# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1822536'
loop_
_audit_author_name
_audit_author_address
'Junliang Zhang' 'East China Normal University'
_audit_update_record             
;
2018-02-07 deposited with the CCDC.	2019-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 Cl O3'
_chemical_formula_weight         354.81

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.4519(10)
_cell_length_b                   8.3981(4)
_cell_length_c                   29.0733(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 133.170(2)
_cell_angle_gamma                90.00
_cell_volume                     3641.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7105
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      20.91

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1488
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9012
_exptl_absorpt_correction_T_max  0.9478
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker smart apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41183
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.40
_diffrn_reflns_theta_max         25.01
_reflns_number_total             6401
_reflns_number_gt                4303
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0581P)²+2.1310P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6401
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1453
_refine_ls_wR_factor_gt          0.1227
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.38700(10) -1.50047(15) 0.03104(7) 0.1507(6) Uani 1 1 d . . .
O1 O 0.25420(14) -0.8379(2) -0.11646(9) 0.0655(5) Uani 1 1 d . . .
O2 O 0.19408(13) -1.0586(2) -0.17436(9) 0.0629(5) Uani 1 1 d . . .
O3 O -0.14163(12) -0.6901(2) -0.21414(8) 0.0626(5) Uani 1 1 d . . .
H3B H -0.1618 -0.6481 -0.2471 0.094 Uiso 1 1 calc R . .
C1 C 0.1162(2) -1.2857(4) -0.12198(14) 0.0679(8) Uani 1 1 d . . .
H1A H 0.0596 -1.2419 -0.1536 0.082 Uiso 1 1 calc R . .
C2 C 0.1259(3) -1.4495(4) -0.11156(19) 0.0912(12) Uani 1 1 d . . .
H2A H 0.0755 -1.5147 -0.1365 0.109 Uiso 1 1 calc R . .
C3 C 0.2083(4) -1.5151(4) -0.0652(2) 0.0984(14) Uani 1 1 d . . .
H3A H 0.2145 -1.6246 -0.0586 0.118 Uiso 1 1 calc R . .
C4 C 0.2819(3) -1.4186(4) -0.02845(17) 0.0807(10) Uani 1 1 d . . .
C5 C 0.2739(2) -1.2564(3) -0.03800(14) 0.0608(7) Uani 1 1 d . . .
H5A H 0.3247 -1.1921 -0.0125 0.073 Uiso 1 1 calc R . .
C6 C 0.19055(18) -1.1889(3) -0.08549(12) 0.0486(6) Uani 1 1 d . . .
C7 C 0.18594(16) -1.0104(3) -0.09657(11) 0.0434(6) Uani 1 1 d . . .
H7A H 0.2309 -0.9598 -0.0552 0.052 Uiso 1 1 calc R . .
C8 C 0.09632(15) -0.9324(3) -0.12911(10) 0.0432(6) Uani 1 1 d . . .
C9 C 0.03718(17) -0.8914(3) -0.19159(11) 0.0544(7) Uani 1 1 d . . .
H9A H 0.0510 -0.9173 -0.2152 0.065 Uiso 1 1 calc R . .
C10 C -0.04335(17) -0.8118(3) -0.22113(12) 0.0539(7) Uani 1 1 d . . .
H10A H -0.0821 -0.7868 -0.2638 0.065 Uiso 1 1 calc R . .
C11 C -0.06519(16) -0.7710(3) -0.18805(11) 0.0463(6) Uani 1 1 d . . .
C12 C -0.00866(15) -0.8135(3) -0.12370(11) 0.0428(6) Uani 1 1 d . . .
C13 C -0.03063(17) -0.7751(3) -0.08821(12) 0.0523(6) Uani 1 1 d . . .
H13A H -0.0824 -0.7174 -0.1070 0.063 Uiso 1 1 calc R . .
C14 C 0.02291(19) -0.8216(3) -0.02724(13) 0.0608(7) Uani 1 1 d . . .
H14A H 0.0072 -0.7972 -0.0046 0.073 Uiso 1 1 calc R . .
C15 C 0.10186(19) -0.9063(4) 0.00170(12) 0.0611(7) Uani 1 1 d . . .
H15A H 0.1382 -0.9382 0.0435 0.073 Uiso 1 1 calc R . .
C16 C 0.12613(17) -0.9425(3) -0.03047(11) 0.0506(6) Uani 1 1 d . . .
H16A H 0.1791 -0.9981 -0.0102 0.061 Uiso 1 1 calc R . .
C17 C 0.07238(15) -0.8973(3) -0.09421(10) 0.0413(5) Uani 1 1 d . . .
C18 C 0.21157(16) -0.9746(3) -0.13375(11) 0.0439(6) Uani 1 1 d . . .
C19 C 0.2710(2) -0.7709(4) -0.15447(15) 0.0727(9) Uani 1 1 d . . .
H19A H 0.2662 -0.8551 -0.1800 0.087 Uiso 1 1 calc R . .
C20 C 0.2021(3) -0.6474(5) -0.19622(18) 0.1073(14) Uani 1 1 d . . .
H20A H 0.1437 -0.6956 -0.2241 0.161 Uiso 1 1 calc R . .
H20B H 0.2126 -0.5988 -0.2205 0.161 Uiso 1 1 calc R . .
H20C H 0.2052 -0.5678 -0.1711 0.161 Uiso 1 1 calc R . .
C21 C 0.3646(3) -0.7078(5) -0.10854(19) 0.1074(13) Uani 1 1 d . . .
H21A H 0.4055 -0.7930 -0.0823 0.161 Uiso 1 1 calc R . .
H21B H 0.3695 -0.6275 -0.0828 0.161 Uiso 1 1 calc R . .
H21C H 0.3789 -0.6622 -0.1310 0.161 Uiso 1 1 calc R . .
Cl2 Cl 0.09627(8) -0.82341(13) -0.36563(5) 0.1216(4) Uani 1 1 d . . .
O4 O 0.29378(13) -0.3932(2) -0.37557(8) 0.0610(5) Uani 1 1 d . . .
O5 O 0.25473(13) -0.1554(2) -0.36699(8) 0.0612(5) Uani 1 1 d . . .
O6 O 0.63059(13) -0.0272(3) -0.08053(8) 0.0744(6) Uani 1 1 d . . .
H6A H 0.6545 0.0134 -0.0915 0.112 Uiso 1 1 calc R . .
C22 C 0.3730(2) -0.6154(4) -0.24154(14) 0.0669(8) Uani 1 1 d . . .
H22A H 0.4306 -0.5733 -0.2155 0.080 Uiso 1 1 calc R . .
C23 C 0.3606(3) -0.7792(4) -0.23952(17) 0.0828(10) Uani 1 1 d . . .
H23A H 0.4101 -0.8452 -0.2120 0.099 Uiso 1 1 calc R . .
C24 C 0.2755(3) -0.8425(4) -0.27805(18) 0.0838(11) Uani 1 1 d . . .
H24A H 0.2674 -0.9509 -0.2769 0.101 Uiso 1 1 calc R . .
C25 C 0.2039(2) -0.7451(4) -0.31756(15) 0.0720(9) Uani 1 1 d . . .
C26 C 0.2147(2) -0.5847(3) -0.32021(13) 0.0580(7) Uani 1 1 d . . .
H26A H 0.1645 -0.5203 -0.3479 0.070 Uiso 1 1 calc R . .
C27 C 0.29962(18) -0.5175(3) -0.28215(11) 0.0490(6) Uani 1 1 d . . .
C28 C 0.30657(16) -0.3393(3) -0.28805(11) 0.0440(6) Uani 1 1 d . . .
