# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_x

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 N2 O'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C18 H16 N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         276.33
_chemical_compound_source        'see text'

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

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   4.9330(2)
_cell_length_b                   15.0363(7)
_cell_length_c                   18.3873(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.938(5)
_cell_angle_gamma                90
_cell_volume                     1363.07(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    21681
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      26.0
_cell_special_details            
;
;

_exptl_crystal_description       block
_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.085
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction,2009)'
_exptl_absorpt_correction_T_min  0.9750
_exptl_absorpt_correction_T_max  0.9833

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Oxford Xcalibur,Eos(Nova) CCD detector'
_diffrn_measurement_method       'fω scans'
_diffrn_reflns_number            21681
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_reduction_process 
;
;
# number of unique reflections
_reflns_number_total             2671
# number of observed reflections (> n sig(I))
_reflns_number_gt                2173
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlisPro RED (Oxford Diffraction, 2009)'
_computing_structure_solution    'SHELXS97  (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

#===============================================================================

# 8. REFINEMENT DATA
_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)+(0.0452P)²+0.2407P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2671
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1090
_refine_ls_wR_factor_gt          0.1016
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.045

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
O1 O 0.6939(2) 0.71757(7) 0.72223(6) 0.0236(3) Uani 1 1 d . . .
N2 N 0.5065(2) 0.42448(8) 0.88713(7) 0.0164(3) Uani 1 1 d . . .
N3 N 0.3029(2) 0.45506(8) 0.92869(7) 0.0181(3) Uani 1 1 d . . .
C4 C 0.2646(3) 0.54054(10) 0.90548(8) 0.0162(3) Uani 1 1 d . . .
C5 C 0.0797(3) 0.60681(10) 0.92673(9) 0.0184(4) Uani 1 1 d . . .
H5 H -0.0439 0.5963 0.9628 0.022 Uiso 1 1 calc R . .
C6 C 0.9955(3) 0.56929(10) 0.68466(9) 0.0210(4) Uani 1 1 d . . .
H6 H 1.0080 0.6214 0.6578 0.025 Uiso 1 1 calc R . .
C7 C 0.4519(3) 0.27939(10) 0.95191(9) 0.0190(4) Uani 1 1 d . . .
H7A H 0.2652 0.2739 0.9342 0.023 Uiso 1 1 calc R . .
H7B H 0.4527 0.3090 0.9988 0.023 Uiso 1 1 calc R . .
C8 C 0.6557(3) 0.64851(10) 0.75662(9) 0.0183(4) Uani 1 1 d . . .
C9 C 0.8153(3) 0.56541(10) 0.74141(9) 0.0176(4) Uani 1 1 d . . .
C10 C 0.4440(3) 0.56077(10) 0.85043(9) 0.0156(3) Uani 1 1 d . . .
C11 C 0.5976(3) 0.48566(10) 0.83897(9) 0.0161(4) Uani 1 1 d . . .
C12 C 0.4556(3) 0.64242(10) 0.81426(9) 0.0160(3) Uani 1 1 d . . .
C13 C 0.2747(3) 0.70683(10) 0.83585(9) 0.0193(4) Uani 1 1 d . . .
H13 H 0.2736 0.7626 0.8139 0.023 Uiso 1 1 calc R . .
C14 C 0.6111(3) 0.33398(10) 0.89879(9) 0.0183(4) Uani 1 1 d . . .
H14A H 0.7981 0.3377 0.9166 0.022 Uiso 1 1 calc R . .
H14B H 0.6098 0.3033 0.8524 0.022 Uiso 1 1 calc R . .
C15 C 0.0908(3) 0.68764(11) 0.89153(9) 0.0201(4) Uani 1 1 d . . .
H15 H -0.0287 0.7321 0.9050 0.024 Uiso 1 1 calc R . .
C16 C 0.9650(3) 0.41337(10) 0.76482(9) 0.0183(4) Uani 1 1 d . . .
H16 H 0.9581 0.3611 0.7917 0.022 Uiso 1 1 calc R . .
C17 C 0.7960(3) 0.48478(10) 0.78219(8) 0.0162(4) Uani 1 1 d . . .
C18 C 0.5784(3) 0.18710(10) 0.96040(9) 0.0232(4) Uani 1 1 d . . .
H18A H 0.5639 0.1564 0.9141 0.028 Uiso 1 1 calc R . .
H18B H 0.7697 0.1935 0.9733 0.028 Uiso 1 1 calc R . .
C19 C 1.1419(3) 0.41978(10) 0.70824(9) 0.0213(4) Uani 1 1 d . . .
H19 H 1.2523 0.3718 0.6974 0.026 Uiso 1 1 calc R . .
C20 C 1.1560(3) 0.49736(11) 0.66745(9) 0.0232(4) Uani 1 1 d . . .
H20 H 1.2726 0.5009 0.6289 0.028 Uiso 1 1 calc R . .
C21 C 0.4449(4) 0.13098(11) 1.01788(10) 0.0302(4) Uani 1 1 d . . .
H21A H 0.2597 0.1195 1.0031 0.045 Uiso 1 1 calc R . .
H21B H 0.4502 0.1624 1.0634 0.045 Uiso 1 1 calc R . .
H21C H 0.5404 0.0757 1.0235 0.045 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0259(6) 0.0205(6) 0.0245(7) 0.0050(5) 0.0034(5) 0.0005(5)
N2 0.0153(6) 0.0163(7) 0.0177(8) -0.0006(5) 0.0027(5) 0.0007(5)
N3 0.0166(7) 0.0204(7) 0.0174(8) -0.0026(6) 0.0030(6) 0.0012(5)
C4 0.0138(7) 0.0175(8) 0.0170(9) -0.0025(6) -0.0015(6) -0.0018(6)
C5 0.0154(8) 0.0230(9) 0.0168(9) -0.0045(7) 0.0009(7) -0.0002(6)
C6 0.0214(8) 0.0210(9) 0.0207(9) 0.0020(7) 0.0014(7) -0.0036(7)
C7 0.0179(8) 0.0189(8) 0.0204(9) 0.0004(7) 0.0035(7) 0.0001(6)
C8 0.0166(8) 0.0193(8) 0.0189(9) -0.0002(7) -0.0030(7) -0.0020(6)
C9 0.0160(8) 0.0189(8) 0.0176(9) -0.0019(7) -0.0011(7) -0.0026(6)
C10 0.0130(7) 0.0164(8) 0.0174(9) -0.0020(6) -0.0015(6) -0.0005(6)
C11 0.0140(7) 0.0161(8) 0.0181(9) -0.0002(6) -0.0008(6) -0.0026(6)
C12 0.0151(8) 0.0154(8) 0.0173(9) -0.0007(6) -0.0029(6) -0.0008(6)
C13 0.0198(8) 0.0159(8) 0.0220(9) -0.0002(7) -0.0034(7) 0.0002(6)
C14 0.0179(8) 0.0172(8) 0.0200(9) -0.0003(7) 0.0029(7) 0.0017(6)
C15 0.0169(8) 0.0202(8) 0.0230(10) -0.0045(7) -0.0007(7) 0.0040(6)
C16 0.0170(8) 0.0166(8) 0.0212(9) -0.0017(7) 0.0016(7) -0.0024(6)
C17 0.0135(7) 0.0200(8) 0.0152(9) -0.0031(6) -0.0004(6) -0.0024(6)
C18 0.0258(9) 0.0201(9) 0.0239(10) 0.0014(7) 0.0051(7) 0.0022(7)
C19 0.0180(8) 0.0205(9) 0.0256(10) -0.0059(7) 0.0032(7) -0.0011(6)
C20 0.0220(9) 0.0271(9) 0.0209(10) -0.0027(7) 0.0083(7) -0.0033(7)
C21 0.0375(10) 0.0210(10) 0.0328(11) 0.0037(8) 0.0101(9) 0.0027(8)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.2336(18) . ?
N2 N3 1.3626(17) . ?
N2 C11 1.3635(19) . ?
N2 C14 1.4684(19) . ?
N3 C4 1.365(2) . ?
C4 C10 1.400(2) . ?
C4 C5 1.415(2) . ?
C5 C15 1.379(2) . ?
C6 C20 1.383(2) . ?
C6 C9 1.395(2) . ?
C7 C14 1.515(2) . ?
C7 C18 1.527(2) . ?
C8 C12 1.475(2) . ?
C8 C9 1.508(2) . ?
C9 C17 1.430(2) . ?
C10 C11 1.380(2) . ?
C10 C12 1.398(2) . ?
C11 C17 1.455(2) . ?
C12 C13 1.384(2) . ?
C13 C15 1.420(2) . ?
C16 C19 1.384(2) . ?
C16 C17 1.403(2) . ?
C18 C21 1.520(2) . ?
C19 C20 1.390(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 N2 C11 113.69(12) . . ?
N3 N2 C14 119.53(12) . . ?
C11 N2 C14 126.74(12) . . ?
N2 N3 C4 103.83(12) . . ?
N3 C4 C10 110.28(13) . . ?
N3 C4 C5 131.31(14) . . ?
C10 C4 C5 118.41(14) . . ?
C15 C5 C4 117.05(14) . . ?
C20 C6 C9 121.51(15) . . ?
C14 C7 C18 109.83(12) . . ?
O1 C8 C12 122.55(14) . . ?
O1 C8 C9 120.84(14) . . ?
C12 C8 C9 116.60(13) . . ?
C6 C9 C17 118.88(13) . . ?
C6 C9 C8 117.00(14) . . ?
C17 C9 C8 124.11(14) . . ?
C11 C10 C12 127.90(14) . . ?
C11 C10 C4 107.23(13) . . ?
C12 C10 C4 124.87(14) . . ?
N2 C11 C10 104.97(13) . . ?
N2 C11 C17 134.76(14) . . ?
C10 C11 C17 120.21(14) . . ?
C13 C12 C10 116.16(14) . . ?
C13 C12 C8 128.02(14) . . ?
C10 C12 C8 115.81(13) . . ?
C12 C13 C15 119.88(15) . . ?
N2 C14 C7 114.13(12) . . ?
C5 C15 C13 123.64(14) . . ?
C19 C16 C17 120.84(15) . . ?
C16 C17 C9 118.61(14) . . ?
C16 C17 C11 126.14(14) . . ?
C9 C17 C11 115.25(13) . . ?
C21 C18 C7 112.98(13) . . ?
C16 C19 C20 120.56(14) . . ?
C6 C20 C19 119.56(15) . . ?

