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#$Date: 2025-06-02 21:20:34 +0300 (Mon, 02 Jun 2025) $
#$Revision: 299904 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/77/1567784.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1567784
loop_
_publ_author_name
'Wang, Wang'
'Cai, Yanyao'
'Guo, Renyu'
'Brown, M. Kevin'
_publ_section_title
;
 Synthesis of Complex Bicyclic Scaffolds by Intermolecular Photosensitized
 Dearomative Cycloadditions of Activated Alkenes and Naphthalenes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC04789F
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H26 N O, Cl, 0.5(H2 O)'
_chemical_formula_sum            'C21 H27 Cl N O1.5'
_chemical_formula_weight         352.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     intrinsic
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-05-04 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.5120(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.0511(5)
_cell_length_b                   7.7600(3)
_cell_length_c                   17.0992(6)
_cell_measurement_reflns_used    9940
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.54
_cell_volume                     1888.96(12)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS, 2019)'
_computing_data_collection       'BIS v6.2.14 (Bruker_AXS, 2020)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS, 2019)'
_computing_molecular_graphics
;
C. B. Hübschle, G. M. Sheldrick and B. Dittrich
"ShelXle: a Qt graphical user interface for SHELXL"
J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_publication_material  'APEX4 v2021.6-RC4 (Bruker AXS, 2021)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
'1 deg frames measured 3 and 2 s, detector distance of 40 mm'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0957
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            75469
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.530
_diffrn_reflns_theta_min         2.372
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
L. Krause, R. Herbst-Irmer, G.M. Sheldrick, D. Stalke,
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination"
J. Appl. Cryst. (2015), 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       block
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.33(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         8672
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0412
_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)+(0.0754P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1130
_reflns_Friedel_coverage         0.861
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                7487
_reflns_number_total             8672
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc04789f2.cif
_cod_data_source_block           22062
_cod_depositor_comments
;

2025-06-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C42 H54 Cl2 N2 O3'
_cod_original_formula_weight         705.77
_cod_original_formula_moiety         ' 2(C21 H26 N O), 2 Cl, H2 O'
_cod_original_formula_units_Z            2
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1567784
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.940
_shelx_estimated_absorpt_t_max   0.975
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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 0.37684(4) 0.76130(10) 0.44627(4) 0.03078(17) Uani 1 1 d . . . . .
Cl2 Cl 0.11392(4) 0.74676(10) 0.56430(4) 0.03481(18) Uani 1 1 d . . . . .
O1W O 0.22807(16) 0.9586(3) 0.48824(14) 0.0470(6) Uani 1 1 d . . . . .
H1W H 0.272004 0.879541 0.481721 0.16(3) Uiso 1 1 d R . . . .
H2W H 0.193904 0.897541 0.509819 0.24(4) Uiso 1 1 d R . . . .
O1A O 0.62544(12) 0.3378(3) 0.97043(12) 0.0319(5) Uani 1 1 d . . . . .
N1A N 0.09176(18) 0.3705(4) 0.50419(15) 0.0290(5) Uani 1 1 d . . . . .
H1AA H 0.091(2) 0.475(5) 0.521(2) 0.035 Uiso 1 1 d . U . . .
H1AB H 0.035(2) 0.327(4) 0.4878(19) 0.035 Uiso 1 1 d . U . . .
C1A C 0.22652(17) 0.3341(4) 0.83324(16) 0.0228(6) Uani 1 1 d . . . . .
H1A H 0.214014 0.365965 0.883510 0.027 Uiso 1 1 calc R U . . .
C2A C 0.16698(17) 0.4565(4) 0.75540(16) 0.0241(5) Uani 1 1 d . . . . .
H2AA H 0.142643 0.552684 0.777049 0.029 Uiso 1 1 calc R U . . .
H2AB H 0.207117 0.505906 0.731175 0.029 Uiso 1 1 calc R U . . .
C3A C 0.08422(16) 0.3590(4) 0.68214(15) 0.0228(5) Uani 1 1 d . . . . .
H3A H 0.041603 0.440178 0.635301 0.027 Uiso 1 1 calc R U . . .
C4A C 0.03135(15) 0.2617(4) 0.72178(14) 0.0234(5) Uani 1 1 d . . . . .
C5A C -0.06351(16) 0.2753(4) 0.69699(15) 0.0244(5) Uani 1 1 d . . . . .
