# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_Z-4
_database_code_depnum_ccdc_archive 'CCDC 1961684'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2021-03-05 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT910_compound_Z-4        
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).  25 Note  
RESPONSE: Indeed 25 Bragg reflections  as listed below were 
omitted due to a theta(min)limit set too high  (From CIF:  3.77)
The very low-order reflections are essentially hidden by the beamstop
which has a finite size and a fixed setting and the strategy software
does not readily allow us to set up  additional images with the detector
 at a larger distance from the crystal with the beamstop setting 
changed accordingly. These very few missing reflections do not preclude 
at all the structure solution and refinement meeting the iUCR & Chemistry 
criteria.  
;
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
(Z)-12-tosyl-12,13-dihydro-11H-dibenzo[c,h][1,2,6]triazonine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H19 N3 O2 S'
_chemical_formula_sum            'C21 H19 N3 O2 S'
_chemical_formula_weight         377.45

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'
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'
S S 0.1246 0.1234 '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'

_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                   12.1589(9)
_cell_length_b                   12.2886(9)
_cell_length_c                   13.5265(10)
_cell_angle_alpha                81.017(7)
_cell_angle_beta                 89.628(8)
_cell_angle_gamma                71.449(6)
_cell_volume                     1890.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3401
_cell_measurement_theta_min      3.8
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    0.192
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.748
_exptl_absorpt_process_details   'Reqab (Rigaku, 2009)'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_detector                 'Dectris PILATUS3 R 200K-A area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'Hybrid Photon Counting area detector'

_diffrn_measurement_device       'kappa gonio four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'

_diffrn_radiation_collimation    .
_diffrn_radiation_monochromator  
'Rigaku Integrated Confocal MaxFlux double bounce multi-layer mirror optics'
_diffrn_radiation_probe          x-ray

_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Rigaku micromax 003'
_diffrn_reflns_number            52160
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.771
_diffrn_reflns_theta_max         27.455
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_measurement_details      
;
scan:
	Number of images: 720
	           Slice: 0.0000 - 360.0000
	     Image width: 0.5000
	        Exp time: 30.0000
	   Rotation axis: Phi
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 30.0000
	          2theta: 5.0000
scan:
	Number of images: 720
	           Slice: 0.0000 - 360.0000
	     Image width: 0.5000
	        Exp time: 30.0000
	   Rotation axis: Phi
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 30.0000
	          2theta: 5.0000
scan:
	Number of images: 720
	           Slice: 0.0000 - 360.0000
	     Image width: 0.5000
	        Exp time: 30.0000
	   Rotation axis: Phi
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 30.0000
	          2theta: 5.0000

