# 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_sb833_hy_compound_3b
_database_code_depnum_ccdc_archive 'CCDC 1510209'
_audit_update_record             
;
2016-10-17 deposited with the CCDC.
2016-12-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 ethyl (E)-4-(pyrrolidin-1-yldiazenyl)benzoate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H17 N3 O2'
_chemical_formula_sum            'C13 H17 N3 O2'
_chemical_formula_weight         247.29

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   7.8721(3)
_cell_length_b                   8.4927(3)
_cell_length_c                   10.4598(4)
_cell_angle_alpha                68.931(2)
_cell_angle_beta                 89.853(2)
_cell_angle_gamma                77.388(2)
_cell_volume                     634.58(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    4756
_cell_measurement_theta_min      4.6
_cell_measurement_theta_max      72.1

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.727
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8560
_exptl_absorpt_correction_T_max  0.9812
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
;
 dx = 40 mm, 1 deg., 12+1 runs, 2498 frames, 12/14/16/18/20 sec./frame
;



_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE with Photon100 detector'
_diffrn_measurement_method       'rotation in φ and ω, 1°, shutterless'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            10221
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.546
_diffrn_reflns_theta_max         72.123
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2484
_reflns_number_gt                2065
_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       'APEX3 v2015.9-RC2 (Bruker AXS)'
_computing_cell_refinement       'APEX3 v2015.9-RC2 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Shelxtl
_computing_publication_material  publCIF

_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)+(0.0434P)²+0.1649P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_ls_extinction_coef       0.0038(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2484
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
C1 C 0.59939(17) 0.35824(16) 0.18957(13) 0.0200(3) Uani 1 1 d . . . . .
H1 H 0.5206 0.3622 0.1192 0.024 Uiso 1 1 calc R U . . .
C2 C 0.56750(16) 0.48916(16) 0.24197(13) 0.0201(3) Uani 1 1 d . . . . .
H2 H 0.4667 0.5818 0.2079 0.024 Uiso 1 1 calc R U . . .
C3 C 0.68263(16) 0.48590(16) 0.34467(12) 0.0177(3) Uani 1 1 d . . . . .
C4 C 0.82999(16) 0.34853(16) 0.39400(12) 0.0187(3) Uani 1 1 d . . . . .
H4 H 0.9091 0.3453 0.4638 0.022 Uiso 1 1 calc R U . . .
C5 C 0.86181(16) 0.21711(16) 0.34210(12) 0.0192(3) Uani 1 1 d . . . . .
H5 H 0.9624 0.1243 0.3765 0.023 Uiso 1 1 calc R U . . .
C6 C 0.74603(16) 0.22037(15) 0.23892(12) 0.0175(3) Uani 1 1 d . . . . .
N7 N 0.76625(14) 0.09407(13) 0.17741(10) 0.0185(2) Uani 1 1 d . . . . .
N8 N 0.89560(14) -0.03492(13) 0.23793(10) 0.0185(2) Uani 1 1 d . . . . .
N9 N 0.92350(14) -0.15262(13) 0.18265(10) 0.0198(2) Uani 1 1 d . . . . .
C10 C 1.06667(17) -0.30696(16) 0.24032(13) 0.0203(3) Uani 1 1 d . . . . .
H10A H 1.0319 -0.3965 0.3198 0.024 Uiso 1 1 calc R U . . .
H10B H 1.1716 -0.2778 0.2693 0.024 Uiso 1 1 calc R U . . .
C11 C 1.09878(17) -0.36693(17) 0.11976(13) 0.0217(3) Uani 1 1 d . . . . .
H11A H 1.1450 -0.4941 0.1523 0.026 Uiso 1 1 calc R U . . .
H11B H 1.1824 -0.3089 0.0604 0.026 Uiso 1 1 calc R U . . .
C12 C 0.91751(17) -0.31346(17) 0.04227(13) 0.0216(3) Uani 1 1 d . . . . .
H12A H 0.9279 -0.2951 -0.0561 0.026 Uiso 1 1 calc R U . . .
H12B H 0.8510 -0.4037 0.0823 0.026 Uiso 1 1 calc R U . . .
