# 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_2013288_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 N2 O4'
_chemical_formula_weight         284.27

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

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P21/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                   7.9465(5)
_cell_length_b                   18.6642(12)
_cell_length_c                   8.8245(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.265(5)
_cell_angle_gamma                90.00
_cell_volume                     1303.28(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9790
_exptl_absorpt_correction_T_max  0.9968
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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_reflns_number            8943
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2301
_reflns_number_gt                1666
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0582P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2301
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1739
_refine_ls_wR_factor_gt          0.1619
_refine_ls_goodness_of_fit_ref   1.790
_refine_ls_restrained_S_all      1.790
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2719(2) 0.42695(10) 0.0996(2) 0.0458(5) Uani 1 1 d . . .
O3 O 0.0360(2) 0.65175(10) 0.2233(2) 0.0662(6) Uani 1 1 d . . .
O1 O 0.3843(2) 0.50657(8) -0.31851(17) 0.0500(5) Uani 1 1 d . . .
O2 O 0.2904(2) 0.61386(10) -0.2674(2) 0.0686(6) Uani 1 1 d . . .
C7 C 0.3062(3) 0.45444(11) -0.0342(2) 0.0376(5) Uani 1 1 d . . .
O4 O 0.0089(3) 0.56165(11) 0.3832(2) 0.0770(7) Uani 1 1 d . . .
C3 C 0.5487(3) 0.32726(13) -0.3468(3) 0.0556(7) Uani 1 1 d . . .
H1 H 0.6016 0.2999 -0.4166 0.067 Uiso 1 1 calc R . .
C2 C 0.5030(3) 0.39680(14) -0.3821(3) 0.0505(7) Uani 1 1 d . . .
H10 H 0.5247 0.4166 -0.4750 0.061 Uiso 1 1 calc R . .
C1 C 0.4242(3) 0.43684(12) -0.2773(2) 0.0412(6) Uani 1 1 d . . .
C6 C 0.3899(3) 0.40871(12) -0.1377(2) 0.0401(6) Uani 1 1 d . . .
C8 C 0.1936(3) 0.46884(13) 0.1955(2) 0.0455(6) Uani 1 1 d . . .
C9 C 0.1452(3) 0.54054(12) 0.1584(2) 0.0428(6) Uani 1 1 d . . .
C13 C 0.0578(3) 0.58407(15) 0.2671(3) 0.0526(7) Uani 1 1 d . . .
C14 C -0.0400(4) 0.69699(17) 0.3333(4) 0.0904(11) Uani 1 1 d . . .
H8A H -0.1546 0.6812 0.3438 0.108 Uiso 1 1 calc R . .
H8B H 0.0242 0.6932 0.4319 0.108 Uiso 1 1 calc R . .
C15 C -0.0413(5) 0.76701(19) 0.2847(6) 0.154(2) Uani 1 1 d . . .
H9A H 0.0724 0.7824 0.2742 0.231 Uiso 1 1 calc R . .
H9B H -0.0901 0.7968 0.3577 0.231 Uiso 1 1 calc R . .
H9C H -0.1070 0.7707 0.1882 0.231 Uiso 1 1 calc R . .
C12 C 0.3108(3) 0.55310(13) -0.2230(3) 0.0477(6) Uani 1 1 d . . .
C11 C 0.2660(3) 0.52454(12) -0.0792(2) 0.0390(6) Uani 1 1 d . . .
C10 C 0.1847(3) 0.56705(12) 0.0212(3) 0.0431(6) Uani 1 1 d . . .
H5 H 0.1569 0.6141 -0.0052 0.052 Uiso 1 1 calc R . .
N2 N 0.1663(3) 0.43854(12) 0.3276(2) 0.0674(7) Uani 1 1 d . . .
H7 H 0.1981 0.3952 0.3464 0.081 Uiso 1 1 calc R . .
H6 H 0.1167 0.4624 0.3942 0.081 Uiso 1 1 calc R . .
C5 C 0.4387(3) 0.33813(13) -0.1050(3) 0.0532(7) Uani 1 1 d . . .
H9 H 0.4180 0.3183 -0.0119 0.064 Uiso 1 1 calc R . .
C4 C 0.5166(3) 0.29752(14) -0.2078(3) 0.0595(7) Uani 1 1 d . . .
