# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_5FU-35DHBA
_database_code_depnum_ccdc_archive 'CCDC 1970719'
loop_
_audit_author_name
_audit_author_address
'Xia-Lin Dai'
;Sun Yat sen University
China
;
_audit_update_record             
;
2019-12-09 deposited with the CCDC.	2020-04-23 downloaded from the CCDC.
;
_audit_creation_date             2019-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H3 F N2 O2, C7 H6 O4'
_chemical_formula_sum            'C11 H9 F N2 O6'
_chemical_formula_weight         284.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8352(6)
_cell_length_b                   8.9191(7)
_cell_length_c                   9.4663(7)
_cell_angle_alpha                111.550(7)
_cell_angle_beta                 107.076(7)
_cell_angle_gamma                100.662(6)
_cell_volume                     555.34(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3598
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      78.5570
_cell_measurement_theta_min      5.4680
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.319
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5446
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.650
_diffrn_reflns_theta_min         5.471
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  68.00   0.50    0.50    --    0.00  57.00-150.00  192
  2  ω    -29.00  41.00   0.50    0.50    --    0.00  37.00   0.00  140
  3  ω     51.00  85.00   0.50    0.50    --    0.00  37.00   0.00   68
  4  ω    -27.00  10.00   0.50    0.50    --    0.00  57.00 120.00   74
  5  ω     75.00 113.00   0.50    0.50    --  106.20 -82.00 150.00   76
  6  ω     95.00 124.00   0.50    0.50    --  106.20  61.00-150.00   58
  7  ω     96.00 141.00   0.50    0.50    --  106.20  45.00-180.00   90
  8  ω     20.00  68.00   0.50    0.50    --  106.20 -45.00-120.00   96
  9  ω    106.00 132.00   0.50    0.50    --  106.20 -77.00 -90.00   52
 10  ω     33.00  73.00   0.50    0.50    --  106.20 -82.00 -30.00   80
 11  ω     82.00 148.00   0.50    0.50    --  106.20  45.00-150.00  132
 12  ω     80.00 179.00   0.50    0.50    --  106.20  45.00 150.00  198
 13  ω     38.00 137.00   0.50    0.50    --  106.20 -82.00  60.00  198
 14  ω    122.00 196.00   0.50    0.50    --  106.20  45.00  60.00  148
 15  ω     37.00  70.00   0.50    0.50    --  106.20 -82.00-120.00   66
 16  ω     17.00  91.00   0.50    0.50    --  106.20 -77.00 -90.00  148
 17  ω     86.00 162.00   0.50    0.50    --  106.20  45.00 120.00  152
 18  ω     78.00 132.00   0.50    0.50    --  106.20 -82.00-120.00  108
 19  ω    171.00 196.00   0.50    0.50    --  106.20  61.00-150.00   50
 20  ω     78.00 134.00   0.50    0.50    --  106.20 -45.00-120.00  112
 21  ω    150.00 192.00   0.50    0.50    --  106.20  45.00-180.00   84
 22  ω     90.00 130.00   0.50    0.50    --  106.20 -82.00 -30.00   80
 23  ω     96.00 141.00   0.50    0.50    --  106.20 -77.00  30.00   90
 24  ω    153.00 191.00   0.50    0.50    --  106.20  45.00-150.00   76
 25  ω     28.00  54.00   0.50    0.50    --  106.20 -77.00  30.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0968933000
_diffrn_orient_matrix_UB_12      0.0298948000
_diffrn_orient_matrix_UB_13      0.1231715000
_diffrn_orient_matrix_UB_21      0.1941652000
_diffrn_orient_matrix_UB_22      0.0696631000
_diffrn_orient_matrix_UB_23      0.1443483000
_diffrn_orient_matrix_UB_31      0.0192005000
_diffrn_orient_matrix_UB_32      0.1814906000
_diffrn_orient_matrix_UB_33      0.0169744000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2062
_reflns_number_total             2323
_reflns_odcompleteness_completeness 99.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.924
_refine_diff_density_rms         0.205
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0900
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1971P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2227
