# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# 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_mo_ncsu_pn33_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2266091'
loop_
_audit_author_name
_audit_author_address
'Phattananawee Nalaoh'
;The University of Tennessee, Knoxville
United States of America
;
_audit_update_record             
;
2023-06-26 deposited with the CCDC.	2023-06-28 downloaded from the CCDC.
;
_audit_creation_date             2023-05-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H11 N O5'
_chemical_formula_sum            'C10 H11 N O5'
_chemical_formula_weight         225.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_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                   6.4414(14)
_cell_length_b                   11.785(3)
_cell_length_c                   13.959(3)
_cell_angle_alpha                92.212(7)
_cell_angle_beta                 96.911(8)
_cell_angle_gamma                94.926(8)
_cell_volume                     1046.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2731
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      3.34
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0951 before and 0.0593 after correction.
The Ratio of minimum to maximum transmission is 0.8724.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.306
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.018
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0822
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13728
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.423
_diffrn_reflns_theta_min         2.331
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3015
_reflns_number_total             4249
_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 V8.40B (Bruker, 2016)'
_computing_data_collection       'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1156
_refine_ls_R_factor_gt           0.0749
_refine_ls_restrained_S_all      1.110
_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)+(0.0269P)²+1.4927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1391
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C12(H12), C14(H14), N1(H1), N2(H2A)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3053(5) 0.7185(2) 0.6066(2) 0.0150(7) Uani 1 1 d . . . . .
C2 C 0.2702(5) 0.6246(2) 0.5393(2) 0.0142(7) Uani 1 1 d . . . . .
H2 H 0.270990 0.546632 0.554024 0.017 Uiso 1 1 calc R . . . .
C3 C 0.2351(5) 0.6653(2) 0.4494(2) 0.0145(7) Uani 1 1 d . . . . .
C4 C 0.2913(5) 0.8156(3) 0.5531(2) 0.0148(7) Uani 1 1 d . . . . .
H4 H 0.308044 0.891950 0.579130 0.018 Uiso 1 1 calc R . . . .
C5 C 0.3490(5) 0.7196(3) 0.7117(2) 0.0158(7) Uani 1 1 d . . . . .
C6 C 0.3693(6) 0.6037(3) 0.7547(2) 0.0227(8) Uani 1 1 d . . . . .
H6A H 0.229054 0.560595 0.748314 0.027 Uiso 1 1 calc R . . . .
H6B H 0.460795 0.560107 0.717916 0.027 Uiso 1 1 calc R . . . .
C7 C 0.4591(6) 0.6139(3) 0.8590(3) 0.0222(8) Uani 1 1 d . . . . .
C8 C 0.7812(6) 0.6417(3) 0.9635(3) 0.0315(9) Uani 1 1 d . . . . .
H8A H 0.932774 0.648595 0.959959 0.047 Uiso 1 1 calc GR . . . .
H8B H 0.742984 0.573019 0.997263 0.047 Uiso 1 1 calc GR . . . .
H8C H 0.743702 0.708901 0.998849 0.047 Uiso 1 1 calc GR . . . .
C9 C 0.1889(5) 0.6047(2) 0.3559(2) 0.0145(7) Uani 1 1 d . . . . .
C10 C 0.1147(6) 0.6240(3) 0.1871(2) 0.0278(9) Uani 1 1 d . . . . .
H10A H 0.091731 0.683711 0.141071 0.042 Uiso 1 1 calc GR . . . .
H10B H -0.013666 0.572369 0.184657 0.042 Uiso 1 1 calc GR . . . .
H10C H 0.229793 0.580873 0.170177 0.042 Uiso 1 1 calc GR . . . .
C11 C 0.1792(5) 0.1169(2) 0.3472(2) 0.0155(7) Uani 1 1 d . . . . .
C12 C 0.1717(5) 0.2329(2) 0.3338(2) 0.0147(7) Uani 1 1 d . . . . .
H12 H 0.149965 0.267302 0.273346 0.018 Uiso 1 1 calc R . . . .
C13 C 0.2267(5) 0.2107(3) 0.4921(2) 0.0154(7) Uani 1 1 d . . . . .
C14 C 0.2133(5) 0.1042(3) 0.4476(2) 0.0153(7) Uani 1 1 d . . . . .
H14 H 0.224978 0.034416 0.478855 0.018 Uiso 1 1 calc R . . . .
C15 C 0.1675(5) 0.0261(3) 0.2728(2) 0.0158(7) Uani 1 1 d . . . . .
C16 C 0.1193(6) 0.0571(3) 0.1682(2) 0.0232(8) Uani 1 1 d . . . . .
H16A H -0.024642 0.081403 0.157333 0.028 Uiso 1 1 calc R . . . .
H16B H 0.218518 0.121845 0.154996 0.028 Uiso 1 1 calc R . . . .
C17 C 0.1371(6) -0.0423(3) 0.1002(2) 0.0216(8) Uani 1 1 d . . . . .
C18 C 0.3767(7) -0.1408(3) 0.0204(3) 0.0336(10) Uani 1 1 d . . . . .
H18A H 0.528445 -0.140766 0.019015 0.050 Uiso 1 1 calc GR . . . .
H18B H 0.307564 -0.132169 -0.045109 0.050 Uiso 1 1 calc GR . . . .
H18C H 0.322054 -0.212878 0.044611 0.050 Uiso 1 1 calc GR . . . .
C19 C 0.2664(5) 0.2465(3) 0.5943(2) 0.0181(7) Uani 1 1 d . . . . .
C20 C 0.3297(6) 0.1787(3) 0.7519(2) 0.0302(9) Uani 1 1 d . . . . .
H20A H 0.358824 0.107819 0.783430 0.045 Uiso 1 1 calc GR . . . .
H20B H 0.206366 0.208237 0.775283 0.045 Uiso 1 1 calc GR . . . .
H20C H 0.451275 0.235102 0.767245 0.045 Uiso 1 1 calc GR . . . .
N1 N 0.2504(4) 0.7839(2) 0.45955(19) 0.0144(6) Uani 1 1 d . . . . .
H1 H 0.235588 0.830486 0.411892 0.017 Uiso 1 1 calc R . . . .
N2 N 0.2005(4) 0.2877(2) 0.42083(18) 0.0137(6) Uani 1 1 d . . . . .
