# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_rn_bp_sc86_a
_database_code_depnum_ccdc_archive 'CCDC 2326700'
loop_
_audit_author_name
_audit_author_address
'Ramalingam Natarajan'
;CSIR Indian Institute of Chemical Biology
India
;
_audit_update_record             
;
2024-01-19 deposited with the CCDC.	2025-09-23 downloaded from the CCDC.
;
_audit_creation_date             2023-02-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        RN_BP_SC186
_chemical_formula_moiety         'C17 H12 Cl N O2'
_chemical_formula_sum            'C17 H12 Cl N O2'
_chemical_formula_weight         297.73
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   5.5582(4)
_cell_length_b                   16.5166(12)
_cell_length_c                   14.6656(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.907(2)
_cell_angle_gamma                90
_cell_volume                     1346.17(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9229
_cell_measurement_temperature    117.0
_cell_measurement_theta_max      68.54
_cell_measurement_theta_min      4.03
_shelx_estimated_absorpt_T_max   0.905
_shelx_estimated_absorpt_T_min   0.862
_exptl_absorpt_coefficient_mu    2.543
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1258 before and 0.0829 after correction.
The Ratio of minimum to maximum transmission is 0.8445.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            46415
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.500
_diffrn_reflns_theta_min         4.031
_diffrn_ambient_temperature      117.0
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'Bruker Photon III'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX3_IMuS Diamond_Photon III'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_type              'Incoatec I\ms Diamond'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2386
_reflns_number_total             2432
_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       'Bruker SAINT V8.38A (Bruker AXS)'
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'Bruker SAINT V8.38A (Bruker AXS)'
_computing_molecular_graphics    'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_publication_material  'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick 2018)'
_computing_structure_solution    'SHELXT 2018/2(Sheldrick 2014)'
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2432
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.102
_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)+(0.0505P)²+0.7089P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.0976
_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
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C16(H16), C17(H17), C14(H14), C8(H8), C6(H6), C7(H7), C5(H5)
;
_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
Cl1 Cl -0.01469(7) 0.35553(2) 0.44368(3) 0.02457(16) Uani 1 1 d . . . . .
O1 O 0.60640(19) 0.56916(7) 0.22949(8) 0.0217(3) Uani 1 1 d . . . . .
O2 O 0.6666(2) 0.67969(7) 0.15036(8) 0.0269(3) Uani 1 1 d . . . . .
N1 N 0.5479(2) 0.75803(8) 0.45940(9) 0.0223(3) Uani 1 1 d . . . . .
H1 H 0.669810 0.765114 0.497561 0.027 Uiso 1 1 calc R U . . .
C13 C 0.2412(3) 0.55117(9) 0.31641(11) 0.0186(3) Uani 1 1 d . . . . .
C1 C 0.2918(3) 0.69745(10) 0.36100(11) 0.0189(3) Uani 1 1 d . . . . .
C12 C 0.4505(3) 0.51987(10) 0.27967(11) 0.0193(3) Uani 1 1 d . . . . .
C3 C 0.3824(3) 0.81616(10) 0.43479(11) 0.0203(3) Uani 1 1 d . . . . .
C2 C 0.2159(3) 0.77990(10) 0.37320(11) 0.0192(3) Uani 1 1 d . . . . .
C4 C 0.4925(3) 0.68701(10) 0.41489(11) 0.0205(3) Uani 1 1 d . . . . .
H4 H 0.580644 0.637944 0.420699 0.025 Uiso 1 1 calc R U . . .
C16 C 0.3783(3) 0.38918(10) 0.34352(11) 0.0215(4) Uani 1 1 d . . . . .
H16 H 0.423318 0.334333 0.353316 0.026 Uiso 1 1 calc R U . . .
C17 C 0.5215(3) 0.44015(10) 0.29205(11) 0.0216(4) Uani 1 1 d . . . . .
H17 H 0.665553 0.420674 0.265800 0.026 Uiso 1 1 calc R U . . .
C14 C 0.0989(3) 0.49966(10) 0.36771(11) 0.0200(3) Uani 1 1 d . . . . .
H14 H -0.045183 0.519108 0.393934 0.024 Uiso 1 1 calc R U . . .
C9 C 0.1761(3) 0.63794(9) 0.29562(11) 0.0195(4) Uani 1 1 d . . . . .
H9 H -0.002660 0.644057 0.298171 0.023 Uiso 1 1 calc R U . . .
C11 C 0.5218(3) 0.63838(9) 0.18902(11) 0.0207(4) Uani 1 1 d . . . . .
C15 C 0.1685(3) 0.41974(10) 0.38039(11) 0.0199(3) Uani 1 1 d . . . . .
C8 C 0.3643(3) 0.89748(10) 0.46031(11) 0.0235(4) Uani 1 1 d . . . . .
H8 H 0.479751 0.921775 0.500178 0.028 Uiso 1 1 calc R U . . .
C10 C 0.2580(3) 0.65498(10) 0.19720(11) 0.0221(4) Uani 1 1 d . . . . .
H10A H 0.166548 0.620198 0.153992 0.027 Uiso 1 1 calc R U . . .
H10B H 0.224679 0.712203 0.181367 0.027 Uiso 1 1 calc R U . . .
C6 C 0.0002(3) 0.90546(10) 0.36664(12) 0.0254(4) Uani 1 1 d . . . . .
H6 H -0.132366 0.936808 0.345156 0.030 Uiso 1 1 calc R U . . .
C7 C 0.1722(3) 0.94104(10) 0.42528(12) 0.0247(4) Uani 1 1 d . . . . .
H7 H 0.155850 0.996498 0.441226 0.030 Uiso 1 1 calc R U . . .
