# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_zhaopf_0415
_database_code_depnum_ccdc_archive 'CCDC 2011405'
loop_
_audit_author_name
_audit_author_address
'Yanli Xu'
;Lan Zhou University
China
;
_audit_update_record             
;
2020-06-22 deposited with the CCDC.	2021-01-22 downloaded from the CCDC.
;
_audit_creation_date             2019-04-17
_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         'C25 H21 Br O4'
_chemical_formula_sum            'C25 H21 Br O4'
_chemical_formula_weight         465.33
_chemical_absolute_configuration ?
_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'
Br Br -0.2901 2.4595 '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      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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   10.0294(4)
_cell_length_b                   10.8154(6)
_cell_length_c                   19.2909(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2092.51(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1446
_cell_measurement_temperature    292.90(10)
_cell_measurement_theta_max      25.1950
_cell_measurement_theta_min      3.7630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.994
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0754
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6822
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.484
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.90(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -52.00   97.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000    0.0000 149

#__ type_ start__ end____ width___ exp.time_
  2 omega  -23.00   18.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000  120.0000 41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0256249000
_diffrn_orient_matrix_UB_12      0.0309670000
_diffrn_orient_matrix_UB_13      -0.0295366000
_diffrn_orient_matrix_UB_21      -0.0531303000
_diffrn_orient_matrix_UB_22      -0.0431836000
_diffrn_orient_matrix_UB_23      -0.0017642000
_diffrn_orient_matrix_UB_31      -0.0389924000
_diffrn_orient_matrix_UB_32      0.0384271000
_diffrn_orient_matrix_UB_33      0.0218426000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3158
_reflns_number_total             4113
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 
;
 Flack x determined using 1031 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4113
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0486
_refine_ls_restrained_S_all      1.038
_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)+(0.0323P)²+0.1072P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0975
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C15(H15A,H15B), C24(H24A,H24B), C28(H28A,H28B), C0AA(H0AA,H0AB)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C11(H11), C12(H12), C14(H14), C16(H16), C20(H20), C21(H21), C22(H22),
 C23(H23), C26(H26), C29(H29)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.20962(7) -0.82194(8) -0.22640(4) 0.0526(2) Uani 1 1 d . . . . .
O1 O -0.6864(4) -0.9027(3) -0.46536(18) 0.0276(9) Uani 1 1 d . . . . .
C2 C -0.3871(6) -0.8356(6) -0.2589(3) 0.0310(14) Uani 1 1 d . . . . .
O3 O -0.8592(4) -0.9469(4) -0.30014(19) 0.0394(11) Uani 1 1 d . . . . .
C4 C -0.7875(6) -0.8755(5) -0.3317(3) 0.0252(12) Uani 1 1 d . . . . .
C5 C -0.9816(5) -0.8585(5) -0.4135(3) 0.0278(14) Uani 1 1 d . . . . .
H5A H -1.039826 -0.855465 -0.373361 0.033 Uiso 1 1 calc R . . . .
H5B H -1.021398 -0.806871 -0.449028 0.033 Uiso 1 1 calc R . . . .
C6 C -0.5587(5) -0.7722(5) -0.3371(3) 0.0253(13) Uani 1 1 d . . . . .
H6 H -0.587979 -0.721533 -0.372929 0.030 Uiso 1 1 calc R . . . .
O7 O -0.7524(3) -0.7218(3) -0.50329(19) 0.0283(10) Uani 1 1 d . . . . .
C8 C -0.8486(5) -1.1779(5) -0.5876(2) 0.0242(12) Uani 1 1 d . . . . .
O9 O -0.9445(4) -0.9169(3) -0.55632(19) 0.0289(9) Uani 1 1 d . . . . .
C10 C -0.9568(5) -1.0049(5) -0.5177(3) 0.0235(12) Uani 1 1 d . . . . .
C11 C -0.4713(6) -0.9218(5) -0.2290(3) 0.0315(13) Uani 1 1 d . . . . .
H11 H -0.441879 -0.971829 -0.192914 0.038 Uiso 1 1 calc R . . . .
C12 C -0.7326(5) -1.1090(5) -0.6019(3) 0.0271(13) Uani 1 1 d . . . . .
H12 H -0.723743 -1.029954 -0.583488 0.033 Uiso 1 1 calc R . . . .
C13 C -0.8583(6) -1.2999(5) -0.6166(3) 0.0298(14) Uani 1 1 d . . . . .
C14 C -0.6006(6) -0.9322(5) -0.2540(2) 0.0264(14) Uani 1 1 d . . . . .
H14 H -0.658231 -0.989768 -0.234316 0.032 Uiso 1 1 calc R . . . .
