# Electronic Supplementary Material (ESI) for ChemComm.
# 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 
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data_200917ys
_database_code_depnum_ccdc_archive 'CCDC 2087713'
loop_
_audit_author_name
_audit_author_address
'Cis-disphenylcyclopropyl carbagermatrane'
;The University of Science and Technology of China
China
;
_audit_update_record             
;
2021-06-03 deposited with the CCDC.	2021-07-07 downloaded from the CCDC.
;
_audit_creation_date             2020-09-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H31 Ge N'
_chemical_formula_sum            'C24 H31 Ge N'
_chemical_formula_weight         406.09
_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 0.0148 0.0070 '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'
Ge Ge -1.5487 0.7176 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 '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                   15.7360(11)
_cell_length_b                   10.2256(7)
_cell_length_c                   14.5955(11)
_cell_angle_alpha                90
_cell_angle_beta                 117.508(3)
_cell_angle_gamma                90
_cell_volume                     2083.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9871
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.956
_cell_measurement_theta_min      4.796
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.874
_exptl_absorpt_coefficient_mu    1.381
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1933 before and 0.0919 after correction. The Ratio of minimum to maximum transmission is 0.6742. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20026
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.931
_diffrn_reflns_theta_min         4.795
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3610
_reflns_number_total             3925
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 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         0.776
_refine_diff_density_min         -1.008
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3925
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0747P)²+0.7049P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1175
_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:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B),
 C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
;
_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
Ge1 Ge 0.80962(2) 0.59566(2) 0.70213(2) 0.02465(13) Uani 1 1 d . . . . .
N1 N 0.83113(13) 0.35309(17) 0.66437(14) 0.0324(4) Uani 1 1 d . . . . .
C1 C 0.78943(13) 0.78312(18) 0.72899(15) 0.0267(4) Uani 1 1 d . . . . .
C2 C 0.86018(15) 0.8487(2) 0.82717(17) 0.0321(5) Uani 1 1 d . . . . .
H2A H 0.871234 0.943600 0.824448 0.038 Uiso 1 1 calc R . . . .
H2B H 0.917439 0.798141 0.874344 0.038 Uiso 1 1 calc R . . . .
C3 C 0.76430(14) 0.80615(19) 0.81712(15) 0.0267(4) Uani 1 1 d . . . . .
H3 H 0.767531 0.725380 0.857236 0.032 Uiso 1 1 calc R . . . .
C4 C 0.69115(14) 0.90199(18) 0.81203(17) 0.0267(5) Uani 1 1 d . . . . .
C5 C 0.61891(15) 0.8589(2) 0.83424(17) 0.0326(5) Uani 1 1 d . . . . .
H5 H 0.617714 0.769777 0.852096 0.039 Uiso 1 1 calc R . . . .
C6 C 0.54867(16) 0.9432(3) 0.83087(19) 0.0406(5) Uani 1 1 d . . . . .
H6 H 0.499712 0.911431 0.845878 0.049 Uiso 1 1 calc R . . . .
C7 C 0.54953(17) 1.0734(2) 0.80573(19) 0.0411(6) Uani 1 1 d . . . . .
H7 H 0.501564 1.131458 0.803713 0.049 Uiso 1 1 calc R . . . .
C8 C 0.62046(19) 1.1180(2) 0.78369(19) 0.0399(5) Uani 1 1 d . . . . .
H8 H 0.621507 1.207322 0.766316 0.048 Uiso 1 1 calc R . . . .
C9 C 0.69072(15) 1.0330(2) 0.78669(17) 0.0341(5) Uani 1 1 d . . . . .
H9 H 0.739253 1.065157 0.771148 0.041 Uiso 1 1 calc R . . . .
C10 C 0.74329(15) 0.8645(2) 0.63274(16) 0.0285(4) Uani 1 1 d . . . . .
C11 C 0.64416(16) 0.8685(2) 0.57202(18) 0.0347(5) Uani 1 1 d . . . . .
H11 H 0.603980 0.823185 0.593870 0.042 Uiso 1 1 calc R . . . .
