# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_cd16706
_database_code_depnum_ccdc_archive 'CCDC 1519502'
_audit_update_record             
;
2016-11-28 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 N O3'
_chemical_formula_weight         229.23

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.4606(16)
_cell_length_b                   8.7844(15)
_cell_length_c                   13.698(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.450(4)
_cell_angle_gamma                90
_cell_volume                     1138.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1386
_cell_measurement_theta_min      5.510
_cell_measurement_theta_max      46.856

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6770
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6256
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.153
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2117
_reflns_number_gt                1522
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0557P)²+0.1448P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2117
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1177
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.004
_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
N1 N 0.87249(17) -0.19125(17) 0.60881(10) 0.0523(4) Uani 1 1 d . . . . .
O1 O 0.63082(16) -0.17347(18) 0.61170(11) 0.0765(5) Uani 1 1 d . . . . .
O2 O 0.70912(13) 0.15051(15) 0.58716(9) 0.0589(4) Uani 1 1 d . . . . .
O3 O 0.76285(16) 0.01656(16) 0.82732(10) 0.0694(4) Uani 1 1 d . . . . .
C1 C 0.9873(2) -0.0904(2) 0.62121(11) 0.0458(4) Uani 1 1 d . . . . .
C2 C 1.1287(2) -0.1194(2) 0.61178(13) 0.0562(5) Uani 1 1 d . . . . .
H2 H 1.1609 -0.2161 0.5959 0.067 Uiso 1 1 calc R U . . .
C3 C 1.2218(2) 0.0003(2) 0.62667(14) 0.0615(5) Uani 1 1 d . . . . .
H3 H 1.3182 -0.0164 0.6206 0.074 Uiso 1 1 calc R U . . .
C4 C 1.1748(2) 0.1433(2) 0.65016(13) 0.0608(5) Uani 1 1 d . . . . .
H4 H 1.2395 0.2220 0.6596 0.073 Uiso 1 1 calc R U . . .
C5 C 1.0317(2) 0.1711(2) 0.65986(12) 0.0543(5) Uani 1 1 d . . . . .
H5 H 0.9995 0.2677 0.6760 0.065 Uiso 1 1 calc R U . . .
C6 C 0.93835(18) 0.0532(2) 0.64517(11) 0.0451(4) Uani 1 1 d . . . . .
C7 C 0.7819(2) 0.0457(2) 0.65154(12) 0.0498(5) Uani 1 1 d . . . . .
C8 C 0.7476(2) -0.1189(2) 0.62076(12) 0.0546(5) Uani 1 1 d . . . . .
C9 C 0.8837(2) -0.3501(2) 0.58160(16) 0.0716(6) Uani 1 1 d . . . . .
H9A H 0.7945 -0.3996 0.5906 0.107 Uiso 1 1 calc R U . . .
H9B H 0.9550 -0.3985 0.6218 0.107 Uiso 1 1 calc R U . . .
H9C H 0.9088 -0.3575 0.5143 0.107 Uiso 1 1 calc R U . . .
C10 C 0.7215(2) 0.0794(2) 0.75265(14) 0.0539(5) Uani 1 1 d . . . . .
C11 C 0.6165(2) 0.1922(2) 0.73519(15) 0.0627(6) Uani 1 1 d . . . . .
H11 H 0.5578 0.2333 0.7819 0.075 Uiso 1 1 calc R U . . .
C12 C 0.61576(19) 0.2297(2) 0.64069(15) 0.0582(5) Uani 1 1 d . . . . .
C13 C 0.5351(2) 0.3444(3) 0.58263(19) 0.0811(7) Uani 1 1 d . . . . .
H13A H 0.5997 0.4131 0.5525 0.122 Uiso 1 1 calc R U . . .
H13B H 0.4744 0.4004 0.6248 0.122 Uiso 1 1 calc R U . . .
H13C H 0.4790 0.2939 0.5331 0.122 Uiso 1 1 calc R U . . .


_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 C8 1.355(2) . ?
N1 C1 1.409(2) . ?
N1 C9 1.449(2) . ?
O1 C8 1.208(2) . ?
O2 C12 1.354(2) . ?
O2 C7 1.438(2) . ?
O3 C10 1.218(2) . ?
