# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_zhangzh_0906
_database_code_depnum_ccdc_archive 'CCDC 1899674'
_audit_update_record             
;
2019-02-26 deposited with the CCDC.	2019-05-06 downloaded from the CCDC.
;
_audit_creation_date             2018-11-09
_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         'C17 H23 N O4'
_chemical_formula_sum            'C17 H23 N O4'
_chemical_formula_weight         305.36
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.0924(10)
_cell_length_b                   16.7422(11)
_cell_length_c                   8.2780(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.825(9)
_cell_angle_gamma                90
_cell_volume                     1595.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1456
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9450
_cell_measurement_theta_min      3.7370
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            5995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         3.540
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -101.00  -62.00   1.0000    5.0600
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  178.0000  -90.0000 39

#__ type_ start__ end____ width___ exp.time_
  2 omega  -20.00    6.00   1.0000    5.0600
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  -99.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   61.00   99.00   1.0000    5.0600
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000   60.0000 38

#__ type_ start__ end____ width___ exp.time_
  4 omega  -41.00   90.00   1.0000    5.0600
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000 -150.0000 131
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0081509000
_diffrn_orient_matrix_UB_12      0.0125886000
_diffrn_orient_matrix_UB_13      0.0773825000
_diffrn_orient_matrix_UB_21      -0.0306498000
_diffrn_orient_matrix_UB_22      0.0341220000
_diffrn_orient_matrix_UB_23      -0.0412970000
_diffrn_orient_matrix_UB_31      -0.0528483000
_diffrn_orient_matrix_UB_32      -0.0217170000
_diffrn_orient_matrix_UB_33      -0.0201078000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2097
_reflns_number_total             3132
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3132
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0579
_refine_ls_restrained_S_all      1.051
_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)+(0.0470P)²+0.3565P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1514
_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:
 C1(H1), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C14(H14A,H14B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.37718(13) 0.10162(9) 0.2518(2) 0.0421(4) Uani 1 1 d . . . . .
O2 O 0.06950(12) 0.00702(9) 0.3019(2) 0.0461(4) Uani 1 1 d . . . . .
O3 O 0.20818(15) -0.08577(10) 0.4114(2) 0.0504(5) Uani 1 1 d . . . . .
H3 H 0.267941 -0.105319 0.401453 0.076 Uiso 1 1 calc GR . . . .
O4 O 0.36370(14) -0.10982(10) 0.2398(2) 0.0524(5) Uani 1 1 d . . . . .
N1 N 0.30545(15) -0.06734(11) -0.0321(2) 0.0388(5) Uani 1 1 d . . . . .
C1 C 0.23061(17) -0.00183(12) 0.1824(3) 0.0317(5) Uani 1 1 d . . . . .
H1 H 0.185991 0.028948 0.083135 0.038 Uiso 1 1 calc R . . . .
C2 C 0.14638(18) -0.04723(13) 0.2586(3) 0.0391(5) Uani 1 1 d . . . . .
C3 C 0.11341(18) 0.07934(13) 0.3754(3) 0.0383(5) Uani 1 1 d . . . . .
C4 C 0.0412(2) 0.12488(15) 0.4402(3) 0.0480(6) Uani 1 1 d . . . . .
H4 H -0.030483 0.105106 0.441020 0.058 Uiso 1 1 calc R . . . .
C5 C 0.0769(2) 0.19966(15) 0.5033(4) 0.0537(7) Uani 1 1 d . . . . .
H5 H 0.029253 0.230238 0.548419 0.064 Uiso 1 1 calc R . . . .
C6 C 0.1824(2) 0.23001(14) 0.5005(3) 0.0490(6) Uani 1 1 d . . . . .
H6 H 0.204148 0.281497 0.539550 0.059 Uiso 1 1 calc R . . . .
C7 C 0.25632(19) 0.18361(13) 0.4392(3) 0.0385(5) Uani 1 1 d . . . . .
C8 C 0.3715(2) 0.21550(14) 0.4321(3) 0.0504(6) Uani 1 1 d . . . . .
H8A H 0.413955 0.237287 0.542181 0.060 Uiso 1 1 calc R . . . .
H8B H 0.357515 0.258688 0.350162 0.060 Uiso 1 1 calc R . . . .
C9 C 0.44528(19) 0.15248(15) 0.3837(3) 0.0496(6) Uani 1 1 d . . . . .
H9A H 0.504823 0.178310 0.345951 0.059 Uiso 1 1 calc R . . . .
H9B H 0.483640 0.120453 0.482644 0.059 Uiso 1 1 calc R . . . .
C10 C 0.30245(16) 0.05445(12) 0.3180(3) 0.0334(5) Uani 1 1 d . . . . .
H10 H 0.350197 0.022750 0.413515 0.040 Uiso 1 1 calc R . . . .
C11 C 0.22258(18) 0.10690(12) 0.3798(3) 0.0337(5) Uani 1 1 d . . . . .
C12 C 0.0690(2) -0.10553(15) 0.1349(4) 0.0533(7) Uani 1 1 d . . . . .
H12A H 0.012400 -0.127006 0.182816 0.080 Uiso 1 1 calc GR . . . .
H12B H 0.115370 -0.148166 0.112553 0.080 Uiso 1 1 calc GR . . . .
H12C H 0.030162 -0.078385 0.030808 0.080 Uiso 1 1 calc GR . . . .
C13 C 0.30614(18) -0.06287(12) 0.1296(3) 0.0354(5) Uani 1 1 d . . . . .
C14 C 0.2478(2) -0.01125(14) -0.1675(3) 0.0478(6) Uani 1 1 d . . . . .
H14A H 0.175310 0.006147 -0.151496 0.057 Uiso 1 1 calc R . . . .
H14B H 0.229346 -0.038521 -0.275854 0.057 Uiso 1 1 calc R . . . .
