# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_cu_201118_sc_g_11_cu_0ma
_database_code_depnum_ccdc_archive 'CCDC 2145003'
loop_
_audit_author_name
_audit_author_address
'axially chiral aryl diene'
;Hangzhou Normal University
China
;
_audit_update_record             
;
2022-01-27 deposited with the CCDC.	2022-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 O3'
_chemical_formula_weight         244.28

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'

_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.
;

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                   8.8975(4)
_cell_length_b                   21.5517(9)
_cell_length_c                   6.9771(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1337.90(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.679
_shelx_estimated_absorpt_T_min   0.736
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11542
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         5.378
_diffrn_reflns_theta_max         72.501
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2628
_reflns_number_gt                2543
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_max     0.984
_reflns_Friedel_fraction_full    0.994

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0345P)²+0.2035P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1021 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2628
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0744
_refine_ls_wR_factor_gt          0.0732
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.32767(17) 0.16010(6) 0.6478(2) 0.0515(4) Uani 1 1 d . . . . .
O2 O 0.53899(15) 0.42332(6) 1.09094(18) 0.0364(3) Uani 1 1 d . . . . .
O3 O 0.73911(15) 0.47314(6) 0.9701(2) 0.0387(3) Uani 1 1 d . . . . .
C1 C 0.19517(18) 0.25467(7) 0.6897(2) 0.0275(3) Uani 1 1 d . . . . .
C2 C 0.10072(19) 0.23051(8) 0.8309(2) 0.0315(4) Uani 1 1 d . . . . .
H2 H 0.108766 0.188146 0.867170 0.038 Uiso 1 1 calc R U . . .
C3 C -0.0040(2) 0.26814(9) 0.9175(2) 0.0350(4) Uani 1 1 d . . . . .
H3 H -0.068040 0.251863 1.014181 0.042 Uiso 1 1 calc R U . . .
C4 C -0.01600(19) 0.32996(8) 0.8636(3) 0.0337(4) Uani 1 1 d . . . . .
H4 H -0.088637 0.355550 0.924542 0.040 Uiso 1 1 calc R U . . .
C5 C 0.07585(18) 0.35533(8) 0.7224(2) 0.0297(4) Uani 1 1 d . . . . .
C6 C 0.18437(18) 0.31726(7) 0.6349(2) 0.0254(3) Uani 1 1 d . . . . .
C7 C 0.3082(2) 0.21334(8) 0.6008(3) 0.0340(4) Uani 1 1 d . . . . .
H7 H 0.368999 0.229697 0.500876 0.041 Uiso 1 1 calc R U . . .
C8 C 0.0580(2) 0.42231(8) 0.6667(3) 0.0412(4) Uani 1 1 d . . . . .
H8A H 0.148027 0.445475 0.704362 0.062 Uiso 1 1 calc R U . . .
H8B H -0.030001 0.439762 0.731875 0.062 Uiso 1 1 calc R U . . .
H8C H 0.044166 0.425362 0.527703 0.062 Uiso 1 1 calc R U . . .
C9 C 0.28296(19) 0.34301(7) 0.4800(2) 0.0278(3) Uani 1 1 d . . . . .
C10 C 0.4096(2) 0.37433(8) 0.5190(3) 0.0305(4) Uani 1 1 d . . . . .
H10 H 0.469946 0.387736 0.414586 0.037 Uiso 1 1 calc R U . . .
C11 C 0.45956(19) 0.38884(7) 0.7113(2) 0.0287(3) Uani 1 1 d . . . . .
H11 H 0.401761 0.373105 0.814974 0.034 Uiso 1 1 calc R U . . .
C12 C 0.58114(19) 0.42279(8) 0.7541(3) 0.0325(4) Uani 1 1 d . . . . .
H12 H 0.646075 0.436646 0.654868 0.039 Uiso 1 1 calc R U . . .
C13 C 0.61395(19) 0.43855(7) 0.9543(3) 0.0293(4) Uani 1 1 d . . . . .
C14 C 0.7769(2) 0.49203(10) 1.1628(3) 0.0465(5) Uani 1 1 d . . . . .
H14A H 0.864892 0.519348 1.159561 0.070 Uiso 1 1 calc R U . . .
H14B H 0.799651 0.455272 1.240264 0.070 Uiso 1 1 calc R U . . .
H14C H 0.691706 0.514285 1.219471 0.070 Uiso 1 1 calc R U . . .
C15 C 0.2275(2) 0.33347(9) 0.2796(3) 0.0357(4) Uani 1 1 d . . . . .
