# 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 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_zak2
_database_code_depnum_ccdc_archive 'CCDC 1545936'
_audit_update_record             
;
2017-04-25 deposited with the CCDC.	2022-05-23 downloaded from the CCDC.
;
_audit_creation_date             2017-04-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 O'
_chemical_formula_sum            'C23 H20 O'
_chemical_formula_weight         312.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'N2 O3 C15 H12 s1'
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      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                   5.7804(3)
_cell_length_b                   8.8933(7)
_cell_length_c                   16.3510(11)
_cell_angle_alpha                87.212(6)
_cell_angle_beta                 84.983(5)
_cell_angle_gamma                89.862(6)
_cell_volume                     836.34(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2355
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.3240
_cell_measurement_theta_min      3.3080
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       tables
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7027
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_min         3.313
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -79.00   32.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241    0.0000   90.0000 111

#__ type_ start__ end____ width___ exp.time_
  2 omega  -80.00    4.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -77.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega  -90.00  -58.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  178.0000  -60.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega  -25.00   64.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000  120.0000 89

#__ type_ start__ end____ width___ exp.time_
  5 omega   -7.00   93.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000 -120.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0744056000
_diffrn_orient_matrix_UB_12      -0.0262706000
_diffrn_orient_matrix_UB_13      0.0345057000
_diffrn_orient_matrix_UB_21      0.0311825000
_diffrn_orient_matrix_UB_22      0.0627455000
_diffrn_orient_matrix_UB_23      0.0218843000
_diffrn_orient_matrix_UB_31      -0.0930843000
_diffrn_orient_matrix_UB_32      0.0418223000
_diffrn_orient_matrix_UB_33      -0.0152057000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3205
_reflns_number_total             3839
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3839
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0533
_refine_ls_restrained_S_all      1.030
_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)+(0.0705P)²+0.2764P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1470
_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:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C23(H23), C15(H15), C21(H21), C8(H8), C11(H11), C2(H2), C19(H19),
 C14(H14), C9(H9), C20(H20), C7(H7), C3(H3), C13(H13), C10(H10), C16(H16),
 C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
C5 C 0.1916(2) 0.97337(16) 0.29130(9) 0.0183(3) Uani 1 1 d . . . . .
H5 H 0.0368 0.9361 0.3118 0.022 Uiso 1 1 calc R . . . .
C17 C 0.5526(2) 0.80637(16) 0.29828(9) 0.0201(3) Uani 1 1 d . . . . .
H17 H 0.5725 0.8104 0.2412 0.024 Uiso 1 1 calc R . . . .
C18 C -0.0830(2) 1.29505(16) -0.02597(9) 0.0187(3) Uani 1 1 d . . . . .
C6 C 0.2023(2) 1.13861(16) 0.31245(8) 0.0175(3) Uani 1 1 d . . . . .
C23 C -0.2595(3) 1.39179(18) -0.04827(9) 0.0227(3) Uani 1 1 d . . . . .
H23 H -0.4047 1.3859 -0.0189 0.027 Uiso 1 1 calc R . . . .
O1 O -0.33584(18) 1.16479(15) 0.07474(8) 0.0341(3) Uani 1 1 d . . . . .
C15 C 0.6832(3) 0.71874(17) 0.42805(10) 0.0243(3) Uani 1 1 d . . . . .
H15 H 0.7883 0.6651 0.4580 0.029 Uiso 1 1 calc R . . . .
C1 C -0.1339(3) 1.18894(17) 0.04760(9) 0.0222(3) Uani 1 1 d . . . . .
C12 C 0.3668(2) 0.88167(16) 0.33770(9) 0.0185(3) Uani 1 1 d . . . . .
C21 C -0.0066(3) 1.50462(18) -0.15815(9) 0.0255(3) Uani 1 1 d . . . . .
H21 H 0.0198 1.5752 -0.2018 0.031 Uiso 1 1 calc R . . . .
C8 C 0.4112(3) 1.37344(18) 0.31308(9) 0.0232(3) Uani 1 1 d . . . . .
H8 H 0.5442 1.4302 0.2978 0.028 Uiso 1 1 calc R . . . .
C11 C 0.0170(2) 1.20374(17) 0.35803(9) 0.0199(3) Uani 1 1 d . . . . .
H11 H -0.1165 1.1473 0.3732 0.024 Uiso 1 1 calc R . . . .
C4 C 0.2179(3) 0.95256(17) 0.19780(9) 0.0209(3) Uani 1 1 d . . . . .
H4A H 0.3670 0.9927 0.1751 0.025 Uiso 1 1 calc R . . . .
H4B H 0.2160 0.8459 0.1880 0.025 Uiso 1 1 calc R . . . .
C2 C 0.0636(3) 1.11915(17) 0.08739(9) 0.0220(3) Uani 1 1 d . . . . .
H2 H 0.2145 1.1388 0.0649 0.026 Uiso 1 1 calc R . . . .
C19 C 0.1333(3) 1.30286(17) -0.07160(9) 0.0216(3) Uani 1 1 d . . . . .
H19 H 0.2525 1.2385 -0.0579 0.026 Uiso 1 1 calc R . . . .
C14 C 0.4982(3) 0.79324(18) 0.46830(10) 0.0289(4) Uani 1 1 d . . . . .
H14 H 0.4795 0.7894 0.5254 0.035 Uiso 1 1 calc R . . . .
C9 C 0.2263(3) 1.43714(17) 0.35935(9) 0.0235(3) Uani 1 1 d . . . . .
H9 H 0.2355 1.5357 0.3753 0.028 Uiso 1 1 calc R . . . .
