# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_solid10
_database_code_depnum_ccdc_archive 'CCDC 1474399'
_audit_update_record             
;
2017-06-24 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;

_audit_creation_method           'SHELXTL-NT2000 ver.6.12'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H6 N O3, C5 H7 N2'
_chemical_formula_sum            'C12 H13 N3 O3'
_chemical_formula_weight         247.25

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

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

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

_cell_length_a                   8.4909(18)
_cell_length_b                   17.309(4)
_cell_length_c                   8.0641(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.652(4)
_cell_angle_gamma                90.00
_cell_volume                     1160.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1001
_cell_measurement_theta_min      3.67
_cell_measurement_theta_max      24.34

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.458
_exptl_crystal_size_mid          0.329
_exptl_crystal_size_min          0.248
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10338
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_av_R_equivalents  0.0782
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.353
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1985
_reflns_number_gt                1586
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0485P)²+1.9749P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1985
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1246
_refine_ls_R_factor_gt           0.1004
_refine_ls_wR_factor_ref         0.1879
_refine_ls_wR_factor_gt          0.1768
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_restrained_S_all      1.208
_refine_ls_shift/su_max          0.042
_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
O1 O 0.3408(4) 0.61888(19) 0.2280(4) 0.0399(9) Uani 1 1 d . . . . .
O2 O 0.1606(4) 0.52664(19) 0.2303(4) 0.0460(10) Uani 1 1 d . . . . .
C1 C 0.4747(5) 0.6168(3) 0.7539(6) 0.0376(12) Uani 1 1 d . . . . .
H7 H 0.5515 0.6509 0.8110 0.045 Uiso 1 1 calc R U . . .
N2 N 1.1105(4) 0.6813(2) 0.9815(5) 0.0359(10) Uani 1 1 d . . . . .
H2 H 1.1881 0.6588 1.0495 0.043 Uiso 1 1 calc R U . . .
O3 O 0.5154(4) 0.6685(2) 0.4940(4) 0.0461(10) Uani 1 1 d . . . . .
H3 H 0.4775 0.6659 0.3922 0.069 Uiso 1 1 calc R U . . .
C2 C 0.2476(5) 0.5165(2) 0.5885(5) 0.0302(11) Uani 1 1 d . . . . .
H9 H 0.1704 0.4823 0.5323 0.036 Uiso 1 1 calc R U . . .
N1 N 0.7368(5) 0.7880(2) 0.6672(5) 0.0393(10) Uani 1 1 d . . . . .
H1A H 0.7296 0.8376 0.6659 0.047 Uiso 1 1 calc R U . . .
H1B H 0.6646 0.7608 0.6028 0.047 Uiso 1 1 calc R U . . .
C3 C 0.2843(5) 0.5152(2) 0.7650(5) 0.0279(10) Uani 1 1 d . . . . .
C4 C 0.3209(5) 0.5663(2) 0.4937(5) 0.0255(10) Uani 1 1 d . . . . .
C5 C 0.2697(5) 0.5690(3) 0.3048(5) 0.0283(10) Uani 1 1 d . . . . .
N3 N 0.2079(4) 0.4630(2) 0.8583(5) 0.0360(10) Uani 1 1 d . . . . .
H3A H 0.2327 0.4629 0.9671 0.043 Uiso 1 1 calc R U . . .
H3B H 0.1367 0.4314 0.8062 0.043 Uiso 1 1 calc R U . . .
C6 C 0.3999(5) 0.5671(3) 0.8453(6) 0.0345(11) Uani 1 1 d . . . . .
H8 H 0.4268 0.5680 0.9629 0.041 Uiso 1 1 calc R U . . .
C7 C 0.8590(5) 0.7536(2) 0.7685(5) 0.0274(10) Uani 1 1 d . . . . .
C8 C 0.9799(5) 0.7962(3) 0.8762(5) 0.0339(11) Uani 1 1 d . . . . .
H13 H 0.9767 0.8499 0.8762 0.041 Uiso 1 1 calc R U . . .
C9 C 0.4388(5) 0.6175(3) 0.5780(5) 0.0309(11) Uani 1 1 d . . . . .
C10 C 1.1010(5) 0.7581(3) 0.9797(6) 0.0366(12) Uani 1 1 d . . . . .
H12 H 1.1796 0.7865 1.0514 0.044 Uiso 1 1 calc R U . . .
C11 C 0.8775(5) 0.6721(2) 0.7720(5) 0.0296(10) Uani 1 1 d . . . . .
H10 H 0.8036 0.6414 0.6999 0.036 Uiso 1 1 calc R U . . .
C12 C 1.0005(5) 0.6389(3) 0.8784(6) 0.0359(12) Uani 1 1 d . . . . .
H11 H 1.0096 0.5854 0.8806 0.043 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.282(5) . ?
O2 C5 1.237(5) . ?
C1 C6 1.370(6) . ?
C1 C9 1.389(6) . ?
C1 H7 0.9300 . ?
N2 C10 1.332(6) . ?
N2 C12 1.338(6) . ?
N2 H2 0.8600 . ?
O3 C9 1.356(5) . ?
O3 H3 0.8200 . ?
C2 C4 1.382(6) . ?
C2 C3 1.394(6) . ?
C2 H9 0.9300 . ?
N1 C7 1.325(5) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
C3 C6 1.389(6) . ?
C3 N3 1.414(5) . ?
C4 C9 1.406(6) . ?
C4 C5 1.498(6) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
C6 H8 0.9300 . ?
C7 C8 1.411(6) . ?
C7 C11 1.421(6) . ?
C8 C10 1.357(6) . ?
C8 H13 0.9300 . ?
C10 H12 0.9300 . ?
C11 C12 1.339(6) . ?
C11 H10 0.9300 . ?
C12 H11 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C9 121.7(4) . . ?
C6 C1 H7 119.2 . . ?
C9 C1 H7 119.2 . . ?
C10 N2 C12 120.5(4) . . ?
C10 N2 H2 119.7 . . ?
C12 N2 H2 119.7 . . ?
C9 O3 H3 109.5 . . ?
C4 C2 C3 122.8(4) . . ?
C4 C2 H9 118.6 . . ?
C3 C2 H9 118.6 . . ?
C7 N1 H1A 120.0 . . ?
C7 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C6 C3 C2 117.2(4) . . ?
C6 C3 N3 121.4(4) . . ?
C2 C3 N3 121.4(4) . . ?
C2 C4 C9 118.8(4) . . ?
C2 C4 C5 120.8(4) . . ?
C9 C4 C5 120.3(4) . . ?
O2 C5 O1 122.9(4) . . ?
O2 C5 C4 120.7(4) . . ?
O1 C5 C4 116.3(4) . . ?
C3 N3 H3A 120.0 . . ?
C3 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C1 C6 C3 121.0(4) . . ?
C1 C6 H8 119.5 . . ?
C3 C6 H8 119.5 . . ?
N1 C7 C8 121.8(4) . . ?
N1 C7 C11 121.9(4) . . ?
C8 C7 C11 116.3(4) . . ?
C10 C8 C7 119.5(4) . . ?
C10 C8 H13 120.3 . . ?
C7 C8 H13 120.3 . . ?
O3 C9 C1 119.2(4) . . ?
O3 C9 C4 122.4(4) . . ?
C1 C9 C4 118.5(4) . . ?
N2 C10 C8 121.9(4) . . ?
N2 C10 H12 119.1 . . ?
C8 C10 H12 119.1 . . ?
C12 C11 C7 120.5(4) . . ?
C12 C11 H10 119.8 . . ?
C7 C11 H10 119.8 . . ?
N2 C12 C11 121.3(4) . . ?
N2 C12 H11 119.3 . . ?
C11 C12 H11 119.3 . . ?

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
C4 C2 C3 C6 0.1(6) . . . . ?
C4 C2 C3 N3 -179.5(4) . . . . ?
C3 C2 C4 C9 0.7(6) . . . . ?
C3 C2 C4 C5 -176.0(4) . . . . ?
C2 C4 C5 O2 0.1(6) . . . . ?
C9 C4 C5 O2 -176.5(4) . . . . ?
C2 C4 C5 O1 177.7(4) . . . . ?
C9 C4 C5 O1 1.1(6) . . . . ?
C9 C1 C6 C3 -0.1(7) . . . . ?
C2 C3 C6 C1 -0.4(6) . . . . ?
N3 C3 C6 C1 179.2(4) . . . . ?
N1 C7 C8 C10 178.8(4) . . . . ?
C11 C7 C8 C10 -2.5(6) . . . . ?
C6 C1 C9 O3 179.4(4) . . . . ?
C6 C1 C9 C4 0.8(7) . . . . ?
C2 C4 C9 O3 -179.6(4) . . . . ?
C5 C4 C9 O3 -2.9(6) . . . . ?
C2 C4 C9 C1 -1.1(6) . . . . ?
C5 C4 C9 C1 175.5(4) . . . . ?
C12 N2 C10 C8 0.8(7) . . . . ?
C7 C8 C10 N2 0.8(7) . . . . ?
N1 C7 C11 C12 -178.6(4) . . . . ?
C8 C7 C11 C12 2.8(6) . . . . ?
C10 N2 C12 C11 -0.6(7) . . . . ?
C7 C11 C12 N2 -1.3(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H11 O2 0.93 2.48 3.220(6) 137.2 3_666
C6 H8 O1 0.93 2.55 3.347(6) 143.9 1_556
N3 H3B O2 0.86 2.59 3.071(5) 116.8 3_566
N3 H3A O2 0.86 2.57 3.295(5) 142.2 1_556
N1 H1B O3 0.86 2.12 2.950(5) 163.5 .
N1 H1A N3 0.86 2.25 3.078(5) 161.0 2_656
O3 H3 O1 0.82 1.77 2.501(4) 146.9 .
N2 H2 O1 0.86 1.87 2.715(5) 169.5 1_656
C12 H11 O2 0.93 2.48 3.220(6) 137.2 3_666
C6 H8 O1 0.93 2.55 3.347(6) 143.9 1_556
N3 H3B O2 0.86 2.59 3.071(5) 116.8 3_566
N3 H3A O2 0.86 2.57 3.295(5) 142.2 1_556
N1 H1B O3 0.86 2.12 2.950(5) 163.5 .
N1 H1A N3 0.86 2.25 3.078(5) 161.0 2_656
O3 H3 O1 0.82 1.77 2.501(4) 146.9 .
N2 H2 O1 0.86 1.87 2.715(5) 169.5 1_656
N1 H1B O3 0.86 2.12 2.950(5) 163.5 .
N2 H2 O2 0.86 2.75 3.322(5) 125.4 1_656
N2 H2 O1 0.86 1.87 2.715(5) 169.5 1_656
O3 H3 O1 0.82 1.77 2.501(4) 146.9 .
N1 H1A N3 0.86 2.25 3.078(5) 161.0 2_656
N3 H3A O2 0.86 2.57 3.295(5) 142.2 1_556
N3 H3B O2 0.86 2.59 3.071(5) 116.8 3_566
C12 H11 O2 0.93 2.48 3.220(6) 137.2 3_666
C6 H8 O1 0.93 2.55 3.347(6) 143.9 1_556
N2 H2 O1 0.86 1.87 2.715(5) 169.5 1_656
O3 H3 O1 0.82 1.77 2.501(4) 146.9 .
N1 H1A N3 0.86 2.25 3.078(5) 161.0 2_656
N1 H1B O3 0.86 2.12 2.950(5) 163.5 .
N3 H3A O2 0.86 2.57 3.295(5) 142.2 1_556
N3 H3B O2 0.86 2.59 3.071(5) 116.8 3_566
C6 H8 O1 0.93 2.55 3.347(6) 143.9 1_556
C12 H11 O2 0.93 2.48 3.220(6) 137.2 3_666

_refine_diff_density_max         0.333
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_solid2
_database_code_depnum_ccdc_archive 'CCDC 1474388'
_audit_update_record             
;
2017-06-24 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;

_audit_creation_method           'SHELXTL-NT2000 ver.6.12'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H8 N O3, H O4 S, H2 O'
_chemical_formula_sum            'C7 H11 N O8 S'
_chemical_formula_weight         269.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   12.419(3)
_cell_length_b                   6.8084(14)
_cell_length_c                   13.235(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.272(3)
_cell_angle_gamma                90.00
_cell_volume                     1056.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1725
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      27.13

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.385
_exptl_crystal_size_mid          0.355
_exptl_crystal_size_min          0.298
_exptl_absorpt_coefficient_mu    0.340
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.731
_exptl_absorpt_correction_T_max  0.775
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5282
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.737
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_full        24.993
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1848
_reflns_number_gt                1671
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0398P)²+0.9379P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1848
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1077
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.162
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.002