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
C11 N2 N3 C4 -0.27(17) . . . . ?
C14 N2 N3 C4 177.86(13) . . . . ?
N2 N3 C4 C10 0.05(16) . . . . ?
N2 N3 C4 C5 179.00(16) . . . . ?
N3 C4 C5 C15 -179.25(15) . . . . ?
C10 C4 C5 C15 -0.4(2) . . . . ?
C20 C6 C9 C17 -0.4(2) . . . . ?
C20 C6 C9 C8 178.45(15) . . . . ?
O1 C8 C9 C6 -3.3(2) . . . . ?
C12 C8 C9 C6 176.99(14) . . . . ?
O1 C8 C9 C17 175.53(15) . . . . ?
C12 C8 C9 C17 -4.2(2) . . . . ?
N3 C4 C10 C11 0.17(18) . . . . ?
C5 C4 C10 C11 -178.94(14) . . . . ?
N3 C4 C10 C12 179.19(14) . . . . ?
C5 C4 C10 C12 0.1(2) . . . . ?
N3 N2 C11 C10 0.37(18) . . . . ?
C14 N2 C11 C10 -177.59(14) . . . . ?
N3 N2 C11 C17 -176.72(16) . . . . ?
C14 N2 C11 C17 5.3(3) . . . . ?
C12 C10 C11 N2 -179.29(15) . . . . ?
C4 C10 C11 N2 -0.31(17) . . . . ?
C12 C10 C11 C17 -1.7(3) . . . . ?
C4 C10 C11 C17 177.30(14) . . . . ?
C11 C10 C12 C13 179.09(15) . . . . ?
C4 C10 C12 C13 0.3(2) . . . . ?
C11 C10 C12 C8 0.4(2) . . . . ?
C4 C10 C12 C8 -178.46(14) . . . . ?
O1 C8 C12 C13 4.1(3) . . . . ?
C9 C8 C12 C13 -176.16(15) . . . . ?
O1 C8 C12 C10 -177.34(15) . . . . ?
C9 C8 C12 C10 2.4(2) . . . . ?
C10 C12 C13 C15 -0.3(2) . . . . ?
C8 C12 C13 C15 178.21(15) . . . . ?
N3 N2 C14 C7 6.9(2) . . . . ?
C11 N2 C14 C7 -175.21(15) . . . . ?
C18 C7 C14 N2 -179.61(13) . . . . ?
C4 C5 C15 C13 0.3(2) . . . . ?
C12 C13 C15 C5 0.1(2) . . . . ?
C19 C16 C17 C9 -1.7(2) . . . . ?
C19 C16 C17 C11 178.42(15) . . . . ?
C6 C9 C17 C16 1.8(2) . . . . ?
C8 C9 C17 C16 -176.99(14) . . . . ?
C6 C9 C17 C11 -178.27(14) . . . . ?
C8 C9 C17 C11 3.0(2) . . . . ?
N2 C11 C17 C16 -3.3(3) . . . . ?
C10 C11 C17 C16 179.91(15) . . . . ?
N2 C11 C17 C9 176.72(16) . . . . ?
C10 C11 C17 C9 0.0(2) . . . . ?
C14 C7 C18 C21 174.97(14) . . . . ?
C17 C16 C19 C20 0.1(2) . . . . ?
C9 C6 C20 C19 -1.1(3) . . . . ?
C16 C19 C20 C6 1.3(2) . . . . ?


#===END
_database_code_depnum_ccdc_archive 'CCDC 990535'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_x

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 N2 O'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C18 H16 N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         276.33
_chemical_compound_source        'see text'

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

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_number      19

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z

_cell_length_a                   4.9093(5)
_cell_length_b                   14.694(2)
_cell_length_c                   19.032(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1372.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(1)
_cell_measurement_reflns_used    9877
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      27.0
_cell_special_details            
;
;
_exptl_crystal_description       block
_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.084
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction,2009)'
_exptl_absorpt_correction_T_min  0.9752
_exptl_absorpt_correction_T_max  0.9834
#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      290(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Oxford Xcalibur,Eos(Nova) CCD detector'
_diffrn_measurement_method       'fω scans'
_diffrn_reflns_number            9877
_diffrn_reflns_av_R_equivalents  0.0936
_diffrn_reflns_av_sigmaI/netI    0.1259
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_reduction_process 
;
;
# number of unique reflections
_reflns_number_total             3001
# number of observed reflections (> n sig(I))
_reflns_number_gt                1861
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlisPro RED (Oxford Diffraction, 2009)'
_computing_structure_solution    'SHELXS97  (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

#===============================================================================

# 8. REFINEMENT DATA
_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 > 2σ(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)+(0.1000P)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     SHELXL
_refine_ls_extinction_coef       0.013(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(4)
_refine_ls_number_reflns         3001
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1205
_refine_ls_R_factor_gt           0.0669
_refine_ls_wR_factor_ref         0.1926
_refine_ls_wR_factor_gt          0.1516
_refine_ls_goodness_of_fit_ref   0.863
_refine_ls_restrained_S_all      0.863
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.054

