#------------------------------------------------------------------------------
#$Date: 2021-11-13 00:55:10 +0200 (Sat, 13 Nov 2021) $
#$Revision: 270625 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/92/7129229.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_7129229
loop_
_publ_author_name
'Hu, Linfeng'
'Cao, Weidi'
'Wang, Kaixuan'
'Liu, Xiaohua'
'Feng, Xiaoming'
_publ_section_title
;
 Asymmetric synthesis of dihydrocarbazoles through Friedel-Crafts
 alkylation/annulation sequential reaction of indoles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC05099K
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H21 N3 O3'
_chemical_formula_sum            'C23 H21 N3 O3'
_chemical_formula_weight         387.43
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-11-09 deposited with the CCDC.	2021-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.2220(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9940(4)
_cell_length_b                   7.9399(2)
_cell_length_c                   18.0476(5)
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      80.51
_cell_measurement_theta_min      3.32
_cell_volume                     2016.14(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      143(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0801
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            40560
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         81.381
_diffrn_reflns_theta_min         2.609
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7970
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       flake
_exptl_crystal_F_000             816
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EA, Hexane'
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.069
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
; 
 Flack x determined using 2812 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.06(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     535
_refine_ls_number_reflns         8393
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0296P)²+1.2515P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1117
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_full    0.956
_reflns_Friedel_fraction_max     0.904
_reflns_number_gt                7234
_reflns_number_total             8393
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc05099k2.cif
_cod_data_source_block           hlf004
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7129229
_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   0.861
_shelx_estimated_absorpt_t_max   0.953
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
O1A O 0.93478(16) 0.6615(3) -0.12444(14) 0.0267(5) Uani 1 1 d . . . . .
O2A O 0.77800(17) 0.6475(3) -0.19172(14) 0.0305(5) Uani 1 1 d . . . . .
O3A O 0.73922(17) 0.3306(3) 0.11236(14) 0.0306(5) Uani 1 1 d . . . . .
N1A N 0.64851(19) 0.5284(3) -0.07204(16) 0.0229(5) Uani 1 1 d . . . . .
N2A N 0.65408(19) 0.3939(4) -0.01831(16) 0.0236(6) Uani 1 1 d . . . . .
N3A N 0.9281(2) 0.5683(4) 0.13314(17) 0.0253(6) Uani 1 1 d D . . . .
H3NA H 0.920(3) 0.527(6) 0.1731(19) 0.031(11) Uiso 1 1 d D . . . .
C1A C 1.0594(3) 0.5540(6) -0.1641(3) 0.0389(9) Uani 1 1 d . . . . .
H1AA H 1.074724 0.487266 -0.203807 0.058 Uiso 1 1 calc R U . . .
H1AB H 1.084772 0.497823 -0.112717 0.058 Uiso 1 1 calc R U . . .
H1AC H 1.087880 0.666189 -0.160512 0.058 Uiso 1 1 calc R U . . .
C2A C 0.9528(2) 0.5706(5) -0.1877(2) 0.0293(7) Uani 1 1 d . . . . .
H2AA H 0.926669 0.633438 -0.238017 0.035 Uiso 1 1 calc R U . . .
H2AB H 0.922747 0.458006 -0.194744 0.035 Uiso 1 1 calc R U . . .
C3A C 0.8438(2) 0.6871(4) -0.13333(19) 0.0224(6) Uani 1 1 d . . . . .
C4A C 0.8357(2) 0.7800(4) -0.06187(19) 0.0220(6) Uani 1 1 d . . . . .
H4AA H 0.861130 0.896333 -0.062406 0.026 Uiso 1 1 calc R U . . .
C5A C 0.7305(2) 0.7978(4) -0.0684(2) 0.0238(6) Uani 1 1 d . . . . .
H5AA H 0.722184 0.900432 -0.040331 0.029 Uiso 1 1 calc R U . . .
H5AB H 0.689507 0.807800 -0.124553 0.029 Uiso 1 1 calc R U . . .