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
S1 S 0.62682(5) 0.19970(11) 0.35526(5) 0.0243(2) Uani 1 1 d . . . . .
O1 O 1.17968(16) 0.6188(3) 0.32723(15) 0.0374(5) Uani 1 1 d . . . . .
O2 O 1.09085(17) 0.6279(3) 0.44871(15) 0.0366(5) Uani 1 1 d . . . . .
H2 H 1.1566 0.6283 0.4903 0.055 Uiso 1 1 calc R U . . .
O3 O 1.05742(17) 0.6004(4) 0.12384(15) 0.0378(5) Uani 1 1 d . . . . .
H3 H 1.1168 0.6032 0.1749 0.057 Uiso 1 1 calc R U . . .
O6 O 0.55333(17) 0.2675(3) 0.24584(15) 0.0335(5) Uani 1 1 d . . . . .
H15 H 0.5711 0.2076 0.2000 0.050 Uiso 1 1 calc R U . . .
O8 O 0.69942(16) 0.3666(3) 0.40580(15) 0.0333(5) Uani 1 1 d . . . . .
O7 O 0.54893(17) 0.1528(3) 0.41421(15) 0.0363(5) Uani 1 1 d . . . . .
O5 O 0.69436(16) 0.0334(3) 0.34469(16) 0.0357(5) Uani 1 1 d . . . . .
C1 C 0.9785(2) 0.6238(4) 0.2681(2) 0.0255(6) Uani 1 1 d . . . . .
O4 O 0.5949(2) 0.1243(5) 0.0924(2) 0.0516(7) Uani 1 1 d . . . . .
N1 N 0.67273(19) 0.6667(3) 0.24992(19) 0.0303(6) Uani 1 1 d . . . . .
H1A H 0.6722 0.5751 0.2978 0.045 Uiso 1 1 calc R U . . .
H1B H 0.6106 0.6545 0.1926 0.045 Uiso 1 1 calc R U . . .
H1C H 0.6736 0.7852 0.2786 0.045 Uiso 1 1 calc R U . . .
C2 C 0.9681(2) 0.6120(4) 0.1593(2) 0.0267(6) Uani 1 1 d . . . . .
C3 C 0.8801(2) 0.6382(4) 0.2966(2) 0.0259(6) Uani 1 1 d . . . . .
H3A H 0.8857 0.6449 0.3683 0.031 Uiso 1 1 calc R U . . .
C4 C 0.7640(2) 0.6280(4) 0.1112(2) 0.0324(7) Uani 1 1 d . . . . .
H4 H 0.6921 0.6289 0.0592 0.039 Uiso 1 1 calc R U . . .
C5 C 0.7749(2) 0.6423(4) 0.2183(2) 0.0263(6) Uani 1 1 d . . . . .
C6 C 0.8604(2) 0.6123(4) 0.0821(2) 0.0323(7) Uani 1 1 d . . . . .
H6 H 0.8533 0.6017 0.0101 0.039 Uiso 1 1 calc R U . . .
C7 C 1.0919(2) 0.6220(4) 0.3505(2) 0.0257(6) Uani 1 1 d . . . . .
H2W H 0.664(4) 0.116(6) 0.113(3) 0.066(14) Uiso 1 1 d . . . . .
H1W H 0.572(5) 0.194(8) 0.038(4) 0.10(2) 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
S1 O5 1.443(2) . ?
S1 O7 1.465(2) . ?
S1 O8 1.467(2) . ?
S1 O6 1.5070(19) . ?
O1 C7 1.227(3) . ?
O2 C7 1.305(3) . ?
O2 H2 0.8200 . ?
O3 C2 1.341(3) . ?
O3 H3 0.8200 . ?
O6 H15 0.8200 . ?
C1 C3 1.396(4) . ?
C1 C2 1.405(4) . ?
C1 C7 1.470(4) . ?
O4 H2W 0.81(4) . ?
O4 H1W 0.83(5) . ?
N1 C5 1.471(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C2 C6 1.390(4) . ?
C3 C5 1.374(4) . ?
C3 H3A 0.9300 . ?
C4 C6 1.377(4) . ?
C4 C5 1.382(4) . ?
C4 H4 0.9300 . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 S1 O7 112.81(13) . . ?
O5 S1 O8 111.25(12) . . ?
O7 S1 O8 109.91(12) . . ?
O5 S1 O6 109.53(12) . . ?
O7 S1 O6 106.37(12) . . ?
O8 S1 O6 106.67(12) . . ?
C7 O2 H2 109.5 . . ?
C2 O3 H3 109.5 . . ?
S1 O6 H15 109.5 . . ?
C3 C1 C2 119.2(3) . . ?
C3 C1 C7 120.7(2) . . ?
C2 C1 C7 120.1(2) . . ?
H2W O4 H1W 111(5) . . ?
C5 N1 H1A 109.5 . . ?
C5 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C5 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
O3 C2 C6 116.7(2) . . ?
O3 C2 C1 123.7(2) . . ?
C6 C2 C1 119.6(3) . . ?
C5 C3 C1 119.8(3) . . ?
C5 C3 H3A 120.1 . . ?
C1 C3 H3A 120.1 . . ?
C6 C4 C5 119.5(3) . . ?
C6 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C3 C5 C4 121.3(3) . . ?
C3 C5 N1 118.8(2) . . ?
C4 C5 N1 119.9(2) . . ?
C4 C6 C2 120.6(3) . . ?
C4 C6 H6 119.7 . . ?
C2 C6 H6 119.7 . . ?
O1 C7 O2 123.5(3) . . ?
O1 C7 C1 121.8(2) . . ?
O2 C7 C1 114.6(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
C3 C1 C2 O3 179.1(3) . . . . ?
C7 C1 C2 O3 -0.6(4) . . . . ?
C3 C1 C2 C6 -0.9(4) . . . . ?
C7 C1 C2 C6 179.5(3) . . . . ?
C2 C1 C3 C5 -0.5(4) . . . . ?
C7 C1 C3 C5 179.1(3) . . . . ?
C1 C3 C5 C4 1.5(4) . . . . ?
C1 C3 C5 N1 -177.2(2) . . . . ?
C6 C4 C5 C3 -1.0(4) . . . . ?
C6 C4 C5 N1 177.7(3) . . . . ?
C5 C4 C6 C2 -0.4(5) . . . . ?
O3 C2 C6 C4 -178.6(3) . . . . ?
C1 C2 C6 C4 1.3(4) . . . . ?
C3 C1 C7 O1 -176.5(3) . . . . ?
C2 C1 C7 O1 3.2(4) . . . . ?
C3 C1 C7 O2 2.2(4) . . . . ?
C2 C1 C7 O2 -178.1(3) . . . . ?

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
O4 H1W O7 0.83(5) 1.88(6) 2.703(4) 169(5) 4_565
O4 H1W S1 0.83(5) 2.81(5) 3.502(3) 142(5) 4_565
O4 H2W O1 0.81(4) 1.84(4) 2.646(3) 173(4) 2_745
C6 H6 O5 0.93 2.59 3.291(3) 133.1 4_565
N1 H1C O5 0.89 1.88 2.767(3) 173.2 1_565
N1 H1B O7 0.89 2.02 2.891(3) 166.5 2_655
N1 H1B S1 0.89 2.82 3.523(2) 136.8 2_655
N1 H1A O8 0.89 1.96 2.844(3) 169.9 .
N1 H1A O6 0.89 2.52 3.088(3) 121.9 .
N1 H1A S1 0.89 2.78 3.592(3) 152.8 .
O6 H15 O4 0.82 1.65 2.456(3) 168.6 .
O3 H3 O5 0.82 2.49 3.006(3) 122.1 2_755
O3 H3 O1 0.82 1.91 2.621(3) 144.5 .
O2 H2 O8 0.82 1.86 2.680(3) 175.0 3_766
O2 H2 S1 0.82 3.03 3.794(2) 157.0 3_766

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_solid7
_database_code_depnum_ccdc_archive 'CCDC 1474396'
_audit_update_record             
;
2017-06-24 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;

_audit_creation_method           'SHELXTL-NT2000 ver.6.12'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 N2, 2(C7 H7 N O3)'
_chemical_formula_sum            'C24 H22 N4 O6'
_chemical_formula_weight         462.46

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           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'

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

_cell_length_a                   8.187(5)
_cell_length_b                   15.276(10)
_cell_length_c                   17.425(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2179(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    524
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      27.36

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.443
_exptl_crystal_size_mid          0.319
_exptl_crystal_size_min          0.226
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14217
_diffrn_reflns_av_unetI/netI     0.0957
_diffrn_reflns_av_R_equivalents  0.1111
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.338
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1924
_reflns_number_gt                1053
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0784P)²+1.0178P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1924
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1736
_refine_ls_R_factor_gt           0.0954
_refine_ls_wR_factor_ref         0.2069
_refine_ls_wR_factor_gt          0.1719
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.1204(4) 0.1125(2) 0.67875(19) 0.0591(11) Uani 1 1 d . . . . .
O2 O 1.0231(4) 0.0816(2) 0.56353(17) 0.0423(9) Uani 1 1 d . . . . .
O3 O 0.9311(4) 0.1403(3) 0.7893(2) 0.0785(14) Uani 1 1 d . . . . .
H3 H 1.0180 0.1346 0.7664 0.118 Uiso 1 1 calc R U . . .
N1 N 0.3414(5) 0.2262(3) 0.9620(3) 0.0536(13) Uani 1 1 d . . . . .
N2 N 0.4056(4) 0.1031(2) 0.5910(2) 0.0389(11) Uani 1 1 d . . . . .
H2A H 0.3148 0.0966 0.6185 0.058 Uiso 1 1 calc R U . . .
H2B H 0.4205 0.0560 0.5617 0.058 Uiso 1 1 calc R U . . .
H2C H 0.3966 0.1503 0.5613 0.058 Uiso 1 1 calc R U . . .
C1 C 1.0030(6) 0.1027(3) 0.6318(3) 0.0363(12) Uani 1 1 d . . . . .
C2 C 0.8334(5) 0.1158(3) 0.6624(3) 0.0329(11) Uani 1 1 d . . . . .
C3 C 0.8078(6) 0.1303(3) 0.7403(3) 0.0496(15) Uani 1 1 d . . . . .
C4 C 0.6480(6) 0.1362(4) 0.7681(3) 0.0685(19) Uani 1 1 d . . . . .
H7 H 0.6295 0.1468 0.8199 0.082 Uiso 1 1 calc R U . . .
C5 C 0.5191(6) 0.1263(4) 0.7192(3) 0.0544(15) Uani 1 1 d . . . . .
H6 H 0.4130 0.1284 0.7382 0.065 Uiso 1 1 calc R U . . .
C6 C 0.5445(5) 0.1135(3) 0.6424(3) 0.0339(11) Uani 1 1 d . . . . .
C7 C 0.7018(5) 0.1077(3) 0.6144(2) 0.0310(11) Uani 1 1 d . . . . .
H5 H 0.7187 0.0981 0.5623 0.037 Uiso 1 1 calc R U . . .
C8 C 0.2842(7) 0.1849(4) 0.9018(3) 0.0601(16) Uani 1 1 d . . . . .
H8 H 0.2668 0.2172 0.8573 0.072 Uiso 1 1 calc R U . . .
C9 C 0.3602(6) 0.1790(4) 1.0250(3) 0.0555(15) Uani 1 1 d . . . . .
H11 H 0.3978 0.2068 1.0690 0.067 Uiso 1 1 calc R U . . .
C10 C 0.3269(6) 0.0901(3) 1.0288(3) 0.0520(15) Uani 1 1 d . . . . .
H10 H 0.3437 0.0597 1.0743 0.062 Uiso 1 1 calc R U . . .
C11 C 0.2688(5) 0.0471(3) 0.9650(3) 0.0383(12) Uani 1 1 d . . . . .
C12 C 0.2483(7) 0.0967(4) 0.9002(3) 0.0562(15) Uani 1 1 d . . . . .
H9 H 0.2104 0.0710 0.8552 0.067 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.271(5) . ?
O2 C1 1.243(5) . ?
O3 C3 1.331(6) . ?
O3 H3 0.8200 . ?
N1 C8 1.311(6) . ?
N1 C9 1.322(6) . ?
N2 C6 1.457(5) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
C1 C2 1.501(6) . ?
C2 C7 1.369(6) . ?
C2 C3 1.390(6) . ?
C3 C4 1.399(7) . ?
C4 C5 1.364(6) . ?
C4 H7 0.9300 . ?
C5 C6 1.368(6) . ?
C5 H6 0.9300 . ?
C6 C7 1.380(6) . ?
C7 H5 0.9300 . ?
C8 C12 1.379(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.386(7) . ?
C9 H11 0.9300 . ?
C10 C11 1.375(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(6) . ?
C11 C11 1.473(9) 2 ?
C12 H9 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O3 H3 109.5 . . ?
C8 N1 C9 116.3(5) . . ?
C6 N2 H2A 109.5 . . ?
C6 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C6 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
O2 C1 O1 123.2(4) . . ?
O2 C1 C2 119.8(4) . . ?
O1 C1 C2 117.1(4) . . ?
C7 C2 C3 119.5(4) . . ?
C7 C2 C1 119.9(4) . . ?
C3 C2 C1 120.5(4) . . ?
O3 C3 C2 122.1(4) . . ?
O3 C3 C4 118.7(5) . . ?
C2 C3 C4 119.3(4) . . ?
C5 C4 C3 120.0(5) . . ?
C5 C4 H7 120.0 . . ?
C3 C4 H7 120.0 . . ?
C4 C5 C6 120.5(5) . . ?
C4 C5 H6 119.7 . . ?
C6 C5 H6 119.7 . . ?
C5 C6 C7 119.8(4) . . ?
C5 C6 N2 119.9(4) . . ?
C7 C6 N2 120.3(4) . . ?
C2 C7 C6 120.8(4) . . ?
C2 C7 H5 119.6 . . ?
C6 C7 H5 119.6 . . ?
N1 C8 C12 124.2(5) . . ?
N1 C8 H8 117.9 . . ?
C12 C8 H8 117.9 . . ?
N1 C9 C10 123.5(5) . . ?
N1 C9 H11 118.3 . . ?
C10 C9 H11 118.3 . . ?
C11 C10 C9 119.8(5) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C12 C11 C10 116.4(5) . . ?
C12 C11 C11 121.0(3) . 2 ?
C10 C11 C11 122.6(3) . 2 ?
C11 C12 C8 119.8(5) . . ?
C11 C12 H9 120.1 . . ?
C8 C12 H9 120.1 . . ?

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
O2 C1 C2 C7 -2.4(6) . . . . ?
O1 C1 C2 C7 178.8(4) . . . . ?
O2 C1 C2 C3 173.2(4) . . . . ?
O1 C1 C2 C3 -5.5(6) . . . . ?
C7 C2 C3 O3 -178.7(5) . . . . ?
C1 C2 C3 O3 5.6(8) . . . . ?
C7 C2 C3 C4 0.1(8) . . . . ?
C1 C2 C3 C4 -175.6(5) . . . . ?
O3 C3 C4 C5 179.9(5) . . . . ?
C2 C3 C4 C5 1.0(9) . . . . ?
C3 C4 C5 C6 -2.1(9) . . . . ?
C4 C5 C6 C7 2.1(8) . . . . ?
C4 C5 C6 N2 180.0(5) . . . . ?
C3 C2 C7 C6 -0.2(7) . . . . ?
C1 C2 C7 C6 175.6(4) . . . . ?
C5 C6 C7 C2 -0.9(7) . . . . ?
N2 C6 C7 C2 -178.8(4) . . . . ?
C9 N1 C8 C12 -1.9(8) . . . . ?
C8 N1 C9 C10 1.7(8) . . . . ?
N1 C9 C10 C11 -1.0(8) . . . . ?
C9 C10 C11 C12 0.4(7) . . . . ?
C9 C10 C11 C11 179.8(5) . . . 2 ?
C10 C11 C12 C8 -0.6(7) . . . . ?
C11 C11 C12 C8 179.9(5) 2 . . . ?
N1 C8 C12 C11 1.5(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5 H6 O1 0.93 2.62 3.345(6) 135.2 1_455
N2 H2C N1 0.89 1.98 2.816(6) 155.4 4_556
N2 H2B O2 0.89 2.37 2.878(5) 116.3 6_556
N2 H2B O2 0.89 2.15 2.920(5) 144.1 2_655
N2 H2A O2 0.89 2.58 3.185(5) 125.6 1_455
N2 H2A O1 0.89 1.92 2.794(5) 166.3 1_455
O3 H3 O1 0.82 1.77 2.508(5) 148.0 .
C5 H6 O1 0.93 2.62 3.345(6) 135.2 1_455
N2 H2C N1 0.89 1.98 2.816(6) 155.4 4_556
N2 H2B O2 0.89 2.37 2.878(5) 116.3 6_556
N2 H2B O2 0.89 2.15 2.920(5) 144.1 2_655
N2 H2A O2 0.89 2.58 3.185(5) 125.6 1_455
N2 H2A O1 0.89 1.92 2.794(5) 166.3 1_455
O3 H3 O1 0.82 1.77 2.508(5) 148.0 .
O3 H3 O1 0.82 1.77 2.508(5) 148.0 .
C5 H6 O1 0.93 2.62 3.345(6) 135.2 1_455
N2 H2C N1 0.89 1.98 2.816(6) 155.4 4_556
N2 H2B O2 0.89 2.37 2.878(5) 116.3 6_556
N2 H2B O2 0.89 2.15 2.920(5) 144.1 2_655
N2 H2A O2 0.89 2.58 3.185(5) 125.6 1_455
N2 H2A O1 0.89 1.92 2.794(5) 166.3 1_455
O3 H3 O1 0.82 1.77 2.508(5) 148.0 .
N2 H2A O1 0.89 1.92 2.794(5) 166.3 1_455
N2 H2A O2 0.89 2.58 3.185(5) 125.6 1_455
N2 H2B O2 0.89 2.15 2.920(5) 144.1 2_655
N2 H2B O2 0.89 2.37 2.878(5) 116.3 6_556
N2 H2C N1 0.89 1.98 2.816(6) 155.4 4_556
C5 H6 O1 0.93 2.62 3.345(6) 135.2 1_455