H28A H 0.2601 -0.2881 -0.2917 0.053 Uiso 1 1 calc R . .
C29 C 0.39560(16) -0.2622(3) -0.23170(11) 0.0443(6) Uani 1 1 d . . .
C30 C 0.45763(17) -0.2184(3) -0.23383(11) 0.0528(6) Uani 1 1 d . . .
H30A H 0.4467 -0.2411 -0.2699 0.063 Uiso 1 1 calc R . .
C31 C 0.53710(18) -0.1407(3) -0.18367(12) 0.0575(7) Uani 1 1 d . . .
H31A H 0.5779 -0.1127 -0.1868 0.069 Uiso 1 1 calc R . .
C32 C 0.55521(16) -0.1057(3) -0.13018(11) 0.0510(6) Uani 1 1 d . . .
C33 C 0.49471(16) -0.1523(3) -0.12415(11) 0.0463(6) Uani 1 1 d . . .
C34 C 0.51274(19) -0.1213(3) -0.06848(12) 0.0597(7) Uani 1 1 d . . .
H34A H 0.5651 -0.0686 -0.0349 0.072 Uiso 1 1 calc R . .
C35 C 0.4536(2) -0.1683(4) -0.06390(13) 0.0665(8) Uani 1 1 d . . .
H35A H 0.4657 -0.1463 -0.0274 0.080 Uiso 1 1 calc R . .
C36 C 0.37550(19) -0.2489(3) -0.11329(13) 0.0600(7) Uani 1 1 d . . .
H36A H 0.3362 -0.2819 -0.1093 0.072 Uiso 1 1 calc R . .
C37 C 0.35623(17) -0.2796(3) -0.16738(12) 0.0503(6) Uani 1 1 d . . .
H37A H 0.3035 -0.3332 -0.2000 0.060 Uiso 1 1 calc R . .
C38 C 0.41447(16) -0.2319(3) -0.17529(11) 0.0424(5) Uani 1 1 d . . .
C39 C 0.28474(16) -0.3016(3) -0.34833(11) 0.0434(6) Uani 1 1 d . . .
C40 C 0.2368(2) -0.0901(3) -0.42178(13) 0.0622(8) Uani 1 1 d . . .
H40A H 0.2647 -0.1581 -0.4317 0.075 Uiso 1 1 calc R . .
C41 C 0.2788(3) 0.0706(5) -0.40259(18) 0.1094(14) Uani 1 1 d . . .
H41A H 0.3422 0.0607 -0.3673 0.164 Uiso 1 1 calc R . .
H41B H 0.2534 0.1353 -0.3909 0.164 Uiso 1 1 calc R . .
H41C H 0.2678 0.1194 -0.4372 0.164 Uiso 1 1 calc R . .
C42 C 0.1385(3) -0.0892(6) -0.47545(16) 0.1113(14) Uani 1 1 d . . .
H42A H 0.1164 -0.1966 -0.4857 0.167 Uiso 1 1 calc R . .
H42B H 0.1241 -0.0404 -0.5113 0.167 Uiso 1 1 calc R . .
H42C H 0.1110 -0.0299 -0.4642 0.167 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
Cl1 C4 1.732(4) . ?
O1 C18 1.315(3) . ?
O1 C19 1.476(3) . ?
O2 C18 1.200(3) . ?
O3 C11 1.364(3) . ?
O3 H3B 0.8200 . ?
C1 C6 1.375(4) . ?
C1 C2 1.393(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.362(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.364(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.378(4) . ?
C5 C6 1.383(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.523(3) . ?
C7 C18 1.519(3) . ?
C7 C8 1.520(3) . ?
C7 H7A 0.9800 . ?
C8 C9 1.369(3) . ?
C8 C17 1.427(3) . ?
C9 C10 1.401(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.353(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.415(3) . ?
C12 C13 1.416(3) . ?
C12 C17 1.426(3) . ?
C13 C14 1.355(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.401(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.360(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.414(3) . ?
C16 H16A 0.9300 . ?
C19 C20 1.482(5) . ?
C19 C21 1.493(5) . ?
C19 H19A 0.9800 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
Cl2 C25 1.738(3) . ?
O4 C39 1.206(3) . ?
O5 C39 1.312(3) . ?
O5 C40 1.474(3) . ?
O6 C32 1.360(3) . ?
O6 H6A 0.8200 . ?
C22 C27 1.377(4) . ?
C22 C23 1.408(4) . ?
C22 H22A 0.9300 . ?
C23 C24 1.378(5) . ?
C23 H23A 0.9300 . ?
C24 C25 1.354(5) . ?
C24 H24A 0.9300 . ?
C25 C26 1.376(4) . ?
C26 C27 1.389(4) . ?
C26 H26A 0.9300 . ?
C27 C28 1.524(3) . ?
C28 C39 1.517(3) . ?
C28 C29 1.529(3) . ?
C28 H28A 0.9800 . ?
C29 C30 1.363(3) . ?
C29 C38 1.428(3) . ?
C30 C31 1.397(4) . ?
C30 H30A 0.9300 . ?
C31 C32 1.362(3) . ?
C31 H31A 0.9300 . ?
C32 C33 1.419(3) . ?
C33 C34 1.417(3) . ?
C33 C38 1.418(3) . ?
C34 C35 1.362(4) . ?
C34 H34A 0.9300 . ?
C35 C36 1.390(4) . ?
C35 H35A 0.9300 . ?
C36 C37 1.359(3) . ?
C36 H36A 0.9300 . ?
C37 C38 1.417(3) . ?
C37 H37A 0.9300 . ?
C40 C42 1.479(4) . ?
C40 C41 1.487(4) . ?
C40 H40A 0.9800 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 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
C18 O1 C19 118.7(2) . . ?
C11 O3 H3B 109.5 . . ?
C6 C1 C2 119.9(3) . . ?
C6 C1 H1A 120.0 . . ?
C2 C1 H1A 120.0 . . ?
C3 C2 C1 120.7(4) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
C2 C3 C4 119.4(3) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C3 C4 C5 121.0(3) . . ?
C3 C4 Cl1 119.8(3) . . ?
C5 C4 Cl1 119.3(3) . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C1 C6 C5 119.0(3) . . ?
C1 C6 C7 122.9(3) . . ?
C5 C6 C7 118.0(2) . . ?
C18 C7 C8 109.15(18) . . ?
C18 C7 C6 110.10(19) . . ?
C8 C7 C6 115.4(2) . . ?
C18 C7 H7A 107.3 . . ?
C8 C7 H7A 107.3 . . ?
C6 C7 H7A 107.3 . . ?
C9 C8 C17 118.0(2) . . ?
C9 C8 C7 121.9(2) . . ?
C17 C8 C7 120.1(2) . . ?
C8 C9 C10 122.3(2) . . ?
C8 C9 H9A 118.8 . . ?
C10 C9 H9A 118.8 . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10A 119.8 . . ?
C9 C10 H10A 119.8 . . ?
C10 C11 O3 122.8(2) . . ?
C10 C11 C12 120.5(2) . . ?
O3 C11 C12 116.7(2) . . ?
C11 C12 C13 121.8(2) . . ?
C11 C12 C17 118.8(2) . . ?
C13 C12 C17 119.5(2) . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13A 119.6 . . ?
C12 C13 H13A 119.6 . . ?
C13 C14 C15 120.0(2) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 H15A 119.5 . . ?
C14 C15 H15A 119.5 . . ?
C15 C16 C17 121.3(2) . . ?
C15 C16 H16A 119.4 . . ?
C17 C16 H16A 119.4 . . ?
C16 C17 C12 117.5(2) . . ?
C16 C17 C8 122.6(2) . . ?
