# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
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data_17demb02
_database_code_depnum_ccdc_archive 'CCDC 1547129'
_audit_update_record             
;
2017-04-28 deposited with the CCDC.
2018-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 N2 O'
_chemical_formula_sum            'C16 H12 N2 O'
_chemical_formula_weight         248.28

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   3.9878(2)
_cell_length_b                   12.0606(7)
_cell_length_c                   24.7189(14)
_cell_angle_alpha                90
_cell_angle_beta                 93.930(3)
_cell_angle_gamma                90
_cell_volume                     1186.07(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9935
_cell_measurement_theta_min      3.58
_cell_measurement_theta_max      68.27

_exptl_crystal_description       'transparent plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.379
_exptl_crystal_size_mid          0.282
_exptl_crystal_size_min          0.046
_exptl_absorpt_coefficient_mu    0.707
_shelx_estimated_absorpt_T_min   0.775
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25948
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.791
_diffrn_reflns_theta_max         68.210
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             4148
_reflns_number_gt                3806
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.819
_reflns_Friedel_fraction_max     0.906
_reflns_Friedel_fraction_full    0.909

_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       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 (1.5Ueq for methyl groups) of the connected C atoms.

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0527P)²+0.1415P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1493 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4148
_refine_ls_number_parameters     345
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0966
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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 0.2398(6) 0.68861(19) -0.20232(9) 0.0358(5) Uani 1 1 d . . . . .
O1B O 0.4782(6) 0.9272(2) 0.68607(9) 0.0375(5) Uani 1 1 d . . . . .
N1A N 0.8309(6) 0.5563(2) -0.00537(10) 0.0266(5) Uani 1 1 d . . . . .
N2A N 0.5563(6) 0.7217(2) -0.00540(10) 0.0273(5) Uani 1 1 d . . . . .
N1B N 0.8580(6) 0.8269(2) 0.48211(10) 0.0259(5) Uani 1 1 d . . . . .
N2B N 0.5929(6) 0.9924(2) 0.48969(10) 0.0273(6) Uani 1 1 d . . . . .
C1A C 0.7785(8) 0.7467(3) 0.11303(13) 0.0298(7) Uani 1 1 d . . . . .
H1A H 0.6462 0.8056 0.0975 0.036 Uiso 1 1 calc R U . . .
C2A C 0.8914(8) 0.7519(3) 0.16697(13) 0.0334(7) Uani 1 1 d . . . . .
H2A H 0.8377 0.8140 0.1884 0.040 Uiso 1 1 calc R U . . .
C3A C 1.0865(8) 0.6648(3) 0.19008(14) 0.0357(7) Uani 1 1 d . . . . .
H3A H 1.1652 0.6683 0.2272 0.043 Uiso 1 1 calc R U . . .
C4A C 1.1648(8) 0.5737(3) 0.15906(14) 0.0342(7) Uani 1 1 d . . . . .
H4A H 1.2957 0.5152 0.1753 0.041 Uiso 1 1 calc R U . . .
C5A C 1.1342(8) 0.4742(3) 0.07009(13) 0.0318(7) Uani 1 1 d . . . . .
H5A H 1.2667 0.4152 0.0854 0.038 Uiso 1 1 calc R U . . .
C6A C 1.0254(8) 0.4698(3) 0.01714(13) 0.0303(7) Uani 1 1 d . . . . .
H6A H 1.0810 0.4083 -0.0045 0.036 Uiso 1 1 calc R U . . .
C7A C 0.7424(7) 0.6492(3) 0.02427(13) 0.0266(6) Uani 1 1 d . . . . .
C8A C 0.7074(8) 0.5097(3) -0.10556(13) 0.0311(7) Uani 1 1 d . . . . .
H8A H 0.8215 0.4406 -0.1056 0.037 Uiso 1 1 calc R U . . .
C9A C 0.5491(8) 0.5533(3) -0.15249(13) 0.0322(7) Uani 1 1 d . . . . .
H9A H 0.5556 0.5134 -0.1855 0.039 Uiso 1 1 calc R U . . .
C10A C 0.3773(8) 0.6565(3) -0.15214(13) 0.0301(7) Uani 1 1 d . . . . .
C11A C 0.3610(8) 0.7174(3) -0.10493(12) 0.0285(7) Uani 1 1 d . . . . .
H11A H 0.2433 0.7859 -0.1048 0.034 Uiso 1 1 calc R U . . .
C12A C 1.0530(7) 0.5668(3) 0.10384(13) 0.0303(7) Uani 1 1 d . . . . .