C15 C 0.3208(3) 0.06030(18) -0.1715(4) 0.0838(10) Uani 1 1 d . . . . .
H15A H 0.278724 0.095621 -0.260472 0.126 Uiso 1 1 calc GR . . . .
H15B H 0.391228 0.043630 -0.192012 0.126 Uiso 1 1 calc GR . . . .
H15C H 0.339212 0.087601 -0.064530 0.126 Uiso 1 1 calc GR . . . .
C16 C 0.3726(2) -0.13120(14) -0.0796(4) 0.0546(7) Uani 1 1 d . . . . .
H16A H 0.434148 -0.148288 0.020094 0.066 Uiso 1 1 calc R . . . .
H16B H 0.408234 -0.110747 -0.161389 0.066 Uiso 1 1 calc R . . . .
C17 C 0.2973(3) -0.20168(16) -0.1547(5) 0.0771(10) Uani 1 1 d . . . . .
H17A H 0.235594 -0.184783 -0.252511 0.116 Uiso 1 1 calc GR . . . .
H17B H 0.264882 -0.223668 -0.072023 0.116 Uiso 1 1 calc GR . . . .
H17C H 0.343203 -0.241566 -0.187635 0.116 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 C9 1.430(3) . ?
O1 C10 1.430(2) . ?
O2 C2 1.422(2) . ?
O2 C3 1.386(3) . ?
O3 H3 0.8200 . ?
O3 C2 1.413(3) . ?
O4 C13 1.243(3) . ?
N1 C13 1.338(3) . ?
N1 C14 1.465(3) . ?
N1 C16 1.467(3) . ?
C1 H1 0.9800 . ?
C1 C2 1.551(3) . ?
C1 C10 1.519(3) . ?
C1 C13 1.521(3) . ?
C2 C12 1.513(3) . ?
C3 C4 1.385(3) . ?
C3 C11 1.388(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.381(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.392(3) . ?
C7 C8 1.510(3) . ?
C7 C11 1.391(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.513(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10 0.9800 . ?
C10 C11 1.506(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.494(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.504(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C10 O1 C9 108.67(16) . . ?
C3 O2 C2 118.47(15) . . ?
C2 O3 H3 109.5 . . ?
C13 N1 C14 125.81(18) . . ?
C13 N1 C16 118.3(2) . . ?
C14 N1 C16 115.79(19) . . ?
C2 C1 H1 109.7 . . ?
C10 C1 H1 109.7 . . ?
C10 C1 C2 107.56(17) . . ?
C10 C1 C13 111.80(16) . . ?
C13 C1 H1 109.7 . . ?
C13 C1 C2 108.32(16) . . ?
O2 C2 C1 110.54(16) . . ?
O2 C2 C12 105.43(17) . . ?
O3 C2 O2 105.86(18) . . ?
O3 C2 C1 110.77(17) . . ?
O3 C2 C12 111.06(18) . . ?
C12 C2 C1 112.82(19) . . ?
O2 C3 C11 122.36(18) . . ?
C4 C3 O2 116.67(19) . . ?
C4 C3 C11 120.9(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.2(2) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.9(2) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.1(2) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C8 121.3(2) . . ?
C11 C7 C6 119.5(2) . . ?
C11 C7 C8 119.15(19) . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C7 C8 C9 112.93(19) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
O1 C9 C8 111.66(18) . . ?
O1 C9 H9A 109.3 . . ?
O1 C9 H9B 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
O1 C10 C1 110.18(17) . . ?
O1 C10 H10 108.8 . . ?
O1 C10 C11 110.76(16) . . ?
C1 C10 H10 108.8 . . ?
C11 C10 C1 109.37(16) . . ?
C11 C10 H10 108.8 . . ?
C3 C11 C7 119.31(19) . . ?
C3 C11 C10 120.07(18) . . ?
C7 C11 C10 120.61(18) . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O4 C13 N1 121.96(19) . . ?
O4 C13 C1 117.7(2) . . ?
N1 C13 C1 120.31(19) . . ?
N1 C14 H14A 109.1 . . ?
N1 C14 H14B 109.1 . . ?
N1 C14 C15 112.6(2) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16A 109.3 . . ?
N1 C16 H16B 109.3 . . ?
N1 C16 C17 111.6(2) . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 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 C10 C11 C3 150.4(2) . . . . ?
O1 C10 C11 C7 -28.6(3) . . . . ?
O2 C3 C4 C5 -175.3(2) . . . . ?
O2 C3 C11 C7 173.2(2) . . . . ?
O2 C3 C11 C10 -5.8(3) . . . . ?
C1 C10 C11 C3 28.8(3) . . . . ?
C1 C10 C11 C7 -150.3(2) . . . . ?
C2 O2 C3 C4 -170.1(2) . . . . ?
C2 O2 C3 C11 12.1(3) . . . . ?
C2 C1 C10 O1 -176.53(16) . . . . ?
C2 C1 C10 C11 -54.6(2) . . . . ?
C2 C1 C13 O4 -56.5(2) . . . . ?
C2 C1 C13 N1 120.6(2) . . . . ?
C3 O2 C2 O3 79.7(2) . . . . ?
C3 O2 C2 C1 -40.3(3) . . . . ?
C3 O2 C2 C12 -162.51(19) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C4 C3 C11 C7 -4.5(4) . . . . ?
C4 C3 C11 C10 176.4(2) . . . . ?
C4 C5 C6 C7 -2.5(4) . . . . ?
C5 C6 C7 C8 179.1(2) . . . . ?
C5 C6 C7 C11 0.5(4) . . . . ?
C6 C7 C8 C9 172.4(2) . . . . ?
C6 C7 C11 C3 2.9(3) . . . . ?
C6 C7 C11 C10 -178.0(2) . . . . ?
C7 C8 C9 O1 40.9(3) . . . . ?
C8 C7 C11 C3 -175.7(2) . . . . ?
C8 C7 C11 C10 3.4(3) . . . . ?
C9 O1 C10 C1 -178.68(16) . . . . ?
C9 O1 C10 C11 60.2(2) . . . . ?
C10 O1 C9 C8 -68.2(2) . . . . ?
C10 C1 C2 O2 62.0(2) . . . . ?
C10 C1 C2 O3 -55.0(2) . . . . ?
C10 C1 C2 C12 179.82(17) . . . . ?
C10 C1 C13 O4 61.9(2) . . . . ?
C10 C1 C13 N1 -121.1(2) . . . . ?
C11 C3 C4 C5 2.6(4) . . . . ?
C11 C7 C8 C9 -9.0(3) . . . . ?
C13 N1 C14 C15 84.6(3) . . . . ?
C13 N1 C16 C17 97.1(3) . . . . ?
C13 C1 C2 O2 -176.95(17) . . . . ?
C13 C1 C2 O3 66.0(2) . . . . ?
C13 C1 C2 C12 -59.2(2) . . . . ?
C13 C1 C10 O1 64.7(2) . . . . ?
C13 C1 C10 C11 -173.36(17) . . . . ?
C14 N1 C13 O4 -175.0(2) . . . . ?
C14 N1 C13 C1 8.0(3) . . . . ?
C14 N1 C16 C17 -85.9(3) . . . . ?
C16 N1 C13 O4 1.7(3) . . . . ?
C16 N1 C13 C1 -175.25(18) . . . . ?
C16 N1 C14 C15 -92.2(3) . . . . ?