C12 C 0.6033(2) 0.9385(3) 0.47940(19) 0.0459(6) Uani 1 1 d . . . . .
H12 H 0.535620 0.941472 0.439251 0.055 Uiso 1 1 calc R . . . .
C13 C 0.6606(2) 1.0033(2) 0.4459(2) 0.0511(7) Uani 1 1 d . . . . .
H13 H 0.632727 1.049588 0.382281 0.061 Uiso 1 1 calc R . . . .
C14 C 0.7584(2) 1.0004(2) 0.50521(19) 0.0469(6) Uani 1 1 d . . . . .
H14 H 0.798175 1.045258 0.482565 0.056 Uiso 1 1 calc R . . . .
C15 C 0.79945(18) 0.9324(2) 0.59799(19) 0.0366(5) Uani 1 1 d . . . . .
H15 H 0.867142 0.932279 0.638508 0.044 Uiso 1 1 calc R . . . .
C16 C 0.91045(17) 0.5309(2) 0.83655(17) 0.0388(5) Uani 1 1 d . . . . .
H16A H 0.973775 0.556591 0.843361 0.047 Uiso 1 1 calc R . . . .
H16B H 0.902585 0.574648 0.892683 0.047 Uiso 1 1 calc R . . . .
C17 C 0.9098(2) 0.3828(2) 0.8513(2) 0.0483(7) Uani 1 1 d . . . . .
H17A H 0.966779 0.357595 0.916028 0.058 Uiso 1 1 calc R . . . .
H17B H 0.852058 0.358255 0.857871 0.058 Uiso 1 1 calc R . . . .
C18 C 0.91050(18) 0.3085(2) 0.76141(19) 0.0427(6) Uani 1 1 d . . . . .
H18A H 0.972041 0.323465 0.759986 0.051 Uiso 1 1 calc R . . . .
H18B H 0.904101 0.213606 0.770107 0.051 Uiso 1 1 calc R . . . .
C19 C 0.73821(18) 0.2962(2) 0.6408(2) 0.0408(6) Uani 1 1 d . . . . .
H19A H 0.738803 0.264235 0.705087 0.049 Uiso 1 1 calc R . . . .
H19B H 0.725017 0.221034 0.593386 0.049 Uiso 1 1 calc R . . . .
C20 C 0.66042(17) 0.3991(2) 0.5906(2) 0.0388(6) Uani 1 1 d . . . . .
H20A H 0.597884 0.361660 0.577737 0.047 Uiso 1 1 calc R . . . .
H20B H 0.656157 0.424757 0.523172 0.047 Uiso 1 1 calc R . . . .
C21 C 0.68128(15) 0.5198(2) 0.65897(19) 0.0351(5) Uani 1 1 d . . . . .
H21A H 0.675229 0.496051 0.721459 0.042 Uiso 1 1 calc R . . . .
H21B H 0.632350 0.587192 0.621153 0.042 Uiso 1 1 calc R . . . .
C22 C 0.85266(17) 0.3625(2) 0.57787(18) 0.0371(5) Uani 1 1 d . . . . .
H22A H 0.792490 0.359604 0.512046 0.044 Uiso 1 1 calc R . . . .
H22B H 0.893061 0.287580 0.579087 0.044 Uiso 1 1 calc R . . . .
C23 C 0.90526(16) 0.4903(2) 0.58526(19) 0.0371(5) Uani 1 1 d . . . . .
H23A H 0.915404 0.499885 0.523515 0.045 Uiso 1 1 calc R . . . .
H23B H 0.968890 0.487867 0.646878 0.045 Uiso 1 1 calc R . . . .
C24 C 0.84885(16) 0.60763(19) 0.59285(18) 0.0311(5) Uani 1 1 d . . . . .
H24A H 0.790759 0.618417 0.525738 0.037 Uiso 1 1 calc R . . . .
H24B H 0.888491 0.687132 0.604757 0.037 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
Ge1 C1 2.0110(19) . ?
Ge1 C16 1.982(2) . ?
Ge1 C21 1.975(2) . ?