;
_reflns_number_total             8484
_reflns_number_gt                7314
_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       
;
CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0758P)²+0.1960P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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_number_reflns         8476
_refine_ls_number_parameters     489
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1217
_refine_ls_wR_factor_gt          0.1180
_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
N1_1 N -0.00270(13) 0.37654(11) -0.05881(10) 0.0637(3) Uani 1 1 d . . . . .
C1_1 C -0.04381(12) 0.28203(12) -0.01409(12) 0.0551(3) Uani 1 1 d . . . . .
S1_1 S 0.05218(3) 0.31263(3) 0.33558(3) 0.05256(11) Uani 1 1 d . . . . .
O1_1 O -0.04224(11) 0.27234(10) 0.36938(10) 0.0718(3) Uani 1 1 d . . . . .
N2_1 N 0.10345(13) 0.36319(10) -0.05313(10) 0.0601(3) Uani 1 1 d . . . . .
C2_1 C -0.06508(11) 0.26816(12) 0.08772(12) 0.0501(3) Uani 1 1 d . . . . .
O2_1 O 0.16642(11) 0.25562(11) 0.37985(9) 0.0721(3) Uani 1 1 d . . . . .
N3_1 N 0.06121(9) 0.30317(10) 0.21566(9) 0.0465(2) Uani 1 1 d . . . . .
C3_1 C -0.04896(11) 0.35024(12) 0.15462(12) 0.0526(3) Uani 1 1 d . . . . .
H3A_1 H -0.051048 0.422974 0.113360 0.063 Uiso 1 1 calc R U . . .
H3B_1 H -0.113181 0.366873 0.198905 0.063 Uiso 1 1 calc R U . . .
C4_1 C 0.16348(11) 0.32194(11) 0.16439(11) 0.0477(3) Uani 1 1 d . . . . .
H4_1 H 0.222539 0.317216 0.214217 0.057 Uiso 1 1 calc R U . . .
H14B_1 H 0.140678 0.399327 0.125015 0.057 Uiso 1 1 calc R U . . .
C5_1 C 0.21390(10) 0.23306(10) 0.09654(10) 0.0428(3) Uani 1 1 d . . . . .
C6_1 C 0.18362(11) 0.25227(11) -0.00518(10) 0.0469(3) Uani 1 1 d . . . . .
C7_1 C 0.01376(11) 0.46131(12) 0.34659(10) 0.0469(3) Uani 1 1 d . . . . .
C8_1 C -0.10204(13) 0.52822(14) 0.34826(14) 0.0604(4) Uani 1 1 d . . . . .
H8_1 H -0.160286 0.494634 0.345334 0.073 Uiso 1 1 calc R U . . .
C9_1 C -0.13011(13) 0.64492(14) 0.35429(15) 0.0641(4) Uani 1 1 d . . . . .
H9_1 H -0.207847 0.689654 0.354233 0.077 Uiso 1 1 calc R U . . .
C10_1 C -0.04524(14) 0.69704(13) 0.36044(11) 0.0554(3) Uani 1 1 d . . . . .
C11_1 C 0.06909(15) 0.62931(16) 0.35859(16) 0.0697(4) Uani 1 1 d . . . . .
H11_1 H 0.127247 0.662948 0.361822 0.084 Uiso 1 1 calc R U . . .
C12_1 C 0.09936(13) 0.51214(15) 0.35204(15) 0.0664(4) Uani 1 1 d . . . . .
H12_1 H 0.177138 0.467806 0.351304 0.080 Uiso 1 1 calc R U . . .
C13_1 C -0.07718(18) 0.82444(16) 0.36815(17) 0.0784(5) Uani 1 1 d . . . . .
H13_1 H -0.012383 0.838950 0.397137 0.118 Uiso 1 1 calc R U . . .
H21B_1 H -0.142464 0.845410 0.409697 0.118 Uiso 1 1 calc R U . . .
H21C_1 H -0.097025 0.870018 0.302515 0.118 Uiso 1 1 calc R U . . .
C14_1 C -0.10777(13) 0.17866(14) 0.12666(14) 0.0617(4) Uani 1 1 d . . . . .
H14_1 H -0.120976 0.166853 0.194696 0.074 Uiso 1 1 calc R U . . .
C15_1 C -0.13099(15) 0.10681(17) 0.06610(18) 0.0745(5) Uani 1 1 d . . . . .
H15_1 H -0.158999 0.047116 0.093671 0.089 Uiso 1 1 calc R U . . .
C16_1 C -0.11274(16) 0.12359(17) -0.03437(18) 0.0772(5) Uani 1 1 d . . . . .
H16_1 H -0.129359 0.075808 -0.074979 0.093 Uiso 1 1 calc R U . . .
C17_1 C -0.06968(15) 0.21130(16) -0.07576(14) 0.0703(5) Uani 1 1 d . . . . .
H17_1 H -0.058041 0.223083 -0.144098 0.084 Uiso 1 1 calc R U . . .
C18_1 C 0.23602(13) 0.17119(13) -0.06654(11) 0.0536(3) Uani 1 1 d . . . . .
H18_1 H 0.216475 0.187034 -0.134826 0.064 Uiso 1 1 calc R U . . .
C19_1 C 0.31738(13) 0.06686(12) -0.02521(12) 0.0535(3) Uani 1 1 d . . . . .
H19_1 H 0.351988 0.011604 -0.065435 0.064 Uiso 1 1 calc R U . . .
C20_1 C 0.34704(12) 0.04501(12) 0.07580(12) 0.0519(3) Uani 1 1 d . . . . .
H20_1 H 0.401566 -0.025289 0.103646 0.062 Uiso 1 1 calc R U . . .
C21_1 C 0.29616(11) 0.12711(11) 0.13617(11) 0.0468(3) Uani 1 1 d . . . . .
H21_1 H 0.317232 0.111275 0.204172 0.056 Uiso 1 1 calc R U . . .
O1_2 O 0.66150(10) 0.19556(9) 0.24897(8) 0.0611(3) Uani 1 1 d . . . . .
S1_2 S 0.54923(3) 0.26945(3) 0.26871(2) 0.04381(10) Uani 1 1 d . . . . .
C1_2 C 0.68573(13) 0.24249(13) 0.61329(11) 0.0517(3) Uani 1 1 d . . . . .
N1_2 N 0.60449(15) 0.35339(12) 0.62880(10) 0.0648(3) Uani 1 1 d . . . . .
O2_2 O 0.44886(10) 0.23593(10) 0.25338(8) 0.0599(3) Uani 1 1 d . . . . .
C2_2 C 0.71347(12) 0.22102(12) 0.51681(10) 0.0476(3) Uani 1 1 d . . . . .
N3_2 N 0.55371(9) 0.28451(10) 0.38593(8) 0.0466(2) Uani 1 1 d . . . . .
C4_2 C 0.44324(12) 0.32783(12) 0.43523(10) 0.0509(3) Uani 1 1 d . . . . .
H4A_2 H 0.379046 0.337622 0.388819 0.061 Uiso 1 1 calc R U . . .
H4B_2 H 0.436025 0.403304 0.452782 0.061 Uiso 1 1 calc R U . . .
C5_2 C 0.43630(11) 0.24520(11) 0.52888(9) 0.0444(3) Uani 1 1 d . . . . .
C6_2 C 0.46377(12) 0.26246(12) 0.62402(10) 0.0490(3) Uani 1 1 d . . . . .
C7_2 C 0.52690(11) 0.40777(11) 0.19494(8) 0.0402(2) Uani 1 1 d . . . . .
C8_2 C 0.62131(12) 0.44147(14) 0.16463(12) 0.0585(4) Uani 1 1 d . . . . .
H8_2 H 0.696191 0.391394 0.182242 0.070 Uiso 1 1 calc R U . . .
C9_2 C 0.60447(15) 0.55013(15) 0.10786(13) 0.0637(4) Uani 1 1 d . . . . .
H9_2 H 0.668472 0.572899 0.088611 0.076 Uiso 1 1 calc R U . . .
C10_2 C 0.49403(14) 0.62507(11) 0.07948(10) 0.0514(3) Uani 1 1 d . . . . .
C11_2 C 0.40069(14) 0.58940(13) 0.11044(12) 0.0595(4) Uani 1 1 d . . . . .
H11_2 H 0.325774 0.638920 0.092062 0.071 Uiso 1 1 calc R U . . .
C12_2 C 0.41597(12) 0.48144(13) 0.16833(11) 0.0527(3) Uani 1 1 d . . . . .
H12_2 H 0.352052 0.459164 0.188873 0.063 Uiso 1 1 calc R U . . .
C13_2 C 0.4765(2) 0.74194(14) 0.01533(13) 0.0747(5) Uani 1 1 d . . . . .
H21D_2 H 0.518032 0.731225 -0.044888 0.112 Uiso 1 1 calc R U . . .
H21E_2 H 0.505075 0.789306 0.051686 0.112 Uiso 1 1 calc R U . . .
H21F_2 H 0.395248 0.779613 -0.001608 0.112 Uiso 1 1 calc R U . . .
C14_2 C 0.79570(13) 0.11577(14) 0.50546(13) 0.0578(3) Uani 1 1 d . . . . .
H14_2 H 0.815137 0.099914 0.441419 0.069 Uiso 1 1 calc R U . . .
C15_2 C 0.84924(14) 0.03397(15) 0.58812(15) 0.0684(4) Uani 1 1 d . . . . .
H15_2 H 0.903666 -0.036357 0.579522 0.082 Uiso 1 1 calc R U . . .
C16_2 C 0.82097(15) 0.05793(17) 0.68355(15) 0.0728(5) Uani 1 1 d . . . . .
H16_2 H 0.856719 0.003304 0.739080 0.087 Uiso 1 1 calc R U . . .
C17_2 C 0.74067(16) 0.16156(17) 0.69694(12) 0.0661(4) Uani 1 1 d . . . . .
H17_2 H 0.723011 0.177718 0.761181 0.079 Uiso 1 1 calc R U . . .
C18_2 C 0.45384(14) 0.18683(15) 0.70922(11) 0.0607(4) Uani 1 1 d . . . . .
H18_2 H 0.467718 0.201651 0.772521 0.073 Uiso 1 1 calc R U . . .
C19_2 C 0.42352(14) 0.09036(15) 0.69953(12) 0.0651(4) Uani 1 1 d . . . . .
H19_2 H 0.419761 0.038380 0.756309 0.078 Uiso 1 1 calc R U . . .
C20_2 C 0.39870(13) 0.07014(14) 0.60644(13) 0.0597(4) Uani 1 1 d . . . . .
H20_2 H 0.378660 0.004420 0.600289 0.072 Uiso 1 1 calc R U . . .
C21_2 C 0.40359(12) 0.14813(13) 0.52139(11) 0.0510(3) Uani 1 1 d . . . . .
H21_2 H 0.384727 0.135126 0.458720 0.061 Uiso 1 1 calc R U . . .
C3_2 C 0.65621(13) 0.30800(13) 0.42514(10) 0.0520(3) Uani 1 1 d . . . . .
H14C_2 H 0.632100 0.385736 0.442126 0.062 Uiso 1 1 calc R U . . .
H14D_2 H 0.712127 0.304961 0.373308 0.062 Uiso 1 1 calc R U . . .
N2_2 N 0.49867(14) 0.36341(11) 0.63459(10) 0.0652(4) 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
N1_1 N2_1 1.249(2) . ?
N1_1 C1_1 1.453(2) . ?
C1_1 C2_1 1.394(2) . ?
C1_1 C17_1 1.398(2) . ?
S1_1 O2_1 1.4281(12) . ?
S1_1 O1_1 1.4339(12) . ?
S1_1 N3_1 1.6448(12) . ?
S1_1 C7_1 1.7661(14) . ?
N2_1 C6_1 1.4544(17) . ?
C2_1 C14_1 1.391(2) . ?
C2_1 C3_1 1.5126(19) . ?
N3_1 C3_1 1.4775(17) . ?
N3_1 C4_1 1.4838(17) . ?
C4_1 C5_1 1.5135(18) . ?
C5_1 C6_1 1.3908(19) . ?
C5_1 C21_1 1.3940(18) . ?
C6_1 C18_1 1.391(2) . ?
C7_1 C12_1 1.381(2) . ?
C7_1 C8_1 1.3885(19) . ?
C8_1 C9_1 1.380(2) . ?
C9_1 C10_1 1.386(2) . ?
C10_1 C11_1 1.377(2) . ?
C10_1 C13_1 1.509(2) . ?
C11_1 C12_1 1.385(2) . ?
C14_1 C15_1 1.385(2) . ?
C15_1 C16_1 1.370(3) . ?
C16_1 C17_1 1.384(3) . ?
C18_1 C19_1 1.382(2) . ?
C19_1 C20_1 1.378(2) . ?
C20_1 C21_1 1.386(2) . ?
O1_2 S1_2 1.4288(11) . ?
S1_2 O2_2 1.4324(10) . ?
S1_2 N3_2 1.6280(11) . ?
S1_2 C7_2 1.7716(12) . ?
C1_2 C2_2 1.390(2) . ?
C1_2 C17_2 1.397(2) . ?
C1_2 N1_2 1.452(2) . ?
N1_2 N2_2 1.256(2) . ?
C2_2 C14_2 1.390(2) . ?
C2_2 C3_2 1.5128(18) . ?
N3_2 C4_2 1.4753(17) . ?
N3_2 C3_2 1.4843(17) . ?
C4_2 C5_2 1.5147(18) . ?
C5_2 C21_2 1.390(2) . ?
C5_2 C6_2 1.3960(18) . ?
C6_2 C18_2 1.394(2) . ?
C6_2 N2_2 1.460(2) . ?
C7_2 C12_2 1.3769(18) . ?
C7_2 C8_2 1.3787(18) . ?
C8_2 C9_2 1.387(2) . ?
C9_2 C10_2 1.381(2) . ?
C10_2 C11_2 1.381(2) . ?
C10_2 C13_2 1.510(2) . ?
C11_2 C12_2 1.389(2) . ?
C14_2 C15_2 1.388(2) . ?
C15_2 C16_2 1.385(3) . ?
C16_2 C17_2 1.374(3) . ?
C18_2 C19_2 1.373(3) . ?
C19_2 C20_2 1.374(2) . ?
C20_2 C21_2 1.392(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2_1 N1_1 C1_1 119.12(12) . . ?
C2_1 C1_1 C17_1 120.77(16) . . ?
C2_1 C1_1 N1_1 119.97(13) . . ?
C17_1 C1_1 N1_1 119.09(16) . . ?
O2_1 S1_1 O1_1 120.31(8) . . ?
O2_1 S1_1 N3_1 106.34(7) . . ?
O1_1 S1_1 N3_1 106.14(7) . . ?
O2_1 S1_1 C7_1 107.88(7) . . ?
O1_1 S1_1 C7_1 107.88(7) . . ?
N3_1 S1_1 C7_1 107.72(6) . . ?
N1_1 N2_1 C6_1 119.47(12) . . ?
C14_1 C2_1 C1_1 117.98(14) . . ?
C14_1 C2_1 C3_1 119.76(15) . . ?
C1_1 C2_1 C3_1 122.19(14) . . ?
C3_1 N3_1 C4_1 114.87(12) . . ?
C3_1 N3_1 S1_1 116.30(9) . . ?
C4_1 N3_1 S1_1 117.78(9) . . ?
N3_1 C3_1 C2_1 113.11(10) . . ?
N3_1 C4_1 C5_1 111.82(10) . . ?
C6_1 C5_1 C21_1 117.54(12) . . ?
C6_1 C5_1 C4_1 123.13(12) . . ?
C21_1 C5_1 C4_1 119.32(12) . . ?
C5_1 C6_1 C18_1 121.69(12) . . ?
C5_1 C6_1 N2_1 120.74(12) . . ?
C18_1 C6_1 N2_1 117.32(13) . . ?
C12_1 C7_1 C8_1 119.57(14) . . ?
C12_1 C7_1 S1_1 119.86(11) . . ?
C8_1 C7_1 S1_1 120.56(11) . . ?
C9_1 C8_1 C7_1 119.54(14) . . ?
C8_1 C9_1 C10_1 121.58(14) . . ?
C11_1 C10_1 C9_1 118.03(14) . . ?
C11_1 C10_1 C13_1 120.97(15) . . ?
C9_1 C10_1 C13_1 121.00(15) . . ?
C10_1 C11_1 C12_1 121.43(15) . . ?
C7_1 C12_1 C11_1 119.84(14) . . ?
C15_1 C14_1 C2_1 121.29(18) . . ?
C16_1 C15_1 C14_1 120.05(18) . . ?
C15_1 C16_1 C17_1 120.33(16) . . ?
C16_1 C17_1 C1_1 119.51(18) . . ?
C19_1 C18_1 C6_1 119.48(14) . . ?
C20_1 C19_1 C18_1 119.79(13) . . ?
C19_1 C20_1 C21_1 120.44(13) . . ?
C20_1 C21_1 C5_1 121.02(13) . . ?
O1_2 S1_2 O2_2 119.76(7) . . ?
O1_2 S1_2 N3_2 106.76(6) . . ?
O2_2 S1_2 N3_2 106.72(6) . . ?
O1_2 S1_2 C7_2 107.68(6) . . ?
O2_2 S1_2 C7_2 107.64(6) . . ?
N3_2 S1_2 C7_2 107.77(6) . . ?
C2_2 C1_2 C17_2 120.96(15) . . ?
C2_2 C1_2 N1_2 120.20(12) . . ?
C17_2 C1_2 N1_2 118.70(14) . . ?
N2_2 N1_2 C1_2 118.75(13) . . ?
C1_2 C2_2 C14_2 118.34(13) . . ?
C1_2 C2_2 C3_2 121.90(13) . . ?
C14_2 C2_2 C3_2 119.76(13) . . ?
C4_2 N3_2 C3_2 117.29(12) . . ?
C4_2 N3_2 S1_2 118.62(9) . . ?
C3_2 N3_2 S1_2 118.16(9) . . ?
N3_2 C4_2 C5_2 111.67(10) . . ?
C21_2 C5_2 C6_2 118.19(12) . . ?
C21_2 C5_2 C4_2 120.05(12) . . ?
C6_2 C5_2 C4_2 121.75(13) . . ?
C18_2 C6_2 C5_2 120.65(14) . . ?
C18_2 C6_2 N2_2 119.68(13) . . ?
C5_2 C6_2 N2_2 119.63(12) . . ?
C12_2 C7_2 C8_2 120.14(12) . . ?
C12_2 C7_2 S1_2 120.26(10) . . ?
C8_2 C7_2 S1_2 119.60(10) . . ?
C7_2 C8_2 C9_2 119.91(14) . . ?
C10_2 C9_2 C8_2 120.98(14) . . ?
C9_2 C10_2 C11_2 118.13(13) . . ?
C9_2 C10_2 C13_2 120.65(15) . . ?
C11_2 C10_2 C13_2 121.21(15) . . ?
C10_2 C11_2 C12_2 121.64(14) . . ?
C7_2 C12_2 C11_2 119.19(13) . . ?
C15_2 C14_2 C2_2 121.09(16) . . ?
C16_2 C15_2 C14_2 119.48(17) . . ?
C17_2 C16_2 C15_2 120.65(15) . . ?
C16_2 C17_2 C1_2 119.46(17) . . ?
C19_2 C18_2 C6_2 119.86(14) . . ?
C18_2 C19_2 C20_2 120.41(14) . . ?
C19_2 C20_2 C21_2 119.91(15) . . ?
C5_2 C21_2 C20_2 120.87(14) . . ?
N3_2 C3_2 C2_2 111.88(10) . . ?
N1_2 N2_2 C6_2 117.84(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2_1 N1_1 C1_1 C2_1 83.86(18) . . . . ?
N2_1 N1_1 C1_1 C17_1 -100.84(17) . . . . ?
C1_1 N1_1 N2_1 C6_1 2.2(2) . . . . ?
C17_1 C1_1 C2_1 C14_1 2.8(2) . . . . ?
N1_1 C1_1 C2_1 C14_1 178.05(13) . . . . ?
C17_1 C1_1 C2_1 C3_1 -174.06(13) . . . . ?
N1_1 C1_1 C2_1 C3_1 1.16(19) . . . . ?
O2_1 S1_1 N3_1 C3_1 176.33(10) . . . . ?
O1_1 S1_1 N3_1 C3_1 47.11(11) . . . . ?
C7_1 S1_1 N3_1 C3_1 -68.24(11) . . . . ?
O2_1 S1_1 N3_1 C4_1 -41.43(12) . . . . ?
O1_1 S1_1 N3_1 C4_1 -170.64(10) . . . . ?
C7_1 S1_1 N3_1 C4_1 74.01(10) . . . . ?
C4_1 N3_1 C3_1 C2_1 84.53(15) . . . . ?
S1_1 N3_1 C3_1 C2_1 -132.13(11) . . . . ?
C14_1 C2_1 C3_1 N3_1 82.45(16) . . . . ?
C1_1 C2_1 C3_1 N3_1 -100.71(15) . . . . ?
C3_1 N3_1 C4_1 C5_1 -80.98(14) . . . . ?
S1_1 N3_1 C4_1 C5_1 136.25(10) . . . . ?
N3_1 C4_1 C5_1 C6_1 94.05(15) . . . . ?
N3_1 C4_1 C5_1 C21_1 -87.05(14) . . . . ?
C21_1 C5_1 C6_1 C18_1 -2.31(19) . . . . ?
C4_1 C5_1 C6_1 C18_1 176.61(12) . . . . ?
C21_1 C5_1 C6_1 N2_1 -176.46(12) . . . . ?
C4_1 C5_1 C6_1 N2_1 2.46(19) . . . . ?
N1_1 N2_1 C6_1 C5_1 -91.77(17) . . . . ?
N1_1 N2_1 C6_1 C18_1 93.83(17) . . . . ?
O2_1 S1_1 C7_1 C12_1 26.85(15) . . . . ?
O1_1 S1_1 C7_1 C12_1 158.24(14) . . . . ?
N3_1 S1_1 C7_1 C12_1 -87.58(14) . . . . ?
O2_1 S1_1 C7_1 C8_1 -154.16(13) . . . . ?
O1_1 S1_1 C7_1 C8_1 -22.77(15) . . . . ?
N3_1 S1_1 C7_1 C8_1 91.42(13) . . . . ?
C12_1 C7_1 C8_1 C9_1 0.7(3) . . . . ?
S1_1 C7_1 C8_1 C9_1 -178.33(14) . . . . ?
C7_1 C8_1 C9_1 C10_1 -1.1(3) . . . . ?
C8_1 C9_1 C10_1 C11_1 1.1(3) . . . . ?
C8_1 C9_1 C10_1 C13_1 -179.32(18) . . . . ?
C9_1 C10_1 C11_1 C12_1 -0.8(3) . . . . ?
C13_1 C10_1 C11_1 C12_1 179.67(19) . . . . ?
C8_1 C7_1 C12_1 C11_1 -0.3(3) . . . . ?
S1_1 C7_1 C12_1 C11_1 178.68(15) . . . . ?
C10_1 C11_1 C12_1 C7_1 0.4(3) . . . . ?
C1_1 C2_1 C14_1 C15_1 -1.4(2) . . . . ?
C3_1 C2_1 C14_1 C15_1 175.60(14) . . . . ?
C2_1 C14_1 C15_1 C16_1 -0.4(3) . . . . ?
C14_1 C15_1 C16_1 C17_1 0.8(3) . . . . ?
C15_1 C16_1 C17_1 C1_1 0.6(3) . . . . ?
C2_1 C1_1 C17_1 C16_1 -2.5(2) . . . . ?
N1_1 C1_1 C17_1 C16_1 -177.76(14) . . . . ?
C5_1 C6_1 C18_1 C19_1 2.3(2) . . . . ?
N2_1 C6_1 C18_1 C19_1 176.68(13) . . . . ?
C6_1 C18_1 C19_1 C20_1 -1.0(2) . . . . ?
C18_1 C19_1 C20_1 C21_1 -0.2(2) . . . . ?
C19_1 C20_1 C21_1 C5_1 0.2(2) . . . . ?
C6_1 C5_1 C21_1 C20_1 1.03(19) . . . . ?
C4_1 C5_1 C21_1 C20_1 -177.94(12) . . . . ?
C2_2 C1_2 N1_2 N2_2 91.83(18) . . . . ?
C17_2 C1_2 N1_2 N2_2 -92.31(17) . . . . ?
C17_2 C1_2 C2_2 C14_2 1.3(2) . . . . ?
N1_2 C1_2 C2_2 C14_2 177.08(13) . . . . ?
C17_2 C1_2 C2_2 C3_2 -179.23(13) . . . . ?
N1_2 C1_2 C2_2 C3_2 -3.46(19) . . . . ?
O1_2 S1_2 N3_2 C4_2 -162.86(10) . . . . ?
O2_2 S1_2 N3_2 C4_2 -33.67(12) . . . . ?
C7_2 S1_2 N3_2 C4_2 81.70(11) . . . . ?
O1_2 S1_2 N3_2 C3_2 44.96(12) . . . . ?
O2_2 S1_2 N3_2 C3_2 174.14(10) . . . . ?
C7_2 S1_2 N3_2 C3_2 -70.49(11) . . . . ?
C3_2 N3_2 C4_2 C5_2 -82.99(15) . . . . ?
S1_2 N3_2 C4_2 C5_2 124.59(11) . . . . ?
N3_2 C4_2 C5_2 C21_2 -81.68(16) . . . . ?
N3_2 C4_2 C5_2 C6_2 97.32(15) . . . . ?
C21_2 C5_2 C6_2 C18_2 -2.6(2) . . . . ?
C4_2 C5_2 C6_2 C18_2 178.35(13) . . . . ?
C21_2 C5_2 C6_2 N2_2 179.89(13) . . . . ?
C4_2 C5_2 C6_2 N2_2 0.87(19) . . . . ?
O1_2 S1_2 C7_2 C12_2 155.29(11) . . . . ?
O2_2 S1_2 C7_2 C12_2 24.89(13) . . . . ?
N3_2 S1_2 C7_2 C12_2 -89.88(12) . . . . ?
O1_2 S1_2 C7_2 C8_2 -24.97(13) . . . . ?
O2_2 S1_2 C7_2 C8_2 -155.37(12) . . . . ?
N3_2 S1_2 C7_2 C8_2 89.86(12) . . . . ?
C12_2 C7_2 C8_2 C9_2 0.5(2) . . . . ?
S1_2 C7_2 C8_2 C9_2 -179.26(13) . . . . ?
C7_2 C8_2 C9_2 C10_2 -1.1(3) . . . . ?
C8_2 C9_2 C10_2 C11_2 0.9(2) . . . . ?
C8_2 C9_2 C10_2 C13_2 -178.35(16) . . . . ?
C9_2 C10_2 C11_2 C12_2 -0.1(2) . . . . ?
C13_2 C10_2 C11_2 C12_2 179.12(14) . . . . ?
C8_2 C7_2 C12_2 C11_2 0.3(2) . . . . ?
S1_2 C7_2 C12_2 C11_2 -179.98(12) . . . . ?
C10_2 C11_2 C12_2 C7_2 -0.5(2) . . . . ?
C1_2 C2_2 C14_2 C15_2 -0.2(2) . . . . ?
C3_2 C2_2 C14_2 C15_2 -179.64(13) . . . . ?
C2_2 C14_2 C15_2 C16_2 -0.5(2) . . . . ?
C14_2 C15_2 C16_2 C17_2 0.0(3) . . . . ?
C15_2 C16_2 C17_2 C1_2 1.1(3) . . . . ?
C2_2 C1_2 C17_2 C16_2 -1.8(2) . . . . ?
N1_2 C1_2 C17_2 C16_2 -177.62(15) . . . . ?
C5_2 C6_2 C18_2 C19_2 4.0(2) . . . . ?
N2_2 C6_2 C18_2 C19_2 -178.57(14) . . . . ?
C6_2 C18_2 C19_2 C20_2 -2.4(2) . . . . ?
C18_2 C19_2 C20_2 C21_2 -0.4(2) . . . . ?
C6_2 C5_2 C21_2 C20_2 -0.2(2) . . . . ?
C4_2 C5_2 C21_2 C20_2 178.86(13) . . . . ?
C19_2 C20_2 C21_2 C5_2 1.7(2) . . . . ?
C4_2 N3_2 C3_2 C2_2 81.79(15) . . . . ?
S1_2 N3_2 C3_2 C2_2 -125.66(11) . . . . ?
C1_2 C2_2 C3_2 N3_2 -93.71(15) . . . . ?
C14_2 C2_2 C3_2 N3_2 85.74(16) . . . . ?
C1_2 N1_2 N2_2 C6_2 -0.7(2) . . . . ?
C18_2 C6_2 N2_2 N1_2 94.40(18) . . . . ?
C5_2 C6_2 N2_2 N1_2 -88.09(17) . . . . ?

