.0663(9) Uani 1 1 d . . .
H1A H 0.2436 0.6194 -0.1779 0.080 Uiso 1 1 calc R . .
H1B H 0.1128 0.7004 -0.1913 0.080 Uiso 1 1 calc R . .
N2 N -0.0341(3) 0.6821(3) 0.27864(16) 0.0664(9) Uani 1 1 d . . .
H2 H -0.0491 0.7590 0.2500 0.080 Uiso 1 1 calc R . .
C1 C 0.0758(4) 0.6091(3) 0.1335(2) 0.0457(8) Uani 1 1 d . . .
C2 C 0.1943(4) 0.5511(3) 0.0939(2) 0.0525(8) Uani 1 1 d . . .
H2A H 0.2534 0.4988 0.1320 0.063 Uiso 1 1 calc R . .
C3 C 0.2266(4) 0.5692(3) -0.0003(2) 0.0530(9) Uani 1 1 d . . .
H3 H 0.3092 0.5325 -0.0242 0.064 Uiso 1 1 calc R . .
C4 C 0.1386(3) 0.6408(3) -0.0599(2) 0.0489(8) Uani 1 1 d . . .
C5 C 0.0188(4) 0.6991(3) -0.0211(2) 0.0577(9) Uani 1 1 d . . .
H5 H -0.0412 0.7496 -0.0598 0.069 Uiso 1 1 calc R . .
C6 C -0.0122(4) 0.6830(3) 0.0740(2) 0.0559(9) Uani 1 1 d . . .
H6 H -0.0932 0.7223 0.0986 0.067 Uiso 1 1 calc R . .
C7 C 0.0405(4) 0.5844(3) 0.2349(2) 0.0497(8) Uani 1 1 d . . .
C8 C -0.0920(5) 0.6610(4) 0.3759(2) 0.0802(12) Uani 1 1 d . . .
H8A H -0.1821 0.7064 0.3806 0.096 Uiso 1 1 calc R . .
H8B H -0.1063 0.5632 0.3868 0.096 Uiso 1 1 calc R . .
C9 C 0.0023(4) 0.7164(4) 0.4499(2) 0.0708(11) Uani 1 1 d . . .
H9A H 0.0153 0.8146 0.4397 0.085 Uiso 1 1 calc R . .
H9B H 0.0928 0.6721 0.4446 0.085 Uiso 1 1 calc R . .
C10 C -0.0566(4) 0.6924(4) 0.5503(2) 0.0637(10) Uani 1 1 d . . .
C11 C -0.1162(6) 0.5686(4) 0.5772(3) 0.0914(15) Uani 1 1 d . . .
H11 H -0.1189 0.4959 0.5341 0.110 Uiso 1 1 calc R . .
C12 C -0.1718(5) 0.5512(5) 0.6672(3) 0.0914(14) Uani 1 1 d . . .
H12 H -0.2129 0.4678 0.6842 0.110 Uiso 1 1 calc R . .
C13 C -0.1660(5) 0.6570(5) 0.7305(3) 0.0826(13) Uani 1 1 d . . .
H13 H -0.2026 0.6468 0.7913 0.099 Uiso 1 1 calc R . .
C14 C -0.1069(5) 0.7761(5) 0.7041(3) 0.0831(13) Uani 1 1 d . . .
H14 H -0.1024 0.8477 0.7480 0.100 Uiso 1 1 calc R . .
C15 C -0.0533(4) 0.7971(4) 0.6160(2) 0.0734(11) Uani 1 1 d . . .
H15 H -0.0145 0.8820 0.6001 0.088 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.238(3) . ?
N1 C4 1.375(4) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 C7 1.337(4) . ?
N2 C8 1.491(4) . ?
N2 H2 0.8600 . ?
C1 C2 1.383(5) . ?
C1 C6 1.387(4) . ?
C1 C7 1.486(4) . ?
C2 C3 1.373(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.376(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(4) . ?
C5 C6 1.380(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.479(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.539(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C15 1.372(5) . ?
C10 C11 1.381(6) . ?
C11 C12 1.384(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.360(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.338(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.357(5) . ?
C14 H14 0.9300 . ?
C15 H15 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
C4 N1 H1A 120.0 . . ?
C4 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C7 N2 C8 121.6(3) . . ?
C7 N2 H2 119.2 . . ?
C8 N2 H2 119.2 . . ?
C2 C1 C6 117.8(3) . . ?
C2 C1 C7 120.5(3) . . ?
C6 C1 C7 121.6(3) . . ?
C3 C2 C1 121.5(3) . . ?
C3 C2 H2A 119.3 . . ?
C1 C2 H2A 119.3 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
N1 C4 C3 121.0(3) . . ?
N1 C4 C5 120.9(3) . . ?
C3 C4 C5 118.1(3) . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 120.8(3) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
O1 C7 N2 122.1(3) . . ?
O1 C7 C1 121.2(3) . . ?
N2 C7 C1 116.7(3) . . ?
C9 C8 N2 111.7(4) . . ?
C9 C8 H8A 109.3 . . ?
N2 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
N2 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C10 111.5(3) . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C15 C10 C11 117.9(3) . . ?
C15 C10 C9 119.8(3) . . ?
C11 C10 C9 122.2(3) . . ?
C10 C11 C12 121.0(4) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 119.5(4) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 119.1(4) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 122.9(4) . . ?
C13 C14 H14 118.6 . . ?
C15 C14 H14 118.6 . . ?
C14 C15 C10 119.7(4) . . ?
C14 C15 H15 120.2 . . ?
C10 C15 H15 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.9(4) . . . . ?
C7 C1 C2 C3 178.0(3) . . . . ?
C1 C2 C3 C4 -2.9(5) . . . . ?
C2 C3 C4 N1 -178.0(3) . . . . ?
C2 C3 C4 C5 2.5(5) . . . . ?
N1 C4 C5 C6 179.2(3) . . . . ?
C3 C4 C5 C6 -1.3(5) . . . . ?
C4 C5 C6 C1 0.4(5) . . . . ?
C2 C1 C6 C5 -0.7(5) . . . . ?
C7 C1 C6 C5 -176.7(3) . . . . ?
C8 N2 C7 O1 -7.9(5) . . . . ?
C8 N2 C7 C1 171.7(3) . . . . ?
C2 C1 C7 O1 -27.8(4) . . . . ?
C6 C1 C7 O1 148.2(3) . . . . ?
C2 C1 C7 N2 152.6(3) . . . . ?
C6 C1 C7 N2 -31.4(4) . . . . ?
C7 N2 C8 C9 94.4(4) . . . . ?
N2 C8 C9 C10 -179.1(3) . . . . ?
C8 C9 C10 C15 -135.3(4) . . . . ?
C8 C9 C10 C11 43.4(5) . . . . ?
C15 C10 C11 C12 0.6(7) . . . . ?
C9 C10 C11 C12 -178.2(4) . . . . ?
C10 C11 C12 C13 -0.9(8) . . . . ?
C11 C12 C13 C14 0.3(7) . . . . ?
C12 C13 C14 C15 0.7(7) . . . . ?
C13 C14 C15 C10 -1.1(6) . . . . ?
C11 C10 C15 C14 0.4(6) . . . . ?
C9 C10 C15 C14 179.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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_Compound_2_pyrrolidine
_database_code_depnum_ccdc_archive 'CCDC 1425935'
_audit_update_record             
;
2015-12-13 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H19 N3 O'
_chemical_formula_sum            'C13 H19 N3 O'
_chemical_formula_weight         233.31

