# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_cxy0591
_database_code_depnum_ccdc_archive 'CCDC 1906351'
loop_
_audit_author_name
_audit_author_address
'Xiaoyong Chang'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2019-03-28 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;
_audit_creation_date             2018-12-19
_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         'C13 H16 O2'
_chemical_formula_sum            'C13 H16 O2'
_chemical_formula_weight         204.26
_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   6.2989(3)
_cell_length_b                   10.0377(5)
_cell_length_c                   17.5539(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1109.87(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9821
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.63
_cell_measurement_theta_min      4.40
_shelx_estimated_absorpt_T_max   0.850
_shelx_estimated_absorpt_T_min   0.774
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0823 before and 0.0515 after correction. The Ratio of minimum to maximum transmission is 0.8461. 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    1.222
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16724
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.606
_diffrn_reflns_theta_min         5.039
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2016
_reflns_number_total             2026
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Flack x determined using 825 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(8)
_refine_ls_extinction_coef       0.025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2026
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0268
_refine_ls_restrained_S_all      1.098
_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)+(0.0318P)²+0.2051P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0676
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.01017(17) 0.59839(11) 0.29393(7) 0.0241(3) Uani 1 1 d . . . . .
H1 H -0.116566 0.612168 0.281300 0.036 Uiso 1 1 calc GR . . . .
O2 O 0.58889(18) 0.67726(12) 0.26886(6) 0.0265(3) Uani 1 1 d . . . . .
C1 C 0.0164(3) 0.37452(15) 0.58007(9) 0.0243(4) Uani 1 1 d . . . . .
H1A H -0.058949 0.342750 0.623279 0.029 Uiso 1 1 calc R . . . .
C2 C 0.2186(3) 0.42828(16) 0.58843(10) 0.0250(4) Uani 1 1 d . . . . .
H2 H 0.282073 0.432756 0.637457 0.030 Uiso 1 1 calc R . . . .
C3 C 0.3279(3) 0.47548(15) 0.52513(9) 0.0219(4) Uani 1 1 d . . . . .
H3 H 0.466028 0.511909 0.531417 0.026 Uiso 1 1 calc R . . . .
C4 C 0.2380(3) 0.47019(14) 0.45239(9) 0.0190(3) Uani 1 1 d . . . . .
C5 C 0.3558(3) 0.52125(15) 0.38311(9) 0.0200(4) Uani 1 1 d . . . . .
H5A H 0.316110 0.466441 0.338444 0.024 Uiso 1 1 calc R . . . .
H5B H 0.510253 0.510226 0.391537 0.024 Uiso 1 1 calc R . . . .
C6 C 0.3095(2) 0.66875(15) 0.36517(8) 0.0181(4) Uani 1 1 d . . . . .
C7 C 0.4200(2) 0.71760(15) 0.29313(9) 0.0195(3) Uani 1 1 d . . . . .
C8 C 0.2885(3) 0.82615(16) 0.25609(9) 0.0238(4) Uani 1 1 d . . . . .
H8A H 0.254503 0.802784 0.202677 0.029 Uiso 1 1 calc R . . . .
H8B H 0.365557 0.912116 0.256700 0.029 Uiso 1 1 calc R . . . .
C9 C 0.0856(3) 0.83458(15) 0.30424(9) 0.0234(4) Uani 1 1 d . . . . .
H9A H -0.040973 0.846902 0.271532 0.028 Uiso 1 1 calc R . . . .
H9B H 0.093634 0.909156 0.341032 0.028 Uiso 1 1 calc R . . . .
C10 C -0.0744(3) 0.36761(15) 0.50805(9) 0.0230(4) Uani 1 1 d . . . . .
H10 H -0.211716 0.329946 0.501832 0.028 Uiso 1 1 calc R . . . .
C11 C 0.0353(2) 0.41578(14) 0.44507(9) 0.0213(4) Uani 1 1 d . . . . .
H11 H -0.028955 0.411538 0.396165 0.026 Uiso 1 1 calc R . . . .
C12 C 0.3906(3) 0.75957(16) 0.42956(9) 0.0245(4) Uani 1 1 d . . . . .
H12A H 0.542983 0.744842 0.436981 0.037 Uiso 1 1 calc GR . . . .
H12B H 0.314664 0.738742 0.476818 0.037 Uiso 1 1 calc GR . . . .