C1 C2 1.370(3) . ?
C1 C6 1.386(2) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.486(3) . ?
C7 C8 1.539(3) . ?
C7 C10 1.540(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.420(3) . ?
C11 C12 1.336(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.482(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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
C8 N1 C1 111.26(16) . . ?
C8 N1 C9 123.53(16) . . ?
C1 N1 C9 125.14(16) . . ?
C12 O2 C7 107.79(14) . . ?
C2 C1 C6 121.61(18) . . ?
C2 C1 N1 128.56(17) . . ?
C6 C1 N1 109.83(16) . . ?
C1 C2 C3 117.66(18) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 121.40(19) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 120.44(19) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 118.64(18) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 120.25(17) . . ?
C5 C6 C7 131.47(17) . . ?
C1 C6 C7 108.27(15) . . ?
O2 C7 C6 113.46(14) . . ?
O2 C7 C8 109.83(15) . . ?
C6 C7 C8 103.20(15) . . ?
O2 C7 C10 104.23(15) . . ?
C6 C7 C10 115.90(15) . . ?
C8 C7 C10 110.27(15) . . ?
O1 C8 N1 126.83(19) . . ?
O1 C8 C7 125.94(19) . . ?
N1 C8 C7 107.20(16) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C10 C11 131.77(17) . . ?
O3 C10 C7 123.36(18) . . ?
C11 C10 C7 104.87(16) . . ?
C12 C11 C10 108.76(17) . . ?
C12 C11 H11 125.6 . . ?
C10 C11 H11 125.6 . . ?
C11 C12 O2 114.25(18) . . ?
C11 C12 C13 132.6(2) . . ?
O2 C12 C13 113.10(18) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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 C1 C2 -177.64(16) . . . . ?
C9 N1 C1 C2 -0.8(3) . . . . ?
C8 N1 C1 C6 1.86(19) . . . . ?
C9 N1 C1 C6 178.73(16) . . . . ?
C6 C1 C2 C3 -0.2(2) . . . . ?
N1 C1 C2 C3 179.20(16) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 0.0(2) . . . . ?
C4 C5 C6 C7 178.90(17) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
N1 C1 C6 C5 -179.33(14) . . . . ?
C2 C1 C6 C7 -178.90(14) . . . . ?
N1 C1 C6 C7 1.56(18) . . . . ?
C12 O2 C7 C6 -129.16(15) . . . . ?
C12 O2 C7 C8 115.93(16) . . . . ?
C12 O2 C7 C10 -2.19(18) . . . . ?
C5 C6 C7 O2 58.4(2) . . . . ?
C1 C6 C7 O2 -122.67(15) . . . . ?
C5 C6 C7 C8 177.14(17) . . . . ?
C1 C6 C7 C8 -3.88(17) . . . . ?
C5 C6 C7 C10 -62.2(2) . . . . ?
C1 C6 C7 C10 116.75(17) . . . . ?
C1 N1 C8 O1 177.50(17) . . . . ?
C9 N1 C8 O1 0.6(3) . . . . ?
C1 N1 C8 C7 -4.32(18) . . . . ?
C9 N1 C8 C7 178.76(16) . . . . ?
O2 C7 C8 O1 -55.6(2) . . . . ?
C6 C7 C8 O1 -176.84(18) . . . . ?
C10 C7 C8 O1 58.8(2) . . . . ?
O2 C7 C8 N1 126.24(15) . . . . ?
C6 C7 C8 N1 4.96(17) . . . . ?
C10 C7 C8 N1 -119.45(16) . . . . ?
O2 C7 C10 O3 -176.72(17) . . . . ?
C6 C7 C10 O3 -51.3(2) . . . . ?
C8 C7 C10 O3 65.5(2) . . . . ?
O2 C7 C10 C11 3.09(19) . . . . ?
C6 C7 C10 C11 128.52(17) . . . . ?
C8 C7 C10 C11 -114.73(18) . . . . ?
O3 C10 C11 C12 176.9(2) . . . . ?
C7 C10 C11 C12 -2.9(2) . . . . ?
C10 C11 C12 O2 1.7(2) . . . . ?
C10 C11 C12 C13 -176.5(2) . . . . ?