C15 C -0.8687(6) -0.6638(5) -0.3686(3) 0.0329(14) Uani 1 1 d . . . . .
H15A H -0.962379 -0.652453 -0.357888 0.040 Uiso 1 1 calc R . . . .
H15B H -0.818278 -0.649356 -0.326502 0.040 Uiso 1 1 calc R . . . .
C16 C -1.0736(7) -1.3287(6) -0.5618(3) 0.0417(16) Uani 1 1 d . . . . .
H16 H -1.148268 -1.377440 -0.553443 0.050 Uiso 1 1 calc R . . . .
C17 C -0.7540(5) -0.8128(5) -0.4559(3) 0.0220(12) Uani 1 1 d . . . . .
C18 C -0.6454(6) -0.8574(5) -0.3083(3) 0.0241(13) Uani 1 1 d . . . . .
C19 C -0.8458(5) -0.8006(5) -0.3928(3) 0.0223(12) Uani 1 1 d . . . . .
C20 C -0.4289(5) -0.7612(5) -0.3134(3) 0.0272(13) Uani 1 1 d . . . . .
H20 H -0.370653 -0.704789 -0.333569 0.033 Uiso 1 1 calc R . . . .
C21 C -1.0636(6) -1.2091(5) -0.5320(3) 0.0370(16) Uani 1 1 d . . . . .
H21 H -1.131220 -1.180526 -0.503163 0.044 Uiso 1 1 calc R . . . .
C22 C -0.6422(7) -1.2757(6) -0.6707(3) 0.0396(16) Uani 1 1 d . . . . .
H22 H -0.573626 -1.307232 -0.697951 0.048 Uiso 1 1 calc R . . . .
C23 C -0.7530(6) -1.3446(6) -0.6575(3) 0.0357(16) Uani 1 1 d . . . . .
H23 H -0.759122 -1.423669 -0.676184 0.043 Uiso 1 1 calc R . . . .
C24 C -0.9791(6) -0.9914(5) -0.4401(3) 0.0297(14) Uani 1 1 d . . . . .
H24A H -0.908930 -1.035778 -0.416071 0.036 Uiso 1 1 calc R . . . .
H24B H -1.063038 -1.030520 -0.428310 0.036 Uiso 1 1 calc R . . . .
C26 C -0.6331(6) -1.1560(6) -0.6424(3) 0.0365(15) Uani 1 1 d . . . . .
H26 H -0.558025 -1.108190 -0.651338 0.044 Uiso 1 1 calc R . . . .
C27 C -0.9557(6) -1.1350(5) -0.5453(3) 0.0258(13) Uani 1 1 d . . . . .
C28 C -0.8364(6) -0.6143(6) -0.4944(3) 0.0430(17) Uani 1 1 d . . . . .
H28A H -0.928233 -0.636151 -0.504299 0.052 Uiso 1 1 calc R . . . .
H28B H -0.809492 -0.550412 -0.526755 0.052 Uiso 1 1 calc R . . . .
C29 C -0.9728(7) -1.3718(6) -0.6028(3) 0.0400(17) Uani 1 1 d . . . . .
H29 H -0.979798 -1.450304 -0.622081 0.048 Uiso 1 1 calc R . . . .
C0AA C -0.8266(8) -0.5673(6) -0.4239(3) 0.052(2) Uani 1 1 d . . . . .
H0AA H -0.882796 -0.494732 -0.419470 0.063 Uiso 1 1 calc R . . . .
H0AB H -0.735325 -0.542076 -0.415089 0.063 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 C2 1.893(5) . ?
O1 C17 1.199(6) . ?
C2 C11 1.384(8) . ?
C2 C20 1.388(7) . ?
O3 C4 1.218(6) . ?
C4 C18 1.509(8) . ?
C4 C19 1.546(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C19 1.551(7) . ?
C5 C24 1.527(7) . ?
C6 H6 0.9300 . ?
C6 C18 1.383(7) . ?
C6 C20 1.385(7) . ?
O7 C17 1.343(6) . ?
O7 C28 1.446(6) . ?
C8 C12 1.409(7) . ?
C8 C13 1.436(8) . ?
C8 C27 1.427(8) . ?
O9 C10 1.214(6) . ?
C10 C24 1.520(7) . ?
C10 C27 1.505(7) . ?
C11 H11 0.9300 . ?
C11 C14 1.388(7) . ?
C12 H12 0.9300 . ?
C12 C26 1.365(8) . ?
C13 C23 1.404(8) . ?
C13 C29 1.412(8) . ?
C14 H14 0.9300 . ?
C14 C18 1.398(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C19 1.568(7) . ?
C15 C0AA 1.551(8) . ?
