# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_003DER
_database_code_depnum_ccdc_archive 'CCDC 2227147'
loop_
_audit_author_name
_audit_author_address
'Jeng-Liang Han'
;National Chung Hsing University
Taiwan
;
_audit_update_record             
;
2022-12-17 deposited with the CCDC.	2023-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C42 H29 Br2 N O5'
_chemical_formula_sum            'C42 H29 Br2 N O5'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         787.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   22.2390(6)
_cell_length_b                   9.4028(3)
_cell_length_c                   16.3805(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.6868(13)
_cell_angle_gamma                90
_cell_volume                     3423.82(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9395
_cell_measurement_theta_min      2.648
_cell_measurement_theta_max      27.834
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_F_000             1592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    2.416
_shelx_estimated_absorpt_T_min   0.430
_shelx_estimated_absorpt_T_max   0.670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5887
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            70351
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.626
_diffrn_reflns_theta_max         27.913
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8177
_reflns_number_gt                6692
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0361P)²+3.8608P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8177
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0855
_refine_ls_wR_factor_gt          0.0792
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.50025(2) 0.27478(3) 0.47763(2) 0.03289(7) Uani 1 1 d . . . . .
Br2 Br 0.75137(2) 0.93013(3) 0.37277(2) 0.03636(8) Uani 1 1 d . . . . .
O1 O 0.20360(7) 0.4619(2) 0.43364(10) 0.0291(4) Uani 1 1 d . . . . .
O2 O 0.24162(6) 0.56758(16) 0.32304(9) 0.0195(3) Uani 1 1 d . . . . .
O3 O 0.14176(7) 0.37781(17) 0.27045(10) 0.0265(3) Uani 1 1 d . . . . .
O4 O 0.44751(6) 0.93129(16) 0.32144(9) 0.0212(3) Uani 1 1 d . . . . .
O5 O 0.46428(7) 0.70217(16) 0.28873(10) 0.0255(3) Uani 1 1 d . . . . .
N N 0.08889(8) 0.5871(2) 0.25297(11) 0.0214(4) Uani 1 1 d . . . . .
C1 C 0.35723(9) 0.4947(2) 0.37129(12) 0.0192(4) Uani 1 1 d . . . . .
H1A H 0.351568 0.570535 0.333519 0.023 Uiso 1 1 calc R U . . .
C2 C 0.41492(9) 0.4478(2) 0.39200(13) 0.0207(4) Uani 1 1 d . . . . .
H2A H 0.449112 0.491899 0.369476 0.025 Uiso 1 1 calc R U . . .
C3 C 0.42147(9) 0.3356(2) 0.44614(13) 0.0204(4) Uani 1 1 d . . . . .
C4 C 0.37282(10) 0.2679(2) 0.47953(14) 0.0253(5) Uani 1 1 d . . . . .
H4A H 0.378589 0.189522 0.515477 0.030 Uiso 1 1 calc R U . . .
C5 C 0.31546(10) 0.3167(2) 0.45957(13) 0.0249(5) Uani 1 1 d . . . . .
H5A H 0.281440 0.272453 0.482469 0.030 Uiso 1 1 calc R U . . .
C6 C 0.30773(9) 0.4304(2) 0.40598(12) 0.0184(4) Uani 1 1 d . . . . .
C7 C 0.24563(9) 0.4842(2) 0.39092(12) 0.0194(4) Uani 1 1 d . . . . .
C8 C 0.18406(9) 0.6118(2) 0.30162(12) 0.0183(4) Uani 1 1 d . . . . .
C9 C 0.16316(9) 0.7441(2) 0.29877(12) 0.0182(4) Uani 1 1 d . . . . .
C10 C 0.09891(9) 0.7373(2) 0.26756(14) 0.0209(4) Uani 1 1 d . . . . .
H10A H 0.071156 0.774279 0.308692 0.025 Uiso 1 1 calc R U . . .
H10B H 0.093345 0.792689 0.216487 0.025 Uiso 1 1 calc R U . . .
C11 C 0.13758(9) 0.5067(2) 0.27371(12) 0.0196(4) Uani 1 1 d . . . . .
C12 C 0.03051(9) 0.5293(3) 0.22893(13) 0.0239(4) Uani 1 1 d . . . . .
H12A H 0.036075 0.432679 0.206397 0.029 Uiso 1 1 calc R U . . .
H12B H 0.012474 0.589335 0.184992 0.029 Uiso 1 1 calc R U . . .
C13 C -0.01261(9) 0.5213(2) 0.29854(13) 0.0209(4) Uani 1 1 d . . . . .
C14 C -0.06575(10) 0.5983(3) 0.29610(16) 0.0280(5) Uani 1 1 d . . . . .
H14A H -0.074586 0.660317 0.251553 0.034 Uiso 1 1 calc R U . . .
C15 C -0.10620(11) 0.5848(3) 0.35894(19) 0.0389(7) Uani 1 1 d . . . . .
H15A H -0.142665 0.637528 0.357117 0.047 Uiso 1 1 calc R U . . .
C16 C -0.09343(13) 0.4951(3) 0.42389(18) 0.0425(7) Uani 1 1 d . . . . .
H16A H -0.121349 0.485205 0.466321 0.051 Uiso 1 1 calc R U . . .
C17 C -0.03984(12) 0.4193(3) 0.42724(15) 0.0363(6) Uani 1 1 d . . . . .
H17A H -0.030935 0.358168 0.472181 0.044 Uiso 1 1 calc R U . . .
