# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

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

data_shelxl
_audit_block_doi                 10.5517/cc1271zb
_database_code_depnum_ccdc_archive 'CCDC 989891'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/cg401532j 2014
_audit_update_record             
;
2014-03-04 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 N2 O2'
_chemical_formula_sum            'C15 H16 N2 O2'
_chemical_formula_weight         256.30

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_space_group_name_Hall           '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.9920(1)
_cell_length_b                   11.1848(2)
_cell_length_c                   13.2362(2)
_cell_angle_alpha                107.4105(6)
_cell_angle_beta                 94.4240(6)
_cell_angle_gamma                115.7150(7)
_cell_volume                     1357.82(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    6182
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9432
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 18
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12360
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0619
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         27.50
_reflns_number_total             6242
_reflns_number_gt                4294
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'COLLECT (Nonius, 1997)'
_computing_cell_refinement       'DENZO-SMN (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Nonius, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Bruker, 1995)'
_computing_publication_material  'SHELX-97 and local procedures'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0673P)²+0.0633P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6242
_refine_ls_number_parameters     347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1137
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1B N 0.65122(12) -0.00103(13) 0.33342(10) 0.0194(3) Uani 1 1 d . . .
N1A N 0.86530(12) 0.48778(13) 0.16105(10) 0.0208(3) Uani 1 1 d . . .
C2A C 0.74470(14) 0.41065(14) 0.08283(12) 0.0172(3) Uani 1 1 d . . .
C2B C 0.70990(14) 0.10426(15) 0.43344(12) 0.0174(3) Uani 1 1 d . . .
C3A C 0.73642(14) 0.31564(15) -0.01940(12) 0.0175(3) Uani 1 1 d . . .
C3B C 0.84500(14) 0.14362(15) 0.49106(12) 0.0184(3) Uani 1 1 d . . .
C4B C 0.92000(15) 0.08487(15) 0.43711(12) 0.0217(3) Uani 1 1 d . . .
H4B H 1.0128 0.1152 0.4721 0.026 Uiso 1 1 calc R . .
C4A C 0.84827(15) 0.29076(16) -0.03419(13) 0.0237(4) Uani 1 1 d . . .
H4A H 0.8427 0.2237 -0.1010 0.028 Uiso 1 1 calc R . .
C5A C 0.96831(16) 0.36466(17) 0.04937(13) 0.0272(4) Uani 1 1 d . . .
H5A H 1.0448 0.3468 0.0422 0.033 Uiso 1 1 calc R . .
C5B C 0.86179(16) -0.01795(16) 0.33235(13) 0.0259(4) Uani 1 1 d . . .
H5B H 0.9134 -0.0574 0.2939 0.031 Uiso 1 1 calc R . .
C6A C 0.97299(15) 0.46440(17) 0.14271(13) 0.0252(4) Uani 1 1 d . . .
H6A H 1.0576 0.5202 0.1976 0.030 Uiso 1 1 calc R . .
C6B C 0.72628(15) -0.06015(16) 0.28671(13) 0.0240(3) Uani 1 1 d . . .
H6B H 0.6827 -0.1361 0.2176 0.029 Uiso 1 1 calc R . .
N7B N 0.63493(12) 0.16894(12) 0.47715(10) 0.0177(3) Uani 1 1 d . . .
N7A N 0.63310(12) 0.43023(12) 0.10653(9) 0.0173(3) Uani 1 1 d . . .
C8B C 0.70378(14) 0.31661(15) 0.54751(12) 0.0183(3) Uani 1 1 d . . .
C8A C 0.49418(14) 0.31297(15) 0.06420(11) 0.0177(3) Uani 1 1 d . . .
C9B C 0.80669(15) 0.41901(15) 0.51889(12) 0.0211(3) Uani 1 1 d . . .
H9B H 0.8350 0.3907 0.4538 0.025 Uiso 1 1 calc R . .
C9A C 0.46651(15) 0.17740(15) 0.05905(12) 0.0221(3) Uani 1 1 d . . .
H9A H 0.5402 0.1618 0.0829 0.027 Uiso 1 1 calc R . .
C10B C 0.86799(16) 0.56241(16) 0.58532(13) 0.0258(4) Uani 1 1 d . . .
H10B H 0.9390 0.6320 0.5660 0.031 Uiso 1 1 calc R . .
C10A C 0.33160(17) 0.06462(17) 0.01915(13) 0.0286(4) Uani 1 1 d . . .
H10A H 0.3136 -0.0281 0.0149 0.034 Uiso 1 1 calc R . .
C11B C 0.82606(16) 0.60438(16) 0.67951(13) 0.0259(4) Uani 1 1 d . . .
H11B H 0.8676 0.7027 0.7245 0.031 Uiso 1 1 calc R . .
C11A C 0.22350(16) 0.08636(17) -0.01429(13) 0.0305(4) Uani 1 1 d . . .
H11A H 0.1312 0.0091 -0.0417 0.037 Uiso 1 1 calc R . .
C12B C 0.72355(15) 0.50309(16) 0.70815(12) 0.0244(4) Uani 1 1 d . . .
H12B H 0.6944 0.5320 0.7726 0.029 Uiso 1 1 calc R . .
C12A C 0.25073(15) 0.22203(17) -0.00753(13) 0.0266(4) Uani 1 1 d . . .
H12A H 0.1762 0.2374 -0.0299 0.032 Uiso 1 1 calc R . .
C13A C 0.38505(15) 0.33573(16) 0.03135(12) 0.0214(3) Uani 1 1 d . . .
H13A H 0.4025 0.4283 0.0356 0.026 Uiso 1 1 calc R . .
C13B C 0.66303(15) 0.35906(16) 0.64297(12) 0.0207(3) Uani 1 1 d . . .
H13B H 0.5939 0.2896 0.6636 0.025 Uiso 1 1 calc R . .
C14A C 0.61842(14) 0.25190(15) -0.11588(12) 0.0177(3) Uani 1 1 d . . .
C14B C 0.90294(15) 0.23334(15) 0.60978(12) 0.0199(3) Uani 1 1 d . . .
O15B O 0.83698(10) 0.21745(11) 0.67838(8) 0.0253(3) Uani 1 1 d . . .
O15A O 0.56763(10) 0.31984(10) -0.14043(8) 0.0217(2) Uani 1 1 d . . .
O16A O 0.57921(10) 0.11620(10) -0.17302(8) 0.0220(2) Uani 1 1 d . . .
H16A H 0.5096 0.0832 -0.2242 0.033 Uiso 1 1 calc R . .
O16B O 1.03689(10) 0.32787(11) 0.63102(8) 0.0252(3) Uani 1 1 d . . .
H16B H 1.0656 0.3790 0.6978 0.038 Uiso 1 1 calc R . .
C17B C 0.48543(14) 0.10856(15) 0.42943(12) 0.0191(3) Uani 1 1 d . . .
H17A H 0.4381 0.1225 0.4892 0.023 Uiso 1 1 calc R . .
H17B H 0.4452 0.0045 0.3892 0.023 Uiso 1 1 calc R . .
C17A C 0.65284(15) 0.54932(15) 0.20472(12) 0.0201(3) Uani 1 1 d . . .
H17C H 0.5867 0.5834 0.1891 0.024 Uiso 1 1 calc R . .
H17D H 0.7482 0.6294 0.2218 0.024 Uiso 1 1 calc R . .
C18B C 0.45679(15) 0.17556(16) 0.35223(12) 0.0230(3) Uani 1 1 d . . .
H18A H 0.5005 0.1581 0.2906 0.028 Uiso 1 1 calc R . .
H18B H 0.4999 0.2802 0.3914 0.028 Uiso 1 1 calc R . .
C18A C 0.63100(15) 0.50766(16) 0.30366(12) 0.0229(3) Uani 1 1 d . . .
H18C H 0.6946 0.4701 0.3177 0.027 Uiso 1 1 calc R . .
H18D H 0.5344 0.4303 0.2878 0.027 Uiso 1 1 calc R . .
C19B C 0.30165(16) 0.11544(17) 0.30775(13) 0.0284(4) Uani 1 1 d . . .
H19A H 0.2593 0.0126 0.2661 0.043 Uiso 1 1 calc R . .
H19B H 0.2879 0.1629 0.2600 0.043 Uiso 1 1 calc R . .
H19C H 0.2579 0.1321 0.3685 0.043 Uiso 1 1 calc R . .
C19A C 0.65698(16) 0.63249(18) 0.40538(13) 0.0303(4) Uani 1 1 d . . .
H19D H 0.7548 0.7058 0.4253 0.045 Uiso 1 1 calc R . .
H19E H 0.6353 0.5990 0.4655 0.045 Uiso 1 1 calc R . .
H19F H 0.5975 0.6730 0.3908 0.045 Uiso 1 1 calc R . .


_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
N1B C6B 1.3446(19) . ?
N1B C2B 1.3534(18) . ?
N1A C6A 1.3429(19) . ?
N1A C2A 1.3546(18) . ?
C2A N7A 1.3792(18) . ?
C2A C3A 1.416(2) . ?
C2B N7B 1.3703(18) . ?
C2B C3B 1.4274(19) . ?
C3A C4A 1.389(2) . ?
C3A C14A 1.4895(19) . ?
C3B C4B 1.379(2) . ?
C3B C14B 1.493(2) . ?
C4B C5B 1.388(2) . ?
C4B H4B 0.9500 . ?
C4A C5A 1.389(2) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.375(2) . ?
C5A H5A 0.9500 . ?
C5B C6B 1.374(2) . ?
C5B H5B 0.9500 . ?
C6A H6A 0.9500 . ?
C6B H6B 0.9500 . ?
N7B C8B 1.4332(18) . ?
N7B C17B 1.4755(17) . ?
N7A C8A 1.4340(17) . ?
N7A C17A 1.4766(18) . ?
C8B C13B 1.391(2) . ?
C8B C9B 1.391(2) . ?
C8A C9A 1.390(2) . ?
C8A C13A 1.3940(19) . ?
C9B C10B 1.388(2) . ?
C9B H9B 0.9500 . ?
C9A C10A 1.388(2) . ?
C9A H9A 0.9500 . ?
C10B C11B 1.383(2) . ?
C10B H10B 0.9500 . ?
C10A C11A 1.379(2) . ?
C10A H10A 0.9500 . ?
C11B C12B 1.383(2) . ?
C11B H11B 0.9500 . ?
C11A C12A 1.386(2) . ?
C11A H11A 0.9500 . ?
C12B C13B 1.390(2) . ?
C12B H12B 0.9500 . ?
C12A C13A 1.387(2) . ?
C12A H12A 0.9500 . ?
C13A H13A 0.9500 . ?
C13B H13B 0.9500 . ?
C14A O15A 1.2176(16) . ?
C14A O16A 1.3254(16) . ?
C14B O15B 1.2116(17) . ?
C14B O16B 1.3312(17) . ?
O16A H16A 0.8400 . ?
O16B H16B 0.8400 . ?
C17B C18B 1.523(2) . ?
C17B H17A 0.9900 . ?
C17B H17B 0.9900 . ?
C17A C18A 1.519(2) . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C18B C19B 1.523(2) . ?
C18B H18A 0.9900 . ?
C18B H18B 0.9900 . ?
C18A C19A 1.521(2) . ?
C18A H18C 0.9900 . ?
C18A H18D 0.9900 . ?
C19B H19A 0.9800 . ?
C19B H19B 0.9800 . ?
C19B H19C 0.9800 . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 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
C6B N1B C2B 118.75(13) . . ?
C6A N1A C2A 118.70(13) . . ?
N1A C2A N7A 117.48(13) . . ?
N1A C2A C3A 120.34(13) . . ?
N7A C2A C3A 122.17(12) . . ?
N1B C2B N7B 117.97(12) . . ?
N1B C2B C3B 120.19(13) . . ?
N7B C2B C3B 121.84(13) . . ?
C4A C3A C2A 119.11(13) . . ?
C4A C3A C14A 117.95(13) . . ?
C2A C3A C14A 122.66(12) . . ?
C4B C3B C2B 118.32(13) . . ?
C4B C3B C14B 118.27(13) . . ?
C2B C3B C14B 123.11(13) . . ?
C3B C4B C5B 120.87(14) . . ?
C3B C4B H4B 119.6 . . ?
C5B C4B H4B 119.6 . . ?
C3A C4A C5A 119.50(15) . . ?
C3A C4A H4A 120.3 . . ?
C5A C4A H4A 120.3 . . ?
C6A C5A C4A 117.94(14) . . ?
C6A C5A H5A 121.0 . . ?
C4A C5A H5A 121.0 . . ?
C6B C5B C4B 117.04(14) . . ?
C6B C5B H5B 121.5 . . ?
C4B C5B H5B 121.5 . . ?
N1A C6A C5A 123.99(14) . . ?
N1A C6A H6A 118.0 . . ?
C5A C6A H6A 118.0 . . ?
N1B C6B C5B 124.32(14) . . ?
N1B C6B H6B 117.8 . . ?
C5B C6B H6B 117.8 . . ?
C2B N7B C8B 120.64(11) . . ?
C2B N7B C17B 121.67(12) . . ?
C8B N7B C17B 114.97(11) . . ?
C2A N7A C8A 120.41(12) . . ?
C2A N7A C17A 120.36(11) . . ?
C8A N7A C17A 115.29(11) . . ?
C13B C8B C9B 119.55(14) . . ?
C13B C8B N7B 119.72(13) . . ?
C9B C8B N7B 120.66(13) . . ?
C9A C8A C13A 119.56(13) . . ?
C9A C8A N7A 120.50(13) . . ?
C13A C8A N7A 119.90(13) . . ?
C10B C9B C8B 120.06(14) . . ?
C10B C9B H9B 120.0 . . ?
C8B C9B H9B 120.0 . . ?
C10A C9A C8A 120.26(14) . . ?
C10A C9A H9A 119.9 . . ?
C8A C9A H9A 119.9 . . ?
C11B C10B C9B 120.24(14) . . ?
C11B C10B H10B 119.9 . . ?
C9B C10B H10B 119.9 . . ?
C11A C10A C9A 120.37(15) . . ?
C11A C10A H10A 119.8 . . ?
C9A C10A H10A 119.8 . . ?
C12B C11B C10B 119.93(15) . . ?
C12B C11B H11B 120.0 . . ?
C10B C11B H11B 120.0 . . ?
C10A C11A C12A 119.38(15) . . ?
C10A C11A H11A 120.3 . . ?
C12A C11A H11A 120.3 . . ?
C11B C12B C13B 120.24(14) . . ?
C11B C12B H12B 119.9 . . ?
C13B C12B H12B 119.9 . . ?
C11A C12A C13A 121.02(15) . . ?
C11A C12A H12A 119.5 . . ?
C13A C12A H12A 119.5 . . ?
C12A C13A C8A 119.39(14) . . ?
C12A C13A H13A 120.3 . . ?
C8A C13A H13A 120.3 . . ?
C12B C13B C8B 119.98(14) . . ?
C12B C13B H13B 120.0 . . ?
C8B C13B H13B 120.0 . . ?
O15A C14A O16A 124.39(13) . . ?
O15A C14A C3A 122.93(13) . . ?
O16A C14A C3A 112.64(12) . . ?
O15B C14B O16B 124.50(14) . . ?
O15B C14B C3B 123.78(13) . . ?
O16B C14B C3B 111.66(12) . . ?
C14A O16A H16A 109.5 . . ?
C14B O16B H16B 109.5 . . ?
N7B C17B C18B 113.31(12) . . ?
N7B C17B H17A 108.9 . . ?
C18B C17B H17A 108.9 . . ?
N7B C17B H17B 108.9 . . ?
C18B C17B H17B 108.9 . . ?
H17A C17B H17B 107.7 . . ?
N7A C17A C18A 112.92(12) . . ?
N7A C17A H17C 109.0 . . ?
C18A C17A H17C 109.0 . . ?
N7A C17A H17D 109.0 . . ?
C18A C17A H17D 109.0 . . ?
H17C C17A H17D 107.8 . . ?
C17B C18B C19B 112.17(13) . . ?
C17B C18B H18A 109.2 . . ?
C19B C18B H18A 109.2 . . ?
C17B C18B H18B 109.2 . . ?
C19B C18B H18B 109.2 . . ?
H18A C18B H18B 107.9 . . ?
C17A C18A C19A 112.49(13) . . ?
C17A C18A H18C 109.1 . . ?
C19A C18A H18C 109.1 . . ?
C17A C18A H18D 109.1 . . ?
C19A C18A H18D 109.1 . . ?
H18C C18A H18D 107.8 . . ?
C18B C19B H19A 109.5 . . ?
C18B C19B H19B 109.5 . . ?
H19A C19B H19B 109.5 . . ?
C18B C19B H19C 109.5 . . ?
H19A C19B H19C 109.5 . . ?
H19B C19B H19C 109.5 . . ?
C18A C19A H19D 109.5 . . ?
C18A C19A H19E 109.5 . . ?
H19D C19A H19E 109.5 . . ?
C18A C19A H19F 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 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
C6A N1A C2A N7A 175.95(12) . . . . ?
C6A N1A C2A C3A -4.9(2) . . . . ?
C6B N1B C2B N7B 176.32(12) . . . . ?
C6B N1B C2B C3B -4.6(2) . . . . ?
N1A C2A C3A C4A 7.0(2) . . . . ?
N7A C2A C3A C4A -173.88(13) . . . . ?
N1A C2A C3A C14A -166.66(13) . . . . ?
N7A C2A C3A C14A 12.4(2) . . . . ?
N1B C2B C3B C4B 8.0(2) . . . . ?
N7B C2B C3B C4B -173.03(13) . . . . ?
N1B C2B C3B C14B -165.62(13) . . . . ?
N7B C2B C3B C14B 13.4(2) . . . . ?
C2B C3B C4B C5B -4.8(2) . . . . ?
C14B C3B C4B C5B 169.14(13) . . . . ?
C2A C3A C4A C5A -3.2(2) . . . . ?
C14A C3A C4A C5A 170.79(14) . . . . ?
C3A C4A C5A C6A -2.4(2) . . . . ?
C3B C4B C5B C6B -1.5(2) . . . . ?
C2A N1A C6A C5A -1.0(2) . . . . ?
C4A C5A C6A N1A 4.8(2) . . . . ?
C2B N1B C6B C5B -2.1(2) . . . . ?
C4B C5B C6B N1B 5.2(2) . . . . ?
N1B C2B N7B C8B -147.82(13) . . . . ?
C3B C2B N7B C8B 33.16(19) . . . . ?
N1B C2B N7B C17B 12.55(19) . . . . ?
C3B C2B N7B C17B -166.47(12) . . . . ?
N1A C2A N7A C8A -145.59(13) . . . . ?
C3A C2A N7A C8A 35.31(19) . . . . ?
N1A C2A N7A C17A 11.01(19) . . . . ?
C3A C2A N7A C17A -168.09(12) . . . . ?
C2B N7B C8B C13B -135.55(14) . . . . ?
C17B N7B C8B C13B 62.84(17) . . . . ?
C2B N7B C8B C9B 47.42(19) . . . . ?
C17B N7B C8B C9B -114.19(14) . . . . ?
C2A N7A C8A C9A 39.23(19) . . . . ?
C17A N7A C8A C9A -118.49(14) . . . . ?
C2A N7A C8A C13A -142.96(14) . . . . ?
C17A N7A C8A C13A 59.32(17) . . . . ?
C13B C8B C9B C10B 0.0(2) . . . . ?
N7B C8B C9B C10B 177.02(12) . . . . ?
C13A C8A C9A C10A 1.5(2) . . . . ?
N7A C8A C9A C10A 179.27(13) . . . . ?
C8B C9B C10B C11B -0.8(2) . . . . ?
C8A C9A C10A C11A -0.9(2) . . . . ?
C9B C10B C11B C12B 0.6(2) . . . . ?
C9A C10A C11A C12A -0.1(2) . . . . ?
C10B C11B C12B C13B 0.4(2) . . . . ?
C10A C11A C12A C13A 0.6(2) . . . . ?
C11A C12A C13A C8A -0.1(2) . . . . ?
C9A C8A C13A C12A -1.0(2) . . . . ?
N7A C8A C13A C12A -178.79(13) . . . . ?
C11B C12B C13B C8B -1.2(2) . . . . ?
C9B C8B C13B C12B 1.0(2) . . . . ?
N7B C8B C13B C12B -176.10(12) . . . . ?
C4A C3A C14A O15A -131.84(15) . . . . ?
C2A C3A C14A O15A 41.9(2) . . . . ?
C4A C3A C14A O16A 45.94(17) . . . . ?
C2A C3A C14A O16A -140.29(13) . . . . ?
C4B C3B C14B O15B -130.21(15) . . . . ?
C2B C3B C14B O15B 43.4(2) . . . . ?
C4B C3B C14B O16B 46.98(18) . . . . ?
C2B C3B C14B O16B -139.43(13) . . . . ?
C2B N7B C17B C18B -96.49(15) . . . . ?
C8B N7B C17B C18B 64.92(16) . . . . ?
C2A N7A C17A C18A -91.83(15) . . . . ?
C8A N7A C17A C18A 65.90(15) . . . . ?
N7B C17B C18B C19B -177.73(12) . . . . ?
N7A C17A C18A C19A 177.80(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_k09121
_audit_block_doi                 10.5517/cc12720d
_database_code_depnum_ccdc_archive 'CCDC 989892'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/cg401532j 2014
_audit_update_record             
;
2014-03-04 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 N2 O2'
_chemical_formula_sum            'C15 H16 N2 O2'
_chemical_formula_weight         256.30

