# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_djp_4e_2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2253530'
loop_
_audit_author_name
_audit_author_address
'jiping du'
;Sichuan university
China
;
_audit_update_record             
;
2023-04-03 deposited with the CCDC.	2023-06-09 downloaded from the CCDC.
;
_audit_creation_date             2022-12-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H12 O2'
_chemical_formula_sum            'C17 H12 O2'
_chemical_formula_weight         248.27
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   17.755(7)
_cell_length_b                   5.479(2)
_cell_length_c                   6.556(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.98(2)
_cell_angle_gamma                90
_cell_volume                     618.9(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2454
_cell_measurement_temperature    287(2)
_cell_measurement_theta_max      72.182
_cell_measurement_theta_min      5.135
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.809
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.5907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1312 before and 0.0806 after correction.
The Ratio of minimum to maximum transmission is 0.7839.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2945
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.032
_diffrn_reflns_theta_max         67.032
_diffrn_reflns_theta_min         5.134
_diffrn_ambient_temperature      287.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    0.930
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                1027
_reflns_number_total             1062
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         0.208
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 421 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     87
_refine_ls_number_reflns         1062
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.123
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0227P)²+0.4241P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0951
_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 Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C7(H7)
;
_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 0.37518(12) 0.7424(5) -0.0236(3) 0.0483(7) Uani 1 1 d . . . . .
C1 C 0.29740(16) 0.2001(7) 0.3823(5) 0.0420(8) Uani 1 1 d . . . . .
H1 H 0.2539 0.0996 0.3500 0.050 Uiso 1 1 calc R . . . .
C2 C 0.31201(17) 0.3578(6) 0.2329(5) 0.0394(8) Uani 1 1 d . . . . .
H2 H 0.2786 0.3668 0.0999 0.047 Uiso 1 1 calc R . . . .
C3 C 0.37818(15) 0.5037(5) 0.2859(4) 0.0302(7) Uani 1 1 d . . . . .
C4 C 0.42899(14) 0.4921(5) 0.4846(4) 0.0273(6) Uani 1 1 d . . . . .
C5 C 0.5000 0.6565(8) 0.5000 0.0277(9) Uani 1 2 d S T P . .
C6 C 0.41322(16) 0.3359(6) 0.6342(4) 0.0331(7) Uani 1 1 d . . . . .
H6 H 0.4461 0.3283 0.7680 0.040 Uiso 1 1 calc R . . . .
C7 C 0.34733(16) 0.1903(6) 0.5813(5) 0.0399(8) Uani 1 1 d . . . . .
H7 H 0.3364 0.0842 0.6811 0.048 Uiso 1 1 calc R . . . .
C8 C 0.40515(15) 0.6891(6) 0.1562(4) 0.0319(6) Uani 1 1 d . . . . .
C9 C 0.47744(15) 0.8064(5) 0.2943(4) 0.0311(7) Uani 1 1 d . . . . .
H9A H 0.4669 0.9744 0.3248 0.037 Uiso 1 1 calc R . . . .
H9B H 0.5195 0.8047 0.2233 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
O1 C8 1.206(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.378(4) . ?
C1 C7 1.390(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.394(4) . ?
C3 C4 1.395(4) . ?
C3 C8 1.477(4) . ?
C4 C5 1.533(4) . ?
C4 C6 1.381(4) . ?
C5 C4 1.533(4) 2_656 ?
C5 C9 1.547(4) . ?
C5 C9 1.547(4) 2_656 ?
C6 H6 0.9300 . ?
C6 C7 1.389(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.523(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.8 . . ?
C2 C1 C7 120.3(3) . . ?
C7 C1 H1 119.8 . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.3(3) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 C8 128.4(2) . . ?
C4 C3 C8 110.0(2) . . ?
C3 C4 C5 111.8(2) . . ?
C6 C4 C3 119.7(2) . . ?
C6 C4 C5 128.5(2) . . ?
C4 C5 C4 108.0(3) . 2_656 ?
C4 C5 C9 102.64(14) . . ?
C4 C5 C9 102.64(14) 2_656 2_656 ?
C4 C5 C9 113.89(14) . 2_656 ?
C4 C5 C9 113.89(14) 2_656 . ?
C9 C5 C9 115.9(3) 2_656 . ?
C4 C6 H6 120.6 . . ?
C4 C6 C7 118.8(3) . . ?
C7 C6 H6 120.6 . . ?
C1 C7 H7 119.3 . . ?
C6 C7 C1 121.3(3) . . ?
