# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_cmpd1
_database_code_depnum_ccdc_archive 'CCDC 1578343'
_audit_update_record             
;
2017-10-06 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H9 N O3'
_chemical_formula_weight         143.14
_chemical_oxdiff_usercomment     'S Williams/ Amani, ID AM-1-15'

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   8.5061(2)
_cell_length_b                   15.9215(4)
_cell_length_c                   9.6417(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1305.77(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    130.00(10)
_cell_measurement_reflns_used    7360
_cell_measurement_theta_min      4.2360
_cell_measurement_theta_max      36.0330

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.611
_exptl_crystal_size_mid          0.475
_exptl_crystal_size_min          0.401
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.51711
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.608
_oxdiff_exptl_absorpt_empirical_full_max 1.855
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      130.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_reflns_number            16434
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.194
_diffrn_reflns_theta_max         36.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6071
_reflns_number_gt                5610
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_max     0.929
_reflns_Friedel_fraction_full    0.999

_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0504P)²+0.1315P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2245 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         6071
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0977
_refine_ls_wR_factor_gt          0.0952
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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 0.17980(15) 0.35670(8) 0.35748(13) 0.0200(2) Uani 1 1 d . . . . .
H1 H 0.262666 0.363258 0.284713 0.024 Uiso 1 1 calc R U . . .
C1A C 0.83547(14) 0.62450(7) 0.59157(12) 0.01694(19) Uani 1 1 d . . . . .
H1A H 0.769469 0.605146 0.671225 0.020 Uiso 1 1 calc R U . . .
C2 C 0.21592(13) 0.41006(7) 0.48214(12) 0.01609(18) Uani 1 1 d . . . . .
C2A C 0.78435(14) 0.58317(7) 0.45882(12) 0.01641(19) Uani 1 1 d . . . . .
C3 C 0.10045(14) 0.40406(8) 0.59940(13) 0.0202(2) Uani 1 1 d . . . . .
H3A H 0.011449 0.442742 0.582156 0.024 Uiso 1 1 calc R U . . .
H3B H 0.152084 0.421244 0.686940 0.024 Uiso 1 1 calc R U . . .
C3A C 0.88198(15) 0.60013(9) 0.33217(13) 0.0218(2) Uani 1 1 d . . . . .
H3A1 H 0.840142 0.650051 0.283329 0.026 Uiso 1 1 calc R U . . .
H3A2 H 0.875026 0.551587 0.268306 0.026 Uiso 1 1 calc R U . . .
C4 C 0.03834(15) 0.31362(9) 0.61368(14) 0.0217(2) Uani 1 1 d . . . . .
H4A H 0.112748 0.280274 0.670266 0.026 Uiso 1 1 calc R U . . .
H4B H -0.064109 0.314485 0.662379 0.026 Uiso 1 1 calc R U . . .
C4A C 1.05494(14) 0.61545(8) 0.37099(14) 0.0206(2) Uani 1 1 d . . . . .
H4A1 H 1.111201 0.561038 0.373302 0.025 Uiso 1 1 calc R U . . .
H4A2 H 1.104756 0.650886 0.298967 0.025 Uiso 1 1 calc R U . . .
C5 C 0.01837(15) 0.27224(8) 0.47290(14) 0.0207(2) Uani 1 1 d . . . . .
H5 H -0.023696 0.213898 0.482784 0.025 Uiso 1 1 calc R U . . .
C5A C 1.07099(14) 0.65822(8) 0.51085(13) 0.0202(2) Uani 1 1 d . . . . .
H5A H 1.184167 0.667626 0.534224 0.024 Uiso 1 1 calc R U . . .
C6 C -0.08276(15) 0.32382(9) 0.37363(14) 0.0216(2) Uani 1 1 d . . . . .
H6A H -0.137852 0.287056 0.306583 0.026 Uiso 1 1 calc R U . . .
H6B H -0.161575 0.357366 0.425014 0.026 Uiso 1 1 calc R U . . .
C6A C 0.97772(17) 0.74013(8) 0.52280(14) 0.0228(2) Uani 1 1 d . . . . .
H6A1 H 1.029502 0.779649 0.587591 0.027 Uiso 1 1 calc R U . . .
H6A2 H 0.966536 0.767554 0.431179 0.027 Uiso 1 1 calc R U . . .
N1 N 0.34079(12) 0.45449(7) 0.47578(11) 0.01829(17) Uani 1 1 d . . . . .
N1A N 0.65783(12) 0.53982(7) 0.46555(11) 0.01865(18) Uani 1 1 d . . . . .
O1 O 0.36390(12) 0.50354(7) 0.59525(11) 0.02487(19) Uani 1 1 d . . . . .
O1A O 0.61634(13) 0.50483(7) 0.33638(11) 0.0265(2) Uani 1 1 d . . . . .
O5 O 0.16806(12) 0.27204(6) 0.40116(12) 0.0248(2) Uani 1 1 d . . . . .
O5A O 0.99560(11) 0.60700(6) 0.61538(10) 0.02134(18) Uani 1 1 d . . . . .
O6 O 0.02873(12) 0.37756(7) 0.30402(10) 0.0250(2) Uani 1 1 d . . . . .
O6A O 0.82629(11) 0.71353(6) 0.57586(10) 0.02136(17) Uani 1 1 d . . . . .
H3 H 0.458(3) 0.5218(14) 0.585(3) 0.035(6) Uiso 1 1 d . . . . .
H3C H 0.526(3) 0.4800(16) 0.349(3) 0.045(7) Uiso 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 O5 1.4157(16) . ?
C1 O6 1.4238(16) . ?
C1 C2 1.5036(17) . ?
C1 H1 1.0000 . ?
C1A O5A 1.4091(15) . ?
C1A O6A 1.4278(14) . ?
C1A C2A 1.5033(17) . ?
C1A H1A 1.0000 . ?
C2 N1 1.2776(15) . ?
C2 C3 1.5007(17) . ?
C2A N1A 1.2802(15) . ?
C2A C3A 1.5012(17) . ?
C3 C4 1.5399(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C4A 1.5375(18) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C4 C5 1.518(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4A C5A 1.5168(19) . ?
C4A H4A1 0.9900 . ?
C4A H4A2 0.9900 . ?
C5 O5 1.4490(16) . ?
C5 C6 1.5266(18) . ?
C5 H5 1.0000 . ?
C5A O5A 1.4463(15) . ?
C5A C6A 1.531(2) . ?
C5A H5A 1.0000 . ?
C6 O6 1.4428(16) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6A O6A 1.4493(16) . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?
N1 O1 1.4055(14) . ?
N1A O1A 1.4092(14) . ?
O1 H3 0.85(2) . ?
O1A H3C 0.87(3) . ?

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
O5 C1 O6 105.43(10) . . ?
O5 C1 C2 108.33(10) . . ?
O6 C1 C2 110.00(10) . . ?
O5 C1 H1 111.0 . . ?
O6 C1 H1 111.0 . . ?
C2 C1 H1 111.0 . . ?
O5A C1A O6A 105.45(9) . . ?
O5A C1A C2A 109.38(10) . . ?
O6A C1A C2A 109.17(9) . . ?
O5A C1A H1A 110.9 . . ?
O6A C1A H1A 110.9 . . ?
C2A C1A H1A 110.9 . . ?
N1 C2 C3 127.99(11) . . ?
N1 C2 C1 116.38(11) . . ?
C3 C2 C1 115.63(10) . . ?
N1A C2A C3A 127.10(11) . . ?
N1A C2A C1A 115.85(10) . . ?
C3A C2A C1A 116.99(10) . . ?
C2 C3 C4 110.58(10) . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C2A C3A C4A 111.09(10) . . ?
C2A C3A H3A1 109.4 . . ?
C4A C3A H3A1 109.4 . . ?
C2A C3A H3A2 109.4 . . ?
C4A C3A H3A2 109.4 . . ?
H3A1 C3A H3A2 108.0 . . ?
C5 C4 C3 111.36(10) . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C5A C4A C3A 111.95(10) . . ?
C5A C4A H4A1 109.2 . . ?
C3A C4A H4A1 109.2 . . ?
C5A C4A H4A2 109.2 . . ?
C3A C4A H4A2 109.2 . . ?
H4A1 C4A H4A2 107.9 . . ?
O5 C5 C4 109.23(10) . . ?
O5 C5 C6 101.37(10) . . ?
C4 C5 C6 112.96(11) . . ?
O5 C5 H5 111.0 . . ?
C4 C5 H5 111.0 . . ?
C6 C5 H5 111.0 . . ?
O5A C5A C4A 109.06(10) . . ?
O5A C5A C6A 101.42(10) . . ?
C4A C5A C6A 113.74(10) . . ?
O5A C5A H5A 110.7 . . ?
C4A C5A H5A 110.7 . . ?
C6A C5A H5A 110.7 . . ?
O6 C6 C5 103.90(10) . . ?
O6 C6 H6A 111.0 . . ?
C5 C6 H6A 111.0 . . ?
O6 C6 H6B 111.0 . . ?
C5 C6 H6B 111.0 . . ?
H6A C6 H6B 109.0 . . ?
O6A C6A C5A 103.78(10) . . ?
O6A C6A H6A1 111.0 . . ?
C5A C6A H6A1 111.0 . . ?
O6A C6A H6A2 111.0 . . ?
C5A C6A H6A2 111.0 . . ?
H6A1 C6A H6A2 109.0 . . ?
C2 N1 O1 112.62(10) . . ?
C2A N1A O1A 112.27(10) . . ?
N1 O1 H3 103.1(17) . . ?
N1A O1A H3C 106.2(17) . . ?
C1 O5 C5 101.65(9) . . ?
C1A O5A C5A 101.75(9) . . ?
C1 O6 C6 106.65(10) . . ?
C1A O6A C6A 106.19(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
O5 C1 C2 N1 122.77(11) . . . . ?
O6 C1 C2 N1 -122.46(11) . . . . ?
O5 C1 C2 C3 -56.93(14) . . . . ?
O6 C1 C2 C3 57.84(14) . . . . ?
O5A C1A C2A N1A 130.66(11) . . . . ?
O6A C1A C2A N1A -114.43(11) . . . . ?
O5A C1A C2A C3A -52.03(13) . . . . ?
O6A C1A C2A C3A 62.89(14) . . . . ?
N1 C2 C3 C4 -143.21(12) . . . . ?
C1 C2 C3 C4 36.45(15) . . . . ?
N1A C2A C3A C4A -152.58(12) . . . . ?
C1A C2A C3A C4A 30.45(15) . . . . ?
C2 C3 C4 C5 -36.53(14) . . . . ?
C2A C3A C4A C5A -32.84(15) . . . . ?
C3 C4 C5 O5 58.30(13) . . . . ?
C3 C4 C5 C6 -53.69(14) . . . . ?
C3A C4A C5A O5A 57.88(13) . . . . ?
C3A C4A C5A C6A -54.51(14) . . . . ?
O5 C5 C6 O6 -27.30(13) . . . . ?
C4 C5 C6 O6 89.44(12) . . . . ?
O5A C5A C6A O6A -26.49(12) . . . . ?
C4A C5A C6A O6A 90.43(12) . . . . ?
C3 C2 N1 O1 -1.50(17) . . . . ?
C1 C2 N1 O1 178.84(10) . . . . ?
C3A C2A N1A O1A 1.69(18) . . . . ?
C1A C2A N1A O1A 178.68(10) . . . . ?
O6 C1 O5 C5 -44.40(12) . . . . ?
C2 C1 O5 C5 73.33(12) . . . . ?
C4 C5 O5 C1 -76.14(12) . . . . ?
C6 C5 O5 C1 43.30(12) . . . . ?
O6A C1A O5A C5A -45.31(12) . . . . ?
C2A C1A O5A C5A 71.97(11) . . . . ?
C4A C5A O5A C1A -76.91(12) . . . . ?
C6A C5A O5A C1A 43.39(12) . . . . ?
O5 C1 O6 C6 26.63(13) . . . . ?
C2 C1 O6 C6 -89.97(12) . . . . ?
C5 C6 O6 C1 1.11(13) . . . . ?
O5A C1A O6A C6A 27.87(12) . . . . ?
C2A C1A O6A C6A -89.55(11) . . . . ?
C5A C6A O6A C1A -0.07(12) . . . . ?

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
C1A H1A O1A 1.00 2.56 3.1591(15) 118.4 2_665
C3 H3A O5A 0.99 2.64 3.3555(17) 129.4 1_455
C3A H3A1 O5 0.99 2.63 3.5685(17) 157.3 3_655
C5A H5A O6A 1.00 2.48 3.0958(15) 119.1 4_566
O1 H3 N1A 0.85(2) 2.08(2) 2.8546(15) 151(2) .
O1A H3C N1 0.87(3) 2.03(3) 2.8182(15) 149(2) .

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_cmpd5
_database_code_depnum_ccdc_archive 'CCDC 1578347'
_audit_update_record             
;
2017-10-06 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H12 N2 O6'
_chemical_formula_weight         292.25
_chemical_oxdiff_usercomment     'aALHIFTHI/SPENCER  SAMPLE AM-1-40'

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.3112(2)
_cell_length_b                   12.3133(3)
_cell_length_c                   13.9596(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1256.71(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    130.01(10)
_cell_measurement_reflns_used    7594
_cell_measurement_theta_min      4.2970
_cell_measurement_theta_max      40.3790

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.763
_exptl_crystal_size_mid          0.589
_exptl_crystal_size_min          0.367
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.84778
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.762
_oxdiff_exptl_absorpt_empirical_full_max 1.414
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      130.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_reflns_number            23595
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.554
_diffrn_reflns_theta_max         40.932
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             8050
_reflns_number_gt                7038
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.785
_reflns_Friedel_fraction_max     0.968
_reflns_Friedel_fraction_full    0.999