C16 H16 0.9300 . ?
C16 C21 1.419(8) . ?
C16 C29 1.365(9) . ?
C17 C19 1.532(7) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C21 C27 1.371(8) . ?
C22 H22 0.9300 . ?
C22 C23 1.362(8) . ?
C22 C26 1.408(8) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C26 H26 0.9300 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C0AA 1.455(8) . ?
C29 H29 0.9300 . ?
C0AA H0AA 0.9700 . ?
C0AA H0AB 0.9700 . ?

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 C2 Br1 119.3(4) . . ?
C11 C2 C20 121.4(5) . . ?
C20 C2 Br1 119.3(4) . . ?
O3 C4 C18 119.3(5) . . ?
O3 C4 C19 119.4(5) . . ?
C18 C4 C19 121.2(5) . . ?
H5A C5 H5B 107.3 . . ?
C19 C5 H5A 108.1 . . ?
C19 C5 H5B 108.1 . . ?
C24 C5 H5A 108.1 . . ?
C24 C5 H5B 108.1 . . ?
C24 C5 C19 116.9(5) . . ?
C18 C6 H6 119.5 . . ?
C18 C6 C20 121.0(5) . . ?
C20 C6 H6 119.5 . . ?
C17 O7 C28 120.1(4) . . ?
C12 C8 C13 117.8(5) . . ?
C12 C8 C27 124.1(5) . . ?
C27 C8 C13 118.1(5) . . ?
O9 C10 C24 122.9(5) . . ?
O9 C10 C27 121.0(5) . . ?
C27 C10 C24 116.1(5) . . ?
C2 C11 H11 120.6 . . ?
C2 C11 C14 118.7(5) . . ?
C14 C11 H11 120.6 . . ?
C8 C12 H12 119.4 . . ?
C26 C12 C8 121.2(6) . . ?
C26 C12 H12 119.4 . . ?
C23 C13 C8 118.9(6) . . ?
C23 C13 C29 121.9(6) . . ?
C29 C13 C8 119.1(6) . . ?
C11 C14 H14 119.6 . . ?
C11 C14 C18 120.9(6) . . ?
C18 C14 H14 119.6 . . ?
H15A C15 H15B 107.8 . . ?
C19 C15 H15A 109.0 . . ?
C19 C15 H15B 109.0 . . ?
C0AA C15 H15A 109.0 . . ?
C0AA C15 H15B 109.0 . . ?
C0AA C15 C19 113.0(5) . . ?
C21 C16 H16 120.2 . . ?
C29 C16 H16 120.2 . . ?
C29 C16 C21 119.6(6) . . ?
O1 C17 O7 119.0(5) . . ?
O1 C17 C19 122.0(5) . . ?
O7 C17 C19 119.0(4) . . ?
C6 C18 C4 124.1(5) . . ?
C6 C18 C14 119.0(5) . . ?
C14 C18 C4 116.9(5) . . ?
C4 C19 C5 108.4(5) . . ?
C4 C19 C15 108.8(4) . . ?
C5 C19 C15 109.2(4) . . ?
C17 C19 C4 109.5(4) . . ?
C17 C19 C5 106.8(4) . . ?
C17 C19 C15 114.0(4) . . ?
C2 C20 H20 120.5 . . ?
C6 C20 C2 119.0(5) . . ?
C6 C20 H20 120.5 . . ?
C16 C21 H21 119.6 . . ?
C27 C21 C16 120.8(6) . . ?
C27 C21 H21 119.6 . . ?
C23 C22 H22 120.6 . . ?
C23 C22 C26 118.9(6) . . ?
C26 C22 H22 120.6 . . ?
C13 C23 H23 119.0 . . ?
C22 C23 C13 122.1(6) . . ?
C22 C23 H23 119.0 . . ?
C5 C24 H24A 108.5 . . ?
C5 C24 H24B 108.5 . . ?
C10 C24 C5 115.1(5) . . ?
C10 C24 H24A 108.5 . . ?
C10 C24 H24B 108.5 . . ?
H24A C24 H24B 107.5 . . ?
C12 C26 C22 121.2(6) . . ?
C12 C26 H26 119.4 . . ?
C22 C26 H26 119.4 . . ?
C8 C27 C10 120.8(5) . . ?
C21 C27 C8 120.7(5) . . ?
C21 C27 C10 118.3(5) . . ?
O7 C28 H28A 109.5 . . ?
O7 C28 H28B 109.5 . . ?
O7 C28 C0AA 110.7(5) . . ?
H28A C28 H28B 108.1 . . ?
C0AA C28 H28A 109.5 . . ?
C0AA C28 H28B 109.5 . . ?
C13 C29 H29 119.2 . . ?