_olex2_date_sample_data_collection 2018-09-06
_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_zhangzh_0523
_database_code_depnum_ccdc_archive 'CCDC 1899677'
_audit_update_record             
;
2019-02-26 deposited with the CCDC.	2019-05-06 downloaded from the CCDC.
;
_audit_creation_date             2018-05-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H13 F3 O5'
_chemical_formula_sum            'C14 H13 F3 O5'
_chemical_formula_weight         318.24
_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'
F F 0.0727 0.0534 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.4241(6)
_cell_length_b                   10.1906(11)
_cell_length_c                   11.3167(14)
_cell_angle_alpha                68.951(11)
_cell_angle_beta                 83.144(9)
_cell_angle_gamma                83.818(8)
_cell_volume                     684.79(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1758
_cell_measurement_temperature    294.9(7)
_cell_measurement_theta_max      69.7930
_cell_measurement_theta_min      7.7920
_exptl_absorpt_coefficient_mu    1.250
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.543
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4363
_diffrn_reflns_theta_full        66.60
_diffrn_reflns_theta_max         66.60
_diffrn_reflns_theta_min         4.20
_diffrn_ambient_temperature      294.9(7)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   29.00   66.50   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega  -26.00   28.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000   30.0000 36

#__ type_ start__ end____ width___ exp.time_
  3 omega  -76.00  -43.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -57.0000  -90.0000 22

#__ type_ start__ end____ width___ exp.time_
  4 omega  -75.00  -42.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  150.0000 22

#__ type_ start__ end____ width___ exp.time_
  5 omega  -38.00   11.50   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -57.0000  -90.0000 33

#__ type_ start__ end____ width___ exp.time_
  6 omega  -15.00   37.50   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
  7 omega   12.00   85.50   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000  120.0000 49

#__ type_ start__ end____ width___ exp.time_
  8 omega   42.00  114.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 48

#__ type_ start__ end____ width___ exp.time_
  9 omega  -15.00   81.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000  -90.0000 64

#__ type_ start__ end____ width___ exp.time_
 10 omega   85.00  172.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -180.0000 58

#__ type_ start__ end____ width___ exp.time_
 11 omega  142.00  169.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   90.0000 -178.0000 18

#__ type_ start__ end____ width___ exp.time_
 12 omega   85.00  145.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  150.0000 40

#__ type_ start__ end____ width___ exp.time_
 13 omega   42.00   87.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000    0.0000 30

#__ type_ start__ end____ width___ exp.time_
 14 omega  144.00  171.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   90.0000 18

#__ type_ start__ end____ width___ exp.time_
 15 omega   50.00  140.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   60.0000 60

#__ type_ start__ end____ width___ exp.time_
 16 omega   43.00  163.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -12.0000  150.0000 80

#__ type_ start__ end____ width___ exp.time_
 17 omega   47.00  101.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   30.0000 36

#__ type_ start__ end____ width___ exp.time_
 18 omega   71.00  129.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  150.0000 39

#__ type_ start__ end____ width___ exp.time_
 19 omega  107.00  146.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   40.00  101.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -120.0000 41

#__ type_ start__ end____ width___ exp.time_
 21 omega   42.00   93.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  150.0000 34

#__ type_ start__ end____ width___ exp.time_
 22 omega   54.00   84.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 20

#__ type_ start__ end____ width___ exp.time_
 23 omega   66.00   93.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 18

#__ type_ start__ end____ width___ exp.time_
 24 omega  101.00  126.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   90.0000 -178.0000 17

#__ type_ start__ end____ width___ exp.time_
 25 omega   52.00  115.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 42

#__ type_ start__ end____ width___ exp.time_
 26 omega   57.00  105.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
 27 omega   86.00  129.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000    0.0000 29

#__ type_ start__ end____ width___ exp.time_
 28 omega   68.00   93.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  120.0000 17

#__ type_ start__ end____ width___ exp.time_
 29 omega   44.00  114.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 47

#__ type_ start__ end____ width___ exp.time_
 30 omega   69.00   94.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 17