C18 C 0.00064(10) 0.4327(3) 0.36503(14) 0.0260(5) Uani 1 1 d . . . . .
H18A H 0.037489 0.381578 0.367629 0.031 Uiso 1 1 calc R U . . .
C19 C 0.19069(9) 0.8860(2) 0.32067(12) 0.0179(4) Uani 1 1 d . . . . .
H19A H 0.177731 0.952282 0.275780 0.022 Uiso 1 1 calc R U . . .
C20 C 0.16350(9) 0.9457(2) 0.39844(13) 0.0195(4) Uani 1 1 d . . . . .
C21 C 0.15530(10) 1.0921(2) 0.40394(14) 0.0252(5) Uani 1 1 d . . . . .
H21A H 0.167484 1.151797 0.360646 0.030 Uiso 1 1 calc R U . . .
C22 C 0.12957(11) 1.1516(3) 0.47184(16) 0.0317(5) Uani 1 1 d . . . . .
H22A H 0.123897 1.251558 0.475016 0.038 Uiso 1 1 calc R U . . .
C23 C 0.11203(11) 1.0640(3) 0.53556(16) 0.0353(6) Uani 1 1 d . . . . .
H23A H 0.093866 1.104170 0.582013 0.042 Uiso 1 1 calc R U . . .
C24 C 0.12108(12) 0.9185(3) 0.53113(15) 0.0335(6) Uani 1 1 d . . . . .
H24A H 0.110044 0.858992 0.575088 0.040 Uiso 1 1 calc R U . . .
C25 C 0.14646(11) 0.8596(3) 0.46192(14) 0.0279(5) Uani 1 1 d . . . . .
H25A H 0.152022 0.759663 0.458508 0.033 Uiso 1 1 calc R U . . .
C26 C 0.25942(9) 0.8868(2) 0.32161(13) 0.0190(4) Uani 1 1 d . . . . .
C27 C 0.29320(9) 0.8993(2) 0.39286(13) 0.0229(4) Uani 1 1 d . . . . .
H27A H 0.273486 0.902211 0.443501 0.027 Uiso 1 1 calc R U . . .
C28 C 0.35661(10) 0.9079(2) 0.39243(13) 0.0235(4) Uani 1 1 d . . . . .
H28A H 0.379230 0.914430 0.442392 0.028 Uiso 1 1 calc R U . . .
C29 C 0.38503(9) 0.9067(2) 0.32024(13) 0.0199(4) Uani 1 1 d . . . . .
C30 C 0.35304(9) 0.8946(2) 0.24442(13) 0.0187(4) Uani 1 1 d . . . . .
C31 C 0.28922(9) 0.8828(2) 0.24544(13) 0.0187(4) Uani 1 1 d . . . . .
C32 C 0.25729(9) 0.8711(2) 0.16881(13) 0.0224(4) Uani 1 1 d . . . . .
H32A H 0.214799 0.860363 0.167819 0.027 Uiso 1 1 calc R U . . .
C33 C 0.28678(10) 0.8752(3) 0.09708(14) 0.0284(5) Uani 1 1 d . . . . .
H33A H 0.264562 0.867772 0.046831 0.034 Uiso 1 1 calc R U . . .
C34 C 0.34970(10) 0.8902(3) 0.09652(14) 0.0268(5) Uani 1 1 d . . . . .
H34A H 0.369632 0.894708 0.046080 0.032 Uiso 1 1 calc R U . . .
C35 C 0.38214(10) 0.8984(2) 0.16849(13) 0.0225(4) Uani 1 1 d . . . . .
H35A H 0.424686 0.906767 0.167712 0.027 Uiso 1 1 calc R U . . .
C36 C 0.48363(9) 0.8180(2) 0.30596(12) 0.0189(4) Uani 1 1 d . . . . .
C37 C 0.54837(9) 0.8550(2) 0.31451(12) 0.0184(4) Uani 1 1 d . . . . .
C38 C 0.59009(10) 0.7505(2) 0.29555(14) 0.0253(5) Uani 1 1 d . . . . .
H38A H 0.576617 0.662683 0.272977 0.030 Uiso 1 1 calc R U . . .
C39 C 0.65110(10) 0.7736(3) 0.30932(15) 0.0292(5) Uani 1 1 d . . . . .
H39A H 0.679648 0.702389 0.296693 0.035 Uiso 1 1 calc R U . . .
C40 C 0.66944(9) 0.9026(3) 0.34184(13) 0.0251(5) Uani 1 1 d . . . . .
C41 C 0.62895(10) 1.0106(2) 0.35761(13) 0.0232(4) Uani 1 1 d . . . . .
H41A H 0.642722 1.099927 0.377754 0.028 Uiso 1 1 calc R U . . .
C42 C 0.56803(10) 0.9861(2) 0.34354(13) 0.0214(4) Uani 1 1 d . . . . .
H42A H 0.539739 1.059210 0.353787 0.026 Uiso 1 1 calc R U . . .


_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 1.900(2) . ?
Br2 C40 1.894(2) . ?
O1 C7 1.203(3) . ?
O2 C7 1.361(2) . ?
O2 C8 1.382(2) . ?
O3 C11 1.217(3) . ?
O4 C36 1.362(3) . ?
O4 C29 1.408(2) . ?
O5 C36 1.202(3) . ?
N C11 1.356(3) . ?
N C10 1.449(3) . ?
N C12 1.451(3) . ?
