# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_9AA
_database_code_depnum_ccdc_archive 'CCDC 2270291'
_audit_update_record             
;
2024-01-23 deposited with the CCDC.	2024-01-31 downloaded from the CCDC.
;
_audit_creation_date             2023-01-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_formula_moiety         'Cl, H2 O, C13 H11 N2'
_chemical_formula_sum            'C13 H13 Cl N2 O'
_chemical_formula_weight         248.70
loop_
_atom_type_symbol
_atom_type_scat_source
H 'DiSCaMB, J. Appl. Cryst. 2018, DOI:10.1107/S1600576717015825'
O 'DiSCaMB, J. Appl. Cryst. 2018, DOI:10.1107/S1600576717015825'
C 'DiSCaMB, J. Appl. Cryst. 2018, DOI:10.1107/S1600576717015825'
Cl 'DiSCaMB, J. Appl. Cryst. 2018, DOI:10.1107/S1600576717015825'
N 'DiSCaMB, J. Appl. Cryst. 2018, DOI:10.1107/S1600576717015825'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.7880(5)
_cell_length_b                   8.7699(5)
_cell_length_c                   9.7291(6)
_cell_angle_alpha                111.057(2)
_cell_angle_beta                 96.558(2)
_cell_angle_gamma                104.436(2)
_cell_volume                     585.08(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9427
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      48.63
_cell_measurement_theta_min      2.30
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_T_max  0.9870
_exptl_absorpt_correction_T_min  0.9546
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0454 before and 0.0398 after correction.
The Ratio of minimum to maximum transmission is 0.9672.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             260.394
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.178
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            11578
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         48.76
_diffrn_reflns_theta_min         2.30
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              16
_reflns_limit_k_min              -18
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                9998
_reflns_number_total             11578
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.3603
_refine_diff_density_min         -0.2864
_refine_diff_density_rms         0.0366
_refine_ls_d_res_high            0.4726
_refine_ls_d_res_low             8.8456
_refine_ls_goodness_of_fit_ref   1.1780
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     193
_refine_ls_number_reflns         11578
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0186
_refine_ls_R_factor_gt           0.0139
_refine_ls_restrained_S_all      1.1780
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0083P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0387
_refine_ls_wR_factor_ref         0.0426
_refine_special_details          
;
Electron Density Partition Based Refinement (EDPBR):
  .  Aspherical atomic scattering factors obtained from
     selected partitioning of molecular electron density
     derived from molecular wavefunction. Crystal field
     effect is modelled in the course of wavefunction
     calculations by embedding the system in a cluster of
Hirshfeld partition derived atomic multipoles for
molecules within certain radius from the system or
performing wave function calculations for a cluster of
molecules surrounding the system. Software used for
quantum mechanical calculations: ORCA 5.0. Software
used to partition electron density:HORTON. 
  .  Partitioning of molecular electron density: Iterative
     Hirshfeld
  .  Level of theory: DFT(B3LYP)/cc-pVDZ
  .  Cluster of multipoles: radius=16.0 angstrom, lmax=1
  .  Cluster of molecules: yes
  .  ADPs were computed and refined only for C, N and O, 
      while H atoms were estimated using SHADE3 server60 
      and fixed during the refinements.
  .  Refinement based on Fsqd as implemented in olex2.refine. DiSCaMB library used to obtain
aspherical atomic scattering factors.
;
_olex2_refinement_description    
;
1. Others
 Fixed U11: H16(0.041734) H14(0.028708) H13(0.031712) H12(0.024091)
 H11(0.030177) H5(0.033814) H2(0.025258) H9(0.022299) H4(0.038171) H8(0.027659)
 H10(0.032882) H3(0.024341) H15(0.045892)
 Fixed U12: H16(-0.007636) H14(0.005661) H13(0.00867) H12(0.011761)
 H11(0.007465) H5(0.004735) H2(0.006579) H9(0.011721) H4(0.005164) H8(0.006232)
 H10(0.009835) H3(0.008861) H15(-0.014892)
 Fixed U13: H16(0.003145) H14(-0.008295) H13(-0.003699) H12(-0.004746) H11(-
 0.00713) H5(-0.00735) H2(-0.00677) H9(-0.001557) H4(0.005896) H8(-0.01045)
 H10(0.00344) H3(0.004083) H15(0.001002)
 Fixed U22: H16(0.049776) H14(0.039354) H13(0.039277) H12(0.03881)
 H11(0.041415) H5(0.043915) H2(0.041345) H9(0.041277) H4(0.044175) H8(0.042375)
 H10(0.040685) H3(0.041361) H15(0.042462)
 Fixed U23: H16(-0.017851) H14(-0.002744) H13(-0.009855) H12(-0.005324) H11(-
 0.005311) H5(-0.003708) H2(-0.004159) H9(-0.004276) H4(-0.00824) H8(-0.003528)
