# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1406156'
_audit_update_record             
;
2015-06-11 deposited with the CCDC.
2015-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            Benzoyl-Oxyma
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 N2 O4'
_chemical_formula_weight         246.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   11.88670(10)
_cell_length_b                   8.05560(10)
_cell_length_c                   12.38530(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.0640(10)
_cell_angle_gamma                90
_cell_volume                     1171.14(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    130.0(1)
_cell_measurement_reflns_used    6118
_cell_measurement_theta_min      3.6070
_cell_measurement_theta_max      76.8740

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4876
_exptl_crystal_size_mid          0.4399
_exptl_crystal_size_min          0.3178
_exptl_absorpt_coefficient_mu    0.904
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.92972
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130.0(1)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8000
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         5.620
_diffrn_reflns_theta_max         77.038
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2434
_reflns_number_gt                2347
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0555P)²+0.2682P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0088(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2434
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0966
_refine_ls_wR_factor_gt          0.0955
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.36492(8) 0.56893(12) 0.52548(8) 0.0202(2) Uani 1 1 d . . . . .
C2 C 0.37123(8) 0.74062(12) 0.47692(8) 0.0195(2) Uani 1 1 d . . . . .
C3 C 0.36467(8) 0.88668(12) 0.54338(8) 0.0227(2) Uani 1 1 d . . . . .
C4 C 0.40045(8) 0.91286(12) 0.22980(8) 0.0213(2) Uani 1 1 d . . . . .
C5 C 0.39791(8) 1.08596(11) 0.19009(8) 0.0191(2) Uani 1 1 d . . . . .
C6 C 0.38732(8) 1.22355(12) 0.25624(8) 0.0210(2) Uani 1 1 d . . . . .
H6 H 0.3788 1.2092 0.3290 0.025 Uiso 1 1 calc R U . . .
C7 C 0.38963(8) 1.38194(12) 0.21254(8) 0.0233(2) Uani 1 1 d . . . . .
H7 H 0.3831 1.4741 0.2563 0.028 Uiso 1 1 calc R U . . .
C8 C 0.40169(9) 1.40332(12) 0.10346(9) 0.0247(2) Uani 1 1 d . . . . .
H8 H 0.4034 1.5098 0.0747 0.030 Uiso 1 1 calc R U . . .
C9 C 0.41127(9) 1.26591(13) 0.03723(8) 0.0245(2) Uani 1 1 d . . . . .
H9 H 0.4189 1.2803 -0.0358 0.029 Uiso 1 1 calc R U . . .
C10 C 0.40935(8) 1.10796(12) 0.08058(8) 0.0214(2) Uani 1 1 d . . . . .
H10 H 0.4157 1.0160 0.0366 0.026 Uiso 1 1 calc R U . . .
C11 C 0.34023(9) 0.42539(13) 0.68734(8) 0.0265(2) Uani 1 1 d . . . . .
H11A H 0.3594 0.4448 0.7654 0.032 Uiso 1 1 calc R U . . .
H11B H 0.3944 0.3462 0.6664 0.032 Uiso 1 1 calc R U . . .
C12 C 0.22237(10) 0.35464(15) 0.66227(9) 0.0332(3) Uani 1 1 d . . . . .
H12A H 0.2080 0.3187 0.5875 0.050 Uiso 1 1 calc R U . . .
H12B H 0.1679 0.4381 0.6738 0.050 Uiso 1 1 calc R U . . .
H12C H 0.2158 0.2618 0.7095 0.050 Uiso 1 1 calc R U . . .
N1 N 0.36112(8) 1.00297(12) 0.59590(8) 0.0322(2) Uani 1 1 d . . . . .
N2 N 0.38220(7) 0.74453(10) 0.37582(7) 0.0207(2) Uani 1 1 d . . . . .
O2 O 0.34845(6) 0.58205(8) 0.62839(6) 0.02332(19) Uani 1 1 d . . . . .
O1 O 0.37343(7) 0.44405(9) 0.47521(6) 0.0285(2) Uani 1 1 d . . . . .
O3 O 0.38413(6) 0.90725(8) 0.33902(5) 0.02031(18) Uani 1 1 d . . . . .
O4 O 0.41532(8) 0.79155(9) 0.17884(6) 0.0356(2) 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
C1 O1 1.1957(12) . ?
C1 O2 1.3239(12) . ?
C1 C2 1.5148(13) . ?
C2 N2 1.2796(12) . ?
C2 C3 1.4450(13) . ?
C3 N1 1.1451(14) . ?
C4 O4 1.1916(12) . ?
C4 O3 1.3971(11) . ?
C4 C5 1.4773(13) . ?
C5 C10 1.3955(13) . ?
C5 C6 1.3957(13) . ?
C6 C7 1.3879(13) . ?
C7 C8 1.3915(14) . ?
C8 C9 1.3931(14) . ?
C9 C10 1.3827(14) . ?
C11 O2 1.4689(11) . ?
C11 C12 1.4990(16) . ?
N2 O3 1.3892(10) . ?