_refine_ls_wR_factor_ref         0.2295
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C6(H6A), C8(H8), C10(H10), C4(H4A)
2.b Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4), O6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 1.52919(16) 0.68257(15) 1.05494(16) 0.0288(4) Uani 1 1 d . . . . .
O1 O 0.86132(19) 0.78382(16) 0.89178(17) 0.0188(4) Uani 1 1 d . . . . .
O5 O 0.65290(18) 0.35891(16) 0.67333(18) 0.0203(4) Uani 1 1 d . . . . .
O3 O 0.09392(17) -0.19078(15) 0.28027(17) 0.0196(4) Uani 1 1 d . . . . .
H3 H 0.187445 -0.210041 0.326680 0.029 Uiso 1 1 calc GR . . . .
O4 O -0.16717(19) 0.26089(16) 0.37666(19) 0.0235(4) Uani 1 1 d . . . . .
H4 H -0.265024 0.179950 0.315038 0.035 Uiso 1 1 calc GR . . . .
O6 O 0.51615(18) 0.55957(16) 0.69095(17) 0.0213(4) Uani 1 1 d . . . . .
H6 H 0.621661 0.621563 0.761935 0.032 Uiso 1 1 calc GR . . . .
O2 O 1.49972(19) 1.00509(17) 1.16599(18) 0.0273(4) Uani 1 1 d . . . . .
N2 N 1.0296(2) 0.60022(19) 0.8698(2) 0.0172(4) Uani 1 1 d . . . . .
H2 H 0.927903 0.513883 0.807327 0.021 Uiso 1 1 calc R . . . .
N1 N 1.1822(2) 0.89146(18) 1.01691(19) 0.0163(4) Uani 1 1 d . . . . .
H1 H 1.175854 0.992817 1.043789 0.020 Uiso 1 1 calc R . . . .
C9 C -0.0180(2) 0.2030(2) 0.3989(2) 0.0154(4) Uani 1 1 d . . . . .
C1 C 1.0152(3) 0.7585(2) 0.9239(2) 0.0149(4) Uani 1 1 d . . . . .
C6 C 0.2999(2) 0.1003(2) 0.4544(2) 0.0161(4) Uani 1 1 d . . . . .
H6A H 0.406215 0.066035 0.472238 0.019 Uiso 1 1 calc R . . . .
C8 C -0.0386(2) 0.0308(2) 0.3249(2) 0.0151(4) Uani 1 1 d . . . . .
H8 H -0.157624 -0.050308 0.256128 0.018 Uiso 1 1 calc R . . . .
C5 C 0.3183(2) 0.27352(19) 0.5278(2) 0.0139(4) Uani 1 1 d . . . . .
C7 C 0.1219(2) -0.0189(2) 0.3551(2) 0.0148(4) Uani 1 1 d . . . . .
C11 C 0.5106(2) 0.3991(2) 0.6357(2) 0.0148(4) Uani 1 1 d . . . . .
C10 C 0.1610(3) 0.3265(2) 0.5006(2) 0.0157(4) Uani 1 1 d . . . . .
H10 H 0.174159 0.441850 0.548843 0.019 Uiso 1 1 calc R . . . .
C2 C 1.3605(2) 0.8778(2) 1.0717(2) 0.0176(4) Uani 1 1 d . . . . .
C3 C 1.3603(3) 0.7052(2) 1.0087(2) 0.0190(4) Uani 1 1 d . . . . .
C4 C 1.1998(3) 0.5713(2) 0.9103(2) 0.0196(4) Uani 1 1 d . . . . .
H4A H 1.203974 0.460505 0.870234 0.023 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.345(2) . ?
O1 C1 1.238(2) . ?
O5 C11 1.228(2) . ?
O3 H3 0.8200 . ?
O3 C7 1.3735(19) . ?
O4 H4 0.8200 . ?
O4 C9 1.3549(19) . ?
O6 H6 0.8200 . ?
O6 C11 1.318(2) . ?
O2 C2 1.225(2) . ?
N2 H2 0.8600 . ?
N2 C1 1.353(2) . ?
N2 C4 1.375(2) . ?
N1 H1 0.8600 . ?
N1 C1 1.370(2) . ?
N1 C2 1.385(2) . ?
C9 C8 1.388(2) . ?
C9 C10 1.401(2) . ?
C6 H6A 0.9300 . ?
C6 C5 1.400(2) . ?
C6 C7 1.381(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.396(2) . ?
C5 C11 1.483(2) . ?
C5 C10 1.388(2) . ?
C10 H10 0.9300 . ?
C2 C3 1.431(3) . ?
C3 C4 1.347(3) . ?
C4 H4A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O3 H3 109.5 . . ?
C9 O4 H4 109.5 . . ?
C11 O6 H6 109.5 . . ?
C1 N2 H2 118.5 . . ?
C1 N2 C4 122.92(16) . . ?
C4 N2 H2 118.5 . . ?
C1 N1 H1 117.0 . . ?
C1 N1 C2 126.05(15) . . ?
C2 N1 H1 117.0 . . ?
O4 C9 C8 122.50(16) . . ?
O4 C9 C10 116.54(15) . . ?
C8 C9 C10 120.96(16) . . ?
O1 C1 N2 122.73(16) . . ?
O1 C1 N1 121.29(16) . . ?
N2 C1 N1 115.98(15) . . ?
C5 C6 H6A 120.4 . . ?
C7 C6 H6A 120.4 . . ?
C7 C6 C5 119.10(15) . . ?
C9 C8 H8 120.5 . . ?
C9 C8 C7 119.07(17) . . ?
C7 C8 H8 120.5 . . ?
C6 C5 C11 118.17(14) . . ?
C10 C5 C6 121.02(16) . . ?
C10 C5 C11 120.81(14) . . ?
O3 C7 C6 122.06(14) . . ?
O3 C7 C8 116.83(16) . . ?
C6 C7 C8 121.11(16) . . ?
O5 C11 O6 122.31(16) . . ?
O5 C11 C5 123.58(14) . . ?
O6 C11 C5 114.10(13) . . ?
C9 C10 H10 120.6 . . ?
C5 C10 C9 118.72(15) . . ?
C5 C10 H10 120.6 . . ?
O2 C2 N1 120.86(16) . . ?
O2 C2 C3 125.80(16) . . ?
N1 C2 C3 113.33(16) . . ?
F1 C3 C2 116.52(16) . . ?
F1 C3 C4 121.23(17) . . ?
C4 C3 C2 122.24(16) . . ?
N2 C4 H4A 120.4 . . ?
C3 C4 N2 119.22(17) . . ?
C3 C4 H4A 120.4 . . ?