 H10(-0.008475) H3(-0.006095) H15(-0.009608)
 Fixed U33: H16(0.03108) H14(0.01886) H13(0.01935) H12(0.0271) H11(0.01866)
 H5(0.01874) H2(0.02376) H9(0.03529) H4(0.01933) H8(0.02451) H10(0.02294)
 H3(0.0321) H15(0.03117)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Cl1 Cl 1.061866(6) 0.731645(5) 0.897100(4) 0.015108(11) Uani 1.000000 .
O1 O 0.92282(2) 0.330530(19) 0.802027(15) 0.01767(2) Uani 1.000000 .
N2 N 0.641137(19) 0.241262(18) 0.559012(15) 0.012603(19) Uani 1.000000 .
N1 N 0.22826(2) 0.09310(2) 0.186825(16) 0.01493(2) Uani 1.000000 .
C13 C 0.36067(2) 0.140382(19) 0.306183(16) 0.01098(2) Uani 1.000000 .
C12 C 0.50519(2) 0.064885(19) 0.295390(16) 0.01101(2) Uani 1.000000 .
C1 C 0.36349(2) 0.268815(19) 0.449626(16) 0.01112(2) Uani 1.000000 .
C11 C 0.51531(2) -0.06187(2) 0.158645(18) 0.01341(2) Uani 1.000000 .
C6 C 0.50640(2) 0.315335(19) 0.574387(16) 0.01157(2) Uani 1.000000 .
C5 C 0.51107(2) 0.43913(2) 0.717547(18) 0.01455(2) Uani 1.000000 .
C2 C 0.22516(2) 0.34834(2) 0.471496(18) 0.01358(2) Uani 1.000000 .
C9 C 0.79742(2) -0.07012(2) 0.28315(2) 0.01529(2) Uani 1.000000 .
C4 C 0.37419(3) 0.51279(2) 0.734866(19) 0.01592(2) Uani 1.000000 .
C8 C 0.79128(2) 0.05175(2) 0.417264(19) 0.01402(2) Uani 1.000000 .
C7 C 0.64497(2) 0.120883(19) 0.424993(17) 0.01136(2) Uani 1.000000 .
C10 C 0.65815(2) -0.12770(2) 0.15271(2) 0.01515(2) Uani 1.000000 .
C3 C 0.23016(2) 0.46736(2) 0.61117(2) 0.01559(2) Uani 1.000000 .
H16 H 0.9221(9) 0.3097(8) 0.8911(8) 0.040863 Uani 1.000000 .
H14 H 0.7434(7) 0.2773(7) 0.6552(6) 0.028974 Uani 1.000000 .
H13 H 0.2123(8) -0.0097(7) 0.0884(6) 0.030113 Uani 1.000000 .
H12 H 0.1323(7) 0.1546(7) 0.1895(6) 0.030000 Uani 1.000000 .
H11 H 0.4085(7) -0.1085(6) 0.0578(5) 0.030084 Uani 1.000000 .
H5 H 0.6239(7) 0.4737(7) 0.8094(5) 0.032156 Uani 1.000000 .
H2 H 0.1138(6) 0.3150(6) 0.3769(5) 0.030121 Uani 1.000000 .
H9 H 0.9082(7) -0.1239(7) 0.2765(6) 0.032955 Uani 1.000000 .
H4 H 0.3739(7) 0.6041(7) 0.8425(5) 0.033892 Uani 1.000000 .
H8 H 0.8970(7) 0.0989(6) 0.5169(6) 0.031514 Uani 1.000000 .
H10 H 0.6658(7) -0.2252(7) 0.0485(5) 0.032169 Uani 1.000000 .
H3 H 0.1255(7) 0.5292(6) 0.6287(6) 0.032601 Uani 1.000000 .
H15 H 0.9814(9) 0.4536(8) 0.8361(7) 0.039842 Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H16 0.948(7) . ?
O1 H15 0.973(6) . ?
N2 C6 1.3607(2) . ?
N2 C7 1.3605(2) . ?
N2 H14 1.050(5) . ?
N1 C13 1.3233(2) . ?
N1 H13 1.021(5) . ?
N1 H12 1.022(5) . ?
C13 C12 1.4370(2) . ?
C13 C1 1.4380(2) . ?
C12 C11 1.4201(2) . ?
C12 C7 1.4110(2) . ?
C1 C6 1.4098(2) . ?
C1 C2 1.4187(2) . ?
C11 C10 1.3730(2) . ?
C11 H11 1.085(4) . ?
C6 C5 1.4149(2) . ?
C5 C4 1.3742(3) . ?
C5 H5 1.075(5) . ?
C2 C3 1.3733(2) . ?
C2 H2 1.088(5) . ?
C9 C8 1.3729(3) . ?
C9 C10 1.4120(3) . ?
C9 H9 1.079(5) . ?
C4 C3 1.4105(3) . ?
C4 H4 1.066(4) . ?
C8 C7 1.4153(2) . ?
C8 H8 1.072(5) . ?
C10 H10 1.085(5) . ?
C3 H3 1.083(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
H15 O1 H16 105.7(5) . . ?
C7 N2 C6 122.289(13) . . ?
H14 N2 C6 118.1(3) . . ?
H14 N2 C7 119.6(3) . . ?
H13 N1 C13 122.3(3) . . ?
H12 N1 C13 121.7(3) . . ?
H12 N1 H13 116.0(4) . . ?
C12 C13 N1 120.780(13) . . ?
C1 C13 N1 120.763(14) . . ?
C1 C13 C12 118.457(13) . . ?
C11 C12 C13 122.712(13) . . ?
C7 C12 C13 118.871(13) . . ?
C7 C12 C11 118.405(13) . . ?
C6 C1 C13 119.133(13) . . ?
C2 C1 C13 122.391(13) . . ?
C2 C1 C6 118.461(13) . . ?
C10 C11 C12 120.730(14) . . ?
H11 C11 C12 119.8(3) . . ?
H11 C11 C10 119.4(3) . . ?
C1 C6 N2 120.498(13) . . ?
C5 C6 N2 119.103(14) . . ?
C5 C6 C1 120.399(14) . . ?
C4 C5 C6 119.578(15) . . ?
H5 C5 C6 118.3(3) . . ?
H5 C5 C4 122.1(3) . . ?
C3 C2 C1 120.700(15) . . ?
H2 C2 C1 119.9(2) . . ?
H2 C2 C3 119.4(2) . . ?
C10 C9 C8 120.434(15) . . ?
H9 C9 C8 120.3(3) . . ?
H9 C9 C10 119.2(3) . . ?
C3 C4 C5 120.677(15) . . ?
H4 C4 C5 120.6(3) . . ?
H4 C4 C3 118.8(3) . . ?
C7 C8 C9 119.899(14) . . ?
H8 C8 C9 121.5(3) . . ?
H8 C8 C7 118.5(3) . . ?
C12 C7 N2 120.733(14) . . ?
C8 C7 N2 119.014(13) . . ?
C8 C7 C12 120.252(14) . . ?
C9 C10 C11 120.278(15) . . ?
H10 C10 C11 120.9(3) . . ?
H10 C10 C9 118.8(3) . . ?
C4 C3 C2 120.181(16) . . ?
H3 C3 C2 121.2(3) . . ?
H3 C3 C4 118.6(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
N2 C6 C1 C13 0.771(17) . . . . ?
N2 C6 C1 C2 179.406(15) . . . . ?
N2 C6 C5 C4 -179.002(16) . . . . ?
N2 C7 C12 C13 1.577(17) . . . . ?
N2 C7 C12 C11 -179.590(15) . . . . ?
N2 C7 C8 C9 179.862(16) . . . . ?
N1 C13 C12 C11 0.339(19) . . . . ?
N1 C13 C12 C7 179.119(15) . . . . ?
N1 C13 C1 C6 179.740(15) . . . . ?
N1 C13 C1 C2 1.161(18) . . . . ?
C13 C12 C11 C10 178.517(16) . . . . ?
C13 C12 C7 C8 -178.640(14) . . . . ?
C13 C1 C6 C5 -178.899(15) . . . . ?
C13 C1 C2 C3 178.342(16) . . . . ?
C12 C11 C10 C9 0.075(19) . . . . ?
C12 C7 C8 C9 0.076(17) . . . . ?
C1 C6 C5 C4 0.673(17) . . . . ?
C1 C2 C3 C4 0.349(19) . . . . ?
C11 C10 C9 C8 0.20(2) . . . . ?
C6 C5 C4 C3 -0.574(19) . . . . ?
C5 C4 C3 C2 0.07(2) . . . . ?