C7 O2 C12 C11 0.5(2) . . . . ?
C7 O2 C12 C13 178.99(16) . . . . ?

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.115
_refine_diff_density_rms         0.031

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_mjl18313_0m
_database_code_depnum_ccdc_archive 'CCDC 1856499'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2018-07-18 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;
_audit_creation_date             2018-07-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H13 N O3'
_chemical_formula_sum            'C15 H13 N O3'
_chemical_formula_weight         255.26
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.27760(10)
_cell_length_b                   10.8907(2)
_cell_length_c                   22.1326(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1272.11(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9882
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.911
_cell_measurement_theta_min      3.475
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.943
_exptl_absorpt_coefficient_mu    0.493
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1784 before and 0.0553 after correction. The Ratio of minimum to maximum transmission is 0.8367. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13350
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.886
_diffrn_reflns_theta_min         3.475
_diffrn_ambient_temperature      170.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                2322
_reflns_number_total             2370
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 931 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0327
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0468P)²+0.2934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0878
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O1 O 1.1204(3) 0.78152(13) 0.41357(6) 0.0325(4) Uani 1 1 d . . . . .
H1 H 1.130084 0.753401 0.448839 0.049 Uiso 1 1 calc GR . . . .
O2 O 0.6393(3) 0.84756(13) 0.48171(6) 0.0350(4) Uani 1 1 d . . . . .
O3 O 0.7720(4) 0.32518(14) 0.41295(9) 0.0504(5) Uani 1 1 d . . . . .
N1 N 0.5996(3) 0.93970(14) 0.38952(7) 0.0253(4) Uani 1 1 d . . . . .
C1 C 0.4324(4) 1.04318(18) 0.40345(10) 0.0342(5) Uani 1 1 d . . . . .
H1A H 0.533415 1.112550 0.419445 0.041 Uiso 1 1 calc R . . . .
H1B H 0.308195 1.018615 0.434704 0.041 Uiso 1 1 calc R . . . .
C2 C 0.2954(5) 1.0825(2) 0.34702(11) 0.0429(5) Uani 1 1 d . . . . .
H2A H 0.199177 1.158504 0.355754 0.052 Uiso 1 1 calc R . . . .
H2B H 0.171692 1.018037 0.335847 0.052 Uiso 1 1 calc R . . . .
C3 C 0.4702(5) 1.1059(2) 0.29328(11) 0.0401(5) Uani 1 1 d . . . . .
H3A H 0.367052 1.120430 0.256614 0.048 Uiso 1 1 calc R . . . .
H3B H 0.572458 1.180531 0.300961 0.048 Uiso 1 1 calc R . . . .
C4 C 0.6444(4) 0.99824(18) 0.28275(8) 0.0290(4) Uani 1 1 d . . . . .
C5 C 0.7692(4) 0.96824(19) 0.22924(9) 0.0340(5) Uani 1 1 d . . . . .
H5 H 0.739288 1.016334 0.194146 0.041 Uiso 1 1 calc R . . . .
C6 C 0.9357(5) 0.87008(19) 0.22589(9) 0.0358(5) Uani 1 1 d . . . . .
H6 H 1.020419 0.853365 0.188929 0.043 Uiso 1 1 calc R . . . .
C7 C 0.9808(4) 0.79537(18) 0.27601(9) 0.0307(4) Uani 1 1 d . . . . .
H7 H 1.095837 0.728453 0.273679 0.037 Uiso 1 1 calc R . . . .
C8 C 0.8545(4) 0.82109(16) 0.32876(8) 0.0238(4) Uani 1 1 d . . . . .
C9 C 0.6949(4) 0.92149(17) 0.33109(8) 0.0235(4) Uani 1 1 d . . . . .
C10 C 0.6870(4) 0.85374(16) 0.42784(8) 0.0248(4) Uani 1 1 d . . . . .
C11 C 0.8706(4) 0.76769(16) 0.39191(8) 0.0243(4) Uani 1 1 d . . . . .
C12 C 0.7823(4) 0.63953(17) 0.39674(8) 0.0261(4) Uani 1 1 d . . . . .
C13 C 0.7146(4) 0.53616(17) 0.40507(9) 0.0290(4) Uani 1 1 d . . . . .