C1 C6 1.392(3) . ?
C1 C2 1.389(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.383(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.382(3) . ?
C4 C5 1.385(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.391(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.485(3) . ?
C8 C9 1.328(3) . ?
C8 C11 1.492(3) . ?
C9 C10 1.505(3) . ?
C9 C19 1.507(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C12 C13 1.513(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.386(3) . ?
C13 C18 1.396(3) . ?
C14 C15 1.393(4) . ?
C14 H14A 0.9500 . ?
C15 C16 1.381(4) . ?
C15 H15A 0.9500 . ?
C16 C17 1.389(4) . ?
C16 H16A 0.9500 . ?
C17 C18 1.385(3) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 C26 1.528(3) . ?
C19 C20 1.533(3) . ?
C19 H19A 1.0000 . ?
C20 C25 1.379(3) . ?
C20 C21 1.392(3) . ?
C21 C22 1.384(3) . ?
C21 H21A 0.9500 . ?
C22 C23 1.394(4) . ?
C22 H22A 0.9500 . ?
C23 C24 1.385(4) . ?
C23 H23A 0.9500 . ?
C24 C25 1.396(3) . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9500 . ?
C26 C27 1.374(3) . ?
C26 C31 1.431(3) . ?
C27 C28 1.413(3) . ?
C27 H27A 0.9500 . ?
C28 C29 1.357(3) . ?
C28 H28A 0.9500 . ?
C29 C30 1.418(3) . ?
C30 C35 1.419(3) . ?
C30 C31 1.424(3) . ?
C31 C32 1.428(3) . ?
C32 C33 1.363(3) . ?
C32 H32A 0.9500 . ?
C33 C34 1.407(3) . ?
C33 H33A 0.9500 . ?
C34 C35 1.366(3) . ?
C34 H34A 0.9500 . ?
C35 H35A 0.9500 . ?
C36 C37 1.484(3) . ?
C37 C42 1.387(3) . ?
C37 C38 1.393(3) . ?
C38 C39 1.386(3) . ?
C38 H38A 0.9500 . ?
C39 C40 1.382(4) . ?
C39 H39A 0.9500 . ?
C40 C41 1.386(3) . ?
C41 C42 1.387(3) . ?
C41 H41A 0.9500 . ?
C42 H42A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 C8 114.76(15) . . ?
C36 O4 C29 117.14(16) . . ?
C11 N C10 112.63(17) . . ?
C11 N C12 124.11(19) . . ?
C10 N C12 122.80(18) . . ?
C6 C1 C2 119.89(19) . . ?
C6 C1 H1A 120.1 . . ?
C2 C1 H1A 120.1 . . ?
C3 C2 C1 118.53(19) . . ?
C3 C2 H2A 120.7 . . ?
C1 C2 H2A 120.7 . . ?
C4 C3 C2 122.42(19) . . ?
C4 C3 Br1 118.72(16) . . ?
C2 C3 Br1 118.85(16) . . ?
C3 C4 C5 118.7(2) . . ?
C3 C4 H4A 120.6 . . ?
C5 C4 H4A 120.6 . . ?
C4 C5 C6 119.9(2) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C1 C6 C5 120.48(19) . . ?
C1 C6 C7 121.81(19) . . ?
C5 C6 C7 117.64(18) . . ?
O1 C7 O2 122.85(19) . . ?
O1 C7 C6 125.38(19) . . ?
O2 C7 C6 111.73(17) . . ?
C9 C8 O2 127.71(19) . . ?
C9 C8 C11 111.78(18) . . ?
O2 C8 C11 120.44(18) . . ?
C8 C9 C10 107.47(18) . . ?
C8 C9 C19 132.95(18) . . ?
C10 C9 C19 119.57(18) . . ?
N C10 C9 103.71(17) . . ?
N C10 H10A 111.0 . . ?
C9 C10 H10A 111.0 . . ?
N C10 H10B 111.0 . . ?
C9 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
O3 C11 N 127.3(2) . . ?
O3 C11 C8 128.3(2) . . ?
N C11 C8 104.36(18) . . ?
N C12 C13 113.31(18) . . ?
N C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
N C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C18 119.7(2) . . ?
C14 C13 C12 120.7(2) . . ?
C18 C13 C12 119.6(2) . . ?
C13 C14 C15 120.0(2) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C15 C16 C17 120.1(2) . . ?
C15 C16 H16A 120.0 . . ?
C17 C16 H16A 120.0 . . ?
C16 C17 C18 120.0(3) . . ?
C16 C17 H17A 120.0 . . ?
C18 C17 H17A 120.0 . . ?
C17 C18 C13 120.1(2) . . ?
C17 C18 H18A 119.9 . . ?
C13 C18 H18A 119.9 . . ?
C9 C19 C26 113.98(17) . . ?
C9 C19 C20 110.78(16) . . ?
C26 C19 C20 114.12(17) . . ?
C9 C19 H19A 105.7 . . ?
C26 C19 H19A 105.7 . . ?
C20 C19 H19A 105.7 . . ?
C25 C20 C21 119.5(2) . . ?
C25 C20 C19 122.4(2) . . ?
C21 C20 C19 118.15(19) . . ?
C22 C21 C20 120.6(2) . . ?
C22 C21 H21A 119.7 . . ?
C20 C21 H21A 119.7 . . ?
C21 C22 C23 119.6(2) . . ?
C21 C22 H22A 120.2 . . ?
C23 C22 H22A 120.2 . . ?