H12C H 0.365707 0.852928 0.415887 0.037 Uiso 1 1 calc GR . . . .
C13 C 0.0775(2) 0.69953(14) 0.34581(9) 0.0195(3) Uani 1 1 d . . . . .
H13 H -0.013944 0.703040 0.392350 0.023 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 H1 0.8400 . ?
O1 C13 1.4282(18) . ?
O2 C7 1.2155(19) . ?
C1 H1A 0.9500 . ?
C1 C2 1.391(3) . ?
C1 C10 1.390(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(2) . ?
C4 C5 1.514(2) . ?
C4 C11 1.394(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.542(2) . ?
C6 C7 1.524(2) . ?
C6 C12 1.539(2) . ?
C6 C13 1.532(2) . ?
C7 C8 1.515(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.535(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C13 1.540(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(2) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 1.0000 . ?

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 O1 H1 109.5 . . ?
C2 C1 H1A 120.2 . . ?
C10 C1 H1A 120.2 . . ?
C10 C1 C2 119.51(16) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.09(15) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.07(15) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 121.46(14) . . ?
C11 C4 C3 118.05(14) . . ?
C11 C4 C5 120.50(14) . . ?
C4 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C4 C5 C6 113.34(13) . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C7 C6 C5 113.07(13) . . ?
C7 C6 C12 105.49(12) . . ?
C7 C6 C13 100.76(12) . . ?
C12 C6 C5 110.84(12) . . ?
C13 C6 C5 114.82(13) . . ?
C13 C6 C12 111.10(13) . . ?
O2 C7 C6 125.68(14) . . ?
O2 C7 C8 124.57(14) . . ?
C8 C7 C6 109.74(13) . . ?
C7 C8 H8A 110.8 . . ?
C7 C8 H8B 110.8 . . ?
C7 C8 C9 104.98(13) . . ?
H8A C8 H8B 108.8 . . ?
C9 C8 H8A 110.8 . . ?
C9 C8 H8B 110.8 . . ?
C8 C9 H9A 111.0 . . ?
C8 C9 H9B 111.0 . . ?
C8 C9 C13 103.89(12) . . ?
H9A C9 H9B 109.0 . . ?
C13 C9 H9A 111.0 . . ?
C13 C9 H9B 111.0 . . ?
C1 C10 H10 120.0 . . ?
C1 C10 C11 120.08(15) . . ?
C11 C10 H10 120.0 . . ?
C4 C11 H11 119.4 . . ?
C10 C11 C4 121.20(15) . . ?
C10 C11 H11 119.4 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 C6 106.33(12) . . ?
O1 C13 C9 109.47(12) . . ?
O1 C13 H13 112.0 . . ?
C6 C13 C9 104.53(12) . . ?
C6 C13 H13 112.0 . . ?
C9 C13 H13 112.0 . . ?

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
O2 C7 C8 C9 176.29(14) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C1 C10 C11 C4 0.7(2) . . . . ?
C2 C1 C10 C11 -0.8(2) . . . . ?
C2 C3 C4 C5 -179.96(14) . . . . ?
C2 C3 C4 C11 -0.2(2) . . . . ?
C3 C4 C5 C6 -91.48(17) . . . . ?
C3 C4 C11 C10 -0.2(2) . . . . ?
C4 C5 C6 C7 -177.14(13) . . . . ?
C4 C5 C6 C12 64.64(18) . . . . ?
C4 C5 C6 C13 -62.27(17) . . . . ?
C5 C4 C11 C10 179.55(14) . . . . ?
C5 C6 C7 O2 -30.7(2) . . . . ?
C5 C6 C7 C8 149.95(13) . . . . ?
C5 C6 C13 O1 -45.16(16) . . . . ?
C5 C6 C13 C9 -160.93(12) . . . . ?
C6 C7 C8 C9 -4.32(17) . . . . ?
C7 C6 C13 O1 76.67(13) . . . . ?
C7 C6 C13 C9 -39.10(14) . . . . ?
C7 C8 C9 C13 -20.20(16) . . . . ?
C8 C9 C13 O1 -75.89(15) . . . . ?
C8 C9 C13 C6 37.67(15) . . . . ?
C10 C1 C2 C3 0.4(2) . . . . ?
C11 C4 C5 C6 88.76(16) . . . . ?