C20 C 0.1694(3) 1.40731(18) -0.13751(9) 0.0244(3) Uani 1 1 d . . . . .
H20 H 0.3129 1.4120 -0.1681 0.029 Uiso 1 1 calc R . . . .
C7 C 0.3996(2) 1.22615(17) 0.28943(9) 0.0207(3) Uani 1 1 d . . . . .
H7 H 0.5241 1.1854 0.2580 0.025 Uiso 1 1 calc R . . . .
C3 C 0.0289(3) 1.02931(17) 0.15442(9) 0.0213(3) Uani 1 1 d . . . . .
H3 H -0.1236 1.0127 0.1761 0.026 Uiso 1 1 calc R . . . .
C13 C 0.3416(3) 0.87324(18) 0.42360(9) 0.0258(3) Uani 1 1 d . . . . .
H13 H 0.2178 0.9220 0.4512 0.031 Uiso 1 1 calc R . . . .
C10 C 0.0280(3) 1.35197(18) 0.38142(9) 0.0231(3) Uani 1 1 d . . . . .
H10 H -0.0975 1.3937 0.4118 0.028 Uiso 1 1 calc R . . . .
C16 C 0.7098(3) 0.72488(17) 0.34302(10) 0.0221(3) Uani 1 1 d . . . . .
H16 H 0.8325 0.6747 0.3157 0.027 Uiso 1 1 calc R . . . .
C22 C -0.2216(3) 1.49644(18) -0.11359(10) 0.0259(3) Uani 1 1 d . . . . .
H22 H -0.3403 1.5611 -0.1275 0.031 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
C5 H5 0.9800 . ?
C5 C6 1.5285(19) . ?
C5 C12 1.5284(19) . ?
C5 C4 1.543(2) . ?
C17 H17 0.9300 . ?
C17 C12 1.391(2) . ?
C17 C16 1.395(2) . ?
C18 C23 1.395(2) . ?
C18 C1 1.501(2) . ?
C18 C19 1.399(2) . ?
C6 C11 1.392(2) . ?
C6 C7 1.396(2) . ?
C23 H23 0.9300 . ?
C23 C22 1.385(2) . ?
O1 C1 1.2274(18) . ?
C15 H15 0.9300 . ?
C15 C14 1.389(2) . ?
C15 C16 1.384(2) . ?
C1 C2 1.483(2) . ?
C12 C13 1.398(2) . ?
C21 H21 0.9300 . ?
C21 C20 1.387(2) . ?
C21 C22 1.385(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.390(2) . ?
C8 C7 1.387(2) . ?
C11 H11 0.9300 . ?
C11 C10 1.393(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.499(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.325(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.390(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.386(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.387(2) . ?
C20 H20 0.9300 . ?
C7 H7 0.9300 . ?
C3 H3 0.9300 . ?
C13 H13 0.9300 . ?
C10 H10 0.9300 . ?
C16 H16 0.9300 . ?
C22 H22 0.9300 . ?

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
C6 C5 H5 106.9 . . ?
C6 C5 C4 112.61(11) . . ?
C12 C5 H5 106.9 . . ?
C12 C5 C6 109.90(11) . . ?
C12 C5 C4 113.14(12) . . ?
C4 C5 H5 106.9 . . ?
C12 C17 H17 119.4 . . ?
C12 C17 C16 121.10(14) . . ?
C16 C17 H17 119.4 . . ?
C23 C18 C1 117.88(13) . . ?
C23 C18 C19 119.05(13) . . ?
C19 C18 C1 123.05(13) . . ?
C11 C6 C5 120.32(13) . . ?
C11 C6 C7 118.39(13) . . ?
C7 C6 C5 121.24(13) . . ?
C18 C23 H23 119.6 . . ?
C22 C23 C18 120.90(14) . . ?
C22 C23 H23 119.6 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C16 C15 C14 119.52(14) . . ?
O1 C1 C18 119.81(13) . . ?
O1 C1 C2 121.52(14) . . ?
C2 C1 C18 118.64(12) . . ?
C17 C12 C5 122.94(13) . . ?
C17 C12 C13 118.06(13) . . ?
C13 C12 C5 119.00(13) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C22 C21 C20 119.87(14) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.78(14) . . ?
C6 C11 H11 119.4 . . ?
C6 C11 C10 121.19(14) . . ?
C10 C11 H11 119.4 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C3 C4 C5 112.49(12) . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.19(14) . . ?
C3 C2 H2 119.4 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.70(14) . . ?
C20 C19 H19 120.2 . . ?
C15 C14 H14 119.9 . . ?
C13 C14 C15 120.25(14) . . ?
C13 C14 H14 119.9 . . ?
C8 C9 H9 120.4 . . ?
C10 C9 C8 119.24(14) . . ?
C10 C9 H9 120.4 . . ?
C21 C20 C19 120.64(14) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.45(13) . . ?
C8 C7 H7 119.8 . . ?
C4 C3 H3 117.7 . . ?
C2 C3 C4 124.67(14) . . ?
C2 C3 H3 117.7 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.02(14) . . ?
C14 C13 H13 119.5 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 C11 119.94(14) . . ?
C9 C10 H10 120.0 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 C17 120.04(14) . . ?
C15 C16 H16 120.0 . . ?
C23 C22 H22 120.1 . . ?
C21 C22 C23 119.83(15) . . ?
C21 C22 H22 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C6 C11 C10 176.77(13) . . . . ?
C5 C6 C7 C8 -176.39(13) . . . . ?
C5 C12 C13 C14 -179.03(14) . . . . ?
C5 C4 C3 C2 131.13(16) . . . . ?
C17 C12 C13 C14 0.5(2) . . . . ?
