# 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. 
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data_180804zrl_0m
_database_code_depnum_ccdc_archive 'CCDC 1895258'
loop_
_audit_author_name
_audit_author_address
'Yankai Liu'
;Ocean University of China
China
;
_audit_update_record             
;
2019-02-02 deposited with the CCDC.	2019-04-19 downloaded from the CCDC.
;
_audit_creation_date             2018-08-04
_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         'C21 H21 Cl O5'
_chemical_formula_sum            'C21 H21 Cl O5'
_chemical_formula_weight         388.83
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.1480 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.229(4)
_cell_length_b                   11.212(6)
_cell_length_c                   22.921(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1857.8(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2146
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.831
_cell_measurement_theta_min      2.542
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.1095 before and 0.0591 after correction. The Ratio of minimum to maximum transmission is 0.6706. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0916
_diffrn_reflns_av_unetI/netI     0.0870
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9387
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.014
_diffrn_reflns_theta_max         25.014
_diffrn_reflns_theta_min         2.541
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2359
_reflns_number_total             3263
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details 
;
 Flack x determined using 753 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0738
_refine_ls_restrained_S_all      1.002
_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)+(0.1261P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1835
_refine_ls_wR_factor_ref         0.2015
_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 Riding coordinates:
 O2(H2)
2.b Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C9(H9)
2.c Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B), C17(H17A,H17B)
2.d Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C6(H6), C18(H18), C19(H19), C20(H20), C21(H21)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.1826(3) 0.6207(2) 0.24052(9) 0.0783(8) Uani 1 1 d . . . . .
O1 O 0.4662(6) 0.2507(3) 0.48164(17) 0.0381(11) Uani 1 1 d . . . . .
O2 O 0.2765(6) 0.2258(4) 0.4007(2) 0.0428(11) Uani 1 1 d . . . . .
H2 H 0.196227 0.201440 0.422961 0.064 Uiso 1 1 d R . . . .
O3 O 0.4723(8) 0.0155(4) 0.3820(2) 0.0516(13) Uani 1 1 d . . . . .
O4 O 0.5042(8) 0.0198(4) 0.4782(2) 0.0543(13) Uani 1 1 d . . . . .
O5 O 0.4809(7) 0.4001(4) 0.54263(17) 0.0410(11) Uani 1 1 d . . . . .
C1 C 1.0079(11) 0.5503(6) 0.2791(3) 0.0490(18) Uani 1 1 d . . . . .
C2 C 1.0549(11) 0.4686(7) 0.3217(3) 0.0572(19) Uani 1 1 d . . . . .
H2A H 1.178099 0.448218 0.327875 0.069 Uiso 1 1 calc R . . . .
C3 C 0.9185(10) 0.4180(6) 0.3547(3) 0.0460(17) Uani 1 1 d . . . . .
H3 H 0.951125 0.364261 0.383843 0.055 Uiso 1 1 calc R . . . .
C4 C 0.7345(9) 0.4439(5) 0.3461(3) 0.0352(14) Uani 1 1 d . . . . .
C5 C 0.6908(9) 0.5229(6) 0.3014(3) 0.0419(16) Uani 1 1 d . . . . .
H5 H 0.567666 0.540724 0.293505 0.050 Uiso 1 1 calc R . . . .
C6 C 0.8306(12) 0.5755(6) 0.2684(3) 0.0524(19) Uani 1 1 d . . . . .
H6 H 0.800272 0.628477 0.238729 0.063 Uiso 1 1 calc R . . . .
C7 C 0.5833(9) 0.3910(5) 0.3832(2) 0.0353(14) Uani 1 1 d . . . . .
H7 H 0.464021 0.414140 0.366400 0.042 Uiso 1 1 calc R . . . .
C8 C 0.5919(9) 0.4387(5) 0.4455(3) 0.0342(14) Uani 1 1 d . . . . .
H8 H 0.715099 0.421837 0.461367 0.041 Uiso 1 1 calc R . . . .
C9 C 0.4511(9) 0.3765(5) 0.4829(3) 0.0352(14) Uani 1 1 d . . . . .
H9 H 0.326010 0.401013 0.471592 0.042 Uiso 1 1 calc R . . . .
C10 C 0.4493(8) 0.2033(5) 0.4245(3) 0.0338(14) Uani 1 1 d . . . . .
C11 C 0.4805(9) 0.0689(5) 0.4328(3) 0.0390(15) Uani 1 1 d . . . . .
C12 C 0.4948(12) -0.1139(5) 0.3828(3) 0.0516(18) Uani 1 1 d . . . . .
H12A H 0.394042 -0.150775 0.404169 0.062 Uiso 1 1 calc R . . . .
H12B H 0.610370 -0.135257 0.401569 0.062 Uiso 1 1 calc R . . . .
C13 C 0.4945(15) -0.1551(6) 0.3215(3) 0.079(3) Uani 1 1 d . . . . .
H13A H 0.593383 -0.117050 0.300660 0.118 Uiso 1 1 calc GR . . . .
H13B H 0.378505 -0.134899 0.303634 0.118 Uiso 1 1 calc GR . . . .
H13C H 0.511270 -0.239976 0.320446 0.118 Uiso 1 1 calc GR . . . .
C14 C 0.5933(9) 0.2551(5) 0.3843(3) 0.0374(15) Uani 1 1 d . . . . .
H14A H 0.574408 0.224508 0.345191 0.045 Uiso 1 1 calc R . . . .
H14B H 0.715242 0.230504 0.397222 0.045 Uiso 1 1 calc R . . . .