#__ type_ start__ end____ width___ exp.time_
 31 omega   72.00   99.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000 -120.0000 18
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0803328000
_diffrn_orient_matrix_UB_12      -0.1317185000
_diffrn_orient_matrix_UB_13      -0.0330514000
_diffrn_orient_matrix_UB_21      -0.0426705000
_diffrn_orient_matrix_UB_22      0.0805929000
_diffrn_orient_matrix_UB_23      -0.1397672000
_diffrn_orient_matrix_UB_31      0.2243941000
_diffrn_orient_matrix_UB_32      0.0502252000
_diffrn_orient_matrix_UB_33      -0.0284862000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1958
_reflns_number_total             2341
_reflns_odcompleteness_completeness 96.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0658P)²+0.1636P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1220
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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:
 C8(H8), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F1 F -0.1794(3) -0.13481(19) 1.02279(13) 0.0815(5) Uani 1 d . . .
F2 F -0.4742(2) -0.12284(16) 0.94771(14) 0.0707(4) Uani 1 d . . .
F3 F -0.2269(3) -0.27282(14) 0.92460(16) 0.0789(5) Uani 1 d . . .
O1 O -0.2572(2) 0.09558(14) 0.81446(15) 0.0510(4) Uani 1 d . . .
O2 O 0.33425(18) 0.06494(13) 0.62424(12) 0.0415(3) Uani 1 d . . .
O3 O -0.28026(19) -0.04973(16) 0.70087(13) 0.0486(4) Uani 1 d . . .
H3 H -0.4033 -0.0184 0.7017 0.073 Uiso 1 calc . . GR
O4 O 0.1078(2) -0.21923(14) 0.66450(14) 0.0508(4) Uani 1 d . . .
O5 O 0.2388(3) -0.26762(15) 0.85101(16) 0.0611(4) Uani 1 d . . .
C1 C -0.1426(3) 0.21189(19) 0.75478(18) 0.0396(4) Uani 1 d . . .
C2 C -0.2145(3) 0.3325(2) 0.7808(2) 0.0516(5) Uani 1 d . . .
H2 H -0.3372 0.3341 0.8331 0.062 Uiso 1 calc . . R
C3 C -0.1001(4) 0.4506(2) 0.7274(2) 0.0570(6) Uani 1 d . . .
H3A H -0.1475 0.5328 0.7431 0.068 Uiso 1 calc . . R
C4 C 0.0838(4) 0.4477(2) 0.6512(2) 0.0530(5) Uani 1 d . . .
H4 H 0.1595 0.5277 0.6166 0.064 Uiso 1 calc . . R
C5 C 0.1565(3) 0.32645(19) 0.62560(17) 0.0410(4) Uani 1 d . . .
C6 C 0.3648(3) 0.3169(2) 0.5502(2) 0.0485(5) Uani 1 d . . .
H6A H 0.3729 0.3992 0.4731 0.058 Uiso 1 calc . . R
H6B H 0.4780 0.3169 0.5997 0.058 Uiso 1 calc . . R
C7 C 0.3938(3) 0.1857(2) 0.51544(19) 0.0471(5) Uani 1 d . . .
H7A H 0.3080 0.1971 0.4470 0.057 Uiso 1 calc . . R
H7B H 0.5396 0.1713 0.4861 0.057 Uiso 1 calc . . R
C8 C 0.1117(2) 0.07412(17) 0.65216(16) 0.0328(4) Uani 1 d . . .
H8 H 0.0424 0.0703 0.5810 0.039 Uiso 1 calc . . R
C9 C 0.0389(3) 0.20846(17) 0.67583(16) 0.0349(4) Uani 1 d . . .
C10 C 0.0527(2) -0.04933(17) 0.77173(16) 0.0332(4) Uani 1 d . . .
H10 H 0.1185 -0.0424 0.8429 0.040 Uiso 1 calc . . R
C11 C -0.1882(3) -0.03374(18) 0.79792(17) 0.0365(4) Uani 1 d . . .
C12 C -0.2670(3) -0.1415(2) 0.9255(2) 0.0509(5) Uani 1 d . . .
C13 C 0.1316(3) -0.18796(18) 0.75386(17) 0.0367(4) Uani 1 d . . .
C14 C 0.3297(5) -0.4015(3) 0.8443(3) 0.0935(11) Uani 1 d . . .
H14A H 0.3952 -0.3877 0.7604 0.140 Uiso 1 calc . . GR
H14B H 0.2211 -0.4657 0.8634 0.140 Uiso 1 calc . . GR
H14C H 0.4328 -0.4399 0.9049 0.140 Uiso 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
F1 C12 1.320(3) . ?
F2 C12 1.331(2) . ?
F3 C12 1.339(3) . ?
O1 C1 1.377(2) . ?
O1 C11 1.414(2) . ?
O2 C7 1.441(2) . ?
O2 C8 1.4273(19) . ?
O3 H3 0.8200 . ?
O3 C11 1.374(2) . ?
O4 C13 1.194(2) . ?
O5 C13 1.327(2) . ?
O5 C14 1.449(3) . ?
C1 C2 1.384(2) . ?
C1 C9 1.387(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(3) . ?
C3 H3A 0.9300 . ?
C3 C4 1.381(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(3) . ?
C5 C6 1.513(3) . ?
C5 C9 1.393(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.510(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8 0.9800 . ?
C8 C9 1.503(2) . ?
C8 C10 1.521(2) . ?
C10 H10 0.9800 . ?
C10 C11 1.542(2) . ?
C10 C13 1.523(2) . ?
C11 C12 1.534(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
C1 O1 C11 119.85(13) . . ?
C8 O2 C7 109.39(13) . . ?
C11 O3 H3 109.5 . . ?
C13 O5 C14 115.50(17) . . ?
O1 C1 C2 116.34(17) . . ?
O1 C1 C9 122.34(15) . . ?
C2 C1 C9 121.28(18) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.63(19) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 C2 120.76(18) . . ?
C4 C3 H3A 119.6 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.58(19) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 121.74(17) . . ?
C4 C5 C9 119.01(18) . . ?
C9 C5 C6 119.18(16) . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 C5 112.17(15) . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
O2 C7 C6 110.11(16) . . ?
O2 C7 H7A 109.6 . . ?
O2 C7 H7B 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.2 . . ?
O2 C8 H8 109.6 . . ?
O2 C8 C9 110.93(13) . . ?
O2 C8 C10 108.78(13) . . ?
C9 C8 H8 109.6 . . ?
C9 C8 C10 108.31(14) . . ?
C10 C8 H8 109.6 . . ?
C1 C9 C5 119.67(16) . . ?
C1 C9 C8 119.10(15) . . ?
C5 C9 C8 121.14(16) . . ?
C8 C10 H10 108.9 . . ?
C8 C10 C11 106.61(13) . . ?
C8 C10 C13 110.10(14) . . ?
C11 C10 H10 108.9 . . ?
C13 C10 H10 108.9 . . ?
C13 C10 C11 113.35(13) . . ?
O1 C11 C10 112.20(13) . . ?
O1 C11 C12 101.96(15) . . ?
O3 C11 O1 111.76(15) . . ?
O3 C11 C10 108.80(13) . . ?
O3 C11 C12 109.86(15) . . ?
C12 C11 C10 112.16(15) . . ?
F1 C12 F2 107.76(17) . . ?
F1 C12 F3 107.54(19) . . ?
F1 C12 C11 112.99(17) . . ?
F2 C12 F3 106.80(16) . . ?
F2 C12 C11 110.95(18) . . ?
F3 C12 C11 110.54(16) . . ?
O4 C13 O5 124.72(16) . . ?
O4 C13 C10 125.71(16) . . ?
O5 C13 C10 109.52(15) . . ?
O5 C14 H14A 109.5 . . ?
O5 C14 H14B 109.5 . . ?
O5 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 C1 C2 C3 177.35(19) . . . . ?
O1 C1 C9 C5 -175.29(16) . . . . ?
O1 C1 C9 C8 1.2(3) . . . . ?
O1 C11 C12 F1 -63.4(2) . . . . ?
O1 C11 C12 F2 57.76(19) . . . . ?
O1 C11 C12 F3 176.06(15) . . . . ?
O2 C8 C9 C1 -152.18(16) . . . . ?
O2 C8 C9 C5 24.3(2) . . . . ?
O2 C8 C10 C11 179.63(12) . . . . ?
O2 C8 C10 C13 -57.03(17) . . . . ?
O3 C11 C12 F1 177.98(16) . . . . ?
O3 C11 C12 F2 -60.9(2) . . . . ?
O3 C11 C12 F3 57.4(2) . . . . ?
C1 O1 C11 O3 -93.87(19) . . . . ?
C1 O1 C11 C10 28.7(2) . . . . ?
C1 O1 C11 C12 148.84(16) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C1 C9 C5 2.7(3) . . . . ?
C2 C1 C9 C8 179.16(16) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 C6 -175.6(2) . . . . ?
C3 C4 C5 C9 1.4(3) . . . . ?
C4 C5 C6 C7 -170.27(18) . . . . ?
C4 C5 C9 C1 -2.9(3) . . . . ?
C4 C5 C9 C8 -179.38(16) . . . . ?
C5 C6 C7 O2 -45.5(2) . . . . ?
C6 C5 C9 C1 174.13(16) . . . . ?
C6 C5 C9 C8 -2.3(3) . . . . ?
C7 O2 C8 C9 -57.63(18) . . . . ?
C7 O2 C8 C10 -176.66(14) . . . . ?
C8 O2 C7 C6 70.28(19) . . . . ?
C8 C10 C11 O1 -58.86(18) . . . . ?
C8 C10 C11 O3 65.32(17) . . . . ?
C8 C10 C11 C12 -172.93(14) . . . . ?
C8 C10 C13 O4 -48.5(2) . . . . ?
C8 C10 C13 O5 129.04(16) . . . . ?
C9 C1 C2 C3 -0.7(3) . . . . ?
C9 C5 C6 C7 12.7(2) . . . . ?
C9 C8 C10 C11 58.97(16) . . . . ?
C9 C8 C10 C13 -177.69(12) . . . . ?
C10 C8 C9 C1 -32.9(2) . . . . ?
C10 C8 C9 C5 143.58(16) . . . . ?
C10 C11 C12 F1 56.8(2) . . . . ?
C10 C11 C12 F2 177.98(14) . . . . ?
C10 C11 C12 F3 -63.7(2) . . . . ?
C11 O1 C1 C2 -176.83(17) . . . . ?
C11 O1 C1 C9 1.2(3) . . . . ?
C11 C10 C13 O4 70.8(2) . . . . ?
C11 C10 C13 O5 -111.64(17) . . . . ?
C13 C10 C11 O1 179.84(14) . . . . ?
C13 C10 C11 O3 -55.97(19) . . . . ?
C13 C10 C11 C12 65.77(19) . . . . ?
C14 O5 C13 O4 -0.4(3) . . . . ?
C14 O5 C13 C10 -178.0(2) . . . . ?