C18 C23 C22 C21 0.7(2) . . . . ?
C18 C1 C2 C3 177.31(14) . . . . ?
C18 C19 C20 C21 0.4(2) . . . . ?
C6 C5 C12 C17 -117.38(15) . . . . ?
C6 C5 C12 C13 62.15(17) . . . . ?
C6 C5 C4 C3 -61.00(16) . . . . ?
C6 C11 C10 C9 -0.1(2) . . . . ?
C23 C18 C1 O1 16.2(2) . . . . ?
C23 C18 C1 C2 -161.91(14) . . . . ?
C23 C18 C19 C20 0.7(2) . . . . ?
O1 C1 C2 C3 -0.8(2) . . . . ?
C15 C14 C13 C12 -0.5(3) . . . . ?
C1 C18 C23 C22 177.55(14) . . . . ?
C1 C18 C19 C20 -178.05(14) . . . . ?
C1 C2 C3 C4 179.11(14) . . . . ?
C12 C5 C6 C11 -111.58(14) . . . . ?
C12 C5 C6 C7 66.04(16) . . . . ?
C12 C5 C4 C3 173.62(12) . . . . ?
C12 C17 C16 C15 -0.4(2) . . . . ?
C8 C9 C10 C11 0.8(2) . . . . ?
C11 C6 C7 C8 1.3(2) . . . . ?
C4 C5 C6 C11 121.29(14) . . . . ?
C4 C5 C6 C7 -61.09(17) . . . . ?
C4 C5 C12 C17 9.45(19) . . . . ?
C4 C5 C12 C13 -171.03(13) . . . . ?
C19 C18 C23 C22 -1.2(2) . . . . ?
C19 C18 C1 O1 -165.07(15) . . . . ?
C19 C18 C1 C2 16.8(2) . . . . ?
C14 C15 C16 C17 0.5(2) . . . . ?
C9 C8 C7 C6 -0.6(2) . . . . ?
C20 C21 C22 C23 0.4(2) . . . . ?
C7 C6 C11 C10 -0.9(2) . . . . ?
C7 C8 C9 C10 -0.4(2) . . . . ?
C16 C17 C12 C5 179.46(13) . . . . ?
C16 C17 C12 C13 -0.1(2) . . . . ?
C16 C15 C14 C13 0.0(2) . . . . ?
C22 C21 C20 C19 -1.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_9827-12954_mok144(1)
_database_code_depnum_ccdc_archive 'CCDC 2153106'
loop_
_audit_author_name
_audit_author_address
'Aleksander Vasilyev'
;Saint Petersburg State  University
Russia
;
_audit_update_record             
;
2022-02-18 deposited with the CCDC.	2022-05-23 downloaded from the CCDC.
;
_audit_creation_date             2022-02-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H24 O'
_chemical_formula_sum            'C25 H24 O'
_chemical_formula_weight         340.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         'O C20'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.4843(7)
_cell_length_b                   5.6568(6)
_cell_length_c                   34.252(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.212(8)
_cell_angle_gamma                90
_cell_volume                     1826.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3119
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.6970
_cell_measurement_theta_min      2.5590
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.562
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.50a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            9481
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.374
_diffrn_reflns_theta_min         2.595
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -80.00 -42.00   0.50    5.06    --  -38.95 116.00 -53.00   76
  2  ω    -25.00   5.00   0.50    5.06    --  -38.95 116.00 -53.00   60
  3  ω    -88.00 -61.00   0.50    5.06    --  -38.95 165.00  93.00   54
  4  ω     54.00  90.00   0.50    5.06    --   38.95 165.00  93.00   72
  5  ω      5.00  30.00   0.50    5.06    --   38.95-116.00-142.00   50
  6  ω     45.00  71.00   0.50   10.00    --  100.00-116.00-142.00   52
  7  ω     79.00 136.00   0.50   10.00    --  100.00 116.00 -53.00  114
  8  ω     41.00 145.00   0.50   10.00    --  100.00-165.00  70.00  208
  9  ω     77.00 102.00   0.50   10.00    --  100.00 165.00  93.00   50
 10  ω     -9.00  25.00   0.50    5.06    --  -38.95  32.00  90.00   68
 11  ω    -55.00 -20.00   0.50    5.06    --  -38.95 -21.00-180.00   70
 12  ω   -109.00 -66.00   0.50    5.06    --  -38.95 -21.00-180.00   86
 13  ω    -15.00  24.00   0.50    5.06    --  -38.95  32.00 120.00   78
 14  ω    -72.00 -47.00   0.50    5.06    --  -38.95-165.00  70.00   50
 15  ω    -54.00 -13.00   0.50    5.06    --  -38.95 -77.00  60.00   82
 16  ω    -52.00 -15.00   0.50    5.06    --  -38.95  32.00  90.00   74
 17  ω   -104.00 -58.00   0.50    5.06    --  -38.95 -77.00  60.00   92
 18  ω    -13.00  22.00   0.50    5.06    --   38.95 -43.00 -60.00   70
 19  ω    -27.00  -1.00   0.50    5.06    --   38.95 -77.00-180.00   52
 20  ω     47.00  92.00   0.50    5.06    --   38.95-138.00  90.00   90
 21  ω     31.00  56.00   0.50    5.06    --   38.95 -77.00-180.00   50
 22  ω     22.00  49.00   0.50    5.06    --   38.95 -32.00 150.00   54
 23  ω    -25.00   1.00   0.50    5.06    --   38.95 -32.00 150.00   52
 24  ω     86.00 111.00   0.50   10.00    --  100.00-111.00   0.00   50
 25  ω     44.00  70.00   0.50   10.00    --  100.00-111.00   0.00   52