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_space_group_name_Hall           '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6119(2)
_cell_length_b                   11.0473(2)
_cell_length_c                   14.6432(3)
_cell_angle_alpha                74.6603(8)
_cell_angle_beta                 72.0162(8)
_cell_angle_gamma                64.8393(9)
_cell_volume                     1322.47(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    6010
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9745
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 18
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11999
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.48
_diffrn_reflns_theta_max         27.46
_reflns_number_total             6044
_reflns_number_gt                4911
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'COLLECT (Nonius, 1997)'
_computing_cell_refinement       'DENZO-SMN (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Nonius, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Bruker, 1995)'
_computing_publication_material  'SHELX-97 and local procedures'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0505P)²+0.4223P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6044
_refine_ls_number_parameters     347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1080
_refine_ls_wR_factor_gt          0.1007
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N 1.13435(12) 0.34952(11) 0.31644(8) 0.0214(2) Uani 1 1 d . . .
N1B N 0.95742(13) 0.16623(11) 0.11032(8) 0.0230(2) Uani 1 1 d . . .
C2B C 0.79965(15) 0.21533(12) 0.12467(9) 0.0196(3) Uani 1 1 d . . .
C2A C 0.99474(15) 0.36531(12) 0.38063(9) 0.0193(3) Uani 1 1 d . . .
C3A C 0.85497(15) 0.41151(12) 0.34671(9) 0.0202(3) Uani 1 1 d . . .
C3B C 0.70166(15) 0.21067(12) 0.21960(9) 0.0193(3) Uani 1 1 d . . .
C4A C 0.86524(16) 0.42795(13) 0.24772(10) 0.0237(3) Uani 1 1 d . . .
H4A H 0.7733 0.4525 0.2245 0.028 Uiso 1 1 calc R . .
C4B C 0.77376(15) 0.13712(12) 0.29651(9) 0.0210(3) Uani 1 1 d . . .
H4B H 0.7111 0.1266 0.3603 0.025 Uiso 1 1 calc R . .
C5A C 1.00952(16) 0.40842(14) 0.18317(10) 0.0252(3) Uani 1 1 d . . .
H5A H 1.0193 0.4189 0.1152 0.030 Uiso 1 1 calc R . .
C5B C 0.93675(15) 0.07898(13) 0.28061(10) 0.0231(3) Uani 1 1 d . . .
H5B H 0.9879 0.0255 0.3320 0.028 Uiso 1 1 calc R . .
C6A C 1.13875(16) 0.37315(13) 0.22085(9) 0.0238(3) Uani 1 1 d . . .
H6A H 1.2371 0.3650 0.1766 0.029 Uiso 1 1 calc R . .
C6B C 1.02200(16) 0.10186(13) 0.18719(10) 0.0241(3) Uani 1 1 d . . .
H6B H 1.1335 0.0699 0.1769 0.029 Uiso 1 1 calc R . .
N7A N 0.99547(12) 0.33542(10) 0.47832(7) 0.0189(2) Uani 1 1 d . . .
N7B N 0.73840(13) 0.27196(11) 0.04184(7) 0.0209(2) Uani 1 1 d . . .
C8B C 0.60635(15) 0.25103(13) 0.03386(9) 0.0210(3) Uani 1 1 d . . .
C8A C 0.88210(14) 0.28715(12) 0.54911(9) 0.0187(3) Uani 1 1 d . . .
C9B C 0.50443(16) 0.34744(14) -0.02365(9) 0.0247(3) Uani 1 1 d . . .
H9B H 0.5220 0.4279 -0.0567 0.030 Uiso 1 1 calc R . .
C9A C 0.80826(15) 0.33962(13) 0.63602(9) 0.0232(3) Uani 1 1 d . . .
H9A H 0.8334 0.4073 0.6484 0.028 Uiso 1 1 calc R . .
C10A C 0.69831(16) 0.29324(15) 0.70445(10) 0.0290(3) Uani 1 1 d . . .
H10A H 0.6484 0.3291 0.7637 0.035 Uiso 1 1 calc R . .
C10B C 0.37756(17) 0.32574(15) -0.03259(10) 0.0287(3) Uani 1 1 d . . .
H10B H 0.3092 0.3918 -0.0721 0.034 Uiso 1 1 calc R . .
C11A C 0.66079(16) 0.19456(15) 0.68680(11) 0.0307(3) Uani 1 1 d . . .
H11A H 0.5844 0.1637 0.7335 0.037 Uiso 1 1 calc R . .
C11B C 0.34858(17) 0.20944(15) 0.01514(10) 0.0285(3) Uani 1 1 d . . .
H11B H 0.2609 0.1958 0.0091 0.034 Uiso 1 1 calc R . .
C12A C 0.73470(16) 0.14132(14) 0.60114(10) 0.0276(3) Uani 1 1 d . . .
H12A H 0.7091 0.0736 0.5892 0.033 Uiso 1 1 calc R . .
C12B C 0.45018(16) 0.11357(14) 0.07182(10) 0.0265(3) Uani 1 1 d . . .
H12B H 0.4314 0.0337 0.1052 0.032 Uiso 1 1 calc R . .
C13B C 0.57903(16) 0.13259(13) 0.08050(9) 0.0232(3) Uani 1 1 d . . .
H13B H 0.6490 0.0648 0.1183 0.028 Uiso 1 1 calc R . .
C13A C 0.84655(15) 0.18634(13) 0.53222(9) 0.0216(3) Uani 1 1 d . . .
H13A H 0.8984 0.1484 0.4739 0.026 Uiso 1 1 calc R . .
C14A C 0.69549(15) 0.45526(12) 0.41101(9) 0.0206(3) Uani 1 1 d . . .
C14B C 0.52881(15) 0.29070(13) 0.24092(9) 0.0201(3) Uani 1 1 d . . .
O15A O 0.65993(10) 0.52532(9) 0.47318(7) 0.0235(2) Uani 1 1 d . . .
O15B O 0.46726(11) 0.40355(9) 0.19905(7) 0.0245(2) Uani 1 1 d . . .
O16A O 0.59648(11) 0.41610(10) 0.39237(7) 0.0262(2) Uani 1 1 d . . .
H16A H 0.5094 0.4414 0.4323 0.039 Uiso 1 1 calc R . .
O16B O 0.44926(11) 0.22602(9) 0.31288(7) 0.0249(2) Uani 1 1 d . . .
H16B H 0.3520 0.2703 0.3184 0.037 Uiso 1 1 calc R . .
C17A C 1.13510(14) 0.31569(12) 0.51091(9) 0.0198(3) Uani 1 1 d . . .
H17A H 1.1001 0.3565 0.5707 0.024 Uiso 1 1 calc R . .
H17B H 1.1977 0.3636 0.4603 0.024 Uiso 1 1 calc R . .
C17B C 0.84399(16) 0.30555(13) -0.04922(9) 0.0238(3) Uani 1 1 d . . .
H17C H 0.9152 0.3371 -0.0338 0.029 Uiso 1 1 calc R . .
H17D H 0.7796 0.3813 -0.0910 0.029 Uiso 1 1 calc R . .
C18A C 1.23952(15) 0.16712(13) 0.53145(10) 0.0218(3) Uani 1 1 d . . .
H18A H 1.2770 0.1266 0.4713 0.026 Uiso 1 1 calc R . .
H18B H 1.1766 0.1186 0.5811 0.026 Uiso 1 1 calc R . .
C18B C 0.94347(17) 0.18747(14) -0.10578(10) 0.0271(3) Uani 1 1 d . . .
H18C H 0.9950 0.1067 -0.0614 0.033 Uiso 1 1 calc R . .
H18D H 0.8741 0.1659 -0.1314 0.033 Uiso 1 1 calc R . .
C19B C 1.06902(18) 0.21994(16) -0.18979(10) 0.0323(3) Uani 1 1 d . . .
H19A H 1.0188 0.3030 -0.2317 0.048 Uiso 1 1 calc R . .
H19B H 1.1251 0.1450 -0.2275 0.048 Uiso 1 1 calc R . .
H19C H 1.1440 0.2327 -0.1642 0.048 Uiso 1 1 calc R . .
C19A C 1.38127(15) 0.14872(14) 0.56731(10) 0.0260(3) Uani 1 1 d . . .
H19D H 1.4504 0.1875 0.5154 0.039 Uiso 1 1 calc R . .
H19E H 1.4397 0.0520 0.5857 0.039 Uiso 1 1 calc R . .
H19F H 1.3449 0.1948 0.6239 0.039 Uiso 1 1 calc R . .