_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    shelxt
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0542P)²+0.0640P] 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_abs_structure_details 
;
 Flack x determined using 2752 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         8050
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1077
_refine_ls_wR_factor_gt          0.1008
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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 0.72298(14) 1.07302(8) 0.63371(7) 0.01828(15) Uani 1 1 d . . . . .
H1 H 0.781444 1.091306 0.694794 0.022 Uiso 1 1 calc R U . . .
C2 C 0.68236(14) 0.95260(8) 0.62754(7) 0.01759(15) Uani 1 1 d . . . . .
C3 C 0.59237(16) 0.91672(10) 0.53632(8) 0.02180(18) Uani 1 1 d . . . . .
H3A H 0.461547 0.928870 0.540621 0.026 Uiso 1 1 calc R U . . .
H3B H 0.612731 0.839587 0.527036 0.026 Uiso 1 1 calc R U . . .
C4 C 0.66996(17) 0.97980(9) 0.45060(8) 0.02145(18) Uani 1 1 d . . . . .
H4A H 0.781630 0.945039 0.428975 0.026 Uiso 1 1 calc R U . . .
H4B H 0.582662 0.977765 0.398311 0.026 Uiso 1 1 calc R U . . .
C5 C 0.71028(15) 1.09722(9) 0.47635(7) 0.02050(17) Uani 1 1 d . . . . .
H5 H 0.760161 1.136533 0.421182 0.025 Uiso 1 1 calc R U . . .
C6 C 0.54807(18) 1.15735(11) 0.51883(9) 0.0257(2) Uani 1 1 d . . . . .
H6A H 0.557429 1.234798 0.507120 0.031 Uiso 1 1 calc R U . . .
H6B H 0.433928 1.130942 0.492146 0.031 Uiso 1 1 calc R U . . .
C7 C 0.78847(15) 0.71877(8) 0.74565(7) 0.01842(16) Uani 1 1 d . . . . .
C8 C 0.75391(13) 0.60258(8) 0.72325(7) 0.01588(14) Uani 1 1 d . . . . .
C9 C 0.80702(14) 0.52596(8) 0.79109(7) 0.01698(15) Uani 1 1 d . . . . .
H9 H 0.862942 0.547021 0.847967 0.020 Uiso 1 1 calc R U . . .
C10 C 0.77428(14) 0.41771(8) 0.77147(7) 0.01756(15) Uani 1 1 d . . . . .
C11 C 0.69482(16) 0.38230(9) 0.68685(7) 0.02058(17) Uani 1 1 d . . . . .
H11 H 0.674862 0.308803 0.675624 0.025 Uiso 1 1 calc R U . . .
C12 C 0.64598(16) 0.45989(9) 0.61944(8) 0.02092(18) Uani 1 1 d . . . . .
H12 H 0.594659 0.438253 0.561549 0.025 Uiso 1 1 calc R U . . .
C13 C 0.67314(14) 0.56966(9) 0.63774(7) 0.01847(15) Uani 1 1 d . . . . .
H13 H 0.637307 0.621185 0.592791 0.022 Uiso 1 1 calc R U . . .
N1 N 0.73645(13) 0.89742(7) 0.69947(7) 0.02017(15) Uani 1 1 d . . . . .
N2 N 0.82272(15) 0.33671(8) 0.84410(7) 0.02273(17) Uani 1 1 d . . . . .
O1 O 0.69937(12) 0.78393(6) 0.68274(6) 0.02145(15) Uani 1 1 d . . . . .
O2 O 0.88496(16) 0.74959(8) 0.80961(7) 0.0315(2) Uani 1 1 d . . . . .
O3 O 0.89767(16) 0.36794(9) 0.91740(6) 0.02981(19) Uani 1 1 d . . . . .
O4 O 0.7840(2) 0.24178(9) 0.82860(8) 0.0429(3) Uani 1 1 d . . . . .
O5 O 0.83691(11) 1.09939(7) 0.55601(6) 0.01967(13) Uani 1 1 d . . . . .
O6 O 0.55966(12) 1.13367(7) 0.62037(6) 0.02321(15) 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 O5 1.4056(13) . ?
C1 O6 1.4206(14) . ?
C1 C2 1.5147(14) . ?
C1 H1 0.9800 . ?
C2 N1 1.2753(13) . ?
C2 C3 1.4998(14) . ?
C3 C4 1.5352(16) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.5187(16) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O5 1.4472(13) . ?
C5 C6 1.5187(17) . ?
C5 H5 0.9800 . ?
C6 O6 1.4496(15) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O2 1.1996(14) . ?
C7 O1 1.3563(13) . ?
C7 C8 1.4860(14) . ?
C8 C9 1.3920(13) . ?
C8 C13 1.3921(13) . ?
C9 C10 1.3816(14) . ?
C9 H9 0.9300 . ?
C10 C11 1.3867(14) . ?
C10 N2 1.4657(14) . ?
C11 C12 1.3877(15) . ?
C11 H11 0.9300 . ?
C12 C13 1.3898(15) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
N1 O1 1.4425(12) . ?
N2 O4 1.2222(15) . ?
N2 O3 1.2228(15) . ?

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
O5 C1 O6 105.99(8) . . ?
O5 C1 C2 107.36(8) . . ?
O6 C1 C2 110.02(9) . . ?
O5 C1 H1 111.1 . . ?
O6 C1 H1 111.1 . . ?
C2 C1 H1 111.1 . . ?
N1 C2 C3 130.36(10) . . ?
N1 C2 C1 114.58(9) . . ?
C3 C2 C1 115.01(9) . . ?
C2 C3 C4 110.52(9) . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C3 111.65(9) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
O5 C5 C6 100.98(8) . . ?
O5 C5 C4 108.88(9) . . ?
C6 C5 C4 113.89(10) . . ?
O5 C5 H5 110.9 . . ?
C6 C5 H5 110.9 . . ?
C4 C5 H5 110.9 . . ?
O6 C6 C5 103.78(9) . . ?
O6 C6 H6A 111.0 . . ?
C5 C6 H6A 111.0 . . ?
O6 C6 H6B 111.0 . . ?
C5 C6 H6B 111.0 . . ?
H6A C6 H6B 109.0 . . ?
O2 C7 O1 125.26(10) . . ?
O2 C7 C8 124.14(10) . . ?
O1 C7 C8 110.59(8) . . ?
C9 C8 C13 120.28(9) . . ?
C9 C8 C7 117.51(9) . . ?
C13 C8 C7 122.21(9) . . ?
C10 C9 C8 118.08(9) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C9 C10 C11 123.01(9) . . ?
C9 C10 N2 118.52(9) . . ?
C11 C10 N2 118.46(9) . . ?
C10 C11 C12 117.97(10) . . ?
C10 C11 H11 121.0 . . ?
C12 C11 H11 121.0 . . ?
C11 C12 C13 120.54(9) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 120.09(9) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C2 N1 O1 109.29(8) . . ?
O4 N2 O3 123.57(11) . . ?
O4 N2 C10 118.19(11) . . ?
O3 N2 C10 118.24(10) . . ?
C7 O1 N1 112.22(8) . . ?
C1 O5 C5 102.10(8) . . ?
C1 O6 C6 106.44(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
O5 C1 C2 N1 119.15(10) . . . . ?
O6 C1 C2 N1 -125.94(10) . . . . ?
O5 C1 C2 C3 -58.40(11) . . . . ?
O6 C1 C2 C3 56.51(12) . . . . ?
N1 C2 C3 C4 -139.38(12) . . . . ?
C1 C2 C3 C4 37.70(13) . . . . ?
C2 C3 C4 C5 -36.93(13) . . . . ?
C3 C4 C5 O5 57.50(12) . . . . ?
C3 C4 C5 C6 -54.32(12) . . . . ?
O5 C5 C6 O6 -29.43(11) . . . . ?
C4 C5 C6 O6 87.08(11) . . . . ?
O2 C7 C8 C9 13.01(16) . . . . ?
O1 C7 C8 C9 -168.31(9) . . . . ?
O2 C7 C8 C13 -166.42(12) . . . . ?
O1 C7 C8 C13 12.26(14) . . . . ?
C13 C8 C9 C10 -1.08(15) . . . . ?
C7 C8 C9 C10 179.47(9) . . . . ?
C8 C9 C10 C11 1.38(16) . . . . ?
C8 C9 C10 N2 -177.50(9) . . . . ?
C9 C10 C11 C12 -0.21(16) . . . . ?
N2 C10 C11 C12 178.67(10) . . . . ?
C10 C11 C12 C13 -1.26(17) . . . . ?
C11 C12 C13 C8 1.54(17) . . . . ?
C9 C8 C13 C12 -0.34(16) . . . . ?
C7 C8 C13 C12 179.08(10) . . . . ?
C3 C2 N1 O1 0.29(16) . . . . ?
C1 C2 N1 O1 -176.80(9) . . . . ?
C9 C10 N2 O4 175.93(12) . . . . ?
C11 C10 N2 O4 -3.01(17) . . . . ?
C9 C10 N2 O3 -3.19(15) . . . . ?
C11 C10 N2 O3 177.88(11) . . . . ?
O2 C7 O1 N1 1.35(16) . . . . ?
C8 C7 O1 N1 -177.31(8) . . . . ?
C2 N1 O1 C7 166.34(9) . . . . ?
O6 C1 O5 C5 -43.08(10) . . . . ?
C2 C1 O5 C5 74.48(10) . . . . ?
C6 C5 O5 C1 43.92(10) . . . . ?
C4 C5 O5 C1 -76.24(10) . . . . ?
O5 C1 O6 C6 23.68(11) . . . . ?
C2 C1 O6 C6 -92.09(10) . . . . ?
C5 C6 O6 C1 4.32(12) . . . . ?

_refine_diff_density_max         0.417
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_cmpd6
_database_code_depnum_ccdc_archive 'CCDC 1578349'
_audit_update_record             
;
2017-10-06 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H12 N2 O6'
_chemical_formula_weight         292.25
_chemical_oxdiff_usercomment     'sjw am  AM-1-25'

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   11.6567(5)
_cell_length_b                   12.4748(5)
_cell_length_c                   17.6511(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.457(4)
_cell_angle_gamma                90
_cell_volume                     2538.82(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    130.00(10)
_cell_measurement_reflns_used    4657
_cell_measurement_theta_min      3.5260
_cell_measurement_theta_max      33.2080

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.438
_exptl_crystal_size_mid          0.372
_exptl_crystal_size_min          0.037
_exptl_absorpt_coefficient_mu    0.123
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.30859
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.492
_oxdiff_exptl_absorpt_empirical_full_max 2.450
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      130.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_reflns_number            23391
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.266
_diffrn_reflns_theta_max         29.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.825
_diffrn_reflns_point_group_measured_fraction_full 0.872
_reflns_number_total             12230
_reflns_number_gt                9425
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.588
_reflns_Friedel_fraction_max     0.638
_reflns_Friedel_fraction_full    0.736