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
O3 H3 O5 0.82 1.99 2.7294(18) 150.5 2_656
O4 H4 O2 0.82 1.90 2.7187(19) 175.1 1_344
O6 H6 O1 0.82 1.86 2.6673(19) 167.4 .
N2 H2 O5 0.86 2.04 2.879(2) 164.4 .
N1 H1 O1 0.86 1.96 2.820(2) 174.4 2_777

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
F1 C3 C4 N2 178.23(15) . . . . ?
O4 C9 C8 C7 -179.40(15) . . . . ?
O4 C9 C10 C5 179.70(15) . . . . ?
O2 C2 C3 F1 -1.6(3) . . . . ?
O2 C2 C3 C4 177.4(2) . . . . ?
N1 C2 C3 F1 179.03(15) . . . . ?
N1 C2 C3 C4 -2.1(3) . . . . ?
C9 C8 C7 O3 179.42(14) . . . . ?
C9 C8 C7 C6 -1.3(3) . . . . ?
C1 N2 C4 C3 0.3(3) . . . . ?
C1 N1 C2 O2 -173.84(17) . . . . ?
C1 N1 C2 C3 5.6(3) . . . . ?
C6 C5 C11 O5 -5.2(3) . . . . ?
C6 C5 C11 O6 175.82(15) . . . . ?
C6 C5 C10 C9 0.6(3) . . . . ?
C8 C9 C10 C5 -0.7(3) . . . . ?
C5 C6 C7 O3 -179.60(15) . . . . ?
C5 C6 C7 C8 1.1(3) . . . . ?
C7 C6 C5 C11 179.18(14) . . . . ?
C7 C6 C5 C10 -0.8(3) . . . . ?
C11 C5 C10 C9 -179.37(15) . . . . ?
C10 C9 C8 C7 1.1(3) . . . . ?
C10 C5 C11 O5 174.78(16) . . . . ?
C10 C5 C11 O6 -4.2(2) . . . . ?
C2 N1 C1 O1 174.19(17) . . . . ?
C2 N1 C1 N2 -6.0(3) . . . . ?
C2 C3 C4 N2 -0.6(3) . . . . ?
C4 N2 C1 O1 -177.47(16) . . . . ?
C4 N2 C1 N1 2.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.602
_oxdiff_exptl_absorpt_empirical_full_min 0.485
####################################################################### 
# 
# 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_5FU-34DHBA-2H2O
_database_code_depnum_ccdc_archive 'CCDC 1970722'
loop_
_audit_author_name
_audit_author_address
'Xia-Lin Dai'
;Sun Yat Sen University
China
;
_audit_update_record             
;
2019-12-09 deposited with the CCDC.	2020-04-23 downloaded from the CCDC.
;
_audit_creation_date             2019-09-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H3 F N2 O2, C7 H6 O4, 2(H2 O)'
_chemical_formula_sum            'C11 H13 F N2 O8'
_chemical_formula_weight         320.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2314(4)
_cell_length_b                   9.9761(6)
_cell_length_c                   10.2732(5)
_cell_angle_alpha                103.754(5)
_cell_angle_beta                 102.275(5)
_cell_angle_gamma                108.186(5)
_cell_volume                     650.05(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4295
_cell_measurement_temperature    150(10)
_cell_measurement_theta_max      65.3760
_cell_measurement_theta_min      4.6270
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.880
_exptl_absorpt_coefficient_mu    1.315
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10247
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        63.677
_diffrn_reflns_theta_max         63.677
_diffrn_reflns_theta_min         4.662
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      150(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5058
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -35.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7938  -38.0000  -60.0000 102

#__ type_ start__ end____ width___ exp.time_
  2 omega   14.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7938   38.0000  120.0000 103

#__ type_ start__ end____ width___ exp.time_
  3 omega   44.00  124.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7938  167.0000  -28.0000 80

#__ type_ start__ end____ width___ exp.time_
  4 omega -158.00  -94.00   1.0000    2.0850
omega____ theta____ kappa____ phi______ frames
    -      -83.0000 -126.0000 -180.0000 64

#__ type_ start__ end____ width___ exp.time_
  5 omega -122.00  -19.00   1.0000    2.0850
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  126.0000 -150.0000 103

#__ type_ start__ end____ width___ exp.time_
  6 omega  -69.00   -5.00   1.0000    2.0850
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   30.0000 -180.0000 64

#__ type_ start__ end____ width___ exp.time_
  7 omega -122.00  -19.00   1.0000    2.0850
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  126.0000   90.0000 103