C13 C 0.82748(17) -0.14376(16) 0.05946(13) 0.0211(3) Uani 1 1 d . . . . .
H13A H 0.8385 -0.0416 -0.0214 0.025 Uiso 1 1 calc R U . . .
H13B H 0.7022 -0.1385 0.0733 0.025 Uiso 1 1 calc R U . . .
C14 C 0.65579(16) 0.62421(16) 0.40349(12) 0.0180(3) Uani 1 1 d . . . . .
O14 O 0.75038(12) 0.62401(12) 0.49418(9) 0.0262(2) Uani 1 1 d . . . . .
O15 O 0.51412(11) 0.75223(11) 0.34281(9) 0.0209(2) Uani 1 1 d . . . . .
C15 C 0.47936(17) 0.89093(16) 0.39647(13) 0.0198(3) Uani 1 1 d . . . . .
H15A H 0.5866 0.9324 0.4011 0.024 Uiso 1 1 calc R U . . .
H15B H 0.4396 0.8490 0.4901 0.024 Uiso 1 1 calc R U . . .
C16 C 0.33920(18) 1.03513(17) 0.30029(15) 0.0275(3) Uani 1 1 d . . . . .
H16A H 0.3122 1.1315 0.3333 0.041 Uiso 1 1 calc R U . . .
H16B H 0.3802 1.0755 0.2081 0.041 Uiso 1 1 calc R U . . .
H16C H 0.2339 0.9925 0.2968 0.041 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
C1 C2 1.3839(17) . ?
C1 C6 1.3958(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.3959(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3972(18) . ?
C3 C14 1.4878(16) . ?
C4 C5 1.3842(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.4031(18) . ?
C5 H5 0.9500 . ?
C6 N7 1.4180(15) . ?
N7 N8 1.2866(15) . ?
N8 N9 1.3042(14) . ?
N9 C10 1.4635(16) . ?
N9 C13 1.4655(15) . ?
C10 C11 1.5223(17) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5356(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5334(17) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 O14 1.2067(15) . ?
C14 O15 1.3442(15) . ?
O15 C15 1.4530(14) . ?
C15 C16 1.5030(18) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C2 C1 C6 120.74(12) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C1 C2 C3 120.36(12) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 119.11(11) . . ?
C2 C3 C14 122.60(11) . . ?
C4 C3 C14 118.29(11) . . ?
C5 C4 C3 120.63(11) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.25(11) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.90(11) . . ?
C1 C6 N7 115.97(11) . . ?
C5 C6 N7 125.13(11) . . ?
N8 N7 C6 111.25(10) . . ?
N7 N8 N9 113.80(10) . . ?
N8 N9 C10 120.01(10) . . ?
N8 N9 C13 125.88(10) . . ?
C10 N9 C13 114.06(9) . . ?
N9 C10 C11 102.30(10) . . ?
N9 C10 H10A 111.3 . . ?
C11 C10 H10A 111.3 . . ?
N9 C10 H10B 111.3 . . ?
C11 C10 H10B 111.3 . . ?
H10A C10 H10B 109.2 . . ?
C10 C11 C12 103.87(10) . . ?
C10 C11 H11A 111.0 . . ?
C12 C11 H11A 111.0 . . ?
C10 C11 H11B 111.0 . . ?
C12 C11 H11B 111.0 . . ?
H11A C11 H11B 109.0 . . ?
C13 C12 C11 105.04(10) . . ?
C13 C12 H12A 110.7 . . ?
C11 C12 H12A 110.7 . . ?
C13 C12 H12B 110.7 . . ?
C11 C12 H12B 110.7 . . ?
H12A C12 H12B 108.8 . . ?
N9 C13 C12 102.80(10) . . ?
N9 C13 H13A 111.2 . . ?
C12 C13 H13A 111.2 . . ?
N9 C13 H13B 111.2 . . ?
C12 C13 H13B 111.2 . . ?
H13A C13 H13B 109.1 . . ?
O14 C14 O15 123.28(11) . . ?
O14 C14 C3 124.47(11) . . ?
O15 C14 C3 112.25(10) . . ?
C14 O15 C15 115.06(9) . . ?
O15 C15 C16 107.12(10) . . ?
O15 C15 H15A 110.3 . . ?