H5A H -0.101309 0.356537 0.653448 0.029 Uiso 1 1 calc R U . . .
C6A C -0.10317(19) 0.1684(4) 0.73664(17) 0.0288(6) Uani 1 1 d . . . . .
H6A H -0.168245 0.176877 0.720117 0.035 Uiso 1 1 calc R U . . .
C7A C -0.04752(18) 0.0497(4) 0.80021(17) 0.0298(6) Uani 1 1 d . . . . .
H7A H -0.074906 -0.023990 0.826388 0.036 Uiso 1 1 calc R U . . .
C8A C 0.04801(18) 0.0383(4) 0.82570(17) 0.0301(6) Uani 1 1 d . . . . .
H8A H 0.086124 -0.041521 0.869939 0.036 Uiso 1 1 calc R U . . .
C9A C 0.08737(17) 0.1440(4) 0.78620(16) 0.0245(6) Uani 1 1 d . . . . .
C10A C 0.18885(17) 0.1467(4) 0.80465(16) 0.0238(6) Uani 1 1 d . . . . .
H10A H 0.226760 0.062062 0.851906 0.029 Uiso 1 1 calc R U . . .
C11A C 0.19373(17) 0.1059(4) 0.71929(16) 0.0262(6) Uani 1 1 d . . . . .
H11C H 0.180349 -0.017850 0.704942 0.031 Uiso 1 1 calc R U . . .
H11D H 0.257732 0.130234 0.727279 0.031 Uiso 1 1 calc R U . . .
C12A C 0.12116(16) 0.2168(4) 0.64244(15) 0.0245(6) Uani 1 1 d . . . . .
H12A H 0.066855 0.140431 0.605725 0.029 Uiso 1 1 calc R U . . .
C13A C 0.16321(17) 0.2785(5) 0.58418(17) 0.0310(7) Uani 1 1 d . . . . .
H13C H 0.216307 0.357199 0.618272 0.037 Uiso 1 1 calc R U . . .
H13D H 0.187984 0.178454 0.565520 0.037 Uiso 1 1 calc R U . . .
C14A C 0.1132(3) 0.3717(5) 0.4286(2) 0.0490(9) Uani 1 1 d . . . . .
H14D H 0.061941 0.428503 0.378080 0.073 Uiso 1 1 calc R U . . .
H14E H 0.119789 0.252945 0.412764 0.073 Uiso 1 1 calc R U . . .
H14F H 0.171907 0.434431 0.445005 0.073 Uiso 1 1 calc R U . . .
C15A C 0.33272(17) 0.3384(4) 0.86750(15) 0.0223(5) Uani 1 1 d . . . . .
C16A C 0.38926(16) 0.2633(5) 0.94913(14) 0.0256(5) Uani 1 1 d . . . . .
H16A H 0.360192 0.212725 0.980949 0.031 Uiso 1 1 calc R U . . .
C17A C 0.48664(16) 0.2597(5) 0.98571(15) 0.0264(5) Uani 1 1 d . . . . .
H17A H 0.523190 0.207459 1.041546 0.032 Uiso 1 1 calc R U . . .
C18A C 0.52963(16) 0.3326(4) 0.94017(16) 0.0247(6) Uani 1 1 d . . . . .
C19A C 0.47593(18) 0.4093(4) 0.85901(17) 0.0294(6) Uani 1 1 d . . . . .
H19A H 0.505437 0.460251 0.827662 0.035 Uiso 1 1 calc R U . . .
C20A C 0.37874(18) 0.4114(4) 0.82369(16) 0.0270(6) Uani 1 1 d . . . . .
H20A H 0.342544 0.464199 0.767948 0.032 Uiso 1 1 calc R U . . .
C21A C 0.68140(17) 0.2545(5) 1.05228(17) 0.0362(6) Uani 1 1 d . . . . .
H21D H 0.748014 0.270718 1.068709 0.054 Uiso 1 1 calc R U . . .
H21E H 0.666786 0.131116 1.046612 0.054 Uiso 1 1 calc R U . . .
H21F H 0.667970 0.304313 1.097921 0.054 Uiso 1 1 calc R U . . .
O1B O 1.11817(12) 0.6566(3) 0.97345(12) 0.0326(5) Uani 1 1 d . . . . .
N1B N 0.58097(16) 0.6507(3) 0.49382(14) 0.0248(5) Uani 1 1 d . . . . .