_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    shelxt
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0523P)²] 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_abs_structure_details 
;
 Flack x determined using 2589 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(6)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         12230
_refine_ls_number_parameters     757
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1240
_refine_ls_wR_factor_gt          0.1125
_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_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 0.7463(3) 0.5042(3) 0.82806(16) 0.0221(7) Uani 1 1 d . . . . .
H1 H 0.730372 0.427078 0.824019 0.027 Uiso 1 1 calc R U . . .
C1A C 0.2580(3) 0.4873(3) 0.83798(16) 0.0227(7) Uani 1 1 d . . . . .
H1A H 0.250093 0.565384 0.833752 0.027 Uiso 1 1 calc R U . . .
C1B C 0.3926(3) 0.7021(3) 0.55741(18) 0.0280(8) Uani 1 1 d . . . . .
H1B H 0.374870 0.768652 0.528510 0.034 Uiso 1 1 calc R U . . .
C1C C 0.9033(3) 0.2969(3) 0.56784(18) 0.0284(8) Uani 1 1 d . . . . .
H1C H 0.898949 0.223472 0.547973 0.034 Uiso 1 1 calc R U . . .
C2 C 0.6784(3) 0.5562(3) 0.88516(16) 0.0197(6) Uani 1 1 d . . . . .
C2A C 0.1793(3) 0.4418(3) 0.89062(18) 0.0220(7) Uani 1 1 d . . . . .
C2B C 0.4909(3) 0.6421(3) 0.52930(17) 0.0221(7) Uani 1 1 d . . . . .
C2C C 0.9874(3) 0.3635(3) 0.53037(17) 0.0236(7) Uani 1 1 d . . . . .
C3 C 0.6848(3) 0.6760(3) 0.89079(19) 0.0289(8) Uani 1 1 d . . . . .
H3A H 0.748520 0.696176 0.929952 0.035 Uiso 1 1 calc R U . . .
H3B H 0.613662 0.703252 0.905960 0.035 Uiso 1 1 calc R U . . .
C3A C 0.1821(3) 0.3215(3) 0.8974(2) 0.0262(7) Uani 1 1 d . . . . .
H3A1 H 0.134930 0.289808 0.853219 0.031 Uiso 1 1 calc R U . . .
H3A2 H 0.150581 0.299711 0.942939 0.031 Uiso 1 1 calc R U . . .
C3B C 0.5216(3) 0.5372(3) 0.56839(18) 0.0281(7) Uani 1 1 d . . . . .
H3B1 H 0.575611 0.549593 0.614851 0.034 Uiso 1 1 calc R U . . .
H3B2 H 0.559560 0.491662 0.535067 0.034 Uiso 1 1 calc R U . . .
C3C C 0.9959(3) 0.4782(3) 0.55578(17) 0.0270(7) Uani 1 1 d . . . . .
H3C1 H 0.932065 0.518760 0.528198 0.032 Uiso 1 1 calc R U . . .
H3C2 H 1.067816 0.508900 0.544171 0.032 Uiso 1 1 calc R U . . .
C4 C 0.7029(3) 0.7273(3) 0.81374(18) 0.0332(8) Uani 1 1 d . . . . .
H4A H 0.628073 0.738692 0.782707 0.040 Uiso 1 1 calc R U . . .
H4B H 0.740010 0.796531 0.823305 0.040 Uiso 1 1 calc R U . . .
C4A C 0.3080(3) 0.2824(2) 0.90231(17) 0.0248(6) Uani 1 1 d . . . . .
H4A1 H 0.346841 0.290222 0.954509 0.030 Uiso 1 1 calc R U . . .
H4A2 H 0.308169 0.206958 0.889108 0.030 Uiso 1 1 calc R U . . .
C4B C 0.4140(3) 0.4803(3) 0.58840(19) 0.0343(8) Uani 1 1 d . . . . .
H4B1 H 0.377068 0.440877 0.544059 0.041 Uiso 1 1 calc R U . . .
H4B2 H 0.436919 0.429316 0.629305 0.041 Uiso 1 1 calc R U . . .
C4C C 0.9924(3) 0.4859(3) 0.64241(16) 0.0290(7) Uani 1 1 d . . . . .
H4C1 H 1.069401 0.472702 0.670001 0.035 Uiso 1 1 calc R U . . .
H4C2 H 0.969527 0.557776 0.654821 0.035 Uiso 1 1 calc R U . . .
C5 C 0.7767(3) 0.6574(3) 0.77031(17) 0.0279(7) Uani 1 1 d . . . . .
H5 H 0.788821 0.691190 0.722018 0.033 Uiso 1 1 calc R U . . .
C5A C 0.3740(3) 0.3450(3) 0.84886(17) 0.0243(6) Uani 1 1 d . . . . .
H5A H 0.453594 0.318416 0.851430 0.029 Uiso 1 1 calc R U . . .
C5B C 0.3285(3) 0.5591(3) 0.61330(18) 0.0333(8) Uani 1 1 d . . . . .
H5B H 0.260429 0.521828 0.626942 0.040 Uiso 1 1 calc R U . . .
C5C C 0.9083(3) 0.4059(3) 0.66805(17) 0.0315(8) Uani 1 1 d . . . . .
H5C H 0.906299 0.411644 0.723208 0.038 Uiso 1 1 calc R U . . .
C6 C 0.8914(3) 0.6239(3) 0.81671(18) 0.0305(7) Uani 1 1 d . . . . .
H6A H 0.950372 0.613962 0.783834 0.037 Uiso 1 1 calc R U . . .
H6B H 0.918231 0.677103 0.855337 0.037 Uiso 1 1 calc R U . . .
C6A C 0.3127(3) 0.3470(3) 0.76710(18) 0.0332(8) Uani 1 1 d . . . . .
H6A1 H 0.367681 0.356607 0.731419 0.040 Uiso 1 1 calc R U . . .
H6A2 H 0.269957 0.281024 0.754647 0.040 Uiso 1 1 calc R U . . .
C6B C 0.3797(3) 0.6341(3) 0.67687(18) 0.0336(8) Uani 1 1 d . . . . .
H6B1 H 0.320808 0.657897 0.706643 0.040 Uiso 1 1 calc R U . . .
H6B2 H 0.441725 0.599442 0.710750 0.040 Uiso 1 1 calc R U . . .
C6C C 0.7876(3) 0.4142(3) 0.62309(18) 0.0317(8) Uani 1 1 d . . . . .
H6C1 H 0.729785 0.388647 0.653066 0.038 Uiso 1 1 calc R U . . .
H6C2 H 0.769615 0.487702 0.607671 0.038 Uiso 1 1 calc R U . . .
C7 C 0.5052(3) 0.4804(3) 1.01583(15) 0.0177(6) Uani 1 1 d . . . . .
C7A C -0.0075(3) 0.5264(3) 1.00967(17) 0.0224(7) Uani 1 1 d . . . . .
C7B C 0.7012(3) 0.6640(3) 0.41433(16) 0.0211(7) Uani 1 1 d . . . . .
C7C C 1.1977(3) 0.3392(3) 0.41590(16) 0.0255(7) Uani 1 1 d . . . . .
C8 C 0.4185(3) 0.5403(3) 1.05371(15) 0.0193(6) Uani 1 1 d . . . . .
C8A C -0.0874(3) 0.4655(3) 1.05290(16) 0.0203(7) Uani 1 1 d . . . . .
C8B C 0.7710(3) 0.5781(3) 0.38249(16) 0.0206(6) Uani 1 1 d . . . . .
C8C C 1.2647(3) 0.4237(3) 0.38186(16) 0.0243(7) Uani 1 1 d . . . . .
C9 C 0.4005(3) 0.6504(3) 1.04530(15) 0.0196(6) Uani 1 1 d . . . . .
H9 H 0.446293 0.690824 1.017089 0.024 Uiso 1 1 calc R U . . .
C9A C -0.0984(3) 0.3546(3) 1.04855(17) 0.0217(7) Uani 1 1 d . . . . .
H9A H -0.050779 0.315051 1.021083 0.026 Uiso 1 1 calc R U . . .
C9B C 0.8613(3) 0.6100(3) 0.34428(17) 0.0236(7) Uani 1 1 d . . . . .
H9B H 0.879220 0.682368 0.341105 0.028 Uiso 1 1 calc R U . . .
C9C C 1.2305(3) 0.5309(3) 0.37816(18) 0.0295(8) Uani 1 1 d . . . . .
H9C H 1.164914 0.551360 0.398900 0.035 Uiso 1 1 calc R U . . .
C10 C 0.3140(3) 0.6996(3) 1.07919(16) 0.0214(6) Uani 1 1 d . . . . .
H10 H 0.302101 0.773236 1.075094 0.026 Uiso 1 1 calc R U . . .
C10A C -0.1805(3) 0.3026(3) 1.08524(17) 0.0220(7) Uani 1 1 d . . . . .
H10A H -0.188503 0.228403 1.082989 0.026 Uiso 1 1 calc R U . . .
C10B C 0.9248(3) 0.5338(3) 0.31082(17) 0.0252(7) Uani 1 1 d . . . . .
H10B H 0.985812 0.553869 0.285368 0.030 Uiso 1 1 calc R U . . .
C10C C 1.2922(3) 0.6075(3) 0.34419(18) 0.0297(8) Uani 1 1 d . . . . .
H10C H 1.268986 0.678913 0.341323 0.036 Uiso 1 1 calc R U . . .
C11 C 0.2459(3) 0.6366(3) 1.11916(16) 0.0200(6) Uani 1 1 d . . . . .
C11A C -0.2500(3) 0.3648(3) 1.12530(16) 0.0206(6) Uani 1 1 d . . . . .
C11B C 0.8947(3) 0.4274(3) 0.31639(17) 0.0249(7) Uani 1 1 d . . . . .
C11C C 1.3899(3) 0.5739(3) 0.31462(17) 0.0267(7) Uani 1 1 d . . . . .
C12 C 0.2631(3) 0.5277(3) 1.12939(17) 0.0256(7) Uani 1 1 d . . . . .
H12 H 0.217122 0.487713 1.157725 0.031 Uiso 1 1 calc R U . . .
C12A C -0.2373(3) 0.4745(3) 1.13281(17) 0.0239(7) Uani 1 1 d . . . . .
H12A H -0.283114 0.513756 1.161686 0.029 Uiso 1 1 calc R U . . .
C12B C 0.8065(3) 0.3942(3) 0.35503(17) 0.0266(7) Uani 1 1 d . . . . .
H12B H 0.789507 0.321768 0.358814 0.032 Uiso 1 1 calc R U . . .
C12C C 1.4272(3) 0.4688(3) 0.31800(18) 0.0298(8) Uani 1 1 d . . . . .
H12C H 1.493373 0.449015 0.297775 0.036 Uiso 1 1 calc R U . . .
C13 C 0.3505(3) 0.4800(3) 1.09630(17) 0.0234(7) Uani 1 1 d . . . . .
H13 H 0.364066 0.406806 1.102561 0.028 Uiso 1 1 calc R U . . .
C13A C -0.1548(3) 0.5244(3) 1.09631(17) 0.0243(7) Uani 1 1 d . . . . .
H13A H -0.144357 0.598172 1.100927 0.029 Uiso 1 1 calc R U . . .
C13B C 0.7442(3) 0.4704(3) 0.38788(17) 0.0243(7) Uani 1 1 d . . . . .
H13B H 0.683926 0.449617 0.413776 0.029 Uiso 1 1 calc R U . . .
C13C C 1.3643(3) 0.3937(3) 0.35201(16) 0.0269(7) Uani 1 1 d . . . . .
H13C H 1.388570 0.322600 0.355032 0.032 Uiso 1 1 calc R U . . .
N1 N 0.6268(2) 0.4898(2) 0.92354(13) 0.0200(5) Uani 1 1 d . . . . .
N1A N 0.1255(2) 0.5116(2) 0.92435(15) 0.0252(6) Uani 1 1 d . . . . .
N1B N 0.5376(2) 0.6885(2) 0.47710(15) 0.0248(6) Uani 1 1 d . . . . .
N1C N 1.0411(3) 0.3128(3) 0.48383(16) 0.0302(7) Uani 1 1 d . . . . .
N2 N 0.1496(3) 0.6866(2) 1.15196(15) 0.0252(6) Uani 1 1 d . . . . .
N2A N -0.3436(2) 0.3123(2) 1.15865(14) 0.0252(6) Uani 1 1 d . . . . .
N2B N 0.9589(3) 0.3453(3) 0.27993(15) 0.0306(7) Uani 1 1 d . . . . .
N2C N 1.4551(3) 0.6548(3) 0.27662(15) 0.0339(8) Uani 1 1 d . . . . .
O1 O 0.56433(19) 0.54830(18) 0.97511(11) 0.0209(5) Uani 1 1 d . . . . .
O1A O 0.0580(2) 0.45759(19) 0.97519(12) 0.0242(5) Uani 1 1 d . . . . .
O1B O 0.6236(2) 0.6167(2) 0.45381(12) 0.0251(5) Uani 1 1 d . . . . .
O1C O 1.1173(2) 0.3876(2) 0.45317(12) 0.0298(6) Uani 1 1 d . . . . .
O2 O 0.5206(2) 0.38595(19) 1.02087(11) 0.0228(5) Uani 1 1 d . . . . .
O2A O -0.0028(2) 0.62313(19) 1.00699(13) 0.0273(5) Uani 1 1 d . . . . .
O2B O 0.7130(2) 0.7581(2) 0.40635(13) 0.0281(5) Uani 1 1 d . . . . .
O2C O 1.2118(2) 0.2445(2) 0.41109(12) 0.0310(6) Uani 1 1 d . . . . .
O3 O 0.1329(2) 0.7833(2) 1.14240(15) 0.0360(6) Uani 1 1 d . . . . .
O3A O -0.3961(2) 0.3658(2) 1.20088(13) 0.0379(6) Uani 1 1 d . . . . .
O3B O 0.9217(3) 0.2532(3) 0.27669(16) 0.0476(8) Uani 1 1 d . . . . .
O3C O 1.5442(2) 0.6264(3) 0.25381(15) 0.0423(7) Uani 1 1 d . . . . .
O4 O 0.0900(2) 0.6290(2) 1.18682(14) 0.0352(6) Uani 1 1 d . . . . .
O4A O -0.3660(2) 0.2188(2) 1.14233(13) 0.0308(6) Uani 1 1 d . . . . .
O4B O 1.0452(2) 0.3727(3) 0.25312(14) 0.0411(7) Uani 1 1 d . . . . .
O4C O 1.4156(3) 0.7463(3) 0.26972(16) 0.0456(7) Uani 1 1 d . . . . .
O5 O 0.7183(2) 0.55448(19) 0.75658(11) 0.0266(5) Uani 1 1 d . . . . .
O5A O 0.37258(18) 0.45754(18) 0.86815(12) 0.0230(5) Uani 1 1 d . . . . .
O5B O 0.2952(2) 0.6345(2) 0.55124(13) 0.0356(6) Uani 1 1 d . . . . .
O5C O 0.9409(2) 0.2983(2) 0.64759(12) 0.0334(6) Uani 1 1 d . . . . .
O6 O 0.8654(2) 0.5234(2) 0.85183(12) 0.0271(5) Uani 1 1 d . . . . .
O6A O 0.2349(2) 0.4373(2) 0.76473(12) 0.0335(6) Uani 1 1 d . . . . .
O6B O 0.4235(2) 0.7232(2) 0.63685(12) 0.0320(6) Uani 1 1 d . . . . .
O6C O 0.7923(2) 0.3464(2) 0.55700(13) 0.0321(6) 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 O5 1.404(3) . ?
C1 O6 1.410(4) . ?
C1 C2 1.516(4) . ?
C1 H1 0.9800 . ?
C1A O5A 1.413(4) . ?
C1A O6A 1.425(4) . ?
C1A C2A 1.509(4) . ?
C1A H1A 0.9800 . ?
C1B O5B 1.406(4) . ?
C1B O6B 1.420(4) . ?
C1B C2B 1.513(5) . ?
C1B H1B 0.9800 . ?
C1C O5C 1.412(4) . ?
C1C O6C 1.421(4) . ?
C1C C2C 1.509(5) . ?
C1C H1C 0.9800 . ?
C2 N1 1.275(4) . ?
C2 C3 1.499(5) . ?
C2A N1A 1.271(4) . ?
C2A C3A 1.505(5) . ?
C2B N1B 1.276(4) . ?
C2B C3B 1.497(5) . ?
C2C N1C 1.272(4) . ?
C2C C3C 1.499(5) . ?
C3 C4 1.545(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3A C4A 1.537(4) . ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?
C3B C4B 1.527(5) . ?
C3B H3B1 0.9700 . ?
C3B H3B2 0.9700 . ?
C3C C4C 1.539(4) . ?
C3C H3C1 0.9700 . ?
C3C H3C2 0.9700 . ?
C4 C5 1.510(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4A C5A 1.518(4) . ?
C4A H4A1 0.9700 . ?
C4A H4A2 0.9700 . ?
C4B C5B 1.510(5) . ?
C4B H4B1 0.9700 . ?
C4B H4B2 0.9700 . ?
C4C C5C 1.514(5) . ?
C4C H4C1 0.9700 . ?
C4C H4C2 0.9700 . ?
C5 O5 1.456(4) . ?
C5 C6 1.521(5) . ?
C5 H5 0.9800 . ?
C5A O5A 1.446(4) . ?
C5A C6A 1.514(4) . ?
C5A H5A 0.9800 . ?
C5B O5B 1.453(4) . ?
C5B C6B 1.514(5) . ?
C5B H5B 0.9800 . ?
C5C O5C 1.455(4) . ?
C5C C6C 1.514(5) . ?
C5C H5C 0.9800 . ?
C6 O6 1.450(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6A O6A 1.443(4) . ?
C6A H6A1 0.9700 . ?
C6A H6A2 0.9700 . ?
C6B O6B 1.449(4) . ?
C6B H6B1 0.9700 . ?
C6B H6B2 0.9700 . ?
C6C O6C 1.449(4) . ?
C6C H6C1 0.9700 . ?
C6C H6C2 0.9700 . ?
C7 O2 1.194(4) . ?
C7 O1 1.361(4) . ?
C7 C8 1.493(4) . ?
C7A O2A 1.209(4) . ?
C7A O1A 1.351(4) . ?
C7A C8A 1.495(5) . ?
C7B O2B 1.193(4) . ?
C7B O1B 1.355(4) . ?
C7B C8B 1.503(5) . ?
C7C O2C 1.198(4) . ?
C7C O1C 1.363(4) . ?
C7C C8C 1.490(5) . ?
C8 C13 1.391(4) . ?
C8 C9 1.394(5) . ?
C8A C13A 1.386(4) . ?
C8A C9A 1.391(5) . ?
C8B C13B 1.386(5) . ?
C8B C9B 1.389(4) . ?
C8C C13C 1.395(5) . ?
C8C C9C 1.395(5) . ?
C9 C10 1.389(4) . ?
C9 H9 0.9300 . ?
C9A C10A 1.393(4) . ?
C9A H9A 0.9300 . ?
C9B C10B 1.389(5) . ?
C9B H9B 0.9300 . ?
C9C C10C 1.385(5) . ?
C9C H9C 0.9300 . ?
C10 C11 1.382(4) . ?
C10 H10 0.9300 . ?
C10A C11A 1.388(4) . ?
C10A H10A 0.9300 . ?
C10B C11B 1.379(5) . ?
C10B H10B 0.9300 . ?
C10C C11C 1.385(5) . ?
C10C H10C 0.9300 . ?
C11 C12 1.380(5) . ?
C11 N2 1.476(4) . ?
C11A C12A 1.381(5) . ?
C11A N2A 1.468(4) . ?
C11B C12B 1.378(5) . ?
C11B N2B 1.472(4) . ?
C11C C12C 1.379(5) . ?
C11C N2C 1.483(5) . ?
C12 C13 1.382(5) . ?
C12 H12 0.9300 . ?
C12A C13A 1.383(5) . ?
C12A H12A 0.9300 . ?
C12B C13B 1.375(5) . ?
C12B H12B 0.9300 . ?
C12C C13C 1.380(5) . ?
C12C H12C 0.9300 . ?
C13 H13 0.9300 . ?
C13A H13A 0.9300 . ?
C13B H13B 0.9300 . ?
C13C H13C 0.9300 . ?
N1 O1 1.445(3) . ?
N1A O1A 1.444(3) . ?
N1B O1B 1.448(3) . ?
N1C O1C 1.447(4) . ?
N2 O4 1.226(4) . ?
N2 O3 1.229(4) . ?
N2A O4A 1.221(4) . ?
N2A O3A 1.229(4) . ?
N2B O4B 1.221(4) . ?
N2B O3B 1.226(4) . ?
N2C O3C 1.220(4) . ?
N2C O4C 1.230(4) . ?

