# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_200715_3da_0m
_database_code_depnum_ccdc_archive 'CCDC 2022239'
loop_
_audit_author_name
_audit_author_address
'Yaqiong Li'
;Zhejiang University
China
;
_audit_update_record             
;
2020-08-08 deposited with the CCDC.	2021-02-24 downloaded from the CCDC.
;
_audit_creation_date             2020-07-15
_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        
(4-Chlorophenyl)(3,5-diphenylcyclopent-2-en-1-yl)methanone
_chemical_formula_moiety         'C24 H19 Cl O'
_chemical_formula_sum            'C24 H19 Cl O'
_chemical_formula_weight         358.84
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.972(3)
_cell_length_b                   9.389(3)
_cell_length_c                   13.279(5)
_cell_angle_alpha                85.406(17)
_cell_angle_beta                 84.165(19)
_cell_angle_gamma                67.620(18)
_cell_volume                     913.3(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8739
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   0.951
_shelx_estimated_absorpt_T_min   0.906
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0957 before and 0.0396 after correction.
The Ratio of minimum to maximum transmission is 0.9620.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15237
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.113
_diffrn_reflns_theta_min         2.752
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3609
_reflns_number_total             4019
_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       SAINT
_computing.data_collection       Bruker
_computing.data_reduction        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 (Sheldrick, 2015)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4019
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²+0.2756P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0972
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C12(H12), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.12630(7) 0.23714(5) 0.04991(3) 0.06369(15) Uani 1 1 d . . . . .
O1 O 0.24924(14) 0.39583(11) 0.51132(7) 0.0432(2) Uani 1 1 d . . . . .
C1 C 0.08362(18) 0.52243(15) 0.26516(11) 0.0385(3) Uani 1 1 d . . . . .
H1 H 0.023198 0.629419 0.276013 0.046 Uiso 1 1 calc R . . . .
C2 C 0.0642(2) 0.46431(16) 0.17646(11) 0.0446(3) Uani 1 1 d . . . . .
H2 H -0.010292 0.530251 0.126965 0.053 Uiso 1 1 calc R . . . .
C3 C 0.1546(2) 0.30944(16) 0.16100(10) 0.0408(3) Uani 1 1 d . . . . .
C4 C 0.26403(19) 0.21085(16) 0.23203(11) 0.0418(3) Uani 1 1 d . . . . .
H4 H 0.326599 0.104445 0.219949 0.050 Uiso 1 1 calc R . . . .
C5 C 0.28036(17) 0.27026(14) 0.32072(11) 0.0362(3) Uani 1 1 d . . . . .
H5 H 0.354120 0.203650 0.370277 0.043 Uiso 1 1 calc R . . . .
C6 C 0.19028(15) 0.42643(13) 0.33863(9) 0.0307(2) Uani 1 1 d . . . . .
C7 C 0.20655(16) 0.48443(14) 0.43749(10) 0.0317(3) Uani 1 1 d . . . . .
C8 C 0.17423(16) 0.65337(13) 0.44255(9) 0.0302(2) Uani 1 1 d . . . . .
H8 H 0.064930 0.716778 0.405574 0.036 Uiso 1 1 calc R . . . .
C9 C 0.34193(15) 0.68995(13) 0.39502(9) 0.0285(2) Uani 1 1 d . . . . .
H9 H 0.452871 0.606587 0.420446 0.034 Uiso 1 1 calc R . . . .
C10 C 0.31711(18) 0.83773(14) 0.44772(9) 0.0329(3) Uani 1 1 d . . . . .
H10A H 0.435639 0.846388 0.453596 0.039 Uiso 1 1 calc R . . . .
H10B H 0.237584 0.930814 0.410690 0.039 Uiso 1 1 calc R . . . .
C11 C 0.22836(15) 0.81518(13) 0.55092(9) 0.0295(2) Uani 1 1 d . . . . .
C12 C 0.15221(16) 0.71154(14) 0.54750(9) 0.0331(3) Uani 1 1 d . . . . .
H12 H 0.091499 0.678449 0.604315 0.040 Uiso 1 1 calc R . . . .
C13 C 0.37006(16) 0.69656(13) 0.28089(9) 0.0293(2) Uani 1 1 d . . . . .
C14 C 0.24840(19) 0.80820(15) 0.22072(10) 0.0386(3) Uani 1 1 d . . . . .
H14 H 0.143736 0.884695 0.251710 0.046 Uiso 1 1 calc R . . . .
C15 C 0.2776(2) 0.80951(17) 0.11619(11) 0.0488(4) Uani 1 1 d . . . . .
H15 H 0.192488 0.886170 0.076073 0.059 Uiso 1 1 calc R . . . .
C16 C 0.4300(2) 0.6999(2) 0.06977(11) 0.0524(4) Uani 1 1 d . . . . .
H16 H 0.450216 0.701541 -0.001994 0.063 Uiso 1 1 calc R . . . .
C17 C 0.5523(2) 0.58837(19) 0.12825(11) 0.0506(4) Uani 1 1 d . . . . .