C12 C6 C7 O2 90.61(18) . . . . ?
C12 C6 C7 C8 -88.76(15) . . . . ?
C12 C6 C13 O1 -171.93(12) . . . . ?
C12 C6 C13 C9 72.30(15) . . . . ?
C13 C6 C7 O2 -153.73(14) . . . . ?
C13 C6 C7 C8 26.90(15) . . . . ?

_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_cxy0647_0m
_database_code_depnum_ccdc_archive 'CCDC 1906354'
loop_
_audit_author_name
_audit_author_address
'Xiaoyong Chang'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2019-03-28 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;
_audit_creation_date             2019-03-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H18 O2'
_chemical_formula_sum            'C13 H18 O2'
_chemical_formula_weight         206.27
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.9109(7)
_cell_length_b                   9.9938(9)
_cell_length_c                   8.2507(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.496(5)
_cell_angle_gamma                90
_cell_volume                     569.30(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6265
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.50
_cell_measurement_theta_min      5.37
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0999 before and 0.0755 after correction. The Ratio of minimum to maximum transmission is 0.7536. 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    1.203
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7567
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.490
_diffrn_reflns_theta_min         5.366
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.871
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                1988
_reflns_number_total             2079
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 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         0.206
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 892 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       0.017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2079
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.073
_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)+(0.0452P)²+0.1863P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1018
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C8(H8A,H8B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2A), C3(H3), C9(H9), C10(H10)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_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 0.9179(3) 0.43432(19) 0.4225(2) 0.0287(5) Uani 1 1 d . . . . .
H1 H 0.987663 0.365626 0.419374 0.043 Uiso 1 1 calc GR . . . .
O2 O 0.9005(3) 0.69100(19) 0.5363(2) 0.0310(5) Uani 1 1 d . . . . .
H2 H 0.961610 0.630574 0.489608 0.046 Uiso 1 1 calc GR . . . .
C1 C 0.2726(5) 0.3262(3) 0.0046(3) 0.0337(7) Uani 1 1 d . . . . .
H1A H 0.204082 0.270119 -0.071113 0.040 Uiso 1 1 calc R . . . .
C2 C 0.1765(4) 0.4264(3) 0.0844(3) 0.0323(6) Uani 1 1 d . . . . .
H2A H 0.041141 0.438252 0.064736 0.039 Uiso 1 1 calc R . . . .
C3 C 0.2774(4) 0.5096(3) 0.1931(3) 0.0282(6) Uani 1 1 d . . . . .
H3 H 0.209710 0.578089 0.246920 0.034 Uiso 1 1 calc R . . . .
C4 C 0.4764(4) 0.4946(3) 0.2249(3) 0.0247(6) Uani 1 1 d . . . . .
C5 C 0.5869(4) 0.5877(3) 0.3400(3) 0.0261(6) Uani 1 1 d . . . . .
H5A H 0.513408 0.672375 0.346908 0.031 Uiso 1 1 calc R . . . .
H5B H 0.712781 0.608976 0.293282 0.031 Uiso 1 1 calc R . . . .
C6 C 0.6258(4) 0.5333(3) 0.5135(3) 0.0241(6) Uani 1 1 d . . . . .
C7 C 0.7564(4) 0.4088(2) 0.5224(3) 0.0246(6) Uani 1 1 d . . . . .
H7 H 0.684138 0.326386 0.486892 0.029 Uiso 1 1 calc R . . . .
C8 C 0.8251(4) 0.4005(3) 0.7011(3) 0.0293(6) Uani 1 1 d . . . . .
H8A H 0.957478 0.362707 0.711656 0.035 Uiso 1 1 calc R . . . .
H8B H 0.737010 0.343473 0.762554 0.035 Uiso 1 1 calc R . . . .
C9 C 0.4699(5) 0.3083(3) 0.0360(3) 0.0319(7) Uani 1 1 d . . . . .
H9 H 0.536262 0.238578 -0.016763 0.038 Uiso 1 1 calc R . . . .
C10 C 0.5702(4) 0.3919(3) 0.1441(3) 0.0278(6) Uani 1 1 d . . . . .
H10 H 0.705476 0.379201 0.163651 0.033 Uiso 1 1 calc R . . . .
C11 C 0.7444(4) 0.6320(3) 0.6221(3) 0.0263(6) Uani 1 1 d . . . . .
