# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_LTV_11_250724_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2374048'
loop_
_audit_author_name
_audit_author_address
'JYOTHYLAKSHMI JAYAKUMAR'
;RESEARCH SCHOLAR
India
;
_audit_update_record             
;
2024-07-28 deposited with the CCDC.	2024-09-17 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            'C16 H16 Cl N O'
_chemical_formula_weight         273.75

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                   5.6237(3)
_cell_length_b                   7.7655(5)
_cell_length_c                   16.0712(10)
_cell_angle_alpha                83.991(3)
_cell_angle_beta                 84.029(3)
_cell_angle_gamma                82.486(3)
_cell_volume                     689.08(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    6899
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      23.59

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.054
_exptl_absorpt_coefficient_mu    0.268
_shelx_estimated_absorpt_T_min   0.912
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27989
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.559
_diffrn_reflns_theta_max         28.279
_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             3416
_reflns_number_gt                2067
_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    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_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)+(0.0762P)²+0.3295P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3416
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1069
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1884
_refine_ls_wR_factor_gt          0.1545
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
Cl1_1 Cl -0.42788(15) 0.82827(12) 0.90564(6) 0.0903(4) Uani 1 1 d . . . . .
O1_1 O 0.7473(4) 0.6986(2) 0.60691(13) 0.0764(6) Uani 1 1 d . . . . .
N1_1 N 0.3484(3) 0.2941(2) 0.79695(11) 0.0460(5) Uani 1 1 d . . . . .
C1_1 C 0.1777(4) 0.4228(3) 0.82395(13) 0.0442(5) Uani 1 1 d . . . . .
C2_1 C -0.0087(5) 0.3756(3) 0.88559(14) 0.0516(6) Uani 1 1 d . . . . .
C3_1 C -0.1868(5) 0.5032(4) 0.90908(16) 0.0612(7) Uani 1 1 d . . . . .
H3_1 H -0.309642 0.474171 0.949372 0.073 Uiso 1 1 calc R U . . .
C4_1 C -0.1897(5) 0.6758(4) 0.87444(17) 0.0592(7) Uani 1 1 d . . . . .
C5_1 C -0.0121(5) 0.7262(3) 0.81726(16) 0.0561(6) Uani 1 1 d . . . . .
H5_1 H -0.014319 0.842357 0.795887 0.067 Uiso 1 1 calc R U . . .
C6_1 C 0.1766(4) 0.5998(3) 0.79050(14) 0.0477(6) Uani 1 1 d . . . . .
C7_1 C 0.3657(4) 0.6392(3) 0.72977(15) 0.0496(6) Uani 1 1 d . . . . .
H7_1 H 0.372871 0.753690 0.706942 0.060 Uiso 1 1 calc R U . . .
C8_1 C 0.5382(4) 0.5107(3) 0.70427(13) 0.0443(5) Uani 1 1 d . . . . .
C9_1 C 0.5219(4) 0.3366(3) 0.73910(13) 0.0427(5) Uani 1 1 d . . . . .
C10_1 C 0.7401(4) 0.5516(3) 0.64032(15) 0.0509(6) Uani 1 1 d . . . . .
C11_1 C 0.9313(4) 0.4043(3) 0.62119(15) 0.0503(6) Uani 1 1 d . . . . .
H11A_1 H 1.050257 0.394998 0.661519 0.060 Uiso 1 1 calc R U . . .
H11B_1 H 1.011593 0.431147 0.565845 0.060 Uiso 1 1 calc R U . . .
C12_1 C 0.8350(4) 0.2280(3) 0.62361(14) 0.0459(5) Uani 1 1 d . . . . .
C13_1 C 0.7060(4) 0.1910(3) 0.71110(14) 0.0501(6) Uani 1 1 d . . . . .
H13A_1 H 0.626990 0.087019 0.711599 0.060 Uiso 1 1 calc R U . . .
H13B_1 H 0.825544 0.166453 0.751477 0.060 Uiso 1 1 calc R U . . .
C14_1 C -0.0071(6) 0.1904(4) 0.92358(17) 0.0705(8) Uani 1 1 d . . . . .
H14A_1 H 0.021511 0.113137 0.879748 0.106 Uiso 1 1 calc R U . . .
H14B_1 H -0.159940 0.176061 0.954415 0.106 Uiso 1 1 calc R U . . .
H14C_1 H 0.118140 0.163590 0.960850 0.106 Uiso 1 1 calc R U . . .
C15_1 C 1.0459(5) 0.0856(4) 0.60940(18) 0.0617(7) Uani 1 1 d . . . . .
H15A_1 H 1.129264 0.109522 0.555014 0.093 Uiso 1 1 calc R U . . .
H15B_1 H 0.986424 -0.025453 0.612377 0.093 Uiso 1 1 calc R U . . .
H15C_1 H 1.154635 0.083320 0.651881 0.093 Uiso 1 1 calc R U . . .
C16_1 C 0.6642(5) 0.2339(4) 0.55551(16) 0.0602(7) Uani 1 1 d . . . . .
H16A_1 H 0.749303 0.257691 0.501424 0.090 Uiso 1 1 calc R U . . .
H16B_1 H 0.532745 0.324204 0.564227 0.090 Uiso 1 1 calc R U . . .
H16C_1 H 0.603026 0.123559 0.557958 0.090 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_1 C4_1 1.737(3) . ?
O1_1 C10_1 1.213(3) . ?
N1_1 C9_1 1.325(3) . ?
N1_1 C1_1 1.364(3) . ?
C1_1 C6_1 1.422(3) . ?
C1_1 C2_1 1.422(3) . ?
C2_1 C3_1 1.367(3) . ?
C2_1 C14_1 1.502(3) . ?
C3_1 C4_1 1.395(4) . ?
C4_1 C5_1 1.353(4) . ?
C5_1 C6_1 1.413(3) . ?
C6_1 C7_1 1.409(3) . ?
C7_1 C8_1 1.361(3) . ?
C8_1 C9_1 1.419(3) . ?
C8_1 C10_1 1.493(3) . ?
C9_1 C13_1 1.502(3) . ?
C10_1 C11_1 1.497(3) . ?
C11_1 C12_1 1.533(3) . ?
C12_1 C16_1 1.523(3) . ?
C12_1 C15_1 1.528(3) . ?
C12_1 C13_1 1.531(3) . ?