H15A H 0.221263 0.288928 0.252553 0.053 Uiso 1 1 calc R U . . .
H15B H 0.297314 0.353024 0.189259 0.053 Uiso 1 1 calc R U . . .
H15C H 0.127788 0.352222 0.265856 0.053 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 C7 1.206(2) . ?
O2 C13 1.209(2) . ?
O3 C13 1.344(2) . ?
O3 C14 1.445(2) . ?
C1 C2 1.396(2) . ?
C1 C6 1.405(2) . ?
C1 C7 1.480(2) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.406(2) . ?
C5 C8 1.503(2) . ?
C6 C9 1.498(2) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.342(2) . ?
C9 C15 1.497(2) . ?
C10 C11 1.447(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.340(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.467(2) . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C13 O3 C14 115.13(15) . . ?
C2 C1 C6 120.60(15) . . ?
C2 C1 C7 118.73(15) . . ?
C6 C1 C7 120.67(15) . . ?
C3 C2 C1 119.87(16) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.94(16) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 121.56(16) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C6 118.77(15) . . ?
C4 C5 C8 119.85(16) . . ?
C6 C5 C8 121.38(16) . . ?
C1 C6 C5 119.25(15) . . ?
C1 C6 C9 120.77(14) . . ?
C5 C6 C9 119.94(14) . . ?
O1 C7 C1 123.78(17) . . ?
O1 C7 H7 118.1 . . ?
C1 C7 H7 118.1 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C15 122.37(15) . . ?
C10 C9 C6 122.12(15) . . ?
C15 C9 C6 115.47(14) . . ?
C9 C10 C11 123.69(15) . . ?
C9 C10 H10 118.2 . . ?
C11 C10 H10 118.2 . . ?
C12 C11 C10 124.92(16) . . ?
C12 C11 H11 117.5 . . ?
C10 C11 H11 117.5 . . ?
C11 C12 C13 119.96(15) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
O2 C13 O3 122.91(16) . . ?
O2 C13 C12 125.32(15) . . ?
O3 C13 C12 111.76(14) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_refine_diff_density_max         0.110
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_201118_sc_g_11_cu_0ma_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2145004'
loop_
_audit_author_name
_audit_author_address
'axially chiral aryl diene'
;Hangzhou Normal University
China
;
_audit_update_record             
;
2022-01-27 deposited with the CCDC.	2022-02-25 downloaded from the CCDC.
;
_audit_creation_date             2020-11-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 O3'
_chemical_formula_sum            'C15 H16 O3'
_chemical_formula_weight         244.28
_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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
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                   8.8975(4)
_cell_length_b                   21.5517(9)
_cell_length_c                   6.9771(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1337.90(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8957
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      72.50
_cell_measurement_theta_min      4.10
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.736
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1687 before and 0.0545 after correction.
The Ratio of minimum to maximum transmission is 0.8458.
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    1.213
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11542
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.501
_diffrn_reflns_theta_min         5.378
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                2543
_reflns_number_total             2628
_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 (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.110
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 1021 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   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2628
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0294
_refine_ls_restrained_S_all      1.070
_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)+(0.0345P)²+0.2035P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0744
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7), C10(H10), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_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 0.32767(17) 0.16010(6) 0.6478(2) 0.0515(4) Uani 1 1 d . . . . .
O2 O 0.53899(15) 0.42332(6) 1.09094(18) 0.0364(3) Uani 1 1 d . . . . .
O3 O 0.73911(15) 0.47314(6) 0.9701(2) 0.0387(3) Uani 1 1 d . . . . .
C1 C 0.19517(18) 0.25467(7) 0.6897(2) 0.0275(3) Uani 1 1 d . . . . .
C2 C 0.10072(19) 0.23051(8) 0.8309(2) 0.0315(4) Uani 1 1 d . . . . .
H2 H 0.108766 0.188146 0.867170 0.038 Uiso 1 1 calc R . . . .
C3 C -0.0040(2) 0.26814(9) 0.9175(2) 0.0350(4) Uani 1 1 d . . . . .
H3 H -0.068040 0.251863 1.014181 0.042 Uiso 1 1 calc R . . . .
C4 C -0.01600(19) 0.32996(8) 0.8636(3) 0.0337(4) Uani 1 1 d . . . . .
H4 H -0.088637 0.355550 0.924542 0.040 Uiso 1 1 calc R . . . .