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
_geom_hbond_publ_flag
C3_1 H3A_1 N2_1 0.97 2.50 3.4267(19) 159.9 2_565 yes
C4_1 H4_1 O2_1 0.97 2.42 2.898(2) 110.3 . yes
C4_1 H4_1 O2_2 0.97 2.64 3.4540(17) 142.0 . yes

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.061






####################################################################### 
# 
# 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_E-2a
_database_code_depnum_ccdc_archive 'CCDC 2007075'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2021-03-05 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
;
tert-butyl(E)-11,13-dihydro-12H-dibenzo[c,h][1,2,6]triazonine-12-carboxylate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H21 N3 O2'
_chemical_formula_sum            'C19 H21 N3 O2'
_chemical_formula_weight         323.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_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                   13.7733(4)
_cell_length_b                   10.3424(3)
_cell_length_c                   12.3133(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.874(3)
_cell_angle_gamma                90
_cell_volume                     1753.08(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9463
_cell_measurement_theta_min      3.9330
_cell_measurement_theta_max      29.2490

_exptl_crystal_description       chunk
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.38180
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_detector                 'Dectris PILATUS3 R 200K-A area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'Hybrid Photon Counting area detector'

_diffrn_measurement_device       'kappa gonio four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'

_diffrn_radiation_collimation    
'Rigaku Integrated Confocal MaxFlux double bounce multi-layer mirror optics'
_diffrn_radiation_monochromator  none
_diffrn_radiation_probe          x-ray

_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Rigaku micromax 003'
_diffrn_reflns_number            19111
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.671
_diffrn_reflns_theta_max         27.100
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3825
_reflns_number_gt                3293
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1028P)²+0.0795P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_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_number_reflns         3825
_refine_ls_number_parameters     410
_refine_ls_number_restraints     441
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1444
_refine_ls_wR_factor_gt          0.1384
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.71158(12) 0.54257(16) 0.72357(11) 0.0329(4) Uani 0.794(4) 1 d D . P A 1
C1 C 0.79672(17) 0.6122(2) 0.69699(18) 0.0305(5) Uani 0.794(4) 1 d D . P A 1
O1 O 0.8783(4) 0.3149(7) 0.5712(6) 0.0451(13) Uani 0.794(4) 1 d D . P A 1
N2 N 0.65163(12) 0.54193(15) 0.64475(11) 0.0307(4) Uani 0.794(4) 1 d D . P A 1
C2 C 0.8354(3) 0.6017(5) 0.5932(3) 0.0289(7) Uani 0.794(4) 1 d D . P A 1
O2 O 0.7405(4) 0.1990(4) 0.5328(7) 0.0329(8) Uani 0.794(4) 1 d D . P A 1
C3 C 0.79189(16) 0.5353(3) 0.49211(19) 0.0312(4) Uani 0.794(4) 1 d D . P A 1
H3A H 0.745128 0.596400 0.457214 0.037 Uiso 0.794(4) 1 calc R U P A 1
H3B H 0.845008 0.522682 0.440904 0.037 Uiso 0.794(4) 1 calc R U P A 1
N3 N 0.7416(2) 0.4097(3) 0.5031(3) 0.0263(4) Uani 0.794(4) 1 d D . P A 1
C4 C 0.6394(2) 0.3981(4) 0.4650(3) 0.0276(6) Uani 0.794(4) 1 d D . P A 1
H4A H 0.634090 0.327395 0.410929 0.033 Uiso 0.794(4) 1 calc R U P A 1
H4AB H 0.619567 0.479335 0.428043 0.033 Uiso 0.794(4) 1 calc R U P A 1
C5 C 0.5696(3) 0.3708(5) 0.5561(3) 0.0261(7) Uani 0.794(4) 1 d D . P A 1
C6 C 0.5768(2) 0.4470(3) 0.6499(2) 0.0292(6) Uani 0.794(4) 1 d D . P A 1
C7 C 0.7942(4) 0.3074(4) 0.5391(7) 0.0286(6) Uani 0.794(4) 1 d D . P A 1
C8 C 0.7776(3) 0.0747(4) 0.5752(3) 0.0370(10) Uani 0.794(4) 1 d D . P A 1
C9 C 0.7857(5) 0.0845(4) 0.6980(3) 0.0648(8) Uani 0.794(4) 1 d D . P A 1
H9A H 0.803664 -0.000017 0.728628 0.097 Uiso 0.794(4) 1 calc R U P A 1
H9B H 0.723161 0.111613 0.726073 0.097 Uiso 0.794(4) 1 calc R U P A 1
H9C H 0.835662 0.148160 0.718771 0.097 Uiso 0.794(4) 1 calc R U P A 1
C10 C 0.6972(3) -0.0165(4) 0.5400(4) 0.0447(7) Uani 0.794(4) 1 d D . P A 1
H10A H 0.713315 -0.104233 0.564599 0.067 Uiso 0.794(4) 1 calc R U P A 1
H10B H 0.689682 -0.015524 0.460576 0.067 Uiso 0.794(4) 1 calc R U P A 1
H10C H 0.636296 0.011044 0.571899 0.067 Uiso 0.794(4) 1 calc R U P A 1
C11 C 0.8726(2) 0.0391(4) 0.5266(4) 0.0560(8) Uani 0.794(4) 1 d D . P A 1
H11A H 0.889043 -0.050450 0.545681 0.084 Uiso 0.794(4) 1 calc R U P A 1
H11B H 0.923725 0.096934 0.554917 0.084 Uiso 0.794(4) 1 calc R U P A 1
H11C H 0.866929 0.047471 0.447323 0.084 Uiso 0.794(4) 1 calc R U P A 1
C12 C 0.9264(3) 0.6585(7) 0.5794(5) 0.0375(8) Uani 0.794(4) 1 d D . P A 1
H12 H 0.956411 0.649750 0.511392 0.045 Uiso 0.794(4) 1 calc R U P A 1
C13 C 0.9740(5) 0.7273(9) 0.6621(5) 0.0404(10) Uani 0.794(4) 1 d D . P A 1
H13 H 1.035500 0.765157 0.649696 0.048 Uiso 0.794(4) 1 calc R U P A 1
C14 C 0.9325(3) 0.7411(7) 0.7627(4) 0.0434(10) Uani 0.794(4) 1 d D . P A 1
H14 H 0.962976 0.792893 0.817629 0.052 Uiso 0.794(4) 1 calc R U P A 1
C15 C 0.8455(2) 0.6779(3) 0.7817(2) 0.0384(6) Uani 0.794(4) 1 d D . P A 1
H15 H 0.819371 0.679304 0.852148 0.046 Uiso 0.794(4) 1 calc R U P A 1
C16 C 0.5172(3) 0.4257(3) 0.7371(3) 0.0359(6) Uani 0.794(4) 1 d D . P A 1
H16 H 0.524403 0.476458 0.801149 0.043 Uiso 0.794(4) 1 calc R U P A 1
C17 C 0.4471(3) 0.3298(3) 0.7298(4) 0.0378(7) Uani 0.794(4) 1 d D . P A 1
H17 H 0.405673 0.314495 0.788621 0.045 Uiso 0.794(4) 1 calc R U P A 1
C18 C 0.4379(4) 0.2565(6) 0.6361(4) 0.0367(9) Uani 0.794(4) 1 d D . P A 1
H18 H 0.389454 0.191246 0.630763 0.044 Uiso 0.794(4) 1 calc R U P A 1
C19 C 0.4993(2) 0.2770(3) 0.5484(3) 0.0296(5) Uani 0.794(4) 1 d D . P A 1
H19 H 0.492093 0.226163 0.484426 0.036 Uiso 0.794(4) 1 calc R U P A 1
N1B N 0.6958(5) 0.5848(6) 0.6456(4) 0.0392(16) Uani 0.206(4) 1 d D . P A 2
C1B C 0.7898(6) 0.6368(8) 0.6618(8) 0.0298(18) Uani 0.206(4) 1 d D . P A 2
O1B O 0.8837(13) 0.327(3) 0.581(2) 0.036(3) Uani 0.206(4) 1 d D . P A 2
N2B N 0.6703(6) 0.5067(7) 0.7160(5) 0.0424(16) Uani 0.206(4) 1 d D . P A 2
C2B C 0.8552(11) 0.6142(19) 0.5800(12) 0.025(2) Uani 0.206(4) 1 d D . P A 2
O2B O 0.7468(17) 0.2193(16) 0.536(3) 0.035(3) Uani 0.206(4) 1 d D . P A 2
C3B C 0.8143(8) 0.5388(13) 0.4805(9) 0.0312(4) Uani 0.206(4) 1 d D . P A 2
H13C H 0.776843 0.599974 0.433584 0.037 Uiso 0.206(4) 1 calc R U P A 2
H13D H 0.869800 0.508062 0.438385 0.037 Uiso 0.206(4) 1 calc R U P A 2
N3B N 0.7543(9) 0.4317(12) 0.5009(13) 0.0263(4) Uani 0.206(4) 1 d D . P A 2
C4B C 0.6518(10) 0.418(2) 0.4815(13) 0.039(3) Uani 0.206(4) 1 d D . P A 2
H4BA H 0.642515 0.347755 0.427125 0.047 Uiso 0.206(4) 1 calc R U P A 2
H4BB H 0.628348 0.498408 0.446442 0.047 Uiso 0.206(4) 1 calc R U P A 2
C5B C 0.5847(13) 0.389(2) 0.5734(12) 0.030(3) Uani 0.206(4) 1 d D . P A 2
C6B C 0.5892(9) 0.4309(14) 0.6788(9) 0.032(2) Uani 0.206(4) 1 d D . P A 2
C7B C 0.8019(16) 0.3243(18) 0.543(3) 0.0286(6) Uani 0.206(4) 1 d D . P A 2
C8B C 0.7773(10) 0.0953(16) 0.5854(14) 0.032(3) Uani 0.206(4) 1 d D . P A 2
C9B C 0.795(2) 0.110(2) 0.7063(14) 0.0648(8) Uani 0.206(4) 1 d D . P A 2
H9BA H 0.781286 0.027677 0.742316 0.097 Uiso 0.206(4) 1 calc R U P A 2
H9BB H 0.751546 0.176998 0.733751 0.097 Uiso 0.206(4) 1 calc R U P A 2
H9BC H 0.862433 0.134794 0.721480 0.097 Uiso 0.206(4) 1 calc R U P A 2
C10B C 0.6944(15) 0.006(2) 0.558(2) 0.072(5) Uani 0.206(4) 1 d D . P A 2
H10D H 0.699031 -0.070758 0.604589 0.108 Uiso 0.206(4) 1 calc R U P A 2
H10E H 0.696982 -0.020111 0.481726 0.108 Uiso 0.206(4) 1 calc R U P A 2
H10F H 0.632837 0.050568 0.570069 0.108 Uiso 0.206(4) 1 calc R U P A 2
C11B C 0.8680(15) 0.051(2) 0.528(2) 0.118(8) Uani 0.206(4) 1 d D . P A 2
H11D H 0.883634 -0.038396 0.549622 0.177 Uiso 0.206(4) 1 calc R U P A 2
H11E H 0.922658 0.107318 0.548086 0.177 Uiso 0.206(4) 1 calc R U P A 2
H11F H 0.855981 0.054011 0.449054 0.177 Uiso 0.206(4) 1 calc R U P A 2
C12B C 0.9434(14) 0.670(3) 0.5902(18) 0.039(3) Uani 0.206(4) 1 d D . P A 2
H12B H 0.986538 0.660868 0.532047 0.047 Uiso 0.206(4) 1 calc R U P A 2
C13B C 0.975(2) 0.739(4) 0.681(2) 0.045(4) Uani 0.206(4) 1 d D . P A 2
H13B H 1.034085 0.785649 0.681727 0.054 Uiso 0.206(4) 1 calc R U P A 2
C14B C 0.9159(15) 0.739(3) 0.7684(17) 0.058(5) Uani 0.206(4) 1 d D . P A 2
H14B H 0.939782 0.764261 0.838359 0.070 Uiso 0.206(4) 1 calc R U P A 2
C15B C 0.8218(8) 0.6995(11) 0.7516(8) 0.045(2) Uani 0.206(4) 1 d D . P A 2
H15B H 0.776649 0.717691 0.806323 0.054 Uiso 0.206(4) 1 calc R U P A 2
C16B C 0.5254(10) 0.3897(12) 0.7565(11) 0.039(3) Uani 0.206(4) 1 d D . P A 2
H16B H 0.532045 0.420144 0.829130 0.047 Uiso 0.206(4) 1 calc R U P A 2
C17B C 0.4535(14) 0.3056(17) 0.7280(16) 0.0378(7) Uani 0.206(4) 1 d D . P A 2
H17B H 0.408284 0.280302 0.780586 0.045 Uiso 0.206(4) 1 calc R U P A 2
C18B C 0.4447(15) 0.255(2) 0.6228(15) 0.042(4) Uani 0.206(4) 1 d D . P A 2
H18B H 0.393866 0.198791 0.599120 0.050 Uiso 0.206(4) 1 calc R U P A 2
C19B C 0.5180(12) 0.2968(18) 0.5568(13) 0.061(5) Uani 0.206(4) 1 d D . P A 2
H19B H 0.521248 0.252931 0.489242 0.073 Uiso 0.206(4) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.253(2) . ?
N1 C1 1.423(3) . ?
C1 C15 1.399(3) . ?
C1 C2 1.405(4) . ?
O1 C7 1.214(4) . ?
N2 C6 1.426(3) . ?
C2 C12 1.399(4) . ?
C2 C3 1.527(4) . ?
O2 C7 1.344(3) . ?
O2 C8 1.473(4) . ?
C3 N3 1.480(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
N3 C7 1.349(3) . ?
N3 C4 1.474(3) . ?
C4 C5 1.527(3) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C5 C19 1.372(4) . ?
C5 C6 1.399(3) . ?
C6 C16 1.391(4) . ?
C8 C11 1.503(4) . ?
C8 C10 1.507(4) . ?
C8 C9 1.516(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.389(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.384(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.409(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N1B N2B 1.244(10) . ?
N1B C1B 1.411(10) . ?
C1B C15B 1.344(11) . ?
C1B C2B 1.393(11) . ?
O1B C7B 1.203(15) . ?
N2B C6B 1.427(12) . ?
C2B C12B 1.346(13) . ?
C2B C3B 1.544(13) . ?
O2B C7B 1.327(13) . ?
O2B C8B 1.477(14) . ?
C3B N3B 1.409(11) . ?
C3B H13C 0.9900 . ?
C3B H13D 0.9900 . ?
N3B C7B 1.384(14) . ?
N3B C4B 1.431(13) . ?
C4B C5B 1.515(14) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C5B C19B 1.334(12) . ?
C5B C6B 1.368(12) . ?
C6B C16B 1.387(13) . ?
C8B C10B 1.499(14) . ?
C8B C9B 1.508(15) . ?
C8B C11B 1.528(15) . ?
C9B H9BA 0.9800 . ?
C9B H9BB 0.9800 . ?
C9B H9BC 0.9800 . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B C13B 1.380(15) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.372(15) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.366(14) . ?
C14B H14B 0.9500 . ?
C15B H15B 0.9500 . ?
C16B C17B 1.355(15) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.398(15) . ?
C17B H17B 0.9500 . ?
C18B C19B 1.385(15) . ?
C18B H18B 0.9500 . ?
C19B H19B 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
N2 N1 C1 110.58(18) . . ?
C15 C1 C2 121.9(2) . . ?
C15 C1 N1 117.0(2) . . ?
C2 C1 N1 120.7(2) . . ?
N1 N2 C6 115.3(2) . . ?
C12 C2 C1 116.5(3) . . ?
C12 C2 C3 114.7(3) . . ?
C1 C2 C3 128.7(3) . . ?
C7 O2 C8 121.6(4) . . ?
N3 C3 C2 119.5(3) . . ?
N3 C3 H3A 107.4 . . ?
C2 C3 H3A 107.4 . . ?
N3 C3 H3B 107.4 . . ?
C2 C3 H3B 107.4 . . ?
H3A C3 H3B 107.0 . . ?
C7 N3 C4 122.5(3) . . ?
C7 N3 C3 118.1(3) . . ?
C4 N3 C3 119.2(3) . . ?
N3 C4 C5 113.5(3) . . ?
N3 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
N3 C4 H4AB 108.9 . . ?
C5 C4 H4AB 108.9 . . ?
H4A C4 H4AB 107.7 . . ?
C19 C5 C6 119.1(3) . . ?
C19 C5 C4 122.6(3) . . ?
C6 C5 C4 118.2(3) . . ?
C16 C6 C5 121.3(3) . . ?
C16 C6 N2 126.1(3) . . ?
C5 C6 N2 112.5(2) . . ?
O1 C7 O2 126.1(4) . . ?
O1 C7 N3 123.6(4) . . ?
O2 C7 N3 110.3(3) . . ?
O2 C8 C11 111.7(4) . . ?
O2 C8 C10 101.6(3) . . ?
C11 C8 C10 111.9(3) . . ?
O2 C8 C9 108.0(4) . . ?
C11 C8 C9 112.2(4) . . ?
C10 C8 C9 111.0(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C2 121.9(4) . . ?
C13 C12 H12 119.0 . . ?
C2 C12 H12 119.0 . . ?
C14 C13 C12 120.5(4) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 118.9(4) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C14 C15 C1 119.9(3) . . ?
C14 C15 H15 120.1 . . ?
C1 C15 H15 120.1 . . ?
C17 C16 C6 119.4(3) . . ?
C17 C16 H16 120.3 . . ?
C6 C16 H16 120.3 . . ?
C18 C17 C16 119.4(4) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 121.1(4) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C5 C19 C18 119.6(3) . . ?
C5 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
N2B N1B C1B 115.3(8) . . ?
C15B C1B C2B 118.3(9) . . ?
C15B C1B N1B 125.1(9) . . ?
C2B C1B N1B 116.5(8) . . ?
N1B N2B C6B 111.6(8) . . ?
C12B C2B C1B 117.6(12) . . ?
C12B C2B C3B 126.5(12) . . ?
C1B C2B C3B 115.5(10) . . ?
C7B O2B C8B 121.7(15) . . ?
N3B C3B C2B 117.2(11) . . ?
N3B C3B H13C 108.0 . . ?
C2B C3B H13C 108.0 . . ?
N3B C3B H13D 108.0 . . ?
C2B C3B H13D 108.0 . . ?
H13C C3B H13D 107.2 . . ?
C7B N3B C3B 115.1(13) . . ?
C7B N3B C4B 115.7(13) . . ?
C3B N3B C4B 129.2(13) . . ?
N3B C4B C5B 121.2(13) . . ?
N3B C4B H4BA 107.0 . . ?
C5B C4B H4BA 107.0 . . ?
N3B C4B H4BB 107.0 . . ?
C5B C4B H4BB 107.0 . . ?
H4BA C4B H4BB 106.8 . . ?
C19B C5B C6B 112.4(12) . . ?
C19B C5B C4B 117.4(12) . . ?
C6B C5B C4B 129.5(12) . . ?
C5B C6B C16B 123.1(11) . . ?
C5B C6B N2B 119.3(10) . . ?
C16B C6B N2B 117.0(10) . . ?
O1B C7B O2B 125.1(17) . . ?
O1B C7B N3B 123.4(17) . . ?
O2B C7B N3B 111.5(13) . . ?
O2B C8B C10B 103.7(14) . . ?
O2B C8B C9B 110.9(17) . . ?
C10B C8B C9B 112.2(14) . . ?
O2B C8B C11B 107.3(16) . . ?
C10B C8B C11B 109.8(15) . . ?
C9B C8B C11B 112.5(17) . . ?
C8B C9B H9BA 109.5 . . ?
C8B C9B H9BB 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
C8B C9B H9BC 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
C8B C10B H10D 109.5 . . ?
C8B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
C8B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C8B C11B H11D 109.5 . . ?
C8B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C8B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C2B C12B C13B 123.6(17) . . ?
C2B C12B H12B 118.2 . . ?
C13B C12B H12B 118.2 . . ?
C14B C13B C12B 117.2(17) . . ?
C14B C13B H13B 121.4 . . ?
C12B C13B H13B 121.4 . . ?
C15B C14B C13B 117.5(16) . . ?
C15B C14B H14B 121.2 . . ?
C13B C14B H14B 121.2 . . ?
C1B C15B C14B 123.4(12) . . ?
C1B C15B H15B 118.3 . . ?
C14B C15B H15B 118.3 . . ?
C17B C16B C6B 119.5(13) . . ?
C17B C16B H16B 120.2 . . ?
C6B C16B H16B 120.2 . . ?
C16B C17B C18B 121.3(15) . . ?
C16B C17B H17B 119.3 . . ?
C18B C17B H17B 119.3 . . ?
C19B C18B C17B 112.7(13) . . ?
C19B C18B H18B 123.7 . . ?
C17B C18B H18B 123.7 . . ?
C5B C19B C18B 130.0(13) . . ?
C5B C19B H19B 115.0 . . ?
C18B C19B H19B 115.0 . . ?