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '

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

_cell_length_a                   6.391(3)
_cell_length_b                   13.847(7)
_cell_length_c                   14.418(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1276.0(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1807
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      21.44

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9929
_exptl_absorpt_correction_T_max  0.9980
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6182
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_sigmaI/netI    0.0612
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2235
_reflns_number_gt                1343
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_cell_refinement       'SAINT (APEX2, Bruker, 2006)'
_computing_data_reduction        'SAINT (APEX2, Bruker, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0709P)²+0.1372P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(3)
_refine_ls_number_reflns         2235
_refine_ls_number_parameters     176
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1493
_refine_ls_wR_factor_gt          0.1232
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0624(4) 0.47343(17) 0.20626(16) 0.0913(8) Uani 1 1 d . . .
N1 N 1.2335(5) 0.67627(17) -0.17868(17) 0.0748(8) Uani 1 1 d . . .
H1A H 1.3541 0.6591 -0.1994 0.090 Uiso 1 1 calc R . .
H1B H 1.1558 0.7144 -0.2108 0.090 Uiso 1 1 calc R . .
N2 N 0.8064(7) 0.5806(2) 0.2117(2) 0.1063(14) Uani 1 1 d D . .
N3 N 0.5275(5) 0.6929(2) 0.3299(2) 0.0810(9) Uani 1 1 d . . .
C1 C 1.0315(5) 0.57870(19) 0.07922(19) 0.0567(8) Uani 1 1 d . . .
C2 C 1.2225(5) 0.5508(2) 0.0417(2) 0.0654(8) Uani 1 1 d . A .
H2 H 1.3081 0.5093 0.0754 0.078 Uiso 1 1 calc R . .
C3 C 1.2874(5) 0.5819(2) -0.0422(2) 0.0664(8) Uani 1 1 d . . .
H3 H 1.4166 0.5617 -0.0647 0.080 Uiso 1 1 calc R A .
C4 C 1.1659(5) 0.6433(2) -0.0955(2) 0.0570(8) Uani 1 1 d . A .
C5 C 0.9750(5) 0.6721(2) -0.0586(2) 0.0629(9) Uani 1 1 d . . .
H5 H 0.8896 0.7136 -0.0923 0.075 Uiso 1 1 calc R A .
C6 C 0.9113(5) 0.6406(2) 0.0259(2) 0.0636(9) Uani 1 1 d . A .
H6 H 0.7827 0.6612 0.0487 0.076 Uiso 1 1 calc R . .
C7 C 0.9691(6) 0.5404(2) 0.1703(2) 0.0671(9) Uani 1 1 d . A .
C8 C 0.6773(19) 0.5395(6) 0.2883(5) 0.072(2) Uani 0.55 1 d PDU A 1
H8A H 0.7404 0.4806 0.3118 0.087 Uiso 0.55 1 calc PR A 1
H8B H 0.5374 0.5247 0.2664 0.087 Uiso 0.55 1 calc PR A 1
C9 C 0.6694(12) 0.6158(4) 0.3635(4) 0.0733(17) Uani 0.60 1 d PDU A 1
H9A H 0.6167 0.5883 0.4208 0.088 Uiso 0.60 1 calc PR A 1
H9B H 0.8081 0.6417 0.3748 0.088 Uiso 0.60 1 calc PR A 1
C8' C 0.7737(17) 0.5583(11) 0.3093(8) 0.086(4) Uani 0.45 1 d PDU A 2
H8'1 H 0.8587 0.5994 0.3487 0.103 Uiso 0.45 1 calc PR A 2
H8'2 H 0.8065 0.4913 0.3224 0.103 Uiso 0.45 1 calc PR A 2
C9' C 0.5475(17) 0.5779(8) 0.3230(9) 0.083(3) Uani 0.40 1 d PDU A 2
H9'1 H 0.4977 0.5476 0.3795 0.099 Uiso 0.40 1 calc PR A 2
H9'2 H 0.4667 0.5535 0.2711 0.099 Uiso 0.40 1 calc PR A 2
C10 C 0.3040(7) 0.6840(3) 0.3238(3) 0.1150(14) Uani 1 1 d . A .
H10A H 0.2499 0.6459 0.3748 0.138 Uiso 1 1 calc R . .
H10B H 0.2637 0.6537 0.2658 0.138 Uiso 1 1 calc R . .
C11 C 0.2254(7) 0.7833(3) 0.3284(3) 0.1109(13) Uani 1 1 d . . .
H11A H 0.0929 0.7857 0.3611 0.133 Uiso 1 1 calc R A .
H11B H 0.2060 0.8095 0.2666 0.133 Uiso 1 1 calc R . .
C12 C 0.3864(8) 0.8381(3) 0.3790(3) 0.1072(14) Uani 1 1 d . A .
H12A H 0.3289 0.8660 0.4352 0.129 Uiso 1 1 calc R . .
H12B H 0.4423 0.8896 0.3407 0.129 Uiso 1 1 calc R . .
C13 C 0.5511(7) 0.7664(4) 0.4013(3) 0.1115(15) Uani 1 1 d . A .
H13A H 0.6890 0.7956 0.3987 0.134 Uiso 1 1 calc R . .
H13B H 0.5297 0.7392 0.4626 0.134 Uiso 1 1 calc R . .
H1N H 0.771(7) 0.625(3) 0.190(3) 0.110(16) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.218(4) . ?
N1 C4 1.354(4) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 C7 1.322(5) . ?
N2 C8' 1.456(11) . ?
N2 C8 1.492(9) . ?
N2 H1N 0.73(4) . ?
N3 C10 1.436(5) . ?
N3 C13 1.456(5) . ?
N3 C9 1.482(7) . ?
N3 C9' 1.600(11) . ?
C1 C6 1.384(4) . ?
C1 C2 1.390(4) . ?
C1 C7 1.472(4) . ?
C2 C3 1.350(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(4) . ?
C5 C6 1.357(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.515(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C8' C9' 1.484(12) . ?
C8' H8'1 0.9700 . ?
C8' H8'2 0.9700 . ?
C9' H9'1 0.9700 . ?
C9' H9'2 0.9700 . ?
C10 C11 1.465(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.472(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.483(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

