#------------------------------------------------------------------------------
#$Date: 2021-04-05 18:15:00 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263824 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/78/7157888.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_7157888
loop_
_publ_author_name
'Marquès, Clàudia'
'Diaba, Faïza'
'Roca, Jaume'
'Bonjoch, Josep'
_publ_section_title
;
 Synthesis and reactivity of hydroindole enelactams leading to densely
 functionalized scaffolds.
;
_journal_issue                   10
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2284
_journal_page_last               2301
_journal_paper_doi               10.1039/d1ob00060h
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C21 H27 N O5'
_chemical_formula_sum            'C21 H27 N O5'
_chemical_formula_weight         373.43
_chemical_name_systematic        c-18b
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-11-30 deposited with the CCDC.	2021-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                107.614(4)
_cell_angle_beta                 91.299(4)
_cell_angle_gamma                93.979(4)
_cell_formula_units_Z            4
_cell_length_a                   9.6698(8)
_cell_length_b                   13.6733(12)
_cell_length_c                   15.2154(12)
_cell_measurement_reflns_used    9825
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.04
_cell_measurement_theta_min      2.48
_cell_volume                     1910.8(3)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            77889
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.071
_diffrn_reflns_theta_min         2.404
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.680
_exptl_crystal_size_mid          0.365
_exptl_crystal_size_min          0.257
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         12102
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0533P)²+0.7740P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1196
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10099
_reflns_number_total             12102
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00060h2.cif
_cod_data_source_block           D43XB112_0m_a
_cod_depositor_comments
'Adding full bibliography for 7157888--7157889.cif.'
_cod_database_code               7157888
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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 1.01338(8) 0.34578(6) 0.13373(6) 0.01900(16) Uani 1 1 d . . . . .
O2A O 0.88404(10) -0.08503(6) 0.19561(6) 0.02560(19) Uani 1 1 d . . . . .
O3A O 0.98297(10) -0.11217(6) 0.05533(6) 0.02393(18) Uani 1 1 d . . . . .
O4A O 0.92143(9) 0.36929(7) 0.36413(6) 0.02571(19) Uani 1 1 d . . . . .
O5A O 1.15356(8) 0.36479(6) 0.37452(5) 0.01763(15) Uani 1 1 d . . . . .
N1A N 0.83844(9) 0.22793(7) 0.14556(6) 0.01335(16) Uani 1 1 d . . . . .
C1A C 0.96403(10) 0.28120(8) 0.16740(7) 0.01359(18) Uani 1 1 d . . . . .
C2A C 1.03477(10) 0.24750(8) 0.24341(7) 0.01475(18) Uani 1 1 d . . . . .
H2A H 1.133393 0.233983 0.229200 0.018 Uiso 1 1 calc R U . . .
C3A C 0.94815(11) 0.14624(8) 0.23994(7) 0.01461(18) Uani 1 1 d . . . . .
C4A C 1.01226(11) 0.05852(8) 0.16608(7) 0.01566(19) Uani 1 1 d . . . . .
H4AA H 1.042624 0.084845 0.115175 0.019 Uiso 1 1 calc R U . . .
H4AB H 1.095826 0.039777 0.194130 0.019 Uiso 1 1 calc R U . . .
C5A C 0.91543(12) -0.03804(8) 0.12575(7) 0.0184(2) Uani 1 1 d . . . . .
C6A C 0.88182(13) -0.19403(9) 0.15297(9) 0.0233(2) Uani 1 1 d . . . . .
H6AA H 0.790221 -0.222847 0.122207 0.028 Uiso 1 1 calc R U . . .
H6AB H 0.904791 -0.229748 0.198476 0.028 Uiso 1 1 calc R U . . .
C7A C 0.99316(12) -0.20212(9) 0.08355(8) 0.0207(2) Uani 1 1 d . . . . .
H7AA H 1.086022 -0.202263 0.112262 0.025 Uiso 1 1 calc R U . . .
