# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_k07235
_database_code_depnum_ccdc_archive 'CCDC 1856977'
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2018). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2018-08-28 deposited with the CCDC.
2018-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3

_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N2 O2'
_chemical_formula_sum            'C12 H10 N2 O2'
_chemical_formula_weight         214.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   10.8415(2)
_cell_length_b                   13.7771(4)
_cell_length_c                   6.9369(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.685(1)
_cell_angle_gamma                90
_cell_volume                     1010.84(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    4588
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 2006)'
_exptl_absorpt_special_details   
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by x-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the x-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;

_exptl_special_details           
; 
The crystal was mounted using polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
Diffraction data were collected with the crystal at 90K, which is standard 
practice in this laboratory for the majority of flash-cooled crystals. 
;

_diffrn_ambient_temperature      90.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed-tube'
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'φ and ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 9.1
_diffrn_reflns_number            8954
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.925
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000

_reflns_number_total             2310
_reflns_number_gt                1596
_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       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 2006)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 2006)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'

_refine_special_details          
; 
Refinement progress was checked using Platon (Spek, 2009) and by 
an R-tensor (Parkin, 2000). The final model was further checked 
with the IUCr utility checkCIF. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0841P)²+0.0085P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2310
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1421
_refine_ls_wR_factor_gt          0.1247
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.05407(12) 0.12545(9) 0.29447(19) 0.0179(3) Uani 1 1 d . . . . .
H1 H 0.005689 0.074500 0.257533 0.021 Uiso 1 1 calc R U . . .
C2 C 0.00741(16) 0.21502(11) 0.2538(2) 0.0178(4) Uani 1 1 d . . . . .
H2 H -0.078649 0.221939 0.187516 0.021 Uiso 1 1 calc R U . . .
C3 C 0.07888(15) 0.29720(11) 0.3039(2) 0.0156(4) Uani 1 1 d . . . . .
C4 C 0.20871(15) 0.28639(11) 0.3998(2) 0.0148(4) Uani 1 1 d . . . . .
C5 C 0.25301(15) 0.19029(11) 0.4456(2) 0.0171(4) Uani 1 1 d . . . . .
H5 H 0.337882 0.179763 0.514357 0.021 Uiso 1 1 calc R U . . .
C6 C 0.17474(15) 0.11341(11) 0.3917(2) 0.0171(4) Uani 1 1 d . . . . .
H6 H 0.205970 0.049631 0.423407 0.021 Uiso 1 1 calc R U . . .
C7 C 0.01294(15) 0.39378(12) 0.2533(2) 0.0177(4) Uani 1 1 d . . . . .
O8 O -0.10061(10) 0.39367(8) 0.17233(18) 0.0258(3) Uani 1 1 d . . . . .
O9 O 0.08187(10) 0.46942(8) 0.29992(17) 0.0227(3) Uani 1 1 d . . . . .
N10 N 0.28230(12) 0.36554(9) 0.44537(18) 0.0171(3) Uani 1 1 d . . . . .
H10 H 0.246033 0.421660 0.408201 0.021 Uiso 1 1 calc R U . . .
C11 C 0.41098(15) 0.36945(11) 0.5459(2) 0.0169(4) Uani 1 1 d . . . . .
C12 C 0.44572(16) 0.44114(11) 0.6897(2) 0.0189(4) Uani 1 1 d . . . . .
H12 H 0.383955 0.484826 0.717047 0.023 Uiso 1 1 calc R U . . .
C13 C 0.56988(15) 0.44862(12) 0.7923(2) 0.0219(4) Uani 1 1 d . . . . .
H13 H 0.592912 0.497539 0.890053 0.026 Uiso 1 1 calc R U . . .
C14 C 0.66124(16) 0.38556(12) 0.7541(3) 0.0246(4) Uani 1 1 d . . . . .
H14 H 0.746026 0.389806 0.827620 0.030 Uiso 1 1 calc R U . . .
C15 C 0.62718(16) 0.31610(12) 0.6070(3) 0.0227(4) Uani 1 1 d . . . . .
H15 H 0.689449 0.273265 0.578348 0.027 Uiso 1 1 calc R U . . .
C16 C 0.50334(16) 0.30871(11) 0.5018(3) 0.0200(4) Uani 1 1 d . . . . .
H16 H 0.481436 0.262011 0.399175 0.024 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 C2 1.3400(19) . ?
N1 C6 1.3440(19) . ?
N1 H1 0.8800 . ?
C2 C3 1.373(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.426(2) . ?
C3 C7 1.515(2) . ?
C4 N10 1.3471(18) . ?
C4 C5 1.420(2) . ?
C5 C6 1.357(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O8 1.2358(18) . ?
C7 O9 1.2818(19) . ?
N10 C11 1.4170(19) . ?
N10 H10 0.8800 . ?
C11 C16 1.390(2) . ?
C11 C12 1.396(2) . ?
C12 C13 1.381(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

