# Electronic Supplementary Material (ESI) for ChemComm.
# 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_BP_261_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2323124'
loop_
_audit_author_name
_audit_author_address
'Babula Das'
;IIT Guwahati
India
;
_audit_update_record             
;
2024-01-02 deposited with the CCDC.	2024-03-19 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            'C19 H17 Cl N2 O4'
_chemical_formula_weight         372.79

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                   9.6699(15)
_cell_length_b                   9.6753(15)
_cell_length_c                   10.4512(16)
_cell_angle_alpha                76.908(4)
_cell_angle_beta                 71.347(4)
_cell_angle_gamma                71.318(4)
_cell_volume                     869.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9892
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      25.08

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_F_000             388
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.248
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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            19625
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.753
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_full        24.991
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             3007
_reflns_number_gt                2768
_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)+(0.0421P)²+0.3615P] 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         3007
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0966
_refine_ls_wR_factor_gt          0.0927
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 Cl 1.01573(6) 0.30837(5) 0.97290(5) 0.06336(18) Uani 1 1 d . . . . .
O1 O 0.75824(13) 0.86778(14) 0.40289(13) 0.0520(3) Uani 1 1 d . . . . .
O2 O 0.69315(13) 0.98508(13) 0.21017(12) 0.0501(3) Uani 1 1 d . . . . .
O3 O 0.37263(15) 1.02285(13) 0.23388(14) 0.0566(3) Uani 1 1 d . . . . .
O4 O 0.46824(17) 0.79019(14) 0.19295(13) 0.0611(4) Uani 1 1 d . . . . .
N1 N 0.44362(15) 0.53864(14) 0.68314(13) 0.0407(3) Uani 1 1 d . . . . .
H1 H 0.475152 0.444271 0.699050 0.049 Uiso 1 1 calc R U . . .
N2 N 0.56464(15) 0.72501(14) 0.58215(13) 0.0404(3) Uani 1 1 d . . . . .
H2 H 0.651590 0.742143 0.562315 0.048 Uiso 1 1 calc R U . . .
C1 C 0.63819(17) 0.55560(16) 0.77675(15) 0.0357(3) Uani 1 1 d . . . . .
C2 C 0.63764(19) 0.58952(19) 0.89850(16) 0.0447(4) Uani 1 1 d . . . . .
H2A H 0.559294 0.664380 0.939677 0.054 Uiso 1 1 calc R U . . .
C3 C 0.7531(2) 0.5126(2) 0.95929(17) 0.0492(4) Uani 1 1 d . . . . .
H3 H 0.752504 0.535185 1.041383 0.059 Uiso 1 1 calc R U . . .
C4 C 0.86838(19) 0.40281(18) 0.89754(17) 0.0427(4) Uani 1 1 d . . . . .
C5 C 0.8718(2) 0.36664(19) 0.77620(19) 0.0498(4) Uani 1 1 d . . . . .
H5 H 0.950651 0.292079 0.735135 0.060 Uiso 1 1 calc R U . . .
C6 C 0.7553(2) 0.44368(18) 0.71705(17) 0.0467(4) Uani 1 1 d . . . . .
H6 H 0.755561 0.419893 0.635581 0.056 Uiso 1 1 calc R U . . .
C7 C 0.51156(17) 0.63768(16) 0.71160(15) 0.0367(3) Uani 1 1 d . . . . .
H7 H 0.433603 0.703594 0.773488 0.044 Uiso 1 1 calc R U . . .
C8 C 0.32325(17) 0.61086(16) 0.62796(14) 0.0354(3) Uani 1 1 d . . . . .
C9 C 0.33262(16) 0.74215(16) 0.53808(14) 0.0336(3) Uani 1 1 d . . . . .
C10 C 0.47951(16) 0.77909(15) 0.49338(15) 0.0334(3) Uani 1 1 d . . . . .
C11 C 0.19308(19) 0.5625(2) 0.66082(17) 0.0457(4) Uani 1 1 d . . . . .
H11 H 0.189388 0.471674 0.713429 0.055 Uiso 1 1 calc R U . . .
C12 C 0.20480(17) 0.82992(17) 0.49625(16) 0.0393(3) Uani 1 1 d . . . . .
H12 H 0.208063 0.919684 0.441321 0.047 Uiso 1 1 calc R U . . .
C13 C 0.07362(18) 0.7853(2) 0.53532(18) 0.0470(4) Uani 1 1 d . . . . .
H13 H -0.011687 0.845449 0.508432 0.056 Uiso 1 1 calc R U . . .
C14 C 0.06976(19) 0.6504(2) 0.61477(18) 0.0515(4) Uani 1 1 d . . . . .
H14 H -0.017198 0.618417 0.637527 0.062 Uiso 1 1 calc R U . . .
C15 C 0.52967(17) 0.85948(16) 0.36822(15) 0.0362(3) Uani 1 1 d . . . . .
C16 C 0.66889(17) 0.90112(16) 0.33379(16) 0.0391(4) Uani 1 1 d . . . . .
C17 C 0.8269(2) 1.0365(2) 0.1675(2) 0.0561(5) Uani 1 1 d . . . . .
H17A H 0.824365 1.092127 0.233834 0.084 Uiso 1 1 calc R U . . .
H17B H 0.830856 1.097939 0.080948 0.084 Uiso 1 1 calc R U . . .
H17C H 0.914994 0.953671 0.159044 0.084 Uiso 1 1 calc R U . . .
C18 C 0.45542(18) 0.88427(17) 0.25701(16) 0.0406(4) Uani 1 1 d . . . . .
C19 C 0.2906(3) 1.0511(3) 0.1325(3) 0.0795(7) Uani 1 1 d . . . . .
H19A H 0.361195 1.039898 0.044414 0.119 Uiso 1 1 calc R U . . .
H19B H 0.225466 1.149692 0.131332 0.119 Uiso 1 1 calc R U . . .
H19C H 0.230700 0.982434 0.154612 0.119 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 C4 1.7444(16) . ?
O1 C16 1.2195(19) . ?
O2 C16 1.3553(19) . ?
O2 C17 1.436(2) . ?
O3 C18 1.337(2) . ?
O3 C19 1.447(2) . ?
O4 C18 1.201(2) . ?
N1 C8 1.3789(19) . ?
N1 C7 1.448(2) . ?
N2 C10 1.3435(18) . ?
N2 C7 1.4573(19) . ?
C1 C2 1.382(2) . ?
C1 C6 1.383(2) . ?
C1 C7 1.503(2) . ?
C2 C3 1.382(2) . ?
C3 C4 1.371(3) . ?
C4 C5 1.378(2) . ?
C5 C6 1.380(2) . ?
C8 C11 1.396(2) . ?
C8 C9 1.408(2) . ?
C9 C12 1.395(2) . ?
C9 C10 1.479(2) . ?
C10 C15 1.388(2) . ?
C11 C14 1.382(2) . ?
C12 C13 1.379(2) . ?
C13 C14 1.384(3) . ?
C15 C16 1.441(2) . ?
C15 C18 1.490(2) . ?