C15 C 0.4981(9) 0.5217(5) 0.5559(3) 0.0385(15) Uani 1 1 d . . . . .
C16 C 0.5314(10) 0.6067(6) 0.5136(3) 0.0436(16) Uani 1 1 d . . . . .
C17 C 0.5559(13) 0.5718(5) 0.4508(3) 0.0473(18) Uani 1 1 d . . . . .
H17A H 0.659027 0.615613 0.434251 0.057 Uiso 1 1 calc R . . . .
H17B H 0.445429 0.592473 0.429028 0.057 Uiso 1 1 calc R . . . .
C18 C 0.5440(12) 0.7246(6) 0.5320(3) 0.0504(18) Uani 1 1 d . . . . .
H18 H 0.567717 0.783862 0.504592 0.060 Uiso 1 1 calc R . . . .
C19 C 0.5223(12) 0.7558(7) 0.5894(3) 0.059(2) Uani 1 1 d . . . . .
H19 H 0.524088 0.835651 0.600327 0.071 Uiso 1 1 calc R . . . .
C20 C 0.4978(12) 0.6677(6) 0.6309(3) 0.056(2) Uani 1 1 d . . . . .
H20 H 0.489216 0.687668 0.670184 0.067 Uiso 1 1 calc R . . . .
C21 C 0.4861(11) 0.5489(6) 0.6136(3) 0.0507(18) Uani 1 1 d . . . . .
H21 H 0.470299 0.488886 0.641132 0.061 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 C1 1.733(7) . ?
O1 C9 1.415(7) . ?
O1 C10 1.418(7) . ?
O2 H2 0.8201 . ?
O2 C10 1.387(7) . ?
O3 C11 1.310(8) . ?
O3 C12 1.460(7) . ?
O4 C11 1.190(8) . ?
O5 C9 1.411(7) . ?
O5 C15 1.402(7) . ?
C1 C2 1.381(11) . ?
C1 C6 1.335(11) . ?
C2 H2A 0.9300 . ?
C2 C3 1.365(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(10) . ?
C4 C5 1.391(9) . ?
C4 C7 1.506(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.393(10) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C7 C8 1.526(8) . ?
C7 C14 1.526(8) . ?
C8 H8 0.9800 . ?
C8 C9 1.501(8) . ?
C8 C17 1.520(9) . ?
C9 H9 0.9800 . ?
C10 C11 1.535(8) . ?
C10 C14 1.507(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.478(9) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.382(9) . ?
C15 C21 1.358(9) . ?
C16 C17 1.501(9) . ?
C16 C18 1.390(9) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18 0.9300 . ?
C18 C19 1.370(10) . ?
C19 H19 0.9300 . ?
C19 C20 1.383(11) . ?
C20 H20 0.9300 . ?
C20 C21 1.392(9) . ?
C21 H21 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 C10 112.7(4) . . ?
C10 O2 H2 109.3 . . ?
C11 O3 C12 116.0(5) . . ?
C15 O5 C9 114.0(4) . . ?
C2 C1 Cl1 118.9(6) . . ?
C6 C1 Cl1 120.6(6) . . ?
C6 C1 C2 120.4(7) . . ?
C1 C2 H2A 120.4 . . ?
C3 C2 C1 119.3(7) . . ?
C3 C2 H2A 120.4 . . ?
C2 C3 H3 118.9 . . ?
C2 C3 C4 122.1(7) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 C5 117.3(6) . . ?
C3 C4 C7 122.5(6) . . ?
C5 C4 C7 120.1(6) . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.3(7) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 120.5(7) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C4 C7 H7 108.2 . . ?
C4 C7 C8 111.2(5) . . ?
C4 C7 C14 111.6(5) . . ?
C8 C7 H7 108.2 . . ?
C14 C7 H7 108.2 . . ?
C14 C7 C8 109.4(5) . . ?
C7 C8 H8 108.4 . . ?
C9 C8 C7 110.1(5) . . ?
C9 C8 H8 108.4 . . ?
C9 C8 C17 107.1(5) . . ?
C17 C8 C7 114.3(5) . . ?
C17 C8 H8 108.4 . . ?
O1 C9 C8 113.5(5) . . ?
O1 C9 H9 110.2 . . ?
O5 C9 O1 101.2(4) . . ?
O5 C9 C8 111.3(5) . . ?
O5 C9 H9 110.2 . . ?
C8 C9 H9 110.2 . . ?
O1 C10 C11 104.0(5) . . ?
O1 C10 C14 111.1(5) . . ?
O2 C10 O1 111.9(5) . . ?
O2 C10 C11 111.1(5) . . ?
O2 C10 C14 108.1(5) . . ?
C14 C10 C11 110.6(5) . . ?
O3 C11 C10 109.4(5) . . ?
O4 C11 O3 124.9(6) . . ?
O4 C11 C10 125.7(6) . . ?
O3 C12 H12A 110.2 . . ?
O3 C12 H12B 110.2 . . ?
O3 C12 C13 107.4(5) . . ?
H12A C12 H12B 108.5 . . ?
C13 C12 H12A 110.2 . . ?
C13 C12 H12B 110.2 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 C14 H14A 109.4 . . ?
C7 C14 H14B 109.4 . . ?
C10 C14 C7 111.3(5) . . ?
C10 C14 H14A 109.4 . . ?
C10 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 O5 122.2(5) . . ?
C21 C15 O5 115.1(5) . . ?
C21 C15 C16 122.6(6) . . ?