H7AB H 0.975331 -0.265426 0.030533 0.025 Uiso 1 1 calc R U . . .
C8A C 0.78393(12) -0.01188(9) 0.08360(8) 0.0209(2) Uani 1 1 d . . . . .
H8AA H 0.721093 -0.075033 0.057816 0.025 Uiso 1 1 calc R U . . .
H8AB H 0.807876 0.016443 0.032718 0.025 Uiso 1 1 calc R U . . .
C9A C 0.71091(11) 0.06714(9) 0.15747(8) 0.0193(2) Uani 1 1 d . . . . .
H9AA H 0.628391 0.086080 0.128488 0.023 Uiso 1 1 calc R U . . .
H9AB H 0.678162 0.035119 0.204325 0.023 Uiso 1 1 calc R U . . .
C10A C 0.80309(10) 0.16467(8) 0.20556(7) 0.01421(18) Uani 1 1 d . . . . .
H10A H 0.754030 0.206857 0.259474 0.017 Uiso 1 1 calc R U . . .
C11A C 0.73865(11) 0.24674(9) 0.08095(7) 0.01649(19) Uani 1 1 d . . . . .
H11A H 0.711585 0.181086 0.032205 0.020 Uiso 1 1 calc R U . . .
H11B H 0.783713 0.294759 0.050950 0.020 Uiso 1 1 calc R U . . .
C12A C 0.60877(10) 0.29146(8) 0.12535(7) 0.01547(19) Uani 1 1 d . . . . .
C13A C 0.47976(11) 0.25805(10) 0.07986(8) 0.0219(2) Uani 1 1 d . . . . .
H13A H 0.472779 0.203957 0.023038 0.026 Uiso 1 1 calc R U . . .
C14A C 0.36046(12) 0.30325(11) 0.11691(9) 0.0257(2) Uani 1 1 d . . . . .
H14A H 0.272879 0.280095 0.085158 0.031 Uiso 1 1 calc R U . . .
C15A C 0.36961(12) 0.38158(10) 0.19965(9) 0.0236(2) Uani 1 1 d . . . . .
H15A H 0.288614 0.413014 0.224440 0.028 Uiso 1 1 calc R U . . .
C16A C 0.49780(12) 0.41442(9) 0.24670(9) 0.0227(2) Uani 1 1 d . . . . .
H16A H 0.504070 0.467711 0.304040 0.027 Uiso 1 1 calc R U . . .
C17A C 0.61719(11) 0.36911(8) 0.20971(8) 0.0190(2) Uani 1 1 d . . . . .
H17A H 0.704408 0.391332 0.242185 0.023 Uiso 1 1 calc R U . . .
C18A C 1.02762(11) 0.33355(8) 0.33353(7) 0.01619(19) Uani 1 1 d . . . . .
C19A C 1.15920(11) 0.45006(8) 0.46057(7) 0.0179(2) Uani 1 1 d . . . . .
H19A H 1.106931 0.429178 0.508045 0.021 Uiso 1 1 calc R U . . .
H19B H 1.117402 0.509961 0.450214 0.021 Uiso 1 1 calc R U . . .
C20A C 1.30940(12) 0.47790(10) 0.49212(8) 0.0232(2) Uani 1 1 d . . . . .
H20A H 1.349848 0.417973 0.501744 0.035 Uiso 1 1 calc R U . . .
H20B H 1.316307 0.534566 0.550142 0.035 Uiso 1 1 calc R U . . .
H20C H 1.359847 0.499292 0.444996 0.035 Uiso 1 1 calc R U . . .
C21A C 0.94373(13) 0.12594(9) 0.33326(7) 0.0212(2) Uani 1 1 d . . . . .
H21A H 0.886493 0.061917 0.326792 0.032 Uiso 1 1 calc R U . . .
H21B H 0.903752 0.183215 0.378210 0.032 Uiso 1 1 calc R U . . .
H21C H 1.038111 0.119656 0.354637 0.032 Uiso 1 1 calc R U . . .
