# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_tz-1
_database_code_depnum_ccdc_archive 'CCDC 1949691'
_audit_update_record             
;
2019-08-27 deposited with the CCDC.	2022-12-04 downloaded from the CCDC.
;
_audit_creation_date             2018-11-01
_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         'C22 H18 O2'
_chemical_formula_sum            'C22 H18 O2'
_chemical_formula_weight         314.36
_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'
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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   16.6597(9)
_cell_length_b                   9.1073(4)
_cell_length_c                   10.5974(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.571(5)
_cell_angle_gamma                90
_cell_volume                     1602.78(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3745
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.1210
_cell_measurement_theta_min      2.4330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5926
_diffrn_reflns_point_group_measured_fraction_full 0.777
_diffrn_reflns_point_group_measured_fraction_max 0.646
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.301
_diffrn_reflns_theta_min         2.453
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  58.00   1.00    2.50    --  -11.43  57.00  30.00   91
  2  ω    -74.00  17.00   1.00    2.50    --  -11.43 -77.00 120.00   91
  3  ω    -81.00  17.00   1.00    2.50    --  -11.43 -57.00-120.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0322620000
_diffrn_orient_matrix_UB_12      -0.0435437000
_diffrn_orient_matrix_UB_13      -0.0189436000
_diffrn_orient_matrix_UB_21      0.0012552000
_diffrn_orient_matrix_UB_22      0.0429513000
_diffrn_orient_matrix_UB_23      -0.0555772000
_diffrn_orient_matrix_UB_31      0.0279459000
_diffrn_orient_matrix_UB_32      0.0483326000
_diffrn_orient_matrix_UB_33      0.0324650000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.464
_reflns_Friedel_fraction_full    0.554
_reflns_Friedel_fraction_max     0.410
_reflns_number_gt                2758
_reflns_number_total             2822
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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         0.191
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 846 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2822
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.058
_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)+(0.0376P)²+0.4721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0758
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C6(H6), C19(H19), C17(H17), C4(H4), C2(H2), C3(H3), C5(H5),
 C12(H12), C13(H13), C20(H20), C14(H14), C11(H11)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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
O1 O 0.56412(8) 0.70472(14) 0.72693(13) 0.0199(3) Uani 1 1 d . . . . .
O2 O 0.67625(9) 0.60928(15) 0.65704(14) 0.0258(3) Uani 1 1 d . . . . .
C15 C 0.61204(11) 0.66641(19) 0.63210(19) 0.0181(4) Uani 1 1 d . . . . .
C21 C 0.49381(11) 0.76964(19) 0.67049(19) 0.0176(4) Uani 1 1 d . . . . .
C10 C 0.62462(12) 0.9600(2) 0.4645(2) 0.0207(4) Uani 1 1 d . . . . .
H10 H 0.596210 0.991210 0.531613 0.025 Uiso 1 1 calc R . . . .
C6 C 0.52877(12) 0.3374(2) 0.56535(19) 0.0199(4) Uani 1 1 d . . . . .
H6 H 0.584301 0.325415 0.576989 0.024 Uiso 1 1 calc R . . . .
C19 C 0.36486(12) 0.87668(19) 0.6631(2) 0.0198(4) Uani 1 1 d . . . . .
H19 H 0.321098 0.910774 0.703872 0.024 Uiso 1 1 calc R . . . .
C1 C 0.49669(12) 0.45316(19) 0.49014(19) 0.0180(4) Uani 1 1 d . . . . .
C16 C 0.49367(11) 0.77559(19) 0.54029(19) 0.0161(4) Uani 1 1 d . . . . .
C17 C 0.42783(11) 0.8344(2) 0.4690(2) 0.0174(4) Uani 1 1 d . . . . .
H17 H 0.427626 0.840631 0.381385 0.021 Uiso 1 1 calc R . . . .
C4 C 0.39551(12) 0.2582(2) 0.6076(2) 0.0218(4) Uani 1 1 d . . . . .
H4 H 0.361930 0.194633 0.647481 0.026 Uiso 1 1 calc R . . . .
C9 C 0.62217(11) 0.8114(2) 0.42925(19) 0.0171(4) Uani 1 1 d . . . . .
C2 C 0.41308(12) 0.4676(2) 0.4734(2) 0.0204(4) Uani 1 1 d . . . . .
H2 H 0.390726 0.542208 0.422021 0.024 Uiso 1 1 calc R . . . .
C3 C 0.36269(12) 0.3721(2) 0.5323(2) 0.0227(4) Uani 1 1 d . . . . .
H3 H 0.307144 0.384168 0.521386 0.027 Uiso 1 1 calc R . . . .
C5 C 0.47841(12) 0.2400(2) 0.6230(2) 0.0220(4) Uani 1 1 d . . . . .
H5 H 0.500394 0.162739 0.671658 0.026 Uiso 1 1 calc R . . . .
C12 C 0.71134(12) 1.0159(2) 0.3001(2) 0.0235(4) Uani 1 1 d . . . . .
H12 H 0.740311 1.083621 0.256241 0.028 Uiso 1 1 calc R . . . .