C14 C 0.6356(4) 0.41250(17) 0.42198(9) 0.0302(4) Uani 1 1 d . . . . .
C15 C 0.3828(6) 0.4011(2) 0.45052(14) 0.0524(7) Uani 1 1 d . . . . .
H15A H 0.251233 0.406245 0.419368 0.079 Uiso 1 1 calc GR . . . .
H15B H 0.359365 0.467632 0.479791 0.079 Uiso 1 1 calc GR . . . .
H15C H 0.370494 0.321812 0.471266 0.079 Uiso 1 1 calc GR . . . .


_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 H1 0.8400 . ?
O1 C11 1.411(2) . ?
O2 C10 1.221(2) . ?
O3 C14 1.209(3) . ?
N1 C1 1.464(2) . ?
N1 C9 1.402(2) . ?
N1 C10 1.345(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.505(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.527(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.508(3) . ?
C4 C5 1.394(3) . ?
C4 C9 1.384(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.396(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.373(3) . ?
C8 C9 1.381(3) . ?
C8 C11 1.516(2) . ?
C10 C11 1.565(3) . ?
C11 C12 1.475(2) . ?
C12 C13 1.196(3) . ?
C13 C14 1.459(3) . ?
C14 C15 1.481(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C11 O1 H1 109.5 . . ?
C9 N1 C1 121.29(15) . . ?
C10 N1 C1 127.57(16) . . ?
C10 N1 C9 111.12(15) . . ?
N1 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
N1 C1 C2 109.51(17) . . ?
H1A C1 H1B 108.2 . . ?
C2 C1 H1A 109.8 . . ?
C2 C1 H1B 109.8 . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C1 C2 C3 113.8(2) . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 111.03(17) . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C5 C4 C3 126.98(17) . . ?
C9 C4 C3 117.89(18) . . ?
C9 C4 C5 115.10(18) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.72(17) . . ?
C6 C5 H5 119.1 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.01(19) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 120.9 . . ?
C8 C7 C6 118.29(19) . . ?
C8 C7 H7 120.9 . . ?
C7 C8 C9 119.29(16) . . ?
C7 C8 C11 132.72(18) . . ?
C9 C8 C11 107.66(15) . . ?
C4 C9 N1 123.97(18) . . ?
C8 C9 N1 111.43(15) . . ?
C8 C9 C4 124.53(17) . . ?
O2 C10 N1 125.72(18) . . ?
O2 C10 C11 126.23(17) . . ?
N1 C10 C11 107.98(15) . . ?
O1 C11 C8 108.93(15) . . ?
O1 C11 C10 110.00(15) . . ?
O1 C11 C12 111.80(15) . . ?
C8 C11 C10 101.77(14) . . ?
C12 C11 C8 114.34(15) . . ?
C12 C11 C10 109.52(15) . . ?
C13 C12 C11 175.2(2) . . ?
C12 C13 C14 174.0(2) . . ?
O3 C14 C13 120.89(19) . . ?
O3 C14 C15 122.73(19) . . ?
C13 C14 C15 116.38(18) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cd16781
_database_code_depnum_ccdc_archive 'CCDC 1524876'
_audit_update_record             
;
2016-12-29 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 N O5'
_chemical_formula_weight         273.24

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.0859(16)
_cell_length_b                   9.2256(13)
_cell_length_c                   12.6525(18)
_cell_angle_alpha                90
_cell_angle_beta                 101.245(3)
_cell_angle_gamma                90
_cell_volume                     1269.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2295
_cell_measurement_theta_min      5.502
_cell_measurement_theta_max      51.979

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6821
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7057
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.873
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2350
_reflns_number_gt                1892
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0628P)²+0.1544P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2350
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1174
_refine_ls_wR_factor_gt          0.1097
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
N1 N 0.11669(11) 0.28586(15) 0.92125(11) 0.0455(3) Uani 1 1 d . . . . .
O1 O 0.20405(12) 0.51161(14) 0.95522(11) 0.0638(4) Uani 1 1 d . . . . .
O2 O 0.21822(11) 0.44253(13) 0.72807(9) 0.0542(3) Uani 1 1 d . . . . .