O1B O 0.46204(8) 0.65255(6) 0.37096(5) 0.01786(15) Uani 1 1 d . . . . .
O2B O 0.38484(11) 1.07750(7) 0.30185(6) 0.0278(2) Uani 1 1 d . . . . .
O3B O 0.49822(10) 1.11196(6) 0.44328(6) 0.02606(19) Uani 1 1 d . . . . .
O4B O 0.57834(9) 0.64378(7) 0.12069(6) 0.02592(19) Uani 1 1 d . . . . .
O5B O 0.35095(8) 0.62410(6) 0.14503(5) 0.01736(15) Uani 1 1 d . . . . .
N1B N 0.30205(9) 0.76433(7) 0.35643(6) 0.01330(16) Uani 1 1 d . . . . .
C1B C 0.41900(10) 0.71485(8) 0.33584(7) 0.01338(18) Uani 1 1 d . . . . .
C2B C 0.49038(10) 0.75096(8) 0.26109(7) 0.01442(18) Uani 1 1 d . . . . .
H2B H 0.590415 0.771421 0.280389 0.017 Uiso 1 1 calc R U . . .
C3B C 0.41630(11) 0.84870(8) 0.26210(7) 0.01466(18) Uani 1 1 d . . . . .
C4B C 0.49706(11) 0.93988(8) 0.33556(7) 0.01674(19) Uani 1 1 d . . . . .
H4BA H 0.527465 0.915841 0.387538 0.020 Uiso 1 1 calc R U . . .
H4BB H 0.581457 0.960837 0.307986 0.020 Uiso 1 1 calc R U . . .
C5B C 0.41568(13) 1.03381(8) 0.37361(8) 0.0202(2) Uani 1 1 d . . . . .
C6B C 0.40584(13) 1.18636(9) 0.34042(9) 0.0233(2) Uani 1 1 d . . . . .
H6BA H 0.321749 1.215829 0.370161 0.028 Uiso 1 1 calc R U . . .
H6BB H 0.432018 1.219364 0.292916 0.028 Uiso 1 1 calc R U . . .
C7B C 0.52389(12) 1.19871(9) 0.41077(8) 0.0208(2) Uani 1 1 d . . . . .
H7BA H 0.614741 1.197336 0.381882 0.025 Uiso 1 1 calc R U . . .
H7BB H 0.521964 1.263961 0.461618 0.025 Uiso 1 1 calc R U . . .
C8B C 0.28422(12) 1.00410(9) 0.41535(8) 0.0216(2) Uani 1 1 d . . . . .
H8BA H 0.231439 1.065367 0.439832 0.026 Uiso 1 1 calc R U . . .
H8BB H 0.308572 0.977830 0.467146 0.026 Uiso 1 1 calc R U . . .
C9B C 0.19500(12) 0.92118(9) 0.34182(8) 0.0193(2) Uani 1 1 d . . . . .
H9BA H 0.112014 0.900117 0.370679 0.023 Uiso 1 1 calc R U . . .
H9BB H 0.162726 0.950929 0.293943 0.023 Uiso 1 1 calc R U . . .
C10B C 0.27072(10) 0.82591(8) 0.29555(7) 0.01415(18) Uani 1 1 d . . . . .
H10B H 0.211965 0.781466 0.241336 0.017 Uiso 1 1 calc R U . . .
C11B C 0.20461(10) 0.74369(9) 0.42145(7) 0.01633(19) Uani 1 1 d . . . . .
H11C H 0.194990 0.808386 0.471638 0.020 Uiso 1 1 calc R U . . .
H11D H 0.242759 0.694076 0.449441 0.020 Uiso 1 1 calc R U . . .
C12B C 0.06270(10) 0.70073(8) 0.37734(7) 0.01562(19) Uani 1 1 d . . . . .
C13B C 0.04798(11) 0.61622(9) 0.29799(8) 0.0197(2) Uani 1 1 d . . . . .