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
C2 N1 C6 120.01(13) . . ?
C2 N1 H1 120.0 . . ?
C6 N1 H1 120.0 . . ?
N1 C2 C3 122.69(15) . . ?
N1 C2 H2 118.7 . . ?
C3 C2 H2 118.7 . . ?
C2 C3 C4 118.44(14) . . ?
C2 C3 C7 117.02(14) . . ?
C4 C3 C7 124.54(13) . . ?
N10 C4 C5 123.25(15) . . ?
N10 C4 C3 119.86(14) . . ?
C5 C4 C3 116.88(14) . . ?
C6 C5 C4 120.36(15) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
N1 C6 C5 121.52(14) . . ?
N1 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
O8 C7 O9 125.67(15) . . ?
O8 C7 C3 118.46(14) . . ?
O9 C7 C3 115.87(13) . . ?
C4 N10 C11 127.92(13) . . ?
C4 N10 H10 116.0 . . ?
C11 N10 H10 116.0 . . ?
C16 C11 C12 119.28(15) . . ?
C16 C11 N10 123.23(14) . . ?
C12 C11 N10 117.43(14) . . ?
C13 C12 C11 120.03(16) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.75(16) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C15 119.11(16) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C16 C15 C14 120.60(16) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 120.13(15) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 1.4(3) . . . . ?
N1 C2 C3 C4 1.2(3) . . . . ?
N1 C2 C3 C7 -178.50(14) . . . . ?
C2 C3 C4 N10 177.96(14) . . . . ?
C7 C3 C4 N10 -2.3(2) . . . . ?
C2 C3 C4 C5 -3.1(2) . . . . ?
C7 C3 C4 C5 176.59(15) . . . . ?
N10 C4 C5 C6 -178.53(15) . . . . ?
C3 C4 C5 C6 2.6(2) . . . . ?
C2 N1 C6 C5 -2.0(2) . . . . ?
C4 C5 C6 N1 -0.1(3) . . . . ?
C2 C3 C7 O8 0.7(2) . . . . ?
C4 C3 C7 O8 -179.06(14) . . . . ?
C2 C3 C7 O9 -179.38(14) . . . . ?
C4 C3 C7 O9 0.9(2) . . . . ?
C5 C4 N10 C11 -1.2(3) . . . . ?
C3 C4 N10 C11 177.61(14) . . . . ?
C4 N10 C11 C16 46.1(2) . . . . ?
C4 N10 C11 C12 -136.82(17) . . . . ?
C16 C11 C12 C13 -2.7(2) . . . . ?
N10 C11 C12 C13 -179.88(15) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C12 C13 C14 C15 1.8(3) . . . . ?
C13 C14 C15 C16 -1.0(2) . . . . ?
C14 C15 C16 C11 -1.6(2) . . . . ?
C12 C11 C16 C15 3.4(2) . . . . ?
N10 C11 C16 C15 -179.54(14) . . . . ?

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
_geom_hbond_publ_flag
N1 H1 O9 0.88 1.73 2.6073(17) 175.5 2_545 yes
C6 H6 O8 0.95 2.46 3.139(2) 128.7 2_545 yes
N10 H10 O9 0.88 1.89 2.6124(16) 138.0 . yes

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_k11019
_database_code_depnum_ccdc_archive 'CCDC 1856979'
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2016). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2018-07-20 deposited with the CCDC.
2018-09-12 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_CHEMW03_k11019              
;
PROBLEM: The ratio of given/expected molecular weight as
RESPONSE: ...
;
_vrf_PLAT041_k11019              
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check
RESPONSE: Hydrogen atoms for the solvent were not included in the model
but are included in the atom count, hence the apparent discrepancy.
;
_vrf_PLAT068_k11019              
;
PROBLEM: Reported F000 Differs from Calcd (or Missing)...     Please Check
RESPONSE: Hydrogen atoms for the solvent were not included in the model
but are included in F(000), hence the apparent discrepancy.
;
_vrf_PLAT309_k11019              
;
PROBLEM: Single Bonded Oxygen (C-O > 1.3 Ang) ...........        O1S Check 
RESPONSE: The disordered solvent channel is almost certainly much more 
complicated than is modelled here.  The solvent coordinates in this structure 
are merely an approximation using the known solvent species to account for 
the observed disordered electron density.  An alternative would have been 
to use SQUEEZE, but the end result would have been little different.
;
_vrf_PLAT911_k11019              
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          4 Report
RESPONSE: Several reflections that were behind the beamstop or that overloaded 
the detector were eliminated by the scaling/merging software.
;
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/1

_shelx_SHELXL_version_number     2018/1

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N2 O2, C O'
_chemical_formula_sum            'C13 H14 N2 O3'
_chemical_formula_weight         246.26

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

_cell_length_a                   11.5260(2)
_cell_length_b                   7.2220(2)
_cell_length_c                   26.9490(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2243.26(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    2966
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       slab
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by x-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the x-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;

_exptl_special_details           
; 
The crystal was mounted using polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
Diffraction data were collected with the crystal at 90K, which is standard 
practice in this laboratory for the majority of flash-cooled crystals. 
;

_diffrn_ambient_temperature      90.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed-tube'
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'φ and ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 9.1
_diffrn_reflns_number            17307
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.024
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_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             2564
_reflns_number_gt                1811
_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       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 2006)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 2006)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'