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
O5 C1 O6 106.3(2) . . ?
O5 C1 C2 109.3(3) . . ?
O6 C1 C2 108.4(2) . . ?
O5 C1 H1 110.9 . . ?
O6 C1 H1 110.9 . . ?
C2 C1 H1 110.9 . . ?
O5A C1A O6A 105.6(3) . . ?
O5A C1A C2A 107.2(2) . . ?
O6A C1A C2A 110.1(3) . . ?
O5A C1A H1A 111.3 . . ?
O6A C1A H1A 111.3 . . ?
C2A C1A H1A 111.3 . . ?
O5B C1B O6B 105.8(3) . . ?
O5B C1B C2B 108.7(3) . . ?
O6B C1B C2B 108.7(3) . . ?
O5B C1B H1B 111.2 . . ?
O6B C1B H1B 111.2 . . ?
C2B C1B H1B 111.2 . . ?
O5C C1C O6C 105.8(3) . . ?
O5C C1C C2C 107.7(3) . . ?
O6C C1C C2C 109.9(3) . . ?
O5C C1C H1C 111.1 . . ?
O6C C1C H1C 111.1 . . ?
C2C C1C H1C 111.1 . . ?
N1 C2 C3 129.4(3) . . ?
N1 C2 C1 114.1(3) . . ?
C3 C2 C1 116.4(3) . . ?
N1A C2A C3A 130.7(3) . . ?
N1A C2A C1A 114.6(3) . . ?
C3A C2A C1A 114.6(3) . . ?
N1B C2B C3B 129.1(3) . . ?
N1B C2B C1B 115.8(3) . . ?
C3B C2B C1B 115.0(3) . . ?
N1C C2C C3C 130.6(3) . . ?
N1C C2C C1C 115.0(3) . . ?
C3C C2C C1C 114.4(3) . . ?
C2 C3 C4 111.5(3) . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C2A C3A C4A 109.3(3) . . ?
C2A C3A H3A1 109.8 . . ?
C4A C3A H3A1 109.8 . . ?
C2A C3A H3A2 109.8 . . ?
C4A C3A H3A2 109.8 . . ?
H3A1 C3A H3A2 108.3 . . ?
C2B C3B C4B 111.3(3) . . ?
C2B C3B H3B1 109.4 . . ?
C4B C3B H3B1 109.4 . . ?
C2B C3B H3B2 109.4 . . ?
C4B C3B H3B2 109.4 . . ?
H3B1 C3B H3B2 108.0 . . ?
C2C C3C C4C 110.3(3) . . ?
C2C C3C H3C1 109.6 . . ?
C4C C3C H3C1 109.6 . . ?
C2C C3C H3C2 109.6 . . ?
C4C C3C H3C2 109.6 . . ?
H3C1 C3C H3C2 108.1 . . ?
C5 C4 C3 111.7(3) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C5A C4A C3A 111.7(3) . . ?
C5A C4A H4A1 109.3 . . ?
C3A C4A H4A1 109.3 . . ?
C5A C4A H4A2 109.3 . . ?
C3A C4A H4A2 109.3 . . ?
H4A1 C4A H4A2 107.9 . . ?
C5B C4B C3B 111.4(3) . . ?
C5B C4B H4B1 109.4 . . ?
C3B C4B H4B1 109.4 . . ?
C5B C4B H4B2 109.4 . . ?
C3B C4B H4B2 109.4 . . ?
H4B1 C4B H4B2 108.0 . . ?
C5C C4C C3C 111.7(3) . . ?
C5C C4C H4C1 109.3 . . ?
C3C C4C H4C1 109.3 . . ?
C5C C4C H4C2 109.3 . . ?
C3C C4C H4C2 109.3 . . ?
H4C1 C4C H4C2 107.9 . . ?
O5 C5 C4 107.8(3) . . ?
O5 C5 C6 101.6(3) . . ?
C4 C5 C6 114.0(3) . . ?
O5 C5 H5 111.0 . . ?
C4 C5 H5 111.0 . . ?
C6 C5 H5 111.0 . . ?
O5A C5A C6A 100.9(3) . . ?
O5A C5A C4A 109.2(2) . . ?
C6A C5A C4A 112.9(3) . . ?
O5A C5A H5A 111.1 . . ?
C6A C5A H5A 111.1 . . ?
C4A C5A H5A 111.1 . . ?
O5B C5B C4B 108.5(3) . . ?
O5B C5B C6B 101.0(3) . . ?
C4B C5B C6B 114.4(3) . . ?
O5B C5B H5B 110.8 . . ?
C4B C5B H5B 110.8 . . ?
C6B C5B H5B 110.8 . . ?
O5C C5C C6C 101.0(3) . . ?
O5C C5C C4C 109.2(3) . . ?
C6C C5C C4C 113.0(3) . . ?
O5C C5C H5C 111.1 . . ?
C6C C5C H5C 111.1 . . ?
C4C C5C H5C 111.1 . . ?
O6 C6 C5 104.2(3) . . ?
O6 C6 H6A 110.9 . . ?
C5 C6 H6A 110.9 . . ?
O6 C6 H6B 110.9 . . ?
C5 C6 H6B 110.9 . . ?
H6A C6 H6B 108.9 . . ?
O6A C6A C5A 104.3(3) . . ?
O6A C6A H6A1 110.9 . . ?
C5A C6A H6A1 110.9 . . ?
O6A C6A H6A2 110.9 . . ?
C5A C6A H6A2 110.9 . . ?
H6A1 C6A H6A2 108.9 . . ?
O6B C6B C5B 104.0(2) . . ?
O6B C6B H6B1 111.0 . . ?
C5B C6B H6B1 111.0 . . ?
O6B C6B H6B2 111.0 . . ?
C5B C6B H6B2 111.0 . . ?
H6B1 C6B H6B2 109.0 . . ?
O6C C6C C5C 103.9(3) . . ?
O6C C6C H6C1 111.0 . . ?
C5C C6C H6C1 111.0 . . ?
O6C C6C H6C2 111.0 . . ?
C5C C6C H6C2 111.0 . . ?
H6C1 C6C H6C2 109.0 . . ?
O2 C7 O1 124.9(3) . . ?
O2 C7 C8 124.4(3) . . ?
O1 C7 C8 110.7(3) . . ?
O2A C7A O1A 125.8(3) . . ?
O2A C7A C8A 124.2(3) . . ?
O1A C7A C8A 110.1(3) . . ?
O2B C7B O1B 125.8(3) . . ?
O2B C7B C8B 125.4(3) . . ?
O1B C7B C8B 108.8(3) . . ?
O2C C7C O1C 125.7(3) . . ?
O2C C7C C8C 125.7(3) . . ?
O1C C7C C8C 108.7(3) . . ?
C13 C8 C9 120.2(3) . . ?
C13 C8 C7 116.6(3) . . ?
C9 C8 C7 123.1(3) . . ?
C13A C8A C9A 120.2(3) . . ?
C13A C8A C7A 117.3(3) . . ?
C9A C8A C7A 122.4(3) . . ?
C13B C8B C9B 120.4(3) . . ?
C13B C8B C7B 121.7(3) . . ?
C9B C8B C7B 117.9(3) . . ?
C13C C8C C9C 119.2(4) . . ?
C13C C8C C7C 118.6(3) . . ?
C9C C8C C7C 122.2(3) . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C8A C9A C10A 120.1(3) . . ?
C8A C9A H9A 119.9 . . ?
C10A C9A H9A 119.9 . . ?
C8B C9B C10B 120.0(3) . . ?
C8B C9B H9B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C10C C9C C8C 121.2(3) . . ?
C10C C9C H9C 119.4 . . ?
C8C C9C H9C 119.4 . . ?
C11 C10 C9 118.4(3) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C11A C10A C9A 118.0(3) . . ?
C11A C10A H10A 121.0 . . ?
C9A C10A H10A 121.0 . . ?
C11B C10B C9B 118.1(3) . . ?
C11B C10B H10B 120.9 . . ?
C9B C10B H10B 120.9 . . ?
C9C C10C C11C 117.5(4) . . ?
C9C C10C H10C 121.2 . . ?
C11C C10C H10C 121.2 . . ?
C12 C11 C10 122.9(3) . . ?
C12 C11 N2 118.0(3) . . ?
C10 C11 N2 119.1(3) . . ?
C12A C11A C10A 122.7(3) . . ?
C12A C11A N2A 118.6(3) . . ?
C10A C11A N2A 118.6(3) . . ?
C12B C11B C10B 122.7(3) . . ?
C12B C11B N2B 118.1(3) . . ?
C10B C11B N2B 119.2(3) . . ?
C12C C11C C10C 122.9(4) . . ?
C12C C11C N2C 119.1(3) . . ?
C10C C11C N2C 117.9(4) . . ?
C11 C12 C13 118.1(3) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?
C11A C12A C13A 118.3(3) . . ?
C11A C12A H12A 120.8 . . ?
C13A C12A H12A 120.8 . . ?
C13B C12B C11B 118.7(3) . . ?
C13B C12B H12B 120.7 . . ?
C11B C12B H12B 120.7 . . ?
C11C C12C C13C 118.7(3) . . ?
C11C C12C H12C 120.7 . . ?
C13C C12C H12C 120.7 . . ?
C12 C13 C8 120.6(3) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
C12A C13A C8A 120.6(3) . . ?
C12A C13A H13A 119.7 . . ?
C8A C13A H13A 119.7 . . ?
C12B C13B C8B 120.2(3) . . ?
C12B C13B H13B 119.9 . . ?
C8B C13B H13B 119.9 . . ?
C12C C13C C8C 120.5(4) . . ?
C12C C13C H13C 119.8 . . ?
C8C C13C H13C 119.8 . . ?
C2 N1 O1 109.1(3) . . ?
C2A N1A O1A 108.8(3) . . ?
C2B N1B O1B 108.1(3) . . ?
C2C N1C O1C 108.0(3) . . ?
O4 N2 O3 123.7(3) . . ?
O4 N2 C11 117.9(3) . . ?
O3 N2 C11 118.4(3) . . ?
O4A N2A O3A 123.7(3) . . ?
O4A N2A C11A 118.5(3) . . ?
O3A N2A C11A 117.8(3) . . ?
O4B N2B O3B 123.4(3) . . ?
O4B N2B C11B 118.3(3) . . ?
O3B N2B C11B 118.2(3) . . ?
O3C N2C O4C 124.1(4) . . ?
O3C N2C C11C 118.0(4) . . ?
O4C N2C C11C 117.9(3) . . ?
C7 O1 N1 111.1(2) . . ?
C7A O1A N1A 112.3(3) . . ?
C7B O1B N1B 114.8(3) . . ?
C7C O1C N1C 113.5(3) . . ?
C1 O5 C5 101.7(2) . . ?
C1A O5A C5A 102.1(2) . . ?
C1B O5B C5B 101.9(2) . . ?
C1C O5C C5C 101.8(2) . . ?
C1 O6 C6 106.2(2) . . ?
C1A O6A C6A 106.4(2) . . ?
C1B O6B C6B 106.5(3) . . ?
C1C O6C C6C 106.6(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
O5 C1 C2 N1 131.2(3) . . . . ?
O6 C1 C2 N1 -113.4(3) . . . . ?
O5 C1 C2 C3 -51.1(4) . . . . ?
O6 C1 C2 C3 64.3(4) . . . . ?
O5A C1A C2A N1A 116.3(3) . . . . ?
O6A C1A C2A N1A -129.4(3) . . . . ?
O5A C1A C2A C3A -60.8(4) . . . . ?
O6A C1A C2A C3A 53.5(4) . . . . ?
O5B C1B C2B N1B 126.1(3) . . . . ?
O6B C1B C2B N1B -119.2(3) . . . . ?
O5B C1B C2B C3B -55.4(3) . . . . ?
O6B C1B C2B C3B 59.3(4) . . . . ?
O5C C1C C2C N1C 118.4(3) . . . . ?
O6C C1C C2C N1C -126.8(3) . . . . ?
O5C C1C C2C C3C -60.1(4) . . . . ?
O6C C1C C2C C3C 54.7(3) . . . . ?
N1 C2 C3 C4 -152.9(3) . . . . ?
C1 C2 C3 C4 29.8(4) . . . . ?
N1A C2A C3A C4A -135.3(3) . . . . ?
C1A C2A C3A C4A 41.3(4) . . . . ?
N1B C2B C3B C4B -146.2(3) . . . . ?
C1B C2B C3B C4B 35.5(4) . . . . ?
N1C C2C C3C C4C -138.7(3) . . . . ?
C1C C2C C3C C4C 39.6(4) . . . . ?
C2 C3 C4 C5 -33.9(4) . . . . ?
C2A C3A C4A C5A -39.5(4) . . . . ?
C2B C3B C4B C5B -37.3(4) . . . . ?
C2C C3C C4C C5C -38.2(4) . . . . ?
C3 C4 C5 O5 59.3(4) . . . . ?
C3 C4 C5 C6 -52.7(4) . . . . ?
C3A C4A C5A O5A 58.4(3) . . . . ?
C3A C4A C5A C6A -52.9(4) . . . . ?
C3B C4B C5B O5B 59.1(4) . . . . ?
C3B C4B C5B C6B -52.7(4) . . . . ?
C3C C4C C5C O5C 57.5(3) . . . . ?
C3C C4C C5C C6C -54.1(4) . . . . ?
O5 C5 C6 O6 -24.9(3) . . . . ?
C4 C5 C6 O6 90.8(3) . . . . ?
O5A C5A C6A O6A -29.6(3) . . . . ?
C4A C5A C6A O6A 86.8(3) . . . . ?
O5B C5B C6B O6B -28.7(3) . . . . ?
C4B C5B C6B O6B 87.5(3) . . . . ?
O5C C5C C6C O6C -29.9(3) . . . . ?
C4C C5C C6C O6C 86.7(3) . . . . ?
O2 C7 C8 C13 -1.2(4) . . . . ?
O1 C7 C8 C13 178.9(2) . . . . ?
O2 C7 C8 C9 -178.4(3) . . . . ?
O1 C7 C8 C9 1.8(4) . . . . ?
O2A C7A C8A C13A -4.2(4) . . . . ?
O1A C7A C8A C13A 175.4(3) . . . . ?
O2A C7A C8A C9A 173.5(3) . . . . ?
O1A C7A C8A C9A -6.9(4) . . . . ?
O2B C7B C8B C13B -173.4(3) . . . . ?
O1B C7B C8B C13B 6.9(4) . . . . ?
O2B C7B C8B C9B 3.9(5) . . . . ?
O1B C7B C8B C9B -175.7(3) . . . . ?
O2C C7C C8C C13C -10.8(5) . . . . ?
O1C C7C C8C C13C 169.4(2) . . . . ?
O2C C7C C8C C9C 168.4(3) . . . . ?
O1C C7C C8C C9C -11.4(4) . . . . ?
C13 C8 C9 C10 -0.4(4) . . . . ?
C7 C8 C9 C10 176.7(3) . . . . ?
C13A C8A C9A C10A 2.6(5) . . . . ?
C7A C8A C9A C10A -175.0(3) . . . . ?
C13B C8B C9B C10B 0.4(4) . . . . ?
C7B C8B C9B C10B -177.0(3) . . . . ?
C13C C8C C9C C10C 1.2(5) . . . . ?
C7C C8C C9C C10C -178.0(3) . . . . ?
C8 C9 C10 C11 -1.5(4) . . . . ?
C8A C9A C10A C11A 0.3(4) . . . . ?
C8B C9B C10B C11B 0.5(4) . . . . ?
C8C C9C C10C C11C -0.6(5) . . . . ?
C9 C10 C11 C12 2.6(5) . . . . ?
C9 C10 C11 N2 -176.7(3) . . . . ?
C9A C10A C11A C12A -2.9(4) . . . . ?
C9A C10A C11A N2A 174.8(3) . . . . ?
C9B C10B C11B C12B -1.5(5) . . . . ?
C9B C10B C11B N2B 178.6(3) . . . . ?
C9C C10C C11C C12C -0.2(5) . . . . ?
C9C C10C C11C N2C 178.7(3) . . . . ?
C10 C11 C12 C13 -1.7(5) . . . . ?
N2 C11 C12 C13 177.6(3) . . . . ?
C10A C11A C12A C13A 2.6(5) . . . . ?
N2A C11A C12A C13A -175.2(3) . . . . ?
C10B C11B C12B C13B 1.5(5) . . . . ?
N2B C11B C12B C13B -178.6(3) . . . . ?
C10C C11C C12C C13C 0.3(5) . . . . ?
N2C C11C C12C C13C -178.6(3) . . . . ?
C11 C12 C13 C8 -0.3(5) . . . . ?
C9 C8 C13 C12 1.3(4) . . . . ?
C7 C8 C13 C12 -175.9(3) . . . . ?
C11A C12A C13A C8A 0.5(4) . . . . ?
C9A C8A C13A C12A -3.0(5) . . . . ?
C7A C8A C13A C12A 174.7(3) . . . . ?
C11B C12B C13B C8B -0.6(5) . . . . ?
C9B C8B C13B C12B -0.3(5) . . . . ?
C7B C8B C13B C12B 177.0(3) . . . . ?
C11C C12C C13C C8C 0.4(5) . . . . ?
C9C C8C C13C C12C -1.1(4) . . . . ?
C7C C8C C13C C12C 178.2(3) . . . . ?
C3 C2 N1 O1 3.3(5) . . . . ?
C1 C2 N1 O1 -179.3(2) . . . . ?
C3A C2A N1A O1A -0.9(5) . . . . ?
C1A C2A N1A O1A -177.4(2) . . . . ?
C3B C2B N1B O1B 5.6(4) . . . . ?
C1B C2B N1B O1B -176.1(3) . . . . ?
C3C C2C N1C O1C -1.8(5) . . . . ?
C1C C2C N1C O1C 179.9(2) . . . . ?
C12 C11 N2 O4 0.2(4) . . . . ?
C10 C11 N2 O4 179.6(3) . . . . ?
C12 C11 N2 O3 -179.2(3) . . . . ?
C10 C11 N2 O3 0.2(4) . . . . ?
C12A C11A N2A O4A 169.1(3) . . . . ?
C10A C11A N2A O4A -8.7(4) . . . . ?
C12A C11A N2A O3A -10.0(4) . . . . ?
C10A C11A N2A O3A 172.2(3) . . . . ?
C12B C11B N2B O4B -171.9(3) . . . . ?
C10B C11B N2B O4B 8.0(4) . . . . ?
C12B C11B N2B O3B 9.5(4) . . . . ?
C10B C11B N2B O3B -170.6(3) . . . . ?
C12C C11C N2C O3C -4.5(4) . . . . ?
C10C C11C N2C O3C 176.6(3) . . . . ?
C12C C11C N2C O4C 175.1(3) . . . . ?
C10C C11C N2C O4C -3.8(4) . . . . ?
O2 C7 O1 N1 14.4(4) . . . . ?
C8 C7 O1 N1 -165.7(2) . . . . ?
C2 N1 O1 C7 178.3(2) . . . . ?
O2A C7A O1A N1A -8.2(4) . . . . ?
C8A C7A O1A N1A 172.2(2) . . . . ?
C2A N1A O1A C7A -176.1(3) . . . . ?
O2B C7B O1B N1B 10.1(4) . . . . ?
C8B C7B O1B N1B -170.3(2) . . . . ?
C2B N1B O1B C7B -163.2(3) . . . . ?
O2C C7C O1C N1C -4.1(4) . . . . ?
C8C C7C O1C N1C 175.7(2) . . . . ?
C2C N1C O1C C7C 166.4(3) . . . . ?
O6 C1 O5 C5 -44.4(3) . . . . ?
C2 C1 O5 C5 72.5(3) . . . . ?
C4 C5 O5 C1 -78.5(3) . . . . ?
C6 C5 O5 C1 41.6(3) . . . . ?
O6A C1A O5A C5A -43.1(3) . . . . ?
C2A C1A O5A C5A 74.2(3) . . . . ?
C6A C5A O5A C1A 44.0(3) . . . . ?
C4A C5A O5A C1A -75.1(3) . . . . ?
O6B C1B O5B C5B -43.6(3) . . . . ?
C2B C1B O5B C5B 73.0(3) . . . . ?
C4B C5B O5B C1B -76.7(3) . . . . ?
C6B C5B O5B C1B 43.8(3) . . . . ?
O6C C1C O5C C5C -43.0(3) . . . . ?
C2C C1C O5C C5C 74.4(3) . . . . ?
C6C C5C O5C C1C 44.2(3) . . . . ?
C4C C5C O5C C1C -75.1(3) . . . . ?
O5 C1 O6 C6 28.1(3) . . . . ?
C2 C1 O6 C6 -89.3(3) . . . . ?
C5 C6 O6 C1 -1.0(3) . . . . ?
O5A C1A O6A C6A 23.6(3) . . . . ?
C2A C1A O6A C6A -91.7(3) . . . . ?
C5A C6A O6A C1A 4.3(3) . . . . ?
O5B C1B O6B C6B 24.8(3) . . . . ?
C2B C1B O6B C6B -91.7(3) . . . . ?
C5B C6B O6B C1B 3.3(4) . . . . ?
O5C C1C O6C C6C 23.6(4) . . . . ?
C2C C1C O6C C6C -92.4(3) . . . . ?
C5C C6C O6C C1C 4.7(4) . . . . ?