H13B H 0.128022 0.585882 0.270267 0.024 Uiso 1 1 calc R U . . .
C14B C -0.08331(12) 0.57589(9) 0.25901(9) 0.0228(2) Uani 1 1 d . . . . .
H14B H -0.092654 0.518619 0.204527 0.027 Uiso 1 1 calc R U . . .
C15B C -0.20096(12) 0.61957(9) 0.29996(9) 0.0225(2) Uani 1 1 d . . . . .
H15B H -0.290572 0.591566 0.273744 0.027 Uiso 1 1 calc R U . . .
C16B C -0.18752(11) 0.70378(10) 0.37884(8) 0.0216(2) Uani 1 1 d . . . . .
H16B H -0.267799 0.733444 0.406825 0.026 Uiso 1 1 calc R U . . .
C17B C -0.05588(11) 0.74489(9) 0.41706(8) 0.0193(2) Uani 1 1 d . . . . .
H17B H -0.046756 0.803395 0.470520 0.023 Uiso 1 1 calc R U . . .
C18B C 0.48061(11) 0.66689(8) 0.16862(7) 0.01607(19) Uani 1 1 d . . . . .
C19B C 0.33394(12) 0.54709(9) 0.05370(7) 0.0182(2) Uani 1 1 d . . . . .
H19C H 0.386281 0.487005 0.052457 0.022 Uiso 1 1 calc R U . . .
H19D H 0.369553 0.576857 0.006062 0.022 Uiso 1 1 calc R U . . .
C20B C 0.18148(12) 0.51447(10) 0.03488(9) 0.0238(2) Uani 1 1 d . . . . .
H20D H 0.130441 0.574782 0.037873 0.036 Uiso 1 1 calc R U . . .
H20E H 0.148025 0.483092 0.081233 0.036 Uiso 1 1 calc R U . . .
H20F H 0.166720 0.464317 -0.026716 0.036 Uiso 1 1 calc R U . . .
C21B C 0.40808(13) 0.86675(9) 0.16768(7) 0.0204(2) Uani 1 1 d . . . . .
H21D H 0.502068 0.878032 0.147989 0.031 Uiso 1 1 calc R U . . .
H21E H 0.357078 0.927420 0.172099 0.031 Uiso 1 1 calc R U . . .
H21F H 0.359836 0.806363 0.122508 0.031 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'
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
C5A O2A C6A 106.81(8) . . ?
C7A O3A C5A 108.22(8) . . ?
C18A O5A C19A 115.91(8) . . ?
C1A N1A C11A 122.64(9) . . ?
C1A N1A C10A 113.44(8) . . ?
C11A N1A C10A 122.95(8) . . ?
O1A C1A N1A 126.71(10) . . ?
O1A C1A C2A 125.35(9) . . ?
N1A C1A C2A 107.94(9) . . ?
C18A C2A C1A 107.45(8) . . ?
C18A C2A C3A 114.06(9) . . ?
C1A C2A C3A 103.18(8) . . ?
C18A C2A H2A 110.6 . . ?
C1A C2A H2A 110.6 . . ?
C3A C2A H2A 110.6 . . ?
C21A C3A C10A 112.00(9) . . ?
C21A C3A C4A 111.83(8) . . ?
C10A C3A C4A 110.57(8) . . ?
C21A C3A C2A 113.38(9) . . ?
C10A C3A C2A 102.15(8) . . ?
C4A C3A C2A 106.39(8) . . ?
C5A C4A C3A 114.70(9) . . ?
C5A C4A H4AA 108.6 . . ?
C3A C4A H4AA 108.6 . . ?
C5A C4A H4AB 108.6 . . ?
C3A C4A H4AB 108.6 . . ?
H4AA C4A H4AB 107.6 . . ?
O2A C5A O3A 106.52(8) . . ?
O2A C5A C4A 109.80(9) . . ?
O3A C5A C4A 110.03(9) . . ?
O2A C5A C8A 111.26(9) . . ?
