# 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_mx01_11

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H16 N2 O2'
_chemical_formula_sum            'C17 H16 N2 O2'
_chemical_formula_weight         280.32

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   10.8379(2)
_cell_length_b                   7.0007(1)
_cell_length_c                   18.8456(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.548(1)
_cell_angle_gamma                90.00
_cell_volume                     1428.46(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    8016
_cell_measurement_theta_min      1.8771
_cell_measurement_theta_max      32.1955

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_min  0.95108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_detector_area_resol_mean 10.3389
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14965
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0147
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3264
_reflns_number_gt                2897
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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)+(0.0482P)²+0.5036P] 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         3264
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.1000
_refine_ls_wR_factor_gt          0.0964
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
O1 O -0.10113(7) 0.28605(11) -0.02482(4) 0.02007(18) Uani 1 1 d . . .
O2 O 0.21294(7) 0.18118(12) 0.17945(4) 0.02444(19) Uani 1 1 d . . .
N1 N -0.12743(9) 0.29885(15) -0.14151(5) 0.0267(2) Uani 1 1 d . . .
N2 N -0.00314(9) 0.25065(15) -0.12411(5) 0.0264(2) Uani 1 1 d . . .
C1 C -0.18026(10) 0.31780(15) -0.08218(6) 0.0215(2) Uani 1 1 d . . .
C2 C 0.00710(10) 0.24543(15) -0.05576(6) 0.0194(2) Uani 1 1 d . . .
C3 C 0.11669(10) 0.20558(14) -0.01015(5) 0.0183(2) Uani 1 1 d . . .
C4 C 0.10814(10) 0.20720(15) 0.06357(5) 0.0191(2) Uani 1 1 d . . .
H4 H 0.0308 0.2303 0.0838 0.023 Uiso 1 1 calc R . .
C5 C 0.21276(10) 0.17495(15) 0.10740(5) 0.0187(2) Uani 1 1 d . . .
C6 C 0.32803(10) 0.14133(14) 0.07780(5) 0.0181(2) Uani 1 1 d . . .
C7 C 0.33305(10) 0.13902(15) 0.00393(6) 0.0200(2) Uani 1 1 d . . .
H7 H 0.4101 0.1159 -0.0167 0.024 Uiso 1 1 calc R . .
C8 C 0.22926(10) 0.16944(15) -0.04039(5) 0.0203(2) Uani 1 1 d . . .
H8 H 0.2349 0.1657 -0.0905 0.024 Uiso 1 1 calc R . .
C9 C 0.44202(10) 0.11612(15) 0.12390(5) 0.0189(2) Uani 1 1 d . . .
C10 C 0.44964(11) -0.02258(16) 0.17719(6) 0.0233(2) Uani 1 1 d . . .
H10 H 0.3804 -0.1015 0.1854 0.028 Uiso 1 1 calc R . .
C11 C 0.55816(11) -0.04516(18) 0.21817(6) 0.0272(3) Uani 1 1 d . . .
H11 H 0.5640 -0.1427 0.2532 0.033 Uiso 1 1 calc R . .
C12 C 0.65821(11) 0.07391(18) 0.20831(6) 0.0266(3) Uani 1 1 d . . .
H12 H 0.7316 0.0581 0.2372 0.032 Uiso 1 1 calc R . .
C13 C 0.65242(10) 0.21633(18) 0.15665(6) 0.0249(2) Uani 1 1 d . . .
C14 C 0.54409(10) 0.23322(16) 0.11405(6) 0.0215(2) Uani 1 1 d . . .
H14 H 0.5398 0.3267 0.0775 0.026 Uiso 1 1 calc R . .
C15 C -0.30921(10) 0.36910(17) -0.06839(6) 0.0261(3) Uani 1 1 d . . .
H15A H -0.3099 0.4753 -0.0345 0.039 Uiso 1 1 calc R . .
H15B H -0.3511 0.2586 -0.0485 0.039 Uiso 1 1 calc R . .
H15C H -0.3522 0.4075 -0.1130 0.039 Uiso 1 1 calc R . .
C16 C 0.09713(11) 0.21263(19) 0.21137(6) 0.0268(3) Uani 1 1 d . . .