C13A C 0.8564(7) 0.6557(3) 0.08078(13) 0.0277(6) Uani 1 1 d . . . . .
C14A C 0.6915(7) 0.5720(3) -0.05821(12) 0.0273(7) Uani 1 1 d . . . . .
C15A C 0.5247(7) 0.6747(3) -0.05698(12) 0.0267(7) Uani 1 1 d . . . . .
C16A C 0.0782(9) 0.7948(3) -0.20510(14) 0.0371(7) Uani 1 1 d . . . . .
H16A H -0.1129 0.7945 -0.1822 0.056 Uiso 1 1 calc R U . . .
H16B H -0.0018 0.8105 -0.2427 0.056 Uiso 1 1 calc R U . . .
H16C H 0.2388 0.8521 -0.1923 0.056 Uiso 1 1 calc R U . . .
C1B C 0.6841(7) 1.0328(3) 0.37108(13) 0.0293(7) Uani 1 1 d . . . . .
H1B H 0.5643 1.0887 0.3888 0.035 Uiso 1 1 calc R U . . .
C2B C 0.7475(8) 1.0458(3) 0.31701(13) 0.0335(7) Uani 1 1 d . . . . .
H2B H 0.6730 1.1105 0.2979 0.040 Uiso 1 1 calc R U . . .
C3B C 0.9215(8) 0.9633(3) 0.29079(13) 0.0355(8) Uani 1 1 d . . . . .
H3B H 0.9674 0.9727 0.2539 0.043 Uiso 1 1 calc R U . . .
C4B C 1.0273(8) 0.8683(3) 0.31802(13) 0.0354(8) Uani 1 1 d . . . . .
H4B H 1.1419 0.8125 0.2994 0.042 Uiso 1 1 calc R U . . .
C5B C 1.0812(8) 0.7561(3) 0.40338(13) 0.0327(7) Uani 1 1 d . . . . .
H5B H 1.1966 0.6993 0.3856 0.039 Uiso 1 1 calc R U . . .
C6B C 1.0280(8) 0.7440(3) 0.45607(13) 0.0304(7) Uani 1 1 d . . . . .
H6B H 1.1055 0.6798 0.4753 0.036 Uiso 1 1 calc R U . . .
C7B C 0.7417(7) 0.9240(3) 0.45656(12) 0.0255(6) Uani 1 1 d . . . . .
C8B C 0.8346(8) 0.7644(3) 0.58013(13) 0.0313(7) Uani 1 1 d . . . . .
H8B H 0.9422 0.6947 0.5768 0.038 Uiso 1 1 calc R U . . .
C9B C 0.7275(8) 0.8007(3) 0.62928(13) 0.0333(7) Uani 1 1 d . . . . .
H9B H 0.7646 0.7550 0.6604 0.040 Uiso 1 1 calc R U . . .
C10B C 0.5650(8) 0.9036(3) 0.63419(12) 0.0303(7) Uani 1 1 d . . . . .
C11B C 0.5019(8) 0.9732(3) 0.58968(12) 0.0284(7) Uani 1 1 d . . . . .
H11B H 0.3875 1.0418 0.5929 0.034 Uiso 1 1 calc R U . . .
C12B C 0.9681(7) 0.8529(3) 0.37296(13) 0.0304(7) Uani 1 1 d . . . . .
C13B C 0.7946(7) 0.9383(3) 0.39981(12) 0.0270(6) Uani 1 1 d . . . . .
C14B C 0.7774(7) 0.8349(3) 0.53589(12) 0.0267(6) Uani 1 1 d . . . . .
C15B C 0.6139(7) 0.9382(3) 0.53989(12) 0.0268(6) Uani 1 1 d . . . . .
C16B C 0.3108(9) 1.0292(3) 0.69387(14) 0.0376(8) Uani 1 1 d . . . . .
H16D H 0.4579 1.0908 0.6852 0.056 Uiso 1 1 calc R U . . .
H16E H 0.2547 1.0351 0.7317 0.056 Uiso 1 1 calc R U . . .
H16F H 0.1040 1.0321 0.6701 0.056 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C10A 1.377(4) . ?
O1A C16A 1.433(4) . ?
O1B C10B 1.381(4) . ?
O1B C16B 1.419(4) . ?
N1A C6A 1.393(4) . ?
N1A C7A 1.397(4) . ?
N1A C14A 1.397(4) . ?
N2A C7A 1.333(4) . ?
N2A C15A 1.393(4) . ?
N1B C6B 1.390(4) . ?
N1B C14B 1.392(4) . ?
N1B C7B 1.395(4) . ?
N2B C7B 1.331(4) . ?
N2B C15B 1.400(4) . ?
