# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# 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_4clhbp_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2256862'
loop_
_audit_author_name
_audit_author_address
'SUMIT KAMBLE'
;CSIR CSMCRI Bhavnagar Gujarat
India
;
_audit_update_record             
;
2023-04-17 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;
_audit_creation_date             2023-04-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H25 Cl O2'
_chemical_formula_sum            'C21 H25 Cl O2'
_chemical_formula_weight         344.86
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.0699(12)
_cell_length_b                   16.684(3)
_cell_length_c                   9.459(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.436(6)
_cell_angle_gamma                90
_cell_volume                     938.9(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2165
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.97
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.939
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1238
_diffrn_reflns_av_unetI/netI     0.1283
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11874
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.979
_diffrn_reflns_theta_max         24.979
_diffrn_reflns_theta_min         2.197
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.924
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2180
_reflns_number_total             3297
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 
;
 Flack x determined using 734 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3297
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0582
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²+0.3188P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1509
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C00C(H00C), C17(H17), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C),
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.1930(3) 0.68331(13) 0.0107(2) 0.0396(5) Uani 1 1 d . . . . .
O1 O 1.1331(9) 0.3498(3) 0.6051(6) 0.0311(14) Uani 1 1 d . . . . .
H1 H 1.126(12) 0.322(4) 0.547(8) 0.02(3) Uiso 1 1 d . . . . .
C1 C 1.0105(11) 0.4165(4) 0.5544(7) 0.0224(16) Uani 1 1 d . . . . .
C2 C 0.8476(11) 0.4164(4) 0.4271(7) 0.0210(15) Uani 1 1 d . . . . .
O2 O 0.7783(8) 0.6979(3) 0.4767(5) 0.0333(13) Uani 1 1 d . . . . .
C3 C 0.7343(10) 0.4883(4) 0.3895(7) 0.0216(15) Uani 1 1 d . . . . .
H3 H 0.620918 0.490437 0.304479 0.026 Uiso 1 1 calc R . . . .
C6 C 1.0647(11) 0.4850(4) 0.6434(7) 0.0214(15) Uani 1 1 d . . . . .
C5 C 0.9466(11) 0.5553(4) 0.5973(8) 0.0251(16) Uani 1 1 d . . . . .
H5 H 0.980062 0.602849 0.652785 0.030 Uiso 1 1 calc R . . . .
C4 C 0.7827(11) 0.5574(4) 0.4733(7) 0.0235(16) Uani 1 1 d . . . . .
C7 C 0.7919(11) 0.3423(4) 0.3309(7) 0.0229(16) Uani 1 1 d . . . . .
C8 C 0.7033(12) 0.2742(4) 0.4175(8) 0.0299(18) Uani 1 1 d . . . . .
H8A H 0.655784 0.228476 0.353580 0.045 Uiso 1 1 calc GR . . . .
H8B H 0.575094 0.293890 0.456165 0.045 Uiso 1 1 calc GR . . . .
H8C H 0.823224 0.257243 0.497187 0.045 Uiso 1 1 calc GR . . . .
C00C C 0.0872(11) 0.6000(4) 0.2142(7) 0.0270(17) Uani 1 1 d . . . . .
H00C H -0.029705 0.561260 0.204434 0.032 Uiso 1 1 calc R . . . .
C9 C 0.9949(11) 0.3162(4) 0.2676(8) 0.0295(17) Uani 1 1 d . . . . .
H9A H 0.963412 0.264210 0.219751 0.044 Uiso 1 1 calc GR . . . .
H9B H 1.127572 0.311645 0.345341 0.044 Uiso 1 1 calc GR . . . .
H9C H 1.023163 0.356175 0.197364 0.044 Uiso 1 1 calc GR . . . .
C10 C 0.6037(11) 0.3595(4) 0.2004(7) 0.0288(18) Uani 1 1 d . . . . .
H10A H 0.653623 0.400793 0.140090 0.043 Uiso 1 1 calc GR . . . .
H10B H 0.469954 0.378406 0.233851 0.043 Uiso 1 1 calc GR . . . .
H10C H 0.567365 0.310332 0.144006 0.043 Uiso 1 1 calc GR . . . .
C11 C 1.2375(11) 0.4818(4) 0.7847(7) 0.0263(16) Uani 1 1 d . . . . .
C12 C 1.1592(11) 0.4232(5) 0.8908(7) 0.0343(19) Uani 1 1 d . . . . .
H12A H 1.156708 0.368555 0.852495 0.052 Uiso 1 1 calc GR . . . .
H12B H 1.007958 0.438067 0.903124 0.052 Uiso 1 1 calc GR . . . .
H12C H 1.263235 0.425698 0.984267 0.052 Uiso 1 1 calc GR . . . .
C13 C 1.4724(11) 0.4583(4) 0.7601(8) 0.0323(18) Uani 1 1 d . . . . .