C15 C16 C17 120.9(6) . . ?
C15 C16 C18 117.0(6) . . ?
C18 C16 C17 122.1(6) . . ?
C8 C17 H17A 109.5 . . ?
C8 C17 H17B 109.5 . . ?
C16 C17 C8 110.6(5) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C16 C18 H18 119.1 . . ?
C19 C18 C16 121.8(7) . . ?
C19 C18 H18 119.1 . . ?
C18 C19 H19 120.2 . . ?
C18 C19 C20 119.5(7) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 120.2 . . ?
C19 C20 C21 119.6(7) . . ?
C21 C20 H20 120.2 . . ?
C15 C21 C20 119.2(7) . . ?
C15 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?

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
Cl1 C1 C2 C3 176.2(6) . . . . ?
Cl1 C1 C6 C5 -177.0(5) . . . . ?
O1 C10 C11 O3 -178.5(5) . . . . ?
O1 C10 C11 O4 3.1(9) . . . . ?
O1 C10 C14 C7 -56.0(7) . . . . ?
O2 C10 C11 O3 60.9(7) . . . . ?
O2 C10 C11 O4 -117.4(7) . . . . ?
O2 C10 C14 C7 67.2(7) . . . . ?
O5 C15 C16 C17 -1.6(11) . . . . ?
O5 C15 C16 C18 179.4(7) . . . . ?
O5 C15 C21 C20 -178.7(7) . . . . ?
C1 C2 C3 C4 1.4(11) . . . . ?
C2 C1 C6 C5 2.3(11) . . . . ?
C2 C3 C4 C5 1.1(11) . . . . ?
C2 C3 C4 C7 -178.4(7) . . . . ?
C3 C4 C5 C6 -2.0(10) . . . . ?
C3 C4 C7 C8 68.1(8) . . . . ?
C3 C4 C7 C14 -54.4(8) . . . . ?
C4 C5 C6 C1 0.3(11) . . . . ?
C4 C7 C8 C9 -174.9(5) . . . . ?
C4 C7 C8 C17 64.5(7) . . . . ?
C4 C7 C14 C10 176.4(5) . . . . ?
C5 C4 C7 C8 -111.4(7) . . . . ?
C5 C4 C7 C14 126.1(6) . . . . ?
C6 C1 C2 C3 -3.1(11) . . . . ?
C7 C4 C5 C6 177.5(6) . . . . ?
C7 C8 C9 O1 54.3(7) . . . . ?
C7 C8 C9 O5 167.8(5) . . . . ?
C7 C8 C17 C16 169.3(6) . . . . ?
C8 C7 C14 C10 52.9(8) . . . . ?
C9 O1 C10 O2 -63.1(6) . . . . ?
C9 O1 C10 C11 176.9(5) . . . . ?
C9 O1 C10 C14 57.8(6) . . . . ?
C9 O5 C15 C16 -16.0(9) . . . . ?
C9 O5 C15 C21 166.2(6) . . . . ?
C9 C8 C17 C16 47.1(8) . . . . ?
C10 O1 C9 O5 -177.4(4) . . . . ?
C10 O1 C9 C8 -58.0(7) . . . . ?
C11 O3 C12 C13 -176.1(7) . . . . ?
C11 C10 C14 C7 -171.0(5) . . . . ?
C12 O3 C11 O4 -0.1(11) . . . . ?
C12 O3 C11 C10 -178.5(6) . . . . ?
C14 C7 C8 C9 -51.2(7) . . . . ?
C14 C7 C8 C17 -171.8(6) . . . . ?
C14 C10 C11 O3 -59.1(7) . . . . ?
C14 C10 C11 O4 122.5(8) . . . . ?
C15 O5 C9 O1 172.0(5) . . . . ?
C15 O5 C9 C8 51.1(7) . . . . ?
C15 C16 C17 C8 -15.7(10) . . . . ?
C15 C16 C18 C19 -0.7(12) . . . . ?
C16 C15 C21 C20 3.5(12) . . . . ?
C16 C18 C19 C20 3.8(13) . . . . ?
C17 C8 C9 O1 179.2(5) . . . . ?
C17 C8 C9 O5 -67.4(7) . . . . ?
C17 C16 C18 C19 -179.7(8) . . . . ?
C18 C16 C17 C8 163.2(7) . . . . ?
C18 C19 C20 C21 -3.2(13) . . . . ?
C19 C20 C21 C15 -0.3(13) . . . . ?
C21 C15 C16 C17 176.0(7) . . . . ?
C21 C15 C16 C18 -3.0(11) . . . . ?

_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_190122lxj_0m
_database_code_depnum_ccdc_archive 'CCDC 1895260'
loop_
_audit_author_name
_audit_author_address
'Yankai Liu'
;Ocean University of China
China
;
_audit_update_record             
;
2019-02-02 deposited with the CCDC.	2019-04-19 downloaded from the CCDC.
;
_audit_creation_date             2019-01-26
_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         'C20 H18 O4'
_chemical_formula_sum            'C20 H18 O4'
_chemical_formula_weight         322.34
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.3231(13)
_cell_length_b                   8.3376(10)
_cell_length_c                   10.6510(13)
_cell_angle_alpha                90
_cell_angle_beta                 116.926(2)
_cell_angle_gamma                90
_cell_volume                     817.35(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2591
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      27.451
_cell_measurement_theta_min      2.280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.0726 before and 0.0293 after correction. The Ratio of minimum to maximum transmission is 0.9225. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0125
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4947
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.530
_diffrn_reflns_theta_min         3.251
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    0.895
_reflns_Friedel_fraction_max     0.804
_reflns_number_gt                3014
_reflns_number_total             3389
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1155 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3389
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.048
_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)+(0.0446P)²+0.0950P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0905
_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
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17),
 C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.51601(15) 0.54271(19) 0.62911(15) 0.0424(4) Uani 1 1 d . . . . .
