# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_HL2
_database_code_depnum_ccdc_archive 'CCDC 1904523'
loop_
_audit_author_name
_audit_author_address
'Clara S. B. Gomes'
;LAQV REQUIMTE FCT Universidade NOVA de Lisboa
Portugal
;
_audit_update_record             
;
2019-03-20 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H12 N2 O3'
_chemical_formula_sum            'C16 H12 N2 O3'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         280.28

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

_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'
_chemical_absolute_configuration ?

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'

_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.
;

_cell_length_a                   12.099(3)
_cell_length_b                   17.373(6)
_cell_length_c                   20.130(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.231(11)
_cell_angle_gamma                90
_cell_volume                     4228(2)
_cell_formula_units_Z            12
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2829
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      18.62
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             1752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7110
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28193
_diffrn_reflns_av_unetI/netI     0.0832
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.317
_diffrn_reflns_theta_max         25.704
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8014
_reflns_number_gt                3258
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2019
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.1049P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8014
_refine_ls_number_parameters     540
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.1746
_refine_ls_R_factor_gt           0.0670
_refine_ls_wR_factor_ref         0.2128
_refine_ls_wR_factor_gt          0.1754
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_restrained_S_all      0.940
_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
O1A O 0.0186(2) 0.16904(17) 0.68686(14) 0.0999(8) Uani 1 1 d . U . . .
O2A O -0.00561(17) -0.01725(15) 0.86555(11) 0.0788(7) Uani 1 1 d . . . . .
O3A O -0.0424(2) -0.08130(17) 0.97801(12) 0.0976(9) Uani 1 1 d . . . . .
H30A H -0.012307 -0.051941 0.952418 0.146 Uiso 1 1 calc R U . . .
N1A N -0.0834(2) 0.05088(16) 0.75657(14) 0.0631(7) Uani 1 1 d . . . . .
N2A N -0.146867(17) -0.001128(16) 0.790627(15) 0.0624(7) Uani 1 1 d D . . . .
C1A C -0.0803(3) 0.1386(2) 0.66562(19) 0.0765(10) Uani 1 1 d . U . . .
C2A C -0.1193(4) 0.1760(3) 0.6117(2) 0.1165(16) Uani 1 1 d . . . . .
H2A H -0.186215 0.167784 0.588472 0.140 Uiso 1 1 calc R U . . .
C3A C -0.0362(4) 0.2316(3) 0.5971(3) 0.1219(13) Uani 1 1 d . U . . .
H3A H -0.037384 0.265039 0.561045 0.146 Uiso 1 1 calc R U . . .
C4A C 0.0415(4) 0.2266(3) 0.6438(2) 0.1219(13) Uani 1 1 d . U . . .
H4A H 0.103720 0.258016 0.647069 0.146 Uiso 1 1 calc R U . . .
C5A C -0.1305(3) 0.0797(2) 0.70512(19) 0.0744(10) Uani 1 1 d . . . . .
H5A H -0.200691 0.062058 0.692133 0.089 Uiso 1 1 calc R U . . .
C6A C -0.1023(2) -0.03246(19) 0.84600(16) 0.0584(8) Uani 1 1 d . . . . .
C7A C -0.1702(2) -0.08765(19) 0.88262(15) 0.0567(8) Uani 1 1 d . . . . .
C8A C -0.1358(3) -0.1098(2) 0.94829(18) 0.0727(10) Uani 1 1 d . . . . .
C9A C -0.1972(3) -0.1594(3) 0.9829(2) 0.0931(12) Uani 1 1 d . . . . .
H9A H -0.173062 -0.173513 1.025575 0.112 Uiso 1 1 calc R U . . .
C10A C -0.2962(3) -0.1903(2) 0.9563(2) 0.0953(13) Uani 1 1 d . . . . .
C11A C -0.3607(4) -0.2422(4) 0.9920(3) 0.1780(16) Uani 1 1 d . U . . .
H11A H -0.338398 -0.257848 1.034649 0.214 Uiso 1 1 calc R U . . .
C12A C -0.456141(17) -0.268749(16) 0.962811(17) 0.1780(16) Uani 1 1 d D U . . .