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
O O -0.1200(6) 0.8919(2) 0.67856(13) 0.0404(8) Uani 1 1 d . . .
C2 C 0.0086(7) 0.8037(2) 0.85586(18) 0.0229(8) Uani 1 1 d . . .
N3 N -0.2585(6) 0.6726(2) 0.90563(14) 0.0276(7) Uani 1 1 d . . .
C4 C -0.3492(7) 0.7175(2) 0.79541(18) 0.0246(8) Uani 1 1 d . . .
C5 C -0.1441(7) 0.8420(3) 0.73039(18) 0.0267(8) Uani 1 1 d . . .
C6 C -0.1899(7) 0.7313(2) 0.85577(17) 0.0237(8) Uani 1 1 d . . .
C7 C -0.3403(7) 0.7667(3) 0.73264(17) 0.0255(8) Uani 1 1 d . . .
N8 N -0.4647(6) 0.6208(2) 0.87727(16) 0.0286(7) Uani 1 1 d . . .
C9 C 0.3866(8) 0.9450(3) 0.8499(2) 0.0335(9) Uani 1 1 d . . .
H9 H 0.5145 0.9917 0.8479 0.040 Uiso 1 1 calc R . .
C10 C 0.3619(8) 0.8926(3) 0.90975(19) 0.0305(9) Uani 1 1 d . . .
H10 H 0.4722 0.9049 0.9483 0.037 Uiso 1 1 calc R . .
C11 C 0.1754(8) 0.8219(3) 0.91339(19) 0.0291(9) Uani 1 1 d . . .
H11 H 0.1617 0.7868 0.9539 0.035 Uiso 1 1 calc R . .
C12 C -0.7078(8) 0.6669(3) 0.69559(19) 0.0332(9) Uani 1 1 d . . .
H12 H -0.8292 0.6503 0.6603 0.040 Uiso 1 1 calc R . .
C13 C 0.0290(7) 0.8573(2) 0.79472(18) 0.0239(8) Uani 1 1 d . . .
C14 C -0.5242(7) 0.6470(3) 0.80973(18) 0.0254(8) Uani 1 1 d . . .
C15 C -0.5264(8) 0.7397(3) 0.68248(18) 0.0289(9) Uani 1 1 d . . .
H15 H -0.5325 0.7696 0.6395 0.035 Uiso 1 1 calc R . .
C16 C -0.5932(8) 0.5519(2) 0.92064(19) 0.0298(9) Uani 1 1 d . . .
H16B H -0.7463 0.5262 0.8953 0.036 Uiso 1 1 calc R . .
H16A H -0.6635 0.5804 0.9629 0.036 Uiso 1 1 calc R . .
C17 C -0.7139(8) 0.6190(3) 0.75843(19) 0.0314(9) Uani 1 1 d . . .
H17 H -0.8352 0.5715 0.7662 0.038 Uiso 1 1 calc R . .
C18 C -0.5277(8) 0.4119(3) 0.99481(19) 0.0333(9) Uani 1 1 d . . .
H18B H -0.5983 0.4470 1.0339 0.040 Uiso 1 1 calc R . .
H18A H -0.6790 0.3799 0.9733 0.040 Uiso 1 1 calc R . .
C19 C -0.3226(9) 0.3437(3) 1.0217(2) 0.0403(11) Uani 1 1 d . . .
H19A H -0.2529 0.3087 0.9830 0.060 Uiso 1 1 calc R . .
H19B H -0.4090 0.3038 1.0548 0.060 Uiso 1 1 calc R . .
H19C H -0.1754 0.3752 1.0443 0.060 Uiso 1 1 calc R . .
C20 C -0.4003(8) 0.4761(3) 0.94119(18) 0.0312(9) Uani 1 1 d . . .
H20A H -0.2355 0.5022 0.9608 0.037 Uiso 1 1 calc R . .
H20B H -0.3503 0.4418 0.8996 0.037 Uiso 1 1 calc R . .
C21 C 0.2207(8) 0.9278(3) 0.7931(2) 0.0315(9) Uani 1 1 d . . .
H21 H 0.2363 0.9636 0.7530 0.038 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O 0.0417(17) 0.0460(18) 0.0335(15) 0.0144(13) 0.0043(13) 0.0027(15)
C2 0.0193(17) 0.0255(19) 0.0240(17) -0.0028(15) 0.0058(15) 0.0046(15)
N3 0.0271(16) 0.0277(18) 0.0279(16) 0.0001(14) -0.0010(14) -0.0024(14)
C4 0.0237(18) 0.0256(19) 0.0245(17) -0.0054(15) 0.0015(16) 0.0042(16)
C5 0.0224(18) 0.028(2) 0.0297(19) 0.0044(15) 0.0103(16) 0.0059(17)
C6 0.0212(18) 0.027(2) 0.0227(17) 0.0020(15) 0.0001(15) 0.0033(15)
C7 0.0248(19) 0.030(2) 0.0214(17) -0.0028(15) 0.0030(15) 0.0029(17)
N8 0.0264(16) 0.0282(18) 0.0313(16) 0.0018(13) -0.0027(14) -0.0053(14)
C9 0.029(2) 0.026(2) 0.045(2) -0.0038(18) 0.006(2) -0.0043(16)
C10 0.0271(19) 0.032(2) 0.033(2) -0.0071(16) -0.0023(17) 0.0011(18)
C11 0.0255(19) 0.031(2) 0.0309(19) -0.0047(17) 0.0029(17) 0.0030(17)
C12 0.028(2) 0.040(2) 0.032(2) -0.0140(18) -0.0061(18) 0.0060(19)
C13 0.0191(17) 0.027(2) 0.0254(18) 0.0021(15) 0.0043(15) 0.0052(15)
C14 0.0203(17) 0.031(2) 0.0248(18) -0.0043(15) 0.0020(15) 0.0017(16)
C15 0.0279(19) 0.035(2) 0.0241(18) -0.0010(15) -0.0003(16) 0.0108(18)
C16 0.028(2) 0.025(2) 0.037(2) -0.0006(16) 0.0034(18) -0.0044(17)
C17 0.0234(19) 0.033(2) 0.038(2) -0.0063(18) -0.0011(17) 0.0031(17)
C18 0.033(2) 0.032(2) 0.035(2) 0.0003(17) 0.0067(18) -0.0054(18)
C19 0.045(3) 0.037(3) 0.039(2) 0.0044(18) -0.002(2) 0.002(2)
C20 0.035(2) 0.027(2) 0.032(2) -0.0018(16) 0.0036(18) -0.0075(18)
C21 0.0266(19) 0.031(2) 0.037(2) 0.0034(18) 0.0055(18) 0.0061(17)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O C5 1.235(4) . ?
C2 C11 1.393(5) . ?
C2 C13 1.409(5) . ?
C2 C6 1.443(5) . ?
N3 C6 1.326(4) . ?
N3 N8 1.377(4) . ?
C4 C14 1.373(5) . ?
C4 C7 1.397(5) . ?
C4 C6 1.405(5) . ?
C5 C7 1.467(5) . ?
C5 C13 1.507(5) . ?
C7 C15 1.380(5) . ?
N8 C14 1.374(4) . ?
N8 C16 1.450(5) . ?
C9 C21 1.377(5) . ?
C9 C10 1.381(5) . ?
C10 C11 1.387(5) . ?
C12 C17 1.388(5) . ?
C12 C15 1.413(5) . ?
C13 C21 1.400(5) . ?
C14 C17 1.411(5) . ?
C16 C20 1.514(5) . ?
C18 C19 1.510(6) . ?
C18 C20 1.523(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C2 C13 120.0(3) . . ?
C11 C2 C6 122.6(3) . . ?
C13 C2 C6 117.4(3) . . ?
C6 N3 N8 105.4(3) . . ?
C14 C4 C7 125.4(3) . . ?
C14 C4 C6 107.2(3) . . ?
C7 C4 C6 127.4(3) . . ?
O C5 C7 122.3(3) . . ?
O C5 C13 120.4(3) . . ?
C7 C5 C13 117.3(3) . . ?
N3 C6 C4 110.5(3) . . ?
N3 C6 C2 130.6(3) . . ?
C4 C6 C2 118.9(3) . . ?
C15 C7 C4 114.9(3) . . ?
C15 C7 C5 129.2(3) . . ?
C4 C7 C5 115.8(3) . . ?
C14 N8 N3 111.6(3) . . ?
C14 N8 C16 129.5(3) . . ?
N3 N8 C16 118.9(3) . . ?
C21 C9 C10 119.5(4) . . ?
C9 C10 C11 121.2(4) . . ?
C10 C11 C2 119.5(3) . . ?
C17 C12 C15 123.3(3) . . ?
C21 C13 C2 118.7(3) . . ?
C21 C13 C5 118.1(3) . . ?
C2 C13 C5 123.2(3) . . ?
C4 C14 N8 105.4(3) . . ?
C4 C14 C17 119.7(3) . . ?
N8 C14 C17 134.9(4) . . ?
C7 C15 C12 120.9(3) . . ?
N8 C16 C20 112.9(3) . . ?
C12 C17 C14 115.7(4) . . ?
C19 C18 C20 111.3(3) . . ?
C16 C20 C18 111.8(3) . . ?
C9 C21 C13 121.1(4) . . ?

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
N8 N3 C6 C4 -0.3(4) . . . . ?
N8 N3 C6 C2 178.3(3) . . . . ?
C14 C4 C6 N3 0.3(4) . . . . ?
C7 C4 C6 N3 178.8(3) . . . . ?
C14 C4 C6 C2 -178.4(3) . . . . ?
C7 C4 C6 C2 0.1(6) . . . . ?
C11 C2 C6 N3 1.7(6) . . . . ?
C13 C2 C6 N3 -177.9(4) . . . . ?
C11 C2 C6 C4 -179.8(3) . . . . ?
C13 C2 C6 C4 0.5(5) . . . . ?
C14 C4 C7 C15 -0.1(5) . . . . ?
C6 C4 C7 C15 -178.3(4) . . . . ?
C14 C4 C7 C5 177.4(3) . . . . ?
C6 C4 C7 C5 -0.9(5) . . . . ?
O C5 C7 C15 -1.5(6) . . . . ?
C13 C5 C7 C15 178.0(4) . . . . ?
O C5 C7 C4 -178.5(3) . . . . ?
C13 C5 C7 C4 1.0(5) . . . . ?
C6 N3 N8 C14 0.1(4) . . . . ?
C6 N3 N8 C16 -177.3(3) . . . . ?
C21 C9 C10 C11 1.0(6) . . . . ?
C9 C10 C11 C2 -0.4(5) . . . . ?
C13 C2 C11 C10 -0.4(5) . . . . ?
C6 C2 C11 C10 180.0(3) . . . . ?
C11 C2 C13 C21 0.7(5) . . . . ?
C6 C2 C13 C21 -179.7(3) . . . . ?
C11 C2 C13 C5 -180.0(3) . . . . ?
C6 C2 C13 C5 -0.3(5) . . . . ?
O C5 C13 C21 -1.6(5) . . . . ?
C7 C5 C13 C21 178.9(3) . . . . ?
O C5 C13 C2 179.0(3) . . . . ?
C7 C5 C13 C2 -0.5(5) . . . . ?
C7 C4 C14 N8 -178.8(3) . . . . ?
C6 C4 C14 N8 -0.2(4) . . . . ?
C7 C4 C14 C17 0.3(6) . . . . ?
C6 C4 C14 C17 178.9(3) . . . . ?
N3 N8 C14 C4 0.1(4) . . . . ?
C16 N8 C14 C4 177.2(3) . . . . ?
N3 N8 C14 C17 -178.8(4) . . . . ?
C16 N8 C14 C17 -1.7(7) . . . . ?
C4 C7 C15 C12 -0.3(5) . . . . ?
C5 C7 C15 C12 -177.4(3) . . . . ?
C17 C12 C15 C7 0.5(6) . . . . ?
C14 N8 C16 C20 118.1(4) . . . . ?
N3 N8 C16 C20 -65.0(4) . . . . ?
C15 C12 C17 C14 -0.3(5) . . . . ?
C4 C14 C17 C12 -0.1(5) . . . . ?
N8 C14 C17 C12 178.6(4) . . . . ?
N8 C16 C20 C18 172.0(3) . . . . ?
C19 C18 C20 C16 -172.9(3) . . . . ?
C10 C9 C21 C13 -0.7(6) . . . . ?
C2 C13 C21 C9 -0.1(5) . . . . ?
C5 C13 C21 C9 -179.5(3) . . . . ?


#===END
_database_code_depnum_ccdc_archive 'CCDC 990059'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_x

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 N2 O'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C17 H14 N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         262.30
_chemical_compound_source        'see text'

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

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3'
_symmetry_Int_Tables_number      148

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -y,x-y,z
3 -x+y,-x,z
4 -x,-y,-z
5 y,-x+y,-z
6 x-y,x,-z
7 1/3+x,2/3+y,2/3+z
8 1/3-y,2/3+x-y,2/3+z
9 1/3-x+y,2/3-x,2/3+z
10 1/3-x,2/3-y,2/3-z
11 1/3+y,2/3-x+y,2/3-z
12 1/3+x-y,2/3+x,2/3-z
13 2/3+x,1/3+y,1/3+z
14 2/3-y,1/3+x-y,1/3+z
15 2/3-x+y,1/3-x,1/3+z
16 2/3-x,1/3-y,1/3-z
17 2/3+y,1/3-x+y,1/3-z
18 2/3+x-y,1/3+x,1/3-z

_cell_length_a                   27.7895(8)
_cell_length_b                   27.7895(8)
_cell_length_c                   8.9482(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     5984.5(3)
_cell_formula_units_Z            18
_cell_measurement_temperature    120(1)
_cell_measurement_reflns_used    13435
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      27.0
_cell_special_details            
;
;
_exptl_crystal_description       block
_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             2484
_exptl_absorpt_coefficient_mu    0.083
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction,2009)'
_exptl_absorpt_correction_T_min  0.9755
_exptl_absorpt_correction_T_max  0.9836