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
C4 N1 H1A 120.0 . . ?
C4 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C7 N2 C8' 117.4(6) . . ?
C7 N2 C8 127.5(5) . . ?
C8' N2 C8 28.8(5) . . ?
C7 N2 H1N 114(3) . . ?
C8' N2 H1N 123(3) . . ?
C8 N2 H1N 118(3) . . ?
C10 N3 C13 101.9(3) . . ?
C10 N3 C9 124.5(4) . . ?
C13 N3 C9 102.1(4) . . ?
C10 N3 C9' 89.5(5) . . ?
C13 N3 C9' 137.0(5) . . ?
C9 N3 C9' 41.8(4) . . ?
C6 C1 C2 116.3(3) . . ?
C6 C1 C7 124.6(3) . . ?
C2 C1 C7 119.0(3) . . ?
C3 C2 C1 122.0(3) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
N1 C4 C3 121.3(3) . . ?
N1 C4 C5 121.5(3) . . ?
C3 C4 C5 117.2(3) . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 122.1(3) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
O1 C7 N2 120.9(3) . . ?
O1 C7 C1 121.4(3) . . ?
N2 C7 C1 117.7(3) . . ?
N2 C8 C9 106.3(6) . . ?
N2 C8 H8A 110.5 . . ?
C9 C8 H8A 110.5 . . ?
N2 C8 H8B 110.5 . . ?
C9 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
N3 C9 C8 106.8(6) . . ?
N3 C9 H9A 110.4 . . ?
C8 C9 H9A 110.4 . . ?
N3 C9 H9B 110.4 . . ?
C8 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
N2 C8' C9' 103.3(9) . . ?
N2 C8' H8'1 111.1 . . ?
C9' C8' H8'1 111.1 . . ?
N2 C8' H8'2 111.1 . . ?
C9' C8' H8'2 111.1 . . ?
H8'1 C8' H8'2 109.1 . . ?
C8' C9' N3 105.6(9) . . ?
C8' C9' H9'1 110.6 . . ?
N3 C9' H9'1 110.6 . . ?
C8' C9' H9'2 110.6 . . ?
N3 C9' H9'2 110.6 . . ?
H9'1 C9' H9'2 108.8 . . ?
N3 C10 C11 105.0(3) . . ?
N3 C10 H10A 110.8 . . ?
C11 C10 H10A 110.8 . . ?
N3 C10 H10B 110.8 . . ?
C11 C10 H10B 110.8 . . ?
H10A C10 H10B 108.8 . . ?
C10 C11 C12 105.5(4) . . ?
C10 C11 H11A 110.6 . . ?
C12 C11 H11A 110.6 . . ?
C10 C11 H11B 110.6 . . ?
C12 C11 H11B 110.6 . . ?
H11A C11 H11B 108.8 . . ?
C11 C12 C13 105.0(3) . . ?
C11 C12 H12A 110.8 . . ?
C13 C12 H12A 110.8 . . ?
C11 C12 H12B 110.8 . . ?
C13 C12 H12B 110.8 . . ?
H12A C12 H12B 108.8 . . ?
N3 C13 C12 104.0(3) . . ?
N3 C13 H13A 111.0 . . ?
C12 C13 H13A 111.0 . . ?
N3 C13 H13B 111.0 . . ?
C12 C13 H13B 111.0 . . ?
H13A C13 H13B 109.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.2(4) . . . . ?
C7 C1 C2 C3 178.8(3) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C3 C4 N1 178.4(3) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
N1 C4 C5 C6 -178.3(3) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C4 C5 C6 C1 -0.1(5) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
C7 C1 C6 C5 -178.6(3) . . . . ?
C8' N2 C7 O1 14.1(9) . . . . ?
C8 N2 C7 O1 -18.1(8) . . . . ?
C8' N2 C7 C1 -166.5(7) . . . . ?
C8 N2 C7 C1 161.3(6) . . . . ?
C6 C1 C7 O1 166.6(3) . . . . ?
C2 C1 C7 O1 -12.3(4) . . . . ?
C6 C1 C7 N2 -12.8(5) . . . . ?
C2 C1 C7 N2 168.3(3) . . . . ?
C7 N2 C8 C9 128.3(7) . . . . ?
C8' N2 C8 C9 49.3(13) . . . . ?
C10 N3 C9 C8 72.7(7) . . . . ?
C13 N3 C9 C8 -173.5(6) . . . . ?
C9' N3 C9 C8 34.6(6) . . . . ?
N2 C8 C9 N3 73.6(9) . . . . ?
C7 N2 C8' C9' -157.4(8) . . . . ?
C8 N2 C8' C9' -38.7(11) . . . . ?
N2 C8' C9' N3 -77.6(12) . . . . ?
C10 N3 C9' C8' 169.5(8) . . . . ?
C13 N3 C9' C8' -83.4(10) . . . . ?
C9 N3 C9' C8' -41.0(6) . . . . ?
C13 N3 C10 C11 41.7(4) . . . . ?
C9 N3 C10 C11 155.6(4) . . . . ?
C9' N3 C10 C11 179.9(6) . . . . ?
N3 C10 C11 C12 -25.8(5) . . . . ?
C10 C11 C12 C13 -0.1(5) . . . . ?
C10 N3 C13 C12 -41.4(4) . . . . ?
C9 N3 C13 C12 -171.1(4) . . . . ?
C9' N3 C13 C12 -143.7(6) . . . . ?
C11 C12 C13 N3 25.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_compound_3_dimethyl
_database_code_depnum_ccdc_archive 'CCDC 1425936'
_audit_update_record             
;
2015-09-18 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H17 N3 O'
_chemical_formula_sum            'C11 H17 N3 O'
_chemical_formula_weight         207.28

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '

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

_cell_length_a                   5.9755(3)
_cell_length_b                   13.1272(8)
_cell_length_c                   14.4992(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1137.34(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3980
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      33.10