_olex2_date_sample_data_collection 2018-05-23
_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_zhangzh_0907
_database_code_depnum_ccdc_archive 'CCDC 1899676'
_audit_update_record             
;
2019-02-26 deposited with the CCDC.	2019-05-06 downloaded from the CCDC.
;
_audit_creation_date             2018-11-09
_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         'C17 H20 O4'
_chemical_formula_sum            'C17 H20 O4'
_chemical_formula_weight         288.33
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.1636(11)
_cell_length_b                   10.2486(7)
_cell_length_c                   12.3402(11)
_cell_angle_alpha                90
_cell_angle_beta                 110.011(10)
_cell_angle_gamma                90
_cell_volume                     1445.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1067
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.8820
_cell_measurement_theta_min      3.8960
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5398
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.006
_diffrn_reflns_theta_min         3.352
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -95.00  -60.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  178.0000  -90.0000 35

#__ type_ start__ end____ width___ exp.time_
  2 omega  -46.00   28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000   60.0000 74

#__ type_ start__ end____ width___ exp.time_
  3 omega  -22.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   19.0000 -120.0000 120
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0304056000
_diffrn_orient_matrix_UB_12      0.0488562000
_diffrn_orient_matrix_UB_13      -0.0191331000
_diffrn_orient_matrix_UB_21      -0.0414772000
_diffrn_orient_matrix_UB_22      -0.0051386000
_diffrn_orient_matrix_UB_23      -0.0565784000
_diffrn_orient_matrix_UB_31      -0.0348400000
_diffrn_orient_matrix_UB_32      0.0487453000
_diffrn_orient_matrix_UB_33      0.0131576000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1825
_reflns_number_total             2846
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2846
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0532
_refine_ls_restrained_S_all      1.032
_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)+(0.0494P)²+0.2871P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1438
_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:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,
 H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.25623(14) -0.14825(17) 0.00046(14) 0.0523(5) Uani 1 1 d . . . . .
H1 H 0.285291 -0.171252 -0.047408 0.078 Uiso 1 1 calc GR . . . .
O2 O 0.34205(14) 0.05379(15) 0.04352(13) 0.0453(4) Uani 1 1 d . . . . .
O3 O 0.13068(14) -0.00466(15) 0.24292(13) 0.0423(4) Uani 1 1 d . . . . .
O4 O 0.33335(17) -0.22765(17) 0.34342(16) 0.0627(6) Uani 1 1 d . . . . .
C1 C 0.29715(18) -0.07113(19) 0.19321(17) 0.0310(5) Uani 1 1 d . . . . .
C2 C 0.33804(19) -0.0763(2) 0.08707(18) 0.0354(5) Uani 1 1 d . . . . .
C3 C 0.2582(2) 0.1433(2) 0.04235(18) 0.0387(5) Uani 1 1 d . . . . .
C4 C 0.2598(2) 0.2621(2) -0.0104(2) 0.0494(6) Uani 1 1 d . . . . .
H4 H 0.311359 0.275823 -0.050208 0.059 Uiso 1 1 calc R . . . .
C5 C 0.1852(2) 0.3593(2) -0.0039(2) 0.0567(7) Uani 1 1 d . . . . .
H5 H 0.185867 0.438793 -0.039998 0.068 Uiso 1 1 calc R . . . .
C6 C 0.1087(2) 0.3406(2) 0.0557(2) 0.0528(7) Uani 1 1 d . . . . .
H6 H 0.059834 0.408142 0.061218 0.063 Uiso 1 1 calc R . . . .
C7 C 0.1047(2) 0.2211(2) 0.10758(19) 0.0420(6) Uani 1 1 d . . . . .
C8 C 0.17812(19) 0.1214(2) 0.09853(17) 0.0350(5) Uani 1 1 d . . . . .
C9 C 0.17481(18) -0.0104(2) 0.15048(18) 0.0330(5) Uani 1 1 d . . . . .
H9 H 0.123377 -0.066997 0.090412 0.040 Uiso 1 1 calc R . . . .
C10 C 0.0270(2) 0.1989(2) 0.1785(2) 0.0515(7) Uani 1 1 d . . . . .
H10A H -0.050595 0.232577 0.137018 0.062 Uiso 1 1 calc R . . . .
H10B H 0.058060 0.246764 0.250433 0.062 Uiso 1 1 calc R . . . .
C11 C 0.0181(2) 0.0560(2) 0.2045(2) 0.0489(6) Uani 1 1 d . . . . .
H11A H -0.017287 0.047164 0.263652 0.059 Uiso 1 1 calc R . . . .
H11B H -0.031927 0.012112 0.135645 0.059 Uiso 1 1 calc R . . . .
C12 C 0.3857(2) 0.0109(2) 0.28787(19) 0.0400(6) Uani 1 1 d . . . . .
H12A H 0.381067 0.100884 0.262234 0.048 Uiso 1 1 calc R . . . .
H12B H 0.364284 0.008749 0.356709 0.048 Uiso 1 1 calc R . . . .
C13 C 0.5114(2) -0.0365(2) 0.3182(2) 0.0518(7) Uani 1 1 d . . . . .
H13A H 0.519012 -0.121191 0.355183 0.062 Uiso 1 1 calc R . . . .
H13B H 0.563258 0.023611 0.372828 0.062 Uiso 1 1 calc R . . . .
C14 C 0.5486(2) -0.0474(3) 0.2123(2) 0.0549(7) Uani 1 1 d . . . . .
H14A H 0.554908 0.039238 0.183321 0.066 Uiso 1 1 calc R . . . .
H14B H 0.624942 -0.088436 0.233924 0.066 Uiso 1 1 calc R . . . .
C15 C 0.4608(2) -0.1273(2) 0.1175(2) 0.0464(6) Uani 1 1 d . . . . .
H15A H 0.483131 -0.125883 0.049166 0.056 Uiso 1 1 calc R . . . .
H15B H 0.463139 -0.217199 0.142689 0.056 Uiso 1 1 calc R . . . .
C16 C 0.2836(2) -0.2064(2) 0.2415(2) 0.0404(6) Uani 1 1 d . . . . .
C17 C 0.2055(2) -0.3086(2) 0.1691(3) 0.0637(8) Uani 1 1 d . . . . .
H17A H 0.232400 -0.332116 0.107081 0.096 Uiso 1 1 calc GR . . . .
H17B H 0.127108 -0.275459 0.138007 0.096 Uiso 1 1 calc GR . . . .
H17C H 0.206642 -0.384169 0.215442 0.096 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 C2 1.396(3) . ?
O2 C2 1.445(2) . ?
O2 C3 1.368(3) . ?
O3 C9 1.418(2) . ?
O3 C11 1.429(3) . ?
O4 C16 1.214(3) . ?
C1 C2 1.553(3) . ?
C1 C9 1.531(3) . ?
C1 C12 1.540(3) . ?
C1 C16 1.540(3) . ?
C2 C15 1.503(3) . ?
C3 C4 1.384(3) . ?
C3 C8 1.394(3) . ?
C4 C5 1.368(3) . ?
C5 C6 1.383(4) . ?
C6 C7 1.390(3) . ?
C7 C8 1.386(3) . ?
C7 C10 1.509(3) . ?
C8 C9 1.501(3) . ?
C10 C11 1.512(3) . ?
C12 C13 1.524(3) . ?
C13 C14 1.528(3) . ?
C14 C15 1.524(3) . ?
C16 C17 1.489(3) . ?