 26  ω    126.00 152.00   0.50   10.00    --  100.00  93.00 -90.00   52
 27  ω    120.00 156.00   0.50   10.00    --  100.00  45.00   0.00   72
 28  ω     81.00 145.00   0.50   10.00    --  100.00  93.00  60.00  128
 29  ω     43.00 114.00   0.50   10.00    --  100.00 -61.00-180.00  142
 30  ω     88.00 115.00   0.50   10.00    --  100.00 -37.00 150.00   54
 31  ω     90.00 139.00   0.50   10.00    --  100.00  53.00 -60.00   98
 32  ω     34.00  74.00   0.50   10.00    --  100.00 -37.00 150.00   80
 33  ω     73.00 115.00   0.50   10.00    --  100.00 -37.00-180.00   84
 34  ω    123.00 156.00   0.50   10.00    --  100.00  77.00   0.00   66
 35  ω     42.00  92.00   0.50   10.00    --  100.00-111.00  60.00  100
 36  ω     82.00 126.00   0.50   10.00    --  100.00 -77.00-150.00   88
 37  ω     65.00 111.00   0.50   10.00    --  100.00-111.00-120.00   92
 38  ω     81.00 107.00   0.50   10.00    --  100.00  93.00-150.00   52
 39  ω     82.00 130.00   0.50   10.00    --  100.00 -86.00-150.00   96
 40  ω    104.00 129.00   0.50   10.00    --  100.00  30.00-150.00   50
 41  ω     74.00 113.00   0.50   10.00    --  100.00  77.00   0.00   78
 42  ω     62.00  94.00   0.50   10.00    --  100.00 -93.00-180.00   64
 43  ω     75.00 154.00   0.50   10.00    --  100.00  77.00  30.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1278044000
_diffrn_orient_matrix_UB_12      0.0346939000
_diffrn_orient_matrix_UB_13      -0.0236479000
_diffrn_orient_matrix_UB_21      -0.0320956000
_diffrn_orient_matrix_UB_22      0.2662568000
_diffrn_orient_matrix_UB_23      -0.0031684000
_diffrn_orient_matrix_UB_31      0.0967191000
_diffrn_orient_matrix_UB_32      0.0427016000
_diffrn_orient_matrix_UB_33      0.0385104000
_diffrn_oxdiff_ac3_digest_frames 
;
01520a606ba4b885a96d88cc74f79e945f019736c67
;
_diffrn_oxdiff_ac3_digest_hkl    
;
010975947a84ec0074c0850ae88aeb23171b98
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2781
_reflns_number_total             3436
_reflns_odcompleteness_completeness 95.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_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    ?
_refine_diff_density_max         0.781
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.120
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3436
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1501
_refine_ls_R_factor_gt           0.1357
_refine_ls_restrained_S_all      1.136
_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)+(0.0708P)²+23.7981P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3563
_refine_ls_wR_factor_ref         0.3642
_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 Ternary CH refined with riding coordinates:
 C8(H8), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C5(H5), C14(H14), C13(H13), C6(H6), C15(H15), C12(H12), C22(H22),
 C25(H25), C26(H26), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_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
O18 O 0.3847(6) -0.1082(10) 0.72573(15) 0.0382(13) Uani 1 1 d . . . . .
C10 C 0.5367(7) 0.1599(12) 0.58663(17) 0.0227(14) Uani 1 1 d . . . . .
C3 C 0.2444(7) 0.4581(13) 0.56267(18) 0.0248(14) Uani 1 1 d . . . . .
C7 C 0.2271(7) 0.3456(13) 0.63052(18) 0.0255(14) Uani 1 1 d . . . . .
C11 C 0.6077(7) -0.0062(13) 0.56668(18) 0.0262(14) Uani 1 1 d . . . . .
H11 H 0.5602 -0.1455 0.5569 0.031 Uiso 1 1 calc R . . . .
C5 C 0.0942(7) 0.6738(13) 0.60248(19) 0.0283(15) Uani 1 1 d . . . . .
H5 H 0.0301 0.8003 0.6052 0.034 Uiso 1 1 calc R . . . .
C14 C 0.7470(7) 0.4026(13) 0.5936(2) 0.0285(15) Uani 1 1 d . . . . .
H14 H 0.7935 0.5437 0.6029 0.034 Uiso 1 1 calc R . . . .
C2 C 0.2836(7) 0.3163(13) 0.59510(18) 0.0251(14) Uani 1 1 d . . . . .
C13 C 0.8204(7) 0.2339(14) 0.5744(2) 0.0294(16) Uani 1 1 d . . . . .
H13 H 0.9171 0.2577 0.5706 0.035 Uiso 1 1 calc R . . . .
C21 C 0.5178(7) 0.1902(13) 0.76140(19) 0.0279(15) Uani 1 1 d . . . . .
C8 C 0.2818(7) 0.1643(13) 0.66092(18) 0.0267(15) Uani 1 1 d . . . . .
H8 H 0.2028 0.0552 0.6660 0.032 Uiso 1 1 calc R . . . .
C20 C 0.3045(7) 0.4197(14) 0.52393(19) 0.0299(16) Uani 1 1 d . . . . .
H20A H 0.3835 0.5290 0.5219 0.045 Uiso 1 1 calc GR . . . .
H20B H 0.2304 0.4486 0.5022 0.045 Uiso 1 1 calc GR . . . .
H20C H 0.3384 0.2566 0.5226 0.045 Uiso 1 1 calc GR . . . .
C9 C 0.3949(7) 0.0250(14) 0.6412(2) 0.0307(16) Uani 1 1 d . . . . .