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      120(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Oxford Xcalibur,Eos(Nova) CCD detector'
_diffrn_measurement_method       'fω scans'
_diffrn_reflns_number            13435
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_reduction_process 
;
;
# number of unique reflections
_reflns_number_total             2914
# number of observed reflections (> n sig(I))
_reflns_number_gt                2239
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlisPro RED (Oxford Diffraction, 2009)'
_computing_structure_solution    'SHELXS97  (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

#===============================================================================

# 8. REFINEMENT DATA
_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)+(0.1000P)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         2914
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1644
_refine_ls_wR_factor_gt          0.1518
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.048

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
O O 0.59554(5) 0.47401(5) 0.76025(14) 0.0367(3) Uani 1 1 d . . .
N2 N 0.42895(6) 0.52395(6) 0.75578(16) 0.0296(4) Uani 1 1 d . . .
N3 N 0.45396(5) 0.56719(6) 0.85527(15) 0.0304(4) Uani 1 1 d . . .
C4 C 0.46472(6) 0.50522(6) 0.73978(17) 0.0247(4) Uani 1 1 d . . .
C5 C 0.51219(6) 0.53641(6) 0.82770(17) 0.0232(4) Uani 1 1 d . . .
C6 C 0.50501(6) 0.57648(7) 0.90120(17) 0.0254(4) Uani 1 1 d . . .
C7 C 0.50645(6) 0.45003(6) 0.65987(17) 0.0252(4) Uani 1 1 d . . .
C8 C 0.50485(7) 0.40690(7) 0.57586(19) 0.0301(4) Uani 1 1 d . . .
H8 H 0.5340 0.3996 0.5831 0.036 Uiso 1 1 calc R . .
C9 C 0.46116(6) 0.46016(6) 0.64942(17) 0.0250(4) Uani 1 1 d . . .
C10 C 0.55706(7) 0.48402(7) 0.75696(18) 0.0263(4) Uani 1 1 d . . .
C11 C 0.55857(6) 0.53001(6) 0.84348(17) 0.0233(4) Uani 1 1 d . . .
C12 C 0.59983(7) 0.56721(7) 0.93951(17) 0.0264(4) Uani 1 1 d . . .
H12 H 0.6317 0.5649 0.9551 0.032 Uiso 1 1 calc R . .
C13 C 0.54674(7) 0.61429(7) 0.99689(18) 0.0287(4) Uani 1 1 d . . .
H13 H 0.5435 0.6419 1.0469 0.034 Uiso 1 1 calc R . .
C14 C 0.59316(7) 0.60827(7) 1.01299(18) 0.0285(4) Uani 1 1 d . . .
H14 H 0.6215 0.6328 1.0760 0.034 Uiso 1 1 calc R . .
C15 C 0.42605(8) 0.59756(8) 0.9002(2) 0.0401(5) Uani 1 1 d . . .
H15A H 0.4290 0.6027 1.0078 0.048 Uiso 1 1 calc R . .
H15B H 0.3869 0.5756 0.8754 0.048 Uiso 1 1 calc R . .
C16 C 0.41702(7) 0.38553(7) 0.46987(19) 0.0327(4) Uani 1 1 d . . .
H16 H 0.3876 0.3644 0.4053 0.039 Uiso 1 1 calc R . .
C17 C 0.46053(8) 0.37469(7) 0.48187(19) 0.0334(4) Uani 1 1 d . . .
H17 H 0.4599 0.3460 0.4271 0.040 Uiso 1 1 calc R . .
C18 C 0.41699(7) 0.42752(7) 0.55329(17) 0.0292(4) Uani 1 1 d . . .
H18 H 0.3874 0.4341 0.5453 0.035 Uiso 1 1 calc R . .
C19 C 0.45008(9) 0.65335(8) 0.8260(3) 0.0523(6) Uani 1 1 d . . .
H19A H 0.4457 0.6484 0.7185 0.063 Uiso 1 1 calc R . .
H19B H 0.4895 0.6750 0.8477 0.063 Uiso 1 1 calc R . .
C20 C 0.42165(10) 0.68449(10) 0.8799(4) 0.0824(10) Uani 1 1 d . . .
H20A H 0.4401 0.7213 0.8384 0.124 Uiso 1 1 calc R . .
H20B H 0.4233 0.6867 0.9870 0.124 Uiso 1 1 calc R . .
H20C H 0.3835 0.6652 0.8484 0.124 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O 0.0335(7) 0.0412(7) 0.0422(8) -0.0033(6) -0.0029(6) 0.0237(6)
N2 0.0240(7) 0.0281(7) 0.0341(8) 0.0047(6) 0.0015(6) 0.0111(6)
N3 0.0261(7) 0.0298(8) 0.0359(8) 0.0025(6) 0.0023(6) 0.0145(6)
C4 0.0206(8) 0.0238(8) 0.0251(8) 0.0075(6) 0.0031(6) 0.0077(6)
C5 0.0224(8) 0.0222(8) 0.0221(8) 0.0071(6) 0.0045(6) 0.0089(6)
C6 0.0240(8) 0.0265(8) 0.0251(8) 0.0070(6) 0.0035(6) 0.0122(7)
C7 0.0265(8) 0.0220(8) 0.0212(8) 0.0065(6) 0.0045(6) 0.0075(7)
C8 0.0340(9) 0.0267(8) 0.0278(9) 0.0054(7) 0.0068(7) 0.0138(7)
C9 0.0228(8) 0.0229(8) 0.0232(8) 0.0088(6) 0.0036(6) 0.0069(6)
C10 0.0267(8) 0.0267(8) 0.0254(8) 0.0066(7) 0.0038(6) 0.0131(7)
C11 0.0239(8) 0.0241(8) 0.0206(8) 0.0077(6) 0.0034(6) 0.0110(6)
C12 0.0236(8) 0.0311(9) 0.0240(8) 0.0065(7) 0.0004(6) 0.0133(7)
C13 0.0321(9) 0.0272(8) 0.0257(8) 0.0031(7) 0.0029(7) 0.0140(7)
C14 0.0271(9) 0.0290(9) 0.0234(8) 0.0014(7) -0.0029(7) 0.0095(7)
C15 0.0337(10) 0.0390(10) 0.0549(12) 0.0009(9) 0.0007(9) 0.0237(9)
C16 0.0321(9) 0.0262(9) 0.0244(8) 0.0053(7) -0.0005(7) 0.0030(7)
C17 0.0402(10) 0.0241(8) 0.0265(9) 0.0036(7) 0.0049(7) 0.0090(8)
C18 0.0252(8) 0.0286(9) 0.0261(9) 0.0089(7) 0.0020(7) 0.0078(7)
C19 0.0448(12) 0.0401(11) 0.0765(16) 0.0071(10) -0.0028(11) 0.0245(10)
C20 0.0417(13) 0.0429(13) 0.170(3) 0.0090(16) -0.0013(16) 0.0266(11)

_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
O C10 1.2324(19) . ?
N2 C4 1.341(2) . ?
N2 N3 1.3728(19) . ?
N3 C6 1.372(2) . ?
N3 C15 1.459(2) . ?
C4 C5 1.402(2) . ?
C4 C9 1.452(2) . ?
C5 C6 1.391(2) . ?
C5 C11 1.394(2) . ?
C6 C13 1.401(2) . ?
C7 C8 1.397(2) . ?
C7 C9 1.423(2) . ?
C7 C10 1.515(2) . ?
C8 C17 1.387(2) . ?
C9 C18 1.399(2) . ?
C10 C11 1.477(2) . ?
C11 C12 1.392(2) . ?
C12 C14 1.407(2) . ?
C13 C14 1.389(2) . ?
C15 C19 1.502(3) . ?
C16 C18 1.386(2) . ?
C16 C17 1.389(3) . ?
C19 C20 1.513(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N2 N3 105.07(13) . . ?
C6 N3 N2 112.48(13) . . ?
C6 N3 C15 127.37(15) . . ?
N2 N3 C15 120.15(14) . . ?
N2 C4 C5 110.55(14) . . ?
N2 C4 C9 130.57(15) . . ?
C5 C4 C9 118.88(14) . . ?
C6 C5 C11 124.50(15) . . ?
C6 C5 C4 107.04(13) . . ?
C11 C5 C4 128.46(15) . . ?
N3 C6 C5 104.86(14) . . ?
N3 C6 C13 135.60(15) . . ?
C5 C6 C13 119.54(14) . . ?
C8 C7 C9 118.85(15) . . ?
C8 C7 C10 117.70(15) . . ?
C9 C7 C10 123.44(14) . . ?
C17 C8 C7 121.13(16) . . ?
C18 C9 C7 119.23(15) . . ?
C18 C9 C4 124.13(15) . . ?
C7 C9 C4 116.63(14) . . ?
O C10 C11 122.03(15) . . ?
O C10 C7 120.83(15) . . ?
C11 C10 C7 117.12(13) . . ?
C12 C11 C5 116.03(15) . . ?
C12 C11 C10 128.53(14) . . ?
C5 C11 C10 115.44(14) . . ?
C11 C12 C14 119.82(14) . . ?
C14 C13 C6 116.32(15) . . ?
C13 C14 C12 123.79(15) . . ?
N3 C15 C19 112.60(16) . . ?
C18 C16 C17 120.54(16) . . ?
C8 C17 C16 119.72(16) . . ?
C16 C18 C9 120.51(16) . . ?
C15 C19 C20 111.07(19) . . ?

