# Supplementary Information (SI) for CrystEngComm.
# 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_Cl_Hanthraimmida_35pdc
_database_code_depnum_ccdc_archive 'CCDC 2396359'
loop_
_audit_author_name
_audit_author_address
'Jubaraj Bikash Baruah'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2024-11-02 deposited with the CCDC.	2025-02-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_Cl_Hanthraimmida_35pdc 
;
PROBLEM: Hirshfeld Test Diff for    O4       --C26      .        8.0 s.u.
RESPONSE: Due to room temperature data where disorder could not be resolved,
;
# Added during the CSD deposition process: Saturday 02 November 2024 01:53 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H38 Cl N5 O12'
_chemical_formula_weight         756.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.0457(16)
_cell_length_b                   31.235(4)
_cell_length_c                   11.3942(17)
_cell_angle_alpha                90
_cell_angle_beta                 117.679(5)
_cell_angle_gamma                90
_cell_volume                     3481.3(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9854
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      26.39

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_F_000             1584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.183
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6635
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;
 SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction 
 --------------------------------------------------------------------------

 Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            80041
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.082
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6122
_reflns_number_gt                4999
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0768P)²+7.2369P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6122
_refine_ls_number_parameters     494
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0832
_refine_ls_wR_factor_ref         0.2147
_refine_ls_wR_factor_gt          0.2077
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.89927(14) 0.26180(3) 0.83478(17) 0.0802(5) Uani 1 1 d . . . . .
O6 O 0.7641(3) 0.76000(8) 0.6675(3) 0.0462(7) Uani 1 1 d . . . . .
O2 O 0.6884(3) 0.43245(9) 0.3488(3) 0.0554(8) Uani 1 1 d . . . . .
O5 O 0.7847(3) 0.70062(9) 0.5693(3) 0.0529(7) Uani 1 1 d . . . . .
O1 O 0.6497(3) 0.43384(9) 0.5239(3) 0.0562(8) Uani 1 1 d . . . . .
N5 N 0.7669(3) 0.69615(9) 0.9773(3) 0.0355(7) Uani 1 1 d . . . . .
N3 N 0.7623(3) 0.47200(9) 0.7642(3) 0.0391(7) Uani 1 1 d . . . . .
H3A H 0.765473 0.500479 0.766426 0.047 Uiso 1 1 calc R U . . .
H3B H 0.743442 0.463872 0.682596 0.047 Uiso 1 1 calc R U . . .
O7 O 0.7852(4) 0.55985(9) 0.8087(4) 0.0744(10) Uani 1 1 d . . . . .
N4 N 0.5711(3) 0.30439(10) 0.4937(3) 0.0430(8) Uani 1 1 d . . . . .
H4 H 0.560052 0.291150 0.554220 0.052 Uiso 1 1 calc R U . . .
N2 N 0.3934(3) 0.41246(11) 0.7304(4) 0.0534(9) Uani 1 1 d . . . . .
O4 O 0.5425(4) 0.23571(11) 0.1785(3) 0.0683(9) Uani 1 1 d . . . . .
O8 O 0.7252(4) 0.56648(10) 0.9677(4) 0.0809(11) Uani 1 1 d . . . . .
O3 O 0.5551(4) 0.29452(12) 0.0737(3) 0.0720(10) Uani 1 1 d . . . . .
C35 C 0.7735(4) 0.71632(10) 0.8777(3) 0.0330(7) Uani 1 1 d . . . . .
H35 H 0.777233 0.746074 0.879040 0.040 Uiso 1 1 calc R U . . .
C23 C 0.6157(3) 0.36891(11) 0.4083(3) 0.0328(7) Uani 1 1 d . . . . .
O11 O 0.9097(4) 0.48108(13) 0.3824(4) 0.0761(10) Uani 1 1 d G . . . .
H11A H 0.881407 0.486457 0.300700 0.114 Uiso 1 1 d G U . . .
H11B H 0.843141 0.468272 0.385265 0.114 Uiso 1 1 d G U . . .
C30 C 0.7750(3) 0.69498(10) 0.7724(3) 0.0311(7) Uani 1 1 d . . . . .
C31 C 0.7724(3) 0.65054(10) 0.7739(3) 0.0338(8) Uani 1 1 d . . . . .
H31 H 0.776246 0.635095 0.705976 0.041 Uiso 1 1 calc R U . . .
C24 C 0.6023(4) 0.34672(11) 0.2982(3) 0.0337(7) Uani 1 1 d . . . . .
H24 H 0.612353 0.361068 0.231716 0.040 Uiso 1 1 calc R U . . .
C25 C 0.5742(4) 0.30352(11) 0.2859(3) 0.0339(8) Uani 1 1 d . . . . .
C21 C 0.8867(4) 0.38260(12) 0.9511(4) 0.0407(9) Uani 1 1 d . . . . .
C29 C 0.7760(4) 0.71934(11) 0.6597(3) 0.0355(8) Uani 1 1 d . . . . .
O9 O 0.5565(4) 0.44959(15) 0.0841(4) 0.0885(12) Uani 1 1 d G . . . .
H9A H 0.598436 0.441593 0.164503 0.133 Uiso 1 1 d G U . . .
H9B H 0.472392 0.448358 0.064579 0.133 Uiso 1 1 d G U . . .
C8 C 0.9078(4) 0.40676(11) 0.8578(4) 0.0379(8) Uani 1 1 d . . . . .
C22 C 0.6539(4) 0.41597(12) 0.4280(4) 0.0407(9) Uani 1 1 d . . . . .
C32 C 0.7640(4) 0.62920(10) 0.8760(4) 0.0358(8) Uani 1 1 d . . . . .
C34 C 0.7606(4) 0.65342(11) 0.9755(4) 0.0381(8) Uani 1 1 d . . . . .
H34 H 0.753594 0.639458 1.044240 0.046 Uiso 1 1 calc R U . . .
C28 C 0.5980(4) 0.34653(11) 0.5038(3) 0.0364(8) Uani 1 1 d . . . . .
H28 H 0.604926 0.361188 0.577694 0.044 Uiso 1 1 calc R U . . .
C6 C 0.6501(4) 0.45777(12) 0.7913(4) 0.0413(9) Uani 1 1 d . . . . .
H6A H 0.668287 0.467596 0.878704 0.050 Uiso 1 1 calc R U . . .
H6B H 0.648035 0.426726 0.791696 0.050 Uiso 1 1 calc R U . . .
C27 C 0.5619(4) 0.28343(12) 0.3873(4) 0.0434(9) Uani 1 1 d . . . . .
H27 H 0.546494 0.254057 0.381759 0.052 Uiso 1 1 calc R U . . .
O10 O 0.7995(5) 0.49774(12) 0.1200(4) 0.0944(14) Uani 1 1 d G . . . .
H10A H 0.774745 0.521316 0.078166 0.142 Uiso 1 1 d G U . . .
H10B H 0.725614 0.483784 0.095465 0.142 Uiso 1 1 d G U . . .
C14 C 0.9317(4) 0.34038(12) 0.7536(4) 0.0467(10) Uani 1 1 d . . . . .
C9 C 0.9345(4) 0.38604(12) 0.7620(4) 0.0419(9) Uani 1 1 d . . . . .
C15 C 0.9023(4) 0.31750(12) 0.8438(5) 0.0499(11) Uani 1 1 d . . . . .
C33 C 0.7583(4) 0.58092(12) 0.8846(4) 0.0473(10) Uani 1 1 d . . . . .
C16 C 0.8822(4) 0.33662(12) 0.9427(4) 0.0474(10) Uani 1 1 d . . . . .
C7 C 0.9011(4) 0.45494(11) 0.8597(4) 0.0436(9) Uani 1 1 d . . . . .
H7A H 0.923482 0.464350 0.948593 0.052 Uiso 1 1 calc R U . . .
H7B H 0.969019 0.466759 0.837329 0.052 Uiso 1 1 calc R U . . .
C5 C 0.5127(4) 0.47410(13) 0.6913(5) 0.0539(11) Uani 1 1 d . . . . .
H5A H 0.492711 0.463653 0.604039 0.065 Uiso 1 1 calc R U . . .
H5B H 0.514617 0.505128 0.689339 0.065 Uiso 1 1 calc R U . . .
C10 C 0.9665(4) 0.40892(15) 0.6716(5) 0.0557(11) Uani 1 1 d . . . . .
H10 H 0.967548 0.438686 0.673623 0.067 Uiso 1 1 calc R U . . .
C20 C 0.8726(4) 0.40118(14) 1.0582(4) 0.0526(10) Uani 1 1 d . . . . .
H20 H 0.876377 0.430819 1.066884 0.063 Uiso 1 1 calc R U . . .