C6A C 0.7029(2) 0.6463(4) -0.03271(19) 0.0228(6) Uani 1 1 d . . . . .
C7A C 0.7531(2) 0.6050(4) 0.05315(19) 0.0225(6) Uani 1 1 d . . . . .
C8A C 0.7176(2) 0.4261(4) 0.05531(19) 0.0239(6) Uani 1 1 d . . . . .
C9A C 0.7236(2) 0.7137(5) 0.1113(2) 0.0298(7) Uani 1 1 d . . . . .
H9AA H 0.654879 0.704212 0.099278 0.045 Uiso 1 1 calc R U . . .
H9AB H 0.740183 0.831607 0.106478 0.045 Uiso 1 1 calc R U . . .
H9AC H 0.757032 0.674660 0.165380 0.045 Uiso 1 1 calc R U . . .
C11A C 0.6031(2) 0.2442(4) -0.0484(2) 0.0232(6) Uani 1 1 d . . . . .
C12A C 0.5633(3) 0.2229(5) -0.1297(2) 0.0312(8) Uani 1 1 d . . . . .
H12A H 0.571593 0.306855 -0.164191 0.037 Uiso 1 1 calc R U . . .
C13A C 0.5111(3) 0.0780(5) -0.1604(2) 0.0372(9) Uani 1 1 d . . . . .
H13A H 0.483273 0.064223 -0.215967 0.045 Uiso 1 1 calc R U . . .
C14A C 0.4996(3) -0.0465(5) -0.1103(2) 0.0355(8) Uani 1 1 d . . . . .
H14A H 0.464513 -0.145730 -0.131182 0.043 Uiso 1 1 calc R U . . .
C15A C 0.5401(2) -0.0235(5) -0.0295(2) 0.0316(8) Uani 1 1 d . . . . .
H15A H 0.532368 -0.108275 0.004960 0.038 Uiso 1 1 calc R U . . .
C16A C 0.5917(2) 0.1206(5) 0.0025(2) 0.0275(7) Uani 1 1 d . . . . .
H16A H 0.618741 0.134591 0.058073 0.033 Uiso 1 1 calc R U . . .
C21A C 0.8570(2) 0.6199(4) 0.06560(19) 0.0228(6) Uani 1 1 d . . . . .
C22A C 0.8944(2) 0.6998(4) 0.01558(18) 0.0209(6) Uani 1 1 d . . . . .
C23A C 0.9963(2) 0.7013(4) 0.05513(19) 0.0237(6) Uani 1 1 d . . . . .
C24A C 1.0730(2) 0.7683(4) 0.0376(2) 0.0261(7) Uani 1 1 d . . . . .
H24A H 1.063345 0.823324 -0.011275 0.031 Uiso 1 1 calc R U . . .
C25A C 1.1634(2) 0.7525(5) 0.0932(2) 0.0296(7) Uani 1 1 d . . . . .
H25A H 1.215736 0.799885 0.082319 0.035 Uiso 1 1 calc R U . . .
C26A C 1.1799(2) 0.6686(5) 0.1650(2) 0.0314(8) Uani 1 1 d . . . . .
H26A H 1.242903 0.659414 0.201562 0.038 Uiso 1 1 calc R U . . .
C27A C 1.1054(2) 0.5989(5) 0.1832(2) 0.0299(7) Uani 1 1 d . . . . .
H27A H 1.116147 0.540265 0.231381 0.036 Uiso 1 1 calc R U . . .
C28A C 1.0142(2) 0.6180(4) 0.12839(19) 0.0246(6) Uani 1 1 d . . . . .
O1B O 0.47051(17) 0.3471(3) 0.39168(14) 0.0304(5) Uani 1 1 d . . . . .
O2B O 0.5758(2) 0.3664(4) 0.32883(16) 0.0381(6) Uani 1 1 d . . . . .
O3B O 0.86417(19) 0.6925(4) 0.61698(16) 0.0369(6) Uani 1 1 d . . . . .