#===END
_database_code_depnum_ccdc_archive 'CCDC 990060'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_exp_6458_red

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 N2 O'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C17 H14 N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         262.30
_chemical_compound_source        'see text'

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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_number      19

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z

_cell_length_a                   5.4152(4)
_cell_length_b                   15.1404(14)
_cell_length_c                   15.6780(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1285.41(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(1)
_cell_measurement_reflns_used    7350
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.0
_cell_special_details            
;
;
_exptl_crystal_description       block
_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.086
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction,2009)'
_exptl_absorpt_correction_T_min  0.9747
_exptl_absorpt_correction_T_max  0.9830

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      120(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Oxford Xcalibur,Eos(Nova) CCD detector'
_diffrn_measurement_method       'fω scans'
_diffrn_reflns_number            7350
_diffrn_reflns_av_R_equivalents  0.1096
_diffrn_reflns_av_sigmaI/netI    0.1759
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_reduction_process 
;
;
# number of unique reflections
_reflns_number_total             2757
# number of observed reflections (> n sig(I))
_reflns_number_gt                1501
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlisPro RED (Oxford Diffraction, 2009)'
_computing_structure_solution    'SHELXS97  (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

#===============================================================================

# 8. REFINEMENT DATA
_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 > 2σ(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)+(0.0162P)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     SHELXL
_refine_ls_extinction_coef       0.0052(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(4)
_refine_ls_number_reflns         2757
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1538
_refine_ls_R_factor_gt           0.0709
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1005
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_restrained_S_all      0.915
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.058

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
O O 0.7414(5) 0.78803(18) 0.19579(19) 0.0325(8) Uani 1 1 d . . .
C C 0.7897(8) 0.7265(3) 0.2453(3) 0.0255(10) Uani 1 1 d . . .
C0AA C 1.2109(8) 0.6458(3) 0.4196(3) 0.0274(11) Uani 1 1 d . . .
C1AA C 0.6923(7) 0.5672(3) 0.2955(3) 0.0198(9) Uani 1 1 d . . .
C2AA C 0.4492(7) 0.6370(3) 0.1833(3) 0.0264(11) Uani 1 1 d . . .
H2AA H 0.4151 0.6856 0.1490 0.032 Uiso 1 1 calc R . .
C3AA C 0.6428(7) 0.6407(3) 0.2422(3) 0.0207(10) Uani 1 1 d . . .
C4AA C 0.8931(7) 0.5776(3) 0.3551(3) 0.0243(10) Uani 1 1 d . . .
C5AA C 1.0248(7) 0.6558(3) 0.3580(3) 0.0233(10) Uani 1 1 d . . .
N N 1.1996(6) 0.5638(2) 0.4559(2) 0.0280(9) Uani 1 1 d . . .
C6AA C 1.1546(7) 0.7999(3) 0.3225(3) 0.0268(11) Uani 1 1 d . . .
H6AA H 1.1405 0.8517 0.2910 0.032 Uiso 1 1 calc R . .
C7AA C 0.3074(7) 0.5608(3) 0.1759(3) 0.0254(10) Uani 1 1 d . . .
H7AA H 0.1799 0.5582 0.1362 0.030 Uiso 1 1 calc R . .
C8AA C 0.9405(7) 0.4333(3) 0.4391(3) 0.0268(11) Uani 1 1 d . . .
H8AB H 1.0792 0.4066 0.4686 0.032 Uiso 1 1 calc R . .
H8AA H 0.9066 0.3986 0.3885 0.032 Uiso 1 1 calc R . .
N0AA N 1.0044(6) 0.5244(2) 0.4142(2) 0.0266(9) Uani 1 1 d . . .
C9AA C 1.3753(7) 0.7161(3) 0.4331(3) 0.0293(11) Uani 1 1 d . . .
H9AA H 1.5022 0.7119 0.4728 0.035 Uiso 1 1 calc R . .
C0BA C 0.7152(7) 0.4326(3) 0.4971(3) 0.0285(11) Uani 1 1 d . . .
H0BB H 0.5872 0.4699 0.4731 0.034 Uiso 1 1 calc R . .
H0BA H 0.7591 0.4559 0.5527 0.034 Uiso 1 1 calc R . .
C1BA C 0.9919(7) 0.7308(3) 0.3079(3) 0.0236(10) Uani 1 1 d . . .
C2BA C 1.3415(8) 0.7922(3) 0.3847(3) 0.0317(11) Uani 1 1 d . . .
H2BA H 1.4463 0.8399 0.3938 0.038 Uiso 1 1 calc R . .
C3BA C 0.5436(7) 0.4919(3) 0.2865(3) 0.0261(11) Uani 1 1 d . . .
H3BA H 0.5727 0.4431 0.3211 0.031 Uiso 1 1 calc R . .
C4BA C 0.3563(8) 0.4887(3) 0.2277(3) 0.0296(11) Uani 1 1 d . . .
H4BA H 0.2613 0.4378 0.2226 0.036 Uiso 1 1 calc R . .
C5BA C 0.6186(8) 0.3380(3) 0.5064(3) 0.0329(12) Uani 1 1 d . . .
H5BA H 0.4790 0.3376 0.5441 0.049 Uiso 1 1 calc R . .
H5BC H 0.7465 0.3011 0.5294 0.049 Uiso 1 1 calc R . .
H5BB H 0.5698 0.3159 0.4515 0.049 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O 0.0446(19) 0.0173(16) 0.0358(19) -0.0010(15) 0.0015(16) -0.0025(16)
C 0.034(2) 0.016(2) 0.026(2) -0.007(2) 0.007(2) 0.003(2)
C0AA 0.027(2) 0.023(2) 0.031(3) -0.002(2) 0.007(2) 0.006(2)
C1AA 0.020(2) 0.015(2) 0.025(2) -0.0068(19) 0.004(2) -0.0015(19)
C2AA 0.034(3) 0.022(2) 0.023(2) 0.001(2) 0.003(2) 0.002(2)
C3AA 0.023(2) 0.014(2) 0.025(2) -0.0019(19) 0.005(2) 0.0014(19)
C4AA 0.018(2) 0.022(2) 0.033(3) 0.002(2) 0.000(2) 0.006(2)
C5AA 0.020(2) 0.025(2) 0.024(2) -0.002(2) 0.001(2) 0.001(2)
N 0.0215(18) 0.027(2) 0.035(2) 0.0018(18) -0.0002(18) 0.0009(18)
C6AA 0.026(2) 0.021(2) 0.034(3) -0.008(2) 0.009(2) -0.002(2)
C7AA 0.026(2) 0.027(2) 0.023(2) -0.002(2) -0.002(2) -0.002(2)
C8AA 0.031(2) 0.017(2) 0.033(3) 0.002(2) -0.003(2) 0.003(2)
N0AA 0.0249(19) 0.022(2) 0.033(2) 0.0032(18) -0.0013(18) 0.0008(17)
C9AA 0.021(2) 0.040(3) 0.027(3) -0.008(2) 0.001(2) 0.001(2)
C0BA 0.030(2) 0.023(2) 0.033(3) 0.001(2) 0.002(2) 0.001(2)
C1BA 0.023(2) 0.018(2) 0.029(3) -0.002(2) 0.003(2) 0.0048(19)
C2BA 0.027(2) 0.031(3) 0.037(3) -0.011(2) 0.005(2) -0.008(2)
C3BA 0.023(2) 0.017(2) 0.039(3) 0.000(2) 0.003(2) 0.000(2)
C4BA 0.029(2) 0.027(3) 0.033(3) -0.001(2) 0.001(2) -0.003(2)
C5BA 0.033(3) 0.026(3) 0.040(3) 0.000(2) 0.001(2) 0.002(2)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O C 1.241(5) . ?
C C1BA 1.471(6) . ?
C C3AA 1.524(5) . ?
C0AA N 1.368(5) . ?
C0AA C9AA 1.403(6) . ?
C0AA C5AA 1.404(6) . ?
C1AA C3BA 1.403(5) . ?
C1AA C3AA 1.417(5) . ?
C1AA C4AA 1.442(5) . ?
C2AA C7AA 1.391(5) . ?
C2AA C3AA 1.398(5) . ?
C4AA N0AA 1.368(5) . ?
C4AA C5AA 1.383(6) . ?
C5AA C1BA 1.393(6) . ?
N N0AA 1.379(5) . ?
C6AA C1BA 1.386(5) . ?
C6AA C2BA 1.411(6) . ?
C7AA C4BA 1.386(5) . ?
C8AA N0AA 1.474(5) . ?
C8AA C0BA 1.521(5) . ?
C9AA C2BA 1.391(6) . ?
C0BA C5BA 1.533(5) . ?
C3BA C4BA 1.371(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O C C1BA 122.7(4) . . ?
O C C3AA 120.6(4) . . ?
C1BA C C3AA 116.6(4) . . ?
N C0AA C9AA 130.9(4) . . ?
N C0AA C5AA 110.6(4) . . ?
C9AA C0AA C5AA 118.5(4) . . ?
C3BA C1AA C3AA 118.1(4) . . ?
C3BA C1AA C4AA 125.9(4) . . ?
C3AA C1AA C4AA 116.1(4) . . ?
C7AA C2AA C3AA 120.1(4) . . ?
C2AA C3AA C1AA 120.0(4) . . ?
C2AA C3AA C 116.5(4) . . ?
C1AA C3AA C 123.5(4) . . ?
N0AA C4AA C5AA 104.7(4) . . ?
N0AA C4AA C1AA 135.0(4) . . ?
C5AA C4AA C1AA 120.2(4) . . ?
C4AA C5AA C1BA 127.8(4) . . ?
C4AA C5AA C0AA 107.5(4) . . ?
C1BA C5AA C0AA 124.6(4) . . ?
C0AA N N0AA 103.3(3) . . ?
C1BA C6AA C2BA 120.5(4) . . ?
C4BA C7AA C2AA 119.9(4) . . ?
N0AA C8AA C0BA 110.7(3) . . ?
C4AA N0AA N 113.9(3) . . ?
C4AA N0AA C8AA 128.8(4) . . ?
N N0AA C8AA 117.3(3) . . ?
C2BA C9AA C0AA 117.5(4) . . ?
C8AA C0BA C5BA 109.7(3) . . ?
C6AA C1BA C5AA 116.1(4) . . ?
C6AA C1BA C 128.1(4) . . ?
C5AA C1BA C 115.8(4) . . ?
C9AA C2BA C6AA 122.7(4) . . ?
C4BA C3BA C1AA 121.4(4) . . ?
C3BA C4BA C7AA 120.5(4) . . ?