C1A C2A 1.379(5) . ?
C1A C13A 1.405(4) . ?
C1A H1A 0.9500 . ?
C2A C3A 1.405(5) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.388(5) . ?
C3A H3A 0.9500 . ?
C4A C12A 1.409(5) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.352(4) . ?
C5A C12A 1.444(5) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A C13A 1.441(4) . ?
C8A C9A 1.386(5) . ?
C8A C14A 1.396(4) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.422(5) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.384(4) . ?
C11A C15A 1.411(4) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.424(4) . ?
C14A C15A 1.407(4) . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C1B C2B 1.386(4) . ?
C1B C13B 1.398(4) . ?
C1B H1B 0.9500 . ?
C2B C3B 1.397(5) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.380(5) . ?
C3B H3B 0.9500 . ?
C4B C12B 1.407(4) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.342(5) . ?
C5B C12B 1.445(5) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B C13B 1.443(4) . ?
C8B C9B 1.386(5) . ?
C8B C14B 1.391(4) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.409(5) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.394(4) . ?
C11B C15B 1.403(4) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.430(4) . ?
C14B C15B 1.413(4) . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10A O1A C16A 116.4(3) . . ?
C10B O1B C16B 117.1(3) . . ?
C6A N1A C7A 123.0(3) . . ?
C6A N1A C14A 130.5(3) . . ?
C7A N1A C14A 106.4(2) . . ?
C7A N2A C15A 104.4(2) . . ?
C6B N1B C14B 130.1(3) . . ?
C6B N1B C7B 123.5(3) . . ?
C14B N1B C7B 106.4(2) . . ?
C7B N2B C15B 104.7(2) . . ?
C2A C1A C13A 120.9(3) . . ?
C2A C1A H1A 119.5 . . ?
C13A C1A H1A 119.5 . . ?
C1A C2A C3A 119.6(3) . . ?
C1A C2A H2A 120.2 . . ?
C3A C2A H2A 120.2 . . ?
C4A C3A C2A 120.4(3) . . ?
C4A C3A H3A 119.8 . . ?
C2A C3A H3A 119.8 . . ?
C3A C4A C12A 120.9(3) . . ?
C3A C4A H4A 119.5 . . ?
C12A C4A H4A 119.5 . . ?
C6A C5A C12A 121.4(3) . . ?
C6A C5A H5A 119.3 . . ?
C12A C5A H5A 119.3 . . ?
C5A C6A N1A 119.3(3) . . ?
C5A C6A H6A 120.3 . . ?
N1A C6A H6A 120.3 . . ?
N2A C7A N1A 112.9(3) . . ?
N2A C7A C13A 128.6(3) . . ?
N1A C7A C13A 118.5(3) . . ?
C9A C8A C14A 117.0(3) . . ?
C9A C8A H8A 121.5 . . ?
C14A C8A H8A 121.5 . . ?
C8A C9A C10A 121.3(3) . . ?
C8A C9A H9A 119.4 . . ?
C10A C9A H9A 119.4 . . ?
O1A C10A C11A 124.9(3) . . ?
O1A C10A C9A 113.8(3) . . ?
C11A C10A C9A 121.3(3) . . ?
C10A C11A C15A 117.9(3) . . ?
C10A C11A H11A 121.0 . . ?
C15A C11A H11A 121.0 . . ?
C4A C12A C13A 118.2(3) . . ?
C4A C12A C5A 122.5(3) . . ?
C13A C12A C5A 119.3(3) . . ?
C1A C13A C12A 119.9(3) . . ?
C1A C13A C7A 121.7(3) . . ?
C12A C13A C7A 118.4(3) . . ?
N1A C14A C8A 132.3(3) . . ?
N1A C14A C15A 104.9(3) . . ?
C8A C14A C15A 122.7(3) . . ?
N2A C15A C14A 111.4(3) . . ?
N2A C15A C11A 128.9(3) . . ?
C14A C15A C11A 119.7(3) . . ?
O1A C16A H16A 109.5 . . ?
O1A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
O1A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C2B C1B C13B 120.6(3) . . ?
C2B C1B H1B 119.7 . . ?
C13B C1B H1B 119.7 . . ?
C1B C2B C3B 119.8(3) . . ?
C1B C2B H2B 120.1 . . ?
C3B C2B H2B 120.1 . . ?
C4B C3B C2B 120.6(3) . . ?
C4B C3B H3B 119.7 . . ?
C2B C3B H3B 119.7 . . ?
C3B C4B C12B 121.0(3) . . ?
C3B C4B H4B 119.5 . . ?
C12B C4B H4B 119.5 . . ?
