# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 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_aa_a
_database_code_depnum_ccdc_archive 'CCDC 1915584'
loop_
_audit_author_name
_audit_author_address
'Tingting Zhang'
;Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2019-05-13 deposited with the CCDC.	2019-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H13 N O2'
_chemical_formula_sum            'C19 H13 N O2'
_chemical_formula_weight         287.30

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   27.6342(16)
_cell_length_b                   8.7182(5)
_cell_length_c                   12.6486(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.026(2)
_cell_angle_gamma                90
_cell_volume                     2991.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9965
_cell_measurement_theta_min      3.26
_cell_measurement_theta_max      64.87

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   0.6714
_exptl_transmission_factor_max   0.7526
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.668
_shelx_estimated_absorpt_T_min   0.867
_shelx_estimated_absorpt_T_max   0.889
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_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            46055
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.259
_diffrn_reflns_theta_max         65.139
_diffrn_reflns_theta_full        65.139
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5080
_reflns_number_gt                3716
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0485P)²+0.9006P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.00200(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5080
_refine_ls_number_parameters     400
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1253
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.54060(6) 0.60955(19) 0.09368(12) 0.0712(4) Uani 1 1 d . . . . .
H1 H 0.528431 0.594541 0.030154 0.107 Uiso 1 1 calc R U . . .
C1 C 0.65295(7) 0.5959(3) 0.18505(15) 0.0536(5) Uani 1 1 d . . . . .
N1 N 0.62325(6) 0.6613(2) 0.25114(13) 0.0558(4) Uani 1 1 d . . . . .
O2 O 0.50338(6) 0.38813(19) 0.11025(12) 0.0750(5) Uani 1 1 d . . . . .
C2 C 0.65392(8) 0.4470(3) 0.14881(18) 0.0661(6) Uani 1 1 d . . . . .
H2 H 0.631987 0.373658 0.164999 0.079 Uiso 1 1 calc R U . . .
N2 N 0.87221(6) 0.6549(2) 0.64922(13) 0.0552(4) Uani 1 1 d . . . . .
O3 O 0.95081(6) 0.52471(19) 0.57555(15) 0.0801(5) Uani 1 1 d . . . . .
H3A H 0.966122 0.462204 0.546345 0.120 Uiso 1 1 calc R U . . .
C3 C 0.68862(10) 0.4108(3) 0.0877(2) 0.0820(7) Uani 1 1 d . . . . .
H3 H 0.690318 0.310771 0.063161 0.098 Uiso 1 1 calc R U . . .
O4 O 0.99680(7) 0.6862(2) 0.50338(16) 0.0919(6) Uani 1 1 d . . . . .
C4 C 0.72096(10) 0.5192(4) 0.0618(2) 0.0872(8) Uani 1 1 d . . . . .
H4 H 0.743749 0.491045 0.019953 0.105 Uiso 1 1 calc R U . . .
C7 C 0.67537(7) 0.8470(3) 0.21392(17) 0.0609(6) Uani 1 1 d . . . . .
C6 C 0.68559(7) 0.7081(3) 0.16073(16) 0.0585(5) Uani 1 1 d . . . . .
C5 C 0.71986(8) 0.6677(4) 0.09714(19) 0.0748(7) Uani 1 1 d . . . . .
H5 H 0.741541 0.740390 0.079111 0.090 Uiso 1 1 calc R U . . .
C9 C 0.67669(11) 1.1023(3) 0.2793(2) 0.0908(9) Uani 1 1 d . . . . .
H9 H 0.690655 1.199708 0.285853 0.109 Uiso 1 1 calc R U . . .
C8 C 0.69565(10) 0.9932(3) 0.2218(2) 0.0789(7) Uani 1 1 d . . . . .
H8 H 0.721892 1.016406 0.188268 0.095 Uiso 1 1 calc R U . . .
C10 C 0.63690(11) 1.0710(3) 0.3284(2) 0.0877(8) Uani 1 1 d . . . . .
H10 H 0.623754 1.149133 0.364228 0.105 Uiso 1 1 calc R U . . .
C11 C 0.61639(9) 0.9254(3) 0.3249(2) 0.0741(7) Uani 1 1 d . . . . .
H11 H 0.590168 0.903310 0.358819 0.089 Uiso 1 1 calc R U . . .
C12 C 0.63680(7) 0.8148(3) 0.26867(16) 0.0573(5) Uani 1 1 d . . . . .
C15 C 0.58529(10) 0.4892(4) 0.48816(19) 0.0887(9) Uani 1 1 d . . . . .
H15 H 0.595809 0.489461 0.562534 0.106 Uiso 1 1 calc R U . . .
C14 C 0.61036(9) 0.5733(3) 0.42408(17) 0.0759(7) Uani 1 1 d . . . . .
H14 H 0.638169 0.628743 0.455407 0.091 Uiso 1 1 calc R U . . .
C13 C 0.59462(7) 0.5763(3) 0.31325(16) 0.0555(5) Uani 1 1 d . . . . .
C16 C 0.54486(10) 0.4050(3) 0.44259(19) 0.0840(8) Uani 1 1 d . . . . .
H16 H 0.528149 0.347359 0.486014 0.101 Uiso 1 1 calc R U . . .
C17 C 0.52885(8) 0.4055(3) 0.33247(17) 0.0686(6) Uani 1 1 d . . . . .
H17 H 0.501628 0.346802 0.302112 0.082 Uiso 1 1 calc R U . . .
C18 C 0.55290(7) 0.4927(2) 0.26614(15) 0.0527(5) Uani 1 1 d . . . . .
C19 C 0.53132(7) 0.4961(2) 0.14968(16) 0.0515(5) Uani 1 1 d . . . . .
C20 C 0.83684(7) 0.6237(3) 0.55753(16) 0.0549(5) Uani 1 1 d . . . . .
C21 C 0.82528(8) 0.7070(3) 0.46260(17) 0.0680(6) Uani 1 1 d . . . . .
H21 H 0.842483 0.795567 0.452019 0.082 Uiso 1 1 calc R U . . .
C22 C 0.78733(8) 0.6532(3) 0.38461(19) 0.0773(7) Uani 1 1 d . . . . .
H22 H 0.778713 0.706981 0.320257 0.093 Uiso 1 1 calc R U . . .
C23 C 0.76176(9) 0.5215(3) 0.3996(2) 0.0797(7) Uani 1 1 d . . . . .
H23 H 0.736505 0.487766 0.345072 0.096 Uiso 1 1 calc R U . . .
C24 C 0.77303(8) 0.4395(3) 0.4938(2) 0.0720(7) Uani 1 1 d . . . . .
H24 H 0.755484 0.351099 0.503187 0.086 Uiso 1 1 calc R U . . .
C25 C 0.81117(7) 0.4901(3) 0.57551(17) 0.0569(5) Uani 1 1 d . . . . .
C26 C 0.83164(7) 0.4396(2) 0.68392(17) 0.0555(5) Uani 1 1 d . . . . .
C27 C 0.82101(8) 0.3199(3) 0.7484(2) 0.0714(6) Uani 1 1 d . . . . .
H27 H 0.796251 0.249804 0.722115 0.086 Uiso 1 1 calc R U . . .
C28 C 0.84776(10) 0.3066(3) 0.8520(2) 0.0792(7) Uani 1 1 d . . . . .
H28 H 0.840761 0.227198 0.895848 0.095 Uiso 1 1 calc R U . . .
C29 C 0.88486(9) 0.4099(3) 0.8915(2) 0.0750(7) Uani 1 1 d . . . . .
H29 H 0.902531 0.397622 0.961323 0.090 Uiso 1 1 calc R U . . .
C30 C 0.89633(8) 0.5304(3) 0.83028(17) 0.0624(6) Uani 1 1 d . . . . .
H30 H 0.921202 0.599686 0.857324 0.075 Uiso 1 1 calc R U . . .
C31 C 0.86905(7) 0.5437(2) 0.72618(16) 0.0537(5) Uani 1 1 d . . . . .
C32 C 0.90441(7) 0.7844(2) 0.66197(16) 0.0543(5) Uani 1 1 d . . . . .
C33 C 0.89210(9) 0.9103(3) 0.7171(2) 0.0781(7) Uani 1 1 d . . . . .
H33 H 0.863921 0.907463 0.747132 0.094 Uiso 1 1 calc R U . . .
C34 C 0.92100(10) 1.0409(3) 0.7283(2) 0.0849(8) Uani 1 1 d . . . . .
H34 H 0.912321 1.124426 0.766411 0.102 Uiso 1 1 calc R U . . .
C35 C 0.96217(9) 1.0479(3) 0.6838(2) 0.0733(7) Uani 1 1 d . . . . .
H35 H 0.981407 1.136218 0.690571 0.088 Uiso 1 1 calc R U . . .
C36 C 0.97484(8) 0.9231(3) 0.62889(18) 0.0631(6) Uani 1 1 d . . . . .
H36 H 1.002922 0.928110 0.598582 0.076 Uiso 1 1 calc R U . . .
C37 C 0.94693(7) 0.7895(2) 0.61727(15) 0.0515(5) Uani 1 1 d . . . . .
C38 C 0.96604(7) 0.6605(3) 0.56039(17) 0.0569(5) 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
O1 C19 1.271(2) . ?
O1 H1 0.8200 . ?
C1 C2 1.379(3) . ?
C1 N1 1.400(3) . ?
C1 C6 1.404(3) . ?
N1 C12 1.396(3) . ?
N1 C13 1.425(2) . ?
O2 C19 1.258(2) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9300 . ?
N2 C31 1.388(3) . ?
N2 C20 1.393(2) . ?
N2 C32 1.427(3) . ?
O3 C38 1.283(3) . ?