C26 C 0.5554(4) 0.27817(13) 0.1687(4) 0.0497(10) Uani 1 1 d . . . . .
C4 C 0.4011(5) 0.45975(14) 0.7243(5) 0.0579(12) Uani 1 1 d . . . . .
H4A H 0.418141 0.471790 0.809040 0.069 Uiso 1 1 calc R U . . .
H4B H 0.313910 0.470637 0.657564 0.069 Uiso 1 1 calc R U . . .
C17 C 0.8588(5) 0.31312(15) 1.0380(6) 0.0646(13) Uani 1 1 d . . . . .
H17 H 0.852290 0.283438 1.031828 0.078 Uiso 1 1 calc R U . . .
C13 C 0.9600(5) 0.32024(16) 0.6565(5) 0.0641(13) Uani 1 1 d . . . . .
H13 H 0.956993 0.290547 0.649656 0.077 Uiso 1 1 calc R U . . .
C11 C 0.9952(5) 0.38848(19) 0.5833(5) 0.0716(14) Uani 1 1 d . . . . .
H11 H 1.017995 0.404169 0.527008 0.086 Uiso 1 1 calc R U . . .
C12 C 0.9907(5) 0.3433(2) 0.5758(6) 0.0782(16) Uani 1 1 d . . . . .
H12 H 1.009373 0.329548 0.513698 0.094 Uiso 1 1 calc R U . . .
C3 C 0.4498(6) 0.38811(17) 0.8410(6) 0.0732(14) Uani 1 1 d . . . . .
H3 H 0.495995 0.398019 0.927734 0.088 Uiso 1 1 calc R U . . .
C19 C 0.8539(5) 0.37758(18) 1.1477(5) 0.0689(13) Uani 1 1 d . . . . .
H19 H 0.846326 0.390922 1.216976 0.083 Uiso 1 1 calc R U . . .
O12 O 0.8495(6) 0.5549(3) 0.6071(5) 0.133(2) Uani 1 1 d G . . . .
H12A H 0.850424 0.558318 0.681575 0.199 Uiso 1 1 d G U . . .
H12B H 0.912762 0.536960 0.622316 0.199 Uiso 1 1 d G U . . .
N1 N 0.3543(7) 0.3484(2) 0.6650(10) 0.129(3) Uani 1 1 d . . . . .
H1 H 0.326059 0.326221 0.614798 0.154 Uiso 1 1 calc R U . . .
C18 C 0.8461(5) 0.33291(18) 1.1359(6) 0.0749(16) Uani 1 1 d . . . . .
H18 H 0.831856 0.316762 1.196927 0.090 Uiso 1 1 calc R U . . .
C1 C 0.3364(5) 0.3869(2) 0.6254(6) 0.0843(19) Uani 1 1 d . . . . .
H1A H 0.290929 0.395783 0.537508 0.101 Uiso 1 1 calc R U . . .
C2 C 0.4273(8) 0.34785(18) 0.8035(11) 0.106(3) Uani 1 1 d . . . . .
H2 H 0.454391 0.323833 0.858011 0.128 Uiso 1 1 calc R U . . .
H6 H 0.764(6) 0.773(2) 0.599(6) 0.10(2) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C15 1.742(4) . ?
O6 C29 1.284(4) . ?
O6 H6 0.87(6) . ?
O2 C22 1.242(5) . ?
O5 C29 1.227(4) . ?
O1 C22 1.248(5) . ?
N5 C35 1.330(4) . ?
N5 C34 1.336(5) . ?
N3 C6 1.478(5) . ?
N3 C7 1.506(5) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
O7 C33 1.228(5) . ?
N4 C27 1.339(5) . ?
N4 C28 1.342(5) . ?
N4 H4 0.8600 . ?
N2 C1 1.328(6) . ?
N2 C3 1.351(6) . ?
N2 C4 1.483(6) . ?
O4 C26 1.344(5) . ?
O8 C33 1.247(5) . ?
O3 C26 1.195(5) . ?
C35 C30 1.380(5) . ?
C35 H35 0.9300 . ?
C23 C24 1.380(5) . ?
C23 C28 1.381(5) . ?
C23 C22 1.517(5) . ?
O11 H11A 0.8503 . ?
O11 H11B 0.8504 . ?
C30 C31 1.389(5) . ?
C30 C29 1.497(5) . ?
C31 C32 1.381(5) . ?
C31 H31 0.9300 . ?
C24 C25 1.377(5) . ?
C24 H24 0.9300 . ?
C25 C27 1.377(5) . ?
C25 C26 1.481(5) . ?
C21 C8 1.409(5) . ?
C21 C20 1.424(6) . ?
C21 C16 1.439(5) . ?
O9 H9A 0.8498 . ?
O9 H9B 0.8500 . ?
C8 C9 1.412(5) . ?
C8 C7 1.507(5) . ?
C32 C34 1.378(5) . ?
C32 C33 1.515(5) . ?
C34 H34 0.9300 . ?
C28 H28 0.9300 . ?
C6 C5 1.502(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C27 H27 0.9300 . ?
O10 H10A 0.8503 . ?
O10 H10B 0.8499 . ?
C14 C15 1.409(6) . ?
C14 C13 1.427(6) . ?
C14 C9 1.429(5) . ?
C9 C10 1.427(6) . ?
C15 C16 1.382(6) . ?
C16 C17 1.430(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C5 C4 1.513(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C10 C11 1.348(7) . ?
C10 H10 0.9300 . ?
C20 C19 1.349(6) . ?
C20 H20 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C17 C18 1.338(8) . ?
C17 H17 0.9300 . ?
C13 C12 1.330(8) . ?
C13 H13 0.9300 . ?
C11 C12 1.413(8) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C3 C2 1.314(8) . ?
C3 H3 0.9300 . ?
C19 C18 1.401(8) . ?
C19 H19 0.9300 . ?
O12 H12A 0.8502 . ?
O12 H12B 0.8494 . ?
N1 C1 1.266(10) . ?
N1 C2 1.400(11) . ?
N1 H1 0.8600 . ?
C18 H18 0.9300 . ?
C1 H1A 0.9300 . ?
C2 H2 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C29 O6 H6 110(4) . . ?
C35 N5 C34 118.9(3) . . ?
C6 N3 C7 114.4(3) . . ?
C6 N3 H3A 108.7 . . ?
C7 N3 H3A 108.7 . . ?
C6 N3 H3B 108.7 . . ?
C7 N3 H3B 108.7 . . ?
H3A N3 H3B 107.6 . . ?
C27 N4 C28 118.5(3) . . ?
C27 N4 H4 120.7 . . ?
C28 N4 H4 120.7 . . ?
C1 N2 C3 108.8(5) . . ?
C1 N2 C4 124.7(5) . . ?
C3 N2 C4 126.4(4) . . ?
N5 C35 C30 122.8(3) . . ?
N5 C35 H35 118.6 . . ?
C30 C35 H35 118.6 . . ?
C24 C23 C28 117.9(3) . . ?
C24 C23 C22 121.7(3) . . ?
C28 C23 C22 120.4(3) . . ?
H11A O11 H11B 104.5 . . ?
C35 C30 C31 117.6(3) . . ?
C35 C30 C29 120.5(3) . . ?
C31 C30 C29 121.8(3) . . ?
C32 C31 C30 120.2(3) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C25 C24 C23 120.6(3) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C27 C25 C24 117.8(3) . . ?
C27 C25 C26 119.1(3) . . ?
C24 C25 C26 123.1(3) . . ?
C8 C21 C20 123.4(3) . . ?
C8 C21 C16 119.8(4) . . ?
C20 C21 C16 116.7(4) . . ?
O5 C29 O6 125.5(3) . . ?
O5 C29 C30 120.8(3) . . ?
O6 C29 C30 113.6(3) . . ?
H9A O9 H9B 104.5 . . ?
C21 C8 C9 120.3(3) . . ?
C21 C8 C7 119.8(3) . . ?
C9 C8 C7 119.9(3) . . ?
O2 C22 O1 126.9(4) . . ?
O2 C22 C23 116.9(3) . . ?
O1 C22 C23 116.2(3) . . ?
C34 C32 C31 117.8(3) . . ?
C34 C32 C33 118.4(3) . . ?
C31 C32 C33 123.8(3) . . ?
N5 C34 C32 122.7(3) . . ?
N5 C34 H34 118.7 . . ?
C32 C34 H34 118.7 . . ?
N4 C28 C23 122.4(3) . . ?
N4 C28 H28 118.8 . . ?
C23 C28 H28 118.8 . . ?
N3 C6 C5 113.0(3) . . ?