C13A C -0.4922(5) -0.2502(4) 0.8982(3) 0.1780(16) Uani 1 1 d . U . . .
H13A H -0.556944 -0.271142 0.879534 0.214 Uiso 1 1 calc R U . . .
C14A C -0.4300(3) -0.2007(3) 0.8633(2) 0.1088(15) Uani 1 1 d . . . . .
H14A H -0.452848 -0.187303 0.820235 0.131 Uiso 1 1 calc R U . . .
C15A C -0.3316(3) -0.1692(2) 0.8912(2) 0.0782(10) Uani 1 1 d . . . . .
C16A C -0.2655(2) -0.11840(19) 0.85593(17) 0.0639(9) Uani 1 1 d . . . . .
H16A H -0.287564 -0.105216 0.812643 0.077 Uiso 1 1 calc R U . . .
O1B O 0.3667(2) -0.13644(16) 0.73446(14) 0.0908(8) Uani 1 1 d . . . . .
O2B O 0.33138(17) 0.13390(14) 0.78819(12) 0.0809(7) Uani 1 1 d . . . . .
O3B O 0.2976(2) 0.27764(17) 0.78227(16) 0.1162(10) Uani 1 1 d . . . . .
H30B H 0.329752 0.236794 0.776474 0.174 Uiso 1 1 calc R U . . .
N1B N 0.2565(2) -0.00872(18) 0.78326(13) 0.0656(8) Uani 1 1 d . . . . .
N2B N 0.190413(17) 0.051650(16) 0.802823(15) 0.0641(7) Uani 1 1 d D . . . .
C1B C 0.2652(3) -0.1421(2) 0.76025(18) 0.0739(10) Uani 1 1 d . . . . .
C2B C 0.2304(4) -0.2150(3) 0.7562(2) 0.1054(14) Uani 1 1 d . . . . .
H2B H 0.162563 -0.233538 0.769350 0.126 Uiso 1 1 calc R U . . .
C3B C 0.3147(5) -0.2582(3) 0.7285(3) 0.1223(17) Uani 1 1 d . . . . .
H3B H 0.314650 -0.311059 0.720937 0.147 Uiso 1 1 calc R U . . .
C4B C 0.3933(4) -0.2097(3) 0.7154(2) 0.1082(15) Uani 1 1 d . . . . .
H4B H 0.458841 -0.223058 0.695659 0.130 Uiso 1 1 calc R U . . .
C5B C 0.2105(3) -0.0740(2) 0.78154(17) 0.0686(10) Uani 1 1 d . . . . .
H5B H 0.137888 -0.077974 0.794713 0.082 Uiso 1 1 calc R U . . .
C6B C 0.2340(3) 0.1223(2) 0.80384(15) 0.0605(9) Uani 1 1 d . . . . .
C7B C 0.1639(3) 0.1867(2) 0.82353(16) 0.0622(9) Uani 1 1 d . . . . .
C8B C 0.2005(3) 0.2639(2) 0.80934(19) 0.0813(11) Uani 1 1 d . . . . .
C9B C 0.1329(4) 0.3235(3) 0.8235(2) 0.1080(14) Uani 1 1 d . . . . .
H9B H 0.155318 0.372961 0.812516 0.130 Uiso 1 1 calc R U . . .
C10B C 0.0335(4) 0.3149(3) 0.8530(2) 0.1009(15) Uani 1 1 d . . . . .
C11B C -0.0379(5) 0.3763(3) 0.8685(3) 0.152(3) Uani 1 1 d . . . . .
H11B H -0.019934 0.426667 0.857459 0.183 Uiso 1 1 calc R U . . .
C12B C -0.1339(6) 0.3608(5) 0.9000(4) 0.182(4) Uani 1 1 d . . . . .
H12B H -0.178535 0.402170 0.910779 0.218 Uiso 1 1 calc R U . . .
C13B C -0.1689(5) 0.2880(5) 0.9169(4) 0.171(3) Uani 1 1 d . . . . .
H13B H -0.235576 0.280573 0.937478 0.205 Uiso 1 1 calc R U . . .
C14B C -0.1015(4) 0.2265(3) 0.9023(2) 0.1282(19) Uani 1 1 d . . . . .