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
N2 N1 C1 C15 148.19(19) . . . . ?
N2 N1 C1 C2 -39.2(4) . . . . ?
C1 N1 N2 C6 163.2(2) . . . . ?
C15 C1 C2 C12 1.1(6) . . . . ?
N1 C1 C2 C12 -171.1(4) . . . . ?
C15 C1 C2 C3 -179.3(4) . . . . ?
N1 C1 C2 C3 8.4(6) . . . . ?
C12 C2 C3 N3 139.0(4) . . . . ?
C1 C2 C3 N3 -40.6(6) . . . . ?
C2 C3 N3 C7 -63.8(6) . . . . ?
C2 C3 N3 C4 121.9(4) . . . . ?
C7 N3 C4 C5 70.7(7) . . . . ?
C3 N3 C4 C5 -115.3(4) . . . . ?
N3 C4 C5 C19 -133.2(4) . . . . ?
N3 C4 C5 C6 48.2(6) . . . . ?
C19 C5 C6 C16 2.8(7) . . . . ?
C4 C5 C6 C16 -178.5(4) . . . . ?
C19 C5 C6 N2 -178.6(4) . . . . ?
C4 C5 C6 N2 0.0(6) . . . . ?
N1 N2 C6 C16 51.2(4) . . . . ?
N1 N2 C6 C5 -127.3(3) . . . . ?
C8 O2 C7 O1 5.7(14) . . . . ?
C8 O2 C7 N3 -175.0(7) . . . . ?
C4 N3 C7 O1 -179.7(7) . . . . ?
C3 N3 C7 O1 6.2(11) . . . . ?
C4 N3 C7 O2 0.9(9) . . . . ?
C3 N3 C7 O2 -173.2(5) . . . . ?
C7 O2 C8 C11 -55.3(9) . . . . ?
C7 O2 C8 C10 -174.7(7) . . . . ?
C7 O2 C8 C9 68.4(8) . . . . ?
C1 C2 C12 C13 -3.1(9) . . . . ?
C3 C2 C12 C13 177.3(7) . . . . ?
C2 C12 C13 C14 0.5(13) . . . . ?
C12 C13 C14 C15 4.2(12) . . . . ?
C13 C14 C15 C1 -6.1(9) . . . . ?
C2 C1 C15 C14 3.5(5) . . . . ?
N1 C1 C15 C14 176.0(4) . . . . ?
C5 C6 C16 C17 -2.0(5) . . . . ?
N2 C6 C16 C17 179.7(3) . . . . ?
C6 C16 C17 C18 0.3(6) . . . . ?
C16 C17 C18 C19 0.6(8) . . . . ?
C6 C5 C19 C18 -1.9(7) . . . . ?
C4 C5 C19 C18 179.5(5) . . . . ?
C17 C18 C19 C5 0.2(8) . . . . ?
N2B N1B C1B C15B -56.0(11) . . . . ?
N2B N1B C1B C2B 120.3(13) . . . . ?
C1B N1B N2B C6B -162.7(9) . . . . ?
C15B C1B C2B C12B -8(3) . . . . ?
N1B C1B C2B C12B 175.8(19) . . . . ?
C15B C1B C2B C3B 178.5(12) . . . . ?
N1B C1B C2B C3B 2(2) . . . . ?
C12B C2B C3B N3B 144(2) . . . . ?
C1B C2B C3B N3B -43(2) . . . . ?
C2B C3B N3B C7B -72(2) . . . . ?
C2B C3B N3B C4B 109.3(19) . . . . ?
C7B N3B C4B C5B 61(3) . . . . ?
C3B N3B C4B C5B -121(2) . . . . ?
N3B C4B C5B C19B -134(2) . . . . ?
N3B C4B C5B C6B 36(4) . . . . ?
C19B C5B C6B C16B -5(3) . . . . ?
C4B C5B C6B C16B -175.8(19) . . . . ?
C19B C5B C6B N2B 165.9(16) . . . . ?
C4B C5B C6B N2B -5(3) . . . . ?
N1B N2B C6B C5B 39.0(18) . . . . ?
N1B N2B C6B C16B -149.3(10) . . . . ?
C8B O2B C7B O1B 8(5) . . . . ?
C8B O2B C7B N3B -173(3) . . . . ?
C3B N3B C7B O1B 14(5) . . . . ?
C4B N3B C7B O1B -167(3) . . . . ?
C3B N3B C7B O2B -165(2) . . . . ?
C4B N3B C7B O2B 14(4) . . . . ?
C7B O2B C8B C10B 179(3) . . . . ?
C7B O2B C8B C9B 59(3) . . . . ?
C7B O2B C8B C11B -64(3) . . . . ?
C1B C2B C12B C13B 5(4) . . . . ?
C3B C2B C12B C13B 178(3) . . . . ?
C2B C12B C13B C14B 7(6) . . . . ?
C12B C13B C14B C15B -17(5) . . . . ?
C2B C1B C15B C14B -2(2) . . . . ?
N1B C1B C15B C14B 174(2) . . . . ?
C13B C14B C15B C1B 15(4) . . . . ?
C5B C6B C16B C17B -1(2) . . . . ?
N2B C6B C16B C17B -172.6(14) . . . . ?
C6B C16B C17B C18B 3(3) . . . . ?
C16B C17B C18B C19B 2(3) . . . . ?
C6B C5B C19B C18B 12(4) . . . . ?
C4B C5B C19B C18B -176(2) . . . . ?
C17B C18B C19B C5B -11(4) . . . . ?