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_solid4
_database_code_depnum_ccdc_archive 'CCDC 1474393'
_audit_update_record             
;
2017-06-24 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;

_audit_creation_method           'SHELXTL-NT2000 ver.6.12'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H8 N O3, C2 Cl3 O2'
_chemical_formula_sum            'C9 H8 Cl3 N O5'
_chemical_formula_weight         316.47

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   16.767(4)
_cell_length_b                   6.8109(14)
_cell_length_c                   22.399(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2558.0(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5438
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      27.42

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.486
_exptl_crystal_size_mid          0.378
_exptl_crystal_size_min          0.271
_exptl_absorpt_coefficient_mu    0.723
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.720
_exptl_absorpt_correction_T_max  0.812
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20905
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.818
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2245
_reflns_number_gt                2001
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0980P)²+8.0522P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2245
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0970
_refine_ls_wR_factor_ref         0.2298
_refine_ls_wR_factor_gt          0.2266
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_restrained_S_all      1.130
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.020

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
Cl1 Cl 0.3160(2) 0.6751(5) 0.31545(14) 0.1512(16) Uani 1 1 d . . . . .
Cl2 Cl 0.48226(18) 0.7351(5) 0.28398(9) 0.1226(12) Uani 1 1 d . . . . .
Cl3 Cl 0.38955(14) 1.0441(3) 0.33066(9) 0.0885(7) Uani 1 1 d . . . . .
O1 O 0.4684(2) 0.8475(5) 0.42707(16) 0.0479(9) Uani 1 1 d . . . . .
O2 O 0.4237(2) 0.5465(5) 0.40892(17) 0.0468(9) Uani 1 1 d . . . . .
O3 O 0.3772(2) 0.2109(6) 0.0220(2) 0.0582(11) Uani 1 1 d . . . . .
O4 O 0.2854(2) 0.1052(6) -0.04184(16) 0.0480(9) Uani 1 1 d . . . . .
H4 H 0.3245 0.0905 -0.0634 0.072 Uiso 1 1 calc R U . . .
O5 O 0.3339(2) 0.3133(6) 0.12987(19) 0.0572(11) Uani 1 1 d . . . . .
H5 H 0.3656 0.2978 0.1024 0.086 Uiso 1 1 calc R U . . .
N1 N 0.0200(2) 0.2342(6) 0.05155(19) 0.0407(10) Uani 1 1 d . . . . .
H1A H -0.0026 0.1290 0.0680 0.061 Uiso 1 1 calc R U . . .
H1B H 0.0190 0.2226 0.0120 0.061 Uiso 1 1 calc R U . . .
H1C H -0.0068 0.3413 0.0623 0.061 Uiso 1 1 calc R U . . .
C1 C 0.3077(3) 0.1817(6) 0.0092(2) 0.0402(11) Uani 1 1 d . . . . .
C2 C 0.2433(3) 0.2237(6) 0.0516(2) 0.0358(11) Uani 1 1 d . . . . .
C3 C 0.2597(3) 0.2900(7) 0.1095(2) 0.0428(12) Uani 1 1 d . . . . .
C4 C 0.1956(4) 0.3294(7) 0.1478(2) 0.0475(13) Uani 1 1 d . . . . .
H6 H 0.2061 0.3695 0.1867 0.057 Uiso 1 1 calc R U . . .
C5 C 0.1172(4) 0.3104(7) 0.1293(2) 0.0468(13) Uani 1 1 d . . . . .
H7 H 0.0751 0.3378 0.1551 0.056 Uiso 1 1 calc R U . . .
C6 C 0.1036(3) 0.2503(6) 0.0721(2) 0.0367(11) Uani 1 1 d . . . . .
C7 C 0.1638(3) 0.2040(6) 0.0336(2) 0.0332(10) Uani 1 1 d . . . . .
H8 H 0.1519 0.1593 -0.0046 0.040 Uiso 1 1 calc R U . . .
C8 C 0.4358(3) 0.7222(7) 0.3969(2) 0.0330(10) Uani 1 1 d . . . . .
C9 C 0.4055(4) 0.7899(9) 0.3335(2) 0.0535(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
Cl1 C9 1.740(6) . ?
Cl2 C9 1.739(7) . ?
Cl3 C9 1.753(6) . ?
O1 C8 1.218(6) . ?
O2 C8 1.243(6) . ?
O3 C1 1.216(6) . ?
O4 C1 1.311(6) . ?
O4 H4 0.8200 . ?
O5 C3 1.335(6) . ?
O5 H5 0.8200 . ?
N1 C6 1.480(6) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C1 C2 1.466(7) . ?
C2 C7 1.399(7) . ?
C2 C3 1.402(7) . ?
C3 C4 1.400(8) . ?
C4 C5 1.385(8) . ?
C4 H6 0.9300 . ?
C5 C6 1.364(7) . ?
C5 H7 0.9300 . ?
C6 C7 1.365(7) . ?
C7 H8 0.9300 . ?
C8 C9 1.577(7) . ?

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
C1 O4 H4 109.5 . . ?
C3 O5 H5 109.5 . . ?
C6 N1 H1A 109.5 . . ?
C6 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C6 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
O3 C1 O4 122.9(5) . . ?
O3 C1 C2 121.5(5) . . ?
O4 C1 C2 115.6(4) . . ?
C7 C2 C3 118.9(5) . . ?
C7 C2 C1 119.8(4) . . ?
C3 C2 C1 121.2(5) . . ?
O5 C3 C4 118.9(5) . . ?
O5 C3 C2 122.5(5) . . ?
C4 C3 C2 118.6(5) . . ?
C5 C4 C3 121.8(5) . . ?
C5 C4 H6 119.1 . . ?
C3 C4 H6 119.1 . . ?
C6 C5 C4 117.9(5) . . ?
C6 C5 H7 121.1 . . ?
C4 C5 H7 121.1 . . ?
C5 C6 C7 122.7(5) . . ?
C5 C6 N1 118.2(4) . . ?
C7 C6 N1 119.1(4) . . ?
C6 C7 C2 120.1(4) . . ?
C6 C7 H8 120.0 . . ?
C2 C7 H8 120.0 . . ?
O1 C8 O2 128.9(5) . . ?
O1 C8 C9 116.1(4) . . ?
O2 C8 C9 115.1(4) . . ?
C8 C9 Cl2 105.8(4) . . ?
C8 C9 Cl1 110.8(4) . . ?
Cl2 C9 Cl1 113.2(4) . . ?
C8 C9 Cl3 111.8(4) . . ?
Cl2 C9 Cl3 107.6(3) . . ?
Cl1 C9 Cl3 107.7(4) . . ?

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
O3 C1 C2 C7 174.7(5) . . . . ?
O4 C1 C2 C7 -7.6(6) . . . . ?
O3 C1 C2 C3 -3.2(7) . . . . ?
O4 C1 C2 C3 174.5(4) . . . . ?
C7 C2 C3 O5 -179.8(4) . . . . ?
C1 C2 C3 O5 -1.9(7) . . . . ?
C7 C2 C3 C4 1.5(7) . . . . ?
C1 C2 C3 C4 179.4(4) . . . . ?
O5 C3 C4 C5 179.2(5) . . . . ?
C2 C3 C4 C5 -2.0(7) . . . . ?
C3 C4 C5 C6 0.4(7) . . . . ?
C4 C5 C6 C7 1.8(7) . . . . ?
C4 C5 C6 N1 -178.6(4) . . . . ?
C5 C6 C7 C2 -2.2(7) . . . . ?
N1 C6 C7 C2 178.1(4) . . . . ?
C3 C2 C7 C6 0.5(7) . . . . ?
C1 C2 C7 C6 -177.4(4) . . . . ?
O1 C8 C9 Cl2 93.5(5) . . . . ?
O2 C8 C9 Cl2 -85.9(5) . . . . ?
O1 C8 C9 Cl1 -143.4(4) . . . . ?
O2 C8 C9 Cl1 37.2(6) . . . . ?
O1 C8 C9 Cl3 -23.3(6) . . . . ?
O2 C8 C9 Cl3 157.3(4) . . . . ?

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
C7 H8 O1 0.93 2.53 3.276(6) 137.1 2_564
N1 H1C O2 0.89 1.93 2.813(5) 171.3 6_556
N1 H1B O1 0.89 1.97 2.850(6) 168.5 2_564
N1 H1A O1 0.89 1.98 2.813(5) 155.0 6_546
N1 H1A Cl3 0.89 2.96 3.663(5) 137.3 6_546
O5 H5 O3 0.82 1.91 2.618(6) 144.6 .
O4 H4 O2 0.82 2.01 2.768(5) 154.4 7_565
C7 H8 O1 0.93 2.53 3.276(6) 137.1 2_564
N1 H1B O1 0.89 1.97 2.850(6) 168.5 2_564
N1 H1C O2 0.89 1.93 2.813(5) 171.3 6_556
O5 H5 O3 0.82 1.91 2.618(6) 144.6 .
O4 H4 O2 0.82 2.01 2.768(5) 154.4 7_565
N1 H1A O1 0.89 1.98 2.813(5) 155.0 6_546

_refine_diff_density_max         0.816
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.095

####################################################################### 
# 
# 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_solid1
_database_code_depnum_ccdc_archive 'CCDC 1474387'
_audit_update_record             
;
2017-06-24 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;

_audit_creation_method           'SHELXTL-NT2000 ver.6.12'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C7 H8 N O3), O4 S, H2 O'
_chemical_formula_sum            'C14 H18 N2 O11 S'
_chemical_formula_weight         422.36

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.710(4)
_cell_length_b                   11.379(7)
_cell_length_c                   12.011(7)
_cell_angle_alpha                108.276(10)
_cell_angle_beta                 90.859(11)
_cell_angle_gamma                102.008(10)
_cell_volume                     848.6(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    488
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      24.85

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.434
_exptl_crystal_size_mid          0.335
_exptl_crystal_size_min          0.281
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7666
_diffrn_reflns_av_unetI/netI     0.1795
_diffrn_reflns_av_R_equivalents  0.1160
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.934
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2959
_reflns_number_gt                1405
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0271P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2959
_refine_ls_number_parameters     267
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1374
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.1172
_refine_ls_wR_factor_gt          0.0992
_refine_ls_goodness_of_fit_ref   0.839
_refine_ls_restrained_S_all      0.839
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001

