# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_ch15990

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H12 N2 O'
_chemical_formula_sum            'C17 H12 N2 O'
_chemical_formula_weight         260.29

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   'C 2/c'

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                   18.520
_cell_length_b                   6.966
_cell_length_c                   19.193
_cell_angle_alpha                90.00
_cell_angle_beta                 97.37
_cell_angle_gamma                90.00
_cell_volume                     2455.6
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9549
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8373
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         25.06
_reflns_number_total             2178
_reflns_number_gt                1623
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR2002 (Giacovazzo et al, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0967P)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         2178
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1545
_refine_ls_wR_factor_gt          0.1205
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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
C1 C 0.39982(10) 0.2803(2) 0.04666(10) 0.0278(5) Uani 1 1 d . . .
C2 C 0.39495(9) 0.3081(2) -0.02997(9) 0.0246(4) Uani 1 1 d . . .
C3 C 0.32863(10) 0.3479(2) -0.06750(10) 0.0274(4) Uani 1 1 d . . .
H3 H 0.2864 0.3565 -0.0444 0.033 Uiso 1 1 calc R . .
C4 C 0.32359(9) 0.3758(2) -0.14016(9) 0.0259(4) Uani 1 1 d . . .
C5 C 0.25797(10) 0.4263(2) -0.18221(10) 0.0319(5) Uani 1 1 d . . .
H5 H 0.2143 0.4376 -0.1615 0.038 Uiso 1 1 calc R . .
C6 C 0.25707(10) 0.4591(2) -0.25239(10) 0.0356(5) Uani 1 1 d . . .
H6 H 0.2130 0.4958 -0.2801 0.043 Uiso 1 1 calc R . .
C7 C 0.32123(10) 0.4388(2) -0.28403(10) 0.0378(5) Uani 1 1 d . . .
H7 H 0.3200 0.4622 -0.3329 0.045 Uiso 1 1 calc R . .
C8 C 0.38517(10) 0.3860(2) -0.24537(10) 0.0343(5) Uani 1 1 d . . .
H8 H 0.4276 0.3697 -0.2677 0.041 Uiso 1 1 calc R . .
C9 C 0.38850(10) 0.3554(2) -0.17202(9) 0.0266(4) Uani 1 1 d . . .
C10 C 0.45674(9) 0.2906(2) -0.06581(9) 0.0238(4) Uani 1 1 d . . .
C11 C 0.52679(9) 0.2464(2) -0.02460(10) 0.0258(4) Uani 1 1 d . . .
C12 C 0.58996(10) 0.2246(2) -0.05655(10) 0.0294(4) Uani 1 1 d . . .