_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 C6A 1.3448(17) . ?
N1A C2A 1.3504(16) . ?
N1B C6B 1.3381(18) . ?
N1B C2B 1.3424(17) . ?
C2B N7B 1.3912(16) . ?
C2B C3B 1.4202(17) . ?
C2A N7A 1.3819(16) . ?
C2A C3A 1.4167(18) . ?
C3A C4A 1.3897(18) . ?
C3A C14A 1.4796(18) . ?
C3B C4B 1.3885(18) . ?
C3B C14B 1.4887(18) . ?
C4A C5A 1.3810(19) . ?
C4A H4A 0.9500 . ?
C4B C5B 1.3854(18) . ?
C4B H4B 0.9500 . ?
C5A C6A 1.3773(19) . ?
C5A H5A 0.9500 . ?
C5B C6B 1.3812(19) . ?
C5B H5B 0.9500 . ?
C6A H6A 0.9500 . ?
C6B H6B 0.9500 . ?
N7A C8A 1.4319(16) . ?
N7A C17A 1.4726(15) . ?
N7B C8B 1.4260(16) . ?
N7B C17B 1.4726(16) . ?
C8B C9B 1.3968(19) . ?
C8B C13B 1.3986(18) . ?
C8A C13A 1.3927(18) . ?
C8A C9A 1.3936(18) . ?
C9B C10B 1.388(2) . ?
C9B H9B 0.9500 . ?
C9A C10A 1.3850(19) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.388(2) . ?
C10A H10A 0.9500 . ?
C10B C11B 1.388(2) . ?
C10B H10B 0.9500 . ?
C11A C12A 1.382(2) . ?
C11A H11A 0.9500 . ?
C11B C12B 1.386(2) . ?
C11B H11B 0.9500 . ?
C12A C13A 1.3931(19) . ?
C12A H12A 0.9500 . ?
C12B C13B 1.3880(19) . ?
C12B H12B 0.9500 . ?
C13B H13B 0.9500 . ?
C13A H13A 0.9500 . ?
C14A O15A 1.2248(15) . ?
C14A O16A 1.3192(15) . ?
C14B O15B 1.2135(15) . ?
C14B O16B 1.3320(15) . ?
O16A H16A 0.8400 . ?
O16B H16B 0.8400 . ?
C17A C18A 1.5219(17) . ?
C17A H17A 0.9900 . ?
C17A H17B 0.9900 . ?
C17B C18B 1.5245(18) . ?
C17B H17C 0.9900 . ?
C17B H17D 0.9900 . ?
C18A C19A 1.5242(18) . ?
C18A H18A 0.9900 . ?
C18A H18B 0.9900 . ?
C18B C19B 1.5219(19) . ?
C18B H18C 0.9900 . ?
C18B H18D 0.9900 . ?
C19B H19A 0.9800 . ?
C19B H19B 0.9800 . ?
C19B H19C 0.9800 . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 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
C6A N1A C2A 118.99(11) . . ?
C6B N1B C2B 118.38(11) . . ?
N1B C2B N7B 116.34(11) . . ?
N1B C2B C3B 121.39(12) . . ?
N7B C2B C3B 122.26(11) . . ?
N1A C2A N7A 117.43(11) . . ?
N1A C2A C3A 119.92(11) . . ?
N7A C2A C3A 122.65(11) . . ?
C4A C3A C2A 119.32(12) . . ?
C4A C3A C14A 117.57(11) . . ?
C2A C3A C14A 122.88(11) . . ?
C4B C3B C2B 117.83(11) . . ?
C4B C3B C14B 118.88(11) . . ?
C2B C3B C14B 123.04(11) . . ?
C5A C4A C3A 119.80(12) . . ?
C5A C4A H4A 120.1 . . ?
C3A C4A H4A 120.1 . . ?
C5B C4B C3B 120.23(12) . . ?
C5B C4B H4B 119.9 . . ?
C3B C4B H4B 119.9 . . ?
C6A C5A C4A 117.60(12) . . ?
C6A C5A H5A 121.2 . . ?
C4A C5A H5A 121.2 . . ?
C6B C5B C4B 117.41(12) . . ?
C6B C5B H5B 121.3 . . ?
C4B C5B H5B 121.3 . . ?
N1A C6A C5A 124.08(12) . . ?
N1A C6A H6A 118.0 . . ?
C5A C6A H6A 118.0 . . ?
N1B C6B C5B 124.12(12) . . ?
N1B C6B H6B 117.9 . . ?
C5B C6B H6B 117.9 . . ?
C2A N7A C8A 121.41(10) . . ?
C2A N7A C17A 120.89(10) . . ?
C8A N7A C17A 115.65(10) . . ?
C2B N7B C8B 120.81(10) . . ?
C2B N7B C17B 117.67(11) . . ?
C8B N7B C17B 117.27(10) . . ?
C9B C8B C13B 118.76(12) . . ?
C9B C8B N7B 120.17(12) . . ?
C13B C8B N7B 121.04(12) . . ?
C13A C8A C9A 119.60(12) . . ?
C13A C8A N7A 120.32(11) . . ?
C9A C8A N7A 120.08(11) . . ?
C10B C9B C8B 120.04(13) . . ?
C10B C9B H9B 120.0 . . ?
C8B C9B H9B 120.0 . . ?
C10A C9A C8A 120.13(12) . . ?
C10A C9A H9A 119.9 . . ?
C8A C9A H9A 119.9 . . ?
C9A C10A C11A 120.23(13) . . ?
C9A C10A H10A 119.9 . . ?
C11A C10A H10A 119.9 . . ?
C11B C10B C9B 121.25(13) . . ?
C11B C10B H10B 119.4 . . ?
C9B C10B H10B 119.4 . . ?
C12A C11A C10A 119.87(13) . . ?
C12A C11A H11A 120.1 . . ?
C10A C11A H11A 120.1 . . ?
C12B C11B C10B 118.66(13) . . ?
C12B C11B H11B 120.7 . . ?
C10B C11B H11B 120.7 . . ?
C11A C12A C13A 120.36(13) . . ?
C11A C12A H12A 119.8 . . ?
C13A C12A H12A 119.8 . . ?
C11B C12B C13B 120.91(13) . . ?
C11B C12B H12B 119.5 . . ?
C13B C12B H12B 119.5 . . ?
C12B C13B C8B 120.35(12) . . ?
C12B C13B H13B 119.8 . . ?
C8B C13B H13B 119.8 . . ?
C8A C13A C12A 119.79(12) . . ?
C8A C13A H13A 120.1 . . ?
C12A C13A H13A 120.1 . . ?
O15A C14A O16A 124.14(12) . . ?
O15A C14A C3A 121.97(11) . . ?
O16A C14A C3A 113.84(11) . . ?
O15B C14B O16B 123.60(12) . . ?
O15B C14B C3B 123.91(12) . . ?
O16B C14B C3B 112.47(10) . . ?
C14A O16A H16A 109.5 . . ?
C14B O16B H16B 109.5 . . ?
N7A C17A C18A 112.75(10) . . ?
N7A C17A H17A 109.0 . . ?
C18A C17A H17A 109.0 . . ?
N7A C17A H17B 109.0 . . ?
C18A C17A H17B 109.0 . . ?
H17A C17A H17B 107.8 . . ?
N7B C17B C18B 113.76(11) . . ?
N7B C17B H17C 108.8 . . ?
C18B C17B H17C 108.8 . . ?
N7B C17B H17D 108.8 . . ?
C18B C17B H17D 108.8 . . ?
H17C C17B H17D 107.7 . . ?
C17A C18A C19A 111.94(10) . . ?
C17A C18A H18A 109.2 . . ?
C19A C18A H18A 109.2 . . ?
C17A C18A H18B 109.2 . . ?
C19A C18A H18B 109.2 . . ?
H18A C18A H18B 107.9 . . ?
C19B C18B C17B 111.64(11) . . ?
C19B C18B H18C 109.3 . . ?
C17B C18B H18C 109.3 . . ?
C19B C18B H18D 109.3 . . ?
C17B C18B H18D 109.3 . . ?
H18C C18B H18D 108.0 . . ?
C18B C19B H19A 109.5 . . ?
C18B C19B H19B 109.5 . . ?
H19A C19B H19B 109.5 . . ?
C18B C19B H19C 109.5 . . ?
H19A C19B H19C 109.5 . . ?
H19B C19B H19C 109.5 . . ?
C18A C19A H19D 109.5 . . ?
C18A C19A H19E 109.5 . . ?
H19D C19A H19E 109.5 . . ?
C18A C19A H19F 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 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
C6B N1B C2B N7B -175.11(11) . . . . ?
C6B N1B C2B C3B 5.62(18) . . . . ?
C6A N1A C2A N7A 177.70(11) . . . . ?
C6A N1A C2A C3A -2.58(18) . . . . ?
N1A C2A C3A C4A 6.00(18) . . . . ?
N7A C2A C3A C4A -174.30(11) . . . . ?
N1A C2A C3A C14A -168.37(11) . . . . ?
N7A C2A C3A C14A 11.34(19) . . . . ?
N1B C2B C3B C4B -8.78(18) . . . . ?
N7B C2B C3B C4B 171.99(11) . . . . ?
N1B C2B C3B C14B 165.40(11) . . . . ?
N7B C2B C3B C14B -13.83(18) . . . . ?
C2A C3A C4A C5A -4.55(19) . . . . ?
C14A C3A C4A C5A 170.11(12) . . . . ?
C2B C3B C4B C5B 4.49(18) . . . . ?
C14B C3B C4B C5B -169.94(11) . . . . ?
C3A C4A C5A C6A -0.13(19) . . . . ?
C3B C4B C5B C6B 2.44(18) . . . . ?
C2A N1A C6A C5A -2.39(19) . . . . ?
C4A C5A C6A N1A 3.8(2) . . . . ?
C2B N1B C6B C5B 1.96(19) . . . . ?
C4B C5B C6B N1B -6.0(2) . . . . ?
N1A C2A N7A C8A -150.30(11) . . . . ?
C3A C2A N7A C8A 29.99(17) . . . . ?
N1A C2A N7A C17A 12.73(17) . . . . ?
C3A C2A N7A C17A -166.98(11) . . . . ?
N1B C2B N7B C8B 140.62(12) . . . . ?
C3B C2B N7B C8B -40.12(17) . . . . ?
N1B C2B N7B C17B -15.61(16) . . . . ?
C3B C2B N7B C17B 163.66(11) . . . . ?
C2B N7B C8B C9B 152.17(12) . . . . ?
C17B N7B C8B C9B -51.51(16) . . . . ?
C2B N7B C8B C13B -29.88(17) . . . . ?
C17B N7B C8B C13B 126.43(13) . . . . ?
C2A N7A C8A C13A 45.07(16) . . . . ?
C17A N7A C8A C13A -118.80(12) . . . . ?
C2A N7A C8A C9A -135.82(12) . . . . ?
C17A N7A C8A C9A 60.31(15) . . . . ?
C13B C8B C9B C10B 0.92(19) . . . . ?
N7B C8B C9B C10B 178.91(11) . . . . ?
C13A C8A C9A C10A -1.04(19) . . . . ?
N7A C8A C9A C10A 179.85(12) . . . . ?
C8A C9A C10A C11A -0.1(2) . . . . ?
C8B C9B C10B C11B 0.3(2) . . . . ?
C9A C10A C11A C12A 0.7(2) . . . . ?
C9B C10B C11B C12B -0.6(2) . . . . ?
C10A C11A C12A C13A -0.1(2) . . . . ?
C10B C11B C12B C13B -0.4(2) . . . . ?
C11B C12B C13B C8B 1.6(2) . . . . ?
C9B C8B C13B C12B -1.86(19) . . . . ?
N7B C8B C13B C12B -179.83(11) . . . . ?
C9A C8A C13A C12A 1.63(18) . . . . ?
N7A C8A C13A C12A -179.25(11) . . . . ?
C11A C12A C13A C8A -1.06(19) . . . . ?
C4A C3A C14A O15A -132.32(13) . . . . ?
C2A C3A C14A O15A 42.14(19) . . . . ?
C4A C3A C14A O16A 45.34(16) . . . . ?
C2A C3A C14A O16A -140.20(12) . . . . ?
C4B C3B C14B O15B 138.82(13) . . . . ?
C2B C3B C14B O15B -35.31(19) . . . . ?
C4B C3B C14B O16B -39.61(16) . . . . ?
C2B C3B C14B O16B 146.27(12) . . . . ?
C2A N7A C17A C18A -97.33(13) . . . . ?
C8A N7A C17A C18A 66.63(14) . . . . ?
C2B N7B C17B C18B 86.12(14) . . . . ?
C8B N7B C17B C18B -70.96(15) . . . . ?
N7A C17A C18A C19A -178.68(10) . . . . ?
N7B C17B C18B C19B -170.56(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_shelxl
_audit_block_doi                 10.5517/cc12721f
_database_code_depnum_ccdc_archive 'CCDC 989893'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/cg401532j 2014
_audit_update_record             
;
2014-03-04 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 N2 O2'
_chemical_formula_sum            'C14 H14 N2 O2'
_chemical_formula_weight         242.27

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.3769(2)
_cell_length_b                   8.8497(2)
_cell_length_c                   13.5431(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.8897(8)
_cell_angle_gamma                90.00
_cell_volume                     1234.72(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    3000
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9739
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 18
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5422
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         27.47
_reflns_number_total             2819
_reflns_number_gt                2358
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'COLLECT (Nonius, 1997)'
_computing_cell_refinement       'DENZO-SMN (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Nonius, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Bruker, 1995)'
_computing_publication_material  'SHELX-97 and local procedures'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0364P)²+0.7540P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2819
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1019
_refine_ls_wR_factor_gt          0.0964
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.28535(11) 0.31758(13) 0.30187(8) 0.0164(2) Uani 1 1 d . . .
C2 C 0.28529(12) 0.26848(15) 0.20754(9) 0.0136(3) Uani 1 1 d . . .
C3 C 0.21398(12) 0.34823(15) 0.12735(9) 0.0144(3) Uani 1 1 d . . .
C4 C 0.13645(13) 0.46855(15) 0.14959(10) 0.0181(3) Uani 1 1 d . . .
H4 H 0.0829 0.5181 0.0976 0.022 Uiso 1 1 calc R . .
C5 C 0.13655(14) 0.51709(16) 0.24720(10) 0.0208(3) Uani 1 1 d . . .
H5 H 0.0848 0.6001 0.2632 0.025 Uiso 1 1 calc R . .
C6 C 0.21478(14) 0.43993(16) 0.31978(10) 0.0193(3) Uani 1 1 d . . .
H6 H 0.2191 0.4752 0.3863 0.023 Uiso 1 1 calc R . .
N7 N 0.35727(10) 0.14036(13) 0.19346(8) 0.0146(2) Uani 1 1 d . . .
C8 C 0.30678(13) 0.02378(15) 0.12685(9) 0.0147(3) Uani 1 1 d . . .
C9 C 0.17491(13) -0.00995(16) 0.11361(10) 0.0193(3) Uani 1 1 d . . .
H9 H 0.1160 0.0497 0.1455 0.023 Uiso 1 1 calc R . .
C10 C 0.12896(14) -0.13098(17) 0.05371(11) 0.0233(3) Uani 1 1 d . . .
H10 H 0.0387 -0.1529 0.0447 0.028 Uiso 1 1 calc R . .
C11 C 0.21375(15) -0.21991(16) 0.00707(11) 0.0234(3) Uani 1 1 d . . .
H11 H 0.1821 -0.3027 -0.0334 0.028 Uiso 1 1 calc R . .
C12 C 0.34515(15) -0.18641(16) 0.02028(10) 0.0222(3) Uani 1 1 d . . .
H12 H 0.4039 -0.2466 -0.0114 0.027 Uiso 1 1 calc R . .
C13 C 0.39165(14) -0.06547(16) 0.07952(10) 0.0184(3) Uani 1 1 d . . .
H13 H 0.4819 -0.0434 0.0879 0.022 Uiso 1 1 calc R . .
C14 C 0.21886(13) 0.32196(15) 0.01869(10) 0.0147(3) Uani 1 1 d . . .
O15 O 0.33210(9) 0.27297(11) -0.00515(7) 0.0167(2) Uani 1 1 d . . .
H15 H 0.3257 0.2557 -0.0665 0.025 Uiso 1 1 calc R . .
O16 O 0.12745(9) 0.35223(12) -0.04263(7) 0.0210(2) Uani 1 1 d . . .
C17 C 0.46093(13) 0.09366(16) 0.27169(10) 0.0171(3) Uani 1 1 d . . .
H17A H 0.4880 0.1822 0.3138 0.020 Uiso 1 1 calc R . .
H17B H 0.5370 0.0597 0.2400 0.020 Uiso 1 1 calc R . .
C18 C 0.42004(15) -0.03289(16) 0.33755(10) 0.0233(3) Uani 1 1 d . . .
H18A H 0.3420 -0.0022 0.3666 0.035 Uiso 1 1 calc R . .
H18B H 0.4903 -0.0535 0.3909 0.035 Uiso 1 1 calc R . .
H18C H 0.4014 -0.1243 0.2975 0.035 Uiso 1 1 calc R . .