H13A H 1.465139 0.405223 0.714899 0.048 Uiso 1 1 calc GR . . . .
H13B H 1.578286 0.456796 0.852923 0.048 Uiso 1 1 calc GR . . . .
H13C H 1.523310 0.497759 0.696906 0.048 Uiso 1 1 calc GR . . . .
C14 C 1.2656(13) 0.5646(4) 0.8586(8) 0.037(2) Uani 1 1 d . . . . .
H14A H 1.319436 0.603267 0.795218 0.055 Uiso 1 1 calc GR . . . .
H14B H 1.374817 0.560585 0.949718 0.055 Uiso 1 1 calc GR . . . .
H14C H 1.120573 0.582409 0.877738 0.055 Uiso 1 1 calc GR . . . .
C15 C 0.6794(11) 0.6367(4) 0.4280(7) 0.0239(16) Uani 1 1 d . . . . .
C16 C 0.4608(11) 0.6443(4) 0.3237(8) 0.0246(16) Uani 1 1 d . . . . .
C17 C 0.2883(11) 0.5878(4) 0.3106(7) 0.0281(17) Uani 1 1 d . . . . .
H17 H 0.308882 0.540657 0.368162 0.034 Uiso 1 1 calc R . . . .
C18 C 0.0592(11) 0.6689(5) 0.1327(7) 0.0295(18) Uani 1 1 d . . . . .
C19 C 0.2248(11) 0.7268(4) 0.1443(7) 0.0274(17) Uani 1 1 d . . . . .
H19 H 0.201380 0.774355 0.088050 0.033 Uiso 1 1 calc R . . . .
C20 C 0.4258(12) 0.7136(4) 0.2401(7) 0.0288(18) Uani 1 1 d . . . . .
H20 H 0.541900 0.752599 0.248965 0.035 Uiso 1 1 calc R . . . .


_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 C18 1.742(6) . ?
O1 C1 1.371(8) . ?
C1 C2 1.398(8) . ?
C1 C6 1.418(9) . ?
C2 C3 1.394(9) . ?
C2 C7 1.532(9) . ?
O2 C15 1.227(8) . ?
C3 C4 1.396(9) . ?
C6 C5 1.399(9) . ?
C6 C11 1.528(9) . ?
C5 C4 1.380(9) . ?
C4 C15 1.490(9) . ?
C7 C8 1.559(9) . ?
C7 C9 1.536(9) . ?
C7 C10 1.533(9) . ?
C00C C17 1.387(9) . ?
C00C C18 1.376(9) . ?
C11 C12 1.543(9) . ?
C11 C13 1.541(10) . ?
C11 C14 1.541(10) . ?
C15 C16 1.494(9) . ?
C16 C17 1.397(9) . ?
C16 C20 1.393(9) . ?
C18 C19 1.383(9) . ?
C19 C20 1.386(10) . ?

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
O1 C1 C2 122.8(6) . . ?
O1 C1 C6 113.6(6) . . ?
C2 C1 C6 123.7(6) . . ?
C1 C2 C7 123.3(6) . . ?
C3 C2 C1 116.5(6) . . ?
C3 C2 C7 120.2(6) . . ?
C2 C3 C4 121.9(6) . . ?
C1 C6 C11 122.0(6) . . ?
C5 C6 C1 116.5(6) . . ?
C5 C6 C11 121.4(6) . . ?
C4 C5 C6 121.6(6) . . ?
C3 C4 C15 122.7(6) . . ?
C5 C4 C3 119.9(6) . . ?
C5 C4 C15 117.2(6) . . ?
C2 C7 C8 109.5(5) . . ?
C2 C7 C9 111.1(6) . . ?
C2 C7 C10 111.7(6) . . ?
C9 C7 C8 112.6(6) . . ?
C10 C7 C8 106.2(5) . . ?
C10 C7 C9 105.5(5) . . ?
C18 C00C C17 119.1(6) . . ?
C6 C11 C12 110.1(5) . . ?
C6 C11 C13 111.9(6) . . ?
C6 C11 C14 111.2(6) . . ?
C13 C11 C12 110.5(6) . . ?
C13 C11 C14 105.9(6) . . ?
C14 C11 C12 107.1(6) . . ?
O2 C15 C4 119.0(5) . . ?
O2 C15 C16 118.7(6) . . ?
C4 C15 C16 122.3(6) . . ?
C17 C16 C15 123.5(6) . . ?
C20 C16 C15 117.5(6) . . ?
C20 C16 C17 118.9(6) . . ?
C00C C17 C16 120.4(6) . . ?
C00C C18 Cl1 118.7(5) . . ?
C00C C18 C19 122.2(6) . . ?
C19 C18 Cl1 119.1(5) . . ?
C18 C19 C20 118.2(6) . . ?
C19 C20 C16 121.2(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate'