C16 C15 H15A 110.3 . . ?
O15 C15 H15B 110.3 . . ?
C16 C15 H15B 110.3 . . ?
H15A C15 H15B 108.5 . . ?
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 . . ?

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 0.46(19) . . . . ?
C1 C2 C3 C4 -0.18(18) . . . . ?
C1 C2 C3 C14 179.28(11) . . . . ?
C2 C3 C4 C5 -0.06(18) . . . . ?
C14 C3 C4 C5 -179.54(11) . . . . ?
C3 C4 C5 C6 0.03(18) . . . . ?
C2 C1 C6 C5 -0.48(18) . . . . ?
C2 C1 C6 N7 -179.69(11) . . . . ?
C4 C5 C6 C1 0.23(18) . . . . ?
C4 C5 C6 N7 179.37(11) . . . . ?
C1 C6 N7 N8 -174.17(10) . . . . ?
C5 C6 N7 N8 6.67(16) . . . . ?
C6 N7 N8 N9 -177.97(10) . . . . ?
N7 N8 N9 C10 179.89(10) . . . . ?
N7 N8 N9 C13 2.83(17) . . . . ?
N8 N9 C10 C11 -158.29(11) . . . . ?
C13 N9 C10 C11 19.10(13) . . . . ?
N9 C10 C11 C12 -31.83(12) . . . . ?
C10 C11 C12 C13 34.18(13) . . . . ?
N8 N9 C13 C12 179.13(11) . . . . ?
C10 N9 C13 C12 1.92(14) . . . . ?
C11 C12 C13 N9 -22.20(13) . . . . ?
C2 C3 C14 O14 178.41(12) . . . . ?
C4 C3 C14 O14 -2.13(18) . . . . ?
C2 C3 C14 O15 -2.36(16) . . . . ?
C4 C3 C14 O15 177.11(10) . . . . ?
O14 C14 O15 C15 -1.33(17) . . . . ?
C3 C14 O15 C15 179.42(10) . . . . ?
C14 O15 C15 C16 169.64(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H10A O14 0.99 2.51 3.1603(15) 122.6 2_756
C11 H11B N7 0.99 2.60 3.4698(16) 147.3 2_755

_refine_diff_density_max         0.244
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_sb840_hy_compound_3c_5
_database_code_depnum_ccdc_archive 'CCDC 1510210'
_audit_update_record             
;
2016-10-17 deposited with the CCDC.
2016-12-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'4-(3,4-dihydro-1H-isoquinolin-2-ylazo)-benzoic acid ethyl ester'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H19 N3 O2'
_chemical_formula_sum            'C18 H19 N3 O2'
_chemical_formula_weight         309.36

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'
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                   5.9831(5)
_cell_length_b                   33.308(3)
_cell_length_c                   7.7858(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.355(2)
_cell_angle_gamma                90
_cell_volume                     1548.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9292
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      72.1

_exptl_crystal_description       plates
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.712
_shelx_estimated_absorpt_T_min   0.848
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8705
_exptl_absorpt_correction_T_max  0.9582
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
;
 dx = 50 mm, 1 deg., 18+1 runs, 2904 frames, 10/15/20 sec./frame
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE with Photon100 detector'
_diffrn_measurement_method       'rotation in φ and ω, 1°, shutterless'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            22876
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.653
_diffrn_reflns_theta_max         72.173
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3057
_reflns_number_gt                2951
_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       'APEX3 v2015.9-RC2 (Bruker AXS)'
_computing_cell_refinement       'APEX3 v2015.9-RC2 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Shelxtl
_computing_publication_material  publCIF

_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)+(0.0402P)²+0.6671P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0037(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3057
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0901
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_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
C1 C 0.41922(18) 0.57050(3) 0.13138(14) 0.0189(2) Uani 1 1 d . . . . .
H1 H 0.3146 0.5494 0.1093 0.023 Uiso 1 1 calc R U . . .
C2 C 0.35916(18) 0.60966(3) 0.09128(14) 0.0186(2) Uani 1 1 d . . . . .
H2 H 0.2139 0.6153 0.0413 0.022 Uiso 1 1 calc R U . . .