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
S1 S 0.28812(19) 0.58442(12) 0.15108(10) 0.0283(3) Uani 1 1 d . . . . .
O6 O 0.1309(4) 0.6005(3) 0.2368(2) 0.0315(8) Uani 1 1 d . . . . .
O3 O 0.3201(5) 0.6947(3) 0.1065(2) 0.0363(9) Uani 1 1 d . . . . .
O1 O 0.2338(5) 0.8477(3) 0.4849(3) 0.0451(10) Uani 1 1 d . . . . .
O10 O 0.3409(5) 1.0070(3) 0.7011(3) 0.0420(9) Uani 1 1 d . . . . .
H10 H 0.3119 0.9872 0.6301 0.063 Uiso 1 1 calc R U . . .
O5 O 0.4829(4) 0.5852(3) 0.2104(2) 0.0379(9) Uani 1 1 d . . . . .
O4 O 0.2158(5) 0.4679(3) 0.0532(3) 0.0467(10) Uani 1 1 d . . . . .
C1 C 0.2580(6) 0.7790(5) 0.6530(4) 0.0258(11) Uani 1 1 d . . . . .
O2 O 0.1893(6) 0.6403(3) 0.4588(3) 0.0469(10) Uani 1 1 d . . . . .
H2 H 0.1790 0.6353 0.3893 0.070 Uiso 1 1 calc R U . . .
C2 C 0.3142(7) 0.8137(5) 0.8908(4) 0.0323(13) Uani 1 1 d . . . . .
H2A H 0.3331 0.8253 0.9708 0.039 Uiso 1 1 calc R U . . .
N1 N 0.2456(5) 0.5829(3) 0.8505(3) 0.0315(10) Uani 1 1 d . . . . .
H1A H 0.1249 0.5301 0.8226 0.047 Uiso 1 1 calc R U . . .
H1B H 0.2548 0.6086 0.9288 0.047 Uiso 1 1 calc R U . . .
H1C H 0.3451 0.5430 0.8247 0.047 Uiso 1 1 calc R U . . .
C3 C 0.3107(7) 0.9017(5) 0.7327(4) 0.0310(12) Uani 1 1 d . . . . .
O8 O 0.3130(6) 0.2396(3) 0.6009(3) 0.0520(10) Uani 1 1 d . . . . .
H8 H 0.3550 0.2940 0.6646 0.078 Uiso 1 1 calc R U . . .
C4 C 0.2653(6) 0.6928(5) 0.8100(4) 0.0282(12) Uani 1 1 d . . . . .
O9 O 0.2893(6) 0.3742(3) 0.3143(3) 0.0529(11) Uani 1 1 d . . . . .
H9 H 0.3270 0.4170 0.3829 0.079 Uiso 1 1 calc R U . . .
N2 N 0.0903(6) -0.1436(4) 0.2468(3) 0.0433(11) Uani 1 1 d . . . . .
H2B H 0.1833 -0.1802 0.2060 0.065 Uiso 1 1 calc R U . . .
H2C H -0.0316 -0.1758 0.2063 0.065 Uiso 1 1 calc R U . . .
H2D H 0.0851 -0.1582 0.3155 0.065 Uiso 1 1 calc R U . . .
O7 O 0.3395(6) 0.4105(4) 0.5416(3) 0.0607(12) Uani 1 1 d . . . . .
C5 C 0.3348(7) 0.9173(5) 0.8518(4) 0.0366(13) Uani 1 1 d . . . . .
H5 H 0.3653 0.9987 0.9062 0.044 Uiso 1 1 calc R U . . .
C6 C 0.1969(6) 0.0739(4) 0.3807(4) 0.0300(12) Uani 1 1 d . . . . .
H6 H 0.1990 0.0426 0.4434 0.036 Uiso 1 1 calc R U . . .
C7 C 0.1464(7) -0.0065(4) 0.2678(4) 0.0300(12) Uani 1 1 d . . . . .
C8 C 0.2422(7) 0.2505(5) 0.3049(5) 0.0379(13) Uani 1 1 d . . . . .
C9 C 0.2454(7) 0.2054(5) 0.3995(4) 0.0335(13) Uani 1 1 d . . . . .
C10 C 0.2240(7) 0.7593(5) 0.5245(4) 0.0328(13) Uani 1 1 d . . . . .
C11 C 0.1421(6) 0.0371(5) 0.1723(4) 0.0342(13) Uani 1 1 d . . . . .
H11 H 0.1054 -0.0198 0.0966 0.041 Uiso 1 1 calc R U . . .
C12 C 0.1926(7) 0.1654(5) 0.1911(4) 0.0367(13) Uani 1 1 d . . . . .
H12 H 0.1937 0.1957 0.1276 0.044 Uiso 1 1 calc R U . . .
C13 C 0.2344(6) 0.6745(4) 0.6918(4) 0.0285(12) Uani 1 1 d . . . . .
H13 H 0.1981 0.5928 0.6381 0.034 Uiso 1 1 calc R U . . .
C14 C 0.3027(7) 0.2955(5) 0.5186(5) 0.0402(14) Uani 1 1 d . . . . .
O11 O 0.2425(7) 0.2343(4) 0.9168(3) 0.0492(11) Uani 1 1 d D . . . .
H1W H 0.355(10) 0.236(6) 0.912(6) 0.09(3) Uiso 1 1 d . . . . .
H2W H 0.26(2) 0.292(7) 0.903(11) 0.33(9) Uiso 1 1 d 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
S1 O4 1.454(3) . ?
S1 O5 1.476(3) . ?
S1 O6 1.484(3) . ?
S1 O3 1.490(3) . ?
O1 C10 1.231(5) . ?
O10 C3 1.344(5) . ?
O10 H10 0.8200 . ?
C1 C13 1.387(6) . ?
C1 C3 1.392(6) . ?
C1 C10 1.495(6) . ?
O2 C10 1.306(5) . ?
O2 H2 0.8200 . ?
C2 C5 1.381(6) . ?
C2 C4 1.382(6) . ?
C2 H2A 0.9300 . ?
N1 C4 1.460(5) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C3 C5 1.388(6) . ?
O8 C14 1.340(5) . ?
O8 H8 0.8200 . ?
C4 C13 1.375(5) . ?
O9 C8 1.344(5) . ?
O9 H9 0.8200 . ?
N2 C7 1.464(5) . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
N2 H2D 0.8900 . ?
O7 C14 1.220(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.368(6) . ?
C6 C9 1.406(6) . ?
C6 H6 0.9300 . ?
C7 C11 1.388(6) . ?
C8 C9 1.387(6) . ?
C8 C12 1.392(6) . ?
C9 C14 1.465(6) . ?
C11 C12 1.372(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
O11 H2W 0.71(2) . ?
O11 H1W 0.75(6) . ?
O11 H2W 0.71(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
O4 S1 O5 111.72(18) . . ?
O4 S1 O6 109.8(2) . . ?
O5 S1 O6 109.90(18) . . ?
O4 S1 O3 109.2(2) . . ?
O5 S1 O3 108.60(19) . . ?
O6 S1 O3 107.54(18) . . ?
C3 O10 H10 109.5 . . ?
C13 C1 C3 120.6(4) . . ?
C13 C1 C10 119.6(4) . . ?
C3 C1 C10 119.7(4) . . ?
C10 O2 H2 109.5 . . ?
C5 C2 C4 119.4(4) . . ?
C5 C2 H2A 120.3 . . ?
C4 C2 H2A 120.3 . . ?
C4 N1 H1A 109.5 . . ?
C4 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C4 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
O10 C3 C5 117.6(4) . . ?
O10 C3 C1 123.8(5) . . ?
C5 C3 C1 118.6(4) . . ?
C14 O8 H8 109.5 . . ?
C13 C4 C2 120.8(4) . . ?
C13 C4 N1 119.5(4) . . ?
C2 C4 N1 119.7(4) . . ?
C8 O9 H9 109.5 . . ?
C7 N2 H2B 109.5 . . ?
C7 N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C7 N2 H2D 109.5 . . ?
H2B N2 H2D 109.5 . . ?
H2C N2 H2D 109.5 . . ?
C2 C5 C3 121.0(5) . . ?
C2 C5 H5 119.5 . . ?
C3 C5 H5 119.5 . . ?
C7 C6 C9 118.2(4) . . ?
C7 C6 H6 120.9 . . ?
C9 C6 H6 120.9 . . ?
C6 C7 C11 122.3(5) . . ?
C6 C7 N2 119.0(4) . . ?
C11 C7 N2 118.6(4) . . ?
O9 C8 C9 124.2(5) . . ?
O9 C8 C12 115.8(5) . . ?
C9 C8 C12 119.9(5) . . ?
C8 C9 C6 120.1(4) . . ?
C8 C9 C14 119.6(5) . . ?
C6 C9 C14 120.3(5) . . ?
O1 C10 O2 123.5(5) . . ?
O1 C10 C1 122.9(5) . . ?
O2 C10 C1 113.6(4) . . ?
C12 C11 C7 119.1(4) . . ?
C12 C11 H11 120.4 . . ?
C7 C11 H11 120.4 . . ?
C11 C12 C8 120.3(5) . . ?
C11 C12 H12 119.9 . . ?
C8 C12 H12 119.9 . . ?
C4 C13 C1 119.5(4) . . ?
C4 C13 H13 120.2 . . ?
C1 C13 H13 120.2 . . ?
O7 C14 O8 122.7(5) . . ?
O7 C14 C9 123.7(5) . . ?
O8 C14 C9 113.6(5) . . ?
H2W O11 H1W 88(10) . . ?
H1W O11 H2W 88(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
C13 C1 C3 O10 178.3(4) . . . . ?
C10 C1 C3 O10 -2.4(6) . . . . ?
C13 C1 C3 C5 -1.4(6) . . . . ?
C10 C1 C3 C5 177.9(4) . . . . ?
C5 C2 C4 C13 -0.9(7) . . . . ?
C5 C2 C4 N1 179.3(4) . . . . ?
C4 C2 C5 C3 -1.1(7) . . . . ?
O10 C3 C5 C2 -177.5(4) . . . . ?
C1 C3 C5 C2 2.2(7) . . . . ?
C9 C6 C7 C11 0.1(6) . . . . ?
C9 C6 C7 N2 -178.4(4) . . . . ?
O9 C8 C9 C6 -178.9(4) . . . . ?
C12 C8 C9 C6 -0.6(7) . . . . ?
O9 C8 C9 C14 0.1(7) . . . . ?
C12 C8 C9 C14 178.5(4) . . . . ?
C7 C6 C9 C8 -0.2(6) . . . . ?
C7 C6 C9 C14 -179.3(4) . . . . ?
C13 C1 C10 O1 176.8(5) . . . . ?
C3 C1 C10 O1 -2.5(7) . . . . ?
C13 C1 C10 O2 -5.1(6) . . . . ?
C3 C1 C10 O2 175.6(4) . . . . ?
C6 C7 C11 C12 0.9(7) . . . . ?
N2 C7 C11 C12 179.4(4) . . . . ?
C7 C11 C12 C8 -1.7(7) . . . . ?
O9 C8 C12 C11 -179.9(4) . . . . ?
C9 C8 C12 C11 1.6(7) . . . . ?
C2 C4 C13 C1 1.7(6) . . . . ?
N1 C4 C13 C1 -178.5(4) . . . . ?
C3 C1 C13 C4 -0.5(6) . . . . ?
C10 C1 C13 C4 -179.9(4) . . . . ?
C8 C9 C14 O7 3.6(7) . . . . ?
C6 C9 C14 O7 -177.3(5) . . . . ?
C8 C9 C14 O8 -175.8(4) . . . . ?
C6 C9 C14 O8 3.3(6) . . . . ?

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
O11 H2W O4 0.71(2) 2.31(12) 2.694(5) 116(12) 1_556
O11 H1W O3 0.75(6) 2.20(7) 2.920(6) 160(7) 2_666
C13 H13 O7 0.93 2.43 3.209(6) 141.7 .
C6 H6 O1 0.93 2.48 3.245(6) 140.3 1_545
N2 H2D O1 0.89 2.23 3.041(5) 151.5 1_545
N2 H2C O11 0.89 1.89 2.748(6) 162.4 2_556
N2 H2B O3 0.89 1.95 2.814(5) 162.8 1_545
N2 H2B S1 0.89 2.79 3.491(4) 136.4 1_545
O9 H9 O7 0.82 2.58 3.142(5) 126.6 2_666
O9 H9 O7 0.82 1.93 2.636(5) 143.4 .
O8 H8 O5 0.82 1.83 2.631(4) 164.2 2_666
O8 H8 S1 0.82 3.01 3.720(4) 145.5 2_666
N1 H1C O5 0.89 1.99 2.850(4) 161.7 2_666
N1 H1B O4 0.89 2.49 3.095(5) 125.8 1_556
N1 H1B O3 0.89 2.05 2.926(4) 169.1 1_556
N1 H1B S1 0.89 2.78 3.612(4) 156.3 1_556
N1 H1A O6 0.89 1.97 2.862(5) 174.3 2_566
N1 H1A S1 0.89 2.87 3.686(4) 152.4 2_566
C2 H2A O3 0.93 2.52 3.281(6) 139.4 1_556
O2 H2 O6 0.82 1.76 2.570(4) 170.7 .
O2 H2 S1 0.82 2.87 3.644(4) 157.4 .
O10 H10 O1 0.82 1.93 2.645(5) 145.1 .

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_solid5
_database_code_depnum_ccdc_archive 'CCDC 1474394'
_audit_update_record             
;
2017-06-24 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;

_audit_creation_method           'SHELXTL-NT2000 ver.6.12'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H8 N O3, C H3 O3 S'
_chemical_formula_sum            'C8 H11 N O6 S'
_chemical_formula_weight         249.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a                   6.6805(7)
_cell_length_b                   18.0494(18)
_cell_length_c                   8.8346(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.660(2)
_cell_angle_gamma                90.00
_cell_volume                     1058.08(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7125
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      28.23

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.382
_exptl_crystal_size_mid          0.315
_exptl_crystal_size_min          0.221
_exptl_absorpt_coefficient_mu    0.320
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.731
_exptl_absorpt_correction_T_max  0.775
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10015
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.257
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_full        24.989
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1848
_reflns_number_gt                1797
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0448P)²+0.5429P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1855
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0855
_refine_ls_wR_factor_gt          0.0846
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.004

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
S1 S 0.20419(6) 0.35761(2) 0.95089(4) 0.02958(17) Uani 1 1 d . . . . .
O1 O 0.7866(2) 0.55756(7) 0.67059(14) 0.0388(3) Uani 1 1 d . . . . .
H1 H 0.8003 0.5825 0.7487 0.058 Uiso 1 1 calc R U . . .
O2 O 0.6720(2) 0.47407(7) 0.82607(13) 0.0410(3) Uani 1 1 d . . . . .
O3 O 0.6239(3) 0.33594(7) 0.72800(15) 0.0485(4) Uani 1 1 d . . . . .
H3 H 0.6221 0.3695 0.7903 0.073 Uiso 1 1 calc R U . . .
O4 O 0.4185(2) 0.35941(7) 1.00219(16) 0.0440(4) Uani 1 1 d . . . . .
O5 O 0.1431(2) 0.41312(8) 0.83700(16) 0.0516(4) Uani 1 1 d . . . . .
O6 O 0.0861(2) 0.36082(7) 1.08017(16) 0.0441(4) Uani 1 1 d . . . . .
N1 N 0.7424(2) 0.44003(8) 0.15115(15) 0.0307(3) Uani 1 1 d . . . . .
H1A H 0.7639 0.4887 0.1519 0.046 Uiso 1 1 calc R U . . .
H1B H 0.6294 0.4299 0.0910 0.046 Uiso 1 1 calc R U . . .
H1C H 0.8454 0.4170 0.1162 0.046 Uiso 1 1 calc R U . . .
C1 C 0.7214(2) 0.49077(9) 0.70157(18) 0.0297(4) Uani 1 1 d . . . . .
C2 C 0.6621(3) 0.36419(9) 0.59289(19) 0.0327(4) Uani 1 1 d . . . . .
C3 C 0.7404(2) 0.46351(9) 0.42584(17) 0.0268(4) Uani 1 1 d . . . . .
H3A H 0.7725 0.5128 0.4101 0.032 Uiso 1 1 calc R U . . .
C4 C 0.6812(3) 0.34034(10) 0.32812(19) 0.0338(4) Uani 1 1 d . . . . .
H4 H 0.6723 0.3077 0.2462 0.041 Uiso 1 1 calc R U . . .
C5 C 0.7231(2) 0.41457(9) 0.30666(17) 0.0271(4) Uani 1 1 d . . . . .
C6 C 0.7096(2) 0.43882(9) 0.57168(18) 0.0272(4) Uani 1 1 d . . . . .
C7 C 0.6528(3) 0.31536(10) 0.4705(2) 0.0374(4) Uani 1 1 d . . . . .
H7 H 0.6272 0.2654 0.4854 0.045 Uiso 1 1 calc R U . . .
C8 C 0.1526(3) 0.27162(11) 0.8629(3) 0.0500(5) Uani 1 1 d . . . . .
H8A H 0.0132 0.2696 0.8220 0.075 Uiso 1 1 calc R U . . .
H8B H 0.1809 0.2328 0.9366 0.075 Uiso 1 1 calc R U . . .
H8C H 0.2355 0.2654 0.7821 0.075 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O5 1.4448(14) . ?
S1 O4 1.4513(14) . ?
S1 O6 1.4625(14) . ?
S1 C8 1.7520(19) . ?
O1 C1 1.321(2) . ?
O1 H1 0.8200 . ?
O2 C1 1.222(2) . ?
O3 C2 1.349(2) . ?
O3 H3 0.8200 . ?
N1 C5 1.468(2) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C1 C6 1.477(2) . ?
C2 C7 1.391(2) . ?
C2 C6 1.401(2) . ?
C3 C5 1.369(2) . ?
C3 C6 1.401(2) . ?
C3 H3A 0.9300 . ?
C4 C7 1.370(2) . ?
C4 C5 1.386(2) . ?
C4 H4 0.9300 . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 S1 O4 113.00(9) . . ?
O5 S1 O6 112.46(9) . . ?
O4 S1 O6 110.93(8) . . ?
O5 S1 C8 106.28(10) . . ?
O4 S1 C8 107.13(9) . . ?
O6 S1 C8 106.58(9) . . ?
C1 O1 H1 109.5 . . ?
C2 O3 H3 109.5 . . ?
C5 N1 H1A 109.5 . . ?
C5 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C5 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
O2 C1 O1 122.78(15) . . ?
O2 C1 C6 123.16(16) . . ?
O1 C1 C6 114.05(14) . . ?
O3 C2 C7 116.90(16) . . ?
O3 C2 C6 123.40(15) . . ?
C7 C2 C6 119.70(15) . . ?
C5 C3 C6 119.58(15) . . ?
C5 C3 H3A 120.2 . . ?
C6 C3 H3A 120.2 . . ?
C7 C4 C5 119.70(16) . . ?
C7 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C3 C5 C4 121.26(15) . . ?
C3 C5 N1 120.59(14) . . ?
C4 C5 N1 118.12(14) . . ?
C3 C6 C2 119.24(15) . . ?
C3 C6 C1 120.82(15) . . ?
C2 C6 C1 119.92(15) . . ?
C4 C7 C2 120.45(16) . . ?
C4 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
S1 C8 H8A 109.5 . . ?
S1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
S1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C3 C5 C4 -1.9(2) . . . . ?
C6 C3 C5 N1 176.21(14) . . . . ?
C7 C4 C5 C3 1.2(3) . . . . ?
C7 C4 C5 N1 -176.95(16) . . . . ?
C5 C3 C6 C2 0.2(2) . . . . ?
C5 C3 C6 C1 -178.17(14) . . . . ?
O3 C2 C6 C3 -177.94(16) . . . . ?
C7 C2 C6 C3 2.1(3) . . . . ?
O3 C2 C6 C1 0.5(3) . . . . ?
C7 C2 C6 C1 -179.47(16) . . . . ?
O2 C1 C6 C3 170.83(16) . . . . ?
O1 C1 C6 C3 -8.0(2) . . . . ?
O2 C1 C6 C2 -7.5(3) . . . . ?
O1 C1 C6 C2 173.67(15) . . . . ?
C5 C4 C7 C2 1.2(3) . . . . ?
O3 C2 C7 C4 177.21(18) . . . . ?
C6 C2 C7 C4 -2.9(3) . . . . ?