H2A H 0.202473 0.361920 0.431020 0.016 Uiso 1 1 calc R . . . .
O1 O 0.2896(4) 0.15624(18) 0.64865(16) 0.0236(6) Uani 1 1 d . . . . .
O2 O 0.6691(4) 0.63361(19) 0.86665(17) 0.0255(6) Uani 1 1 d . . . . .
O3 O 0.1683(4) 0.67546(17) 0.28341(15) 0.0183(5) Uani 1 1 d . . . . .
O4 O 0.3683(4) 0.80624(18) 0.76393(16) 0.0215(5) Uani 1 1 d . . . . .
O5 O 0.3608(4) 0.60606(19) 0.92691(18) 0.0288(6) Uani 1 1 d . . . . .
O6 O 0.1701(4) 0.50131(17) 0.34406(16) 0.0225(6) Uani 1 1 d . . . . .
O7 O 0.3353(4) -0.04706(19) 0.08309(17) 0.0277(6) Uani 1 1 d . . . . .
O8 O 0.1929(4) -0.07300(17) 0.29224(16) 0.0206(5) Uani 1 1 d . . . . .
O9 O -0.0061(4) -0.11051(19) 0.06654(18) 0.0298(6) Uani 1 1 d . . . . .
O10 O 0.2784(4) 0.34464(18) 0.62622(16) 0.0218(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.409(4) . ?
C1 C4 1.394(4) . ?
C1 C5 1.459(4) . ?
C2 C3 1.361(4) . ?
C3 C9 1.449(4) . ?
C3 N1 1.394(4) . ?
C4 N1 1.333(4) . ?
C5 C6 1.523(4) . ?
C5 O4 1.220(4) . ?
C6 C7 1.497(5) . ?
C7 O2 1.344(4) . ?
C7 O5 1.203(4) . ?
C8 O2 1.450(4) . ?
C9 O3 1.337(4) . ?
C9 O6 1.218(3) . ?
C10 O3 1.444(4) . ?
C11 C12 1.392(4) . ?
C11 C14 1.408(4) . ?
C11 C15 1.453(4) . ?
C12 N2 1.339(4) . ?
C13 C14 1.370(4) . ?
C13 C19 1.458(5) . ?
C13 N2 1.377(4) . ?
C15 C16 1.521(4) . ?
C15 O8 1.230(3) . ?
C16 C17 1.499(4) . ?
C17 O7 1.333(4) . ?
C17 O9 1.207(4) . ?
C18 O7 1.445(4) . ?
C19 O1 1.339(4) . ?
C19 O10 1.215(4) . ?
C20 O1 1.444(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C5 129.0(3) . . ?
C4 C1 C2 106.3(3) . . ?
C4 C1 C5 124.7(3) . . ?
C3 C2 C1 108.0(3) . . ?
C2 C3 C9 130.1(3) . . ?
C2 C3 N1 107.7(3) . . ?
N1 C3 C9 122.2(3) . . ?
N1 C4 C1 109.0(3) . . ?
C1 C5 C6 115.8(3) . . ?
O4 C5 C1 123.7(3) . . ?
O4 C5 C6 120.5(3) . . ?
C7 C6 C5 112.2(3) . . ?
O2 C7 C6 109.8(3) . . ?
O5 C7 C6 126.0(3) . . ?
O5 C7 O2 124.2(3) . . ?
O3 C9 C3 112.3(2) . . ?
O6 C9 C3 124.2(3) . . ?
O6 C9 O3 123.5(3) . . ?
C12 C11 C14 106.8(3) . . ?
C12 C11 C15 127.1(3) . . ?
C14 C11 C15 126.0(3) . . ?
N2 C12 C11 108.0(3) . . ?
C14 C13 C19 130.4(3) . . ?
C14 C13 N2 107.5(3) . . ?
N2 C13 C19 122.1(3) . . ?
C13 C14 C11 107.6(3) . . ?
C11 C15 C16 117.7(3) . . ?
O8 C15 C11 122.1(3) . . ?
O8 C15 C16 120.2(3) . . ?
C17 C16 C15 111.1(3) . . ?
O7 C17 C16 110.6(3) . . ?
O9 C17 C16 125.4(3) . . ?
O9 C17 O7 124.0(3) . . ?
O1 C19 C13 110.6(3) . . ?
O10 C19 C13 125.0(3) . . ?
O10 C19 O1 124.4(3) . . ?
C4 N1 C3 109.0(2) . . ?
C12 N2 C13 110.0(2) . . ?
C19 O1 C20 116.9(3) . . ?
C7 O2 C8 116.7(3) . . ?
C9 O3 C10 116.9(2) . . ?
C17 O7 C18 116.7(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
C1 C2 C3 C9 -179.2(3) . . . . ?
C1 C2 C3 N1 0.7(3) . . . . ?
C1 C4 N1 C3 0.5(3) . . . . ?
C1 C5 C6 C7 167.6(3) . . . . ?
C2 C1 C4 N1 0.0(3) . . . . ?
C2 C1 C5 C6 3.0(5) . . . . ?
C2 C1 C5 O4 -176.7(3) . . . . ?
C2 C3 C9 O3 -178.7(3) . . . . ?
C2 C3 C9 O6 1.5(5) . . . . ?
C2 C3 N1 C4 -0.8(3) . . . . ?
C3 C9 O3 C10 -177.9(3) . . . . ?
C4 C1 C2 C3 -0.5(4) . . . . ?
C4 C1 C5 C6 -176.7(3) . . . . ?
C4 C1 C5 O4 3.5(5) . . . . ?
C5 C1 C2 C3 179.7(3) . . . . ?
C5 C1 C4 N1 179.8(3) . . . . ?
C5 C6 C7 O2 -80.9(3) . . . . ?
C5 C6 C7 O5 99.1(4) . . . . ?
C6 C7 O2 C8 -177.9(3) . . . . ?
C9 C3 N1 C4 179.2(3) . . . . ?
C11 C12 N2 C13 -0.1(3) . . . . ?
C11 C15 C16 C17 173.5(3) . . . . ?
C12 C11 C14 C13 -0.3(4) . . . . ?
C12 C11 C15 C16 -6.9(5) . . . . ?
C12 C11 C15 O8 173.9(3) . . . . ?
C13 C19 O1 C20 -179.9(3) . . . . ?
C14 C11 C12 N2 0.3(4) . . . . ?