C6B C5B C12B 121.9(3) . . ?
C6B C5B H5B 119.1 . . ?
C12B C5B H5B 119.1 . . ?
C5B C6B N1B 119.1(3) . . ?
C5B C6B H6B 120.4 . . ?
N1B C6B H6B 120.4 . . ?
N2B C7B N1B 113.0(3) . . ?
N2B C7B C13B 128.7(3) . . ?
N1B C7B C13B 118.3(3) . . ?
C9B C8B C14B 116.9(3) . . ?
C9B C8B H8B 121.5 . . ?
C14B C8B H8B 121.5 . . ?
C8B C9B C10B 121.6(3) . . ?
C8B C9B H9B 119.2 . . ?
C10B C9B H9B 119.2 . . ?
O1B C10B C11B 124.4(3) . . ?
O1B C10B C9B 114.1(3) . . ?
C11B C10B C9B 121.5(3) . . ?
C10B C11B C15B 117.4(3) . . ?
C10B C11B H11B 121.3 . . ?
C15B C11B H11B 121.3 . . ?
C4B C12B C13B 118.1(3) . . ?
C4B C12B C5B 122.8(3) . . ?
C13B C12B C5B 119.0(3) . . ?
C1B C13B C12B 119.8(3) . . ?
C1B C13B C7B 122.0(3) . . ?
C12B C13B C7B 118.2(3) . . ?
C8B C14B N1B 132.2(3) . . ?
C8B C14B C15B 122.4(3) . . ?
N1B C14B C15B 105.4(3) . . ?
N2B C15B C11B 129.3(3) . . ?
N2B C15B C14B 110.5(3) . . ?
C11B C15B C14B 120.2(3) . . ?
O1B C16B H16D 109.5 . . ?
O1B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
O1B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13A C1A C2A C3A -0.2(5) . . . . ?
C1A C2A C3A C4A -0.2(5) . . . . ?
C2A C3A C4A C12A 0.4(5) . . . . ?
C12A C5A C6A N1A 0.0(4) . . . . ?
C7A N1A C6A C5A 0.4(4) . . . . ?
C14A N1A C6A C5A 179.5(3) . . . . ?
C15A N2A C7A N1A -0.7(3) . . . . ?
C15A N2A C7A C13A 179.4(3) . . . . ?
C6A N1A C7A N2A 179.9(3) . . . . ?
C14A N1A C7A N2A 0.5(3) . . . . ?
C6A N1A C7A C13A -0.2(4) . . . . ?
C14A N1A C7A C13A -179.5(2) . . . . ?
C14A C8A C9A C10A -0.3(4) . . . . ?
C16A O1A C10A C11A 2.0(4) . . . . ?
C16A O1A C10A C9A -176.9(3) . . . . ?
C8A C9A C10A O1A 178.8(3) . . . . ?
C8A C9A C10A C11A -0.1(5) . . . . ?
O1A C10A C11A C15A -177.9(3) . . . . ?
C9A C10A C11A C15A 0.8(4) . . . . ?
C3A C4A C12A C13A -0.2(4) . . . . ?
C3A C4A C12A C5A 179.0(3) . . . . ?
C6A C5A C12A C4A -179.6(3) . . . . ?
C6A C5A C12A C13A -0.4(4) . . . . ?
C2A C1A C13A C12A 0.3(4) . . . . ?
C2A C1A C13A C7A -179.6(3) . . . . ?
C4A C12A C13A C1A -0.1(4) . . . . ?
C5A C12A C13A C1A -179.4(3) . . . . ?
C4A C12A C13A C7A 179.8(3) . . . . ?
C5A C12A C13A C7A 0.6(4) . . . . ?
N2A C7A C13A C1A -0.4(5) . . . . ?
N1A C7A C13A C1A 179.7(3) . . . . ?
N2A C7A C13A C12A 179.7(3) . . . . ?
N1A C7A C13A C12A -0.2(4) . . . . ?
C6A N1A C14A C8A -2.2(5) . . . . ?
C7A N1A C14A C8A 177.0(3) . . . . ?
C6A N1A C14A C15A -179.4(3) . . . . ?
C7A N1A C14A C15A -0.2(3) . . . . ?
C9A C8A C14A N1A -176.9(3) . . . . ?
C9A C8A C14A C15A -0.1(4) . . . . ?
C7A N2A C15A C14A 0.6(3) . . . . ?
C7A N2A C15A C11A -177.9(3) . . . . ?
N1A C14A C15A N2A -0.2(3) . . . . ?
C8A C14A C15A N2A -177.8(3) . . . . ?
N1A C14A C15A C11A 178.4(3) . . . . ?