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
_geom_hbond_publ_flag
C9 H9C O1 0.98 2.59 3.142(8) 116.0 . yes
C11 H11B O1 0.98 2.35 2.906(8) 115.2 . yes
C11B H11E O1B 0.98 2.37 2.94(4) 116.2 . yes

_refine_diff_density_max         0.332
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.074






####################################################################### 
# 
# 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_E-2c
_database_code_depnum_ccdc_archive 'CCDC 2056225'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2021-03-05 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3

_chemical_name_systematic        
;
'ethyl (E)-11,13-dihydro-12H-dibenzo[c,h][1,2,6]triazonine-12-carboxylate'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 N3 O2'
_chemical_formula_sum            'C17 H17 N3 O2'
_chemical_formula_weight         295.33

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   5.0393(3)
_cell_length_b                   11.5613(6)
_cell_length_c                   26.3881(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1537.41(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4102
_cell_measurement_theta_min      3.6750
_cell_measurement_theta_max      25.4810

_exptl_crystal_description       stick
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.43897
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_detector                 'Dectris PILATUS3 R 200K-A area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'Hybrid Photon Counting area detector'

_diffrn_measurement_device       'kappa gonio four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'

_diffrn_radiation_collimation    
'Rigaku Integrated Confocal MaxFlux double bounce multi-layer mirror optics'
_diffrn_radiation_monochromator  none
_diffrn_radiation_probe          x-ray

_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Rigaku micromax 003'
_diffrn_reflns_number            9387
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.524
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             3072
_reflns_number_gt                2567
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.653
_reflns_Friedel_fraction_max     0.944
_reflns_Friedel_fraction_full    0.968

_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0606P)²+0.0035P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.025(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(17)
_chemical_absolute_configuration .
_refine_ls_number_reflns         3063
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.0985
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
O1 O 0.4802(4) 0.55052(14) 0.45809(5) 0.0675(5) Uani 1 1 d . . . . .
C1 C 0.5269(4) 0.26939(16) 0.37894(7) 0.0463(5) Uani 1 1 d . . . . .
N1 N 0.3689(4) 0.32032(13) 0.33992(6) 0.0487(4) Uani 1 1 d . . . . .
O2 O 0.3263(3) 0.67523(11) 0.39924(5) 0.0568(4) Uani 1 1 d . . . . .
C2 C 0.7302(4) 0.33187(18) 0.40294(7) 0.0477(5) Uani 1 1 d . . . . .
N2 N 0.5084(4) 0.38277(13) 0.31221(6) 0.0456(4) Uani 1 1 d . . . . .
N3 N 0.6296(4) 0.54398(13) 0.37705(6) 0.0451(4) Uani 1 1 d . . . . .
C3 C 0.8242(5) 0.45380(18) 0.39053(8) 0.0532(5) Uani 1 1 d . . . . .
H3A H 0.923241 0.481685 0.419587 0.064 Uiso 1 1 calc R U . . .
H3AB H 0.948740 0.447766 0.362632 0.064 Uiso 1 1 calc R U . . .
C4 C 0.6491(5) 0.60324(17) 0.32773(7) 0.0505(5) Uani 1 1 d . . . . .
H4A H 0.820129 0.584675 0.312963 0.061 Uiso 1 1 calc R U . . .
H4AB H 0.646357 0.685969 0.333831 0.061 Uiso 1 1 calc R U . . .
C5 C 0.4365(4) 0.57548(15) 0.28903(7) 0.0444(5) Uani 1 1 d . . . . .
C6 C 0.3644(5) 0.46068(16) 0.28042(7) 0.0448(5) Uani 1 1 d . . . . .
C7 C 0.4803(5) 0.58616(16) 0.41507(7) 0.0469(5) Uani 1 1 d . . . . .
C11 C 0.6025(6) 0.1056(2) 0.43240(9) 0.0696(7) Uani 1 1 d . . . . .
H11 H 0.560121 0.030538 0.442195 0.083 Uiso 1 1 calc R U . . .
C10 C 0.4599(6) 0.15971(18) 0.39497(9) 0.0598(6) Uani 1 1 d . . . . .
H10 H 0.316424 0.121939 0.380239 0.072 Uiso 1 1 calc R U . . .
C9 C 0.0447(9) 0.8342(3) 0.41643(12) 0.1019(12) Uani 1 1 d . . . . .
H9A H -0.043499 0.876557 0.442796 0.153 Uiso 1 1 calc R U . . .
H9B H -0.083323 0.809031 0.391843 0.153 Uiso 1 1 calc R U . . .
H9C H 0.173449 0.883098 0.400315 0.153 Uiso 1 1 calc R U . . .
C8 C 0.1770(7) 0.7341(2) 0.43812(10) 0.0729(8) Uani 1 1 d . . . . .
H8A H 0.295372 0.758612 0.465045 0.088 Uiso 1 1 calc R U . . .
H8AB H 0.046445 0.681893 0.452478 0.088 Uiso 1 1 calc R U . . .
C15 C 0.0635(6) 0.5171(2) 0.21521(9) 0.0649(7) Uani 1 1 d . . . . .
H15 H -0.059336 0.498117 0.190246 0.078 Uiso 1 1 calc R U . . .
C12 C 0.8076(6) 0.1631(2) 0.45516(9) 0.0702(7) Uani 1 1 d . . . . .
H12 H 0.907461 0.126562 0.480102 0.084 Uiso 1 1 calc R U . . .
C16 C 0.1320(6) 0.63085(19) 0.22314(8) 0.0611(6) Uani 1 1 d . . . . .
H16 H 0.055648 0.688534 0.203375 0.073 Uiso 1 1 calc R U . . .
C13 C 0.8665(5) 0.2748(2) 0.44123(8) 0.0628(6) Uani 1 1 d . . . . .
H13 H 1.002334 0.313491 0.458032 0.075 Uiso 1 1 calc R U . . .
C17 C 0.3134(5) 0.66002(17) 0.26024(8) 0.0549(6) Uani 1 1 d . . . . .
H17 H 0.353357 0.737455 0.265958 0.066 Uiso 1 1 calc R U . . .
C14 C 0.1777(5) 0.43063(18) 0.24447(7) 0.0562(6) Uani 1 1 d . . . . .
H14 H 0.129238 0.353701 0.239926 0.067 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
O1 C7 1.207(2) . ?
C1 C10 1.379(3) . ?
C1 C2 1.404(3) . ?
C1 N1 1.429(3) . ?
N1 N2 1.245(2) . ?
O2 C7 1.355(3) . ?
O2 C8 1.443(3) . ?
C2 C13 1.389(3) . ?
C2 C3 1.523(3) . ?
N2 C6 1.429(3) . ?
N3 C7 1.346(3) . ?
N3 C4 1.474(2) . ?
N3 C3 1.475(3) . ?
C3 H3A 0.9700 . ?
C3 H3AB 0.9700 . ?
C4 C5 1.514(3) . ?
C4 H4A 0.9700 . ?
C4 H4AB 0.9700 . ?
C5 C17 1.385(3) . ?
C5 C6 1.395(3) . ?
C6 C14 1.381(3) . ?
C11 C12 1.368(4) . ?
C11 C10 1.372(3) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C9 C8 1.453(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 H8A 0.9700 . ?
C8 H8AB 0.9700 . ?
C15 C16 1.376(4) . ?
C15 C14 1.388(3) . ?
C15 H15 0.9300 . ?
C12 C13 1.376(4) . ?
C12 H12 0.9300 . ?
C16 C17 1.381(3) . ?
C16 H16 0.9300 . ?
C13 H13 0.9300 . ?
C17 H17 0.9300 . ?
C14 H14 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
C10 C1 C2 120.88(19) . . ?
C10 C1 N1 117.6(2) . . ?
C2 C1 N1 121.30(18) . . ?
N2 N1 C1 110.35(17) . . ?
C7 O2 C8 115.96(16) . . ?
C13 C2 C1 116.4(2) . . ?
C13 C2 C3 116.2(2) . . ?
C1 C2 C3 127.32(19) . . ?
N1 N2 C6 115.06(18) . . ?
C7 N3 C4 121.80(16) . . ?
C7 N3 C3 116.62(16) . . ?
C4 N3 C3 119.83(17) . . ?
N3 C3 C2 119.97(18) . . ?
N3 C3 H3A 107.3 . . ?
C2 C3 H3A 107.3 . . ?
N3 C3 H3AB 107.3 . . ?
C2 C3 H3AB 107.3 . . ?
H3A C3 H3AB 106.9 . . ?
N3 C4 C5 116.73(16) . . ?
N3 C4 H4A 108.1 . . ?
C5 C4 H4A 108.1 . . ?
N3 C4 H4AB 108.1 . . ?
C5 C4 H4AB 108.1 . . ?
H4A C4 H4AB 107.3 . . ?
C17 C5 C6 117.75(19) . . ?
C17 C5 C4 122.50(18) . . ?
C6 C5 C4 119.72(18) . . ?
C14 C6 C5 121.94(19) . . ?
C14 C6 N2 126.22(18) . . ?
C5 C6 N2 111.84(18) . . ?
O1 C7 N3 125.3(2) . . ?
O1 C7 O2 123.29(19) . . ?
N3 C7 O2 111.45(16) . . ?
C12 C11 C10 119.3(2) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C10 C1 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
C1 C10 H10 119.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C8 C9 109.6(2) . . ?
O2 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
O2 C8 H8AB 109.8 . . ?
C9 C8 H8AB 109.8 . . ?
H8A C8 H8AB 108.2 . . ?
C16 C15 C14 120.0(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C11 C12 C13 120.2(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C15 C16 C17 120.5(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C12 C13 C2 122.3(3) . . ?
C12 C13 H13 118.9 . . ?
C2 C13 H13 118.9 . . ?
C16 C17 C5 120.87(19) . . ?
C16 C17 H17 119.6 . . ?
C5 C17 H17 119.6 . . ?
C6 C14 C15 118.9(2) . . ?
C6 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?

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
C10 C1 N1 N2 -146.22(19) . . . . ?
C2 C1 N1 N2 38.6(2) . . . . ?
C10 C1 C2 C13 3.4(3) . . . . ?
N1 C1 C2 C13 178.39(19) . . . . ?
C10 C1 C2 C3 -178.8(2) . . . . ?
N1 C1 C2 C3 -3.8(3) . . . . ?
C1 N1 N2 C6 -164.57(15) . . . . ?
C7 N3 C3 C2 73.3(2) . . . . ?
C4 N3 C3 C2 -121.5(2) . . . . ?
C13 C2 C3 N3 -142.9(2) . . . . ?
C1 C2 C3 N3 39.3(3) . . . . ?
C7 N3 C4 C5 -86.0(2) . . . . ?
C3 N3 C4 C5 109.6(2) . . . . ?
N3 C4 C5 C17 135.9(2) . . . . ?
N3 C4 C5 C6 -46.0(3) . . . . ?
C17 C5 C6 C14 0.2(3) . . . . ?
C4 C5 C6 C14 -177.96(19) . . . . ?
C17 C5 C6 N2 179.33(18) . . . . ?
C4 C5 C6 N2 1.2(3) . . . . ?
N1 N2 C6 C14 -58.9(3) . . . . ?
N1 N2 C6 C5 122.01(18) . . . . ?
C4 N3 C7 O1 -170.4(2) . . . . ?
C3 N3 C7 O1 -5.5(3) . . . . ?
C4 N3 C7 O2 9.6(3) . . . . ?
C3 N3 C7 O2 174.50(17) . . . . ?
C8 O2 C7 O1 5.7(3) . . . . ?
C8 O2 C7 N3 -174.3(2) . . . . ?
C12 C11 C10 C1 2.3(4) . . . . ?
C2 C1 C10 C11 -4.6(3) . . . . ?
N1 C1 C10 C11 -179.8(2) . . . . ?
C7 O2 C8 C9 174.1(3) . . . . ?
C10 C11 C12 C13 1.2(4) . . . . ?
C14 C15 C16 C17 -0.3(4) . . . . ?
C11 C12 C13 C2 -2.4(4) . . . . ?
C1 C2 C13 C12 0.1(3) . . . . ?
C3 C2 C13 C12 -177.9(2) . . . . ?
C15 C16 C17 C5 2.2(4) . . . . ?
C6 C5 C17 C16 -2.1(3) . . . . ?
C4 C5 C17 C16 176.0(2) . . . . ?
C5 C6 C14 C15 1.6(3) . . . . ?
N2 C6 C14 C15 -177.4(2) . . . . ?
C16 C15 C14 C6 -1.6(4) . . . . ?

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
_geom_hbond_publ_flag
C3 H3AB N1 0.97 2.65 3.421(3) 136.8 1_655 yes

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.064




####################################################################### 
# 
# 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_Z-2c
_database_code_depnum_ccdc_archive 'CCDC 2056226'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2021-03-05 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
;
'ethyl (Z)-11,13-dihydro-12H-dibenzo[c,h][1,2,6]triazonine-12-carboxylate'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 N3 O2'
_chemical_formula_sum            'C17 H17 N3 O2'
_chemical_formula_weight         295.33

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   12.2994(4)
_cell_length_b                   9.1580(3)
_cell_length_c                   26.4451(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2978.73(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8476
_cell_measurement_theta_min      2.8850
_cell_measurement_theta_max      29.2570

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.89421
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_detector                 'Dectris PILATUS3 R 200K-A area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'Hybrid Photon Counting area detector'

_diffrn_measurement_device       'kappa gonio four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'

_diffrn_radiation_collimation    
'Rigaku Integrated Confocal MaxFlux double bounce multi-layer mirror optics'
_diffrn_radiation_monochromator  none
_diffrn_radiation_probe          x-ray