C12 C17 C8 119.8(2) . . ?
O2 C18 O1 124.2(2) . . ?
O2 C18 C7 124.6(2) . . ?
O1 C18 C7 111.2(2) . . ?
O1 C19 C20 107.5(3) . . ?
O1 C19 C21 106.2(3) . . ?
C20 C19 C21 113.8(3) . . ?
O1 C19 H19A 109.7 . . ?
C20 C19 H19A 109.7 . . ?
C21 C19 H19A 109.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C39 O5 C40 119.67(19) . . ?
C32 O6 H6A 109.5 . . ?
C27 C22 C23 119.8(3) . . ?
C27 C22 H22A 120.1 . . ?
C23 C22 H22A 120.1 . . ?
C24 C23 C22 120.5(3) . . ?
C24 C23 H23A 119.8 . . ?
C22 C23 H23A 119.8 . . ?
C25 C24 C23 119.2(3) . . ?
C25 C24 H24A 120.4 . . ?
C23 C24 H24A 120.4 . . ?
C24 C25 C26 121.1(3) . . ?
C24 C25 Cl2 119.6(3) . . ?
C26 C25 Cl2 119.3(3) . . ?
C25 C26 C27 121.0(3) . . ?
C25 C26 H26A 119.5 . . ?
C27 C26 H26A 119.5 . . ?
C22 C27 C26 118.4(3) . . ?
C22 C27 C28 123.5(3) . . ?
C26 C27 C28 118.1(2) . . ?
C39 C28 C27 111.04(19) . . ?
C39 C28 C29 110.06(19) . . ?
C27 C28 C29 115.4(2) . . ?
C39 C28 H28A 106.6 . . ?
C27 C28 H28A 106.6 . . ?
C29 C28 H28A 106.6 . . ?
C30 C29 C38 118.4(2) . . ?
C30 C29 C28 121.9(2) . . ?
C38 C29 C28 119.6(2) . . ?
C29 C30 C31 122.2(2) . . ?
C29 C30 H30A 118.9 . . ?
C31 C30 H30A 118.9 . . ?
C32 C31 C30 120.4(2) . . ?
C32 C31 H31A 119.8 . . ?
C30 C31 H31A 119.8 . . ?
O6 C32 C31 122.8(2) . . ?
O6 C32 C33 117.0(2) . . ?
C31 C32 C33 120.2(2) . . ?
C34 C33 C38 119.6(2) . . ?
C34 C33 C32 121.5(2) . . ?
C38 C33 C32 118.8(2) . . ?
C35 C34 C33 120.2(3) . . ?
C35 C34 H34A 119.9 . . ?
C33 C34 H34A 119.9 . . ?
C34 C35 C36 120.7(2) . . ?
C34 C35 H35A 119.7 . . ?
C36 C35 H35A 119.7 . . ?
C37 C36 C35 120.4(3) . . ?
C37 C36 H36A 119.8 . . ?
C35 C36 H36A 119.8 . . ?
C36 C37 C38 121.6(2) . . ?
C36 C37 H37A 119.2 . . ?
C38 C37 H37A 119.2 . . ?
C37 C38 C33 117.5(2) . . ?
C37 C38 C29 122.6(2) . . ?
C33 C38 C29 119.9(2) . . ?
O4 C39 O5 124.3(2) . . ?
O4 C39 C28 124.7(2) . . ?
O5 C39 C28 111.0(2) . . ?
O5 C40 C42 107.2(2) . . ?
O5 C40 C41 106.2(2) . . ?
C42 C40 C41 114.2(3) . . ?
O5 C40 H40A 109.7 . . ?
C42 C40 H40A 109.7 . . ?
C41 C40 H40A 109.7 . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C40 C42 H42A 109.5 . . ?
C40 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C40 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 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
C6 C1 C2 C3 0.5(5) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C2 C3 C4 Cl1 179.6(3) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
Cl1 C4 C5 C6 179.7(2) . . . . ?
C2 C1 C6 C5 -1.3(4) . . . . ?
C2 C1 C6 C7 176.3(3) . . . . ?
C4 C5 C6 C1 1.1(4) . . . . ?
C4 C5 C6 C7 -176.5(2) . . . . ?
C1 C6 C7 C18 -98.7(3) . . . . ?
C5 C6 C7 C18 78.9(3) . . . . ?
C1 C6 C7 C8 25.4(3) . . . . ?
C5 C6 C7 C8 -157.0(2) . . . . ?
C18 C7 C8 C9 21.6(3) . . . . ?
C6 C7 C8 C9 -103.0(3) . . . . ?
C18 C7 C8 C17 -157.2(2) . . . . ?
C6 C7 C8 C17 78.2(3) . . . . ?
C17 C8 C9 C10 2.4(4) . . . . ?
C7 C8 C9 C10 -176.5(2) . . . . ?
C8 C9 C10 C11 0.6(4) . . . . ?
C9 C10 C11 O3 178.3(2) . . . . ?
C9 C10 C11 C12 -2.4(4) . . . . ?
C10 C11 C12 C13 -178.8(2) . . . . ?
O3 C11 C12 C13 0.6(3) . . . . ?
C10 C11 C12 C17 1.1(4) . . . . ?
O3 C11 C12 C17 -179.6(2) . . . . ?
C11 C12 C13 C14 177.8(2) . . . . ?
C17 C12 C13 C14 -2.1(4) . . . . ?
C12 C13 C14 C15 1.1(4) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C14 C15 C16 C17 -0.5(4) . . . . ?
C15 C16 C17 C12 -0.5(4) . . . . ?
C15 C16 C17 C8 179.5(2) . . . . ?
C11 C12 C17 C16 -178.1(2) . . . . ?
C13 C12 C17 C16 1.8(3) . . . . ?
C11 C12 C17 C8 1.9(3) . . . . ?
C13 C12 C17 C8 -178.2(2) . . . . ?
C9 C8 C17 C16 176.4(2) . . . . ?
C7 C8 C17 C16 -4.8(3) . . . . ?
C9 C8 C17 C12 -3.6(3) . . . . ?
C7 C8 C17 C12 175.3(2) . . . . ?
C19 O1 C18 O2 8.9(4) . . . . ?
C19 O1 C18 C7 -170.0(2) . . . . ?
C8 C7 C18 O2 -92.5(3) . . . . ?
C6 C7 C18 O2 35.2(3) . . . . ?
C8 C7 C18 O1 86.4(2) . . . . ?
C6 C7 C18 O1 -145.9(2) . . . . ?
C18 O1 C19 C20 99.8(3) . . . . ?
C18 O1 C19 C21 -138.1(3) . . . . ?
C27 C22 C23 C24 0.2(4) . . . . ?
C22 C23 C24 C25 -0.5(5) . . . . ?
C23 C24 C25 C26 0.6(5) . . . . ?
C23 C24 C25 Cl2 -179.2(2) . . . . ?
C24 C25 C26 C27 -0.3(4) . . . . ?
Cl2 C25 C26 C27 179.47(19) . . . . ?
C23 C22 C27 C26 0.0(4) . . . . ?
C23 C22 C27 C28 -179.4(2) . . . . ?
C25 C26 C27 C22 0.0(4) . . . . ?
C25 C26 C27 C28 179.4(2) . . . . ?
C22 C27 C28 C39 105.2(3) . . . . ?
C26 C27 C28 C39 -74.2(3) . . . . ?
C22 C27 C28 C29 -21.0(3) . . . . ?
C26 C27 C28 C29 159.6(2) . . . . ?
C39 C28 C29 C30 -21.2(3) . . . . ?
C27 C28 C29 C30 105.5(3) . . . . ?