C3 C 0.51146(18) 0.64099(3) 0.12411(14) 0.0171(2) Uani 1 1 d . . . . .
C4 C 0.72527(18) 0.63232(3) 0.19665(14) 0.0179(2) Uani 1 1 d . . . . .
H4 H 0.8300 0.6534 0.2179 0.022 Uiso 1 1 calc R U . . .
C5 C 0.78560(17) 0.59321(3) 0.23781(14) 0.0171(2) Uani 1 1 d . . . . .
H5 H 0.9304 0.5876 0.2888 0.020 Uiso 1 1 calc R U . . .
C6 C 0.63290(18) 0.56175(3) 0.20426(13) 0.0164(2) Uani 1 1 d . . . . .
N7 N 0.67445(15) 0.52113(3) 0.24925(12) 0.0180(2) Uani 1 1 d . . . . .
N8 N 0.88258(15) 0.51201(3) 0.24968(12) 0.0193(2) Uani 1 1 d . . . . .
N9 N 0.92555(15) 0.47484(3) 0.29978(14) 0.0219(2) Uani 1 1 d . . . . .
C10 C 0.74797(18) 0.44828(3) 0.35049(15) 0.0201(2) Uani 1 1 d . . . . .
H10A H 0.6216 0.4497 0.2627 0.024 Uiso 1 1 calc R U . . .
H10B H 0.6930 0.4579 0.4608 0.024 Uiso 1 1 calc R U . . .
C11 C 0.82150(17) 0.40520(3) 0.37105(13) 0.0165(2) Uani 1 1 d . . . . .
C12 C 0.68743(19) 0.37871(3) 0.45825(14) 0.0198(2) Uani 1 1 d . . . . .
H12 H 0.5574 0.3884 0.5092 0.024 Uiso 1 1 calc R U . . .
C13 C 0.7429(2) 0.33831(3) 0.47102(15) 0.0234(3) Uani 1 1 d . . . . .
H13 H 0.6510 0.3205 0.5308 0.028 Uiso 1 1 calc R U . . .
C14 C 0.9324(2) 0.32390(4) 0.39660(16) 0.0252(3) Uani 1 1 d . . . . .
H14 H 0.9691 0.2962 0.4036 0.030 Uiso 1 1 calc R U . . .
C15 C 1.06777(19) 0.35030(3) 0.31191(15) 0.0226(3) Uani 1 1 d . . . . .
H15 H 1.1988 0.3405 0.2626 0.027 Uiso 1 1 calc R U . . .
C16 C 1.01425(18) 0.39095(3) 0.29814(14) 0.0174(2) Uani 1 1 d . . . . .
C17 C 1.15983(18) 0.42033(3) 0.20867(15) 0.0204(2) Uani 1 1 d . . . . .
H17A H 1.1044 0.4233 0.0870 0.024 Uiso 1 1 calc R U . . .
H17B H 1.3153 0.4101 0.2107 0.024 Uiso 1 1 calc R U . . .
C18 C 1.15675(17) 0.46098(3) 0.29774(15) 0.0195(2) Uani 1 1 d . . . . .
H18A H 1.2226 0.4586 0.4170 0.023 Uiso 1 1 calc R U . . .
H18B H 1.2468 0.4805 0.2355 0.023 Uiso 1 1 calc R U . . .
C19 C 0.44608(18) 0.68357(3) 0.09243(15) 0.0199(2) Uani 1 1 d . . . . .
O19 O 0.57260(14) 0.71178(3) 0.10620(14) 0.0334(2) Uani 1 1 d . . . . .
O20 O 0.22631(13) 0.68689(2) 0.05077(11) 0.0225(2) Uani 1 1 d . . . . .
C20 C 0.1361(2) 0.72718(3) 0.02814(16) 0.0256(3) Uani 1 1 d . . . . .
H20A H -0.0063 0.7260 -0.0431 0.031 Uiso 1 1 calc R U . . .
H20B H 0.2427 0.7439 -0.0329 0.031 Uiso 1 1 calc R U . . .
C21 C 0.0955(2) 0.74586(4) 0.19857(17) 0.0272(3) Uani 1 1 d . . . . .
H21A H 0.0348 0.7730 0.1805 0.041 Uiso 1 1 calc R U . . .