C24 C23 C22 120.0(2) . . ?
C24 C23 H23A 120.0 . . ?
C22 C23 H23A 120.0 . . ?
C23 C24 C25 119.8(2) . . ?
C23 C24 H24A 120.1 . . ?
C25 C24 H24A 120.1 . . ?
C20 C25 C24 120.4(2) . . ?
C20 C25 H25A 119.8 . . ?
C24 C25 H25A 119.8 . . ?
C27 C26 C31 119.16(18) . . ?
C27 C26 C19 122.05(18) . . ?
C31 C26 C19 118.69(18) . . ?
C26 C27 C28 121.43(19) . . ?
C26 C27 H27A 119.3 . . ?
C28 C27 H27A 119.3 . . ?
C29 C28 C27 119.6(2) . . ?
C29 C28 H28A 120.2 . . ?
C27 C28 H28A 120.2 . . ?
C28 C29 O4 118.12(19) . . ?
C28 C29 C30 121.96(19) . . ?
O4 C29 C30 119.67(18) . . ?
C29 C30 C35 122.39(19) . . ?
C29 C30 C31 118.08(18) . . ?
C35 C30 C31 119.50(19) . . ?
C30 C31 C32 117.75(19) . . ?
C30 C31 C26 119.71(19) . . ?
C32 C31 C26 122.51(18) . . ?
C33 C32 C31 121.1(2) . . ?
C33 C32 H32A 119.5 . . ?
C31 C32 H32A 119.5 . . ?
C32 C33 C34 120.8(2) . . ?
C32 C33 H33A 119.6 . . ?
C34 C33 H33A 119.6 . . ?
C35 C34 C33 120.0(2) . . ?
C35 C34 H34A 120.0 . . ?
C33 C34 H34A 120.0 . . ?
C34 C35 C30 120.8(2) . . ?
C34 C35 H35A 119.6 . . ?
C30 C35 H35A 119.6 . . ?
O5 C36 O4 122.92(19) . . ?
O5 C36 C37 125.08(19) . . ?
O4 C36 C37 112.00(17) . . ?
C42 C37 C38 119.9(2) . . ?
C42 C37 C36 122.42(19) . . ?
C38 C37 C36 117.67(19) . . ?
C39 C38 C37 120.6(2) . . ?
C39 C38 H38A 119.7 . . ?
C37 C38 H38A 119.7 . . ?
C40 C39 C38 118.5(2) . . ?
C40 C39 H39A 120.8 . . ?
C38 C39 H39A 120.8 . . ?
C39 C40 C41 121.9(2) . . ?
C39 C40 Br2 119.59(17) . . ?
C41 C40 Br2 118.37(18) . . ?
C42 C41 C40 119.0(2) . . ?
C42 C41 H41A 120.5 . . ?
C40 C41 H41A 120.5 . . ?
C41 C42 C37 120.1(2) . . ?
C41 C42 H42A 120.0 . . ?
C37 C42 H42A 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.1(3) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C1 C2 C3 Br1 -177.96(16) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
Br1 C3 C4 C5 176.98(17) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C2 C1 C6 C5 -1.8(3) . . . . ?
C2 C1 C6 C7 175.01(19) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
C4 C5 C6 C7 -176.1(2) . . . . ?
C8 O2 C7 O1 -7.0(3) . . . . ?
C8 O2 C7 C6 174.96(17) . . . . ?
C1 C6 C7 O1 -158.8(2) . . . . ?
C5 C6 C7 O1 18.1(3) . . . . ?
C1 C6 C7 O2 19.2(3) . . . . ?
C5 C6 C7 O2 -163.86(19) . . . . ?
C7 O2 C8 C9 117.0(2) . . . . ?
C7 O2 C8 C11 -66.2(2) . . . . ?
O2 C8 C9 C10 176.90(19) . . . . ?
C11 C8 C9 C10 -0.1(2) . . . . ?
O2 C8 C9 C19 -3.9(4) . . . . ?
C11 C8 C9 C19 179.1(2) . . . . ?
C11 N C10 C9 1.9(2) . . . . ?
C12 N C10 C9 174.40(18) . . . . ?
C8 C9 C10 N -1.0(2) . . . . ?
C19 C9 C10 N 179.64(17) . . . . ?
C10 N C11 O3 177.7(2) . . . . ?
C12 N C11 O3 5.3(3) . . . . ?
C10 N C11 C8 -1.9(2) . . . . ?
C12 N C11 C8 -174.31(18) . . . . ?
C9 C8 C11 O3 -178.4(2) . . . . ?
O2 C8 C11 O3 4.4(3) . . . . ?
C9 C8 C11 N 1.2(2) . . . . ?
O2 C8 C11 N -176.01(17) . . . . ?
C11 N C12 C13 96.1(3) . . . . ?
C10 N C12 C13 -75.6(3) . . . . ?
N C12 C13 C14 117.6(2) . . . . ?
N C12 C13 C18 -64.0(3) . . . . ?
C18 C13 C14 C15 -1.3(3) . . . . ?
C12 C13 C14 C15 177.1(2) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C14 C15 C16 C17 0.8(4) . . . . ?
C15 C16 C17 C18 -0.5(4) . . . . ?
C16 C17 C18 C13 -0.6(4) . . . . ?
C14 C13 C18 C17 1.6(3) . . . . ?
C12 C13 C18 C17 -176.9(2) . . . . ?
C8 C9 C19 C26 21.7(3) . . . . ?