C39 C28 C29 C38 157.6(2) . . . . ?
C27 C28 C29 C38 -75.7(3) . . . . ?
C38 C29 C30 C31 -2.1(4) . . . . ?
C28 C29 C30 C31 176.7(2) . . . . ?
C29 C30 C31 C32 0.0(4) . . . . ?
C30 C31 C32 O6 -178.5(3) . . . . ?
C30 C31 C32 C33 2.0(4) . . . . ?
O6 C32 C33 C34 -1.2(4) . . . . ?
C31 C32 C33 C34 178.4(3) . . . . ?
O6 C32 C33 C38 178.9(2) . . . . ?
C31 C32 C33 C38 -1.6(4) . . . . ?
C38 C33 C34 C35 0.4(4) . . . . ?
C32 C33 C34 C35 -179.6(3) . . . . ?
C33 C34 C35 C36 0.8(4) . . . . ?
C34 C35 C36 C37 -1.1(4) . . . . ?
C35 C36 C37 C38 0.3(4) . . . . ?
C36 C37 C38 C33 0.8(4) . . . . ?
C36 C37 C38 C29 -179.8(2) . . . . ?
C34 C33 C38 C37 -1.1(3) . . . . ?
C32 C33 C38 C37 178.8(2) . . . . ?
C34 C33 C38 C29 179.5(2) . . . . ?
C32 C33 C38 C29 -0.6(3) . . . . ?
C30 C29 C38 C37 -177.0(2) . . . . ?
C28 C29 C38 C37 4.2(3) . . . . ?
C30 C29 C38 C33 2.4(3) . . . . ?
C28 C29 C38 C33 -176.5(2) . . . . ?
C40 O5 C39 O4 -5.1(4) . . . . ?
C40 O5 C39 C28 174.8(2) . . . . ?
C27 C28 C39 O4 -26.1(3) . . . . ?
C29 C28 C39 O4 103.0(3) . . . . ?
C27 C28 C39 O5 154.0(2) . . . . ?
C29 C28 C39 O5 -76.9(2) . . . . ?
C39 O5 C40 C42 104.6(3) . . . . ?
C39 O5 C40 C41 -133.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_z_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1822537'
loop_
_audit_author_name
_audit_author_address
'Junliang Zhang' 'East China Normal University'
_audit_update_record             
;
2018-02-07 deposited with the CCDC.	2019-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 Br O3'
_chemical_formula_weight         399.27

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.2815(13)
_cell_length_b                   26.184(4)
_cell_length_c                   8.2635(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.173(5)
_cell_angle_gamma                90.00
_cell_volume                     1832.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4830
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      22.7

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    2.260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4363
_exptl_absorpt_correction_T_max  0.5703
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20367
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3185
_reflns_number_gt                2327
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1714P)²+2.1324P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3185
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1079
_refine_ls_R_factor_gt           0.0870
_refine_ls_wR_factor_ref         0.2576
_refine_ls_wR_factor_gt          0.2372
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.61791(9) 0.21453(3) 0.09334(11) 0.0792(4) Uani 1 1 d . . .
O1 O 0.0986(5) 0.46971(17) -0.3671(6) 0.0653(12) Uani 1 1 d . . .
H1A H 0.1458 0.4970 -0.3517 0.098 Uiso 1 1 calc R . .
O2 O -0.1617(5) 0.41047(17) -0.3620(5) 0.0527(10) Uani 1 1 d . . .
O3 O -0.2015(5) 0.43025(16) -0.6410(5) 0.0503(10) Uani 1 1 d . . .
C1 C 0.4066(6) 0.3562(2) -0.0792(7) 0.0420(12) Uani 1 1 d . . .
C2 C 0.5123(7) 0.3172(3) 0.0181(8) 0.0525(15) Uani 1 1 d . . .
H2A H 0.6051 0.3254 0.1151 0.063 Uiso 1 1 calc R . .
C3 C 0.4766(7) 0.2680(3) -0.0319(9) 0.0546(15) Uani 1 1 d . . .
C4 C 0.3377(7) 0.2538(2) -0.1754(9) 0.0553(15) Uani 1 1 d . . .
H4A H 0.3159 0.2196 -0.2060 0.066 Uiso 1 1 calc R . .
C5 C 0.2344(7) 0.2910(2) -0.2699(8) 0.0460(13) Uani 1 1 d . . .
H5A H 0.1422 0.2817 -0.3659 0.055 Uiso 1 1 calc R . .
C6 C 0.2639(6) 0.3432(2) -0.2257(7) 0.0386(12) Uani 1 1 d . . .
C7 C 0.1575(6) 0.3830(2) -0.3207(7) 0.0388(12) Uani 1 1 d . . .
C8 C 0.2006(6) 0.4324(2) -0.2716(7) 0.0439(13) Uani 1 1 d . . .
C9 C 0.3417(7) 0.4451(2) -0.1286(8) 0.0489(14) Uani 1 1 d . . .
H9A H 0.3659 0.4792 -0.0980 0.059 Uiso 1 1 calc R . .
C10 C 0.4445(6) 0.4077(2) -0.0334(7) 0.0459(13) Uani 1 1 d . . .
H10A H 0.5388 0.4163 0.0609 0.055 Uiso 1 1 calc R . .
C11 C 0.0185(6) 0.3578(2) -0.6462(7) 0.0423(12) Uani 1 1 d . . .
C12 C 0.1091(8) 0.3877(3) -0.7058(9) 0.0626(17) Uani 1 1 d . . .
H12A H 0.1678 0.4147 -0.6372 0.075 Uiso 1 1 calc R . .
C13 C 0.1121(10) 0.3773(3) -0.8670(11) 0.072(2) Uani 1 1 d . . .
H13A H 0.1736 0.3973 -0.9069 0.087 Uiso 1 1 calc R . .
C14 C 0.0261(10) 0.3378(4) -0.9703(10) 0.073(2) Uani 1 1 d . . .
H14A H 0.0283 0.3313 -1.0799 0.088 Uiso 1 1 calc R . .
C15 C -0.0615(9) 0.3085(3) -0.9119(9) 0.0618(17) Uani 1 1 d . . .
H15A H -0.1214 0.2819 -0.9821 0.074 Uiso 1 1 calc R . .
C16 C -0.0626(7) 0.3176(2) -0.7493(7) 0.0471(13) Uani 1 1 d . . .
H16A H -0.1197 0.2960 -0.7079 0.056 Uiso 1 1 calc R . .
C17 C 0.0018(6) 0.3692(2) -0.4746(7) 0.0392(12) Uani 1 1 d . . .
H17A H -0.0327 0.3371 -0.4404 0.047 Uiso 1 1 calc R . .
C18 C -0.1303(6) 0.4075(2) -0.5038(7) 0.0421(13) Uani 1 1 d . . .
C19 C -0.2754(8) 0.4491(3) -0.3626(10) 0.0627(18) Uani 1 1 d . . .
H19A H -0.2696 0.4787 -0.4326 0.075 Uiso 1 1 calc R . .
C20 C -0.2231(13) 0.4646(5) -0.1706(14) 0.113(4) Uani 1 1 d . . .
H20A H -0.1182 0.4785 -0.1272 0.170 Uiso 1 1 calc R . .
H20B H -0.2239 0.4353 -0.1013 0.170 Uiso 1 1 calc R . .
H20C H -0.2940 0.4900 -0.1613 0.170 Uiso 1 1 calc R . .
C21 C -0.4410(10) 0.4268(4) -0.4432(15) 0.092(3) Uani 1 1 d . . .
H21A H -0.4677 0.4178 -0.5647 0.137 Uiso 1 1 calc R . .