O3 H3A 0.8200 . ?
C3 C4 1.382(4) . ?
C3 H3 0.9300 . ?
O4 C38 1.236(2) . ?
C4 C5 1.372(4) . ?
C4 H4 0.9300 . ?
C7 C8 1.388(3) . ?
C7 C12 1.406(3) . ?
C7 C6 1.440(3) . ?
C6 C5 1.400(3) . ?
C5 H5 0.9300 . ?
C9 C8 1.361(4) . ?
C9 C10 1.389(4) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C10 C11 1.387(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(3) . ?
C11 H11 0.9300 . ?
C15 C16 1.368(3) . ?
C15 C14 1.375(3) . ?
C15 H15 0.9300 . ?
C14 C13 1.386(3) . ?
C14 H14 0.9300 . ?
C13 C18 1.398(3) . ?
C16 C17 1.378(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.391(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.480(3) . ?
C20 C21 1.387(3) . ?
C20 C25 1.405(3) . ?
C21 C22 1.377(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.380(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.373(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.399(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.448(3) . ?
C26 C27 1.390(3) . ?
C26 C31 1.402(3) . ?
C27 C28 1.381(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.384(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.377(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.391(3) . ?
C30 H30 0.9300 . ?
C32 C33 1.377(3) . ?
C32 C37 1.399(3) . ?
C33 C34 1.382(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.364(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.372(3) . ?
C35 H35 0.9300 . ?
C36 C37 1.389(3) . ?
C36 H36 0.9300 . ?
C37 C38 1.486(3) . ?

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
C19 O1 H1 109.5 . . ?
C2 C1 N1 129.25(19) . . ?
C2 C1 C6 121.9(2) . . ?
N1 C1 C6 108.77(19) . . ?
C12 N1 C1 108.38(16) . . ?
C12 N1 C13 124.83(17) . . ?
C1 N1 C13 124.64(18) . . ?
C3 C2 C1 117.5(2) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C31 N2 C20 108.63(17) . . ?
C31 N2 C32 126.47(17) . . ?
C20 N2 C32 124.84(17) . . ?
C38 O3 H3A 109.5 . . ?
C2 C3 C4 121.8(3) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C8 C7 C12 118.8(2) . . ?
C8 C7 C6 133.9(2) . . ?
C12 C7 C6 107.29(19) . . ?
C5 C6 C1 119.0(2) . . ?
C5 C6 C7 134.0(2) . . ?
C1 C6 C7 106.99(18) . . ?
C4 C5 C6 118.9(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C8 C9 C10 121.3(3) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C9 C8 C7 119.3(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C11 C10 C9 121.3(3) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C12 C11 C10 116.8(2) . . ?
C12 C11 H11 121.6 . . ?
C10 C11 H11 121.6 . . ?
C11 C12 N1 128.9(2) . . ?
C11 C12 C7 122.5(2) . . ?
N1 C12 C7 108.57(19) . . ?
C16 C15 C14 120.0(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C14 C13 120.7(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C13 C18 119.66(19) . . ?
C14 C13 N1 117.89(18) . . ?
C18 C13 N1 122.41(17) . . ?
C15 C16 C17 120.2(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C18 120.9(2) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C13 118.56(18) . . ?
C17 C18 C19 117.59(18) . . ?
C13 C18 C19 123.80(18) . . ?
O2 C19 O1 122.35(18) . . ?
O2 C19 C18 118.64(19) . . ?
O1 C19 C18 118.98(18) . . ?
C21 C20 N2 128.9(2) . . ?
C21 C20 C25 122.3(2) . . ?
N2 C20 C25 108.82(18) . . ?
C22 C21 C20 117.4(2) . . ?
C22 C21 H21 121.3 . . ?
C20 C21 H21 121.3 . . ?
C21 C22 C23 121.6(2) . . ?
C21 C22 H22 119.2 . . ?
C23 C22 H22 119.2 . . ?
C24 C23 C22 121.0(2) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C25 119.4(2) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C24 C25 C20 118.3(2) . . ?
C24 C25 C26 134.9(2) . . ?
C20 C25 C26 106.71(18) . . ?
C27 C26 C31 119.0(2) . . ?
C27 C26 C25 134.1(2) . . ?
C31 C26 C25 106.86(18) . . ?
C28 C27 C26 119.0(2) . . ?
C28 C27 H27 120.5 . . ?
C26 C27 H27 120.5 . . ?
C27 C28 C29 120.9(2) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 H28 119.6 . . ?
C30 C29 C28 121.8(2) . . ?
C30 C29 H29 119.1 . . ?
C28 C29 H29 119.1 . . ?
C29 C30 C31 117.0(2) . . ?
C29 C30 H30 121.5 . . ?
C31 C30 H30 121.5 . . ?
N2 C31 C30 128.8(2) . . ?
N2 C31 C26 108.98(18) . . ?
C30 C31 C26 122.2(2) . . ?
C33 C32 C37 119.1(2) . . ?
C33 C32 N2 118.60(18) . . ?
C37 C32 N2 122.24(18) . . ?
C32 C33 C34 121.0(2) . . ?
C32 C33 H33 119.5 . . ?
C34 C33 H33 119.5 . . ?
C35 C34 C33 120.4(2) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C34 C35 C36 119.1(2) . . ?
C34 C35 H35 120.4 . . ?
C36 C35 H35 120.4 . . ?
C35 C36 C37 121.9(2) . . ?
C35 C36 H36 119.1 . . ?
C37 C36 H36 119.1 . . ?
C36 C37 C32 118.46(19) . . ?
C36 C37 C38 116.40(17) . . ?
C32 C37 C38 125.11(18) . . ?
O4 C38 O3 122.5(2) . . ?
O4 C38 C37 119.5(2) . . ?
O3 C38 C37 117.97(17) . . ?

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
C2 C1 N1 C12 178.1(2) . . . . ?
C6 C1 N1 C12 0.2(2) . . . . ?
C2 C1 N1 C13 14.1(3) . . . . ?
C6 C1 N1 C13 -163.79(17) . . . . ?
N1 C1 C2 C3 -177.2(2) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
N1 C1 C6 C5 178.58(18) . . . . ?
C2 C1 C6 C7 -178.13(19) . . . . ?
N1 C1 C6 C7 0.0(2) . . . . ?
C8 C7 C6 C5 0.2(4) . . . . ?
C12 C7 C6 C5 -178.4(2) . . . . ?
C8 C7 C6 C1 178.5(2) . . . . ?
C12 C7 C6 C1 -0.1(2) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C1 C6 C5 C4 -0.9(3) . . . . ?
C7 C6 C5 C4 177.2(2) . . . . ?
C10 C9 C8 C7 -1.2(4) . . . . ?
C12 C7 C8 C9 -2.1(3) . . . . ?
C6 C7 C8 C9 179.5(2) . . . . ?
C8 C9 C10 C11 3.0(4) . . . . ?
C9 C10 C11 C12 -1.3(4) . . . . ?
C10 C11 C12 N1 -179.1(2) . . . . ?
C10 C11 C12 C7 -2.1(3) . . . . ?
C1 N1 C12 C11 177.1(2) . . . . ?
C13 N1 C12 C11 -19.0(3) . . . . ?
C1 N1 C12 C7 -0.2(2) . . . . ?
C13 N1 C12 C7 163.68(18) . . . . ?
C8 C7 C12 C11 3.8(3) . . . . ?
C6 C7 C12 C11 -177.31(19) . . . . ?
C8 C7 C12 N1 -178.63(19) . . . . ?
C6 C7 C12 N1 0.2(2) . . . . ?
C16 C15 C14 C13 1.2(5) . . . . ?
C15 C14 C13 C18 -0.2(4) . . . . ?
C15 C14 C13 N1 -177.8(2) . . . . ?
C12 N1 C13 C14 -53.4(3) . . . . ?
C1 N1 C13 C14 107.9(2) . . . . ?
C12 N1 C13 C18 129.0(2) . . . . ?
C1 N1 C13 C18 -69.6(3) . . . . ?
C14 C15 C16 C17 -0.7(5) . . . . ?
C15 C16 C17 C18 -0.9(4) . . . . ?
C16 C17 C18 C13 1.9(4) . . . . ?
C16 C17 C18 C19 -175.6(2) . . . . ?
C14 C13 C18 C17 -1.4(3) . . . . ?
N1 C13 C18 C17 176.2(2) . . . . ?
C14 C13 C18 C19 176.0(2) . . . . ?
N1 C13 C18 C19 -6.5(3) . . . . ?
C17 C18 C19 O2 -22.4(3) . . . . ?
C13 C18 C19 O2 160.2(2) . . . . ?
C17 C18 C19 O1 155.8(2) . . . . ?
C13 C18 C19 O1 -21.6(3) . . . . ?
C31 N2 C20 C21 177.2(2) . . . . ?
C32 N2 C20 C21 -0.1(3) . . . . ?
C31 N2 C20 C25 -0.7(2) . . . . ?
C32 N2 C20 C25 -178.05(17) . . . . ?
N2 C20 C21 C22 -178.1(2) . . . . ?
C25 C20 C21 C22 -0.4(3) . . . . ?
C20 C21 C22 C23 -0.2(4) . . . . ?
C21 C22 C23 C24 0.6(4) . . . . ?
C22 C23 C24 C25 -0.3(4) . . . . ?
C23 C24 C25 C20 -0.3(3) . . . . ?
C23 C24 C25 C26 176.9(2) . . . . ?
C21 C20 C25 C24 0.7(3) . . . . ?
N2 C20 C25 C24 178.77(18) . . . . ?
C21 C20 C25 C26 -177.26(19) . . . . ?
N2 C20 C25 C26 0.8(2) . . . . ?