H1BA H 0.588(2) 0.538(5) 0.5061(18) 0.030 Uiso 1 1 d . U . . .
H1BB H 0.528(2) 0.690(4) 0.4843(18) 0.030 Uiso 1 1 d . U . . .
C1B C 0.71767(17) 0.6627(4) 0.82261(16) 0.0233(6) Uani 1 1 d . . . . .
H1B H 0.702335 0.624132 0.870287 0.028 Uiso 1 1 calc R U . . .
C2B C 0.66042(17) 0.5479(4) 0.74103(16) 0.0253(6) Uani 1 1 d . . . . .
H2BA H 0.701466 0.508446 0.715661 0.030 Uiso 1 1 calc R U . . .
H2BB H 0.637243 0.444904 0.759194 0.030 Uiso 1 1 calc R U . . .
C3B C 0.57631(16) 0.6489(3) 0.67062(15) 0.0210(5) Uani 1 1 d . . . . .
H3B H 0.533956 0.570893 0.621839 0.025 Uiso 1 1 calc R U . . .
C4B C 0.52348(16) 0.7370(4) 0.71219(14) 0.0210(5) Uani 1 1 d . . . . .
C5B C 0.42772(16) 0.7264(4) 0.68532(16) 0.0248(6) Uani 1 1 d . . . . .
H5B H 0.389145 0.652028 0.638301 0.030 Uiso 1 1 calc R U . . .
C6B C 0.38872(18) 0.8261(4) 0.72816(17) 0.0283(6) Uani 1 1 d . . . . .
H6B H 0.323448 0.817879 0.710825 0.034 Uiso 1 1 calc R U . . .
C7B C 0.44412(19) 0.9361(4) 0.79532(17) 0.0305(6) Uani 1 1 d . . . . .
H7B H 0.416806 1.003062 0.824051 0.037 Uiso 1 1 calc R U . . .
C8B C 0.54013(19) 0.9501(4) 0.82153(16) 0.0289(6) Uani 1 1 d . . . . .
H8B H 0.578126 1.026825 0.867554 0.035 Uiso 1 1 calc R U . . .
C9B C 0.57937(17) 0.8507(4) 0.77961(15) 0.0230(5) Uani 1 1 d . . . . .
C10B C 0.68074(17) 0.8500(4) 0.79791(17) 0.0244(6) Uani 1 1 d . . . . .
H10B H 0.718594 0.930617 0.847319 0.029 Uiso 1 1 calc R U . . .
C11B C 0.68701(17) 0.9016(4) 0.71418(15) 0.0242(6) Uani 1 1 d . . . . .
H11A H 0.750887 0.877488 0.721767 0.029 Uiso 1 1 calc R U . . .
H11B H 0.674723 1.026513 0.703216 0.029 Uiso 1 1 calc R U . . .
C12B C 0.61339(16) 0.7974(3) 0.63455(15) 0.0222(6) Uani 1 1 d . . . . .
H12B H 0.559182 0.876404 0.601099 0.027 Uiso 1 1 calc R U . . .
C13B C 0.65249(16) 0.7466(5) 0.57230(16) 0.0284(6) Uani 1 1 d . . . . .
H13A H 0.672117 0.851424 0.552163 0.034 Uiso 1 1 calc R U . . .
H13B H 0.708631 0.673091 0.604073 0.034 Uiso 1 1 calc R U . . .
C14B C 0.5860(2) 0.6808(4) 0.40984(18) 0.0364(7) Uani 1 1 d . . . . .
H14A H 0.536007 0.615845 0.362067 0.055 Uiso 1 1 calc R U . . .
H14B H 0.647214 0.642448 0.416730 0.055 Uiso 1 1 calc R U . . .
H14C H 0.578171 0.804026 0.395638 0.055 Uiso 1 1 calc R U . . .
C15B C 0.82439(17) 0.6564(4) 0.86051(15) 0.0231(5) Uani 1 1 d . . . . .
C16B C 0.87272(17) 0.5902(4) 0.81782(16) 0.0262(6) Uani 1 1 d . . . . .
H16B H 0.838374 0.542941 0.760399 0.031 Uiso 1 1 calc R U . . .
C17B C 0.97036(18) 0.5914(4) 0.85715(17) 0.0289(6) Uani 1 1 d . . . . .
H17B H 1.001668 0.544124 0.826612 0.035 Uiso 1 1 calc R U . . .