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
C7AA C2AA C3AA C1AA -1.0(6) . . . . ?
C7AA C2AA C3AA C 179.4(4) . . . . ?
C3BA C1AA C3AA C2AA 0.5(6) . . . . ?
C4AA C1AA C3AA C2AA -179.1(4) . . . . ?
C3BA C1AA C3AA C 180.0(4) . . . . ?
C4AA C1AA C3AA C 0.4(5) . . . . ?
O C C3AA C2AA -2.1(6) . . . . ?
C1BA C C3AA C2AA 179.4(4) . . . . ?
O C C3AA C1AA 178.4(4) . . . . ?
C1BA C C3AA C1AA -0.1(5) . . . . ?
C3BA C1AA C4AA N0AA 2.9(7) . . . . ?
C3AA C1AA C4AA N0AA -177.6(4) . . . . ?
C3BA C1AA C4AA C5AA -179.5(4) . . . . ?
C3AA C1AA C4AA C5AA 0.1(6) . . . . ?
N0AA C4AA C5AA C1BA 177.4(4) . . . . ?
C1AA C4AA C5AA C1BA -0.9(7) . . . . ?
N0AA C4AA C5AA C0AA -0.1(5) . . . . ?
C1AA C4AA C5AA C0AA -178.3(3) . . . . ?
N C0AA C5AA C4AA -0.4(5) . . . . ?
C9AA C0AA C5AA C4AA 178.3(4) . . . . ?
N C0AA C5AA C1BA -177.9(4) . . . . ?
C9AA C0AA C5AA C1BA 0.7(6) . . . . ?
C9AA C0AA N N0AA -177.8(4) . . . . ?
C5AA C0AA N N0AA 0.6(4) . . . . ?
C3AA C2AA C7AA C4BA 0.8(6) . . . . ?
C5AA C4AA N0AA N 0.5(5) . . . . ?
C1AA C4AA N0AA N 178.4(4) . . . . ?
C5AA C4AA N0AA C8AA 179.3(4) . . . . ?
C1AA C4AA N0AA C8AA -2.8(7) . . . . ?
C0AA N N0AA C4AA -0.7(4) . . . . ?
C0AA N N0AA C8AA -179.7(4) . . . . ?
C0BA C8AA N0AA C4AA -76.8(5) . . . . ?
C0BA C8AA N0AA N 102.0(4) . . . . ?
N C0AA C9AA C2BA 179.0(4) . . . . ?
C5AA C0AA C9AA C2BA 0.6(6) . . . . ?
N0AA C8AA C0BA C5BA 167.8(4) . . . . ?
C2BA C6AA C1BA C5AA 0.3(6) . . . . ?
C2BA C6AA C1BA C -179.0(4) . . . . ?
C4AA C5AA C1BA C6AA -178.3(4) . . . . ?
C0AA C5AA C1BA C6AA -1.2(6) . . . . ?
C4AA C5AA C1BA C 1.1(7) . . . . ?
C0AA C5AA C1BA C 178.2(4) . . . . ?
O C C1BA C6AA 0.2(7) . . . . ?
C3AA C C1BA C6AA 178.8(4) . . . . ?
O C C1BA C5AA -179.1(4) . . . . ?
C3AA C C1BA C5AA -0.6(5) . . . . ?
C0AA C9AA C2BA C6AA -1.5(7) . . . . ?
C1BA C6AA C2BA C9AA 1.0(6) . . . . ?
C3AA C1AA C3BA C4BA 0.3(6) . . . . ?
C4AA C1AA C3BA C4BA 179.9(4) . . . . ?
C1AA C3BA C4BA C7AA -0.6(6) . . . . ?
C2AA C7AA C4BA C3BA 0.1(6) . . . . ?

#===END
_database_code_depnum_ccdc_archive 'CCDC 990061'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_d_76_3_red

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 N2 O'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C16 H12 N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         248.28
_chemical_compound_source        'see text'

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

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 21'
_symmetry_Int_Tables_number      4

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

_cell_length_a                   4.0054(4)
_cell_length_b                   15.3131(18)
_cell_length_c                   9.7743(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.953(10)
_cell_angle_gamma                90
_cell_volume                     596.27(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(1)
_cell_measurement_reflns_used    5071
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      25.00
_cell_special_details            
;
;
_exptl_crystal_description       block
_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             260
_exptl_absorpt_coefficient_mu    0.088
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction,2009)'
_exptl_absorpt_correction_T_min  0.9740
_exptl_absorpt_correction_T_max  0.9826

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      290(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Oxford Xcalibur,Eos(Nova) CCD detector'
_diffrn_measurement_method       'fω scans'
_diffrn_reflns_number            5071
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_sigmaI/netI    0.0878
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_reduction_process 
;
;
# number of unique reflections
_reflns_number_total             2053
# number of observed reflections (> n sig(I))
_reflns_number_gt                1332
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlisPro RED (Oxford Diffraction, 2009)'
_computing_structure_solution    'SHELXS97  (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

#===============================================================================

# 8. REFINEMENT DATA
_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)+(0.0389P)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     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(4)
_refine_ls_number_reflns         2053
_refine_ls_number_parameters     174
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.1391
_refine_ls_wR_factor_gt          0.1151
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.041

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
C C 0.6421(10) 0.1152(3) 0.9533(5) 0.0479(11) Uani 1 1 d . . .
C2BA C 0.8700(11) 0.0322(3) 0.7654(4) 0.0550(12) Uani 1 1 d . . .
H2BA H 0.8110 0.0805 0.7103 0.066 Uiso 1 1 calc R . .
C0AA C 0.9035(9) -0.0390(3) 0.9883(4) 0.0413(10) Uani 1 1 d . . .
C1AA C 0.6651(10) 0.0401(3) 1.1741(4) 0.0426(10) Uani 1 1 d . . .
C2AA C 0.4139(10) 0.1792(3) 1.1660(5) 0.0545(12) Uani 1 1 d . . .
H2AA H 0.3450 0.2303 1.1199 0.065 Uiso 1 1 calc R . .
C3AA C 0.8088(10) 0.0337(3) 0.9040(4) 0.0443(10) Uani 1 1 d . . .
C4AA C 0.5672(10) 0.1145(3) 1.0971(4) 0.0463(11) Uani 1 1 d . . .
O O 0.5786(8) 0.1773(2) 0.8757(4) 0.0715(10) Uani 1 1 d . . .
C6AA C 0.8284(9) -0.0333(2) 1.1286(4) 0.0393(10) Uani 1 1 d . . .
C5AA C 1.1104(11) -0.1107(3) 0.7935(4) 0.0567(13) Uani 1 1 d . . .
H5AA H 1.2085 -0.1589 0.7559 0.068 Uiso 1 1 calc R . .
C7AA C 0.4578(10) 0.0956(3) 1.3798(5) 0.0593(13) Uani 1 1 d . . .
H7AA H 0.4179 0.0900 1.4714 0.071 Uiso 1 1 calc R . .
C8AA C 1.0139(12) -0.0381(4) 0.7096(5) 0.0640(14) Uani 1 1 d . . .
H8AA H 1.0482 -0.0383 0.6169 0.077 Uiso 1 1 calc R . .
C9AA C 0.3603(10) 0.1691(3) 1.3051(5) 0.0602(13) Uani 1 1 d . . .
H9AA H 0.2549 0.2139 1.3484 0.072 Uiso 1 1 calc R . .
C0BA C 1.0601(11) -0.1105(3) 0.9302(4) 0.0470(11) Uani 1 1 d . . .
H0BA H 1.1301 -0.1580 0.9852 0.056 Uiso 1 1 calc R . .
C1BA C 0.6204(10) 0.0290(3) 1.3122(4) 0.0469(11) Uani 1 1 d . . .
N1AA N 0.7481(9) -0.0510(3) 1.3564(3) 0.0509(9) Uani 1 1 d . . .
N2AA N 0.8696(8) -0.0852(2) 1.2420(3) 0.0451(9) Uani 1 1 d . . .
C3BA C 1.0292(11) -0.1725(3) 1.2514(4) 0.0540(12) Uani 1 1 d . . .
H3BB H 1.2499 -0.1685 1.2192 0.065 Uiso 1 1 calc R . .
H3BA H 0.8960 -0.2125 1.1911 0.065 Uiso 1 1 calc R . .
C4BA C 1.0647(14) -0.2093(4) 1.3960(5) 0.0892(19) Uani 1 1 d . . .
H4BB H 1.1894 -0.2629 1.3979 0.134 Uiso 1 1 calc R . .
H4BA H 0.8460 -0.2203 1.4243 0.134 Uiso 1 1 calc R . .
H4BC H 1.1811 -0.1680 1.4576 0.134 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C 0.048(3) 0.035(3) 0.059(3) 0.002(2) -0.006(2) -0.006(2)
C2BA 0.062(3) 0.056(3) 0.045(3) 0.006(2) -0.001(2) -0.005(3)
C0AA 0.038(2) 0.042(3) 0.043(2) 0.003(2) -0.0031(18) -0.0018(19)
C1AA 0.039(2) 0.038(2) 0.049(2) -0.002(2) -0.0057(19) -0.008(2)
C2AA 0.050(3) 0.041(3) 0.070(3) 0.000(3) -0.003(2) 0.004(2)
C3AA 0.045(2) 0.041(3) 0.045(2) -0.002(2) -0.0032(19) -0.0095(19)
C4AA 0.041(2) 0.044(3) 0.053(3) 0.000(2) -0.002(2) -0.005(2)
O 0.086(2) 0.047(2) 0.081(2) 0.0241(19) 0.0066(18) 0.0090(18)
C6AA 0.042(2) 0.036(3) 0.039(2) -0.001(2) -0.0010(17) -0.0062(19)
C5AA 0.065(3) 0.058(3) 0.047(3) -0.010(2) 0.007(2) -0.005(2)
C7AA 0.050(3) 0.076(4) 0.053(3) -0.013(3) 0.006(2) -0.009(2)
C8AA 0.076(3) 0.071(4) 0.045(3) -0.003(3) 0.006(2) -0.005(3)
C9AA 0.055(3) 0.049(3) 0.074(4) -0.015(3) -0.003(3) 0.009(2)
C0BA 0.050(2) 0.043(3) 0.047(3) -0.004(2) 0.000(2) 0.000(2)
C1BA 0.046(2) 0.042(3) 0.052(3) -0.007(2) -0.001(2) -0.009(2)
N1AA 0.058(2) 0.049(2) 0.0449(19) -0.0019(18) 0.0016(17) -0.0033(19)
N2AA 0.051(2) 0.037(2) 0.045(2) 0.0031(16) -0.0028(16) -0.0024(16)
C3BA 0.066(3) 0.041(3) 0.054(3) 0.000(2) -0.002(2) 0.004(2)
C4BA 0.122(5) 0.071(4) 0.074(4) 0.030(3) 0.010(3) 0.027(4)