C10 C9 C19 C26 -159.15(18) . . . . ?
C8 C9 C19 C20 -108.6(3) . . . . ?
C10 C9 C19 C20 70.5(2) . . . . ?
C9 C19 C20 C25 34.8(3) . . . . ?
C26 C19 C20 C25 -95.5(2) . . . . ?
C9 C19 C20 C21 -144.43(19) . . . . ?
C26 C19 C20 C21 85.3(2) . . . . ?
C25 C20 C21 C22 -0.8(3) . . . . ?
C19 C20 C21 C22 178.4(2) . . . . ?
C20 C21 C22 C23 0.4(4) . . . . ?
C21 C22 C23 C24 0.8(4) . . . . ?
C22 C23 C24 C25 -1.5(4) . . . . ?
C21 C20 C25 C24 0.1(3) . . . . ?
C19 C20 C25 C24 -179.1(2) . . . . ?
C23 C24 C25 C20 1.1(4) . . . . ?
C9 C19 C26 C27 -110.4(2) . . . . ?
C20 C19 C26 C27 18.2(3) . . . . ?
C9 C19 C26 C31 73.3(2) . . . . ?
C20 C19 C26 C31 -158.07(19) . . . . ?
C31 C26 C27 C28 -0.1(3) . . . . ?
C19 C26 C27 C28 -176.4(2) . . . . ?
C26 C27 C28 C29 1.3(3) . . . . ?
C27 C28 C29 O4 173.07(19) . . . . ?
C27 C28 C29 C30 -1.2(3) . . . . ?
C36 O4 C29 C28 108.2(2) . . . . ?
C36 O4 C29 C30 -77.4(2) . . . . ?
C28 C29 C30 C35 177.7(2) . . . . ?
O4 C29 C30 C35 3.5(3) . . . . ?
C28 C29 C30 C31 -0.2(3) . . . . ?
O4 C29 C30 C31 -174.34(18) . . . . ?
C29 C30 C31 C32 179.77(19) . . . . ?
C35 C30 C31 C32 1.8(3) . . . . ?
C29 C30 C31 C26 1.4(3) . . . . ?
C35 C30 C31 C26 -176.54(19) . . . . ?
C27 C26 C31 C30 -1.2(3) . . . . ?
C19 C26 C31 C30 175.20(18) . . . . ?
C27 C26 C31 C32 -179.5(2) . . . . ?
C19 C26 C31 C32 -3.1(3) . . . . ?
C30 C31 C32 C33 -1.8(3) . . . . ?
C26 C31 C32 C33 176.5(2) . . . . ?
C31 C32 C33 C34 0.4(4) . . . . ?
C32 C33 C34 C35 1.2(4) . . . . ?
C33 C34 C35 C30 -1.2(4) . . . . ?
C29 C30 C35 C34 -178.2(2) . . . . ?
C31 C30 C35 C34 -0.4(3) . . . . ?
C29 O4 C36 O5 2.8(3) . . . . ?
C29 O4 C36 C37 -176.11(17) . . . . ?
O5 C36 C37 C42 -172.5(2) . . . . ?
O4 C36 C37 C42 6.5(3) . . . . ?
O5 C36 C37 C38 4.8(3) . . . . ?
O4 C36 C37 C38 -176.27(18) . . . . ?
C42 C37 C38 C39 3.3(3) . . . . ?
C36 C37 C38 C39 -174.0(2) . . . . ?
C37 C38 C39 C40 -0.3(3) . . . . ?
C38 C39 C40 C41 -2.8(3) . . . . ?
C38 C39 C40 Br2 173.00(17) . . . . ?
C39 C40 C41 C42 2.8(3) . . . . ?
Br2 C40 C41 C42 -173.05(16) . . . . ?
C40 C41 C42 C37 0.3(3) . . . . ?
C38 C37 C42 C41 -3.3(3) . . . . ?
C36 C37 C42 C41 173.92(19) . . . . ?

_refine_diff_density_max         1.267
_refine_diff_density_min         -0.840
_refine_diff_density_rms         0.066


_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/c
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_SKY_4Cl
_database_code_depnum_ccdc_archive 'CCDC 2256393'
loop_
_audit_author_name
_audit_author_address
'Jeng-Liang Han'
;National Chung Hsing University
Taiwan
;
_audit_update_record             
;
2023-04-14 deposited with the CCDC.	2023-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C28 H20 Cl N O2'
_chemical_formula_sum            'C28 H20 Cl N O2'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         437.90

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   10.6868(7)
_cell_length_b                   9.8097(5)
_cell_length_c                   11.0347(7)
_cell_angle_alpha                90
_cell_angle_beta                 110.720(2)
_cell_angle_gamma                90
_cell_volume                     1081.99(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9991
_cell_measurement_theta_min      2.865
_cell_measurement_theta_max      27.861
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.203
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6932
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29069
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.865
_diffrn_reflns_theta_max         27.911
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5155
_reflns_number_gt                4583
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.890
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.997

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0406P)²+0.0343P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1980 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.007(17)
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)
_symmetry_int_tables_number      ?
_chemical_absolute_configuration unk
_refine_ls_number_reflns         5155
_refine_ls_number_parameters     289
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0721
_refine_ls_wR_factor_gt          0.0693
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl 0.45027(5) 0.32590(5) 0.40412(5) 0.03766(14) Uani 1 1 d . . . . .
O1 O 0.16101(12) 1.07407(12) 0.45685(12) 0.0207(3) Uani 1 1 d . . . . .