_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_9aa
_database_code_depnum_ccdc_archive 'CCDC 2270292'
loop_
_audit_author_name
_audit_author_address
'Sylwia Pawledzio'
;University of Warsaw
Poland
;
_audit_update_record             
;
2023-06-15 deposited with the CCDC.	2024-01-31 downloaded from the CCDC.
;
_audit_creation_date             2023-06-15
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.11.02 svn.ra8b101fa for OlexSys, GUI svn.r6635)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl, H2 O, C13 H11 N2'
_chemical_formula_sum            'C13 H13 Cl N2 O'
_chemical_formula_weight         248.70
_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 0.0033 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'

_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                   7.7880(5)
_cell_length_b                   8.7699(5)
_cell_length_c                   9.7291(6)
_cell_angle_alpha                111.057(2)
_cell_angle_beta                 96.558(2)
_cell_angle_gamma                104.436(2)
_cell_volume                     585.08(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9427
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      48.63
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_T_max  0.9870
_exptl_absorpt_correction_T_min  0.9546
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0454 before and 0.0398 after correction.
The Ratio of minimum to maximum transmission is 0.9672.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.178
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            11565
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         48.758
_diffrn_reflns_theta_min         2.302
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9961
_reflns_number_total             11565
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         11565
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0213
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+0.0155P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0740
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
Cl1 Cl 1.06187(2) 0.73162(2) 0.89708(2) 0.01519(2) Uani 1 1 d . . . . .
O1 O 0.92275(4) 0.33028(3) 0.80177(3) 0.01772(4) Uani 1 1 d . . . . .
N2 N 0.64113(3) 0.24125(3) 0.55901(2) 0.01271(3) Uani 1 1 d . . . . .
N1 N 0.22827(3) 0.09312(3) 0.18680(3) 0.01505(3) Uani 1 1 d . . . . .
C13 C 0.36070(3) 0.14039(3) 0.30623(3) 0.01111(3) Uani 1 1 d . . . . .
C12 C 0.50521(3) 0.06493(3) 0.29538(3) 0.01118(3) Uani 1 1 d . . . . .
C1 C 0.36346(3) 0.26882(3) 0.44959(3) 0.01128(3) Uani 1 1 d . . . . .
C11 C 0.51534(4) -0.06182(3) 0.15867(3) 0.01348(3) Uani 1 1 d . . . . .
C6 C 0.50640(3) 0.31535(3) 0.57437(3) 0.01175(3) Uani 1 1 d . . . . .
C5 C 0.51104(4) 0.43916(4) 0.71756(3) 0.01471(4) Uani 1 1 d . . . . .
C2 C 0.22512(4) 0.34832(4) 0.47151(3) 0.01368(3) Uani 1 1 d . . . . .
C9 C 0.79732(4) -0.07015(4) 0.28310(3) 0.01545(4) Uani 1 1 d . . . . .
C4 C 0.37422(4) 0.51274(4) 0.73482(3) 0.01605(4) Uani 1 1 d . . . . .
C8 C 0.79129(4) 0.05174(4) 0.41722(3) 0.01418(4) Uani 1 1 d . . . . .
C7 C 0.64501(3) 0.12080(3) 0.42499(3) 0.01149(3) Uani 1 1 d . . . . .
C10 C 0.65822(4) -0.12766(4) 0.15269(3) 0.01526(4) Uani 1 1 d . . . . .
C3 C 0.23010(4) 0.46736(4) 0.61112(3) 0.01569(4) Uani 1 1 d . . . . .
H1C H 0.9156(15) 0.3112(14) 0.8742(13) 0.048(3) Uiso 1 1 d . . . . .
H2 H 0.7259(15) 0.2703(15) 0.6444(14) 0.055(3) Uiso 1 1 d . . . . .
H1A H 0.2189(13) 0.0015(12) 0.1006(11) 0.037(2) Uiso 1 1 d . . . . .
H1B H 0.1434(14) 0.1456(13) 0.1925(12) 0.044(3) Uiso 1 1 d . . . . .
H11 H 0.4280(12) -0.1038(12) 0.0683(11) 0.032(2) Uiso 1 1 d . . . . .
H5 H 0.6097(12) 0.4653(12) 0.8023(11) 0.031(2) Uiso 1 1 d . . . . .
H2A H 0.1258(14) 0.3178(13) 0.3842(12) 0.042(2) Uiso 1 1 d . . . . .
H9 H 0.8940(13) -0.1218(12) 0.2781(11) 0.038(2) Uiso 1 1 d . . . . .
H4 H 0.3710(11) 0.5915(11) 0.8338(10) 0.0267(19) Uiso 1 1 d . . . . .
H8 H 0.8859(12) 0.0917(11) 0.5122(10) 0.0276(19) Uiso 1 1 d . . . . .
H10 H 0.6660(11) -0.2184(11) 0.0550(10) 0.0270(19) Uiso 1 1 d . . . . .
H3 H 0.1339(13) 0.5209(13) 0.6267(12) 0.039(2) Uiso 1 1 d . . . . .
H1D H 0.9722(13) 0.4386(13) 0.8298(12) 0.040(2) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1C 0.786(12) . ?
O1 H1D 0.856(10) . ?
N2 C6 1.3608(3) . ?
N2 C7 1.3609(3) . ?
N2 H2 0.911(12) . ?
N1 C13 1.3239(3) . ?
N1 H1A 0.909(10) . ?
N1 H1B 0.891(11) . ?
C13 C12 1.4367(3) . ?
C13 C1 1.4376(3) . ?
C12 C11 1.4199(3) . ?
C12 C7 1.4114(3) . ?
C1 C6 1.4101(3) . ?
C1 C2 1.4187(4) . ?
C11 C10 1.3733(4) . ?
C11 H11 0.937(9) . ?
C6 C5 1.4152(4) . ?
C5 C4 1.3733(4) . ?
C5 H5 0.977(9) . ?
C2 C3 1.3731(4) . ?
C2 H2A 0.987(10) . ?
C9 C8 1.3727(4) . ?
C9 C10 1.4112(4) . ?
C9 H9 0.969(10) . ?
C4 C3 1.4111(4) . ?
C4 H4 0.970(9) . ?
C8 C7 1.4146(4) . ?
C8 H8 1.002(9) . ?
C10 H10 1.017(9) . ?
C3 H3 0.977(10) . ?

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
H1C O1 H1D 108.4(10) . . ?
C6 N2 C7 122.31(2) . . ?
C6 N2 H2 117.0(7) . . ?
C7 N2 H2 120.6(7) . . ?
C13 N1 H1A 119.9(6) . . ?
C13 N1 H1B 120.3(7) . . ?
H1A N1 H1B 119.6(9) . . ?
N1 C13 C12 120.75(2) . . ?
N1 C13 C1 120.74(2) . . ?
C12 C13 C1 118.50(2) . . ?
C11 C12 C13 122.74(2) . . ?
C7 C12 C13 118.89(2) . . ?
C7 C12 C11 118.36(2) . . ?
C6 C1 C13 119.10(2) . . ?
C6 C1 C2 118.45(2) . . ?
C2 C1 C13 122.43(2) . . ?
C12 C11 H11 122.8(6) . . ?
C10 C11 C12 120.76(2) . . ?
C10 C11 H11 116.4(6) . . ?
N2 C6 C1 120.50(2) . . ?
N2 C6 C5 119.11(2) . . ?
C1 C6 C5 120.39(2) . . ?
C6 C5 H5 118.2(6) . . ?
C4 C5 C6 119.57(3) . . ?
C4 C5 H5 122.2(6) . . ?
C1 C2 H2A 118.9(6) . . ?
C3 C2 C1 120.73(2) . . ?
C3 C2 H2A 120.4(6) . . ?
C8 C9 C10 120.48(2) . . ?
C8 C9 H9 120.3(6) . . ?
C10 C9 H9 119.2(6) . . ?
C5 C4 C3 120.72(3) . . ?
C5 C4 H4 120.4(5) . . ?
C3 C4 H4 118.7(5) . . ?
C9 C8 C7 119.88(2) . . ?
C9 C8 H8 122.1(5) . . ?
C7 C8 H8 118.0(5) . . ?
N2 C7 C12 120.68(2) . . ?
N2 C7 C8 119.05(2) . . ?
C12 C7 C8 120.28(2) . . ?
C11 C10 C9 120.24(3) . . ?
C11 C10 H10 121.0(5) . . ?
C9 C10 H10 118.7(5) . . ?
C2 C3 C4 120.13(3) . . ?
C2 C3 H3 120.8(6) . . ?
C4 C3 H3 119.1(6) . . ?