C5 C 0.0205(3) 0.82563(10) 0.33968(11) 0.0221(4) Uani 1 1 d . . . . .
H5 H -0.095250 0.802144 0.299331 0.026 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C15 1.7471(16) . ?
O1 C12 1.4054(19) . ?
O1 C11 1.3680(19) . ?
O2 C11 1.204(2) . ?
N1 H1 0.8800 . ?
N1 C3 1.374(2) . ?
N1 C4 1.375(2) . ?
C13 C12 1.389(2) . ?
C13 C14 1.391(2) . ?
C13 C9 1.508(2) . ?
C1 C2 1.438(2) . ?
C1 C4 1.368(2) . ?
C1 C9 1.510(2) . ?
C12 C17 1.386(2) . ?
C3 C2 1.416(2) . ?
C3 C8 1.398(2) . ?
C2 C5 1.405(2) . ?
C4 H4 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.389(2) . ?
C16 C15 1.389(2) . ?
C17 H17 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.387(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.546(2) . ?
C11 C10 1.498(2) . ?
C8 H8 0.9500 . ?
C8 C7 1.380(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C6 H6 0.9500 . ?
C6 C7 1.405(3) . ?
C6 C5 1.382(2) . ?
C7 H7 0.9500 . ?
C5 H5 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
C11 O1 C12 120.05(12) . . ?
C3 N1 H1 125.4 . . ?
C3 N1 C4 109.14(13) . . ?
C4 N1 H1 125.4 . . ?
C12 C13 C14 117.97(14) . . ?
C12 C13 C9 118.35(14) . . ?
C14 C13 C9 123.63(14) . . ?
C2 C1 C9 124.94(14) . . ?
C4 C1 C2 106.61(14) . . ?
C4 C1 C9 128.32(15) . . ?
C13 C12 O1 120.96(14) . . ?
C17 C12 O1 116.27(14) . . ?
C17 C12 C13 122.75(15) . . ?
N1 C3 C2 107.46(14) . . ?
N1 C3 C8 130.67(15) . . ?
C8 C3 C2 121.88(15) . . ?
C3 C2 C1 106.85(14) . . ?
C5 C2 C1 133.82(15) . . ?
C5 C2 C3 119.31(15) . . ?
N1 C4 H4 125.0 . . ?
C1 C4 N1 109.94(14) . . ?
C1 C4 H4 125.0 . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C15 C16 C17 118.89(15) . . ?
C12 C17 C16 118.86(15) . . ?
C12 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.67(15) . . ?
C15 C14 H14 120.2 . . ?
C13 C9 C1 113.07(13) . . ?
C13 C9 H9 108.9 . . ?
C13 C9 C10 106.76(13) . . ?
C1 C9 H9 108.9 . . ?
C1 C9 C10 110.21(13) . . ?
C10 C9 H9 108.9 . . ?
O1 C11 C10 116.64(14) . . ?
O2 C11 O1 116.75(15) . . ?
O2 C11 C10 126.61(15) . . ?
C16 C15 Cl1 119.11(13) . . ?
C14 C15 Cl1 119.04(12) . . ?
C14 C15 C16 121.85(15) . . ?
C3 C8 H8 121.3 . . ?
C7 C8 C3 117.36(16) . . ?
C7 C8 H8 121.3 . . ?
C9 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
C11 C10 C9 110.15(13) . . ?
C11 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.10(16) . . ?
C8 C7 C6 121.67(16) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C2 C5 H5 120.7 . . ?
C6 C5 C2 118.63(15) . . ?
C6 C5 H5 120.7 . . ?

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 C12 C17 C16 178.03(14) . . . . ?
O1 C11 C10 C9 43.64(18) . . . . ?
O2 C11 C10 C9 -136.47(16) . . . . ?
N1 C3 C2 C1 -0.86(17) . . . . ?
N1 C3 C2 C5 177.63(14) . . . . ?
N1 C3 C8 C7 -178.63(16) . . . . ?
C13 C12 C17 C16 -0.2(2) . . . . ?
C13 C14 C15 Cl1 -179.11(11) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C13 C9 C10 C11 -57.03(17) . . . . ?
C1 C2 C5 C6 179.36(17) . . . . ?
C1 C9 C10 C11 66.13(17) . . . . ?
C12 O1 C11 O2 176.90(13) . . . . ?
C12 O1 C11 C10 -3.2(2) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
C12 C13 C9 C1 -86.56(18) . . . . ?
C12 C13 C9 C10 34.79(19) . . . . ?
C3 N1 C4 C1 -0.03(19) . . . . ?
C3 C2 C5 C6 1.4(2) . . . . ?
C3 C8 C7 C6 0.3(2) . . . . ?
C2 C1 C4 N1 -0.51(18) . . . . ?
C2 C1 C9 C13 -162.83(15) . . . . ?
C2 C1 C9 C10 77.78(19) . . . . ?
C2 C3 C8 C7 2.0(2) . . . . ?
C4 N1 C3 C2 0.57(18) . . . . ?
C4 N1 C3 C8 -178.87(16) . . . . ?
C4 C1 C2 C3 0.84(17) . . . . ?
C4 C1 C2 C5 -177.33(17) . . . . ?
C4 C1 C9 C13 21.7(2) . . . . ?
C4 C1 C9 C10 -97.69(19) . . . . ?
C17 C16 C15 Cl1 179.01(12) . . . . ?
C17 C16 C15 C14 -0.4(2) . . . . ?
C14 C13 C12 O1 -178.05(13) . . . . ?
C14 C13 C12 C17 0.1(2) . . . . ?
C14 C13 C9 C1 95.84(18) . . . . ?
C14 C13 C9 C10 -142.80(15) . . . . ?