Ge1 C24 1.962(2) . ?
N1 C18 1.463(3) . ?
N1 C19 1.459(3) . ?
N1 C22 1.454(3) . ?
C1 C2 1.506(3) . ?
C1 C3 1.528(3) . ?
C1 C10 1.500(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.511(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.487(3) . ?
C4 C5 1.390(3) . ?
C4 C9 1.389(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.383(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.374(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.391(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.394(3) . ?
C10 C15 1.391(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.397(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.378(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.374(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(3) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.531(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.520(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.521(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.524(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.524(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.527(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 Ge1 C1 104.58(9) . . ?
C21 Ge1 C1 101.91(8) . . ?
C21 Ge1 C16 114.69(10) . . ?
C24 Ge1 C1 103.67(8) . . ?
C24 Ge1 C16 114.63(10) . . ?
C24 Ge1 C21 115.11(10) . . ?
C19 N1 C18 114.8(2) . . ?
C22 N1 C18 115.10(18) . . ?
C22 N1 C19 115.55(19) . . ?
C2 C1 Ge1 119.73(14) . . ?
C2 C1 C3 59.71(13) . . ?
C3 C1 Ge1 115.88(13) . . ?
C10 C1 Ge1 113.43(14) . . ?
C10 C1 C2 118.00(17) . . ?
C10 C1 C3 120.09(16) . . ?
C1 C2 H2A 117.7 . . ?
C1 C2 H2B 117.7 . . ?
C1 C2 C3 60.87(13) . . ?
H2A C2 H2B 114.8 . . ?
C3 C2 H2A 117.7 . . ?
C3 C2 H2B 117.7 . . ?
C1 C3 H3 113.7 . . ?
C2 C3 C1 59.42(13) . . ?
C2 C3 H3 113.7 . . ?
C4 C3 C1 123.68(17) . . ?
C4 C3 C2 122.02(17) . . ?
C4 C3 H3 113.7 . . ?
C5 C4 C3 118.47(18) . . ?
C9 C4 C3 123.88(19) . . ?
C9 C4 C5 117.66(19) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.2(2) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.4(2) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.3(2) . . ?
C9 C8 H8 119.8 . . ?
C4 C9 C8 121.1(2) . . ?
C4 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C11 C10 C1 121.81(19) . . ?
C15 C10 C1 120.28(19) . . ?
C15 C10 C11 117.8(2) . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.7(2) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.5(2) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 119.4 . . ?
C14 C15 C10 121.2(2) . . ?
C14 C15 H15 119.4 . . ?
Ge1 C16 H16A 108.6 . . ?
Ge1 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C17 C16 Ge1 114.54(17) . . ?
C17 C16 H16A 108.6 . . ?
C17 C16 H16B 108.6 . . ?
C16 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 C16 111.7(2) . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
N1 C18 C17 109.68(19) . . ?
N1 C18 H18A 109.7 . . ?
N1 C18 H18B 109.7 . . ?
C17 C18 H18A 109.7 . . ?
C17 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
N1 C19 H19A 109.8 . . ?
N1 C19 H19B 109.8 . . ?
N1 C19 C20 109.50(19) . . ?
H19A C19 H19B 108.2 . . ?
C20 C19 H19A 109.8 . . ?
C20 C19 H19B 109.8 . . ?
C19 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
C19 C20 C21 111.3(2) . . ?
H20A C20 H20B 108.0 . . ?
C21 C20 H20A 109.4 . . ?
C21 C20 H20B 109.4 . . ?
Ge1 C21 H21A 108.8 . . ?
Ge1 C21 H21B 108.8 . . ?
C20 C21 Ge1 113.95(15) . . ?
C20 C21 H21A 108.8 . . ?
C20 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
N1 C22 H22A 109.8 . . ?
N1 C22 H22B 109.8 . . ?
N1 C22 C23 109.38(18) . . ?
H22A C22 H22B 108.2 . . ?
C23 C22 H22A 109.8 . . ?
C23 C22 H22B 109.8 . . ?
C22 C23 H23A 109.4 . . ?