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
N2 C6 C5 C4 -178.99(2) . . . . ?
N1 C13 C12 C11 0.28(4) . . . . ?
N1 C13 C12 C7 179.14(2) . . . . ?
N1 C13 C1 C6 179.77(2) . . . . ?
N1 C13 C1 C2 1.21(4) . . . . ?
C13 C12 C11 C10 178.53(2) . . . . ?
C13 C12 C7 N2 1.50(4) . . . . ?
C13 C12 C7 C8 -178.63(2) . . . . ?
C13 C1 C6 N2 0.76(4) . . . . ?
C13 C1 C6 C5 -178.88(2) . . . . ?
C13 C1 C2 C3 178.34(2) . . . . ?
C12 C13 C1 C6 -0.44(3) . . . . ?
C12 C13 C1 C2 -178.99(2) . . . . ?
C12 C11 C10 C9 0.14(4) . . . . ?
C1 C13 C12 C11 -179.52(2) . . . . ?
C1 C13 C12 C7 -0.66(3) . . . . ?
C1 C6 C5 C4 0.66(4) . . . . ?
C1 C2 C3 C4 0.32(4) . . . . ?
C11 C12 C7 N2 -179.60(2) . . . . ?
C11 C12 C7 C8 0.27(4) . . . . ?
C6 N2 C7 C12 -1.22(4) . . . . ?
C6 N2 C7 C8 178.91(2) . . . . ?
C6 C1 C2 C3 -0.22(4) . . . . ?
C6 C5 C4 C3 -0.57(4) . . . . ?
C5 C4 C3 C2 0.08(5) . . . . ?
C2 C1 C6 N2 179.37(2) . . . . ?
C2 C1 C6 C5 -0.27(4) . . . . ?
C9 C8 C7 N2 179.86(2) . . . . ?
C9 C8 C7 C12 -0.01(4) . . . . ?
C8 C9 C10 C11 0.13(4) . . . . ?
C7 N2 C6 C1 0.06(4) . . . . ?
C7 N2 C6 C5 179.71(2) . . . . ?
C7 C12 C11 C10 -0.34(4) . . . . ?
C10 C9 C8 C7 -0.19(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'


# start Validation Reply Form
_vrf_PLAT934_9aa                 
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          3 Check 
RESPONSE: This might be a consequence of low-quality crystal.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_9aa_neutral
_database_code_depnum_ccdc_archive 'CCDC 2270293'
_audit_update_record             
;
2024-01-23 deposited with the CCDC.	2024-01-31 downloaded from the CCDC.
;
_audit_creation_date             2023-01-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_formula_moiety         '2(C6.5 H5 N), H O0.5'
_chemical_formula_sum            'C13 H11 N2 O0.5'
_chemical_formula_weight         203.245
loop_
_atom_type_symbol
_atom_type_scat_source
H 'DiSCaMB, J. Appl. Cryst. 2018, DOI:10.1107/S1600576717015825'
O 'DiSCaMB, J. Appl. Cryst. 2018, DOI:10.1107/S1600576717015825'
C 'DiSCaMB, J. Appl. Cryst. 2018, DOI:10.1107/S1600576717015825'
N 'DiSCaMB, J. Appl. Cryst. 2018, DOI:10.1107/S1600576717015825'

_space_group_crystal_system      tetragonal
_space_group_IT_number           142
_space_group_name_H-M_alt        'I 41/a c d'
_space_group_name_Hall           '-I 4bd 2c'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -y+1/4,x+3/4,z+1/4
3 y+1/4,-x+1/4,z+3/4
4 x,-y,-z+1/2
5 -x+1/2,y,-z
6 -x,-y+1/2,z
7 y+1/4,x+3/4,-z+3/4
8 -y+1/4,-x+1/4,-z+1/4
9 -x,-y,-z
10 y-1/4,-x-3/4,-z-1/4
11 -y-1/4,x-1/4,-z-3/4
12 -x,y,z-1/2
13 x-1/2,-y,z
14 x,y-1/2,-z
15 -y-1/4,-x-3/4,z-3/4
16 y-1/4,x-1/4,z-1/4
17 x+1/2,y+1/2,z+1/2
18 -y+3/4,x+5/4,z+3/4
19 y+3/4,-x+3/4,z+5/4
20 x+1/2,-y+1/2,-z+1
21 -x+1,y+1/2,-z+1/2
22 -x+1/2,-y+1,z+1/2
23 y+3/4,x+5/4,-z+5/4
24 -y+3/4,-x+3/4,-z+3/4
25 -x+1/2,-y+1/2,-z+1/2
26 y+1/4,-x-1/4,-z+1/4
27 -y+1/4,x+1/4,-z-1/4
28 -x+1/2,y+1/2,z
29 x,-y+1/2,z+1/2
30 x+1/2,y,-z+1/2
31 -y+1/4,-x-1/4,z-1/4
32 y+1/4,x+1/4,z+1/4