C9 C13 C12 O1 4.2(2) . . . . ?
C9 C13 C12 C17 -177.64(15) . . . . ?
C9 C13 C14 C15 177.46(14) . . . . ?
C9 C1 C2 C3 -175.46(14) . . . . ?
C9 C1 C2 C5 6.4(3) . . . . ?
C9 C1 C4 N1 175.62(15) . . . . ?
C11 O1 C12 C13 -22.8(2) . . . . ?
C11 O1 C12 C17 158.97(14) . . . . ?
C15 C16 C17 C12 0.3(2) . . . . ?
C8 C3 C2 C1 178.63(15) . . . . ?
C8 C3 C2 C5 -2.9(2) . . . . ?
C7 C6 C5 C2 0.9(2) . . . . ?
C5 C6 C7 C8 -1.8(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_rn_bp_sc235_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2326704'
loop_
_audit_author_name
_audit_author_address
'Ramalingam Natarajan'
;CSIR Indian Institute of Chemical Biology
India
;
_audit_update_record             
;
2024-01-19 deposited with the CCDC.	2025-09-23 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V131 by Daniel Kratzert, Freiburg 2023, 
https://dkratzert.de/finalcif.html
;
_audit_creation_date             2023-12-08
_diffrn_source_power             0.06
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
O1A_3: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within
2A
Uanis(O1B_4) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 O1A_3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(O1B)=1-FVAR(1)
 Sof(O1A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C7(H7), C9(H9), C11(H11), C15(H15), C17(H17),
 C18(H18), N1(H1), C3(H3), C4(H4), C7(H7), C9(H9), C11(H11), C15(H15), C17(H17),
  C18(H18)
5.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        RN_BP_SC235
_chemical_name_common            ?
_chemical_formula_sum            'C18 H12 Cl N O4'
_chemical_formula_moiety         'C18 H12 Cl N O3, O'
_chemical_formula_weight         341.74
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_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'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   14.6606(14)
_cell_length_b                   7.2869(7)
_cell_length_c                   16.3207(16)
_cell_angle_alpha                90
_cell_angle_beta                 111.475(5)
_cell_angle_gamma                90
_cell_volume                     1622.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120.0
_cell_measurement_reflns_used    9865
_cell_measurement_theta_min      2.9095
_cell_measurement_theta_max      67.008
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    2.282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5503
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction: 
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.804
_shelx_estimated_absorpt_T_max   0.978
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      120.0
_diffrn_ambient_environment      ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms Diamond'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.2
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_type            'Bruker Photon III'
_diffrn_detector_area_resol_mean 7.407
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support ?
_diffrn_reflns_number            52627
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_theta_min         3.473
_diffrn_reflns_theta_max         68.046
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_point_group_measured_fraction_full 0.912
_reflns_number_total             5379
_reflns_number_gt                4903
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_max     0.831
_reflns_Friedel_fraction_full    0.835
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_cell_refinement       'Bruker SAINT V8.38A (Bruker AXS)'
_computing_data_reduction        'Bruker SAINT V8.38A (Bruker AXS)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0661P)²+2.4309P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5379
_refine_ls_number_parameters     447
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0625
_refine_ls_wR_factor_ref         0.1607
_refine_ls_wR_factor_gt          0.1571
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   0.141(8)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1793 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

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'
Cl Cl 0.3639 0.7018 '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'

_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_
_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_1 Cl -0.34965(11) 0.1667(3) 0.49283(11) 0.0443(4) Uani 1 1 d . . . . .
O1_1 O 0.3230(3) 0.1881(7) 0.4906(3) 0.0438(12) Uani 1 1 d . . . . .
O2_1 O 0.0203(3) 0.4422(6) 0.7479(3) 0.0406(11) Uani 1 1 d . . . . .
O3_1 O 0.1676(3) 0.5599(7) 0.7857(3) 0.0464(13) Uani 1 1 d . . . . .
N1_1 N -0.0525(4) 0.4468(8) 0.3329(4) 0.0386(13) Uani 1 1 d . . . . .
H1_1 H -0.090530 0.473979 0.278541 0.046 Uiso 1 1 calc R U . . .
C1_1 C 0.3890(5) 0.1661(13) 0.4457(5) 0.0500(18) Uani 1 1 d . . . . .
H1A_1 H 0.453827 0.132355 0.488053 0.075 Uiso 1 1 calc R U . . .
H1B_1 H 0.393739 0.281656 0.416831 0.075 Uiso 1 1 calc R U . . .
H1C_1 H 0.364936 0.069182 0.401393 0.075 Uiso 1 1 calc R U . . .
C2_1 C 0.2302(5) 0.2551(9) 0.4430(5) 0.0383(16) Uani 1 1 d . . . . .
C3_1 C 0.1950(5) 0.2797(10) 0.3520(5) 0.0424(17) Uani 1 1 d . . . . .
H3_1 H 0.235833 0.252735 0.319842 0.051 Uiso 1 1 calc R U . . .
C4_1 C 0.0998(5) 0.3442(10) 0.3082(5) 0.0406(16) Uani 1 1 d . . . . .
H4_1 H 0.074361 0.361086 0.246215 0.049 Uiso 1 1 calc R U . . .
C5_1 C 0.0435(4) 0.3828(9) 0.3589(4) 0.0365(15) Uani 1 1 d . . . . .
C6_1 C 0.0793(5) 0.3591(9) 0.4510(4) 0.0355(15) Uani 1 1 d . . . . .
C7_1 C 0.1737(5) 0.2954(9) 0.4923(5) 0.0364(15) Uani 1 1 d . . . . .
H7_1 H 0.199776 0.279241 0.554327 0.044 Uiso 1 1 calc R U . . .