_refine_special_details          
; 
Refinement progress was checked using Platon (Spek, 2009) and by 
an R-tensor (Parkin, 2000). The final model was further checked 
with the IUCr utility checkCIF. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0542P)²+0.6517P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2564
_refine_ls_number_parameters     182
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1173
_refine_ls_wR_factor_gt          0.1002
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.45443(11) 0.64967(19) 0.55415(5) 0.0241(3) Uani 1 1 d . . . . .
H1 H 0.516962 0.678846 0.537120 0.029 Uiso 1 1 calc R U . . .
C2 C 0.34944(12) 0.6854(2) 0.53537(6) 0.0216(3) Uani 1 1 d . . . . .
H2 H 0.344256 0.738579 0.503206 0.026 Uiso 1 1 calc R U . . .
C3 C 0.24883(12) 0.6481(2) 0.56072(5) 0.0196(3) Uani 1 1 d . . . . .
C4 C 0.25729(13) 0.5749(2) 0.60995(5) 0.0196(3) Uani 1 1 d . . . . .
C5 C 0.37002(13) 0.5307(2) 0.62735(6) 0.0218(3) Uani 1 1 d . . . . .
H5 H 0.379455 0.473885 0.658886 0.026 Uiso 1 1 calc R U . . .
C6 C 0.46492(14) 0.5693(2) 0.59900(6) 0.0241(4) Uani 1 1 d . . . . .
H6 H 0.539928 0.538894 0.611133 0.029 Uiso 1 1 calc R U . . .
N7 N 0.15961(11) 0.54884(18) 0.63654(5) 0.0217(3) Uani 1 1 d . . . . .
H7 H 0.094737 0.571256 0.620399 0.026 Uiso 1 1 calc R U . . .
C8 C 0.14500(13) 0.4912(2) 0.68625(6) 0.0204(3) Uani 1 1 d . . . . .
C9 C 0.04114(13) 0.3999(2) 0.69765(6) 0.0225(3) Uani 1 1 d . . . . .
H9 H -0.014807 0.378318 0.672419 0.027 Uiso 1 1 calc R U . . .
C10 C 0.02011(14) 0.3413(2) 0.74569(6) 0.0244(4) Uani 1 1 d . . . . .
H10 H -0.050288 0.278884 0.753227 0.029 Uiso 1 1 calc R U . . .
C11 C 0.10047(14) 0.3725(2) 0.78283(6) 0.0245(4) Uani 1 1 d . . . . .
H11 H 0.086455 0.328675 0.815531 0.029 Uiso 1 1 calc R U . . .
C12 C 0.20146(13) 0.4679(2) 0.77207(6) 0.0235(4) Uani 1 1 d . . . . .
H12 H 0.256108 0.491633 0.797677 0.028 Uiso 1 1 calc R U . . .
C13 C 0.22374(13) 0.5295(2) 0.72398(6) 0.0216(3) Uani 1 1 d . . . . .
H13 H 0.292442 0.597340 0.717013 0.026 Uiso 1 1 calc R U . . .
C14 C 0.13565(13) 0.6863(2) 0.53472(6) 0.0229(3) Uani 1 1 d . . . . .
O15 O 0.04243(9) 0.64475(17) 0.55602(4) 0.0297(3) Uani 1 1 d . . . . .
O16 O 0.14343(9) 0.75888(17) 0.49233(4) 0.0305(3) Uani 1 1 d . . . . .
O1S O 0.2610(2) 0.1561(4) 0.39939(9) 0.0462(9) Uani 0.521(4) 1 d D . P A 1
C1S C 0.1604(7) 0.2718(9) 0.3954(7) 0.0427(15) Uani 0.521(4) 1 d D U P A 1
O2S O 0.1608(2) 0.5129(4) 0.39316(9) 0.0312(8) Uani 0.479(4) 1 d D . P A 2
C2S C 0.1773(9) 0.3112(7) 0.3953(9) 0.055(2) Uani 0.479(4) 1 d D U P A 2


_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 C2 1.3368(19) . ?
N1 C6 1.346(2) . ?
N1 H1 0.8800 . ?
C2 C3 1.373(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.432(2) . ?
C3 C14 1.506(2) . ?
C4 N7 1.3476(19) . ?
C4 C5 1.418(2) . ?
C5 C6 1.363(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
N7 C8 1.4131(19) . ?
N7 H7 0.8800 . ?
C8 C13 1.391(2) . ?
C8 C9 1.401(2) . ?
C9 C10 1.384(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.394(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O15 1.2545(18) . ?
C14 O16 1.2603(19) . ?
O1S C1S 1.433(5) . ?
O2S C2S 1.470(5) . ?

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
C2 N1 C6 120.28(13) . . ?
C2 N1 H1 119.9 . . ?
C6 N1 H1 119.9 . . ?
N1 C2 C3 122.59(14) . . ?
N1 C2 H2 118.7 . . ?
C3 C2 H2 118.7 . . ?
C2 C3 C4 118.44(13) . . ?
C2 C3 C14 117.67(13) . . ?
C4 C3 C14 123.89(13) . . ?
N7 C4 C5 123.95(14) . . ?
N7 C4 C3 119.17(13) . . ?
C5 C4 C3 116.87(13) . . ?
C6 C5 C4 120.27(14) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
N1 C6 C5 121.29(14) . . ?
N1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C4 N7 C8 130.14(13) . . ?
C4 N7 H7 114.9 . . ?
C8 N7 H7 114.9 . . ?
C13 C8 C9 119.41(14) . . ?
C13 C8 N7 123.84(14) . . ?
C9 C8 N7 116.64(13) . . ?
C10 C9 C8 119.94(14) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 120.68(15) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 119.55(15) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 120.59(15) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C8 C13 C12 119.73(14) . . ?
C8 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
O15 C14 O16 125.11(14) . . ?
O15 C14 C3 119.03(14) . . ?
O16 C14 C3 115.86(13) . . ?