C18B C 1.02227(18) 0.6609(4) 0.94037(17) 0.0261(6) Uani 1 1 d . . . . .
C19B C 0.97576(17) 0.7297(4) 0.98456(16) 0.0273(6) Uani 1 1 d . . . . .
H19B H 1.010182 0.778470 1.041617 0.033 Uiso 1 1 calc R U . . .
C20B C 0.87837(16) 0.7260(4) 0.94410(15) 0.0252(6) Uani 1 1 d . . . . .
H20B H 0.847092 0.772994 0.974742 0.030 Uiso 1 1 calc R U . . .
C21B C 1.17210(18) 0.7350(5) 1.05772(17) 0.0361(7) Uani 1 1 d . . . . .
H21A H 1.239061 0.727370 1.073918 0.054 Uiso 1 1 calc R U . . .
H21B H 1.160155 0.675158 1.102011 0.054 Uiso 1 1 calc R U . . .
H21C H 1.154055 0.856397 1.055000 0.054 Uiso 1 1 calc R U . . .
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'
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
H1W O1W H2W 108.5 . . ?
C18A O1A C21A 116.4(2) . . ?
C14A N1A C13A 114.3(2) . . ?
C14A N1A H1AA 109(2) . . ?
C13A N1A H1AA 106(2) . . ?
C14A N1A H1AB 110.3(19) . . ?
C13A N1A H1AB 110(2) . . ?
H1AA N1A H1AB 107(3) . . ?
C15A C1A C2A 116.8(2) . . ?
C15A C1A C10A 110.0(2) . . ?
C2A C1A C10A 107.8(2) . . ?
C15A C1A H1A 107.3 . . ?
C2A C1A H1A 107.3 . . ?
C10A C1A H1A 107.3 . . ?
C3A C2A C1A 110.8(2) . . ?
C3A C2A H2AA 109.5 . . ?
C1A C2A H2AA 109.5 . . ?
C3A C2A H2AB 109.5 . . ?
C1A C2A H2AB 109.5 . . ?
H2AA C2A H2AB 108.1 . . ?
C4A C3A C2A 109.46(19) . . ?
C4A C3A C12A 104.4(2) . . ?
C2A C3A C12A 110.2(2) . . ?
C4A C3A H3A 110.9 . . ?
C2A C3A H3A 110.9 . . ?
C12A C3A H3A 110.9 . . ?
C5A C4A C9A 120.6(3) . . ?
C5A C4A C3A 126.3(3) . . ?
C9A C4A C3A 113.0(2) . . ?
C4A C5A C6A 119.3(3) . . ?
C4A C5A H5A 120.3 . . ?
C6A C5A H5A 120.3 . . ?
C7A C6A C5A 120.1(2) . . ?
C7A C6A H6A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
C6A C7A C8A 120.3(3) . . ?
C6A C7A H7A 119.8 . . ?
C8A C7A H7A 119.8 . . ?
C9A C8A C7A 119.6(3) . . ?
C9A C8A H8A 120.2 . . ?
C7A C8A H8A 120.2 . . ?
C8A C9A C4A 120.0(2) . . ?
C8A C9A C10A 126.7(2) . . ?
C4A C9A C10A 113.3(2) . . ?
C9A C10A C11A 108.9(2) . . ?
C9A C10A C1A 107.6(2) . . ?
C11A C10A C1A 107.9(2) . . ?
C9A C10A H10A 110.8 . . ?
C11A C10A H10A 110.8 . . ?
C1A C10A H10A 110.8 . . ?
C10A C11A C12A 110.1(2) . . ?
C10A C11A H11C 109.6 . . ?
C12A C11A H11C 109.6 . . ?
C10A C11A H11D 109.6 . . ?
C12A C11A H11D 109.6 . . ?
H11C C11A H11D 108.2 . . ?
C13A C12A C3A 116.1(2) . . ?
C13A C12A C11A 110.1(2) . . ?
C3A C12A C11A 108.25(19) . . ?
C13A C12A H12A 107.3 . . ?
C3A C12A H12A 107.3 . . ?
C11A C12A H12A 107.3 . . ?
N1A C13A C12A 111.4(2) . . ?
N1A C13A H13C 109.3 . . ?
C12A C13A H13C 109.3 . . ?
N1A C13A H13D 109.3 . . ?