H21B H -0.5150 0.4516 -0.4375 0.137 Uiso 1 1 calc R . .
H21C H -0.4450 0.3968 -0.3782 0.137 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
Br1 C3 1.907(6) . ?
O1 C8 1.365(7) . ?
O1 H1A 0.8200 . ?
O2 C18 1.321(7) . ?
O2 C19 1.461(7) . ?
O3 C18 1.209(7) . ?
C1 C10 1.406(8) . ?
C1 C2 1.416(8) . ?
C1 C6 1.422(7) . ?
C2 C3 1.354(10) . ?
C2 H2A 0.9300 . ?
C3 C4 1.398(9) . ?
C4 C5 1.366(8) . ?
C4 H4A 0.9300 . ?
C5 C6 1.411(8) . ?
C5 H5A 0.9300 . ?
C6 C7 1.430(7) . ?
C7 C8 1.365(8) . ?
C7 C17 1.527(7) . ?
C8 C9 1.399(8) . ?
C9 C10 1.369(8) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C16 1.371(8) . ?
C11 C12 1.378(9) . ?
C11 C17 1.518(8) . ?
C12 C13 1.371(10) . ?
C12 H12A 0.9300 . ?
C13 C14 1.370(12) . ?
C13 H13A 0.9300 . ?
C14 C15 1.343(11) . ?
C14 H14A 0.9300 . ?
C15 C16 1.370(9) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 C18 1.526(8) . ?
C17 H17A 0.9800 . ?
C19 C20 1.513(12) . ?
C19 C21 1.521(11) . ?
C19 H19A 0.9800 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C8 O1 H1A 109.5 . . ?
C18 O2 C19 117.3(5) . . ?
C10 C1 C2 120.0(5) . . ?
C10 C1 C6 120.2(5) . . ?
C2 C1 C6 119.9(5) . . ?
C3 C2 C1 119.2(5) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 H2A 120.4 . . ?
C2 C3 C4 122.5(6) . . ?
C2 C3 Br1 120.3(4) . . ?
C4 C3 Br1 117.2(5) . . ?
C5 C4 C3 118.9(6) . . ?
C5 C4 H4A 120.6 . . ?
C3 C4 H4A 120.6 . . ?
C4 C5 C6 121.8(5) . . ?
C4 C5 H5A 119.1 . . ?
C6 C5 H5A 119.1 . . ?
C5 C6 C1 117.8(5) . . ?
C5 C6 C7 123.2(5) . . ?
C1 C6 C7 119.0(5) . . ?
C8 C7 C6 118.4(5) . . ?
C8 C7 C17 122.3(5) . . ?
C6 C7 C17 119.3(5) . . ?
O1 C8 C7 117.2(5) . . ?
O1 C8 C9 120.4(5) . . ?
C7 C8 C9 122.4(5) . . ?
C10 C9 C8 120.4(6) . . ?
C10 C9 H9A 119.8 . . ?
C8 C9 H9A 119.8 . . ?
C9 C10 C1 119.5(5) . . ?
C9 C10 H10A 120.2 . . ?
C1 C10 H10A 120.2 . . ?
C16 C11 C12 118.3(6) . . ?
C16 C11 C17 119.3(5) . . ?
C12 C11 C17 122.3(5) . . ?
C13 C12 C11 119.5(7) . . ?
C13 C12 H12A 120.3 . . ?
C11 C12 H12A 120.3 . . ?
C14 C13 C12 121.1(7) . . ?
C14 C13 H13A 119.4 . . ?
C12 C13 H13A 119.4 . . ?
C15 C14 C13 119.4(7) . . ?
C15 C14 H14A 120.3 . . ?
C13 C14 H14A 120.3 . . ?
C14 C15 C16 120.2(7) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C11 C16 C15 121.4(6) . . ?
C11 C16 H16A 119.3 . . ?
C15 C16 H16A 119.3 . . ?
C11 C17 C18 111.3(4) . . ?
C11 C17 C7 113.6(4) . . ?
C18 C17 C7 113.6(4) . . ?
C11 C17 H17A 105.8 . . ?
C18 C17 H17A 105.8 . . ?
C7 C17 H17A 105.8 . . ?
O3 C18 O2 124.6(5) . . ?
O3 C18 C17 124.6(5) . . ?
O2 C18 C17 110.6(5) . . ?
O2 C19 C20 105.1(6) . . ?
O2 C19 C21 109.5(6) . . ?
C20 C19 C21 113.3(7) . . ?
O2 C19 H19A 109.6 . . ?
C20 C19 H19A 109.6 . . ?
C21 C19 H19A 109.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C10 C1 C2 C3 -177.6(5) . . . . ?
C6 C1 C2 C3 0.9(8) . . . . ?
C1 C2 C3 C4 -0.8(9) . . . . ?
C1 C2 C3 Br1 178.9(5) . . . . ?
C2 C3 C4 C5 0.5(10) . . . . ?
Br1 C3 C4 C5 -179.2(5) . . . . ?
C3 C4 C5 C6 -0.4(10) . . . . ?
C4 C5 C6 C1 0.6(9) . . . . ?
C4 C5 C6 C7 -179.3(5) . . . . ?
C10 C1 C6 C5 177.7(5) . . . . ?
C2 C1 C6 C5 -0.8(8) . . . . ?
C10 C1 C6 C7 -2.4(8) . . . . ?
C2 C1 C6 C7 179.1(5) . . . . ?
C5 C6 C7 C8 -177.3(5) . . . . ?
C1 C6 C7 C8 2.8(8) . . . . ?
C5 C6 C7 C17 1.7(8) . . . . ?
C1 C6 C7 C17 -178.2(5) . . . . ?
C6 C7 C8 O1 178.5(5) . . . . ?
C17 C7 C8 O1 -0.5(8) . . . . ?
C6 C7 C8 C9 -2.3(9) . . . . ?
C17 C7 C8 C9 178.7(5) . . . . ?
O1 C8 C9 C10 -179.6(6) . . . . ?
C7 C8 C9 C10 1.2(9) . . . . ?
C8 C9 C10 C1 -0.6(9) . . . . ?
C2 C1 C10 C9 179.8(5) . . . . ?
C6 C1 C10 C9 1.3(8) . . . . ?
C16 C11 C12 C13 1.8(10) . . . . ?
C17 C11 C12 C13 -176.2(6) . . . . ?
C11 C12 C13 C14 0.2(12) . . . . ?
C12 C13 C14 C15 -0.7(12) . . . . ?
C13 C14 C15 C16 -1.0(11) . . . . ?
C12 C11 C16 C15 -3.5(9) . . . . ?
C17 C11 C16 C15 174.6(5) . . . . ?
C14 C15 C16 C11 3.1(10) . . . . ?
C16 C11 C17 C18 -92.0(6) . . . . ?
C12 C11 C17 C18 85.9(7) . . . . ?
C16 C11 C17 C7 138.2(5) . . . . ?
C12 C11 C17 C7 -43.8(7) . . . . ?
C8 C7 C17 C11 98.8(6) . . . . ?
C6 C7 C17 C11 -80.1(6) . . . . ?
C8 C7 C17 C18 -29.8(7) . . . . ?
C6 C7 C17 C18 151.3(5) . . . . ?
C19 O2 C18 O3 -9.0(8) . . . . ?
C19 O2 C18 C17 174.4(5) . . . . ?
C11 C17 C18 O3 -7.4(7) . . . . ?
C7 C17 C18 O3 122.4(6) . . . . ?
C11 C17 C18 O2 169.3(4) . . . . ?
C7 C17 C18 O2 -60.9(6) . . . . ?
C18 O2 C19 C20 -148.9(7) . . . . ?