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
C3 O2 C2 120.20(16) . . ?
C9 O3 C11 109.55(16) . . ?
C9 C1 C2 106.11(16) . . ?
C9 C1 C12 112.58(17) . . ?
C9 C1 C16 106.24(17) . . ?
C12 C1 C2 108.42(17) . . ?
C12 C1 C16 109.73(18) . . ?
C16 C1 C2 113.78(17) . . ?
O1 C2 O2 107.98(18) . . ?
O1 C2 C1 108.29(16) . . ?
O1 C2 C15 113.24(18) . . ?
O2 C2 C1 110.09(16) . . ?
O2 C2 C15 104.85(17) . . ?
C15 C2 C1 112.27(18) . . ?
O2 C3 C4 117.7(2) . . ?
O2 C3 C8 122.14(19) . . ?
C4 C3 C8 120.0(2) . . ?
C5 C4 C3 119.8(2) . . ?
C4 C5 C6 120.7(2) . . ?
C5 C6 C7 120.2(2) . . ?
C6 C7 C10 121.8(2) . . ?
C8 C7 C6 119.1(2) . . ?
C8 C7 C10 119.0(2) . . ?
C3 C8 C9 118.86(19) . . ?
C7 C8 C3 120.0(2) . . ?
C7 C8 C9 121.1(2) . . ?
O3 C9 C1 109.30(16) . . ?
O3 C9 C8 112.28(17) . . ?
C8 C9 C1 110.38(17) . . ?
C7 C10 C11 111.9(2) . . ?
O3 C11 C10 111.2(2) . . ?
C13 C12 C1 113.24(18) . . ?
C12 C13 C14 112.3(2) . . ?
C15 C14 C13 111.2(2) . . ?
C2 C15 C14 112.34(19) . . ?
O4 C16 C1 118.8(2) . . ?
O4 C16 C17 119.0(2) . . ?
C17 C16 C1 122.1(2) . . ?

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 C2 C15 C14 -179.93(19) . . . . ?
O2 C2 C15 C14 62.6(2) . . . . ?
O2 C3 C4 C5 -173.6(2) . . . . ?
O2 C3 C8 C7 171.73(19) . . . . ?
O2 C3 C8 C9 -7.1(3) . . . . ?
C1 C2 C15 C14 -56.9(2) . . . . ?
C1 C12 C13 C14 53.6(3) . . . . ?
C2 O2 C3 C4 -173.87(19) . . . . ?
C2 O2 C3 C8 10.4(3) . . . . ?
C2 C1 C9 O3 178.93(15) . . . . ?
C2 C1 C9 C8 -57.1(2) . . . . ?
C2 C1 C12 C13 -54.0(2) . . . . ?
C2 C1 C16 O4 127.1(2) . . . . ?
C2 C1 C16 C17 -57.0(3) . . . . ?
C3 O2 C2 O1 80.0(2) . . . . ?
C3 O2 C2 C1 -38.0(3) . . . . ?
C3 O2 C2 C15 -158.98(19) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C3 C8 C9 O3 154.55(19) . . . . ?
C3 C8 C9 C1 32.3(3) . . . . ?
C4 C3 C8 C7 -3.9(3) . . . . ?
C4 C3 C8 C9 177.3(2) . . . . ?
C4 C5 C6 C7 -1.6(4) . . . . ?
C5 C6 C7 C8 0.0(4) . . . . ?
C5 C6 C7 C10 176.8(2) . . . . ?
C6 C7 C8 C3 2.7(3) . . . . ?
C6 C7 C8 C9 -178.4(2) . . . . ?
C6 C7 C10 C11 168.0(2) . . . . ?
C7 C8 C9 O3 -24.3(3) . . . . ?
C7 C8 C9 C1 -146.5(2) . . . . ?
C7 C10 C11 O3 46.4(3) . . . . ?
C8 C3 C4 C5 2.2(3) . . . . ?
C8 C7 C10 C11 -15.2(3) . . . . ?
C9 O3 C11 C10 -68.2(2) . . . . ?
C9 C1 C2 O1 -57.5(2) . . . . ?
C9 C1 C2 O2 60.3(2) . . . . ?
C9 C1 C2 C15 176.75(17) . . . . ?
C9 C1 C12 C13 -171.11(18) . . . . ?
C9 C1 C16 O4 -116.5(2) . . . . ?
C9 C1 C16 C17 59.3(3) . . . . ?
C10 C7 C8 C3 -174.2(2) . . . . ?
C10 C7 C8 C9 4.6(3) . . . . ?
C11 O3 C9 C1 178.08(17) . . . . ?
C11 O3 C9 C8 55.3(2) . . . . ?
C12 C1 C2 O1 -178.66(17) . . . . ?
C12 C1 C2 O2 -60.8(2) . . . . ?
C12 C1 C2 C15 55.6(2) . . . . ?
C12 C1 C9 O3 -62.6(2) . . . . ?
C12 C1 C9 C8 61.3(2) . . . . ?
C12 C1 C16 O4 5.4(3) . . . . ?
C12 C1 C16 C17 -178.7(2) . . . . ?
C12 C13 C14 C15 -51.7(3) . . . . ?
C13 C14 C15 C2 53.8(3) . . . . ?
C16 C1 C2 O1 59.0(2) . . . . ?
C16 C1 C2 O2 176.80(18) . . . . ?
C16 C1 C2 C15 -66.8(2) . . . . ?
C16 C1 C9 O3 57.5(2) . . . . ?
C16 C1 C9 C8 -178.53(17) . . . . ?
C16 C1 C12 C13 70.8(2) . . . . ?