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 O2 127.30(9) . . ?
O1 C1 C2 123.22(9) . . ?
O2 C1 C2 109.48(8) . . ?
N2 C2 C3 124.08(9) . . ?
N2 C2 C1 115.47(8) . . ?
C3 C2 C1 120.45(8) . . ?
N1 C3 C2 178.98(11) . . ?
O4 C4 O3 122.76(9) . . ?
O4 C4 C5 126.49(9) . . ?
O3 C4 C5 110.74(8) . . ?
C10 C5 C6 120.08(9) . . ?
C10 C5 C4 116.32(8) . . ?
C6 C5 C4 123.58(9) . . ?
C7 C6 C5 119.47(9) . . ?
C6 C7 C8 120.25(9) . . ?
C7 C8 C9 120.25(9) . . ?
C10 C9 C8 119.65(9) . . ?
C9 C10 C5 120.29(9) . . ?
O2 C11 C12 110.91(8) . . ?
C2 N2 O3 110.72(8) . . ?
C1 O2 C11 116.20(7) . . ?
N2 O3 C4 111.12(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N2 2.52(14) . . . . ?
O2 C1 C2 N2 -177.15(8) . . . . ?
O1 C1 C2 C3 -177.61(9) . . . . ?
O2 C1 C2 C3 2.72(12) . . . . ?
O4 C4 C5 C10 2.90(16) . . . . ?
O3 C4 C5 C10 -177.87(8) . . . . ?
O4 C4 C5 C6 -175.73(10) . . . . ?
O3 C4 C5 C6 3.51(13) . . . . ?
C10 C5 C6 C7 -0.76(14) . . . . ?
C4 C5 C6 C7 177.82(9) . . . . ?
C5 C6 C7 C8 0.40(14) . . . . ?
C6 C7 C8 C9 0.15(15) . . . . ?
C7 C8 C9 C10 -0.34(15) . . . . ?
C8 C9 C10 C5 -0.02(15) . . . . ?
C6 C5 C10 C9 0.57(14) . . . . ?
C4 C5 C10 C9 -178.11(9) . . . . ?
C3 C2 N2 O3 -1.40(13) . . . . ?
C1 C2 N2 O3 178.45(7) . . . . ?
O1 C1 O2 C11 0.28(15) . . . . ?
C2 C1 O2 C11 179.93(7) . . . . ?
C12 C11 O2 C1 -82.31(11) . . . . ?
C2 N2 O3 C4 177.74(7) . . . . ?
O4 C4 O3 N2 -2.94(14) . . . . ?
C5 C4 O3 N2 177.80(7) . . . . ?

_refine_diff_density_max         0.349
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.038



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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1406157'
_audit_update_record             
;
2015-06-11 deposited with the CCDC.
2015-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            Benzoyl-tButylOxyma
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N2 O4'
_chemical_formula_weight         274.27
_chemical_oxdiff_usercomment     'Satvika Burungpalli/SJW'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   5.90200(10)
_cell_length_b                   21.5230(3)
_cell_length_c                   11.2041(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.073(2)
_cell_angle_gamma                90
_cell_volume                     1391.76(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    130.0(1)
_cell_measurement_reflns_used    4743
_cell_measurement_theta_min      4.0420
_cell_measurement_theta_max      76.5290