H12 H 0.5876 0.2411 -0.1059 0.035 Uiso 1 1 calc R . .
C13 C 0.65564(10) 0.1796(2) -0.01765(11) 0.0341(5) Uani 1 1 d . . .
H13 H 0.6981 0.1641 -0.0401 0.041 Uiso 1 1 calc R . .
C14 C 0.65901(10) 0.1572(2) 0.05447(11) 0.0352(5) Uani 1 1 d . . .
H14 H 0.7042 0.1269 0.0815 0.042 Uiso 1 1 calc R . .
C15 C 0.59757(10) 0.1785(2) 0.08760(10) 0.0326(5) Uani 1 1 d . . .
H15 H 0.6009 0.1632 0.1371 0.039 Uiso 1 1 calc R . .
C16 C 0.53045(10) 0.2223(2) 0.04862(10) 0.0264(4) Uani 1 1 d . . .
C17 C 0.47316(11) 0.2080(3) 0.15790(10) 0.0388(5) Uani 1 1 d . . .
N1 N 0.46765(8) 0.23969(17) 0.08204(8) 0.0283(4) Uani 1 1 d . . .
N2 N 0.45408(8) 0.31188(18) -0.13481(8) 0.0274(4) Uani 1 1 d . . .
O1 O 0.34598(7) 0.29242(17) 0.07778(7) 0.0374(4) Uani 1 1 d . . .
H17A H 0.5045 0.3044 0.1860 0.045 Uiso 1 1 d R . .
H17B H 0.4207 0.2190 0.1735 0.045 Uiso 1 1 d R . .
H17C H 0.4873 0.0757 0.1705 0.045 Uiso 1 1 d 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
C1 0.0316(11) 0.0231(8) 0.0302(11) -0.0035(7) 0.0094(9) -0.0059(7)
C2 0.0277(10) 0.0191(7) 0.0282(10) -0.0026(7) 0.0082(8) -0.0038(7)
C3 0.0280(10) 0.0238(7) 0.0325(11) -0.0022(7) 0.0122(8) -0.0021(7)
C4 0.0287(10) 0.0191(7) 0.0305(11) -0.0016(7) 0.0059(8) -0.0027(7)
C5 0.0306(11) 0.0280(8) 0.0378(12) 0.0001(8) 0.0072(9) 0.0006(7)
C6 0.0348(11) 0.0318(9) 0.0389(12) 0.0049(8) -0.0002(9) -0.0015(8)
C7 0.0422(12) 0.0404(9) 0.0303(11) 0.0050(8) 0.0031(9) -0.0072(9)
C8 0.0325(11) 0.0414(10) 0.0303(12) 0.0002(8) 0.0084(9) -0.0076(8)
C9 0.0295(10) 0.0231(8) 0.0277(10) -0.0019(7) 0.0053(8) -0.0064(7)
C10 0.0288(10) 0.0186(7) 0.0249(10) -0.0037(7) 0.0065(8) -0.0059(7)
C11 0.0277(10) 0.0199(7) 0.0303(11) -0.0043(7) 0.0063(8) -0.0067(7)
C12 0.0307(11) 0.0279(8) 0.0304(11) -0.0043(7) 0.0068(8) -0.0066(7)
C13 0.0280(11) 0.0315(8) 0.0440(13) -0.0053(8) 0.0095(9) -0.0050(7)
C14 0.0284(11) 0.0313(8) 0.0440(13) 0.0012(8) -0.0027(9) -0.0052(7)
C15 0.0376(11) 0.0283(8) 0.0311(11) 0.0014(7) 0.0012(9) -0.0071(8)
C16 0.0307(10) 0.0188(7) 0.0303(11) -0.0028(7) 0.0063(8) -0.0058(7)
C17 0.0450(13) 0.0469(10) 0.0252(11) 0.0025(8) 0.0075(9) -0.0051(9)
N1 0.0337(9) 0.0281(7) 0.0241(9) 0.0001(6) 0.0073(7) -0.0046(6)
N2 0.0267(9) 0.0304(7) 0.0260(9) -0.0028(6) 0.0067(7) -0.0053(6)
O1 0.0355(8) 0.0481(7) 0.0312(8) -0.0029(6) 0.0148(6) -0.0035(6)