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_cmpd3
_database_code_depnum_ccdc_archive 'CCDC 1578345'
_audit_update_record             
;
2017-10-06 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H13 N O3'
_chemical_formula_weight         219.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   5.94890(10)
_cell_length_b                   8.10590(10)
_cell_length_c                   22.3033(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1075.49(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    130.0(1)
_cell_measurement_reflns_used    5653
_cell_measurement_theta_min      3.9480
_cell_measurement_theta_max      76.8700

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.377
_exptl_crystal_size_mid          0.292
_exptl_crystal_size_min          0.133
_exptl_absorpt_coefficient_mu    0.808
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.85896
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.677
_oxdiff_exptl_absorpt_empirical_full_max 1.247
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      130.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_reflns_number            8000
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.964
_diffrn_reflns_theta_max         76.758
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2254
_reflns_number_gt                2239
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.673
_reflns_Friedel_fraction_max     0.984
_reflns_Friedel_fraction_full    1.000

_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0414P)²+0.2029P] 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_abs_structure_details 
;
 Flack x determined using 897 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2254
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0716
_refine_ls_wR_factor_gt          0.0715
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_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 0.1688(2) 0.45728(18) 0.66664(7) 0.0212(3) Uani 1 1 d . . . . .
H1 H 0.061944 0.540562 0.649831 0.025 Uiso 1 1 calc R U . . .
C2 C 0.4077(2) 0.50019(18) 0.65076(7) 0.0209(3) Uani 1 1 d . . . . .
C3 C 0.5836(3) 0.3747(2) 0.66617(9) 0.0302(4) Uani 1 1 d . . . . .
H3A H 0.648108 0.401400 0.705926 0.036 Uiso 1 1 calc R U . . .
H3B H 0.706419 0.380696 0.636284 0.036 Uiso 1 1 calc R U . . .
C4 C 0.4893(3) 0.1978(2) 0.66750(8) 0.0298(4) Uani 1 1 d . . . . .
H4A H 0.504996 0.147711 0.627231 0.036 Uiso 1 1 calc R U . . .
H4B H 0.577905 0.130671 0.696064 0.036 Uiso 1 1 calc R U . . .
C5 C 0.2434(3) 0.19497(19) 0.68593(7) 0.0266(3) Uani 1 1 d . . . . .
H5 H 0.183393 0.079750 0.685457 0.032 Uiso 1 1 calc R U . . .
C6 C 0.1949(4) 0.2784(2) 0.74600(8) 0.0345(4) Uani 1 1 d . . . . .
H6A H 0.063501 0.227308 0.765931 0.041 Uiso 1 1 calc R U . . .
H6B H 0.326434 0.270961 0.773045 0.041 Uiso 1 1 calc R U . . .
C7 C 0.6866(3) 0.81298(18) 0.57861(6) 0.0207(3) Uani 1 1 d . . . . .
C8 C 0.8921(3) 0.89231(19) 0.58348(7) 0.0240(3) Uani 1 1 d . . . . .
H8 H 1.001285 0.855387 0.611512 0.029 Uiso 1 1 calc R U . . .
C9 C 0.9357(3) 1.0268(2) 0.54663(8) 0.0272(3) Uani 1 1 d . . . . .
H9 H 1.075575 1.082797 0.549585 0.033 Uiso 1 1 calc R U . . .
C10 C 0.7762(3) 1.0799(2) 0.50557(7) 0.0273(3) Uani 1 1 d . . . . .
H10 H 0.806822 1.171826 0.480462 0.033 Uiso 1 1 calc R U . . .
C11 C 0.5720(3) 0.99843(19) 0.50125(7) 0.0258(3) Uani 1 1 d . . . . .
H11 H 0.463169 1.034990 0.473065 0.031 Uiso 1 1 calc R U . . .
C12 C 0.5248(3) 0.86344(19) 0.53784(7) 0.0224(3) Uani 1 1 d . . . . .
H12 H 0.384969 0.807359 0.534900 0.027 Uiso 1 1 calc R U . . .
N1 N 0.4312(2) 0.64178(17) 0.62658(6) 0.0219(3) Uani 1 1 d . . . . .
O5 O 0.11922(19) 0.29888(13) 0.64504(5) 0.0249(2) Uani 1 1 d . . . . .
O6 O 0.1486(2) 0.44787(14) 0.73021(5) 0.0282(3) Uani 1 1 d . . . . .
O1 O 0.66264(18) 0.67402(14) 0.61465(5) 0.0239(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 O5 1.4027(17) . ?
C1 O6 1.4250(18) . ?
C1 C2 1.506(2) . ?
C1 H1 1.0000 . ?
C2 N1 1.276(2) . ?
C2 C3 1.499(2) . ?
C3 C4 1.540(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.519(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 O5 1.4448(19) . ?
C5 C6 1.529(2) . ?
C5 H5 1.0000 . ?
C6 O6 1.444(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.386(2) . ?
C7 C12 1.386(2) . ?
C7 O1 1.3911(17) . ?
C8 C9 1.390(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.394(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
N1 O1 1.4266(16) . ?

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
O5 C1 O6 105.97(12) . . ?
O5 C1 C2 109.21(12) . . ?
O6 C1 C2 109.00(12) . . ?
O5 C1 H1 110.8 . . ?
O6 C1 H1 110.8 . . ?
C2 C1 H1 110.8 . . ?
N1 C2 C3 129.11(14) . . ?
N1 C2 C1 114.24(13) . . ?
C3 C2 C1 116.64(13) . . ?
C2 C3 C4 112.43(13) . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C3 111.72(13) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
O5 C5 C4 108.22(13) . . ?
O5 C5 C6 101.45(13) . . ?
C4 C5 C6 114.36(15) . . ?
O5 C5 H5 110.8 . . ?
C4 C5 H5 110.8 . . ?
C6 C5 H5 110.8 . . ?
O6 C6 C5 104.07(13) . . ?
O6 C6 H6A 110.9 . . ?
C5 C6 H6A 110.9 . . ?
O6 C6 H6B 110.9 . . ?
C5 C6 H6B 110.9 . . ?
H6A C6 H6B 109.0 . . ?
C8 C7 C12 121.82(14) . . ?
C8 C7 O1 114.89(13) . . ?
C12 C7 O1 123.16(14) . . ?
C7 C8 C9 118.85(14) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C10 C9 C8 120.38(15) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 119.86(15) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.68(15) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C7 C12 C11 118.41(14) . . ?
C7 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C2 N1 O1 110.44(12) . . ?
C1 O5 C5 102.09(11) . . ?
C1 O6 C6 106.11(12) . . ?
C7 O1 N1 110.79(11) . . ?

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
O5 C1 C2 N1 131.12(13) . . . . ?
O6 C1 C2 N1 -113.53(14) . . . . ?
O5 C1 C2 C3 -49.95(17) . . . . ?
O6 C1 C2 C3 65.40(17) . . . . ?
N1 C2 C3 C4 -154.04(16) . . . . ?
C1 C2 C3 C4 27.2(2) . . . . ?
C2 C3 C4 C5 -30.4(2) . . . . ?
C3 C4 C5 O5 56.72(17) . . . . ?
C3 C4 C5 C6 -55.52(19) . . . . ?
O5 C5 C6 O6 -26.06(17) . . . . ?
C4 C5 C6 O6 90.17(18) . . . . ?
C12 C7 C8 C9 0.4(2) . . . . ?
O1 C7 C8 C9 176.40(13) . . . . ?
C7 C8 C9 C10 -0.3(2) . . . . ?
C8 C9 C10 C11 0.1(2) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
C8 C7 C12 C11 -0.3(2) . . . . ?
O1 C7 C12 C11 -175.96(13) . . . . ?
C10 C11 C12 C7 0.1(2) . . . . ?
C3 C2 N1 O1 -0.4(2) . . . . ?
C1 C2 N1 O1 178.35(12) . . . . ?
O6 C1 O5 C5 -44.20(15) . . . . ?
C2 C1 O5 C5 73.09(14) . . . . ?
C4 C5 O5 C1 -78.28(15) . . . . ?
C6 C5 O5 C1 42.36(15) . . . . ?
O5 C1 O6 C6 26.98(17) . . . . ?
C2 C1 O6 C6 -90.44(15) . . . . ?
C5 C6 O6 C1 0.28(18) . . . . ?
C8 C7 O1 N1 155.66(13) . . . . ?
C12 C7 O1 N1 -28.45(18) . . . . ?
C2 N1 O1 C7 169.00(12) . . . . ?

