# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_CLT-BB-H2O
_database_code_depnum_ccdc_archive 'CCDC 2070859'
loop_
_audit_author_name
_audit_author_address
'Abhimanew Dhir'
;Indian Institute of Science
India
;
_audit_update_record             
;
2021-03-16 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H28 Cl N5 O'
_chemical_formula_weight         522.03

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      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                   8.695(9)
_cell_length_b                   11.849(13)
_cell_length_c                   13.515(14)
_cell_angle_alpha                71.182(11)
_cell_angle_beta                 88.994(11)
_cell_angle_gamma                80.250(11)
_cell_volume                     1298(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    3644
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      28.2

_exptl_crystal_description       Block
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             548
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.182
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.111
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7235
_diffrn_reflns_av_unetI/netI     0.2760
_diffrn_reflns_av_R_equivalents  0.1790
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.122
_diffrn_reflns_theta_max         24.498
_diffrn_reflns_theta_full        24.498
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             4140
_reflns_number_gt                1667
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0914P)²] 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     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.018(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4140
_refine_ls_number_parameters     349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2314
_refine_ls_R_factor_gt           0.1016
_refine_ls_wR_factor_ref         0.2649
_refine_ls_wR_factor_gt          0.2055
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_restrained_S_all      0.953
_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
CL01 Cl 0.8863(2) 0.25582(18) 0.30397(16) 0.0396(7) Uani 1 1 d . . . . .
O1 O 0.5686(6) 0.7694(5) 0.0411(5) 0.0464(17) Uani 1 1 d G . . . .
H1A H 0.592290 0.708695 0.096050 0.070 Uiso 1 1 d G U . . .
H1B H 0.470162 0.777495 0.033161 0.070 Uiso 1 1 d G U . . .
N1 N 0.6022(7) 0.4012(5) 0.3562(4) 0.0271(16) Uani 1 1 d . . . . .
N4 N 1.2276(7) 0.8018(5) 0.0454(5) 0.0301(16) Uani 1 1 d . . . . .
N5 N 0.6910(7) 0.9914(5) -0.0410(5) 0.0313(16) Uani 1 1 d . . . . .
H5A H 0.668215 0.920387 -0.012279 0.038 Uiso 1 1 d R U . . .
H5B H 0.632228 1.042080 -0.017106 0.038 Uiso 1 1 d R U . . .
N2 N 0.6130(8) 0.5703(5) 0.2252(5) 0.0379(18) Uani 1 1 d . . . . .
C14 C 0.5900(9) 0.2057(6) 0.3355(6) 0.0278(19) Uani 1 1 d . . . . .
N3 N 1.1678(9) 0.3213(6) 0.1037(6) 0.054(2) Uani 1 1 d . . . . .
H3A H 1.261713 0.280164 0.108726 0.065 Uiso 1 1 d R U . . .
H3B H 1.120853 0.288609 0.160680 0.065 Uiso 1 1 d R U . . .
C28 C 1.2022(9) 0.6806(7) 0.0613(6) 0.029(2) Uani 1 1 d . . . . .
C8 C 0.6667(9) 0.2175(7) 0.5133(6) 0.0284(19) Uani 1 1 d . . . . .
C13 C 0.7696(8) 0.1098(6) 0.5328(6) 0.032(2) Uani 1 1 d . . . . .
H13 H 0.782952 0.073766 0.480733 0.038 Uiso 1 1 calc R U . . .
C29 C 1.1116(10) 0.8918(7) 0.0265(5) 0.029(2) Uani 1 1 d . . . . .
C1 C 0.5635(9) 0.2793(6) 0.4117(6) 0.0263(19) Uani 1 1 d . . . . .
C31 C 0.8423(9) 0.9908(6) -0.0165(5) 0.0255(19) Uani 1 1 d . . . . .
C2 C 0.3921(9) 0.2936(7) 0.4452(6) 0.0281(19) Uani 1 1 d . . . . .
C30 C 0.9511(9) 0.8893(7) 0.0108(6) 0.0278(19) Uani 1 1 d . . . . .