_olex2_date_sample_data_collection 2018-09-07
_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_1
_database_code_depnum_ccdc_archive 'CCDC 1899675'
_audit_update_record             
;
2019-02-26 deposited with the CCDC.	2019-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 O4'
_chemical_formula_weight         274.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.6075(10)
_cell_length_b                   9.2096(12)
_cell_length_c                   19.424(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.561(2)
_cell_angle_gamma                90
_cell_volume                     1345.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2384
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      28.44

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   0.6785
_exptl_transmission_factor_max   0.7458
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 'fine-focus sealed tube'
_diffrn_reflns_number            6636
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.453
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2357
_reflns_number_gt                1847
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_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)+(0.1000P)²+0.2003P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2357
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1506
_refine_ls_wR_factor_gt          0.1348
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_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
C1 C 0.7222(2) 0.30836(19) 0.12049(9) 0.0460(5) Uani 1 1 d . . . . .
C2 C 0.7282(3) 0.1738(2) 0.08918(12) 0.0633(6) Uani 1 1 d . . . . .
H2 H 0.7226 0.0891 0.1148 0.076 Uiso 1 1 calc R U . . .
C3 C 0.7424(3) 0.1675(3) 0.01980(14) 0.0825(8) Uani 1 1 d . . . . .
H3 H 0.7458 0.0777 -0.0019 0.099 Uiso 1 1 calc R U . . .
C4 C 0.7518(3) 0.2923(4) -0.01790(12) 0.0792(8) Uani 1 1 d . . . . .
H4 H 0.7634 0.2859 -0.0648 0.095 Uiso 1 1 calc R U . . .
C5 C 0.7442(2) 0.4294(3) 0.01276(9) 0.0592(6) Uani 1 1 d . . . . .
C6 C 0.7653(3) 0.5662(3) -0.02683(10) 0.0732(7) Uani 1 1 d . . . . .
H6A H 0.6719 0.5706 -0.0666 0.088 Uiso 1 1 calc R U . . .
H6B H 0.8782 0.5628 -0.0444 0.088 Uiso 1 1 calc R U . . .
C7 C 0.7588(3) 0.7027(3) 0.01580(11) 0.0734(7) Uani 1 1 d . . . . .
H7A H 0.8239 0.7790 -0.0039 0.088 Uiso 1 1 calc R U . . .
H7B H 0.6362 0.7340 0.0131 0.088 Uiso 1 1 calc R U . . .
C8 C 0.7247(2) 0.58267(18) 0.11867(8) 0.0401(4) Uani 1 1 d . . . . .
H8 H 0.6024 0.6192 0.1130 0.048 Uiso 1 1 calc R U . . .
C9 C 0.7270(2) 0.4371(2) 0.08360(9) 0.0440(5) Uani 1 1 d . . . . .
C10 C 0.7951(2) 0.56745(16) 0.19620(8) 0.0357(4) Uani 1 1 d . . . . .
C11 C 0.6893(2) 0.44133(16) 0.22394(8) 0.0388(4) Uani 1 1 d . . . . .
C12 C 0.7411(3) 0.4150(2) 0.30119(9) 0.0529(5) Uani 1 1 d . . . . .
H12A H 0.8660 0.3893 0.3110 0.064 Uiso 1 1 calc R U . . .
H12B H 0.6724 0.3348 0.3156 0.064 Uiso 1 1 calc R U . . .
C13 C 0.7069(3) 0.5514(2) 0.34195(10) 0.0656(6) Uani 1 1 d . . . . .
H13A H 0.5798 0.5669 0.3383 0.079 Uiso 1 1 calc R U . . .
H13B H 0.7535 0.5370 0.3907 0.079 Uiso 1 1 calc R U . . .
C14 C 0.7926(3) 0.6860(2) 0.31552(9) 0.0562(5) Uani 1 1 d . . . . .
H14A H 0.7505 0.7717 0.3371 0.067 Uiso 1 1 calc R U . . .
H14B H 0.9205 0.6806 0.3289 0.067 Uiso 1 1 calc R U . . .
C15 C 0.7500(2) 0.69968(17) 0.23783(9) 0.0411(4) Uani 1 1 d . . . . .
C16 C 0.9963(2) 0.54100(19) 0.20745(9) 0.0469(5) Uani 1 1 d . . . . .
H16A H 1.0230 0.4603 0.1795 0.070 Uiso 1 1 calc R U . . .
H16B H 1.0359 0.5199 0.2557 0.070 Uiso 1 1 calc R U . . .
H16C H 1.0559 0.6262 0.1942 0.070 Uiso 1 1 calc R U . . .
O1 O 0.72098(18) 0.30668(12) 0.19132(6) 0.0491(4) Uani 1 1 d . . . . .
O2 O 0.83301(18) 0.68234(14) 0.08768(6) 0.0549(4) Uani 1 1 d . . . . .
O3 O 0.50997(14) 0.48060(13) 0.20702(6) 0.0449(4) Uani 1 1 d . . . . .
H3A H 0.4500 0.4329 0.2306 0.067 Uiso 1 1 calc R U . . .
O4 O 0.68157(17) 0.80777(13) 0.21008(7) 0.0521(4) Uani 1 1 d . . . . .