C6 C7 H7 119.3 . . ?
O1 C8 C3 127.0(3) . . ?
O1 C8 C9 126.0(3) . . ?
C3 C8 C9 107.0(2) . . ?
C5 C9 H9A 110.2 . . ?
C5 C9 H9B 110.2 . . ?
C8 C9 C5 107.3(2) . . ?
C8 C9 H9A 110.2 . . ?
C8 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?

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
O1 C8 C9 C5 -172.6(3) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C1 C2 C3 C8 -178.5(3) . . . . ?
C2 C1 C7 C6 -0.7(5) . . . . ?
C2 C3 C4 C5 176.1(3) . . . . ?
C2 C3 C4 C6 -1.0(4) . . . . ?
C2 C3 C8 O1 -2.3(5) . . . . ?
C2 C3 C8 C9 176.3(3) . . . . ?
C3 C4 C5 C4 -110.5(2) . . . 2_656 ?
C3 C4 C5 C9 10.1(3) . . . . ?
C3 C4 C5 C9 136.2(2) . . . 2_656 ?
C3 C4 C6 C7 1.1(4) . . . . ?
C3 C8 C9 C5 8.7(3) . . . . ?
C4 C3 C8 O1 179.0(3) . . . . ?
C4 C3 C8 C9 -2.4(3) . . . . ?
C4 C5 C9 C8 105.4(3) 2_656 . . . ?
C4 C5 C9 C8 -11.1(3) . . . . ?
C4 C6 C7 C1 -0.2(5) . . . . ?
C5 C4 C6 C7 -175.5(3) . . . . ?
C6 C4 C5 C4 66.3(3) . . . 2_656 ?
C6 C4 C5 C9 -47.0(4) . . . 2_656 ?
C6 C4 C5 C9 -173.1(3) . . . . ?
C7 C1 C2 C3 0.7(5) . . . . ?
C8 C3 C4 C5 -5.1(3) . . . . ?
C8 C3 C4 C6 177.8(3) . . . . ?
C9 C5 C9 C8 -135.8(2) 2_656 . . . ?

_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_cu_djp_4e_2_150k_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2253531'
loop_
_audit_author_name
_audit_author_address
'jiping du'
;Sichuan university
China
;
_audit_update_record             
;
2023-04-03 deposited with the CCDC.	2023-06-09 downloaded from the CCDC.
;
_audit_creation_date             2023-03-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H12 O2'
_chemical_formula_sum            'C17 H12 O2'
_chemical_formula_weight         248.27
_chemical_absolute_configuration ad
_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 0.0181 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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   17.6508(8)
_cell_length_b                   5.4506(2)
_cell_length_c                   6.5314(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.9500(10)
_cell_angle_gamma                90
_cell_volume                     609.84(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5436
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      71.920
_cell_measurement_theta_min      5.164
_shelx_estimated_absorpt_T_max   0.914
_shelx_estimated_absorpt_T_min   0.771
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1184 before and 0.0434 after correction.
The Ratio of minimum to maximum transmission is 0.8313.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5405
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.913
_diffrn_reflns_theta_min         5.164
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    0.943
_reflns_Friedel_fraction_max     0.933
_reflns_number_gt                1156
_reflns_number_total             1159
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 498 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     87
_refine_ls_number_reflns         1159
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0257
_refine_ls_restrained_S_all      1.106
_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)+(0.0271P)²+0.2596P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0657
_refine_ls_wR_factor_ref         0.0658
_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 Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C7(H7)
;
_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 0.62469(7) 0.2558(3) 1.02622(18) 0.0290(3) Uani 1 1 d . . . . .
C1 C 0.70326(9) 0.8022(3) 0.6184(3) 0.0261(4) Uani 1 1 d . . . . .
H1 H 0.7479 0.9056 0.6516 0.031 Uiso 1 1 calc R U . . .
C2 C 0.68854(10) 0.6434(3) 0.7691(3) 0.0241(4) Uani 1 1 d . . . . .
H2 H 0.7226 0.6352 0.9059 0.029 Uiso 1 1 calc R U . . .
C3 C 0.62217(9) 0.4956(3) 0.7145(2) 0.0185(4) Uani 1 1 d . . . . .
C4 C 0.57127(8) 0.5056(3) 0.5155(2) 0.0169(3) Uani 1 1 d . . . . .
C5 C 0.5000 0.3410(4) 0.5000 0.0169(5) Uani 1 2 d S T P . .