C16 C29 C13 121.6(6) . . ?
C16 C29 H29 119.2 . . ?
C15 C0AA H0AA 109.0 . . ?
C15 C0AA H0AB 109.0 . . ?
C28 C0AA C15 112.9(5) . . ?
C28 C0AA H0AA 109.0 . . ?
C28 C0AA H0AB 109.0 . . ?
H0AA C0AA H0AB 107.8 . . ?

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
Br1 C2 C11 C14 -179.1(4) . . . . ?
Br1 C2 C20 C6 179.7(4) . . . . ?
O1 C17 C19 C4 28.8(7) . . . . ?
O1 C17 C19 C5 -88.3(6) . . . . ?
O1 C17 C19 C15 151.0(5) . . . . ?
C2 C11 C14 C18 0.1(8) . . . . ?
O3 C4 C18 C6 -175.0(5) . . . . ?
O3 C4 C18 C14 4.9(7) . . . . ?
O3 C4 C19 C5 -14.4(7) . . . . ?
O3 C4 C19 C15 104.3(5) . . . . ?
O3 C4 C19 C17 -130.6(5) . . . . ?
O7 C17 C19 C4 -153.4(4) . . . . ?
O7 C17 C19 C5 89.4(5) . . . . ?
O7 C17 C19 C15 -31.2(6) . . . . ?
O7 C28 C0AA C15 -59.5(7) . . . . ?
C8 C12 C26 C22 -0.6(9) . . . . ?
C8 C13 C23 C22 -0.1(8) . . . . ?
C8 C13 C29 C16 -1.0(8) . . . . ?
O9 C10 C24 C5 -1.4(8) . . . . ?
O9 C10 C27 C8 53.7(7) . . . . ?
O9 C10 C27 C21 -122.7(6) . . . . ?
C11 C2 C20 C6 1.3(9) . . . . ?
C11 C14 C18 C4 -179.9(5) . . . . ?
C11 C14 C18 C6 0.0(8) . . . . ?
C12 C8 C13 C23 -0.1(7) . . . . ?
C12 C8 C13 C29 179.5(5) . . . . ?
C12 C8 C27 C10 5.7(8) . . . . ?
C12 C8 C27 C21 -178.0(5) . . . . ?
C13 C8 C12 C26 0.5(8) . . . . ?
C13 C8 C27 C10 -175.4(4) . . . . ?
C13 C8 C27 C21 0.9(8) . . . . ?
C16 C21 C27 C8 -2.0(9) . . . . ?
C16 C21 C27 C10 174.4(5) . . . . ?
C17 O7 C28 C0AA 46.7(7) . . . . ?
C18 C4 C19 C5 168.6(4) . . . . ?
C18 C4 C19 C15 -72.7(6) . . . . ?
C18 C4 C19 C17 52.5(6) . . . . ?
C18 C6 C20 C2 -1.3(8) . . . . ?
C19 C4 C18 C6 2.0(8) . . . . ?
C19 C4 C18 C14 -178.1(4) . . . . ?
C19 C5 C24 C10 -87.9(6) . . . . ?
C19 C15 C0AA C28 27.9(8) . . . . ?
C20 C2 C11 C14 -0.7(9) . . . . ?
C20 C6 C18 C4 -179.5(5) . . . . ?
C20 C6 C18 C14 0.6(8) . . . . ?
C21 C16 C29 C13 -0.1(9) . . . . ?
C23 C13 C29 C16 178.7(5) . . . . ?
C23 C22 C26 C12 0.4(9) . . . . ?
C24 C5 C19 C4 -62.9(6) . . . . ?
C24 C5 C19 C15 178.7(4) . . . . ?
C24 C5 C19 C17 55.0(6) . . . . ?
C24 C10 C27 C8 -128.5(5) . . . . ?
C24 C10 C27 C21 55.1(7) . . . . ?
C26 C22 C23 C13 0.0(9) . . . . ?
C27 C8 C12 C26 179.3(5) . . . . ?
C27 C8 C13 C23 -179.0(5) . . . . ?
C27 C8 C13 C29 0.6(7) . . . . ?
C27 C10 C24 C5 -179.2(5) . . . . ?
C28 O7 C17 O1 177.9(5) . . . . ?
C28 O7 C17 C19 0.0(7) . . . . ?
C29 C13 C23 C22 -179.8(5) . . . . ?
C29 C16 C21 C27 1.6(9) . . . . ?
C0AA C15 C19 C4 138.1(5) . . . . ?
C0AA C15 C19 C5 -103.7(6) . . . . ?
C0AA C15 C19 C17 15.6(7) . . . . ?