C8A C14A C15A C11A 0.9(4) . . . . ?
C10A C11A C15A N2A 177.2(3) . . . . ?
C10A C11A C15A C14A -1.2(4) . . . . ?
C13B C1B C2B C3B 0.5(5) . . . . ?
C1B C2B C3B C4B 0.8(5) . . . . ?
C2B C3B C4B C12B -1.1(5) . . . . ?
C12B C5B C6B N1B 0.3(5) . . . . ?
C14B N1B C6B C5B -178.8(3) . . . . ?
C7B N1B C6B C5B -1.0(4) . . . . ?
C15B N2B C7B N1B 0.4(3) . . . . ?
C15B N2B C7B C13B -179.4(3) . . . . ?
C6B N1B C7B N2B -178.6(3) . . . . ?
C14B N1B C7B N2B -0.3(3) . . . . ?
C6B N1B C7B C13B 1.3(4) . . . . ?
C14B N1B C7B C13B 179.6(2) . . . . ?
C14B C8B C9B C10B 0.6(4) . . . . ?
C16B O1B C10B C11B 0.6(4) . . . . ?
C16B O1B C10B C9B -179.4(3) . . . . ?
C8B C9B C10B O1B -179.4(3) . . . . ?
C8B C9B C10B C11B 0.6(5) . . . . ?
O1B C10B C11B C15B 178.4(3) . . . . ?
C9B C10B C11B C15B -1.5(4) . . . . ?
C3B C4B C12B C13B 0.1(5) . . . . ?
C3B C4B C12B C5B -178.5(3) . . . . ?
C6B C5B C12B C4B 178.6(3) . . . . ?
C6B C5B C12B C13B 0.0(5) . . . . ?
C2B C1B C13B C12B -1.4(4) . . . . ?
C2B C1B C13B C7B 178.0(3) . . . . ?
C4B C12B C13B C1B 1.1(4) . . . . ?
C5B C12B C13B C1B 179.8(3) . . . . ?
C4B C12B C13B C7B -178.4(3) . . . . ?
C5B C12B C13B C7B 0.3(4) . . . . ?
N2B C7B C13B C1B -0.6(5) . . . . ?
N1B C7B C13B C1B 179.6(3) . . . . ?
N2B C7B C13B C12B 178.9(3) . . . . ?
N1B C7B C13B C12B -0.9(4) . . . . ?
C9B C8B C14B N1B 177.9(3) . . . . ?
C9B C8B C14B C15B -0.9(4) . . . . ?
C6B N1B C14B C8B -0.8(5) . . . . ?
C7B N1B C14B C8B -178.9(3) . . . . ?
C6B N1B C14B C15B 178.2(3) . . . . ?
C7B N1B C14B C15B 0.0(3) . . . . ?
C7B N2B C15B C11B 178.9(3) . . . . ?
C7B N2B C15B C14B -0.4(3) . . . . ?
C10B C11B C15B N2B -178.0(3) . . . . ?
C10B C11B C15B C14B 1.3(4) . . . . ?
C8B C14B C15B N2B 179.3(3) . . . . ?
N1B C14B C15B N2B 0.2(3) . . . . ?
C8B C14B C15B C11B -0.1(4) . . . . ?
N1B C14B C15B C11B -179.2(3) . . . . ?

_refine_diff_density_max         0.148
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_17demb03
_database_code_depnum_ccdc_archive 'CCDC 1811816'
_audit_update_record             
;
2017-12-20 deposited with the CCDC.
2018-11-28 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT097_17demb03            
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.02 eA-3  
RESPONSE: The identified residual electron density is positioned near the 
center of of the C13b ring and not likely associated with a missing atom
in the atom list.  This Alert Level B error is an artifact from a 
weekly diffracting crystal and possible spurious weak reflections due
to crystal twinning.  The R values also reflect this observation. 
;
_vrf_PLAT230_17demb03            
;
PROBLEM: Hirshfeld Test Diff for   C9B      --C10B      .        7.5 s.u.  
RESPONSE: This Alert Level B error is an artifact from a 
weekly diffracting crystal and possible spurious weak reflections
dur to crystal twinning.  The R values also reflect this observation.
;
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 N2'
_chemical_formula_sum            'C17 H14 N2'
_chemical_formula_weight         246.30

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

_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                   13.2669(8)
_cell_length_b                   11.5841(7)
_cell_length_c                   16.4623(11)
_cell_angle_alpha                90
_cell_angle_beta                 100.794(4)
_cell_angle_gamma                90
_cell_volume                     2485.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3679
_cell_measurement_theta_min      4.70
_cell_measurement_theta_max      67.71

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.191
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.094
_exptl_absorpt_coefficient_mu    0.606
_shelx_estimated_absorpt_T_min   0.893
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6355
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
_exptl_absorpt_special_details   ?