_symmetry_Int_Tables_number      142
_cell_length_a                   24.310(3)
_cell_length_b                   24.310(3)
_cell_length_c                   14.016(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8283.6(17)
_cell_formula_units_Z            32
_cell_measurement_reflns_used    1781
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      70.3960
_cell_measurement_theta_min      5.1310
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_size_max          0.136
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.077
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             3425.332
_diffrn_ambient_temperature      100.00(10)
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.9989
_diffrn_reflns_Laue_measured_fraction_max 0.9791
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7758
_diffrn_reflns_point_group_measured_fraction_full 0.9989
_diffrn_reflns_point_group_measured_fraction_max 0.9791
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.07
_diffrn_reflns_theta_min         1.68
_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.9791
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              29
_reflns_limit_h_min              0
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                1476
_reflns_number_total             2017
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.2143
_refine_diff_density_min         -0.2639
_refine_diff_density_rms         0.0471
_refine_ls_d_res_high            0.8085
_refine_ls_d_res_low             12.1552
_refine_ls_goodness_of_fit_ref   0.9110
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2017
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0305
_refine_ls_restrained_S_all      0.9110
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0597P)²+1.2548P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0941
_refine_special_details          
;
Electron Density Partition Based Refinement (EDPBR):
  .  Aspherical atomic scattering factors obtained from
     selected partitioning of molecular electron density
     derived from molecular wavefunction. Crystal field
     effect is modelled in the course of wavefunction
     calculations by embedding the system in a cluster of
Hirshfeld partition derived atomic multipoles for
molecules within certain radius from the system or
performing wave function calculations for a cluster of
molecules surrounding the system. Software used for
quantum mechanical calculations: ORCA 5.0. Software
used to partition electron density:HORTON. 
  .  Partitioning of molecular electron density: Iterative
     Hirshfeld
  .  Level of theory: DFT(B3LYP)/cc-pVDZ
  .  Cluster of multipoles: radius=16.0 angstrom, lmax=1
  .  Cluster of molecules: yes
  .  ADPs were computed and refined only for C, N and O, 
      while H atoms were estimated using SHADE3 server60 
      and fixed during the refinements.
  .  Refinement based on Fsqd as implemented in olex2.refine. DiSCaMB library used to obtain
aspherical atomic scattering factors.
;
_olex2_refinement_description    
;
1. Others
 Fixed U11: H2A(0.03362) H3A(0.03312) H4A(0.04402) H5A(0.03765) H12A(0.02698)
 H12B(0.04254) H2B(0.0389) H3B(0.05389) H4B(0.05936) H5B(0.04063) H15(0.03755)
 Fixed U12: H2A(0.00324) H3A(-0.00447) H4A(-0.0021) H5A(0.00647) H12A(-
 0.00327) H12B(-0.00819) H2B(-0.00747) H3B(-0.00007) H4B(-0.00234) H5B(-
 0.00782) H15(-0.00381)
 Fixed U13: H2A(-0.00086) H3A(0.0036) H4A(0.00395) H5A(-0.00011) H12A(-
 0.00272) H12B(-0.00341) H2B(-0.00357) H3B(-0.00773) H4B(0.00614) H5B(0.00575)
 H15(0.00564)
 Fixed U22: H2A(0.03267) H3A(0.03616) H4A(0.02857) H5A(0.03496) H12A(0.03491)
 H12B(0.04159) H2B(0.04068) H3B(0.04352) H4B(0.03952) H5B(0.03806) H15(0.03357)
 Fixed U23: H2A(-0.00254) H3A(-0.00477) H4A(-0.00127) H5A(-0.00091) H12A(-
 0.00116) H12B(-0.00396) H2B(-0.00107) H3B(-0.001) H4B(0.00448) H5B(-0.00063)
 H15(0.00306)
 Fixed U33: H2A(0.05319) H3A(0.059) H4A(0.05066) H5A(0.04561) H12A(0.04666)
 H12B(0.03099) H2B(0.03902) H3B(0.03046) H4B(0.03098) H5B(0.04083) H15(0.03108)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
N1A N 0.56103(4) 0.68897(4) 0.625 0.0191(3) Uani 1.000000 2 S T P
N2A N 0.68322(4) 0.56678(4) 0.625 0.0204(3) Uani 1.000000 2 S T P
C1A C 0.58606(5) 0.59299(5) 0.62433(9) 0.0168(3) Uani 1.000000 1 . . .
C2A C 0.53068(5) 0.57381(5) 0.62201(10) 0.0212(3) Uani 1.000000 1 . . .
H2A H 0.4979(8) 0.6045(8) 0.6202(14) 0.039827 Uani 1.000000 1 . . .
C3A C 0.51864(6) 0.51893(6) 0.62126(10) 0.0261(3) Uani 1.000000 1 . . .
H3A H 0.4763(8) 0.5062(8) 0.6212(13) 0.042760 Uani 1.000000 1 . . .
C4A C 0.56154(6) 0.47961(6) 0.62281(11) 0.0272(3) Uani 1.000000 1 . . .
H4A H 0.5525(8) 0.4343(8) 0.6239(13) 0.041083 Uani 1.000000 1 . . .
C5A C 0.61511(6) 0.49650(5) 0.62492(11) 0.0242(3) Uani 1.000000 1 . . .
H5A H 0.6485(8) 0.4674(8) 0.6254(13) 0.039407 Uani 1.000000 1 . . .
C6A C 0.62929(5) 0.55342(5) 0.62499(9) 0.0184(3) Uani 1.000000 1 . . .
C13A C 0.60013(5) 0.64987(5) 0.625 0.0166(3) Uani 1.000000 2 S T P
H12A H 0.5206(8) 0.6802(9) 0.6242(15) 0.036183 Uani 1.000000 1 . . .
H12B H 0.7060(9) 0.4485(9) 0.4364(13) 0.038373 Uani 1.000000 1 . . .
N1B N 0.68612(5) 0.43612(5) 0.375 0.0264(4) Uani 1.000000 2 S T P
N2B N 0.56411(4) 0.31411(4) 0.375 0.0183(3) Uani 1.000000 2 S T P
C1B C 0.63643(5) 0.36534(5) 0.45849(9) 0.0174(3) Uani 1.000000 1 . . .
C2B C 0.66803(5) 0.37057(5) 0.54362(9) 0.0203(3) Uani 1.000000 1 . . .
H2B H 0.7026(8) 0.3981(7) 0.5461(13) 0.039533 Uani 1.000000 1 . . .
C3B C 0.65614(6) 0.34000(6) 0.62303(9) 0.0233(3) Uani 1.000000 1 . . .
H3B H 0.6787(8) 0.3437(8) 0.6865(13) 0.042623 Uani 1.000000 1 . . .
C4B C 0.61164(6) 0.30239(6) 0.62128(9) 0.0245(3) Uani 1.000000 1 . . .
H4B H 0.6020(8) 0.2769(8) 0.6858(14) 0.043287 Uani 1.000000 1 . . .
C5B C 0.58125(6) 0.29540(5) 0.53991(10) 0.0221(3) Uani 1.000000 1 . . .
H5B H 0.5478(8) 0.2651(8) 0.5358(13) 0.039840 Uani 1.000000 1 . . .
C6B C 0.59316(5) 0.32599(5) 0.45507(9) 0.0176(3) Uani 1.000000 1 . . .
C13B C 0.64727(5) 0.39727(5) 0.375 0.0186(4) Uani 1.000000 2 S T P
O1 O 0.25 0.49862(5) 0.5 0.0200(3) Uani 1.000000 2 S T P
H15 H 0.2706(9) 0.4752(9) 0.4577(14) 0.034067 Uani 1.000000 1 . . .