_olex2_date_sample_data_collection 2019-04-15
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xuyl_0218
_database_code_depnum_ccdc_archive 'CCDC 2011408'
loop_
_audit_author_name
_audit_author_address
'Yanli Xu'
;Lan Zhou University
China
;
_audit_update_record             
;
2020-06-22 deposited with the CCDC.	2021-01-22 downloaded from the CCDC.
;
_audit_creation_date             2020-05-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C25 H23 Cl N2 O3'
_chemical_formula_sum            'C25 H23 Cl N2 O3'
_chemical_formula_weight         434.90
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   7.04410(19)
_cell_length_b                   16.2447(4)
_cell_length_c                   18.7200(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2142.11(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1999
_cell_measurement_temperature    293.44(10)
_cell_measurement_theta_max      68.7660
_cell_measurement_theta_min      5.4380
_exptl_absorpt_coefficient_mu    1.823
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5081
_diffrn_reflns_theta_full        66.56
_diffrn_reflns_theta_max         66.56
_diffrn_reflns_theta_min         3.60
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.44(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0367
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     97.00 126.00   1.00    1.00    --   54.00  38.00 -90.00   29
  2  ω    110.00 136.00   1.00    1.00    --  108.00  93.00 -28.00   26
  3  ω    139.00 165.00   1.00    1.00    --  108.00 107.00  60.00   26
  4  ω    104.00 162.00   1.00    1.00    --  108.00  38.00 150.00   58
  5  ω     48.00 122.00   1.00    1.00    --   54.00  57.00 150.00   74
  6  ω     48.00 115.00   1.00    1.00    --  108.00-111.00 -90.00   67
  7  ω     57.00 111.00   1.00    1.00    --   54.00-125.00-150.00   54
  8  ω     12.00  51.00   1.00    1.00    --    0.00  57.00-180.00   39
  9  ω    -20.00  17.00   1.00    1.00    --    0.00 -57.00  30.00   37
 10  ω    -57.00 -29.00   1.00    1.00    --    0.00 -57.00  30.00   28
 11  ω     88.00 175.00   1.00    1.00    --  108.00  63.00-150.00   87
 12  ω     40.00 110.00   1.00    1.00    --  108.00-111.00 120.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2080368000
_diffrn_orient_matrix_UB_12      0.0278815000
_diffrn_orient_matrix_UB_13      0.0076669000
_diffrn_orient_matrix_UB_21      0.0421897000
_diffrn_orient_matrix_UB_22      -0.0314179000
_diffrn_orient_matrix_UB_23      -0.0760989000
_diffrn_orient_matrix_UB_31      -0.0528809000
_diffrn_orient_matrix_UB_32      0.0848722000
_diffrn_orient_matrix_UB_33      -0.0306369000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2793
_reflns_number_total             3222
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0464P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1031
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C23(H23A,H23B), C12(H12A,H12B), C13(H13A,H13B), C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C2(H2), C9(H9), C20(H20), C3(H3A), C6(H6), C22(H22), C21(H21),
  C4(H4), C19(H19), C8(H8)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.17972(12) 0.01057(5) 0.70199(5) 0.0682(3) Uani 1 d . . .
O3 O -0.6826(4) 0.16378(15) 0.97443(12) 0.0683(7) Uani 1 d . . .
H3 H -0.6802 0.1962 1.0080 0.102 Uiso 1 calc . . GR
O1 O -0.2048(3) 0.33444(12) 0.67491(13) 0.0653(6) Uani 1 d . . .
O2 O -0.1939(4) 0.24913(11) 0.89939(11) 0.0589(6) Uani 1 d . . .
N1 N -0.0040(4) 0.13525(15) 0.88778(13) 0.0572(7) Uani 1 d . . .
H1 H 0.0802 0.1486 0.9190 0.069 Uiso 1 calc . . R
N2 N 0.0034(4) 0.06201(13) 0.84778(13) 0.0509(6) Uani 1 d . . .
C7 C 0.0888(8) 0.4611(2) 0.44196(19) 0.0824(13) Uani 1 d . . .
H7 H 0.0893 0.4958 0.4024 0.099 Uiso 1 calc . . R
C1 C 0.0890(4) 0.29852(15) 0.61979(13) 0.0405(6) Uani 1 d . . .
C16 C -0.1444(4) 0.06120(14) 0.80750(13) 0.0380(6) Uani 1 d . . .
C24 C -0.4984(5) 0.06879(17) 0.90693(17) 0.0560(8) Uani 1 d . . .
H24A H -0.6122 0.0360 0.9007 0.067 Uiso 1 calc . . R
H24B H -0.3919 0.0311 0.9102 0.067 Uiso 1 calc . . R
C10 C 0.0834(5) 0.35611(16) 0.56110(14) 0.0447(7) Uani 1 d . . .