O3 O 0.29536(15) 0.61181(16) 0.63468(12) 0.0822(5) Uani 1 1 d . . . . .
O4 O 0.41721(11) 0.48833(14) 0.76737(10) 0.0587(4) Uani 1 1 d . . . . .
O5 O 0.37223(11) 0.21492(14) 1.01991(10) 0.0633(4) Uani 1 1 d . . . . .
C1 C 0.13593(13) 0.16620(17) 0.85813(13) 0.0438(4) Uani 1 1 d . . . . .
C2 C 0.07925(16) 0.0332(2) 0.85177(15) 0.0574(5) Uani 1 1 d . . . . .
H2 H 0.0199 0.0122 0.8923 0.069 Uiso 1 1 calc R U . . .
C3 C 0.11358(18) -0.0683(2) 0.78284(16) 0.0639(5) Uani 1 1 d . . . . .
H3 H 0.0765 -0.1592 0.7772 0.077 Uiso 1 1 calc R U . . .
C4 C 0.20108(19) -0.0387(2) 0.72231(15) 0.0609(5) Uani 1 1 d . . . . .
H4 H 0.2220 -0.1091 0.6764 0.073 Uiso 1 1 calc R U . . .
C5 C 0.25849(15) 0.09606(19) 0.72932(13) 0.0507(4) Uani 1 1 d . . . . .
H5 H 0.3179 0.1170 0.6889 0.061 Uiso 1 1 calc R U . . .
C6 C 0.22477(14) 0.19707(17) 0.79764(12) 0.0420(4) Uani 1 1 d . . . . .
C7 C 0.26454(13) 0.35059(17) 0.82060(12) 0.0420(4) Uani 1 1 d . . . . .
C8 C 0.19370(14) 0.39608(18) 0.90997(13) 0.0451(4) Uani 1 1 d . . . . .
C9 C 0.03706(16) 0.2852(2) 0.99920(16) 0.0599(5) Uani 1 1 d . . . . .
H9A H 0.0679 0.2174 1.0556 0.090 Uiso 1 1 calc R U . . .
H9B H -0.0445 0.2574 0.9644 0.090 Uiso 1 1 calc R U . . .
H9C H 0.0349 0.3804 1.0294 0.090 Uiso 1 1 calc R U . . .
C10 C 0.30781(18) 0.52233(19) 0.70263(15) 0.0566(5) Uani 1 1 d . . . . .
C11 C 0.39917(14) 0.38785(16) 0.84339(13) 0.0436(4) Uani 1 1 d . . . . .
C12 C 0.49167(15) 0.34375(19) 0.91876(14) 0.0502(4) Uani 1 1 d . . . . .
H12 H 0.5706 0.3763 0.9166 0.060 Uiso 1 1 calc R U . . .
C13 C 0.47458(15) 0.24542(19) 1.00568(14) 0.0494(4) Uani 1 1 d . . . . .
C14 C 0.58717(17) 0.1880(2) 1.07679(17) 0.0709(6) Uani 1 1 d . . . . .
H14A H 0.5681 0.1597 1.1447 0.106 Uiso 1 1 calc R U . . .
H14B H 0.6494 0.2618 1.0884 0.106 Uiso 1 1 calc R U . . .
H14C H 0.6167 0.1055 1.0432 0.106 Uiso 1 1 calc R U . . .


_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 C8 1.353(2) . ?
N1 C1 1.403(2) . ?
N1 C9 1.446(2) . ?
O1 C8 1.205(2) . ?
O2 C10 1.325(2) . ?
O2 C7 1.4558(18) . ?
O3 C10 1.180(2) . ?
O4 C10 1.361(2) . ?
O4 C11 1.3783(19) . ?
O5 C13 1.216(2) . ?
C1 C2 1.374(2) . ?
C1 C6 1.390(2) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.495(2) . ?
C7 C11 1.504(2) . ?
C7 C8 1.555(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C11 C12 1.321(2) . ?
C12 C13 1.466(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.486(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
C8 N1 C1 111.24(13) . . ?
C8 N1 C9 123.83(15) . . ?
C1 N1 C9 124.44(14) . . ?
C10 O2 C7 110.82(13) . . ?
C10 O4 C11 109.97(13) . . ?
C2 C1 C6 121.07(16) . . ?