C8_1 C 0.0010(5) 0.4102(10) 0.4798(4) 0.0348(15) Uani 1 1 d . . . . .
C9_1 C -0.0780(5) 0.4606(9) 0.4046(4) 0.0379(15) Uani 1 1 d . . . . .
H9_1 H -0.140334 0.498924 0.403673 0.045 Uiso 1 1 calc R U . . .
C10_1 C 0.0066(5) 0.4184(9) 0.5716(5) 0.0364(15) Uani 1 1 d . . . . .
C11_1 C 0.0896(5) 0.4770(10) 0.6363(4) 0.0378(15) Uani 1 1 d . . . . .
H11_1 H 0.144781 0.507093 0.621678 0.045 Uiso 1 1 calc R U . . .
C12_1 C 0.0972(5) 0.4953(10) 0.7259(5) 0.0412(15) Uani 1 1 d . . . . .
C13_1 C -0.0654(4) 0.3780(9) 0.6844(4) 0.0351(15) Uani 1 1 d . . . . .
C14_1 C -0.0751(5) 0.3637(9) 0.5971(4) 0.0338(14) Uani 1 1 d . . . . .
C15_1 C -0.1651(5) 0.2946(9) 0.5378(5) 0.0371(15) Uani 1 1 d . . . . .
H15_1 H -0.174681 0.281902 0.477294 0.045 Uiso 1 1 calc R U . . .
C16_1 C -0.2404(4) 0.2444(9) 0.5669(5) 0.0353(15) Uani 1 1 d . . . . .
C17_1 C -0.2268(5) 0.2611(10) 0.6551(5) 0.0409(16) Uani 1 1 d . . . . .
H17_1 H -0.277779 0.226859 0.674929 0.049 Uiso 1 1 calc R U . . .
C18_1 C -0.1375(5) 0.3287(10) 0.7153(5) 0.0403(16) Uani 1 1 d . . . . .
H18_1 H -0.127222 0.339971 0.776053 0.048 Uiso 1 1 calc R U . . .
Cl1_2 Cl 0.69284(13) 0.4911(2) -0.19078(13) 0.0490(5) Uani 1 1 d . . . . .
O1_2 O 0.3386(4) 0.4751(8) 0.2329(3) 0.0506(13) Uani 1 1 d . . . . .
O2_2 O 0.3020(3) 0.2150(7) -0.2334(3) 0.0439(12) Uani 1 1 d . . . . .
O3_2 O 0.1905(4) 0.1199(7) -0.1831(4) 0.0541(14) Uani 1 1 d . . . . .
N1_2 N 0.6469(4) 0.2276(7) 0.1475(4) 0.0373(13) Uani 1 1 d . . . . .
H1_2 H 0.708154 0.200908 0.179521 0.045 Uiso 1 1 calc R U . . .
C1_2 C 0.2464(5) 0.4951(12) 0.1631(5) 0.0523(19) Uani 1 1 d . . . . .
H1A_2 H 0.196220 0.525324 0.187434 0.078 Uiso 1 1 calc R U . . .
H1B_2 H 0.228952 0.379924 0.129994 0.078 Uiso 1 1 calc R U . . .
H1C_2 H 0.250294 0.593824 0.123754 0.078 Uiso 1 1 calc R U . . .
C2_2 C 0.4140(5) 0.4151(9) 0.2087(5) 0.0393(16) Uani 1 1 d . . . . .
C3_2 C 0.5042(5) 0.3878(10) 0.2808(5) 0.0458(18) Uani 1 1 d . . . . .
H3_2 H 0.508145 0.412735 0.339161 0.055 Uiso 1 1 calc R U . . .
C4_2 C 0.5856(5) 0.3254(10) 0.2662(5) 0.0426(17) Uani 1 1 d . . . . .
H4_2 H 0.646173 0.307032 0.313591 0.051 Uiso 1 1 calc R U . . .
C5_2 C 0.5764(5) 0.2906(9) 0.1808(5) 0.0394(16) Uani 1 1 d . . . . .
C6_2 C 0.4891(5) 0.3161(9) 0.1081(4) 0.0349(15) Uani 1 1 d . . . . .
C7_2 C 0.4063(5) 0.3817(9) 0.1220(5) 0.0387(16) Uani 1 1 d . . . . .
H7_2 H 0.346553 0.402918 0.074022 0.046 Uiso 1 1 calc R U . . .
C8_2 C 0.5086(5) 0.2669(9) 0.0301(4) 0.0325(14) Uani 1 1 d . . . . .
C9_2 C 0.6063(5) 0.2147(9) 0.0596(5) 0.0385(16) Uani 1 1 d . . . . .
H9_2 H 0.639688 0.175210 0.022658 0.046 Uiso 1 1 calc R U . . .
C10_2 C 0.4386(5) 0.2586(9) -0.0595(4) 0.0323(14) Uani 1 1 d . . . . .
C11_2 C 0.3433(5) 0.2022(9) -0.0776(5) 0.0417(16) Uani 1 1 d . . . . .
H11_2 H 0.323199 0.178085 -0.029502 0.050 Uiso 1 1 calc R U . . .
C12_2 C 0.2742(5) 0.1783(10) -0.1639(5) 0.0403(15) Uani 1 1 d . . . . .
C13_2 C 0.3954(5) 0.2796(9) -0.2199(5) 0.0405(16) Uani 1 1 d . . . . .
C14_2 C 0.4661(5) 0.3038(9) -0.1346(4) 0.0344(14) Uani 1 1 d . . . . .
C15_2 C 0.5566(5) 0.3729(9) -0.1279(5) 0.0392(16) Uani 1 1 d . . . . .