C18 C -0.0388(4) -0.03794(15) 0.71167(15) 0.0457(7) Uani 1 d . . .
C17 C -0.1769(4) -0.00883(14) 0.75866(14) 0.0382(6) Uani 1 d . . .
C23 C -0.4720(4) 0.12241(16) 0.84052(15) 0.0458(7) Uani 1 d . . .
H23A H -0.5297 0.1756 0.8498 0.055 Uiso 1 calc . . R
H23B H -0.5416 0.0973 0.8015 0.055 Uiso 1 calc . . R
C15 C -0.1554(5) 0.18223(15) 0.87248(14) 0.0447(7) Uani 1 d . . .
C12 C -0.0766(4) 0.20904(16) 0.71541(15) 0.0457(7) Uani 1 d . . .
H12A H -0.0344 0.1623 0.6873 0.055 Uiso 1 calc . . R
H12B H 0.0136 0.2167 0.7540 0.055 Uiso 1 calc . . R
C2 C 0.2525(5) 0.25504(19) 0.63097(16) 0.0531(7) Uani 1 d . . .
H2 H 0.2558 0.2175 0.6685 0.064 Uiso 1 calc . . R
C9 C -0.0797(6) 0.40315(17) 0.54209(17) 0.0588(9) Uani 1 d . . .
H9 H -0.1894 0.3991 0.5695 0.071 Uiso 1 calc . . R
C20 C -0.2449(6) -0.14447(17) 0.66967(19) 0.0682(10) Uani 1 d . . .
H20 H -0.2678 -0.1893 0.6399 0.082 Uiso 1 calc . . R
C11 C -0.0756(4) 0.28548(15) 0.66837(14) 0.0422(6) Uani 1 d . . .
C3 C 0.4152(5) 0.2641(2) 0.58883(19) 0.0638(9) Uani 1 d . . .
H3A H 0.5242 0.2338 0.5986 0.077 Uiso 1 calc . . R
C14 C -0.2676(4) 0.13691(14) 0.81570(13) 0.0379(6) Uani 1 d . . .
C5 C 0.2478(5) 0.36382(18) 0.51810(15) 0.0528(8) Uani 1 d . . .
C6 C 0.2458(6) 0.4183(2) 0.45853(18) 0.0694(10) Uani 1 d . . .
H6 H 0.3544 0.4242 0.4308 0.083 Uiso 1 calc . . R
C22 C -0.3502(5) -0.05041(15) 0.75935(17) 0.0502(7) Uani 1 d . . .
H22 H -0.4451 -0.0332 0.7905 0.060 Uiso 1 calc . . R
C21 C -0.3838(6) -0.11715(17) 0.71440(19) 0.0639(9) Uani 1 d . . .
H21 H -0.5015 -0.1431 0.7149 0.077 Uiso 1 calc . . R
C13 C -0.2698(4) 0.18961(15) 0.74705(14) 0.0438(7) Uani 1 d . . .
H13A H -0.3444 0.1610 0.7112 0.053 Uiso 1 calc . . R
H13B H -0.3338 0.2411 0.7575 0.053 Uiso 1 calc . . R
C4 C 0.4109(5) 0.3181(2) 0.53326(17) 0.0619(9) Uani 1 d . . .
H4 H 0.5183 0.3247 0.5049 0.074 Uiso 1 calc . . R
C25 C -0.5139(5) 0.1141(2) 0.97551(16) 0.0610(9) Uani 1 d . . .
H25A H -0.5197 0.0755 1.0149 0.073 Uiso 1 calc . . R
H25B H -0.4033 0.1489 0.9821 0.073 Uiso 1 calc . . R
C19 C -0.0703(6) -0.10582(16) 0.66834(17) 0.0577(9) Uani 1 d . . .
H19 H 0.0255 -0.1252 0.6386 0.069 Uiso 1 calc . . R
C8 C -0.0765(7) 0.4542(2) 0.48387(19) 0.0793(13) Uani 1 d . . .
H8 H -0.1840 0.4845 0.4720 0.095 Uiso 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 C18 1.739(3) . ?
O3 H3 0.8200 . ?
O3 C25 1.436(4) . ?
O1 C11 1.215(3) . ?
O2 C15 1.228(3) . ?
N1 H1 0.8600 . ?
N1 N2 1.407(3) . ?
N1 C15 1.342(4) . ?
N2 C16 1.286(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.343(6) . ?
C7 C8 1.409(6) . ?
C1 C10 1.444(3) . ?
C1 C2 1.367(4) . ?
C1 C11 1.489(4) . ?
C16 C17 1.477(3) . ?