N3 C6 H6A 109.0 . . ?
C5 C6 H6A 109.0 . . ?
N3 C6 H6B 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
N4 C27 C25 122.8(3) . . ?
N4 C27 H27 118.6 . . ?
C25 C27 H27 118.6 . . ?
H10A O10 H10B 104.5 . . ?
C15 C14 C13 123.3(4) . . ?
C15 C14 C9 117.5(4) . . ?
C13 C14 C9 119.1(4) . . ?
C8 C9 C10 122.6(4) . . ?
C8 C9 C14 120.2(4) . . ?
C10 C9 C14 117.1(4) . . ?
C16 C15 C14 123.7(3) . . ?
C16 C15 Cl1 118.3(3) . . ?
C14 C15 Cl1 117.9(3) . . ?
O7 C33 O8 126.4(4) . . ?
O7 C33 C32 117.2(4) . . ?
O8 C33 C32 116.4(4) . . ?
C15 C16 C17 123.5(4) . . ?
C15 C16 C21 118.1(4) . . ?
C17 C16 C21 118.4(4) . . ?
N3 C7 C8 112.5(3) . . ?
N3 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
N3 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C6 C5 C4 111.4(4) . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C11 C10 C9 121.7(4) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C19 C20 C21 122.8(4) . . ?
C19 C20 H20 118.6 . . ?
C21 C20 H20 118.6 . . ?
O3 C26 O4 122.8(4) . . ?
O3 C26 C25 121.8(4) . . ?
O4 C26 C25 115.4(4) . . ?
N2 C4 C5 112.2(3) . . ?
N2 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
N2 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C18 C17 C16 121.4(4) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C12 C13 C14 121.0(5) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C10 C11 C12 120.3(5) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.9(5) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C2 C3 N2 107.5(6) . . ?
C2 C3 H3 126.3 . . ?
N2 C3 H3 126.3 . . ?
C20 C19 C18 119.7(5) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
H12A O12 H12B 104.5 . . ?
C1 N1 C2 109.1(5) . . ?
C1 N1 H1 125.5 . . ?
C2 N1 H1 125.5 . . ?
C17 C18 C19 121.0(5) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
N1 C1 N2 108.6(7) . . ?
N1 C1 H1A 125.7 . . ?
N2 C1 H1A 125.7 . . ?
C3 C2 N1 106.1(6) . . ?
C3 C2 H2 127.0 . . ?
N1 C2 H2 127.0 . . ?

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
C34 N5 C35 C30 -0.4(5) . . . . ?
N5 C35 C30 C31 -1.4(5) . . . . ?
N5 C35 C30 C29 177.2(3) . . . . ?
C35 C30 C31 C32 2.1(5) . . . . ?
C29 C30 C31 C32 -176.5(3) . . . . ?
C28 C23 C24 C25 -0.9(5) . . . . ?
C22 C23 C24 C25 176.7(3) . . . . ?
C23 C24 C25 C27 -0.8(5) . . . . ?
C23 C24 C25 C26 178.5(3) . . . . ?
C35 C30 C29 O5 176.1(3) . . . . ?
C31 C30 C29 O5 -5.4(5) . . . . ?
C35 C30 C29 O6 -5.4(5) . . . . ?
C31 C30 C29 O6 173.1(3) . . . . ?
C20 C21 C8 C9 173.7(4) . . . . ?
C16 C21 C8 C9 -4.7(5) . . . . ?
C20 C21 C8 C7 -6.6(5) . . . . ?
C16 C21 C8 C7 175.0(3) . . . . ?
C24 C23 C22 O2 -8.2(5) . . . . ?
C28 C23 C22 O2 169.4(3) . . . . ?
C24 C23 C22 O1 173.0(3) . . . . ?
C28 C23 C22 O1 -9.4(5) . . . . ?
C30 C31 C32 C34 -1.0(5) . . . . ?
C30 C31 C32 C33 179.0(3) . . . . ?
C35 N5 C34 C32 1.6(5) . . . . ?
C31 C32 C34 N5 -0.9(5) . . . . ?
C33 C32 C34 N5 179.1(3) . . . . ?
C27 N4 C28 C23 0.3(5) . . . . ?
C24 C23 C28 N4 1.2(5) . . . . ?
C22 C23 C28 N4 -176.5(3) . . . . ?
C7 N3 C6 C5 -177.9(3) . . . . ?
C28 N4 C27 C25 -2.2(6) . . . . ?
C24 C25 C27 N4 2.5(6) . . . . ?
C26 C25 C27 N4 -176.8(4) . . . . ?
C21 C8 C9 C10 -175.3(4) . . . . ?
C7 C8 C9 C10 5.0(6) . . . . ?
C21 C8 C9 C14 4.0(5) . . . . ?
C7 C8 C9 C14 -175.7(3) . . . . ?
C15 C14 C9 C8 -0.3(5) . . . . ?
C13 C14 C9 C8 -179.5(4) . . . . ?
C15 C14 C9 C10 179.1(4) . . . . ?
C13 C14 C9 C10 -0.2(5) . . . . ?
C13 C14 C15 C16 176.3(4) . . . . ?
C9 C14 C15 C16 -3.0(6) . . . . ?
C13 C14 C15 Cl1 -0.5(5) . . . . ?
C9 C14 C15 Cl1 -179.7(3) . . . . ?
C34 C32 C33 O7 -167.6(4) . . . . ?
C31 C32 C33 O7 12.4(6) . . . . ?
C34 C32 C33 O8 13.0(6) . . . . ?
C31 C32 C33 O8 -166.9(4) . . . . ?
C14 C15 C16 C17 -176.9(4) . . . . ?
Cl1 C15 C16 C17 -0.1(5) . . . . ?
C14 C15 C16 C21 2.3(6) . . . . ?
Cl1 C15 C16 C21 179.1(3) . . . . ?
C8 C21 C16 C15 1.5(5) . . . . ?
C20 C21 C16 C15 -176.9(3) . . . . ?
C8 C21 C16 C17 -179.2(4) . . . . ?
C20 C21 C16 C17 2.4(5) . . . . ?
C6 N3 C7 C8 61.3(4) . . . . ?
C21 C8 C7 N3 -95.4(4) . . . . ?
C9 C8 C7 N3 84.4(4) . . . . ?
N3 C6 C5 C4 -178.6(3) . . . . ?
C8 C9 C10 C11 178.2(4) . . . . ?
C14 C9 C10 C11 -1.1(6) . . . . ?
C8 C21 C20 C19 -179.3(4) . . . . ?
C16 C21 C20 C19 -0.9(6) . . . . ?
C27 C25 C26 O3 174.5(4) . . . . ?
C24 C25 C26 O3 -4.8(6) . . . . ?
C27 C25 C26 O4 -7.3(5) . . . . ?
C24 C25 C26 O4 173.5(4) . . . . ?
C1 N2 C4 C5 -77.8(5) . . . . ?
C3 N2 C4 C5 97.6(5) . . . . ?
C6 C5 C4 N2 -58.4(5) . . . . ?
C15 C16 C17 C18 176.9(4) . . . . ?
C21 C16 C17 C18 -2.3(7) . . . . ?
C15 C14 C13 C12 -178.3(4) . . . . ?
C9 C14 C13 C12 0.9(6) . . . . ?
C9 C10 C11 C12 1.7(7) . . . . ?
C14 C13 C12 C11 -0.4(8) . . . . ?
C10 C11 C12 C13 -0.9(8) . . . . ?
C1 N2 C3 C2 0.1(6) . . . . ?
C4 N2 C3 C2 -176.0(5) . . . . ?
C21 C20 C19 C18 -0.8(7) . . . . ?
C16 C17 C18 C19 0.6(8) . . . . ?
C20 C19 C18 C17 1.0(8) . . . . ?
C2 N1 C1 N2 -0.2(7) . . . . ?
C3 N2 C1 N1 0.1(6) . . . . ?
C4 N2 C1 N1 176.2(4) . . . . ?
N2 C3 C2 N1 -0.2(7) . . . . ?
C1 N1 C2 C3 0.2(8) . . . . ?