_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Rigaku micromax 003'
_diffrn_reflns_number            20421
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.878
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3045
_reflns_number_gt                2766
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0506P)²+1.0701P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0024(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3045
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1060
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
O1 O 0.43835(9) 0.71538(10) 0.55651(4) 0.0497(3) Uani 1 1 d . . . . .
N1 N 0.42617(10) 0.39147(16) 0.72853(4) 0.0478(3) Uani 1 1 d . . . . .
C1 C 0.52108(10) 0.44703(16) 0.70255(4) 0.0357(3) Uani 1 1 d . . . . .
C3 C 0.40000(11) 0.62257(15) 0.65345(6) 0.0399(3) Uani 1 1 d . . . . .
H3A H 0.348462 0.610015 0.681874 0.048 Uiso 1 1 calc R U . . .
H3AB H 0.406773 0.728526 0.646733 0.048 Uiso 1 1 calc R U . . .
N3 N 0.35506(8) 0.55136(11) 0.60852(4) 0.0324(2) Uani 1 1 d . . . . .
C2 C 0.51047(10) 0.56349(14) 0.66921(5) 0.0340(3) Uani 1 1 d . . . . .
O2 O 0.34189(7) 0.52621(10) 0.52466(3) 0.0384(2) Uani 1 1 d . . . . .
N2 N 0.37222(10) 0.29025(16) 0.70977(4) 0.0454(3) Uani 1 1 d . . . . .
C5 C 0.36667(9) 0.28082(13) 0.61647(4) 0.0284(3) Uani 1 1 d . . . . .
C4 C 0.29471(10) 0.41497(14) 0.61447(5) 0.0330(3) Uani 1 1 d . . . . .
H4A H 0.243289 0.404743 0.585891 0.040 Uiso 1 1 calc R U . . .
H4AB H 0.251460 0.420101 0.645995 0.040 Uiso 1 1 calc R U . . .
C7 C 0.38305(10) 0.60669(13) 0.56269(5) 0.0342(3) Uani 1 1 d . . . . .
C6 C 0.40684(10) 0.22659(14) 0.66194(5) 0.0332(3) Uani 1 1 d . . . . .
C11 C 0.70681(11) 0.57031(16) 0.66268(6) 0.0445(3) Uani 1 1 d . . . . .
H11 H 0.770643 0.612968 0.648875 0.053 Uiso 1 1 calc R U . . .
C10 C 0.60528(11) 0.62401(15) 0.64938(6) 0.0414(3) Uani 1 1 d . . . . .
H10 H 0.600321 0.703379 0.626364 0.050 Uiso 1 1 calc R U . . .
C9 C 0.28830(16) 0.6786(2) 0.45343(6) 0.0653(5) Uani 1 1 d . . . . .
H9A H 0.305388 0.700598 0.418038 0.098 Uiso 1 1 calc R U . . .
H9B H 0.290848 0.768811 0.473341 0.098 Uiso 1 1 calc R U . . .
H9C H 0.215348 0.636061 0.455574 0.098 Uiso 1 1 calc R U . . .
C8 C 0.36955(12) 0.57263(18) 0.47373(6) 0.0467(4) Uani 1 1 d . . . . .
H8A H 0.372728 0.486191 0.451294 0.056 Uiso 1 1 calc R U . . .
H8AB H 0.442377 0.618667 0.473955 0.056 Uiso 1 1 calc R U . . .
C15 C 0.50025(12) 0.03464(15) 0.61913(7) 0.0498(4) Uani 1 1 d . . . . .
H15 H 0.546346 -0.048573 0.619800 0.060 Uiso 1 1 calc R U . . .
C12 C 0.71494(11) 0.45498(17) 0.69597(5) 0.0431(3) Uani 1 1 d . . . . .
H12 H 0.784466 0.417794 0.704852 0.052 Uiso 1 1 calc R U . . .
C16 C 0.46139(14) 0.08607(16) 0.57381(7) 0.0498(4) Uani 1 1 d . . . . .
H16 H 0.479972 0.037617 0.543242 0.060 Uiso 1 1 calc R U . . .
C13 C 0.62293(12) 0.39359(17) 0.71633(5) 0.0431(3) Uani 1 1 d . . . . .
H13 H 0.628705 0.315143 0.739686 0.052 Uiso 1 1 calc R U . . .
C17 C 0.39543(11) 0.20789(14) 0.57254(5) 0.0379(3) Uani 1 1 d . . . . .
H17 H 0.369215 0.242449 0.540942 0.046 Uiso 1 1 calc R U . . .
C14 C 0.47274(11) 0.10298(15) 0.66326(6) 0.0439(4) Uani 1 1 d . . . . .
H14 H 0.498432 0.066341 0.694673 0.053 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
O1 C7 1.2166(16) . ?
N1 N2 1.2433(19) . ?
N1 C1 1.4469(18) . ?
C1 C2 1.390(2) . ?
C1 C13 1.3935(19) . ?
C3 N3 1.4638(17) . ?
C3 C2 1.5206(17) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
N3 C7 1.3579(17) . ?
N3 C4 1.4615(16) . ?
C2 C10 1.394(2) . ?
O2 C7 1.3458(17) . ?
O2 C8 1.4528(17) . ?
N2 C6 1.4563(18) . ?
C5 C17 1.3858(18) . ?
C5 C6 1.3918(17) . ?
C5 C4 1.5150(17) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C6 C14 1.3927(19) . ?
C11 C12 1.378(2) . ?
C11 C10 1.3874(19) . ?
C11 H11 0.9500 . ?
C10 H10 0.9500 . ?
C9 C8 1.493(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C15 C14 1.367(2) . ?
C15 C16 1.374(2) . ?
C15 H15 0.9500 . ?
C12 C13 1.374(2) . ?
C12 H12 0.9500 . ?
C16 C17 1.380(2) . ?
C16 H16 0.9500 . ?
C13 H13 0.9500 . ?
C17 H17 0.9500 . ?
C14 H14 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
N2 N1 C1 120.21(11) . . ?
C2 C1 C13 121.32(13) . . ?
C2 C1 N1 119.69(12) . . ?
C13 C1 N1 118.52(12) . . ?
N3 C3 C2 113.66(10) . . ?
N3 C3 H3A 108.8 . . ?
C2 C3 H3A 108.8 . . ?
N3 C3 H3AB 108.8 . . ?
C2 C3 H3AB 108.8 . . ?
H3A C3 H3AB 107.7 . . ?
C7 N3 C4 122.95(11) . . ?
C7 N3 C3 117.55(11) . . ?
C4 N3 C3 119.02(11) . . ?
C1 C2 C10 117.73(12) . . ?
C1 C2 C3 122.05(12) . . ?
C10 C2 C3 120.20(12) . . ?
C7 O2 C8 116.39(11) . . ?
N1 N2 C6 119.28(11) . . ?
C17 C5 C6 117.49(12) . . ?
C17 C5 C4 120.71(11) . . ?
C6 C5 C4 121.79(11) . . ?
N3 C4 C5 113.58(9) . . ?
N3 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
N3 C4 H4AB 108.8 . . ?
C5 C4 H4AB 108.8 . . ?
H4A C4 H4AB 107.7 . . ?
O1 C7 O2 123.92(13) . . ?
O1 C7 N3 124.54(13) . . ?
O2 C7 N3 111.55(11) . . ?
C5 C6 C14 121.22(13) . . ?
C5 C6 N2 120.25(11) . . ?
C14 C6 N2 118.28(12) . . ?
C12 C11 C10 119.92(14) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C10 C2 121.11(14) . . ?
C11 C10 H10 119.4 . . ?
C2 C10 H10 119.4 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C8 C9 111.53(12) . . ?
O2 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
O2 C8 H8AB 109.3 . . ?
C9 C8 H8AB 109.3 . . ?
H8A C8 H8AB 108.0 . . ?
C14 C15 C16 120.12(13) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C13 C12 C11 120.28(13) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C15 C16 C17 120.20(14) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C12 C13 C1 119.62(13) . . ?
C12 C13 H13 120.2 . . ?
C1 C13 H13 120.2 . . ?
C16 C17 C5 121.30(13) . . ?
C16 C17 H17 119.4 . . ?
C5 C17 H17 119.4 . . ?
C15 C14 C6 119.66(13) . . ?
C15 C14 H14 120.2 . . ?
C6 C14 H14 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
N2 N1 C1 C2 91.50(17) . . . . ?
N2 N1 C1 C13 -96.20(16) . . . . ?
C2 C3 N3 C7 -87.55(14) . . . . ?
C2 C3 N3 C4 84.66(15) . . . . ?
C13 C1 C2 C10 0.89(19) . . . . ?
N1 C1 C2 C10 172.96(12) . . . . ?
C13 C1 C2 C3 179.56(12) . . . . ?
N1 C1 C2 C3 -8.36(18) . . . . ?
N3 C3 C2 C1 -89.67(15) . . . . ?
N3 C3 C2 C10 88.97(15) . . . . ?
C1 N1 N2 C6 1.18(19) . . . . ?
C7 N3 C4 C5 87.62(13) . . . . ?
C3 N3 C4 C5 -84.15(13) . . . . ?
C17 C5 C4 N3 -89.10(14) . . . . ?
C6 C5 C4 N3 90.52(13) . . . . ?
C8 O2 C7 O1 1.91(18) . . . . ?
C8 O2 C7 N3 -178.11(10) . . . . ?
C4 N3 C7 O1 -175.70(11) . . . . ?
C3 N3 C7 O1 -3.82(18) . . . . ?
C4 N3 C7 O2 4.31(15) . . . . ?
C3 N3 C7 O2 176.19(10) . . . . ?
C17 C5 C6 C14 -0.51(17) . . . . ?
C4 C5 C6 C14 179.86(11) . . . . ?
C17 C5 C6 N2 -174.66(11) . . . . ?
C4 C5 C6 N2 5.71(17) . . . . ?
N1 N2 C6 C5 -91.66(15) . . . . ?
N1 N2 C6 C14 94.01(16) . . . . ?
C12 C11 C10 C2 0.1(2) . . . . ?
C1 C2 C10 C11 -0.3(2) . . . . ?
C3 C2 C10 C11 -179.04(13) . . . . ?
C7 O2 C8 C9 -90.08(16) . . . . ?
C10 C11 C12 C13 -0.5(2) . . . . ?
C14 C15 C16 C17 0.7(2) . . . . ?
C11 C12 C13 C1 1.0(2) . . . . ?
C2 C1 C13 C12 -1.2(2) . . . . ?
N1 C1 C13 C12 -173.41(13) . . . . ?
C15 C16 C17 C5 -0.1(2) . . . . ?
C6 C5 C17 C16 0.01(18) . . . . ?
C4 C5 C17 C16 179.64(12) . . . . ?
C16 C15 C14 C6 -1.2(2) . . . . ?
C5 C6 C14 C15 1.12(19) . . . . ?
N2 C6 C14 C15 175.39(13) . . . . ?

_refine_diff_density_max         0.207
_refine_diff_density_min         -0.145
_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_Z-2a
_database_code_depnum_ccdc_archive 'CCDC 2007074'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2021-03-05 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT910_compound_Z-2a       
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).  17 Note  
RESPONSE: Indeed 17 Bragg reflections  as listed below were omitted 
due to a theta(min) limit set too high  (From CIF: Theta(Min) = 3.562).
The very low-order reflections are essentially hidden by the beamstop 
which has a finite size and a fixed setting and the strategy software
does not readily allow us to set up additional images with the detector
at a larger distance from the crystal with the beamstop setting changed
accordingly. These very few missing reflections do not preclude at
all the structure solution and refinement meeting the iUCR & Chemistry
criteria.
;
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3

_chemical_name_systematic        
;
'tert-butyl(Z)-11,13-dihydro-12H-dibenzo[c,h][1,2,6]triazonine-12-carboxylate'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H21 N3 O2'
_chemical_formula_sum            'C19 H21 N3 O2'
_chemical_formula_weight         323.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_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                   9.4527(2)
_cell_length_b                   11.1113(3)
_cell_length_c                   17.2833(5)
_cell_angle_alpha                72.180(2)
_cell_angle_beta                 86.927(2)
_cell_angle_gamma                81.304(2)
_cell_volume                     1708.28(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9101
_cell_measurement_theta_min      3.3350
_cell_measurement_theta_max      29.5150

_exptl_crystal_description       flake
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.78712
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_detector                 'Dectris PILATUS3 R 200K-A area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'Hybrid Photon Counting area detector'

_diffrn_measurement_device       'kappa gonio four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'

_diffrn_radiation_collimation    
'Rigaku Integrated Confocal MaxFlux double bounce multi-layer mirror optics'
_diffrn_radiation_monochromator  none
_diffrn_radiation_probe          x-ray