_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 C6 1.3454(18) . ?
N1 C2 1.3493(16) . ?
C2 N7 1.3835(17) . ?
C2 C3 1.4256(18) . ?
C3 C4 1.3893(19) . ?
C3 C14 1.4967(17) . ?
C4 C5 1.3898(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
N7 C8 1.4280(17) . ?
N7 C17 1.4755(16) . ?
C8 C9 1.3911(19) . ?
C8 C13 1.3949(19) . ?
C9 C10 1.393(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O16 1.2133(16) . ?
C14 O15 1.3282(16) . ?
O15 H15 0.8400 . ?
C17 C18 1.523(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C6 N1 C2 119.43(12) . . ?
N1 C2 N7 117.10(11) . . ?
N1 C2 C3 120.20(12) . . ?
N7 C2 C3 122.70(11) . . ?
C4 C3 C2 118.39(12) . . ?
C4 C3 C14 114.90(11) . . ?
C2 C3 C14 126.62(12) . . ?
C3 C4 C5 120.58(13) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 117.28(13) . . ?
C6 C5 H5 121.4 . . ?
C4 C5 H5 121.4 . . ?
N1 C6 C5 123.84(13) . . ?
N1 C6 H6 118.1 . . ?
C5 C6 H6 118.1 . . ?
C2 N7 C8 121.06(11) . . ?
C2 N7 C17 119.32(11) . . ?
C8 N7 C17 115.59(11) . . ?
C9 C8 C13 119.00(12) . . ?
C9 C8 N7 121.14(12) . . ?
C13 C8 N7 119.69(12) . . ?
C8 C9 C10 120.19(13) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.65(14) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 119.18(13) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 120.51(13) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 120.46(13) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
O16 C14 O15 123.19(12) . . ?
O16 C14 C3 121.52(12) . . ?
O15 C14 C3 115.15(11) . . ?
C14 O15 H15 109.5 . . ?
N7 C17 C18 113.33(11) . . ?
N7 C17 H17A 108.9 . . ?
C18 C17 H17A 108.9 . . ?
N7 C17 H17B 108.9 . . ?
C18 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 N7 -178.66(12) . . . . ?
C6 N1 C2 C3 1.79(19) . . . . ?
N1 C2 C3 C4 -5.51(19) . . . . ?
N7 C2 C3 C4 174.97(12) . . . . ?
N1 C2 C3 C14 170.74(12) . . . . ?
N7 C2 C3 C14 -8.8(2) . . . . ?
C2 C3 C4 C5 5.0(2) . . . . ?
C14 C3 C4 C5 -171.71(12) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C2 N1 C6 C5 2.7(2) . . . . ?
C4 C5 C6 N1 -3.2(2) . . . . ?
N1 C2 N7 C8 136.62(12) . . . . ?
C3 C2 N7 C8 -43.85(18) . . . . ?
N1 C2 N7 C17 -19.82(17) . . . . ?
C3 C2 N7 C17 159.72(12) . . . . ?
C2 N7 C8 C9 -33.38(18) . . . . ?
C17 N7 C8 C9 123.88(13) . . . . ?
C2 N7 C8 C13 151.33(12) . . . . ?
C17 N7 C8 C13 -51.41(16) . . . . ?
C13 C8 C9 C10 -0.1(2) . . . . ?
N7 C8 C9 C10 -175.47(12) . . . . ?
C8 C9 C10 C11 0.4(2) . . . . ?
C9 C10 C11 C12 -0.4(2) . . . . ?
C10 C11 C12 C13 0.1(2) . . . . ?
C11 C12 C13 C8 0.2(2) . . . . ?
C9 C8 C13 C12 -0.2(2) . . . . ?
N7 C8 C13 C12 175.23(12) . . . . ?
C4 C3 C14 O16 -30.46(18) . . . . ?
C2 C3 C14 O16 153.18(13) . . . . ?
C4 C3 C14 O15 145.45(12) . . . . ?
C2 C3 C14 O15 -30.91(19) . . . . ?
C2 N7 C17 C18 99.70(14) . . . . ?
C8 N7 C17 C18 -57.98(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O15 H15 N1 0.84 1.90 2.7210(14) 167.2 4_565

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_k06339
_audit_block_doi                 10.5517/cc12722g
_database_code_depnum_ccdc_archive 'CCDC 989894'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/cg401532j 2014
_audit_update_record             
;
2014-03-04 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 N2 O2'
_chemical_formula_sum            'C14 H14 N2 O2'
_chemical_formula_weight         242.27

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   9.283(1)
_cell_length_b                   14.248(2)
_cell_length_c                   37.628(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4976.8(10)
_cell_formula_units_Z            16
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    6367
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2048
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9573
_exptl_absorpt_correction_T_max  0.9826
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 18
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10732
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_theta_min         1.08
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5699
_reflns_number_gt                3795
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'COLLECT (Nonius, 1997)'
_computing_cell_refinement       'DENZO-SMN (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Nonius, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Bruker, 1995)'
_computing_publication_material  'SHELX-97 and local procedures'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0731P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5699
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1262
_refine_ls_wR_factor_gt          0.1062
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N 0.27311(14) -0.05421(8) 0.04353(3) 0.0225(3) Uani 1 1 d . . .
C2A C 0.21902(16) 0.03369(10) 0.04298(4) 0.0198(3) Uani 1 1 d . . .
C3A C 0.31220(16) 0.11204(10) 0.03990(4) 0.0211(3) Uani 1 1 d . . .
C4A C 0.45956(16) 0.09683(10) 0.04146(4) 0.0248(4) Uani 1 1 d . . .
H4A H 0.5238 0.1487 0.0408 0.030 Uiso 1 1 calc R . .
C5A C 0.51379(17) 0.00641(11) 0.04396(4) 0.0266(4) Uani 1 1 d . . .
H5A H 0.6144 -0.0048 0.0458 0.032 Uiso 1 1 calc R . .
C6A C 0.41747(17) -0.06602(11) 0.04361(4) 0.0251(4) Uani 1 1 d . . .
H6A H 0.4541 -0.1283 0.0434 0.030 Uiso 1 1 calc R . .
N7A N 0.07146(13) 0.04333(8) 0.04551(3) 0.0206(3) Uani 1 1 d . . .
C8A C 0.00953(16) 0.12306(10) 0.06311(4) 0.0211(3) Uani 1 1 d . . .
C9A C -0.11351(16) 0.16412(11) 0.04886(4) 0.0243(3) Uani 1 1 d . . .
H9A H -0.1526 0.1412 0.0272 0.029 Uiso 1 1 calc R . .
C10A C -0.17897(17) 0.23841(11) 0.06620(4) 0.0267(4) Uani 1 1 d . . .
H10A H -0.2633 0.2662 0.0565 0.032 Uiso 1 1 calc R . .
C11A C -0.12146(17) 0.27255(11) 0.09782(4) 0.0262(4) Uani 1 1 d . . .
H11A H -0.1659 0.3239 0.1096 0.031 Uiso 1 1 calc R . .
C12A C 0.00018(16) 0.23162(11) 0.11199(4) 0.0252(4) Uani 1 1 d . . .
H12A H 0.0396 0.2550 0.1335 0.030 Uiso 1 1 calc R . .
C13A C 0.06558(16) 0.15620(10) 0.09490(4) 0.0232(3) Uani 1 1 d . . .
H13A H 0.1484 0.1275 0.1050 0.028 Uiso 1 1 calc R . .
C14A C -0.02053(17) -0.04114(10) 0.04659(4) 0.0249(4) Uani 1 1 d . . .
H14A H 0.0212 -0.0900 0.0310 0.030 Uiso 1 1 calc R . .
H14B H -0.1174 -0.0253 0.0374 0.030 Uiso 1 1 calc R . .
C15A C 0.26035(16) 0.20902(10) 0.03227(4) 0.0225(3) Uani 1 1 d . . .
O16A O 0.33022(11) 0.27200(7) 0.05157(3) 0.0281(3) Uani 1 1 d . . .
H16A H 0.3006 0.3260 0.0464 0.042 Uiso 1 1 calc R . .
O17A O 0.16902(11) 0.22769(7) 0.01022(3) 0.0260(3) Uani 1 1 d . . .
C18A C -0.03443(18) -0.07972(11) 0.08415(4) 0.0315(4) Uani 1 1 d . . .
H18A H 0.0617 -0.0891 0.0943 0.047 Uiso 1 1 calc R . .
H18B H -0.0857 -0.1398 0.0835 0.047 Uiso 1 1 calc R . .
H18C H -0.0883 -0.0351 0.0989 0.047 Uiso 1 1 calc R . .
N1B N 0.19775(14) -0.21539(9) 0.18700(3) 0.0278(3) Uani 1 1 d . . .
C2B C 0.25895(17) -0.13026(10) 0.19111(4) 0.0223(3) Uani 1 1 d . . .
C3B C 0.17833(16) -0.04748(10) 0.18660(4) 0.0224(3) Uani 1 1 d . . .
C4B C 0.03661(17) -0.05533(11) 0.17549(4) 0.0271(4) Uani 1 1 d . . .
H4B H -0.0180 -0.0004 0.1706 0.033 Uiso 1 1 calc R . .
C5B C -0.02574(18) -0.14302(12) 0.17154(4) 0.0320(4) Uani 1 1 d . . .
H5B H -0.1234 -0.1494 0.1644 0.038 Uiso 1 1 calc R . .
C6B C 0.05757(19) -0.22036(12) 0.17831(4) 0.0313(4) Uani 1 1 d . . .
H6B H 0.0140 -0.2806 0.1768 0.038 Uiso 1 1 calc R . .
N7B N 0.40481(13) -0.13077(8) 0.19981(3) 0.0240(3) Uani 1 1 d . . .
C8B C 0.49916(16) -0.06083(10) 0.18665(4) 0.0231(3) Uani 1 1 d . . .
C9B C 0.48605(17) -0.02943(10) 0.15165(4) 0.0252(4) Uani 1 1 d . . .
H9B H 0.4133 -0.0549 0.1367 0.030 Uiso 1 1 calc R . .
C10B C 0.57822(18) 0.03856(11) 0.13854(4) 0.0289(4) Uani 1 1 d . . .
H10B H 0.5670 0.0602 0.1148 0.035 Uiso 1 1 calc R . .
C11B C 0.68652(17) 0.07547(12) 0.15955(4) 0.0311(4) Uani 1 1 d . . .
H11B H 0.7500 0.1218 0.1504 0.037 Uiso 1 1 calc R . .
C12B C 0.70079(17) 0.04369(11) 0.19415(4) 0.0301(4) Uani 1 1 d . . .
H12B H 0.7750 0.0684 0.2088 0.036 Uiso 1 1 calc R . .
C13B C 0.60837(17) -0.02345(11) 0.20763(4) 0.0268(4) Uani 1 1 d . . .
H13B H 0.6195 -0.0443 0.2315 0.032 Uiso 1 1 calc R . .
C14B C 0.45398(18) -0.19362(11) 0.22855(4) 0.0288(4) Uani 1 1 d . . .
H14C H 0.3730 -0.2345 0.2358 0.035 Uiso 1 1 calc R . .
H14D H 0.4818 -0.1552 0.2494 0.035 Uiso 1 1 calc R . .
C15B C 0.23357(17) 0.04749(10) 0.19718(4) 0.0224(3) Uani 1 1 d . . .
O16B O 0.18862(12) 0.11427(7) 0.17522(3) 0.0310(3) Uani 1 1 d . . .
H16B H 0.2177 0.1667 0.1825 0.047 Uiso 1 1 calc R . .
O17B O 0.30522(11) 0.06137(7) 0.22339(3) 0.0268(3) Uani 1 1 d . . .
C18B C 0.58001(18) -0.25436(12) 0.21791(5) 0.0347(4) Uani 1 1 d . . .
H18D H 0.5529 -0.2933 0.1975 0.052 Uiso 1 1 calc R . .
H18E H 0.6072 -0.2948 0.2379 0.052 Uiso 1 1 calc R . .
H18F H 0.6618 -0.2144 0.2114 0.052 Uiso 1 1 calc R . .