H14B H -0.121929 0.176813 0.913818 0.154 Uiso 1 1 calc R U . . .
C15B C -0.0021(3) 0.2389(3) 0.86995(18) 0.0880(13) Uani 1 1 d . . . . .
C16B C 0.0654(3) 0.1764(2) 0.85389(16) 0.0722(10) Uani 1 1 d . . . . .
H16B H 0.042814 0.126775 0.864089 0.087 Uiso 1 1 calc R U . . .
O1C O 0.7125(2) 0.0592(2) 0.93781(15) 0.1253(12) Uani 1 1 d . . . . .
O2C O 0.65186(17) -0.02733(14) 0.70795(11) 0.0743(7) Uani 1 1 d . . . . .
O3C O 0.5771(3) -0.1138(2) 0.60906(18) 0.1641(17) Uani 1 1 d . . . . .
H30C H 0.612325 -0.106598 0.644142 0.246 Uiso 1 1 calc R U . . .
N1C N 0.5898(2) 0.03992(17) 0.81932(14) 0.0688(8) Uani 1 1 d . . . . .
N2C N 0.518730(18) 0.032743(16) 0.764248(17) 0.0688(8) Uani 1 1 d . . . . .
C1C C 0.6045(3) 0.0707(3) 0.9339(2) 0.1030(15) Uani 1 1 d . . . . .
C2C C 0.5694(4) 0.0899(5) 0.9943(3) 0.181(3) Uani 1 1 d . . . . .
H2C H 0.497102 0.101706 1.004778 0.218 Uiso 1 1 calc R U . . .
C3C C 0.7440(5) 0.0696(4) 1.0036(3) 0.164(3) Uani 1 1 d . . . . .
H3C H 0.815866 0.063664 1.020894 0.197 Uiso 1 1 calc R U . . .
C4C C 0.6605(5) 0.0888(5) 1.0381(3) 0.196(4) Uani 1 1 d . . . . .
H4C H 0.661430 0.099760 1.083372 0.235 Uiso 1 1 calc R U . . .
C5C C 0.5459(3) 0.0604(3) 0.8721(2) 0.0950(14) Uani 1 1 d . . . . .
H5C H 0.470049 0.069485 0.870505 0.114 Uiso 1 1 calc R U . . .
C6C C 0.5565(2) -0.00027(19) 0.70914(17) 0.0601(9) Uani 1 1 d . . . . .
C7C C 0.4806(2) -0.0031(2) 0.65000(16) 0.0602(9) Uani 1 1 d . . . . .
C8C C 0.4958(3) -0.0588(3) 0.6017(2) 0.1002(14) Uani 1 1 d . . . . .
C9C C 0.426435(16) -0.060399(15) 0.546068(17) 0.137(2) Uani 1 1 d D . . . .
C10C C 0.3395(3) -0.0102(3) 0.5367(2) 0.0875(12) Uani 1 1 d . . . . .
C11C C 0.2672(5) -0.0133(4) 0.4800(2) 0.1336(19) Uani 1 1 d . . . . .
H11C H 0.280755 -0.048290 0.446273 0.160 Uiso 1 1 calc R U . . .
C12C C 0.1803(5) 0.0329(4) 0.4741(3) 0.1316(19) Uani 1 1 d . . . . .
H12C H 0.132223 0.028968 0.437077 0.158 Uiso 1 1 calc R U . . .
C13C C 0.1607(4) 0.0860(4) 0.5218(3) 0.152(2) Uani 1 1 d . . . . .
H13C H 0.099629 0.118421 0.517465 0.183 Uiso 1 1 calc R U . . .
C14C C 0.2314(4) 0.0914(4) 0.5761(2) 0.143(2) Uani 1 1 d . . . . .
H14C H 0.218665 0.128791 0.607933 0.171 Uiso 1 1 calc R U . . .
C15C C 0.3210(3) 0.0431(2) 0.58520(19) 0.0784(11) Uani 1 1 d . . . . .
C16C C 0.3954(3) 0.0455(2) 0.64067(18) 0.0778(10) Uani 1 1 d . . . . .
H16C H 0.384755 0.082970 0.672756 0.093 Uiso 1 1 calc R U . . .