H11 H 0.657804 0.703848 0.662250 0.032 Uiso 1 1 calc R . . . .
C12 C 0.8228(4) 0.5469(3) 0.7649(4) 0.0303(6) Uani 1 1 d . . . . .
H12A H 0.737922 0.554677 0.858109 0.036 Uiso 1 1 calc R . . . .
H12B H 0.955026 0.576025 0.799905 0.036 Uiso 1 1 calc R . . . .
C13 C 0.4335(4) 0.5030(3) 0.5933(3) 0.0286(6) Uani 1 1 d . . . . .
H13A H 0.367970 0.428647 0.536180 0.043 Uiso 1 1 calc GR . . . .
H13B H 0.350478 0.582478 0.587392 0.043 Uiso 1 1 calc GR . . . .
H13C H 0.459558 0.478447 0.707178 0.043 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 H1 0.8400 . ?
O1 C7 1.439(3) . ?
O2 H2 0.8400 . ?
O2 C11 1.442(3) . ?
C1 H1A 0.9500 . ?
C1 C2 1.384(4) . ?
C1 C9 1.388(5) . ?
C2 H2A 0.9500 . ?
C2 C3 1.388(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.397(4) . ?
C4 C5 1.512(4) . ?
C4 C10 1.399(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.544(4) . ?
C6 C7 1.538(3) . ?
C6 C11 1.544(4) . ?
C6 C13 1.539(4) . ?
C7 H7 1.0000 . ?
C7 C8 1.531(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C12 1.556(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(4) . ?
C10 H10 0.9500 . ?
C11 H11 1.0000 . ?
C11 C12 1.533(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
C7 O1 H1 109.5 . . ?
C11 O2 H2 109.5 . . ?
C2 C1 H1A 120.3 . . ?
C2 C1 C9 119.5(3) . . ?
C9 C1 H1A 120.3 . . ?
C1 C2 H2A 119.9 . . ?
C1 C2 C3 120.2(3) . . ?
C3 C2 H2A 119.9 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.3(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 121.2(2) . . ?
C3 C4 C10 117.5(3) . . ?
C10 C4 C5 121.3(2) . . ?
C4 C5 H5A 108.4 . . ?
C4 C5 H5B 108.4 . . ?
C4 C5 C6 115.4(2) . . ?
H5A C5 H5B 107.5 . . ?
C6 C5 H5A 108.4 . . ?
C6 C5 H5B 108.4 . . ?
C7 C6 C5 114.0(2) . . ?
C7 C6 C11 101.2(2) . . ?
C7 C6 C13 109.6(2) . . ?
C11 C6 C5 112.3(2) . . ?
C13 C6 C5 110.3(2) . . ?
C13 C6 C11 108.9(2) . . ?
O1 C7 C6 107.3(2) . . ?
O1 C7 H7 111.6 . . ?
O1 C7 C8 110.2(2) . . ?
C6 C7 H7 111.6 . . ?
C8 C7 C6 104.3(2) . . ?
C8 C7 H7 111.6 . . ?
C7 C8 H8A 110.6 . . ?
C7 C8 H8B 110.6 . . ?
C7 C8 C12 105.6(2) . . ?
H8A C8 H8B 108.8 . . ?
C12 C8 H8A 110.6 . . ?
C12 C8 H8B 110.6 . . ?
C1 C9 H9 119.9 . . ?
C10 C9 C1 120.1(3) . . ?
C10 C9 H9 119.9 . . ?
C4 C10 H10 119.3 . . ?
C9 C10 C4 121.3(3) . . ?
C9 C10 H10 119.3 . . ?
O2 C11 C6 111.4(2) . . ?
O2 C11 H11 109.9 . . ?
O2 C11 C12 111.0(2) . . ?
C6 C11 H11 109.9 . . ?
C12 C11 C6 104.6(2) . . ?
C12 C11 H11 109.9 . . ?
C8 C12 H12A 110.6 . . ?
C8 C12 H12B 110.6 . . ?
C11 C12 C8 105.7(2) . . ?
C11 C12 H12A 110.6 . . ?
C11 C12 H12B 110.6 . . ?
H12A C12 H12B 108.7 . . ?
C6 C13 H13A 109.5 . . ?
C6 C13 H13B 109.5 . . ?
C6 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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 C7 C8 C12 87.1(3) . . . . ?