N1B N 0.8333(2) 0.6154(4) 0.48640(17) 0.0263(6) Uani 1 1 d . . . . .
N2B N 0.7939(2) 0.4749(4) 0.43732(17) 0.0264(6) Uani 1 1 d . . . . .
N3B N 0.6949(2) 0.4654(4) 0.64798(17) 0.0252(6) Uani 1 1 d D . . . .
H3NB H 0.737(2) 0.514(5) 0.6867(17) 0.016(9) Uiso 1 1 d D . . . .
C1B C 0.3119(3) 0.4419(5) 0.3522(2) 0.0379(9) Uani 1 1 d . . . . .
H1BA H 0.260197 0.499125 0.311136 0.057 Uiso 1 1 calc R U . . .
H1BB H 0.328675 0.506192 0.401534 0.057 Uiso 1 1 calc R U . . .
H1BC H 0.291280 0.328600 0.360651 0.057 Uiso 1 1 calc R U . . .
C2B C 0.3976(3) 0.4292(5) 0.3267(2) 0.0318(8) Uani 1 1 d . . . . .
H2BA H 0.382573 0.361734 0.277761 0.038 Uiso 1 1 calc R U . . .
H2BB H 0.418810 0.542563 0.316952 0.038 Uiso 1 1 calc R U . . .
C3B C 0.5554(2) 0.3241(4) 0.3851(2) 0.0265(7) Uani 1 1 d . . . . .
C4B C 0.6206(2) 0.2331(4) 0.4577(2) 0.0249(7) Uani 1 1 d . . . . .
H4BA H 0.592564 0.119461 0.459323 0.030 Uiso 1 1 calc R U . . .
C5B C 0.7200(2) 0.2062(5) 0.4515(2) 0.0270(7) Uani 1 1 d . . . . .
H5BA H 0.751714 0.107995 0.483669 0.032 Uiso 1 1 calc R U . . .
H5BB H 0.714199 0.185247 0.395966 0.032 Uiso 1 1 calc R U . . .
C6B C 0.7761(2) 0.3618(4) 0.4812(2) 0.0253(7) Uani 1 1 d . . . . .
C7B C 0.8011(2) 0.4125(4) 0.5658(2) 0.0252(7) Uani 1 1 d . . . . .
C9B C 0.8365(2) 0.5916(4) 0.5629(2) 0.0262(7) Uani 1 1 d . . . . .
C10B C 0.8806(2) 0.3063(5) 0.6235(2) 0.0317(8) Uani 1 1 d . . . . .
H10A H 0.892688 0.345666 0.677571 0.048 Uiso 1 1 calc R U . . .
H10B H 0.938620 0.317688 0.610580 0.048 Uiso 1 1 calc R U . . .
H10C H 0.861154 0.187806 0.619166 0.048 Uiso 1 1 calc R U . . .
C11B C 0.8544(2) 0.7612(4) 0.4506(2) 0.0273(7) Uani 1 1 d . . . . .
C12B C 0.8175(3) 0.7790(5) 0.3691(2) 0.0362(8) Uani 1 1 d . . . . .
H12B H 0.778482 0.693189 0.337414 0.043 Uiso 1 1 calc R U . . .
C13B C 0.8379(3) 0.9225(6) 0.3343(3) 0.0464(10) Uani 1 1 d . . . . .
H13B H 0.812272 0.934363 0.278530 0.056 Uiso 1 1 calc R U . . .
C14B C 0.8945(3) 1.0480(6) 0.3789(3) 0.0450(10) Uani 1 1 d . . . . .
H14B H 0.908531 1.145303 0.354321 0.054 Uiso 1 1 calc R U . . .
C15B C 0.9309(3) 1.0303(5) 0.4604(3) 0.0402(9) Uani 1 1 d . . . . .
H15B H 0.969635 1.116832 0.491726 0.048 Uiso 1 1 calc R U . . .