C16 C14 1.513(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C23 1.529(4) . ?
C24 C25 1.484(4) . ?
C10 C9 1.425(5) . ?
C10 C5 1.416(4) . ?
C18 C17 1.395(4) . ?
C18 C19 1.387(4) . ?
C17 C22 1.395(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C14 1.532(4) . ?
C15 C14 1.515(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.522(3) . ?
C12 C13 1.518(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.399(5) . ?
C9 H9 0.9300 . ?
C9 C8 1.370(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.362(5) . ?
C20 C19 1.381(5) . ?
C3 H3A 0.9300 . ?
C3 C4 1.361(5) . ?
C14 C13 1.544(3) . ?
C5 C6 1.423(4) . ?
C5 C4 1.397(5) . ?
C6 H6 0.9300 . ?
C22 H22 0.9300 . ?
C22 C21 1.393(4) . ?
C21 H21 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C4 H4 0.9300 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C19 H19 0.9300 . ?
C8 H8 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
C25 O3 H3 109.5 . . ?
N2 N1 H1 123.3 . . ?
C15 N1 H1 123.3 . . ?
C15 N1 N2 113.4(2) . . ?
C16 N2 N1 106.9(2) . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.7(3) . . ?
C8 C7 H7 119.6 . . ?
C10 C1 C11 122.4(3) . . ?
C2 C1 C10 118.3(3) . . ?
C2 C1 C11 119.3(2) . . ?
N2 C16 C17 119.8(2) . . ?
N2 C16 C14 113.4(2) . . ?
C17 C16 C14 126.9(2) . . ?
H24A C24 H24B 107.5 . . ?
C23 C24 H24A 108.4 . . ?
C23 C24 H24B 108.4 . . ?
C25 C24 H24A 108.4 . . ?
C25 C24 H24B 108.4 . . ?
C25 C24 C23 115.4(2) . . ?
C9 C10 C1 124.1(3) . . ?
C5 C10 C1 117.9(3) . . ?
C5 C10 C9 118.0(3) . . ?
C17 C18 Cl1 122.0(2) . . ?
C19 C18 Cl1 116.2(3) . . ?
C19 C18 C17 121.8(3) . . ?
C18 C17 C16 122.9(3) . . ?
C22 C17 C16 120.2(3) . . ?
C22 C17 C18 116.9(2) . . ?
C24 C23 H23A 108.1 . . ?
C24 C23 H23B 108.1 . . ?
C24 C23 C14 116.6(3) . . ?
H23A C23 H23B 107.3 . . ?
C14 C23 H23A 108.1 . . ?
C14 C23 H23B 108.1 . . ?
O2 C15 N1 126.2(3) . . ?
O2 C15 C14 127.1(3) . . ?
N1 C15 C14 106.7(2) . . ?
H12A C12 H12B 107.7 . . ?
C11 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C13 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C13 C12 C11 113.5(2) . . ?
C1 C2 H2 118.3 . . ?
C1 C2 C3 123.3(3) . . ?
C3 C2 H2 118.3 . . ?
C10 C9 H9 119.7 . . ?
C8 C9 C10 120.7(4) . . ?
C8 C9 H9 119.7 . . ?
C21 C20 H20 119.9 . . ?
C21 C20 C19 120.2(3) . . ?
C19 C20 H20 119.9 . . ?
O1 C11 C1 123.5(2) . . ?
O1 C11 C12 118.2(3) . . ?
C1 C11 C12 118.2(2) . . ?
C2 C3 H3A 120.6 . . ?
C4 C3 C2 118.7(3) . . ?
C4 C3 H3A 120.6 . . ?
C16 C14 C23 116.4(2) . . ?
C16 C14 C15 99.6(2) . . ?
C16 C14 C13 111.9(2) . . ?
C23 C14 C13 109.1(2) . . ?
C15 C14 C23 110.6(2) . . ?
C15 C14 C13 108.7(2) . . ?
C10 C5 C6 119.5(3) . . ?
C4 C5 C10 120.7(3) . . ?
C4 C5 C6 119.8(3) . . ?
C7 C6 C5 120.8(4) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C17 C22 H22 119.3 . . ?
C17 C22 C21 121.4(3) . . ?
C21 C22 H22 119.3 . . ?
C20 C21 C22 120.2(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C12 C13 C14 115.5(2) . . ?
C12 C13 H13A 108.4 . . ?
C12 C13 H13B 108.4 . . ?
C14 C13 H13A 108.4 . . ?
C14 C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
O3 C25 C24 109.1(3) . . ?
O3 C25 H25A 109.9 . . ?
O3 C25 H25B 109.9 . . ?
C24 C25 H25A 109.9 . . ?