C22 C23 H23B 109.4 . . ?
C22 C23 C24 111.36(18) . . ?
H23A C23 H23B 108.0 . . ?
C24 C23 H23A 109.4 . . ?
C24 C23 H23B 109.4 . . ?
Ge1 C24 H24A 108.5 . . ?
Ge1 C24 H24B 108.5 . . ?
C23 C24 Ge1 114.94(15) . . ?
C23 C24 H24A 108.5 . . ?
C23 C24 H24B 108.5 . . ?
H24A C24 H24B 107.5 . . ?

_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_201211ys
_database_code_depnum_ccdc_archive 'CCDC 2087719'
loop_
_audit_author_name
_audit_author_address
'Cis-disphenylcyclopropyl p-methoxybenzene'
;The University of Science and Technology of China
China
;
_audit_update_record             
;
2021-06-03 deposited with the CCDC.	2021-07-07 downloaded from the CCDC.
;
_audit_creation_date             2020-12-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 O'
_chemical_formula_sum            'C22 H20 O'
_chemical_formula_weight         300.38
_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 0.0148 0.0070 '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 0.0412 0.0250 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   32.854(6)
_cell_length_b                   5.8699(12)
_cell_length_c                   34.286(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6612(2)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    3581
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      45.044
_cell_measurement_theta_min      3.235
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.357
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.1560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1789 before and 0.1147 after correction. The Ratio of minimum to maximum transmission is 0.1881. 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    1.207
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2560
_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  0.1322
_diffrn_reflns_av_unetI/netI     0.1568
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            21701
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.052
_diffrn_reflns_theta_min         3.242
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2563
_reflns_number_total             6044
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 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         0.367
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         6044
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2265
_refine_ls_R_factor_gt           0.1063
_refine_ls_restrained_S_all      0.977
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1564P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2407
_refine_ls_wR_factor_ref         0.3178
_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:
 C3(H3), C3A(H3A)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C1A(H1AA,H1AB)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C5A(H5A), C6A(H6A),
  C7A(H7A), C8A(H8A), C9A(H9A), C11A(H11A), C12A(H12A), C13A(H13A), C14A(H14A),
 C15A(H15A), C17A(H17A), C18A(H18A), C20A(H20A), C21A(H21A)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C22A(H22D,H22E,H22F)
;
_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 0.44737(12) 0.0333(8) 0.67665(11) 0.0570(12) Uani 1 1 d . . . . .
C1 C 0.43693(16) 0.6597(9) 0.51914(16) 0.0433(15) Uani 1 1 d . . . . .
H1A H 0.455213 0.727236 0.538963 0.052 Uiso 1 1 calc R . . . .
H1B H 0.423095 0.771607 0.502080 0.052 Uiso 1 1 calc R . . . .
C2 C 0.41363(15) 0.4475(8) 0.53029(15) 0.0315(12) Uani 1 1 d . . . . .
C3 C 0.44940(15) 0.4348(8) 0.50124(16) 0.0386(14) Uani 1 1 d . . . . .
H3 H 0.474804 0.369808 0.512814 0.046 Uiso 1 1 calc R . . . .
C4 C 0.44436(16) 0.3817(9) 0.45904(17) 0.0399(14) Uani 1 1 d . . . . .
C5 C 0.42490(18) 0.5265(10) 0.43289(17) 0.0524(16) Uani 1 1 d . . . . .
H5 H 0.413533 0.665168 0.442156 0.063 Uiso 1 1 calc R . . . .
C6 C 0.4217(2) 0.4735(12) 0.39386(19) 0.0601(18) Uani 1 1 d . . . . .
H6 H 0.408217 0.574656 0.376536 0.072 Uiso 1 1 calc R . . . .
C7 C 0.43851(19) 0.2697(12) 0.37979(19) 0.0582(18) Uani 1 1 d . . . . .
H7 H 0.436938 0.233737 0.352817 0.070 Uiso 1 1 calc R . . . .
C8 C 0.45722(19) 0.1226(11) 0.4052(2) 0.0563(18) Uani 1 1 d . . . . .