O2 O 0.74073(16) 0.5114(2) 0.79331(16) 0.0533(5) Uani 1 1 d . . . . .
O3 O 0.17294(18) 0.6382(3) 0.3534(2) 0.0662(6) Uani 1 1 d . . . . .
O4 O 0.23266(19) 0.5323(3) 0.5646(2) 0.0622(5) Uani 1 1 d . . . . .
C1 C 0.2661(2) 0.5820(3) 0.4784(2) 0.0406(5) Uani 1 1 d . . . . .
C2 C 0.6182(2) 0.5702(3) 0.2924(2) 0.0346(4) Uani 1 1 d . . . . .
C3 C 0.4182(2) 0.5900(2) 0.4964(2) 0.0362(5) Uani 1 1 d . . . . .
C4 C 0.6067(2) 0.6441(3) 0.4175(2) 0.0351(4) Uani 1 1 d . . . . .
H4 H 0.635774 0.759321 0.423443 0.042 Uiso 1 1 calc R . . . .
C5 C 0.7088(2) 0.5637(3) 0.5570(2) 0.0358(4) Uani 1 1 d . . . . .
H5 H 0.705847 0.445220 0.541317 0.043 Uiso 1 1 calc R . . . .
C6 C 0.8902(2) 0.5115(3) 0.8423(2) 0.0428(5) Uani 1 1 d . . . . .
C7 C 0.6592(2) 0.5965(3) 0.6678(2) 0.0397(5) Uani 1 1 d . . . . .
H7 H 0.665933 0.714042 0.688284 0.048 Uiso 1 1 calc R . . . .
C8 C 0.5910(2) 0.4082(3) 0.2629(2) 0.0433(5) Uani 1 1 d . . . . .
H8 H 0.564747 0.343612 0.321263 0.052 Uiso 1 1 calc R . . . .
C9 C 0.4530(2) 0.6389(3) 0.3972(2) 0.0379(5) Uani 1 1 d . . . . .
H9 H 0.377296 0.672292 0.309249 0.045 Uiso 1 1 calc R . . . .
C10 C 0.6555(2) 0.6620(3) 0.2054(2) 0.0447(5) Uani 1 1 d . . . . .
H10 H 0.674621 0.773262 0.223498 0.054 Uiso 1 1 calc R . . . .
C11 C 0.9556(2) 0.5642(3) 0.7617(2) 0.0428(5) Uani 1 1 d . . . . .
C12 C 0.6650(3) 0.5917(4) 0.0916(3) 0.0559(7) Uani 1 1 d . . . . .
H12 H 0.690625 0.655470 0.032325 0.067 Uiso 1 1 calc R . . . .
C13 C 1.1068(3) 0.5606(3) 0.8220(3) 0.0515(6) Uani 1 1 d . . . . .
H13 H 1.154239 0.596552 0.768807 0.062 Uiso 1 1 calc R . . . .
C14 C 0.6379(3) 0.4316(4) 0.0639(3) 0.0567(7) Uani 1 1 d . . . . .
H14 H 0.644328 0.384512 -0.014266 0.068 Uiso 1 1 calc R . . . .
C15 C 0.6013(3) 0.3393(3) 0.1501(3) 0.0534(6) Uani 1 1 d . . . . .
H15 H 0.583104 0.227906 0.131904 0.064 Uiso 1 1 calc R . . . .
C16 C 0.8652(2) 0.6197(3) 0.6126(2) 0.0513(6) Uani 1 1 d . . . . .
H16A H 0.906781 0.576814 0.551991 0.062 Uiso 1 1 calc R . . . .
H16B H 0.867674 0.738244 0.609106 0.062 Uiso 1 1 calc R . . . .
C17 C 0.9709(3) 0.4522(4) 0.9772(3) 0.0579(7) Uani 1 1 d . . . . .
H17 H 0.924090 0.413093 1.030012 0.069 Uiso 1 1 calc R . . . .
C18 C 1.1196(3) 0.4510(4) 1.0334(3) 0.0641(8) Uani 1 1 d . . . . .
H18 H 1.175857 0.411727 1.126306 0.077 Uiso 1 1 calc R . . . .
C19 C 1.1887(3) 0.5058(4) 0.9572(3) 0.0601(7) Uani 1 1 d . . . . .
H19 H 1.291791 0.505702 0.997598 0.072 Uiso 1 1 calc R . . . .
C20 C 0.0212(3) 0.6393(5) 0.3215(3) 0.0746(10) Uani 1 1 d . . . . .
H20A H -0.036448 0.682882 0.226767 0.112 Uiso 1 1 calc GR . . . .
H20B H 0.007771 0.706187 0.390337 0.112 Uiso 1 1 calc GR . . . .
H20C H -0.010583 0.529541 0.325684 0.112 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 C3 1.372(3) . ?
O1 C7 1.416(2) . ?
O2 C6 1.387(2) . ?
O2 C7 1.407(3) . ?
O3 C1 1.326(3) . ?
O3 C20 1.444(3) . ?
O4 C1 1.192(3) . ?
C1 C3 1.494(3) . ?
C2 C4 1.520(3) . ?
C2 C8 1.387(3) . ?