#__ type_ start__ end____ width___ exp.time_
  8 omega   63.00  165.00   1.0000    2.0850
omega____ theta____ kappa____ phi______ frames
    -       90.6218   45.0000  -30.0000 102

#__ type_ start__ end____ width___ exp.time_
  9 omega   60.00  165.00   1.0000    2.0850
omega____ theta____ kappa____ phi______ frames
    -       90.6218   61.0000   60.0000 105

#__ type_ start__ end____ width___ exp.time_
 10 omega   16.00  121.00   1.0000    2.0850
omega____ theta____ kappa____ phi______ frames
    -       90.6218  -61.0000   90.0000 105

#__ type_ start__ end____ width___ exp.time_
 11 omega    7.00   84.00   1.0000    2.0850
omega____ theta____ kappa____ phi______ frames
    -       90.6218  -95.0000    0.0000 77

#__ type_ start__ end____ width___ exp.time_
 12 omega   16.00   97.00   1.0000    2.0850
omega____ theta____ kappa____ phi______ frames
    -       90.6218 -126.0000  120.0000 81

#__ type_ start__ end____ width___ exp.time_
 13 omega   57.00  169.00   1.0000    2.0850
omega____ theta____ kappa____ phi______ frames
    -       90.6218   77.0000    0.0000 112

#__ type_ start__ end____ width___ exp.time_
 14 omega   11.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7938   57.0000 -120.0000 104

#__ type_ start__ end____ width___ exp.time_
 15 omega    7.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7938   77.0000  -30.0000 113

#__ type_ start__ end____ width___ exp.time_
 16 omega   11.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7938   57.0000  150.0000 104

#__ type_ start__ end____ width___ exp.time_
 17 omega -162.00  -49.00   1.0000    2.0850
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   90.0000 113

#__ type_ start__ end____ width___ exp.time_
 18 omega -162.00  -49.00   1.0000    2.0850
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -30.0000 113

#__ type_ start__ end____ width___ exp.time_
 19 omega -162.00  -49.00   1.0000    2.0850
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -90.0000 113

#__ type_ start__ end____ width___ exp.time_
 20 omega -162.00  -49.00   1.0000    2.0850
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  150.0000 113

#__ type_ start__ end____ width___ exp.time_
 21 omega -162.00  -49.00   1.0000    2.0850
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -150.0000 113

#__ type_ start__ end____ width___ exp.time_
 22 omega   16.00   73.00   1.0000    2.0850
omega____ theta____ kappa____ phi______ frames
    -       90.6218  -45.0000  -30.0000 57

#__ type_ start__ end____ width___ exp.time_
 23 omega   60.00  165.00   1.0000    2.0850
omega____ theta____ kappa____ phi______ frames
    -       90.6218   61.0000  120.0000 105

#__ type_ start__ end____ width___ exp.time_
 24 omega   60.00  165.00   1.0000    2.0850
omega____ theta____ kappa____ phi______ frames
    -       90.6218   61.0000 -120.0000 105