_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Rigaku micromax 003'
_diffrn_reflns_number            27891
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.562
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             7635
_reflns_number_gt                6204
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0607P)²+0.4646P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_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_number_reflns         7611
_refine_ls_number_parameters     439
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1217
_refine_ls_wR_factor_gt          0.1149
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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_1 C 0.23977(14) 0.59984(12) 0.24760(8) 0.0219(3) Uani 1 1 d . . . . .
N1_1 N 0.24794(13) 0.70512(11) 0.27995(7) 0.0270(3) Uani 1 1 d . . . . .
O1_1 O 0.00295(11) 0.27481(9) 0.42778(6) 0.0273(2) Uani 1 1 d . . . . .
C2_1 C 0.14748(13) 0.51103(12) 0.28295(8) 0.0194(3) Uani 1 1 d . . . . .
N2_1 N 0.32667(13) 0.68586(11) 0.33955(7) 0.0271(3) Uani 1 1 d . . . . .
O2_1 O 0.12456(10) 0.26768(8) 0.54003(6) 0.0232(2) Uani 1 1 d . . . . .
C3_1 C 0.05081(14) 0.52151(12) 0.35412(8) 0.0207(3) Uani 1 1 d . . . . .
H3A_1 H 0.033161 0.612122 0.353068 0.025 Uiso 1 1 calc R U . . .
H3B_1 H -0.042451 0.496542 0.346514 0.025 Uiso 1 1 calc R U . . .
N3_1 N 0.10522(11) 0.44425(10) 0.43427(7) 0.0196(2) Uani 1 1 d . . . . .
C4_1 C 0.20919(14) 0.49370(12) 0.47210(8) 0.0207(3) Uani 1 1 d . . . . .
H13C_1 H 0.208386 0.451985 0.531572 0.025 Uiso 1 1 calc R U . . .
H13D_1 H 0.180117 0.586536 0.462202 0.025 Uiso 1 1 calc R U . . .
C5_1 C 0.35977(14) 0.47112(13) 0.43971(8) 0.0219(3) Uani 1 1 d . . . . .
C6_1 C 0.41088(14) 0.56120(13) 0.37329(8) 0.0243(3) Uani 1 1 d . . . . .
C7_1 C 0.07326(13) 0.32321(12) 0.46428(8) 0.0204(3) Uani 1 1 d . . . . .
C8_1 C 0.12371(16) 0.13021(12) 0.58171(9) 0.0259(3) Uani 1 1 d . . . . .
C9_1 C 0.21903(19) 0.05460(15) 0.53363(10) 0.0378(4) Uani 1 1 d . . . . .
H9A_1 H 0.179113 0.073606 0.479324 0.057 Uiso 1 1 calc R U . . .
H9B_1 H 0.223763 -0.036958 0.561959 0.057 Uiso 1 1 calc R U . . .
H9C_1 H 0.315471 0.078568 0.528704 0.057 Uiso 1 1 calc R U . . .
C10_1 C -0.02764(17) 0.09789(15) 0.59254(10) 0.0354(4) Uani 1 1 d . . . . .
H10A_1 H -0.070100 0.114642 0.539109 0.053 Uiso 1 1 calc R U . . .
H10B_1 H -0.084919 0.150648 0.622310 0.053 Uiso 1 1 calc R U . . .
H10C_1 H -0.025779 0.007460 0.623198 0.053 Uiso 1 1 calc R U . . .
C11_1 C 0.18999(17) 0.11361(14) 0.66316(9) 0.0299(3) Uani 1 1 d . . . . .
H11A_1 H 0.202081 0.023113 0.695006 0.045 Uiso 1 1 calc R U . . .
H11B_1 H 0.127138 0.163270 0.692768 0.045 Uiso 1 1 calc R U . . .
H11C_1 H 0.283494 0.143744 0.654231 0.045 Uiso 1 1 calc R U . . .
C12_1 C 0.14263(14) 0.41353(12) 0.24838(8) 0.0213(3) Uani 1 1 d . . . . .
H12_1 H 0.082672 0.350256 0.272060 0.026 Uiso 1 1 calc R U . . .
C13_1 C 0.22366(15) 0.40733(13) 0.18013(8) 0.0246(3) Uani 1 1 d . . . . .
H13_1 H 0.219672 0.339691 0.157824 0.029 Uiso 1 1 calc R U . . .
C14_1 C 0.31056(14) 0.49969(14) 0.14434(8) 0.0254(3) Uani 1 1 d . . . . .
H14_1 H 0.364707 0.496132 0.096972 0.031 Uiso 1 1 calc R U . . .
C15_1 C 0.31850(14) 0.59725(13) 0.17764(8) 0.0246(3) Uani 1 1 d . . . . .
H15_1 H 0.376896 0.661427 0.153008 0.030 Uiso 1 1 calc R U . . .
C16_1 C 0.54865(15) 0.54089(16) 0.34269(9) 0.0320(3) Uani 1 1 d . . . . .
H16_1 H 0.582416 0.604525 0.298189 0.038 Uiso 1 1 calc R U . . .
C17_1 C 0.63582(15) 0.42739(17) 0.37760(10) 0.0346(4) Uani 1 1 d . . . . .
H17_1 H 0.729071 0.411911 0.356121 0.041 Uiso 1 1 calc R U . . .
C18_1 C 0.58764(16) 0.33568(16) 0.44408(10) 0.0330(3) Uani 1 1 d . . . . .
H18_1 H 0.648079 0.257988 0.468355 0.040 Uiso 1 1 calc R U . . .
C19_1 C 0.45049(15) 0.35823(14) 0.47487(9) 0.0261(3) Uani 1 1 d . . . . .
H19_1 H 0.418195 0.295693 0.520576 0.031 Uiso 1 1 calc R U . . .
O1_2 O 0.55014(10) 0.79800(9) 0.12932(6) 0.0281(2) Uani 1 1 d . . . . .
C1_2 C 0.81537(15) 1.18754(12) 0.12211(8) 0.0239(3) Uani 1 1 d . . . . .
N1_2 N 0.70032(15) 1.28946(11) 0.08654(7) 0.0298(3) Uani 1 1 d . . . . .
O2_2 O 0.77010(10) 0.81179(8) 0.06957(6) 0.0229(2) Uani 1 1 d . . . . .
C2_2 C 0.84281(15) 1.08215(12) 0.09272(8) 0.0224(3) Uani 1 1 d . . . . .
N3_2 N 0.62839(12) 0.98974(10) 0.07282(7) 0.0210(2) Uani 1 1 d . . . . .
C4_2 C 0.49499(14) 1.05800(13) 0.09495(8) 0.0236(3) Uani 1 1 d . . . . .
H4_2 H 0.416032 1.009342 0.093788 0.028 Uiso 1 1 calc R U . . .
H13B_2 H 0.474768 1.142069 0.053066 0.028 Uiso 1 1 calc R U . . .
C5_2 C 0.49437(14) 1.07952(12) 0.17727(9) 0.0228(3) Uani 1 1 d . . . . .
C6_2 C 0.54143(15) 1.18822(13) 0.18652(9) 0.0247(3) Uani 1 1 d . . . . .
C7_2 C 0.64252(13) 0.85996(12) 0.09415(8) 0.0200(3) Uani 1 1 d . . . . .
C8_2 C 0.80830(14) 0.67301(12) 0.08210(8) 0.0217(3) Uani 1 1 d . . . . .
C9_2 C 0.8030(2) 0.59953(17) 0.17120(10) 0.0435(4) Uani 1 1 d . . . . .
H9A_2 H 0.851412 0.512069 0.179820 0.065 Uiso 1 1 calc R U . . .
H9B_2 H 0.702996 0.597473 0.189113 0.065 Uiso 1 1 calc R U . . .
H9C_2 H 0.851071 0.641316 0.202570 0.065 Uiso 1 1 calc R U . . .
C10_2 C 0.95978(16) 0.66452(14) 0.04850(11) 0.0346(3) Uani 1 1 d . . . . .
H10A_2 H 0.994994 0.575918 0.050755 0.052 Uiso 1 1 calc R U . . .
H10B_2 H 1.021786 0.692989 0.081049 0.052 Uiso 1 1 calc R U . . .
H10C_2 H 0.960444 0.719180 -0.008018 0.052 Uiso 1 1 calc R U . . .
C11_2 C 0.71026(17) 0.62951(14) 0.03284(11) 0.0341(3) Uani 1 1 d . . . . .
H11A_2 H 0.741235 0.539327 0.037555 0.051 Uiso 1 1 calc R U . . .
H11B_2 H 0.714058 0.680874 -0.024321 0.051 Uiso 1 1 calc R U . . .
H11C_2 H 0.611973 0.640160 0.053394 0.051 Uiso 1 1 calc R U . . .
C12_2 C 0.96647(15) 0.99616(13) 0.11929(9) 0.0253(3) Uani 1 1 d . . . . .
H12_2 H 0.986875 0.923185 0.100743 0.030 Uiso 1 1 calc R U . . .
C13_2 C 1.06060(16) 1.01462(14) 0.17225(9) 0.0298(3) Uani 1 1 d . . . . .
H13_2 H 1.144249 0.954746 0.189688 0.036 Uiso 1 1 calc R U . . .
C14_2 C 1.03164(17) 1.12130(14) 0.19959(9) 0.0310(3) Uani 1 1 d . . . . .
H14_2 H 1.095981 1.134816 0.235485 0.037 Uiso 1 1 calc R U . . .
C15_2 C 0.90922(17) 1.20767(13) 0.17454(9) 0.0297(3) Uani 1 1 d . . . . .
H15_2 H 0.889348 1.280610 0.193145 0.036 Uiso 1 1 calc R U . . .
C16_2 C 0.53082(16) 1.21176(14) 0.26134(9) 0.0301(3) Uani 1 1 d . . . . .
H16_2 H 0.561611 1.286358 0.266644 0.036 Uiso 1 1 calc R U . . .
C17_2 C 0.47575(16) 1.12703(15) 0.32771(9) 0.0317(3) Uani 1 1 d . . . . .
H17_2 H 0.469103 1.143050 0.378811 0.038 Uiso 1 1 calc R U . . .
C18_2 C 0.42985(15) 1.01812(15) 0.32011(9) 0.0306(3) Uani 1 1 d . . . . .
H18_2 H 0.391851 0.959646 0.365881 0.037 Uiso 1 1 calc R U . . .
C3_2 C 0.74323(15) 1.06242(12) 0.03335(8) 0.0230(3) Uani 1 1 d . . . . .
H3A_2 H 0.700115 1.146865 -0.002018 0.028 Uiso 1 1 calc R U . . .
H3B_2 H 0.799776 1.016940 -0.001745 0.028 Uiso 1 1 calc R U . . .
C19_2 C 0.43986(14) 0.99523(13) 0.24519(9) 0.0266(3) Uani 1 1 d . . . . .
H19_2 H 0.408794 0.920460 0.240337 0.032 Uiso 1 1 calc R U . . .
N2_2 N 0.57702(14) 1.28922(11) 0.11560(8) 0.0296(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
C1_1 C15_1 1.3911(19) . ?
C1_1 C2_1 1.3936(18) . ?
C1_1 N1_1 1.4557(17) . ?
N1_1 N2_1 1.2490(17) . ?
O1_1 C7_1 1.2206(16) . ?
C2_1 C12_1 1.3953(17) . ?
C2_1 C3_1 1.5155(17) . ?
N2_1 C6_1 1.4540(19) . ?
O2_1 C7_1 1.3465(16) . ?
O2_1 C8_1 1.4770(16) . ?
C3_1 N3_1 1.4614(17) . ?
C3_1 H3A_1 0.9900 . ?
C3_1 H3B_1 0.9900 . ?
N3_1 C7_1 1.3594(16) . ?
N3_1 C4_1 1.4654(16) . ?
C4_1 C5_1 1.5148(18) . ?
C4_1 H13C_1 0.9900 . ?
C4_1 H13D_1 0.9900 . ?
C5_1 C6_1 1.3917(19) . ?
C5_1 C19_1 1.394(2) . ?
C6_1 C16_1 1.392(2) . ?
C8_1 C10_1 1.515(2) . ?
C8_1 C11_1 1.519(2) . ?
C8_1 C9_1 1.525(2) . ?
C9_1 H9A_1 0.9800 . ?
C9_1 H9B_1 0.9800 . ?
C9_1 H9C_1 0.9800 . ?
C10_1 H10A_1 0.9800 . ?
C10_1 H10B_1 0.9800 . ?
C10_1 H10C_1 0.9800 . ?
C11_1 H11A_1 0.9800 . ?
C11_1 H11B_1 0.9800 . ?
C11_1 H11C_1 0.9800 . ?
C12_1 C13_1 1.3855(19) . ?
C12_1 H12_1 0.9500 . ?
C13_1 C14_1 1.387(2) . ?
C13_1 H13_1 0.9500 . ?
C14_1 C15_1 1.3867(19) . ?
C14_1 H14_1 0.9500 . ?
C15_1 H15_1 0.9500 . ?
C16_1 C17_1 1.381(2) . ?
C16_1 H16_1 0.9500 . ?
C17_1 C18_1 1.391(2) . ?
C17_1 H17_1 0.9500 . ?
C18_1 C19_1 1.391(2) . ?
C18_1 H18_1 0.9500 . ?
C19_1 H19_1 0.9500 . ?
O1_2 C7_2 1.2144(16) . ?
C1_2 C15_2 1.389(2) . ?
C1_2 C2_2 1.3981(18) . ?
C1_2 N1_2 1.4547(19) . ?
N1_2 N2_2 1.2442(18) . ?
O2_2 C7_2 1.3455(15) . ?
O2_2 C8_2 1.4801(14) . ?
C2_2 C12_2 1.393(2) . ?
C2_2 C3_2 1.5135(19) . ?
N3_2 C7_2 1.3619(16) . ?
N3_2 C3_2 1.4644(17) . ?
N3_2 C4_2 1.4657(16) . ?
C4_2 C5_2 1.5127(18) . ?
C4_2 H4_2 0.9900 . ?
C4_2 H13B_2 0.9900 . ?
C5_2 C19_2 1.389(2) . ?
C5_2 C6_2 1.4038(18) . ?
C6_2 C16_2 1.391(2) . ?
C6_2 N2_2 1.4502(19) . ?
C8_2 C9_2 1.508(2) . ?
C8_2 C11_2 1.513(2) . ?
C8_2 C10_2 1.5165(19) . ?
C9_2 H9A_2 0.9800 . ?
C9_2 H9B_2 0.9800 . ?
C9_2 H9C_2 0.9800 . ?
C10_2 H10A_2 0.9800 . ?
C10_2 H10B_2 0.9800 . ?
C10_2 H10C_2 0.9800 . ?
C11_2 H11A_2 0.9800 . ?
C11_2 H11B_2 0.9800 . ?
C11_2 H11C_2 0.9800 . ?
C12_2 C13_2 1.389(2) . ?
C12_2 H12_2 0.9500 . ?
C13_2 C14_2 1.391(2) . ?
C13_2 H13_2 0.9500 . ?
C14_2 C15_2 1.382(2) . ?
C14_2 H14_2 0.9500 . ?
C15_2 H15_2 0.9500 . ?
C16_2 C17_2 1.377(2) . ?
C16_2 H16_2 0.9500 . ?
C17_2 C18_2 1.390(2) . ?
C17_2 H17_2 0.9500 . ?
C18_2 C19_2 1.390(2) . ?
C18_2 H18_2 0.9500 . ?
C3_2 H3A_2 0.9900 . ?
C3_2 H3B_2 0.9900 . ?
C19_2 H19_2 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
C15_1 C1_1 C2_1 121.95(12) . . ?
C15_1 C1_1 N1_1 117.71(12) . . ?
C2_1 C1_1 N1_1 120.17(12) . . ?
N2_1 N1_1 C1_1 118.62(12) . . ?
C1_1 C2_1 C12_1 117.51(12) . . ?
C1_1 C2_1 C3_1 121.95(11) . . ?
C12_1 C2_1 C3_1 120.50(11) . . ?
N1_1 N2_1 C6_1 119.72(11) . . ?
C7_1 O2_1 C8_1 121.55(10) . . ?
N3_1 C3_1 C2_1 115.51(10) . . ?
N3_1 C3_1 H3A_1 108.4 . . ?
C2_1 C3_1 H3A_1 108.4 . . ?
N3_1 C3_1 H3B_1 108.4 . . ?
C2_1 C3_1 H3B_1 108.4 . . ?
H3A_1 C3_1 H3B_1 107.5 . . ?
C7_1 N3_1 C3_1 118.17(10) . . ?
C7_1 N3_1 C4_1 123.07(11) . . ?
C3_1 N3_1 C4_1 118.04(10) . . ?
N3_1 C4_1 C5_1 112.57(10) . . ?
N3_1 C4_1 H13C_1 109.1 . . ?
C5_1 C4_1 H13C_1 109.1 . . ?
N3_1 C4_1 H13D_1 109.1 . . ?
C5_1 C4_1 H13D_1 109.1 . . ?
H13C_1 C4_1 H13D_1 107.8 . . ?
C6_1 C5_1 C19_1 118.01(12) . . ?
C6_1 C5_1 C4_1 121.16(12) . . ?
C19_1 C5_1 C4_1 120.82(12) . . ?
C5_1 C6_1 C16_1 121.58(14) . . ?
C5_1 C6_1 N2_1 120.29(12) . . ?
C16_1 C6_1 N2_1 117.78(13) . . ?
O1_1 C7_1 O2_1 125.45(12) . . ?
O1_1 C7_1 N3_1 123.78(12) . . ?
O2_1 C7_1 N3_1 110.72(11) . . ?
O2_1 C8_1 C10_1 111.05(11) . . ?
O2_1 C8_1 C11_1 102.12(10) . . ?
C10_1 C8_1 C11_1 111.07(12) . . ?
O2_1 C8_1 C9_1 108.34(12) . . ?
C10_1 C8_1 C9_1 112.75(13) . . ?
C11_1 C8_1 C9_1 110.98(12) . . ?
C8_1 C9_1 H9A_1 109.5 . . ?
C8_1 C9_1 H9B_1 109.5 . . ?
H9A_1 C9_1 H9B_1 109.5 . . ?
C8_1 C9_1 H9C_1 109.5 . . ?
H9A_1 C9_1 H9C_1 109.5 . . ?
H9B_1 C9_1 H9C_1 109.5 . . ?
C8_1 C10_1 H10A_1 109.5 . . ?
C8_1 C10_1 H10B_1 109.5 . . ?
H10A_1 C10_1 H10B_1 109.5 . . ?
C8_1 C10_1 H10C_1 109.5 . . ?
H10A_1 C10_1 H10C_1 109.5 . . ?
H10B_1 C10_1 H10C_1 109.5 . . ?
C8_1 C11_1 H11A_1 109.5 . . ?
C8_1 C11_1 H11B_1 109.5 . . ?
H11A_1 C11_1 H11B_1 109.5 . . ?
C8_1 C11_1 H11C_1 109.5 . . ?
H11A_1 C11_1 H11C_1 109.5 . . ?
H11B_1 C11_1 H11C_1 109.5 . . ?
C13_1 C12_1 C2_1 121.19(12) . . ?
C13_1 C12_1 H12_1 119.4 . . ?
C2_1 C12_1 H12_1 119.4 . . ?
C12_1 C13_1 C14_1 120.11(12) . . ?
C12_1 C13_1 H13_1 119.9 . . ?
C14_1 C13_1 H13_1 119.9 . . ?
C13_1 C14_1 C15_1 120.05(12) . . ?
C13_1 C14_1 H14_1 120.0 . . ?
C15_1 C14_1 H14_1 120.0 . . ?
C14_1 C15_1 C1_1 119.09(12) . . ?
C14_1 C15_1 H15_1 120.5 . . ?
C1_1 C15_1 H15_1 120.5 . . ?
C17_1 C16_1 C6_1 119.40(15) . . ?
C17_1 C16_1 H16_1 120.3 . . ?
C6_1 C16_1 H16_1 120.3 . . ?
C16_1 C17_1 C18_1 120.25(13) . . ?
C16_1 C17_1 H17_1 119.9 . . ?
C18_1 C17_1 H17_1 119.9 . . ?
C17_1 C18_1 C19_1 119.69(15) . . ?
C17_1 C18_1 H18_1 120.2 . . ?
C19_1 C18_1 H18_1 120.2 . . ?
C18_1 C19_1 C5_1 121.04(14) . . ?
C18_1 C19_1 H19_1 119.5 . . ?
C5_1 C19_1 H19_1 119.5 . . ?
C15_2 C1_2 C2_2 121.40(13) . . ?
C15_2 C1_2 N1_2 118.49(12) . . ?
C2_2 C1_2 N1_2 119.24(12) . . ?
N2_2 N1_2 C1_2 121.30(12) . . ?
C7_2 O2_2 C8_2 121.12(10) . . ?
C12_2 C2_2 C1_2 117.61(13) . . ?
C12_2 C2_2 C3_2 120.90(12) . . ?
C1_2 C2_2 C3_2 121.48(12) . . ?
C7_2 N3_2 C3_2 122.88(11) . . ?
C7_2 N3_2 C4_2 117.97(11) . . ?
C3_2 N3_2 C4_2 119.05(10) . . ?
N3_2 C4_2 C5_2 115.33(11) . . ?
N3_2 C4_2 H4_2 108.4 . . ?
C5_2 C4_2 H4_2 108.4 . . ?
N3_2 C4_2 H13B_2 108.4 . . ?
C5_2 C4_2 H13B_2 108.4 . . ?
H4_2 C4_2 H13B_2 107.5 . . ?
C19_2 C5_2 C6_2 118.09(12) . . ?
C19_2 C5_2 C4_2 120.61(12) . . ?
C6_2 C5_2 C4_2 121.21(13) . . ?
C16_2 C6_2 C5_2 120.74(14) . . ?
C16_2 C6_2 N2_2 118.19(12) . . ?
C5_2 C6_2 N2_2 120.11(12) . . ?
O1_2 C7_2 O2_2 125.49(11) . . ?
O1_2 C7_2 N3_2 123.71(12) . . ?
O2_2 C7_2 N3_2 110.79(11) . . ?
O2_2 C8_2 C9_2 110.71(11) . . ?
O2_2 C8_2 C11_2 109.80(11) . . ?
C9_2 C8_2 C11_2 111.62(13) . . ?
O2_2 C8_2 C10_2 102.11(10) . . ?
C9_2 C8_2 C10_2 111.68(13) . . ?
C11_2 C8_2 C10_2 110.53(12) . . ?
C8_2 C9_2 H9A_2 109.5 . . ?
C8_2 C9_2 H9B_2 109.5 . . ?
H9A_2 C9_2 H9B_2 109.5 . . ?
C8_2 C9_2 H9C_2 109.5 . . ?
H9A_2 C9_2 H9C_2 109.5 . . ?
H9B_2 C9_2 H9C_2 109.5 . . ?
C8_2 C10_2 H10A_2 109.5 . . ?
C8_2 C10_2 H10B_2 109.5 . . ?
H10A_2 C10_2 H10B_2 109.5 . . ?
C8_2 C10_2 H10C_2 109.5 . . ?
H10A_2 C10_2 H10C_2 109.5 . . ?
H10B_2 C10_2 H10C_2 109.5 . . ?
C8_2 C11_2 H11A_2 109.5 . . ?
C8_2 C11_2 H11B_2 109.5 . . ?
H11A_2 C11_2 H11B_2 109.5 . . ?
C8_2 C11_2 H11C_2 109.5 . . ?
H11A_2 C11_2 H11C_2 109.5 . . ?
H11B_2 C11_2 H11C_2 109.5 . . ?
C13_2 C12_2 C2_2 121.55(13) . . ?
C13_2 C12_2 H12_2 119.2 . . ?
C2_2 C12_2 H12_2 119.2 . . ?
C12_2 C13_2 C14_2 119.59(14) . . ?
C12_2 C13_2 H13_2 120.2 . . ?
C14_2 C13_2 H13_2 120.2 . . ?
C15_2 C14_2 C13_2 120.00(14) . . ?
C15_2 C14_2 H14_2 120.0 . . ?
C13_2 C14_2 H14_2 120.0 . . ?
C14_2 C15_2 C1_2 119.83(13) . . ?
C14_2 C15_2 H15_2 120.1 . . ?
C1_2 C15_2 H15_2 120.1 . . ?
C17_2 C16_2 C6_2 120.07(13) . . ?
C17_2 C16_2 H16_2 120.0 . . ?
C6_2 C16_2 H16_2 120.0 . . ?
C16_2 C17_2 C18_2 120.15(13) . . ?
C16_2 C17_2 H17_2 119.9 . . ?
C18_2 C17_2 H17_2 119.9 . . ?
C19_2 C18_2 C17_2 119.64(14) . . ?
C19_2 C18_2 H18_2 120.2 . . ?
C17_2 C18_2 H18_2 120.2 . . ?
N3_2 C3_2 C2_2 113.48(11) . . ?
N3_2 C3_2 H3A_2 108.9 . . ?
C2_2 C3_2 H3A_2 108.9 . . ?
N3_2 C3_2 H3B_2 108.9 . . ?
C2_2 C3_2 H3B_2 108.9 . . ?
H3A_2 C3_2 H3B_2 107.7 . . ?
C5_2 C19_2 C18_2 121.30(13) . . ?
C5_2 C19_2 H19_2 119.4 . . ?
C18_2 C19_2 H19_2 119.4 . . ?
N1_2 N2_2 C6_2 121.75(12) . . ?