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
C4 H4 O3 0.93 2.61 3.313(2) 132.3 4_565
N1 H1C O6 0.89 1.96 2.836(2) 169.0 1_654
N1 H1B O4 0.89 1.99 2.8051(19) 151.6 1_554
N1 H1A O5 0.89 1.88 2.758(2) 170.0 3_666
N1 H1A S1 0.89 2.93 3.7889(15) 161.5 3_666
O3 H3 O4 0.82 2.45 2.9497(19) 120.7 .
O3 H3 O2 0.82 1.94 2.6467(19) 144.6 .
O1 H1 O6 0.82 1.91 2.7033(18) 163.0 3_667
O1 H1 S1 0.82 2.87 3.6719(13) 166.7 3_667
O1 H1 S1 0.82 2.87 3.6719(13) 166.7 3_667
O1 H1 O6 0.82 1.91 2.7033(18) 163.0 3_667
O3 H3 O2 0.82 1.94 2.6467(19) 144.6 .
O3 H3 O4 0.82 2.45 2.9497(19) 120.7 .
N1 H1A S1 0.89 2.93 3.7889(15) 161.5 3_666
N1 H1A O5 0.89 1.88 2.758(2) 170.0 3_666
N1 H1B O4 0.89 1.99 2.8051(19) 151.6 1_554
N1 H1C O6 0.89 1.96 2.836(2) 169.0 1_654
C4 H4 O3 0.93 2.61 3.313(2) 132.3 4_565

_refine_diff_density_max         0.342
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_solid3
_database_code_depnum_ccdc_archive 'CCDC 1474389'
_audit_update_record             
;
2017-06-24 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;

_audit_creation_method           'SHELXTL-NT2000 ver.6.12'
_chemical_name_systematic        
; 
 ? 
;

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H8 N O3, N O3, H2 O'
_chemical_formula_sum            'C7 H10 N2 O7'
_chemical_formula_weight         234.15

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

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

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

_cell_length_a                   5.261(3)
_cell_length_b                   35.453(20)
_cell_length_c                   5.591(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.839(11)
_cell_angle_gamma                90.00
_cell_volume                     1012.6(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    964
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      23.95

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.433
_exptl_crystal_size_mid          0.361
_exptl_crystal_size_min          0.319
_exptl_absorpt_coefficient_mu    0.140
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3701
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         3.448
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1776
_reflns_number_gt                1282
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0670P)²+0.7226P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1573
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0788
_refine_ls_wR_factor_ref         0.1685
_refine_ls_wR_factor_gt          0.1585
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.144
_refine_ls_shift/su_max          0.042
_refine_ls_shift/su_mean         0.013

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
O6 O 0.7942(6) 0.21707(7) 0.1819(5) 0.0451(8) Uani 1 1 d . . . . .
O7 O 0.4944(6) 0.20208(8) 0.4812(6) 0.0505(8) Uani 1 1 d . . . . .
H7 H 0.5821 0.2156 0.4128 0.076 Uiso 1 1 calc R U . . .
O5 O 0.9324(6) 0.17034(7) -0.0189(5) 0.0407(8) Uani 1 1 d . . . . .
H5 H 0.9976 0.1879 -0.0784 0.061 Uiso 1 1 calc R U . . .
C1 C 0.6600(7) 0.15475(10) 0.2454(6) 0.0274(8) Uani 1 1 d . . . . .
O3 O 0.6761(5) 0.02761(8) 0.7395(5) 0.0441(8) Uani 1 1 d . . . . .
O4 O 0.1605(8) 0.22348(9) 0.7922(6) 0.0480(9) Uani 1 1 d . . . . .
C2 C 0.6698(7) 0.11641(10) 0.1859(7) 0.0293(9) Uani 1 1 d . . . . .
H2 H 0.7664 0.1086 0.0757 0.035 Uiso 1 1 calc R U . . .
C3 C 0.5362(7) 0.09054(10) 0.2910(6) 0.0267(8) Uani 1 1 d . . . . .
N2 N 0.5458(6) 0.05043(8) 0.2329(5) 0.0346(8) Uani 1 1 d . . . . .
H2A H 0.3926 0.0433 0.1375 0.052 Uiso 1 1 calc R U . . .
H2B H 0.5790 0.0371 0.3718 0.052 Uiso 1 1 calc R U . . .
H2C H 0.6717 0.0464 0.1542 0.052 Uiso 1 1 calc R U . . .
N1 N 0.9102(7) 0.03661(9) 0.8064(6) 0.0363(8) Uani 1 1 d . . . . .
C4 C 0.3949(8) 0.10164(11) 0.4583(7) 0.0389(10) Uani 1 1 d . . . . .
H4 H 0.3066 0.0837 0.5292 0.047 Uiso 1 1 calc R U . . .
C5 C 0.8019(7) 0.18341(10) 0.1346(7) 0.0283(8) Uani 1 1 d . . . . .
O2 O 1.0011(6) 0.04388(9) 1.0319(6) 0.0580(10) Uani 1 1 d . . . . .
C6 C 0.5136(7) 0.16582(10) 0.4122(7) 0.0328(9) Uani 1 1 d . . . . .
C7 C 0.3841(8) 0.13900(11) 0.5204(7) 0.0396(10) Uani 1 1 d . . . . .
H7A H 0.2906 0.1463 0.6344 0.048 Uiso 1 1 calc R U . . .
O1 O 1.0473(8) 0.03828(12) 0.6587(8) 0.0862(13) Uani 1 1 d . . . . .
H1W H 0.261(9) 0.2210(12) 0.690(8) 0.048(13) Uiso 1 1 d . . . . .
H2W H 0.065(9) 0.2393(14) 0.713(8) 0.047(15) 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
O6 C5 1.225(4) . ?
O7 C6 1.353(4) . ?
O7 H7 0.8200 . ?
O5 C5 1.305(4) . ?
O5 H5 0.8200 . ?
C1 C6 1.401(5) . ?
C1 C2 1.403(5) . ?
C1 C5 1.482(5) . ?
O3 N1 1.240(4) . ?
O4 H1W 0.87(5) . ?
O4 H2W 0.81(5) . ?
C2 C3 1.370(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(5) . ?
C3 N2 1.462(5) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
N1 O1 1.221(5) . ?
N1 O2 1.264(4) . ?
C4 C7 1.374(5) . ?
C4 H4 0.9300 . ?
C6 C7 1.390(5) . ?
C7 H7A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O7 H7 109.5 . . ?
C5 O5 H5 109.5 . . ?
C6 C1 C2 119.1(3) . . ?
C6 C1 C5 119.9(3) . . ?
C2 C1 C5 121.0(3) . . ?
H1W O4 H2W 96(4) . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 N2 120.5(3) . . ?
C4 C3 N2 118.6(3) . . ?
C3 N2 H2A 109.5 . . ?
C3 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C3 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
O1 N1 O3 120.9(4) . . ?
O1 N1 O2 121.4(4) . . ?
O3 N1 O2 117.7(4) . . ?
C7 C4 C3 120.4(3) . . ?
C7 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
O6 C5 O5 122.5(3) . . ?
O6 C5 C1 122.1(3) . . ?
O5 C5 C1 115.3(3) . . ?
O7 C6 C7 116.6(3) . . ?
O7 C6 C1 123.1(3) . . ?
C7 C6 C1 120.2(3) . . ?
C4 C7 C6 119.7(4) . . ?
C4 C7 H7A 120.1 . . ?
C6 C7 H7A 120.1 . . ?

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
C6 C1 C2 C3 0.1(5) . . . . ?
C5 C1 C2 C3 -179.9(3) . . . . ?
C1 C2 C3 C4 -1.0(5) . . . . ?
C1 C2 C3 N2 -179.5(3) . . . . ?
C2 C3 C4 C7 0.6(6) . . . . ?
N2 C3 C4 C7 179.1(3) . . . . ?
C6 C1 C5 O6 -0.7(5) . . . . ?
C2 C1 C5 O6 179.3(4) . . . . ?
C6 C1 C5 O5 -179.9(3) . . . . ?
C2 C1 C5 O5 0.1(5) . . . . ?
C2 C1 C6 O7 179.6(3) . . . . ?
C5 C1 C6 O7 -0.3(6) . . . . ?
C2 C1 C6 C7 1.2(5) . . . . ?
C5 C1 C6 C7 -178.8(3) . . . . ?
C3 C4 C7 C6 0.7(6) . . . . ?
O7 C6 C7 C4 179.8(4) . . . . ?
C1 C6 C7 C4 -1.6(6) . . . . ?

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
O4 H2W O6 0.81(5) 2.08(5) 2.823(5) 152(4) 4_466
O4 H1W O7 0.87(5) 2.00(5) 2.854(4) 166(4) .
C4 H4 O1 0.93 2.33 3.259(5) 172.8 1_455
N2 H2C O2 0.89 2.01 2.888(5) 168.3 1_554
N2 H2C N1 0.89 2.58 3.433(5) 161.6 1_554
N2 H2C O3 0.89 2.42 3.105(4) 134.2 1_554
N2 H2B O1 0.89 2.60 3.132(5) 119.3 .
N2 H2B N1 0.89 2.63 3.355(5) 139.3 .
N2 H2B O3 0.89 2.02 2.867(4) 157.4 .
N2 H2A O2 0.89 2.00 2.826(5) 153.4 1_454
C2 H2 O2 0.93 2.64 3.333(5) 131.4 1_554
O5 H5 O4 0.82 1.77 2.591(4) 175.3 1_654
O7 H7 O6 0.82 1.90 2.614(4) 145.2 .
O7 H7 O6 0.82 1.90 2.614(4) 145.2 .
O5 H5 O4 0.82 1.77 2.591(4) 175.3 1_654
C2 H2 O2 0.93 2.64 3.333(5) 131.4 1_554
N2 H2A O2 0.89 2.00 2.826(5) 153.4 1_454
N2 H2B O3 0.89 2.02 2.867(4) 157.4 .
N2 H2B N1 0.89 2.63 3.355(5) 139.3 .
N2 H2B O1 0.89 2.60 3.132(5) 119.3 .
N2 H2C O3 0.89 2.42 3.105(4) 134.2 1_554
N2 H2C N1 0.89 2.58 3.433(5) 161.6 1_554
N2 H2C O2 0.89 2.01 2.888(5) 168.3 1_554
C4 H4 O1 0.93 2.33 3.259(5) 172.8 1_455
O4 H1W O7 0.87(5) 2.00(5) 2.854(4) 166(4) .
O4 H2W O6 0.81(5) 2.08(5) 2.823(5) 152(4) 4_466
O7 H7 O6 0.82 1.90 2.614(4) 145.2 .
O5 H5 O4 0.82 1.77 2.591(4) 175.3 1_654
C2 H2 O2 0.93 2.64 3.333(5) 131.4 1_554
N2 H2A O2 0.89 2.00 2.826(5) 153.4 1_454
N2 H2B O3 0.89 2.02 2.867(4) 157.4 .
N2 H2B N1 0.89 2.63 3.355(5) 139.3 .
N2 H2B O1 0.89 2.60 3.132(5) 119.3 .
N2 H2C O3 0.89 2.42 3.105(4) 134.2 1_554
N2 H2C N1 0.89 2.58 3.433(5) 161.6 1_554
N2 H2C O2 0.89 2.01 2.888(5) 168.3 1_554
C4 H4 O1 0.93 2.33 3.259(5) 172.8 1_455
O4 H1W O7 0.87(5) 2.00(5) 2.854(4) 166(4) .
O4 H2W O6 0.81(5) 2.08(5) 2.823(5) 152(4) 4_466

_refine_diff_density_max         0.231
_refine_diff_density_min         -0.202
_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_solid8
_database_code_depnum_ccdc_archive 'CCDC 1474397'
_audit_update_record             
;
2017-06-24 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;

_audit_creation_method           'SHELXTL-NT2000 ver.6.12'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N2, 0.5(C12 H12 N2), C7 H6 N O3'
_chemical_formula_sum            'C25 H22 N4 O3'
_chemical_formula_weight         426.47