H20B H 0.110600 0.040100 0.815500 0.118(13) Uiso 1 1 d D . . . .
H20C H 0.433900 0.042200 0.766300 0.137(15) Uiso 1 1 d . . . . .
H20A H -0.230100 -0.012200 0.775900 0.168(19) Uiso 1 1 d D . . . .
H12A H -0.494600 -0.281898 0.990100 0.34(4) Uiso 1 1 d D . . . .
H9C H 0.453100 -0.093805 0.501305 0.26(3) Uiso 1 1 d 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
O1A C4A 1.359(5) . ?
O1A C1A 1.362(4) . ?
O2A C6A 1.248(3) . ?
O3A C8A 1.353(4) . ?
O3A H30A 0.8200 . ?
N1A C5A 1.265(4) . ?
N1A N2A 1.384(3) . ?
N2A C6A 1.335(3) . ?
N2A H20A 1.0563 . ?
C1A C2A 1.336(5) . ?
C1A C5A 1.445(5) . ?
C2A C3A 1.431(6) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.306(6) . ?
C3A H3A 0.9300 . ?
C4A H4A 0.9300 . ?
C5A H5A 0.9300 . ?
C6A C7A 1.478(4) . ?
C7A C16A 1.362(4) . ?
C7A C8A 1.423(4) . ?
C8A C9A 1.349(5) . ?
C9A C10A 1.399(5) . ?
C9A H9A 0.9300 . ?
C10A C11A 1.408(6) . ?
C10A C15A 1.411(5) . ?
C11A C12A 1.356(6) . ?
C11A H11A 0.9300 . ?
C12A C13A 1.393(6) . ?
C12A H12A 0.76835 . ?
C13A C14A 1.356(6) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.407(5) . ?
C14A H14A 0.9300 . ?
C15A C16A 1.402(4) . ?
C16A H16A 0.9300 . ?
O1B C1B 1.355(4) . ?
O1B C4B 1.371(5) . ?
O2B C6B 1.248(3) . ?
O3B C8B 1.336(4) . ?
O3B H30B 0.8200 . ?
N1B C5B 1.263(4) . ?
N1B N2B 1.385(3) . ?
N2B C6B 1.336(3) . ?
N2B H20B 1.0281 . ?
C1B C2B 1.335(5) . ?
C1B C5B 1.430(5) . ?
C2B C3B 1.400(6) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.306(6) . ?
C3B H3B 0.9300 . ?
C4B H4B 0.9300 . ?
C5B H5B 0.9300 . ?
C6B C7B 1.467(4) . ?
C7B C16B 1.372(4) . ?
C7B C8B 1.444(5) . ?
C8B C9B 1.356(5) . ?
C9B C10B 1.370(6) . ?
C9B H9B 0.9300 . ?
C10B C11B 1.416(6) . ?
C10B C15B 1.435(6) . ?
C11B C12B 1.372(9) . ?
C11B H11B 0.9300 . ?
C12B C13B 1.380(10) . ?
C12B H12B 0.9300 . ?
C13B C14B 1.383(7) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.405(6) . ?
C14B H14B 0.9300 . ?
C15B C16B 1.403(5) . ?
C16B H16B 0.9300 . ?
O1C C1C 1.321(4) . ?
O1C C3C 1.375(5) . ?
O2C C6C 1.247(3) . ?
O3C C8C 1.376(5) . ?
O3C H30C 0.8200 . ?
N1C C5C 1.258(4) . ?
N1C N2C 1.382(3) . ?
N2C C6C 1.345(3) . ?
N2C H20C 1.0418 . ?
C1C C2C 1.346(6) . ?
C1C C5C 1.420(5) . ?
C2C C4C 1.384(6) . ?
C2C H2C 0.9300 . ?
C3C C4C 1.292(6) . ?
C3C H3C 0.9300 . ?
C4C H4C 0.9300 . ?
C5C H5C 0.9300 . ?
C6C C7C 1.476(4) . ?
C7C C16C 1.339(4) . ?
C7C C8C 1.390(5) . ?
C8C C9C 1.372(4) . ?
C9C C10C 1.374(4) . ?
C9C H9C 1.1294 . ?
C10C C15C 1.370(5) . ?
C10C C11C 1.412(6) . ?