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 C13A 1.344(2) . ?
N1A H12A 1.01(2) . ?
N1A H12A 1.01(2) 8_666 ?
N2A C6A 1.3508(15) 8_666 ?
N2A C6A 1.3508(15) . ?
C1A C2A 1.4252(17) . ?
C1A C6A 1.4248(17) . ?
C1A C13A 1.4246(14) . ?
C2A H2A 1.091(19) . ?
C2A C3A 1.3657(19) . ?
C3A H3A 1.074(19) . ?
C3A C4A 1.415(2) . ?
C4A H4A 1.124(19) . ?
C4A C5A 1.3658(19) . ?
C5A H5A 1.077(19) . ?
C5A C6A 1.4260(17) . ?
H12B N1B 1.031(19) 7_545 ?
N1B C13B 1.336(2) . ?
N2B C6B 1.3572(14) 7_545 ?
N2B C6B 1.3572(14) . ?
C1B C2B 1.4248(17) . ?
C1B C6B 1.4226(16) . ?
C1B C13B 1.4288(15) 7_545 ?
C2B H2B 1.075(17) . ?
C2B C3B 1.3693(18) . ?
C3B H3B 1.050(18) . ?
C3B C4B 1.417(2) . ?
C4B H4B 1.121(19) . ?
C4B C5B 1.369(2) . ?
C5B H5B 1.098(19) . ?
C5B C6B 1.4320(18) . ?
O1 H15 0.96(2) . ?
O1 H15 0.96(2) 5_556 ?

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
H12A N1A C13A 122.8(12) . . ?
H12A N1A C13A 122.8(12) 8_666 . ?
H12A N1A H12A 114(2) 8_666 . ?
C6A N2A C6A 117.82(15) 8_666 . ?
C6A C1A C2A 118.43(11) . . ?
C13A C1A C2A 123.00(12) . . ?
C13A C1A C6A 118.57(12) . . ?
H2A C2A C1A 117.8(10) . . ?
C3A C2A C1A 121.47(12) . . ?
C3A C2A H2A 120.7(10) . . ?
H3A C3A C2A 119.1(11) . . ?
C4A C3A C2A 120.13(13) . . ?
C4A C3A H3A 120.8(11) . . ?
H4A C4A C3A 121.2(10) . . ?
C5A C4A C3A 120.00(13) . . ?
C5A C4A H4A 118.8(10) . . ?
H5A C5A C4A 121.4(10) . . ?
C6A C5A C4A 121.48(13) . . ?
C6A C5A H5A 117.2(10) . . ?
C1A C6A N2A 123.62(12) . . ?
C5A C6A N2A 117.90(12) . . ?
C5A C6A C1A 118.48(11) . . ?
C1A C13A N1A 121.10(8) . . ?
C1A C13A N1A 121.10(8) 8_666 . ?
C1A C13A C1A 117.79(16) 8_666 . ?
H12B N1B H12B 115(2) . 7_545 ?
C13B N1B H12B 122.5(11) . 7_545 ?
C13B N1B H12B 122.5(11) . . ?
C6B N2B C6B 117.54(15) . 7_545 ?
C6B C1B C2B 119.13(11) . . ?
C13B C1B C2B 122.55(11) 7_545 . ?
C13B C1B C6B 118.30(12) 7_545 . ?
H2B C2B C1B 120.3(10) . . ?
C3B C2B C1B 121.23(12) . . ?
C3B C2B H2B 118.5(10) . . ?
H3B C3B C2B 122.2(11) . . ?
C4B C3B C2B 119.83(12) . . ?
C4B C3B H3B 118.0(11) . . ?
H4B C4B C3B 120.2(10) . . ?
C5B C4B C3B 120.43(12) . . ?
C5B C4B H4B 119.4(10) . . ?
H5B C5B C4B 121.8(10) . . ?
C6B C5B C4B 121.20(12) . . ?
C6B C5B H5B 117.0(10) . . ?
C1B C6B N2B 123.76(12) . 7_545 ?
C5B C6B N2B 118.09(11) . 7_545 ?
C5B C6B C1B 118.08(11) . . ?
C1B C13B N1B 120.97(8) 7_545 . ?
C1B C13B N1B 120.97(8) . . ?
C1B C13B C1B 118.06(15) . 7_545 ?
H15 O1 H15 108(2) 5_556 . ?

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
N1A C13A C1A C2A 1.09(6) . . . . ?
N1A C13A C1A C2A 1.09(6) . . 8_666 8_666 ?
N1A C13A C1A C6A -179.60(8) . . 8_666 8_666 ?
N1A C13A C1A C6A -179.60(8) . . . . ?
N2A C6A C1A C2A 178.47(12) 8_666 . . . ?
N2A C6A C1A C2A 178.47(12) . . . . ?
N2A C6A C1A C13A -0.87(13) . . . . ?
N2A C6A C1A C13A -0.87(13) 8_666 . . . ?
N2A C6A C5A C4A -178.55(12) . . . . ?
N2A C6A C5A C4A -178.55(12) 8_666 . . . ?
C1A C2A C3A C4A 0.01(16) . . . . ?
C1A C6A C5A C4A 0.99(15) . . . . ?
C1A C13A C1A C2A -178.91(6) . . 8_666 8_666 ?
C1A C13A C1A C6A 0.40(8) . . 8_666 8_666 ?
C2A C3A C4A C5A -0.09(17) . . . . ?
C3A C4A C5A C6A -0.42(18) . . . . ?
N1B C13B C1B C2B -3.82(6) . . 7_545 7_545 ?
N1B C13B C1B C2B -3.82(6) . . . . ?
N1B C13B C1B C6B 177.70(8) . . . . ?
N1B C13B C1B C6B 177.70(8) . . 7_545 7_545 ?
N1B C13B C1B C13B -0(90000000000000) . . . 7_545 ?
N2B C6B C1B C2B -173.54(10) 7_545 . . . ?
N2B C6B C1B C2B -173.54(10) . . . . ?
N2B C6B C1B C13B 4.99(11) . 7_545 7_545 . ?
N2B C6B C1B C13B 4.99(11) . . . 7_545 ?
N2B C6B C5B C4B 175.18(10) . . . . ?
N2B C6B C5B C4B 175.18(10) 7_545 . . . ?
C1B C2B C3B C4B -0.07(15) . . . . ?
C1B C6B C5B C4B -2.06(13) . . . . ?
C1B C13B C1B C2B 176.18(6) 7_545 . . . ?
C1B C13B C1B C6B -2.30(8) 7_545 . . . ?
C1B C13B C1B C13B 0(90000000000000) . 7_545 7_545 . ?
C2B C3B C4B C5B 1.62(16) . . . . ?
C3B C4B C5B C6B -0.52(15) . . . . ?