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.401(3)
_cell_length_b                   9.361(4)
_cell_length_c                   14.212(6)
_cell_angle_alpha                101.827(8)
_cell_angle_beta                 96.580(8)
_cell_angle_gamma                106.511(8)
_cell_volume                     1030.9(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1151
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      25.39

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.489
_exptl_crystal_size_mid          0.381
_exptl_crystal_size_min          0.253
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9953
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.489
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3612
_reflns_number_gt                2086
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1311P)²+0.3497P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3612
_refine_ls_number_parameters     291
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1341
_refine_ls_R_factor_gt           0.0823
_refine_ls_wR_factor_ref         0.2572
_refine_ls_wR_factor_gt          0.2271
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.263
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.003

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
N4 N 0.3624(4) 0.4412(4) 0.2509(2) 0.0408(8) Uani 1 1 d . . . . .
H50 H 0.4333 0.4409 0.2995 0.049 Uiso 1 1 calc R U . . .
N2 N -0.4053(4) 0.4561(4) 0.4042(2) 0.0452(8) Uani 1 1 d . . . . .
C1 C 0.1380(4) 0.4440(4) 0.0948(2) 0.0380(9) Uani 1 1 d . . . . .
C2 C 0.2435(5) 0.5796(4) 0.1586(3) 0.0437(9) Uani 1 1 d . . . . .
H18 H 0.2395 0.6740 0.1491 0.052 Uiso 1 1 calc R U . . .
C3 C 0.0162(4) 0.4409(4) 0.0106(2) 0.0397(9) Uani 1 1 d . . . . .
H19 H -0.0432 0.3452 -0.0312 0.048 Uiso 1 1 calc R U . . .
C4 C 0.3533(5) 0.5741(4) 0.2358(3) 0.0435(10) Uani 1 1 d . . . . .
H15 H 0.4230 0.6656 0.2785 0.052 Uiso 1 1 calc R U . . .
N3 N 0.4376(5) 0.6517(4) 0.9525(3) 0.0625(10) Uani 1 1 d . . . . .
C5 C -0.1569(6) 0.4915(7) 0.5635(3) 0.0674(14) Uani 1 1 d . . . . .
C6 C -0.3040(5) 0.5959(5) 0.4523(3) 0.0531(11) Uani 1 1 d . . . . .
H14 H -0.3160 0.6816 0.4324 0.064 Uiso 1 1 calc R U . . .
C7 C 0.2377(5) 0.4808(5) 0.8153(3) 0.0497(10) Uani 1 1 d . . . . .
H9 H 0.1853 0.3795 0.7796 0.060 Uiso 1 1 calc R U . . .
C8 C 0.3565(5) 0.5124(5) 0.8983(3) 0.0482(10) Uani 1 1 d . . . . .
H10 H 0.3806 0.4302 0.9170 0.058 Uiso 1 1 calc R U . . .
C9 C 0.2634(5) 0.3090(5) 0.1920(3) 0.0451(10) Uani 1 1 d . . . . .
H16 H 0.2708 0.2168 0.2038 0.054 Uiso 1 1 calc R U . . .
C10 C -0.3830(5) 0.3359(5) 0.4350(3) 0.0502(10) Uani 1 1 d . . . . .
H13 H -0.4525 0.2376 0.4016 0.060 Uiso 1 1 calc R U . . .
C11 C 0.1962(5) 0.5973(6) 0.7850(3) 0.0566(12) Uani 1 1 d . . . . .
C12 C 0.1493(5) 0.3067(4) 0.1133(3) 0.0438(9) Uani 1 1 d . . . . .
H17 H 0.0799 0.2132 0.0726 0.053 Uiso 1 1 calc R U . . .
C13 C -0.1792(5) 0.6154(6) 0.5328(3) 0.0728(15) Uani 1 1 d . . . . .
H11 H -0.1105 0.7140 0.5660 0.087 Uiso 1 1 calc R U . . .
C14 C -0.2641(5) 0.3507(6) 0.5122(3) 0.0608(12) Uani 1 1 d . . . . .
H12 H -0.2552 0.2631 0.5306 0.073 Uiso 1 1 calc R U . . .
C15 C 0.2836(8) 0.7435(6) 0.8412(4) 0.0937(19) Uani 1 1 d . . . . .
H8 H 0.2650 0.8287 0.8237 0.112 Uiso 1 1 calc R U . . .
C16 C 0.3970(7) 0.7624(6) 0.9224(4) 0.096(2) Uani 1 1 d . . . . .
H7 H 0.4506 0.8624 0.9599 0.116 Uiso 1 1 calc R U . . .
O2 O 1.3145(4) 0.9822(4) 0.2688(2) 0.0709(9) Uani 1 1 d . . . . .
C17 C 0.7415(5) 0.9244(4) 0.3087(3) 0.0466(10) Uani 1 1 d . . . . .
O3 O 1.0910(4) 0.9280(3) 0.1221(2) 0.0605(8) Uani 1 1 d . . . . .
H3 H 1.1866 0.9491 0.1533 0.091 Uiso 1 1 calc R U . . .
N1 N 0.6215(4) 0.9181(4) 0.3687(3) 0.0591(10) Uani 1 1 d . . . . .
H1A H 0.6508 0.9289 0.4304 0.071 Uiso 1 1 calc R U . . .
H1B H 0.5180 0.9035 0.3442 0.071 Uiso 1 1 calc R U . . .
C18 C 0.6945(5) 0.8988(5) 0.2076(3) 0.0535(11) Uani 1 1 d . . . . .
H6 H 0.5820 0.8800 0.1809 0.064 Uiso 1 1 calc R U . . .
C19 C 1.0298(5) 0.9495(4) 0.2849(3) 0.0446(10) Uani 1 1 d . . . . .
C20 C 0.9092(5) 0.9477(4) 0.3447(3) 0.0474(10) Uani 1 1 d . . . . .
H4 H 0.9431 0.9628 0.4116 0.057 Uiso 1 1 calc R U . . .
C21 C 0.9800(5) 0.9271(4) 0.1844(3) 0.0452(10) Uani 1 1 d . . . . .
C22 C 1.2109(5) 0.9745(5) 0.3279(3) 0.0567(11) Uani 1 1 d . . . . .
C23 C 0.8102(5) 0.9008(5) 0.1470(3) 0.0539(11) Uani 1 1 d . . . . .
H5 H 0.7752 0.8845 0.0801 0.065 Uiso 1 1 calc R U . . .
O1 O 1.2498(4) 0.9870(5) 0.4159(3) 0.0910(12) Uani 1 1 d . . . . .
C27 C -0.0324(7) 0.4925(11) 0.6452(4) 0.126(3) Uani 1 1 d D . . . .
H20 H -0.0403 0.3943 0.6524 0.151 Uiso 1 1 calc R U . . .
C26 C 0.0741(7) 0.5885(10) 0.7031(4) 0.113(3) Uani 1 1 d D . . . .
H21 H 0.0820 0.6855 0.6936 0.136 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N4 C9 1.325(5) . ?
N4 C4 1.327(5) . ?
N4 H50 0.8600 . ?
N2 C6 1.331(5) . ?
N2 C10 1.340(5) . ?
C1 C2 1.387(5) . ?
C1 C12 1.390(5) . ?
C1 C3 1.472(5) . ?
C2 C4 1.368(5) . ?
C2 H18 0.9300 . ?
C3 C3 1.295(7) 2_565 ?
C3 H19 0.9300 . ?
C4 H15 0.9300 . ?
N3 C8 1.311(5) . ?
N3 C16 1.313(6) . ?
C5 C14 1.364(7) . ?
C5 C13 1.371(7) . ?
C5 C27 1.469(7) . ?
C6 C13 1.405(6) . ?
C6 H14 0.9300 . ?
C7 C11 1.368(6) . ?
C7 C8 1.376(5) . ?
C7 H9 0.9300 . ?
C8 H10 0.9300 . ?
C9 C12 1.380(5) . ?
C9 H16 0.9300 . ?
C10 C14 1.352(5) . ?
C10 H13 0.9300 . ?
C11 C15 1.377(7) . ?
C11 C26 1.433(6) . ?
C12 H17 0.9300 . ?
C13 H11 0.9300 . ?
C14 H12 0.9300 . ?
C15 C16 1.355(7) . ?
C15 H8 0.9300 . ?
C16 H7 0.9300 . ?
O2 C22 1.275(5) . ?
C17 C20 1.382(5) . ?
C17 N1 1.389(5) . ?
C17 C18 1.398(5) . ?
O3 C21 1.358(5) . ?
O3 H3 0.8200 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
C18 C23 1.369(6) . ?
C18 H6 0.9300 . ?
C19 C20 1.393(6) . ?
C19 C21 1.396(5) . ?
C19 C22 1.506(6) . ?
C20 H4 0.9300 . ?
C21 C23 1.398(5) . ?
C22 O1 1.229(5) . ?
C23 H5 0.9300 . ?
C27 C26 1.164(8) . ?
C27 H20 0.9300 . ?
C26 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N4 C4 120.7(3) . . ?
C9 N4 H50 119.6 . . ?
C4 N4 H50 119.6 . . ?
C6 N2 C10 117.7(3) . . ?
C2 C1 C12 117.3(3) . . ?
C2 C1 C3 122.8(3) . . ?
C12 C1 C3 119.8(3) . . ?
C4 C2 C1 119.8(4) . . ?
C4 C2 H18 120.1 . . ?
C1 C2 H18 120.1 . . ?
C3 C3 C1 126.1(4) 2_565 . ?
C3 C3 H19 116.9 2_565 . ?
C1 C3 H19 116.9 . . ?
N4 C4 C2 121.4(3) . . ?
N4 C4 H15 119.3 . . ?
C2 C4 H15 119.3 . . ?
C8 N3 C16 115.0(4) . . ?
C14 C5 C13 116.0(4) . . ?
C14 C5 C27 116.2(6) . . ?
C13 C5 C27 127.8(6) . . ?
N2 C6 C13 120.6(4) . . ?
N2 C6 H14 119.7 . . ?
C13 C6 H14 119.7 . . ?
C11 C7 C8 120.5(4) . . ?
C11 C7 H9 119.8 . . ?
C8 C7 H9 119.8 . . ?
N3 C8 C7 123.8(4) . . ?
N3 C8 H10 118.1 . . ?
C7 C8 H10 118.1 . . ?
N4 C9 C12 120.7(4) . . ?
N4 C9 H16 119.7 . . ?
C12 C9 H16 119.7 . . ?
N2 C10 C14 123.1(4) . . ?
N2 C10 H13 118.4 . . ?
C14 C10 H13 118.4 . . ?
C7 C11 C15 115.5(4) . . ?
C7 C11 C26 129.1(6) . . ?
C15 C11 C26 115.5(5) . . ?
C9 C12 C1 120.0(3) . . ?
C9 C12 H17 120.0 . . ?
C1 C12 H17 120.0 . . ?
C5 C13 C6 121.2(4) . . ?
C5 C13 H11 119.4 . . ?
C6 C13 H11 119.4 . . ?
C10 C14 C5 121.3(5) . . ?
C10 C14 H12 119.4 . . ?
C5 C14 H12 119.4 . . ?
C16 C15 C11 119.5(4) . . ?
C16 C15 H8 120.3 . . ?
C11 C15 H8 120.3 . . ?
N3 C16 C15 125.6(5) . . ?
N3 C16 H7 117.2 . . ?
C15 C16 H7 117.2 . . ?
C20 C17 N1 122.2(4) . . ?
C20 C17 C18 117.0(4) . . ?
N1 C17 C18 120.7(4) . . ?
C21 O3 H3 109.5 . . ?
C17 N1 H1A 120.0 . . ?
C17 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C23 C18 C17 121.6(4) . . ?
C23 C18 H6 119.2 . . ?
C17 C18 H6 119.2 . . ?
C20 C19 C21 119.0(4) . . ?
C20 C19 C22 120.6(4) . . ?
C21 C19 C22 120.5(4) . . ?
C17 C20 C19 122.8(4) . . ?
C17 C20 H4 118.6 . . ?
C19 C20 H4 118.6 . . ?
O3 C21 C19 122.0(4) . . ?
O3 C21 C23 119.2(4) . . ?
C19 C21 C23 118.8(4) . . ?
O1 C22 O2 124.4(4) . . ?
O1 C22 C19 119.2(5) . . ?
O2 C22 C19 116.5(4) . . ?
C18 C23 C21 120.8(4) . . ?
C18 C23 H5 119.6 . . ?
C21 C23 H5 119.6 . . ?
C26 C27 C5 134.5(9) . . ?
C26 C27 H20 112.8 . . ?
C5 C27 H20 112.8 . . ?
C27 C26 C11 137.1(9) . . ?
C27 C26 H21 111.5 . . ?
C11 C26 H21 111.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 C1 C2 C4 0.3(6) . . . . ?
C3 C1 C2 C4 179.6(3) . . . . ?
C2 C1 C3 C3 -4.8(7) . . . 2_565 ?
C12 C1 C3 C3 174.5(5) . . . 2_565 ?
C9 N4 C4 C2 -0.8(6) . . . . ?
C1 C2 C4 N4 0.4(6) . . . . ?
C10 N2 C6 C13 -0.4(6) . . . . ?
C16 N3 C8 C7 0.4(7) . . . . ?
C11 C7 C8 N3 -0.6(6) . . . . ?
C4 N4 C9 C12 0.4(6) . . . . ?
C6 N2 C10 C14 0.4(6) . . . . ?
C8 C7 C11 C15 1.6(6) . . . . ?
C8 C7 C11 C26 -178.2(4) . . . . ?
N4 C9 C12 C1 0.4(6) . . . . ?
C2 C1 C12 C9 -0.7(6) . . . . ?
C3 C1 C12 C9 180.0(3) . . . . ?
C14 C5 C13 C6 -0.9(7) . . . . ?
C27 C5 C13 C6 179.5(4) . . . . ?
N2 C6 C13 C5 0.7(6) . . . . ?
N2 C10 C14 C5 -0.7(7) . . . . ?
C13 C5 C14 C10 0.9(7) . . . . ?
C27 C5 C14 C10 -179.5(4) . . . . ?
C7 C11 C15 C16 -2.3(8) . . . . ?
C26 C11 C15 C16 177.5(5) . . . . ?
C8 N3 C16 C15 -1.3(9) . . . . ?
C11 C15 C16 N3 2.3(11) . . . . ?
C20 C17 C18 C23 -1.7(6) . . . . ?
N1 C17 C18 C23 -178.4(4) . . . . ?
N1 C17 C20 C19 178.0(3) . . . . ?
C18 C17 C20 C19 1.3(6) . . . . ?
C21 C19 C20 C17 0.1(6) . . . . ?
C22 C19 C20 C17 -179.6(3) . . . . ?
C20 C19 C21 O3 179.8(3) . . . . ?
C22 C19 C21 O3 -0.5(5) . . . . ?
C20 C19 C21 C23 -1.1(5) . . . . ?
C22 C19 C21 C23 178.5(3) . . . . ?
C20 C19 C22 O1 2.9(6) . . . . ?
C21 C19 C22 O1 -176.8(4) . . . . ?
C20 C19 C22 O2 -176.6(4) . . . . ?
C21 C19 C22 O2 3.7(6) . . . . ?
C17 C18 C23 C21 0.7(6) . . . . ?
O3 C21 C23 C18 179.9(3) . . . . ?
C19 C21 C23 C18 0.8(6) . . . . ?
C14 C5 C27 C26 -179.4(6) . . . . ?
C13 C5 C27 C26 0.2(10) . . . . ?
C5 C27 C26 C11 178.4(5) . . . . ?
C7 C11 C26 C27 8.4(10) . . . . ?
C15 C11 C26 C27 -171.4(7) . . . . ?