C18 O2 C19 C21 89.1(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         2.036
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.127
####################################################################### 
# 
# 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_z_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1884847'
loop_
_audit_author_name
_audit_author_address
'Lu Liu'
;East China Normal University
China
;
_audit_update_record             
;
2018-12-13 deposited with the CCDC.	2019-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 F O3'
_chemical_formula_weight         338.36

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.0324(7)
_cell_length_b                   10.4173(9)
_cell_length_c                   21.4761(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.076(3)
_cell_angle_gamma                90.00
_cell_volume                     1779.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3884
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      22.46

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9664
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20369
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3149
_reflns_number_gt                2009
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0572P)²+0.0000P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3149
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1165
_refine_ls_wR_factor_gt          0.1036
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.75793(15) 0.04142(12) 0.00918(6) 0.0783(4) Uani 1 1 d . . .
O1 O 0.62419(15) 0.33286(13) 0.18453(6) 0.0631(4) Uani 1 1 d . . .
H1B H 0.6766 0.2668 0.1799 0.095 Uiso 1 1 calc R . .
O2 O 0.57058(16) -0.05075(12) 0.11549(6) 0.0589(4) Uani 1 1 d . . .
O3 O 0.74674(16) 0.10064(13) 0.15933(6) 0.0646(4) Uani 1 1 d . . .
C1 C 0.2360(2) 0.23102(17) 0.08531(8) 0.0469(5) Uani 1 1 d . . .
H1A H 0.2003 0.1767 0.0517 0.056 Uiso 1 1 calc R . .
C2 C 0.1202(2) 0.30088(18) 0.11077(8) 0.0514(5) Uani 1 1 d . . .
H2A H 0.0070 0.2935 0.0946 0.062 Uiso 1 1 calc R . .
C3 C 0.1694(2) 0.38430(17) 0.16131(8) 0.0478(5) Uani 1 1 d . . .
C4 C 0.0522(3) 0.4607(2) 0.18820(10) 0.0628(6) Uani 1 1 d . . .
H4A H -0.0615 0.4560 0.1723 0.075 Uiso 1 1 calc R . .
C5 C 0.1039(3) 0.5402(2) 0.23666(11) 0.0751(7) Uani 1 1 d . . .
H5A H 0.0258 0.5909 0.2534 0.090 Uiso 1 1 calc R . .
C6 C 0.2727(3) 0.5470(2) 0.26190(11) 0.0789(7) Uani 1 1 d . . .
H6A H 0.3061 0.6012 0.2957 0.095 Uiso 1 1 calc R . .
C7 C 0.3897(3) 0.47524(19) 0.23764(10) 0.0648(6) Uani 1 1 d . . .
H7A H 0.5022 0.4808 0.2551 0.078 Uiso 1 1 calc R . .
C8 C 0.3419(2) 0.39271(17) 0.18638(8) 0.0466(4) Uani 1 1 d . . .
C9 C 0.4601(2) 0.31731(16) 0.15851(8) 0.0459(4) Uani 1 1 d . . .
C10 C 0.40980(19) 0.23840(15) 0.10839(7) 0.0416(4) Uani 1 1 d . . .
C11 C 0.5297(2) 0.15869(17) 0.07500(8) 0.0445(4) Uani 1 1 d . . .
H11A H 0.4595 0.1054 0.0442 0.053 Uiso 1 1 calc R . .
C12 C 0.6297(2) 0.06681(19) 0.12109(9) 0.0494(5) Uani 1 1 d . . .
C13 C 0.6547(3) -0.1494(2) 0.15769(11) 0.0714(6) Uani 1 1 d . . .
H13A H 0.6940 -0.1100 0.1985 0.086 Uiso 1 1 calc R . .
C14 C 0.8028(4) -0.1970(3) 0.12998(14) 0.1246(12) Uani 1 1 d . . .
H14A H 0.8802 -0.1277 0.1274 0.187 Uiso 1 1 calc R . .
H14B H 0.7663 -0.2303 0.0886 0.187 Uiso 1 1 calc R . .
H14C H 0.8573 -0.2639 0.1561 0.187 Uiso 1 1 calc R . .
C15 C 0.5259(4) -0.2470(2) 0.16606(15) 0.1197(11) Uani 1 1 d . . .
H15A H 0.4355 -0.2074 0.1838 0.180 Uiso 1 1 calc R . .
H15B H 0.5755 -0.3132 0.1938 0.180 Uiso 1 1 calc R . .
H15C H 0.4833 -0.2839 0.1260 0.180 Uiso 1 1 calc R . .
C16 C 0.6452(2) 0.23579(18) 0.03845(8) 0.0464(5) Uani 1 1 d . . .
C17 C 0.6441(2) 0.3677(2) 0.03348(9) 0.0599(5) Uani 1 1 d . . .
H17A H 0.5752 0.4157 0.0560 0.072 Uiso 1 1 calc R . .
C18 C 0.7447(3) 0.4299(2) -0.00464(11) 0.0747(7) Uani 1 1 d . . .
H18A H 0.7431 0.5191 -0.0070 0.090 Uiso 1 1 calc R . .
C19 C 0.8456(3) 0.3619(3) -0.03856(11) 0.0791(7) Uani 1 1 d . . .
H19A H 0.9109 0.4043 -0.0646 0.095 Uiso 1 1 calc R . .
C20 C 0.8504(3) 0.2310(3) -0.03420(10) 0.0730(6) Uani 1 1 d . . .
H20A H 0.9192 0.1831 -0.0568 0.088 Uiso 1 1 calc R . .
C21 C 0.7516(2) 0.1722(2) 0.00429(9) 0.0563(5) 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
F1 C21 1.367(2) . ?
O1 C9 1.3669(19) . ?
O1 H1B 0.8200 . ?
O2 C12 1.313(2) . ?
O2 C13 1.470(2) . ?
O3 C12 1.211(2) . ?
C1 C2 1.355(2) . ?
C1 C10 1.416(2) . ?
C1 H1A 0.9300 . ?
C2 C3 1.403(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.416(3) . ?
C3 C8 1.417(2) . ?
C4 C5 1.349(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.390(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.360(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.407(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.427(2) . ?
C9 C10 1.369(2) . ?
C10 C11 1.525(2) . ?
C11 C12 1.522(2) . ?
C11 C16 1.525(2) . ?
C11 H11A 0.9800 . ?
C13 C15 1.479(3) . ?
C13 C14 1.488(3) . ?
C13 H13A 0.9800 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C21 1.372(2) . ?
C16 C17 1.378(3) . ?
C17 C18 1.389(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.362(3) . ?
C18 H18A 0.9300 . ?
C19 C20 1.366(3) . ?
C19 H19A 0.9300 . ?
C20 C21 1.369(3) . ?
C20 H20A 0.9300 . ?

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
C9 O1 H1B 109.5 . . ?
C12 O2 C13 117.81(16) . . ?
C2 C1 C10 121.90(16) . . ?
C2 C1 H1A 119.1 . . ?
C10 C1 H1A 119.1 . . ?
C1 C2 C3 120.65(17) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 H2A 119.7 . . ?
C2 C3 C4 122.15(18) . . ?
C2 C3 C8 119.10(16) . . ?
C4 C3 C8 118.75(18) . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 H6A 119.6 . . ?
C5 C6 H6A 119.6 . . ?
C6 C7 C8 120.5(2) . . ?
C6 C7 H7A 119.7 . . ?
C8 C7 H7A 119.7 . . ?
C7 C8 C3 118.68(18) . . ?
C7 C8 C9 122.67(17) . . ?
C3 C8 C9 118.65(16) . . ?