_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
C1 O1 1.229(2) . ?
C1 N1 1.379(2) . ?
C1 C2 1.475(2) . ?
C2 C3 1.370(2) . ?
C2 C10 1.414(2) . ?
C3 C4 1.399(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.414(2) . ?
C4 C9 1.424(2) . ?
C5 C6 1.364(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.409(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.365(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.417(2) . ?
C8 H8 0.9500 . ?
C9 N2 1.362(2) . ?
C10 N2 1.327(2) . ?
C10 C11 1.463(2) . ?
C11 C12 1.397(2) . ?
C11 C16 1.408(2) . ?
C12 C13 1.379(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.400(2) . ?
C15 H15 0.9500 . ?
C16 N1 1.404(2) . ?
C17 N1 1.463(2) . ?
C17 H17A 0.9994 . ?
C17 H17B 1.0548 . ?
C17 H17C 0.9802 . ?

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
O1 C1 N1 121.29(17) . . ?
O1 C1 C2 121.73(16) . . ?
N1 C1 C2 116.97(16) . . ?
C3 C2 C10 119.24(17) . . ?
C3 C2 C1 119.14(16) . . ?
C10 C2 C1 121.60(16) . . ?
C2 C3 C4 119.52(17) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 123.08(17) . . ?
C3 C4 C9 117.52(16) . . ?
C5 C4 C9 119.39(17) . . ?
C6 C5 C4 120.38(18) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.31(18) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.89(18) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 120.32(18) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
N2 C9 C8 118.46(17) . . ?
N2 C9 C4 122.85(16) . . ?
C8 C9 C4 118.68(17) . . ?
N2 C10 C2 123.17(16) . . ?
N2 C10 C11 118.67(16) . . ?
C2 C10 C11 118.16(16) . . ?
C12 C11 C16 119.29(17) . . ?
C12 C11 C10 121.32(17) . . ?
C16 C11 C10 119.37(16) . . ?
C13 C12 C11 121.14(18) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 119.32(18) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 120.90(18) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 120.33(18) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 N1 120.37(17) . . ?
C15 C16 C11 119.02(17) . . ?
N1 C16 C11 120.60(16) . . ?
N1 C17 H17A 113.4 . . ?
N1 C17 H17B 108.8 . . ?
H17A C17 H17B 106.9 . . ?
N1 C17 H17C 111.7 . . ?
H17A C17 H17C 112.3 . . ?
H17B C17 H17C 103.0 . . ?
C1 N1 C16 123.28(16) . . ?
C1 N1 C17 117.65(16) . . ?
C16 N1 C17 119.05(15) . . ?
C10 N2 C9 117.67(16) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.148
_database_code_depnum_ccdc_archive 'CCDC 998615'
#######################################################################
#
#                 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_a15989

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 N O4'
_chemical_formula_sum            'C13 H11 N O4'
_chemical_formula_weight         245.23

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   'P 21/c'

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                   6.6756(2)
_cell_length_b                   8.2693(3)
_cell_length_c                   20.4546(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.578(2)
_cell_angle_gamma                90.00
_cell_volume                     1129.09(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9703
_exptl_absorpt_correction_T_max  0.9882
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7556
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         25.12
_reflns_number_total             1986
_reflns_number_gt                1760
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0601P)²+0.6887P] 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         1986
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1261
_refine_ls_wR_factor_gt          0.1212
_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
C1 C 0.7734(2) 0.58620(19) 0.03201(8) 0.0231(4) Uani 1 1 d . . .
C2 C 0.7304(2) 0.5181(2) -0.02831(8) 0.0263(4) Uani 1 1 d . . .
H2 H 0.7101 0.5845 -0.0657 0.032 Uiso 1 1 calc R . .
C3 C 0.7176(2) 0.3519(2) -0.03317(8) 0.0300(4) Uani 1 1 d . . .
H3 H 0.6901 0.3030 -0.0743 0.036 Uiso 1 1 calc R . .
C4 C 0.7447(3) 0.2563(2) 0.02183(9) 0.0315(4) Uani 1 1 d . . .
H4 H 0.7346 0.1420 0.0184 0.038 Uiso 1 1 calc R . .
C5 C 0.7866(3) 0.3269(2) 0.08191(9) 0.0292(4) Uani 1 1 d . . .
H5 H 0.8044 0.2600 0.1193 0.035 Uiso 1 1 calc R . .
C6 C 0.8032(2) 0.4940(2) 0.08857(8) 0.0243(4) Uani 1 1 d . . .
C7 C 0.8712(3) 0.5603(2) 0.15211(8) 0.0282(4) Uani 1 1 d . . .
H7 H 0.9941 0.6181 0.1519 0.034 Uiso 1 1 calc R . .
C8 C 0.7805(3) 0.5486(2) 0.20983(8) 0.0269(4) Uani 1 1 d . . .
C9 C 0.5723(3) 0.4850(2) 0.21721(8) 0.0307(4) Uani 1 1 d . . .
C10 C 0.5140(3) 0.4273(3) 0.28404(10) 0.0498(6) Uani 1 1 d . . .
H10A H 0.3661 0.4274 0.2871 0.060 Uiso 1 1 calc R . .
H10B H 0.5607 0.3146 0.2900 0.060 Uiso 1 1 calc R . .
C11 C 0.5991(3) 0.5293(3) 0.33751(10) 0.0494(6) Uani 1 1 d . . .
H11A H 0.5364 0.6377 0.3354 0.059 Uiso 1 1 calc R . .
H11B H 0.5639 0.4804 0.3801 0.059 Uiso 1 1 calc R . .
C12 C 0.8204(3) 0.5480(3) 0.33451(9) 0.0496(6) Uani 1 1 d . . .
H12A H 0.8833 0.4433 0.3461 0.059 Uiso 1 1 calc R . .
H12B H 0.8628 0.6281 0.3679 0.059 Uiso 1 1 calc R . .
C13 C 0.8980(3) 0.6007(2) 0.26951(8) 0.0328(4) Uani 1 1 d . . .
N1 N 0.7788(2) 0.76313(18) 0.03586(7) 0.0282(4) Uani 1 1 d . . .
O1 O 0.8094(2) 0.82599(16) 0.08921(7) 0.0468(4) Uani 1 1 d . . .
O2 O 0.7510(2) 0.84108(16) -0.01406(7) 0.0481(4) Uani 1 1 d . . .
O3 O 0.4560(2) 0.48208(19) 0.17139(6) 0.0450(4) Uani 1 1 d . . .
O4 O 1.0513(2) 0.6779(2) 0.26442(7) 0.0510(4) Uani 1 1 d . . .