C11C C12C 1.325(7) . ?
C11C H11C 0.9300 . ?
C12C C13C 1.359(7) . ?
C12C H12C 0.9300 . ?
C13C C14C 1.365(7) . ?
C13C H13C 0.9300 . ?
C14C C15C 1.378(5) . ?
C14C H14C 0.9300 . ?
C15C C16C 1.407(5) . ?
C16C H16C 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
C4A O1A C1A 106.5(4) . . ?
C8A O3A H30A 109.5 . . ?
C5A N1A N2A 115.0(3) . . ?
C6A N2A N1A 117.77(17) . . ?
C6A N2A H20A 120.64 . . ?
N1A N2A H20A 121.38 . . ?
C2A C1A O1A 110.1(4) . . ?
C2A C1A C5A 130.5(4) . . ?
O1A C1A C5A 119.1(3) . . ?
C1A C2A C3A 105.4(4) . . ?
C1A C2A H2A 127.3 . . ?
C3A C2A H2A 127.3 . . ?
C4A C3A C2A 107.5(4) . . ?
C4A C3A H3A 126.3 . . ?
C2A C3A H3A 126.3 . . ?
C3A C4A O1A 110.4(5) . . ?
C3A C4A H4A 124.8 . . ?
O1A C4A H4A 124.8 . . ?
N1A C5A C1A 123.0(3) . . ?
N1A C5A H5A 118.5 . . ?
C1A C5A H5A 118.5 . . ?
O2A C6A N2A 121.3(3) . . ?
O2A C6A C7A 120.8(3) . . ?
N2A C6A C7A 117.8(2) . . ?
C16A C7A C8A 118.2(3) . . ?
C16A C7A C6A 122.4(3) . . ?
C8A C7A C6A 119.4(3) . . ?
C9A C8A O3A 118.3(3) . . ?
C9A C8A C7A 120.4(3) . . ?
O3A C8A C7A 121.4(3) . . ?
C8A C9A C10A 121.9(4) . . ?
C8A C9A H9A 119.1 . . ?
C10A C9A H9A 119.1 . . ?
C9A C10A C11A 122.2(4) . . ?
C9A C10A C15A 118.7(3) . . ?
C11A C10A C15A 119.1(4) . . ?
C12A C11A C10A 118.4(5) . . ?
C12A C11A H11A 120.8 . . ?
C10A C11A H11A 120.8 . . ?
C11A C12A C13A 123.8(3) . . ?
C11A C12A H12A 108.7 . . ?
C13A C12A H12A 124.1 . . ?
C14A C13A C12A 118.0(5) . . ?
C14A C13A H13A 121.0 . . ?
C12A C13A H13A 121.0 . . ?
C13A C14A C15A 121.2(5) . . ?
C13A C14A H14A 119.4 . . ?
C15A C14A H14A 119.4 . . ?
C16A C15A C14A 122.2(4) . . ?
C16A C15A C10A 118.3(3) . . ?
C14A C15A C10A 119.4(4) . . ?
C7A C16A C15A 122.5(3) . . ?
C7A C16A H16A 118.7 . . ?
C15A C16A H16A 118.7 . . ?
C1B O1B C4B 105.4(3) . . ?
C8B O3B H30B 109.5 . . ?
C5B N1B N2B 115.5(2) . . ?
C6B N2B N1B 117.96(18) . . ?
C6B N2B H20B 123.32 . . ?
N1B N2B H20B 118.72 . . ?
C2B C1B O1B 109.5(3) . . ?
C2B C1B C5B 130.9(4) . . ?
O1B C1B C5B 119.4(3) . . ?
C1B C2B C3B 107.5(4) . . ?
C1B C2B H2B 126.2 . . ?
C3B C2B H2B 126.2 . . ?
C4B C3B C2B 106.3(4) . . ?
C4B C3B H3B 126.8 . . ?
C2B C3B H3B 126.8 . . ?
C3B C4B O1B 111.2(4) . . ?
C3B C4B H4B 124.4 . . ?
O1B C4B H4B 124.4 . . ?
N1B C5B C1B 122.9(3) . . ?
N1B C5B H5B 118.6 . . ?
C1B C5B H5B 118.6 . . ?