#__ type_ start__ end____ width___ exp.time_
 25 omega   63.00  165.00   1.0000    2.0850
omega____ theta____ kappa____ phi______ frames
    -       90.6218   45.0000 -180.0000 102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0840556000
_diffrn_orient_matrix_UB_12      -0.1465082000
_diffrn_orient_matrix_UB_13      -0.1248510000
_diffrn_orient_matrix_UB_21      -0.0386455000
_diffrn_orient_matrix_UB_22      -0.0901679000
_diffrn_orient_matrix_UB_23      0.1009729000
_diffrn_orient_matrix_UB_31      -0.2170255000
_diffrn_orient_matrix_UB_32      0.0013433000
_diffrn_orient_matrix_UB_33      -0.0245044000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1783
_reflns_number_total             2111
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.174
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0637P)²+0.1328P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1075
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O8(H8A,H8B), O7(H7A)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2B), N1(H1), C9(H9), C6(H6), C5(H5), C2(H2A)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4), O3(H3), O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.29602(17) 0.94276(11) 0.88408(11) 0.0283(3) Uani 1 1 d . . . . .
O4 O 0.77328(19) 1.61809(13) 0.93946(12) 0.0225(3) Uani 1 1 d . . . . .
H4 H 0.756838 1.672162 0.892902 0.034 Uiso 1 1 calc GR . . . .
O3 O 0.85311(19) 1.47748(12) 1.11720(12) 0.0226(3) Uani 1 1 d . . . . .
H3 H 0.899795 1.441098 1.173407 0.034 Uiso 1 1 calc GR . . . .
N2 N 0.2429(2) 1.14417(15) 0.64361(14) 0.0188(3) Uani 1 1 d . . . . .
H2B H 0.169120 1.130369 0.560333 0.023 Uiso 1 1 calc R . . . .
O5 O 0.4253(2) 1.38316(13) 0.66184(13) 0.0288(3) Uani 1 1 d . . . . .
O2 O 1.4519(2) 2.15394(14) 1.38563(13) 0.0292(4) Uani 1 1 d . . . . .
H2 H 1.510911 2.243219 1.399451 0.044 Uiso 1 1 calc GR . . . .
N1 N 0.5033(2) 1.30357(15) 0.84788(15) 0.0199(4) Uani 1 1 d . . . . .
H1 H 0.595150 1.390388 0.897894 0.024 Uiso 1 1 calc R . . . .
O1 O 1.2800(2) 2.16177(14) 1.18152(13) 0.0287(3) Uani 1 1 d . . . . .
C3 C 0.9270(3) 1.70139(18) 1.06354(16) 0.0167(4) Uani 1 1 d . . . . .
C9 C 0.4746(3) 1.1913(2) 0.90567(18) 0.0201(4) Uani 1 1 d . . . . .
H9 H 0.555276 1.208957 0.996297 0.024 Uiso 1 1 calc R . . . .
C6 C 1.2306(3) 1.85660(19) 1.32339(18) 0.0190(4) Uani 1 1 d . . . . .
H6 H 1.330824 1.908495 1.410588 0.023 Uiso 1 1 calc R . . . .
C10 C 0.3304(3) 1.05648(19) 0.83123(18) 0.0189(4) Uani 1 1 d . . . . .
C5 C 1.1178(3) 1.70540(19) 1.28801(18) 0.0192(4) Uani 1 1 d . . . . .
H5 H 1.143261 1.656302 1.352076 0.023 Uiso 1 1 calc R . . . .
C7 C 1.3101(3) 2.09226(19) 1.26081(17) 0.0188(4) Uani 1 1 d . . . . .
C1 C 1.1932(3) 1.93067(19) 1.22754(17) 0.0173(4) Uani 1 1 d . . . . .
C11 C 0.1990(3) 1.02458(18) 0.69172(17) 0.0171(4) Uani 1 1 d . . . . .
C2 C 1.0411(3) 1.85145(19) 1.09792(17) 0.0175(4) Uani 1 1 d . . . . .
H2A H 1.016236 1.900495 1.033709 0.021 Uiso 1 1 calc R . . . .
C4 C 0.9679(3) 1.62624(19) 1.15900(18) 0.0183(4) Uani 1 1 d . . . . .
C8 C 0.3933(3) 1.28423(19) 0.71510(18) 0.0194(4) Uani 1 1 d . . . . .
O8 O -0.0044(2) 0.36280(15) 0.31573(14) 0.0322(4) Uani 1 1 d . . . . .
H8A H 0.102026 0.424982 0.382429 0.048 Uiso 1 1 d G . . . .
H8B H -0.025725 0.275252 0.319709 0.048 Uiso 1 1 d G . . . .
O7 O 0.2912(2) 0.57217(15) 0.56426(15) 0.0311(4) Uani 1 1 d . . . . .
H7A H 0.338754 0.515647 0.598225 0.047 Uiso 1 1 d G . . . .
O6 O 0.05813(19) 0.90348(13) 0.62046(12) 0.0213(3) Uani 1 1 d . . . . .
H7B H 0.196(6) 0.590(4) 0.601(4) 0.107(14) 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
F1 C10 1.348(2) . ?
O4 H4 0.8200 . ?
O4 C3 1.367(2) . ?
O3 H3 0.8200 . ?
O3 C4 1.361(2) . ?
N2 H2B 0.8600 . ?
N2 C11 1.371(2) . ?
N2 C8 1.378(2) . ?
O5 C8 1.223(2) . ?
O2 H2 0.8200 . ?
O2 C7 1.321(2) . ?
N1 H1 0.8600 . ?
N1 C9 1.369(2) . ?
N1 C8 1.360(2) . ?
O1 C7 1.216(2) . ?
C3 C2 1.378(2) . ?
C3 C4 1.406(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.333(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.385(3) . ?
C6 C1 1.395(2) . ?
C10 C11 1.440(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.383(2) . ?
C7 C1 1.482(2) . ?
C1 C2 1.393(2) . ?
C11 O6 1.236(2) . ?
C2 H2A 0.9300 . ?
O8 H8A 0.8500 . ?
O8 H8B 0.8509 . ?
O7 H7A 0.8495 . ?
O7 H7B 0.89(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O4 H4 109.5 . . ?
C4 O3 H3 109.5 . . ?
C11 N2 H2B 116.7 . . ?
C11 N2 C8 126.62(15) . . ?
C8 N2 H2B 116.7 . . ?
C7 O2 H2 109.5 . . ?
C9 N1 H1 118.5 . . ?
C8 N1 H1 118.5 . . ?
C8 N1 C9 123.07(15) . . ?
O4 C3 C2 123.78(15) . . ?
O4 C3 C4 116.62(14) . . ?
C2 C3 C4 119.60(16) . . ?
N1 C9 H9 120.2 . . ?
C10 C9 N1 119.59(16) . . ?
C10 C9 H9 120.2 . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C1 119.67(16) . . ?
C1 C6 H6 120.2 . . ?
F1 C10 C11 116.08(15) . . ?
C9 C10 F1 121.66(15) . . ?
C9 C10 C11 122.24(16) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.07(16) . . ?
C4 C5 H5 119.5 . . ?
O2 C7 C1 113.24(15) . . ?
O1 C7 O2 123.06(16) . . ?
O1 C7 C1 123.70(16) . . ?
C6 C1 C7 121.53(16) . . ?
C2 C1 C6 119.38(16) . . ?
C2 C1 C7 119.08(15) . . ?
N2 C11 C10 113.22(15) . . ?
O6 C11 N2 121.93(15) . . ?
O6 C11 C10 124.85(15) . . ?
C3 C2 C1 120.92(16) . . ?
C3 C2 H2A 119.5 . . ?
C1 C2 H2A 119.5 . . ?
O3 C4 C3 116.65(15) . . ?
O3 C4 C5 124.03(15) . . ?
C5 C4 C3 119.32(15) . . ?
O5 C8 N2 122.01(16) . . ?
O5 C8 N1 122.79(16) . . ?
N1 C8 N2 115.20(15) . . ?
H8A O8 H8B 109.4 . . ?
H7A O7 H7B 112.4 . . ?