C21B C 0.7085(2) 0.4032(4) 0.58101(19) 0.0236(6) Uani 1 1 d . . . . .
C22B C 0.6289(2) 0.3231(4) 0.53346(19) 0.0234(6) Uani 1 1 d . . . . .
C23B C 0.5600(2) 0.3326(4) 0.57317(19) 0.0242(6) Uani 1 1 d . . . . .
C24B C 0.4681(2) 0.2686(4) 0.5572(2) 0.0262(7) Uani 1 1 d . . . . .
H24B H 0.438009 0.204574 0.510767 0.031 Uiso 1 1 calc R U . . .
C25B C 0.4224(2) 0.3002(5) 0.6100(2) 0.0316(8) Uani 1 1 d . . . . .
H25B H 0.360355 0.256360 0.600089 0.038 Uiso 1 1 calc R U . . .
C26B C 0.4662(3) 0.3967(5) 0.6787(2) 0.0316(8) Uani 1 1 d . . . . .
H26B H 0.432146 0.419959 0.713224 0.038 Uiso 1 1 calc R U . . .
C27B C 0.5573(3) 0.4580(5) 0.6970(2) 0.0298(7) Uani 1 1 d . . . . .
H27B H 0.587014 0.521632 0.743634 0.036 Uiso 1 1 calc R U . . .
C28B C 0.6040(2) 0.4227(4) 0.64410(19) 0.0246(6) Uani 1 1 d . . . . .
C16B C 0.9114(2) 0.8882(5) 0.4969(2) 0.0318(8) Uani 1 1 d . . . . .
H16B H 0.936643 0.877385 0.552779 0.038 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 0.0181 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'
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'
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
C3A O1A C2A 116.2(3) . . ?
C6A N1A N2A 107.1(3) . . ?
C8A N2A C11A 129.3(3) . . ?
C8A N2A N1A 112.3(3) . . ?
C11A N2A N1A 118.1(3) . . ?
C21A N3A C28A 108.3(3) . . ?
O1A C2A C1A 106.7(3) . . ?
O2A C3A O1A 123.9(3) . . ?
O2A C3A C4A 125.7(3) . . ?
O1A C3A C4A 110.4(3) . . ?
C22A C4A C3A 112.8(3) . . ?
C22A C4A C5A 111.2(3) . . ?
C3A C4A C5A 110.8(3) . . ?
C6A C5A C4A 108.8(3) . . ?
N1A C6A C5A 124.7(3) . . ?
N1A C6A C7A 114.0(3) . . ?
C5A C6A C7A 120.4(3) . . ?
C21A C7A C6A 105.1(3) . . ?
C21A C7A C8A 115.1(3) . . ?
C6A C7A C8A 100.0(3) . . ?
C21A C7A C9A 112.5(3) . . ?
C6A C7A C9A 114.9(3) . . ?
C8A C7A C9A 108.7(3) . . ?
O3A C8A N2A 126.4(3) . . ?
O3A C8A C7A 127.2(3) . . ?
N2A C8A C7A 106.4(3) . . ?
C12A C11A C16A 120.2(3) . . ?
C12A C11A N2A 119.0(3) . . ?
C16A C11A N2A 120.8(3) . . ?
C11A C12A C13A 119.9(4) . . ?
C14A C13A C12A 120.4(4) . . ?
C15A C14A C13A 118.9(3) . . ?
C14A C15A C16A 121.6(3) . . ?
C15A C16A C11A 118.9(3) . . ?
C22A C21A N3A 110.7(3) . . ?
C22A C21A C7A 125.3(3) . . ?
N3A C21A C7A 123.8(3) . . ?
C21A C22A C23A 106.4(3) . . ?
C21A C22A C4A 124.3(3) . . ?
C23A C22A C4A 129.1(3) . . ?
C24A C23A C28A 118.8(3) . . ?
C24A C23A C22A 134.7(3) . . ?
C28A C23A C22A 106.5(3) . . ?