C14 C11 C15 C16 177.2(3) . . . . ?
C14 C11 C15 O8 -2.0(5) . . . . ?
C14 C13 C19 O1 -0.7(5) . . . . ?
C14 C13 C19 O10 178.7(3) . . . . ?
C14 C13 N2 C12 -0.1(3) . . . . ?
C15 C11 C12 N2 -176.2(3) . . . . ?
C15 C11 C14 C13 176.2(3) . . . . ?
C15 C16 C17 O7 -85.1(3) . . . . ?
C15 C16 C17 O9 93.6(4) . . . . ?
C16 C17 O7 C18 178.5(3) . . . . ?
C19 C13 C14 C11 -178.1(3) . . . . ?
C19 C13 N2 C12 178.4(3) . . . . ?
N1 C3 C9 O3 1.3(4) . . . . ?
N1 C3 C9 O6 -178.5(3) . . . . ?
N2 C13 C14 C11 0.2(4) . . . . ?
N2 C13 C19 O1 -178.9(3) . . . . ?
N2 C13 C19 O10 0.6(5) . . . . ?
O4 C5 C6 C7 -12.6(5) . . . . ?
O5 C7 O2 C8 2.2(5) . . . . ?
O6 C9 O3 C10 1.9(5) . . . . ?
O8 C15 C16 C17 -7.3(5) . . . . ?
O9 C17 O7 C18 -0.2(5) . . . . ?
O10 C19 O1 C20 0.6(5) . . . . ?

_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_mo_ncsu_t1_isomer_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2266097'
loop_
_audit_author_name
_audit_author_address
'Phattananawee Nalaoh'
;The University of Tennessee, Knoxville
United States of America
;
_audit_update_record             
;
2023-05-29 deposited with the CCDC.	2023-06-28 downloaded from the CCDC.
;
_audit_creation_date             2023-05-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H11 Cl3 N2 O4'
_chemical_formula_sum            'C15 H11 Cl3 N2 O4'
_chemical_formula_weight         389.61
_chemical_absolute_configuration .
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.5963(5)
_cell_length_b                   12.8953(9)
_cell_length_c                   9.5356(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.461(2)
_cell_angle_gamma                90
_cell_volume                     804.24(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5194
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.70
_cell_measurement_theta_min      2.67
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.881
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1003 before and 0.0550 after correction.
The Ratio of minimum to maximum transmission is 0.8827.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12227
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.671
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.905
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3039
_reflns_number_total             3253
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 1313 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3253
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.039
_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)+(0.0368P)²+0.3342P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0796
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C8(H8), C9(H9)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3280(6) 0.6356(3) 0.6554(4) 0.0141(8) Uani 1 1 d . . . . .
C2 C 0.3577(6) 0.7285(3) 0.7375(5) 0.0187(9) Uani 1 1 d . . . . .
H2 H 0.257553 0.765780 0.780057 0.022 Uiso 1 1 calc R . . . .
C3 C 0.5597(7) 0.7522(3) 0.7420(5) 0.0202(10) Uani 1 1 d . . . . .
H3 H 0.625951 0.810254 0.789242 0.024 Uiso 1 1 calc R . . . .
C4 C 0.5132(6) 0.5096(3) 0.5307(4) 0.0135(8) Uani 1 1 d . . . . .
H4 H 0.604335 0.456920 0.583858 0.016 Uiso 1 1 calc R . . . .
C5 C 0.2856(6) 0.4757(3) 0.5250(4) 0.0118(8) Uani 1 1 d . . . . .
H5 H 0.221810 0.471274 0.424209 0.014 Uiso 1 1 calc R . . . .
C6 C 0.1747(6) 0.5618(3) 0.6031(4) 0.0135(8) Uani 1 1 d . . . . .
C7 C 0.5754(6) 0.5254(3) 0.3849(4) 0.0146(8) Uani 1 1 d . . . . .
C8 C 0.4855(6) 0.5820(3) 0.2707(5) 0.0189(9) Uani 1 1 d . . . . .
H8 H 0.365092 0.622777 0.268154 0.023 Uiso 1 1 calc R . . . .
C9 C 0.6013(6) 0.5692(3) 0.1600(4) 0.0181(9) Uani 1 1 d . . . . .
H9 H 0.575145 0.599625 0.068660 0.022 Uiso 1 1 calc R . . . .
C10 C 0.7632(6) 0.5033(3) 0.2082(4) 0.0132(8) Uani 1 1 d . . . . .
C11 C 0.2605(6) 0.3729(3) 0.5979(4) 0.0150(9) Uani 1 1 d . . . . .
C12 C 0.0153(7) 0.2472(3) 0.6412(5) 0.0242(10) Uani 1 1 d . . . . .
H12A H -0.129022 0.229903 0.613706 0.036 Uiso 1 1 calc GR . . . .
H12B H 0.039016 0.261846 0.742887 0.036 Uiso 1 1 calc GR . . . .
H12C H 0.100674 0.188509 0.619812 0.036 Uiso 1 1 calc GR . . . .
C13 C 0.9303(6) 0.4581(3) 0.1472(4) 0.0157(9) Uani 1 1 d . . . . .
C14 C 0.9588(6) 0.4869(3) -0.0064(4) 0.0166(9) Uani 1 1 d . . . . .
C16 C 0.5124(6) 0.6073(3) 0.6158(4) 0.0126(8) Uani 1 1 d . . . . .
Cl1 Cl 0.98130(17) 0.62383(8) -0.02374(11) 0.0239(3) Uani 1 1 d . . . . .
Cl2 Cl 0.74348(14) 0.43937(9) -0.12051(10) 0.0214(2) Uani 1 1 d . . . . .
Cl4 Cl 1.18195(14) 0.42892(9) -0.05549(10) 0.0228(3) Uani 1 1 d . . . . .
N1 N 0.7417(5) 0.4779(3) 0.3466(4) 0.0125(7) Uani 1 1 d . . . . .
N3 N 0.6536(6) 0.6777(3) 0.6662(4) 0.0168(7) Uani 1 1 d . . . . .
O1 O -0.0086(4) 0.5599(2) 0.6108(3) 0.0182(6) Uani 1 1 d . . . . .
O2 O 0.3882(5) 0.3308(2) 0.6785(3) 0.0215(7) Uani 1 1 d . . . . .