C24 C25 C26 C27 0.2(4) . . . . ?
C20 C25 C26 C27 177.6(2) . . . . ?
C24 C25 C26 C31 -178.1(2) . . . . ?
C20 C25 C26 C31 -0.6(2) . . . . ?
C31 C26 C27 C28 -0.3(3) . . . . ?
C25 C26 C27 C28 -178.4(2) . . . . ?
C26 C27 C28 C29 -0.4(4) . . . . ?
C27 C28 C29 C30 0.7(4) . . . . ?
C28 C29 C30 C31 -0.3(3) . . . . ?
C20 N2 C31 C30 -178.68(19) . . . . ?
C32 N2 C31 C30 -1.4(3) . . . . ?
C20 N2 C31 C26 0.3(2) . . . . ?
C32 N2 C31 C26 177.60(17) . . . . ?
C29 C30 C31 N2 178.45(19) . . . . ?
C29 C30 C31 C26 -0.4(3) . . . . ?
C27 C26 C31 N2 -178.37(18) . . . . ?
C25 C26 C31 N2 0.2(2) . . . . ?
C27 C26 C31 C30 0.7(3) . . . . ?
C25 C26 C31 C30 179.27(18) . . . . ?
C31 N2 C32 C33 -78.8(3) . . . . ?
C20 N2 C32 C33 98.1(2) . . . . ?
C31 N2 C32 C37 103.5(2) . . . . ?
C20 N2 C32 C37 -79.6(3) . . . . ?
C37 C32 C33 C34 0.2(4) . . . . ?
N2 C32 C33 C34 -177.6(2) . . . . ?
C32 C33 C34 C35 0.7(4) . . . . ?
C33 C34 C35 C36 -0.8(4) . . . . ?
C34 C35 C36 C37 0.0(4) . . . . ?
C35 C36 C37 C32 0.9(3) . . . . ?
C35 C36 C37 C38 -177.2(2) . . . . ?
C33 C32 C37 C36 -0.9(3) . . . . ?
N2 C32 C37 C36 176.73(19) . . . . ?
C33 C32 C37 C38 177.0(2) . . . . ?
N2 C32 C37 C38 -5.3(3) . . . . ?
C36 C37 C38 O4 -18.4(3) . . . . ?
C32 C37 C38 O4 163.6(2) . . . . ?
C36 C37 C38 O3 159.4(2) . . . . ?
C32 C37 C38 O3 -18.5(3) . . . . ?

_refine_diff_density_max         0.154
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.031

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_b
_database_code_depnum_ccdc_archive 'CCDC 1915586'
loop_
_audit_author_name
_audit_author_address
'Tingting Zhang'
;Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2019-05-13 deposited with the CCDC.	2019-07-02 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         'C19 H13 N O2 [+ solvent]'
_chemical_formula_sum            'C19 H13 N O2'
_chemical_formula_weight         287.30

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

_space_group_crystal_system      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                   11.660(2)
_cell_length_b                   15.654(4)
_cell_length_c                   18.325(4)
_cell_angle_alpha                88.065(17)
_cell_angle_beta                 75.24(2)
_cell_angle_gamma                68.408(16)
_cell_volume                     3000.7(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    9080
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      68.19

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   0.5397
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.666
_shelx_estimated_absorpt_T_min   0.867
_shelx_estimated_absorpt_T_max   0.890
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_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            40507
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.499
_diffrn_reflns_theta_max         63.881
_diffrn_reflns_theta_full        63.881
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             9636
_reflns_number_gt                7531
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0469P)²+1.5253P] 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         9636
_refine_ls_number_parameters     795
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0608
_refine_ls_wR_factor_ref         0.1473
_refine_ls_wR_factor_gt          0.1359
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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 0.67477(19) 0.90961(12) 0.58967(11) 0.0634(5) Uani 1 1 d . . . . .
H1 H 0.6612 0.8866 0.5548 0.095 Uiso 1 1 calc R U . . .
C1 C 0.7087(3) 1.21058(16) 0.85978(14) 0.0511(7) Uani 1 1 d . . . . .
N1 N 0.7760(2) 1.19205(14) 0.78319(12) 0.0513(5) Uani 1 1 d . . . . .
O2 O 0.6789(2) 1.01689(13) 0.50698(11) 0.0698(6) Uani 1 1 d . . . . .
C2 C 0.6090(3) 1.18558(19) 0.89925(16) 0.0609(7) Uani 1 1 d . . . . .
H2 H 0.5775 1.1508 0.8755 0.073 Uiso 1 1 calc R U . . .
N2 N 0.4585(2) 0.87166(14) 0.77737(12) 0.0532(5) Uani 1 1 d . . . . .
O3 O 0.3891(2) 0.56564(13) 0.59272(12) 0.0727(6) Uani 1 1 d . . . . .
H3A H 0.3725 0.5399 0.5608 0.109 Uiso 1 1 calc R U . . .
C3 C 0.5579(3) 1.2140(2) 0.97507(17) 0.0754(9) Uani 1 1 d . . . . .
H3 H 0.4902 1.1988 1.0028 0.091 Uiso 1 1 calc R U . . .
N3 N 0.6002(2) 0.63079(14) 0.19434(11) 0.0477(5) Uani 1 1 d . . . . .
O4 O 0.3465(2) 0.68001(14) 0.51590(11) 0.0669(5) Uani 1 1 d . . . . .
C4 C 0.6059(4) 1.2647(2) 1.01024(18) 0.0841(11) Uani 1 1 d . . . . .
H4 H 0.5714 1.2816 1.0617 0.101 Uiso 1 1 calc R U . . .
N4 N -0.0120(2) 0.33370(15) 0.34909(12) 0.0545(5) Uani 1 1 d . . . . .
O5 O 0.6546(2) 0.81044(13) 0.48483(11) 0.0690(6) Uani 1 1 d . . . . .
C5 C 0.7031(4) 1.2907(2) 0.97127(18) 0.0737(9) Uani 1 1 d . . . . .
H5 H 0.7334 1.3258 0.9956 0.088 Uiso 1 1 calc R U . . .
C9 C 1.0257(4) 1.3255(2) 0.7701(3) 0.0813(11) Uani 1 1 d . . . . .
H9 H 1.0804 1.3563 0.7698 0.098 Uiso 1 1 calc R U . . .
O8 O 0.2247(2) 0.60371(13) 0.45110(12) 0.0693(6) Uani 1 1 d . . . . .
H8A H 0.2667 0.6233 0.4709 0.104 Uiso 1 1 calc R U . . .
C8 C 0.9373(3) 1.32561(19) 0.8361(2) 0.0713(9) Uani 1 1 d . . . . .
H8 H 0.9323 1.3563 0.8801 0.086 Uiso 1 1 calc R U . . .
O7 O 0.3201(2) 0.47570(13) 0.50437(12) 0.0677(5) Uani 1 1 d . . . . .
C7 C 0.8551(3) 1.27929(16) 0.83671(17) 0.0551(7) Uani 1 1 d . . . . .
O6 O 0.6299(2) 0.92648(12) 0.40985(11) 0.0695(6) Uani 1 1 d . . . . .
H6 H 0.6507 0.9474 0.4426 0.104 Uiso 1 1 calc R U . . .
C6 C 0.7565(3) 1.26388(17) 0.89409(16) 0.0552(7) Uani 1 1 d . . . . .
C10 C 1.0347(3) 1.2800(2) 0.7037(2) 0.0750(9) Uani 1 1 d . . . . .
H10 H 1.0950 1.2811 0.6596 0.090 Uiso 1 1 calc R U . . .
C12 C 0.8648(3) 1.23425(16) 0.76870(16) 0.0515(6) Uani 1 1 d . . . . .
C11 C 0.9551(3) 1.2332(2) 0.70232(18) 0.0638(8) Uani 1 1 d . . . . .
H11 H 0.9619 1.2020 0.6582 0.077 Uiso 1 1 calc R U . . .
C13 C 0.7554(2) 1.13964(17) 0.72961(14) 0.0477(6) Uani 1 1 d . . . . .
C014 C -0.0520(2) 0.34994(19) 0.28228(15) 0.0541(7) Uani 1 1 d . . . . .
C14 C 0.7486(3) 1.05448(18) 0.74704(15) 0.0541(7) Uani 1 1 d . . . . .
H14 H 0.7597 1.0311 0.7932 0.065 Uiso 1 1 calc R U . . .
C15 C 0.7254(3) 1.00433(17) 0.69575(14) 0.0522(6) Uani 1 1 d . . . . .
H15 H 0.7195 0.9476 0.7077 0.063 Uiso 1 1 calc R U . . .
C16 C 0.7109(2) 1.03840(16) 0.62632(13) 0.0453(6) Uani 1 1 d . . . . .
C17 C 0.7205(2) 1.12288(16) 0.60878(14) 0.0478(6) Uani 1 1 d . . . . .
H17 H 0.7124 1.1454 0.5620 0.057 Uiso 1 1 calc R U . . .
C18 C 0.7419(2) 1.17336(17) 0.66013(14) 0.0487(6) Uani 1 1 d . . . . .
H18 H 0.7474 1.2302 0.6483 0.058 Uiso 1 1 calc R U . . .
C19 C 0.6876(2) 0.98519(17) 0.57069(15) 0.0485(6) Uani 1 1 d . . . . .
C21 C 0.6708(3) 0.7778(2) 0.80213(16) 0.0618(7) Uani 1 1 d . . . . .
H21 H 0.6897 0.7278 0.7691 0.074 Uiso 1 1 calc R U . . .
C20 C 0.5580(3) 0.85367(17) 0.81204(14) 0.0500(6) Uani 1 1 d . . . . .