_refine_diff_density_max         1.385
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.087

####################################################################### 
# 
# 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_Cl_Hanthraimmida_35pdc_14-diITFB
_database_code_depnum_ccdc_archive 'CCDC 2396360'
loop_
_audit_author_name
_audit_author_address
'Jubaraj Bikash Baruah'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2024-11-02 deposited with the CCDC.	2025-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H38 Cl F2 I N5 O12'
_chemical_formula_weight         957.08

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8096(5)
_cell_length_b                   11.2696(6)
_cell_length_c                   21.1324(12)
_cell_angle_alpha                85.724(2)
_cell_angle_beta                 81.896(2)
_cell_angle_gamma                72.086(2)
_cell_volume                     1975.30(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9936
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      28.11

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_F_000             970
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.958
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6853
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction 
 --------------------------------------------------------------------------

 Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48535
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.900
_diffrn_reflns_theta_max         26.018
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7768
_reflns_number_gt                6522
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0153P)²+3.3150P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7768
_refine_ls_number_parameters     545
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.0852
_refine_ls_wR_factor_gt          0.0775
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.20793(3) 0.21710(2) 0.09810(2) 0.04529(9) Uani 1 1 d . . . . .
Cl1 Cl 1.00533(11) 0.67287(10) 0.05685(5) 0.0537(3) Uani 1 1 d . . . . .
O2 O 0.4483(2) 0.53949(19) 0.29140(11) 0.0371(5) Uani 1 1 d . . . . .
F2 F 0.7784(3) 0.0467(2) -0.04632(11) 0.0620(6) Uani 1 1 d . . . . .
F1 F 0.5562(3) 0.21246(19) 0.02660(11) 0.0597(6) Uani 1 1 d . . . . .
O4 O 0.8516(3) 0.7729(2) 0.28635(12) 0.0416(6) Uani 1 1 d . . . . .
H4 H 0.892162 0.823561 0.297085 0.062 Uiso 1 1 calc R U . . .
O9 O 0.9961(3) 0.9121(2) 0.32805(12) 0.0446(6) Uani 1 1 d G . . . .
H9A H 0.994796 0.893400 0.367790 0.067 Uiso 1 1 d G U . . .
H9B H 0.980459 0.990515 0.325689 0.067 Uiso 1 1 d G U . . .
O5 O -0.1428(3) 0.6558(2) 0.47639(12) 0.0473(6) Uani 1 1 d . . . . .
N3 N 0.3210(3) 0.8104(2) 0.26084(12) 0.0306(6) Uani 1 1 d . . . . .
H3A H 0.218639 0.830993 0.278179 0.037 Uiso 1 1 calc R U . . .
H3B H 0.357578 0.727608 0.259562 0.037 Uiso 1 1 calc R U . . .
O3 O 1.0945(3) 0.6942(2) 0.23315(12) 0.0469(6) Uani 1 1 d . . . . .
O8 O -0.0528(3) 0.1499(2) 0.33946(13) 0.0501(7) Uani 1 1 d . . . . .
N5 N 0.2063(3) 0.4605(2) 0.33707(13) 0.0335(6) Uani 1 1 d . . . . .
H5 H 0.287046 0.486285 0.322212 0.040 Uiso 1 1 calc R U . . .
O7 O 0.1822(3) 0.1281(2) 0.28035(13) 0.0560(7) Uani 1 1 d . . . . .
O12 O 0.2071(4) 0.8476(3) 0.53426(14) 0.0682(8) Uani 1 1 d G . . . .
H12A H 0.286010 0.781569 0.536052 0.102 Uiso 1 1 d G U . . .
H12B H 0.153312 0.861029 0.571067 0.102 Uiso 1 1 d G U . . .
O1 O 0.5487(3) 0.3395(2) 0.26864(16) 0.0698(9) Uani 1 1 d . . . . .
N2 N 0.4744(4) 0.9728(2) 0.41109(13) 0.0399(7) Uani 1 1 d . . . . .
N4 N 0.9758(3) 0.3907(3) 0.18124(13) 0.0382(7) Uani 1 1 d . . . . .
O10 O -0.0049(4) 0.8398(3) 0.45211(16) 0.0761(9) Uani 1 1 d G . . . .
H10A H 0.062459 0.837884 0.477610 0.114 Uiso 1 1 d G U . . .
H10B H -0.033510 0.773933 0.457896 0.114 Uiso 1 1 d G U . . .
C6 C 0.4146(4) 0.8537(3) 0.30233(14) 0.0298(7) Uani 1 1 d . . . . .
H6A H 0.375496 0.943966 0.303645 0.036 Uiso 1 1 calc R U . . .
H6B H 0.526561 0.830460 0.283861 0.036 Uiso 1 1 calc R U . . .
C24 C 0.7582(3) 0.5696(3) 0.25976(15) 0.0280(7) Uani 1 1 d . . . . .
H24 H 0.685295 0.629652 0.285978 0.034 Uiso 1 1 calc R U . . .
C30 C -0.0404(4) 0.4918(3) 0.40365(15) 0.0301(7) Uani 1 1 d . . . . .
O6 O -0.2969(4) 0.5444(3) 0.4614(2) 0.1013(14) Uani 1 1 d . . . . .
C23 C 0.7196(4) 0.4659(3) 0.24454(15) 0.0305(7) Uani 1 1 d . . . . .
C25 C 0.9065(3) 0.5828(3) 0.23542(14) 0.0281(7) Uani 1 1 d . . . . .
C21 C 0.6034(4) 0.8919(3) 0.15458(14) 0.0307(7) Uani 1 1 d . . . . .
C7 C 0.3292(4) 0.8645(3) 0.19329(15) 0.0325(7) Uani 1 1 d . . . . .
H7A H 0.296046 0.954800 0.194480 0.039 Uiso 1 1 calc R U . . .
H7B H 0.255043 0.841113 0.170548 0.039 Uiso 1 1 calc R U . . .
C35 C 0.0934(4) 0.5267(3) 0.38042(15) 0.0312(7) Uani 1 1 d . . . . .
H35 H 0.105654 0.598402 0.395295 0.037 Uiso 1 1 calc R U . . .
C8 C 0.4968(4) 0.8193(3) 0.15761(14) 0.0285(7) Uani 1 1 d . . . . .
C9 C 0.5453(4) 0.7045(3) 0.12712(14) 0.0298(7) Uani 1 1 d . . . . .
C16 C 0.7639(4) 0.8458(3) 0.12200(15) 0.0342(7) Uani 1 1 d . . . . .
O11 O 0.4512(4) 0.6265(3) 0.55195(19) 0.0869(12) Uani 1 1 d G . . . .
H11A H 0.536123 0.603393 0.525583 0.130 Uiso 1 1 d G U . . .
H11B H 0.410387 0.566915 0.559667 0.130 Uiso 1 1 d G U . . .
C32 C 0.0679(4) 0.3107(3) 0.33892(15) 0.0295(7) Uani 1 1 d . . . . .
C31 C -0.0526(4) 0.3823(3) 0.38164(15) 0.0314(7) Uani 1 1 d . . . . .
H31 H -0.142916 0.357007 0.395876 0.038 Uiso 1 1 calc R U . . .
C26 C 0.9600(4) 0.6894(3) 0.25074(15) 0.0317(7) Uani 1 1 d . . . . .
C36 C 0.3814(4) 0.0881(3) 0.03837(15) 0.0366(8) Uani 1 1 d . . . . .
C29 C -0.1702(4) 0.5699(3) 0.45147(17) 0.0419(9) Uani 1 1 d . . . . .
C5 C 0.4033(4) 0.7995(3) 0.36952(15) 0.0366(8) Uani 1 1 d . . . . .
H5A H 0.433802 0.709241 0.368288 0.044 Uiso 1 1 calc R U . . .
H5B H 0.293051 0.828906 0.389640 0.044 Uiso 1 1 calc R U . . .
C14 C 0.7045(4) 0.6585(3) 0.09387(14) 0.0341(7) Uani 1 1 d . . . . .
C34 C 0.1958(4) 0.3549(3) 0.31648(15) 0.0330(7) Uani 1 1 d . . . . .
H34 H 0.276382 0.309988 0.286343 0.040 Uiso 1 1 calc R U . . .
C33 C 0.0673(4) 0.1850(3) 0.31703(16) 0.0354(7) Uani 1 1 d . . . . .
C27 C 1.0105(4) 0.4913(3) 0.19631(15) 0.0342(7) Uani 1 1 d . . . . .
H27 H 1.109816 0.500641 0.179658 0.041 Uiso 1 1 calc R U . . .
C22 C 0.5614(4) 0.4443(3) 0.26958(16) 0.0372(8) Uani 1 1 d . . . . .
C10 C 0.4418(4) 0.6277(3) 0.12766(16) 0.0419(8) Uani 1 1 d . . . . .
H10 H 0.338306 0.653927 0.149336 0.050 Uiso 1 1 calc R U . . .
C28 C 0.8333(4) 0.3793(3) 0.20575(16) 0.0373(8) Uani 1 1 d . . . . .
H28 H 0.808523 0.308674 0.196242 0.045 Uiso 1 1 calc R U . . .