H21B H -0.0118 0.7295 0.2582 0.041 Uiso 1 1 calc R U . . .
H21C H 0.2369 0.7474 0.2684 0.041 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
C1 C2 1.3838(15) . ?
C1 C6 1.3986(15) . ?
C1 H1 0.9500 . ?
C2 C3 1.3991(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.3979(15) . ?
C3 C19 1.4881(15) . ?
C4 C5 1.3845(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.4045(15) . ?
C5 H5 0.9500 . ?
C6 N7 1.4161(14) . ?
N7 N8 1.2815(13) . ?
N8 N9 1.3188(13) . ?
N9 C10 1.4549(14) . ?
N9 C18 1.4593(13) . ?
C10 C11 1.5067(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.3951(15) . ?
C11 C16 1.3979(15) . ?
C12 C13 1.3884(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.3886(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3880(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3939(16) . ?
C15 H15 0.9500 . ?
C16 C17 1.5076(15) . ?
C17 C18 1.5218(15) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O19 1.2073(14) . ?
C19 O20 1.3403(14) . ?
O20 C20 1.4532(13) . ?
C20 C21 1.4983(18) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C2 C1 C6 120.46(10) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C1 C2 C3 120.27(10) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 119.39(10) . . ?
C4 C3 C19 119.29(10) . . ?
C2 C3 C19 121.24(10) . . ?
C5 C4 C3 120.52(10) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.06(10) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.30(10) . . ?
C1 C6 N7 116.26(9) . . ?
C5 C6 N7 124.32(10) . . ?
N8 N7 C6 112.55(9) . . ?
N7 N8 N9 113.31(9) . . ?
N8 N9 C10 121.22(9) . . ?
N8 N9 C18 117.54(9) . . ?
C10 N9 C18 121.22(9) . . ?
N9 C10 C11 113.24(9) . . ?
N9 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
N9 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 C16 119.63(10) . . ?
C12 C11 C10 118.77(9) . . ?
C16 C11 C10 121.53(9) . . ?
C13 C12 C11 120.40(10) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.18(11) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 119.52(11) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.93(11) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C11 119.33(10) . . ?
C15 C16 C17 121.99(10) . . ?
C11 C16 C17 118.67(10) . . ?
C16 C17 C18 110.14(9) . . ?
C16 C17 H17A 109.6 . . ?
C18 C17 H17A 109.6 . . ?
C16 C17 H17B 109.6 . . ?
C18 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
N9 C18 C17 108.86(9) . . ?
N9 C18 H18A 109.9 . . ?
C17 C18 H18A 109.9 . . ?
N9 C18 H18B 109.9 . . ?
C17 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
O19 C19 O20 123.95(10) . . ?
O19 C19 C3 124.72(10) . . ?
O20 C19 C3 111.31(9) . . ?
C19 O20 C20 117.23(9) . . ?
O20 C20 C21 110.77(10) . . ?
O20 C20 H20A 109.5 . . ?
C21 C20 H20A 109.5 . . ?
O20 C20 H20B 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.33(16) . . . . ?
C1 C2 C3 C4 0.44(16) . . . . ?
C1 C2 C3 C19 -176.08(10) . . . . ?
C2 C3 C4 C5 -0.80(16) . . . . ?
C19 C3 C4 C5 175.80(10) . . . . ?
C3 C4 C5 C6 1.03(16) . . . . ?
C2 C1 C6 C5 0.55(16) . . . . ?
C2 C1 C6 N7 176.71(10) . . . . ?
C4 C5 C6 C1 -0.90(15) . . . . ?
C4 C5 C6 N7 -176.72(10) . . . . ?
C1 C6 N7 N8 154.20(10) . . . . ?
C5 C6 N7 N8 -29.87(14) . . . . ?
C6 N7 N8 N9 176.76(9) . . . . ?
N7 N8 N9 C10 -0.82(15) . . . . ?
N7 N8 N9 C18 177.46(10) . . . . ?
N8 N9 C10 C11 169.10(10) . . . . ?
C18 N9 C10 C11 -9.11(15) . . . . ?
N9 C10 C11 C12 164.60(10) . . . . ?