C2 C10 1.385(3) . ?
C3 C9 1.325(3) . ?
C4 H4 1.0000 . ?
C4 C5 1.533(3) . ?
C4 C9 1.502(3) . ?
C5 H5 1.0000 . ?
C5 C7 1.508(3) . ?
C5 C16 1.520(3) . ?
C6 C11 1.383(3) . ?
C6 C17 1.385(3) . ?
C7 H7 1.0000 . ?
C8 H8 0.9500 . ?
C8 C15 1.378(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C10 C12 1.389(4) . ?
C11 C13 1.393(3) . ?
C11 C16 1.504(3) . ?
C12 H12 0.9500 . ?
C12 C14 1.368(4) . ?
C13 H13 0.9500 . ?
C13 C19 1.377(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.375(4) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17 0.9500 . ?
C17 C18 1.372(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.379(4) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C7 113.17(16) . . ?
C6 O2 C7 116.25(17) . . ?
C1 O3 C20 117.1(2) . . ?
O3 C1 C3 110.81(19) . . ?
O4 C1 O3 124.4(2) . . ?
O4 C1 C3 124.8(2) . . ?
C8 C2 C4 120.38(19) . . ?
C10 C2 C4 121.2(2) . . ?
C10 C2 C8 118.4(2) . . ?
O1 C3 C1 111.09(18) . . ?
C9 C3 O1 124.83(19) . . ?
C9 C3 C1 124.08(19) . . ?
C2 C4 H4 107.7 . . ?
C2 C4 C5 112.33(16) . . ?
C5 C4 H4 107.7 . . ?
C9 C4 C2 111.02(17) . . ?
C9 C4 H4 107.7 . . ?
C9 C4 C5 110.18(17) . . ?
C4 C5 H5 108.3 . . ?
C7 C5 C4 110.56(16) . . ?
C7 C5 H5 108.3 . . ?
C7 C5 C16 108.44(17) . . ?
C16 C5 C4 112.72(17) . . ?
C16 C5 H5 108.3 . . ?
C11 C6 O2 122.64(19) . . ?
C11 C6 C17 121.6(2) . . ?
C17 C6 O2 115.8(2) . . ?
O1 C7 C5 113.23(17) . . ?
O1 C7 H7 109.5 . . ?
O2 C7 O1 102.32(17) . . ?
O2 C7 C5 112.54(17) . . ?
O2 C7 H7 109.5 . . ?
C5 C7 H7 109.5 . . ?
C2 C8 H8 119.5 . . ?
C15 C8 C2 121.1(2) . . ?
C15 C8 H8 119.5 . . ?
C3 C9 C4 122.98(19) . . ?
C3 C9 H9 118.5 . . ?
C4 C9 H9 118.5 . . ?
C2 C10 H10 119.9 . . ?
C2 C10 C12 120.1(2) . . ?
C12 C10 H10 119.9 . . ?
C6 C11 C13 117.8(2) . . ?
C6 C11 C16 120.6(2) . . ?
C13 C11 C16 121.5(2) . . ?
C10 C12 H12 119.6 . . ?
C14 C12 C10 120.7(2) . . ?
C14 C12 H12 119.6 . . ?
C11 C13 H13 119.4 . . ?
C19 C13 C11 121.3(2) . . ?
C19 C13 H13 119.4 . . ?
C12 C14 H14 120.2 . . ?
C12 C14 C15 119.6(2) . . ?
C15 C14 H14 120.2 . . ?
C8 C15 H15 120.0 . . ?
C14 C15 C8 120.1(3) . . ?
C14 C15 H15 120.0 . . ?
C5 C16 H16A 109.4 . . ?
C5 C16 H16B 109.4 . . ?
C11 C16 C5 111.01(18) . . ?
C11 C16 H16A 109.4 . . ?
C11 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C6 C17 H17 120.5 . . ?
C18 C17 C6 119.0(2) . . ?
C18 C17 H17 120.5 . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 121.0(2) . . ?
C19 C18 H18 119.5 . . ?
C13 C19 C18 119.3(2) . . ?
C13 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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 C3 C9 C4 1.8(3) . . . . ?
O2 C6 C11 C13 179.3(2) . . . . ?
O2 C6 C11 C16 -2.1(4) . . . . ?
O2 C6 C17 C18 -179.0(3) . . . . ?
O3 C1 C3 O1 175.7(2) . . . . ?
O3 C1 C3 C9 -3.3(3) . . . . ?
O4 C1 C3 O1 -4.1(3) . . . . ?
O4 C1 C3 C9 176.9(2) . . . . ?
C1 C3 C9 C4 -179.3(2) . . . . ?
C2 C4 C5 C7 -160.04(18) . . . . ?
C2 C4 C5 C16 78.4(2) . . . . ?
C2 C4 C9 C3 133.2(2) . . . . ?
C2 C8 C15 C14 -0.6(4) . . . . ?
C2 C10 C12 C14 0.0(4) . . . . ?
C3 O1 C7 O2 -170.14(16) . . . . ?
C3 O1 C7 C5 -48.7(2) . . . . ?
C4 C2 C8 C15 -179.8(2) . . . . ?
C4 C2 C10 C12 -179.9(2) . . . . ?
C4 C5 C7 O1 58.4(2) . . . . ?
C4 C5 C7 O2 173.83(18) . . . . ?
C4 C5 C16 C11 168.73(19) . . . . ?
C5 C4 C9 C3 8.1(3) . . . . ?
C6 O2 C7 O1 166.58(18) . . . . ?