N1 N 0.3587(4) 1.1630(3) 0.43835(18) 0.0597(9) Uani 1 1 d . . . . .
H1 H 0.295853 1.227834 0.457737 0.072 Uiso 1 1 calc R U . . .
C15 C 0.8083(4) 0.7305(3) 0.09340(14) 0.0338(7) Uani 1 1 d . . . . .
C4 C 0.5118(4) 0.8364(3) 0.40868(17) 0.0419(8) Uani 1 1 d . . . . .
H4A H 0.500200 0.801684 0.451861 0.050 Uiso 1 1 calc R U . . .
H4B H 0.622781 0.801203 0.390306 0.050 Uiso 1 1 calc R U . . .
C20 C 0.5599(4) 1.0107(3) 0.18307(17) 0.0417(8) Uani 1 1 d . . . . .
H20 H 0.456792 1.043191 0.204249 0.050 Uiso 1 1 calc R U . . .
C37 C 0.5257(4) 0.1075(3) 0.01409(16) 0.0401(8) Uani 1 1 d . . . . .
C38 C 0.6406(4) 0.0213(3) -0.02338(16) 0.0409(8) Uani 1 1 d . . . . .
C13 C 0.7499(5) 0.5426(3) 0.06299(17) 0.0482(9) Uani 1 1 d . . . . .
H13 H 0.852931 0.512651 0.041302 0.058 Uiso 1 1 calc R U . . .
C1 C 0.3562(5) 1.0467(3) 0.45044(17) 0.0448(9) Uani 1 1 d . . . . .
H1A H 0.284939 1.020766 0.480898 0.054 Uiso 1 1 calc R U . . .
C17 C 0.8699(5) 0.9195(4) 0.11989(19) 0.0528(10) Uani 1 1 d . . . . .
H17 H 0.973580 0.890875 0.098630 0.063 Uiso 1 1 calc R U . . .
C11 C 0.4910(5) 0.5183(4) 0.09744(18) 0.0541(10) Uani 1 1 d . . . . .
H11 H 0.420903 0.470875 0.098451 0.065 Uiso 1 1 calc R U . . .
C12 C 0.6467(5) 0.4753(4) 0.06453(19) 0.0580(11) Uani 1 1 d . . . . .
H12 H 0.678679 0.400107 0.043719 0.070 Uiso 1 1 calc R U . . .
C3 C 0.5495(5) 1.0452(3) 0.37295(19) 0.0494(9) Uani 1 1 d . . . . .
H3 H 0.634946 1.016904 0.341022 0.059 Uiso 1 1 calc R U . . .
C19 C 0.6656(5) 1.0769(4) 0.1799(2) 0.0580(11) Uani 1 1 d . . . . .
H19 H 0.634305 1.154051 0.198794 0.070 Uiso 1 1 calc R U . . .
C2 C 0.4812(5) 1.1621(3) 0.3887(2) 0.0529(10) Uani 1 1 d . . . . .
H2 H 0.509298 1.231064 0.370155 0.063 Uiso 1 1 calc R U . . .
C18 C 0.8220(5) 1.0302(4) 0.1483(2) 0.0670(13) Uani 1 1 d . . . . .
H18 H 0.893575 1.076373 0.146954 0.080 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
I1 C36 2.099(3) . ?
Cl1 C15 1.742(3) . ?
O2 C22 1.281(4) . ?
F2 C38 1.348(4) . ?
F1 C37 1.343(4) . ?
O4 C26 1.310(4) . ?
O4 H4 0.8200 . ?
O9 H9A 0.8498 . ?
O9 H9B 0.8502 . ?
O5 C29 1.236(4) . ?
N3 C6 1.484(4) . ?
N3 C7 1.511(4) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
O3 C26 1.208(4) . ?
O8 C33 1.261(4) . ?
N5 C34 1.330(4) . ?
N5 C35 1.332(4) . ?
N5 H5 0.8600 . ?
O7 C33 1.221(4) . ?
O12 H12A 0.8502 . ?
O12 H12B 0.8498 . ?
O1 C22 1.223(4) . ?
N2 C1 1.340(4) . ?
N2 C3 1.354(5) . ?
N2 C4 1.474(4) . ?
N4 C28 1.329(4) . ?
N4 C27 1.332(4) . ?
O10 H10A 0.8502 . ?
O10 H10B 0.8501 . ?
C6 C5 1.506(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C24 C25 1.383(4) . ?
C24 C23 1.384(4) . ?
C24 H24 0.9300 . ?
C30 C35 1.370(4) . ?
C30 C31 1.390(4) . ?
C30 C29 1.513(4) . ?
O6 C29 1.222(4) . ?
C23 C28 1.384(4) . ?
C23 C22 1.504(4) . ?
C25 C27 1.385(4) . ?
C25 C26 1.489(4) . ?
C21 C8 1.415(4) . ?
C21 C20 1.429(4) . ?
C21 C16 1.439(4) . ?
C7 C8 1.512(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C35 H35 0.9300 . ?
C8 C9 1.407(4) . ?
C9 C10 1.435(4) . ?
C9 C14 1.435(4) . ?
C16 C15 1.395(4) . ?
C16 C17 1.423(5) . ?
O11 H11A 0.8499 . ?
O11 H11B 0.8500 . ?
C32 C34 1.380(4) . ?
C32 C31 1.380(4) . ?
C32 C33 1.524(4) . ?
C31 H31 0.9300 . ?
C36 C38 1.371(5) 2_655 ?
C36 C37 1.377(5) . ?
C5 C4 1.513(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C14 C15 1.395(4) . ?
C14 C13 1.423(4) . ?
C34 H34 0.9300 . ?
C27 H27 0.9300 . ?
C10 C11 1.352(5) . ?
C10 H10 0.9300 . ?
C28 H28 0.9300 . ?
N1 C1 1.323(5) . ?
N1 C2 1.393(5) . ?
N1 H1 0.8600 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C20 C19 1.353(5) . ?
C20 H20 0.9300 . ?
C37 C38 1.371(5) . ?
C13 C12 1.347(5) . ?
C13 H13 0.9300 . ?
C1 H1A 0.9300 . ?
C17 C18 1.345(5) . ?
C17 H17 0.9300 . ?
C11 C12 1.404(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C3 C2 1.315(5) . ?
C3 H3 0.9300 . ?
C19 C18 1.403(6) . ?
C19 H19 0.9300 . ?
C2 H2 0.9300 . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C26 O4 H4 109.5 . . ?
H9A O9 H9B 104.5 . . ?
C6 N3 C7 113.6(2) . . ?
C6 N3 H3A 108.8 . . ?
C7 N3 H3A 108.8 . . ?
C6 N3 H3B 108.8 . . ?
C7 N3 H3B 108.8 . . ?
H3A N3 H3B 107.7 . . ?
C34 N5 C35 120.8(3) . . ?
C34 N5 H5 119.6 . . ?
C35 N5 H5 119.6 . . ?
H12A O12 H12B 109.5 . . ?
C1 N2 C3 108.5(3) . . ?
C1 N2 C4 125.3(3) . . ?
C3 N2 C4 126.2(3) . . ?
C28 N4 C27 117.1(3) . . ?
H10A O10 H10B 109.4 . . ?
N3 C6 C5 112.6(2) . . ?
N3 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
N3 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C25 C24 C23 119.1(3) . . ?
C25 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C35 C30 C31 117.6(3) . . ?
C35 C30 C29 121.2(3) . . ?
C31 C30 C29 121.3(3) . . ?
C28 C23 C24 117.9(3) . . ?
C28 C23 C22 119.9(3) . . ?
C24 C23 C22 122.2(3) . . ?
C24 C25 C27 118.3(3) . . ?
C24 C25 C26 122.8(3) . . ?
C27 C25 C26 118.9(3) . . ?
C8 C21 C20 123.0(3) . . ?
C8 C21 C16 119.7(3) . . ?
C20 C21 C16 117.3(3) . . ?
N3 C7 C8 111.9(3) . . ?
N3 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
N3 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N5 C35 C30 121.7(3) . . ?
N5 C35 H35 119.2 . . ?
C30 C35 H35 119.2 . . ?
C9 C8 C21 120.3(3) . . ?
C9 C8 C7 119.2(3) . . ?
C21 C8 C7 120.5(3) . . ?
C8 C9 C10 122.9(3) . . ?
C8 C9 C14 120.3(3) . . ?
C10 C9 C14 116.8(3) . . ?
C15 C16 C17 122.8(3) . . ?
C15 C16 C21 118.2(3) . . ?
C17 C16 C21 119.0(3) . . ?
H11A O11 H11B 109.4 . . ?
C34 C32 C31 117.7(3) . . ?