H30 H 0.920202 0.815401 0.019608 0.033 Uiso 1 1 calc R U . . .
C20 C 0.5614(9) 0.4655(7) 0.2552(6) 0.034(2) Uani 1 1 d . . . . .
H20 H 0.504090 0.439562 0.211856 0.040 Uiso 1 1 calc R U . . .
C22 C 0.6811(9) 0.4724(7) 0.3918(6) 0.032(2) Uani 1 1 d . . . . .
H22 H 0.722549 0.453851 0.459215 0.039 Uiso 1 1 calc R U . . .
C7 C 0.3455(10) 0.1940(7) 0.5228(6) 0.035(2) Uani 1 1 d . . . . .
H7 H 0.417063 0.123504 0.553105 0.042 Uiso 1 1 calc R U . . .
C15 C 0.4719(10) 0.1500(6) 0.3139(6) 0.032(2) Uani 1 1 d . . . . .
H15 H 0.375376 0.160448 0.343546 0.039 Uiso 1 1 calc R U . . .
C9 C 0.6442(9) 0.2684(7) 0.5943(6) 0.032(2) Uani 1 1 d . . . . .
H9 H 0.571284 0.338489 0.585081 0.038 Uiso 1 1 calc R U . . .
C12 C 0.8533(10) 0.0537(7) 0.6261(6) 0.038(2) Uani 1 1 d . . . . .
H12 H 0.920613 -0.019627 0.637880 0.045 Uiso 1 1 calc R U . . .
C19 C 0.7304(10) 0.1906(6) 0.2861(6) 0.032(2) Uani 1 1 d . . . . .
C3 C 0.2824(10) 0.3948(7) 0.4030(6) 0.033(2) Uani 1 1 d . . . . .
H3 H 0.310831 0.461322 0.352220 0.040 Uiso 1 1 calc R U . . .
C4 C 0.1293(10) 0.4004(7) 0.4344(7) 0.040(2) Uani 1 1 d . . . . .
H4 H 0.056253 0.469851 0.403656 0.048 Uiso 1 1 calc R U . . .
C25 C 1.0967(10) 0.6255(7) 0.1298(6) 0.040(2) Uani 1 1 d . . . . .
H25 H 1.031871 0.669645 0.164759 0.048 Uiso 1 1 calc R U . . .
C18 C 0.7542(9) 0.1203(7) 0.2218(6) 0.034(2) Uani 1 1 d . . . . .
H18 H 0.849592 0.110710 0.190651 0.041 Uiso 1 1 calc R U . . .
C10 C 0.7294(10) 0.2151(7) 0.6863(6) 0.036(2) Uani 1 1 d . . . . .
H10 H 0.716274 0.250445 0.738838 0.043 Uiso 1 1 calc R U . . .
C21 C 0.6876(10) 0.5727(7) 0.3121(7) 0.041(2) Uani 1 1 d . . . . .
H21 H 0.736222 0.635684 0.315284 0.049 Uiso 1 1 calc R U . . .
C17 C 0.6364(11) 0.0644(7) 0.2040(6) 0.041(2) Uani 1 1 d . . . . .
H17 H 0.652183 0.016269 0.161074 0.049 Uiso 1 1 calc R U . . .
C11 C 0.8344(9) 0.1095(7) 0.7021(6) 0.036(2) Uani 1 1 d . . . . .
H11 H 0.893462 0.075206 0.764587 0.043 Uiso 1 1 calc R U . . .
C24 C 1.0863(10) 0.5071(7) 0.1467(6) 0.041(2) Uani 1 1 d . . . . .
H24 H 1.018078 0.469928 0.195220 0.050 Uiso 1 1 calc R U . . .
C6 C 0.1932(10) 0.2028(8) 0.5530(6) 0.041(2) Uani 1 1 d . . . . .
H6 H 0.162889 0.137427 0.604126 0.049 Uiso 1 1 calc R U . . .