N9 C10 C11 C16 -18.41(15) . . . . ?
C16 C11 C12 C13 -0.82(16) . . . . ?
C10 C11 C12 C13 176.23(10) . . . . ?
C11 C12 C13 C14 -0.14(17) . . . . ?
C12 C13 C14 C15 1.06(18) . . . . ?
C13 C14 C15 C16 -1.03(18) . . . . ?
C14 C15 C16 C11 0.08(17) . . . . ?
C14 C15 C16 C17 179.27(11) . . . . ?
C12 C11 C16 C15 0.84(16) . . . . ?
C10 C11 C16 C15 -176.12(10) . . . . ?
C12 C11 C16 C17 -178.38(10) . . . . ?
C10 C11 C16 C17 4.66(15) . . . . ?
C15 C16 C17 C18 -145.41(10) . . . . ?
C11 C16 C17 C18 33.79(14) . . . . ?
N8 N9 C18 C17 -131.71(10) . . . . ?
C10 N9 C18 C17 46.57(14) . . . . ?
C16 C17 C18 N9 -56.96(12) . . . . ?
C4 C3 C19 O19 8.97(17) . . . . ?
C2 C3 C19 O19 -174.50(11) . . . . ?
C4 C3 C19 O20 -169.38(10) . . . . ?
C2 C3 C19 O20 7.15(15) . . . . ?
O19 C19 O20 C20 -2.60(17) . . . . ?
C3 C19 O20 C20 175.77(9) . . . . ?
C19 O20 C20 C21 -80.68(12) . . . . ?

_refine_diff_density_max         0.285
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_sb837_hy_compound_6c_1
_database_code_depnum_ccdc_archive 'CCDC 1510211'
_audit_update_record             
;
2016-10-17 deposited with the CCDC.
2016-12-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 ethyl (E)-4-((2-oxopiperidin-1-yl)diazenyl)benzoate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 N3 O3'
_chemical_formula_sum            'C14 H17 N3 O3'
_chemical_formula_weight         275.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.7907(3)
_cell_length_b                   7.0900(2)
_cell_length_c                   12.8103(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.877(1)
_cell_angle_gamma                90
_cell_volume                     1327.27(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9885
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      71.9

_exptl_crystal_description       plates
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.814
_shelx_estimated_absorpt_T_min   0.895
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8739
_exptl_absorpt_correction_T_max  0.9812
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
;
 dx = 40 mm, 1 deg., 15+1 runs, 2682 frames, 12/16/20/24 sec./frame
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE with Photon100 detector'
_diffrn_measurement_method       'rotation in φ and ω, 1°, shutterless'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            20424
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.024
_diffrn_reflns_theta_max         72.118
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2610
_reflns_number_gt                2289
_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       'APEX3 v2015.9-RC2 (Bruker AXS)'
_computing_cell_refinement       'APEX3 v2015.9-RC2 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Shelxtl
_computing_publication_material  publCIF

_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)+(0.0455P)²+0.4246P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2610
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0899
_refine_ls_wR_factor_gt          0.0864
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_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
C1 C 0.70097(8) 0.12147(16) 0.59849(9) 0.0179(3) Uani 1 1 d . . . . .
H1 H 0.7198 0.1183 0.5309 0.021 Uiso 1 1 calc R U . . .
C2 C 0.60875(8) 0.11387(16) 0.60766(9) 0.0171(3) Uani 1 1 d . . . . .
H2 H 0.5642 0.1048 0.5460 0.021 Uiso 1 1 calc R U . . .
C3 C 0.58109(7) 0.11951(16) 0.70676(9) 0.0156(2) Uani 1 1 d . . . . .
C4 C 0.64629(8) 0.13330(16) 0.79779(9) 0.0168(2) Uani 1 1 d . . . . .
H4 H 0.6274 0.1394 0.8653 0.020 Uiso 1 1 calc R U . . .
C5 C 0.73867(8) 0.13807(16) 0.78944(9) 0.0173(2) Uani 1 1 d . . . . .
H5 H 0.7833 0.1441 0.8512 0.021 Uiso 1 1 calc R U . . .
C6 C 0.76578(8) 0.13389(16) 0.68979(9) 0.0161(2) Uani 1 1 d . . . . .