O2 C11 C12 C8 -96.5(3) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C1 C9 C10 C4 0.7(4) . . . . ?
C2 C1 C9 C10 -1.3(4) . . . . ?
C2 C3 C4 C5 178.4(2) . . . . ?
C2 C3 C4 C10 -0.5(4) . . . . ?
C3 C4 C5 C6 98.9(3) . . . . ?
C3 C4 C10 C9 0.2(4) . . . . ?
C4 C5 C6 C7 63.9(3) . . . . ?
C4 C5 C6 C11 178.2(2) . . . . ?
C4 C5 C6 C13 -60.0(3) . . . . ?
C5 C4 C10 C9 -178.6(2) . . . . ?
C5 C6 C7 O1 45.9(3) . . . . ?
C5 C6 C7 C8 162.8(2) . . . . ?
C5 C6 C11 O2 -42.5(3) . . . . ?
C5 C6 C11 C12 -162.5(2) . . . . ?
C6 C7 C8 C12 -27.7(3) . . . . ?
C6 C11 C12 C8 23.8(3) . . . . ?
C7 C6 C11 O2 79.5(2) . . . . ?
C7 C6 C11 C12 -40.5(3) . . . . ?
C7 C8 C12 C11 2.4(3) . . . . ?
C9 C1 C2 C3 1.0(4) . . . . ?
C10 C4 C5 C6 -82.3(3) . . . . ?
C11 C6 C7 O1 -74.9(2) . . . . ?
C11 C6 C7 C8 42.0(2) . . . . ?
C13 C6 C7 O1 170.2(2) . . . . ?
C13 C6 C7 C8 -73.0(3) . . . . ?
C13 C6 C11 O2 -165.1(2) . . . . ?
C13 C6 C11 C12 75.0(3) . . . . ?

_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_cxy0634_0m
_database_code_depnum_ccdc_archive 'CCDC 1906353'
loop_
_audit_author_name
_audit_author_address
'Xiaoyong Chang'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2019-03-28 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;
_audit_creation_date             2019-01-18
_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         'C17 H16 O2'
_chemical_formula_sum            'C17 H16 O2'
_chemical_formula_weight         252.30
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.1412(2)
_cell_length_b                   6.7002(3)
_cell_length_c                   15.7738(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.466(2)
_cell_angle_gamma                90
_cell_volume                     647.08(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7070
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.10
_cell_measurement_theta_min      2.81
_shelx_estimated_absorpt_T_max   0.836
_shelx_estimated_absorpt_T_min   0.768
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1247 before and 0.0730 after correction. The Ratio of minimum to maximum transmission is 0.6526. 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    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7757
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.092
_diffrn_reflns_theta_min         2.810
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.821
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                2270
_reflns_number_total             2302
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1008 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.40(17)
_refine_ls_extinction_coef       0.068(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2302
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.050
_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)+(0.0610P)²+0.1760P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1039
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15),
 C16(H16)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 -0.0368(3) 0.5340(3) 0.12123(11) 0.0214(4) Uani 1 1 d . . . . .
O2 O 0.6130(3) 0.4065(3) 0.21381(13) 0.0268(5) Uani 1 1 d . . . . .
H2 H 0.717305 0.451805 0.188230 0.040 Uiso 1 1 calc GR . . . .
C1 C 0.6052(4) 1.0111(4) 0.09659(16) 0.0221(5) Uani 1 1 d . . . . .
H1 H 0.715365 1.105184 0.085787 0.027 Uiso 1 1 calc R . . . .
C2 C 0.6415(4) 0.8762(4) 0.16320(16) 0.0204(5) Uani 1 1 d . . . . .
H2A H 0.774729 0.878141 0.198123 0.024 Uiso 1 1 calc R . . . .
C3 C 0.4791(4) 0.7384(4) 0.17773(15) 0.0175(5) Uani 1 1 d . . . . .
C4 C 0.4843(4) 0.5677(4) 0.24115(15) 0.0190(6) Uani 1 1 d . . . . .
H4 H 0.540623 0.614412 0.298952 0.023 Uiso 1 1 calc R . . . .
C5 C 0.2417(4) 0.5024(4) 0.24109(15) 0.0170(5) Uani 1 1 d . . . . .
C6 C 0.1996(4) 0.2759(4) 0.24580(15) 0.0178(5) Uani 1 1 d . . . . .