O3 O 1.0492(4) 0.3965(2) 0.2112(3) 0.0197(7) Uani 1 1 d . . . . .
O5 O 0.0677(5) 0.3378(2) 0.5632(3) 0.0192(6) Uani 1 1 d . . . . .
H1 H 0.831(6) 0.438(4) 0.407(4) 0.011(10) Uiso 1 1 d . . . . .
H3A H 0.778(9) 0.669(4) 0.661(6) 0.033(15) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.430(6) . ?
C1 C6 1.431(6) . ?
C1 C16 1.369(5) . ?
C2 C3 1.362(6) . ?
C3 N3 1.396(5) . ?
C4 C5 1.558(5) . ?
C4 C7 1.514(5) . ?
C4 C16 1.500(5) . ?
C5 C6 1.569(5) . ?
C5 C11 1.517(6) . ?
C6 O1 1.221(5) . ?
C7 C8 1.379(6) . ?
C7 N1 1.347(5) . ?
C8 C9 1.391(6) . ?
C9 C10 1.395(6) . ?
C10 C13 1.435(6) . ?
C10 N1 1.385(5) . ?
C11 O2 1.194(5) . ?
C11 O5 1.349(5) . ?
C12 O5 1.451(5) . ?
C13 C14 1.546(6) . ?
C13 O3 1.222(5) . ?
C14 Cl1 1.782(4) . ?
C14 Cl2 1.782(4) . ?
C14 Cl4 1.767(4) . ?
C16 N3 1.344(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 C1 C6 142.0(4) . . ?
C16 C1 C2 108.1(3) . . ?
C16 C1 C6 109.9(3) . . ?
C3 C2 C1 105.6(4) . . ?
C2 C3 N3 109.1(4) . . ?
C7 C4 C5 112.4(3) . . ?
C16 C4 C5 100.5(3) . . ?
C16 C4 C7 113.8(3) . . ?
C4 C5 C6 107.0(3) . . ?
C11 C5 C4 113.0(3) . . ?
C11 C5 C6 108.4(3) . . ?
C1 C6 C5 106.5(3) . . ?
O1 C6 C1 130.7(4) . . ?
O1 C6 C5 122.8(4) . . ?
C8 C7 C4 131.0(4) . . ?
N1 C7 C4 121.0(4) . . ?
N1 C7 C8 108.0(4) . . ?
C7 C8 C9 108.3(4) . . ?
C8 C9 C10 107.1(4) . . ?
C9 C10 C13 135.1(4) . . ?
N1 C10 C9 106.8(3) . . ?
N1 C10 C13 118.0(4) . . ?
O2 C11 C5 125.6(4) . . ?
O2 C11 O5 124.7(4) . . ?
O5 C11 C5 109.6(3) . . ?
C10 C13 C14 118.8(4) . . ?
O3 C13 C10 122.6(4) . . ?
O3 C13 C14 118.7(4) . . ?
C13 C14 Cl1 110.4(3) . . ?
C13 C14 Cl2 108.1(3) . . ?
C13 C14 Cl4 111.0(3) . . ?
Cl1 C14 Cl2 110.7(2) . . ?
Cl4 C14 Cl1 108.2(2) . . ?
Cl4 C14 Cl2 108.5(2) . . ?
C1 C16 C4 116.0(3) . . ?
N3 C16 C1 108.7(3) . . ?
N3 C16 C4 135.2(4) . . ?
C7 N1 C10 109.8(3) . . ?
C16 N3 C3 108.5(3) . . ?
C11 O5 C12 115.1(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
C1 C2 C3 N3 0.0(5) . . . . ?
C1 C16 N3 C3 0.9(5) . . . . ?
C2 C1 C6 C5 -176.5(5) . . . . ?
C2 C1 C6 O1 4.3(9) . . . . ?
C2 C1 C16 C4 178.7(3) . . . . ?
C2 C1 C16 N3 -1.0(4) . . . . ?
C2 C3 N3 C16 -0.6(5) . . . . ?
C4 C5 C6 C1 -2.8(4) . . . . ?
C4 C5 C6 O1 176.5(4) . . . . ?
C4 C5 C11 O2 16.1(6) . . . . ?
C4 C5 C11 O5 -166.8(3) . . . . ?
C4 C7 C8 C9 -178.7(4) . . . . ?
C4 C7 N1 C10 178.8(3) . . . . ?
C4 C16 N3 C3 -178.7(4) . . . . ?
C5 C4 C7 C8 50.6(6) . . . . ?
C5 C4 C7 N1 -127.5(4) . . . . ?
C5 C4 C16 C1 -1.5(4) . . . . ?
C5 C4 C16 N3 178.1(4) . . . . ?
C5 C11 O5 C12 -171.9(3) . . . . ?
C6 C1 C2 C3 179.0(5) . . . . ?
C6 C1 C16 C4 -0.2(5) . . . . ?
C6 C1 C16 N3 -179.9(3) . . . . ?
C6 C5 C11 O2 -102.4(5) . . . . ?
C6 C5 C11 O5 74.7(4) . . . . ?
C7 C4 C5 C6 -118.9(4) . . . . ?
C7 C4 C5 C11 121.8(4) . . . . ?
C7 C4 C16 C1 118.9(4) . . . . ?
C7 C4 C16 N3 -61.5(6) . . . . ?
C7 C8 C9 C10 0.3(5) . . . . ?
C8 C7 N1 C10 0.3(5) . . . . ?
C8 C9 C10 C13 178.1(4) . . . . ?
C8 C9 C10 N1 -0.1(5) . . . . ?
C9 C10 C13 C14 3.0(7) . . . . ?
C9 C10 C13 O3 -175.9(4) . . . . ?
C9 C10 N1 C7 -0.2(4) . . . . ?
C10 C13 C14 Cl1 56.4(4) . . . . ?
C10 C13 C14 Cl2 -64.7(4) . . . . ?
C10 C13 C14 Cl4 176.4(3) . . . . ?
C11 C5 C6 C1 119.5(4) . . . . ?
C11 C5 C6 O1 -61.3(5) . . . . ?
C13 C10 N1 C7 -178.7(3) . . . . ?
C16 C1 C2 C3 0.6(5) . . . . ?
C16 C1 C6 C5 1.9(4) . . . . ?
C16 C1 C6 O1 -177.3(4) . . . . ?