C22 C 0.7545(3) 0.7794(2) 0.84320(18) 0.0716(9) Uani 1 1 d . . . . .
H22 H 0.8304 0.7290 0.8381 0.086 Uiso 1 1 calc R U . . .
C23 C 0.7280(3) 0.8542(2) 0.89181(18) 0.0723(9) Uani 1 1 d . . . . .
H23 H 0.7870 0.8535 0.9179 0.087 Uiso 1 1 calc R U . . .
C26 C 0.4048(3) 0.99451(16) 0.85927(14) 0.0497(6) Uani 1 1 d . . . . .
C25 C 0.5286(3) 0.92911(17) 0.86216(14) 0.0497(6) Uani 1 1 d . . . . .
C24 C 0.6165(3) 0.9288(2) 0.90177(16) 0.0609(7) Uani 1 1 d . . . . .
H24 H 0.5993 0.9788 0.9345 0.073 Uiso 1 1 calc R U . . .
C27 C 0.3237(3) 1.07836(18) 0.89839(16) 0.0596(7) Uani 1 1 d . . . . .
H27 H 0.3481 1.1041 0.9340 0.071 Uiso 1 1 calc R U . . .
C29 C 0.1698(3) 1.08523(19) 0.83010(19) 0.0693(8) Uani 1 1 d . . . . .
H29 H 0.0907 1.1169 0.8207 0.083 Uiso 1 1 calc R U . . .
C28 C 0.2065(3) 1.12273(18) 0.88360(18) 0.0671(8) Uani 1 1 d . . . . .
H28 H 0.1514 1.1785 0.9098 0.081 Uiso 1 1 calc R U . . .
C30 C 0.2476(3) 1.00253(18) 0.79084(17) 0.0610(7) Uani 1 1 d . . . . .
H30 H 0.2222 0.9776 0.7552 0.073 Uiso 1 1 calc R U . . .
C31 C 0.3650(3) 0.95731(16) 0.80589(15) 0.0495(6) Uani 1 1 d . . . . .
C32 C 0.4483(2) 0.81261(17) 0.72387(15) 0.0497(6) Uani 1 1 d . . . . .
C33 C 0.4576(3) 0.72372(17) 0.74103(16) 0.0556(7) Uani 1 1 d . . . . .
H33 H 0.4766 0.7010 0.7858 0.067 Uiso 1 1 calc R U . . .
C34 C 0.4387(3) 0.66914(17) 0.69130(16) 0.0543(7) Uani 1 1 d . . . . .
H34 H 0.4450 0.6095 0.7027 0.065 Uiso 1 1 calc R U . . .
C35 C 0.4103(2) 0.70261(17) 0.62446(14) 0.0480(6) Uani 1 1 d . . . . .
C36 C 0.4046(3) 0.79073(17) 0.60716(15) 0.0535(7) Uani 1 1 d . . . . .
H36 H 0.3875 0.8132 0.5619 0.064 Uiso 1 1 calc R U . . .
C37 C 0.4240(3) 0.84513(18) 0.65623(15) 0.0540(7) Uani 1 1 d . . . . .
H37 H 0.4208 0.9039 0.6439 0.065 Uiso 1 1 calc R U . . .
C38 C 0.3806(3) 0.64727(17) 0.57335(16) 0.0509(6) Uani 1 1 d . . . . .
C39 C 0.5190(2) 0.58299(15) 0.19804(14) 0.0440(6) Uani 1 1 d . . . . .
C40 C 0.4198(3) 0.57946(16) 0.25705(15) 0.0514(6) Uani 1 1 d . . . . .
H40 H 0.4015 0.6091 0.3041 0.062 Uiso 1 1 calc R U . . .
C41 C 0.3490(3) 0.53078(18) 0.24390(16) 0.0576(7) Uani 1 1 d . . . . .
H41 H 0.2814 0.5280 0.2827 0.069 Uiso 1 1 calc R U . . .
C42 C 0.3765(3) 0.48558(18) 0.17371(17) 0.0581(7) Uani 1 1 d . . . . .
H42 H 0.3274 0.4531 0.1662 0.070 Uiso 1 1 calc R U . . .
C43 C 0.4755(3) 0.48858(17) 0.11558(15) 0.0525(7) Uani 1 1 d . . . . .
H43 H 0.4942 0.4576 0.0691 0.063 Uiso 1 1 calc R U . . .
C44 C 0.5480(2) 0.53830(15) 0.12649(14) 0.0441(6) Uani 1 1 d . . . . .
C45 C 0.6508(2) 0.55955(16) 0.07788(14) 0.0455(6) Uani 1 1 d . . . . .
C46 C 0.7211(3) 0.53368(19) 0.00313(15) 0.0585(7) Uani 1 1 d . . . . .
H46 H 0.7042 0.4945 -0.0260 0.070 Uiso 1 1 calc R U . . .
C47 C 0.8154(3) 0.5666(2) -0.02688(17) 0.0701(8) Uani 1 1 d . . . . .
H47 H 0.8614 0.5507 -0.0772 0.084 Uiso 1 1 calc R U . . .
C48 C 0.8438(3) 0.6234(2) 0.01632(17) 0.0704(8) Uani 1 1 d . . . . .
H48 H 0.9093 0.6442 -0.0053 0.084 Uiso 1 1 calc R U . . .
C49 C 0.7766(3) 0.64972(19) 0.09090(16) 0.0585(7) Uani 1 1 d . . . . .
H49 H 0.7957 0.6878 0.1199 0.070 Uiso 1 1 calc R U . . .
C50 C 0.6797(2) 0.61740(16) 0.12107(13) 0.0454(6) Uani 1 1 d . . . . .
C51 C 0.6027(2) 0.68545(16) 0.25393(14) 0.0467(6) Uani 1 1 d . . . . .
C52 C 0.6141(3) 0.64923(17) 0.32320(14) 0.0538(7) Uani 1 1 d . . . . .
H52 H 0.6164 0.5898 0.3318 0.065 Uiso 1 1 calc R U . . .
C53 C 0.6218(3) 0.70214(17) 0.37920(14) 0.0535(7) Uani 1 1 d . . . . .
H53 H 0.6284 0.6785 0.4259 0.064 Uiso 1 1 calc R U . . .
C54 C 0.6199(2) 0.79074(16) 0.36604(14) 0.0455(6) Uani 1 1 d . . . . .
C55 C 0.6069(2) 0.82637(16) 0.29705(14) 0.0466(6) Uani 1 1 d . . . . .
H55 H 0.6044 0.8858 0.2883 0.056 Uiso 1 1 calc R U . . .
C56 C 0.5977(3) 0.77409(16) 0.24154(14) 0.0483(6) Uani 1 1 d . . . . .
H56 H 0.5882 0.7985 0.1955 0.058 Uiso 1 1 calc R U . . .
C57 C 0.6350(3) 0.84567(17) 0.42414(14) 0.0492(6) Uani 1 1 d . . . . .
C58 C -0.0212(3) 0.25000(18) 0.37484(17) 0.0563(7) Uani 1 1 d . . . . .
C59 C 0.0006(3) 0.2080(2) 0.44071(18) 0.0673(8) Uani 1 1 d . . . . .
H59 H 0.0285 0.2333 0.4747 0.081 Uiso 1 1 calc R U . . .
C60 C -0.0211(3) 0.1271(2) 0.4536(2) 0.0839(10) Uani 1 1 d . . . . .
H60 H -0.0084 0.0978 0.4975 0.101 Uiso 1 1 calc R U . . .
C61 C -0.0611(3) 0.0887(2) 0.4030(3) 0.0912(12) Uani 1 1 d . . . . .
H61 H -0.0727 0.0333 0.4128 0.109 Uiso 1 1 calc R U . . .
C62 C -0.0839(3) 0.1308(2) 0.3389(2) 0.0847(11) Uani 1 1 d . . . . .
H62 H -0.1123 0.1050 0.3056 0.102 Uiso 1 1 calc R U . . .
C63 C -0.0640(3) 0.2131(2) 0.32397(18) 0.0630(8) Uani 1 1 d . . . . .
C64 C -0.0852(3) 0.2766(2) 0.26548(17) 0.0617(8) Uani 1 1 d . . . . .
C65 C -0.1258(3) 0.2759(3) 0.2008(2) 0.0838(10) Uani 1 1 d . . . . .
H65 H -0.1470 0.2273 0.1888 0.101 Uiso 1 1 calc R U . . .
C66 C -0.1342(3) 0.3473(3) 0.1547(2) 0.0918(11) Uani 1 1 d . . . . .
H66 H -0.1637 0.3478 0.1120 0.110 Uiso 1 1 calc R U . . .
C67 C -0.0996(3) 0.4189(3) 0.17071(19) 0.0804(10) Uani 1 1 d . . . . .
H67 H -0.1043 0.4659 0.1378 0.096 Uiso 1 1 calc R U . . .
C68 C -0.0584(3) 0.4218(2) 0.23432(16) 0.0644(8) Uani 1 1 d . . . . .
H68 H -0.0355 0.4700 0.2450 0.077 Uiso 1 1 calc R U . . .
C69 C 0.0529(2) 0.38123(17) 0.37642(14) 0.0482(6) Uani 1 1 d . . . . .
C70 C 0.0058(3) 0.47687(17) 0.38340(14) 0.0528(7) Uani 1 1 d . . . . .
H70 H -0.0696 0.5106 0.3704 0.063 Uiso 1 1 calc R U . . .
C71 C 0.0711(3) 0.52164(17) 0.40964(14) 0.0512(6) Uani 1 1 d . . . . .
H71 H 0.0411 0.5856 0.4125 0.061 Uiso 1 1 calc R U . . .
C72 C 0.1810(2) 0.47199(17) 0.43173(13) 0.0476(6) Uani 1 1 d . . . . .