H17 H 0.656943 0.512471 0.096789 0.061 Uiso 1 1 calc R . . . .
C18 C 0.52280(18) 0.58667(15) 0.23322(10) 0.0389(3) Uani 1 1 d . . . . .
H18 H 0.608020 0.509488 0.273001 0.047 Uiso 1 1 calc R . . . .
C19 C 0.23229(15) 0.90051(13) 0.63823(9) 0.0294(2) Uani 1 1 d . . . . .
C20 C 0.20205(17) 0.84910(15) 0.73802(9) 0.0371(3) Uani 1 1 d . . . . .
H20 H 0.170668 0.760879 0.749939 0.044 Uiso 1 1 calc R . . . .
C21 C 0.21752(19) 0.92571(18) 0.81924(10) 0.0450(3) Uani 1 1 d . . . . .
H21 H 0.197063 0.889460 0.886434 0.054 Uiso 1 1 calc R . . . .
C22 C 0.26268(19) 1.05504(18) 0.80334(11) 0.0469(3) Uani 1 1 d . . . . .
H22 H 0.275539 1.105971 0.859367 0.056 Uiso 1 1 calc R . . . .
C23 C 0.28891(18) 1.10949(16) 0.70535(11) 0.0406(3) Uani 1 1 d . . . . .
H23 H 0.317256 1.199294 0.694015 0.049 Uiso 1 1 calc R . . . .
C24 C 0.27376(16) 1.03275(14) 0.62365(10) 0.0333(3) Uani 1 1 d . . . . .
H24 H 0.291930 1.070903 0.556676 0.040 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 C3 1.7415(15) . ?
O1 C7 1.2209(16) . ?
C1 H1 0.9500 . ?
C1 C2 1.383(2) . ?
C1 C6 1.3897(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.377(2) . ?
C3 C4 1.386(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3934(18) . ?
C6 C7 1.4965(18) . ?
C7 C8 1.5130(17) . ?
C8 H8 1.0000 . ?
C8 C9 1.5643(17) . ?
C8 C12 1.5068(18) . ?
C9 H9 1.0000 . ?
C9 C10 1.5402(17) . ?
C9 C13 1.5091(17) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5145(17) . ?
C11 C12 1.3342(17) . ?
C11 C19 1.4705(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3882(18) . ?
C13 C18 1.3925(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.377(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.390(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.4029(18) . ?
C19 C24 1.3962(18) . ?
C20 H20 0.9500 . ?
C20 C21 1.384(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.385(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.3888(18) . ?
C24 H24 0.9500 . ?

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
C2 C1 H1 119.6 . . ?
C2 C1 C6 120.90(12) . . ?
C6 C1 H1 119.6 . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 118.99(13) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 Cl1 118.54(12) . . ?
C2 C3 C4 121.62(13) . . ?
C4 C3 Cl1 119.83(11) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.71(12) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.99(12) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.78(12) . . ?
C1 C6 C7 122.13(11) . . ?
C5 C6 C7 119.06(11) . . ?
O1 C7 C6 120.28(11) . . ?
O1 C7 C8 121.21(12) . . ?
C6 C7 C8 118.48(10) . . ?
C7 C8 H8 109.3 . . ?
C7 C8 C9 111.80(10) . . ?
C9 C8 H8 109.3 . . ?
C12 C8 C7 115.68(10) . . ?
C12 C8 H8 109.3 . . ?
C12 C8 C9 101.26(9) . . ?
C8 C9 H9 106.9 . . ?
C10 C9 C8 102.16(9) . . ?
C10 C9 H9 106.9 . . ?
C13 C9 C8 117.05(10) . . ?
C13 C9 H9 106.9 . . ?
C13 C9 C10 116.12(10) . . ?
C9 C10 H10A 111.2 . . ?
C9 C10 H10B 111.2 . . ?
H10A C10 H10B 109.2 . . ?
C11 C10 C9 102.62(10) . . ?
C11 C10 H10A 111.2 . . ?
C11 C10 H10B 111.2 . . ?
C12 C11 C10 110.18(11) . . ?
C12 C11 C19 128.19(11) . . ?
C19 C11 C10 121.63(10) . . ?
C8 C12 H12 124.1 . . ?
C11 C12 C8 111.75(10) . . ?
C11 C12 H12 124.1 . . ?
C14 C13 C9 122.48(11) . . ?
C14 C13 C18 118.19(12) . . ?
C18 C13 C9 119.32(11) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.85(13) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.39(14) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.56(14) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.09(14) . . ?
C18 C17 H17 120.0 . . ?
C13 C18 H18 119.5 . . ?
C17 C18 C13 120.91(13) . . ?
C17 C18 H18 119.5 . . ?
C20 C19 C11 121.53(11) . . ?
C24 C19 C11 120.35(11) . . ?
C24 C19 C20 118.07(11) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.61(13) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.53(13) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 120.2 . . ?
C23 C22 C21 119.64(13) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 119.97(13) . . ?
C24 C23 H23 120.0 . . ?
C19 C24 H24 119.4 . . ?
C23 C24 C19 121.15(12) . . ?
C23 C24 H24 119.4 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