C16 C4 C5 C6 2.5(4) . . . . ?
C16 C4 C5 C11 -116.8(3) . . . . ?
C16 C4 C7 C8 -62.9(6) . . . . ?
C16 C4 C7 N1 119.0(4) . . . . ?
N1 C7 C8 C9 -0.4(5) . . . . ?
N1 C10 C13 C14 -179.0(3) . . . . ?
N1 C10 C13 O3 2.1(6) . . . . ?
O2 C11 O5 C12 5.3(6) . . . . ?
O3 C13 C14 Cl1 -124.7(3) . . . . ?
O3 C13 C14 Cl2 114.2(4) . . . . ?
O3 C13 C14 Cl4 -4.7(5) . . . . ?

_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_ncsu_t1
_database_code_depnum_ccdc_archive 'CCDC 2266094'
loop_
_audit_author_name
_audit_author_address
'Phattananawee Nalaoh'
;The University of Tennessee, Knoxville
United States of America
;
_audit_update_record             
;
2023-05-29 deposited with the CCDC.	2023-06-28 downloaded from the CCDC.
;
_audit_creation_date             2022-12-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H11 Cl3 N2 O4'
_chemical_formula_sum            'C15 H11 Cl3 N2 O4'
_chemical_formula_weight         389.61
_chemical_absolute_configuration rmad
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.6066(2)
_cell_length_b                   12.8897(5)
_cell_length_c                   9.5387(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.4220(10)
_cell_angle_gamma                90
_cell_volume                     805.48(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6643
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.67
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.889
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1332 before and 0.0457 after correction.
The Ratio of minimum to maximum transmission is 0.8873.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.022
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11749
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.716
_diffrn_reflns_theta_min         2.153
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                3211
_reflns_number_total             3398
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1436 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3398
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0254
_refine_ls_restrained_S_all      1.028
_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)+(0.0241P)²+0.1918P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0550
_refine_ls_wR_factor_ref         0.0566
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.18142(10) 0.57164(6) 1.05509(7) 0.02410(17) Uani 1 1 d . . . . .
Cl2 Cl 0.01895(11) 0.37659(6) 1.02344(7) 0.02448(17) Uani 1 1 d . . . . .
Cl3 Cl 0.25602(10) 0.56106(6) 1.12025(7) 0.02167(16) Uani 1 1 d . . . . .
O1 O 0.9319(3) 0.66255(16) 0.4364(2) 0.0208(4) Uani 1 1 d . . . . .
O2 O -0.0495(3) 0.60387(15) 0.7882(2) 0.0212(5) Uani 1 1 d . . . . .
O3 O 1.0079(3) 0.44019(16) 0.3890(2) 0.0184(4) Uani 1 1 d . . . . .
O4 O 0.6120(3) 0.66956(16) 0.3212(2) 0.0235(5) Uani 1 1 d . . . . .
N1 N 0.2583(4) 0.52281(17) 0.6526(2) 0.0137(5) Uani 1 1 d . . . . .
H1 H 0.168(5) 0.566(3) 0.593(3) 0.024(8) Uiso 1 1 d . . . . .
N2 N 0.3457(4) 0.32287(19) 0.3336(3) 0.0171(5) Uani 1 1 d . . . . .
H2 H 0.213(6) 0.329(3) 0.336(4) 0.028(9) Uiso 1 1 d . . . . .
C1 C 0.9840(5) 0.7530(2) 0.3585(3) 0.0248(7) Uani 1 1 d . . . . .
H1A H 0.961268 0.738137 0.256956 0.037 Uiso 1 1 calc GR . . . .
H1B H 1.127812 0.770655 0.386457 0.037 Uiso 1 1 calc GR . . . .
H1C H 0.898018 0.811568 0.379416 0.037 Uiso 1 1 calc GR . . . .
C2 C 0.7402(4) 0.6271(2) 0.4022(3) 0.0162(6) Uani 1 1 d . . . . .
C3 C 0.7142(4) 0.5248(2) 0.4750(3) 0.0146(6) Uani 1 1 d . . . . .
H3 H 0.777966 0.529392 0.575710 0.018 Uiso 1 1 calc R . . . .
C4 C 0.4872(4) 0.4910(2) 0.4698(3) 0.0133(5) Uani 1 1 d . . . . .
H4 H 0.396545 0.543850 0.416934 0.016 Uiso 1 1 calc R . . . .
C5 C 0.4247(4) 0.4754(2) 0.6147(3) 0.0145(5) Uani 1 1 d . . . . .
C6 C 0.2363(4) 0.4968(2) 0.7918(3) 0.0149(6) Uani 1 1 d . . . . .
C7 C 0.0696(4) 0.5422(2) 0.8522(3) 0.0158(6) Uani 1 1 d . . . . .
C8 C 0.0411(4) 0.5135(2) 1.0070(3) 0.0179(6) Uani 1 1 d . . . . .
C9 C 0.3990(4) 0.4316(2) 0.8394(3) 0.0199(6) Uani 1 1 d . . . . .
H9 H 0.425611 0.401514 0.930839 0.024 Uiso 1 1 calc R . . . .
C10 C 0.5150(4) 0.4186(2) 0.7296(3) 0.0202(6) Uani 1 1 d . . . . .
H10 H 0.635391 0.377893 0.732574 0.024 Uiso 1 1 calc R . . . .
C11 C 0.8246(4) 0.4388(2) 0.3974(3) 0.0146(5) Uani 1 1 d . . . . .
C12 C 0.6722(4) 0.3653(2) 0.3441(3) 0.0148(5) Uani 1 1 d . . . . .
C13 C 0.6417(4) 0.2720(2) 0.2625(3) 0.0201(6) Uani 1 1 d . . . . .
H13 H 0.741446 0.234384 0.220123 0.024 Uiso 1 1 calc R . . . .
C14 C 0.4396(5) 0.2484(2) 0.2583(3) 0.0212(6) Uani 1 1 d . . . . .
H14 H 0.373472 0.190274 0.211308 0.025 Uiso 1 1 calc R . . . .
C15 C 0.4867(4) 0.3933(2) 0.3838(3) 0.0137(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C8 1.763(3) . ?
Cl2 C8 1.780(3) . ?
Cl3 C8 1.778(3) . ?
O1 C1 1.448(3) . ?
O1 C2 1.346(3) . ?
O2 C7 1.224(3) . ?