H15_2 H 0.604993 0.395516 -0.071299 0.047 Uiso 1 1 calc R U . . .
C16_2 C 0.5777(5) 0.4099(10) -0.2027(5) 0.0434(17) Uani 1 1 d . . . . .
C17_2 C 0.5082(6) 0.3821(11) -0.2862(5) 0.0499(19) Uani 1 1 d . . . . .
H17_2 H 0.523241 0.408276 -0.336894 0.060 Uiso 1 1 calc R U . . .
C18_2 C 0.4161(6) 0.3154(11) -0.2949(5) 0.0470(18) Uani 1 1 d . . . . .
H18_2 H 0.367849 0.294570 -0.351681 0.056 Uiso 1 1 calc R U . . .
O1B_4 O 0.1610(7) 0.5731(19) 0.9548(6) 0.151(5) Uani 1 1 d . U . . .
O1A_3 O 0.9004(11) 0.673(3) 0.0443(9) 0.118(6) Uani 0.599(16) 1 d . . P A 1
O1B_3 O 0.9207(13) 0.340(2) 0.9641(12) 0.083(7) Uani 0.401(16) 1 d . . P A 2


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_1 C16_1 1.711(7) . ?
O1_1 C1_1 1.419(8) . ?
O1_1 C2_1 1.385(8) . ?
O2_1 C12_1 1.358(8) . ?
O2_1 C13_1 1.384(8) . ?
O3_1 C12_1 1.225(8) . ?
N1_1 H1_1 0.8800 . ?
N1_1 C5_1 1.393(8) . ?
N1_1 C9_1 1.357(8) . ?
C1_1 H1A_1 0.9800 . ?
C1_1 H1B_1 0.9800 . ?
C1_1 H1C_1 0.9800 . ?
C2_1 C3_1 1.394(10) . ?
C2_1 C7_1 1.380(9) . ?
C3_1 H3_1 0.9500 . ?
C3_1 C4_1 1.396(10) . ?
C4_1 H4_1 0.9500 . ?
C4_1 C5_1 1.394(9) . ?
C5_1 C6_1 1.410(9) . ?
C6_1 C7_1 1.379(9) . ?
C6_1 C8_1 1.439(9) . ?
C7_1 H7_1 0.9500 . ?
C8_1 C9_1 1.394(9) . ?
C8_1 C10_1 1.472(10) . ?
C9_1 H9_1 0.9500 . ?
C10_1 C11_1 1.356(9) . ?
C10_1 C14_1 1.459(9) . ?
C11_1 H11_1 0.9500 . ?
C11_1 C12_1 1.431(10) . ?
C13_1 C14_1 1.384(9) . ?
C13_1 C18_1 1.375(9) . ?
C14_1 C15_1 1.413(9) . ?
C15_1 H15_1 0.9500 . ?
C15_1 C16_1 1.401(9) . ?
C16_1 C17_1 1.384(10) . ?
C17_1 H17_1 0.9500 . ?
C17_1 C18_1 1.408(10) . ?
C18_1 H18_1 0.9500 . ?
Cl1_2 C16_2 1.731(7) . ?
O1_2 C1_2 1.421(9) . ?
O1_2 C2_2 1.374(8) . ?
O2_2 C12_2 1.366(8) . ?
O2_2 C13_2 1.387(9) . ?
O3_2 C12_2 1.226(8) . ?
N1_2 H1_2 0.8800 . ?
N1_2 C5_2 1.408(9) . ?
N1_2 C9_2 1.340(9) . ?
C1_2 H1A_2 0.9800 . ?
C1_2 H1B_2 0.9800 . ?
C1_2 H1C_2 0.9800 . ?
C2_2 C3_2 1.426(10) . ?
C2_2 C7_2 1.398(10) . ?
C3_2 H3_2 0.9500 . ?
C3_2 C4_2 1.377(10) . ?
C4_2 H4_2 0.9500 . ?
C4_2 C5_2 1.374(10) . ?
C5_2 C6_2 1.403(10) . ?
C6_2 C7_2 1.398(9) . ?
C6_2 C8_2 1.448(9) . ?
C7_2 H7_2 0.9500 . ?
C8_2 C9_2 1.386(9) . ?
C8_2 C10_2 1.448(9) . ?
C9_2 H9_2 0.9500 . ?
C10_2 C11_2 1.381(9) . ?
C10_2 C14_2 1.462(9) . ?
C11_2 H11_2 0.9500 . ?
C11_2 C12_2 1.413(10) . ?
C13_2 C14_2 1.410(10) . ?
C13_2 C18_2 1.389(10) . ?
C14_2 C15_2 1.385(10) . ?
C15_2 H15_2 0.9500 . ?
C15_2 C16_2 1.392(10) . ?
C16_2 C17_2 1.385(11) . ?
C17_2 H17_2 0.9500 . ?
C17_2 C18_2 1.392(11) . ?
C18_2 H18_2 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_1 O1_1 C1_1 117.8(5) . . ?
C12_1 O2_1 C13_1 120.8(5) . . ?
C5_1 N1_1 H1_1 125.4 . . ?
C9_1 N1_1 H1_1 125.4 . . ?
C9_1 N1_1 C5_1 109.2(5) . . ?
O1_1 C1_1 H1A_1 109.5 . . ?
O1_1 C1_1 H1B_1 109.5 . . ?
O1_1 C1_1 H1C_1 109.5 . . ?
H1A_1 C1_1 H1B_1 109.5 . . ?
H1A_1 C1_1 H1C_1 109.5 . . ?
H1B_1 C1_1 H1C_1 109.5 . . ?
O1_1 C2_1 C3_1 123.1(6) . . ?