C13 C 0.71039(12) 0.8689(2) 0.2653(2) 0.0233(4) Uani 1 1 d . . . . .
H13 H 0.739295 0.838182 0.198607 0.028 Uiso 1 1 calc R . . . .
C20 C 0.43112(12) 0.8200(2) 0.7360(2) 0.0203(4) Uani 1 1 d . . . . .
H20 H 0.432896 0.816471 0.823876 0.024 Uiso 1 1 calc R . . . .
C18 C 0.36178(11) 0.88414(19) 0.5308(2) 0.0179(4) Uani 1 1 d . . . . .
C7 C 0.55168(12) 0.55876(19) 0.42679(19) 0.0175(4) Uani 1 1 d . . . . .
H7A H 0.527077 0.582600 0.343263 0.021 Uiso 1 1 calc R . . . .
H7B H 0.602217 0.509312 0.415760 0.021 Uiso 1 1 calc R . . . .
C14 C 0.66634(11) 0.7670(2) 0.32989(19) 0.0192(4) Uani 1 1 d . . . . .
H14 H 0.666502 0.668666 0.306301 0.023 Uiso 1 1 calc R . . . .
C11 C 0.66894(13) 1.0614(2) 0.4004(2) 0.0247(4) Uani 1 1 d . . . . .
H11 H 0.670081 1.159454 0.424887 0.030 Uiso 1 1 calc R . . . .
C8 C 0.57006(11) 0.70491(19) 0.50074(19) 0.0162(4) Uani 1 1 d . . . . .
C22 C 0.28860(12) 0.9453(2) 0.4551(2) 0.0235(4) Uani 1 1 d . . . . .
H22A H 0.241825 0.930613 0.500967 0.035 Uiso 1 1 calc GR . . . .
H22B H 0.281458 0.895654 0.375076 0.035 Uiso 1 1 calc GR . . . .
H22C H 0.296027 1.048372 0.441221 0.035 Uiso 1 1 calc GR . . . .


_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
O1 C15 1.377(2) . ?
O1 C21 1.403(2) . ?
O2 C15 1.200(2) . ?
C15 C8 1.547(3) . ?
C21 C16 1.381(3) . ?
C21 C20 1.378(3) . ?
C10 C9 1.404(3) . ?
C10 C11 1.392(3) . ?
C6 C1 1.402(3) . ?
C6 C5 1.395(3) . ?
C19 C20 1.395(3) . ?
C19 C18 1.401(3) . ?
C1 C2 1.396(3) . ?
C1 C7 1.521(3) . ?
C16 C17 1.389(3) . ?
C16 C8 1.515(3) . ?
C17 C18 1.400(3) . ?
C4 C3 1.393(3) . ?
C4 C5 1.388(3) . ?
C9 C14 1.392(3) . ?
C9 C8 1.540(3) . ?
C2 C3 1.391(3) . ?
C12 C13 1.388(3) . ?
C12 C11 1.385(3) . ?
C13 C14 1.396(3) . ?
C18 C22 1.511(3) . ?
C7 C8 1.562(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
C15 O1 C21 107.96(15) . . ?
O1 C15 C8 110.63(15) . . ?
O2 C15 O1 120.49(18) . . ?
O2 C15 C8 128.86(18) . . ?
C16 C21 O1 112.18(16) . . ?
C20 C21 O1 124.48(18) . . ?
C20 C21 C16 123.33(18) . . ?
C11 C10 C9 121.00(19) . . ?
C5 C6 C1 120.80(18) . . ?
C20 C19 C18 122.45(18) . . ?
C6 C1 C7 120.72(17) . . ?
C2 C1 C6 118.31(18) . . ?
C2 C1 C7 120.96(17) . . ?
C21 C16 C17 119.81(17) . . ?
C21 C16 C8 108.98(16) . . ?
C17 C16 C8 131.14(19) . . ?
C16 C17 C18 119.12(19) . . ?
C5 C4 C3 119.86(18) . . ?
C10 C9 C8 118.80(17) . . ?
C14 C9 C10 118.36(18) . . ?
C14 C9 C8 122.83(16) . . ?
C3 C2 C1 121.06(18) . . ?
C2 C3 C4 119.94(19) . . ?
C4 C5 C6 120.00(18) . . ?
C11 C12 C13 119.73(19) . . ?
C12 C13 C14 120.4(2) . . ?
C21 C20 C19 116.25(19) . . ?
C19 C18 C22 120.84(17) . . ?
C17 C18 C19 119.01(17) . . ?
C17 C18 C22 120.14(18) . . ?
C1 C7 C8 114.72(16) . . ?
C9 C14 C13 120.54(18) . . ?
C12 C11 C10 119.91(19) . . ?
C15 C8 C7 108.34(14) . . ?
C16 C8 C15 100.18(16) . . ?
C16 C8 C9 112.80(14) . . ?
C16 C8 C7 111.43(15) . . ?
C9 C8 C15 110.68(15) . . ?
C9 C8 C7 112.65(16) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.402
_oxdiff_exptl_absorpt_empirical_full_min 0.764