C25A C24A C23A 118.5(3) . . ?
C24A C25A C26A 121.9(3) . . ?
C27A C26A C25A 120.7(3) . . ?
C26A C27A C28A 117.6(3) . . ?
N3A C28A C27A 129.4(3) . . ?
N3A C28A C23A 108.1(3) . . ?
C27A C28A C23A 122.4(3) . . ?
C3B O1B C2B 117.7(3) . . ?
C9B N1B C11B 129.4(3) . . ?
C9B N1B N2B 112.4(3) . . ?
C11B N1B N2B 118.0(3) . . ?
C6B N2B N1B 107.1(3) . . ?
C28B N3B C21B 108.0(3) . . ?
O1B C2B C1B 105.4(3) . . ?
O2B C3B O1B 124.5(3) . . ?
O2B C3B C4B 125.8(3) . . ?
O1B C3B C4B 109.8(3) . . ?
C22B C4B C3B 112.5(3) . . ?
C22B C4B C5B 110.5(3) . . ?
C3B C4B C5B 110.6(3) . . ?
C6B C5B C4B 107.4(3) . . ?
N2B C6B C5B 124.8(3) . . ?
N2B C6B C7B 114.2(3) . . ?
C5B C6B C7B 120.2(3) . . ?
C6B C7B C21B 104.6(3) . . ?
C6B C7B C9B 100.5(3) . . ?
C21B C7B C9B 113.9(3) . . ?
C6B C7B C10B 113.9(3) . . ?
C21B C7B C10B 113.5(3) . . ?
C9B C7B C10B 109.7(3) . . ?
O3B C9B N1B 126.6(3) . . ?
O3B C9B C7B 127.6(3) . . ?
N1B C9B C7B 105.7(3) . . ?
C12B C11B C16B 119.9(3) . . ?
C12B C11B N1B 119.8(3) . . ?
C16B C11B N1B 120.3(3) . . ?
C13B C12B C11B 119.6(4) . . ?
C14B C13B C12B 121.3(4) . . ?
C13B C14B C15B 118.9(4) . . ?
C16B C15B C14B 121.1(4) . . ?
C22B C21B N3B 110.7(3) . . ?
C22B C21B C7B 124.8(3) . . ?
N3B C21B C7B 124.4(3) . . ?
C21B C22B C23B 106.5(3) . . ?
C21B C22B C4B 124.8(3) . . ?
C23B C22B C4B 128.6(3) . . ?
C24B C23B C28B 119.2(3) . . ?
C24B C23B C22B 134.2(3) . . ?
C28B C23B C22B 106.5(3) . . ?
C25B C24B C23B 118.7(3) . . ?
C24B C25B C26B 121.0(3) . . ?
C27B C26B C25B 121.6(3) . . ?
C26B C27B C28B 117.1(3) . . ?
N3B C28B C27B 129.5(3) . . ?
N3B C28B C23B 108.3(3) . . ?
C27B C28B C23B 122.2(3) . . ?
C15B C16B C11B 119.2(4) . . ?
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
O1A C3A 1.333(4) . ?
O1A C2A 1.453(4) . ?
O2A C3A 1.210(4) . ?
O3A C8A 1.229(4) . ?
N1A C6A 1.283(4) . ?
N1A N2A 1.425(4) . ?
N2A C8A 1.365(4) . ?
N2A C11A 1.416(4) . ?
N3A C21A 1.376(4) . ?
N3A C28A 1.380(4) . ?
C1A C2A 1.510(5) . ?
C3A C4A 1.527(4) . ?
C4A C22A 1.511(4) . ?
C4A C5A 1.548(4) . ?
C5A C6A 1.489(4) . ?
C6A C7A 1.506(4) . ?
C7A C21A 1.500(4) . ?
C7A C8A 1.522(5) . ?
C7A C9A 1.537(5) . ?
C11A C12A 1.389(5) . ?
C11A C16A 1.394(5) . ?
C12A C13A 1.394(5) . ?