C7_1 C2_1 O1_1 115.1(6) . . ?
C7_1 C2_1 C3_1 121.8(6) . . ?
C2_1 C3_1 H3_1 120.0 . . ?
C2_1 C3_1 C4_1 119.9(6) . . ?
C4_1 C3_1 H3_1 120.0 . . ?
C3_1 C4_1 H4_1 121.2 . . ?
C5_1 C4_1 C3_1 117.6(6) . . ?
C5_1 C4_1 H4_1 121.2 . . ?
N1_1 C5_1 C4_1 129.7(6) . . ?
N1_1 C5_1 C6_1 107.8(6) . . ?
C4_1 C5_1 C6_1 122.5(6) . . ?
C5_1 C6_1 C8_1 106.6(6) . . ?
C7_1 C6_1 C5_1 118.5(6) . . ?
C7_1 C6_1 C8_1 134.9(6) . . ?
C2_1 C7_1 H7_1 120.1 . . ?
C6_1 C7_1 C2_1 119.7(6) . . ?
C6_1 C7_1 H7_1 120.1 . . ?
C6_1 C8_1 C10_1 126.1(6) . . ?
C9_1 C8_1 C6_1 106.6(6) . . ?
C9_1 C8_1 C10_1 127.2(6) . . ?
N1_1 C9_1 C8_1 109.7(6) . . ?
N1_1 C9_1 H9_1 125.2 . . ?
C8_1 C9_1 H9_1 125.2 . . ?
C11_1 C10_1 C8_1 120.4(6) . . ?
C11_1 C10_1 C14_1 117.4(6) . . ?
C14_1 C10_1 C8_1 122.2(6) . . ?
C10_1 C11_1 H11_1 118.7 . . ?
C10_1 C11_1 C12_1 122.5(6) . . ?
C12_1 C11_1 H11_1 118.7 . . ?
O2_1 C12_1 C11_1 118.8(6) . . ?
O3_1 C12_1 O2_1 115.9(6) . . ?
O3_1 C12_1 C11_1 125.3(6) . . ?
C14_1 C13_1 O2_1 121.3(5) . . ?
C18_1 C13_1 O2_1 115.0(6) . . ?
C18_1 C13_1 C14_1 123.7(6) . . ?
C13_1 C14_1 C10_1 119.1(6) . . ?
C13_1 C14_1 C15_1 116.8(6) . . ?
C15_1 C14_1 C10_1 124.1(6) . . ?
C14_1 C15_1 H15_1 119.5 . . ?
C16_1 C15_1 C14_1 121.1(6) . . ?
C16_1 C15_1 H15_1 119.5 . . ?
C15_1 C16_1 Cl1_1 119.8(5) . . ?
C17_1 C16_1 Cl1_1 120.3(5) . . ?
C17_1 C16_1 C15_1 119.9(6) . . ?
C16_1 C17_1 H17_1 120.0 . . ?
C16_1 C17_1 C18_1 120.0(6) . . ?
C18_1 C17_1 H17_1 120.0 . . ?
C13_1 C18_1 C17_1 118.6(6) . . ?
C13_1 C18_1 H18_1 120.7 . . ?
C17_1 C18_1 H18_1 120.7 . . ?
C2_2 O1_2 C1_2 115.6(6) . . ?
C12_2 O2_2 C13_2 120.8(5) . . ?
C5_2 N1_2 H1_2 125.2 . . ?
C9_2 N1_2 H1_2 125.2 . . ?
C9_2 N1_2 C5_2 109.6(6) . . ?
O1_2 C1_2 H1A_2 109.5 . . ?
O1_2 C1_2 H1B_2 109.5 . . ?
O1_2 C1_2 H1C_2 109.5 . . ?
H1A_2 C1_2 H1B_2 109.5 . . ?
H1A_2 C1_2 H1C_2 109.5 . . ?
H1B_2 C1_2 H1C_2 109.5 . . ?
O1_2 C2_2 C3_2 114.0(6) . . ?
O1_2 C2_2 C7_2 124.8(6) . . ?
C7_2 C2_2 C3_2 121.2(6) . . ?
C2_2 C3_2 H3_2 119.9 . . ?
C4_2 C3_2 C2_2 120.2(7) . . ?
C4_2 C3_2 H3_2 119.9 . . ?
C3_2 C4_2 H4_2 121.0 . . ?
C5_2 C4_2 C3_2 117.9(7) . . ?
C5_2 C4_2 H4_2 121.0 . . ?
C4_2 C5_2 N1_2 129.7(7) . . ?
C4_2 C5_2 C6_2 123.6(6) . . ?
C6_2 C5_2 N1_2 106.8(6) . . ?
C5_2 C6_2 C8_2 107.3(6) . . ?
C7_2 C6_2 C5_2 119.1(6) . . ?
C7_2 C6_2 C8_2 133.6(6) . . ?
C2_2 C7_2 C6_2 118.0(6) . . ?
C2_2 C7_2 H7_2 121.0 . . ?
C6_2 C7_2 H7_2 121.0 . . ?
C6_2 C8_2 C10_2 127.1(6) . . ?
C9_2 C8_2 C6_2 105.9(6) . . ?
C9_2 C8_2 C10_2 126.8(6) . . ?
N1_2 C9_2 C8_2 110.5(6) . . ?
N1_2 C9_2 H9_2 124.8 . . ?
C8_2 C9_2 H9_2 124.8 . . ?
C8_2 C10_2 C14_2 121.8(6) . . ?
C11_2 C10_2 C8_2 121.0(6) . . ?
C11_2 C10_2 C14_2 117.2(6) . . ?
C10_2 C11_2 H11_2 118.3 . . ?
C10_2 C11_2 C12_2 123.4(7) . . ?