O1 C9 C10 123.61(16) . . ?
O1 C9 C8 115.06(15) . . ?
C10 C9 C8 121.31(15) . . ?
C9 C10 C1 118.37(15) . . ?
C9 C10 C11 124.07(15) . . ?
C1 C10 C11 117.55(15) . . ?
C12 C11 C16 111.26(13) . . ?
C12 C11 C10 110.30(14) . . ?
C16 C11 C10 115.16(14) . . ?
C12 C11 H11A 106.5 . . ?
C16 C11 H11A 106.5 . . ?
C10 C11 H11A 106.5 . . ?
O3 C12 O2 124.75(18) . . ?
O3 C12 C11 123.13(18) . . ?
O2 C12 C11 112.09(16) . . ?
O2 C13 C15 106.69(18) . . ?
O2 C13 C14 108.09(18) . . ?
C15 C13 C14 115.5(2) . . ?
O2 C13 H13A 108.8 . . ?
C15 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 115.91(17) . . ?
C21 C16 C11 119.37(17) . . ?
C17 C16 C11 124.58(16) . . ?
C16 C17 C18 120.9(2) . . ?
C16 C17 H17A 119.6 . . ?
C18 C17 H17A 119.6 . . ?
C19 C18 C17 120.7(2) . . ?
C19 C18 H18A 119.6 . . ?
C17 C18 H18A 119.6 . . ?
C18 C19 C20 119.7(2) . . ?
C18 C19 H19A 120.1 . . ?
C20 C19 H19A 120.1 . . ?
C19 C20 C21 118.3(2) . . ?
C19 C20 H20A 120.8 . . ?
C21 C20 H20A 120.8 . . ?
F1 C21 C20 118.29(19) . . ?
F1 C21 C16 117.32(16) . . ?
C20 C21 C16 124.4(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
C10 C1 C2 C3 0.3(3) . . . . ?
C1 C2 C3 C4 178.67(17) . . . . ?
C1 C2 C3 C8 -1.3(3) . . . . ?
C2 C3 C4 C5 -179.81(18) . . . . ?
C8 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C7 1.0(4) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C7 C8 C3 -1.1(3) . . . . ?
C6 C7 C8 C9 178.79(19) . . . . ?
C2 C3 C8 C7 -179.09(17) . . . . ?
C4 C3 C8 C7 0.9(3) . . . . ?
C2 C3 C8 C9 1.0(2) . . . . ?
C4 C3 C8 C9 -178.93(16) . . . . ?
C7 C8 C9 O1 -1.2(2) . . . . ?
C3 C8 C9 O1 178.68(14) . . . . ?
C7 C8 C9 C10 -179.62(17) . . . . ?
C3 C8 C9 C10 0.2(2) . . . . ?
O1 C9 C10 C1 -179.56(15) . . . . ?
C8 C9 C10 C1 -1.3(2) . . . . ?
O1 C9 C10 C11 -0.4(3) . . . . ?
C8 C9 C10 C11 177.90(15) . . . . ?
C2 C1 C10 C9 1.0(3) . . . . ?
C2 C1 C10 C11 -178.19(16) . . . . ?
C9 C10 C11 C12 59.1(2) . . . . ?
C1 C10 C11 C12 -121.70(17) . . . . ?
C9 C10 C11 C16 -67.8(2) . . . . ?
C1 C10 C11 C16 111.37(17) . . . . ?
C13 O2 C12 O3 -1.4(3) . . . . ?
C13 O2 C12 C11 -179.46(15) . . . . ?
C16 C11 C12 O3 52.7(2) . . . . ?
C10 C11 C12 O3 -76.4(2) . . . . ?
C16 C11 C12 O2 -129.22(16) . . . . ?
C10 C11 C12 O2 101.71(17) . . . . ?
C12 O2 C13 C15 151.7(2) . . . . ?
C12 O2 C13 C14 -83.4(2) . . . . ?
C12 C11 C16 C21 56.8(2) . . . . ?
C10 C11 C16 C21 -176.77(15) . . . . ?
C12 C11 C16 C17 -127.62(19) . . . . ?
C10 C11 C16 C17 -1.2(2) . . . . ?
C21 C16 C17 C18 0.6(3) . . . . ?
C11 C16 C17 C18 -175.09(17) . . . . ?
C16 C17 C18 C19 0.7(3) . . . . ?
C17 C18 C19 C20 -1.2(3) . . . . ?
C18 C19 C20 C21 0.4(3) . . . . ?
C19 C20 C21 F1 -179.27(19) . . . . ?
C19 C20 C21 C16 1.0(3) . . . . ?
C17 C16 C21 F1 178.76(16) . . . . ?
C11 C16 C21 F1 -5.3(2) . . . . ?
C17 C16 C21 C20 -1.5(3) . . . . ?
C11 C16 C21 C20 174.48(17) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_z_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1822538'
loop_
_audit_author_name
_audit_author_address
'Junliang Zhang' 'East China Normal University'
_audit_update_record             
;
2018-02-07 deposited with the CCDC.	2019-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H12 O2'
_chemical_formula_weight         260.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.0083(11)
_cell_length_b                   17.6321(17)
_cell_length_c                   6.9894(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.387(3)
_cell_angle_gamma                90.00
_cell_volume                     1342.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3018
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      22.09

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9611
_exptl_absorpt_correction_T_max  0.9827
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15530
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2375
_reflns_number_gt                1721
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0351P)²+0.2420P] 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
_refine_ls_extinction_coef       0.0120(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2375
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0810
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.13484(9) 0.07595(6) 0.36075(16) 0.0550(3) Uani 1 1 d . . .
O1 O 0.17809(12) 0.18896(7) 0.4990(2) 0.0813(4) Uani 1 1 d . . .
C1 C 0.18045(14) -0.06711(9) -0.0093(2) 0.0523(4) Uani 1 1 d . . .
C2 C 0.13680(17) -0.13901(10) -0.0777(3) 0.0669(5) Uani 1 1 d . . .
H2A H 0.1690 -0.1614 -0.1798 0.080 Uiso 1 1 calc R . .
C3 C 0.04876(17) -0.17588(10) 0.0029(3) 0.0698(5) Uani 1 1 d . . .
H3A H 0.0216 -0.2232 -0.0443 0.084 Uiso 1 1 calc R . .
C4 C -0.00160(15) -0.14355(10) 0.1561(3) 0.0637(5) Uani 1 1 d . . .
H4A H -0.0621 -0.1694 0.2098 0.076 Uiso 1 1 calc R . .
C5 C 0.03720(14) -0.07448(9) 0.2274(2) 0.0544(4) Uani 1 1 d . . .
H5A H 0.0032 -0.0533 0.3294 0.065 Uiso 1 1 calc R . .
C6 C 0.12866(13) -0.03499(8) 0.1471(2) 0.0457(4) Uani 1 1 d . . .
C7 C 0.17600(13) 0.03622(8) 0.2092(2) 0.0444(4) Uani 1 1 d . . .
C8 C 0.26484(13) 0.07375(8) 0.1326(2) 0.0463(4) Uani 1 1 d . . .
C9 C 0.31534(15) 0.04124(10) -0.0205(2) 0.0589(5) Uani 1 1 d . . .
H9A H 0.3766 0.0662 -0.0744 0.071 Uiso 1 1 calc R . .
C10 C 0.27311(16) -0.02767(11) -0.0891(2) 0.0630(5) Uani 1 1 d . . .
H10A H 0.3061 -0.0494 -0.1913 0.076 Uiso 1 1 calc R . .
C11 C 0.19839(15) 0.14352(9) 0.3816(3) 0.0564(4) Uani 1 1 d . . .