H6A H 0.043671 0.250984 0.228294 0.021 Uiso 1 1 calc R . . . .
H6B H 0.286867 0.208630 0.203995 0.021 Uiso 1 1 calc R . . . .
C7 C 0.2526(4) 0.1804(4) 0.33173(15) 0.0178(5) Uani 1 1 d . . . . .
C8 C 0.0936(4) 0.1667(4) 0.38991(17) 0.0221(6) Uani 1 1 d . . . . .
H8 H -0.047304 0.221588 0.375965 0.027 Uiso 1 1 calc R . . . .
C9 C 0.1390(5) 0.0734(4) 0.46838(17) 0.0299(7) Uani 1 1 d . . . . .
H9 H 0.029628 0.066830 0.507700 0.036 Uiso 1 1 calc R . . . .
C10 C 0.3419(5) -0.0093(4) 0.48916(18) 0.0324(7) Uani 1 1 d . . . . .
H10 H 0.372339 -0.073420 0.542477 0.039 Uiso 1 1 calc R . . . .
C11 C 0.4574(4) 0.0973(4) 0.35346(17) 0.0220(6) Uani 1 1 d . . . . .
H11 H 0.567957 0.105767 0.314716 0.026 Uiso 1 1 calc R . . . .
C12 C 0.5017(5) 0.0020(4) 0.43144(18) 0.0291(6) Uani 1 1 d . . . . .
H12 H 0.641412 -0.055462 0.445221 0.035 Uiso 1 1 calc R . . . .
C13 C 0.1395(4) 0.5843(4) 0.15593(14) 0.0163(5) Uani 1 1 d . . . . .
C14 C 0.2844(4) 0.7397(4) 0.12638(15) 0.0177(5) Uani 1 1 d . . . . .
C15 C 0.4080(4) 1.0103(4) 0.04501(16) 0.0224(6) Uani 1 1 d . . . . .
H15 H 0.386530 1.103020 -0.000423 0.027 Uiso 1 1 calc R . . . .
C16 C 0.2452(4) 0.8755(4) 0.05994(16) 0.0204(6) Uani 1 1 d . . . . .
H16 H 0.110504 0.875299 0.025967 0.024 Uiso 1 1 calc R . . . .
C17 C 0.1336(4) 0.6175(4) 0.31102(16) 0.0193(5) Uani 1 1 d . . . . .
H17A H 0.155374 0.761048 0.303381 0.029 Uiso 1 1 calc GR . . . .
H17B H 0.199664 0.576677 0.366888 0.029 Uiso 1 1 calc GR . . . .
H17C H -0.023190 0.588021 0.307333 0.029 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 C13 1.222(3) . ?
O2 H2 0.8400 . ?
O2 C4 1.425(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.391(4) . ?
C1 C15 1.406(4) . ?
C2 H2A 0.9500 . ?
C2 C3 1.391(4) . ?
C3 C4 1.518(3) . ?
C3 C14 1.391(3) . ?
C4 H4 1.0000 . ?
C4 C5 1.553(3) . ?
C5 C6 1.542(3) . ?
C5 C13 1.539(3) . ?
C5 C17 1.538(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.511(3) . ?
C7 C8 1.394(4) . ?
C7 C11 1.393(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.395(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.380(4) . ?
C10 H10 0.9500 . ?
C10 C12 1.392(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.394(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.469(3) . ?
C14 C16 1.395(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.381(4) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C4 O2 H2 109.5 . . ?
C2 C1 H1 119.5 . . ?
C2 C1 C15 121.0(2) . . ?
C15 C1 H1 119.5 . . ?
C1 C2 H2A 120.6 . . ?
C1 C2 C3 118.7(2) . . ?
C3 C2 H2A 120.6 . . ?
C2 C3 C4 129.1(2) . . ?
C14 C3 C2 119.7(2) . . ?
C14 C3 C4 111.2(2) . . ?
O2 C4 C3 110.81(19) . . ?
O2 C4 H4 110.7 . . ?
O2 C4 C5 109.94(19) . . ?
C3 C4 H4 110.7 . . ?
C3 C4 C5 103.96(18) . . ?
C5 C4 H4 110.7 . . ?
C6 C5 C4 116.2(2) . . ?
C13 C5 C4 103.05(18) . . ?