O2B C6B N2B 121.3(3) . . ?
O2B C6B C7B 120.4(3) . . ?
N2B C6B C7B 118.2(3) . . ?
C16B C7B C8B 119.2(3) . . ?
C16B C7B C6B 122.8(3) . . ?
C8B C7B C6B 118.0(3) . . ?
O3B C8B C9B 119.7(4) . . ?
O3B C8B C7B 121.9(3) . . ?
C9B C8B C7B 118.4(4) . . ?
C8B C9B C10B 123.6(5) . . ?
C8B C9B H9B 118.2 . . ?
C10B C9B H9B 118.2 . . ?
C9B C10B C11B 124.5(6) . . ?
C9B C10B C15B 118.8(4) . . ?
C11B C10B C15B 116.7(5) . . ?
C12B C11B C10B 119.2(7) . . ?
C12B C11B H11B 120.4 . . ?
C10B C11B H11B 120.4 . . ?
C11B C12B C13B 124.6(7) . . ?
C11B C12B H12B 117.7 . . ?
C13B C12B H12B 117.7 . . ?
C12B C13B C14B 117.8(7) . . ?
C12B C13B H13B 121.1 . . ?
C14B C13B H13B 121.1 . . ?
C13B C14B C15B 120.2(6) . . ?
C13B C14B H14B 119.9 . . ?
C15B C14B H14B 119.9 . . ?
C16B C15B C14B 120.3(5) . . ?
C16B C15B C10B 118.2(4) . . ?
C14B C15B C10B 121.4(4) . . ?
C7B C16B C15B 121.7(4) . . ?
C7B C16B H16B 119.1 . . ?
C15B C16B H16B 119.1 . . ?
C1C O1C C3C 105.8(3) . . ?
C8C O3C H30C 109.5 . . ?
C5C N1C N2C 115.7(2) . . ?
C6C N2C N1C 118.66(17) . . ?
C6C N2C H20C 117.85 . . ?
N1C N2C H20C 122.47 . . ?
O1C C1C C2C 109.3(4) . . ?
O1C C1C C5C 119.4(3) . . ?
C2C C1C C5C 131.2(4) . . ?
C1C C2C C4C 107.5(4) . . ?
C1C C2C H2C 126.3 . . ?
C4C C2C H2C 126.3 . . ?
C4C C3C O1C 111.1(4) . . ?
C4C C3C H3C 124.5 . . ?
O1C C3C H3C 124.5 . . ?
C3C C4C C2C 106.3(5) . . ?
C3C C4C H4C 126.9 . . ?
C2C C4C H4C 126.9 . . ?
N1C C5C C1C 124.3(3) . . ?
N1C C5C H5C 117.9 . . ?
C1C C5C H5C 117.9 . . ?
O2C C6C N2C 121.4(3) . . ?
O2C C6C C7C 121.3(3) . . ?
N2C C6C C7C 117.3(2) . . ?
C16C C7C C8C 117.5(3) . . ?
C16C C7C C6C 123.0(3) . . ?
C8C C7C C6C 119.5(3) . . ?
C9C C8C O3C 119.1(3) . . ?
C9C C8C C7C 119.5(3) . . ?
O3C C8C C7C 121.4(4) . . ?
C8C C9C C10C 122.7(3) . . ?
C8C C9C H9C 118.47 . . ?
C10C C9C H9C 117.22 . . ?
C15C C10C C9C 118.4(3) . . ?
C15C C10C C11C 119.3(4) . . ?
C9C C10C C11C 122.3(4) . . ?
C12C C11C C10C 120.9(5) . . ?
C12C C11C H11C 119.6 . . ?
C10C C11C H11C 119.6 . . ?
C11C C12C C13C 120.6(5) . . ?
C11C C12C H12C 119.7 . . ?
C13C C12C H12C 119.7 . . ?
C12C C13C C14C 119.4(5) . . ?
C12C C13C H13C 120.3 . . ?
C14C C13C H13C 120.3 . . ?
C13C C14C C15C 122.1(5) . . ?
C13C C14C H14C 119.0 . . ?
C15C C14C H14C 119.0 . . ?
C10C C15C C14C 117.7(4) . . ?