_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            36041
_diffrn_reflns_av_unetI/netI     0.0660
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.391
_diffrn_reflns_theta_max         68.213
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4524
_reflns_number_gt                3189
_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       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms (Uiso = 1.5xUeqiv for methyl groups).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1476P)²+2.1076P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4524
_refine_ls_number_parameters     347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0861
_refine_ls_wR_factor_ref         0.2635
_refine_ls_wR_factor_gt          0.2373
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
N1A N 0.71294(18) 0.36504(19) 0.24602(14) 0.0244(5) Uani 1 1 d . . . . .
C1A C 0.7978(2) 0.6203(3) 0.13382(18) 0.0320(7) Uani 1 1 d . . . . .
H1A H 0.8688 0.6245 0.1574 0.038 Uiso 1 1 calc R U . . .
N2A N 0.87609(19) 0.4327(2) 0.25839(15) 0.0288(6) Uani 1 1 d . . . . .
C2A C 0.7557(3) 0.6980(3) 0.0749(2) 0.0406(8) Uani 1 1 d . . . . .
H2A H 0.7975 0.7562 0.0575 0.049 Uiso 1 1 calc R U . . .
C3A C 0.6492(3) 0.6921(3) 0.0392(2) 0.0399(8) Uani 1 1 d . . . . .
H3A H 0.6205 0.7460 -0.0022 0.048 Uiso 1 1 calc R U . . .
C4A C 0.5889(3) 0.6099(3) 0.0642(2) 0.0393(8) Uani 1 1 d . . . . .
H4A H 0.5181 0.6067 0.0398 0.047 Uiso 1 1 calc R U . . .
C5A C 0.5661(3) 0.4423(3) 0.1552(2) 0.0372(8) Uani 1 1 d . . . . .
H5A H 0.4947 0.4405 0.1327 0.045 Uiso 1 1 calc R U . . .
C6A C 0.6075(2) 0.3639(3) 0.21434(19) 0.0335(7) Uani 1 1 d . . . . .
H6A H 0.5646 0.3088 0.2338 0.040 Uiso 1 1 calc R U . . .
C7A C 0.7781(2) 0.4482(2) 0.22053(18) 0.0298(7) Uani 1 1 d . . . . .
C8A C 0.7517(2) 0.1970(2) 0.35040(18) 0.0296(7) Uani 1 1 d . . . . .
C9A C 0.8361(3) 0.1487(3) 0.4041(2) 0.0372(8) Uani 1 1 d . . . . .
C10A C 0.9357(3) 0.1958(3) 0.4088(2) 0.0374(8) Uani 1 1 d . . . . .
H10A H 0.9911 0.1609 0.4456 0.045 Uiso 1 1 calc R U . . .
C11A C 0.9566(3) 0.2888(3) 0.3634(2) 0.0370(8) Uani 1 1 d . . . . .
H11A H 1.0244 0.3178 0.3681 0.044 Uiso 1 1 calc R U . . .
C12A C 0.6305(2) 0.5273(3) 0.12705(19) 0.0312(7) Uani 1 1 d . . . . .
C13A C 0.7358(2) 0.5331(3) 0.15998(18) 0.0301(7) Uani 1 1 d . . . . .
C14A C 0.7750(2) 0.2949(3) 0.30398(18) 0.0312(7) Uani 1 1 d . . . . .
C15A C 0.8737(3) 0.3396(3) 0.30955(19) 0.0331(7) Uani 1 1 d . . . . .
C16A C 0.6447(3) 0.1505(3) 0.3410(2) 0.0434(8) Uani 1 1 d . . . . .
H16A H 0.5998 0.2097 0.3576 0.065 Uiso 1 1 calc R U . . .
H16B H 0.6447 0.0822 0.3761 0.065 Uiso 1 1 calc R U . . .
H16C H 0.6196 0.1293 0.2831 0.065 Uiso 1 1 calc R U . . .
C17A C 0.8233(3) 0.0469(3) 0.4584(2) 0.0456(9) Uani 1 1 d . . . . .
H17A H 0.8899 0.0267 0.4922 0.068 Uiso 1 1 calc R U . . .
H17B H 0.7966 -0.0191 0.4237 0.068 Uiso 1 1 calc R U . . .
H17C H 0.7751 0.0669 0.4945 0.068 Uiso 1 1 calc R U . . .