C13A C14A 1.390(6) . ?
C14A C15A 1.385(6) . ?
C15A C16A 1.390(5) . ?
C21A C22A 1.371(4) . ?
C22A C23A 1.446(4) . ?
C23A C24A 1.399(5) . ?
C23A C28A 1.419(5) . ?
C24A C25A 1.385(5) . ?
C25A C26A 1.400(5) . ?
C26A C27A 1.384(5) . ?
C27A C28A 1.392(5) . ?
O1B C3B 1.332(4) . ?
O1B C2B 1.452(4) . ?
O2B C3B 1.205(4) . ?
O3B C9B 1.219(4) . ?
N1B C9B 1.377(4) . ?
N1B C11B 1.414(4) . ?
N1B N2B 1.420(4) . ?
N2B C6B 1.285(4) . ?
N3B C28B 1.382(4) . ?
N3B C21B 1.385(4) . ?
C1B C2B 1.511(6) . ?
C3B C4B 1.519(5) . ?
C4B C22B 1.510(4) . ?
C4B C5B 1.547(4) . ?
C5B C6B 1.487(5) . ?
C6B C7B 1.496(5) . ?
C7B C21B 1.506(4) . ?
C7B C9B 1.526(5) . ?
C7B C10B 1.535(5) . ?
C11B C12B 1.388(5) . ?
C11B C16B 1.398(5) . ?
C12B C13B 1.386(6) . ?
C13B C14B 1.374(7) . ?
C14B C15B 1.389(7) . ?
C15B C16B 1.387(5) . ?
C21B C22B 1.364(5) . ?
C22B C23B 1.448(4) . ?
C23B C24B 1.401(5) . ?
C23B C28B 1.415(5) . ?
C24B C25B 1.376(5) . ?
C25B C26B 1.413(6) . ?
C26B C27B 1.378(5) . ?
C27B C28B 1.394(5) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1A N2A C8A -3.4(3) . . . . ?
C6A N1A N2A C11A -177.3(3) . . . . ?
C3A O1A C2A C1A -178.9(3) . . . . ?
C2A O1A C3A O2A -4.1(5) . . . . ?
C2A O1A C3A C4A 178.8(3) . . . . ?
O2A C3A C4A C22A 132.8(3) . . . . ?
O1A C3A C4A C22A -50.1(4) . . . . ?
O2A C3A C4A C5A 7.5(4) . . . . ?
O1A C3A C4A C5A -175.4(3) . . . . ?
C22A C4A C5A C6A -37.8(4) . . . . ?
C3A C4A C5A C6A 88.4(3) . . . . ?
N2A N1A C6A C5A 169.4(3) . . . . ?
N2A N1A C6A C7A 0.5(4) . . . . ?
C4A C5A C6A N1A -107.1(4) . . . . ?
C4A C5A C6A C7A 61.1(4) . . . . ?
N1A C6A C7A C21A 121.7(3) . . . . ?
C5A C6A C7A C21A -47.7(4) . . . . ?
N1A C6A C7A C8A 2.1(3) . . . . ?
C5A C6A C7A C8A -167.3(3) . . . . ?
N1A C6A C7A C9A -114.1(3) . . . . ?
C5A C6A C7A C9A 76.5(4) . . . . ?
C11A N2A C8A O3A -4.3(5) . . . . ?
N1A N2A C8A O3A -177.3(3) . . . . ?
C11A N2A C8A C7A 177.7(3) . . . . ?
N1A N2A C8A C7A 4.7(3) . . . . ?
C21A C7A C8A O3A 66.1(4) . . . . ?
C6A C7A C8A O3A 178.1(3) . . . . ?
C9A C7A C8A O3A -61.1(4) . . . . ?
C21A C7A C8A N2A -115.9(3) . . . . ?
C6A C7A C8A N2A -3.9(3) . . . . ?
C9A C7A C8A N2A 116.9(3) . . . . ?
C8A N2A C11A C12A -162.0(3) . . . . ?