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 N1 C2 C3 2.0(2) . . . . ?
N1 C2 C3 C4 2.5(2) . . . . ?
N1 C2 C3 C14 -177.21(14) . . . . ?
C2 C3 C4 N7 175.75(14) . . . . ?
C14 C3 C4 N7 -4.6(2) . . . . ?
C2 C3 C4 C5 -5.4(2) . . . . ?
C14 C3 C4 C5 174.24(14) . . . . ?
N7 C4 C5 C6 -176.95(15) . . . . ?
C3 C4 C5 C6 4.3(2) . . . . ?
C2 N1 C6 C5 -3.2(2) . . . . ?
C4 C5 C6 N1 0.0(2) . . . . ?
C5 C4 N7 C8 6.0(3) . . . . ?
C3 C4 N7 C8 -175.28(14) . . . . ?
C4 N7 C8 C13 31.2(2) . . . . ?
C4 N7 C8 C9 -152.71(15) . . . . ?
C13 C8 C9 C10 -3.0(2) . . . . ?
N7 C8 C9 C10 -179.27(14) . . . . ?
C8 C9 C10 C11 0.3(2) . . . . ?
C9 C10 C11 C12 1.8(2) . . . . ?
C10 C11 C12 C13 -1.2(2) . . . . ?
C9 C8 C13 C12 3.5(2) . . . . ?
N7 C8 C13 C12 179.53(14) . . . . ?
C11 C12 C13 C8 -1.4(2) . . . . ?
C2 C3 C14 O15 176.40(15) . . . . ?
C4 C3 C14 O15 -3.3(2) . . . . ?
C2 C3 C14 O16 -3.5(2) . . . . ?
C4 C3 C14 O16 176.80(14) . . . . ?

_refine_diff_density_max         0.327
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_k09231
_database_code_depnum_ccdc_archive 'CCDC 1856980'
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2018). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2018-07-20 deposited with the CCDC.
2018-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3

_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 Cl N2 O2'
_chemical_formula_sum            'C13 H11 Cl N2 O2'
_chemical_formula_weight         262.69

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'
Cl Cl 0.1484 0.1585 '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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   12.2170(2)
_cell_length_b                   10.6890(2)
_cell_length_c                   18.2180(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.039(1)
_cell_angle_gamma                90
_cell_volume                     2379.04(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    3250
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.316
_shelx_estimated_absorpt_T_min   0.884
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.884
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 2006)'
_exptl_absorpt_special_details   
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by x-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the x-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;

_exptl_special_details           
; 
The crystal was mounted using polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
Diffraction data were collected with the crystal at 90K, which is standard 
practice in this laboratory for the majority of flash-cooled crystals. 
;

_diffrn_ambient_temperature      90.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed-tube'
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'φ and ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 9.1
_diffrn_reflns_number            7208
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.236
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_full        25.242
_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             2733
_reflns_number_gt                2335
_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       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 2006)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 2006)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'