O2 O 0.36588(14) 1.16473(14) 0.69976(13) 0.0290(3) Uani 1 1 d . . . . .
N N 0.35260(16) 0.94310(16) 0.76508(14) 0.0232(3) Uani 1 1 d . . . . .
C1 C 0.06833(17) 1.00693(18) 0.35248(17) 0.0186(3) Uani 1 1 d . . . . .
C2 C 0.00861(18) 1.0923(2) 0.24302(17) 0.0211(4) Uani 1 1 d . . . . .
C3 C 0.04341(19) 1.23113(19) 0.24102(19) 0.0241(4) Uani 1 1 d . . . . .
H3A H 0.109071 1.270478 0.315006 0.029 Uiso 1 1 calc R U . . .
C4 C -0.0170(2) 1.3095(2) 0.13289(19) 0.0309(4) Uani 1 1 d . . . . .
H4A H 0.006907 1.402765 0.132630 0.037 Uiso 1 1 calc R U . . .
C5 C -0.1143(2) 1.2524(2) 0.0224(2) 0.0351(5) Uani 1 1 d . . . . .
H5A H -0.155641 1.307082 -0.052138 0.042 Uiso 1 1 calc R U . . .
C6 C -0.1491(2) 1.1187(2) 0.0224(2) 0.0358(5) Uani 1 1 d . . . . .
H6A H -0.214552 1.081221 -0.052848 0.043 Uiso 1 1 calc R U . . .
C7 C -0.08971(19) 1.0342(2) 0.13222(19) 0.0275(4) Uani 1 1 d . . . . .
C8 C -0.1243(2) 0.8955(2) 0.1360(2) 0.0347(5) Uani 1 1 d . . . . .
H8A H -0.191005 0.855914 0.062901 0.042 Uiso 1 1 calc R U . . .
C9 C -0.06360(19) 0.8182(2) 0.24252(19) 0.0301(4) Uani 1 1 d . . . . .
H9A H -0.088518 0.725140 0.241738 0.036 Uiso 1 1 calc R U . . .
C10 C 0.03578(18) 0.87146(19) 0.35503(17) 0.0211(4) Uani 1 1 d . . . . .
C11 C 0.09896(18) 0.77879(17) 0.47063(18) 0.0202(4) Uani 1 1 d . . . . .
H11A H 0.026855 0.740898 0.498943 0.024 Uiso 1 1 calc R U . . .
C12 C 0.19107(17) 0.86376(17) 0.57809(16) 0.0194(3) Uani 1 1 d . . . . .
C13 C 0.21598(18) 0.99391(17) 0.56389(17) 0.0191(4) Uani 1 1 d . . . . .
C14 C 0.31910(18) 1.04992(18) 0.68101(17) 0.0217(4) Uani 1 1 d . . . . .
C15 C 0.27936(18) 0.8192(2) 0.71074(17) 0.0231(4) Uani 1 1 d . . . . .
H15A H 0.225864 0.787324 0.762404 0.028 Uiso 1 1 calc R U . . .
H15B H 0.340752 0.745428 0.706059 0.028 Uiso 1 1 calc R U . . .
C16 C 0.17845(18) 0.66060(17) 0.44343(17) 0.0196(4) Uani 1 1 d . . . . .
C17 C 0.25299(19) 0.67778(18) 0.36361(17) 0.0231(4) Uani 1 1 d . . . . .
H17A H 0.246523 0.760827 0.317497 0.028 Uiso 1 1 calc R U . . .
C18 C 0.33640(19) 0.5755(2) 0.35053(18) 0.0255(4) Uani 1 1 d . . . . .
H18A H 0.387215 0.587830 0.296022 0.031 Uiso 1 1 calc R U . . .
C19 C 0.34474(18) 0.45487(19) 0.41800(18) 0.0237(4) Uani 1 1 d . . . . .
C20 C 0.2722(2) 0.43405(19) 0.49813(19) 0.0255(4) Uani 1 1 d . . . . .
H20A H 0.278889 0.350773 0.543946 0.031 Uiso 1 1 calc R U . . .
C21 C 0.18902(19) 0.53844(19) 0.50984(19) 0.0248(4) Uani 1 1 d . . . . .
H21A H 0.138382 0.525842 0.564474 0.030 Uiso 1 1 calc R U . . .
C22 C 0.46051(19) 0.9490(2) 0.88945(16) 0.0245(4) Uani 1 1 d . . . . .
H22A H 0.521917 1.023841 0.887528 0.029 Uiso 1 1 calc R U . . .
H22B H 0.511642 0.862677 0.903008 0.029 Uiso 1 1 calc R U . . .
C23 C 0.41492(18) 0.97126(19) 1.00289(17) 0.0212(4) Uani 1 1 d . . . . .
C24 C 0.4710(2) 0.8967(2) 1.11575(18) 0.0269(4) Uani 1 1 d . . . . .
H24A H 0.535850 0.828653 1.120577 0.032 Uiso 1 1 calc R U . . .
C25 C 0.4330(2) 0.9205(2) 1.22195(19) 0.0308(4) Uani 1 1 d . . . . .
H25A H 0.471666 0.868708 1.298924 0.037 Uiso 1 1 calc R U . . .
C26 C 0.3388(2) 1.0197(2) 1.2158(2) 0.0307(4) Uani 1 1 d . . . . .
H26A H 0.313916 1.037374 1.288801 0.037 Uiso 1 1 calc R U . . .