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9779
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5135
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1995
_reflns_number_gt                1918
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_cell_refinement       'SAINT (APEX2, Bruker, 2006)'
_computing_data_reduction        'SAINT (APEX2, Bruker, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0390P)²+0.2790P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(16)
_refine_ls_number_reflns         1995
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0824
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4884(2) 1.06356(8) 0.18268(7) 0.0274(3) Uani 1 1 d . A 4
N2 N 0.2676(2) 0.92501(9) 0.20264(9) 0.0231(3) Uani 1 1 d . A 4
H2 H 0.2326 0.8638 0.1826 0.028 Uiso 1 1 calc R A 4
N3 N -0.0088(2) 0.79576(9) 0.32929(8) 0.0224(3) Uani 1 1 d . A 4
N1 N 0.7456(2) 0.81933(9) -0.18320(9) 0.0229(3) Uani 1 1 d . A 4
H1A H 0.8802 0.8360 -0.2027 0.027 Uiso 1 1 calc R A 4
H1B H 0.6613 0.7784 -0.2164 0.027 Uiso 1 1 calc R A 4
C4 C 0.6671(2) 0.85720(11) -0.10071(10) 0.0190(3) Uani 1 1 d . A 4
C5 C 0.4555(3) 0.82893(10) -0.06729(10) 0.0196(3) Uani 1 1 d . A 4
H5 H 0.3644 0.7840 -0.1024 0.024 Uiso 1 1 calc R A 4
C6 C 0.3787(2) 0.86580(11) 0.01612(10) 0.0185(3) Uani 1 1 d . A 4
H6 H 0.2354 0.8455 0.0377 0.022 Uiso 1 1 calc R A 4
C1 C 0.5075(2) 0.93243(10) 0.06949(10) 0.0181(3) Uani 1 1 d . A 4
C7 C 0.4222(2) 0.97933(11) 0.15625(10) 0.0189(3) Uani 1 1 d . A 4
C8 C 0.1559(3) 0.96386(12) 0.28493(11) 0.0269(4) Uani 1 1 d . A 4
H8A H 0.0064 0.9903 0.2677 0.032 Uiso 1 1 calc R A 4
H8B H 0.2438 1.0212 0.3104 0.032 Uiso 1 1 calc R A 4
C9 C 0.1290(3) 0.88284(12) 0.35847(10) 0.0244(4) Uani 1 1 d . A 4
H9A H 0.2790 0.8576 0.3763 0.029 Uiso 1 1 calc R A 4
H9B H 0.0601 0.9141 0.4137 0.029 Uiso 1 1 calc R A 4
C11 C -0.2430(3) 0.82415(14) 0.31641(15) 0.0380(4) Uani 1 1 d . A 4
H11A H -0.3298 0.7638 0.2991 0.057 Uiso 1 1 calc R A 4
H11B H -0.2542 0.8754 0.2675 0.057 Uiso 1 1 calc R A 4
H11C H -0.3023 0.8523 0.3740 0.057 Uiso 1 1 calc R A 4
C10 C 0.0064(3) 0.71539(13) 0.39947(12) 0.0358(4) Uani 1 1 d . A 4
H10A H -0.0421 0.7425 0.4592 0.054 Uiso 1 1 calc R A 4
H10B H 0.1616 0.6918 0.4041 0.054 Uiso 1 1 calc R A 4
H10C H -0.0902 0.6583 0.3819 0.054 Uiso 1 1 calc R A 4
C3 C 0.7981(2) 0.92251(11) -0.04646(10) 0.0209(3) Uani 1 1 d . A 4
H3 H 0.9432 0.9414 -0.0671 0.025 Uiso 1 1 calc R A 4
C2 C 0.7194(3) 0.95982(11) 0.03657(10) 0.0201(3) Uani 1 1 d . A 4
H2A H 0.8103 1.0047 0.0718 0.024 Uiso 1 1 calc R A 4


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.2354(18) . ?
N2 C7 1.347(2) . ?
N2 C8 1.4592(19) . ?
N2 H2 0.8800 . ?
N3 C11 1.460(2) . ?
N3 C10 1.469(2) . ?
N3 C9 1.471(2) . ?
N1 C4 1.378(2) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
C4 C3 1.402(2) . ?
C4 C5 1.404(2) . ?
C5 C6 1.381(2) . ?
C5 H5 0.9500 . ?
C6 C1 1.398(2) . ?
C6 H6 0.9500 . ?
C1 C2 1.400(2) . ?
C1 C7 1.490(2) . ?
C8 C9 1.515(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C3 C2 1.382(2) . ?
C3 H3 0.9500 . ?
C2 H2A 0.9500 . ?

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
C7 N2 C8 122.48(13) . . ?
C7 N2 H2 118.8 . . ?
C8 N2 H2 118.8 . . ?
C11 N3 C10 109.34(14) . . ?
C11 N3 C9 112.02(12) . . ?
C10 N3 C9 108.93(13) . . ?
C4 N1 H1A 120.0 . . ?
C4 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
N1 C4 C3 121.16(14) . . ?
N1 C4 C5 120.73(13) . . ?
C3 C4 C5 118.08(14) . . ?
C6 C5 C4 120.58(14) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 121.40(14) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
C6 C1 C2 118.00(13) . . ?
C6 C1 C7 122.51(13) . . ?
C2 C1 C7 119.39(13) . . ?
O1 C7 N2 122.59(14) . . ?
O1 C7 C1 121.47(13) . . ?
N2 C7 C1 115.93(12) . . ?
N2 C8 C9 112.25(13) . . ?
N2 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N2 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N3 C9 C8 113.75(13) . . ?
N3 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
N3 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C2 C3 C4 121.00(14) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C2 C1 120.91(13) . . ?
C3 C2 H2A 119.5 . . ?
C1 C2 H2A 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C4 C5 C6 178.99(13) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
C5 C6 C1 C2 -1.0(2) . . . . ?
C5 C6 C1 C7 175.40(12) . . . . ?
C8 N2 C7 O1 3.8(2) . . . . ?
C8 N2 C7 C1 -175.32(13) . . . . ?
C6 C1 C7 O1 -150.68(14) . . . . ?
C2 C1 C7 O1 25.6(2) . . . . ?
C6 C1 C7 N2 28.40(19) . . . . ?
C2 C1 C7 N2 -155.28(13) . . . . ?
C7 N2 C8 C9 -139.39(14) . . . . ?
C11 N3 C9 C8 -67.95(18) . . . . ?
C10 N3 C9 C8 170.96(14) . . . . ?
N2 C8 C9 N3 -61.58(18) . . . . ?
N1 C4 C3 C2 -179.56(13) . . . . ?
C5 C4 C3 C2 -1.4(2) . . . . ?
C4 C3 C2 C1 0.8(2) . . . . ?
C6 C1 C2 C3 0.4(2) . . . . ?
C7 C1 C2 C3 -176.10(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.033
####################################################################### 
# 
# 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_compound_4_morpholine
_database_code_depnum_ccdc_archive 'CCDC 1425937'
_audit_update_record             
;
2015-09-18 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H19 N3 O2'
_chemical_formula_sum            'C13 H19 N3 O2'
_chemical_formula_weight         249.31