C12_2 C11_2 H11_2 118.3 . . ?
O2_2 C12_2 C11_2 118.8(6) . . ?
O3_2 C12_2 O2_2 115.5(6) . . ?
O3_2 C12_2 C11_2 125.7(7) . . ?
O2_2 C13_2 C14_2 121.7(6) . . ?
O2_2 C13_2 C18_2 116.4(7) . . ?
C18_2 C13_2 C14_2 121.9(7) . . ?
C13_2 C14_2 C10_2 118.1(6) . . ?
C15_2 C14_2 C10_2 124.4(6) . . ?
C15_2 C14_2 C13_2 117.4(6) . . ?
C14_2 C15_2 H15_2 119.5 . . ?
C14_2 C15_2 C16_2 121.0(7) . . ?
C16_2 C15_2 H15_2 119.5 . . ?
C15_2 C16_2 Cl1_2 119.2(6) . . ?
C17_2 C16_2 Cl1_2 119.7(6) . . ?
C17_2 C16_2 C15_2 121.0(7) . . ?
C16_2 C17_2 H17_2 120.4 . . ?
C16_2 C17_2 C18_2 119.2(7) . . ?
C18_2 C17_2 H17_2 120.4 . . ?
C13_2 C18_2 C17_2 119.5(7) . . ?
C13_2 C18_2 H18_2 120.3 . . ?
C17_2 C18_2 H18_2 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1_1 C16_1 C17_1 C18_1 -178.7(5) . . . . ?
O1_1 C2_1 C3_1 C4_1 178.6(6) . . . . ?
O1_1 C2_1 C7_1 C6_1 -178.6(6) . . . . ?
O2_1 C13_1 C14_1 C10_1 -0.3(9) . . . . ?
O2_1 C13_1 C14_1 C15_1 179.3(6) . . . . ?
O2_1 C13_1 C18_1 C17_1 -179.7(6) . . . . ?
N1_1 C5_1 C6_1 C7_1 179.7(6) . . . . ?
N1_1 C5_1 C6_1 C8_1 0.4(7) . . . . ?
C1_1 O1_1 C2_1 C3_1 8.2(10) . . . . ?
C1_1 O1_1 C2_1 C7_1 -172.2(6) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.4(10) . . . . ?
C3_1 C2_1 C7_1 C6_1 1.0(10) . . . . ?
C3_1 C4_1 C5_1 N1_1 -179.6(7) . . . . ?
C3_1 C4_1 C5_1 C6_1 0.0(10) . . . . ?
C4_1 C5_1 C6_1 C7_1 0.0(10) . . . . ?
C4_1 C5_1 C6_1 C8_1 -179.3(6) . . . . ?
C5_1 N1_1 C9_1 C8_1 1.3(8) . . . . ?
C5_1 C6_1 C7_1 C2_1 -0.5(10) . . . . ?
C5_1 C6_1 C8_1 C9_1 0.4(8) . . . . ?
C5_1 C6_1 C8_1 C10_1 -176.0(6) . . . . ?
C6_1 C8_1 C9_1 N1_1 -1.1(8) . . . . ?
C6_1 C8_1 C10_1 C11_1 36.9(11) . . . . ?
C6_1 C8_1 C10_1 C14_1 -142.7(7) . . . . ?
C7_1 C2_1 C3_1 C4_1 -1.0(11) . . . . ?
C7_1 C6_1 C8_1 C9_1 -178.8(8) . . . . ?
C7_1 C6_1 C8_1 C10_1 4.8(13) . . . . ?
C8_1 C6_1 C7_1 C2_1 178.6(7) . . . . ?
C8_1 C10_1 C11_1 C12_1 177.1(6) . . . . ?
C8_1 C10_1 C14_1 C13_1 -178.9(6) . . . . ?
C8_1 C10_1 C14_1 C15_1 1.6(10) . . . . ?
C9_1 N1_1 C5_1 C4_1 178.6(7) . . . . ?
C9_1 N1_1 C5_1 C6_1 -1.1(7) . . . . ?
C9_1 C8_1 C10_1 C11_1 -138.8(8) . . . . ?
C9_1 C8_1 C10_1 C14_1 41.6(11) . . . . ?
C10_1 C8_1 C9_1 N1_1 175.3(6) . . . . ?
C10_1 C11_1 C12_1 O2_1 3.8(10) . . . . ?
C10_1 C11_1 C12_1 O3_1 -174.4(7) . . . . ?
C10_1 C14_1 C15_1 C16_1 179.9(6) . . . . ?
C11_1 C10_1 C14_1 C13_1 1.5(9) . . . . ?
C11_1 C10_1 C14_1 C15_1 -178.0(7) . . . . ?
C12_1 O2_1 C13_1 C14_1 0.8(9) . . . . ?
C12_1 O2_1 C13_1 C18_1 180.0(6) . . . . ?
C13_1 O2_1 C12_1 O3_1 175.9(6) . . . . ?
C13_1 O2_1 C12_1 C11_1 -2.4(9) . . . . ?
C13_1 C14_1 C15_1 C16_1 0.3(9) . . . . ?
C14_1 C10_1 C11_1 C12_1 -3.3(10) . . . . ?
C14_1 C13_1 C18_1 C17_1 -0.6(10) . . . . ?
C14_1 C15_1 C16_1 Cl1_1 178.3(5) . . . . ?
C14_1 C15_1 C16_1 C17_1 -0.5(10) . . . . ?
C15_1 C16_1 C17_1 C18_1 0.1(10) . . . . ?
C16_1 C17_1 C18_1 C13_1 0.4(10) . . . . ?
C18_1 C13_1 C14_1 C10_1 -179.4(6) . . . . ?