H9A H 0.3762 -0.1469 0.6424 0.037 Uiso 1 1 calc R . . . .
H9B H 0.4905 0.0568 0.6548 0.037 Uiso 1 1 calc R . . . .
C6 C 0.1319(7) 0.5272(14) 0.63430(19) 0.0285(15) Uani 1 1 d . . . . .
H6 H 0.0929 0.5511 0.6584 0.034 Uiso 1 1 calc R . . . .
C15 C 0.6052(7) 0.3651(14) 0.59938(19) 0.0286(15) Uani 1 1 d . . . . .
H15 H 0.5553 0.4824 0.6122 0.034 Uiso 1 1 calc R . . . .
C1 C 0.3858(7) 0.1090(13) 0.59738(18) 0.0256(15) Uani 1 1 d . . . . .
H1 H 0.3432 -0.0206 0.5801 0.031 Uiso 1 1 calc R . . . .
C4 C 0.1480(7) 0.6404(12) 0.56642(18) 0.0244(14) Uani 1 1 d . . . . .
C12 C 0.7503(8) 0.0311(15) 0.5608(2) 0.0330(17) Uani 1 1 d . . . . .
H12 H 0.7992 -0.0847 0.5473 0.040 Uiso 1 1 calc R . . . .
C19 C 0.1039(7) 0.8044(14) 0.5325(2) 0.0306(16) Uani 1 1 d . . . . .
H19A H 0.1879 0.8542 0.5204 0.046 Uiso 1 1 calc GR . . . .
H19B H 0.0569 0.9437 0.5422 0.046 Uiso 1 1 calc GR . . . .
H19C H 0.0382 0.7219 0.5131 0.046 Uiso 1 1 calc GR . . . .
C17 C 0.4120(8) 0.1033(14) 0.7286(2) 0.0323(17) Uani 1 1 d . . . . .
C22 C 0.5032(8) 0.4095(13) 0.77871(19) 0.0302(16) Uani 1 1 d . . . . .
H22 H 0.4297 0.5139 0.7686 0.036 Uiso 1 1 calc R . . . .
C16 C 0.3419(9) 0.2805(15) 0.6996(2) 0.0386(19) Uani 1 1 d . . . . .
H16A H 0.4122 0.4020 0.6941 0.046 Uiso 1 1 calc R . . . .
H16B H 0.2642 0.3607 0.7115 0.046 Uiso 1 1 calc R . . . .
C25 C 0.7267(8) 0.1162(17) 0.8057(2) 0.041(2) Uani 1 1 d . . . . .
H25 H 0.8053 0.0182 0.8142 0.049 Uiso 1 1 calc R . . . .
C26 C 0.6302(8) 0.0449(15) 0.7746(2) 0.0356(17) Uani 1 1 d . . . . .
H26 H 0.6411 -0.1039 0.7625 0.043 Uiso 1 1 calc R . . . .
C23 C 0.5971(8) 0.4753(15) 0.8110(2) 0.0356(17) Uani 1 1 d . . . . .
H23 H 0.5843 0.6211 0.8239 0.043 Uiso 1 1 calc R . . . .
C24 C 0.7089(8) 0.3296(17) 0.8242(2) 0.041(2) Uani 1 1 d . . . . .
H24 H 0.7734 0.3756 0.8461 0.049 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
O18 C17 1.226(9) . ?
C10 C11 1.379(9) . ?
C10 C15 1.377(10) . ?
C10 C1 1.544(9) . ?
C3 C2 1.388(9) . ?
C3 C20 1.515(9) . ?
C3 C4 1.393(10) . ?
C7 C2 1.388(9) . ?
C7 C8 1.513(9) . ?
C7 C6 1.383(10) . ?
C11 H11 0.9500 . ?
C11 C12 1.405(10) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(10) . ?
C5 C4 1.400(9) . ?
C14 H14 0.9500 . ?
C14 C13 1.389(10) . ?
C14 C15 1.397(9) . ?
C2 C1 1.518(10) . ?
C13 H13 0.9500 . ?
C13 C12 1.381(10) . ?
C21 C17 1.506(10) . ?
C21 C22 1.388(10) . ?
C21 C26 1.383(10) . ?
C8 H8 1.0000 . ?
C8 C9 1.544(9) . ?
C8 C16 1.533(10) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C1 1.567(9) . ?
C6 H6 0.9500 . ?
C15 H15 0.9500 . ?
C1 H1 1.0000 . ?
C4 C19 1.509(9) . ?
C12 H12 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C17 C16 1.514(10) . ?
C22 H22 0.9500 . ?
C22 C23 1.393(10) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C25 H25 0.9500 . ?
C25 C26 1.385(10) . ?
C25 C24 1.383(13) . ?
C26 H26 0.9500 . ?
C23 H23 0.9500 . ?
C23 C24 1.380(12) . ?
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
C11 C10 C1 120.4(6) . . ?
C15 C10 C11 119.5(6) . . ?
C15 C10 C1 119.9(6) . . ?
C2 C3 C20 121.6(6) . . ?
C2 C3 C4 118.4(6) . . ?
C4 C3 C20 120.0(6) . . ?
C2 C7 C8 112.6(6) . . ?
C6 C7 C2 119.2(6) . . ?
C6 C7 C8 128.2(6) . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.8(7) . . ?
C12 C11 H11 120.1 . . ?
C6 C5 H5 119.1 . . ?
C6 C5 C4 121.7(7) . . ?
C4 C5 H5 119.1 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.1(7) . . ?
C15 C14 H14 119.9 . . ?
C3 C2 C7 122.4(6) . . ?
C3 C2 C1 127.0(6) . . ?