O3 C11 1.224(3) . ?
O4 C2 1.203(4) . ?
N1 H1 0.95(3) . ?
N1 C5 1.348(3) . ?
N1 C6 1.395(3) . ?
N2 H2 0.88(4) . ?
N2 C14 1.392(4) . ?
N2 C15 1.344(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.509(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.556(4) . ?
C3 C11 1.565(4) . ?
C4 H4 1.0000 . ?
C4 C5 1.506(4) . ?
C4 C15 1.502(4) . ?
C5 C10 1.387(4) . ?
C6 C7 1.432(4) . ?
C6 C9 1.394(4) . ?
C7 C8 1.557(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.427(4) . ?
C12 C13 1.433(4) . ?
C12 C15 1.376(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.365(4) . ?
C14 H14 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 O1 C1 115.3(2) . . ?
C5 N1 H1 125.1(19) . . ?
C5 N1 C6 109.6(2) . . ?
C6 N1 H1 125.3(19) . . ?
C14 N2 H2 126(2) . . ?
C15 N2 H2 125(2) . . ?
C15 N2 C14 108.3(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 110.2(2) . . ?
O4 C2 O1 124.3(3) . . ?
O4 C2 C3 125.5(3) . . ?
C2 C3 H3 109.4 . . ?
C2 C3 C4 113.4(2) . . ?
C2 C3 C11 108.3(2) . . ?
C4 C3 H3 109.4 . . ?
C4 C3 C11 107.0(2) . . ?
C11 C3 H3 109.4 . . ?
C3 C4 H4 109.7 . . ?
C5 C4 C3 112.7(2) . . ?
C5 C4 H4 109.7 . . ?
C15 C4 C3 100.8(2) . . ?
C15 C4 H4 109.7 . . ?
C15 C4 C5 114.1(2) . . ?
N1 C5 C4 121.0(2) . . ?
N1 C5 C10 108.0(2) . . ?
C10 C5 C4 130.9(2) . . ?
N1 C6 C7 117.7(2) . . ?
C9 C6 N1 106.5(2) . . ?
C9 C6 C7 135.7(3) . . ?
O2 C7 C6 122.8(2) . . ?
O2 C7 C8 118.6(2) . . ?
C6 C7 C8 118.6(2) . . ?
Cl1 C8 Cl2 108.50(15) . . ?
Cl1 C8 Cl3 108.82(15) . . ?
Cl3 C8 Cl2 110.87(16) . . ?
C7 C8 Cl1 110.7(2) . . ?
C7 C8 Cl2 109.91(19) . . ?
C7 C8 Cl3 108.06(19) . . ?
C6 C9 H9 126.1 . . ?
C10 C9 C6 107.8(2) . . ?
C10 C9 H9 126.1 . . ?
C5 C10 H10 126.0 . . ?
C9 C10 C5 108.0(3) . . ?
C9 C10 H10 126.0 . . ?
O3 C11 C3 123.1(2) . . ?
O3 C11 C12 130.2(3) . . ?
C12 C11 C3 106.7(2) . . ?
C11 C12 C13 142.5(3) . . ?
C15 C12 C11 109.9(2) . . ?
C15 C12 C13 107.6(2) . . ?
C12 C13 H13 127.1 . . ?
C14 C13 C12 105.8(2) . . ?
C14 C13 H13 127.1 . . ?
N2 C14 H14 125.3 . . ?
C13 C14 N2 109.3(2) . . ?
C13 C14 H14 125.3 . . ?
N2 C15 C4 135.5(2) . . ?
N2 C15 C12 109.0(2) . . ?
C12 C15 C4 115.5(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 166.6(2) . . . . ?
O1 C2 C3 C11 -74.8(3) . . . . ?
O2 C7 C8 Cl1 4.9(3) . . . . ?
O2 C7 C8 Cl2 124.7(2) . . . . ?
O2 C7 C8 Cl3 -114.2(2) . . . . ?
O3 C11 C12 C13 -2.9(6) . . . . ?
O3 C11 C12 C15 177.6(3) . . . . ?
O4 C2 C3 C4 -15.9(4) . . . . ?
O4 C2 C3 C11 102.7(3) . . . . ?
N1 C5 C10 C9 0.4(3) . . . . ?
N1 C6 C7 O2 -1.8(4) . . . . ?
N1 C6 C7 C8 179.5(2) . . . . ?
N1 C6 C9 C10 -0.4(3) . . . . ?
C1 O1 C2 O4 -5.4(4) . . . . ?
C1 O1 C2 C3 172.0(2) . . . . ?
C2 C3 C4 C5 -121.8(2) . . . . ?
C2 C3 C4 C15 116.2(2) . . . . ?
C2 C3 C11 O3 60.9(3) . . . . ?
C2 C3 C11 C12 -119.1(2) . . . . ?
C3 C4 C5 N1 127.5(3) . . . . ?
C3 C4 C5 C10 -50.5(4) . . . . ?
C3 C4 C15 N2 -178.4(3) . . . . ?
C3 C4 C15 C12 1.9(3) . . . . ?
C3 C11 C12 C13 177.1(3) . . . . ?
C3 C11 C12 C15 -2.3(3) . . . . ?
C4 C3 C11 O3 -176.5(2) . . . . ?
C4 C3 C11 C12 3.4(3) . . . . ?
C4 C5 C10 C9 178.6(3) . . . . ?
C5 N1 C6 C7 178.5(2) . . . . ?
C5 N1 C6 C9 0.7(3) . . . . ?
C5 C4 C15 N2 60.6(4) . . . . ?
C5 C4 C15 C12 -119.1(3) . . . . ?
C6 N1 C5 C4 -179.1(2) . . . . ?
C6 N1 C5 C10 -0.7(3) . . . . ?
C6 C7 C8 Cl1 -176.3(2) . . . . ?
C6 C7 C8 Cl2 -56.5(3) . . . . ?
C6 C7 C8 Cl3 64.6(3) . . . . ?
C6 C9 C10 C5 0.0(3) . . . . ?
C7 C6 C9 C10 -177.7(3) . . . . ?
C9 C6 C7 O2 175.3(3) . . . . ?
C9 C6 C7 C8 -3.4(5) . . . . ?
C11 C3 C4 C5 118.9(2) . . . . ?
C11 C3 C4 C15 -3.1(2) . . . . ?