C73 C 0.2269(3) 0.37645(17) 0.42520(14) 0.0517(6) Uani 1 1 d . . . . .
H73 H 0.3001 0.3427 0.4404 0.062 Uiso 1 1 calc R U . . .
C74 C 0.1650(3) 0.33148(17) 0.39652(14) 0.0508(6) Uani 1 1 d . . . . .
H74 H 0.1983 0.2675 0.3905 0.061 Uiso 1 1 calc R U . . .
C75 C 0.2482(3) 0.51830(18) 0.46469(15) 0.0524(7) 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
O1 C19 1.273(3) . ?
O1 H1 0.8200 . ?
C1 C2 1.384(4) . ?
C1 C6 1.399(3) . ?
C1 N1 1.403(3) . ?
N1 C12 1.390(3) . ?
N1 C13 1.419(3) . ?
O2 C19 1.266(3) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9300 . ?
N2 C31 1.393(3) . ?
N2 C20 1.396(3) . ?
N2 C32 1.425(3) . ?
O3 C38 1.289(3) . ?
O3 H3A 0.8200 . ?
C3 C4 1.380(5) . ?
C3 H3 0.9300 . ?
N3 C39 1.395(3) . ?
N3 C50 1.396(3) . ?
N3 C51 1.422(3) . ?
O4 C38 1.247(3) . ?
C4 C5 1.366(5) . ?
C4 H4 0.9300 . ?
N4 C014 1.401(3) . ?
N4 C58 1.409(3) . ?
N4 C69 1.418(3) . ?
O5 C57 1.260(3) . ?
C5 C6 1.401(4) . ?
C5 H5 0.9300 . ?
C9 C8 1.374(5) . ?
C9 C10 1.393(5) . ?
C9 H9 0.9300 . ?
O8 C75 1.291(3) . ?
O8 H8A 0.8200 . ?
C8 C7 1.396(4) . ?
C8 H8 0.9300 . ?
O7 C75 1.242(3) . ?
C7 C12 1.411(4) . ?
C7 C6 1.435(4) . ?
O6 C57 1.266(3) . ?
O6 H6 0.8200 . ?
C10 C11 1.382(4) . ?
C10 H10 0.9300 . ?
C12 C11 1.387(4) . ?
C11 H11 0.9300 . ?
C13 C18 1.386(3) . ?
C13 C14 1.386(3) . ?
C014 C68 1.396(4) . ?
C014 C64 1.405(4) . ?
C14 C15 1.382(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.389(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.388(3) . ?
C16 C19 1.473(3) . ?
C17 C18 1.374(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C21 C22 1.382(4) . ?
C21 C20 1.385(4) . ?
C21 H21 0.9300 . ?
C20 C25 1.404(3) . ?
C22 C23 1.387(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.365(4) . ?
C23 H23 0.9300 . ?
C26 C27 1.391(4) . ?
C26 C31 1.407(3) . ?
C26 C25 1.443(4) . ?
C25 C24 1.397(4) . ?
C24 H24 0.9300 . ?
C27 C28 1.378(4) . ?
C27 H27 0.9300 . ?
C29 C30 1.372(4) . ?
C29 C28 1.388(4) . ?
C29 H29 0.9300 . ?
C28 H28 0.9300 . ?
C30 C31 1.385(4) . ?
C30 H30 0.9300 . ?
C32 C37 1.380(4) . ?
C32 C33 1.387(3) . ?
C33 C34 1.380(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.386(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.386(3) . ?
C35 C38 1.479(3) . ?
C36 C37 1.372(3) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C39 C40 1.384(4) . ?
C39 C44 1.409(3) . ?
C40 C41 1.377(4) . ?
C40 H40 0.9300 . ?
C41 C42 1.394(4) . ?
C41 H41 0.9300 . ?
C42 C43 1.371(4) . ?
C42 H42 0.9300 . ?
C43 C44 1.393(3) . ?
C43 H43 0.9300 . ?
C44 C45 1.439(4) . ?
C45 C46 1.390(4) . ?
C45 C50 1.403(3) . ?
C46 C47 1.367(4) . ?
C46 H46 0.9300 . ?
C47 C48 1.387(4) . ?
C47 H47 0.9300 . ?
C48 C49 1.381(4) . ?
C48 H48 0.9300 . ?
C49 C50 1.386(4) . ?
C49 H49 0.9300 . ?
C51 C56 1.381(3) . ?
C51 C52 1.390(3) . ?
C52 C53 1.381(3) . ?
C52 H52 0.9300 . ?
C53 C54 1.393(3) . ?
C53 H53 0.9300 . ?
C54 C55 1.386(3) . ?
C54 C57 1.475(3) . ?
C55 C56 1.375(3) . ?
C55 H55 0.9300 . ?
C56 H56 0.9300 . ?
C58 C59 1.390(4) . ?
C58 C63 1.392(4) . ?
C59 C60 1.381(4) . ?
C59 H59 0.9300 . ?
C60 C61 1.379(5) . ?
C60 H60 0.9300 . ?
C61 C62 1.365(5) . ?
C61 H61 0.9300 . ?
C62 C63 1.397(4) . ?
C62 H62 0.9300 . ?
C63 C64 1.443(4) . ?
C64 C65 1.386(4) . ?
C65 C66 1.367(5) . ?
C65 H65 0.9300 . ?
C66 C67 1.386(5) . ?
C66 H66 0.9300 . ?
C67 C68 1.377(4) . ?
C67 H67 0.9300 . ?
C68 H68 0.9300 . ?
C69 C74 1.388(4) . ?
C69 C70 1.390(3) . ?
C70 C71 1.380(4) . ?
C70 H70 0.9300 . ?
C71 C72 1.386(4) . ?
C71 H71 0.9300 . ?
C72 C73 1.389(3) . ?
C72 C75 1.481(4) . ?
C73 C74 1.373(3) . ?
C73 H73 0.9300 . ?
C74 H74 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
C19 O1 H1 109.5 . . ?
C2 C1 C6 122.1(3) . . ?
C2 C1 N1 129.3(2) . . ?
C6 C1 N1 108.6(2) . . ?
C12 N1 C1 108.6(2) . . ?
C12 N1 C13 126.0(2) . . ?
C1 N1 C13 125.4(2) . . ?
C3 C2 C1 117.7(3) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C31 N2 C20 108.7(2) . . ?
C31 N2 C32 124.1(2) . . ?
C20 N2 C32 127.2(2) . . ?
C38 O3 H3A 109.5 . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C39 N3 C50 108.60(18) . . ?
C39 N3 C51 126.8(2) . . ?
C50 N3 C51 124.6(2) . . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C014 N4 C58 108.0(2) . . ?
C014 N4 C69 125.6(2) . . ?
C58 N4 C69 125.0(2) . . ?
C4 C5 C6 119.1(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C8 C9 C10 121.1(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C75 O8 H8A 109.5 . . ?
C9 C8 C7 119.6(3) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C7 C12 118.6(3) . . ?
C8 C7 C6 134.2(3) . . ?
C12 C7 C6 107.3(2) . . ?
C57 O6 H6 109.5 . . ?
C1 C6 C5 118.6(3) . . ?
C1 C6 C7 107.2(2) . . ?
C5 C6 C7 134.2(3) . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C11 C12 N1 129.8(2) . . ?
C11 C12 C7 121.8(3) . . ?
N1 C12 C7 108.3(2) . . ?
C10 C11 C12 118.1(3) . . ?
C10 C11 H11 121.0 . . ?
C12 C11 H11 121.0 . . ?
C18 C13 C14 120.0(2) . . ?
C18 C13 N1 120.2(2) . . ?
C14 C13 N1 119.7(2) . . ?
C68 C014 N4 130.5(3) . . ?
C68 C014 C64 120.9(3) . . ?
N4 C014 C64 108.6(2) . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 119.5(2) . . ?
C17 C16 C19 119.7(2) . . ?
C15 C16 C19 120.8(2) . . ?
C18 C17 C16 120.4(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C13 120.0(2) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
O2 C19 O1 122.8(2) . . ?
O2 C19 C16 119.1(2) . . ?
O1 C19 C16 118.0(2) . . ?
C22 C21 C20 117.4(3) . . ?
C22 C21 H21 121.3 . . ?
C20 C21 H21 121.3 . . ?
C21 C20 N2 129.8(2) . . ?
C21 C20 C25 121.6(2) . . ?
N2 C20 C25 108.6(2) . . ?
C21 C22 C23 121.7(3) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 H22 119.1 . . ?
C24 C23 C22 120.9(3) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C27 C26 C31 119.2(3) . . ?
C27 C26 C25 133.8(3) . . ?
C31 C26 C25 107.0(2) . . ?
C24 C25 C20 119.4(3) . . ?
C24 C25 C26 133.5(2) . . ?
C20 C25 C26 107.1(2) . . ?
C23 C24 C25 119.0(3) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
C28 C27 C26 119.0(3) . . ?
C28 C27 H27 120.5 . . ?
C26 C27 H27 120.5 . . ?
C30 C29 C28 121.5(3) . . ?
C30 C29 H29 119.3 . . ?
C28 C29 H29 119.3 . . ?
C27 C28 C29 120.9(3) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 H28 119.6 . . ?
C29 C30 C31 117.9(3) . . ?
C29 C30 H30 121.1 . . ?
C31 C30 H30 121.1 . . ?
C30 C31 N2 129.7(2) . . ?
C30 C31 C26 121.6(2) . . ?
N2 C31 C26 108.6(2) . . ?
C37 C32 C33 120.0(2) . . ?
C37 C32 N2 120.0(2) . . ?
C33 C32 N2 120.0(2) . . ?