C18_1 C13_1 C14_1 C15_1 0.2(10) . . . . ?
Cl1_2 C16_2 C17_2 C18_2 179.5(6) . . . . ?
O1_2 C2_2 C3_2 C4_2 179.1(6) . . . . ?
O1_2 C2_2 C7_2 C6_2 -178.3(6) . . . . ?
O2_2 C13_2 C14_2 C10_2 0.1(9) . . . . ?
O2_2 C13_2 C14_2 C15_2 -178.5(6) . . . . ?
O2_2 C13_2 C18_2 C17_2 179.4(6) . . . . ?
N1_2 C5_2 C6_2 C7_2 -179.0(6) . . . . ?
N1_2 C5_2 C6_2 C8_2 0.0(7) . . . . ?
C1_2 O1_2 C2_2 C3_2 -177.0(6) . . . . ?
C1_2 O1_2 C2_2 C7_2 2.9(10) . . . . ?
C2_2 C3_2 C4_2 C5_2 -0.2(10) . . . . ?
C3_2 C2_2 C7_2 C6_2 1.6(10) . . . . ?
C3_2 C4_2 C5_2 N1_2 179.7(7) . . . . ?
C3_2 C4_2 C5_2 C6_2 0.3(11) . . . . ?
C4_2 C5_2 C6_2 C7_2 0.5(10) . . . . ?
C4_2 C5_2 C6_2 C8_2 179.5(6) . . . . ?
C5_2 N1_2 C9_2 C8_2 -0.1(8) . . . . ?
C5_2 C6_2 C7_2 C2_2 -1.4(9) . . . . ?
C5_2 C6_2 C8_2 C9_2 0.0(7) . . . . ?
C5_2 C6_2 C8_2 C10_2 175.1(6) . . . . ?
C6_2 C8_2 C9_2 N1_2 0.1(7) . . . . ?
C6_2 C8_2 C10_2 C11_2 -35.0(10) . . . . ?
C6_2 C8_2 C10_2 C14_2 146.9(6) . . . . ?
C7_2 C2_2 C3_2 C4_2 -0.8(11) . . . . ?
C7_2 C6_2 C8_2 C9_2 178.7(7) . . . . ?
C7_2 C6_2 C8_2 C10_2 -6.1(12) . . . . ?
C8_2 C6_2 C7_2 C2_2 179.9(7) . . . . ?
C8_2 C10_2 C11_2 C12_2 -175.1(6) . . . . ?
C8_2 C10_2 C14_2 C13_2 175.6(6) . . . . ?
C8_2 C10_2 C14_2 C15_2 -5.9(10) . . . . ?
C9_2 N1_2 C5_2 C4_2 -179.4(7) . . . . ?
C9_2 N1_2 C5_2 C6_2 0.1(7) . . . . ?
C9_2 C8_2 C10_2 C11_2 139.2(7) . . . . ?
C9_2 C8_2 C10_2 C14_2 -38.9(10) . . . . ?
C10_2 C8_2 C9_2 N1_2 -175.1(6) . . . . ?
C10_2 C11_2 C12_2 O2_2 -0.9(10) . . . . ?
C10_2 C11_2 C12_2 O3_2 176.1(7) . . . . ?
C10_2 C14_2 C15_2 C16_2 179.0(6) . . . . ?
C11_2 C10_2 C14_2 C13_2 -2.6(9) . . . . ?
C11_2 C10_2 C14_2 C15_2 175.9(6) . . . . ?
C12_2 O2_2 C13_2 C14_2 2.2(9) . . . . ?
C12_2 O2_2 C13_2 C18_2 -179.0(6) . . . . ?
C13_2 O2_2 C12_2 O3_2 -179.2(6) . . . . ?
C13_2 O2_2 C12_2 C11_2 -1.9(9) . . . . ?
C13_2 C14_2 C15_2 C16_2 -2.5(9) . . . . ?
C14_2 C10_2 C11_2 C12_2 3.1(10) . . . . ?
C14_2 C13_2 C18_2 C17_2 -1.9(11) . . . . ?
C14_2 C15_2 C16_2 Cl1_2 -178.5(5) . . . . ?
C14_2 C15_2 C16_2 C17_2 1.3(10) . . . . ?
C15_2 C16_2 C17_2 C18_2 -0.3(11) . . . . ?
C16_2 C17_2 C18_2 C13_2 0.6(11) . . . . ?
C18_2 C13_2 C14_2 C10_2 -178.6(6) . . . . ?
C18_2 C13_2 C14_2 C15_2 2.8(10) . . . . ?


# start Validation Reply Form
_vrf_PLAT306_rn_bp_sc235_0m_a    
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) ....... O1B_4 Check
RESPONSE: The hydrogen atoms of the disordered water molecules could not be
 reliably located from difference Fourier map
;
_vrf_PLAT340_rn_bp_sc235_0m_a    
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.0105 Ang.
RESPONSE: The crystal is thin needle shape with large channels filled with
 disordered water molecule. this affected the precision of the data to the
 present level. Further, -2 0 1, 0 0 1, 1 0 0, 2 0 0, 2 0 1, 2 0 2, 3 0 2
 reflections were affected by beamstop and thus omitted. However, there is no
 ambiguity in the structure and atom type assignment
;
_vrf_PLAT430_rn_bp_sc235_0m_a    
;
PROBLEM: Short Inter D...A Contact O3_1 ..O1B_4 . 2.80 Ang.
RESPONSE: There appears to be strong hydrogen bond between one of the disordered
 water molecule and carbonyl oxygen of the major molecule. However, the
 hydrogen atom of the disordered water molecule could be located reliably.
;



_publcif_funding_html            
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