C11 C12 C13 C14 -179.9(4) . . . . ?
C11 C12 C15 N2 -179.6(2) . . . . ?
C11 C12 C15 C4 0.3(3) . . . . ?
C12 C13 C14 N2 -0.1(3) . . . . ?
C13 C12 C15 N2 0.8(3) . . . . ?
C13 C12 C15 C4 -179.4(2) . . . . ?
C14 N2 C15 C4 179.4(3) . . . . ?
C14 N2 C15 C12 -0.8(3) . . . . ?
C15 N2 C14 C13 0.6(3) . . . . ?
C15 C4 C5 N1 -118.4(3) . . . . ?
C15 C4 C5 C10 63.6(4) . . . . ?
C15 C12 C13 C14 -0.4(3) . . . . ?

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

data_rs061
_database_code_depnum_ccdc_archive 'CCDC 2266093'
loop_
_audit_author_name
_audit_author_address
'Phattananawee Nalaoh'
;The University of Tennessee, Knoxville
United States of America
;
_audit_update_record             
;
2023-05-29 deposited with the CCDC.	2023-06-28 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            Z-15
_chemical_formula_moiety         'C13 H12 N2 O3'
_chemical_formula_sum            'C13 H12 N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         244.25

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.2578(2)
_cell_length_b                   6.8693(2)
_cell_length_c                   14.7437(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.4410(10)
_cell_angle_gamma                90
_cell_volume                     1127.83(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9886
_cell_measurement_theta_min      3.9697
_cell_measurement_theta_max      79.5901
_cell_measurement_temperature    110.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.283
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.098
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512

_exptl_absorpt_coefficient_mu    0.863
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
(Bruker AXS Inc., 2016)
;
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.92

_exptl_special_details           
;
;

_diffrn_ambient_temperature      110.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'multilayer mirror'

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            27604
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_theta_min         3.97
_diffrn_reflns_theta_max         79.87
_diffrn_reflns_theta_full        79.87
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
N-H atoms were placed at calulated positions, and released from geometric
constaints late in the refinement, with the isotropic displacement parameters
set to 1.2 the parent atom.
;

_reflns_number_total             2446
_reflns_number_gt                2399
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0825
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_number_reflns         2446
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0373P)²+0.6384P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.256
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       
'Bruker Instrument Service, BIS, v.6.2.10 (Bruker AXS Inc., 2018)'
_computing_cell_refinement       'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_structure_solution    'XT, VERSION 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, 2019)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.47210(6) 0.69106(11) 0.63460(5) 0.01458(17) Uani d . . . 1 . .
O O2 0.22002(7) 0.79092(13) 0.66650(5) 0.0222(2) Uani d . . . 1 . .
O O3 0.16835(7) 0.95127(11) 0.53374(5) 0.01570(17) Uani d . . . 1 . .
N N1 0.41762(8) 0.76704(13) 0.32107(6) 0.01394(19) Uani d . . . 1 . .
H H1 0.3781(13) 0.765(2) 0.2656(10) 0.017 Uiso d U . . 1 . .
N N2 0.26797(8) 0.33889(13) 0.35298(6) 0.01428(19) Uani d . . . 1 . .
H H2 0.3488(14) 0.335(2) 0.3603(10) 0.017 Uiso d U . . 1 . .
C C1 0.53899(10) 0.81100(16) 0.34405(7) 0.0151(2) Uani d . . . 1 . .
H H1A 0.591361 0.845524 0.301665 0.018 Uiso calc U . R 1 . .
C C2 0.57134(9) 0.79698(15) 0.43679(7) 0.0139(2) Uani d . . . 1 . .
H H2A 0.648598 0.819017 0.47077 0.017 Uiso calc U . R 1 . .
C C3 0.46440(9) 0.74214(15) 0.47190(7) 0.0120(2) Uani d . . . 1 . .
C C4 0.37320(9) 0.72613(15) 0.39903(7) 0.0119(2) Uani d . . . 1 . .
C C5 0.25211(9) 0.67209(15) 0.42266(7) 0.0123(2) Uani d . . . 1 . .
H H5 0.194933 0.781942 0.405484 0.015 Uiso calc U . R 1 . .
C C6 0.19934(9) 0.48808(15) 0.37888(7) 0.0128(2) Uani d . . . 1 . .
C C7 0.08068(9) 0.43418(17) 0.35766(7) 0.0160(2) Uani d . . . 1 . .
H H7 0.013104 0.508968 0.368316 0.019 Uiso calc U . R 1 . .
C C8 0.07765(10) 0.24650(17) 0.31696(7) 0.0181(2) Uani d . . . 1 . .
H H8 0.007856 0.172846 0.295159 0.022 Uiso calc U . R 1 . .
C C9 0.19419(10) 0.19161(16) 0.31502(7) 0.0172(2) Uani d . . . 1 . .
H H9 0.219659 0.07237 0.291507 0.021 Uiso calc U . R 1 . .
C C10 0.41978(9) 0.69904(14) 0.55571(7) 0.0115(2) Uani d . . . 1 . .
C C11 0.28205(9) 0.66088(15) 0.53003(7) 0.0123(2) Uani d . . . 1 . .
H H11 0.2643 0.526117 0.549903 0.015 Uiso calc U . R 1 . .
C C12 0.21903(9) 0.80463(16) 0.58472(7) 0.0138(2) Uani d . . . 1 . .
C C13 0.11574(10) 1.10598(17) 0.58191(8) 0.0200(2) Uani d . . . 1 . .
H H13A 0.099284 1.218708 0.541274 0.03 Uiso calc U . R 1 . .
H H13B 0.171838 1.143604 0.636321 0.03 Uiso calc U . R 1 . .
H H13C 0.040588 1.060045 0.600662 0.03 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C10 . 1.2254(12) ?
O2 C12 . 1.2077(13) ?
O3 C12 . 1.3339(13) ?
O3 C13 . 1.4519(13) ?
N1 C4 . 1.3487(13) ?
N1 C1 . 1.3917(14) ?
N1 H1 . 0.872(15) ?
N2 C6 . 1.3710(14) ?
N2 C9 . 1.3748(14) ?
N2 H2 . 0.901(15) ?
C1 C2 . 1.3658(15) ?
C1 H1A . 0.95 ?
C2 C3 . 1.4290(14) ?