C5 C 0.07585(18) 0.35533(8) 0.7224(2) 0.0297(4) Uani 1 1 d . . . . .
C6 C 0.18437(18) 0.31726(7) 0.6349(2) 0.0254(3) Uani 1 1 d . . . . .
C7 C 0.3082(2) 0.21334(8) 0.6008(3) 0.0340(4) Uani 1 1 d . . . . .
H7 H 0.368999 0.229697 0.500876 0.041 Uiso 1 1 calc R . . . .
C8 C 0.0580(2) 0.42231(8) 0.6667(3) 0.0412(4) Uani 1 1 d . . . . .
H8A H 0.148027 0.445475 0.704362 0.062 Uiso 1 1 calc GR . . . .
H8B H -0.030001 0.439762 0.731875 0.062 Uiso 1 1 calc GR . . . .
H8C H 0.044166 0.425362 0.527703 0.062 Uiso 1 1 calc GR . . . .
C9 C 0.28296(19) 0.34301(7) 0.4800(2) 0.0278(3) Uani 1 1 d . . . . .
C10 C 0.4096(2) 0.37433(8) 0.5190(3) 0.0305(4) Uani 1 1 d . . . . .
H10 H 0.469946 0.387736 0.414586 0.037 Uiso 1 1 calc R . . . .
C11 C 0.45956(19) 0.38884(7) 0.7113(2) 0.0287(3) Uani 1 1 d . . . . .
H11 H 0.401761 0.373105 0.814974 0.034 Uiso 1 1 calc R . . . .
C12 C 0.58114(19) 0.42279(8) 0.7541(3) 0.0325(4) Uani 1 1 d . . . . .
H12 H 0.646075 0.436646 0.654868 0.039 Uiso 1 1 calc R . . . .
C13 C 0.61395(19) 0.43855(7) 0.9543(3) 0.0293(4) Uani 1 1 d . . . . .
C14 C 0.7769(2) 0.49203(10) 1.1628(3) 0.0465(5) Uani 1 1 d . . . . .
H14A H 0.864892 0.519348 1.159561 0.070 Uiso 1 1 calc GR . . . .
H14B H 0.799651 0.455272 1.240264 0.070 Uiso 1 1 calc GR . . . .
H14C H 0.691706 0.514285 1.219471 0.070 Uiso 1 1 calc GR . . . .
C15 C 0.2275(2) 0.33347(9) 0.2796(3) 0.0357(4) Uani 1 1 d . . . . .
H15A H 0.221263 0.288928 0.252553 0.053 Uiso 1 1 calc GR . . . .
H15B H 0.297314 0.353024 0.189259 0.053 Uiso 1 1 calc GR . . . .
H15C H 0.127788 0.352222 0.265856 0.053 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 C7 1.206(2) . ?
O2 C13 1.209(2) . ?
O3 C13 1.344(2) . ?
O3 C14 1.445(2) . ?
C1 C2 1.396(2) . ?
C1 C6 1.405(2) . ?
C1 C7 1.480(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.375(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(2) . ?
C5 C6 1.406(2) . ?
C5 C8 1.503(2) . ?
C6 C9 1.498(2) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.342(2) . ?
C9 C15 1.497(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.447(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.340(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.467(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C13 O3 C14 115.13(15) . . ?
C2 C1 C6 120.60(15) . . ?
C2 C1 C7 118.73(15) . . ?
C6 C1 C7 120.67(15) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.87(16) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.94(16) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.2 . . ?
C3 C4 C5 121.56(16) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C6 118.77(15) . . ?
C4 C5 C8 119.85(16) . . ?
C6 C5 C8 121.38(16) . . ?
C1 C6 C5 119.25(15) . . ?
C1 C6 C9 120.77(14) . . ?
C5 C6 C9 119.94(14) . . ?
O1 C7 C1 123.78(17) . . ?
O1 C7 H7 118.1 . . ?
C1 C7 H7 118.1 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C6 122.12(15) . . ?
C10 C9 C15 122.37(15) . . ?
C15 C9 C6 115.47(14) . . ?
C9 C10 H10 118.2 . . ?
C9 C10 C11 123.69(15) . . ?
C11 C10 H10 118.2 . . ?
C10 C11 H11 117.5 . . ?
C12 C11 C10 124.92(16) . . ?
C12 C11 H11 117.5 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 119.96(15) . . ?
C13 C12 H12 120.0 . . ?
O2 C13 O3 122.91(16) . . ?
O2 C13 C12 125.32(15) . . ?
O3 C13 C12 111.76(14) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