C10C C15C C16C 118.0(4) . . ?
C14C C15C C16C 124.3(4) . . ?
C7C C16C C15C 123.9(4) . . ?
C7C C16C H16C 118.1 . . ?
C15C C16C H16C 118.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5A N1A N2A C6A -178.9(3) . . . . ?
C4A O1A C1A C2A -0.7(5) . . . . ?
C4A O1A C1A C5A -175.2(4) . . . . ?
O1A C1A C2A C3A 2.4(5) . . . . ?
C5A C1A C2A C3A 176.0(4) . . . . ?
C1A C2A C3A C4A -3.2(6) . . . . ?
C2A C3A C4A O1A 2.9(7) . . . . ?
C1A O1A C4A C3A -1.4(6) . . . . ?
N2A N1A C5A C1A 175.8(3) . . . . ?
C2A C1A C5A N1A -178.1(4) . . . . ?
O1A C1A C5A N1A -5.0(6) . . . . ?
N1A N2A C6A O2A -2.0(4) . . . . ?
N1A N2A C6A C7A 179.6(2) . . . . ?
O2A C6A C7A C16A -165.4(3) . . . . ?
N2A C6A C7A C16A 12.9(4) . . . . ?
O2A C6A C7A C8A 14.8(5) . . . . ?
N2A C6A C7A C8A -166.9(3) . . . . ?
C16A C7A C8A C9A -0.6(5) . . . . ?
C6A C7A C8A C9A 179.3(3) . . . . ?
C16A C7A C8A O3A -179.7(3) . . . . ?
C6A C7A C8A O3A 0.1(5) . . . . ?
O3A C8A C9A C10A 178.6(4) . . . . ?
C7A C8A C9A C10A -0.5(6) . . . . ?
C8A C9A C10A C11A 179.9(5) . . . . ?
C8A C9A C10A C15A 0.6(7) . . . . ?
C9A C10A C11A C12A 179.3(4) . . . . ?
C15A C10A C11A C12A -1.4(9) . . . . ?
C10A C11A C12A C13A 2.7(9) . . . . ?
C11A C12A C13A C14A -2.3(9) . . . . ?
C12A C13A C14A C15A 0.4(9) . . . . ?
C13A C14A C15A C16A 179.4(5) . . . . ?
C13A C14A C15A C10A 0.9(7) . . . . ?
C9A C10A C15A C16A 0.3(6) . . . . ?
C11A C10A C15A C16A -179.0(5) . . . . ?
C9A C10A C15A C14A 179.0(4) . . . . ?
C11A C10A C15A C14A -0.4(7) . . . . ?
C8A C7A C16A C15A 1.6(5) . . . . ?
C6A C7A C16A C15A -178.2(3) . . . . ?
C14A C15A C16A C7A 179.9(3) . . . . ?
C10A C15A C16A C7A -1.5(5) . . . . ?
C5B N1B N2B C6B -178.3(3) . . . . ?
C4B O1B C1B C2B -1.0(5) . . . . ?
C4B O1B C1B C5B -176.4(3) . . . . ?
O1B C1B C2B C3B 1.9(5) . . . . ?
C5B C1B C2B C3B 176.6(4) . . . . ?
C1B C2B C3B C4B -2.0(6) . . . . ?
C2B C3B C4B O1B 1.5(6) . . . . ?
C1B O1B C4B C3B -0.3(5) . . . . ?
N2B N1B C5B C1B 177.7(3) . . . . ?
C2B C1B C5B N1B 179.0(4) . . . . ?
O1B C1B C5B N1B -6.7(5) . . . . ?
N1B N2B C6B O2B -0.5(4) . . . . ?
N1B N2B C6B C7B 179.1(2) . . . . ?
O2B C6B C7B C16B -166.3(3) . . . . ?
N2B C6B C7B C16B 14.0(4) . . . . ?
O2B C6B C7B C8B 14.4(4) . . . . ?
N2B C6B C7B C8B -165.2(3) . . . . ?
C16B C7B C8B O3B 177.3(3) . . . . ?
C6B C7B C8B O3B -3.4(5) . . . . ?
C16B C7B C8B C9B -3.4(5) . . . . ?