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
O4 H4 O1 0.82 2.05 2.8527(17) 167.2 2_797
O3 H3 O8 0.82 1.92 2.7352(17) 174.7 1_666
N2 H2B O6 0.86 2.08 2.9247(19) 167.6 2_576
N1 H1 O4 0.86 2.12 2.9213(18) 155.5 .
N1 H1 O3 0.86 2.36 3.0110(19) 132.5 .
O8 H8A O7 0.85 1.97 2.7942(19) 163.8 .
O8 H8B O6 0.85 1.98 2.8160(17) 165.8 2_566
O7 H7A O5 0.85 1.82 2.6699(18) 175.9 1_545

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
F1 C10 C11 N2 -179.43(14) . . . . ?
F1 C10 C11 O6 1.3(3) . . . . ?
O4 C3 C2 C1 178.71(16) . . . . ?
O4 C3 C4 O3 1.2(2) . . . . ?
O4 C3 C4 C5 -178.19(15) . . . . ?
O2 C7 C1 C6 1.6(2) . . . . ?
O2 C7 C1 C2 -178.96(15) . . . . ?
N1 C9 C10 F1 -179.67(15) . . . . ?
N1 C9 C10 C11 -1.3(3) . . . . ?
O1 C7 C1 C6 -178.59(17) . . . . ?
O1 C7 C1 C2 0.8(3) . . . . ?
C9 N1 C8 N2 2.7(2) . . . . ?
C9 N1 C8 O5 -176.83(17) . . . . ?
C9 C10 C11 N2 2.1(2) . . . . ?
C9 C10 C11 O6 -177.11(17) . . . . ?
C6 C5 C4 O3 179.36(16) . . . . ?
C6 C5 C4 C3 -1.3(3) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
C5 C6 C1 C7 -179.97(16) . . . . ?
C5 C6 C1 C2 0.6(3) . . . . ?
C7 C1 C2 C3 -179.18(15) . . . . ?
C1 C6 C5 C4 -0.1(3) . . . . ?
C11 N2 C8 O5 177.79(16) . . . . ?
C11 N2 C8 N1 -1.8(3) . . . . ?
C2 C3 C4 O3 -178.47(15) . . . . ?
C2 C3 C4 C5 2.1(3) . . . . ?
C4 C3 C2 C1 -1.6(3) . . . . ?
C8 N2 C11 C10 -0.5(2) . . . . ?
C8 N2 C11 O6 178.74(16) . . . . ?
C8 N1 C9 C10 -1.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5FU-25DHBA
_database_code_depnum_ccdc_archive 'CCDC 1970721'
loop_
_audit_author_name
_audit_author_address
'Xia-Lin Dai'
;Sun Yat Sen University
China
;
_audit_update_record             
;
2019-12-09 deposited with the CCDC.	2020-04-23 downloaded from the CCDC.
;
_audit_creation_date             2019-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C7 H6 O4, C4 H3 F N2 O2'
_chemical_formula_sum            'C11 H9 F N2 O6'
_chemical_formula_weight         284.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.5121(4)
_cell_length_b                   5.5084(3)
_cell_length_c                   21.2993(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.115(4)
_cell_angle_gamma                90
_cell_volume                     1113.13(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2350
_cell_measurement_temperature    150(10)
_cell_measurement_theta_max      67.0340
_cell_measurement_theta_min      4.1200
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.316
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5282
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.265
_diffrn_reflns_theta_max         67.265
_diffrn_reflns_theta_min         4.162
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      150(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5058
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -22.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.3352  -99.0000   90.0000 97

#__ type_ start__ end____ width___ exp.time_
  2 omega   37.00   88.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       96.5000 -112.0000   90.0000 51

#__ type_ start__ end____ width___ exp.time_
  3 omega   50.00   75.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       96.5000  -45.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega   10.00   82.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       96.5000  -95.0000    0.0000 72

#__ type_ start__ end____ width___ exp.time_
  5 omega   40.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.3352  -99.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega   25.00   75.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       96.5000 -112.0000 -120.0000 50