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '

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

_cell_length_a                   9.3267(14)
_cell_length_b                   9.8628(15)
_cell_length_c                   14.061(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1293.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4142
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      28.05

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9723
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6521
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2263
_reflns_number_gt                2180
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_cell_refinement       'SAINT (APEX2, Bruker, 2006)'
_computing_data_reduction        'SAINT (APEX2, Bruker, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0365P)²+0.2607P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.6(12)
_refine_ls_number_reflns         2263
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0766
_refine_ls_wR_factor_gt          0.0757
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.19658(12) 0.66142(11) 0.47721(8) 0.0304(3) Uani 1 1 d . A 4
O2 O 0.41673(13) 0.87063(12) 0.00693(8) 0.0359(3) Uani 1 1 d . A 4
N1 N 0.41991(15) 0.59809(14) 0.90434(9) 0.0304(3) Uani 1 1 d . A 4
H1A H 0.3957 0.5192 0.9287 0.036 Uiso 1 1 calc R A 4
H1B H 0.4599 0.6602 0.9406 0.036 Uiso 1 1 calc R A 4
N2 N 0.39296(16) 0.79588(13) 0.46907(9) 0.0300(3) Uani 1 1 d . A 4
H2A H 0.4727 0.8213 0.4973 0.036 Uiso 1 1 calc R A 4
N3 N 0.44940(14) 0.84509(14) 0.20796(9) 0.0264(3) Uani 1 1 d . A 4
C1 C 0.34260(16) 0.68087(15) 0.61618(11) 0.0245(3) Uani 1 1 d . A 4
C2 C 0.30412(17) 0.55656(15) 0.65563(11) 0.0267(3) Uani 1 1 d . A 4
H2 H 0.2581 0.4906 0.6170 0.032 Uiso 1 1 calc R A 4
C3 C 0.33169(17) 0.52754(16) 0.74997(11) 0.0263(4) Uani 1 1 d . A 4
H3 H 0.3073 0.4410 0.7748 0.032 Uiso 1 1 calc R A 4
C4 C 0.39516(17) 0.62443(15) 0.80929(11) 0.0250(3) Uani 1 1 d . A 4
C5 C 0.43210(17) 0.75030(15) 0.76996(11) 0.0262(4) Uani 1 1 d . A 4
H5 H 0.4744 0.8179 0.8091 0.031 Uiso 1 1 calc R A 4
C6 C 0.40764(17) 0.77706(15) 0.67507(11) 0.0258(3) Uani 1 1 d . A 4
H6 H 0.4354 0.8622 0.6493 0.031 Uiso 1 1 calc R A 4
C7 C 0.30534(17) 0.71089(14) 0.51534(11) 0.0250(3) Uani 1 1 d . A 4
C8 C 0.36299(19) 0.84836(17) 0.37450(11) 0.0326(4) Uani 1 1 d . A 4
H8A H 0.3879 0.9459 0.3722 0.039 Uiso 1 1 calc R A 4
H8B H 0.2592 0.8396 0.3611 0.039 Uiso 1 1 calc R A 4
C9 C 0.44716(18) 0.77324(16) 0.29880(11) 0.0280(4) Uani 1 1 d . A 4
H9A H 0.5469 0.7603 0.3211 0.034 Uiso 1 1 calc R A 4
H9B H 0.4042 0.6825 0.2893 0.034 Uiso 1 1 calc R A 4
C10 C 0.54456(18) 0.77618(17) 0.14107(12) 0.0308(4) Uani 1 1 d . A 4
H10A H 0.5068 0.6846 0.1269 0.037 Uiso 1 1 calc R A 4
H10B H 0.6410 0.7661 0.1696 0.037 Uiso 1 1 calc R A 4
C11 C 0.55470(19) 0.85759(19) 0.05054(11) 0.0356(4) Uani 1 1 d . A 4
H11A H 0.5934 0.9488 0.0649 0.043 Uiso 1 1 calc R A 4
H11B H 0.6214 0.8123 0.0059 0.043 Uiso 1 1 calc R A 4
C12 C 0.3208(2) 0.93594(17) 0.07129(12) 0.0338(4) Uani 1 1 d . A 4
H12A H 0.2250 0.9432 0.0414 0.041 Uiso 1 1 calc R A 4
H12B H 0.3556 1.0289 0.0843 0.041 Uiso 1 1 calc R A 4
C13 C 0.30779(18) 0.85928(17) 0.16435(11) 0.0303(4) Uani 1 1 d . A 4
H13A H 0.2431 0.9089 0.2080 0.036 Uiso 1 1 calc R A 4
H13B H 0.2662 0.7685 0.1525 0.036 Uiso 1 1 calc R A 4


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.2467(19) . ?
O2 C12 1.426(2) . ?
O2 C11 1.431(2) . ?
N1 C4 1.381(2) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 C7 1.339(2) . ?
N2 C8 1.454(2) . ?
N2 H2A 0.8800 . ?
N3 C10 1.461(2) . ?
N3 C9 1.461(2) . ?
N3 C13 1.463(2) . ?
C1 C2 1.393(2) . ?
C1 C6 1.398(2) . ?
C1 C7 1.490(2) . ?
C2 C3 1.381(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.400(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.402(2) . ?
C5 C6 1.379(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C9 1.516(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.508(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.516(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