C6B C7B C8B C9B 175.8(3) . . . . ?
O3B C8B C9B C10B -178.0(4) . . . . ?
C7B C8B C9B C10B 2.7(6) . . . . ?
C8B C9B C10B C11B 179.6(4) . . . . ?
C8B C9B C10B C15B -0.2(6) . . . . ?
C9B C10B C11B C12B -177.9(5) . . . . ?
C15B C10B C11B C12B 1.8(7) . . . . ?
C10B C11B C12B C13B -1.7(11) . . . . ?
C11B C12B C13B C14B 1.4(13) . . . . ?
C12B C13B C14B C15B -1.3(10) . . . . ?
C13B C14B C15B C16B -178.8(5) . . . . ?
C13B C14B C15B C10B 1.7(7) . . . . ?
C9B C10B C15B C16B -1.6(6) . . . . ?
C11B C10B C15B C16B 178.6(4) . . . . ?
C9B C10B C15B C14B 177.9(4) . . . . ?
C11B C10B C15B C14B -1.9(6) . . . . ?
C8B C7B C16B C15B 1.7(5) . . . . ?
C6B C7B C16B C15B -177.5(3) . . . . ?
C14B C15B C16B C7B -178.7(3) . . . . ?
C10B C15B C16B C7B 0.8(5) . . . . ?
C5C N1C N2C C6C -169.8(3) . . . . ?
C3C O1C C1C C2C 1.7(7) . . . . ?
C3C O1C C1C C5C -177.0(5) . . . . ?
O1C C1C C2C C4C -1.0(8) . . . . ?
C5C C1C C2C C4C 177.5(6) . . . . ?
C1C O1C C3C C4C -1.8(8) . . . . ?
O1C C3C C4C C2C 1.1(10) . . . . ?
C1C C2C C4C C3C -0.1(10) . . . . ?
N2C N1C C5C C1C 179.7(4) . . . . ?
O1C C1C C5C N1C 0.7(8) . . . . ?
C2C C1C C5C N1C -177.7(6) . . . . ?
N1C N2C C6C O2C 3.3(4) . . . . ?
N1C N2C C6C C7C -176.6(2) . . . . ?
O2C C6C C7C C16C -156.9(3) . . . . ?
N2C C6C C7C C16C 23.0(4) . . . . ?
O2C C6C C7C C8C 23.9(5) . . . . ?
N2C C6C C7C C8C -156.2(3) . . . . ?
C16C C7C C8C C9C 2.1(5) . . . . ?
C6C C7C C8C C9C -178.8(3) . . . . ?
C16C C7C C8C O3C -176.1(4) . . . . ?
C6C C7C C8C O3C 3.0(6) . . . . ?
O3C C8C C9C C10C 176.3(4) . . . . ?
C7C C8C C9C C10C -1.9(5) . . . . ?
C8C C9C C10C C15C -0.6(5) . . . . ?
C8C C9C C10C C11C -178.7(4) . . . . ?
C15C C10C C11C C12C -2.1(8) . . . . ?
C9C C10C C11C C12C 176.0(5) . . . . ?
C10C C11C C12C C13C 2.0(9) . . . . ?
C11C C12C C13C C14C -0.1(10) . . . . ?
C12C C13C C14C C15C -1.8(10) . . . . ?
C9C C10C C15C C14C -177.9(4) . . . . ?
C11C C10C C15C C14C 0.2(7) . . . . ?
C9C C10C C15C C16C 2.7(5) . . . . ?
C11C C10C C15C C16C -179.1(4) . . . . ?
C13C C14C C15C C10C 1.6(8) . . . . ?
C13C C14C C15C C16C -179.0(5) . . . . ?
C8C C7C C16C C15C 0.1(5) . . . . ?
C6C C7C C16C C15C -179.0(3) . . . . ?
C10C C15C C16C C7C -2.6(6) . . . . ?
C14C C15C C16C C7C 178.1(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
C5A H5A O2C 0.93 2.40 3.225(4) 148.4 1_455 yes
C5B H5B O2A 0.93 2.52 3.319(4) 144.1 . yes
C5C H5C O2B 0.93 2.57 3.298(5) 135.6 . yes

_refine_diff_density_max         0.238
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.041