C13 C5 C6 109.55(19) . . ?
C17 C5 C4 109.02(19) . . ?
C17 C5 C6 112.1(2) . . ?
C17 C5 C13 106.13(18) . . ?
C5 C6 H6A 108.3 . . ?
C5 C6 H6B 108.3 . . ?
H6A C6 H6B 107.4 . . ?
C7 C6 C5 115.8(2) . . ?
C7 C6 H6A 108.3 . . ?
C7 C6 H6B 108.3 . . ?
C8 C7 C6 120.4(2) . . ?
C11 C7 C6 121.1(2) . . ?
C11 C7 C8 118.5(2) . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C12 119.5(3) . . ?
C12 C10 H10 120.2 . . ?
C7 C11 H11 119.6 . . ?
C7 C11 C12 120.7(2) . . ?
C12 C11 H11 119.6 . . ?
C10 C12 C11 120.2(3) . . ?
C10 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
O1 C13 C5 125.4(2) . . ?
O1 C13 C14 126.2(2) . . ?
C14 C13 C5 108.30(19) . . ?
C3 C14 C13 109.0(2) . . ?
C3 C14 C16 122.1(2) . . ?
C16 C14 C13 128.9(2) . . ?
C1 C15 H15 119.8 . . ?
C16 C15 C1 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C16 H16 121.0 . . ?
C15 C16 C14 118.0(2) . . ?
C15 C16 H16 121.0 . . ?
C5 C17 H17A 109.5 . . ?
C5 C17 H17B 109.5 . . ?
C5 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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 C13 C14 C3 -173.8(2) . . . . ?
O1 C13 C14 C16 7.7(4) . . . . ?
O2 C4 C5 C6 21.8(3) . . . . ?
O2 C4 C5 C13 -98.0(2) . . . . ?
O2 C4 C5 C17 149.60(19) . . . . ?
C1 C2 C3 C4 175.0(2) . . . . ?
C1 C2 C3 C14 -0.7(4) . . . . ?
C1 C15 C16 C14 -1.0(4) . . . . ?
C2 C1 C15 C16 0.4(4) . . . . ?
C2 C3 C4 O2 -74.6(3) . . . . ?
C2 C3 C4 C5 167.3(2) . . . . ?
C2 C3 C14 C13 -178.6(2) . . . . ?
C2 C3 C14 C16 0.0(4) . . . . ?
C3 C4 C5 C6 140.5(2) . . . . ?
C3 C4 C5 C13 20.7(2) . . . . ?
C3 C4 C5 C17 -91.7(2) . . . . ?
C3 C14 C16 C15 0.8(4) . . . . ?
C4 C3 C14 C13 4.9(3) . . . . ?
C4 C3 C14 C16 -176.4(2) . . . . ?
C4 C5 C6 C7 74.7(3) . . . . ?
C4 C5 C13 O1 164.2(2) . . . . ?
C4 C5 C13 C14 -18.8(2) . . . . ?
C5 C6 C7 C8 90.4(3) . . . . ?
C5 C6 C7 C11 -92.1(3) . . . . ?
C5 C13 C14 C3 9.2(3) . . . . ?
C5 C13 C14 C16 -169.3(2) . . . . ?
C6 C5 C13 O1 39.9(3) . . . . ?
C6 C5 C13 C14 -143.1(2) . . . . ?
C6 C7 C8 C9 178.0(2) . . . . ?
C6 C7 C11 C12 -177.2(2) . . . . ?
C7 C8 C9 C10 -0.8(4) . . . . ?
C7 C11 C12 C10 -0.8(4) . . . . ?
C8 C7 C11 C12 0.3(4) . . . . ?
C8 C9 C10 C12 0.4(4) . . . . ?
C9 C10 C12 C11 0.4(4) . . . . ?
C11 C7 C8 C9 0.5(4) . . . . ?
C13 C5 C6 C7 -169.03(19) . . . . ?
C13 C14 C16 C15 179.2(2) . . . . ?
C14 C3 C4 O2 101.4(2) . . . . ?
C14 C3 C4 C5 -16.7(3) . . . . ?
C15 C1 C2 C3 0.5(4) . . . . ?
C17 C5 C6 C7 -51.5(3) . . . . ?
C17 C5 C13 O1 -81.3(3) . . . . ?
C17 C5 C13 C14 95.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