_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 C2A 1.3493(18) . ?
N1A C6A 1.3506(19) . ?
C2A N7A 1.3800(18) . ?
C2A C3A 1.417(2) . ?
C3A C4A 1.386(2) . ?
C3A C15A 1.491(2) . ?
C4A C5A 1.386(2) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.366(2) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
N7A C8A 1.4352(18) . ?
N7A C14A 1.4762(18) . ?
C8A C13A 1.387(2) . ?
C8A C9A 1.391(2) . ?
C9A C10A 1.384(2) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.392(2) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.378(2) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.392(2) . ?
C12A H12A 0.9500 . ?
C13A H13A 0.9500 . ?
C14A C18A 1.522(2) . ?
C14A H14A 0.9900 . ?
C14A H14B 0.9900 . ?
C15A O17A 1.2157(18) . ?
C15A O16A 1.3241(17) . ?
O16A H16A 0.8400 . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
N1B C6B 1.344(2) . ?
N1B C2B 1.3482(18) . ?
C2B N7B 1.393(2) . ?
C2B C3B 1.407(2) . ?
C3B C4B 1.385(2) . ?
C3B C15B 1.501(2) . ?
C4B C5B 1.385(2) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.370(2) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
N7B C8B 1.4161(19) . ?
N7B C14B 1.4764(19) . ?
C8B C13B 1.391(2) . ?
C8B C9B 1.396(2) . ?
C9B C10B 1.383(2) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.383(2) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.385(2) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.381(2) . ?
C12B H12B 0.9500 . ?
C13B H13B 0.9500 . ?
C14B C18B 1.509(2) . ?
C14B H14C 0.9900 . ?
C14B H14D 0.9900 . ?
C15B O17B 1.2059(17) . ?
C15B O16B 1.3277(17) . ?
O16B H16B 0.8400 . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 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
C2A N1A C6A 119.01(13) . . ?
N1A C2A N7A 117.43(13) . . ?
N1A C2A C3A 120.35(13) . . ?
N7A C2A C3A 122.22(13) . . ?
C4A C3A C2A 118.40(13) . . ?
C4A C3A C15A 118.14(13) . . ?
C2A C3A C15A 123.29(13) . . ?
C3A C4A C5A 120.43(14) . . ?
C3A C4A H4A 119.8 . . ?
C5A C4A H4A 119.8 . . ?
C6A C5A C4A 117.63(15) . . ?
C6A C5A H5A 121.2 . . ?
C4A C5A H5A 121.2 . . ?
N1A C6A C5A 123.75(14) . . ?
N1A C6A H6A 118.1 . . ?
C5A C6A H6A 118.1 . . ?
C2A N7A C8A 120.54(12) . . ?
C2A N7A C14A 119.66(12) . . ?
C8A N7A C14A 113.64(11) . . ?
C13A C8A C9A 119.82(14) . . ?
C13A C8A N7A 121.13(13) . . ?
C9A C8A N7A 118.95(13) . . ?
C10A C9A C8A 120.05(14) . . ?
C10A C9A H9A 120.0 . . ?
C8A C9A H9A 120.0 . . ?
C9A C10A C11A 120.12(15) . . ?
C9A C10A H10A 119.9 . . ?
C11A C10A H10A 119.9 . . ?
C12A C11A C10A 119.80(14) . . ?
C12A C11A H11A 120.1 . . ?
C10A C11A H11A 120.1 . . ?
C11A C12A C13A 120.36(14) . . ?
C11A C12A H12A 119.8 . . ?
C13A C12A H12A 119.8 . . ?
C8A C13A C12A 119.84(14) . . ?
C8A C13A H13A 120.1 . . ?
C12A C13A H13A 120.1 . . ?
N7A C14A C18A 111.66(12) . . ?
N7A C14A H14A 109.3 . . ?
C18A C14A H14A 109.3 . . ?
N7A C14A H14B 109.3 . . ?
C18A C14A H14B 109.3 . . ?
H14A C14A H14B 107.9 . . ?
O17A C15A O16A 124.59(14) . . ?
O17A C15A C3A 124.00(13) . . ?
O16A C15A C3A 111.36(13) . . ?
C15A O16A H16A 109.5 . . ?
C14A C18A H18A 109.5 . . ?
C14A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C14A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C6B N1B C2B 118.91(13) . . ?
N1B C2B N7B 115.58(13) . . ?
N1B C2B C3B 121.08(14) . . ?
N7B C2B C3B 123.34(13) . . ?
C4B C3B C2B 118.29(14) . . ?
C4B C3B C15B 118.52(13) . . ?
C2B C3B C15B 122.82(13) . . ?
C5B C4B C3B 120.15(15) . . ?
C5B C4B H4B 119.9 . . ?
C3B C4B H4B 119.9 . . ?
C6B C5B C4B 118.01(15) . . ?
C6B C5B H5B 121.0 . . ?
C4B C5B H5B 121.0 . . ?
N1B C6B C5B 123.34(15) . . ?
N1B C6B H6B 118.3 . . ?
C5B C6B H6B 118.3 . . ?
C2B N7B C8B 121.02(12) . . ?
C2B N7B C14B 118.41(12) . . ?
C8B N7B C14B 119.46(12) . . ?
C13B C8B C9B 118.44(14) . . ?
C13B C8B N7B 121.44(14) . . ?
C9B C8B N7B 120.10(14) . . ?
C10B C9B C8B 120.45(15) . . ?
C10B C9B H9B 119.8 . . ?
C8B C9B H9B 119.8 . . ?
C11B C10B C9B 120.79(15) . . ?
C11B C10B H10B 119.6 . . ?
C9B C10B H10B 119.6 . . ?
C10B C11B C12B 118.87(15) . . ?
C10B C11B H11B 120.6 . . ?
C12B C11B H11B 120.6 . . ?
C13B C12B C11B 120.81(15) . . ?
C13B C12B H12B 119.6 . . ?
C11B C12B H12B 119.6 . . ?
C12B C13B C8B 120.62(15) . . ?
C12B C13B H13B 119.7 . . ?
C8B C13B H13B 119.7 . . ?
N7B C14B C18B 113.15(13) . . ?
N7B C14B H14C 108.9 . . ?
C18B C14B H14C 108.9 . . ?
N7B C14B H14D 108.9 . . ?
C18B C14B H14D 108.9 . . ?
H14C C14B H14D 107.8 . . ?
O17B C15B O16B 124.39(14) . . ?
O17B C15B C3B 123.60(13) . . ?
O16B C15B C3B 111.94(13) . . ?
C15B O16B H16B 109.5 . . ?
C14B C18B H18D 109.5 . . ?
C14B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C14B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 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
C6A N1A C2A N7A -175.44(12) . . . . ?
C6A N1A C2A C3A 4.6(2) . . . . ?
N1A C2A C3A C4A -7.1(2) . . . . ?
N7A C2A C3A C4A 172.98(13) . . . . ?
N1A C2A C3A C15A 168.05(12) . . . . ?
N7A C2A C3A C15A -11.9(2) . . . . ?
C2A C3A C4A C5A 3.6(2) . . . . ?
C15A C3A C4A C5A -171.79(13) . . . . ?
C3A C4A C5A C6A 2.1(2) . . . . ?
C2A N1A C6A C5A 1.5(2) . . . . ?
C4A C5A C6A N1A -4.9(2) . . . . ?
N1A C2A N7A C8A 147.20(12) . . . . ?
C3A C2A N7A C8A -32.8(2) . . . . ?
N1A C2A N7A C14A -3.47(18) . . . . ?
C3A C2A N7A C14A 176.50(13) . . . . ?
C2A N7A C8A C13A -42.7(2) . . . . ?
C14A N7A C8A C13A 109.63(15) . . . . ?
C2A N7A C8A C9A 140.87(14) . . . . ?
C14A N7A C8A C9A -66.82(17) . . . . ?
C13A C8A C9A C10A 0.6(2) . . . . ?
N7A C8A C9A C10A 177.11(13) . . . . ?
C8A C9A C10A C11A 0.3(2) . . . . ?
C9A C10A C11A C12A -0.6(2) . . . . ?
C10A C11A C12A C13A -0.2(2) . . . . ?
C9A C8A C13A C12A -1.3(2) . . . . ?
N7A C8A C13A C12A -177.76(13) . . . . ?
C11A C12A C13A C8A 1.1(2) . . . . ?
C2A N7A C14A C18A 84.99(16) . . . . ?
C8A N7A C14A C18A -67.59(16) . . . . ?
C4A C3A C15A O17A 131.82(16) . . . . ?
C2A C3A C15A O17A -43.3(2) . . . . ?
C4A C3A C15A O16A -45.82(18) . . . . ?
C2A C3A C15A O16A 139.06(14) . . . . ?
C6B N1B C2B N7B -179.47(13) . . . . ?
C6B N1B C2B C3B 0.3(2) . . . . ?
N1B C2B C3B C4B -4.2(2) . . . . ?
N7B C2B C3B C4B 175.49(13) . . . . ?
N1B C2B C3B C15B 168.65(13) . . . . ?
N7B C2B C3B C15B -11.6(2) . . . . ?
C2B C3B C4B C5B 4.6(2) . . . . ?
C15B C3B C4B C5B -168.59(14) . . . . ?
C3B C4B C5B C6B -1.1(2) . . . . ?
C2B N1B C6B C5B 3.5(2) . . . . ?
C4B C5B C6B N1B -3.1(2) . . . . ?
N1B C2B N7B C8B 144.73(14) . . . . ?
C3B C2B N7B C8B -35.0(2) . . . . ?
N1B C2B N7B C14B -47.41(18) . . . . ?
C3B C2B N7B C14B 132.85(15) . . . . ?
C2B N7B C8B C13B 141.35(14) . . . . ?
C14B N7B C8B C13B -26.4(2) . . . . ?
C2B N7B C8B C9B -40.2(2) . . . . ?
C14B N7B C8B C9B 152.07(14) . . . . ?
C13B C8B C9B C10B -1.2(2) . . . . ?
N7B C8B C9B C10B -179.70(13) . . . . ?
C8B C9B C10B C11B 1.2(2) . . . . ?
C9B C10B C11B C12B -0.4(2) . . . . ?
C10B C11B C12B C13B -0.3(2) . . . . ?
C11B C12B C13B C8B 0.2(2) . . . . ?
C9B C8B C13B C12B 0.5(2) . . . . ?
N7B C8B C13B C12B 178.99(14) . . . . ?
C2B N7B C14B C18B 128.82(15) . . . . ?
C8B N7B C14B C18B -63.12(18) . . . . ?
C4B C3B C15B O17B 135.25(16) . . . . ?
C2B C3B C15B O17B -37.6(2) . . . . ?
C4B C3B C15B O16B -41.87(19) . . . . ?
C2B C3B C15B O16B 145.25(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O16A H16A N1A 0.84 1.84 2.6727(16) 169.8 8_665
O16B H16B N1B 0.84 1.86 2.6832(17) 165.3 8_665

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_k09136
_audit_block_doi                 10.5517/cc12723h
_database_code_depnum_ccdc_archive 'CCDC 989895'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/cg401532j 2014
_audit_update_record             
;
2014-03-04 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N2 O2'
_chemical_formula_sum            'C16 H18 N2 O2'
_chemical_formula_weight         270.32

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.1175(2)
_cell_length_b                   11.5416(2)
_cell_length_c                   12.2025(2)
_cell_angle_alpha                105.7668(7)
_cell_angle_beta                 102.7156(7)
_cell_angle_gamma                98.4533(8)
_cell_volume                     1433.77(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    5874
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9674
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_process_details   'Scalepack (Otwinowsky & Minor, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ=55°'
_diffrn_detector_area_resol_mean 18
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11103
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         27.50
_reflns_number_total             6570
_reflns_number_gt                5049
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Collect (Nonius, 2002)'
_computing_cell_refinement       'Denzo-SMN (Nonius, 1997)'
_computing_data_reduction        'Denzo-SMN (Nonius, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 1995)'
_computing_publication_material  
;
 SHELX-97 (Sheldrick, 1997) and local procedures
;

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0529P)²+0.2616P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6570
_refine_ls_number_parameters     365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1108
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O16A O 1.19339(8) 0.19638(8) 0.59835(8) 0.0183(2) Uani 1 1 d . . .
O15A O 1.30012(9) 0.36458(8) 0.57405(8) 0.0197(2) Uani 1 1 d . . .
H15A H 1.2790 0.4016 0.6338 0.029 Uiso 1 1 calc R . .
O16B O 0.75242(9) 0.13873(8) 0.01121(9) 0.0225(2) Uani 1 1 d . . .
O15B O 0.81970(9) 0.23663(8) -0.10744(8) 0.0200(2) Uani 1 1 d . . .
H15B H 0.8050 0.1645 -0.1541 0.030 Uiso 1 1 calc R . .
N1B N 0.77781(10) 0.50697(9) 0.24250(9) 0.0160(2) Uani 1 1 d . . .
N1A N 1.24950(10) -0.01323(10) 0.27465(10) 0.0177(2) Uani 1 1 d . . .
N7B N 0.62020(10) 0.32906(9) 0.13878(9) 0.0151(2) Uani 1 1 d . . .
N7A N 1.07745(10) 0.03855(9) 0.34011(9) 0.0152(2) Uani 1 1 d . . .
C18B C 0.46715(12) 0.44345(12) 0.21866(12) 0.0180(3) Uani 1 1 d . . .
H18A H 0.4027 0.4066 0.1413 0.022 Uiso 1 1 calc R . .
H18B H 0.5159 0.5225 0.2188 0.022 Uiso 1 1 calc R . .
C9A C 0.91685(12) 0.11143(12) 0.43196(11) 0.0181(3) Uani 1 1 d . . .
H9A H 0.8997 0.0359 0.4487 0.022 Uiso 1 1 calc R . .
C14A C 1.25354(11) 0.24381(11) 0.54421(11) 0.0156(3) Uani 1 1 d . . .
C9B C 0.53203(12) 0.30344(12) -0.07132(12) 0.0179(3) Uani 1 1 d . . .
H9B H 0.5814 0.3822 -0.0606 0.021 Uiso 1 1 calc R . .
C13A C 1.03432(13) 0.24340(12) 0.35100(11) 0.0188(3) Uani 1 1 d . . .
H13A H 1.0972 0.2579 0.3118 0.023 Uiso 1 1 calc R . .
C17B C 0.55605(12) 0.35667(12) 0.23301(11) 0.0167(3) Uani 1 1 d . . .
H17A H 0.6207 0.3942 0.3102 0.020 Uiso 1 1 calc R . .
H17B H 0.5071 0.2783 0.2343 0.020 Uiso 1 1 calc R . .
C17A C 0.99846(12) -0.08063(11) 0.25694(11) 0.0167(3) Uani 1 1 d . . .
H17C H 0.9235 -0.1030 0.2844 0.020 Uiso 1 1 calc R . .
H17D H 1.0475 -0.1456 0.2575 0.020 Uiso 1 1 calc R . .
C2A C 1.20514(12) 0.06557(11) 0.35162(11) 0.0150(3) Uani 1 1 d . . .
C6B C 0.89131(12) 0.57869(12) 0.25785(12) 0.0177(3) Uani 1 1 d . . .
H6B H 0.9191 0.6533 0.3223 0.021 Uiso 1 1 calc R . .
C8A C 1.00992(11) 0.13257(11) 0.37514(11) 0.0152(3) Uani 1 1 d . . .
C12B C 0.38446(12) 0.07421(12) -0.10346(12) 0.0185(3) Uani 1 1 d . . .
H12B H 0.3337 -0.0039 -0.1140 0.022 Uiso 1 1 calc R . .
C3B C 0.81620(12) 0.35962(11) 0.07913(11) 0.0153(3) Uani 1 1 d . . .
C18A C 0.95465(12) -0.07696(12) 0.13076(11) 0.0176(3) Uani 1 1 d . . .
H18C H 1.0296 -0.0548 0.1032 0.021 Uiso 1 1 calc R . .
H18D H 0.9057 -0.0120 0.1302 0.021 Uiso 1 1 calc R . .
C13B C 0.46541(12) 0.14255(12) 0.00706(12) 0.0173(3) Uani 1 1 d . . .
H13B H 0.4699 0.1109 0.0717 0.021 Uiso 1 1 calc R . .
C12A C 0.96651(13) 0.33326(13) 0.38431(12) 0.0234(3) Uani 1 1 d . . .
H12A H 0.9838 0.4092 0.3683 0.028 Uiso 1 1 calc R . .
C2B C 0.73790(12) 0.39873(11) 0.15330(11) 0.0146(3) Uani 1 1 d . . .
C5B C 0.96927(12) 0.55035(12) 0.18587(12) 0.0182(3) Uani 1 1 d . . .
H5B H 1.0469 0.6052 0.1975 0.022 Uiso 1 1 calc R . .
C8B C 0.54005(12) 0.25726(11) 0.02363(11) 0.0152(3) Uani 1 1 d . . .
C4B C 0.92975(12) 0.43819(12) 0.09555(12) 0.0177(3) Uani 1 1 d . . .
H4B H 0.9814 0.4152 0.0444 0.021 Uiso 1 1 calc R . .
C3A C 1.28974(12) 0.17021(11) 0.44059(11) 0.0158(3) Uani 1 1 d . . .
C4A C 1.41545(12) 0.19392(12) 0.44058(12) 0.0193(3) Uani 1 1 d . . .
H4A H 1.4722 0.2658 0.4967 0.023 Uiso 1 1 calc R . .
C10B C 0.45136(12) 0.23382(12) -0.18201(12) 0.0201(3) Uani 1 1 d . . .
H10B H 0.4469 0.2650 -0.2469 0.024 Uiso 1 1 calc R . .
C6A C 1.37324(12) 0.01077(12) 0.28067(12) 0.0199(3) Uani 1 1 d . . .
H6A H 1.4030 -0.0470 0.2272 0.024 Uiso 1 1 calc R . .
C11B C 0.37730(12) 0.11930(12) -0.19842(12) 0.0197(3) Uani 1 1 d . . .
H11B H 0.3222 0.0723 -0.2741 0.024 Uiso 1 1 calc R . .
C19A C 0.87307(12) -0.19997(12) 0.04549(12) 0.0197(3) Uani 1 1 d . . .
H19A H 0.9188 -0.2665 0.0510 0.024 Uiso 1 1 calc R . .
H19B H 0.7940 -0.2185 0.0682 0.024 Uiso 1 1 calc R . .
C5A C 1.45944(13) 0.11356(12) 0.35928(12) 0.0216(3) Uani 1 1 d . . .
H5A H 1.5454 0.1290 0.3581 0.026 Uiso 1 1 calc R . .
C20B C 0.30688(15) 0.54986(15) 0.29931(15) 0.0352(4) Uani 1 1 d . . .
H20A H 0.3515 0.6303 0.3008 0.053 Uiso 1 1 calc R . .
H20B H 0.2649 0.5613 0.3630 0.053 Uiso 1 1 calc R . .
H20C H 0.2436 0.5101 0.2228 0.053 Uiso 1 1 calc R . .
C14B C 0.79037(12) 0.23316(12) -0.00790(12) 0.0165(3) Uani 1 1 d . . .
C20A C 0.84108(15) -0.19684(15) -0.08122(13) 0.0318(4) Uani 1 1 d . . .
H20D H 0.7927 -0.1334 -0.0875 0.048 Uiso 1 1 calc R . .
H20E H 0.7906 -0.2775 -0.1344 0.048 Uiso 1 1 calc R . .
H20F H 0.9193 -0.1776 -0.1035 0.048 Uiso 1 1 calc R . .
C19B C 0.40113(13) 0.46878(13) 0.31693(12) 0.0229(3) Uani 1 1 d . . .
H19C H 0.3563 0.3893 0.3197 0.027 Uiso 1 1 calc R . .
H19D H 0.4654 0.5098 0.3939 0.027 Uiso 1 1 calc R . .
C11A C 0.87412(13) 0.31220(13) 0.44054(13) 0.0248(3) Uani 1 1 d . . .
H11A H 0.8279 0.3734 0.4631 0.030 Uiso 1 1 calc R . .
C10A C 0.84926(13) 0.20124(13) 0.46392(12) 0.0227(3) Uani 1 1 d . . .
H10A H 0.7854 0.1866 0.5021 0.027 Uiso 1 1 calc R . .