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
C9_1 N1_1 C1_1 118.74(18) . . ?
N1_1 C1_1 C6_1 122.1(2) . . ?
N1_1 C1_1 C2_1 118.3(2) . . ?
C6_1 C1_1 C2_1 119.5(2) . . ?
C3_1 C2_1 C1_1 118.1(2) . . ?
C3_1 C2_1 C14_1 121.5(2) . . ?
C1_1 C2_1 C14_1 120.4(2) . . ?
C2_1 C3_1 C4_1 122.0(2) . . ?
C5_1 C4_1 C3_1 121.5(2) . . ?
C5_1 C4_1 Cl1_1 119.6(2) . . ?
C3_1 C4_1 Cl1_1 118.9(2) . . ?
C4_1 C5_1 C6_1 119.0(2) . . ?
C7_1 C6_1 C5_1 123.1(2) . . ?
C7_1 C6_1 C1_1 117.1(2) . . ?
C5_1 C6_1 C1_1 119.8(2) . . ?
C8_1 C7_1 C6_1 120.4(2) . . ?
C7_1 C8_1 C9_1 118.8(2) . . ?
C7_1 C8_1 C10_1 120.7(2) . . ?
C9_1 C8_1 C10_1 120.4(2) . . ?
N1_1 C9_1 C8_1 122.7(2) . . ?
N1_1 C9_1 C13_1 117.00(19) . . ?
C8_1 C9_1 C13_1 120.3(2) . . ?
O1_1 C10_1 C8_1 120.6(2) . . ?
O1_1 C10_1 C11_1 122.5(2) . . ?
C8_1 C10_1 C11_1 116.85(19) . . ?
C10_1 C11_1 C12_1 113.70(18) . . ?
C16_1 C12_1 C15_1 109.6(2) . . ?
C16_1 C12_1 C13_1 111.17(19) . . ?
C15_1 C12_1 C13_1 109.2(2) . . ?
C16_1 C12_1 C11_1 110.0(2) . . ?
C15_1 C12_1 C11_1 109.32(19) . . ?
C13_1 C12_1 C11_1 107.51(19) . . ?
C9_1 C13_1 C12_1 114.62(19) . . ?

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.044