C34 C33 C32 119.7(2) . . ?
C34 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
C33 C34 C35 120.4(2) . . ?
C33 C34 H34 119.8 . . ?
C35 C34 H34 119.8 . . ?
C34 C35 C36 119.2(2) . . ?
C34 C35 C38 120.9(2) . . ?
C36 C35 C38 119.9(2) . . ?
C37 C36 C35 120.6(3) . . ?
C37 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C36 C37 C32 120.0(2) . . ?
C36 C37 H37 120.0 . . ?
C32 C37 H37 120.0 . . ?
O4 C38 O3 122.9(2) . . ?
O4 C38 C35 120.7(2) . . ?
O3 C38 C35 116.3(2) . . ?
C40 C39 N3 129.9(2) . . ?
C40 C39 C44 121.7(2) . . ?
N3 C39 C44 108.3(2) . . ?
C41 C40 C39 117.9(2) . . ?
C41 C40 H40 121.0 . . ?
C39 C40 H40 121.0 . . ?
C40 C41 C42 121.3(3) . . ?
C40 C41 H41 119.3 . . ?
C42 C41 H41 119.3 . . ?
C43 C42 C41 120.5(2) . . ?
C43 C42 H42 119.7 . . ?
C41 C42 H42 119.7 . . ?
C42 C43 C44 119.7(2) . . ?
C42 C43 H43 120.2 . . ?
C44 C43 H43 120.2 . . ?
C43 C44 C39 118.8(2) . . ?
C43 C44 C45 133.8(2) . . ?
C39 C44 C45 107.3(2) . . ?
C46 C45 C50 119.4(2) . . ?
C46 C45 C44 133.7(2) . . ?
C50 C45 C44 106.9(2) . . ?
C47 C46 C45 119.1(2) . . ?
C47 C46 H46 120.5 . . ?
C45 C46 H46 120.5 . . ?
C46 C47 C48 121.2(3) . . ?
C46 C47 H47 119.4 . . ?
C48 C47 H47 119.4 . . ?
C49 C48 C47 121.2(3) . . ?
C49 C48 H48 119.4 . . ?
C47 C48 H48 119.4 . . ?
C48 C49 C50 117.7(2) . . ?
C48 C49 H49 121.2 . . ?
C50 C49 H49 121.2 . . ?
C49 C50 N3 129.6(2) . . ?
C49 C50 C45 121.5(2) . . ?
N3 C50 C45 108.8(2) . . ?
C56 C51 C52 120.2(2) . . ?
C56 C51 N3 119.3(2) . . ?
C52 C51 N3 120.5(2) . . ?
C53 C52 C51 119.5(2) . . ?
C53 C52 H52 120.2 . . ?
C51 C52 H52 120.2 . . ?
C52 C53 C54 120.2(2) . . ?
C52 C53 H53 119.9 . . ?
C54 C53 H53 119.9 . . ?
C55 C54 C53 119.6(2) . . ?
C55 C54 C57 119.9(2) . . ?
C53 C54 C57 120.4(2) . . ?
C56 C55 C54 120.2(2) . . ?
C56 C55 H55 119.9 . . ?
C54 C55 H55 119.9 . . ?
C55 C56 C51 120.2(2) . . ?
C55 C56 H56 119.9 . . ?
C51 C56 H56 119.9 . . ?
O5 C57 O6 122.8(2) . . ?
O5 C57 C54 119.4(2) . . ?
O6 C57 C54 117.8(2) . . ?
C59 C58 C63 121.9(3) . . ?
C59 C58 N4 129.3(3) . . ?
C63 C58 N4 108.8(3) . . ?
C60 C59 C58 117.2(3) . . ?
C60 C59 H59 121.4 . . ?
C58 C59 H59 121.4 . . ?
C61 C60 C59 121.7(4) . . ?
C61 C60 H60 119.1 . . ?
C59 C60 H60 119.1 . . ?
C62 C61 C60 120.9(3) . . ?
C62 C61 H61 119.6 . . ?
C60 C61 H61 119.6 . . ?
C61 C62 C63 119.3(3) . . ?
C61 C62 H62 120.4 . . ?
C63 C62 H62 120.4 . . ?
C58 C63 C62 119.1(3) . . ?
C58 C63 C64 107.4(2) . . ?
C62 C63 C64 133.3(3) . . ?
C65 C64 C014 119.7(3) . . ?
C65 C64 C63 133.2(3) . . ?
C014 C64 C63 107.1(2) . . ?
C66 C65 C64 119.3(3) . . ?
C66 C65 H65 120.4 . . ?
C64 C65 H65 120.4 . . ?
C65 C66 C67 121.0(3) . . ?
C65 C66 H66 119.5 . . ?
C67 C66 H66 119.5 . . ?
C68 C67 C66 121.3(4) . . ?
C68 C67 H67 119.3 . . ?
C66 C67 H67 119.3 . . ?
C67 C68 C014 117.8(3) . . ?
C67 C68 H68 121.1 . . ?
C014 C68 H68 121.1 . . ?
C74 C69 C70 119.6(2) . . ?
C74 C69 N4 119.5(2) . . ?
C70 C69 N4 120.9(2) . . ?
C71 C70 C69 119.8(2) . . ?
C71 C70 H70 120.1 . . ?
C69 C70 H70 120.1 . . ?
C70 C71 C72 120.5(2) . . ?
C70 C71 H71 119.7 . . ?
C72 C71 H71 119.7 . . ?
C71 C72 C73 119.3(2) . . ?
C71 C72 C75 121.6(2) . . ?
C73 C72 C75 119.1(2) . . ?
C74 C73 C72 120.5(2) . . ?
C74 C73 H73 119.8 . . ?
C72 C73 H73 119.8 . . ?
C73 C74 C69 120.2(2) . . ?
C73 C74 H74 119.9 . . ?
C69 C74 H74 119.9 . . ?
O7 C75 O8 123.6(2) . . ?
O7 C75 C72 120.1(2) . . ?
O8 C75 C72 116.3(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
C2 C1 N1 C12 177.7(3) . . . . ?
C6 C1 N1 C12 -0.7(3) . . . . ?
C2 C1 N1 C13 -1.7(4) . . . . ?
C6 C1 N1 C13 179.8(2) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
N1 C1 C2 C3 -179.1(3) . . . . ?
C1 C2 C3 C4 -0.8(5) . . . . ?
C2 C3 C4 C5 1.8(5) . . . . ?
C3 C4 C5 C6 -1.1(5) . . . . ?
C10 C9 C8 C7 0.1(5) . . . . ?
C9 C8 C7 C12 -0.6(4) . . . . ?
C9 C8 C7 C6 178.3(3) . . . . ?
C2 C1 C6 C5 1.5(4) . . . . ?
N1 C1 C6 C5 -179.9(2) . . . . ?
C2 C1 C6 C7 -178.0(2) . . . . ?
N1 C1 C6 C7 0.6(3) . . . . ?
C4 C5 C6 C1 -0.5(4) . . . . ?
C4 C5 C6 C7 178.8(3) . . . . ?
C8 C7 C6 C1 -179.3(3) . . . . ?
C12 C7 C6 C1 -0.2(3) . . . . ?
C8 C7 C6 C5 1.4(5) . . . . ?
C12 C7 C6 C5 -179.6(3) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
C1 N1 C12 C11 177.9(3) . . . . ?
C13 N1 C12 C11 -2.7(4) . . . . ?
C1 N1 C12 C7 0.6(3) . . . . ?
C13 N1 C12 C7 -180.0(2) . . . . ?
C8 C7 C12 C11 1.5(4) . . . . ?
C6 C7 C12 C11 -177.8(2) . . . . ?
C8 C7 C12 N1 179.0(2) . . . . ?
C6 C7 C12 N1 -0.2(3) . . . . ?
C9 C10 C11 C12 1.0(4) . . . . ?
N1 C12 C11 C10 -178.6(3) . . . . ?
C7 C12 C11 C10 -1.6(4) . . . . ?
C12 N1 C13 C18 -48.1(4) . . . . ?
C1 N1 C13 C18 131.2(3) . . . . ?
C12 N1 C13 C14 131.9(3) . . . . ?
C1 N1 C13 C14 -48.8(4) . . . . ?
C58 N4 C014 C68 -178.5(3) . . . . ?
C69 N4 C014 C68 -11.5(4) . . . . ?
C58 N4 C014 C64 -0.5(3) . . . . ?
C69 N4 C014 C64 166.5(2) . . . . ?
C18 C13 C14 C15 -1.6(4) . . . . ?
N1 C13 C14 C15 178.4(2) . . . . ?
C13 C14 C15 C16 1.1(4) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C14 C15 C16 C19 179.3(2) . . . . ?
C15 C16 C17 C18 -1.2(4) . . . . ?
C19 C16 C17 C18 179.9(2) . . . . ?
C16 C17 C18 C13 0.7(4) . . . . ?
C14 C13 C18 C17 0.7(4) . . . . ?
N1 C13 C18 C17 -179.3(2) . . . . ?
C17 C16 C19 O2 1.2(4) . . . . ?
C15 C16 C19 O2 -177.8(3) . . . . ?
C17 C16 C19 O1 -177.5(2) . . . . ?
C15 C16 C19 O1 3.5(4) . . . . ?
C22 C21 C20 N2 178.5(3) . . . . ?
C22 C21 C20 C25 -0.4(4) . . . . ?
C31 N2 C20 C21 -180.0(3) . . . . ?
C32 N2 C20 C21 2.4(5) . . . . ?
C31 N2 C20 C25 -1.0(3) . . . . ?
C32 N2 C20 C25 -178.6(2) . . . . ?
C20 C21 C22 C23 -0.9(5) . . . . ?