_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
O16A C14A 1.2111(15) . ?
O15A C14A 1.3314(15) . ?
O15A H15A 0.8400 . ?
O16B C14B 1.2109(15) . ?
O15B C14B 1.3343(16) . ?
O15B H15B 0.8400 . ?
N1B C6B 1.3480(16) . ?
N1B C2B 1.3520(16) . ?
N1A C6A 1.3443(16) . ?
N1A C2A 1.3506(16) . ?
N7B C2B 1.3790(16) . ?
N7B C8B 1.4331(16) . ?
N7B C17B 1.4701(16) . ?
N7A C2A 1.3749(16) . ?
N7A C8A 1.4327(16) . ?
N7A C17A 1.4789(16) . ?
C18B C17B 1.5235(17) . ?
C18B C19B 1.5239(19) . ?
C18B H18A 0.9900 . ?
C18B H18B 0.9900 . ?
C9A C10A 1.3891(19) . ?
C9A C8A 1.3944(18) . ?
C9A H9A 0.9500 . ?
C14A C3A 1.4909(18) . ?
C9B C8B 1.3923(17) . ?
C9B C10B 1.3927(19) . ?
C9B H9B 0.9500 . ?
C13A C8A 1.3909(18) . ?
C13A C12A 1.3946(19) . ?
C13A H13A 0.9500 . ?
C17B H17A 0.9900 . ?
C17B H17B 0.9900 . ?
C17A C18A 1.5235(18) . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C2A C3A 1.4234(17) . ?
C6B C5B 1.3756(19) . ?
C6B H6B 0.9500 . ?
C12B C11B 1.3854(19) . ?
C12B C13B 1.3891(18) . ?
C12B H12B 0.9500 . ?
C3B C4B 1.3818(18) . ?
C3B C2B 1.4216(18) . ?
C3B C14B 1.4970(18) . ?
C18A C19A 1.5245(17) . ?
C18A H18C 0.9900 . ?
C18A H18D 0.9900 . ?
C13B C8B 1.3928(18) . ?
C13B H13B 0.9500 . ?
C12A C11A 1.383(2) . ?
C12A H12A 0.9500 . ?
C5B C4B 1.3884(18) . ?
C5B H5B 0.9500 . ?
C4B H4B 0.9500 . ?
C3A C4A 1.3841(18) . ?
C4A C5A 1.3894(19) . ?
C4A H4A 0.9500 . ?
C10B C11B 1.3887(19) . ?
C10B H10B 0.9500 . ?
C6A C5A 1.3742(19) . ?
C6A H6A 0.9500 . ?
C11B H11B 0.9500 . ?
C19A C20A 1.520(2) . ?
C19A H19A 0.9900 . ?
C19A H19B 0.9900 . ?
C5A H5A 0.9500 . ?
C20B C19B 1.523(2) . ?
C20B H20A 0.9800 . ?
C20B H20B 0.9800 . ?
C20B H20C 0.9800 . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
C20A H20F 0.9800 . ?
C19B H19C 0.9900 . ?
C19B H19D 0.9900 . ?
C11A C10A 1.388(2) . ?
C11A H11A 0.9500 . ?
C10A H10A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14A O15A H15A 109.5 . . ?
C14B O15B H15B 109.5 . . ?
C6B N1B C2B 118.98(11) . . ?
C6A N1A C2A 119.23(11) . . ?
C2B N7B C8B 121.42(10) . . ?
C2B N7B C17B 120.21(10) . . ?
C8B N7B C17B 115.41(10) . . ?
C2A N7A C8A 122.12(10) . . ?
C2A N7A C17A 119.72(10) . . ?
C8A N7A C17A 115.29(10) . . ?
C17B C18B C19B 112.25(11) . . ?
C17B C18B H18A 109.2 . . ?
C19B C18B H18A 109.2 . . ?
C17B C18B H18B 109.2 . . ?
C19B C18B H18B 109.2 . . ?
H18A C18B H18B 107.9 . . ?
C10A C9A C8A 119.70(12) . . ?
C10A C9A H9A 120.1 . . ?
C8A C9A H9A 120.1 . . ?
O16A C14A O15A 124.26(12) . . ?
O16A C14A C3A 122.53(11) . . ?
O15A C14A C3A 113.10(11) . . ?
C8B C9B C10B 119.81(12) . . ?
C8B C9B H9B 120.1 . . ?
C10B C9B H9B 120.1 . . ?
C8A C13A C12A 120.05(13) . . ?
C8A C13A H13A 120.0 . . ?
C12A C13A H13A 120.0 . . ?
N7B C17B C18B 113.66(10) . . ?
N7B C17B H17A 108.8 . . ?
C18B C17B H17A 108.8 . . ?
N7B C17B H17B 108.8 . . ?
C18B C17B H17B 108.8 . . ?
H17A C17B H17B 107.7 . . ?
N7A C17A C18A 112.68(10) . . ?
N7A C17A H17C 109.1 . . ?
C18A C17A H17C 109.1 . . ?
N7A C17A H17D 109.1 . . ?
C18A C17A H17D 109.1 . . ?
H17C C17A H17D 107.8 . . ?
N1A C2A N7A 117.04(11) . . ?
N1A C2A C3A 120.06(11) . . ?
N7A C2A C3A 122.89(11) . . ?
N1B C6B C5B 123.97(12) . . ?
N1B C6B H6B 118.0 . . ?
C5B C6B H6B 118.0 . . ?
C13A C8A C9A 119.73(12) . . ?
C13A C8A N7A 120.80(11) . . ?
C9A C8A N7A 119.45(11) . . ?
C11B C12B C13B 120.36(12) . . ?
C11B C12B H12B 119.8 . . ?
C13B C12B H12B 119.8 . . ?
C4B C3B C2B 118.48(12) . . ?
C4B C3B C14B 117.05(11) . . ?
C2B C3B C14B 124.16(11) . . ?
C17A C18A C19A 112.45(10) . . ?
C17A C18A H18C 109.1 . . ?
C19A C18A H18C 109.1 . . ?
C17A C18A H18D 109.1 . . ?
C19A C18A H18D 109.1 . . ?
H18C C18A H18D 107.8 . . ?
C12B C13B C8B 120.35(12) . . ?
C12B C13B H13B 119.8 . . ?
C8B C13B H13B 119.8 . . ?
C11A C12A C13A 120.20(13) . . ?
C11A C12A H12A 119.9 . . ?
C13A C12A H12A 119.9 . . ?
N1B C2B N7B 117.35(11) . . ?
N1B C2B C3B 120.40(11) . . ?
N7B C2B C3B 122.24(11) . . ?
C6B C5B C4B 117.20(12) . . ?
C6B C5B H5B 121.4 . . ?
C4B C5B H5B 121.4 . . ?
C9B C8B C13B 119.43(12) . . ?
C9B C8B N7B 120.49(11) . . ?
C13B C8B N7B 120.03(11) . . ?
C3B C4B C5B 120.82(12) . . ?
C3B C4B H4B 119.6 . . ?
C5B C4B H4B 119.6 . . ?
C4A C3A C2A 118.64(12) . . ?
C4A C3A C14A 118.09(12) . . ?
C2A C3A C14A 122.59(11) . . ?
C3A C4A C5A 120.63(12) . . ?
C3A C4A H4A 119.7 . . ?
C5A C4A H4A 119.7 . . ?
C11B C10B C9B 120.66(12) . . ?
C11B C10B H10B 119.7 . . ?
C9B C10B H10B 119.7 . . ?
N1A C6A C5A 124.14(12) . . ?
N1A C6A H6A 117.9 . . ?
C5A C6A H6A 117.9 . . ?
C12B C11B C10B 119.39(12) . . ?
C12B C11B H11B 120.3 . . ?
C10B C11B H11B 120.3 . . ?
C20A C19A C18A 111.10(11) . . ?
C20A C19A H19A 109.4 . . ?
C18A C19A H19A 109.4 . . ?
C20A C19A H19B 109.4 . . ?
C18A C19A H19B 109.4 . . ?
H19A C19A H19B 108.0 . . ?
C6A C5A C4A 117.12(12) . . ?
C6A C5A H5A 121.4 . . ?
C4A C5A H5A 121.4 . . ?
C19B C20B H20A 109.5 . . ?
C19B C20B H20B 109.5 . . ?
H20A C20B H20B 109.5 . . ?
C19B C20B H20C 109.5 . . ?
H20A C20B H20C 109.5 . . ?
H20B C20B H20C 109.5 . . ?
O16B C14B O15B 123.92(12) . . ?
O16B C14B C3B 124.31(12) . . ?
O15B C14B C3B 111.71(10) . . ?
C19A C20A H20D 109.5 . . ?
C19A C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
C19A C20A H20F 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
C20B C19B C18B 112.42(12) . . ?
C20B C19B H19C 109.1 . . ?
C18B C19B H19C 109.1 . . ?
C20B C19B H19D 109.1 . . ?
C18B C19B H19D 109.1 . . ?
H19C C19B H19D 107.9 . . ?
C12A C11A C10A 119.71(12) . . ?
C12A C11A H11A 120.1 . . ?
C10A C11A H11A 120.1 . . ?
C11A C10A C9A 120.60(13) . . ?
C11A C10A H10A 119.7 . . ?
C9A C10A H10A 119.7 . . ?

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
C2B N7B C17B C18B 93.15(13) . . . . ?
C8B N7B C17B C18B -67.67(14) . . . . ?
C19B C18B C17B N7B 179.30(11) . . . . ?
C2A N7A C17A C18A -85.07(13) . . . . ?
C8A N7A C17A C18A 76.15(13) . . . . ?
C6A N1A C2A N7A 178.50(11) . . . . ?
C6A N1A C2A C3A -2.28(18) . . . . ?
C8A N7A C2A N1A -152.02(11) . . . . ?
C17A N7A C2A N1A 7.88(17) . . . . ?
C8A N7A C2A C3A 28.78(18) . . . . ?
C17A N7A C2A C3A -171.32(11) . . . . ?
C2B N1B C6B C5B 1.78(19) . . . . ?
C12A C13A C8A C9A 0.45(19) . . . . ?
C12A C13A C8A N7A 179.13(12) . . . . ?
C10A C9A C8A C13A 0.03(19) . . . . ?
C10A C9A C8A N7A -178.67(11) . . . . ?
C2A N7A C8A C13A 41.38(17) . . . . ?
C17A N7A C8A C13A -119.34(13) . . . . ?
C2A N7A C8A C9A -139.93(12) . . . . ?
C17A N7A C8A C9A 59.35(15) . . . . ?
N7A C17A C18A C19A -179.89(10) . . . . ?
C11B C12B C13B C8B 0.14(19) . . . . ?
C8A C13A C12A C11A -0.5(2) . . . . ?
C6B N1B C2B N7B -178.67(10) . . . . ?
C6B N1B C2B C3B 1.85(17) . . . . ?
C8B N7B C2B N1B 145.17(11) . . . . ?
C17B N7B C2B N1B -14.48(16) . . . . ?
C8B N7B C2B C3B -35.36(17) . . . . ?
C17B N7B C2B C3B 164.99(11) . . . . ?
C4B C3B C2B N1B -4.13(18) . . . . ?
C14B C3B C2B N1B 169.26(11) . . . . ?
C4B C3B C2B N7B 176.42(11) . . . . ?
C14B C3B C2B N7B -10.20(19) . . . . ?
N1B C6B C5B C4B -2.95(19) . . . . ?
C10B C9B C8B C13B -1.09(19) . . . . ?
C10B C9B C8B N7B -178.42(11) . . . . ?
C12B C13B C8B C9B 0.58(19) . . . . ?
C12B C13B C8B N7B 177.91(11) . . . . ?
C2B N7B C8B C9B -39.64(17) . . . . ?
C17B N7B C8B C9B 120.93(12) . . . . ?
C2B N7B C8B C13B 143.05(12) . . . . ?
C17B N7B C8B C13B -56.38(15) . . . . ?
C2B C3B C4B C5B 2.91(19) . . . . ?
C14B C3B C4B C5B -170.95(12) . . . . ?
C6B C5B C4B C3B 0.46(19) . . . . ?
N1A C2A C3A C4A 4.77(18) . . . . ?
N7A C2A C3A C4A -176.06(12) . . . . ?
N1A C2A C3A C14A -165.52(11) . . . . ?
N7A C2A C3A C14A 13.65(18) . . . . ?
O16A C14A C3A C4A -128.32(13) . . . . ?
O15A C14A C3A C4A 48.07(16) . . . . ?
O16A C14A C3A C2A 42.02(18) . . . . ?
O15A C14A C3A C2A -141.59(12) . . . . ?
C2A C3A C4A C5A -3.40(19) . . . . ?
C14A C3A C4A C5A 167.33(12) . . . . ?
C8B C9B C10B C11B 0.91(19) . . . . ?
C2A N1A C6A C5A -1.7(2) . . . . ?
C13B C12B C11B C10B -0.33(19) . . . . ?
C9B C10B C11B C12B -0.2(2) . . . . ?
C17A C18A C19A C20A -174.76(12) . . . . ?
N1A C6A C5A C4A 3.0(2) . . . . ?
C3A C4A C5A C6A -0.3(2) . . . . ?
C4B C3B C14B O16B 132.46(14) . . . . ?
C2B C3B C14B O16B -41.01(19) . . . . ?
C4B C3B C14B O15B -44.71(15) . . . . ?
C2B C3B C14B O15B 141.82(12) . . . . ?
C17B C18B C19B C20B -176.90(12) . . . . ?
C13A C12A C11A C10A 0.1(2) . . . . ?
C12A C11A C10A C9A 0.4(2) . . . . ?
C8A C9A C10A C11A -0.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_k10257
_audit_block_doi                 10.5517/cc1k2ysc
_database_code_depnum_ccdc_archive 'CCDC 1432813'
_audit_update_record             
;
2015-10-23 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 N2 O2'
_chemical_formula_sum            'C14 H14 N2 O2'
_chemical_formula_weight         242.27