C2 H2A . 0.95 ?
C3 C4 . 1.3771(14) ?
C3 C10 . 1.4315(14) ?
C4 C5 . 1.5024(14) ?
C5 C6 . 1.5016(14) ?
C5 C11 . 1.5712(13) ?
C5 H5 . 1.0 ?
C6 C7 . 1.3773(14) ?
C7 C8 . 1.4203(16) ?
C7 H7 . 0.95 ?
C8 C9 . 1.3694(16) ?
C8 H8 . 0.95 ?
C9 H9 . 0.95 ?
C10 C11 . 1.5633(13) ?
C11 C12 . 1.5155(14) ?
C11 H11 . 1.0 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 O3 C13 . . 116.65(8) ?
C4 N1 C1 . . 108.14(9) ?
C4 N1 H1 . . 126.5(9) ?
C1 N1 H1 . . 125.4(9) ?
C6 N2 C9 . . 109.39(9) ?
C6 N2 H2 . . 126.0(9) ?
C9 N2 H2 . . 124.6(9) ?
C2 C1 N1 . . 109.66(9) ?
C2 C1 H1A . . 125.2 ?
N1 C1 H1A . . 125.2 ?
C1 C2 C3 . . 105.44(9) ?
C1 C2 H2A . . 127.3 ?
C3 C2 H2A . . 127.3 ?
C4 C3 C2 . . 108.04(9) ?
C4 C3 C10 . . 109.93(9) ?
C2 C3 C10 . . 142.02(10) ?
N1 C4 C3 . . 108.72(9) ?
N1 C4 C5 . . 135.37(9) ?
C3 C4 C5 . . 115.90(9) ?
C6 C5 C4 . . 115.05(8) ?
C6 C5 C11 . . 113.87(8) ?
C4 C5 C11 . . 100.25(8) ?
C6 C5 H5 . . 109.1 ?
C4 C5 H5 . . 109.1 ?
C11 C5 H5 . . 109.1 ?
N2 C6 C7 . . 107.65(9) ?
N2 C6 C5 . . 123.06(9) ?
C7 C6 C5 . . 129.29(10) ?
C6 C7 C8 . . 107.60(10) ?
C6 C7 H7 . . 126.2 ?
C8 C7 H7 . . 126.2 ?
C9 C8 C7 . . 107.16(10) ?
C9 C8 H8 . . 126.4 ?
C7 C8 H8 . . 126.4 ?
C8 C9 N2 . . 108.20(10) ?
C8 C9 H9 . . 125.9 ?
N2 C9 H9 . . 125.9 ?
O1 C10 C3 . . 130.38(10) ?
O1 C10 C11 . . 122.94(9) ?
C3 C10 C11 . . 106.67(8) ?
C12 C11 C10 . . 106.68(8) ?
C12 C11 C5 . . 117.14(8) ?
C10 C11 C5 . . 107.11(8) ?
C12 C11 H11 . . 108.5 ?
C10 C11 H11 . . 108.5 ?
C5 C11 H11 . . 108.5 ?
O2 C12 O3 . . 124.19(10) ?
O2 C12 C11 . . 122.95(10) ?
O3 C12 C11 . . 112.78(8) ?
O3 C13 H13A . . 109.5 ?
O3 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
O3 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 N1 C1 C2 . . . . 0.25(12) ?
N1 C1 C2 C3 . . . . -0.10(12) ?
C1 C2 C3 C4 . . . . -0.09(12) ?
C1 C2 C3 C10 . . . . -179.88(13) ?
C1 N1 C4 C3 . . . . -0.31(12) ?
C1 N1 C4 C5 . . . . 178.85(11) ?
C2 C3 C4 N1 . . . . 0.25(12) ?
C10 C3 C4 N1 . . . . -179.89(9) ?
C2 C3 C4 C5 . . . . -179.09(9) ?
C10 C3 C4 C5 . . . . 0.77(13) ?
N1 C4 C5 C6 . . . . 59.85(16) ?
C3 C4 C5 C6 . . . . -121.04(10) ?
N1 C4 C5 C11 . . . . -177.57(11) ?
C3 C4 C5 C11 . . . . 1.55(11) ?
C9 N2 C6 C7 . . . . 0.41(11) ?
C9 N2 C6 C5 . . . . -179.88(9) ?
C4 C5 C6 N2 . . . . 26.67(14) ?
C11 C5 C6 N2 . . . . -88.27(11) ?
C4 C5 C6 C7 . . . . -153.69(10) ?
C11 C5 C6 C7 . . . . 91.36(13) ?
N2 C6 C7 C8 . . . . -0.42(12) ?
C5 C6 C7 C8 . . . . 179.90(10) ?
C6 C7 C8 C9 . . . . 0.27(12) ?
C7 C8 C9 N2 . . . . -0.02(12) ?
C6 N2 C9 C8 . . . . -0.24(12) ?
C4 C3 C10 O1 . . . . 177.47(11) ?
C2 C3 C10 O1 . . . . -2.7(2) ?
C4 C3 C10 C11 . . . . -2.77(11) ?
C2 C3 C10 C11 . . . . 177.02(13) ?
O1 C10 C11 C12 . . . . 57.27(12) ?
C3 C10 C11 C12 . . . . -122.51(9) ?
O1 C10 C11 C5 . . . . -176.53(9) ?
C3 C10 C11 C5 . . . . 3.68(11) ?
C6 C5 C11 C12 . . . . -119.93(10) ?
C4 C5 C11 C12 . . . . 116.65(9) ?
C6 C5 C11 C10 . . . . 120.37(9) ?
C4 C5 C11 C10 . . . . -3.04(10) ?
C13 O3 C12 O2 . . . . 2.46(15) ?
C13 O3 C12 C11 . . . . -174.31(8) ?
C10 C11 C12 O2 . . . . -72.01(13) ?
C5 C11 C12 O2 . . . . 168.07(10) ?
C10 C11 C12 O3 . . . . 104.81(9) ?
C5 C11 C12 O3 . . . . -15.11(12) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O1 4_575 0.872(15) 2.354(14) 2.9177(11) 122.6(11) ?
N1 H1 O2 4_575 0.872(15) 2.165(15) 2.9686(12) 153.0(13) ?
N2 H2 O1 3_666 0.901(15) 2.014(15) 2.9123(12) 174.1(13) ?