_refine_special_details          
; 
Refinement progress was checked using Platon (Spek, 2009) and by 
an R-tensor (Parkin, 2000). The final model was further checked 
with the IUCr utility checkCIF. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0402P)²+2.4813P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2733
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.21602(3) 0.04826(4) 0.48781(2) 0.02190(12) Uani 1 1 d . . . . .
N1 N 0.61031(10) 0.53312(11) 0.30172(6) 0.0134(3) Uani 1 1 d . . . . .
H1 H 0.6190(14) 0.6053(17) 0.2814(9) 0.016 Uiso 1 1 d . U . . .
C2 C 0.68404(11) 0.44252(13) 0.28796(7) 0.0126(3) Uani 1 1 d . . . . .
H2 H 0.738757 0.457274 0.251954 0.015 Uiso 1 1 calc R U . . .
C3 C 0.68328(11) 0.32980(13) 0.32385(7) 0.0121(3) Uani 1 1 d . . . . .
C4 C 0.60122(11) 0.30977(13) 0.37886(7) 0.0124(3) Uani 1 1 d . . . . .
C5 C 0.52069(11) 0.40437(13) 0.38841(8) 0.0143(3) Uani 1 1 d . . . . .
H5 H 0.461671 0.391462 0.421481 0.017 Uiso 1 1 calc R U . . .
C6 C 0.52812(12) 0.51342(14) 0.35016(8) 0.0151(3) Uani 1 1 d . . . . .
H6 H 0.474732 0.576782 0.357586 0.018 Uiso 1 1 calc R U . . .
N7 N 0.60136(10) 0.20573(11) 0.41953(7) 0.0139(3) Uani 1 1 d . . . . .
H7 H 0.6512(14) 0.1556(17) 0.4097(9) 0.017 Uiso 1 1 d . U . . .
C8 C 0.52109(11) 0.17795(13) 0.47424(8) 0.0131(3) Uani 1 1 d . . . . .
C9 C 0.41729(12) 0.13571(13) 0.45309(8) 0.0140(3) Uani 1 1 d . . . . .
C10 C 0.34510(12) 0.10719(13) 0.51022(8) 0.0157(3) Uani 1 1 d . . . . .
C11 C 0.37133(13) 0.12128(13) 0.58377(8) 0.0172(3) Uani 1 1 d . . . . .
H11 H 0.319319 0.101654 0.620756 0.021 Uiso 1 1 calc R U . . .
C12 C 0.47454(13) 0.16442(14) 0.60254(8) 0.0180(3) Uani 1 1 d . . . . .
H12 H 0.493840 0.174763 0.652697 0.022 Uiso 1 1 calc R U . . .
C13 C 0.54979(12) 0.19252(14) 0.54778(8) 0.0168(3) Uani 1 1 d . . . . .
H13 H 0.620780 0.221653 0.560485 0.020 Uiso 1 1 calc R U . . .
C14 C 0.76885(11) 0.23254(13) 0.30496(7) 0.0129(3) Uani 1 1 d . . . . .
O15 O 0.76923(9) 0.13254(10) 0.34134(6) 0.0182(2) Uani 1 1 d . . . . .
O16 O 0.83393(8) 0.25843(9) 0.25348(6) 0.0173(2) Uani 1 1 d . . . . .
C17 C 0.38475(13) 0.12151(15) 0.37383(8) 0.0193(3) Uani 1 1 d . . . . .
H17A H 0.359296 0.035842 0.365104 0.029 Uiso 1 1 calc R U . . .
H17B H 0.448011 0.138952 0.342402 0.029 Uiso 1 1 calc R U . . .
H17C H 0.325752 0.180493 0.362361 0.029 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
Cl1 C10 1.7463(15) . ?
N1 C2 1.3462(18) . ?
N1 C6 1.3538(18) . ?
N1 H1 0.862(18) . ?
C2 C3 1.371(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.4340(18) . ?
C3 C14 1.5141(19) . ?
C4 N7 1.3363(18) . ?
C4 C5 1.422(2) . ?
C5 C6 1.361(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
N7 C8 1.4299(17) . ?
N7 H7 0.830(18) . ?
C8 C13 1.393(2) . ?
C8 C9 1.400(2) . ?
C9 C10 1.3984(19) . ?
C9 C17 1.505(2) . ?
C10 C11 1.386(2) . ?
C11 C12 1.385(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O15 1.2577(18) . ?
C14 O16 1.2606(16) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 120.41(13) . . ?
C2 N1 H1 118.8(11) . . ?
C6 N1 H1 120.7(11) . . ?
N1 C2 C3 122.59(13) . . ?
N1 C2 H2 118.7 . . ?
C3 C2 H2 118.7 . . ?
C2 C3 C4 118.00(12) . . ?
C2 C3 C14 119.34(12) . . ?
C4 C3 C14 122.65(12) . . ?
N7 C4 C5 121.65(13) . . ?
N7 C4 C3 120.74(13) . . ?
C5 C4 C3 117.62(12) . . ?
C6 C5 C4 120.01(13) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
N1 C6 C5 121.11(13) . . ?
N1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C4 N7 C8 123.97(12) . . ?
C4 N7 H7 114.7(12) . . ?
C8 N7 H7 121.3(12) . . ?
C13 C8 C9 121.87(13) . . ?
C13 C8 N7 118.34(13) . . ?
C9 C8 N7 119.78(12) . . ?
C10 C9 C8 115.92(13) . . ?
C10 C9 C17 121.72(13) . . ?
C8 C9 C17 122.36(13) . . ?
C11 C10 C9 123.39(14) . . ?
C11 C10 Cl1 118.27(11) . . ?
C9 C10 Cl1 118.33(11) . . ?
C12 C11 C10 119.00(13) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 119.81(13) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C8 119.99(14) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
O15 C14 O16 125.20(13) . . ?
O15 C14 C3 117.77(12) . . ?
O16 C14 C3 117.02(12) . . ?
C9 C17 H17A 109.5 . . ?
C9 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C9 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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 N1 C2 C3 -3.1(2) . . . . ?
N1 C2 C3 C4 -1.0(2) . . . . ?
N1 C2 C3 C14 179.75(12) . . . . ?
C2 C3 C4 N7 -174.92(13) . . . . ?
C14 C3 C4 N7 4.3(2) . . . . ?
C2 C3 C4 C5 4.91(19) . . . . ?
C14 C3 C4 C5 -175.84(12) . . . . ?
N7 C4 C5 C6 174.75(13) . . . . ?
C3 C4 C5 C6 -5.1(2) . . . . ?
C2 N1 C6 C5 2.9(2) . . . . ?
C4 C5 C6 N1 1.2(2) . . . . ?
C5 C4 N7 C8 1.6(2) . . . . ?
C3 C4 N7 C8 -178.63(13) . . . . ?
C4 N7 C8 C13 -103.88(16) . . . . ?
C4 N7 C8 C9 76.96(18) . . . . ?
C13 C8 C9 C10 -1.0(2) . . . . ?
N7 C8 C9 C10 178.12(12) . . . . ?
C13 C8 C9 C17 179.03(13) . . . . ?
N7 C8 C9 C17 -1.8(2) . . . . ?
C8 C9 C10 C11 1.3(2) . . . . ?
C17 C9 C10 C11 -178.74(14) . . . . ?
C8 C9 C10 Cl1 -177.58(10) . . . . ?
C17 C9 C10 Cl1 2.38(19) . . . . ?
C9 C10 C11 C12 -0.8(2) . . . . ?
Cl1 C10 C11 C12 178.11(11) . . . . ?
C10 C11 C12 C13 -0.1(2) . . . . ?
C11 C12 C13 C8 0.4(2) . . . . ?
C9 C8 C13 C12 0.2(2) . . . . ?
N7 C8 C13 C12 -178.92(13) . . . . ?
C2 C3 C14 O15 176.61(12) . . . . ?
C4 C3 C14 O15 -2.6(2) . . . . ?
C2 C3 C14 O16 -3.71(19) . . . . ?
C4 C3 C14 O16 177.04(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O15 0.862(18) 2.637(17) 3.1769(15) 121.8(14) 4_655 yes
N1 H1 O16 0.862(18) 1.848(19) 2.6975(16) 168.1(17) 4_655 yes
N7 H7 O15 0.830(18) 1.922(18) 2.6174(16) 140.6(16) . yes

_refine_diff_density_max         0.345
_refine_diff_density_min         -0.336
_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_k11020
_database_code_depnum_ccdc_archive 'CCDC 1856978'
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2018). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2018-08-28 deposited with the CCDC.
2018-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3