C7 C2 C1 110.6(6) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 C14 118.9(6) . . ?
C12 C13 H13 120.5 . . ?
C22 C21 C17 121.4(7) . . ?
C26 C21 C17 118.6(7) . . ?
C26 C21 C22 120.0(7) . . ?
C7 C8 H8 109.3 . . ?
C7 C8 C9 104.3(5) . . ?
C7 C8 C16 111.8(6) . . ?
C9 C8 H8 109.3 . . ?
C16 C8 H8 109.3 . . ?
C16 C8 C9 112.7(6) . . ?
C3 C20 H20A 109.5 . . ?
C3 C20 H20B 109.5 . . ?
C3 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C8 C9 H9A 110.3 . . ?
C8 C9 H9B 110.3 . . ?
C8 C9 C1 107.2(5) . . ?
H9A C9 H9B 108.5 . . ?
C1 C9 H9A 110.3 . . ?
C1 C9 H9B 110.3 . . ?
C7 C6 C5 119.1(6) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C10 C15 C14 120.8(7) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C10 C1 C9 109.2(5) . . ?
C10 C1 H1 108.7 . . ?
C2 C1 C10 116.6(6) . . ?
C2 C1 C9 104.6(5) . . ?
C2 C1 H1 108.7 . . ?
C9 C1 H1 108.7 . . ?
C3 C4 C5 119.1(6) . . ?
C3 C4 C19 121.0(6) . . ?
C5 C4 C19 119.9(6) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(7) . . ?
C13 C12 H12 119.6 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O18 C17 C21 119.8(7) . . ?
O18 C17 C16 121.3(7) . . ?
C21 C17 C16 118.9(7) . . ?
C21 C22 H22 120.2 . . ?
C21 C22 C23 119.5(7) . . ?
C23 C22 H22 120.2 . . ?
C8 C16 H16A 109.1 . . ?
C8 C16 H16B 109.1 . . ?
C17 C16 C8 112.3(7) . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
H16A C16 H16B 107.9 . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C24 C25 C26 120.2(8) . . ?
C21 C26 C25 120.0(8) . . ?
C21 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.3(8) . . ?
C24 C23 H23 119.9 . . ?
C25 C24 H24 120.1 . . ?
C23 C24 C25 119.8(7) . . ?
C23 C24 H24 120.1 . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 3.740
_oxdiff_exptl_absorpt_empirical_full_min 0.681
####################################################################### 
# 
# 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_on2562-72
_database_code_depnum_ccdc_archive 'CCDC 2153107'
loop_
_audit_author_name
_audit_author_address
'Aleksander Vasilyev'
;Saint Petersburg State  University
Russia
;
_audit_update_record             
;
2022-02-18 deposited with the CCDC.	2022-05-23 downloaded from the CCDC.
;
_audit_creation_date             2018-05-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H18 O'
_chemical_formula_sum            'C19 H18 O'
_chemical_formula_weight         262.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         C25
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.8475(4)
_cell_length_b                   16.8287(7)
_cell_length_c                   11.1852(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.026(5)
_cell_angle_gamma                90
_cell_volume                     1419.75(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4220
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.7380
_cell_measurement_theta_min      2.6050
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.825
_exptl_absorpt_coefficient_mu    0.570
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9098
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.086
_diffrn_reflns_theta_min         4.881
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -46.00 -19.00   0.50    0.31    --  -41.35  64.00  67.00   54
  2  ω    -58.00 -23.00   0.50    0.31    --  -41.35 -64.00 -68.00   70
  3  ω   -104.00 -61.00   0.50    0.31    --  -41.35 -64.00 -68.00   86
  4  ω     38.00  88.00   0.50    1.26    --  101.00 -64.00 -68.00  100
  5  ω    123.00 150.00   0.50    1.26    --  101.00  64.00  67.00   54
  6  ω     85.00 119.00   0.50    1.26    --  101.00  64.00  67.00   68
  7  ω    -90.00 -23.00   0.50    0.31    --  -41.35 -65.00  90.00  134
  8  ω    -48.00  22.00   0.50    0.31    --  -41.35  65.00-120.00  140
  9  ω     75.00 104.00   0.50    0.31    --   41.35  43.00-150.00   58
 10  ω    -17.00  58.00   0.50    0.31    --   41.35 -54.00 -30.00  150
 11  ω     66.00 108.00   0.50    0.31    --   41.35  21.00  30.00   84
 12  ω    -11.00  14.00   0.50    0.31    --   41.35 -64.00 -68.00   50
 13  ω     29.00  69.00   0.50    0.31    --   41.35  43.00-150.00   80
 14  ω     51.00  86.00   0.50    0.31    --   41.35  64.00  67.00   70
 15  ω    -12.00  18.00   0.50    0.31    --   41.35 -32.00 120.00   60
 16  ω     32.00  57.00   0.50    0.31    --   41.35  21.00  30.00   50
 17  ω     88.00 157.00   0.50    1.26    --  101.00  17.00 150.00  138
 18  ω    108.00 135.00   0.50    1.26    --  101.00  33.00 -90.00   54
 19  ω     95.00 156.00   0.50    1.26    --  101.00  25.00   0.00  122
 20  ω    102.00 149.00   0.50    1.26    --  101.00  33.00  60.00   94
 21  ω     53.00  83.00   0.50    1.26    --  101.00 -59.00 -30.00   60