_refine_diff_density_max         0.172
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_cmpd4
_database_code_depnum_ccdc_archive 'CCDC 1578346'
_audit_update_record             
;
2017-10-06 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 N2 O5'
_chemical_formula_weight         264.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   6.7738(2)
_cell_length_b                   11.4773(3)
_cell_length_c                   14.8982(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1158.26(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    130.00(10)
_cell_measurement_reflns_used    3192
_cell_measurement_theta_min      4.8530
_cell_measurement_theta_max      76.1760

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.407
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.071
_exptl_absorpt_coefficient_mu    1.020
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.77639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.684
_oxdiff_exptl_absorpt_empirical_full_max 1.232
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      130.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6221
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.864
_diffrn_reflns_theta_max         76.976
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             2287
_reflns_number_gt                2133
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.606
_reflns_Friedel_fraction_max     0.845
_reflns_Friedel_fraction_full    0.925

_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    shelxt
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0478P)²+0.0277P] 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_abs_structure_details 
;
 Flack x determined using 781 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.17(14)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2287
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0795
_refine_ls_wR_factor_gt          0.0759
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 0.6069(3) 0.32553(17) 0.69337(12) 0.0237(4) Uani 1 1 d . . . . .
H1 H 0.682425 0.389033 0.723910 0.028 Uiso 1 1 calc R U . . .
C2 C 0.5177(3) 0.36800(15) 0.60622(12) 0.0195(4) Uani 1 1 d . . . . .
C3 C 0.3965(3) 0.28010(16) 0.55605(12) 0.0208(4) Uani 1 1 d . . . . .
H3A H 0.483949 0.231930 0.517891 0.025 Uiso 1 1 calc R U . . .
H3B H 0.301599 0.320887 0.516449 0.025 Uiso 1 1 calc R U . . .
C4 C 0.2832(3) 0.20105(17) 0.62170(14) 0.0250(4) Uani 1 1 d . . . . .
H4A H 0.159359 0.240131 0.640056 0.030 Uiso 1 1 calc R U . . .
H4B H 0.247801 0.127432 0.591053 0.030 Uiso 1 1 calc R U . . .
C5 C 0.4055(3) 0.17375(17) 0.70459(13) 0.0252(4) Uani 1 1 d . . . . .
H5 H 0.332159 0.120815 0.746182 0.030 Uiso 1 1 calc R U . . .
C6 C 0.6105(3) 0.12570(17) 0.68386(14) 0.0271(4) Uani 1 1 d . . . . .
H6A H 0.659183 0.076370 0.733674 0.032 Uiso 1 1 calc R U . . .
H6B H 0.609320 0.079153 0.627914 0.032 Uiso 1 1 calc R U . . .
C7 C 0.4928(3) 0.61437(15) 0.47658(11) 0.0182(3) Uani 1 1 d . . . . .
C8 C 0.4991(3) 0.70215(15) 0.54084(11) 0.0195(3) Uani 1 1 d . . . . .
H8 H 0.500439 0.683545 0.602975 0.023 Uiso 1 1 calc R U . . .
C9 C 0.5033(3) 0.81692(15) 0.51281(12) 0.0198(3) Uani 1 1 d . . . . .
H9 H 0.507565 0.878445 0.555429 0.024 Uiso 1 1 calc R U . . .
C10 C 0.5013(3) 0.84103(14) 0.42149(12) 0.0191(3) Uani 1 1 d . . . . .
C11 C 0.4961(3) 0.75404(15) 0.35732(11) 0.0202(4) Uani 1 1 d . . . . .
H11 H 0.496268 0.772898 0.295228 0.024 Uiso 1 1 calc R U . . .
C12 C 0.4907(3) 0.63939(15) 0.38503(12) 0.0203(4) Uani 1 1 d . . . . .
H12 H 0.485522 0.578163 0.342187 0.024 Uiso 1 1 calc R U . . .
N1 N 0.5597(2) 0.47248(14) 0.58470(10) 0.0213(3) Uani 1 1 d . . . . .
N2 N 0.5069(2) 0.96230(13) 0.39276(11) 0.0234(3) Uani 1 1 d . . . . .
O1 O 0.48005(19) 0.49825(10) 0.49756(8) 0.0217(3) Uani 1 1 d . . . . .
O2 O 0.4982(2) 0.98361(12) 0.31145(9) 0.0330(3) Uani 1 1 d . . . . .
O3 O 0.5184(2) 1.03904(12) 0.45022(10) 0.0341(4) Uani 1 1 d . . . . .
O5 O 0.4557(2) 0.28282(12) 0.74882(8) 0.0264(3) Uani 1 1 d . . . . .
O6 O 0.73114(19) 0.22868(12) 0.67371(10) 0.0263(3) 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 O5 1.404(2) . ?
C1 O6 1.425(2) . ?
C1 C2 1.513(2) . ?
C1 H1 1.0000 . ?
C2 N1 1.274(2) . ?
C2 C3 1.500(3) . ?
C3 C4 1.539(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.520(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 O5 1.455(2) . ?
C5 C6 1.526(3) . ?
C5 H5 1.0000 . ?
C6 O6 1.445(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O1 1.372(2) . ?
C7 C8 1.390(2) . ?
C7 C12 1.394(2) . ?
C8 C9 1.382(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(2) . ?
C10 N2 1.457(2) . ?
C11 C12 1.380(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
N1 O1 1.4367(19) . ?
N2 O3 1.231(2) . ?
N2 O2 1.237(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 C1 O6 106.24(14) . . ?
O5 C1 C2 109.01(15) . . ?
O6 C1 C2 108.12(15) . . ?
O5 C1 H1 111.1 . . ?
O6 C1 H1 111.1 . . ?
C2 C1 H1 111.1 . . ?
N1 C2 C3 129.07(16) . . ?
N1 C2 C1 115.47(16) . . ?
C3 C2 C1 115.44(15) . . ?
C2 C3 C4 110.64(15) . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C3 111.50(15) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
O5 C5 C4 108.53(15) . . ?
O5 C5 C6 100.96(15) . . ?
C4 C5 C6 113.96(17) . . ?
O5 C5 H5 111.0 . . ?
C4 C5 H5 111.0 . . ?
C6 C5 H5 111.0 . . ?
O6 C6 C5 103.90(14) . . ?
O6 C6 H6A 111.0 . . ?
C5 C6 H6A 111.0 . . ?
O6 C6 H6B 111.0 . . ?
C5 C6 H6B 111.0 . . ?
H6A C6 H6B 109.0 . . ?
O1 C7 C8 123.31(15) . . ?
O1 C7 C12 114.99(15) . . ?
C8 C7 C12 121.66(16) . . ?
C9 C8 C7 118.89(16) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 119.06(16) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C11 C10 C9 122.27(16) . . ?
C11 C10 N2 119.17(15) . . ?
C9 C10 N2 118.56(16) . . ?
C12 C11 C10 118.84(15) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C7 119.28(16) . . ?
C11 C12 H12 120.4 . . ?
C7 C12 H12 120.4 . . ?
C2 N1 O1 109.71(14) . . ?
O3 N2 O2 122.86(16) . . ?
O3 N2 C10 118.76(15) . . ?
O2 N2 C10 118.38(15) . . ?
C7 O1 N1 112.47(13) . . ?
C1 O5 C5 101.78(14) . . ?
C1 O6 C6 106.42(14) . . ?

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
O5 C1 C2 N1 125.86(17) . . . . ?
O6 C1 C2 N1 -119.06(18) . . . . ?
O5 C1 C2 C3 -55.7(2) . . . . ?
O6 C1 C2 C3 59.4(2) . . . . ?
N1 C2 C3 C4 -146.31(19) . . . . ?
C1 C2 C3 C4 35.5(2) . . . . ?
C2 C3 C4 C5 -37.2(2) . . . . ?
C3 C4 C5 O5 59.2(2) . . . . ?
C3 C4 C5 C6 -52.5(2) . . . . ?
O5 C5 C6 O6 -28.91(19) . . . . ?
C4 C5 C6 O6 87.22(18) . . . . ?
O1 C7 C8 C9 -177.23(17) . . . . ?
C12 C7 C8 C9 0.0(3) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C8 C9 C10 N2 -179.70(17) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
N2 C10 C11 C12 -179.92(17) . . . . ?
C10 C11 C12 C7 -0.7(3) . . . . ?
O1 C7 C12 C11 177.83(17) . . . . ?
C8 C7 C12 C11 0.4(3) . . . . ?
C3 C2 N1 O1 -3.0(3) . . . . ?
C1 C2 N1 O1 175.15(15) . . . . ?
C11 C10 N2 O3 -177.51(18) . . . . ?
C9 C10 N2 O3 1.9(3) . . . . ?
C11 C10 N2 O2 3.0(3) . . . . ?
C9 C10 N2 O2 -177.54(17) . . . . ?
C8 C7 O1 N1 -26.0(2) . . . . ?
C12 C7 O1 N1 156.65(15) . . . . ?
C2 N1 O1 C7 170.26(16) . . . . ?
O6 C1 O5 C5 -43.33(16) . . . . ?
C2 C1 O5 C5 72.96(17) . . . . ?
C4 C5 O5 C1 -76.46(17) . . . . ?
C6 C5 O5 C1 43.62(17) . . . . ?
O5 C1 O6 C6 24.40(18) . . . . ?
C2 C1 O6 C6 -92.49(18) . . . . ?
C5 C6 O6 C1 3.69(19) . . . . ?

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_cmpd2
_database_code_depnum_ccdc_archive 'CCDC 1578344'
_audit_update_record             
;
2017-10-06 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H14 Br N O3'
_chemical_formula_weight         312.16
_chemical_oxdiff_usercomment     'Amani/SJW AM-1-31 bromobenzyl'

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   19.6367(8)
_cell_length_b                   6.2680(2)
_cell_length_c                   20.8548(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.680(4)
_cell_angle_gamma                90
_cell_volume                     2530.3(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    130.00(10)
_cell_measurement_reflns_used    3835
_cell_measurement_theta_min      3.6320
_cell_measurement_theta_max      32.8200

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.533
_exptl_crystal_size_mid          0.279
_exptl_crystal_size_min          0.049
_exptl_absorpt_coefficient_mu    3.249
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.310
_exptl_absorpt_correction_T_max  0.853
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.541
_oxdiff_exptl_absorpt_empirical_full_max 1.736
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      130.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_reflns_number            17227
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.341
_diffrn_reflns_theta_max         36.611
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             10861
_reflns_number_gt                8361
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_max     0.780
_reflns_Friedel_fraction_full    0.947

_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    shelxt
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0499P)²+0.2949P] 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-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 2812 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.026(7)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         10861
_refine_ls_number_parameters     326
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1216
_refine_ls_wR_factor_gt          0.1006
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.003
_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 0.5954(2) 0.0918(6) 0.1501(2) 0.0235(7) Uani 1 1 d . . . . .
H1 H 0.626172 0.214119 0.143377 0.028 Uiso 1 1 calc R U . . .
C1A C 0.5751(2) 0.9691(6) 0.65485(19) 0.0231(8) Uani 1 1 d . . . . .
H1A H 0.597583 0.826081 0.654368 0.028 Uiso 1 1 calc R U . . .
C2 C 0.62454(19) -0.0291(6) 0.21085(19) 0.0201(7) Uani 1 1 d . . . . .
C2A C 0.61459(19) 1.1095(6) 0.7065(2) 0.0210(7) Uani 1 1 d . . . . .
C3 C 0.5870(2) -0.2308(7) 0.2226(2) 0.0247(8) Uani 1 1 d . . . . .
H3A H 0.552068 -0.198248 0.250375 0.030 Uiso 1 1 calc R U . . .
H3B H 0.620295 -0.333817 0.246323 0.030 Uiso 1 1 calc R U . . .
C3A C 0.5858(2) 1.3301(7) 0.7094(2) 0.0284(9) Uani 1 1 d . . . . .
H3A1 H 0.601906 1.420899 0.676066 0.034 Uiso 1 1 calc R U . . .
H3A2 H 0.602705 1.393337 0.752607 0.034 Uiso 1 1 calc R U . . .
C4 C 0.5512(2) -0.3327(6) 0.1592(2) 0.0269(7) Uani 1 1 d . . . . .
H4A H 0.583539 -0.433329 0.143477 0.032 Uiso 1 1 calc R U . . .
H4B H 0.510824 -0.415668 0.168025 0.032 Uiso 1 1 calc R U . . .
C4A C 0.5061(2) 1.3237(7) 0.6973(2) 0.0291(8) Uani 1 1 d . . . . .
H4A1 H 0.489862 1.291301 0.738630 0.035 Uiso 1 1 calc R U . . .
H4A2 H 0.487973 1.465759 0.682288 0.035 Uiso 1 1 calc R U . . .
C5 C 0.5271(2) -0.1704(6) 0.1065(2) 0.0270(8) Uani 1 1 d . . . . .
H5 H 0.504826 -0.241707 0.065378 0.032 Uiso 1 1 calc R U . . .
C5A C 0.47785(18) 1.1573(8) 0.64682(19) 0.0253(7) Uani 1 1 d . . . . .
H5A H 0.426232 1.153503 0.640143 0.030 Uiso 1 1 calc R U . . .
C6 C 0.4807(2) 0.0031(7) 0.1267(3) 0.0329(10) Uani 1 1 d . . . . .
H6A H 0.448795 0.059022 0.088571 0.040 Uiso 1 1 calc R U . . .
H6B H 0.453244 -0.052091 0.158837 0.040 Uiso 1 1 calc R U . . .
C6A C 0.50329(19) 1.1801(8) 0.58255(18) 0.0268(7) Uani 1 1 d . . . . .
H6A1 H 0.470607 1.113486 0.546838 0.032 Uiso 1 1 calc R U . . .
H6A2 H 0.509323 1.332150 0.571975 0.032 Uiso 1 1 calc R U . . .
C7 C 0.7499(2) 0.0579(8) 0.3459(2) 0.0252(8) Uani 1 1 d . . . . .
H7A H 0.778350 0.139257 0.319422 0.030 Uiso 1 1 calc R U . . .
H7B H 0.780901 -0.040359 0.374385 0.030 Uiso 1 1 calc R U . . .
C7A C 0.7497(2) 1.0358(8) 0.8339(2) 0.0269(8) Uani 1 1 d . . . . .
H7A1 H 0.781039 1.133810 0.862042 0.032 Uiso 1 1 calc R U . . .
H7A2 H 0.777690 0.953052 0.807364 0.032 Uiso 1 1 calc R U . . .
C8 C 0.71696(18) 0.2103(6) 0.38735(19) 0.0207(7) Uani 1 1 d . . . . .
C8A C 0.71678(19) 0.8852(7) 0.87586(19) 0.0228(8) Uani 1 1 d . . . . .
C9 C 0.70018(19) 0.4175(9) 0.36521(19) 0.0248(7) Uani 1 1 d . . . . .
H9 H 0.712937 0.464999 0.325618 0.030 Uiso 1 1 calc R U . . .
C9A C 0.70139(18) 0.9514(7) 0.93563(19) 0.0225(8) Uani 1 1 d . . . . .
H9A H 0.713900 1.091394 0.950630 0.027 Uiso 1 1 calc R U . . .
C10 C 0.6649(2) 0.5550(7) 0.4008(2) 0.0246(8) Uani 1 1 d . . . . .
H10 H 0.652968 0.695013 0.385401 0.029 Uiso 1 1 calc R U . . .
C10A C 0.6683(2) 0.8183(7) 0.9738(2) 0.0245(8) Uani 1 1 d . . . . .
H10A H 0.658099 0.865194 1.014477 0.029 Uiso 1 1 calc R U . . .
C11 C 0.64744(19) 0.4840(6) 0.45891(19) 0.0215(8) Uani 1 1 d . . . . .
C11A C 0.6504(2) 0.6136(7) 0.95068(19) 0.0222(8) Uani 1 1 d . . . . .
C12 C 0.66450(19) 0.2783(7) 0.48211(19) 0.0217(7) Uani 1 1 d . . . . .
H12 H 0.652667 0.231518 0.522147 0.026 Uiso 1 1 calc R U . . .
C12A C 0.6656(2) 0.5418(7) 0.8921(2) 0.0268(8) Uani 1 1 d . . . . .
H12A H 0.653186 0.401493 0.877370 0.032 Uiso 1 1 calc R U . . .
C13 C 0.69881(18) 0.1447(7) 0.44582(19) 0.0221(8) Uani 1 1 d . . . . .
H13 H 0.710325 0.004453 0.461165 0.026 Uiso 1 1 calc R U . . .
C13A C 0.69941(19) 0.6769(9) 0.85509(19) 0.0255(7) Uani 1 1 d . . . . .
H13A H 0.710856 0.627469 0.815172 0.031 Uiso 1 1 calc R U . . .
N1 N 0.67529(17) 0.0593(6) 0.24716(17) 0.0232(7) Uani 1 1 d . . . . .
N1A N 0.66605(17) 1.0213(6) 0.74219(16) 0.0226(6) Uani 1 1 d . . . . .
O1 O 0.69873(13) -0.0649(6) 0.30336(13) 0.0241(5) Uani 1 1 d . . . . .
O1A O 0.69876(13) 1.1594(6) 0.79127(13) 0.0245(5) Uani 1 1 d . . . . .
O5 O 0.58685(15) -0.0455(5) 0.09609(14) 0.0281(6) Uani 1 1 d . . . . .
O5A O 0.50697(14) 0.9492(5) 0.66787(14) 0.0276(6) Uani 1 1 d . . . . .
O6 O 0.52813(15) 0.1658(5) 0.15508(16) 0.0299(6) Uani 1 1 d . . . . .
O6A O 0.56890(14) 1.0694(5) 0.59281(14) 0.0276(6) Uani 1 1 d . . . . .
Br1 Br 0.60178(2) 0.67350(6) 0.50828(2) 0.02709(10) Uani 1 1 d . . . . .
Br1A Br 0.60476(2) 0.42740(7) 1.00165(2) 0.02887(11) 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 O5 1.405(5) . ?
C1 O6 1.421(5) . ?
C1 C2 1.504(5) . ?
C1 H1 1.0000 . ?
C1A O5A 1.414(5) . ?
C1A O6A 1.425(5) . ?
C1A C2A 1.501(5) . ?
C1A H1A 1.0000 . ?
C2 N1 1.272(5) . ?
C2 C3 1.505(5) . ?
C2A N1A 1.276(5) . ?
C2A C3A 1.499(6) . ?
C3 C4 1.529(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C4A 1.543(6) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C4 C5 1.515(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4A C5A 1.518(6) . ?
C4A H4A1 0.9900 . ?
C4A H4A2 0.9900 . ?
C5 O5 1.456(5) . ?
C5 C6 1.523(6) . ?
C5 H5 1.0000 . ?
C5A O5A 1.462(5) . ?
C5A C6A 1.514(5) . ?
C5A H5A 1.0000 . ?
C6 O6 1.440(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6A O6A 1.447(5) . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?
C7 O1 1.446(5) . ?
C7 C8 1.506(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7A O1A 1.446(5) . ?
C7A C8A 1.505(6) . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C8 C13 1.389(5) . ?
C8 C9 1.399(7) . ?
C8A C9A 1.394(6) . ?
C8A C13A 1.399(7) . ?
C9 C10 1.395(6) . ?
C9 H9 0.9500 . ?
C9A C10A 1.388(6) . ?
C9A H9A 0.9500 . ?
C10 C11 1.387(6) . ?
C10 H10 0.9500 . ?
C10A C11A 1.395(6) . ?
C10A H10A 0.9500 . ?
C11 C12 1.398(6) . ?
C11 Br1 1.893(4) . ?
C11A C12A 1.381(6) . ?
C11A Br1A 1.901(4) . ?
C12 C13 1.378(6) . ?
C12 H12 0.9500 . ?
C12A C13A 1.388(6) . ?
C12A H12A 0.9500 . ?
C13 H13 0.9500 . ?
C13A H13A 0.9500 . ?
N1 O1 1.418(5) . ?
N1A O1A 1.410(4) . ?