H8 H 0.5477 0.2505 -0.1846 0.071 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.338(3) . ?
N1 C8 1.346(3) . ?
O3 C13 1.328(3) . ?
O3 C14 1.458(3) . ?
O1 C12 1.377(3) . ?
O1 C1 1.380(3) . ?
O2 C12 1.206(3) . ?
C7 C11 1.396(3) . ?
C7 C6 1.455(3) . ?
O4 C13 1.203(3) . ?
C3 C2 1.376(3) . ?
C3 C4 1.392(3) . ?
C3 H1 0.9300 . ?
C2 C1 1.382(3) . ?
C2 H10 0.9300 . ?
C1 C6 1.390(3) . ?
C6 C5 1.396(3) . ?
C8 N2 1.332(3) . ?
C8 C9 1.422(3) . ?
C9 C10 1.371(3) . ?
C9 C13 1.478(3) . ?
C14 C15 1.375(5) . ?
C14 H8A 0.9700 . ?
C14 H8B 0.9700 . ?
C15 H9A 0.9600 . ?
C15 H9B 0.9600 . ?
C15 H9C 0.9600 . ?
C12 C11 1.451(3) . ?
C11 C10 1.391(3) . ?
C10 H5 0.9300 . ?
N2 H7 0.8600 . ?
N2 H6 0.8600 . ?
C5 C4 1.372(3) . ?
C5 H9 0.9300 . ?
C4 H8 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C8 118.4(2) . . ?
C13 O3 C14 114.1(2) . . ?
C12 O1 C1 122.24(17) . . ?
N1 C7 C11 123.40(19) . . ?
N1 C7 C6 118.09(19) . . ?
C11 C7 C6 118.51(19) . . ?
C2 C3 C4 120.6(2) . . ?
C2 C3 H1 119.7 . . ?
C4 C3 H1 119.7 . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 H10 120.5 . . ?
C1 C2 H10 120.5 . . ?
O1 C1 C2 116.16(19) . . ?
O1 C1 C6 122.06(19) . . ?
C2 C1 C6 121.8(2) . . ?
C1 C6 C5 117.8(2) . . ?
C1 C6 C7 118.3(2) . . ?
C5 C6 C7 123.95(19) . . ?
N2 C8 N1 115.2(2) . . ?
N2 C8 C9 122.6(2) . . ?
N1 C8 C9 122.2(2) . . ?
C10 C9 C8 117.6(2) . . ?
C10 C9 C13 122.3(2) . . ?
C8 C9 C13 120.0(2) . . ?
O4 C13 O3 122.3(2) . . ?
O4 C13 C9 124.7(3) . . ?
O3 C13 C9 113.0(2) . . ?
C15 C14 O3 109.5(3) . . ?
C15 C14 H8A 109.8 . . ?
O3 C14 H8A 109.8 . . ?
C15 C14 H8B 109.8 . . ?
O3 C14 H8B 109.8 . . ?
H8A C14 H8B 108.2 . . ?
C14 C15 H9A 109.5 . . ?
C14 C15 H9B 109.5 . . ?
H9A C15 H9B 109.5 . . ?
C14 C15 H9C 109.5 . . ?
H9A C15 H9C 109.5 . . ?
H9B C15 H9C 109.5 . . ?
O2 C12 O1 116.5(2) . . ?
O2 C12 C11 126.4(2) . . ?
O1 C12 C11 117.1(2) . . ?
C10 C11 C7 117.5(2) . . ?
C10 C11 C12 120.8(2) . . ?
C7 C11 C12 121.68(19) . . ?
C9 C10 C11 120.9(2) . . ?
C9 C10 H5 119.5 . . ?
C11 C10 H5 119.5 . . ?
C8 N2 H7 120.0 . . ?
C8 N2 H6 120.0 . . ?
H7 N2 H6 120.0 . . ?
C4 C5 C6 121.2(2) . . ?
C4 C5 H9 119.4 . . ?
C6 C5 H9 119.4 . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 H8 120.2 . . ?
C3 C4 H8 120.2 . . ?

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
C8 N1 C7 C11 0.4(3) . . . . ?
C8 N1 C7 C6 -179.6(2) . . . . ?
C4 C3 C2 C1 -0.1(4) . . . . ?
C12 O1 C1 C2 -177.8(2) . . . . ?