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.813
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.86770
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130.0(1)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_reflns_number            9619
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.108
_diffrn_reflns_theta_max         76.984
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2897
_reflns_number_gt                2605
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²+0.4756P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2897
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1042(2) 0.40798(6) 0.61226(11) 0.0250(3) Uani 1 1 d . . . . .
C2 C 0.0546(2) 0.35677(5) 0.58786(10) 0.0222(2) Uani 1 1 d . . . . .
C3 C -0.0225(2) 0.32200(6) 0.47602(11) 0.0251(3) Uani 1 1 d . . . . .
C4 C 0.5786(2) 0.28516(5) 0.68866(10) 0.0216(2) Uani 1 1 d . . . . .
C5 C 0.6803(2) 0.23197(5) 0.63434(10) 0.0215(2) Uani 1 1 d . . . . .
C6 C 0.5669(2) 0.20360(6) 0.52577(11) 0.0241(3) Uani 1 1 d . . . . .
H6 H 0.4171 0.2154 0.4888 0.029 Uiso 1 1 calc R U . . .
C7 C 0.6799(2) 0.15771(6) 0.47383(11) 0.0280(3) Uani 1 1 d . . . . .
H7 H 0.6063 0.1389 0.4013 0.034 Uiso 1 1 calc R U . . .
C8 C 0.9029(2) 0.13966(6) 0.52990(12) 0.0307(3) Uani 1 1 d . . . . .
H8 H 0.9785 0.1092 0.4942 0.037 Uiso 1 1 calc R U . . .
C9 C 1.0132(2) 0.16686(6) 0.63873(13) 0.0307(3) Uani 1 1 d . . . . .
H9 H 1.1614 0.1541 0.6765 0.037 Uiso 1 1 calc R U . . .
C10 C 0.9028(2) 0.21313(6) 0.69128(11) 0.0259(3) Uani 1 1 d . . . . .
H10 H 0.9769 0.2315 0.7642 0.031 Uiso 1 1 calc R U . . .
C11 C -0.1230(2) 0.49807(6) 0.74284(12) 0.0288(3) Uani 1 1 d . . . . .
C12 C -0.1849(4) 0.54331(8) 0.63789(18) 0.0592(5) Uani 1 1 d . . . . .
H12A H -0.2633 0.5785 0.6630 0.089 Uiso 1 1 calc R U . . .
H12B H -0.0461 0.5569 0.6138 0.089 Uiso 1 1 calc R U . . .
H12C H -0.2846 0.5232 0.5702 0.089 Uiso 1 1 calc R U . . .
C13 C -0.3271(3) 0.47565(8) 0.79249(18) 0.0487(4) Uani 1 1 d . . . . .
H13A H -0.4060 0.5106 0.8180 0.073 Uiso 1 1 calc R U . . .
H13B H -0.4316 0.4532 0.7301 0.073 Uiso 1 1 calc R U . . .
H13C H -0.2736 0.4488 0.8610 0.073 Uiso 1 1 calc R U . . .
C14 C 0.0631(3) 0.52502(7) 0.84318(16) 0.0448(4) Uani 1 1 d . . . . .
H14A H 0.0040 0.5612 0.8764 0.067 Uiso 1 1 calc R U . . .
H14B H 0.1081 0.4946 0.9064 0.067 Uiso 1 1 calc R U . . .
H14C H 0.1951 0.5363 0.8103 0.067 Uiso 1 1 calc R U . . .
N1 N -0.0777(2) 0.29623(6) 0.38535(10) 0.0330(3) Uani 1 1 d . . . . .
N2 N 0.24688(18) 0.34640(5) 0.66298(9) 0.0231(2) Uani 1 1 d . . . . .
O1 O -0.29647(18) 0.41224(5) 0.55062(9) 0.0394(3) Uani 1 1 d . . . . .
O2 O -0.00125(15) 0.44340(4) 0.70334(8) 0.0257(2) Uani 1 1 d . . . . .
O3 O 0.35481(14) 0.29588(4) 0.62116(8) 0.0237(2) Uani 1 1 d . . . . .
O4 O 0.66986(16) 0.31684(4) 0.77230(8) 0.0281(2) 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
C1 O1 1.2024(17) . ?
C1 O2 1.3161(15) . ?
C1 C2 1.5082(16) . ?
C2 N2 1.2833(16) . ?
C2 C3 1.4487(17) . ?
C3 N1 1.1434(17) . ?
C4 O4 1.1924(15) . ?
C4 O3 1.3971(14) . ?
C4 C5 1.4811(16) . ?
C5 C10 1.3952(17) . ?
C5 C6 1.4000(16) . ?
C6 C7 1.3862(18) . ?
C6 H6 0.9300 . ?
C7 C8 1.3902(19) . ?
C7 H7 0.9300 . ?
C8 C9 1.3861(19) . ?
C8 H8 0.9300 . ?
C9 C10 1.3868(18) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 O2 1.4932(14) . ?
C11 C13 1.5076(19) . ?
C11 C12 1.511(2) . ?
C11 C14 1.513(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N2 O3 1.3902(13) . ?