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
O5 C1 O6 105.7(3) . . ?
O5 C1 C2 110.1(3) . . ?
O6 C1 C2 109.2(3) . . ?
O5 C1 H1 110.6 . . ?
O6 C1 H1 110.6 . . ?
C2 C1 H1 110.6 . . ?
O5A C1A O6A 105.9(3) . . ?
O5A C1A C2A 107.8(3) . . ?
O6A C1A C2A 110.3(3) . . ?
O5A C1A H1A 110.9 . . ?
O6A C1A H1A 110.9 . . ?
C2A C1A H1A 110.9 . . ?
N1 C2 C1 115.5(3) . . ?
N1 C2 C3 128.7(4) . . ?
C1 C2 C3 115.7(3) . . ?
N1A C2A C3A 130.0(4) . . ?
N1A C2A C1A 115.3(4) . . ?
C3A C2A C1A 114.6(3) . . ?
C2 C3 C4 112.1(3) . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C2A C3A C4A 110.4(4) . . ?
C2A C3A H3A1 109.6 . . ?
C4A C3A H3A1 109.6 . . ?
C2A C3A H3A2 109.6 . . ?
C4A C3A H3A2 109.6 . . ?
H3A1 C3A H3A2 108.1 . . ?
C5 C4 C3 112.9(3) . . ?
C5 C4 H4A 109.0 . . ?
C3 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C5A C4A C3A 111.9(3) . . ?
C5A C4A H4A1 109.2 . . ?
C3A C4A H4A1 109.2 . . ?
C5A C4A H4A2 109.2 . . ?
C3A C4A H4A2 109.2 . . ?
H4A1 C4A H4A2 107.9 . . ?
O5 C5 C4 108.0(3) . . ?
O5 C5 C6 101.1(3) . . ?
C4 C5 C6 114.0(4) . . ?
O5 C5 H5 111.1 . . ?
C4 C5 H5 111.1 . . ?
C6 C5 H5 111.1 . . ?
O5A C5A C6A 100.3(3) . . ?
O5A C5A C4A 109.0(3) . . ?
C6A C5A C4A 114.3(4) . . ?
O5A C5A H5A 110.9 . . ?
C6A C5A H5A 110.9 . . ?
C4A C5A H5A 110.9 . . ?
O6 C6 C5 104.1(3) . . ?
O6 C6 H6A 110.9 . . ?
C5 C6 H6A 110.9 . . ?
O6 C6 H6B 110.9 . . ?
C5 C6 H6B 110.9 . . ?
H6A C6 H6B 109.0 . . ?
O6A C6A C5A 104.0(3) . . ?
O6A C6A H6A1 111.0 . . ?
C5A C6A H6A1 111.0 . . ?
O6A C6A H6A2 111.0 . . ?
C5A C6A H6A2 111.0 . . ?
H6A1 C6A H6A2 109.0 . . ?
O1 C7 C8 111.6(3) . . ?
O1 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
O1 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
O1A C7A C8A 111.9(3) . . ?
O1A C7A H7A1 109.2 . . ?
C8A C7A H7A1 109.2 . . ?
O1A C7A H7A2 109.2 . . ?
C8A C7A H7A2 109.2 . . ?
H7A1 C7A H7A2 107.9 . . ?
C13 C8 C9 118.9(4) . . ?
C13 C8 C7 121.0(4) . . ?
C9 C8 C7 120.0(4) . . ?
C9A C8A C13A 118.4(4) . . ?
C9A C8A C7A 120.8(4) . . ?
C13A C8A C7A 120.8(4) . . ?
C10 C9 C8 120.6(4) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C10A C9A C8A 121.8(4) . . ?
C10A C9A H9A 119.1 . . ?
C8A C9A H9A 119.1 . . ?
C11 C10 C9 119.0(4) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C9A C10A C11A 118.0(4) . . ?
C9A C10A H10A 121.0 . . ?
C11A C10A H10A 121.0 . . ?
C10 C11 C12 121.2(4) . . ?
C10 C11 Br1 118.9(3) . . ?
C12 C11 Br1 119.9(3) . . ?
C12A C11A C10A 121.7(4) . . ?
C12A C11A Br1A 119.1(3) . . ?
C10A C11A Br1A 119.1(3) . . ?
C13 C12 C11 118.8(4) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C11A C12A C13A 119.2(4) . . ?
C11A C12A H12A 120.4 . . ?
C13A C12A H12A 120.4 . . ?
C12 C13 C8 121.6(4) . . ?
C12 C13 H13 119.2 . . ?
C8 C13 H13 119.2 . . ?
C12A C13A C8A 120.8(4) . . ?
C12A C13A H13A 119.6 . . ?
C8A C13A H13A 119.6 . . ?
C2 N1 O1 111.5(3) . . ?
C2A N1A O1A 112.2(3) . . ?
N1 O1 C7 108.1(3) . . ?
N1A O1A C7A 107.5(3) . . ?
C1 O5 C5 101.6(3) . . ?
C1A O5A C5A 101.5(3) . . ?
C1 O6 C6 106.5(3) . . ?
C1A O6A C6A 106.5(3) . . ?

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
O5 C1 C2 N1 132.4(4) . . . . ?
O6 C1 C2 N1 -111.9(4) . . . . ?
O5 C1 C2 C3 -51.3(4) . . . . ?
O6 C1 C2 C3 64.4(4) . . . . ?
O5A C1A C2A N1A 117.8(4) . . . . ?
O6A C1A C2A N1A -127.1(4) . . . . ?
O5A C1A C2A C3A -60.3(4) . . . . ?
O6A C1A C2A C3A 54.9(4) . . . . ?
N1 C2 C3 C4 -156.1(4) . . . . ?
C1 C2 C3 C4 28.2(5) . . . . ?
N1A C2A C3A C4A -139.0(4) . . . . ?
C1A C2A C3A C4A 38.7(5) . . . . ?
C2 C3 C4 C5 -31.4(5) . . . . ?
C2A C3A C4A C5A -36.9(5) . . . . ?
C3 C4 C5 O5 56.7(4) . . . . ?
C3 C4 C5 C6 -54.7(5) . . . . ?
C3A C4A C5A O5A 56.6(5) . . . . ?
C3A C4A C5A C6A -54.7(5) . . . . ?
O5 C5 C6 O6 -27.0(4) . . . . ?
C4 C5 C6 O6 88.5(4) . . . . ?
O5A C5A C6A O6A -32.0(4) . . . . ?
C4A C5A C6A O6A 84.4(4) . . . . ?
O1 C7 C8 C13 85.5(4) . . . . ?
O1 C7 C8 C9 -90.5(5) . . . . ?
O1A C7A C8A C9A -87.6(4) . . . . ?
O1A C7A C8A C13A 90.8(5) . . . . ?
C13 C8 C9 C10 -1.0(6) . . . . ?
C7 C8 C9 C10 175.1(3) . . . . ?
C13A C8A C9A C10A -1.4(6) . . . . ?
C7A C8A C9A C10A 177.1(3) . . . . ?
C8 C9 C10 C11 0.8(6) . . . . ?
C8A C9A C10A C11A -0.1(6) . . . . ?
C9 C10 C11 C12 -0.1(6) . . . . ?
C9 C10 C11 Br1 178.3(3) . . . . ?
C9A C10A C11A C12A 1.0(6) . . . . ?
C9A C10A C11A Br1A -179.9(3) . . . . ?
C10 C11 C12 C13 -0.5(6) . . . . ?
Br1 C11 C12 C13 -178.9(3) . . . . ?
C10A C11A C12A C13A -0.3(6) . . . . ?
Br1A C11A C12A C13A -179.5(3) . . . . ?
C11 C12 C13 C8 0.4(6) . . . . ?
C9 C8 C13 C12 0.3(6) . . . . ?
C7 C8 C13 C12 -175.7(3) . . . . ?
C11A C12A C13A C8A -1.2(6) . . . . ?
C9A C8A C13A C12A 2.0(6) . . . . ?
C7A C8A C13A C12A -176.4(4) . . . . ?
C1 C2 N1 O1 179.4(3) . . . . ?
C3 C2 N1 O1 3.7(6) . . . . ?
C3A C2A N1A O1A 0.3(6) . . . . ?
C1A C2A N1A O1A -177.4(3) . . . . ?
C2 N1 O1 C7 -172.6(3) . . . . ?
C8 C7 O1 N1 83.5(4) . . . . ?
C2A N1A O1A C7A 172.3(3) . . . . ?
C8A C7A O1A N1A -72.7(4) . . . . ?
O6 C1 O5 C5 -44.5(4) . . . . ?
C2 C1 O5 C5 73.3(4) . . . . ?
C4 C5 O5 C1 -76.7(4) . . . . ?
C6 C5 O5 C1 43.2(4) . . . . ?
O6A C1A O5A C5A -42.9(4) . . . . ?
C2A C1A O5A C5A 75.1(4) . . . . ?
C6A C5A O5A C1A 45.4(3) . . . . ?
C4A C5A O5A C1A -75.0(4) . . . . ?
O5 C1 O6 C6 27.0(4) . . . . ?
C2 C1 O6 C6 -91.5(4) . . . . ?
C5 C6 O6 C1 1.0(5) . . . . ?
O5A C1A O6A C6A 22.1(4) . . . . ?
C2A C1A O6A C6A -94.2(4) . . . . ?
C5A C6A O6A C1A 7.0(4) . . . . ?

_refine_diff_density_max         0.858
_refine_diff_density_min         -1.120
_refine_diff_density_rms         0.119

####################################################################### 
# 
# 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_cmpd7
_database_code_depnum_ccdc_archive 'CCDC 1578348'
_audit_update_record             
;
2017-10-06 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H11 N O4'
_chemical_formula_weight         185.18
_chemical_oxdiff_usercomment     'Amani/SJW acetate'

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   5.6704(2)
_cell_length_b                   15.6773(6)
_cell_length_c                   9.7844(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     869.80(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    130.01(10)
_cell_measurement_reflns_used    3738
_cell_measurement_theta_min      4.1850
_cell_measurement_theta_max      35.7390

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.645
_exptl_crystal_size_mid          0.359
_exptl_crystal_size_min          0.054
_exptl_absorpt_coefficient_mu    0.114
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.426
_oxdiff_exptl_absorpt_empirical_full_max 1.729
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      130.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_reflns_number            11016
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.330
_diffrn_reflns_theta_max         36.343
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4053
_reflns_number_gt                3568
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_max     0.943
_reflns_Friedel_fraction_full    1.000