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   34.4290(3)
_cell_length_b                   7.45830(10)
_cell_length_c                   24.2139(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 126.0307(5)
_cell_angle_gamma                90.00
_cell_volume                     5028.25(10)
_cell_formula_units_Z            16
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    6150
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2048
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9660
_exptl_absorpt_correction_T_max  0.9828
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 18
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11044
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.46
_diffrn_reflns_theta_max         27.47
_reflns_number_total             5747
_reflns_number_gt                4394
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'COLLECT (Nonius, 1997)'
_computing_cell_refinement       'DENZO-SMN (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Nonius, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Bruker, 1995)'
_computing_publication_material  'SHELX-97 and local procedures'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0732P)²+1.8305P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5747
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1289
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1B N 0.57821(4) 0.08796(16) 0.18004(6) 0.0178(2) Uani 1 1 d . . .
C2B C 0.61948(5) 0.12572(18) 0.24121(6) 0.0163(3) Uani 1 1 d . . .
C3B C 0.66423(5) 0.11778(18) 0.25075(7) 0.0175(3) Uani 1 1 d . . .
C4B C 0.66452(5) 0.08475(19) 0.19479(7) 0.0196(3) Uani 1 1 d . . .
H4B H 0.6940 0.0862 0.1996 0.024 Uiso 1 1 calc R . .
C5B C 0.62177(5) 0.04950(19) 0.13159(7) 0.0202(3) Uani 1 1 d . . .
H5B H 0.6213 0.0268 0.0926 0.024 Uiso 1 1 calc R . .
C6B C 0.58001(5) 0.04844(18) 0.12724(7) 0.0185(3) Uani 1 1 d . . .
H6B H 0.5509 0.0182 0.0847 0.022 Uiso 1 1 calc R . .
N7B N 0.61740(4) 0.17368(16) 0.29443(6) 0.0200(3) Uani 1 1 d . . .
C8B C 0.64504(5) 0.32506(19) 0.33558(7) 0.0193(3) Uani 1 1 d . . .
C9B C 0.64673(5) 0.4797(2) 0.30526(7) 0.0238(3) Uani 1 1 d . . .
H9B H 0.6298 0.4847 0.2571 0.029 Uiso 1 1 calc R . .
C10B C 0.67297(6) 0.6274(2) 0.34496(8) 0.0276(3) Uani 1 1 d . . .
H10B H 0.6743 0.7325 0.3240 0.033 Uiso 1 1 calc R . .
C11B C 0.69702(5) 0.6214(2) 0.41486(8) 0.0290(4) Uani 1 1 d . . .
H11B H 0.7147 0.7229 0.4419 0.035 Uiso 1 1 calc R . .
C12B C 0.69554(5) 0.4675(2) 0.44582(8) 0.0289(4) Uani 1 1 d . . .
H12B H 0.7121 0.4638 0.4940 0.035 Uiso 1 1 calc R . .
C13B C 0.66981(5) 0.3187(2) 0.40635(7) 0.0241(3) Uani 1 1 d . . .
H13B H 0.6691 0.2128 0.4275 0.029 Uiso 1 1 calc R . .
C14B C 0.71153(5) 0.12896(19) 0.31977(7) 0.0187(3) Uani 1 1 d . . .
O15B O 0.72102(4) 0.04581(14) 0.36923(5) 0.0250(2) Uani 1 1 d . . .
O16B O 0.74215(3) 0.23398(15) 0.31862(5) 0.0257(2) Uani 1 1 d . . .
H16B H 0.7675 0.2439 0.3583 0.039 Uiso 1 1 calc R . .
C17B C 0.57524(5) 0.1258(2) 0.29293(7) 0.0213(3) Uani 1 1 d . . .
H17A H 0.5461 0.1772 0.2513 0.026 Uiso 1 1 calc R . .
H17B H 0.5788 0.1796 0.3330 0.026 Uiso 1 1 calc R . .
C18B C 0.56892(6) -0.0750(2) 0.29350(8) 0.0278(3) Uani 1 1 d . . .
H18A H 0.5611 -0.1270 0.2509 0.042 Uiso 1 1 calc R . .
H18B H 0.5428 -0.0999 0.2976 0.042 Uiso 1 1 calc R . .
H18C H 0.5988 -0.1282 0.3324 0.042 Uiso 1 1 calc R . .
N1A N 0.67766(4) 0.18505(17) 0.56145(6) 0.0200(3) Uani 1 1 d . . .
C2A C 0.63103(5) 0.23372(18) 0.51955(6) 0.0162(3) Uani 1 1 d . . .
C3A C 0.59596(5) 0.10988(18) 0.47082(6) 0.0159(3) Uani 1 1 d . . .
C4A C 0.61145(5) -0.05249(18) 0.46255(7) 0.0182(3) Uani 1 1 d . . .
H4A H 0.5887 -0.1344 0.4287 0.022 Uiso 1 1 calc R . .
C5A C 0.65995(5) -0.0969(2) 0.50328(7) 0.0218(3) Uani 1 1 d . . .
H5A H 0.6712 -0.2058 0.4970 0.026 Uiso 1 1 calc R . .
C6A C 0.69092(5) 0.0238(2) 0.55300(7) 0.0220(3) Uani 1 1 d . . .
H6A H 0.7238 -0.0088 0.5834 0.026 Uiso 1 1 calc R . .
N7A N 0.62002(4) 0.40416(16) 0.52786(6) 0.0193(3) Uani 1 1 d . . .
C8A C 0.57654(5) 0.49090(18) 0.47547(7) 0.0186(3) Uani 1 1 d . . .
C9A C 0.54866(5) 0.57875(19) 0.49147(7) 0.0225(3) Uani 1 1 d . . .
H9A H 0.5592 0.5846 0.5376 0.027 Uiso 1 1 calc R . .
C10A C 0.50558(6) 0.6576(2) 0.44040(8) 0.0267(3) Uani 1 1 d . . .
H10A H 0.4867 0.7175 0.4515 0.032 Uiso 1 1 calc R . .
C11A C 0.48995(6) 0.6491(2) 0.37294(8) 0.0275(3) Uani 1 1 d . . .
H11A H 0.4599 0.6995 0.3377 0.033 Uiso 1 1 calc R . .
C12A C 0.51842(6) 0.56680(19) 0.35718(7) 0.0243(3) Uani 1 1 d . . .
H12A H 0.5080 0.5629 0.3111 0.029 Uiso 1 1 calc R . .
C13A C 0.56200(5) 0.49020(19) 0.40810(7) 0.0203(3) Uani 1 1 d . . .
H13A H 0.5819 0.4375 0.3972 0.024 Uiso 1 1 calc R . .
C14A C 0.54336(5) 0.12870(17) 0.43790(6) 0.0160(3) Uani 1 1 d . . .
O15A O 0.52802(3) 0.16508(14) 0.47050(5) 0.0217(2) Uani 1 1 d . . .
O16A O 0.51644(3) 0.08885(13) 0.37183(4) 0.0192(2) Uani 1 1 d . . .
H16A H 0.4873 0.0937 0.3563 0.029 Uiso 1 1 calc R . .
C17A C 0.65483(5) 0.5072(2) 0.59025(7) 0.0235(3) Uani 1 1 d . . .
H17C H 0.6449 0.6346 0.5826 0.028 Uiso 1 1 calc R . .
H17D H 0.6868 0.5006 0.5991 0.028 Uiso 1 1 calc R . .
C18A C 0.65908(6) 0.4396(2) 0.65294(7) 0.0309(4) Uani 1 1 d . . .
H18D H 0.6276 0.4464 0.6447 0.046 Uiso 1 1 calc R . .
H18E H 0.6822 0.5140 0.6925 0.046 Uiso 1 1 calc R . .
H18F H 0.6702 0.3149 0.6620 0.046 Uiso 1 1 calc R . .


_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
N1B C2B 1.3477(17) . ?
N1B C6B 1.3487(17) . ?
C2B N7B 1.3794(17) . ?
C2B C3B 1.4182(19) . ?
C3B C4B 1.3831(19) . ?
C3B C14B 1.5001(18) . ?
C4B C5B 1.3882(19) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.378(2) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
N7B C8B 1.4344(17) . ?
N7B C17B 1.4743(17) . ?
C8B C9B 1.386(2) . ?
C8B C13B 1.3954(19) . ?
C9B C10B 1.390(2) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.380(2) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.388(2) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.391(2) . ?
C12B H12B 0.9500 . ?
C13B H13B 0.9500 . ?
C14B O15B 1.2104(17) . ?
C14B O16B 1.3267(17) . ?
O16B H16B 0.8400 . ?
C17B C18B 1.515(2) . ?
C17B H17A 0.9900 . ?
C17B H17B 0.9900 . ?
C18B H18A 0.9800 . ?
C18B H18B 0.9800 . ?
C18B H18C 0.9800 . ?
N1A C6A 1.3442(19) . ?
N1A C2A 1.3499(17) . ?
C2A N7A 1.3746(18) . ?
C2A C3A 1.4238(18) . ?
C3A C4A 1.3844(19) . ?
C3A C14A 1.4957(18) . ?
C4A C5A 1.390(2) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.373(2) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
N7A C8A 1.4263(18) . ?
N7A C17A 1.4762(17) . ?
C8A C9A 1.392(2) . ?
C8A C13A 1.3967(19) . ?
C9A C10A 1.385(2) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.389(2) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.387(2) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.386(2) . ?
C12A H12A 0.9500 . ?
C13A H13A 0.9500 . ?
C14A O15A 1.2108(16) . ?
C14A O16A 1.3274(15) . ?
O16A H16A 0.8400 . ?
C17A C18A 1.523(2) . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 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
C2B N1B C6B 118.73(12) . . ?
N1B C2B N7B 118.71(12) . . ?
N1B C2B C3B 120.83(12) . . ?
N7B C2B C3B 120.46(12) . . ?
C4B C3B C2B 118.75(12) . . ?
C4B C3B C14B 118.21(12) . . ?
C2B C3B C14B 122.86(12) . . ?
C3B C4B C5B 119.98(13) . . ?
C3B C4B H4B 120.0 . . ?
C5B C4B H4B 120.0 . . ?
C6B C5B C4B 117.85(13) . . ?
C6B C5B H5B 121.1 . . ?
C4B C5B H5B 121.1 . . ?
N1B C6B C5B 123.63(12) . . ?
N1B C6B H6B 118.2 . . ?
C5B C6B H6B 118.2 . . ?
C2B N7B C8B 118.37(11) . . ?
C2B N7B C17B 120.37(11) . . ?
C8B N7B C17B 116.69(11) . . ?
C9B C8B C13B 119.54(13) . . ?
C9B C8B N7B 120.28(12) . . ?
C13B C8B N7B 120.17(13) . . ?
C8B C9B C10B 120.39(14) . . ?
C8B C9B H9B 119.8 . . ?
C10B C9B H9B 119.8 . . ?
C11B C10B C9B 119.94(15) . . ?
C11B C10B H10B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
C10B C11B C12B 120.22(14) . . ?
C10B C11B H11B 119.9 . . ?
C12B C11B H11B 119.9 . . ?
C11B C12B C13B 119.98(14) . . ?
C11B C12B H12B 120.0 . . ?
C13B C12B H12B 120.0 . . ?
C12B C13B C8B 119.91(14) . . ?
C12B C13B H13B 120.0 . . ?
C8B C13B H13B 120.0 . . ?
O15B C14B O16B 124.59(12) . . ?
O15B C14B C3B 123.93(12) . . ?
O16B C14B C3B 111.39(11) . . ?
C14B O16B H16B 109.5 . . ?
N7B C17B C18B 112.58(12) . . ?
N7B C17B H17A 109.1 . . ?
C18B C17B H17A 109.1 . . ?
N7B C17B H17B 109.1 . . ?
C18B C17B H17B 109.1 . . ?
H17A C17B H17B 107.8 . . ?
C17B C18B H18A 109.5 . . ?
C17B C18B H18B 109.5 . . ?
H18A C18B H18B 109.5 . . ?
C17B C18B H18C 109.5 . . ?
H18A C18B H18C 109.5 . . ?
H18B C18B H18C 109.5 . . ?
C6A N1A C2A 119.11(12) . . ?
N1A C2A N7A 116.56(12) . . ?
N1A C2A C3A 120.14(12) . . ?
N7A C2A C3A 123.29(12) . . ?
C4A C3A C2A 118.45(12) . . ?
C4A C3A C14A 116.98(12) . . ?
C2A C3A C14A 123.47(12) . . ?
C3A C4A C5A 120.64(13) . . ?
C3A C4A H4A 119.7 . . ?
C5A C4A H4A 119.7 . . ?
C6A C5A C4A 117.07(13) . . ?
C6A C5A H5A 121.5 . . ?
C4A C5A H5A 121.5 . . ?
N1A C6A C5A 124.17(13) . . ?
N1A C6A H6A 117.9 . . ?
C5A C6A H6A 117.9 . . ?
C2A N7A C8A 121.65(11) . . ?
C2A N7A C17A 120.22(11) . . ?
C8A N7A C17A 118.01(11) . . ?
C9A C8A C13A 119.64(13) . . ?
C9A C8A N7A 120.04(12) . . ?
C13A C8A N7A 120.31(13) . . ?
C10A C9A C8A 120.20(13) . . ?
C10A C9A H9A 119.9 . . ?
C8A C9A H9A 119.9 . . ?
C9A C10A C11A 120.11(14) . . ?
C9A C10A H10A 119.9 . . ?
C11A C10A H10A 119.9 . . ?
C12A C11A C10A 119.76(14) . . ?
C12A C11A H11A 120.1 . . ?
C10A C11A H11A 120.1 . . ?
C13A C12A C11A 120.53(13) . . ?
C13A C12A H12A 119.7 . . ?
C11A C12A H12A 119.7 . . ?
C12A C13A C8A 119.62(13) . . ?
C12A C13A H13A 120.2 . . ?
C8A C13A H13A 120.2 . . ?
O15A C14A O16A 124.94(12) . . ?
O15A C14A C3A 121.96(12) . . ?
O16A C14A C3A 112.92(11) . . ?
C14A O16A H16A 109.5 . . ?
N7A C17A C18A 113.08(12) . . ?
N7A C17A H17C 109.0 . . ?
C18A C17A H17C 109.0 . . ?
N7A C17A H17D 109.0 . . ?
C18A C17A H17D 109.0 . . ?
H17C C17A H17D 107.8 . . ?
C17A C18A H18D 109.5 . . ?
C17A C18A H18E 109.5 . . ?
H18D C18A H18E 109.5 . . ?
C17A C18A H18F 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 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
C6B N1B C2B N7B 177.24(12) . . . . ?
C6B N1B C2B C3B -2.30(19) . . . . ?
N1B C2B C3B C4B 5.2(2) . . . . ?
N7B C2B C3B C4B -174.34(13) . . . . ?
N1B C2B C3B C14B -169.77(12) . . . . ?
N7B C2B C3B C14B 10.7(2) . . . . ?
C2B C3B C4B C5B -3.9(2) . . . . ?
C14B C3B C4B C5B 171.34(13) . . . . ?
C3B C4B C5B C6B -0.2(2) . . . . ?
C2B N1B C6B C5B -2.0(2) . . . . ?
C4B C5B C6B N1B 3.2(2) . . . . ?
N1B C2B N7B C8B -134.35(13) . . . . ?
C3B C2B N7B C8B 45.19(18) . . . . ?
N1B C2B N7B C17B 20.89(19) . . . . ?
C3B C2B N7B C17B -159.57(13) . . . . ?
C2B N7B C8B C9B 42.53(18) . . . . ?
C17B N7B C8B C9B -113.61(15) . . . . ?
C2B N7B C8B C13B -138.50(14) . . . . ?
C17B N7B C8B C13B 65.35(17) . . . . ?
C13B C8B C9B C10B 0.2(2) . . . . ?
N7B C8B C9B C10B 179.14(13) . . . . ?
C8B C9B C10B C11B -0.8(2) . . . . ?
C9B C10B C11B C12B 0.7(2) . . . . ?
C10B C11B C12B C13B 0.1(2) . . . . ?
C11B C12B C13B C8B -0.8(2) . . . . ?
C9B C8B C13B C12B 0.6(2) . . . . ?
N7B C8B C13B C12B -178.33(13) . . . . ?
C4B C3B C14B O15B -129.07(15) . . . . ?
C2B C3B C14B O15B 45.9(2) . . . . ?
C4B C3B C14B O16B 47.76(17) . . . . ?
C2B C3B C14B O16B -137.25(14) . . . . ?
C2B N7B C17B C18B 63.52(17) . . . . ?
C8B N7B C17B C18B -140.84(12) . . . . ?
C6A N1A C2A N7A -176.18(12) . . . . ?
C6A N1A C2A C3A 5.01(19) . . . . ?
N1A C2A C3A C4A -6.93(19) . . . . ?
N7A C2A C3A C4A 174.35(12) . . . . ?
N1A C2A C3A C14A 160.70(12) . . . . ?
N7A C2A C3A C14A -18.0(2) . . . . ?
C2A C3A C4A C5A 3.09(19) . . . . ?
C14A C3A C4A C5A -165.34(12) . . . . ?
C3A C4A C5A C6A 2.4(2) . . . . ?
C2A N1A C6A C5A 0.8(2) . . . . ?
C4A C5A C6A N1A -4.6(2) . . . . ?
N1A C2A N7A C8A 160.49(12) . . . . ?
C3A C2A N7A C8A -20.74(19) . . . . ?
N1A C2A N7A C17A -15.48(18) . . . . ?
C3A C2A N7A C17A 163.29(13) . . . . ?
C2A N7A C8A C9A 133.56(14) . . . . ?
C17A N7A C8A C9A -50.39(18) . . . . ?
C2A N7A C8A C13A -47.24(19) . . . . ?
C17A N7A C8A C13A 128.81(14) . . . . ?
C13A C8A C9A C10A 3.1(2) . . . . ?
N7A C8A C9A C10A -177.67(13) . . . . ?
C8A C9A C10A C11A 0.1(2) . . . . ?
C9A C10A C11A C12A -2.2(2) . . . . ?
C10A C11A C12A C13A 1.1(2) . . . . ?
C11A C12A C13A C8A 2.1(2) . . . . ?
C9A C8A C13A C12A -4.2(2) . . . . ?
N7A C8A C13A C12A 176.59(13) . . . . ?
C4A C3A C14A O15A 122.20(14) . . . . ?
C2A C3A C14A O15A -45.59(19) . . . . ?
C4A C3A C14A O16A -53.21(16) . . . . ?
C2A C3A C14A O16A 138.99(13) . . . . ?
C2A N7A C17A C18A -73.13(17) . . . . ?
C8A N7A C17A C18A 110.76(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O16B H16B N1A 0.84 1.82 2.6436(15) 167.6 7_656
O16A H16A N1B 0.84 1.88 2.7167(15) 176.1 2_655