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
C1 0.0202(8) 0.0244(9) 0.0248(8) -0.0006(6) 0.0028(6) 0.0009(6)
C2 0.0219(8) 0.0348(9) 0.0223(8) 0.0001(7) 0.0018(6) 0.0007(7)
C3 0.0244(9) 0.0381(10) 0.0277(9) -0.0104(7) 0.0026(7) -0.0013(7)
C4 0.0295(9) 0.0253(9) 0.0399(10) -0.0053(7) 0.0039(7) -0.0011(7)
C5 0.0291(9) 0.0287(9) 0.0299(9) 0.0042(7) 0.0017(7) 0.0008(7)
C6 0.0204(8) 0.0298(9) 0.0227(8) -0.0005(6) 0.0028(6) 0.0006(6)
C7 0.0310(9) 0.0278(9) 0.0257(9) 0.0014(7) -0.0018(7) -0.0036(7)
C8 0.0327(9) 0.0257(9) 0.0221(8) 0.0000(6) -0.0022(7) -0.0003(7)
C9 0.0333(9) 0.0335(10) 0.0254(9) -0.0055(7) 0.0006(7) -0.0016(7)
C10 0.0481(12) 0.0688(15) 0.0326(11) 0.0038(10) 0.0040(9) -0.0210(11)
C11 0.0549(13) 0.0647(15) 0.0287(10) 0.0018(10) 0.0062(9) -0.0105(11)
C12 0.0504(12) 0.0754(16) 0.0229(10) -0.0024(9) -0.0036(8) -0.0124(11)
C13 0.0357(10) 0.0359(10) 0.0267(9) -0.0047(7) -0.0021(7) -0.0033(8)
N1 0.0285(8) 0.0281(8) 0.0281(8) 0.0004(6) 0.0034(6) 0.0004(6)
O1 0.0771(11) 0.0300(7) 0.0334(8) -0.0073(6) -0.0014(7) -0.0028(7)
O2 0.0759(11) 0.0318(8) 0.0366(8) 0.0098(6) -0.0064(7) 0.0023(7)
O3 0.0351(7) 0.0696(10) 0.0301(7) -0.0073(7) -0.0041(6) -0.0062(7)
O4 0.0489(9) 0.0688(11) 0.0353(8) -0.0083(7) -0.0030(6) -0.0247(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
C1 C2 1.383(2) . ?
C1 C6 1.398(2) . ?
C1 N1 1.466(2) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.478(2) . ?
C7 C8 1.335(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.495(2) . ?
C8 C13 1.507(2) . ?
C9 O3 1.211(2) . ?
C9 C10 1.503(3) . ?
C10 C11 1.489(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.487(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.497(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O4 1.211(2) . ?
N1 O2 1.2203(19) . ?
N1 O1 1.2238(19) . ?