_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    shelxt
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0602P)²+0.0486P] 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_abs_structure_details 
;
 Flack x determined using 1346 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(4)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4053
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.002
_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 0.5463(3) 0.57177(8) 0.45897(13) 0.0204(2) Uani 1 1 d . . . . .
H1 H 0.619837 0.563346 0.367069 0.024 Uiso 1 1 calc R U . . .
C2 C 0.6000(2) 0.49733(8) 0.55262(12) 0.0166(2) Uani 1 1 d . . . . .
C3 C 0.4855(2) 0.50048(8) 0.69069(13) 0.0191(2) Uani 1 1 d . . . . .
H3A H 0.588599 0.531999 0.754857 0.023 Uiso 1 1 calc R U . . .
H3B H 0.465993 0.441724 0.725986 0.023 Uiso 1 1 calc R U . . .
C4 C 0.2429(3) 0.54445(8) 0.68380(14) 0.0203(2) Uani 1 1 d . . . . .
H4A H 0.121675 0.501970 0.657887 0.024 Uiso 1 1 calc R U . . .
H4B H 0.201783 0.566969 0.775282 0.024 Uiso 1 1 calc R U . . .
C5 C 0.2412(2) 0.61696(8) 0.58110(13) 0.0185(2) Uani 1 1 d . . . . .
H5 H 0.084347 0.646072 0.579115 0.022 Uiso 1 1 calc R U . . .
C6 C 0.4403(3) 0.68103(8) 0.60283(15) 0.0212(2) Uani 1 1 d . . . . .
H6A H 0.394266 0.738378 0.569887 0.025 Uiso 1 1 calc R U . . .
H6B H 0.483441 0.684862 0.700679 0.025 Uiso 1 1 calc R U . . .
C7 C 0.9736(3) 0.32555(8) 0.56495(14) 0.0196(2) Uani 1 1 d . . . . .
C8 C 1.0345(3) 0.26652(9) 0.67950(15) 0.0244(3) Uani 1 1 d . . . . .
H8A H 1.016537 0.207345 0.648918 0.037 Uiso 1 1 calc R U . . .
H8B H 0.928823 0.277138 0.756911 0.037 Uiso 1 1 calc R U . . .
H8C H 1.198023 0.276341 0.707810 0.037 Uiso 1 1 calc R U . . .
N1 N 0.7452(2) 0.44324(7) 0.50345(11) 0.0196(2) Uani 1 1 d . . . . .
O1 O 0.79711(19) 0.37947(6) 0.60523(10) 0.01940(19) Uani 1 1 d . . . . .
O2 O 1.0640(3) 0.32707(8) 0.45462(12) 0.0369(3) Uani 1 1 d . . . . .
O5 O 0.3016(2) 0.58286(6) 0.44770(10) 0.0229(2) Uani 1 1 d . . . . .
O6 O 0.63375(19) 0.64699(6) 0.52276(12) 0.0236(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 O5 1.4028(18) . ?
C1 O6 1.4234(17) . ?
C1 C2 1.5147(17) . ?
C1 H1 1.0000 . ?
C2 N1 1.2760(16) . ?
C2 C3 1.4998(18) . ?
C3 C4 1.5403(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5172(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 O5 1.4514(16) . ?
C5 C6 1.5257(19) . ?
C5 H5 1.0000 . ?
C6 O6 1.4501(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O2 1.1952(17) . ?
C7 O1 1.3681(16) . ?
C7 C8 1.4939(19) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
N1 O1 1.4414(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
O5 C1 O6 106.05(10) . . ?
O5 C1 C2 110.00(11) . . ?
O6 C1 C2 107.63(11) . . ?
O5 C1 H1 111.0 . . ?
O6 C1 H1 111.0 . . ?
C2 C1 H1 111.0 . . ?
N1 C2 C3 129.85(11) . . ?
N1 C2 C1 114.44(11) . . ?
C3 C2 C1 115.62(11) . . ?
C2 C3 C4 111.23(11) . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C3 111.70(11) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
O5 C5 C4 108.55(10) . . ?
O5 C5 C6 101.16(11) . . ?
C4 C5 C6 113.36(11) . . ?
O5 C5 H5 111.1 . . ?
C4 C5 H5 111.1 . . ?
C6 C5 H5 111.1 . . ?
O6 C6 C5 104.01(11) . . ?
O6 C6 H6A 111.0 . . ?
C5 C6 H6A 111.0 . . ?
O6 C6 H6B 111.0 . . ?
C5 C6 H6B 111.0 . . ?
H6A C6 H6B 109.0 . . ?
O2 C7 O1 124.16(13) . . ?
O2 C7 C8 126.23(13) . . ?
O1 C7 C8 109.62(11) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 N1 O1 109.41(10) . . ?
C7 O1 N1 112.27(10) . . ?
C1 O5 C5 102.01(10) . . ?
C1 O6 C6 106.15(10) . . ?

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
O5 C1 C2 N1 129.94(12) . . . . ?
O6 C1 C2 N1 -114.94(13) . . . . ?
O5 C1 C2 C3 -53.03(15) . . . . ?
O6 C1 C2 C3 62.09(15) . . . . ?
N1 C2 C3 C4 -150.86(14) . . . . ?
C1 C2 C3 C4 32.66(16) . . . . ?
C2 C3 C4 C5 -35.72(15) . . . . ?
C3 C4 C5 O5 59.00(14) . . . . ?
C3 C4 C5 C6 -52.54(15) . . . . ?
O5 C5 C6 O6 -27.20(12) . . . . ?
C4 C5 C6 O6 88.81(13) . . . . ?
C3 C2 N1 O1 -1.13(19) . . . . ?
C1 C2 N1 O1 175.38(11) . . . . ?
O2 C7 O1 N1 -4.8(2) . . . . ?
C8 C7 O1 N1 174.66(11) . . . . ?
C2 N1 O1 C7 -172.46(12) . . . . ?
O6 C1 O5 C5 -44.11(12) . . . . ?
C2 C1 O5 C5 72.00(12) . . . . ?
C4 C5 O5 C1 -76.46(13) . . . . ?
C6 C5 O5 C1 43.04(12) . . . . ?
O5 C1 O6 C6 26.16(13) . . . . ?
C2 C1 O6 C6 -91.55(12) . . . . ?
C5 C6 O6 C1 1.57(13) . . . . ?

_refine_diff_density_max         0.320
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_cmpd8
_database_code_depnum_ccdc_archive 'CCDC 1578350'
_audit_update_record             
;
2017-10-06 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 N3 O8'
_chemical_formula_weight         337.25

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   6.2700(13)
_cell_length_b                   9.4560(19)
_cell_length_c                   23.600(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1399.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    1969
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.87

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.136
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           synchrotron
_diffrn_source                   'MX2 beamline Australian Synchrotron'
_diffrn_measurement_device_type  'ADSC quantum 210r'
_diffrn_measurement_method       'phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23414
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.320
_diffrn_reflns_theta_max         27.871
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3333
_reflns_number_gt                3118
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.996

_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       'Bluice (McPhillips, 2002)'
_computing_cell_refinement       'XSD (Kabsch 1993)'
_computing_data_reduction        'XSD (Kabsch 1993)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0571P)²+0.1695P] 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-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.184(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1255 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3333
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0906
_refine_ls_wR_factor_gt          0.0881
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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 0.8296(3) 0.2773(2) 0.32432(9) 0.0350(4) Uani 1 1 d . . . . .
H1 H 0.896980 0.221968 0.354508 0.042 Uiso 1 1 calc R U . . .
C2 C 0.6225(3) 0.3437(2) 0.34458(8) 0.0300(4) Uani 1 1 d . . . . .
C3 C 0.4951(3) 0.4218(2) 0.30029(8) 0.0317(4) Uani 1 1 d . . . . .
H3A H 0.541355 0.519595 0.298987 0.038 Uiso 1 1 calc R U . . .
H3B H 0.345463 0.420590 0.310733 0.038 Uiso 1 1 calc R U . . .
C4 C 0.5217(3) 0.3550(3) 0.24129(9) 0.0372(5) Uani 1 1 d . . . . .
H4A H 0.420728 0.278032 0.236944 0.045 Uiso 1 1 calc R U . . .
H4B H 0.491081 0.425157 0.212445 0.045 Uiso 1 1 calc R U . . .
C5 C 0.7475(3) 0.2990(2) 0.23309(9) 0.0368(4) Uani 1 1 d . . . . .
H5 H 0.765560 0.259001 0.195078 0.044 Uiso 1 1 calc R U . . .
C6 C 0.9205(3) 0.4079(3) 0.24574(8) 0.0370(5) Uani 1 1 d . . . . .
H6A H 1.046505 0.390883 0.222881 0.044 Uiso 1 1 calc R U . . .
H6B H 0.869565 0.503097 0.238585 0.044 Uiso 1 1 calc R U . . .
C7 C 0.3318(3) 0.3973(2) 0.46580(8) 0.0286(4) Uani 1 1 d . . . . .
C8 C 0.1240(3) 0.4741(2) 0.47356(8) 0.0277(4) Uani 1 1 d . . . . .
C9 C 0.0289(3) 0.5491(2) 0.42927(8) 0.0282(4) Uani 1 1 d . . . . .
H9 H 0.093991 0.554949 0.393934 0.034 Uiso 1 1 calc R U . . .
C10 C -0.1653(3) 0.6146(2) 0.43944(8) 0.0291(4) Uani 1 1 d . . . . .
C11 C -0.2681(3) 0.6096(2) 0.49121(8) 0.0305(4) Uani 1 1 d . . . . .
H11 H -0.397114 0.655783 0.497278 0.037 Uiso 1 1 calc R U . . .
C12 C -0.1689(3) 0.5322(2) 0.53369(8) 0.0309(4) Uani 1 1 d . . . . .
C13 C 0.0249(3) 0.4648(2) 0.52639(8) 0.0297(4) Uani 1 1 d . . . . .
H13 H 0.087531 0.414517 0.555900 0.036 Uiso 1 1 calc R U . . .
N1 N 0.5850(3) 0.33049(18) 0.39756(7) 0.0320(3) Uani 1 1 d . . . . .
N2 N -0.2731(3) 0.68594(17) 0.39178(7) 0.0317(4) Uani 1 1 d . . . . .
N3 N -0.2811(3) 0.5187(2) 0.58839(7) 0.0377(4) Uani 1 1 d . . . . .
O5 O 0.7871(2) 0.19264(17) 0.27649(7) 0.0405(4) Uani 1 1 d . . . . .
O6 O 0.9659(2) 0.38734(18) 0.30545(6) 0.0359(3) Uani 1 1 d . . . . .
O1 O 0.3854(2) 0.40147(17) 0.41018(5) 0.0323(3) Uani 1 1 d . . . . .
O2 O 0.4317(2) 0.34278(16) 0.50324(6) 0.0336(3) Uani 1 1 d . . . . .
O7 O -0.1787(2) 0.69186(16) 0.34646(6) 0.0359(3) Uani 1 1 d . . . . .
O8 O -0.4540(3) 0.73287(19) 0.39995(7) 0.0439(4) Uani 1 1 d . . . . .
O9 O -0.4459(3) 0.5857(2) 0.59514(7) 0.0490(4) Uani 1 1 d . . . . .
O10 O -0.2042(3) 0.4391(2) 0.62386(7) 0.0507(5) 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 O5 1.409(3) . ?
C1 O6 1.418(3) . ?
C1 C2 1.519(3) . ?
C1 H1 0.9800 . ?
C2 N1 1.278(3) . ?
C2 C3 1.509(3) . ?
C3 C4 1.538(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.524(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O5 1.457(3) . ?
C5 C6 1.525(3) . ?
C5 H5 0.9800 . ?
C6 O6 1.451(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O2 1.200(2) . ?
C7 O1 1.356(2) . ?
C7 C8 1.502(3) . ?
C8 C13 1.396(2) . ?
C8 C9 1.397(3) . ?
C9 C10 1.387(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.382(3) . ?
C10 N2 1.475(2) . ?
C11 C12 1.389(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.383(3) . ?
C12 N3 1.476(2) . ?
C13 H13 0.9300 . ?
N1 O1 1.451(2) . ?
N2 O7 1.224(2) . ?
N2 O8 1.234(2) . ?
N3 O9 1.223(3) . ?
N3 O10 1.224(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 C1 O6 106.23(17) . . ?
O5 C1 C2 108.96(17) . . ?
O6 C1 C2 108.14(17) . . ?
O5 C1 H1 111.1 . . ?
O6 C1 H1 111.1 . . ?
C2 C1 H1 111.1 . . ?
N1 C2 C3 128.89(17) . . ?
N1 C2 C1 115.15(17) . . ?
C3 C2 C1 115.89(17) . . ?
C2 C3 C4 111.63(17) . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C3 111.02(16) . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
O5 C5 C4 107.98(17) . . ?
O5 C5 C6 101.96(16) . . ?
C4 C5 C6 113.66(18) . . ?
O5 C5 H5 111.0 . . ?
C4 C5 H5 111.0 . . ?
C6 C5 H5 111.0 . . ?
O6 C6 C5 103.85(17) . . ?
O6 C6 H6A 111.0 . . ?
C5 C6 H6A 111.0 . . ?
O6 C6 H6B 111.0 . . ?
C5 C6 H6B 111.0 . . ?
H6A C6 H6B 109.0 . . ?
O2 C7 O1 126.59(18) . . ?
O2 C7 C8 124.80(17) . . ?
O1 C7 C8 108.61(15) . . ?
C13 C8 C9 120.68(17) . . ?
C13 C8 C7 117.68(16) . . ?
C9 C8 C7 121.62(16) . . ?
C10 C9 C8 118.17(17) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C11 C10 C9 123.17(18) . . ?
C11 C10 N2 118.42(17) . . ?
C9 C10 N2 118.31(16) . . ?
C10 C11 C12 116.56(18) . . ?
C10 C11 H11 121.7 . . ?
C12 C11 H11 121.7 . . ?
C13 C12 C11 123.16(17) . . ?
C13 C12 N3 119.19(17) . . ?
C11 C12 N3 117.62(18) . . ?
C12 C13 C8 118.25(17) . . ?
C12 C13 H13 120.9 . . ?
C8 C13 H13 120.9 . . ?
C2 N1 O1 108.33(15) . . ?
O7 N2 O8 124.39(17) . . ?
O7 N2 C10 117.78(16) . . ?
O8 N2 C10 117.81(17) . . ?
O9 N3 O10 124.23(18) . . ?
O9 N3 C12 118.15(17) . . ?
O10 N3 C12 117.61(17) . . ?
C1 O5 C5 101.72(15) . . ?
C1 O6 C6 106.55(16) . . ?
C7 O1 N1 113.53(14) . . ?

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
O5 C1 C2 N1 130.41(19) . . . . ?
O6 C1 C2 N1 -114.5(2) . . . . ?
O5 C1 C2 C3 -52.4(2) . . . . ?
O6 C1 C2 C3 62.6(2) . . . . ?
N1 C2 C3 C4 -151.2(2) . . . . ?
C1 C2 C3 C4 32.1(2) . . . . ?
C2 C3 C4 C5 -35.5(2) . . . . ?
C3 C4 C5 O5 59.9(2) . . . . ?
C3 C4 C5 C6 -52.4(2) . . . . ?
O5 C5 C6 O6 -25.32(19) . . . . ?
C4 C5 C6 O6 90.6(2) . . . . ?
O2 C7 C8 C13 -9.4(3) . . . . ?
O1 C7 C8 C13 170.98(17) . . . . ?
O2 C7 C8 C9 172.4(2) . . . . ?
O1 C7 C8 C9 -7.2(2) . . . . ?
C13 C8 C9 C10 0.5(3) . . . . ?
C7 C8 C9 C10 178.62(17) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C8 C9 C10 N2 -176.04(17) . . . . ?
C9 C10 C11 C12 -1.2(3) . . . . ?
N2 C10 C11 C12 175.17(17) . . . . ?
C10 C11 C12 C13 1.3(3) . . . . ?
C10 C11 C12 N3 -176.70(17) . . . . ?
C11 C12 C13 C8 -0.6(3) . . . . ?
N3 C12 C13 C8 177.38(18) . . . . ?
C9 C8 C13 C12 -0.3(3) . . . . ?
C7 C8 C13 C12 -178.53(16) . . . . ?
C3 C2 N1 O1 2.1(3) . . . . ?
C1 C2 N1 O1 178.80(16) . . . . ?
C11 C10 N2 O7 178.69(18) . . . . ?
C9 C10 N2 O7 -4.8(3) . . . . ?
C11 C10 N2 O8 -2.9(3) . . . . ?
C9 C10 N2 O8 173.67(18) . . . . ?
C13 C12 N3 O9 175.80(19) . . . . ?
C11 C12 N3 O9 -6.1(3) . . . . ?
C13 C12 N3 O10 -5.2(3) . . . . ?
C11 C12 N3 O10 172.9(2) . . . . ?
O6 C1 O5 C5 -43.57(19) . . . . ?
C2 C1 O5 C5 72.72(19) . . . . ?
C4 C5 O5 C1 -78.47(18) . . . . ?
C6 C5 O5 C1 41.53(18) . . . . ?
O5 C1 O6 C6 27.2(2) . . . . ?
C2 C1 O6 C6 -89.62(19) . . . . ?
C5 C6 O6 C1 -0.3(2) . . . . ?
O2 C7 O1 N1 0.2(3) . . . . ?
C8 C7 O1 N1 179.86(14) . . . . ?
C2 N1 O1 C7 -178.46(17) . . . . ?

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.053