N1B N 0.78951(18) 0.88005(19) 0.25903(14) 0.0239(5) Uani 1 1 d . . . . .
C1B C 0.6925(2) 0.6243(3) 0.36366(18) 0.0293(7) Uani 1 1 d . . . . .
H1B H 0.6219 0.6242 0.3389 0.035 Uiso 1 1 calc R U . . .
N2B N 0.62481(18) 0.8164(2) 0.24001(15) 0.0288(6) Uani 1 1 d . . . . .
C2B C 0.7290(3) 0.5419(3) 0.42075(19) 0.0366(8) Uani 1 1 d . . . . .
H2B H 0.6843 0.4853 0.4361 0.044 Uiso 1 1 calc R U . . .
C3B C 0.8352(3) 0.5421(3) 0.45702(19) 0.0382(8) Uani 1 1 d . . . . .
H3B H 0.8614 0.4850 0.4969 0.046 Uiso 1 1 calc R U . . .
C4B C 0.8992(3) 0.6224(3) 0.43552(19) 0.0369(8) Uani 1 1 d . . . . .
H4B H 0.9698 0.6203 0.4604 0.044 Uiso 1 1 calc R U . . .
C5B C 0.9313(2) 0.7952(3) 0.3531(2) 0.0356(7) Uani 1 1 d . . . . .
H5B H 1.0019 0.7944 0.3780 0.043 Uiso 1 1 calc R U . . .
C6B C 0.8943(2) 0.8771(3) 0.29498(19) 0.0331(7) Uani 1 1 d . . . . .
H6B H 0.9398 0.9322 0.2789 0.040 Uiso 1 1 calc R U . . .
C7B C 0.7201(2) 0.7977(2) 0.28089(18) 0.0300(7) Uani 1 1 d . . . . .
C8B C 0.7598(2) 1.0524(3) 0.15795(18) 0.0293(7) Uani 1 1 d . . . . .
C9B C 0.6786(3) 1.1044(3) 0.1040(2) 0.0393(8) Uani 1 1 d . . . . .
C10B C 0.5782(2) 1.0598(3) 0.09470(19) 0.0347(7) Uani 1 1 d . . . . .
H10B H 0.5253 1.0980 0.0576 0.042 Uiso 1 1 calc R U . . .
C11B C 0.5525(3) 0.9649(3) 0.1358(2) 0.0368(8) Uani 1 1 d . . . . .
H11B H 0.4839 0.9372 0.1274 0.044 Uiso 1 1 calc R U . . .
C12B C 0.8629(2) 0.7111(3) 0.37583(18) 0.0297(7) Uani 1 1 d . . . . .
C13B C 0.7577(2) 0.7100(3) 0.34053(18) 0.0285(7) Uani 1 1 d . . . . .
C14B C 0.7317(2) 0.9527(3) 0.20098(18) 0.0315(7) Uani 1 1 d . . . . .
C15B C 0.6319(3) 0.9100(3) 0.19114(19) 0.0332(7) Uani 1 1 d . . . . .
C16B C 0.8688(3) 1.0948(3) 0.1726(2) 0.0416(8) Uani 1 1 d . . . . .
H16D H 0.9136 1.0336 0.1586 0.062 Uiso 1 1 calc R U . . .
H16E H 0.8902 1.1159 0.2309 0.062 Uiso 1 1 calc R U . . .
H16F H 0.8735 1.1625 0.1379 0.062 Uiso 1 1 calc R U . . .
C17B C 0.6957(3) 1.2106(3) 0.0539(2) 0.0471(10) Uani 1 1 d . . . . .
H17D H 0.7392 1.1902 0.0141 0.071 Uiso 1 1 calc R U . . .
H17E H 0.7295 1.2708 0.0912 0.071 Uiso 1 1 calc R U . . .
H17F H 0.6295 1.2393 0.0243 0.071 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
N1A C14A 1.398(4) . ?
N1A C6A 1.398(4) . ?
N1A C7A 1.409(4) . ?
C1A C2A 1.364(5) . ?
C1A C13A 1.419(4) . ?
N2A C7A 1.345(4) . ?
N2A C15A 1.373(4) . ?
C2A C3A 1.426(5) . ?
C3A C4A 1.356(5) . ?
C4A C12A 1.442(4) . ?
C5A C6A 1.370(5) . ?
C5A C12A 1.436(4) . ?
C7A C13A 1.438(4) . ?
C8A C9A 1.407(5) . ?
C8A C14A 1.433(4) . ?
C8A C16A 1.499(5) . ?
C9A C10A 1.418(5) . ?
C9A C17A 1.508(4) . ?
C10A C11A 1.369(5) . ?