C6 O2 C7 C5 44.7(3) . . . . ?
C6 C11 C13 C19 0.2(4) . . . . ?
C6 C11 C16 C5 -16.7(3) . . . . ?
C6 C17 C18 C19 -0.8(5) . . . . ?
C7 O1 C3 C1 -160.33(17) . . . . ?
C7 O1 C3 C9 18.7(3) . . . . ?
C7 O2 C6 C11 -12.0(3) . . . . ?
C7 O2 C6 C17 169.2(2) . . . . ?
C7 C5 C16 C11 46.0(3) . . . . ?
C8 C2 C4 C5 58.4(2) . . . . ?
C8 C2 C4 C9 -65.5(2) . . . . ?
C8 C2 C10 C12 0.0(3) . . . . ?
C9 C4 C5 C7 -35.7(2) . . . . ?
C9 C4 C5 C16 -157.26(19) . . . . ?
C10 C2 C4 C5 -121.7(2) . . . . ?
C10 C2 C4 C9 114.4(2) . . . . ?
C10 C2 C8 C15 0.3(3) . . . . ?
C10 C12 C14 C15 -0.2(4) . . . . ?
C11 C6 C17 C18 2.2(4) . . . . ?
C11 C13 C19 C18 1.1(5) . . . . ?
C12 C14 C15 C8 0.5(4) . . . . ?
C13 C11 C16 C5 161.8(2) . . . . ?
C16 C5 C7 O1 -177.57(19) . . . . ?
C16 C5 C7 O2 -62.1(2) . . . . ?
C16 C11 C13 C19 -178.3(3) . . . . ?
C17 C6 C11 C13 -1.9(4) . . . . ?
C17 C6 C11 C16 176.7(2) . . . . ?
C17 C18 C19 C13 -0.9(5) . . . . ?
C20 O3 C1 O4 0.4(4) . . . . ?
C20 O3 C1 C3 -179.5(2) . . . . ?

_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_180908lxj_0m
_database_code_depnum_ccdc_archive 'CCDC 1895259'
loop_
_audit_author_name
_audit_author_address
'Yankai Liu'
;Ocean University of China
China
;
_audit_update_record             
;
2019-02-02 deposited with the CCDC.	2019-04-19 downloaded from the CCDC.
;
_audit_creation_date             2018-09-10
_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         'C21 H19 Cl O4'
_chemical_formula_sum            'C21 H19 Cl O4'
_chemical_formula_weight         370.81
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.1480 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.5134(13)
_cell_length_b                   7.5193(9)
_cell_length_c                   22.921(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1812.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3700
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.064
_cell_measurement_theta_min      2.631
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.0824 before and 0.0362 after correction. The Ratio of minimum to maximum transmission is 0.9304. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11022
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.593
_diffrn_reflns_theta_min         2.629
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                3342
_reflns_number_total             4139
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 1173 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0587P)²+0.3719P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1190
_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
2.a Ternary CH refined with riding coordinates:
 C9(H9), C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C14(H14), C3(H3), C21(H21), C5(H5), C19(H19), C20(H20), C2(H2),
 C6(H6)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.01270(10) 0.01922(19) 0.58098(7) 0.0954(5) Uani 1 1 d . . . . .
O4 O 0.28367(19) 0.5390(3) 0.63307(9) 0.0407(5) Uani 1 1 d . . . . .
O1 O 0.2860(2) 0.3702(3) 0.71450(9) 0.0449(5) Uani 1 1 d . . . . .
O2 O 0.1312(3) 0.1420(3) 0.75543(12) 0.0662(8) Uani 1 1 d . . . . .
O3 O 0.2375(3) -0.0930(3) 0.72028(14) 0.0723(8) Uani 1 1 d . . . . .
C16 C 0.4711(3) 0.6938(4) 0.59702(11) 0.0332(6) Uani 1 1 d . . . . .
C15 C 0.3420(3) 0.6565(4) 0.59487(12) 0.0337(6) Uani 1 1 d . . . . .
C4 C 0.6131(3) 0.2084(4) 0.61616(12) 0.0359(6) Uani 1 1 d . . . . .
C9 C 0.3546(3) 0.5017(4) 0.68456(12) 0.0377(6) Uani 1 1 d . . . . .
H9 H 0.357706 0.609170 0.708686 0.045 Uiso 1 1 calc R . . . .
C7 C 0.4824(3) 0.2820(4) 0.62906(12) 0.0344(6) Uani 1 1 d . . . . .
H7 H 0.444121 0.319083 0.592017 0.041 Uiso 1 1 calc R . . . .
C18 C 0.5192(3) 0.8142(4) 0.55645(12) 0.0390(6) Uani 1 1 d . . . . .
H18 H 0.605261 0.842538 0.557286 0.047 Uiso 1 1 calc R . . . .
C17 C 0.5545(3) 0.6082(4) 0.64267(13) 0.0376(6) Uani 1 1 d . . . . .
H17A H 0.573562 0.693988 0.673034 0.045 Uiso 1 1 calc R . . . .
H17B H 0.634208 0.571629 0.625005 0.045 Uiso 1 1 calc R . . . .
C14 C 0.3942(3) 0.1510(4) 0.65740(13) 0.0398(7) Uani 1 1 d . . . . .
H14 H 0.400926 0.031737 0.647158 0.048 Uiso 1 1 calc R . . . .
C10 C 0.3076(3) 0.1973(4) 0.69616(12) 0.0385(6) Uani 1 1 d . . . . .