N7 N 0.86219(6) 0.12985(14) 0.69010(8) 0.0173(2) Uani 1 1 d . . . . .
N8 N 0.88603(6) 0.20032(14) 0.60863(8) 0.0171(2) Uani 1 1 d . . . . .
N9 N 0.97931(6) 0.18998(14) 0.61130(7) 0.0166(2) Uani 1 1 d . . . . .
C10 C 1.03659(8) 0.09977(17) 0.70249(9) 0.0181(3) Uani 1 1 d . . . . .
H10A H 1.0300 -0.0389 0.6966 0.022 Uiso 1 1 calc R U . . .
H10B H 1.0151 0.1397 0.7685 0.022 Uiso 1 1 calc R U . . .
C11 C 1.13643(8) 0.15211(18) 0.70770(9) 0.0203(3) Uani 1 1 d . . . . .
H11A H 1.1741 0.0737 0.7618 0.024 Uiso 1 1 calc R U . . .
H11B H 1.1453 0.2860 0.7289 0.024 Uiso 1 1 calc R U . . .
C12 C 1.16755(8) 0.12219(18) 0.60104(10) 0.0210(3) Uani 1 1 d . . . . .
H12A H 1.1583 -0.0112 0.5791 0.025 Uiso 1 1 calc R U . . .
H12B H 1.2335 0.1518 0.6063 0.025 Uiso 1 1 calc R U . . .
C13 C 1.11212(8) 0.25081(18) 0.51966(9) 0.0203(3) Uani 1 1 d . . . . .
H13A H 1.1353 0.3812 0.5319 0.024 Uiso 1 1 calc R U . . .
H13B H 1.1236 0.2123 0.4486 0.024 Uiso 1 1 calc R U . . .
C14 C 1.00993(8) 0.25271(16) 0.51939(9) 0.0167(2) Uani 1 1 d . . . . .
O14 O 0.95696(6) 0.30891(13) 0.44379(6) 0.0218(2) Uani 1 1 d . . . . .
C15 C 0.48106(8) 0.10711(16) 0.71265(9) 0.0158(2) Uani 1 1 d . . . . .
O15 O 0.42262(5) 0.08047(14) 0.63731(6) 0.0229(2) Uani 1 1 d . . . . .
O16 O 0.46397(5) 0.12775(12) 0.81156(6) 0.0189(2) Uani 1 1 d . . . . .
C16 C 0.36803(7) 0.11703(17) 0.82454(9) 0.0179(3) Uani 1 1 d . . . . .
H16A H 0.3394 0.0024 0.7898 0.022 Uiso 1 1 calc R U . . .
H16B H 0.3344 0.2288 0.7926 0.022 Uiso 1 1 calc R U . . .
C17 C 0.36558(9) 0.11044(19) 0.94150(10) 0.0235(3) Uani 1 1 d . . . . .
H17A H 0.3019 0.1031 0.9538 0.035 Uiso 1 1 calc R U . . .
H17B H 0.3991 -0.0007 0.9720 0.035 Uiso 1 1 calc R U . . .
H17C H 0.3941 0.2246 0.9748 0.035 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
C1 C2 1.3880(16) . ?
C1 C6 1.3959(16) . ?
C1 H1 0.9500 . ?
C2 C3 1.3931(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.3973(16) . ?
C3 C15 1.4956(15) . ?
C4 C5 1.3873(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.3963(16) . ?
C5 H5 0.9500 . ?
C6 N7 1.4256(14) . ?
N7 N8 1.2557(14) . ?
N8 N9 1.3767(13) . ?
N9 C14 1.3978(15) . ?
N9 C10 1.4785(14) . ?
C10 C11 1.5141(16) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5224(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5255(17) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5110(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 O14 1.2150(14) . ?
C15 O15 1.2070(14) . ?
C15 O16 1.3378(14) . ?
O16 C16 1.4559(13) . ?
C16 C17 1.5050(16) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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
C2 C1 C6 119.23(11) . . ?
C2 C1 H1 120.4 . . ?
C6 C1 H1 120.4 . . ?
C1 C2 C3 120.44(10) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 120.04(10) . . ?
C2 C3 C15 118.44(10) . . ?