 22  ω     40.00 114.00   0.50    1.26    --  101.00 -42.00 120.00  148
 23  ω     50.00  92.00   0.50    1.26    --  101.00 -25.00  60.00   84
 24  ω     76.00 111.00   0.50    1.26    --  101.00 -42.00 -60.00   70
 25  ω     92.00 120.00   0.50    1.26    --  101.00  17.00-150.00   56
 26  ω     38.00  69.00   0.50    1.26    --  101.00 -42.00 -60.00   62
 27  ω    123.00 150.00   0.50    1.26    --  101.00  17.00-150.00   54
 28  ω     49.00  85.00   0.50    1.26    --  101.00 -25.00-120.00   72
 29  ω     48.00  87.00   0.50    1.26    --  101.00 -33.00-150.00   78
 30  ω     86.00 111.00   0.50    1.26    --  101.00 -59.00 -30.00   50
 31  ω     53.00 113.00   0.50    1.26    --  101.00 -17.00 120.00  120
 32  ω     87.00 112.00   0.50    1.26    --  101.00  59.00-180.00   50
 33  ω     88.00 151.00   0.50    1.26    --  101.00  42.00  30.00  126
 34  ω     -3.00  22.00   0.50    0.31    --  -41.35  64.00  67.00   50
 35  ω    -93.00 -43.00   0.50    0.31    --  -41.35 -21.00 -30.00  100
 36  ω   -103.00 -78.00   0.50    0.31    --  -41.35 -43.00 150.00   50
 37  ω     24.00  51.00   0.50    0.31    --   41.35  54.00 -60.00   54
 38  ω     30.00  66.00   0.50    0.31    --   41.35  65.00-180.00   72
 39  ω     42.00  84.00   0.50    0.31    --   41.35  32.00  90.00   84
 40  ω     77.00 104.00   0.50    0.31    --   41.35  54.00 -60.00   54
 41  ω     40.00  66.00   0.50    0.31    --   41.35  43.00-180.00   52
 42  ω     79.00 104.00   0.50    0.31    --   41.35  43.00-180.00   50
 43  ω     69.00 104.00   0.50    0.31    --   41.35  65.00-180.00   70
 44  ω     77.00 116.00   0.50    1.26    --  101.00  77.00-180.00   78
 45  ω    127.00 152.00   0.50    1.26    --  101.00  59.00 150.00   50
 46  ω     77.00 104.00   0.50    1.26    --  101.00  77.00 150.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1024394000
_diffrn_orient_matrix_UB_12      -0.0678716000
_diffrn_orient_matrix_UB_13      0.0415762000
_diffrn_orient_matrix_UB_21      0.1352814000
_diffrn_orient_matrix_UB_22      0.0002728000
_diffrn_orient_matrix_UB_23      0.1293274000
_diffrn_orient_matrix_UB_31      -0.1137013000
_diffrn_orient_matrix_UB_32      0.0613876000
_diffrn_orient_matrix_UB_33      0.0456015000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2280
_reflns_number_total             2769
_reflns_odcompleteness_completeness 99.17
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.55
_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 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_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         0.338
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2769
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0684
_refine_ls_restrained_S_all      1.061
_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)+(0.0955P)²+0.9766P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1848
_refine_ls_wR_factor_ref         0.2027
_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 Ternary CH refined with riding coordinates:
 C4(H4), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C9(H9), C12(H12), C16(H16), C11(H11), C10(H10)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_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 0.3342(3) 0.31208(15) 0.5568(2) 0.0692(6) Uani 1 1 d . . . . .
C5 C 0.7028(3) 0.15087(14) 0.5812(2) 0.0415(6) Uani 1 1 d . . . . .
C6 C 0.5318(3) 0.13010(13) 0.5122(2) 0.0427(6) Uani 1 1 d . . . . .
C2 C 0.6216(3) 0.33152(15) 0.5385(2) 0.0428(6) Uani 1 1 d . . . . .
C4 C 0.7874(3) 0.20514(15) 0.5062(2) 0.0426(6) Uani 1 1 d . . . . .
H4 H 0.9134 0.1889 0.5172 0.051 Uiso 1 1 calc R . . . .
C7 C 0.4917(3) 0.16851(15) 0.3847(2) 0.0444(6) Uani 1 1 d . . . . .
H7 H 0.4284 0.1304 0.3187 0.053 Uiso 1 1 calc R . . . .
C13 C 0.6767(3) 0.18674(15) 0.3722(2) 0.0460(6) Uani 1 1 d . . . . .
H13A H 0.6739 0.2330 0.3171 0.055 Uiso 1 1 calc R . . . .
H13B H 0.7257 0.1405 0.3383 0.055 Uiso 1 1 calc R . . . .
C3 C 0.7805(3) 0.29155(15) 0.5436(2) 0.0429(6) Uani 1 1 d . . . . .
C14 C 0.7745(4) 0.12546(14) 0.7037(2) 0.0478(6) Uani 1 1 d . . . . .
C17 C 0.4237(4) 0.08369(14) 0.5644(3) 0.0495(6) Uani 1 1 d . . . . .
C1 C 0.4397(3) 0.29537(15) 0.4975(2) 0.0480(6) Uani 1 1 d . . . . .
C15 C 0.6673(4) 0.07800(15) 0.7539(2) 0.0536(7) Uani 1 1 d . . . . .
H15 H 0.7123 0.0586 0.8363 0.064 Uiso 1 1 calc R . . . .
C8 C 0.3803(3) 0.24433(16) 0.3821(2) 0.0502(6) Uani 1 1 d . . . . .
H8A H 0.3849 0.2766 0.3090 0.060 Uiso 1 1 calc R . . . .
H8B H 0.2552 0.2287 0.3708 0.060 Uiso 1 1 calc R . . . .
C9 C 0.6260(4) 0.41117(16) 0.5763(2) 0.0523(7) Uani 1 1 d . . . . .