C34 C32 C33 119.2(3) . . ?
C31 C32 C33 123.1(3) . . ?
C32 C31 C30 120.8(3) . . ?
C32 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
O3 C26 O4 123.8(3) . . ?
O3 C26 C25 121.8(3) . . ?
O4 C26 C25 114.4(3) . . ?
C38 C36 C37 116.7(3) 2_655 . ?
C38 C36 I1 121.9(2) 2_655 . ?
C37 C36 I1 121.4(2) . . ?
O6 C29 O5 124.8(3) . . ?
O6 C29 C30 116.8(3) . . ?
O5 C29 C30 118.4(3) . . ?
C6 C5 C4 111.1(3) . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C15 C14 C13 122.9(3) . . ?
C15 C14 C9 118.0(3) . . ?
C13 C14 C9 119.1(3) . . ?
N5 C34 C32 121.3(3) . . ?
N5 C34 H34 119.3 . . ?
C32 C34 H34 119.3 . . ?
O7 C33 O8 126.5(3) . . ?
O7 C33 C32 117.6(3) . . ?
O8 C33 C32 115.9(3) . . ?
N4 C27 C25 123.5(3) . . ?
N4 C27 H27 118.2 . . ?
C25 C27 H27 118.2 . . ?
O1 C22 O2 124.4(3) . . ?
O1 C22 C23 119.2(3) . . ?
O2 C22 C23 116.4(3) . . ?
C11 C10 C9 121.6(3) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
N4 C28 C23 124.1(3) . . ?
N4 C28 H28 118.0 . . ?
C23 C28 H28 118.0 . . ?
C1 N1 C2 108.0(3) . . ?
C1 N1 H1 126.0 . . ?
C2 N1 H1 126.0 . . ?
C16 C15 C14 123.4(3) . . ?
C16 C15 Cl1 117.7(2) . . ?
C14 C15 Cl1 118.8(2) . . ?
N2 C4 C5 112.2(3) . . ?
N2 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
N2 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C19 C20 C21 121.4(3) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
F1 C37 C38 118.5(3) . . ?
F1 C37 C36 120.3(3) . . ?
C38 C37 C36 121.2(3) . . ?
F2 C38 C37 118.2(3) . . ?
F2 C38 C36 119.7(3) . 2_655 ?
C37 C38 C36 122.1(3) . 2_655 ?
C12 C13 C14 121.3(3) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
N1 C1 N2 108.0(4) . . ?
N1 C1 H1A 126.0 . . ?
N2 C1 H1A 126.0 . . ?
C18 C17 C16 120.8(3) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C10 C11 C12 120.8(3) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C2 C3 N2 108.5(4) . . ?
C2 C3 H3 125.7 . . ?
N2 C3 H3 125.7 . . ?
C20 C19 C18 120.5(4) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C3 C2 N1 107.0(3) . . ?
C3 C2 H2 126.5 . . ?
N1 C2 H2 126.5 . . ?
C17 C18 C19 121.0(4) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N3 C6 C5 179.5(2) . . . . ?
C25 C24 C23 C28 0.5(5) . . . . ?
C25 C24 C23 C22 179.4(3) . . . . ?
C23 C24 C25 C27 0.4(5) . . . . ?
C23 C24 C25 C26 -178.2(3) . . . . ?
C6 N3 C7 C8 66.2(3) . . . . ?
C34 N5 C35 C30 -2.5(5) . . . . ?
C31 C30 C35 N5 1.7(5) . . . . ?
C29 C30 C35 N5 -178.2(3) . . . . ?
C20 C21 C8 C9 178.3(3) . . . . ?
C16 C21 C8 C9 -2.2(5) . . . . ?
C20 C21 C8 C7 -1.3(5) . . . . ?
C16 C21 C8 C7 178.2(3) . . . . ?
N3 C7 C8 C9 84.7(3) . . . . ?
N3 C7 C8 C21 -95.6(3) . . . . ?
C21 C8 C9 C10 -179.0(3) . . . . ?
C7 C8 C9 C10 0.6(5) . . . . ?
C21 C8 C9 C14 1.4(5) . . . . ?
C7 C8 C9 C14 -178.9(3) . . . . ?
C8 C21 C16 C15 0.9(5) . . . . ?
C20 C21 C16 C15 -179.5(3) . . . . ?
C8 C21 C16 C17 -179.5(3) . . . . ?
C20 C21 C16 C17 0.1(5) . . . . ?
C34 C32 C31 C30 -3.3(5) . . . . ?
C33 C32 C31 C30 175.2(3) . . . . ?
C35 C30 C31 C32 1.2(5) . . . . ?
C29 C30 C31 C32 -178.8(3) . . . . ?
C24 C25 C26 O3 174.1(3) . . . . ?
C27 C25 C26 O3 -4.5(5) . . . . ?
C24 C25 C26 O4 -3.5(5) . . . . ?
C27 C25 C26 O4 177.9(3) . . . . ?
C35 C30 C29 O6 167.9(4) . . . . ?
C31 C30 C29 O6 -12.1(6) . . . . ?
C35 C30 C29 O5 -10.5(5) . . . . ?
C31 C30 C29 O5 169.6(3) . . . . ?
N3 C6 C5 C4 174.9(3) . . . . ?
C8 C9 C14 C15 0.5(5) . . . . ?
C10 C9 C14 C15 -179.1(3) . . . . ?
C8 C9 C14 C13 -179.5(3) . . . . ?
C10 C9 C14 C13 0.9(5) . . . . ?
C35 N5 C34 C32 0.3(5) . . . . ?
C31 C32 C34 N5 2.6(5) . . . . ?
C33 C32 C34 N5 -176.0(3) . . . . ?
C34 C32 C33 O7 0.4(5) . . . . ?
C31 C32 C33 O7 -178.1(3) . . . . ?
C34 C32 C33 O8 179.8(3) . . . . ?
C31 C32 C33 O8 1.3(5) . . . . ?
C28 N4 C27 C25 -0.2(5) . . . . ?
C24 C25 C27 N4 -0.6(5) . . . . ?
C26 C25 C27 N4 178.1(3) . . . . ?
C28 C23 C22 O1 17.4(5) . . . . ?
C24 C23 C22 O1 -161.5(4) . . . . ?
C28 C23 C22 O2 -163.4(3) . . . . ?
C24 C23 C22 O2 17.7(5) . . . . ?
C8 C9 C10 C11 179.4(3) . . . . ?
C14 C9 C10 C11 -1.0(5) . . . . ?
C27 N4 C28 C23 1.2(5) . . . . ?
C24 C23 C28 N4 -1.4(5) . . . . ?
C22 C23 C28 N4 179.7(3) . . . . ?
C17 C16 C15 C14 -178.5(3) . . . . ?
C21 C16 C15 C14 1.1(5) . . . . ?
C17 C16 C15 Cl1 2.9(5) . . . . ?
C21 C16 C15 Cl1 -177.5(2) . . . . ?
C13 C14 C15 C16 178.2(3) . . . . ?
C9 C14 C15 C16 -1.8(5) . . . . ?
C13 C14 C15 Cl1 -3.2(5) . . . . ?
C9 C14 C15 Cl1 176.8(2) . . . . ?
C1 N2 C4 C5 81.6(4) . . . . ?
C3 N2 C4 C5 -96.2(4) . . . . ?
C6 C5 C4 N2 57.6(4) . . . . ?
C8 C21 C20 C19 179.2(4) . . . . ?
C16 C21 C20 C19 -0.4(5) . . . . ?
C38 C36 C37 F1 179.9(3) 2_655 . . . ?
I1 C36 C37 F1 -2.2(5) . . . . ?
C38 C36 C37 C38 0.2(6) 2_655 . . . ?
I1 C36 C37 C38 178.1(3) . . . . ?
F1 C37 C38 F2 -0.6(5) . . . . ?
C36 C37 C38 F2 179.1(3) . . . . ?
F1 C37 C38 C36 -179.9(3) . . . 2_655 ?
C36 C37 C38 C36 -0.3(6) . . . 2_655 ?
C15 C14 C13 C12 179.8(4) . . . . ?
C9 C14 C13 C12 -0.2(6) . . . . ?
C2 N1 C1 N2 1.2(4) . . . . ?
C3 N2 C1 N1 -1.3(4) . . . . ?
C4 N2 C1 N1 -179.4(3) . . . . ?
C15 C16 C17 C18 -179.9(4) . . . . ?
C21 C16 C17 C18 0.6(6) . . . . ?
C9 C10 C11 C12 0.4(6) . . . . ?
C14 C13 C12 C11 -0.5(6) . . . . ?
C10 C11 C12 C13 0.4(7) . . . . ?