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
N1 H1B O2 0.86 2.29 3.069(5) 151.1 1_455
N1 H1A O1 0.86 2.14 2.984(5) 166.1 2_776
O3 H3 O2 0.82 1.77 2.502(4) 147.2 .
C14 H12 O1 0.93 2.62 3.544(6) 176.4 2_666
C9 H16 O3 0.93 2.63 3.330(5) 132.2 1_445
C9 H16 O2 0.93 2.65 3.570(5) 170.2 1_445
C8 H10 N3 0.93 2.64 3.443(5) 145.3 2_667
C4 H15 N1 0.93 2.46 3.380(5) 171.2 .
N4 H50 N2 0.86 1.85 2.706(4) 175.5 1_655
N1 H1B O2 0.86 2.29 3.069(5) 151.1 1_455
N1 H1A O1 0.86 2.14 2.984(5) 166.1 2_776
O3 H3 O2 0.82 1.77 2.502(4) 147.2 .
C14 H12 O1 0.93 2.62 3.544(6) 176.4 2_666
C9 H16 O3 0.93 2.63 3.330(5) 132.2 1_445
C9 H16 O2 0.93 2.65 3.570(5) 170.2 1_445
C8 H10 N3 0.93 2.64 3.443(5) 145.3 2_667
C4 H15 N1 0.93 2.46 3.380(5) 171.2 .
N4 H50 N2 0.86 1.85 2.706(4) 175.5 1_655
N1 H1B O2 0.86 2.29 3.069(5) 151.1 1_455
N1 H1A O1 0.86 2.14 2.984(5) 166.1 2_776
O3 H3 O2 0.82 1.77 2.502(4) 147.2 .
C14 H12 O1 0.93 2.62 3.544(6) 176.4 2_666
C9 H16 O3 0.93 2.63 3.330(5) 132.2 1_445
C9 H16 O2 0.93 2.65 3.570(5) 170.2 1_445
C8 H10 N3 0.93 2.64 3.443(5) 145.3 2_667
C4 H15 N1 0.93 2.46 3.380(5) 171.2 .
N4 H50 N2 0.86 1.85 2.706(4) 175.5 1_655
O3 H3 O2 0.82 1.77 2.502(4) 147.2 .
N1 H1A O1 0.86 2.14 2.984(5) 166.1 2_776
N1 H1B O2 0.86 2.29 3.069(5) 151.1 1_455
C14 H12 O1 0.93 2.62 3.544(6) 176.4 2_666
C9 H16 O3 0.93 2.63 3.330(5) 132.2 1_445
C9 H16 O2 0.93 2.65 3.570(5) 170.2 1_445
C8 H10 N3 0.93 2.64 3.443(5) 145.3 2_667
C4 H15 N1 0.93 2.46 3.380(5) 171.2 .
N4 H50 N2 0.86 1.85 2.706(4) 175.5 1_655
C4 H15 N1 0.93 2.46 3.380(5) 171.2 .
C8 H10 N3 0.93 2.64 3.443(5) 145.3 2_667
C9 H16 O2 0.93 2.65 3.570(5) 170.2 1_445
C9 H16 O3 0.93 2.63 3.330(5) 132.2 1_445
C14 H12 O1 0.93 2.62 3.544(6) 176.4 2_666
O3 H3 O2 0.82 1.77 2.502(4) 147.2 .
N1 H1A O1 0.86 2.14 2.984(5) 166.1 2_776
N1 H1B O2 0.86 2.29 3.069(5) 151.1 1_455
N4 H50 N2 0.86 1.85 2.706(4) 175.5 1_655
C4 H15 N1 0.93 2.46 3.380(5) 171.2 .
C8 H10 N3 0.93 2.64 3.443(5) 145.3 2_667
C9 H16 O2 0.93 2.65 3.570(5) 170.2 1_445
C9 H16 O3 0.93 2.63 3.330(5) 132.2 1_445
C14 H12 O1 0.93 2.62 3.544(6) 176.4 2_666
O3 H3 O2 0.82 1.77 2.502(4) 147.2 .
N1 H1A O1 0.86 2.14 2.984(5) 166.1 2_776
N1 H1B O2 0.86 2.29 3.069(5) 151.1 1_455

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_solid6
_database_code_depnum_ccdc_archive 'CCDC 1474395'
_audit_update_record             
;
2017-06-24 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;

_audit_creation_method           'SHELXTL-NT2000 ver.6.12'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H6 N O3, 0.5(C4 H12 N2)'
_chemical_formula_sum            'C9 H12 N2 O3'
_chemical_formula_weight         196.21

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

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

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

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

_cell_length_a                   6.5529(10)
_cell_length_b                   17.206(3)
_cell_length_c                   8.5190(13)
_cell_angle_alpha                90
_cell_angle_beta                 102.731(3)
_cell_angle_gamma                90
_cell_volume                     936.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2022
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      24.81

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.401
_exptl_crystal_size_mid          0.318
_exptl_crystal_size_min          0.225
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8881
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.722
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_full        24.990
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1643
_reflns_number_gt                1484
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0622P)²+0.9645P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1643
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0767
_refine_ls_wR_factor_ref         0.1748
_refine_ls_wR_factor_gt          0.1696
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_restrained_S_all      1.210
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.009

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0886(4) 0.60242(15) 0.3240(3) 0.0557(8) Uani 1 1 d . . . . .
O2 O 0.1778(4) 0.52323(14) 0.3330(3) 0.0540(7) Uani 1 1 d . . . . .
O3 O -0.0662(3) 0.71954(14) 0.5004(3) 0.0479(7) Uani 1 1 d . . . . .
H3 H -0.1215 0.6877 0.4327 0.072 Uiso 1 1 calc R U . . .
N1 N 0.6831(4) 0.54563(15) 0.0601(3) 0.0383(7) Uani 1 1 d . . . . .
H1A H 0.7001 0.5704 -0.0279 0.046 Uiso 1 1 calc R U . . .
H1B H 0.7847 0.5608 0.1419 0.046 Uiso 1 1 calc R U . . .
N2 N 0.7478(4) 0.63267(15) 0.7888(3) 0.0389(7) Uani 1 1 d . . . . .
H2A H 0.8006 0.5905 0.7609 0.047 Uiso 1 1 calc R U . . .
H2B H 0.8189 0.6608 0.8650 0.047 Uiso 1 1 calc R U . . .
C1 C 0.0982(5) 0.58016(18) 0.3819(3) 0.0347(7) Uani 1 1 d . . . . .
C2 C 0.2204(4) 0.62965(16) 0.5151(3) 0.0290(7) Uani 1 1 d . . . . .
C3 C 0.4273(4) 0.61162(16) 0.5865(3) 0.0303(7) Uani 1 1 d . . . . .
H6 H 0.4888 0.5684 0.5504 0.036 Uiso 1 1 calc R U . . .
C4 C 0.5439(4) 0.65587(17) 0.7092(3) 0.0302(7) Uani 1 1 d . . . . .
C5 C 0.4507(5) 0.72052(18) 0.7617(4) 0.0395(8) Uani 1 1 d . . . . .
H7 H 0.5258 0.7507 0.8454 0.047 Uiso 1 1 calc R U . . .
C6 C 0.2484(5) 0.74014(18) 0.6908(4) 0.0400(8) Uani 1 1 d . . . . .
H8 H 0.1887 0.7838 0.7270 0.048 Uiso 1 1 calc R U . . .
C7 C 0.1314(5) 0.69658(17) 0.5670(3) 0.0327(7) Uani 1 1 d . . . . .
C8 C 0.4778(5) 0.5671(2) 0.0936(4) 0.0428(8) Uani 1 1 d . . . . .
H10A H 0.4698 0.6232 0.1025 0.051 Uiso 1 1 calc R U . . .
H9B H 0.4657 0.5448 0.1957 0.051 Uiso 1 1 calc R U . . .
C9 C 0.7003(5) 0.46089(18) 0.0365(4) 0.0382(8) Uani 1 1 d . . . . .
H11A H 0.6985 0.4340 0.1362 0.046 Uiso 1 1 calc R U . . .
H12B H 0.8320 0.4493 0.0072 0.046 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.273(4) . ?
O2 C1 1.225(4) . ?
O3 C7 1.353(4) . ?
O3 H3 0.8200 . ?
N1 C9 1.480(4) . ?
N1 C8 1.482(4) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N2 C4 1.416(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C1 C2 1.501(4) . ?
C2 C3 1.393(4) . ?
C2 C7 1.405(4) . ?
C3 C4 1.380(4) . ?
C3 H6 0.9300 . ?
C4 C5 1.390(4) . ?
C5 C6 1.372(4) . ?
C5 H7 0.9300 . ?
C6 C7 1.381(4) . ?
C6 H8 0.9300 . ?
C8 C9 1.501(4) 3_665 ?
C8 H10A 0.9700 . ?
C8 H9B 0.9700 . ?
C9 C8 1.501(4) 3_665 ?
C9 H11A 0.9700 . ?
C9 H12B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O3 H3 109.5 . . ?
C9 N1 C8 111.8(2) . . ?
C9 N1 H1A 109.3 . . ?
C8 N1 H1A 109.3 . . ?
C9 N1 H1B 109.3 . . ?
C8 N1 H1B 109.3 . . ?
H1A N1 H1B 107.9 . . ?
C4 N2 H2A 120.0 . . ?
C4 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
O2 C1 O1 123.6(3) . . ?
O2 C1 C2 121.0(3) . . ?
O1 C1 C2 115.4(3) . . ?
C3 C2 C7 118.5(3) . . ?
C3 C2 C1 120.6(3) . . ?
C7 C2 C1 120.9(3) . . ?
C4 C3 C2 122.1(3) . . ?
C4 C3 H6 119.0 . . ?
C2 C3 H6 119.0 . . ?
C3 C4 C5 118.4(3) . . ?
C3 C4 N2 120.9(3) . . ?
C5 C4 N2 120.5(3) . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H7 119.8 . . ?
C4 C5 H7 119.8 . . ?
C5 C6 C7 121.5(3) . . ?
C5 C6 H8 119.2 . . ?
C7 C6 H8 119.2 . . ?
O3 C7 C6 118.7(3) . . ?
O3 C7 C2 122.2(3) . . ?
C6 C7 C2 119.1(3) . . ?
N1 C8 C9 111.6(3) . 3_665 ?
N1 C8 H10A 109.3 . . ?
C9 C8 H10A 109.3 3_665 . ?
N1 C8 H9B 109.3 . . ?
C9 C8 H9B 109.3 3_665 . ?
H10A C8 H9B 108.0 . . ?
N1 C9 C8 110.3(3) . 3_665 ?
N1 C9 H11A 109.6 . . ?
C8 C9 H11A 109.6 3_665 . ?
N1 C9 H12B 109.6 . . ?
C8 C9 H12B 109.6 3_665 . ?
H11A C9 H12B 108.1 . . ?

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
O2 C1 C2 C3 -0.3(4) . . . . ?
O1 C1 C2 C3 -179.2(3) . . . . ?
O2 C1 C2 C7 177.6(3) . . . . ?
O1 C1 C2 C7 -1.3(4) . . . . ?
C7 C2 C3 C4 2.1(4) . . . . ?
C1 C2 C3 C4 -180.0(3) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C2 C3 C4 N2 174.6(3) . . . . ?
C3 C4 C5 C6 -1.0(4) . . . . ?
N2 C4 C5 C6 -176.0(3) . . . . ?
C4 C5 C6 C7 0.4(5) . . . . ?
C5 C6 C7 O3 -179.1(3) . . . . ?
C5 C6 C7 C2 1.5(5) . . . . ?
C3 C2 C7 O3 177.9(3) . . . . ?
C1 C2 C7 O3 0.0(4) . . . . ?
C3 C2 C7 C6 -2.7(4) . . . . ?
C1 C2 C7 C6 179.4(3) . . . . ?
C9 N1 C8 C9 -55.9(4) . . . 3_665 ?
C8 N1 C9 C8 55.1(4) . . . 3_665 ?

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
C8 H9B O2 0.97 2.46 3.219(4) 135.2 .
N2 H2B O3 0.86 2.40 3.199(3) 155.0 4_676
N2 H2A O2 0.86 2.13 2.955(4) 160.6 3_666
N1 H1B O1 0.89 1.74 2.601(3) 160.8 1_655
N1 H1A N2 0.89 1.98 2.863(4) 175.2 1_554
O3 H3 O1 0.82 1.77 2.499(3) 146.6 .
O3 H3 O1 0.82 1.77 2.499(3) 146.6 .
N1 H1A N2 0.89 1.98 2.863(4) 175.2 1_554
N1 H1B O1 0.89 1.74 2.601(3) 160.8 1_655
N2 H2A O2 0.86 2.13 2.955(4) 160.6 3_666
N2 H2B O3 0.86 2.40 3.199(3) 155.0 4_676
C8 H9B O2 0.97 2.46 3.219(4) 135.2 .