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 O2 C11 109.43(12) . . ?
C4 N1 H1A 120.0 . . ?
C4 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C7 N2 C8 123.35(14) . . ?
C7 N2 H2A 118.3 . . ?
C8 N2 H2A 118.3 . . ?
C10 N3 C9 110.24(13) . . ?
C10 N3 C13 108.86(12) . . ?
C9 N3 C13 113.58(12) . . ?
C2 C1 C6 118.25(14) . . ?
C2 C1 C7 119.61(14) . . ?
C6 C1 C7 122.02(14) . . ?
C3 C2 C1 121.13(15) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 120.63(15) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
N1 C4 C3 121.26(14) . . ?
N1 C4 C5 120.48(14) . . ?
C3 C4 C5 118.25(14) . . ?
C6 C5 C4 120.69(14) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 121.00(14) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
O1 C7 N2 122.17(14) . . ?
O1 C7 C1 121.42(14) . . ?
N2 C7 C1 116.39(13) . . ?
N2 C8 C9 111.63(13) . . ?
N2 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
N2 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
N3 C9 C8 112.60(13) . . ?
N3 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
N3 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
N3 C10 C11 109.50(14) . . ?
N3 C10 H10A 109.8 . . ?
C11 C10 H10A 109.8 . . ?
N3 C10 H10B 109.8 . . ?
C11 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
O2 C11 C10 110.67(14) . . ?
O2 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
O2 C12 C13 111.88(13) . . ?
O2 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
O2 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
N3 C13 C12 109.70(14) . . ?
N3 C13 H13A 109.7 . . ?
C12 C13 H13A 109.7 . . ?
N3 C13 H13B 109.7 . . ?
C12 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.2(2) . . . . ?
C7 C1 C2 C3 -177.30(15) . . . . ?
C1 C2 C3 C4 2.1(2) . . . . ?
C2 C3 C4 N1 178.28(14) . . . . ?
C2 C3 C4 C5 -1.1(2) . . . . ?
N1 C4 C5 C6 179.98(15) . . . . ?
C3 C4 C5 C6 -0.6(2) . . . . ?
C4 C5 C6 C1 1.5(2) . . . . ?
C2 C1 C6 C5 -0.5(2) . . . . ?
C7 C1 C6 C5 175.45(15) . . . . ?
C8 N2 C7 O1 6.1(2) . . . . ?
C8 N2 C7 C1 -172.43(14) . . . . ?
C2 C1 C7 O1 30.3(2) . . . . ?
C6 C1 C7 O1 -145.61(15) . . . . ?
C2 C1 C7 N2 -151.14(14) . . . . ?
C6 C1 C7 N2 32.9(2) . . . . ?
C7 N2 C8 C9 -101.03(17) . . . . ?
C10 N3 C9 C8 173.74(13) . . . . ?
C13 N3 C9 C8 -63.79(18) . . . . ?
N2 C8 C9 N3 -164.72(13) . . . . ?
C9 N3 C10 C11 -175.55(13) . . . . ?
C13 N3 C10 C11 59.25(17) . . . . ?
C12 O2 C11 C10 59.19(17) . . . . ?
N3 C10 C11 O2 -60.81(18) . . . . ?
C11 O2 C12 C13 -57.79(17) . . . . ?
C10 N3 C13 C12 -57.30(17) . . . . ?
C9 N3 C13 C12 179.47(13) . . . . ?
O2 C12 C13 N3 57.52(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.031
####################################################################### 
# 
# 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_compound_5_piperidine
_database_code_depnum_ccdc_archive 'CCDC 1425938'
_audit_update_record             
;
2015-09-18 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H21 N3 O'
_chemical_formula_sum            'C14 H21 N3 O'
_chemical_formula_weight         247.34

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   9.624(2)
_cell_length_b                   10.246(3)
_cell_length_c                   13.768(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1357.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1879
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      22.36

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9807
_exptl_absorpt_correction_T_max  0.9945
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5609
_diffrn_reflns_av_R_equivalents  0.0766
_diffrn_reflns_av_sigmaI/netI    0.1015
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2383
_reflns_number_gt                1909
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_cell_refinement       'SAINT (APEX2, Bruker, 2006)'
_computing_data_reduction        'SAINT (APEX2, Bruker, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0815P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    costr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.069(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_number_reflns         2383
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.1626
_refine_ls_wR_factor_gt          0.1486
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2983(2) 0.3243(2) 0.97866(15) 0.0546(6) Uani 1 1 d . . .
N1 N 0.0731(3) 0.4345(3) 1.40552(19) 0.0603(8) Uani 1 1 d . . .
H1A H 0.1077 0.5054 1.4287 0.072 Uiso 1 1 calc R . .
H1B H 0.0225 0.3852 1.4417 0.072 Uiso 1 1 calc R . .
N2 N 0.0931(2) 0.2181(3) 0.97038(17) 0.0493(6) Uani 1 1 d . . .
H2 H 0.0129 0.2073 0.9968 0.059 Uiso 1 1 calc R . .
N3 N 0.0472(2) 0.1447(3) 0.70638(16) 0.0445(6) Uani 1 1 d . . .
C1 C 0.1520(3) 0.3293(3) 1.1175(2) 0.0401(7) Uani 1 1 d . . .
C2 C 0.2076(3) 0.4424(3) 1.1573(2) 0.0456(7) Uani 1 1 d . . .
H2A H 0.2648 0.4951 1.1195 0.055 Uiso 1 1 calc R . .
C3 C 0.1796(3) 0.4778(3) 1.2516(2) 0.0489(8) Uani 1 1 d . . .
H3 H 0.2156 0.5554 1.2760 0.059 Uiso 1 1 calc R . .
C4 C 0.0987(3) 0.3999(3) 1.3105(2) 0.0416(7) Uani 1 1 d . . .
C5 C 0.0454(3) 0.2852(3) 1.2723(2) 0.0462(7) Uani 1 1 d . . .
H5 H -0.0085 0.2309 1.3112 0.055 Uiso 1 1 calc R . .
C6 C 0.0712(3) 0.2509(3) 1.1775(2) 0.0438(7) Uani 1 1 d . . .
H6 H 0.0340 0.1739 1.1530 0.053 Uiso 1 1 calc R . .
C7 C 0.1864(3) 0.2913(3) 1.0168(2) 0.0424(7) Uani 1 1 d . . .
C8 C 0.1197(4) 0.1552(4) 0.8770(2) 0.0565(8) Uani 1 1 d . . .
H8A H 0.0895 0.0650 0.8802 0.068 Uiso 1 1 calc R . .
H8B H 0.2189 0.1555 0.8645 0.068 Uiso 1 1 calc R . .
C9 C 0.0463(3) 0.2220(3) 0.7945(2) 0.0488(7) Uani 1 1 d . . .
H9A H -0.0491 0.2392 0.8132 0.059 Uiso 1 1 calc R . .
H9B H 0.0909 0.3052 0.7818 0.059 Uiso 1 1 calc R . .
C10 C -0.0370(3) 0.2068(3) 0.6324(2) 0.0525(8) Uani 1 1 d . . .
H10A H 0.0045 0.2897 0.6148 0.063 Uiso 1 1 calc R . .
H10B H -0.1289 0.2239 0.6584 0.063 Uiso 1 1 calc R . .
C11 C -0.0497(3) 0.1233(4) 0.5437(2) 0.0596(9) Uani 1 1 d . . .
H11A H -0.1028 0.1698 0.4948 0.072 Uiso 1 1 calc R . .
H11B H -0.1000 0.0443 0.5600 0.072 Uiso 1 1 calc R . .
C12 C 0.0908(4) 0.0872(4) 0.5022(2) 0.0625(9) Uani 1 1 d . . .
H12A H 0.0793 0.0246 0.4500 0.075 Uiso 1 1 calc R . .
H12B H 0.1357 0.1643 0.4761 0.075 Uiso 1 1 calc R . .
C13 C 0.1794(4) 0.0289(4) 0.5816(2) 0.0615(9) Uani 1 1 d . . .
H13A H 0.2725 0.0140 0.5571 0.074 Uiso 1 1 calc R . .
H13B H 0.1409 -0.0547 0.6009 0.074 Uiso 1 1 calc R . .
C14 C 0.1862(3) 0.1187(3) 0.6696(2) 0.0559(8) Uani 1 1 d . . .
H14A H 0.2417 0.0781 0.7200 0.067 Uiso 1 1 calc R . .
H14B H 0.2305 0.2002 0.6515 0.067 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.244(3) . ?
N1 C4 1.377(4) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 C7 1.334(4) . ?
N2 C8 1.461(4) . ?
N2 H2 0.8600 . ?
N3 C9 1.448(4) . ?
N3 C10 1.448(4) . ?
N3 C14 1.456(4) . ?
C1 C2 1.389(4) . ?
C1 C6 1.390(4) . ?
C1 C7 1.477(4) . ?
C2 C3 1.375(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.378(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(4) . ?
C5 C6 1.374(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.503(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.496(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.513(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.509(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.522(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?