O3A C5A C8A 109.01(9) . . ?
C4A C5A C8A 110.15(9) . . ?
O2A C6A C7A 102.15(9) . . ?
O2A C6A H6AA 111.3 . . ?
C7A C6A H6AA 111.3 . . ?
O2A C6A H6AB 111.3 . . ?
C7A C6A H6AB 111.3 . . ?
H6AA C6A H6AB 109.2 . . ?
O3A C7A C6A 103.54(9) . . ?
O3A C7A H7AA 111.1 . . ?
C6A C7A H7AA 111.1 . . ?
O3A C7A H7AB 111.1 . . ?
C6A C7A H7AB 111.1 . . ?
H7AA C7A H7AB 109.0 . . ?
C5A C8A C9A 109.74(9) . . ?
C5A C8A H8AA 109.7 . . ?
C9A C8A H8AA 109.7 . . ?
C5A C8A H8AB 109.7 . . ?
C9A C8A H8AB 109.7 . . ?
H8AA C8A H8AB 108.2 . . ?
C10A C9A C8A 113.49(9) . . ?
C10A C9A H9AA 108.9 . . ?
C8A C9A H9AA 108.9 . . ?
C10A C9A H9AB 108.9 . . ?
C8A C9A H9AB 108.9 . . ?
H9AA C9A H9AB 107.7 . . ?
N1A C10A C9A 113.60(9) . . ?
N1A C10A C3A 102.09(8) . . ?
C9A C10A C3A 114.88(9) . . ?
N1A C10A H10A 108.6 . . ?
C9A C10A H10A 108.6 . . ?
C3A C10A H10A 108.6 . . ?
N1A C11A C12A 113.67(8) . . ?
N1A C11A H11A 108.8 . . ?
C12A C11A H11A 108.8 . . ?
N1A C11A H11B 108.8 . . ?
C12A C11A H11B 108.8 . . ?
H11A C11A H11B 107.7 . . ?
C13A C12A C17A 119.14(10) . . ?
C13A C12A C11A 119.95(10) . . ?
C17A C12A C11A 120.86(9) . . ?
C12A C13A C14A 120.62(11) . . ?
C12A C13A H13A 119.7 . . ?
C14A C13A H13A 119.7 . . ?
C15A C14A C13A 120.06(11) . . ?
C15A C14A H14A 120.0 . . ?
C13A C14A H14A 120.0 . . ?
C14A C15A C16A 119.87(10) . . ?
C14A C15A H15A 120.1 . . ?
C16A C15A H15A 120.1 . . ?
C15A C16A C17A 120.09(11) . . ?
C15A C16A H16A 120.0 . . ?
C17A C16A H16A 120.0 . . ?
C12A C17A C16A 120.21(10) . . ?
C12A C17A H17A 119.9 . . ?
C16A C17A H17A 119.9 . . ?
O4A C18A O5A 124.37(10) . . ?
O4A C18A C2A 124.26(9) . . ?
O5A C18A C2A 111.37(8) . . ?
O5A C19A C20A 107.67(9) . . ?
O5A C19A H19A 110.2 . . ?
C20A C19A H19A 110.2 . . ?
O5A C19A H19B 110.2 . . ?
C20A C19A H19B 110.2 . . ?
H19A C19A H19B 108.5 . . ?
C19A C20A H20A 109.5 . . ?
C19A C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
C19A C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C3A C21A H21A 109.5 . . ?
C3A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
C3A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C6B O2B C5B 107.30(9) . . ?
C7B O3B C5B 108.21(8) . . ?
C18B O5B C19B 114.74(8) . . ?
C1B N1B C11B 122.67(9) . . ?
C1B N1B C10B 113.48(8) . . ?
C11B N1B C10B 122.99(8) . . ?
O1B C1B N1B 126.46(10) . . ?
O1B C1B C2B 125.39(9) . . ?
N1B C1B C2B 108.14(8) . . ?
C18B C2B C1B 111.70(8) . . ?