C11A C15A 1.406(5) . ?
C12A C13A 1.402(4) . ?
C14A C15A 1.395(5) . ?
N1B C14B 1.391(4) . ?
N1B C6B 1.406(4) . ?
N1B C7B 1.419(4) . ?
C1B C2B 1.363(4) . ?
C1B C13B 1.414(4) . ?
N2B C7B 1.333(4) . ?
N2B C15B 1.364(4) . ?
C2B C3B 1.423(5) . ?
C3B C4B 1.350(5) . ?
C4B C12B 1.441(4) . ?
C5B C6B 1.371(5) . ?
C5B C12B 1.429(4) . ?
C7B C13B 1.435(4) . ?
C8B C9B 1.397(5) . ?
C8B C14B 1.441(4) . ?
C8B C16B 1.503(5) . ?
C9B C10B 1.409(5) . ?
C9B C17B 1.522(4) . ?
C10B C11B 1.367(5) . ?
C11B C15B 1.409(4) . ?
C12B C13B 1.408(4) . ?
C14B C15B 1.394(5) . ?

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
C14A N1A C6A 132.0(3) . . ?
C14A N1A C7A 106.6(3) . . ?
C6A N1A C7A 121.4(2) . . ?
C2A C1A C13A 120.1(3) . . ?
C7A N2A C15A 104.9(2) . . ?
C1A C2A C3A 120.2(3) . . ?
C4A C3A C2A 120.3(3) . . ?
C3A C4A C12A 121.0(3) . . ?
C6A C5A C12A 120.0(3) . . ?
C5A C6A N1A 119.9(3) . . ?
N2A C7A N1A 111.4(3) . . ?
N2A C7A C13A 129.1(3) . . ?
N1A C7A C13A 119.5(3) . . ?
C9A C8A C14A 115.1(3) . . ?
C9A C8A C16A 123.3(3) . . ?
C14A C8A C16A 121.6(3) . . ?
C8A C9A C10A 120.4(3) . . ?
C8A C9A C17A 121.2(3) . . ?
C10A C9A C17A 118.4(3) . . ?
C11A C10A C9A 123.7(3) . . ?
C10A C11A C15A 117.4(3) . . ?
C13A C12A C5A 121.2(3) . . ?
C13A C12A C4A 117.8(3) . . ?
C5A C12A C4A 121.0(3) . . ?
C12A C13A C1A 120.6(3) . . ?
C12A C13A C7A 117.8(3) . . ?
C1A C13A C7A 121.6(3) . . ?
C15A C14A N1A 104.7(3) . . ?
C15A C14A C8A 123.5(3) . . ?
N1A C14A C8A 131.7(3) . . ?
N2A C15A C14A 112.4(3) . . ?
N2A C15A C11A 127.6(3) . . ?
C14A C15A C11A 120.0(3) . . ?
C14B N1B C6B 132.7(3) . . ?
C14B N1B C7B 106.3(2) . . ?
C6B N1B C7B 121.0(2) . . ?
C2B C1B C13B 121.4(3) . . ?
C7B N2B C15B 105.3(2) . . ?
C1B C2B C3B 118.9(3) . . ?
C4B C3B C2B 120.8(3) . . ?
C3B C4B C12B 121.6(3) . . ?
C6B C5B C12B 119.5(3) . . ?
C5B C6B N1B 120.5(3) . . ?
N2B C7B N1B 111.2(2) . . ?
N2B C7B C13B 129.4(3) . . ?
N1B C7B C13B 119.4(3) . . ?
C9B C8B C14B 114.7(3) . . ?
C9B C8B C16B 124.4(3) . . ?
C14B C8B C16B 120.8(3) . . ?
C8B C9B C10B 120.8(3) . . ?
C8B C9B C17B 121.1(3) . . ?
C10B C9B C17B 118.1(3) . . ?
C11B C10B C9B 124.0(3) . . ?
C10B C11B C15B 117.2(3) . . ?
C13B C12B C5B 121.8(3) . . ?
C13B C12B C4B 117.0(3) . . ?
C5B C12B C4B 121.2(3) . . ?
C12B C13B C1B 120.2(3) . . ?
C12B C13B C7B 117.8(3) . . ?
C1B C13B C7B 121.9(3) . . ?
N1B C14B C15B 104.8(3) . . ?
N1B C14B C8B 131.5(3) . . ?
C15B C14B C8B 123.7(3) . . ?
N2B C15B C14B 112.5(3) . . ?
N2B C15B C11B 127.9(3) . . ?
C14B C15B C11B 119.6(3) . . ?

_refine_diff_density_max         1.022
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.092