_refine_diff_density_max         0.406
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_solid9
_database_code_depnum_ccdc_archive 'CCDC 1474398'
_audit_update_record             
;
2017-06-24 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;

_audit_creation_method           'SHELXTL-NT2000 ver.6.12'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H15 N2, C7 H6 N O3'
_chemical_formula_sum            'C20 H21 N3 O3'
_chemical_formula_weight         351.40

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

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

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

_cell_length_a                   9.397(3)
_cell_length_b                   8.445(2)
_cell_length_c                   21.930(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.071(5)
_cell_angle_gamma                90
_cell_volume                     1740.0(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3683
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      22.90

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.449
_exptl_crystal_size_mid          0.358
_exptl_crystal_size_min          0.278
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15976
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.858
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3043
_reflns_number_gt                2459
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0563P)²+0.5674P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3043
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1322
_refine_ls_wR_factor_gt          0.1249
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.005

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3793(2) 0.3561(2) 0.05970(9) 0.0549(5) Uani 1 1 d . . . . .
H1A H 0.3889 0.3372 0.0215 0.066 Uiso 1 1 calc R U . . .
H1B H 0.3640 0.4511 0.0720 0.066 Uiso 1 1 calc R U . . .
N2 N 0.9201(2) 0.3408(2) 0.04221(8) 0.0462(5) Uani 1 1 d . . . . .
H2 H 0.9468 0.2878 0.0109 0.055 Uiso 1 1 calc R U . . .
N3 N 0.5196(2) 0.3297(2) 0.44686(8) 0.0497(5) Uani 1 1 d . . . . .
O1 O 0.4560(2) -0.24068(19) 0.04797(8) 0.0684(5) Uani 1 1 d . . . . .
O2 O 0.4305(2) -0.32565(19) 0.14253(8) 0.0710(5) Uani 1 1 d . . . . .
O3 O 0.3862(2) -0.1361(2) 0.22839(7) 0.0675(5) Uani 1 1 d . . . . .
H3 H 0.3957 -0.2218 0.2114 0.101 Uiso 1 1 calc R U . . .
C1 C 0.8367(2) 0.5122(2) 0.14122(9) 0.0401(5) Uani 1 1 d . . . . .
C2 C 0.6252(2) 0.5117(2) 0.35148(9) 0.0420(5) Uani 1 1 d . . . . .
C3 C 0.7307(2) 0.5055(2) 0.24621(9) 0.0450(5) Uani 1 1 d . . . . .
H14A H 0.6503 0.4447 0.2306 0.054 Uiso 1 1 calc R U . . .
H15B H 0.8031 0.4316 0.2603 0.054 Uiso 1 1 calc R U . . .
C4 C 0.7848(3) 0.3851(3) 0.04607(10) 0.0529(6) Uani 1 1 d . . . . .
H19 H 0.7196 0.3572 0.0155 0.063 Uiso 1 1 calc R U . . .
C5 C 0.7417(2) 0.4716(3) 0.09507(10) 0.0505(6) Uani 1 1 d . . . . .
H18 H 0.6472 0.5035 0.0973 0.061 Uiso 1 1 calc R U . . .
C6 C 0.7902(3) 0.6074(2) 0.19499(10) 0.0479(6) Uani 1 1 d . . . . .
H17A H 0.7179 0.6823 0.1816 0.058 Uiso 1 1 calc R U . . .
H16B H 0.8708 0.6674 0.2108 0.058 Uiso 1 1 calc R U . . .
C7 C 0.7079(2) 0.4722(3) 0.40171(10) 0.0504(6) Uani 1 1 d . . . . .
H11 H 0.8020 0.5062 0.4045 0.060 Uiso 1 1 calc R U . . .
C8 C 0.6519(3) 0.3828(3) 0.44783(10) 0.0534(6) Uani 1 1 d . . . . .
H10 H 0.7099 0.3585 0.4814 0.064 Uiso 1 1 calc R U . . .
C9 C 0.6832(3) 0.6075(3) 0.29958(10) 0.0533(6) Uani 1 1 d . . . . .
H12A H 0.7636 0.6694 0.3145 0.064 Uiso 1 1 calc R U . . .
H13B H 0.6104 0.6807 0.2852 0.064 Uiso 1 1 calc R U . . .
C10 C 1.0150(2) 0.3769(3) 0.08579(10) 0.0513(6) Uani 1 1 d . . . . .
H20 H 1.1090 0.3443 0.0822 0.062 Uiso 1 1 calc R U . . .
C11 C 0.9758(2) 0.4608(3) 0.13555(10) 0.0501(6) Uani 1 1 d . . . . .
H21 H 1.0428 0.4839 0.1660 0.060 Uiso 1 1 calc R U . . .
C12 C 0.4879(3) 0.4554(3) 0.35044(11) 0.0602(7) Uani 1 1 d . . . . .
H9 H 0.4274 0.4779 0.3175 0.072 Uiso 1 1 calc R U . . .
C13 C 0.4405(2) 0.3658(3) 0.39810(12) 0.0632(7) Uani 1 1 d . . . . .
H8 H 0.3475 0.3282 0.3961 0.076 Uiso 1 1 calc R U . . .
C14 C 0.4141(2) -0.0491(2) 0.12488(9) 0.0383(5) Uani 1 1 d . . . . .
C15 C 0.4134(2) 0.0769(2) 0.08379(9) 0.0404(5) Uani 1 1 d . . . . .
H5 H 0.4300 0.0565 0.0429 0.048 Uiso 1 1 calc R U . . .
C16 C 0.3887(2) 0.2320(2) 0.10192(10) 0.0425(5) Uani 1 1 d . . . . .
C17 C 0.3895(2) -0.0182(3) 0.18625(10) 0.0453(5) Uani 1 1 d . . . . .
C18 C 0.3642(2) 0.2590(3) 0.16373(10) 0.0527(6) Uani 1 1 d . . . . .
H6 H 0.3475 0.3616 0.1772 0.063 Uiso 1 1 calc R U . . .
C19 C 0.4360(2) -0.2166(3) 0.10261(11) 0.0460(5) Uani 1 1 d . . . . .
C20 C 0.3643(3) 0.1363(3) 0.20476(10) 0.0534(6) Uani 1 1 d . . . . .
H7 H 0.3473 0.1570 0.2456 0.064 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C16 1.400(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 C4 1.330(3) . ?
N2 C10 1.330(3) . ?
N2 H2 0.8600 . ?
N3 C8 1.322(3) . ?
N3 C13 1.326(3) . ?
O1 C19 1.233(3) . ?
O2 C19 1.272(3) . ?
O3 C17 1.359(3) . ?
O3 H3 0.8200 . ?
C1 C5 1.380(3) . ?
C1 C11 1.386(3) . ?
C1 C6 1.499(3) . ?
C2 C12 1.375(3) . ?
C2 C7 1.377(3) . ?
C2 C9 1.506(3) . ?
C3 C9 1.527(3) . ?
C3 C6 1.529(3) . ?
C3 H14A 0.9700 . ?
C3 H15B 0.9700 . ?
C4 C5 1.367(3) . ?
C4 H19 0.9300 . ?
C5 H18 0.9300 . ?
C6 H17A 0.9700 . ?
C6 H16B 0.9700 . ?
C7 C8 1.375(3) . ?
C7 H11 0.9300 . ?
C8 H10 0.9300 . ?
C9 H12A 0.9700 . ?
C9 H13B 0.9700 . ?
C10 C11 1.358(3) . ?
C10 H20 0.9300 . ?
C11 H21 0.9300 . ?
C12 C13 1.371(3) . ?
C12 H9 0.9300 . ?
C13 H8 0.9300 . ?
C14 C15 1.394(3) . ?
C14 C17 1.394(3) . ?
C14 C19 1.512(3) . ?
C15 C16 1.390(3) . ?
C15 H5 0.9300 . ?
C16 C18 1.398(3) . ?
C17 C20 1.388(3) . ?
C18 C20 1.372(3) . ?
C18 H6 0.9300 . ?
C20 H7 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N1 H1A 120.0 . . ?
C16 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C4 N2 C10 121.23(19) . . ?
C4 N2 H2 119.4 . . ?
C10 N2 H2 119.4 . . ?
C8 N3 C13 116.57(19) . . ?
C17 O3 H3 109.5 . . ?
C5 C1 C11 117.05(19) . . ?
C5 C1 C6 121.1(2) . . ?
C11 C1 C6 121.9(2) . . ?
C12 C2 C7 116.4(2) . . ?
C12 C2 C9 121.7(2) . . ?
C7 C2 C9 121.9(2) . . ?
C9 C3 C6 111.20(17) . . ?
C9 C3 H14A 109.4 . . ?
C6 C3 H14A 109.4 . . ?
C9 C3 H15B 109.4 . . ?
C6 C3 H15B 109.4 . . ?
H14A C3 H15B 108.0 . . ?
N2 C4 C5 119.9(2) . . ?
N2 C4 H19 120.1 . . ?
C5 C4 H19 120.1 . . ?
C4 C5 C1 120.8(2) . . ?
C4 C5 H18 119.6 . . ?
C1 C5 H18 119.6 . . ?
C1 C6 C3 113.10(17) . . ?
C1 C6 H17A 109.0 . . ?
C3 C6 H17A 109.0 . . ?
C1 C6 H16B 109.0 . . ?
C3 C6 H16B 109.0 . . ?
H17A C6 H16B 107.8 . . ?
C8 C7 C2 120.2(2) . . ?
C8 C7 H11 119.9 . . ?
C2 C7 H11 119.9 . . ?
N3 C8 C7 123.2(2) . . ?
N3 C8 H10 118.4 . . ?
C7 C8 H10 118.4 . . ?
C2 C9 C3 113.02(17) . . ?
C2 C9 H12A 109.0 . . ?
C3 C9 H12A 109.0 . . ?
C2 C9 H13B 109.0 . . ?
C3 C9 H13B 109.0 . . ?
H12A C9 H13B 107.8 . . ?
N2 C10 C11 120.6(2) . . ?
N2 C10 H20 119.7 . . ?
C11 C10 H20 119.7 . . ?
C10 C11 C1 120.4(2) . . ?
C10 C11 H21 119.8 . . ?
C1 C11 H21 119.8 . . ?
C13 C12 C2 119.8(2) . . ?
C13 C12 H9 120.1 . . ?
C2 C12 H9 120.1 . . ?
N3 C13 C12 123.8(2) . . ?
N3 C13 H8 118.1 . . ?
C12 C13 H8 118.1 . . ?
C15 C14 C17 118.84(19) . . ?
C15 C14 C19 120.30(18) . . ?
C17 C14 C19 120.82(19) . . ?
C16 C15 C14 122.23(19) . . ?
C16 C15 H5 118.9 . . ?
C14 C15 H5 118.9 . . ?
C15 C16 C18 117.5(2) . . ?
C15 C16 N1 121.66(19) . . ?
C18 C16 N1 120.68(19) . . ?
O3 C17 C20 118.9(2) . . ?
O3 C17 C14 121.7(2) . . ?
C20 C17 C14 119.3(2) . . ?
C20 C18 C16 121.0(2) . . ?
C20 C18 H6 119.5 . . ?
C16 C18 H6 119.5 . . ?
O1 C19 O2 123.9(2) . . ?
O1 C19 C14 119.5(2) . . ?
O2 C19 C14 116.6(2) . . ?
C18 C20 C17 121.1(2) . . ?
C18 C20 H7 119.5 . . ?
C17 C20 H7 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N2 C4 C5 1.1(3) . . . . ?
N2 C4 C5 C1 -0.8(3) . . . . ?
C11 C1 C5 C4 -0.3(3) . . . . ?
C6 C1 C5 C4 179.9(2) . . . . ?
C5 C1 C6 C3 86.8(3) . . . . ?
C11 C1 C6 C3 -93.0(2) . . . . ?
C9 C3 C6 C1 -179.3(2) . . . . ?
C12 C2 C7 C8 -0.8(3) . . . . ?
C9 C2 C7 C8 -179.1(2) . . . . ?
C13 N3 C8 C7 0.5(4) . . . . ?
C2 C7 C8 N3 0.4(4) . . . . ?
C12 C2 C9 C3 -80.7(3) . . . . ?
C7 C2 C9 C3 97.5(3) . . . . ?
C6 C3 C9 C2 -179.3(2) . . . . ?
C4 N2 C10 C11 -0.2(3) . . . . ?
N2 C10 C11 C1 -1.0(3) . . . . ?
C5 C1 C11 C10 1.2(3) . . . . ?
C6 C1 C11 C10 -179.0(2) . . . . ?
C7 C2 C12 C13 0.3(3) . . . . ?
C9 C2 C12 C13 178.6(2) . . . . ?
C8 N3 C13 C12 -1.0(4) . . . . ?
C2 C12 C13 N3 0.6(4) . . . . ?
C17 C14 C15 C16 -0.1(3) . . . . ?
C19 C14 C15 C16 177.71(18) . . . . ?
C14 C15 C16 C18 0.0(3) . . . . ?
C14 C15 C16 N1 -175.88(18) . . . . ?
C15 C14 C17 O3 178.8(2) . . . . ?
C19 C14 C17 O3 1.0(3) . . . . ?
C15 C14 C17 C20 0.3(3) . . . . ?
C19 C14 C17 C20 -177.50(19) . . . . ?
C15 C16 C18 C20 -0.1(3) . . . . ?
N1 C16 C18 C20 175.8(2) . . . . ?
C15 C14 C19 O1 1.4(3) . . . . ?
C17 C14 C19 O1 179.1(2) . . . . ?
C15 C14 C19 O2 -177.67(19) . . . . ?
C17 C14 C19 O2 0.1(3) . . . . ?
C16 C18 C20 C17 0.3(4) . . . . ?
O3 C17 C20 C18 -178.9(2) . . . . ?
C14 C17 C20 C18 -0.4(3) . . . . ?

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
C11 H21 O3 0.93 2.60 3.333(3) 135.7 2_655
C10 H20 N1 0.93 2.60 3.486(3) 159.8 1_655
C4 H19 O1 0.93 2.35 3.269(3) 167.7 3_655
O3 H3 O2 0.82 1.78 2.512(2) 147.5 .
N2 H2 N3 0.86 1.86 2.718(2) 175.0 4_665
N1 H1B O2 0.86 2.51 3.275(3) 148.6 1_565
N1 H1A O1 0.86 2.28 3.009(3) 142.9 3_655
C11 H21 O3 0.93 2.60 3.333(3) 135.7 2_655
C10 H20 N1 0.93 2.60 3.486(3) 159.8 1_655
C4 H19 O1 0.93 2.35 3.269(3) 167.7 3_655
O3 H3 O2 0.82 1.78 2.512(2) 147.5 .
N2 H2 N3 0.86 1.86 2.718(2) 175.0 4_665
N1 H1B O2 0.86 2.51 3.275(3) 148.6 1_565
N1 H1A O1 0.86 2.28 3.009(3) 142.9 3_655
N1 H1A O1 0.86 2.28 3.009(3) 142.9 3_655
N1 H1B O2 0.86 2.51 3.275(3) 148.6 1_565
N2 H2 N3 0.86 1.86 2.718(2) 175.0 4_665
O3 H3 O2 0.82 1.78 2.512(2) 147.5 .
C4 H19 O1 0.93 2.35 3.269(3) 167.7 3_655
C10 H20 N1 0.93 2.60 3.486(3) 159.8 1_655
C11 H21 O3 0.93 2.60 3.333(3) 135.7 2_655

_refine_diff_density_max         0.283
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.035