C12A C13A H13D 109.3 . . ?
H13C C13A H13D 108.0 . . ?
N1A C14A H14D 109.5 . . ?
N1A C14A H14E 109.5 . . ?
H14D C14A H14E 109.5 . . ?
N1A C14A H14F 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
C20A C15A C16A 116.6(2) . . ?
C20A C15A C1A 125.4(2) . . ?
C16A C15A C1A 118.1(2) . . ?
C17A C16A C15A 122.4(2) . . ?
C17A C16A H16A 118.8 . . ?
C15A C16A H16A 118.8 . . ?
C18A C17A C16A 119.3(2) . . ?
C18A C17A H17A 120.3 . . ?
C16A C17A H17A 120.3 . . ?
C17A C18A O1A 124.3(2) . . ?
C17A C18A C19A 120.0(2) . . ?
O1A C18A C19A 115.7(2) . . ?
C18A C19A C20A 119.7(2) . . ?
C18A C19A H19A 120.2 . . ?
C20A C19A H19A 120.2 . . ?
C19A C20A C15A 122.0(2) . . ?
C19A C20A H20A 119.0 . . ?
C15A C20A H20A 119.0 . . ?
O1A C21A H21D 109.5 . . ?
O1A C21A H21E 109.5 . . ?
H21D C21A H21E 109.5 . . ?
O1A C21A H21F 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
C18B O1B C21B 116.5(2) . . ?
C14B N1B C13B 115.0(2) . . ?
C14B N1B H1BA 108.8(18) . . ?
C13B N1B H1BA 108.4(19) . . ?
C14B N1B H1BB 104.8(19) . . ?
C13B N1B H1BB 106(2) . . ?
H1BA N1B H1BB 114(3) . . ?
C15B C1B C2B 116.5(2) . . ?
C15B C1B C10B 111.0(2) . . ?
C2B C1B C10B 107.5(2) . . ?
C15B C1B H1B 107.2 . . ?
C2B C1B H1B 107.2 . . ?
C10B C1B H1B 107.2 . . ?
C3B C2B C1B 110.6(2) . . ?
C3B C2B H2BA 109.5 . . ?
C1B C2B H2BA 109.5 . . ?
C3B C2B H2BB 109.5 . . ?
C1B C2B H2BB 109.5 . . ?
H2BA C2B H2BB 108.1 . . ?
C4B C3B C2B 110.1(2) . . ?
C4B C3B C12B 104.7(2) . . ?
C2B C3B C12B 109.24(19) . . ?
C4B C3B H3B 110.9 . . ?
C2B C3B H3B 110.9 . . ?
C12B C3B H3B 110.9 . . ?
C5B C4B C9B 120.0(2) . . ?
C5B C4B C3B 126.7(2) . . ?
C9B C4B C3B 113.0(2) . . ?
C4B C5B C6B 119.3(2) . . ?
C4B C5B H5B 120.4 . . ?
C6B C5B H5B 120.4 . . ?
C7B C6B C5B 120.5(2) . . ?
C7B C6B H6B 119.7 . . ?
C5B C6B H6B 119.7 . . ?
C6B C7B C8B 120.5(2) . . ?
C6B C7B H7B 119.7 . . ?
C8B C7B H7B 119.7 . . ?
C9B C8B C7B 119.2(3) . . ?
C9B C8B H8B 120.4 . . ?
C7B C8B H8B 120.4 . . ?
C8B C9B C4B 120.4(2) . . ?
C8B C9B C10B 126.8(2) . . ?
C4B C9B C10B 112.8(2) . . ?
C9B C10B C11B 109.6(2) . . ?
C9B C10B C1B 107.4(2) . . ?
C11B C10B C1B 108.5(2) . . ?
C9B C10B H10B 110.4 . . ?
C11B C10B H10B 110.4 . . ?
C1B C10B H10B 110.4 . . ?
C10B C11B C12B 109.3(2) . . ?
C10B C11B H11A 109.8 . . ?
C12B C11B H11A 109.8 . . ?
C10B C11B H11B 109.8 . . ?
C12B C11B H11B 109.8 . . ?
H11A C11B H11B 108.3 . . ?
C13B C12B C3B 116.4(2) . . ?
C13B C12B C11B 110.88(19) . . ?
C3B C12B C11B 108.32(19) . . ?
C13B C12B H12B 106.9 . . ?
C3B C12B H12B 106.9 . . ?