C6 C 0.65292(10) 0.8116(3) 0.4173(3) 0.0250(4) Uani 1 1 d . . . . .
H6 H 0.6640 0.9211 0.3152 0.030 Uiso 1 1 calc R U . . .
C7 C 0.58703(9) 0.6637(3) 0.3642(2) 0.0201(4) Uani 1 1 d . . . . .
H7 H 0.5533 0.6705 0.2268 0.024 Uiso 1 1 calc R U . . .
C8 C 0.59479(9) 0.3092(3) 0.8440(2) 0.0195(4) Uani 1 1 d . . . . .
C9 C 0.52260(9) 0.1895(3) 0.7062(2) 0.0185(4) Uani 1 1 d . . . . .
H9A H 0.4794 0.1902 0.7788 0.022 Uiso 1 1 calc R U . . .
H9B H 0.5339 0.0175 0.6749 0.022 Uiso 1 1 calc R U . . .


_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 C8 1.216(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.382(3) . ?
C1 C6 1.398(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.396(2) . ?
C3 C4 1.391(2) . ?
C3 C8 1.476(2) . ?
C4 C5 1.528(2) . ?
C4 C7 1.389(2) . ?
C5 C4 1.528(2) 2_656 ?
C5 C9 1.5481(19) . ?
C5 C9 1.5481(19) 2_656 ?
C6 H6 0.9500 . ?
C6 C7 1.389(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.519(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 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
C2 C1 H1 119.8 . . ?
C2 C1 C6 120.40(16) . . ?
C6 C1 H1 119.8 . . ?
C1 C2 H2 121.0 . . ?
C1 C2 C3 118.04(15) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 C8 128.43(14) . . ?
C4 C3 C2 121.96(14) . . ?
C4 C3 C8 109.60(13) . . ?
C3 C4 C5 112.00(12) . . ?
C7 C4 C3 119.60(14) . . ?
C7 C4 C5 128.30(13) . . ?
C4 C5 C4 108.13(18) . 2_656 ?
C4 C5 C9 102.72(8) . . ?
C4 C5 C9 102.72(8) 2_656 2_656 ?
C4 C5 C9 113.96(8) . 2_656 ?
C4 C5 C9 113.96(8) 2_656 . ?
C9 C5 C9 115.51(19) 2_656 . ?
C1 C6 H6 119.4 . . ?
C7 C6 C1 121.19(16) . . ?
C7 C6 H6 119.4 . . ?
C4 C7 H7 120.6 . . ?
C6 C7 C4 118.80(15) . . ?
C6 C7 H7 120.6 . . ?
O1 C8 C3 126.98(15) . . ?
O1 C8 C9 125.54(16) . . ?
C3 C8 C9 107.47(13) . . ?
C5 C9 H9A 110.4 . . ?
C5 C9 H9B 110.4 . . ?
C8 C9 C5 106.83(13) . . ?
C8 C9 H9A 110.4 . . ?
C8 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?

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
O1 C8 C9 C5 172.20(15) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C1 C2 C3 C8 178.51(16) . . . . ?
C1 C6 C7 C4 0.4(3) . . . . ?
C2 C1 C6 C7 0.3(3) . . . . ?
C2 C3 C4 C5 -175.60(16) . . . . ?
C2 C3 C4 C7 1.1(2) . . . . ?
C2 C3 C8 O1 2.2(3) . . . . ?
C2 C3 C8 C9 -176.46(16) . . . . ?
C3 C4 C5 C4 110.20(13) . . . 2_656 ?
C3 C4 C5 C9 -10.59(16) . . . . ?
C3 C4 C5 C9 -136.29(14) . . . 2_656 ?
C3 C4 C7 C6 -1.1(2) . . . . ?
C3 C8 C9 C5 -9.08(17) . . . . ?
C4 C3 C8 O1 -178.78(16) . . . . ?
C4 C3 C8 C9 2.53(18) . . . . ?
C4 C5 C9 C8 11.51(15) . . . . ?
C4 C5 C9 C8 -105.19(15) 2_656 . . . ?
C5 C4 C7 C6 175.00(15) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
C7 C4 C5 C4 -66.18(15) . . . 2_656 ?
C7 C4 C5 C9 47.3(2) . . . 2_656 ?
C7 C4 C5 C9 173.03(16) . . . . ?
C8 C3 C4 C5 5.33(18) . . . . ?
C8 C3 C4 C7 -177.94(15) . . . . ?
C9 C5 C9 C8 136.19(13) 2_656 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