#__ type_ start__ end____ width___ exp.time_
  7 omega   52.00   78.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       96.5000  -95.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   17.00   50.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       96.5000 -112.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
  9 omega  -24.00   37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.3352  -99.0000 -120.0000 61

#__ type_ start__ end____ width___ exp.time_
 10 omega   78.00  104.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       96.5000   45.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega  118.00  158.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       96.5000   45.0000 -180.0000 40

#__ type_ start__ end____ width___ exp.time_
 12 omega  133.00  159.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       96.5000   61.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   79.00  168.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       96.5000  112.0000 -120.0000 89

#__ type_ start__ end____ width___ exp.time_
 14 omega   79.00  158.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       96.5000  112.0000    0.0000 79

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.3352  126.0000   90.0000 31

#__ type_ start__ end____ width___ exp.time_
 16 omega  135.00  169.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       96.5000   77.0000  150.0000 34

#__ type_ start__ end____ width___ exp.time_
 17 omega   63.00   88.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       96.5000   77.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega   10.00   39.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       96.5000  -95.0000  150.0000 29

#__ type_ start__ end____ width___ exp.time_
 19 omega   76.00  126.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       96.5000   61.0000 -120.0000 50

#__ type_ start__ end____ width___ exp.time_
 20 omega  -86.00  -58.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   54.0000  105.0000 28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0259273000
_diffrn_orient_matrix_UB_12      -0.2338459000
_diffrn_orient_matrix_UB_13      -0.0387858000
_diffrn_orient_matrix_UB_21      0.1457027000
_diffrn_orient_matrix_UB_22      0.0277595000
_diffrn_orient_matrix_UB_23      -0.0264158000
_diffrn_orient_matrix_UB_31      0.0667505000
_diffrn_orient_matrix_UB_32      -0.1509405000
_diffrn_orient_matrix_UB_33      0.0552909000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1712
_reflns_number_total             1995
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         1995
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0601P)²+0.2862P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1121
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C9(H9), N1(H1), N2(H2A)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O4(H4A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.66426(17) 0.5891(3) 0.11724(8) 0.0212(4) Uani 1 1 d . . . . .
C2 C 0.77556(17) 0.4046(3) 0.12811(8) 0.0201(4) Uani 1 1 d . . . . .
C3 C 0.86487(18) 0.4142(3) 0.18380(8) 0.0212(4) Uani 1 1 d . . . . .
C4 C 0.96975(18) 0.2389(3) 0.19308(8) 0.0236(4) Uani 1 1 d . . . . .
H4 H 1.030742 0.244786 0.229179 0.028 Uiso 1 1 calc R . . . .
C5 C 0.98475(18) 0.0569(3) 0.14969(8) 0.0236(4) Uani 1 1 d . . . . .
H5 H 1.054664 -0.059820 0.156935 0.028 Uiso 1 1 calc R . . . .
C6 C 0.89518(18) 0.0474(3) 0.09487(8) 0.0222(4) Uani 1 1 d . . . . .
C7 C 0.79246(17) 0.2218(3) 0.08399(8) 0.0222(4) Uani 1 1 d . . . . .
H7 H 0.734129 0.217592 0.047045 0.027 Uiso 1 1 calc R . . . .
C8 C 0.36699(18) 0.0736(3) 0.08241(8) 0.0232(4) Uani 1 1 d . . . . .
C9 C 0.39818(18) 0.3031(3) 0.17807(8) 0.0243(4) Uani 1 1 d . . . . .
H9 H 0.444906 0.322943 0.217607 0.029 Uiso 1 1 calc R . . . .
C10 C 0.29634(18) 0.4575(3) 0.15831(8) 0.0248(4) Uani 1 1 d . . . . .
C11 C 0.22017(17) 0.4335(3) 0.09719(8) 0.0227(4) Uani 1 1 d . . . . .
F1 F 0.25872(12) 0.6435(2) 0.19448(5) 0.0375(3) Uani 1 1 d . . . . .
N1 N 0.26231(15) 0.2351(3) 0.06407(7) 0.0238(3) Uani 1 1 d . . . . .
H1 H 0.218261 0.209739 0.027987 0.029 Uiso 1 1 calc R . . . .
N2 N 0.43394(15) 0.1153(3) 0.14021(7) 0.0233(3) Uani 1 1 d . . . . .
H2A H 0.501292 0.019925 0.153390 0.028 Uiso 1 1 calc R . . . .
O1 O 0.63995(13) 0.7433(2) 0.15684(6) 0.0261(3) Uani 1 1 d . . . . .
O2 O 0.59114(13) 0.5731(2) 0.06242(6) 0.0279(3) Uani 1 1 d . . . . .
H2 H 0.533602 0.683978 0.059073 0.042 Uiso 1 1 calc GR . . . .
O3 O 0.85467(14) 0.5867(2) 0.22894(6) 0.0272(3) Uani 1 1 d . . . . .
H3 H 0.786019 0.673049 0.219802 0.041 Uiso 1 1 calc GR . . . .
O4 O 0.90299(14) -0.1337(2) 0.05102(6) 0.0298(3) Uani 1 1 d . . . . .
H4A H 0.973753 -0.215657 0.059544 0.045 Uiso 1 1 calc GR . . . .
O5 O 0.39639(14) -0.0968(3) 0.04862(6) 0.0316(3) Uani 1 1 d . . . . .
O6 O 0.12724(14) 0.5702(3) 0.07611(6) 0.0318(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.474(2) . ?
C1 O1 1.231(2) . ?
C1 O2 1.318(2) . ?
C2 C3 1.410(2) . ?
C2 C7 1.394(3) . ?
C3 C4 1.392(3) . ?
C3 O3 1.360(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.396(2) . ?
C6 C7 1.378(2) . ?
C6 O4 1.372(2) . ?
C7 H7 0.9300 . ?
C8 N1 1.371(2) . ?
C8 N2 1.364(2) . ?
C8 O5 1.227(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.335(3) . ?
C9 N2 1.369(2) . ?
C10 C11 1.450(2) . ?
C10 F1 1.345(2) . ?
C11 N1 1.376(2) . ?
C11 O6 1.222(2) . ?
N1 H1 0.8600 . ?
N2 H2A 0.8600 . ?
O2 H2 0.8200 . ?
O3 H3 0.8200 . ?
O4 H4A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 122.45(14) . . ?
O1 C1 O2 122.70(15) . . ?
O2 C1 C2 114.84(15) . . ?
C3 C2 C1 119.27(15) . . ?
C7 C2 C1 120.55(14) . . ?
C7 C2 C3 120.19(15) . . ?
C4 C3 C2 118.40(16) . . ?
O3 C3 C2 123.50(16) . . ?
O3 C3 C4 118.09(14) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.14(15) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.12(16) . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 119.83(16) . . ?
O4 C6 C5 122.47(16) . . ?
O4 C6 C7 117.69(15) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 C2 120.30(15) . . ?
C6 C7 H7 119.9 . . ?
N2 C8 N1 115.48(16) . . ?
O5 C8 N1 121.37(15) . . ?
O5 C8 N2 123.15(16) . . ?
C10 C9 H9 120.0 . . ?
C10 C9 N2 120.08(15) . . ?
N2 C9 H9 120.0 . . ?
C9 C10 C11 121.97(17) . . ?
C9 C10 F1 121.44(15) . . ?
F1 C10 C11 116.58(15) . . ?
N1 C11 C10 112.82(15) . . ?
O6 C11 C10 125.11(17) . . ?
O6 C11 N1 122.06(16) . . ?
C8 N1 C11 126.98(14) . . ?
C8 N1 H1 116.5 . . ?
C11 N1 H1 116.5 . . ?
C8 N2 C9 122.62(15) . . ?
C8 N2 H2A 118.7 . . ?
C9 N2 H2A 118.7 . . ?
C1 O2 H2 109.5 . . ?
C3 O3 H3 109.5 . . ?
C6 O4 H4A 109.5 . . ?