C18B C2B C3B 114.68(8) . . ?
C1B C2B C3B 103.29(8) . . ?
C18B C2B H2B 109.0 . . ?
C1B C2B H2B 109.0 . . ?
C3B C2B H2B 109.0 . . ?
C21B C3B C4B 111.82(9) . . ?
C21B C3B C10B 112.08(8) . . ?
C4B C3B C10B 110.49(8) . . ?
C21B C3B C2B 113.27(9) . . ?
C4B C3B C2B 106.24(8) . . ?
C10B C3B C2B 102.43(8) . . ?
C5B C4B C3B 114.84(9) . . ?
C5B C4B H4BA 108.6 . . ?
C3B C4B H4BA 108.6 . . ?
C5B C4B H4BB 108.6 . . ?
C3B C4B H4BB 108.6 . . ?
H4BA C4B H4BB 107.5 . . ?
O2B C5B O3B 106.42(9) . . ?
O2B C5B C8B 111.32(10) . . ?
O3B C5B C8B 109.14(9) . . ?
O2B C5B C4B 109.71(9) . . ?
O3B C5B C4B 110.21(9) . . ?
C8B C5B C4B 109.98(9) . . ?
O2B C6B C7B 102.32(9) . . ?
O2B C6B H6BA 111.3 . . ?
C7B C6B H6BA 111.3 . . ?
O2B C6B H6BB 111.3 . . ?
C7B C6B H6BB 111.3 . . ?
H6BA C6B H6BB 109.2 . . ?
O3B C7B C6B 103.26(9) . . ?
O3B C7B H7BA 111.1 . . ?
C6B C7B H7BA 111.1 . . ?
O3B C7B H7BB 111.1 . . ?
C6B C7B H7BB 111.1 . . ?
H7BA C7B H7BB 109.1 . . ?
C5B C8B C9B 109.72(9) . . ?
C5B C8B H8BA 109.7 . . ?
C9B C8B H8BA 109.7 . . ?
C5B C8B H8BB 109.7 . . ?
C9B C8B H8BB 109.7 . . ?
H8BA C8B H8BB 108.2 . . ?
C10B C9B C8B 113.63(9) . . ?
C10B C9B H9BA 108.8 . . ?
C8B C9B H9BA 108.8 . . ?
C10B C9B H9BB 108.8 . . ?
C8B C9B H9BB 108.8 . . ?
H9BA C9B H9BB 107.7 . . ?
N1B C10B C9B 114.03(9) . . ?
N1B C10B C3B 102.04(8) . . ?
C9B C10B C3B 114.76(9) . . ?
N1B C10B H10B 108.6 . . ?
C9B C10B H10B 108.6 . . ?
C3B C10B H10B 108.6 . . ?
N1B C11B C12B 113.11(8) . . ?
N1B C11B H11C 109.0 . . ?
C12B C11B H11C 109.0 . . ?
N1B C11B H11D 109.0 . . ?
C12B C11B H11D 109.0 . . ?
H11C C11B H11D 107.8 . . ?
C13B C12B C17B 119.16(10) . . ?
C13B C12B C11B 120.85(9) . . ?
C17B C12B C11B 119.98(10) . . ?
C12B C13B C14B 120.41(10) . . ?
C12B C13B H13B 119.8 . . ?
C14B C13B H13B 119.8 . . ?
C13B C14B C15B 119.95(11) . . ?
C13B C14B H14B 120.0 . . ?
C15B C14B H14B 120.0 . . ?
C16B C15B C14B 120.12(10) . . ?
C16B C15B H15B 119.9 . . ?
C14B C15B H15B 119.9 . . ?
C15B C16B C17B 119.83(10) . . ?
C15B C16B H16B 120.1 . . ?
C17B C16B H16B 120.1 . . ?
C16B C17B C12B 120.51(11) . . ?
C16B C17B H17B 119.7 . . ?
C12B C17B H17B 119.7 . . ?