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
C4 N1 H1A 120.0 . . ?
C4 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C7 N2 C8 123.5(2) . . ?
C7 N2 H2 118.3 . . ?
C8 N2 H2 118.3 . . ?
C9 N3 C10 110.2(2) . . ?
C9 N3 C14 113.4(2) . . ?
C10 N3 C14 110.5(2) . . ?
C2 C1 C6 117.6(3) . . ?
C2 C1 C7 120.3(3) . . ?
C6 C1 C7 122.0(3) . . ?
C3 C2 C1 121.2(3) . . ?
C3 C2 H2A 119.4 . . ?
C1 C2 H2A 119.4 . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
N1 C4 C3 120.7(3) . . ?
N1 C4 C5 120.8(3) . . ?
C3 C4 C5 118.5(3) . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 121.2(3) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
O1 C7 N2 122.2(3) . . ?
O1 C7 C1 121.2(3) . . ?
N2 C7 C1 116.5(2) . . ?
N2 C8 C9 112.5(3) . . ?
N2 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
N2 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
N3 C9 C8 112.4(3) . . ?
N3 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
N3 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
N3 C10 C11 111.7(3) . . ?
N3 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
N3 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 C12 112.0(3) . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 109.2(3) . . ?
C13 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.3 . . ?
C12 C13 C14 111.2(3) . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
N3 C14 C13 110.4(3) . . ?
N3 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
N3 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -2.3(4) . . . . ?
C7 C1 C2 C3 -178.4(3) . . . . ?
C1 C2 C3 C4 2.0(4) . . . . ?
C2 C3 C4 N1 178.7(3) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
N1 C4 C5 C6 -179.9(3) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C4 C5 C6 C1 0.4(4) . . . . ?
C2 C1 C6 C5 1.1(4) . . . . ?
C7 C1 C6 C5 177.1(3) . . . . ?
C8 N2 C7 O1 8.6(4) . . . . ?
C8 N2 C7 C1 -170.0(3) . . . . ?
C2 C1 C7 O1 27.6(4) . . . . ?
C6 C1 C7 O1 -148.3(3) . . . . ?
C2 C1 C7 N2 -153.7(2) . . . . ?
C6 C1 C7 N2 30.4(4) . . . . ?
C7 N2 C8 C9 -106.0(3) . . . . ?
C10 N3 C9 C8 174.0(2) . . . . ?
C14 N3 C9 C8 -61.5(3) . . . . ?
N2 C8 C9 N3 -167.3(2) . . . . ?
C9 N3 C10 C11 -174.5(2) . . . . ?
C14 N3 C10 C11 59.4(3) . . . . ?
N3 C10 C11 C12 -56.1(4) . . . . ?
C10 C11 C12 C13 52.4(4) . . . . ?
C11 C12 C13 C14 -53.2(4) . . . . ?
C9 N3 C14 C13 175.8(3) . . . . ?
C10 N3 C14 C13 -59.9(3) . . . . ?
C12 C13 C14 N3 57.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.098
####################################################################### 
# 
# 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_compound_6_pyridine
_database_code_depnum_ccdc_archive 'CCDC 1442290'
_audit_update_record             
;
2015-12-13 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 N3 O'
_chemical_formula_sum            'C17 H15 N3 O'
_chemical_formula_weight         277.32

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

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   'P-42(1)c '

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

_cell_length_a                   19.628(6)
_cell_length_b                   19.628(6)
_cell_length_c                   8.151(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3140.0(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    926
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      19.11