_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
C O 1.226(5) . ?
C C4AA 1.468(5) . ?
C C3AA 1.517(6) . ?
C2BA C8AA 1.362(6) . ?
C2BA C3AA 1.401(6) . ?
C0AA C0BA 1.410(5) . ?
C0AA C3AA 1.413(5) . ?
C0AA C6AA 1.436(5) . ?
C1AA C1BA 1.390(6) . ?
C1AA C6AA 1.396(6) . ?
C1AA C4AA 1.399(5) . ?
C2AA C4AA 1.377(6) . ?
C2AA C9AA 1.408(6) . ?
C6AA N2AA 1.360(5) . ?
C5AA C0BA 1.372(6) . ?
C5AA C8AA 1.411(7) . ?
C7AA C9AA 1.376(7) . ?
C7AA C1BA 1.410(6) . ?
C1BA N1AA 1.380(5) . ?
N1AA N2AA 1.369(4) . ?
N2AA C3BA 1.481(5) . ?
C3BA C4BA 1.515(6) . ?

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
O C C4AA 123.2(4) . . ?
O C C3AA 120.8(4) . . ?
C4AA C C3AA 116.0(4) . . ?
C8AA C2BA C3AA 121.6(4) . . ?
C0BA C0AA C3AA 118.7(4) . . ?
C0BA C0AA C6AA 125.3(4) . . ?
C3AA C0AA C6AA 116.0(4) . . ?
C1BA C1AA C6AA 108.8(4) . . ?
C1BA C1AA C4AA 124.4(4) . . ?
C6AA C1AA C4AA 126.8(4) . . ?
C4AA C2AA C9AA 120.9(5) . . ?
C2BA C3AA C0AA 119.2(4) . . ?
C2BA C3AA C 116.5(4) . . ?
C0AA C3AA C 124.2(4) . . ?
C2AA C4AA C1AA 115.9(4) . . ?
C2AA C4AA C 127.5(4) . . ?
C1AA C4AA C 116.6(4) . . ?
N2AA C6AA C1AA 103.4(3) . . ?
N2AA C6AA C0AA 136.2(4) . . ?
C1AA C6AA C0AA 120.3(4) . . ?
C0BA C5AA C8AA 120.3(5) . . ?
C9AA C7AA C1BA 117.6(4) . . ?
C2BA C8AA C5AA 119.5(4) . . ?
C7AA C9AA C2AA 122.6(5) . . ?
C5AA C0BA C0AA 120.7(4) . . ?
N1AA C1BA C1AA 109.4(4) . . ?
N1AA C1BA C7AA 132.1(4) . . ?
C1AA C1BA C7AA 118.6(4) . . ?
N2AA N1AA C1BA 103.6(3) . . ?
C6AA N2AA N1AA 114.7(3) . . ?
C6AA N2AA C3BA 126.4(3) . . ?
N1AA N2AA C3BA 118.9(3) . . ?
N2AA C3BA C4BA 113.0(4) . . ?

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
C8AA C2BA C3AA C0AA 1.1(6) . . . . ?
C8AA C2BA C3AA C -179.0(4) . . . . ?
C0BA C0AA C3AA C2BA 0.6(6) . . . . ?
C6AA C0AA C3AA C2BA -179.1(4) . . . . ?
C0BA C0AA C3AA C -179.3(3) . . . . ?
C6AA C0AA C3AA C 0.9(6) . . . . ?
O C C3AA C2BA -2.8(6) . . . . ?
C4AA C C3AA C2BA 177.7(4) . . . . ?
O C C3AA C0AA 177.1(4) . . . . ?
C4AA C C3AA C0AA -2.4(5) . . . . ?
C9AA C2AA C4AA C1AA -0.4(6) . . . . ?
C9AA C2AA C4AA C -179.7(4) . . . . ?
C1BA C1AA C4AA C2AA -0.7(6) . . . . ?
C6AA C1AA C4AA C2AA -179.0(4) . . . . ?
C1BA C1AA C4AA C 178.7(4) . . . . ?
C6AA C1AA C4AA C 0.4(6) . . . . ?
O C C4AA C2AA 1.4(6) . . . . ?
C3AA C C4AA C2AA -179.1(4) . . . . ?
O C C4AA C1AA -177.8(4) . . . . ?
C3AA C C4AA C1AA 1.7(5) . . . . ?
C1BA C1AA C6AA N2AA 0.7(4) . . . . ?
C4AA C1AA C6AA N2AA 179.2(4) . . . . ?
C1BA C1AA C6AA C0AA 179.5(3) . . . . ?
C4AA C1AA C6AA C0AA -2.0(6) . . . . ?
C0BA C0AA C6AA N2AA -0.2(7) . . . . ?
C3AA C0AA C6AA N2AA 179.6(4) . . . . ?
C0BA C0AA C6AA C1AA -178.5(4) . . . . ?
C3AA C0AA C6AA C1AA 1.2(5) . . . . ?
C3AA C2BA C8AA C5AA -1.3(7) . . . . ?
C0BA C5AA C8AA C2BA -0.1(7) . . . . ?
C1BA C7AA C9AA C2AA 0.7(6) . . . . ?
C4AA C2AA C9AA C7AA 0.4(7) . . . . ?
C8AA C5AA C0BA C0AA 1.7(7) . . . . ?
C3AA C0AA C0BA C5AA -2.0(6) . . . . ?
C6AA C0AA C0BA C5AA 177.7(4) . . . . ?
C6AA C1AA C1BA N1AA -0.8(5) . . . . ?
C4AA C1AA C1BA N1AA -179.4(4) . . . . ?
C6AA C1AA C1BA C7AA -179.7(3) . . . . ?
C4AA C1AA C1BA C7AA 1.8(6) . . . . ?
C9AA C7AA C1BA N1AA 179.8(4) . . . . ?
C9AA C7AA C1BA C1AA -1.7(6) . . . . ?
C1AA C1BA N1AA N2AA 0.6(4) . . . . ?
C7AA C1BA N1AA N2AA 179.2(4) . . . . ?
C1AA C6AA N2AA N1AA -0.3(4) . . . . ?
C0AA C6AA N2AA N1AA -178.9(4) . . . . ?
C1AA C6AA N2AA C3BA 179.6(4) . . . . ?
C0AA C6AA N2AA C3BA 1.1(7) . . . . ?
C1BA N1AA N2AA C6AA -0.1(4) . . . . ?
C1BA N1AA N2AA C3BA 179.9(3) . . . . ?
C6AA N2AA C3BA C4BA 174.5(4) . . . . ?
N1AA N2AA C3BA C4BA -5.5(5) . . . . ?

#===END
_database_code_depnum_ccdc_archive 'CCDC 990062'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_jnk_ch3_r

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 N2 O'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C15 H10 N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         234.25
_chemical_compound_source        'see text'

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

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   4.9825(3)
_cell_length_b                   14.7961(9)
_cell_length_c                   15.1704(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.397(5)
_cell_angle_gamma                90
_cell_volume                     1117.40(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(1)
_cell_measurement_reflns_used    11331
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      25.0
_cell_special_details            
;
;
_exptl_crystal_description       block
_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.090
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction,2009)'
_exptl_absorpt_correction_T_min  0.9736
_exptl_absorpt_correction_T_max  0.9823

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      290(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Oxford Xcalibur,Eos(Nova) CCD detector'
_diffrn_measurement_method       'fω scans'
_diffrn_reflns_number            11331
_diffrn_reflns_av_R_equivalents  0.1312
_diffrn_reflns_av_sigmaI/netI    0.0587
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_full        24.97
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_reduction_process 
;
;
# number of unique reflections
_reflns_number_total             1954
# number of observed reflections (> n sig(I))
_reflns_number_gt                1503
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlisPro RED (Oxford Diffraction, 2009)'
_computing_structure_solution    'SHELXS97  (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

#===============================================================================

# 8. REFINEMENT DATA
_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)+(0.1066P)²+0.2367P] 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     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1954
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0661
_refine_ls_wR_factor_ref         0.2007
_refine_ls_wR_factor_gt          0.1844
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.056