C21 C22 C23 C24 1.1(5) . . . . ?
C21 C20 C25 C24 1.5(4) . . . . ?
N2 C20 C25 C24 -177.6(2) . . . . ?
C21 C20 C25 C26 -179.3(2) . . . . ?
N2 C20 C25 C26 1.5(3) . . . . ?
C27 C26 C25 C24 -5.1(5) . . . . ?
C31 C26 C25 C24 177.5(3) . . . . ?
C27 C26 C25 C20 175.9(3) . . . . ?
C31 C26 C25 C20 -1.5(3) . . . . ?
C22 C23 C24 C25 0.0(5) . . . . ?
C20 C25 C24 C23 -1.2(4) . . . . ?
C26 C25 C24 C23 179.9(3) . . . . ?
C31 C26 C27 C28 -0.1(4) . . . . ?
C25 C26 C27 C28 -177.3(3) . . . . ?
C26 C27 C28 C29 -0.6(4) . . . . ?
C30 C29 C28 C27 0.8(5) . . . . ?
C28 C29 C30 C31 -0.3(5) . . . . ?
C29 C30 C31 N2 176.6(3) . . . . ?
C29 C30 C31 C26 -0.4(4) . . . . ?
C20 N2 C31 C30 -177.2(3) . . . . ?
C32 N2 C31 C30 0.5(4) . . . . ?
C20 N2 C31 C26 0.0(3) . . . . ?
C32 N2 C31 C26 177.7(2) . . . . ?
C27 C26 C31 C30 0.6(4) . . . . ?
C25 C26 C31 C30 178.5(2) . . . . ?
C27 C26 C31 N2 -176.9(2) . . . . ?
C25 C26 C31 N2 0.9(3) . . . . ?
C31 N2 C32 C37 54.7(4) . . . . ?
C20 N2 C32 C37 -128.1(3) . . . . ?
C31 N2 C32 C33 -122.7(3) . . . . ?
C20 N2 C32 C33 54.5(4) . . . . ?
C37 C32 C33 C34 -2.0(4) . . . . ?
N2 C32 C33 C34 175.4(2) . . . . ?
C32 C33 C34 C35 -0.1(4) . . . . ?
C33 C34 C35 C36 1.8(4) . . . . ?
C33 C34 C35 C38 -175.6(2) . . . . ?
C34 C35 C36 C37 -1.4(4) . . . . ?
C38 C35 C36 C37 175.9(2) . . . . ?
C35 C36 C37 C32 -0.6(4) . . . . ?
C33 C32 C37 C36 2.3(4) . . . . ?
N2 C32 C37 C36 -175.1(2) . . . . ?
C34 C35 C38 O4 175.1(3) . . . . ?
C36 C35 C38 O4 -2.2(4) . . . . ?
C34 C35 C38 O3 -3.4(4) . . . . ?
C36 C35 C38 O3 179.3(3) . . . . ?
C50 N3 C39 C40 -176.1(3) . . . . ?
C51 N3 C39 C40 3.1(4) . . . . ?
C50 N3 C39 C44 0.4(3) . . . . ?
C51 N3 C39 C44 179.7(2) . . . . ?
N3 C39 C40 C41 176.0(2) . . . . ?
C44 C39 C40 C41 -0.2(4) . . . . ?
C39 C40 C41 C42 0.6(4) . . . . ?
C40 C41 C42 C43 0.0(4) . . . . ?
C41 C42 C43 C44 -0.9(4) . . . . ?
C42 C43 C44 C39 1.3(4) . . . . ?
C42 C43 C44 C45 -175.9(3) . . . . ?
C40 C39 C44 C43 -0.7(4) . . . . ?
N3 C39 C44 C43 -177.7(2) . . . . ?
C40 C39 C44 C45 177.1(2) . . . . ?
N3 C39 C44 C45 0.2(3) . . . . ?
C43 C44 C45 C46 -4.7(5) . . . . ?
C39 C44 C45 C46 177.9(3) . . . . ?
C43 C44 C45 C50 176.6(3) . . . . ?
C39 C44 C45 C50 -0.8(3) . . . . ?
C50 C45 C46 C47 -1.1(4) . . . . ?
C44 C45 C46 C47 -179.7(3) . . . . ?
C45 C46 C47 C48 1.5(5) . . . . ?
C46 C47 C48 C49 -0.9(5) . . . . ?
C47 C48 C49 C50 0.0(5) . . . . ?
C48 C49 C50 N3 178.0(3) . . . . ?
C48 C49 C50 C45 0.4(4) . . . . ?
C39 N3 C50 C49 -178.8(3) . . . . ?
C51 N3 C50 C49 1.9(4) . . . . ?
C39 N3 C50 C45 -0.9(3) . . . . ?
C51 N3 C50 C45 179.8(2) . . . . ?
C46 C45 C50 C49 0.2(4) . . . . ?
C44 C45 C50 C49 179.1(2) . . . . ?
C46 C45 C50 N3 -177.8(2) . . . . ?
C44 C45 C50 N3 1.1(3) . . . . ?
C39 N3 C51 C56 -128.6(3) . . . . ?
C50 N3 C51 C56 50.6(4) . . . . ?
C39 N3 C51 C52 53.4(4) . . . . ?
C50 N3 C51 C52 -127.4(3) . . . . ?
C56 C51 C52 C53 -0.7(4) . . . . ?
N3 C51 C52 C53 177.2(2) . . . . ?
C51 C52 C53 C54 -0.8(4) . . . . ?
C52 C53 C54 C55 1.6(4) . . . . ?
C52 C53 C54 C57 -176.7(3) . . . . ?
C53 C54 C55 C56 -0.9(4) . . . . ?
C57 C54 C55 C56 177.4(2) . . . . ?
C54 C55 C56 C51 -0.6(4) . . . . ?
C52 C51 C56 C55 1.4(4) . . . . ?
N3 C51 C56 C55 -176.5(2) . . . . ?
C55 C54 C57 O5 -175.7(3) . . . . ?
C53 C54 C57 O5 2.6(4) . . . . ?
C55 C54 C57 O6 3.1(4) . . . . ?
C53 C54 C57 O6 -178.6(3) . . . . ?
C014 N4 C58 C59 -175.8(3) . . . . ?
C69 N4 C58 C59 17.0(4) . . . . ?
C014 N4 C58 C63 1.2(3) . . . . ?
C69 N4 C58 C63 -165.9(2) . . . . ?
C63 C58 C59 C60 0.5(4) . . . . ?
N4 C58 C59 C60 177.2(3) . . . . ?
C58 C59 C60 C61 0.8(5) . . . . ?
C59 C60 C61 C62 -1.6(6) . . . . ?
C60 C61 C62 C63 1.2(5) . . . . ?
C59 C58 C63 C62 -0.9(4) . . . . ?
N4 C58 C63 C62 -178.2(3) . . . . ?
C59 C58 C63 C64 175.9(3) . . . . ?
N4 C58 C63 C64 -1.4(3) . . . . ?
C61 C62 C63 C58 0.1(5) . . . . ?
C61 C62 C63 C64 -175.8(3) . . . . ?
C68 C014 C64 C65 -0.5(4) . . . . ?
N4 C014 C64 C65 -178.7(3) . . . . ?
C68 C014 C64 C63 177.9(3) . . . . ?
N4 C014 C64 C63 -0.4(3) . . . . ?
C58 C63 C64 C65 179.2(3) . . . . ?
C62 C63 C64 C65 -4.6(6) . . . . ?
C58 C63 C64 C014 1.1(3) . . . . ?
C62 C63 C64 C014 177.3(3) . . . . ?
C014 C64 C65 C66 -0.8(5) . . . . ?
C63 C64 C65 C66 -178.7(3) . . . . ?
C64 C65 C66 C67 1.8(6) . . . . ?
C65 C66 C67 C68 -1.5(5) . . . . ?
C66 C67 C68 C014 0.2(5) . . . . ?
N4 C014 C68 C67 178.6(3) . . . . ?
C64 C014 C68 C67 0.8(4) . . . . ?
C014 N4 C69 C74 -128.7(3) . . . . ?
C58 N4 C69 C74 36.2(4) . . . . ?
C014 N4 C69 C70 51.3(4) . . . . ?
C58 N4 C69 C70 -143.8(3) . . . . ?
C74 C69 C70 C71 0.5(4) . . . . ?
N4 C69 C70 C71 -179.6(2) . . . . ?
C69 C70 C71 C72 -2.3(4) . . . . ?
C70 C71 C72 C73 1.8(4) . . . . ?
C70 C71 C72 C75 -176.0(2) . . . . ?
C71 C72 C73 C74 0.6(4) . . . . ?
C75 C72 C73 C74 178.5(2) . . . . ?
C72 C73 C74 C69 -2.5(4) . . . . ?
C70 C69 C74 C73 1.9(4) . . . . ?
N4 C69 C74 C73 -178.0(2) . . . . ?
C71 C72 C75 O7 158.0(3) . . . . ?
C73 C72 C75 O7 -19.8(4) . . . . ?
C71 C72 C75 O8 -20.4(4) . . . . ?
C73 C72 C75 O8 161.8(2) . . . . ?

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.213
_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_t_a
_database_code_depnum_ccdc_archive 'CCDC 1915585'
loop_
_audit_author_name
_audit_author_address
'Tingting Zhang'
;Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2019-05-13 deposited with the CCDC.	2019-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H13 N O2'
_chemical_formula_sum            'C19 H13 N O2'
_chemical_formula_weight         287.30

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   4.02120(10)
_cell_length_b                   18.6170(4)
_cell_length_c                   20.8228(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.2040(10)
_cell_angle_gamma                90
_cell_volume                     1554.66(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5203
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      68.11

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   0.6635
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.643
_shelx_estimated_absorpt_T_min   0.893
_shelx_estimated_absorpt_T_max   0.893
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_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            11353
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.188
_diffrn_reflns_theta_max         68.395
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2812
_reflns_number_gt                2288
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.2000P)²] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.031(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2812
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0806
_refine_ls_wR_factor_ref         0.2635
_refine_ls_wR_factor_gt          0.2422
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_restrained_S_all      1.132
_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 0.6599(5) 0.26376(10) 0.68613(9) 0.0533(6) Uani 1 1 d . . . . .