_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_2017_01_11_sp_9aa_n
_database_code_depnum_ccdc_archive 'CCDC 2270294'
loop_
_audit_author_name
_audit_author_address
'Sylwia Pawledzio'
;University of Warsaw
Poland
;
_audit_update_record             
;
2023-06-15 deposited with the CCDC.	2024-01-31 downloaded from the CCDC.
;
_audit_creation_date             2023-01-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C13 H10 N2), H2 O'
_chemical_formula_sum            'C26 H22 N4 O'
_chemical_formula_weight         406.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 H22 N4 O1'
_chemical_oxdiff_usercomment     100K
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      tetragonal
_space_group_IT_number           142
_space_group_name_H-M_alt        'I 41/a c d'
_space_group_name_Hall           '-I 4bd 2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/4, x+3/4, z+1/4'
'-x, -y+1/2, z'
'y+1/4, -x+1/4, z+3/4'
'x, -y, -z+1/2'
'-x+1/2, y, -z'
'y+3/4, x+1/4, -z+1/4'
'-y+1/4, -x+1/4, -z+1/4'
'x+1/2, y+1/2, z+1/2'
'-y+3/4, x+5/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'y+3/4, -x+3/4, z+5/4'
'x+1/2, -y+1/2, -z+1'
'-x+1, y+1/2, -z+1/2'
'y+5/4, x+3/4, -z+3/4'
'-y+3/4, -x+3/4, -z+3/4'
'-x, -y, -z'
'y-1/4, -x-3/4, -z-1/4'
'x, y-1/2, -z'
'-y-1/4, x-1/4, -z-3/4'
'-x, y, z-1/2'
'x-1/2, -y, z'
'-y-3/4, -x-1/4, z-1/4'
'y-1/4, x-1/4, z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/4, -x-1/4, -z+1/4'
'x+1/2, y, -z+1/2'
'-y+1/4, x+1/4, -z-1/4'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'-y-1/4, -x+1/4, z+1/4'
'y+1/4, x+1/4, z+1/4'

_cell_length_a                   24.310(2)
_cell_length_b                   24.310(2)
_cell_length_c                   14.016(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8284(2)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    1781
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      70.3960
_cell_measurement_theta_min      5.1310
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3424
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 -13 -4 0.0374
12 -10 2 0.0464
9 4 7 0.0410
-3 13 5 0.0530
-10 -1 -7 0.0348
5 5 8 0.0462
3 -14 -3 0.0419
2 14 -4 0.0710
14 8 -2 0.0391
16 2 0 0.0295
-16 -2 0 0.0478
-9 -12 3 0.0550
-3 -15 4 0.0581
-1 -2 -9 0.0341
1 0 9 0.0556

_exptl_crystal_size_max          0.136
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.077
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.5332 -13.1490 -4.3073 0.1136 0.4765 0.8718
12.0061 -9.5002 2.2501 0.2309 0.9639 0.1324
8.7156 3.5933 7.2907 0.1386 0.5763 -0.8054
-3.0821 12.8068 5.0139 -0.0880 -0.3695 -0.9251
-10.3716 -0.8653 -6.8365 -0.1743 -0.7259 0.6653
4.9431 4.9467 8.0331 -0.0521 0.4146 -0.8965
3.1018 -13.9859 -3.0711 -0.0435 0.5192 0.8163
1.9038 14.0933 -3.9309 0.6618 -0.6961 -0.2854
13.9270 8.1178 -1.9536 0.9982 0.1132 -0.2790
15.9639 2.0895 0.0185 0.8405 0.5368 -0.2004
-15.9639 -2.0895 -0.0185 -0.8405 -0.5368 0.2004
-8.9069 -12.1134 2.9366 -0.9045 0.2930 0.3319
-2.8953 -15.1012 3.9253 -0.7363 0.6976 0.3351
-0.9683 -1.9062 -9.0165 0.3779 -0.4336 0.8211
0.9827 -0.0990 9.0064 -0.4280 0.5139 -0.7361

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7758
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.458
_diffrn_reflns_theta_min         3.636
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     18.00  44.00   1.00    6.00    --    0.00 -99.00  60.00   26
  2  ω     12.00  43.00   1.00    6.00    --    0.00 -99.00 120.00   31
  3  ω     32.00 128.00   1.00   55.00    --   54.96  37.00-180.00   96
  4  ω     94.00 137.00   1.00   55.00    --   54.96 125.00 120.00   43
  5  ω    101.00 167.00   1.00   90.00    --  109.92 111.00  60.00   66
  6  ω    103.00 164.00   1.00   90.00    --  109.92 111.00-150.00   61
  7  ω    109.00 163.00   1.00   90.00    --  109.92 111.00   0.00   54
  8  ω    133.00 178.00   1.00   90.00    --  109.92 111.00 -90.00   45
  9  ω    111.00 164.00   1.00   90.00    --  109.92 111.00  30.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0493609000
_diffrn_orient_matrix_UB_12      0.0256141000
_diffrn_orient_matrix_UB_13      -0.0526268000
_diffrn_orient_matrix_UB_21      0.0388022000
_diffrn_orient_matrix_UB_22      -0.0400196000
_diffrn_orient_matrix_UB_23      0.0523847000
_diffrn_orient_matrix_UB_31      -0.0069603000
_diffrn_orient_matrix_UB_32      -0.0420252000
_diffrn_orient_matrix_UB_33      -0.0814367000
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1476
_reflns_number_total             2017
_reflns_odcompleteness_completeness 99.90
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2017
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.041
_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)+(0.0812P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1280
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Free rotating group:
 O1(H1A)
1.b Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C2B(H2BA), C3B(H3B), C4B(H4B), C5B(H5B)
;
_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
N1A N 0.56112(5) 0.68888(5) 0.6250 0.0221(4) Uani 1 2 d S T P . .
H1AA H 0.5266(8) 0.6807(8) 0.6244(14) 0.026 Uiso 1 1 d R . . . .
N2A N 0.68337(5) 0.56663(5) 0.6250 0.0238(4) Uani 1 2 d S T P . .
C1A C 0.58600(6) 0.59289(6) 0.62445(10) 0.0198(4) Uani 1 1 d . . . . .
C2A C 0.53084(7) 0.57365(7) 0.62203(11) 0.0243(3) Uani 1 1 d . . . . .
H2A H 0.5022 0.5990 0.6209 0.029 Uiso 1 1 calc R . . . .
C3A C 0.51882(7) 0.51900(7) 0.62127(12) 0.0295(4) Uani 1 1 d . . . . .
H3A H 0.4824 0.5075 0.6197 0.035 Uiso 1 1 calc R . . . .
C4A C 0.56169(8) 0.47978(7) 0.62294(13) 0.0303(4) Uani 1 1 d . . . . .
H4A H 0.5534 0.4424 0.6227 0.036 Uiso 1 1 calc R . . . .
C5A C 0.61505(7) 0.49658(7) 0.62493(13) 0.0274(4) Uani 1 1 d . . . . .
H5A H 0.6429 0.4704 0.6263 0.033 Uiso 1 1 calc R . . . .
C6A C 0.62928(6) 0.55340(6) 0.62499(11) 0.0215(3) Uani 1 1 d . . . . .
C13A C 0.60016(6) 0.64984(6) 0.6250 0.0199(4) Uani 1 2 d S T P . .
N1B N 0.68598(6) 0.43598(6) 0.3750 0.0294(5) Uani 1 2 d S T P . .
H1BA H 0.7019(9) 0.4475(9) 0.4290(14) 0.035 Uiso 1 1 d R . . . .
N2B N 0.56394(5) 0.31394(5) 0.3750 0.0217(4) Uani 1 2 d S T P . .
C1B C 0.63642(6) 0.36541(6) 0.45858(11) 0.0209(3) Uani 1 1 d . . . . .
C2B C 0.66790(6) 0.37049(6) 0.54376(12) 0.0237(3) Uani 1 1 d . . . . .
H2BA H 0.6972 0.3951 0.5455 0.028 Uiso 1 1 calc R . . . .
C3B C 0.65605(7) 0.34007(7) 0.62282(11) 0.0267(4) Uani 1 1 d . . . . .
H3B H 0.6771 0.3440 0.6778 0.032 Uiso 1 1 calc R . . . .
C4B C 0.61165(7) 0.30253(7) 0.62093(11) 0.0277(4) Uani 1 1 d . . . . .
H4B H 0.6030 0.2825 0.6754 0.033 Uiso 1 1 calc R . . . .
C5B C 0.58142(7) 0.29547(6) 0.53994(12) 0.0252(4) Uani 1 1 d . . . . .
H5B H 0.5526 0.2703 0.5398 0.030 Uiso 1 1 calc R . . . .
C6B C 0.59320(6) 0.32603(6) 0.45522(11) 0.0213(3) Uani 1 1 d . . . . .
C13B C 0.64719(6) 0.39719(6) 0.3750 0.0223(5) Uani 1 2 d S T P . .
O1 O 0.2500 0.49886(6) 0.5000 0.0235(3) Uani 1 2 d S T P . .
H1A H 0.2680 0.4787 0.4616 0.035 Uiso 1 1 d G . . . .