C11B C12B H12B 106.9 . . ?
N1B C13B C12B 111.30(19) . . ?
N1B C13B H13A 109.4 . . ?
C12B C13B H13A 109.4 . . ?
N1B C13B H13B 109.4 . . ?
C12B C13B H13B 109.4 . . ?
H13A C13B H13B 108.0 . . ?
N1B C14B H14A 109.5 . . ?
N1B C14B H14B 109.5 . . ?
H14A C14B H14B 109.5 . . ?
N1B C14B H14C 109.5 . . ?
H14A C14B H14C 109.5 . . ?
H14B C14B H14C 109.5 . . ?
C16B C15B C20B 116.7(2) . . ?
C16B C15B C1B 125.4(2) . . ?
C20B C15B C1B 117.8(2) . . ?
C15B C16B C17B 121.5(2) . . ?
C15B C16B H16B 119.3 . . ?
C17B C16B H16B 119.3 . . ?
C18B C17B C16B 120.6(2) . . ?
C18B C17B H17B 119.7 . . ?
C16B C17B H17B 119.7 . . ?
O1B C18B C17B 116.2(2) . . ?
O1B C18B C19B 124.5(2) . . ?
C17B C18B C19B 119.3(2) . . ?
C20B C19B C18B 119.0(2) . . ?
C20B C19B H19B 120.5 . . ?
C18B C19B H19B 120.5 . . ?
C19B C20B C15B 122.9(2) . . ?
C19B C20B H20B 118.6 . . ?
C15B C20B H20B 118.6 . . ?
O1B C21B H21A 109.5 . . ?
O1B C21B H21B 109.5 . . ?
H21A C21B H21B 109.5 . . ?
O1B C21B H21C 109.5 . . ?
H21A C21B H21C 109.5 . . ?
H21B C21B H21C 109.5 . . ?
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
O1W H1W 0.9791 . ?
O1W H2W 0.9211 . ?
O1A C18A 1.378(3) . ?
O1A C21A 1.422(3) . ?
N1A C14A 1.483(3) . ?
N1A C13A 1.499(4) . ?
N1A H1AA 0.87(4) . ?
N1A H1AB 0.89(3) . ?
C1A C15A 1.526(3) . ?
C1A C2A 1.553(4) . ?
C1A C10A 1.564(4) . ?
C1A H1A 1.0000 . ?
C2A C3A 1.539(4) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C3A C4A 1.510(3) . ?
C3A C12A 1.550(3) . ?
C3A H3A 1.0000 . ?
C4A C5A 1.383(3) . ?
C4A C9A 1.393(4) . ?
C5A C6A 1.397(4) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.390(4) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.390(4) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.386(4) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.509(3) . ?
C10A C11A 1.530(3) . ?
C10A H10A 1.0000 . ?
C11A C12A 1.553(4) . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C12A C13A 1.516(3) . ?
C12A H12A 1.0000 . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
C14A H14D 0.9800 . ?
C14A H14E 0.9800 . ?
C14A H14F 0.9800 . ?
C15A C20A 1.392(3) . ?
C15A C16A 1.393(3) . ?
C16A C17A 1.390(3) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.378(4) . ?
C17A H17A 0.9500 . ?
C18A C19A 1.385(4) . ?
C19A C20A 1.389(3) . ?
C19A H19A 0.9500 . ?
C20A H20A 0.9500 . ?
C21A H21D 0.9800 . ?
C21A H21E 0.9800 . ?
C21A H21F 0.9800 . ?
O1B C18B 1.373(3) . ?
O1B C21B 1.430(3) . ?
N1B C14B 1.494(3) . ?
N1B C13B 1.500(3) . ?
N1B H1BA 0.90(4) . ?
N1B H1BB 0.85(3) . ?
C1B C15B 1.527(3) . ?
C1B C2B 1.549(4) . ?
C1B C10B 1.553(4) . ?
C1B H1B 1.0000 . ?
C2B C3B 1.544(3) . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
C3B C4B 1.500(3) . ?
C3B C12B 1.550(3) . ?
C3B H3B 1.0000 . ?
C4B C5B 1.389(3) . ?
C4B C9B 1.399(4) . ?
C5B C6B 1.397(4) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.377(4) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.396(4) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.386(4) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.508(3) . ?
C10B C11B 1.534(4) . ?
C10B H10B 1.0000 . ?