C1 N2 C3 C2 0.9(4) . . . . ?
C4 N2 C3 C2 179.0(3) . . . . ?
C21 C20 C19 C18 0.0(6) . . . . ?
N2 C3 C2 N1 -0.1(4) . . . . ?
C1 N1 C2 C3 -0.7(4) . . . . ?
C16 C17 C18 C19 -1.0(7) . . . . ?
C20 C19 C18 C17 0.8(7) . . . . ?

_refine_diff_density_max         0.470
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_Clanth_35pdc_IFbenz_2MeOH
_database_code_depnum_ccdc_archive 'CCDC 2403207'
loop_
_audit_author_name
_audit_author_address
'Jubaraj Bikash Baruah'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2024-11-15 deposited with the CCDC.	2025-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H33 Cl F4 I2 N4 O6'
_chemical_formula_weight         982.91

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.111(6)
_cell_length_b                   15.861(8)
_cell_length_c                   18.599(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.667(14)
_cell_angle_gamma                90
_cell_volume                     3867(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9917
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.02

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_F_000             1936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    1.764
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3620
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction 
 --------------------------------------------------------------------------

 Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            101867
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.687
_diffrn_reflns_theta_max         27.069
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             8453
_reflns_number_gt                7028
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0520P)²+8.0539P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8453
_refine_ls_number_parameters     486
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1187
_refine_ls_wR_factor_gt          0.1053
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I2 I 0.72201(2) 0.40461(2) 0.52847(2) 0.05439(10) Uani 1 1 d . . . . .
I1 I 0.43776(2) 0.64924(2) 0.28382(2) 0.06701(11) Uani 1 1 d . . . . .
Cl1 Cl 0.63952(11) 1.15236(8) 0.56763(8) 0.0778(4) Uani 1 1 d . . . . .
O3 O 0.62528(19) 0.39445(16) 0.18801(15) 0.0463(6) Uani 1 1 d . . . . .
O4 O 0.4932(2) 0.42860(15) 0.11780(16) 0.0506(7) Uani 1 1 d . . . . .
N3 N 0.6696(2) 0.88677(16) 0.27749(14) 0.0316(5) Uani 1 1 d . . . . .
H3A H 0.657237 0.929399 0.247524 0.038 Uiso 1 1 calc R U . . .
H3B H 0.730721 0.895128 0.297589 0.038 Uiso 1 1 calc R U . . .
N2 N 0.7000(2) 0.67298(17) 0.12035(15) 0.0344(6) Uani 1 1 d . . . . .
O1 O 0.5910(3) -0.00830(17) 0.17649(16) 0.0606(8) Uani 1 1 d . . . . .
O2 O 0.7067(3) 0.0863(2) 0.21022(19) 0.0693(9) Uani 1 1 d . . . . .
N1 N 0.5951(2) 0.57009(19) 0.10415(17) 0.0397(6) Uani 1 1 d . . . . .
F2 F 0.5399(2) 0.35783(15) 0.4173(2) 0.0868(10) Uani 1 1 d . . . . .
F1 F 0.4347(3) 0.4497(2) 0.3217(2) 0.0953(11) Uani 1 1 d . . . . .
N4 N 0.3859(2) 0.18192(19) 0.11749(19) 0.0473(7) Uani 1 1 d . . . . .
C28 C 0.5813(3) 0.2202(2) 0.16615(19) 0.0397(7) Uani 1 1 d . . . . .
H28 H 0.646725 0.233036 0.182603 0.048 Uiso 1 1 calc R U . . .
C6 C 0.6712(2) 0.80615(19) 0.23570(18) 0.0341(6) Uani 1 1 d . . . . .
H6A H 0.604055 0.795546 0.215224 0.041 Uiso 1 1 calc R U . . .
H6B H 0.688228 0.759790 0.267663 0.041 Uiso 1 1 calc R U . . .
C5 C 0.7487(3) 0.8107(2) 0.17600(19) 0.0390(7) Uani 1 1 d . . . . .
H5A H 0.719105 0.841321 0.135720 0.047 Uiso 1 1 calc R U . . .
H5B H 0.807675 0.842156 0.193007 0.047 Uiso 1 1 calc R U . . .
C26 C 0.5152(3) 0.2849(2) 0.14754(17) 0.0352(7) Uani 1 1 d . . . . .
F3 F 0.7182(3) 0.60069(19) 0.4904(3) 0.1210(17) Uani 1 1 d . . . . .
C1 C 0.6653(3) 0.6006(2) 0.14738(19) 0.0371(7) Uani 1 1 d . . . . .
H1 H 0.687584 0.575810 0.190089 0.045 Uiso 1 1 calc R U . . .
C8 C 0.6053(3) 0.9552(2) 0.39073(19) 0.0383(7) Uani 1 1 d . . . . .
C25 C 0.4176(3) 0.2618(2) 0.12337(19) 0.0401(7) Uani 1 1 d . . . . .
H25 H 0.372164 0.304511 0.110687 0.048 Uiso 1 1 calc R U . . .
F4 F 0.6115(3) 0.69191(18) 0.3975(2) 0.1163(15) Uani 1 1 d . . . . .
C3 C 0.6491(3) 0.6876(2) 0.05655(19) 0.0439(8) Uani 1 1 d . . . . .
H3 H 0.657965 0.733401 0.026054 0.053 Uiso 1 1 calc R U . . .
C4 C 0.7835(3) 0.7247(2) 0.1501(2) 0.0409(8) Uani 1 1 d . . . . .
H4A H 0.834833 0.732285 0.113507 0.049 Uiso 1 1 calc R U . . .
H4B H 0.815116 0.694751 0.190027 0.049 Uiso 1 1 calc R U . . .
C7 C 0.5906(3) 0.8864(2) 0.33496(19) 0.0390(7) Uani 1 1 d . . . . .
H7A H 0.592023 0.832106 0.358957 0.047 Uiso 1 1 calc R U . . .
H7B H 0.523852 0.892927 0.312647 0.047 Uiso 1 1 calc R U . . .
C27 C 0.5475(3) 0.3763(2) 0.15224(19) 0.0376(7) Uani 1 1 d . . . . .
C9 C 0.6763(3) 0.9423(2) 0.44750(19) 0.0393(7) Uani 1 1 d . . . . .
C23 C 0.5512(3) 0.1368(2) 0.16061(18) 0.0389(7) Uani 1 1 d . . . . .
C14 C 0.6886(3) 1.0048(3) 0.5035(2) 0.0466(9) Uani 1 1 d . . . . .
C2 C 0.5837(3) 0.6226(2) 0.0466(2) 0.0452(8) Uani 1 1 d . . . . .
H2 H 0.539299 0.615059 0.007726 0.054 Uiso 1 1 calc R U . . .
C21 C 0.5452(3) 1.0284(2) 0.3887(2) 0.0422(8) Uani 1 1 d . . . . .
C10 C 0.7380(3) 0.8680(3) 0.4532(2) 0.0491(9) Uani 1 1 d . . . . .
H10 H 0.732292 0.826620 0.417945 0.059 Uiso 1 1 calc R U . . .
C22 C 0.6234(3) 0.0666(2) 0.18385(19) 0.0461(8) Uani 1 1 d . . . . .
C24 C 0.4522(3) 0.1214(2) 0.1364(2) 0.0461(8) Uani 1 1 d . . . . .
H24 H 0.430692 0.065620 0.133182 0.055 Uiso 1 1 calc R U . . .
C32 C 0.6325(3) 0.4758(2) 0.4565(2) 0.0463(8) Uani 1 1 d . . . . .
C16 C 0.5553(3) 1.0903(2) 0.4459(2) 0.0485(10) Uani 1 1 d . . . . .
C15 C 0.6267(3) 1.0763(2) 0.4998(2) 0.0510(10) Uani 1 1 d . . . . .
C29 C 0.5203(3) 0.5740(3) 0.3565(2) 0.0517(9) Uani 1 1 d . . . . .
C13 C 0.7616(3) 0.9903(3) 0.5594(2) 0.0629(12) Uani 1 1 d . . . . .
H13 H 0.771692 1.031043 0.594727 0.075 Uiso 1 1 calc R U . . .
C30 C 0.5049(3) 0.4879(3) 0.3631(3) 0.0543(10) Uani 1 1 d . . . . .
C20 C 0.4730(3) 1.0456(3) 0.3324(2) 0.0569(10) Uani 1 1 d . . . . .
H20 H 0.465846 1.007346 0.294727 0.068 Uiso 1 1 calc R U . . .
C17 C 0.4898(4) 1.1631(2) 0.4432(3) 0.0626(13) Uani 1 1 d . . . . .