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 C1 C6 122.86(15) . . ?
C2 C1 N1 117.31(14) . . ?
C6 C1 N1 119.78(14) . . ?
C3 C2 C1 118.77(16) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 120.14(16) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 120.20(16) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 121.31(16) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 116.72(15) . . ?
C5 C6 C7 118.51(15) . . ?
C1 C6 C7 124.43(15) . . ?
C8 C7 C6 127.79(16) . . ?
C8 C7 H7 116.1 . . ?
C6 C7 H7 116.1 . . ?
C7 C8 C9 123.00(15) . . ?
C7 C8 C13 117.29(16) . . ?
C9 C8 C13 119.70(14) . . ?
O3 C9 C8 121.22(16) . . ?
O3 C9 C10 121.83(17) . . ?
C8 C9 C10 116.95(15) . . ?
C11 C10 C9 112.85(17) . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C10 113.60(18) . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 114.84(17) . . ?
C11 C12 H12A 108.6 . . ?
C13 C12 H12A 108.6 . . ?
C11 C12 H12B 108.6 . . ?
C13 C12 H12B 108.6 . . ?
H12A C12 H12B 107.5 . . ?
O4 C13 C12 122.02(17) . . ?
O4 C13 C8 120.94(16) . . ?
C12 C13 C8 117.01(16) . . ?
O2 N1 O1 122.98(15) . . ?
O2 N1 C1 118.61(14) . . ?
O1 N1 C1 118.41(14) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.12
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.040
_database_code_depnum_ccdc_archive 'CCDC 998616'
#######################################################################
#
#                 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_a15765

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 N O'
_chemical_formula_sum            'C13 H11 N O'
_chemical_formula_weight         197.23

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   'P 21/c'

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                   8.2359(18)
_cell_length_b                   9.5653(14)
_cell_length_c                   12.615(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.791(7)
_cell_angle_gamma                90.00
_cell_volume                     979.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9708
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6524
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_sigmaI/netI    0.0555
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.51
_diffrn_reflns_theta_max         25.19
_reflns_number_total             1753
_reflns_number_gt                1243
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0665P)²+0.0786P] 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         1753
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1345
_refine_ls_wR_factor_gt          0.1190
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
C1 C 0.8222(2) 0.55207(19) 1.09714(12) 0.0279(5) Uani 1 1 d . . .
C2 C 0.8754(2) 0.6285(2) 1.19250(13) 0.0359(5) Uani 1 1 d . . .
H2 H 0.9493 0.5865 1.2497 0.043 Uiso 1 1 calc R . .
C3 C 0.8222(2) 0.7614(2) 1.20334(15) 0.0407(5) Uani 1 1 d . . .
H3 H 0.8585 0.8110 1.2683 0.049 Uiso 1 1 calc R . .
C4 C 0.7139(2) 0.8266(2) 1.11924(15) 0.0398(5) Uani 1 1 d . . .
H4 H 0.6769 0.9193 1.1280 0.048 Uiso 1 1 calc R . .
C5 C 0.6621(2) 0.75668(19) 1.02538(16) 0.0358(5) Uani 1 1 d . . .
H5 H 0.5906 0.8016 0.9685 0.043 Uiso 1 1 calc R . .
C6 C 0.7140(2) 0.61770(18) 1.01194(13) 0.0274(5) Uani 1 1 d . . .
C7 C 0.6641(2) 0.53882(18) 0.91852(13) 0.0291(5) Uani 1 1 d . . .
H7 H 0.5941 0.5797 0.8589 0.035 Uiso 1 1 calc R . .
C8 C 0.7152(2) 0.40352(19) 0.91237(12) 0.0262(5) Uani 1 1 d . . .
C9 C 0.6612(2) 0.3188(2) 0.81318(13) 0.0325(5) Uani 1 1 d . . .
C10 C 0.7157(2) 0.17005(19) 0.81432(14) 0.0382(5) Uani 1 1 d . . .
H10A H 0.8145 0.1640 0.7795 0.046 Uiso 1 1 calc R . .
H10B H 0.6276 0.1140 0.7708 0.046 Uiso 1 1 calc R . .
C11 C 0.7561(2) 0.10639(19) 0.92572(14) 0.0374(5) Uani 1 1 d . . .
H11A H 0.6537 0.0970 0.9564 0.045 Uiso 1 1 calc R . .
H11B H 0.8027 0.0118 0.9205 0.045 Uiso 1 1 calc R . .
C12 C 0.8782(2) 0.19568(19) 0.99958(14) 0.0348(5) Uani 1 1 d . . .
H12A H 0.8939 0.1563 1.0732 0.042 Uiso 1 1 calc R . .
H12B H 0.9859 0.1932 0.9747 0.042 Uiso 1 1 calc R . .
C13 C 0.8217(2) 0.34474(18) 1.00261(12) 0.0271(5) Uani 1 1 d . . .
N1 N 0.87499(18) 0.41677(15) 1.09107(10) 0.0303(4) Uani 1 1 d . . .
O1 O 0.57953(18) 0.37167(13) 0.73354(9) 0.0504(5) Uani 1 1 d . . .