_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N2 O2'
_chemical_formula_sum            'C12 H10 N2 O2'
_chemical_formula_weight         214.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   13.8180(2)
_cell_length_b                   11.3050(2)
_cell_length_c                   13.5600(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.6860(9)
_cell_angle_gamma                90
_cell_volume                     2018.12(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    4867
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 2006)'
_exptl_absorpt_special_details   
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by x-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the x-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;

_exptl_special_details           
; 
The crystal was mounted using polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
Diffraction data were collected with the crystal at 90K, which is standard 
practice in this laboratory for the majority of flash-cooled crystals. 
;

_diffrn_ambient_temperature      90.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed-tube'
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'φ and ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 9.1
_diffrn_reflns_number            8971
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.375
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_full        25.242
_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             4632
_reflns_number_gt                3502
_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       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 2006)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 2006)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'

_refine_special_details          
; 
Refinement progress was checked using Platon (Spek, 2009) and by 
an R-tensor (Parkin, 2000). The final model was further checked 
with the IUCr utility checkCIF. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0643P)²+0.3355P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4632
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1162
_refine_ls_wR_factor_gt          0.1062
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N 0.09425(8) -0.16234(10) 0.68765(9) 0.0194(3) Uani 1 1 d . . . . .
H1A H 0.084542 -0.229309 0.716347 0.023 Uiso 1 1 calc R U . . .
C2A C 0.04534(10) -0.06371(11) 0.70136(11) 0.0188(3) Uani 1 1 d . . . . .
H2A H 0.000211 -0.068396 0.741918 0.023 Uiso 1 1 calc R U . . .
C3A C 0.05795(10) 0.04324(11) 0.65923(10) 0.0170(3) Uani 1 1 d . . . . .
C4A C 0.12707(10) 0.05046(11) 0.59907(10) 0.0177(3) Uani 1 1 d . . . . .
C5A C 0.17604(11) -0.05598(11) 0.58536(11) 0.0219(3) Uani 1 1 d . . . . .
H5A H 0.221442 -0.055645 0.544963 0.026 Uiso 1 1 calc R U . . .
C6A C 0.15841(10) -0.15825(12) 0.62960(11) 0.0213(3) Uani 1 1 d . . . . .
H6A H 0.191891 -0.228555 0.619562 0.026 Uiso 1 1 calc R U . . .
C7A C 0.00061(10) 0.14944(11) 0.68073(11) 0.0191(3) Uani 1 1 d . . . . .
O8A O -0.05366(7) 0.13279(8) 0.73936(8) 0.0253(2) Uani 1 1 d . . . . .
O9A O 0.01221(7) 0.24680(8) 0.64145(8) 0.0250(2) Uani 1 1 d . . . . .
N10A N 0.14249(9) 0.15415(9) 0.55851(9) 0.0199(3) Uani 1 1 d . . . . .
H10A H 0.106559 0.214577 0.568766 0.024 Uiso 1 1 calc R U . . .
C11A C 0.21093(10) 0.17706(11) 0.50045(10) 0.0191(3) Uani 1 1 d . . . . .
C12A C 0.1752(1) 0.23917(12) 0.40835(11) 0.0217(3) Uani 1 1 d . . . . .
H12A H 0.106120 0.263225 0.384169 0.026 Uiso 1 1 calc R U . . .
C13A C 0.24064(11) 0.26609(12) 0.35159(11) 0.0242(3) Uani 1 1 d . . . . .
H13A H 0.216087 0.308658 0.288484 0.029 Uiso 1 1 calc R U . . .
C14A C 0.34119(11) 0.23148(12) 0.38611(11) 0.0236(3) Uani 1 1 d . . . . .
H14A H 0.385532 0.249215 0.346580 0.028 Uiso 1 1 calc R U . . .
C15A C 0.37684(11) 0.17081(12) 0.47866(11) 0.0236(3) Uani 1 1 d . . . . .
H15A H 0.445967 0.146861 0.502445 0.028 Uiso 1 1 calc R U . . .
C16A C 0.31286(11) 0.14443(11) 0.53729(11) 0.0213(3) Uani 1 1 d . . . . .
H16A H 0.338287 0.104640 0.601713 0.026 Uiso 1 1 calc R U . . .
N1B N 0.40727(9) -0.38298(10) 0.81562(9) 0.0229(3) Uani 1 1 d . . . . .
H1B H 0.429665 -0.451438 0.800607 0.027 Uiso 1 1 calc R U . . .
C2B C 0.43485(10) -0.28246(12) 0.77884(11) 0.0202(3) Uani 1 1 d . . . . .
H2B H 0.477169 -0.287250 0.735326 0.024 Uiso 1 1 calc R U . . .
C3B C 0.40438(10) -0.17318(11) 0.80158(10) 0.0176(3) Uani 1 1 d . . . . .
C4B C 0.34318(10) -0.16624(11) 0.86976(10) 0.0190(3) Uani 1 1 d . . . . .
C5B C 0.31262(11) -0.27470(12) 0.90361(12) 0.0253(3) Uani 1 1 d . . . . .
H5B H 0.269152 -0.274255 0.946077 0.030 Uiso 1 1 calc R U . . .
C6B C 0.34512(11) -0.37925(12) 0.87570(12) 0.0273(3) Uani 1 1 d . . . . .
H6B H 0.323763 -0.451145 0.898847 0.033 Uiso 1 1 calc R U . . .
C7B C 0.44223(10) -0.06520(12) 0.75850(11) 0.0198(3) Uani 1 1 d . . . . .
O8B O 0.49582(8) -0.08352(8) 0.69954(8) 0.0268(2) Uani 1 1 d . . . . .
O9B O 0.41982(7) 0.03504(8) 0.78527(8) 0.0249(2) Uani 1 1 d . . . . .
N10B N 0.31851(9) -0.06027(9) 0.89966(9) 0.0209(3) Uani 1 1 d . . . . .
H10B H 0.333850 0.001724 0.868086 0.025 Uiso 1 1 calc R U . . .
C11B C 0.27029(10) -0.03670(11) 0.97675(11) 0.0192(3) Uani 1 1 d . . . . .
C12B C 0.31970(11) 0.03771(12) 1.05779(11) 0.0224(3) Uani 1 1 d . . . . .
H12B H 0.385233 0.067656 1.062678 0.027 Uiso 1 1 calc R U . . .
C13B C 0.27335(12) 0.06829(12) 1.13159(11) 0.0272(3) Uani 1 1 d . . . . .
H13B H 0.306894 0.120145 1.186458 0.033 Uiso 1 1 calc R U . . .
C14B C 0.17854(12) 0.02377(13) 1.12584(12) 0.0293(4) Uani 1 1 d . . . . .
H14B H 0.147218 0.044282 1.176902 0.035 Uiso 1 1 calc R U . . .
C15B C 0.12965(11) -0.05084(12) 1.04521(12) 0.0264(3) Uani 1 1 d . . . . .
H15B H 0.064711 -0.081850 1.041370 0.032 Uiso 1 1 calc R U . . .
C16B C 0.17451(10) -0.08091(12) 0.96978(11) 0.0219(3) Uani 1 1 d . . . . .
H16B H 0.140085 -0.131158 0.913996 0.026 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
N1A C2A 1.3457(16) . ?
N1A C6A 1.3534(16) . ?
N1A H1A 0.8800 . ?
C2A C3A 1.3708(17) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.4345(17) . ?
C3A C7A 1.5148(17) . ?
C4A N10A 1.3392(16) . ?
C4A C5A 1.4201(18) . ?
C5A C6A 1.3582(18) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A O9A 1.2540(15) . ?
C7A O8A 1.2618(15) . ?
N10A C11A 1.4261(16) . ?
N10A H10A 0.8800 . ?
C11A C12A 1.3862(19) . ?
C11A C16A 1.394(2) . ?
C12A C13A 1.3877(18) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.381(2) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.383(2) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.3890(18) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
N1B C2B 1.3420(17) . ?
N1B C6B 1.3521(17) . ?
N1B H1B 0.8800 . ?
C2B C3B 1.3702(18) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.4323(17) . ?
C3B C7B 1.5135(18) . ?
C4B N10B 1.3415(16) . ?
C4B C5B 1.4178(18) . ?
C5B C6B 1.3583(19) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B O9B 1.2570(15) . ?
C7B O8B 1.2610(15) . ?
N10B C11B 1.4252(16) . ?
N10B H10B 0.8800 . ?
C11B C12B 1.388(2) . ?
C11B C16B 1.3908(18) . ?
C12B C13B 1.3858(19) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.383(2) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.384(2) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.3896(19) . ?
C15B H15B 0.9500 . ?
C16B H16B 0.9500 . ?