H8 H 0.467925 -0.017807 0.396037 0.068 Uiso 1 1 calc R . . . .
C9 C 0.46049(16) 0.1791(10) 0.44442(19) 0.0504(16) Uani 1 1 d . . . . .
H9 H 0.474028 0.077623 0.461664 0.061 Uiso 1 1 calc R . . . .
C10 C 0.37043(14) 0.4326(8) 0.51654(15) 0.0322(12) Uani 1 1 d . . . . .
C11 C 0.34313(15) 0.5975(9) 0.52806(15) 0.0358(13) Uani 1 1 d . . . . .
H11 H 0.352364 0.719742 0.543912 0.043 Uiso 1 1 calc R . . . .
C12 C 0.30243(17) 0.5897(10) 0.51708(16) 0.0456(15) Uani 1 1 d . . . . .
H12 H 0.283922 0.702727 0.525955 0.055 Uiso 1 1 calc R . . . .
C13 C 0.28919(17) 0.4154(10) 0.49310(17) 0.0465(15) Uani 1 1 d . . . . .
H13 H 0.261678 0.411172 0.484594 0.056 Uiso 1 1 calc R . . . .
C14 C 0.31595(16) 0.2479(9) 0.48157(16) 0.0420(14) Uani 1 1 d . . . . .
H14 H 0.306661 0.125531 0.465767 0.050 Uiso 1 1 calc R . . . .
C15 C 0.35658(15) 0.2571(9) 0.49300(15) 0.0407(14) Uani 1 1 d . . . . .
H15 H 0.374949 0.142196 0.484586 0.049 Uiso 1 1 calc R . . . .
C16 C 0.42179(14) 0.3430(9) 0.56999(16) 0.0351(13) Uani 1 1 d . . . . .
C17 C 0.45321(17) 0.4128(10) 0.59381(18) 0.0535(17) Uani 1 1 d . . . . .
H17 H 0.469781 0.536869 0.585793 0.064 Uiso 1 1 calc R . . . .
C18 C 0.46127(17) 0.3077(11) 0.62892(18) 0.0571(18) Uani 1 1 d . . . . .
H18 H 0.483399 0.357471 0.644590 0.068 Uiso 1 1 calc R . . . .
C19 C 0.43674(16) 0.1277(9) 0.64132(16) 0.0398(14) Uani 1 1 d . . . . .
C20 C 0.40526(17) 0.0573(10) 0.61819(17) 0.0462(15) Uani 1 1 d . . . . .
H20 H 0.388585 -0.066127 0.626322 0.055 Uiso 1 1 calc R . . . .
C21 C 0.39749(16) 0.1652(9) 0.58278(16) 0.0431(15) Uani 1 1 d . . . . .
H21 H 0.375233 0.116285 0.567198 0.052 Uiso 1 1 calc R . . . .
C22 C 0.4253(2) -0.1647(11) 0.68824(18) 0.0609(19) Uani 1 1 d . . . . .
H22A H 0.427385 -0.280993 0.667830 0.091 Uiso 1 1 calc GR . . . .
H22B H 0.396637 -0.124874 0.692244 0.091 Uiso 1 1 calc GR . . . .
H22C H 0.436720 -0.224195 0.712597 0.091 Uiso 1 1 calc GR . . . .
O2 O 0.30609(11) 0.8599(6) 0.60472(11) 0.0451(10) Uani 1 1 d . . . . .
C1A C 0.30830(17) 0.3136(9) 0.77096(17) 0.0443(15) Uani 1 1 d . . . . .
H1AA H 0.322586 0.198743 0.787071 0.053 Uiso 1 1 calc R . . . .
H1AB H 0.287699 0.250653 0.752847 0.053 Uiso 1 1 calc R . . . .
C2A C 0.33195(14) 0.5166(8) 0.75785(14) 0.0294(12) Uani 1 1 d . . . . .
C3A C 0.29973(15) 0.5448(8) 0.78925(15) 0.0356(13) Uani 1 1 d . . . . .
H3A H 0.274133 0.616440 0.779331 0.043 Uiso 1 1 calc R . . . .