N1A N2A C11A C12A 10.7(4) . . . . ?
C8A N2A C11A C16A 18.8(5) . . . . ?
N1A N2A C11A C16A -168.5(3) . . . . ?
C16A C11A C12A C13A 0.5(5) . . . . ?
N2A C11A C12A C13A -178.7(3) . . . . ?
C11A C12A C13A C14A -0.8(6) . . . . ?
C12A C13A C14A C15A 0.5(6) . . . . ?
C13A C14A C15A C16A 0.0(5) . . . . ?
C14A C15A C16A C11A -0.3(5) . . . . ?
C12A C11A C16A C15A 0.0(5) . . . . ?
N2A C11A C16A C15A 179.2(3) . . . . ?
C28A N3A C21A C22A 1.2(4) . . . . ?
C28A N3A C21A C7A -173.2(3) . . . . ?
C6A C7A C21A C22A 16.5(4) . . . . ?
C8A C7A C21A C22A 125.5(4) . . . . ?
C9A C7A C21A C22A -109.3(4) . . . . ?
C6A C7A C21A N3A -169.9(3) . . . . ?
C8A C7A C21A N3A -60.9(4) . . . . ?
C9A C7A C21A N3A 64.3(4) . . . . ?
N3A C21A C22A C23A -1.2(4) . . . . ?
C7A C21A C22A C23A 173.2(3) . . . . ?
N3A C21A C22A C4A -176.6(3) . . . . ?
C7A C21A C22A C4A -2.3(5) . . . . ?
C3A C4A C22A C21A -111.9(4) . . . . ?
C5A C4A C22A C21A 13.3(4) . . . . ?
C3A C4A C22A C23A 73.7(4) . . . . ?
C5A C4A C22A C23A -161.2(3) . . . . ?
C21A C22A C23A C24A -176.9(4) . . . . ?
C4A C22A C23A C24A -1.7(6) . . . . ?
C21A C22A C23A C28A 0.7(4) . . . . ?
C4A C22A C23A C28A 175.9(3) . . . . ?
C28A C23A C24A C25A -0.9(5) . . . . ?
C22A C23A C24A C25A 176.4(4) . . . . ?
C23A C24A C25A C26A 1.5(5) . . . . ?
C24A C25A C26A C27A -0.5(6) . . . . ?
C25A C26A C27A C28A -1.0(5) . . . . ?
C21A N3A C28A C27A 177.8(4) . . . . ?
C21A N3A C28A C23A -0.7(4) . . . . ?
C26A C27A C28A N3A -176.8(3) . . . . ?
C26A C27A C28A C23A 1.6(5) . . . . ?
C24A C23A C28A N3A 178.1(3) . . . . ?
C22A C23A C28A N3A 0.0(4) . . . . ?
C24A C23A C28A C27A -0.6(5) . . . . ?
C22A C23A C28A C27A -178.6(3) . . . . ?
C9B N1B N2B C6B -2.7(4) . . . . ?
C11B N1B N2B C6B -176.7(3) . . . . ?
C3B O1B C2B C1B -178.3(3) . . . . ?
C2B O1B C3B O2B -0.2(5) . . . . ?
C2B O1B C3B C4B -178.6(3) . . . . ?
O2B C3B C4B C22B 126.2(4) . . . . ?
O1B C3B C4B C22B -55.4(4) . . . . ?
O2B C3B C4B C5B 2.0(5) . . . . ?
O1B C3B C4B C5B -179.6(3) . . . . ?
C22B C4B C5B C6B -40.1(4) . . . . ?
C3B C4B C5B C6B 85.2(3) . . . . ?
N1B N2B C6B C5B 169.4(3) . . . . ?
N1B N2B C6B C7B 0.3(4) . . . . ?
C4B C5B C6B N2B -103.9(4) . . . . ?
C4B C5B C6B C7B 64.6(4) . . . . ?
N2B C6B C7B C21B 120.2(3) . . . . ?