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
C2A N1A C6A 119.82(11) . . ?
C2A N1A H1A 120.1 . . ?
C6A N1A H1A 120.1 . . ?
N1A C2A C3A 122.72(12) . . ?
N1A C2A H2A 118.6 . . ?
C3A C2A H2A 118.6 . . ?
C2A C3A C4A 118.56(11) . . ?
C2A C3A C7A 118.61(11) . . ?
C4A C3A C7A 122.81(11) . . ?
N10A C4A C5A 123.12(11) . . ?
N10A C4A C3A 119.99(11) . . ?
C5A C4A C3A 116.89(11) . . ?
C6A C5A C4A 120.46(12) . . ?
C6A C5A H5A 119.8 . . ?
C4A C5A H5A 119.8 . . ?
N1A C6A C5A 121.53(12) . . ?
N1A C6A H6A 119.2 . . ?
C5A C6A H6A 119.2 . . ?
O9A C7A O8A 125.14(12) . . ?
O9A C7A C3A 118.17(11) . . ?
O8A C7A C3A 116.66(11) . . ?
C4A N10A C11A 126.92(11) . . ?
C4A N10A H10A 116.5 . . ?
C11A N10A H10A 116.5 . . ?
C12A C11A C16A 120.10(12) . . ?
C12A C11A N10A 118.35(12) . . ?
C16A C11A N10A 121.44(12) . . ?
C11A C12A C13A 119.80(13) . . ?
C11A C12A H12A 120.1 . . ?
C13A C12A H12A 120.1 . . ?
C14A C13A C12A 120.52(13) . . ?
C14A C13A H13A 119.7 . . ?
C12A C13A H13A 119.7 . . ?
C13A C14A C15A 119.50(12) . . ?
C13A C14A H14A 120.2 . . ?
C15A C14A H14A 120.2 . . ?
C14A C15A C16A 120.84(13) . . ?
C14A C15A H15A 119.6 . . ?
C16A C15A H15A 119.6 . . ?
C15A C16A C11A 119.19(13) . . ?
C15A C16A H16A 120.4 . . ?
C11A C16A H16A 120.4 . . ?
C2B N1B C6B 120.11(12) . . ?
C2B N1B H1B 119.9 . . ?
C6B N1B H1B 119.9 . . ?
N1B C2B C3B 122.58(12) . . ?
N1B C2B H2B 118.7 . . ?
C3B C2B H2B 118.7 . . ?
C2B C3B C4B 118.48(12) . . ?
C2B C3B C7B 118.33(11) . . ?
C4B C3B C7B 123.09(11) . . ?
N10B C4B C5B 123.13(12) . . ?
N10B C4B C3B 119.87(11) . . ?
C5B C4B C3B 117.00(11) . . ?
C6B C5B C4B 120.41(12) . . ?
C6B C5B H5B 119.8 . . ?
C4B C5B H5B 119.8 . . ?
N1B C6B C5B 121.29(13) . . ?
N1B C6B H6B 119.4 . . ?
C5B C6B H6B 119.4 . . ?
O9B C7B O8B 125.09(12) . . ?
O9B C7B C3B 118.12(11) . . ?
O8B C7B C3B 116.77(11) . . ?
C4B N10B C11B 127.36(11) . . ?
C4B N10B H10B 116.3 . . ?
C11B N10B H10B 116.3 . . ?
C12B C11B C16B 120.05(12) . . ?
C12B C11B N10B 117.84(12) . . ?
C16B C11B N10B 122.03(13) . . ?
C13B C12B C11B 119.93(13) . . ?
C13B C12B H12B 120.0 . . ?
C11B C12B H12B 120.0 . . ?
C14B C13B C12B 120.40(14) . . ?
C14B C13B H13B 119.8 . . ?
C12B C13B H13B 119.8 . . ?
C13B C14B C15B 119.53(13) . . ?
C13B C14B H14B 120.2 . . ?
C15B C14B H14B 120.2 . . ?
C14B C15B C16B 120.72(13) . . ?
C14B C15B H15B 119.6 . . ?
C16B C15B H15B 119.6 . . ?
C15B C16B C11B 119.35(14) . . ?
C15B C16B H16B 120.3 . . ?
C11B C16B H16B 120.3 . . ?