_exptl_crystal_description       'THIN NEEDLE'
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9880
_exptl_absorpt_correction_T_max  0.9977
_exptl_absorpt_process_details   'SADABS (Bruker)2006'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36254
_diffrn_reflns_av_R_equivalents  0.1064
_diffrn_reflns_av_sigmaI/netI    0.0768
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2748
_reflns_number_gt                1722
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1216P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(4)
_refine_ls_number_reflns         2748
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1354
_refine_ls_R_factor_gt           0.0775
_refine_ls_wR_factor_ref         0.2077
_refine_ls_wR_factor_gt          0.1824
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O O -0.00264(15) 0.79800(17) 0.2679(4) 0.0496(9) Uani 1 1 d . . .
N1 N -0.04862(18) 0.88999(19) 1.0110(4) 0.0537(11) Uani 1 1 d . . .
H1A H -0.0395 0.8677 1.1021 0.064 Uiso 1 1 calc R . .
H1B H -0.0692 0.9298 1.0154 0.064 Uiso 1 1 calc R . .
N2 N 0.08185(17) 0.73754(18) 0.3863(4) 0.0465(10) Uani 1 1 d . . .
H2 H 0.1060 0.7292 0.4751 0.056 Uiso 1 1 calc R . .
N3 N 0.25372(18) 0.69708(19) 0.1500(5) 0.0514(10) Uani 1 1 d . . .
C1 C 0.01063(18) 0.8102(2) 0.5559(6) 0.0381(11) Uani 1 1 d . . .
C2 C -0.0242(2) 0.8708(2) 0.5677(5) 0.0382(10) Uani 1 1 d . . .
H2A H -0.0348 0.8950 0.4702 0.046 Uiso 1 1 calc R . .
C3 C -0.0438(2) 0.8971(2) 0.7147(6) 0.0410(11) Uani 1 1 d . . .
H3 H -0.0668 0.9397 0.7176 0.049 Uiso 1 1 calc R . .
C4 C -0.03072(19) 0.8626(2) 0.8616(6) 0.0378(10) Uani 1 1 d . . .
C5 C 0.0016(2) 0.8003(2) 0.8513(6) 0.0438(11) Uani 1 1 d . . .
H5 H 0.0096 0.7749 0.9486 0.053 Uiso 1 1 calc R . .
C6 C 0.0222(2) 0.7742(2) 0.7035(5) 0.0424(12) Uani 1 1 d . . .
H6 H 0.0446 0.7314 0.7002 0.051 Uiso 1 1 calc R . .
C7 C 0.0293(2) 0.7826(2) 0.3931(6) 0.0415(11) Uani 1 1 d . . .
C8 C 0.0985(2) 0.7030(2) 0.2332(6) 0.0524(13) Uani 1 1 d . . .
H8A H 0.0555 0.6905 0.1773 0.063 Uiso 1 1 calc R . .
H8B H 0.1229 0.6603 0.2593 0.063 Uiso 1 1 calc R . .
C9 C 0.1419(2) 0.7446(3) 0.1152(6) 0.0520(13) Uani 1 1 d . . .
H9A H 0.1420 0.7222 0.0064 0.062 Uiso 1 1 calc R . .
H9B H 0.1215 0.7904 0.1020 0.062 Uiso 1 1 calc R . .
C10 C 0.2141(2) 0.7519(2) 0.1749(5) 0.0476(12) Uani 1 1 d . . .
C11 C 0.3194(3) 0.7016(3) 0.2070(7) 0.0668(16) Uani 1 1 d . . .
H11 H 0.3490 0.6639 0.1896 0.080 Uiso 1 1 calc R . .
C12 C 0.3449(3) 0.7575(3) 0.2880(8) 0.0704(15) Uani 1 1 d . . .
H12 H 0.3909 0.7585 0.3244 0.084 Uiso 1 1 calc R . .
C13 C 0.3023(3) 0.8119(3) 0.3148(8) 0.0723(16) Uani 1 1 d . . .
H13 H 0.3181 0.8507 0.3732 0.087 Uiso 1 1 calc R . .
C14 C 0.2359(3) 0.8097(3) 0.2556(6) 0.0569(13) Uani 1 1 d . . .
H14 H 0.2061 0.8473 0.2705 0.068 Uiso 1 1 calc R . .
C15 C 0.4576(4) 0.8883(4) 0.0631(11) 0.126(3) Uani 1 1 d . . .
C16 C 0.3904(7) 0.9517(6) 0.058(2) 0.205(5) Uani 1 1 d . . .
C17 C 0.4036(5) 1.0186(5) 0.1024(13) 0.137(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O C7 1.235(5) . ?
N1 C4 1.377(5) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 C7 1.360(6) . ?
N2 C8 1.457(6) . ?
N2 H2 0.8800 . ?
N3 C10 1.344(5) . ?
N3 C11 1.374(7) . ?
C1 C2 1.375(6) . ?
C1 C6 1.413(6) . ?
C1 C7 1.479(6) . ?
C2 C3 1.360(6) . ?
C2 H2A 0.9500 . ?
C3 C4 1.400(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(6) . ?
C5 C6 1.369(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C9 1.522(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.506(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C14 1.378(7) . ?
C11 C12 1.375(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(7) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.815(14) . ?
C16 C17 1.386(14) . ?

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
C4 N1 H1A 120.0 . . ?
C4 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C7 N2 C8 120.5(4) . . ?
C7 N2 H2 119.8 . . ?
C8 N2 H2 119.8 . . ?
C10 N3 C11 116.1(4) . . ?
C2 C1 C6 116.9(4) . . ?
C2 C1 C7 120.2(4) . . ?
C6 C1 C7 122.8(4) . . ?
C3 C2 C1 122.1(4) . . ?
C3 C2 H2A 118.9 . . ?
C1 C2 H2A 118.9 . . ?
C2 C3 C4 121.1(4) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
N1 C4 C5 121.2(4) . . ?
N1 C4 C3 121.4(4) . . ?
C5 C4 C3 117.4(4) . . ?
C6 C5 C4 121.4(4) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 121.0(4) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
O C7 N2 120.7(4) . . ?
O C7 C1 121.8(4) . . ?
N2 C7 C1 117.5(4) . . ?
N2 C8 C9 114.7(4) . . ?
N2 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
N2 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C8 112.0(4) . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N3 C10 C14 123.4(4) . . ?
N3 C10 C9 114.8(4) . . ?
C14 C10 C9 121.7(4) . . ?
N3 C11 C12 123.7(5) . . ?
N3 C11 H11 118.1 . . ?
C12 C11 H11 118.1 . . ?
C13 C12 C11 118.4(5) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C12 C13 C14 119.4(6) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C10 C14 C13 118.9(5) . . ?
C10 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C17 C16 C15 120.5(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 3.2(6) . . . . ?
C7 C1 C2 C3 178.4(4) . . . . ?
C1 C2 C3 C4 -1.5(6) . . . . ?
C2 C3 C4 N1 178.0(4) . . . . ?
C2 C3 C4 C5 -1.3(6) . . . . ?
N1 C4 C5 C6 -177.0(4) . . . . ?
C3 C4 C5 C6 2.2(6) . . . . ?
C4 C5 C6 C1 -0.5(6) . . . . ?
C2 C1 C6 C5 -2.2(6) . . . . ?
C7 C1 C6 C5 -177.2(4) . . . . ?
C8 N2 C7 O -4.2(6) . . . . ?
C8 N2 C7 C1 173.6(4) . . . . ?
C2 C1 C7 O -24.3(6) . . . . ?
C6 C1 C7 O 150.5(4) . . . . ?
C2 C1 C7 N2 157.8(4) . . . . ?
C6 C1 C7 N2 -27.3(6) . . . . ?
C7 N2 C8 C9 81.9(5) . . . . ?
N2 C8 C9 C10 71.6(5) . . . . ?
C11 N3 C10 C14 -1.4(6) . . . . ?
C11 N3 C10 C9 -178.4(4) . . . . ?
C8 C9 C10 N3 78.5(5) . . . . ?
C8 C9 C10 C14 -98.5(5) . . . . ?
C10 N3 C11 C12 1.1(7) . . . . ?
N3 C11 C12 C13 0.5(8) . . . . ?
C11 C12 C13 C14 -1.9(8) . . . . ?
N3 C10 C14 C13 0.1(7) . . . . ?
C9 C10 C14 C13 176.8(4) . . . . ?
C12 C13 C14 C10 1.6(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.081