C5B C6B C7B C21B -49.5(4) . . . . ?
N2B C6B C7B C9B 1.9(4) . . . . ?
C5B C6B C7B C9B -167.8(3) . . . . ?
N2B C6B C7B C10B -115.4(3) . . . . ?
C5B C6B C7B C10B 74.9(4) . . . . ?
C11B N1B C9B O3B -4.7(6) . . . . ?
N2B N1B C9B O3B -177.8(3) . . . . ?
C11B N1B C9B C7B 176.9(3) . . . . ?
N2B N1B C9B C7B 3.8(4) . . . . ?
C6B C7B C9B O3B 178.4(3) . . . . ?
C21B C7B C9B O3B 67.1(5) . . . . ?
C10B C7B C9B O3B -61.3(4) . . . . ?
C6B C7B C9B N1B -3.2(3) . . . . ?
C21B C7B C9B N1B -114.5(3) . . . . ?
C10B C7B C9B N1B 117.1(3) . . . . ?
C9B N1B C11B C12B -158.3(3) . . . . ?
N2B N1B C11B C12B 14.5(5) . . . . ?
C9B N1B C11B C16B 21.1(5) . . . . ?
N2B N1B C11B C16B -166.0(3) . . . . ?
C16B C11B C12B C13B 0.3(6) . . . . ?
N1B C11B C12B C13B 179.7(3) . . . . ?
C11B C12B C13B C14B 0.3(6) . . . . ?
C12B C13B C14B C15B -0.6(6) . . . . ?
C13B C14B C15B C16B 0.5(6) . . . . ?
C28B N3B C21B C22B 0.7(4) . . . . ?
C28B N3B C21B C7B -175.3(3) . . . . ?
C6B C7B C21B C22B 15.4(4) . . . . ?
C9B C7B C21B C22B 124.2(4) . . . . ?
C10B C7B C21B C22B -109.3(4) . . . . ?
C6B C7B C21B N3B -169.2(3) . . . . ?
C9B C7B C21B N3B -60.4(4) . . . . ?
C10B C7B C21B N3B 66.1(4) . . . . ?
N3B C21B C22B C23B -0.8(4) . . . . ?
C7B C21B C22B C23B 175.2(3) . . . . ?
N3B C21B C22B C4B -176.8(3) . . . . ?
C7B C21B C22B C4B -0.8(5) . . . . ?
C3B C4B C22B C21B -110.4(4) . . . . ?
C5B C4B C22B C21B 13.8(5) . . . . ?
C3B C4B C22B C23B 74.5(4) . . . . ?
C5B C4B C22B C23B -161.3(3) . . . . ?
C21B C22B C23B C24B -176.3(4) . . . . ?
C4B C22B C23B C24B -0.5(6) . . . . ?
C21B C22B C23B C28B 0.6(4) . . . . ?
C4B C22B C23B C28B 176.4(3) . . . . ?
C28B C23B C24B C25B 2.1(5) . . . . ?
C22B C23B C24B C25B 178.7(4) . . . . ?
C23B C24B C25B C26B 0.7(5) . . . . ?
C24B C25B C26B C27B -2.2(6) . . . . ?
C25B C26B C27B C28B 0.9(5) . . . . ?
C21B N3B C28B C27B -179.4(4) . . . . ?
C21B N3B C28B C23B -0.2(4) . . . . ?
C26B C27B C28B N3B -178.9(3) . . . . ?
C26B C27B C28B C23B 2.0(5) . . . . ?
C24B C23B C28B N3B 177.2(3) . . . . ?
C22B C23B C28B N3B -0.3(4) . . . . ?
C24B C23B C28B C27B -3.5(5) . . . . ?
C22B C23B C28B C27B 179.0(3) . . . . ?
C14B C15B C16B C11B 0.0(6) . . . . ?
C12B C11B C16B C15B -0.4(5) . . . . ?
N1B C11B C16B C15B -179.8(3) . . . . ?