C2 C1 N1 128.14(16) . . ?
C6 C1 N1 110.79(13) . . ?
C1 C2 C3 117.57(18) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 121.82(17) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 120.37(18) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 118.02(17) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 C1 121.15(15) . . ?
C5 C6 C7 131.29(15) . . ?
C1 C6 C7 107.52(14) . . ?
O2 C7 C6 110.57(12) . . ?
O2 C7 C11 101.67(12) . . ?
C6 C7 C11 119.86(13) . . ?
O2 C7 C8 106.17(12) . . ?
C6 C7 C8 103.03(13) . . ?
C11 C7 C8 114.96(13) . . ?
O1 C8 N1 128.19(16) . . ?
O1 C8 C7 124.73(14) . . ?
N1 C8 C7 107.00(14) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C10 O2 125.35(19) . . ?
O3 C10 O4 124.29(18) . . ?
O2 C10 O4 110.35(14) . . ?
C12 C11 O4 120.87(15) . . ?
C12 C11 C7 132.05(15) . . ?
O4 C11 C7 107.07(13) . . ?
C11 C12 C13 122.44(15) . . ?
C11 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
O5 C13 C12 121.00(15) . . ?
O5 C13 C14 121.70(18) . . ?
C12 C13 C14 117.28(16) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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 C1 C2 177.16(15) . . . . ?
C9 N1 C1 C2 4.9(2) . . . . ?
C8 N1 C1 C6 -2.88(17) . . . . ?
C9 N1 C1 C6 -175.10(14) . . . . ?
C6 C1 C2 C3 -0.2(2) . . . . ?
N1 C1 C2 C3 179.76(15) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 0.0(2) . . . . ?
C4 C5 C6 C7 -177.58(15) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
N1 C1 C6 C5 -179.72(13) . . . . ?
C2 C1 C6 C7 178.31(14) . . . . ?
N1 C1 C6 C7 -1.66(16) . . . . ?
C10 O2 C7 C6 -129.85(15) . . . . ?
C10 O2 C7 C11 -1.48(17) . . . . ?
C10 O2 C7 C8 119.08(15) . . . . ?
C5 C6 C7 O2 69.5(2) . . . . ?
C1 C6 C7 O2 -108.26(14) . . . . ?
C5 C6 C7 C11 -48.2(2) . . . . ?
C1 C6 C7 C11 134.05(14) . . . . ?
C5 C6 C7 C8 -177.38(15) . . . . ?
C1 C6 C7 C8 4.83(15) . . . . ?
C1 N1 C8 O1 -177.29(16) . . . . ?
C9 N1 C8 O1 -5.0(3) . . . . ?
C1 N1 C8 C7 5.90(16) . . . . ?
C9 N1 C8 C7 178.18(13) . . . . ?
O2 C7 C8 O1 -67.19(19) . . . . ?
C6 C7 C8 O1 176.54(15) . . . . ?
C11 C7 C8 O1 44.4(2) . . . . ?
O2 C7 C8 N1 109.75(14) . . . . ?
C6 C7 C8 N1 -6.52(15) . . . . ?
C11 C7 C8 N1 -138.69(13) . . . . ?
C7 O2 C10 O3 -175.84(18) . . . . ?
C7 O2 C10 O4 3.2(2) . . . . ?
C11 O4 C10 O3 175.39(18) . . . . ?
C11 O4 C10 O2 -3.7(2) . . . . ?
C10 O4 C11 C12 -176.59(16) . . . . ?
C10 O4 C11 C7 2.59(17) . . . . ?
O2 C7 C11 C12 178.36(17) . . . . ?
C6 C7 C11 C12 -59.5(2) . . . . ?
C8 C7 C11 C12 64.2(2) . . . . ?
O2 C7 C11 O4 -0.69(15) . . . . ?
C6 C7 C11 O4 121.48(15) . . . . ?
C8 C7 C11 O4 -114.88(14) . . . . ?
O4 C11 C12 C13 175.33(15) . . . . ?
C7 C11 C12 C13 -3.6(3) . . . . ?
C11 C12 C13 O5 -9.5(3) . . . . ?
C11 C12 C13 C14 171.97(17) . . . . ?

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-4