C23 C 1.1794(10) 0.4412(7) 0.0903(7) 0.039(2) Uani 1 1 d . . . . .
C16 C 0.4954(11) 0.0798(7) 0.2495(6) 0.042(2) Uani 1 1 d . . . . .
H16 H 0.415346 0.042609 0.236827 0.050 Uiso 1 1 calc R U . . .
C5 C 0.0850(10) 0.3052(8) 0.5096(7) 0.042(2) Uani 1 1 d . . . . .
H5 H -0.017236 0.309607 0.531320 0.050 Uiso 1 1 calc R U . . .
C26 C 1.2829(10) 0.4972(7) 0.0201(6) 0.044(2) Uani 1 1 d . . . . .
H26 H 1.344686 0.454665 -0.017478 0.052 Uiso 1 1 calc R U . . .
C27 C 1.2942(10) 0.6144(7) 0.0061(7) 0.041(2) Uani 1 1 d . . . . .
H27 H 1.364382 0.651193 -0.040959 0.049 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
CL01 C19 1.727(8) . ?
O1 H1A 0.8498 . ?
O1 H1B 0.8500 . ?
N1 C20 1.350(9) . ?
N1 C22 1.372(8) . ?
N1 C1 1.490(8) . ?
N4 C29 1.300(9) . ?
N4 C28 1.436(9) . ?
N5 C31 1.360(9) . ?
N5 H5A 0.8608 . ?
N5 H5B 0.8608 . ?
N2 C20 1.328(9) . ?
N2 C21 1.362(10) . ?
C14 C15 1.393(10) . ?
C14 C19 1.394(10) . ?
C14 C1 1.541(10) . ?
N3 C23 1.394(9) . ?
N3 H3A 0.8692 . ?
N3 H3B 0.8716 . ?
C28 C25 1.381(10) . ?
C28 C27 1.398(11) . ?
C8 C13 1.380(10) . ?
C8 C9 1.407(10) . ?
C8 C1 1.549(9) . ?
C13 C12 1.375(10) . ?
C13 H13 0.9300 . ?
C29 C30 1.423(10) . ?
C29 C31 1.476(9) 2_775 ?
C1 C2 1.548(11) . ?
C31 C30 1.348(10) . ?
C31 C29 1.476(9) 2_775 ?
C2 C3 1.365(10) . ?
C2 C7 1.416(10) . ?
C30 H30 0.9300 . ?
C20 H20 0.9300 . ?
C22 C21 1.331(10) . ?
C22 H22 0.9300 . ?
C7 C6 1.375(11) . ?
C7 H7 0.9300 . ?
C15 C16 1.376(10) . ?
C15 H15 0.9300 . ?
C9 C10 1.364(10) . ?
C9 H9 0.9300 . ?
C12 C11 1.383(11) . ?
C12 H12 0.9300 . ?
C19 C18 1.375(10) . ?
C3 C4 1.387(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.359(11) . ?
C4 H4 0.9300 . ?
C25 C24 1.366(10) . ?
C25 H25 0.9300 . ?
C18 C17 1.374(10) . ?
C18 H18 0.9300 . ?
C10 C11 1.376(11) . ?
C10 H10 0.9300 . ?
C21 H21 0.9300 . ?
C17 C16 1.374(11) . ?
C17 H17 0.9300 . ?
C11 H11 0.9300 . ?
C24 C23 1.412(11) . ?
C24 H24 0.9300 . ?
C6 C5 1.369(10) . ?
C6 H6 0.9300 . ?
C23 C26 1.384(11) . ?
C16 H16 0.9300 . ?
C5 H5 0.9300 . ?
C26 C27 1.361(10) . ?
C26 H26 0.9300 . ?
C27 H27 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
H1A O1 H1B 104.5 . . ?
C20 N1 C22 105.4(6) . . ?
C20 N1 C1 124.4(6) . . ?
C22 N1 C1 130.2(6) . . ?
C29 N4 C28 121.3(7) . . ?
C31 N5 H5A 109.8 . . ?