_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
C1 O1 1.377(2) . ?
C1 C2 1.384(2) . ?
C1 C9 1.388(3) . ?
C2 C3 1.369(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.401(3) . ?
C4 H4 0.9300 . ?
C5 C9 1.403(2) . ?
C5 C6 1.497(3) . ?
C6 C7 1.511(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O2 1.438(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O2 1.425(2) . ?
C8 C9 1.505(2) . ?
C8 C10 1.528(2) . ?
C8 H8 0.9800 . ?
C10 C15 1.529(2) . ?
C10 C16 1.533(2) . ?
C10 C11 1.554(2) . ?
C11 O3 1.4025(19) . ?
C11 O1 1.4292(18) . ?
C11 C12 1.513(2) . ?
C12 C13 1.528(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.525(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.501(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O4 1.212(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O3 H3A 0.8200 . ?

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
O1 C1 C2 115.75(17) . . ?
O1 C1 C9 122.00(14) . . ?
C2 C1 C9 122.16(17) . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 120.5(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 121.3(2) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C9 118.5(2) . . ?
C4 C5 C6 121.70(19) . . ?
C9 C5 C6 119.65(19) . . ?
C5 C6 C7 113.83(16) . . ?
C5 C6 H6A 108.8 . . ?
C7 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
C7 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
O2 C7 C6 112.52(18) . . ?
O2 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
O2 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
O2 C8 C9 109.64(13) . . ?
O2 C8 C10 109.60(13) . . ?
C9 C8 C10 109.77(13) . . ?
O2 C8 H8 109.3 . . ?
C9 C8 H8 109.3 . . ?
C10 C8 H8 109.3 . . ?
C1 C9 C5 118.49(17) . . ?
C1 C9 C8 121.60(14) . . ?
C5 C9 C8 119.82(17) . . ?
C8 C10 C15 112.02(13) . . ?
C8 C10 C16 110.56(13) . . ?
C15 C10 C16 110.42(13) . . ?
C8 C10 C11 106.65(13) . . ?
C15 C10 C11 104.10(12) . . ?
C16 C10 C11 112.91(13) . . ?
O3 C11 O1 110.01(12) . . ?
O3 C11 C12 111.98(14) . . ?
O1 C11 C12 105.32(13) . . ?
O3 C11 C10 105.18(12) . . ?
O1 C11 C10 111.38(13) . . ?
C12 C11 C10 113.07(14) . . ?
C11 C12 C13 110.04(15) . . ?
C11 C12 H12A 109.7 . . ?
C13 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
C13 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C14 C13 C12 112.33(15) . . ?
C14 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C13 111.57(15) . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
O4 C15 C14 122.02(15) . . ?
O4 C15 C10 122.30(15) . . ?
C14 C15 C10 115.66(14) . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 O1 C11 117.37(12) . . ?
C8 O2 C7 109.02(15) . . ?
C11 O3 H3A 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 C1 C2 C3 -175.42(18) . . . . ?
C9 C1 C2 C3 1.2(3) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 -1.1(4) . . . . ?
C3 C4 C5 C9 0.1(3) . . . . ?
C3 C4 C5 C6 176.2(2) . . . . ?
C4 C5 C6 C7 -178.19(18) . . . . ?
C9 C5 C6 C7 -2.1(3) . . . . ?
C5 C6 C7 O2 33.2(2) . . . . ?
O1 C1 C9 C5 174.31(15) . . . . ?
C2 C1 C9 C5 -2.1(3) . . . . ?
O1 C1 C9 C8 -2.2(2) . . . . ?
C2 C1 C9 C8 -178.54(17) . . . . ?
C4 C5 C9 C1 1.4(3) . . . . ?
C6 C5 C9 C1 -174.78(16) . . . . ?
C4 C5 C9 C8 177.92(16) . . . . ?
C6 C5 C9 C8 1.8(2) . . . . ?
O2 C8 C9 C1 144.47(15) . . . . ?
C10 C8 C9 C1 24.0(2) . . . . ?
O2 C8 C9 C5 -32.0(2) . . . . ?
C10 C8 C9 C5 -152.41(15) . . . . ?
O2 C8 C10 C15 75.00(16) . . . . ?
C9 C8 C10 C15 -164.53(13) . . . . ?
O2 C8 C10 C16 -48.63(17) . . . . ?
C9 C8 C10 C16 71.85(16) . . . . ?
O2 C8 C10 C11 -171.72(12) . . . . ?
C9 C8 C10 C11 -51.25(16) . . . . ?
C8 C10 C11 O3 -56.10(15) . . . . ?
C15 C10 C11 O3 62.50(15) . . . . ?
C16 C10 C11 O3 -177.72(12) . . . . ?
C8 C10 C11 O1 63.05(16) . . . . ?
C15 C10 C11 O1 -178.36(12) . . . . ?
C16 C10 C11 O1 -58.58(17) . . . . ?
C8 C10 C11 C12 -178.58(13) . . . . ?
C15 C10 C11 C12 -59.98(17) . . . . ?
C16 C10 C11 C12 59.80(18) . . . . ?
O3 C11 C12 C13 -58.6(2) . . . . ?
O1 C11 C12 C13 -178.18(15) . . . . ?
C10 C11 C12 C13 60.0(2) . . . . ?
C11 C12 C13 C14 -52.1(2) . . . . ?
C12 C13 C14 C15 49.1(2) . . . . ?
C13 C14 C15 O4 124.40(19) . . . . ?
C13 C14 C15 C10 -54.4(2) . . . . ?
C8 C10 C15 O4 -6.6(2) . . . . ?
C16 C10 C15 O4 117.13(18) . . . . ?
C11 C10 C15 O4 -121.42(17) . . . . ?
C8 C10 C15 C14 172.22(14) . . . . ?
C16 C10 C15 C14 -64.08(18) . . . . ?
C11 C10 C15 C14 57.37(18) . . . . ?
C2 C1 O1 C11 -171.28(15) . . . . ?
C9 C1 O1 C11 12.1(2) . . . . ?
O3 C11 O1 C1 73.05(17) . . . . ?
C12 C11 O1 C1 -166.11(15) . . . . ?
C10 C11 O1 C1 -43.17(19) . . . . ?
C9 C8 O2 C7 63.08(18) . . . . ?
C10 C8 O2 C7 -176.36(15) . . . . ?
C6 C7 O2 C8 -65.6(2) . . . . ?

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.047