C12 C 0.29138(14) 0.14665(9) 0.2416(2) 0.0497(4) Uani 1 1 d . . .
H12A H 0.2737 0.1899 0.1538 0.060 Uiso 1 1 calc R . .
C13 C 0.42081(14) 0.15255(8) 0.3478(2) 0.0466(4) Uani 1 1 d . . .
C14 C 0.50012(15) 0.20779(10) 0.3033(2) 0.0586(4) Uani 1 1 d . . .
H14A H 0.4735 0.2436 0.2088 0.070 Uiso 1 1 calc R . .
C15 C 0.61963(16) 0.21033(11) 0.3988(3) 0.0677(5) Uani 1 1 d . . .
H15A H 0.6728 0.2479 0.3676 0.081 Uiso 1 1 calc R . .
C16 C 0.65985(16) 0.15849(11) 0.5375(3) 0.0637(5) Uani 1 1 d . . .
H16A H 0.7405 0.1600 0.5997 0.076 Uiso 1 1 calc R . .
C17 C 0.58098(17) 0.10402(10) 0.5851(3) 0.0677(5) Uani 1 1 d . . .
H17A H 0.6076 0.0689 0.6815 0.081 Uiso 1 1 calc R . .
C18 C 0.46269(16) 0.10100(9) 0.4911(3) 0.0604(5) Uani 1 1 d . . .
H18A H 0.4099 0.0637 0.5244 0.072 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
O2 C11 1.3784(19) . ?
O2 C7 1.3994(17) . ?
O1 C11 1.1912(19) . ?
C1 C2 1.414(2) . ?
C1 C10 1.415(2) . ?
C1 C6 1.422(2) . ?
C2 C3 1.356(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.397(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.361(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.406(2) . ?
C5 H5A 0.9300 . ?
C6 C7 1.404(2) . ?
C7 C8 1.354(2) . ?
C8 C9 1.398(2) . ?
C8 C12 1.501(2) . ?
C9 C10 1.363(2) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C12 1.517(2) . ?
C12 C13 1.511(2) . ?
C12 H12A 0.9800 . ?
C13 C14 1.374(2) . ?
C13 C18 1.381(2) . ?
C14 C15 1.386(2) . ?
C14 H14A 0.9300 . ?
C15 C16 1.359(2) . ?
C15 H15A 0.9300 . ?
C16 C17 1.368(2) . ?
C16 H16A 0.9300 . ?
C17 C18 1.371(2) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?

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
C11 O2 C7 107.30(12) . . ?
C2 C1 C10 122.43(16) . . ?
C2 C1 C6 117.54(15) . . ?
C10 C1 C6 120.02(15) . . ?
C3 C2 C1 121.16(17) . . ?
C3 C2 H2A 119.4 . . ?
C1 C2 H2A 119.4 . . ?
C2 C3 C4 120.70(17) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C5 C4 C3 120.47(17) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
C4 C5 C6 120.11(16) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C7 C6 C5 125.05(14) . . ?
C7 C6 C1 114.93(14) . . ?
C5 C6 C1 120.02(15) . . ?
C8 C7 O2 112.77(13) . . ?
C8 C7 C6 124.87(14) . . ?
O2 C7 C6 122.36(13) . . ?
C7 C8 C9 119.52(14) . . ?
C7 C8 C12 108.41(13) . . ?
C9 C8 C12 132.06(14) . . ?
C10 C9 C8 118.78(15) . . ?
C10 C9 H9A 120.6 . . ?
C8 C9 H9A 120.6 . . ?
C9 C10 C1 121.87(16) . . ?
C9 C10 H10A 119.1 . . ?
C1 C10 H10A 119.1 . . ?
O1 C11 O2 120.72(16) . . ?
O1 C11 C12 129.19(16) . . ?
O2 C11 C12 110.07(13) . . ?
C8 C12 C13 114.08(12) . . ?
C8 C12 C11 101.34(13) . . ?
C13 C12 C11 111.27(13) . . ?
C8 C12 H12A 109.9 . . ?
C13 C12 H12A 109.9 . . ?
C11 C12 H12A 109.9 . . ?
C14 C13 C18 118.35(15) . . ?
C14 C13 C12 121.51(14) . . ?
C18 C13 C12 120.13(14) . . ?
C13 C14 C15 120.25(16) . . ?
C13 C14 H14A 119.9 . . ?
C15 C14 H14A 119.9 . . ?
C16 C15 C14 120.63(17) . . ?
C16 C15 H15A 119.7 . . ?
C14 C15 H15A 119.7 . . ?
C15 C16 C17 119.57(16) . . ?
C15 C16 H16A 120.2 . . ?
C17 C16 H16A 120.2 . . ?
C16 C17 C18 120.17(17) . . ?
C16 C17 H17A 119.9 . . ?
C18 C17 H17A 119.9 . . ?
C17 C18 C13 121.02(16) . . ?
C17 C18 H18A 119.5 . . ?
C13 C18 H18A 119.5 . . ?

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
C10 C1 C2 C3 179.31(17) . . . . ?
C6 C1 C2 C3 0.0(2) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C4 C5 C6 C7 -179.72(15) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C2 C1 C6 C7 179.72(14) . . . . ?
C10 C1 C6 C7 0.4(2) . . . . ?
C2 C1 C6 C5 -0.2(2) . . . . ?
C10 C1 C6 C5 -179.52(14) . . . . ?
C11 O2 C7 C8 1.20(16) . . . . ?
C11 O2 C7 C6 -179.01(13) . . . . ?
C5 C6 C7 C8 179.39(14) . . . . ?
C1 C6 C7 C8 -0.6(2) . . . . ?
C5 C6 C7 O2 -0.4(2) . . . . ?
C1 C6 C7 O2 179.68(12) . . . . ?
O2 C7 C8 C9 -179.98(13) . . . . ?
C6 C7 C8 C9 0.2(2) . . . . ?
O2 C7 C8 C12 1.04(17) . . . . ?
C6 C7 C8 C12 -178.74(13) . . . . ?
C7 C8 C9 C10 0.2(2) . . . . ?
C12 C8 C9 C10 178.92(16) . . . . ?
C8 C9 C10 C1 -0.3(3) . . . . ?
C2 C1 C10 C9 -179.27(17) . . . . ?
C6 C1 C10 C9 0.0(3) . . . . ?
C7 O2 C11 O1 178.17(15) . . . . ?
C7 O2 C11 C12 -2.92(16) . . . . ?
C7 C8 C12 C13 117.08(14) . . . . ?
C9 C8 C12 C13 -61.7(2) . . . . ?
C7 C8 C12 C11 -2.59(16) . . . . ?
C9 C8 C12 C11 178.62(16) . . . . ?
O1 C11 C12 C8 -177.84(18) . . . . ?
O2 C11 C12 C8 3.37(16) . . . . ?
O1 C11 C12 C13 60.5(2) . . . . ?
O2 C11 C12 C13 -118.28(14) . . . . ?
C8 C12 C13 C14 117.73(16) . . . . ?
C11 C12 C13 C14 -128.37(16) . . . . ?
C8 C12 C13 C18 -61.22(19) . . . . ?
C11 C12 C13 C18 52.68(19) . . . . ?
C18 C13 C14 C15 1.1(2) . . . . ?
C12 C13 C14 C15 -177.89(16) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C15 C16 C17 -1.0(3) . . . . ?
C15 C16 C17 C18 1.1(3) . . . . ?
C16 C17 C18 C13 -0.1(3) . . . . ?
C14 C13 C18 C17 -0.9(3) . . . . ?
C12 C13 C18 C17 178.04(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.110
_refine_diff_density_rms         0.026