O4B C18B O5B 123.99(10) . . ?
O4B C18B C2B 123.53(10) . . ?
O5B C18B C2B 112.45(9) . . ?
O5B C19B C20B 107.70(9) . . ?
O5B C19B H19C 110.2 . . ?
C20B C19B H19C 110.2 . . ?
O5B C19B H19D 110.2 . . ?
C20B C19B H19D 110.2 . . ?
H19C C19B H19D 108.5 . . ?
C19B C20B H20D 109.5 . . ?
C19B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C19B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
C3B C21B H21D 109.5 . . ?
C3B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
C3B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 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
O1A C1A 1.2233(13) . ?
O2A C5A 1.4268(13) . ?
O2A C6A 1.4326(14) . ?
O3A C7A 1.4288(14) . ?
O3A C5A 1.4382(13) . ?
O4A C18A 1.2098(13) . ?
O5A C18A 1.3367(12) . ?
O5A C19A 1.4631(13) . ?
N1A C1A 1.3521(13) . ?
N1A C11A 1.4520(13) . ?
N1A C10A 1.4661(13) . ?
C1A C2A 1.5324(14) . ?
C2A C18A 1.5194(14) . ?
C2A C3A 1.5538(15) . ?
C2A H2A 1.0000 . ?
C3A C21A 1.5280(14) . ?
C3A C10A 1.5493(14) . ?
C3A C4A 1.5507(14) . ?
C4A C5A 1.5194(16) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C5A C8A 1.5236(17) . ?
C6A C7A 1.5113(16) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C8A C9A 1.5284(16) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C9A C10A 1.5242(15) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C10A H10A 1.0000 . ?
C11A C12A 1.5175(14) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C12A C13A 1.3909(15) . ?
C12A C17A 1.3927(15) . ?
C13A C14A 1.3958(16) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.3804(19) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.3923(17) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.3969(15) . ?
C16A H16A 0.9500 . ?
C17A H17A 0.9500 . ?
C19A C20A 1.5053(15) . ?
C19A H19A 0.9900 . ?
C19A H19B 0.9900 . ?
C20A H20A 0.9800 . ?
C20A H20B 0.9800 . ?
C20A H20C 0.9800 . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C21A H21C 0.9800 . ?
O1B C1B 1.2243(12) . ?
O2B C6B 1.4231(14) . ?
O2B C5B 1.4291(13) . ?
O3B C7B 1.4259(14) . ?
O3B C5B 1.4353(13) . ?
O4B C18B 1.2075(13) . ?
O5B C18B 1.3393(13) . ?
O5B C19B 1.4653(13) . ?
N1B C1B 1.3523(12) . ?
N1B C11B 1.4562(13) . ?
N1B C10B 1.4675(13) . ?
C1B C2B 1.5305(14) . ?
C2B C18B 1.5199(14) . ?
C2B C3B 1.5557(15) . ?
C2B H2B 1.0000 . ?
C3B C21B 1.5308(14) . ?
C3B C4B 1.5477(14) . ?
C3B C10B 1.5509(14) . ?
C4B C5B 1.5215(16) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C5B C8B 1.5184(18) . ?
C6B C7B 1.5119(16) . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C8B C9B 1.5279(16) . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C9B C10B 1.5262(15) . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C10B H10B 1.0000 . ?
C11B C12B 1.5121(14) . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
C12B C13B 1.3922(16) . ?
C12B C17B 1.3969(15) . ?
C13B C14B 1.3923(16) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.3930(17) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.3853(18) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.3942(16) . ?
C16B H16B 0.9500 . ?
C17B H17B 0.9500 . ?
C19B C20B 1.5056(16) . ?
C19B H19C 0.9900 . ?
C19B H19D 0.9900 . ?
C20B H20D 0.9800 . ?
C20B H20E 0.9800 . ?
C20B H20F 0.9800 . ?
C21B H21D 0.9800 . ?
C21B H21E 0.9800 . ?
C21B H21F 0.9800 . ?