H16C H 0.1096 0.2121 0.2632 0.040 Uiso 1 1 calc R . .
H16A H 0.0392 0.1109 0.1969 0.040 Uiso 1 1 calc R . .
H16B H 0.0634 0.3364 0.1959 0.040 Uiso 1 1 calc R . .
C17 C 0.75882(12) 0.3508(2) 0.14778(8) 0.0418(3) Uani 1 1 d . . .
H17A H 0.7273 0.4809 0.1405 0.063 Uiso 1 1 calc R . .
H17C H 0.8047 0.3120 0.1065 0.063 Uiso 1 1 calc R . .
H17B H 0.8137 0.3473 0.1905 0.063 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 0.0218(4) 0.0211(4) 0.0172(4) -0.0007(3) -0.0002(3) 0.0008(3)
O2 0.0232(4) 0.0371(5) 0.0132(4) -0.0015(3) 0.0025(3) 0.0026(3)
N1 0.0266(5) 0.0319(5) 0.0211(5) 0.0019(4) -0.0033(4) -0.0005(4)
N2 0.0259(5) 0.0348(6) 0.0183(5) 0.0024(4) -0.0005(4) -0.0009(4)
C1 0.0252(5) 0.0171(5) 0.0218(5) 0.0009(4) -0.0044(4) -0.0022(4)
C2 0.0224(5) 0.0179(5) 0.0182(5) -0.0003(4) 0.0030(4) -0.0019(4)
C3 0.0231(5) 0.0158(5) 0.0159(5) 0.0003(4) 0.0003(4) -0.0019(4)
C4 0.0202(5) 0.0200(5) 0.0175(5) -0.0009(4) 0.0034(4) -0.0014(4)
C5 0.0243(5) 0.0183(5) 0.0137(5) -0.0008(4) 0.0026(4) -0.0010(4)
C6 0.0219(5) 0.0148(5) 0.0177(5) -0.0006(4) 0.0012(4) 0.0003(4)
C7 0.0230(5) 0.0181(5) 0.0193(5) -0.0005(4) 0.0050(4) 0.0024(4)
C8 0.0272(5) 0.0196(5) 0.0143(5) -0.0007(4) 0.0034(4) 0.0006(4)
C9 0.0220(5) 0.0193(5) 0.0156(5) -0.0031(4) 0.0027(4) 0.0034(4)
C10 0.0291(6) 0.0212(5) 0.0197(5) 0.0000(4) 0.0004(4) -0.0008(4)
C11 0.0342(6) 0.0267(6) 0.0204(5) 0.0032(4) -0.0019(4) 0.0045(5)
C12 0.0240(6) 0.0353(6) 0.0204(5) -0.0031(5) -0.0023(4) 0.0068(5)
C13 0.0209(5) 0.0315(6) 0.0225(5) -0.0031(4) 0.0036(4) 0.0018(4)
C14 0.0226(5) 0.0233(5) 0.0189(5) 0.0002(4) 0.0043(4) 0.0029(4)
C15 0.0250(6) 0.0213(5) 0.0314(6) -0.0020(4) -0.0036(5) 0.0007(4)
C16 0.0270(6) 0.0375(7) 0.0163(5) -0.0003(4) 0.0068(4) 0.0024(5)
C17 0.0252(6) 0.0575(9) 0.0426(8) 0.0086(7) -0.0005(5) -0.0092(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
O1 C2 1.3630(13) . ?
O1 C1 1.3678(12) . ?
O2 C5 1.3585(12) . ?
O2 C16 1.4327(13) . ?
N1 C1 1.2855(15) . ?
N1 N2 1.4130(14) . ?
N2 C2 1.2884(14) . ?
C1 C15 1.4771(16) . ?
C2 C3 1.4617(15) . ?
C3 C8 1.3926(15) . ?
C3 C4 1.3965(14) . ?
C4 C5 1.3913(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.4104(15) . ?
C6 C7 1.3957(14) . ?
C6 C9 1.4888(14) . ?
C7 C8 1.3873(15) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C14 1.3959(15) . ?
C9 C10 1.3968(15) . ?