C31 N5 H5B 108.3 . . ?
H5A N5 H5B 109.2 . . ?
C20 N2 C21 104.7(6) . . ?
C15 C14 C19 117.0(7) . . ?
C15 C14 C1 120.3(7) . . ?
C19 C14 C1 122.7(7) . . ?
C23 N3 H3A 108.2 . . ?
C23 N3 H3B 112.2 . . ?
H3A N3 H3B 107.7 . . ?
C25 C28 C27 118.8(7) . . ?
C25 C28 N4 123.9(7) . . ?
C27 C28 N4 117.3(7) . . ?
C13 C8 C9 117.8(7) . . ?
C13 C8 C1 123.9(7) . . ?
C9 C8 C1 118.0(7) . . ?
C12 C13 C8 122.6(8) . . ?
C12 C13 H13 118.7 . . ?
C8 C13 H13 118.7 . . ?
N4 C29 C30 127.4(7) . . ?
N4 C29 C31 114.3(7) . 2_775 ?
C30 C29 C31 118.3(7) . 2_775 ?
N1 C1 C14 107.2(6) . . ?
N1 C1 C2 109.2(6) . . ?
C14 C1 C2 111.8(6) . . ?
N1 C1 C8 110.1(6) . . ?
C14 C1 C8 111.7(6) . . ?
C2 C1 C8 106.7(6) . . ?
C30 C31 N5 122.7(7) . . ?
C30 C31 C29 119.6(7) . 2_775 ?
N5 C31 C29 117.6(7) . 2_775 ?
C3 C2 C7 118.1(8) . . ?
C3 C2 C1 124.2(7) . . ?
C7 C2 C1 117.7(7) . . ?
C31 C30 C29 122.0(7) . . ?
C31 C30 H30 119.0 . . ?
C29 C30 H30 119.0 . . ?
N2 C20 N1 111.9(7) . . ?
N2 C20 H20 124.1 . . ?
N1 C20 H20 124.1 . . ?
C21 C22 N1 107.5(7) . . ?
C21 C22 H22 126.2 . . ?
N1 C22 H22 126.2 . . ?
C6 C7 C2 119.2(8) . . ?
C6 C7 H7 120.4 . . ?
C2 C7 H7 120.4 . . ?
C16 C15 C14 121.2(8) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C10 C9 C8 120.1(7) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C13 C12 C11 118.1(8) . . ?
C13 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
C18 C19 C14 121.9(7) . . ?
C18 C19 CL01 115.9(7) . . ?
C14 C19 CL01 122.2(6) . . ?
C2 C3 C4 121.3(7) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 120.6(8) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C24 C25 C28 120.8(8) . . ?
C24 C25 H25 119.6 . . ?
C28 C25 H25 119.6 . . ?
C17 C18 C19 119.6(8) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C9 C10 C11 120.6(8) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C22 C21 N2 110.4(7) . . ?
C22 C21 H21 124.8 . . ?
N2 C21 H21 124.8 . . ?
C18 C17 C16 119.9(8) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C10 C11 C12 120.8(7) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C25 C24 C23 119.8(7) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C5 C6 C7 121.7(8) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C26 C23 N3 119.7(8) . . ?
C26 C23 C24 119.3(7) . . ?
N3 C23 C24 121.0(8) . . ?
C17 C16 C15 120.3(8) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C4 C5 C6 119.1(9) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C27 C26 C23 120.0(8) . . ?
C27 C26 H26 120.0 . . ?
C23 C26 H26 120.0 . . ?
C26 C27 C28 121.2(8) . . ?
C26 C27 H27 119.4 . . ?
C28 C27 H27 119.4 . . ?

_refine_diff_density_max         0.434
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.091
_vrf_PLAT340_CLT-BB-H2O          
;
PROBLEM: Low Bond Precision on  C-C Bonds...          
RESPONSE:
The crystal does not diffract X-ray well due to poor crystal quality even after 
several recrystallization process; however, it represents the best possible data.
;
# end Validation Reply Form