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 O2 128.93(12) . . ?
O1 C1 C2 119.94(11) . . ?
O2 C1 C2 111.13(10) . . ?
N2 C2 C3 123.52(11) . . ?
N2 C2 C1 120.39(11) . . ?
C3 C2 C1 116.08(10) . . ?
N1 C3 C2 177.03(14) . . ?
O4 C4 O3 123.46(11) . . ?
O4 C4 C5 127.57(11) . . ?
O3 C4 C5 108.88(9) . . ?
C10 C5 C6 120.26(11) . . ?
C10 C5 C4 117.41(11) . . ?
C6 C5 C4 122.21(11) . . ?
C7 C6 C5 119.40(11) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C8 120.18(12) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 120.37(12) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.06(12) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C5 119.71(12) . . ?
C9 C10 H10 120.1 . . ?
C5 C10 H10 120.1 . . ?
O2 C11 C13 109.17(10) . . ?
O2 C11 C12 109.26(11) . . ?
C13 C11 C12 114.31(15) . . ?
O2 C11 C14 101.69(10) . . ?
C13 C11 C14 111.12(13) . . ?
C12 C11 C14 110.53(14) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 N2 O3 108.64(10) . . ?
C1 O2 C11 120.90(10) . . ?
N2 O3 C4 113.25(9) . . ?

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
O1 C1 C2 N2 -170.22(12) . . . . ?
O2 C1 C2 N2 10.31(16) . . . . ?
O1 C1 C2 C3 10.63(18) . . . . ?
O2 C1 C2 C3 -168.83(10) . . . . ?
O4 C4 C5 C10 4.90(19) . . . . ?
O3 C4 C5 C10 -178.50(10) . . . . ?
O4 C4 C5 C6 -171.04(12) . . . . ?
O3 C4 C5 C6 5.55(15) . . . . ?
C10 C5 C6 C7 -1.57(18) . . . . ?
C4 C5 C6 C7 174.26(11) . . . . ?
C5 C6 C7 C8 0.65(19) . . . . ?
C6 C7 C8 C9 0.7(2) . . . . ?
C7 C8 C9 C10 -1.1(2) . . . . ?
C8 C9 C10 C5 0.2(2) . . . . ?
C6 C5 C10 C9 1.14(18) . . . . ?
C4 C5 C10 C9 -174.89(11) . . . . ?
C3 C2 N2 O3 -2.88(16) . . . . ?
C1 C2 N2 O3 178.04(10) . . . . ?
O1 C1 O2 C11 -0.6(2) . . . . ?
C2 C1 O2 C11 178.84(10) . . . . ?
C13 C11 O2 C1 64.99(16) . . . . ?
C12 C11 O2 C1 -60.68(16) . . . . ?
C14 C11 O2 C1 -177.54(12) . . . . ?
C2 N2 O3 C4 172.89(10) . . . . ?
O4 C4 O3 N2 -1.37(16) . . . . ?
C5 C4 O3 N2 -178.14(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12C O1 0.96 2.40 3.013(2) 121.4 .
C13 H13B O1 0.96 2.48 3.0730(19) 120.2 .

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.040



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