C11B C12B 1.555(3) . ?
C11B H11A 0.9900 . ?
C11B H11B 0.9900 . ?
C12B C13B 1.516(3) . ?
C12B H12B 1.0000 . ?
C13B H13A 0.9900 . ?
C13B H13B 0.9900 . ?
C14B H14A 0.9800 . ?
C14B H14B 0.9800 . ?
C14B H14C 0.9800 . ?
C15B C16B 1.386(3) . ?
C15B C20B 1.393(3) . ?
C16B C17B 1.391(3) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.384(4) . ?
C17B H17B 0.9500 . ?
C18B C19B 1.391(4) . ?
C19B C20B 1.387(3) . ?
C19B H19B 0.9500 . ?
C20B H20B 0.9500 . ?
C21B H21A 0.9800 . ?
C21B H21B 0.9800 . ?
C21B H21C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1W H1W Cl1 0.98 2.23 3.185(2) 164.0 . yes
O1W H2W Cl2 0.92 2.23 3.155(2) 178.8 . yes
N1A H1AA Cl2 0.87(4) 2.21(4) 3.061(3) 169(3) . yes
N1A H1AB Cl2 0.89(3) 2.21(3) 3.102(3) 173(3) 2_546 yes
C13A H13D O1W 0.99 2.42 3.394(4) 167.6 1_545 yes
N1B H1BA Cl1 0.90(4) 2.27(4) 3.162(3) 172(3) 2_646 yes
N1B H1BB Cl1 0.85(3) 2.27(3) 3.110(2) 171(3) . yes
C14B H14B O1W 0.98 2.38 3.180(4) 138.0 2_646 yes
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
C15A C1A C2A C3A 131.7(2) . . . . ?
C10A C1A C2A C3A 7.2(3) . . . . ?
C1A C2A C3A C4A 50.8(3) . . . . ?
C1A C2A C3A C12A -63.5(3) . . . . ?
C2A C3A C4A C5A 124.3(3) . . . . ?
C12A C3A C4A C5A -117.7(3) . . . . ?
C2A C3A C4A C9A -58.7(3) . . . . ?
C12A C3A C4A C9A 59.3(3) . . . . ?
C9A C4A C5A C6A -0.6(4) . . . . ?
C3A C4A C5A C6A 176.1(3) . . . . ?
C4A C5A C6A C7A -0.1(4) . . . . ?
C5A C6A C7A C8A 1.0(4) . . . . ?
C6A C7A C8A C9A -1.1(4) . . . . ?
C7A C8A C9A C4A 0.5(4) . . . . ?
C7A C8A C9A C10A -178.9(3) . . . . ?
C5A C4A C9A C8A 0.4(4) . . . . ?
C3A C4A C9A C8A -176.7(3) . . . . ?
C5A C4A C9A C10A 179.9(3) . . . . ?
C3A C4A C9A C10A 2.7(3) . . . . ?
C8A C9A C10A C11A 120.5(3) . . . . ?
C4A C9A C10A C11A -59.0(3) . . . . ?
C8A C9A C10A C1A -122.8(3) . . . . ?
C4A C9A C10A C1A 57.7(3) . . . . ?
C15A C1A C10A C9A 170.58(19) . . . . ?
C2A C1A C10A C9A -61.0(3) . . . . ?
C15A C1A C10A C11A -72.1(2) . . . . ?
C2A C1A C10A C11A 56.3(2) . . . . ?
C9A C10A C11A C12A 47.9(3) . . . . ?
C1A C10A C11A C12A -68.6(3) . . . . ?
C4A C3A C12A C13A 169.9(2) . . . . ?
C2A C3A C12A C13A -72.7(3) . . . . ?
C4A C3A C12A C11A -65.8(2) . . . . ?
C2A C3A C12A C11A 51.7(3) . . . . ?
C10A C11A C12A C13A 140.2(2) . . . . ?
C10A C11A C12A C3A 12.4(3) . . . . ?
C14A N1A C13A C12A -156.4(3) . . . . ?
C3A C12A C13A N1A -62.5(3) . . . . ?
C11A C12A C13A N1A 174.1(2) . . . . ?
C2A C1A C15A C20A -15.3(4) . . . . ?
C10A C1A C15A C20A 108.0(3) . . . . ?
C2A C1A C15A C16A 164.9(3) . . . . ?