C24 C25 H25B 109.9 . . ?
H25A C25 H25B 108.3 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.6(3) . . ?
C20 C19 H19 120.2 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.3(4) . . ?
C9 C8 H8 119.8 . . ?

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 C18 C17 C16 -4.6(4) . . . . ?
Cl1 C18 C17 C22 177.0(2) . . . . ?
Cl1 C18 C19 C20 -175.9(3) . . . . ?
O2 C15 C14 C16 -180.0(3) . . . . ?
O2 C15 C14 C23 -56.9(3) . . . . ?
O2 C15 C14 C13 62.9(3) . . . . ?
N1 N2 C16 C17 -180.0(2) . . . . ?
N1 N2 C16 C14 1.1(3) . . . . ?
N1 C15 C14 C16 0.3(3) . . . . ?
N1 C15 C14 C23 123.4(2) . . . . ?
N1 C15 C14 C13 -116.8(2) . . . . ?
N2 N1 C15 O2 -179.4(3) . . . . ?
N2 N1 C15 C14 0.3(3) . . . . ?
N2 C16 C17 C18 -50.7(4) . . . . ?
N2 C16 C17 C22 127.7(3) . . . . ?
N2 C16 C14 C23 -119.8(3) . . . . ?
N2 C16 C14 C15 -0.9(3) . . . . ?
N2 C16 C14 C13 113.8(3) . . . . ?
C1 C10 C9 C8 -177.4(3) . . . . ?
C1 C10 C5 C6 178.2(3) . . . . ?
C1 C10 C5 C4 -1.3(4) . . . . ?
C1 C2 C3 C4 -0.8(5) . . . . ?
C16 C17 C22 C21 -179.3(3) . . . . ?
C16 C14 C13 C12 -49.4(3) . . . . ?
C24 C23 C14 C16 50.4(3) . . . . ?
C24 C23 C14 C15 -62.4(3) . . . . ?
C24 C23 C14 C13 178.1(2) . . . . ?
C10 C1 C2 C3 0.6(4) . . . . ?
C10 C1 C11 O1 -19.5(4) . . . . ?
C10 C1 C11 C12 164.1(2) . . . . ?
C10 C9 C8 C7 -0.2(5) . . . . ?
C10 C5 C6 C7 -1.2(5) . . . . ?
C10 C5 C4 C3 1.1(5) . . . . ?
C18 C17 C22 C21 -0.9(4) . . . . ?
C17 C16 C14 C23 61.4(3) . . . . ?
C17 C16 C14 C15 -179.7(2) . . . . ?
C17 C16 C14 C13 -65.1(3) . . . . ?
C17 C18 C19 C20 2.1(4) . . . . ?
C17 C22 C21 C20 1.6(5) . . . . ?
C23 C24 C25 O3 64.2(4) . . . . ?
C23 C14 C13 C12 -179.7(2) . . . . ?
C15 N1 N2 C16 -0.9(3) . . . . ?
C15 C14 C13 C12 59.6(3) . . . . ?
C2 C1 C10 C9 177.8(3) . . . . ?
C2 C1 C10 C5 0.4(4) . . . . ?
C2 C1 C11 O1 160.1(3) . . . . ?
C2 C1 C11 C12 -16.3(4) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C9 C10 C5 C6 0.7(4) . . . . ?
C9 C10 C5 C4 -178.8(3) . . . . ?
C11 C1 C10 C9 -2.6(4) . . . . ?
C11 C1 C10 C5 180.0(2) . . . . ?
C11 C1 C2 C3 -179.0(3) . . . . ?
C11 C12 C13 C14 -157.0(2) . . . . ?
C14 C16 C17 C18 128.0(3) . . . . ?
C14 C16 C17 C22 -53.6(4) . . . . ?
C5 C10 C9 C8 0.0(4) . . . . ?
C6 C7 C8 C9 -0.3(6) . . . . ?
C6 C5 C4 C3 -178.4(3) . . . . ?
C21 C20 C19 C18 -1.4(5) . . . . ?
C13 C12 C11 O1 19.1(4) . . . . ?
C13 C12 C11 C1 -164.3(2) . . . . ?
C4 C5 C6 C7 178.3(3) . . . . ?
C25 C24 C23 C14 94.5(3) . . . . ?
C19 C18 C17 C16 177.4(2) . . . . ?
C19 C18 C17 C22 -1.0(4) . . . . ?
C19 C20 C21 C22 -0.4(5) . . . . ?
C8 C7 C6 C5 1.0(6) . . . . ?

_olex2_date_sample_data_collection 2020-05-20
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.620
_oxdiff_exptl_absorpt_empirical_full_min 0.794