C12 O1 C1 C6 1.2(3) . . . . ?
C3 C2 C1 O1 178.9(2) . . . . ?
C3 C2 C1 C6 -0.1(4) . . . . ?
O1 C1 C6 C5 -178.5(2) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
O1 C1 C6 C7 1.2(3) . . . . ?
C2 C1 C6 C7 -179.8(2) . . . . ?
N1 C7 C6 C1 179.4(2) . . . . ?
C11 C7 C6 C1 -0.7(3) . . . . ?
N1 C7 C6 C5 -0.9(4) . . . . ?
C11 C7 C6 C5 179.1(2) . . . . ?
C7 N1 C8 N2 -178.8(2) . . . . ?
C7 N1 C8 C9 0.6(4) . . . . ?
N2 C8 C9 C10 177.8(2) . . . . ?
N1 C8 C9 C10 -1.5(4) . . . . ?
N2 C8 C9 C13 -1.3(4) . . . . ?
N1 C8 C9 C13 179.4(2) . . . . ?
C14 O3 C13 O4 4.5(4) . . . . ?
C14 O3 C13 C9 -176.2(2) . . . . ?
C10 C9 C13 O4 173.9(3) . . . . ?
C8 C9 C13 O4 -7.0(4) . . . . ?
C10 C9 C13 O3 -5.4(3) . . . . ?
C8 C9 C13 O3 173.7(2) . . . . ?
C13 O3 C14 C15 173.9(3) . . . . ?
C1 O1 C12 O2 175.9(2) . . . . ?
C1 O1 C12 C11 -3.9(3) . . . . ?
N1 C7 C11 C10 -0.6(3) . . . . ?
C6 C7 C11 C10 179.5(2) . . . . ?
N1 C7 C11 C12 177.8(2) . . . . ?
C6 C7 C11 C12 -2.2(3) . . . . ?
O2 C12 C11 C10 2.9(4) . . . . ?
O1 C12 C11 C10 -177.3(2) . . . . ?
O2 C12 C11 C7 -175.3(2) . . . . ?
O1 C12 C11 C7 4.5(3) . . . . ?
C8 C9 C10 C11 1.4(3) . . . . ?
C13 C9 C10 C11 -179.5(2) . . . . ?
C7 C11 C10 C9 -0.4(3) . . . . ?
C12 C11 C10 C9 -178.7(2) . . . . ?
C1 C6 C5 C4 -0.6(4) . . . . ?
C7 C6 C5 C4 179.7(2) . . . . ?
C6 C5 C4 C3 0.4(4) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 974573'
#######################################################################
#
#                 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_mo_2013422_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 N2 O2'
_chemical_formula_weight         238.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           ?
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.2272(9)
_cell_length_b                   8.0305(13)
_cell_length_c                   13.945(2)
_cell_angle_alpha                88.537(11)
_cell_angle_beta                 82.628(11)
_cell_angle_gamma                74.066(10)
_cell_volume                     558.18(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             278
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9260
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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_reflns_number            5288
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1878
_reflns_number_gt                1475
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0613P)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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.057(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1878
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1351
_refine_ls_wR_factor_gt          0.1242
_refine_ls_goodness_of_fit_ref   1.459
_refine_ls_restrained_S_all      1.459
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3765(3) 0.01759(16) 0.31923(7) 0.0378(4) Uani 1 1 d . . .
C12 C 0.1957(3) -0.1841(2) 0.41292(10) 0.0447(4) Uani 1 1 d . . .
H10 H 0.2744 -0.1485 0.4663 0.054 Uiso 1 1 calc R . .
O1 O 0.4479(2) 0.29242(15) 0.06630(7) 0.0550(4) Uani 1 1 d . . .
O2 O 0.2215(3) 0.15183(16) -0.00579(7) 0.0619(4) Uani 1 1 d . . .
C3 C 0.8086(4) 0.4916(2) 0.21196(12) 0.0554(5) Uani 1 1 d . . .
H1 H 0.8940 0.5795 0.2064 0.067 Uiso 1 1 calc R . .
C2 C 0.6900(4) 0.4553(2) 0.13565(12) 0.0550(5) Uani 1 1 d . . .
H4 H 0.6950 0.5172 0.0785 0.066 Uiso 1 1 calc R . .