C4A C 0.30857(15) 0.6038(9) 0.83054(15) 0.0345(13) Uani 1 1 d . . . . .
C5A C 0.29006(17) 0.7947(9) 0.84642(17) 0.0463(15) Uani 1 1 d . . . . .
H5A H 0.271949 0.880982 0.830668 0.056 Uiso 1 1 calc R . . . .
C6A C 0.29705(18) 0.8641(10) 0.88447(18) 0.0520(17) Uani 1 1 d . . . . .
H6A H 0.283983 0.995401 0.894749 0.062 Uiso 1 1 calc R . . . .
C7A C 0.32388(17) 0.7358(11) 0.90737(18) 0.0508(16) Uani 1 1 d . . . . .
H7A H 0.329191 0.780577 0.933505 0.061 Uiso 1 1 calc R . . . .
C8A C 0.34275(18) 0.5439(10) 0.89222(17) 0.0516(16) Uani 1 1 d . . . . .
H8A H 0.360940 0.458104 0.907962 0.062 Uiso 1 1 calc R . . . .
C9A C 0.33516(17) 0.4776(9) 0.85441(17) 0.0470(15) Uani 1 1 d . . . . .
H9A H 0.348008 0.345196 0.844312 0.056 Uiso 1 1 calc R . . . .
C10A C 0.37634(14) 0.5339(8) 0.76832(14) 0.0302(12) Uani 1 1 d . . . . .
C11A C 0.39189(15) 0.7281(9) 0.78644(15) 0.0360(13) Uani 1 1 d . . . . .
H11A H 0.374090 0.849636 0.793075 0.043 Uiso 1 1 calc R . . . .
C12A C 0.43302(17) 0.7456(11) 0.79484(17) 0.0499(16) Uani 1 1 d . . . . .
H12A H 0.443296 0.880199 0.806676 0.060 Uiso 1 1 calc R . . . .
C13A C 0.45910(18) 0.5689(11) 0.78613(16) 0.0490(16) Uani 1 1 d . . . . .
H13A H 0.487129 0.579578 0.792682 0.059 Uiso 1 1 calc R . . . .
C14A C 0.44442(17) 0.3772(11) 0.76793(17) 0.0477(15) Uani 1 1 d . . . . .
H14A H 0.462517 0.257865 0.760881 0.057 Uiso 1 1 calc R . . . .
C15A C 0.40312(16) 0.3578(9) 0.75982(15) 0.0399(14) Uani 1 1 d . . . . .
H15A H 0.393054 0.221923 0.748269 0.048 Uiso 1 1 calc R . . . .
C16A C 0.32254(15) 0.6093(9) 0.71746(15) 0.0320(12) Uani 1 1 d . . . . .
C17A C 0.33836(16) 0.5019(9) 0.68402(15) 0.0386(13) Uani 1 1 d . . . . .
H17A H 0.353773 0.366031 0.686967 0.046 Uiso 1 1 calc R . . . .
C18A C 0.33219(15) 0.5873(9) 0.64754(16) 0.0400(14) Uani 1 1 d . . . . .
H18A H 0.343373 0.511734 0.625504 0.048 Uiso 1 1 calc R . . . .
C19A C 0.30943(15) 0.7856(9) 0.64261(16) 0.0371(13) Uani 1 1 d . . . . .
C20A C 0.29249(17) 0.8945(9) 0.67448(16) 0.0427(14) Uani 1 1 d . . . . .
H20A H 0.276410 1.027708 0.671259 0.051 Uiso 1 1 calc R . . . .
C21A C 0.29959(15) 0.8039(9) 0.71144(16) 0.0394(14) Uani 1 1 d . . . . .
H21A H 0.288200 0.878926 0.733437 0.047 Uiso 1 1 calc R . . . .
C22A C 0.28426(18) 1.0679(9) 0.59793(17) 0.0519(16) Uani 1 1 d . . . . .
H22D H 0.286254 1.109084 0.570293 0.078 Uiso 1 1 calc GR . . . .