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
C16 O2 C17 116.30(14) . . ?
C18 O3 C19 115.83(16) . . ?
C8 N1 C7 113.22(12) . . ?
C10 N2 C7 120.85(13) . . ?
C2 C1 C6 119.14(15) . . ?
C2 C1 C7 120.30(14) . . ?
C6 C1 C7 120.54(13) . . ?
C3 C2 C1 120.27(16) . . ?
C4 C3 C2 119.44(15) . . ?
C3 C4 C5 121.52(15) . . ?
C3 C4 Cl1 119.32(13) . . ?
C5 C4 Cl1 119.16(14) . . ?
C4 C5 C6 118.44(16) . . ?
C5 C6 C1 121.19(15) . . ?
N1 C7 N2 106.74(12) . . ?
N1 C7 C1 111.82(12) . . ?
N2 C7 C1 111.63(12) . . ?
N1 C8 C11 123.15(14) . . ?
N1 C8 C9 117.24(13) . . ?
C11 C8 C9 119.56(14) . . ?
C12 C9 C8 118.98(13) . . ?
C12 C9 C10 123.61(13) . . ?
C8 C9 C10 117.41(13) . . ?
N2 C10 C15 121.69(13) . . ?
N2 C10 C9 114.81(13) . . ?
C15 C10 C9 123.48(13) . . ?
C14 C11 C8 119.64(16) . . ?
C13 C12 C9 120.83(15) . . ?
C12 C13 C14 119.57(15) . . ?
C11 C14 C13 121.02(15) . . ?
C10 C15 C16 121.11(13) . . ?
C10 C15 C18 120.87(13) . . ?
C16 C15 C18 117.28(13) . . ?
O1 C16 O2 121.65(14) . . ?
O1 C16 C15 126.67(14) . . ?
O2 C16 C15 111.67(13) . . ?
O4 C18 O3 122.51(15) . . ?
O4 C18 C15 123.98(15) . . ?
O3 C18 C15 113.51(14) . . ?

_refine_diff_density_max         0.345
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.032