C8 C 0.4891(3) 0.4472(4) 0.66941(12) 0.0355(6) Uani 1 1 d . . . . .
H8 H 0.533756 0.414494 0.705380 0.043 Uiso 1 1 calc R . . . .
C3 C 0.6775(3) 0.1062(4) 0.65641(13) 0.0455(8) Uani 1 1 d . . . . .
H3 H 0.638269 0.078143 0.691594 0.055 Uiso 1 1 calc R . . . .
C11 C 0.2231(4) 0.0652(4) 0.72488(14) 0.0470(8) Uani 1 1 d . . . . .
C21 C 0.2635(3) 0.7325(4) 0.55324(14) 0.0460(7) Uani 1 1 d . . . . .
H21 H 0.177448 0.704159 0.551964 0.055 Uiso 1 1 calc R . . . .
C5 C 0.6718(3) 0.2429(4) 0.56330(13) 0.0457(8) Uani 1 1 d . . . . .
H5 H 0.628737 0.307878 0.534993 0.055 Uiso 1 1 calc R . . . .
C19 C 0.4424(4) 0.8920(4) 0.51523(14) 0.0495(8) Uani 1 1 d . . . . .
H19 H 0.476410 0.972016 0.488511 0.059 Uiso 1 1 calc R . . . .
C20 C 0.3148(4) 0.8510(5) 0.51366(15) 0.0533(9) Uani 1 1 d . . . . .
H20 H 0.262711 0.903551 0.485741 0.064 Uiso 1 1 calc R . . . .
C2 C 0.7994(3) 0.0442(5) 0.64563(16) 0.0536(8) Uani 1 1 d . . . . .
H2 H 0.841807 -0.024555 0.673176 0.064 Uiso 1 1 calc R . . . .
C6 C 0.7936(4) 0.1822(5) 0.55190(16) 0.0567(9) Uani 1 1 d . . . . .
H6 H 0.832309 0.206512 0.516285 0.068 Uiso 1 1 calc R . . . .
C1 C 0.8565(3) 0.0863(5) 0.59352(18) 0.0573(9) Uani 1 1 d . . . . .
C12 C 0.0377(5) 0.0272(7) 0.7844(2) 0.0962(18) Uani 1 1 d . . . . .
H12A H -0.047309 0.066003 0.773926 0.115 Uiso 1 1 calc R . . . .
H12B H 0.048257 -0.093878 0.770621 0.115 Uiso 1 1 calc R . . . .
C13 C 0.0504(6) 0.0306(9) 0.8442(2) 0.108(2) Uani 1 1 d . . . . .
H13A H 0.135208 -0.004517 0.854675 0.163 Uiso 1 1 calc GR . . . .
H13B H -0.009547 -0.050123 0.861426 0.163 Uiso 1 1 calc GR . . . .
H13C H 0.034486 0.148831 0.858250 0.163 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
Cl1 C1 1.742(4) . ?
O4 C15 1.387(3) . ?
O4 C9 1.424(3) . ?
O1 C9 1.403(3) . ?
O1 C10 1.385(3) . ?
O2 C11 1.326(4) . ?
O2 C12 1.467(4) . ?
O3 C11 1.204(4) . ?
C16 C15 1.387(4) . ?
C16 C18 1.392(4) . ?
C16 C17 1.510(4) . ?
C15 C21 1.385(4) . ?
C4 C7 1.511(4) . ?
C4 C3 1.379(4) . ?
C4 C5 1.384(4) . ?
C9 H9 0.9800 . ?
C9 C8 1.512(4) . ?
C7 H7 0.9800 . ?
C7 C14 1.501(4) . ?
C7 C8 1.550(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.374(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C8 1.521(4) . ?
C14 H14 0.9300 . ?
C14 C10 1.319(4) . ?
C10 C11 1.487(4) . ?
C8 H8 0.9800 . ?
C3 H3 0.9300 . ?
C3 C2 1.386(5) . ?
C21 H21 0.9300 . ?
C21 C20 1.381(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.377(5) . ?
C20 H20 0.9300 . ?
C2 H2 0.9300 . ?
C2 C1 1.373(5) . ?
C6 H6 0.9300 . ?
C6 C1 1.366(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.379(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C15 O4 C9 114.7(2) . . ?
C10 O1 C9 115.4(2) . . ?
C11 O2 C12 118.1(3) . . ?
C15 C16 C18 117.6(3) . . ?
C15 C16 C17 120.4(2) . . ?
C18 C16 C17 122.0(3) . . ?
O4 C15 C16 122.6(2) . . ?
C21 C15 O4 115.7(3) . . ?
C21 C15 C16 121.6(3) . . ?
C3 C4 C7 121.4(3) . . ?
C3 C4 C5 118.1(3) . . ?
C5 C4 C7 120.5(3) . . ?
O4 C9 H9 108.8 . . ?
O4 C9 C8 110.7(2) . . ?
O1 C9 O4 106.0(2) . . ?
O1 C9 H9 108.8 . . ?
O1 C9 C8 113.7(2) . . ?
C8 C9 H9 108.8 . . ?
C4 C7 H7 107.9 . . ?
C4 C7 C8 111.7(2) . . ?
C14 C7 C4 113.9(2) . . ?
C14 C7 H7 107.9 . . ?
C14 C7 C8 107.2(2) . . ?
C8 C7 H7 107.9 . . ?
C16 C18 H18 119.2 . . ?
C19 C18 C16 121.5(3) . . ?
C19 C18 H18 119.2 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 C8 110.9(2) . . ?