C10 C11 1.3870(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.3867(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.3930(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3976(15) . ?
C13 C17 1.5039(17) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17C 0.9800 . ?
C17 H17B 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 102.54(8) . . ?
C5 O2 C16 117.53(8) . . ?
C1 N1 N2 106.24(9) . . ?
C2 N2 N1 106.12(9) . . ?
N1 C1 O1 112.50(10) . . ?
N1 C1 C15 129.76(10) . . ?
O1 C1 C15 117.74(9) . . ?
N2 C2 O1 112.60(10) . . ?
N2 C2 C3 128.68(10) . . ?
O1 C2 C3 118.71(9) . . ?
C8 C3 C4 120.45(10) . . ?
C8 C3 C2 119.85(9) . . ?
C4 C3 C2 119.70(10) . . ?
C5 C4 C3 120.06(10) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
O2 C5 C4 123.58(9) . . ?
O2 C5 C6 116.02(9) . . ?
C4 C5 C6 120.34(9) . . ?
C7 C6 C5 118.09(10) . . ?
C7 C6 C9 120.83(9) . . ?
C5 C6 C9 121.04(9) . . ?
C8 C7 C6 122.16(10) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C3 118.89(9) . . ?
C7 C8 H8 120.6 . . ?
C3 C8 H8 120.6 . . ?
C14 C9 C10 118.81(10) . . ?
C14 C9 C6 119.65(9) . . ?
C10 C9 C6 121.53(10) . . ?
C11 C10 C9 120.08(11) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 120.37(11) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.85(10) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C14 118.20(11) . . ?
C12 C13 C17 121.00(11) . . ?
C14 C13 C17 120.79(11) . . ?
C9 C14 C13 121.63(10) . . ?
C9 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C1 C15 H15A 109.5 . . ?
C1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 H16C 109.5 . . ?
O2 C16 H16A 109.5 . . ?
H16C C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16C C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17C C17 H17B 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 993499'
#######################################################################
#
#                 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_mx20_13

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H15 N3 O2'
_chemical_formula_sum            'C16 H15 N3 O2'
_chemical_formula_weight         281.31

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/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   12.9066(5)
_cell_length_b                   7.1171(2)
_cell_length_c                   15.1189(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.461(2)
_cell_angle_gamma                90.00
_cell_volume                     1361.09(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    5532
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      30.02

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7059
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker AXS, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(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  'Bruker X8 APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11823
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         30.06
_reflns_number_total             3961
_reflns_number_gt                3324
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Apex2 v2.0/2012.1 (Bruker AXS, 2012)'
_computing_cell_refinement       'Bruker Apex2 v2.0/2012.1 (Bruker AXS, 2012)'
_computing_data_reduction        'Bruker Apex2 v2.0/2012.1 (Bruker AXS, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed/POVRay
_computing_publication_material  CIFTAB

_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)+(0.0610P)²+0.3374P] 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         3961
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1118
_refine_ls_wR_factor_gt          0.1048
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
O1 O 0.12195(5) 0.66972(10) 0.21767(4) 0.01788(16) Uani 1 1 d . . .
O2 O -0.01714(5) 0.76307(10) 0.07143(5) 0.01759(16) Uani 1 1 d . . .
N1 N 0.28851(7) 0.71762(15) 0.20959(6) 0.0247(2) Uani 1 1 d . . .
N2 N 0.28149(7) 0.69803(15) 0.30100(6) 0.0251(2) Uani 1 1 d . . .
N3 N 0.04063(8) 0.96919(13) -0.34877(6) 0.0242(2) Uani 1 1 d . . .
C1 C 0.16127(7) 0.70727(13) 0.06590(6) 0.01453(18) Uani 1 1 d . . .
C2 C 0.05678(7) 0.73943(12) 0.01985(6) 0.01375(18) Uani 1 1 d . . .
C3 C 0.03404(7) 0.75112(13) -0.07435(6) 0.01473(18) Uani 1 1 d . . .
H3 H -0.0366 0.7720 -0.1053 0.018 Uiso 1 1 calc R . .