C1 C 0.5636(3) 0.3253(2) 0.14571(10) 0.0438(5) Uani 1 1 d . . .
C6 C 0.5497(3) 0.23269(19) 0.23057(9) 0.0364(4) Uani 1 1 d . . .
C7 C 0.4058(3) 0.10253(19) 0.23598(9) 0.0345(4) Uani 1 1 d . . .
C11 C 0.2383(3) -0.09907(19) 0.32007(10) 0.0379(4) Uani 1 1 d . . .
C13 C 0.1843(4) -0.3682(2) 0.41423(12) 0.0531(5) Uani 1 1 d . . .
H2 H 0.2061 -0.4268 0.3525 0.064 Uiso 1 1 calc R . .
H9 H 0.2604 -0.4414 0.4657 0.064 Uiso 1 1 calc R . .
C14 C -0.0638(4) -0.2303(2) 0.44039(11) 0.0542(5) Uani 1 1 d . . .
H3 H -0.1399 -0.2185 0.5079 0.065 Uiso 1 1 calc R . .
H11 H -0.1943 -0.2039 0.3947 0.065 Uiso 1 1 calc R . .
C8 C 0.2952(3) 0.06928(19) 0.15542(9) 0.0377(4) Uani 1 1 d . . .
C9 C 0.3143(3) 0.1681(2) 0.06660(10) 0.0454(4) Uani 1 1 d . . .
C5 C 0.6740(3) 0.2722(2) 0.30630(10) 0.0432(4) Uani 1 1 d . . .
H6 H 0.6692 0.2113 0.3638 0.052 Uiso 1 1 calc R . .
C4 C 0.8027(3) 0.3995(2) 0.29680(11) 0.0508(5) Uani 1 1 d . . .
H5 H 0.8864 0.4241 0.3475 0.061 Uiso 1 1 calc R . .
C10 C 0.1632(3) -0.0584(2) 0.16333(10) 0.0453(5) Uani 1 1 d . . .
H8 H 0.0927 -0.0852 0.1097 0.054 Uiso 1 1 calc R . .
N2 N 0.1330(3) -0.14425(17) 0.24441(8) 0.0452(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C11 1.3298(17) . ?
N1 C7 1.3444(17) . ?
C12 C11 1.4685(18) . ?
C12 C13 1.496(2) . ?
C12 C14 1.503(2) . ?
C12 H10 0.9800 . ?
O1 C9 1.366(2) . ?
O1 C1 1.3911(18) . ?
O2 C9 1.1994(17) . ?
C3 C2 1.373(2) . ?
C3 C4 1.381(2) . ?
C3 H1 0.9300 . ?
C2 C1 1.377(2) . ?
C2 H4 0.9300 . ?
C1 C6 1.3860(19) . ?
C6 C5 1.3946(19) . ?
C6 C7 1.441(2) . ?
C7 C8 1.3909(18) . ?
C11 N2 1.3511(17) . ?
C13 C14 1.467(2) . ?
C13 H2 0.9700 . ?
C13 H9 0.9700 . ?
C14 H3 0.9700 . ?
C14 H11 0.9700 . ?
C8 C10 1.379(2) . ?
C8 C9 1.4614(19) . ?
C5 C4 1.364(2) . ?
C5 H6 0.9300 . ?
C4 H5 0.9300 . ?
C10 N2 1.3239(19) . ?
C10 H8 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C7 116.66(11) . . ?
C11 C12 C13 119.71(13) . . ?
C11 C12 C14 119.09(13) . . ?
C13 C12 C14 58.57(11) . . ?
C11 C12 H10 115.8 . . ?
C13 C12 H10 115.8 . . ?
C14 C12 H10 115.8 . . ?
C9 O1 C1 122.62(12) . . ?
C2 C3 C4 120.91(15) . . ?
C2 C3 H1 119.5 . . ?
C4 C3 H1 119.5 . . ?
C3 C2 C1 118.49(14) . . ?
C3 C2 H4 120.8 . . ?
C1 C2 H4 120.8 . . ?
C2 C1 C6 121.97(14) . . ?
C2 C1 O1 116.43(13) . . ?
C6 C1 O1 121.60(15) . . ?
C1 C6 C5 117.95(14) . . ?
C1 C6 C7 118.31(12) . . ?
C5 C6 C7 123.74(12) . . ?