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
C10 C 0.1215(4) 0.26218(16) 0.87780(14) 0.0444(6) Uani 1 1 d . . .
C12 C -0.0443(4) 0.25646(16) 0.80154(14) 0.0465(6) Uani 1 1 d . . .
C14 C 0.3207(4) 0.33283(16) 0.88494(14) 0.0445(6) Uani 1 1 d . . .
C5 C 0.4991(5) 0.34430(17) 0.95724(15) 0.0493(6) Uani 1 1 d . . .
H5 H 0.4935 0.3050 1.0049 0.059 Uiso 1 1 calc R . .
C13 C 0.3325(4) 0.39311(16) 0.81258(14) 0.0472(6) Uani 1 1 d . . .
C4 C -0.2188(5) 0.18524(17) 0.81353(16) 0.0510(7) Uani 1 1 d . . .
C8 C 0.5213(5) 0.46267(18) 0.81672(17) 0.0569(7) Uani 1 1 d . . .
H8 H 0.5299 0.5030 0.7699 0.068 Uiso 1 1 calc R . .
N2 N 0.0557(4) 0.19839(14) 0.93528(13) 0.0530(6) Uani 1 1 d . . .
C11 C -0.0442(5) 0.31160(17) 0.72758(15) 0.0509(7) Uani 1 1 d . . .
C9 C 0.1533(5) 0.38578(18) 0.73066(15) 0.0546(7) Uani 1 1 d . . .
C1 C -0.2344(5) 0.2913(2) 0.66138(16) 0.0608(8) Uani 1 1 d . . .
H1 H -0.2443 0.3255 0.6099 0.073 Uiso 1 1 calc R . .
O1 O 0.1737(5) 0.44037(16) 0.67045(13) 0.0815(7) Uani 1 1 d . . .
C3 C -0.4125(5) 0.1648(2) 0.74668(18) 0.0622(8) Uani 1 1 d . . .
H3 H -0.5343 0.1177 0.7521 0.075 Uiso 1 1 calc R . .
C6 C 0.6836(5) 0.41345(19) 0.95849(17) 0.0594(7) Uani 1 1 d . . .
H6 H 0.8022 0.4203 1.0070 0.071 Uiso 1 1 calc R . .
C2 C -0.4119(5) 0.2191(2) 0.67204(18) 0.0676(9) Uani 1 1 d . . .
H2 H -0.5368 0.2068 0.6264 0.081 Uiso 1 1 calc R . .
N1 N -0.1536(4) 0.15203(15) 0.89558(14) 0.0566(6) Uani 1 1 d . . .
C7 C 0.6947(5) 0.47265(19) 0.88872(18) 0.0616(7) Uani 1 1 d . . .
H7 H 0.8196 0.5194 0.8904 0.074 Uiso 1 1 calc R . .
C15 C -0.2754(7) 0.0775(2) 0.9416(2) 0.0847(10) Uani 1 1 d . . .
H15A H -0.4603 0.0718 0.9220 0.127 Uiso 1 1 calc R . .
H15B H -0.2648 0.0890 1.0040 0.127 Uiso 1 1 calc R . .
H15C H -0.1816 0.0226 0.9294 0.127 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C10 0.0428(12) 0.0538(13) 0.0363(11) -0.0059(10) -0.0016(9) 0.0069(10)
C12 0.0422(12) 0.0595(14) 0.0376(12) -0.0096(10) -0.0019(9) 0.0114(10)
C14 0.0424(12) 0.0528(13) 0.0382(12) -0.0055(10) 0.0034(9) 0.0091(10)
C5 0.0486(13) 0.0590(14) 0.0400(12) -0.0040(10) -0.0008(9) 0.0035(11)
C13 0.0449(12) 0.0540(14) 0.0434(12) -0.0015(10) 0.0087(10) 0.0111(10)
C4 0.0466(13) 0.0597(15) 0.0463(13) -0.0156(11) -0.0039(10) 0.0091(11)
C8 0.0603(15) 0.0544(15) 0.0568(15) 0.0038(12) 0.0153(12) 0.0081(12)
N2 0.0534(12) 0.0584(12) 0.0467(11) -0.0015(9) -0.0046(9) -0.0049(9)
C11 0.0498(13) 0.0649(15) 0.0379(12) -0.0069(11) -0.0011(9) 0.0231(11)
C9 0.0554(14) 0.0662(16) 0.0424(13) 0.0039(12) 0.0054(10) 0.0192(12)
C1 0.0610(15) 0.0802(19) 0.0405(13) -0.0134(12) -0.0079(11) 0.0255(14)
O1 0.0947(16) 0.0917(15) 0.0578(12) 0.0261(11) -0.0007(10) 0.0123(12)
C3 0.0511(15) 0.0691(17) 0.0654(17) -0.0246(14) -0.0083(12) 0.0087(12)
C6 0.0529(14) 0.0708(17) 0.0543(15) -0.0136(13) -0.0016(11) -0.0038(12)
C2 0.0592(16) 0.087(2) 0.0551(16) -0.0305(15) -0.0185(12) 0.0235(15)
N1 0.0596(13) 0.0566(13) 0.0531(12) -0.0029(10) -0.0056(9) -0.0062(10)
C7 0.0587(15) 0.0616(17) 0.0649(17) -0.0073(13) 0.0069(12) -0.0073(12)
C15 0.090(2) 0.079(2) 0.084(2) 0.0112(17) -0.0099(17) -0.0270(17)

_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
C10 N2 1.335(3) . ?
C10 C12 1.396(3) . ?
C10 C14 1.443(3) . ?
C12 C4 1.383(4) . ?
C12 C11 1.387(3) . ?
C14 C5 1.393(3) . ?
C14 C13 1.418(3) . ?
C5 C6 1.375(4) . ?
C13 C8 1.394(4) . ?
C13 C9 1.503(4) . ?
C4 N1 1.365(3) . ?
C4 C3 1.404(4) . ?
C8 C7 1.372(4) . ?
N2 N1 1.367(3) . ?
C11 C1 1.385(4) . ?
C11 C9 1.474(4) . ?
C9 O1 1.227(3) . ?
C1 C2 1.400(4) . ?
C3 C2 1.388(4) . ?
C6 C7 1.377(4) . ?
N1 C15 1.452(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C10 C12 110.2(2) . . ?
N2 C10 C14 130.6(2) . . ?
C12 C10 C14 119.2(2) . . ?
C4 C12 C11 125.2(2) . . ?
C4 C12 C10 106.9(2) . . ?
C11 C12 C10 127.9(2) . . ?
C5 C14 C13 119.2(2) . . ?
C5 C14 C10 124.2(2) . . ?
C13 C14 C10 116.6(2) . . ?
C6 C5 C14 120.4(2) . . ?
C8 C13 C14 118.6(2) . . ?
C8 C13 C9 117.8(2) . . ?
C14 C13 C9 123.5(2) . . ?
N1 C4 C12 105.5(2) . . ?
N1 C4 C3 135.4(3) . . ?
C12 C4 C3 119.1(2) . . ?
C7 C8 C13 121.1(2) . . ?
C10 N2 N1 105.70(19) . . ?
C1 C11 C12 115.8(2) . . ?
C1 C11 C9 128.4(2) . . ?
C12 C11 C9 115.8(2) . . ?
O1 C9 C11 122.9(2) . . ?
O1 C9 C13 120.2(3) . . ?
C11 C9 C13 116.9(2) . . ?
C11 C1 C2 119.9(3) . . ?
C2 C3 C4 116.1(3) . . ?
C5 C6 C7 120.7(2) . . ?
C3 C2 C1 123.9(2) . . ?
C4 N1 N2 111.7(2) . . ?
C4 N1 C15 128.6(2) . . ?
N2 N1 C15 119.7(2) . . ?
C8 C7 C6 120.0(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C10 C12 C4 -0.2(3) . . . . ?
C14 C10 C12 C4 -178.30(18) . . . . ?
N2 C10 C12 C11 178.4(2) . . . . ?
C14 C10 C12 C11 0.3(3) . . . . ?
N2 C10 C14 C5 3.3(4) . . . . ?
C12 C10 C14 C5 -179.1(2) . . . . ?
N2 C10 C14 C13 -177.2(2) . . . . ?
C12 C10 C14 C13 0.5(3) . . . . ?
C13 C14 C5 C6 0.2(3) . . . . ?
C10 C14 C5 C6 179.8(2) . . . . ?
C5 C14 C13 C8 -0.7(3) . . . . ?
C10 C14 C13 C8 179.76(18) . . . . ?
C5 C14 C13 C9 178.78(19) . . . . ?
C10 C14 C13 C9 -0.8(3) . . . . ?
C11 C12 C4 N1 -178.1(2) . . . . ?
C10 C12 C4 N1 0.5(2) . . . . ?
C11 C12 C4 C3 0.4(3) . . . . ?
C10 C12 C4 C3 179.13(19) . . . . ?
C14 C13 C8 C7 0.6(3) . . . . ?
C9 C13 C8 C7 -178.9(2) . . . . ?
C12 C10 N2 N1 -0.2(2) . . . . ?
C14 C10 N2 N1 177.6(2) . . . . ?
C4 C12 C11 C1 -0.7(3) . . . . ?
C10 C12 C11 C1 -179.1(2) . . . . ?
C4 C12 C11 C9 177.6(2) . . . . ?
C10 C12 C11 C9 -0.8(3) . . . . ?
C1 C11 C9 O1 -1.0(4) . . . . ?
C12 C11 C9 O1 -179.1(2) . . . . ?
C1 C11 C9 C13 178.5(2) . . . . ?
C12 C11 C9 C13 0.4(3) . . . . ?
C8 C13 C9 O1 -0.7(3) . . . . ?
C14 C13 C9 O1 179.9(2) . . . . ?
C8 C13 C9 C11 179.82(18) . . . . ?
C14 C13 C9 C11 0.4(3) . . . . ?
C12 C11 C1 C2 0.3(3) . . . . ?
C9 C11 C1 C2 -177.8(2) . . . . ?
N1 C4 C3 C2 178.3(2) . . . . ?
C12 C4 C3 C2 0.3(3) . . . . ?
C14 C5 C6 C7 0.3(4) . . . . ?
C4 C3 C2 C1 -0.7(4) . . . . ?
C11 C1 C2 C3 0.4(4) . . . . ?
C12 C4 N1 N2 -0.7(3) . . . . ?
C3 C4 N1 N2 -178.9(2) . . . . ?
C12 C4 N1 C15 179.4(3) . . . . ?
C3 C4 N1 C15 1.2(5) . . . . ?
C10 N2 N1 C4 0.6(3) . . . . ?
C10 N2 N1 C15 -179.5(2) . . . . ?
C13 C8 C7 C6 -0.1(4) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?

#===END
_database_code_depnum_ccdc_archive 'CCDC 983911'