H17A C17 H17B 108.1 . . ?
C8 C17 H17A 109.5 . . ?
C8 C17 H17B 109.5 . . ?
C7 C14 H14 118.5 . . ?
C10 C14 C7 123.0(3) . . ?
C10 C14 H14 118.5 . . ?
O1 C10 C11 113.3(2) . . ?
C14 C10 O1 124.4(3) . . ?
C14 C10 C11 122.3(3) . . ?
C9 C8 C7 108.1(2) . . ?
C9 C8 C17 107.5(2) . . ?
C9 C8 H8 108.8 . . ?
C7 C8 H8 108.8 . . ?
C17 C8 C7 114.7(2) . . ?
C17 C8 H8 108.8 . . ?
C4 C3 H3 119.3 . . ?
C4 C3 C2 121.5(3) . . ?
C2 C3 H3 119.3 . . ?
O2 C11 C10 112.2(3) . . ?
O3 C11 O2 124.7(3) . . ?
O3 C11 C10 123.1(3) . . ?
C15 C21 H21 120.5 . . ?
C20 C21 C15 119.1(3) . . ?
C20 C21 H21 120.5 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.1(3) . . ?
C6 C5 H5 119.5 . . ?
C18 C19 H19 120.2 . . ?
C18 C19 C20 119.7(3) . . ?
C20 C19 H19 120.2 . . ?
C21 C20 H20 119.8 . . ?
C19 C20 C21 120.5(3) . . ?
C19 C20 H20 119.8 . . ?
C3 C2 H2 120.6 . . ?
C1 C2 C3 118.8(3) . . ?
C1 C2 H2 120.6 . . ?
C5 C6 H6 120.3 . . ?
C1 C6 C5 119.3(3) . . ?
C1 C6 H6 120.3 . . ?
C2 C1 Cl1 119.3(3) . . ?
C6 C1 Cl1 119.6(3) . . ?
C6 C1 C2 121.2(3) . . ?
O2 C12 H12A 109.2 . . ?
O2 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 O2 112.0(4) . . ?
C13 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C15 C21 C20 179.9(3) . . . . ?
O4 C9 C8 C7 -58.1(3) . . . . ?
O4 C9 C8 C17 66.2(3) . . . . ?
O1 C9 C8 C7 61.0(3) . . . . ?
O1 C9 C8 C17 -174.7(2) . . . . ?
O1 C10 C11 O2 9.7(4) . . . . ?
O1 C10 C11 O3 -170.5(4) . . . . ?
C16 C15 C21 C20 -1.3(5) . . . . ?
C16 C18 C19 C20 0.0(5) . . . . ?
C16 C17 C8 C9 -47.1(3) . . . . ?
C16 C17 C8 C7 73.1(3) . . . . ?
C15 O4 C9 O1 -174.9(2) . . . . ?
C15 O4 C9 C8 -51.1(3) . . . . ?
C15 C16 C18 C19 -0.8(4) . . . . ?
C15 C16 C17 C8 17.1(4) . . . . ?
C15 C21 C20 C19 0.5(5) . . . . ?
C4 C7 C14 C10 146.0(3) . . . . ?
C4 C7 C8 C9 -174.8(2) . . . . ?
C4 C7 C8 C17 65.3(3) . . . . ?
C4 C3 C2 C1 0.0(5) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
C9 O4 C15 C16 18.1(4) . . . . ?
C9 O4 C15 C21 -163.1(2) . . . . ?
C9 O1 C10 C14 6.3(4) . . . . ?
C9 O1 C10 C11 -174.0(3) . . . . ?
C7 C4 C3 C2 -177.4(3) . . . . ?
C7 C4 C5 C6 177.3(3) . . . . ?
C7 C14 C10 O1 1.2(5) . . . . ?
C7 C14 C10 C11 -178.5(3) . . . . ?
C18 C16 C15 O4 -179.9(2) . . . . ?
C18 C16 C15 C21 1.4(4) . . . . ?
C18 C16 C17 C8 -163.9(2) . . . . ?
C18 C19 C20 C21 0.1(5) . . . . ?
C17 C16 C15 O4 -0.9(4) . . . . ?
C17 C16 C15 C21 -179.6(3) . . . . ?
C17 C16 C18 C19 -179.7(3) . . . . ?
C14 C7 C8 C9 -49.3(3) . . . . ?
C14 C7 C8 C17 -169.2(2) . . . . ?
C14 C10 C11 O2 -170.5(3) . . . . ?
C14 C10 C11 O3 9.2(6) . . . . ?
C10 O1 C9 O4 83.5(3) . . . . ?
C10 O1 C9 C8 -38.3(3) . . . . ?
C8 C7 C14 C10 21.9(4) . . . . ?
C3 C4 C7 C14 -43.8(4) . . . . ?
C3 C4 C7 C8 77.9(3) . . . . ?
C3 C4 C5 C6 -2.3(5) . . . . ?
C3 C2 C1 Cl1 176.6(3) . . . . ?
C3 C2 C1 C6 -2.2(6) . . . . ?
C11 O2 C12 C13 110.5(6) . . . . ?
C5 C4 C7 C14 136.5(3) . . . . ?
C5 C4 C7 C8 -101.8(3) . . . . ?
C5 C4 C3 C2 2.3(5) . . . . ?
C5 C6 C1 Cl1 -176.7(3) . . . . ?
C5 C6 C1 C2 2.1(6) . . . . ?
C12 O2 C11 O3 -2.0(6) . . . . ?
C12 O2 C11 C10 177.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