H22E H 0.296034 1.189760 0.613882 0.078 Uiso 1 1 calc GR . . . .
H22F H 0.255598 1.046941 0.604970 0.078 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 C19 1.377(6) . ?
O1 C22 1.426(7) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.511(7) . ?
C1 C3 1.512(7) . ?
C2 C3 1.542(7) . ?
C2 C10 1.498(6) . ?
C2 C16 1.517(7) . ?
C3 H3 1.0000 . ?
C3 C4 1.489(8) . ?
C4 C5 1.391(8) . ?
C4 C9 1.395(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.378(8) . ?
C6 H6 0.9500 . ?
C6 C7 1.403(8) . ?
C7 H7 0.9500 . ?
C7 C8 1.373(8) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.378(6) . ?
C10 C15 1.385(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.377(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(7) . ?
C16 C21 1.385(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.379(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.395(7) . ?
C19 C20 1.367(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.393(7) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O2 C19A 1.375(6) . ?
O2 C22A 1.435(6) . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
C1A C2A 1.492(7) . ?
C1A C3A 1.521(7) . ?
C2A C3A 1.519(6) . ?
C2A C10A 1.506(6) . ?
C2A C16A 1.519(7) . ?
C3A H3A 1.0000 . ?
C3A C4A 1.486(7) . ?
C4A C5A 1.387(7) . ?
C4A C9A 1.407(7) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.386(8) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.400(8) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.387(8) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.376(7) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.395(7) . ?
C10A C15A 1.388(6) . ?
C11A H11A 0.9500 . ?
C11A C12A 1.385(7) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.378(8) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.374(8) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.390(7) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.408(7) . ?
C16A C21A 1.384(7) . ?
C17A H17A 0.9500 . ?
C17A C18A 1.362(7) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.394(7) . ?
C19A C20A 1.383(7) . ?
C20A H20A 0.9500 . ?
C20A C21A 1.394(7) . ?
C21A H21A 0.9500 . ?
C22A H22D 0.9800 . ?
C22A H22E 0.9800 . ?
C22A H22F 0.9800 . ?

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
C19 O1 C22 116.4(4) . . ?
H1A C1 H1B 114.7 . . ?
C2 C1 H1A 117.6 . . ?
C2 C1 H1B 117.6 . . ?
C2 C1 C3 61.3(3) . . ?
C3 C1 H1A 117.6 . . ?
C3 C1 H1B 117.6 . . ?
C1 C2 C3 59.4(3) . . ?
C1 C2 C16 118.1(4) . . ?
C10 C2 C1 116.7(5) . . ?
C10 C2 C3 121.1(4) . . ?
C10 C2 C16 115.2(4) . . ?
C16 C2 C3 115.2(4) . . ?
C1 C3 C2 59.3(3) . . ?
C1 C3 H3 113.5 . . ?
C2 C3 H3 113.5 . . ?
C4 C3 C1 123.2(5) . . ?
C4 C3 C2 123.6(4) . . ?
C4 C3 H3 113.5 . . ?
C5 C4 C3 123.3(5) . . ?
C5 C4 C9 117.6(6) . . ?
C9 C4 C3 119.0(5) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.5(6) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.8(6) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.6(6) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.0(6) . . ?
C9 C8 H8 120.0 . . ?
C4 C9 H9 119.3 . . ?
C8 C9 C4 121.5(6) . . ?
C8 C9 H9 119.3 . . ?
C11 C10 C2 119.0(5) . . ?
C11 C10 C15 118.4(5) . . ?
C15 C10 C2 122.6(4) . . ?
C10 C11 H11 119.1 . . ?
C10 C11 C12 121.7(5) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.2(5) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.9(5) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.2(5) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 120.5(5) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C2 122.9(5) . . ?
C17 C16 C21 117.9(5) . . ?
C21 C16 C2 119.1(5) . . ?
C16 C17 H17 119.1 . . ?
C16 C17 C18 121.9(5) . . ?
C18 C17 H17 119.1 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.6(5) . . ?
C19 C18 H18 120.2 . . ?