C4 C 0.11452(7) 0.73222(13) -0.12302(6) 0.01528(18) Uani 1 1 d . . .
C5 C 0.21796(8) 0.69754(15) -0.07729(7) 0.01810(19) Uani 1 1 d . . .
H5 H 0.2728 0.6819 -0.1103 0.022 Uiso 1 1 calc R . .
C6 C 0.24048(7) 0.68600(14) 0.01579(7) 0.01728(19) Uani 1 1 d . . .
H6 H 0.3111 0.6632 0.0462 0.021 Uiso 1 1 calc R . .
C7 C 0.19311(7) 0.69957(13) 0.16384(6) 0.01557(18) Uani 1 1 d . . .
C8 C 0.18356(8) 0.67042(15) 0.30194(6) 0.0186(2) Uani 1 1 d . . .
C9 C 0.13131(8) 0.63964(19) 0.37897(7) 0.0263(2) Uani 1 1 d . . .
H9A H 0.1832 0.6537 0.4355 0.039 Uiso 1 1 calc R . .
H9B H 0.1014 0.5127 0.3756 0.039 Uiso 1 1 calc R . .
H9C H 0.0746 0.7321 0.3771 0.039 Uiso 1 1 calc R . .
C10 C -0.12387(7) 0.78993(14) 0.02513(6) 0.01675(19) Uani 1 1 d . . .
H10A H -0.1280 0.9011 -0.0137 0.025 Uiso 1 1 calc R . .
H10B H -0.1693 0.8079 0.0692 0.025 Uiso 1 1 calc R . .
H10C H -0.1476 0.6792 -0.0119 0.025 Uiso 1 1 calc R . .
C11 C 0.09234(7) 0.75573(13) -0.22289(6) 0.01519(18) Uani 1 1 d . . .
C12 C 0.05479(8) 0.92793(14) -0.26064(7) 0.0203(2) Uani 1 1 d . . .
H12 H 0.0382 1.0222 -0.2212 0.024 Uiso 1 1 calc R . .
C13 C 0.06308(9) 0.83237(16) -0.40292(7) 0.0229(2) Uani 1 1 d . . .
H13 H 0.0555 0.8586 -0.4655 0.027 Uiso 1 1 calc R . .
C14 C 0.09674(8) 0.65498(15) -0.37247(7) 0.0198(2) Uani 1 1 d . . .
H14 H 0.1097 0.5621 -0.4141 0.024 Uiso 1 1 calc R . .
C15 C 0.11160(7) 0.61235(14) -0.28090(6) 0.01592(19) Uani 1 1 d . . .
C16 C 0.14207(8) 0.41826(14) -0.24702(7) 0.0210(2) Uani 1 1 d . . .
H16A H 0.1256 0.3287 -0.2971 0.031 Uiso 1 1 calc R . .
H16B H 0.1025 0.3845 -0.2003 0.031 Uiso 1 1 calc R . .
H16C H 0.2180 0.4146 -0.2215 0.031 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 0.0151(3) 0.0272(4) 0.0103(3) 0.0012(3) -0.0001(2) 0.0013(3)
O2 0.0140(3) 0.0273(4) 0.0111(3) 0.0008(3) 0.0016(2) 0.0041(3)
N1 0.0181(4) 0.0418(6) 0.0128(4) 0.0028(4) -0.0004(3) -0.0052(4)
N2 0.0200(4) 0.0418(6) 0.0118(4) 0.0029(4) -0.0007(3) -0.0040(4)
N3 0.0335(5) 0.0224(4) 0.0167(4) 0.0040(3) 0.0051(3) 0.0031(4)
C1 0.0156(4) 0.0153(4) 0.0119(4) 0.0004(3) 0.0007(3) -0.0004(3)
C2 0.0149(4) 0.0138(4) 0.0125(4) -0.0001(3) 0.0025(3) -0.0002(3)
C3 0.0161(4) 0.0154(4) 0.0119(4) 0.0002(3) 0.0008(3) 0.0002(3)
C4 0.0189(4) 0.0147(4) 0.0121(4) 0.0001(3) 0.0026(3) -0.0009(3)