_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 H1AA 0.86(2) . ?
N1A C13A 1.342(3) . ?
N2A C6A 1.3536(19) . ?
N2A C6A 1.3536(19) 8_666 ?
C1A C2A 1.421(2) . ?
C1A C6A 1.424(2) . ?
C1A C13A 1.4268(18) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.360(2) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.413(2) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.360(2) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.424(2) . ?
C13A C1A 1.4268(18) 8_666 ?
N1B H1BA 0.89(2) . ?
N1B C13B 1.333(3) . ?
N2B C6B 1.3625(18) 15_445 ?
N2B C6B 1.3624(18) . ?
C1B C2B 1.424(2) . ?
C1B C6B 1.422(2) . ?
C1B C13B 1.4277(19) . ?
C2B H2BA 0.9300 . ?
C2B C3B 1.363(2) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.414(2) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.363(2) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.430(2) . ?
C13B C1B 1.4277(19) 15_445 ?
O1 H1A 0.8501 . ?

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
C13A N1A H1AA 121.7(14) . . ?
C6A N2A C6A 117.50(19) . 8_666 ?
C2A C1A C6A 118.40(14) . . ?
C2A C1A C13A 123.18(15) . . ?
C6A C1A C13A 118.41(15) . . ?
C1A C2A H2A 119.2 . . ?
C3A C2A C1A 121.63(15) . . ?
C3A C2A H2A 119.2 . . ?
C2A C3A H3A 120.0 . . ?
C2A C3A C4A 120.03(16) . . ?
C4A C3A H3A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C5A C4A C3A 120.08(16) . . ?
C5A C4A H4A 120.0 . . ?
C4A C5A H5A 119.2 . . ?
C4A C5A C6A 121.53(16) . . ?
C6A C5A H5A 119.2 . . ?
N2A C6A C1A 123.88(15) . . ?
N2A C6A C5A 117.81(15) . . ?
C5A C6A C1A 118.31(14) . . ?
N1A C13A C1A 121.04(10) . . ?
N1A C13A C1A 121.04(10) . 8_666 ?
C1A C13A C1A 117.9(2) . 8_666 ?
C13B N1B H1BA 121.8(13) . . ?
C6B N2B C6B 117.12(18) . 15_445 ?
C2B C1B C13B 122.86(14) . . ?
C6B C1B C2B 118.91(14) . . ?
C6B C1B C13B 118.21(14) . . ?
C1B C2B H2BA 119.3 . . ?
C3B C2B C1B 121.41(14) . . ?
C3B C2B H2BA 119.3 . . ?
C2B C3B H3B 120.1 . . ?
C2B C3B C4B 119.76(15) . . ?
C4B C3B H3B 120.1 . . ?
C3B C4B H4B 119.7 . . ?
C5B C4B C3B 120.57(15) . . ?
C5B C4B H4B 119.7 . . ?
C4B C5B H5B 119.4 . . ?
C4B C5B C6B 121.21(15) . . ?
C6B C5B H5B 119.4 . . ?
N2B C6B C1B 123.93(15) . . ?
N2B C6B C5B 117.95(14) . . ?
C1B C6B C5B 118.05(14) . . ?
N1B C13B C1B 120.83(10) . 15_445 ?
N1B C13B C1B 120.83(10) . . ?
C1B C13B C1B 118.34(19) 15_445 . ?

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
C1A C2A C3A C4A 0.0(3) . . . . ?
C2A C1A C6A N2A 178.42(13) . . . . ?
C2A C1A C6A C5A -1.2(2) . . . . ?
C2A C1A C13A N1A 1.25(17) . . . . ?
C2A C1A C13A C1A -178.75(17) . . . 8_666 ?
C2A C3A C4A C5A -0.3(3) . . . . ?
C3A C4A C5A C6A -0.3(3) . . . . ?
C4A C5A C6A N2A -178.63(14) . . . . ?
C4A C5A C6A C1A 1.0(3) . . . . ?
C6A N2A C6A C1A 0.36(11) 8_666 . . . ?
C6A N2A C6A C5A 179.97(17) 8_666 . . . ?
C6A C1A C2A C3A 0.7(2) . . . . ?
C6A C1A C13A N1A -179.68(10) . . . . ?
C6A C1A C13A C1A 0.33(10) . . . 8_666 ?
C13A C1A C2A C3A 179.79(13) . . . . ?
C13A C1A C6A N2A -0.7(2) . . . . ?
C13A C1A C6A C5A 179.68(13) . . . . ?
C1B C2B C3B C4B 0.0(2) . . . . ?
C2B C1B C6B N2B -173.48(12) . . . . ?
C2B C1B C6B C5B 3.5(2) . . . . ?
C2B C1B C13B N1B -3.94(16) . . . . ?
C2B C1B C13B C1B 176.07(16) . . . 15_445 ?
C2B C3B C4B C5B 1.6(2) . . . . ?
C3B C4B C5B C6B -0.7(2) . . . . ?
C4B C5B C6B N2B 175.25(13) . . . . ?
C4B C5B C6B C1B -1.9(2) . . . . ?
C6B N2B C6B C1B -2.52(10) 15_445 . . . ?
C6B N2B C6B C5B -179.51(15) 15_445 . . . ?
C6B C1B C2B C3B -2.6(2) . . . . ?
C6B C1B C13B N1B 177.75(9) . . . . ?
C6B C1B C13B C1B -2.25(9) . . . 15_445 ?
C13B C1B C2B C3B 179.06(13) . . . . ?
C13B C1B C6B N2B 4.90(19) . . . . ?
C13B C1B C6B C5B -178.12(11) . . . . ?


_olex2_date_sample_data_collection 2018-01-11
_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 1.152
_oxdiff_exptl_absorpt_empirical_full_min 0.877