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.064
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_k10044
_audit_block_doi                 10.5517/cc1k2zby
_database_code_depnum_ccdc_archive 'CCDC 1432830'
_audit_update_record             
;
2015-10-23 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N2 O2, C7 H8'
_chemical_formula_sum            'C23 H26 N2 O2'
_chemical_formula_weight         362.46

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.2030(2)
_cell_length_b                   14.0780(2)
_cell_length_c                   13.0633(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.6710(7)
_cell_angle_gamma                90.00
_cell_volume                     1983.71(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    4709
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9696
_exptl_absorpt_correction_T_max  0.9771
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 18
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8901
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4547
_reflns_number_gt                3309
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'COLLECT (Nonius, 1997)'
_computing_cell_refinement       'DENZO-SMN (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Nonius, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Bruker, 1995)'
_computing_publication_material  'SHELX-97 and local procedures'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0844P)²+0.0226P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4547
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1408
_refine_ls_wR_factor_gt          0.1225
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.46132(10) 0.21712(8) 0.23732(8) 0.0194(3) Uani 1 1 d . . .
C1S C 1.04264(14) 0.33886(11) 0.57484(12) 0.0290(4) Uani 1 1 d . . .
C2 C 0.49612(12) 0.12735(9) 0.22473(10) 0.0179(3) Uani 1 1 d . . .
C2S C 0.93357(14) 0.36544(12) 0.50055(12) 0.0306(4) Uani 1 1 d . . .
H2S H 0.8903 0.4204 0.5130 0.037 Uiso 1 1 calc R . .
C3 C 0.46385(12) 0.05168(9) 0.28447(10) 0.0179(3) Uani 1 1 d . . .
C3S C 0.88717(15) 0.31305(12) 0.40886(12) 0.0352(4) Uani 1 1 d . . .
H3S H 0.8126 0.3323 0.3590 0.042 Uiso 1 1 calc R . .
C4 C 0.40735(12) 0.07365(9) 0.36309(10) 0.0200(3) Uani 1 1 d . . .
H4 H 0.3909 0.0248 0.4076 0.024 Uiso 1 1 calc R . .
C4S C 0.94860(16) 0.23303(12) 0.38942(12) 0.0366(4) Uani 1 1 d . . .
H4S H 0.9169 0.1972 0.3263 0.044 Uiso 1 1 calc R . .
C5 C 0.37438(13) 0.16699(9) 0.37747(11) 0.0219(3) Uani 1 1 d . . .
H5 H 0.3354 0.1831 0.4313 0.026 Uiso 1 1 calc R . .
C5S C 1.05681(16) 0.20538(11) 0.46279(13) 0.0356(4) Uani 1 1 d . . .
H5S H 1.0996 0.1503 0.4499 0.043 Uiso 1 1 calc R . .
C6 C 0.40002(12) 0.23476(10) 0.31129(10) 0.0220(3) Uani 1 1 d . . .
H6 H 0.3731 0.2979 0.3178 0.026 Uiso 1 1 calc R . .
C6S C 1.10319(14) 0.25734(11) 0.55469(12) 0.0306(4) Uani 1 1 d . . .
H6S H 1.1772 0.2373 0.6047 0.037 Uiso 1 1 calc R . .
N7 N 0.56260(10) 0.11143(8) 0.15136(8) 0.0190(3) Uani 1 1 d . . .
C7S C 1.09383(17) 0.39748(13) 0.67309(12) 0.0417(4) Uani 1 1 d . . .
H7S1 H 1.1183 0.3556 0.7352 0.063 Uiso 1 1 calc R . .
H7S2 H 1.0303 0.4420 0.6823 0.063 Uiso 1 1 calc R . .
H7S3 H 1.1663 0.4330 0.6659 0.063 Uiso 1 1 calc R . .
C8 C 0.65757(13) 0.04029(9) 0.17065(10) 0.0205(3) Uani 1 1 d . . .
C9 C 0.67472(14) -0.01301(10) 0.08577(11) 0.0256(3) Uani 1 1 d . . .
H9 H 0.6208 -0.0049 0.0165 0.031 Uiso 1 1 calc R . .
C10 C 0.77112(15) -0.07794(10) 0.10342(13) 0.0324(4) Uani 1 1 d . . .
H10 H 0.7834 -0.1138 0.0455 0.039 Uiso 1 1 calc R . .
C11 C 0.84994(15) -0.09131(11) 0.20433(14) 0.0348(4) Uani 1 1 d . . .
H11 H 0.9153 -0.1364 0.2157 0.042 Uiso 1 1 calc R . .
C12 C 0.83230(14) -0.03814(11) 0.28826(13) 0.0307(4) Uani 1 1 d . . .
H12 H 0.8857 -0.0469 0.3577 0.037 Uiso 1 1 calc R . .
C13 C 0.73722(13) 0.02765(10) 0.27142(11) 0.0243(3) Uani 1 1 d . . .
H13 H 0.7264 0.0644 0.3292 0.029 Uiso 1 1 calc R . .
C14 C 0.47166(12) -0.04990(9) 0.25500(10) 0.0191(3) Uani 1 1 d . . .
O15 O 0.43074(9) -0.07840(7) 0.16461(7) 0.0263(3) Uani 1 1 d . . .
O16 O 0.52032(9) -0.10598(6) 0.33745(7) 0.0232(2) Uani 1 1 d . . .
H16 H 0.5213 -0.1623 0.3163 0.035 Uiso 1 1 calc R . .
C17 C 0.57540(13) 0.18715(9) 0.07719(10) 0.0206(3) Uani 1 1 d . . .
H17A H 0.5007 0.2280 0.0620 0.025 Uiso 1 1 calc R . .
H17B H 0.5796 0.1579 0.0093 0.025 Uiso 1 1 calc R . .
C18 C 0.68956(12) 0.24880(9) 0.11949(10) 0.0213(3) Uani 1 1 d . . .
H18A H 0.6860 0.2775 0.1878 0.026 Uiso 1 1 calc R . .
H18B H 0.7644 0.2082 0.1336 0.026 Uiso 1 1 calc R . .
C19 C 0.70100(13) 0.32755(9) 0.04304(11) 0.0226(3) Uani 1 1 d . . .
H19A H 0.6263 0.3683 0.0290 0.027 Uiso 1 1 calc R . .
H19B H 0.7047 0.2990 -0.0253 0.027 Uiso 1 1 calc R . .
C20 C 0.81580(14) 0.38864(11) 0.08643(12) 0.0289(3) Uani 1 1 d . . .
H20A H 0.8124 0.4173 0.1539 0.043 Uiso 1 1 calc R . .
H20B H 0.8187 0.4389 0.0352 0.043 Uiso 1 1 calc R . .
H20C H 0.8902 0.3490 0.0981 0.043 Uiso 1 1 calc R . .


_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 C2 1.3457(17) . ?
N1 C6 1.3511(16) . ?
C1S C2S 1.391(2) . ?
C1S C6S 1.394(2) . ?
C1S C7S 1.503(2) . ?
C2 N7 1.3818(16) . ?
C2 C3 1.4237(18) . ?
C2S C3S 1.383(2) . ?
C2S H2S 0.9500 . ?
C3 C4 1.3793(18) . ?
C3 C14 1.4896(18) . ?
C3S C4S 1.379(2) . ?
C3S H3S 0.9500 . ?
C4 C5 1.3914(18) . ?
C4 H4 0.9500 . ?
C4S C5S 1.383(2) . ?
C4S H4S 0.9500 . ?
C5 C6 1.3691(18) . ?
C5 H5 0.9500 . ?
C5S C6S 1.382(2) . ?
C5S H5S 0.9500 . ?
C6 H6 0.9500 . ?
C6S H6S 0.9500 . ?
N7 C8 1.4330(17) . ?
N7 C17 1.4734(16) . ?
C7S H7S1 0.9800 . ?
C7S H7S2 0.9800 . ?
C7S H7S3 0.9800 . ?
C8 C13 1.388(2) . ?
C8 C9 1.3945(18) . ?
C9 C10 1.386(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O15 1.2136(15) . ?
C14 O16 1.3279(15) . ?
O16 H16 0.8400 . ?
C17 C18 1.5207(19) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.5207(18) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.524(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 118.68(11) . . ?
C2S C1S C6S 118.06(14) . . ?
C2S C1S C7S 120.58(14) . . ?
C6S C1S C7S 121.36(15) . . ?
N1 C2 N7 117.72(11) . . ?
N1 C2 C3 120.73(12) . . ?
N7 C2 C3 121.54(11) . . ?
C3S C2S C1S 120.98(15) . . ?
C3S C2S H2S 119.5 . . ?
C1S C2S H2S 119.5 . . ?
C4 C3 C2 118.41(12) . . ?
C4 C3 C14 118.59(12) . . ?
C2 C3 C14 122.37(11) . . ?
C4S C3S C2S 120.37(16) . . ?
C4S C3S H3S 119.8 . . ?
C2S C3S H3S 119.8 . . ?
C3 C4 C5 120.29(12) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C3S C4S C5S 119.35(15) . . ?
C3S C4S H4S 120.3 . . ?
C5S C4S H4S 120.3 . . ?
C6 C5 C4 117.66(12) . . ?
C6 C5 H5 121.2 . . ?
C4 C5 H5 121.2 . . ?
C6S C5S C4S 120.44(16) . . ?
C6S C5S H5S 119.8 . . ?
C4S C5S H5S 119.8 . . ?
N1 C6 C5 123.88(12) . . ?
N1 C6 H6 118.1 . . ?
C5 C6 H6 118.1 . . ?
C5S C6S C1S 120.80(15) . . ?
C5S C6S H6S 119.6 . . ?
C1S C6S H6S 119.6 . . ?
C2 N7 C8 120.33(10) . . ?
C2 N7 C17 120.35(11) . . ?
C8 N7 C17 114.95(10) . . ?
C1S C7S H7S1 109.5 . . ?
C1S C7S H7S2 109.5 . . ?
H7S1 C7S H7S2 109.5 . . ?
C1S C7S H7S3 109.5 . . ?
H7S1 C7S H7S3 109.5 . . ?
H7S2 C7S H7S3 109.5 . . ?
C13 C8 C9 119.59(13) . . ?
C13 C8 N7 120.86(12) . . ?
C9 C8 N7 119.44(12) . . ?
C10 C9 C8 119.42(14) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 121.01(14) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 119.25(14) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C13 C12 C11 120.28(15) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 120.45(13) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
O15 C14 O16 123.85(12) . . ?
O15 C14 C3 122.39(12) . . ?
O16 C14 C3 113.64(11) . . ?
C14 O16 H16 109.5 . . ?
N7 C17 C18 113.30(11) . . ?
N7 C17 H17A 108.9 . . ?
C18 C17 H17A 108.9 . . ?
N7 C17 H17B 108.9 . . ?
C18 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C17 112.91(11) . . ?
C19 C18 H18A 109.0 . . ?
C17 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C17 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 C20 112.31(12) . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 N7 -177.71(11) . . . . ?
C6 N1 C2 C3 3.00(18) . . . . ?
C6S C1S C2S C3S -0.6(2) . . . . ?
C7S C1S C2S C3S 178.64(14) . . . . ?
N1 C2 C3 C4 -6.54(19) . . . . ?
N7 C2 C3 C4 174.19(11) . . . . ?
N1 C2 C3 C14 164.25(12) . . . . ?
N7 C2 C3 C14 -15.02(19) . . . . ?
C1S C2S C3S C4S 0.0(2) . . . . ?
C2 C3 C4 C5 4.91(19) . . . . ?
C14 C3 C4 C5 -166.23(12) . . . . ?
C2S C3S C4S C5S 0.3(2) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C3S C4S C5S C6S -0.1(2) . . . . ?
C2 N1 C6 C5 2.31(19) . . . . ?
C4 C5 C6 N1 -3.8(2) . . . . ?
C4S C5S C6S C1S -0.5(2) . . . . ?
C2S C1S C6S C5S 0.9(2) . . . . ?
C7S C1S C6S C5S -178.38(14) . . . . ?
N1 C2 N7 C8 144.99(12) . . . . ?
C3 C2 N7 C8 -35.72(17) . . . . ?
N1 C2 N7 C17 -10.38(17) . . . . ?
C3 C2 N7 C17 168.92(12) . . . . ?
C2 N7 C8 C13 -40.04(18) . . . . ?
C17 N7 C8 C13 116.58(13) . . . . ?
C2 N7 C8 C9 143.79(13) . . . . ?
C17 N7 C8 C9 -59.58(16) . . . . ?
C13 C8 C9 C10 0.1(2) . . . . ?
N7 C8 C9 C10 176.28(12) . . . . ?
C8 C9 C10 C11 0.6(2) . . . . ?
C9 C10 C11 C12 -0.6(2) . . . . ?
C10 C11 C12 C13 -0.1(2) . . . . ?
C11 C12 C13 C8 0.8(2) . . . . ?
C9 C8 C13 C12 -0.8(2) . . . . ?
N7 C8 C13 C12 -176.94(12) . . . . ?
C4 C3 C14 O15 123.90(14) . . . . ?
C2 C3 C14 O15 -46.87(19) . . . . ?
C4 C3 C14 O16 -52.28(16) . . . . ?
C2 C3 C14 O16 136.95(13) . . . . ?
C2 N7 C17 C18 90.98(14) . . . . ?
C8 N7 C17 C18 -65.64(14) . . . . ?
N7 C17 C18 C19 -179.21(10) . . . . ?
C17 C18 C19 C20 -179.96(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.087
####################################################################### 
# 
# 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_k08176
_audit_block_doi                 10.5517/cc1k2zrc
_database_code_depnum_ccdc_archive 'CCDC 1432843'
_audit_update_record             
;
2015-10-23 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 F N2 O2'
_chemical_formula_sum            'C13 H11 F N2 O2'
_chemical_formula_weight         246.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P n'
_space_group_name_Hall           'P -2yac'

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

_cell_length_a                   5.3295(1)
_cell_length_b                   8.7988(2)
_cell_length_c                   12.3776(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.7900(11)
_cell_angle_gamma                90.00
_cell_volume                     571.97(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    1380
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9680
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 18
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2517
_diffrn_reflns_av_R_equivalents  0.0107
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         27.43
_reflns_number_total             1301
_reflns_number_gt                1279
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_cell_refinement       'DENZO-SMN (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Nonius, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Bruker, 1995)'
_computing_publication_material  'SHELX-97 and local procedures'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0253P)²+0.1437P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1301
_refine_ls_number_parameters     165
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0612
_refine_ls_wR_factor_gt          0.0609
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_f