O1 C19 C18 115.2(5) . . ?
C20 C19 O1 125.5(5) . . ?
C20 C19 C18 119.3(5) . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.4(5) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 120.9(5) . . ?
C16 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19A O2 C22A 117.6(4) . . ?
H1AA C1A H1AB 114.8 . . ?
C2A C1A H1AA 117.7 . . ?
C2A C1A H1AB 117.7 . . ?
C2A C1A C3A 60.5(3) . . ?
C3A C1A H1AA 117.7 . . ?
C3A C1A H1AB 117.7 . . ?
C1A C2A C3A 60.7(3) . . ?
C1A C2A C10A 119.1(4) . . ?
C1A C2A C16A 117.0(4) . . ?
C3A C2A C16A 117.7(4) . . ?
C10A C2A C3A 119.9(4) . . ?
C10A C2A C16A 113.0(4) . . ?
C1A C3A H3A 113.0 . . ?
C2A C3A C1A 58.8(3) . . ?
C2A C3A H3A 113.0 . . ?
C4A C3A C1A 124.4(5) . . ?
C4A C3A C2A 124.4(4) . . ?
C4A C3A H3A 113.0 . . ?
C5A C4A C3A 118.5(5) . . ?
C5A C4A C9A 118.0(5) . . ?
C9A C4A C3A 123.6(5) . . ?
C4A C5A H5A 118.8 . . ?
C6A C5A C4A 122.3(6) . . ?
C6A C5A H5A 118.8 . . ?
C5A C6A H6A 120.9 . . ?
C5A C6A C7A 118.3(6) . . ?
C7A C6A H6A 120.9 . . ?
C6A C7A H7A 119.7 . . ?
C8A C7A C6A 120.5(6) . . ?
C8A C7A H7A 119.7 . . ?
C7A C8A H8A 119.9 . . ?
C9A C8A C7A 120.1(6) . . ?
C9A C8A H8A 119.9 . . ?
C4A C9A H9A 119.6 . . ?
C8A C9A C4A 120.8(5) . . ?
C8A C9A H9A 119.6 . . ?
C11A C10A C2A 121.0(4) . . ?
C15A C10A C2A 120.9(5) . . ?
C15A C10A C11A 118.0(5) . . ?
C10A C11A H11A 119.7 . . ?
C12A C11A C10A 120.7(5) . . ?
C12A C11A H11A 119.7 . . ?
C11A C12A H12A 119.8 . . ?
C13A C12A C11A 120.4(6) . . ?
C13A C12A H12A 119.8 . . ?
C12A C13A H13A 120.1 . . ?
C14A C13A C12A 119.8(5) . . ?
C14A C13A H13A 120.1 . . ?
C13A C14A H14A 120.0 . . ?
C13A C14A C15A 120.0(5) . . ?
C15A C14A H14A 120.0 . . ?
C10A C15A H15A 119.5 . . ?
C14A C15A C10A 121.1(5) . . ?
C14A C15A H15A 119.5 . . ?
C17A C16A C2A 120.5(5) . . ?
C21A C16A C2A 122.8(5) . . ?
C21A C16A C17A 116.7(5) . . ?
C16A C17A H17A 119.1 . . ?
C18A C17A C16A 121.9(5) . . ?
C18A C17A H17A 119.1 . . ?
C17A C18A H18A 120.1 . . ?
C17A C18A C19A 119.9(5) . . ?
C19A C18A H18A 120.1 . . ?
O2 C19A C18A 115.0(5) . . ?
O2 C19A C20A 124.6(5) . . ?
C20A C19A C18A 120.4(5) . . ?
C19A C20A H20A 120.8 . . ?
C19A C20A C21A 118.3(5) . . ?
C21A C20A H20A 120.8 . . ?
C16A C21A C20A 122.8(5) . . ?
C16A C21A H21A 118.6 . . ?
C20A C21A H21A 118.6 . . ?
O2 C22A H22D 109.5 . . ?
O2 C22A H22E 109.5 . . ?
O2 C22A H22F 109.5 . . ?
H22D C22A H22E 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