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
C15_1 C1_1 N1_1 N2_1 -101.24(15) . . . . ?
C2_1 C1_1 N1_1 N2_1 83.36(16) . . . . ?
C15_1 C1_1 C2_1 C12_1 3.7(2) . . . . ?
N1_1 C1_1 C2_1 C12_1 178.93(12) . . . . ?
C15_1 C1_1 C2_1 C3_1 -173.81(12) . . . . ?
N1_1 C1_1 C2_1 C3_1 1.39(19) . . . . ?
C1_1 N1_1 N2_1 C6_1 1.91(18) . . . . ?
C1_1 C2_1 C3_1 N3_1 -97.01(14) . . . . ?
C12_1 C2_1 C3_1 N3_1 85.52(15) . . . . ?
C2_1 C3_1 N3_1 C7_1 -89.51(14) . . . . ?
C2_1 C3_1 N3_1 C4_1 81.05(14) . . . . ?
C7_1 N3_1 C4_1 C5_1 89.65(15) . . . . ?
C3_1 N3_1 C4_1 C5_1 -80.41(14) . . . . ?
N3_1 C4_1 C5_1 C6_1 90.78(14) . . . . ?
N3_1 C4_1 C5_1 C19_1 -88.14(14) . . . . ?
C19_1 C5_1 C6_1 C16_1 -0.53(19) . . . . ?
C4_1 C5_1 C6_1 C16_1 -179.48(11) . . . . ?
C19_1 C5_1 C6_1 N2_1 -173.61(11) . . . . ?
C4_1 C5_1 C6_1 N2_1 7.44(18) . . . . ?
N1_1 N2_1 C6_1 C5_1 -95.90(15) . . . . ?
N1_1 N2_1 C6_1 C16_1 90.76(15) . . . . ?
C8_1 O2_1 C7_1 O1_1 11.9(2) . . . . ?
C8_1 O2_1 C7_1 N3_1 -170.64(11) . . . . ?
C3_1 N3_1 C7_1 O1_1 0.80(19) . . . . ?
C4_1 N3_1 C7_1 O1_1 -169.25(12) . . . . ?
C3_1 N3_1 C7_1 O2_1 -176.70(10) . . . . ?
C4_1 N3_1 C7_1 O2_1 13.25(16) . . . . ?
C7_1 O2_1 C8_1 C10_1 -61.34(16) . . . . ?
C7_1 O2_1 C8_1 C11_1 -179.81(11) . . . . ?
C7_1 O2_1 C8_1 C9_1 63.00(16) . . . . ?
C1_1 C2_1 C12_1 C13_1 -1.71(19) . . . . ?
C3_1 C2_1 C12_1 C13_1 175.87(12) . . . . ?
C2_1 C12_1 C13_1 C14_1 -0.7(2) . . . . ?
C12_1 C13_1 C14_1 C15_1 1.1(2) . . . . ?
C13_1 C14_1 C15_1 C1_1 0.8(2) . . . . ?
C2_1 C1_1 C15_1 C14_1 -3.3(2) . . . . ?
N1_1 C1_1 C15_1 C14_1 -178.64(12) . . . . ?
C5_1 C6_1 C16_1 C17_1 1.7(2) . . . . ?
N2_1 C6_1 C16_1 C17_1 174.90(12) . . . . ?
C6_1 C16_1 C17_1 C18_1 -1.7(2) . . . . ?
C16_1 C17_1 C18_1 C19_1 0.6(2) . . . . ?
C17_1 C18_1 C19_1 C5_1 0.5(2) . . . . ?
C6_1 C5_1 C19_1 C18_1 -0.56(18) . . . . ?
C4_1 C5_1 C19_1 C18_1 178.39(12) . . . . ?
C15_2 C1_2 N1_2 N2_2 -98.42(16) . . . . ?
C2_2 C1_2 N1_2 N2_2 92.11(16) . . . . ?
C15_2 C1_2 C2_2 C12_2 1.36(19) . . . . ?
N1_2 C1_2 C2_2 C12_2 170.51(12) . . . . ?
C15_2 C1_2 C2_2 C3_2 -177.90(12) . . . . ?
N1_2 C1_2 C2_2 C3_2 -8.75(19) . . . . ?
C7_2 N3_2 C4_2 C5_2 89.73(14) . . . . ?
C3_2 N3_2 C4_2 C5_2 -86.74(15) . . . . ?
N3_2 C4_2 C5_2 C19_2 -94.97(15) . . . . ?
N3_2 C4_2 C5_2 C6_2 88.48(15) . . . . ?
C19_2 C5_2 C6_2 C16_2 -1.3(2) . . . . ?
C4_2 C5_2 C6_2 C16_2 175.34(12) . . . . ?
C19_2 C5_2 C6_2 N2_2 -169.87(12) . . . . ?
C4_2 C5_2 C6_2 N2_2 6.76(19) . . . . ?
C8_2 O2_2 C7_2 O1_2 1.7(2) . . . . ?
C8_2 O2_2 C7_2 N3_2 -177.03(11) . . . . ?
C3_2 N3_2 C7_2 O1_2 177.45(12) . . . . ?
C4_2 N3_2 C7_2 O1_2 1.13(19) . . . . ?
C3_2 N3_2 C7_2 O2_2 -3.75(17) . . . . ?
C4_2 N3_2 C7_2 O2_2 179.92(10) . . . . ?
C7_2 O2_2 C8_2 C9_2 -58.91(17) . . . . ?
C7_2 O2_2 C8_2 C11_2 64.79(15) . . . . ?
C7_2 O2_2 C8_2 C10_2 -177.92(12) . . . . ?
C1_2 C2_2 C12_2 C13_2 -0.8(2) . . . . ?
C3_2 C2_2 C12_2 C13_2 178.45(12) . . . . ?
C2_2 C12_2 C13_2 C14_2 -0.1(2) . . . . ?
C12_2 C13_2 C14_2 C15_2 0.5(2) . . . . ?
C13_2 C14_2 C15_2 C1_2 0.0(2) . . . . ?
C2_2 C1_2 C15_2 C14_2 -1.0(2) . . . . ?
N1_2 C1_2 C15_2 C14_2 -170.23(13) . . . . ?
C5_2 C6_2 C16_2 C17_2 1.0(2) . . . . ?
N2_2 C6_2 C16_2 C17_2 169.81(13) . . . . ?
C6_2 C16_2 C17_2 C18_2 -0.4(2) . . . . ?
C16_2 C17_2 C18_2 C19_2 0.0(2) . . . . ?
C7_2 N3_2 C3_2 C2_2 -88.89(15) . . . . ?
C4_2 N3_2 C3_2 C2_2 87.40(14) . . . . ?
C12_2 C2_2 C3_2 N3_2 91.76(15) . . . . ?
C1_2 C2_2 C3_2 N3_2 -89.01(15) . . . . ?
C6_2 C5_2 C19_2 C18_2 0.9(2) . . . . ?
C4_2 C5_2 C19_2 C18_2 -175.71(12) . . . . ?
C17_2 C18_2 C19_2 C5_2 -0.3(2) . . . . ?
C1_2 N1_2 N2_2 C6_2 0.38(19) . . . . ?
C16_2 C6_2 N2_2 N1_2 100.88(15) . . . . ?
C5_2 C6_2 N2_2 N1_2 -90.25(17) . . . . ?

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
_geom_hbond_publ_flag
C9_1 H9A_1 O1_1 0.98 2.53 3.1073(19) 117.9 . yes
C10_1 H10A_1 O1_1 0.98 2.34 2.9519(19) 119.7 . yes
C15_1 H15_1 O1_2 0.95 2.33 3.2571(16) 163.5 . yes
C9_2 H9B_2 O1_2 0.98 2.43 2.9519(19) 113.0 . yes
C11_2 H11C_2 O1_2 0.98 2.48 3.0593(18) 117.5 . yes

_refine_diff_density_max         0.315
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.049