C4 C3 C15 121.51(10) . . ?
C5 C4 C3 119.89(11) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 119.69(10) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 120.69(10) . . ?
C1 C6 N7 123.94(10) . . ?
C5 C6 N7 115.22(10) . . ?
N8 N7 C6 113.50(9) . . ?
N7 N8 N9 111.53(9) . . ?
N8 N9 C14 114.57(9) . . ?
N8 N9 C10 119.51(9) . . ?
C14 N9 C10 125.62(9) . . ?
N9 C10 C11 111.40(10) . . ?
N9 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
N9 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 C12 110.74(9) . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 C13 108.97(10) . . ?
C11 C12 H12A 109.9 . . ?
C13 C12 H12A 109.9 . . ?
C11 C12 H12B 109.9 . . ?
C13 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
C14 C13 C12 116.03(10) . . ?
C14 C13 H13A 108.3 . . ?
C12 C13 H13A 108.3 . . ?
C14 C13 H13B 108.3 . . ?
C12 C13 H13B 108.3 . . ?
H13A C13 H13B 107.4 . . ?
O14 C14 N9 121.52(10) . . ?
O14 C14 C13 121.77(10) . . ?
N9 C14 C13 116.70(9) . . ?
O15 C15 O16 123.91(10) . . ?
O15 C15 C3 124.11(10) . . ?
O16 C15 C3 111.99(9) . . ?
C15 O16 C16 115.62(9) . . ?
O16 C16 C17 106.80(9) . . ?
O16 C16 H16A 110.4 . . ?
C17 C16 H16A 110.4 . . ?
O16 C16 H16B 110.4 . . ?
C17 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.32(17) . . . . ?
C1 C2 C3 C4 0.13(17) . . . . ?
C1 C2 C3 C15 -178.82(10) . . . . ?
C2 C3 C4 C5 -1.12(17) . . . . ?
C15 C3 C4 C5 177.81(10) . . . . ?
C3 C4 C5 C6 1.63(17) . . . . ?
C2 C1 C6 C5 0.20(17) . . . . ?
C2 C1 C6 N7 175.64(11) . . . . ?
C4 C5 C6 C1 -1.18(17) . . . . ?
C4 C5 C6 N7 -177.00(10) . . . . ?
C1 C6 N7 N8 31.41(16) . . . . ?
C5 C6 N7 N8 -152.92(10) . . . . ?
C6 N7 N8 N9 -178.76(9) . . . . ?
N7 N8 N9 C14 175.30(10) . . . . ?
N7 N8 N9 C10 1.18(14) . . . . ?
N8 N9 C10 C11 -163.07(10) . . . . ?
C14 N9 C10 C11 23.51(16) . . . . ?
N9 C10 C11 C12 -49.78(14) . . . . ?
C10 C11 C12 C13 61.91(13) . . . . ?
C11 C12 C13 C14 -46.71(14) . . . . ?
N8 N9 C14 O14 -0.89(16) . . . . ?
C10 N9 C14 O14 172.82(11) . . . . ?
N8 N9 C14 C13 177.90(10) . . . . ?
C10 N9 C14 C13 -8.39(16) . . . . ?
C12 C13 C14 O14 -160.98(11) . . . . ?
C12 C13 C14 N9 20.23(15) . . . . ?
C2 C3 C15 O15 4.89(17) . . . . ?
C4 C3 C15 O15 -174.05(11) . . . . ?
C2 C3 C15 O16 -175.54(10) . . . . ?
C4 C3 C15 O16 5.52(15) . . . . ?
O15 C15 O16 C16 -0.27(16) . . . . ?
C3 C15 O16 C16 -179.84(9) . . . . ?
C15 O16 C16 C17 170.62(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H10A O14 0.99 2.65 3.4600(15) 138.7 3_756
C10 H10B O14 0.99 2.55 3.5335(14) 171.6 4_566
C11 H11B N7 0.99 2.66 3.6303(16) 166.9 2_756
C13 H13A O14 0.99 2.63 3.3399(16) 128.7 3_766
C17 H17C O15 0.98 2.48 3.3396(15) 146.3 4_566

_refine_diff_density_max         0.325
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.051