C27 C 0.2813(2) 1.0930(2) 1.1025(2) 0.0374(5) Uani 1 1 d . . . . .
H27A H 0.215561 1.160219 1.097257 0.045 Uiso 1 1 calc R U . . .
C28 C 0.3190(2) 1.0689(2) 0.9970(2) 0.0315(5) Uani 1 1 d . . . . .
H28A H 0.278886 1.119600 0.919529 0.038 Uiso 1 1 calc R U . . .


_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
Cl C19 1.7373(19) . ?
O1 C13 1.367(2) . ?
O1 C1 1.391(2) . ?
O2 C14 1.220(2) . ?
N C14 1.361(2) . ?
N C15 1.455(3) . ?
N C22 1.448(2) . ?
C1 C10 1.377(2) . ?
C1 C2 1.422(3) . ?
C2 C3 1.414(3) . ?
C2 C7 1.419(3) . ?
C3 C4 1.374(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.409(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.363(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.419(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.415(3) . ?
C8 C9 1.355(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.418(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.517(3) . ?
C11 C12 1.498(2) . ?
C11 C16 1.528(2) . ?
C11 H11A 1.0000 . ?
C12 C13 1.325(2) . ?
C12 C15 1.499(2) . ?
C13 C14 1.476(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C21 1.388(3) . ?
C16 C17 1.391(2) . ?
C17 C18 1.383(3) . ?
C17 H17A 0.9500 . ?
C18 C19 1.384(3) . ?
C18 H18A 0.9500 . ?
C19 C20 1.382(3) . ?
C20 C21 1.392(3) . ?
C20 H20A 0.9500 . ?
C21 H21A 0.9500 . ?
C22 C23 1.511(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.385(3) . ?
C23 C28 1.387(3) . ?
C24 C25 1.389(3) . ?
C24 H24A 0.9500 . ?
C25 C26 1.384(3) . ?
C25 H25A 0.9500 . ?
C26 C27 1.383(3) . ?
C26 H26A 0.9500 . ?
C27 C28 1.381(3) . ?
C27 H27A 0.9500 . ?
C28 H28A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O1 C1 113.94(13) . . ?
C14 N C15 112.89(15) . . ?
C14 N C22 122.99(17) . . ?
C15 N C22 123.76(15) . . ?
C10 C1 O1 123.46(16) . . ?
C10 C1 C2 123.05(16) . . ?
O1 C1 C2 113.48(15) . . ?
C3 C2 C1 122.63(17) . . ?
C3 C2 C7 119.48(18) . . ?
C1 C2 C7 117.90(17) . . ?
C4 C3 C2 120.49(19) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C6 C5 C4 120.0(2) . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C5 C6 C7 121.5(2) . . ?
C5 C6 H6A 119.3 . . ?
C7 C6 H6A 119.3 . . ?
C8 C7 C6 122.98(19) . . ?
C8 C7 C2 118.85(18) . . ?
C6 C7 C2 118.18(19) . . ?
C9 C8 C7 120.91(19) . . ?
C9 C8 H8A 119.5 . . ?
C7 C8 H8A 119.5 . . ?
C8 C9 C10 122.3(2) . . ?
C8 C9 H9A 118.9 . . ?
C10 C9 H9A 118.9 . . ?
C1 C10 C9 117.03(17) . . ?
C1 C10 C11 123.73(16) . . ?
C9 C10 C11 119.23(17) . . ?
C12 C11 C10 107.73(14) . . ?
C12 C11 C16 108.80(14) . . ?
C10 C11 C16 113.73(14) . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C16 C11 H11A 108.8 . . ?
C13 C12 C11 123.09(16) . . ?
C13 C12 C15 108.26(16) . . ?
C11 C12 C15 128.38(15) . . ?
C12 C13 O1 127.87(16) . . ?
C12 C13 C14 111.97(16) . . ?
O1 C13 C14 120.14(15) . . ?
O2 C14 N 127.02(18) . . ?
O2 C14 C13 128.79(16) . . ?
N C14 C13 104.19(15) . . ?
N C15 C12 102.68(15) . . ?
N C15 H15A 111.2 . . ?
C12 C15 H15A 111.2 . . ?
N C15 H15B 111.2 . . ?
C12 C15 H15B 111.2 . . ?
H15A C15 H15B 109.1 . . ?
C21 C16 C17 118.75(16) . . ?
C21 C16 C11 119.88(16) . . ?
C17 C16 C11 120.99(15) . . ?
C18 C17 C16 120.84(17) . . ?
C18 C17 H17A 119.6 . . ?
C16 C17 H17A 119.6 . . ?
C19 C18 C17 119.03(17) . . ?
C19 C18 H18A 120.5 . . ?
C17 C18 H18A 120.5 . . ?
C18 C19 C20 121.78(17) . . ?
C18 C19 Cl 119.70(14) . . ?
C20 C19 Cl 118.52(15) . . ?
C19 C20 C21 118.16(17) . . ?
C19 C20 H20A 120.9 . . ?
C21 C20 H20A 120.9 . . ?
C16 C21 C20 121.44(17) . . ?
C16 C21 H21A 119.3 . . ?
C20 C21 H21A 119.3 . . ?
N C22 C23 114.13(15) . . ?
N C22 H22A 108.7 . . ?
C23 C22 H22A 108.7 . . ?
N C22 H22B 108.7 . . ?
C23 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C24 C23 C28 118.98(17) . . ?
C24 C23 C22 120.33(16) . . ?