O1 O 0.1990(7) 0.06807(12) 0.46665(9) 0.0806(7) Uani 1 1 d . . . . .
O2 O 0.1382(6) 0.04847(11) 0.57057(9) 0.0754(7) Uani 1 1 d . . . . .
H2A H 0.034730 0.013531 0.555771 0.113 Uiso 1 1 calc R U . . .
C1 C 0.8153(6) 0.22400(13) 0.73659(11) 0.0526(6) Uani 1 1 d . . . . .
C2 C 0.9347(6) 0.15384(14) 0.73737(12) 0.0589(7) Uani 1 1 d . . . . .
H2 H 0.910670 0.124842 0.700959 0.071 Uiso 1 1 calc R U . . .
C3 C 1.0913(7) 0.12884(18) 0.79473(14) 0.0702(8) Uani 1 1 d . . . . .
H3 H 1.174248 0.082199 0.796717 0.084 Uiso 1 1 calc R U . . .
C4 C 1.1269(8) 0.1723(2) 0.84954(14) 0.0800(9) Uani 1 1 d . . . . .
H4 H 1.233112 0.154263 0.887311 0.096 Uiso 1 1 calc R U . . .
C5 C 1.0079(8) 0.2408(2) 0.84829(13) 0.0728(8) Uani 1 1 d . . . . .
H5 H 1.031879 0.269275 0.885004 0.087 Uiso 1 1 calc R U . . .
C6 C 0.8497(6) 0.26783(14) 0.79146(11) 0.0575(7) Uani 1 1 d . . . . .
C7 C 0.7040(6) 0.33647(15) 0.77430(12) 0.0599(7) Uani 1 1 d . . . . .
C8 C 0.6544(9) 0.39999(18) 0.80852(15) 0.0785(9) Uani 1 1 d . . . . .
H8 H 0.726685 0.403589 0.851855 0.094 Uiso 1 1 calc R U . . .
C9 C 0.4976(10) 0.45676(18) 0.7771(2) 0.0879(11) Uani 1 1 d . . . . .
H9 H 0.464891 0.499216 0.799280 0.105 Uiso 1 1 calc R U . . .
C10 C 0.3875(8) 0.45162(17) 0.7127(2) 0.0827(10) Uani 1 1 d . . . . .
H10 H 0.281528 0.490846 0.692544 0.099 Uiso 1 1 calc R U . . .
C11 C 0.4307(7) 0.38960(15) 0.67750(15) 0.0670(7) Uani 1 1 d . . . . .
H11 H 0.354829 0.386493 0.634310 0.080 Uiso 1 1 calc R U . . .
C12 C 0.5905(6) 0.33265(13) 0.70885(12) 0.0545(6) Uani 1 1 d . . . . .
C13 C 0.6109(6) 0.24086(12) 0.62101(11) 0.0505(6) Uani 1 1 d . . . . .
C14 C 0.4593(6) 0.17607(13) 0.60559(11) 0.0508(6) Uani 1 1 d . . . . .
H14 H 0.385920 0.146918 0.637952 0.061 Uiso 1 1 calc R U . . .
C15 C 0.4161(6) 0.15424(13) 0.54145(11) 0.0533(6) Uani 1 1 d . . . . .
C16 C 0.5264(7) 0.19793(15) 0.49318(11) 0.0600(7) Uani 1 1 d . . . . .
H16 H 0.500550 0.183108 0.450449 0.072 Uiso 1 1 calc R U . . .
C17 C 0.6740(7) 0.26313(15) 0.50851(12) 0.0625(7) Uani 1 1 d . . . . .
H17 H 0.743789 0.292646 0.476069 0.075 Uiso 1 1 calc R U . . .
C18 C 0.7181(6) 0.28463(14) 0.57205(12) 0.0586(6) Uani 1 1 d . . . . .
H18 H 0.819633 0.328442 0.582302 0.070 Uiso 1 1 calc R U . . .
C19 C 0.2421(6) 0.08612(14) 0.52417(11) 0.0574(6) 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 C1 1.395(3) . ?
N1 C12 1.402(3) . ?
N1 C13 1.421(3) . ?
O1 C19 1.244(3) . ?
O2 C19 1.288(3) . ?
O2 H2A 0.8200 . ?
C1 C2 1.391(4) . ?
C1 C6 1.403(3) . ?
C2 C3 1.389(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.398(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.360(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.440(4) . ?
C7 C8 1.402(4) . ?
C7 C12 1.407(4) . ?
C8 C9 1.372(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.383(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.386(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(4) . ?
C11 H11 0.9300 . ?
C13 C14 1.379(3) . ?
C13 C18 1.398(3) . ?
C14 C15 1.395(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(4) . ?
C15 C19 1.480(3) . ?
C16 C17 1.378(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.381(4) . ?
C17 H17 0.9300 . ?
C18 H18 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
C1 N1 C12 108.70(19) . . ?
C1 N1 C13 125.6(2) . . ?
C12 N1 C13 125.4(2) . . ?
C19 O2 H2A 109.5 . . ?
C2 C1 N1 130.0(2) . . ?
C2 C1 C6 121.6(2) . . ?
N1 C1 C6 108.5(2) . . ?
C3 C2 C1 117.3(3) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 C7 133.1(3) . . ?
C1 C6 C7 107.5(2) . . ?
C8 C7 C12 119.1(3) . . ?
C8 C7 C6 133.8(3) . . ?
C12 C7 C6 107.0(2) . . ?
C9 C8 C7 119.0(3) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 120.8(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C11 121.8(3) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C12 C11 C10 117.5(3) . . ?
C12 C11 H11 121.2 . . ?
C10 C11 H11 121.2 . . ?
C11 C12 N1 129.9(2) . . ?
C11 C12 C7 121.8(2) . . ?
N1 C12 C7 108.3(2) . . ?
C14 C13 C18 119.7(2) . . ?
C14 C13 N1 120.8(2) . . ?
C18 C13 N1 119.5(2) . . ?
C13 C14 C15 120.0(2) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 C19 119.7(2) . . ?
C14 C15 C19 120.4(2) . . ?
C17 C16 C15 120.1(2) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C13 120.3(2) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
O1 C19 O2 123.0(2) . . ?
O1 C19 C15 119.7(2) . . ?
O2 C19 C15 117.2(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
C12 N1 C1 C2 -179.0(2) . . . . ?
C13 N1 C1 C2 -4.9(4) . . . . ?
C12 N1 C1 C6 -0.8(3) . . . . ?
C13 N1 C1 C6 173.3(2) . . . . ?
N1 C1 C2 C3 177.6(2) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C4 C5 C6 C7 -179.0(3) . . . . ?
C2 C1 C6 C5 0.2(4) . . . . ?
N1 C1 C6 C5 -178.2(2) . . . . ?
C2 C1 C6 C7 179.5(2) . . . . ?
N1 C1 C6 C7 1.2(3) . . . . ?
C5 C6 C7 C8 -3.2(5) . . . . ?
C1 C6 C7 C8 177.6(3) . . . . ?
C5 C6 C7 C12 178.1(3) . . . . ?
C1 C6 C7 C12 -1.1(3) . . . . ?
C12 C7 C8 C9 -0.2(4) . . . . ?
C6 C7 C8 C9 -178.8(3) . . . . ?
C7 C8 C9 C10 0.4(5) . . . . ?
C8 C9 C10 C11 -0.1(5) . . . . ?
C9 C10 C11 C12 -0.4(5) . . . . ?
C10 C11 C12 N1 178.2(2) . . . . ?
C10 C11 C12 C7 0.5(4) . . . . ?
C1 N1 C12 C11 -177.7(3) . . . . ?
C13 N1 C12 C11 8.2(4) . . . . ?
C1 N1 C12 C7 0.1(3) . . . . ?
C13 N1 C12 C7 -174.0(2) . . . . ?
C8 C7 C12 C11 -0.2(4) . . . . ?
C6 C7 C12 C11 178.7(2) . . . . ?
C8 C7 C12 N1 -178.3(2) . . . . ?
C6 C7 C12 N1 0.6(3) . . . . ?
C1 N1 C13 C14 52.9(3) . . . . ?
C12 N1 C13 C14 -134.0(2) . . . . ?
C1 N1 C13 C18 -127.1(3) . . . . ?
C12 N1 C13 C18 46.0(3) . . . . ?
C18 C13 C14 C15 0.5(4) . . . . ?
N1 C13 C14 C15 -179.4(2) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
C13 C14 C15 C19 -177.6(2) . . . . ?
C14 C15 C16 C17 -0.9(4) . . . . ?
C19 C15 C16 C17 176.8(2) . . . . ?
C15 C16 C17 C18 1.2(4) . . . . ?
C16 C17 C18 C13 -0.6(4) . . . . ?
C14 C13 C18 C17 -0.2(4) . . . . ?
N1 C13 C18 C17 179.7(2) . . . . ?
C16 C15 C19 O1 0.8(4) . . . . ?
C14 C15 C19 O1 178.5(2) . . . . ?
C16 C15 C19 O2 -178.4(2) . . . . ?
C14 C15 C19 O2 -0.7(4) . . . . ?

_refine_diff_density_max         1.242
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.152