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 H1 O4 0.86 2.01 2.8707(18) 173.3 3_655
N2 H2A O1 0.86 2.01 2.8399(19) 160.9 1_545
O2 H2 O5 0.82 1.78 2.5977(18) 174.3 1_565
O3 H3 O1 0.82 1.90 2.6124(16) 144.6 .
O4 H4A O6 0.82 1.89 2.7078(17) 174.7 1_645

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
C1 C2 C3 C4 -179.72(16) . . . . ?
C1 C2 C3 O3 -0.1(3) . . . . ?
C1 C2 C7 C6 -178.93(16) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C3 C2 C7 C6 0.9(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C4 C5 C6 O4 -178.12(16) . . . . ?
C5 C6 C7 C2 -1.4(3) . . . . ?
C7 C2 C3 C4 0.4(3) . . . . ?
C7 C2 C3 O3 -179.94(16) . . . . ?
C9 C10 C11 N1 1.4(3) . . . . ?
C9 C10 C11 O6 -179.09(19) . . . . ?
C10 C9 N2 C8 -1.6(3) . . . . ?
C10 C11 N1 C8 -2.1(3) . . . . ?
F1 C10 C11 N1 -178.24(15) . . . . ?
F1 C10 C11 O6 1.2(3) . . . . ?
N1 C8 N2 C9 1.0(3) . . . . ?
N2 C8 N1 C11 1.0(3) . . . . ?
N2 C9 C10 C11 0.2(3) . . . . ?
N2 C9 C10 F1 179.90(16) . . . . ?
O1 C1 C2 C3 -4.8(3) . . . . ?
O1 C1 C2 C7 175.05(16) . . . . ?
O2 C1 C2 C3 176.48(16) . . . . ?
O2 C1 C2 C7 -3.7(2) . . . . ?
O3 C3 C4 C5 179.06(16) . . . . ?
O4 C6 C7 C2 177.33(16) . . . . ?
O5 C8 N1 C11 -179.46(17) . . . . ?
O5 C8 N2 C9 -178.57(17) . . . . ?
O6 C11 N1 C8 178.41(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