C28 C23 C22 120.68(16) . . ?
C23 C24 C25 120.46(18) . . ?
C23 C24 H24A 119.8 . . ?
C25 C24 H24A 119.8 . . ?
C24 C25 C26 120.09(19) . . ?
C24 C25 H25A 120.0 . . ?
C26 C25 H25A 120.0 . . ?
C25 C26 C27 119.55(18) . . ?
C25 C26 H26A 120.2 . . ?
C27 C26 H26A 120.2 . . ?
C28 C27 C26 120.23(19) . . ?
C28 C27 H27A 119.9 . . ?
C26 C27 H27A 119.9 . . ?
C23 C28 C27 120.67(19) . . ?
C23 C28 H28A 119.7 . . ?
C27 C28 H28A 119.7 . . ?

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
C13 O1 C1 C10 -1.0(2) . . . . ?
C13 O1 C1 C2 178.12(14) . . . . ?
C10 C1 C2 C3 -179.54(17) . . . . ?
O1 C1 C2 C3 1.3(2) . . . . ?
C10 C1 C2 C7 0.5(2) . . . . ?
O1 C1 C2 C7 -178.63(15) . . . . ?
C1 C2 C3 C4 179.94(16) . . . . ?
C7 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
C5 C6 C7 C8 179.4(2) . . . . ?
C5 C6 C7 C2 -0.5(3) . . . . ?
C3 C2 C7 C8 -179.49(18) . . . . ?
C1 C2 C7 C8 0.5(3) . . . . ?
C3 C2 C7 C6 0.4(3) . . . . ?
C1 C2 C7 C6 -179.62(17) . . . . ?
C6 C7 C8 C9 179.1(2) . . . . ?
C2 C7 C8 C9 -1.0(3) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
O1 C1 C10 C9 178.09(16) . . . . ?
C2 C1 C10 C9 -0.9(2) . . . . ?
O1 C1 C10 C11 -1.3(3) . . . . ?
C2 C1 C10 C11 179.68(16) . . . . ?
C8 C9 C10 C1 0.4(3) . . . . ?
C8 C9 C10 C11 179.83(18) . . . . ?
C1 C10 C11 C12 3.9(2) . . . . ?
C9 C10 C11 C12 -175.45(15) . . . . ?
C1 C10 C11 C16 -116.76(18) . . . . ?
C9 C10 C11 C16 63.9(2) . . . . ?
C10 C11 C12 C13 -4.9(2) . . . . ?
C16 C11 C12 C13 118.87(18) . . . . ?
C10 C11 C12 C15 -178.19(16) . . . . ?
C16 C11 C12 C15 -54.5(2) . . . . ?
C11 C12 C13 O1 3.4(3) . . . . ?
C15 C12 C13 O1 177.89(16) . . . . ?
C11 C12 C13 C14 -174.89(15) . . . . ?
C15 C12 C13 C14 -0.4(2) . . . . ?
C1 O1 C13 C12 0.0(2) . . . . ?
C1 O1 C13 C14 178.12(14) . . . . ?
C15 N C14 O2 -178.72(17) . . . . ?
C22 N C14 O2 -5.3(3) . . . . ?
C15 N C14 C13 0.7(2) . . . . ?
C22 N C14 C13 174.04(15) . . . . ?
C12 C13 C14 O2 179.22(19) . . . . ?
O1 C13 C14 O2 0.8(3) . . . . ?
C12 C13 C14 N -0.1(2) . . . . ?
O1 C13 C14 N -178.58(15) . . . . ?
C14 N C15 C12 -0.9(2) . . . . ?
C22 N C15 C12 -174.20(15) . . . . ?
C13 C12 C15 N 0.74(19) . . . . ?
C11 C12 C15 N 174.86(16) . . . . ?
C12 C11 C16 C21 89.6(2) . . . . ?
C10 C11 C16 C21 -150.34(17) . . . . ?
C12 C11 C16 C17 -83.3(2) . . . . ?
C10 C11 C16 C17 36.8(2) . . . . ?
C21 C16 C17 C18 -0.1(3) . . . . ?
C11 C16 C17 C18 172.79(16) . . . . ?
C16 C17 C18 C19 0.1(3) . . . . ?
C17 C18 C19 C20 -0.1(3) . . . . ?
C17 C18 C19 Cl -179.33(14) . . . . ?
C18 C19 C20 C21 0.0(3) . . . . ?
Cl C19 C20 C21 179.29(15) . . . . ?
C17 C16 C21 C20 0.1(3) . . . . ?
C11 C16 C21 C20 -172.92(17) . . . . ?
C19 C20 C21 C16 0.0(3) . . . . ?
C14 N C22 C23 101.0(2) . . . . ?
C15 N C22 C23 -86.3(2) . . . . ?
N C22 C23 C24 136.44(18) . . . . ?
N C22 C23 C28 -45.2(3) . . . . ?
C28 C23 C24 C25 -0.9(3) . . . . ?
C22 C23 C24 C25 177.52(19) . . . . ?
C23 C24 C25 C26 -0.2(3) . . . . ?
C24 C25 C26 C27 1.1(3) . . . . ?
C25 C26 C27 C28 -1.0(3) . . . . ?
C24 C23 C28 C27 1.0(3) . . . . ?
C22 C23 C28 C27 -177.4(2) . . . . ?
C26 C27 C28 C23 -0.1(4) . . . . ?

_refine_diff_density_max         0.190
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.036