C10A C1A C15A C16A -71.8(3) . . . . ?
C20A C15A C16A C17A -0.3(5) . . . . ?
C1A C15A C16A C17A 179.6(3) . . . . ?
C15A C16A C17A C18A 0.0(5) . . . . ?
C16A C17A C18A O1A 179.4(3) . . . . ?
C16A C17A C18A C19A 0.3(5) . . . . ?
C21A O1A C18A C17A 3.0(4) . . . . ?
C21A O1A C18A C19A -178.0(3) . . . . ?
C17A C18A C19A C20A -0.4(4) . . . . ?
O1A C18A C19A C20A -179.5(3) . . . . ?
C18A C19A C20A C15A 0.1(5) . . . . ?
C16A C15A C20A C19A 0.2(4) . . . . ?
C1A C15A C20A C19A -179.6(3) . . . . ?
C15B C1B C2B C3B -135.3(2) . . . . ?
C10B C1B C2B C3B -10.1(3) . . . . ?
C1B C2B C3B C4B -48.7(3) . . . . ?
C1B C2B C3B C12B 65.8(3) . . . . ?
C2B C3B C4B C5B -127.4(3) . . . . ?
C12B C3B C4B C5B 115.2(3) . . . . ?
C2B C3B C4B C9B 58.3(3) . . . . ?
C12B C3B C4B C9B -59.0(3) . . . . ?
C9B C4B C5B C6B -2.0(4) . . . . ?
C3B C4B C5B C6B -175.9(3) . . . . ?
C4B C5B C6B C7B 1.1(4) . . . . ?
C5B C6B C7B C8B 0.2(4) . . . . ?
C6B C7B C8B C9B -0.5(4) . . . . ?
C7B C8B C9B C4B -0.4(4) . . . . ?
C7B C8B C9B C10B 179.1(3) . . . . ?
C5B C4B C9B C8B 1.7(4) . . . . ?
C3B C4B C9B C8B 176.3(2) . . . . ?
C5B C4B C9B C10B -177.9(2) . . . . ?
C3B C4B C9B C10B -3.3(3) . . . . ?
C8B C9B C10B C11B -120.1(3) . . . . ?
C4B C9B C10B C11B 59.5(3) . . . . ?
C8B C9B C10B C1B 122.3(3) . . . . ?
C4B C9B C10B C1B -58.2(3) . . . . ?
C15B C1B C10B C9B -168.26(19) . . . . ?
C2B C1B C10B C9B 63.3(3) . . . . ?
C15B C1B C10B C11B 73.4(2) . . . . ?
C2B C1B C10B C11B -55.1(3) . . . . ?
C9B C10B C11B C12B -47.5(3) . . . . ?
C1B C10B C11B C12B 69.5(2) . . . . ?
C4B C3B C12B C13B -167.7(2) . . . . ?
C2B C3B C12B C13B 74.4(3) . . . . ?
C4B C3B C12B C11B 66.6(2) . . . . ?
C2B C3B C12B C11B -51.3(3) . . . . ?
C10B C11B C12B C13B -142.1(2) . . . . ?
C10B C11B C12B C3B -13.2(3) . . . . ?
C14B N1B C13B C12B 146.5(3) . . . . ?
C3B C12B C13B N1B 57.3(3) . . . . ?
C11B C12B C13B N1B -178.3(2) . . . . ?
C2B C1B C15B C16B 15.6(4) . . . . ?
C10B C1B C15B C16B -107.8(3) . . . . ?
C2B C1B C15B C20B -165.9(3) . . . . ?
C10B C1B C15B C20B 70.7(3) . . . . ?
C20B C15B C16B C17B 0.8(4) . . . . ?
C1B C15B C16B C17B 179.3(3) . . . . ?
C15B C16B C17B C18B -0.6(4) . . . . ?
C21B O1B C18B C17B 177.3(3) . . . . ?
C21B O1B C18B C19B -2.6(4) . . . . ?
C16B C17B C18B O1B -179.8(3) . . . . ?
C16B C17B C18B C19B 0.1(4) . . . . ?
O1B C18B C19B C20B -179.8(3) . . . . ?
C17B C18B C19B C20B 0.3(4) . . . . ?
C18B C19B C20B C15B -0.1(5) . . . . ?
C16B C15B C20B C19B -0.4(4) . . . . ?
C1B C15B C20B C19B -179.1(3) . . . . ?