C5 0.0167(4) 0.0231(5) 0.0152(4) 0.0007(4) 0.0049(3) -0.0004(3)
C6 0.0141(4) 0.0212(4) 0.0156(4) 0.0007(4) 0.0006(3) 0.0003(3)
C7 0.0160(4) 0.0173(4) 0.0129(4) 0.0010(3) 0.0016(3) 0.0000(3)
C8 0.0179(4) 0.0248(5) 0.0108(4) 0.0008(3) -0.0023(3) 0.0018(3)
C9 0.0198(5) 0.0454(7) 0.0129(4) 0.0028(4) 0.0012(4) 0.0023(4)
C10 0.0135(4) 0.0215(5) 0.0145(4) 0.0012(3) 0.0011(3) 0.0016(3)
C11 0.0158(4) 0.0178(4) 0.0122(4) 0.0007(3) 0.0034(3) -0.0012(3)
C12 0.0269(5) 0.0190(5) 0.0153(4) 0.0002(4) 0.0048(4) 0.0016(4)
C13 0.0289(5) 0.0266(5) 0.0132(4) 0.0031(4) 0.0043(4) -0.0009(4)
C14 0.0241(5) 0.0223(5) 0.0140(4) -0.0022(4) 0.0062(4) -0.0012(4)
C15 0.0154(4) 0.0181(4) 0.0149(4) -0.0001(3) 0.0046(3) -0.0017(3)
C16 0.0266(5) 0.0184(5) 0.0184(5) 0.0001(4) 0.0054(4) 0.0032(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
O1 C7 1.3595(12) . ?
O1 C8 1.3613(11) . ?
O2 C2 1.3574(11) . ?
O2 C10 1.4285(11) . ?
N1 C7 1.2933(12) . ?
N1 N2 1.4097(12) . ?
N2 C8 1.2819(13) . ?
N3 C13 1.3404(14) . ?
N3 C12 1.3409(12) . ?
C1 C6 1.3964(13) . ?
C1 C2 1.4082(12) . ?
C1 C7 1.4568(12) . ?
C2 C3 1.3983(12) . ?
C3 C4 1.3936(13) . ?
C4 C5 1.3980(13) . ?
C4 C11 1.4894(13) . ?
C5 C6 1.3816(13) . ?
C8 C9 1.4734(14) . ?
C11 C12 1.3974(13) . ?
C11 C15 1.3996(13) . ?
C13 C14 1.3839(15) . ?
C14 C15 1.3927(13) . ?
C15 C16 1.4984(14) . ?

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
C7 O1 C8 102.78(7) . . ?
C2 O2 C10 117.04(7) . . ?
C7 N1 N2 105.94(8) . . ?
C8 N2 N1 106.36(8) . . ?
C13 N3 C12 116.39(9) . . ?
C6 C1 C2 118.80(8) . . ?
C6 C1 C7 117.28(8) . . ?
C2 C1 C7 123.89(8) . . ?
O2 C2 C3 123.26(8) . . ?
O2 C2 C1 116.72(8) . . ?
C3 C2 C1 119.99(8) . . ?
C4 C3 C2 120.29(8) . . ?
C3 C4 C5 119.65(9) . . ?
C3 C4 C11 120.74(8) . . ?
C5 C4 C11 119.57(8) . . ?
C6 C5 C4 120.08(9) . . ?
C5 C6 C1 121.17(9) . . ?
N1 C7 O1 112.33(8) . . ?
N1 C7 C1 125.88(9) . . ?
O1 C7 C1 121.78(8) . . ?
N2 C8 O1 112.59(9) . . ?
N2 C8 C9 129.69(9) . . ?
O1 C8 C9 117.72(9) . . ?
C12 C11 C15 118.29(9) . . ?
C12 C11 C4 119.59(8) . . ?
C15 C11 C4 122.08(8) . . ?
N3 C12 C11 124.44(9) . . ?
N3 C13 C14 123.44(9) . . ?
C13 C14 C15 120.10(9) . . ?
C14 C15 C11 117.23(9) . . ?
C14 C15 C16 121.03(9) . . ?
C11 C15 C16 121.68(8) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.046
_database_code_depnum_ccdc_archive 'CCDC 993500'