H9 H 0.5179 0.4375 0.5735 0.063 Uiso 1 1 calc R . . . .
C12 C 0.9390(4) 0.33364(18) 0.5898(2) 0.0546(7) Uani 1 1 d . . . . .
H12 H 1.0487 0.3074 0.5977 0.066 Uiso 1 1 calc R . . . .
C16 C 0.4970(4) 0.05831(15) 0.6871(2) 0.0542(7) Uani 1 1 d . . . . .
H16 H 0.4272 0.0265 0.7256 0.065 Uiso 1 1 calc R . . . .
C18 C 0.9594(4) 0.14840(18) 0.7759(2) 0.0581(7) Uani 1 1 d . . . . .
H18A H 1.0427 0.1335 0.7287 0.087 Uiso 1 1 calc GR . . . .
H18B H 0.9911 0.1207 0.8561 0.087 Uiso 1 1 calc GR . . . .
H18C H 0.9649 0.2059 0.7900 0.087 Uiso 1 1 calc GR . . . .
C19 C 0.2379(4) 0.06208(17) 0.4922(3) 0.0608(7) Uani 1 1 d . . . . .
H19A H 0.1698 0.1107 0.4638 0.091 Uiso 1 1 calc GR . . . .
H19B H 0.1814 0.0318 0.5456 0.091 Uiso 1 1 calc GR . . . .
H19C H 0.2414 0.0297 0.4200 0.091 Uiso 1 1 calc GR . . . .
C11 C 0.9393(4) 0.41319(19) 0.6245(3) 0.0636(8) Uani 1 1 d . . . . .
H11 H 1.0486 0.4407 0.6535 0.076 Uiso 1 1 calc R . . . .
C10 C 0.7834(5) 0.45193(17) 0.6173(3) 0.0626(8) Uani 1 1 d . . . . .
H10 H 0.7838 0.5063 0.6403 0.075 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
O1 C1 1.228(3) . ?
C5 C6 1.395(3) . ?
C5 C4 1.512(3) . ?
C5 C14 1.397(3) . ?
C6 C7 1.517(3) . ?
C6 C17 1.394(4) . ?
C2 C3 1.405(3) . ?
C2 C1 1.502(4) . ?
C2 C9 1.403(4) . ?
C4 H4 1.0000 . ?
C4 C13 1.542(3) . ?
C4 C3 1.518(3) . ?
C7 H7 1.0000 . ?
C7 C13 1.527(4) . ?
C7 C8 1.542(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C3 C12 1.400(4) . ?
C14 C15 1.386(4) . ?
C14 C18 1.503(4) . ?
C17 C16 1.400(4) . ?
C17 C19 1.503(4) . ?
C1 C8 1.513(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.380(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9 0.9500 . ?
C9 C10 1.376(4) . ?
C12 H12 0.9500 . ?
C12 C11 1.394(4) . ?
C16 H16 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C11 H11 0.9500 . ?
C11 C10 1.369(5) . ?
C10 H10 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
C6 C5 C4 110.3(2) . . ?
C6 C5 C14 122.1(2) . . ?
C14 C5 C4 127.5(2) . . ?
C5 C6 C7 109.4(2) . . ?
C17 C6 C5 120.8(2) . . ?
C17 C6 C7 129.8(2) . . ?
C3 C2 C1 125.2(2) . . ?
C9 C2 C3 119.8(2) . . ?
C9 C2 C1 114.9(2) . . ?
C5 C4 H4 109.7 . . ?
C5 C4 C13 101.63(19) . . ?
C5 C4 C3 111.80(19) . . ?
C13 C4 H4 109.7 . . ?
C3 C4 H4 109.7 . . ?
C3 C4 C13 114.0(2) . . ?
C6 C7 H7 110.6 . . ?
C6 C7 C13 102.44(19) . . ?
C6 C7 C8 109.9(2) . . ?
C13 C7 H7 110.6 . . ?
C13 C7 C8 112.3(2) . . ?
C8 C7 H7 110.6 . . ?
C4 C13 H13A 110.9 . . ?
C4 C13 H13B 110.9 . . ?
C7 C13 C4 104.28(19) . . ?
C7 C13 H13A 110.9 . . ?
C7 C13 H13B 110.9 . . ?
H13A C13 H13B 108.9 . . ?
C2 C3 C4 123.1(2) . . ?
C12 C3 C2 117.5(2) . . ?
C12 C3 C4 119.4(2) . . ?
C5 C14 C18 121.1(2) . . ?
C15 C14 C5 116.6(3) . . ?
C15 C14 C18 122.3(2) . . ?
C6 C17 C16 116.6(3) . . ?
C6 C17 C19 121.5(3) . . ?
C16 C17 C19 121.9(3) . . ?
O1 C1 C2 117.9(2) . . ?
O1 C1 C8 119.8(2) . . ?
C2 C1 C8 122.2(2) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 C14 121.7(2) . . ?
C16 C15 H15 119.2 . . ?
C7 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C1 C8 C7 114.4(2) . . ?
C1 C8 H8A 108.7 . . ?
C1 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C2 C9 H9 119.3 . . ?
C10 C9 C2 121.5(3) . . ?
C10 C9 H9 119.3 . . ?
C3 C12 H12 119.3 . . ?
C11 C12 C3 121.5(3) . . ?
C11 C12 H12 119.3 . . ?
C17 C16 H16 118.9 . . ?
C15 C16 C17 122.1(3) . . ?
C15 C16 H16 118.9 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 C11 H11 119.7 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.7 . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.2(3) . . ?
C11 C10 H10 120.4 . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.942
_oxdiff_exptl_absorpt_empirical_full_min 0.718