H17 H 0.494302 1.202834 0.479809 0.075 Uiso 1 1 calc R U . . .
C31 C 0.5594(3) 0.4408(2) 0.4129(3) 0.0515(9) Uani 1 1 d . . . . .
C11 C 0.8046(3) 0.8564(3) 0.5086(3) 0.0624(11) Uani 1 1 d . . . . .
H11 H 0.842766 0.807074 0.511373 0.075 Uiso 1 1 calc R U . . .
O5 O 0.3402(5) 0.7782(4) 0.1934(4) 0.140(2) Uani 1 1 d . . . . .
H5 H 0.382140 0.805773 0.171031 0.211 Uiso 1 1 calc R U . . .
C33 C 0.6474(4) 0.5617(3) 0.4493(3) 0.0632(12) Uani 1 1 d . . . . .
C18 C 0.4226(4) 1.1752(3) 0.3895(3) 0.0753(16) Uani 1 1 d . . . . .
H18 H 0.380956 1.222627 0.389744 0.090 Uiso 1 1 calc R U . . .
O6 O 0.4696(5) 0.8767(4) 0.1160(3) 0.1209(19) Uani 1 1 d . . . . .
H6 H 0.512482 0.910157 0.131068 0.181 Uiso 1 1 calc R U . . .
C12 C 0.8164(4) 0.9184(4) 0.5619(3) 0.0691(13) Uani 1 1 d . . . . .
H12 H 0.862607 0.909711 0.599513 0.083 Uiso 1 1 calc R U . . .
C19 C 0.4143(4) 1.1169(3) 0.3325(3) 0.0718(14) Uani 1 1 d . . . . .
H19 H 0.368672 1.126960 0.294772 0.086 Uiso 1 1 calc R U . . .
C34 C 0.5922(4) 0.6086(3) 0.4005(3) 0.0653(13) Uani 1 1 d . . . . .
C36 C 0.4637(5) 0.8820(4) 0.0427(4) 0.0922(18) Uani 1 1 d . . . . .
H36A H 0.407188 0.917277 0.029144 0.138 Uiso 1 1 calc R U . . .
H36B H 0.453908 0.826630 0.022897 0.138 Uiso 1 1 calc R U . . .
H36C H 0.525692 0.905663 0.024703 0.138 Uiso 1 1 calc R U . . .
C35 C 0.2691(7) 0.8316(7) 0.2228(6) 0.153(4) Uani 1 1 d . . . . .
H35A H 0.224365 0.800081 0.253205 0.229 Uiso 1 1 calc R U . . .
H35B H 0.230024 0.857918 0.185019 0.229 Uiso 1 1 calc R U . . .
H35C H 0.303356 0.874194 0.250737 0.229 Uiso 1 1 calc R U . . .
H1N H 0.564(4) 0.528(3) 0.112(3) 0.070(16) 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
I2 C32 2.100(4) . ?
I1 C29 2.095(4) . ?
Cl1 C15 1.752(4) . ?
O3 C27 1.245(4) . ?
O4 C27 1.263(4) . ?
N3 C6 1.497(4) . ?
N3 C7 1.497(4) . ?
N2 C1 1.335(4) . ?
N2 C3 1.374(5) . ?
N2 C4 1.471(4) . ?
O1 C22 1.268(5) . ?
O2 C22 1.232(5) . ?
N1 C1 1.308(5) . ?
N1 C2 1.363(5) . ?
F2 C31 1.343(4) . ?
F1 C30 1.338(5) . ?
N4 C25 1.338(5) . ?
N4 C24 1.339(5) . ?
C28 C23 1.385(5) . ?
C28 C26 1.384(5) . ?
C6 C5 1.515(5) . ?
C5 C4 1.519(5) . ?
C26 C25 1.400(5) . ?
C26 C27 1.514(5) . ?
F3 C33 1.346(5) . ?
C8 C21 1.404(5) . ?
C8 C9 1.414(5) . ?
C8 C7 1.516(5) . ?
F4 C34 1.346(5) . ?
C3 C2 1.353(5) . ?
C9 C10 1.433(5) . ?
C9 C14 1.445(5) . ?
C23 C24 1.391(5) . ?
C23 C22 1.520(5) . ?
C14 C15 1.395(6) . ?
C14 C13 1.424(6) . ?
C21 C20 1.430(6) . ?
C21 C16 1.452(5) . ?
C10 C11 1.356(6) . ?
C32 C31 1.367(6) . ?
C32 C33 1.383(5) . ?
C16 C15 1.383(7) . ?
C16 C17 1.438(6) . ?
C29 C34 1.357(6) . ?
C29 C30 1.387(6) . ?
C13 C12 1.348(8) . ?
C30 C31 1.382(6) . ?
C20 C19 1.368(6) . ?
C17 C18 1.337(8) . ?
C11 C12 1.403(7) . ?
O5 C35 1.379(10) . ?
C33 C34 1.373(6) . ?
C18 C19 1.410(8) . ?
O6 C36 1.366(8) . ?

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
C6 N3 C7 112.4(2) . . ?
C1 N2 C3 107.8(3) . . ?
C1 N2 C4 126.3(3) . . ?
C3 N2 C4 125.6(3) . . ?
C1 N1 C2 109.1(3) . . ?
C25 N4 C24 117.3(3) . . ?
C23 C28 C26 120.9(3) . . ?
N3 C6 C5 110.7(3) . . ?
C4 C5 C6 113.3(3) . . ?
C28 C26 C25 117.0(3) . . ?
C28 C26 C27 121.4(3) . . ?
C25 C26 C27 121.5(3) . . ?
N1 C1 N2 109.1(3) . . ?
C21 C8 C9 120.2(3) . . ?
C21 C8 C7 120.7(3) . . ?
C9 C8 C7 118.9(3) . . ?
N4 C25 C26 123.7(3) . . ?
C2 C3 N2 106.9(3) . . ?
N2 C4 C5 113.3(3) . . ?
N3 C7 C8 113.7(3) . . ?
O3 C27 O4 125.0(3) . . ?
O3 C27 C26 118.6(3) . . ?
O4 C27 C26 116.4(3) . . ?
C8 C9 C10 122.7(3) . . ?
C8 C9 C14 120.4(3) . . ?
C10 C9 C14 116.9(4) . . ?
C24 C23 C28 117.1(3) . . ?
C24 C23 C22 122.6(3) . . ?
C28 C23 C22 120.2(3) . . ?
C15 C14 C13 123.5(4) . . ?
C15 C14 C9 117.5(4) . . ?
C13 C14 C9 118.9(4) . . ?
C3 C2 N1 107.1(3) . . ?
C8 C21 C20 122.9(4) . . ?
C8 C21 C16 119.6(4) . . ?
C20 C21 C16 117.5(4) . . ?
C11 C10 C9 121.7(4) . . ?
O2 C22 O1 125.1(4) . . ?
O2 C22 C23 118.2(3) . . ?
O1 C22 C23 116.7(4) . . ?
N4 C24 C23 124.0(3) . . ?
C31 C32 C33 116.2(4) . . ?
C31 C32 I2 122.9(3) . . ?
C33 C32 I2 120.9(3) . . ?
C15 C16 C17 123.6(4) . . ?
C15 C16 C21 118.5(3) . . ?
C17 C16 C21 117.9(4) . . ?
C16 C15 C14 123.7(3) . . ?
C16 C15 Cl1 118.0(3) . . ?
C14 C15 Cl1 118.3(4) . . ?
C34 C29 C30 116.5(4) . . ?
C34 C29 I1 120.6(3) . . ?
C30 C29 I1 122.9(3) . . ?
C12 C13 C14 121.0(4) . . ?
F1 C30 C31 119.2(4) . . ?
F1 C30 C29 119.6(4) . . ?
C31 C30 C29 121.2(4) . . ?
C19 C20 C21 121.6(5) . . ?
C18 C17 C16 121.9(5) . . ?
F2 C31 C32 119.7(4) . . ?
F2 C31 C30 118.2(4) . . ?
C32 C31 C30 122.1(3) . . ?
C10 C11 C12 120.5(5) . . ?
F3 C33 C34 118.8(4) . . ?
F3 C33 C32 119.6(4) . . ?
C34 C33 C32 121.6(4) . . ?
C17 C18 C19 120.8(4) . . ?
C13 C12 C11 120.9(5) . . ?
C20 C19 C18 120.3(5) . . ?
C29 C34 F4 120.1(4) . . ?
C29 C34 C33 122.4(4) . . ?
F4 C34 C33 117.4(4) . . ?

_refine_diff_density_max         1.862
_refine_diff_density_min         -1.515
_refine_diff_density_rms         0.082