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
C6A N1A C2A C3A -0.5(2) . . . . ?
N1A C2A C3A C4A -0.8(2) . . . . ?
N1A C2A C3A C7A -179.03(12) . . . . ?
C2A C3A C4A N10A -178.75(12) . . . . ?
C7A C3A C4A N10A -0.6(2) . . . . ?
C2A C3A C4A C5A 1.55(19) . . . . ?
C7A C3A C4A C5A 179.74(12) . . . . ?
N10A C4A C5A C6A 179.10(13) . . . . ?
C3A C4A C5A C6A -1.2(2) . . . . ?
C2A N1A C6A C5A 0.9(2) . . . . ?
C4A C5A C6A N1A 0.0(2) . . . . ?
C2A C3A C7A O9A -179.65(13) . . . . ?
C4A C3A C7A O9A 2.2(2) . . . . ?
C2A C3A C7A O8A 1.96(19) . . . . ?
C4A C3A C7A O8A -176.24(12) . . . . ?
C5A C4A N10A C11A -2.8(2) . . . . ?
C3A C4A N10A C11A 177.55(12) . . . . ?
C4A N10A C11A C12A 131.98(14) . . . . ?
C4A N10A C11A C16A -51.70(19) . . . . ?
C16A C11A C12A C13A 1.7(2) . . . . ?
N10A C11A C12A C13A 178.03(12) . . . . ?
C11A C12A C13A C14A 0.0(2) . . . . ?
C12A C13A C14A C15A -0.8(2) . . . . ?
C13A C14A C15A C16A -0.1(2) . . . . ?
C14A C15A C16A C11A 1.7(2) . . . . ?
C12A C11A C16A C15A -2.5(2) . . . . ?
N10A C11A C16A C15A -178.77(12) . . . . ?
C6B N1B C2B C3B 1.6(2) . . . . ?
N1B C2B C3B C4B 1.9(2) . . . . ?
N1B C2B C3B C7B 178.31(12) . . . . ?
C2B C3B C4B N10B 175.01(13) . . . . ?
C7B C3B C4B N10B -1.2(2) . . . . ?
C2B C3B C4B C5B -4.1(2) . . . . ?
C7B C3B C4B C5B 179.62(13) . . . . ?
N10B C4B C5B C6B -175.96(14) . . . . ?
C3B C4B C5B C6B 3.2(2) . . . . ?
C2B N1B C6B C5B -2.7(2) . . . . ?
C4B C5B C6B N1B 0.2(2) . . . . ?
C2B C3B C7B O9B -175.22(13) . . . . ?
C4B C3B C7B O9B 1.0(2) . . . . ?
C2B C3B C7B O8B 3.51(19) . . . . ?
C4B C3B C7B O8B 179.75(13) . . . . ?
C5B C4B N10B C11B 8.0(2) . . . . ?
C3B C4B N10B C11B -171.09(13) . . . . ?
C4B N10B C11B C12B 123.53(15) . . . . ?
C4B N10B C11B C16B -59.8(2) . . . . ?
C16B C11B C12B C13B -0.2(2) . . . . ?
N10B C11B C12B C13B 176.55(12) . . . . ?
C11B C12B C13B C14B 0.9(2) . . . . ?
C12B C13B C14B C15B -0.6(2) . . . . ?
C13B C14B C15B C16B -0.4(2) . . . . ?
C14B C15B C16B C11B 1.0(2) . . . . ?
C12B C11B C16B C15B -0.7(2) . . . . ?
N10B C11B C16B C15B -177.35(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H1A O8A 0.88 1.77 2.6450(14) 173.4 2_546 yes
N10A H10A O9A 0.88 1.89 2.6140(14) 137.9 . yes
N1B H1B O8B 0.88 1.81 2.6726(14) 164.5 2_646 yes
N10B H10B O9B 0.88 1.90 2.6164(14) 136.9 . yes

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.049