N1 C7 C8 121.12(14) . . ?
N1 C7 C6 119.52(12) . . ?
C8 C7 C6 119.35(12) . . ?
N1 C11 N2 126.17(12) . . ?
N1 C11 C12 116.03(12) . . ?
N2 C11 C12 117.79(13) . . ?
C14 C13 C12 60.97(12) . . ?
C14 C13 H2 117.7 . . ?
C12 C13 H2 117.7 . . ?
C14 C13 H9 117.7 . . ?
C12 C13 H9 117.7 . . ?
H2 C13 H9 114.8 . . ?
C13 C14 C12 60.47(11) . . ?
C13 C14 H3 117.7 . . ?
C12 C14 H3 117.7 . . ?
C13 C14 H11 117.7 . . ?
C12 C14 H11 117.7 . . ?
H3 C14 H11 114.8 . . ?
C10 C8 C7 117.37(12) . . ?
C10 C8 C9 121.47(13) . . ?
C7 C8 C9 121.16(14) . . ?
O2 C9 O1 116.82(13) . . ?
O2 C9 C8 126.25(16) . . ?
O1 C9 C8 116.92(12) . . ?
C4 C5 C6 120.62(13) . . ?
C4 C5 H6 119.7 . . ?
C6 C5 H6 119.7 . . ?
C5 C4 C3 120.04(14) . . ?
C5 C4 H5 120.0 . . ?
C3 C4 H5 120.0 . . ?
N2 C10 C8 122.52(12) . . ?
N2 C10 H8 118.7 . . ?
C8 C10 H8 118.7 . . ?
C10 N2 C11 116.08(13) . . ?

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
C4 C3 C2 C1 0.3(3) . . . . ?
C3 C2 C1 C6 1.0(3) . . . . ?
C3 C2 C1 O1 -179.59(14) . . . . ?
C9 O1 C1 C2 -179.42(15) . . . . ?
C9 O1 C1 C6 0.0(3) . . . . ?
C2 C1 C6 C5 -1.4(3) . . . . ?
O1 C1 C6 C5 179.17(13) . . . . ?
C2 C1 C6 C7 177.97(15) . . . . ?
O1 C1 C6 C7 -1.5(2) . . . . ?
C11 N1 C7 C8 0.2(2) . . . . ?
C11 N1 C7 C6 179.02(13) . . . . ?
C1 C6 C7 N1 -176.31(13) . . . . ?
C5 C6 C7 N1 3.0(2) . . . . ?
C1 C6 C7 C8 2.5(2) . . . . ?
C5 C6 C7 C8 -178.18(14) . . . . ?
C7 N1 C11 N2 2.4(2) . . . . ?
C7 N1 C11 C12 -176.85(12) . . . . ?
C13 C12 C11 N1 -147.00(16) . . . . ?
C14 C12 C11 N1 144.70(15) . . . . ?
C13 C12 C11 N2 33.6(2) . . . . ?
C14 C12 C11 N2 -34.7(2) . . . . ?
C11 C12 C13 C14 -107.90(16) . . . . ?
C11 C12 C14 C13 108.94(16) . . . . ?
N1 C7 C8 C10 -2.3(2) . . . . ?
C6 C7 C8 C10 178.90(13) . . . . ?
N1 C7 C8 C9 176.61(13) . . . . ?
C6 C7 C8 C9 -2.2(2) . . . . ?
C1 O1 C9 O2 179.61(14) . . . . ?
C1 O1 C9 C8 0.3(3) . . . . ?
C10 C8 C9 O2 0.5(3) . . . . ?
C7 C8 C9 O2 -178.44(16) . . . . ?
C10 C8 C9 O1 179.64(14) . . . . ?
C7 C8 C9 O1 0.8(2) . . . . ?
C1 C6 C5 C4 0.6(3) . . . . ?
C7 C6 C5 C4 -178.74(15) . . . . ?
C6 C5 C4 C3 0.6(3) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C7 C8 C10 N2 2.0(3) . . . . ?
C9 C8 C10 N2 -176.92(13) . . . . ?
C8 C10 N2 C11 0.3(2) . . . . ?
N1 C11 N2 C10 -2.8(2) . . . . ?
C12 C11 N2 C10 176.53(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.954
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.954
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.044
_database_code_depnum_ccdc_archive 'CCDC 974574'