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
C1 0.0291(11) 0.0297(11) 0.0261(10) 0.0008(8) 0.0082(8) -0.0027(9)
C2 0.0415(12) 0.0398(13) 0.0260(10) -0.0021(8) 0.0046(8) -0.0047(10)
C3 0.0447(13) 0.0429(14) 0.0369(11) -0.0110(9) 0.0138(9) -0.0093(10)
C4 0.0407(13) 0.0307(12) 0.0508(13) -0.0081(9) 0.0162(10) -0.0023(9)
C5 0.0319(11) 0.0311(12) 0.0450(11) 0.0016(9) 0.0082(9) 0.0009(9)
C6 0.0260(11) 0.0282(11) 0.0294(10) 0.0020(8) 0.0081(8) -0.0034(8)
C7 0.0259(10) 0.0318(12) 0.0287(10) 0.0057(8) 0.0025(7) -0.0012(8)
C8 0.0247(10) 0.0302(11) 0.0241(9) 0.0015(7) 0.0051(7) -0.0033(8)
C9 0.0319(11) 0.0354(12) 0.0298(10) 0.0013(8) 0.0040(8) -0.0051(9)
C10 0.0397(13) 0.0351(12) 0.0379(11) -0.0090(9) 0.0014(9) -0.0029(9)
C11 0.0381(12) 0.0277(12) 0.0469(12) -0.0008(9) 0.0090(9) 0.0015(9)
C12 0.0381(12) 0.0323(12) 0.0339(10) 0.0028(8) 0.0054(8) 0.0054(9)
C13 0.0264(10) 0.0301(11) 0.0259(9) 0.0037(8) 0.0074(7) -0.0015(8)
N1 0.0348(10) 0.0309(10) 0.0246(8) 0.0012(6) 0.0036(7) 0.0002(7)
O1 0.0660(11) 0.0461(10) 0.0321(8) 0.0019(6) -0.0117(7) -0.0013(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
C1 N1 1.372(2) . ?
C1 C2 1.412(2) . ?
C1 C6 1.420(2) . ?
C2 C3 1.360(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.410(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.364(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.415(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.401(2) . ?
C7 C8 1.367(2) . ?
C7 H7 0.9500 . ?
C8 C13 1.429(2) . ?
C8 C9 1.493(2) . ?
C9 O1 1.2194(19) . ?
C9 C10 1.492(3) . ?
C10 C11 1.516(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.514(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.502(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N1 1.321(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
N1 C1 C2 118.70(15) . . ?
N1 C1 C6 122.60(15) . . ?
C2 C1 C6 118.68(17) . . ?
C3 C2 C1 120.73(17) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.77(17) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 120.03(18) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.59(17) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 123.73(16) . . ?
C7 C6 C1 117.08(16) . . ?
C5 C6 C1 119.19(16) . . ?
C8 C7 C6 120.55(15) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C13 118.72(15) . . ?
C7 C8 C9 120.67(15) . . ?
C13 C8 C9 120.61(16) . . ?
O1 C9 C10 121.75(16) . . ?
O1 C9 C8 120.63(17) . . ?
C10 C9 C8 117.59(15) . . ?
C9 C10 C11 114.23(15) . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C10 111.23(16) . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 C11 111.99(15) . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
N1 C13 C8 122.58(16) . . ?
N1 C13 C12 117.15(14) . . ?
C8 C13 C12 120.27(15) . . ?
C13 N1 C1 118.44(14) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.19
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.045
_database_code_depnum_ccdc_archive 'CCDC 998617'
