#------------------------------------------------------------------------------
#$Date: 2022-11-11 04:23:04 +0200 (Fri, 11 Nov 2022) $
#$Revision: 279227 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/58/7245804.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_7245804
loop_
_publ_author_name
'Chen, Zuliang'
'Yan, Keyi'
'Luo, Hui'
'Yan, Jun'
'Zeng, Yang'
_publ_section_title
;
 Lewis acid-catalyzed [4 + 2] cycloaddition of donor--acceptor
 cyclobutanes with iminooxindoles: access to
 spiro[piperidine-3,2′-oxindoles]
;
_journal_issue                   49
_journal_name_full               'RSC Advances'
_journal_page_first              32097
_journal_page_last               32101
_journal_paper_doi               10.1039/D2RA04730F
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C29 H28 N2 O6'
_chemical_formula_sum            'C29 H28 N2 O6'
_chemical_formula_weight         500.53
_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
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc29ys46
_audit_creation_date             2021-04-29
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2022-01-22 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                108.892(4)
_cell_angle_beta                 90.756(4)
_cell_angle_gamma                111.651(4)
_cell_formula_units_Z            2
_cell_length_a                   9.3636(4)
_cell_length_b                   11.4375(5)
_cell_length_c                   13.7029(6)
_cell_measurement_reflns_used    4271
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.9950
_cell_measurement_theta_min      2.9870
_cell_volume                     1275.75(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     40.00  65.00   1.00    5.00    --  -11.27  77.00 -60.00   25
  2  ω      0.00  88.00   1.00    5.00    --   11.90  77.00 -30.00   88
  3  ω    -21.00  83.00   1.00    5.00    --   11.90  77.00 120.00  104
  4  ω    -30.00  -3.00   1.00    5.00    --  -11.27  77.00 -60.00   27
  5  ω    -42.00  58.00   1.00    5.00    --  -11.27  77.00-150.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0750727000
_diffrn_orient_matrix_UB_12      -0.0389827000
_diffrn_orient_matrix_UB_13      0.0074004000
_diffrn_orient_matrix_UB_21      0.0322228000
_diffrn_orient_matrix_UB_22      0.0017120000
_diffrn_orient_matrix_UB_23      0.0478308000
_diffrn_orient_matrix_UB_31      -0.0110807000
_diffrn_orient_matrix_UB_32      0.0597130000
_diffrn_orient_matrix_UB_33      0.0268386000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9987
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.048
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4489
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0429
_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)+(0.0394P)²+0.4204P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1018
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3683
_reflns_number_total             4489
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra04730f2.cif
_cod_data_source_block           3-8
_cod_database_code               7245804
_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.
;
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C5(H5), C6(H6), C15(H15), C16(H16), C17(H17),
 C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_date_sample_data_collection 2021-04-29
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.978
_oxdiff_exptl_absorpt_empirical_full_min 0.718
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
O1 O -0.12671(14) 0.02285(12) 0.42854(10) 0.0282(3) Uani 1 1 d . . . . .
O2 O 0.29446(14) 0.81332(12) 0.91190(9) 0.0262(3) Uani 1 1 d . . . . .
O3 O 0.48730(14) 1.05340(12) 0.81875(9) 0.0278(3) Uani 1 1 d . . . . .
O4 O 0.69275(13) 1.00543(11) 0.76980(9) 0.0264(3) Uani 1 1 d . . . . .
O5 O 0.51093(14) 0.87475(11) 0.56096(9) 0.0241(3) Uani 1 1 d . . . . .
O6 O 0.51889(14) 0.68235(12) 0.56292(9) 0.0244(3) Uani 1 1 d . . . . .
N1 N 0.34497(15) 0.59759(13) 0.72874(10) 0.0168(3) Uani 1 1 d . . . . .
N2 N 0.55079(16) 0.85892(14) 0.95874(11) 0.0223(3) Uani 1 1 d . . . . .
H2 H 0.560889 0.906745 1.023432 0.027 Uiso 1 1 calc R U . . .
C1 C 0.10386(18) 0.42234(16) 0.62348(12) 0.0186(4) Uani 1 1 d . . . . .
C2 C -0.04256(19) 0.34162(17) 0.63587(13) 0.0226(4) Uani 1 1 d . . . . .
H2A H -0.091428 0.377178 0.689345 0.027 Uiso 1 1 calc R U . . .
C3 C -0.1166(2) 0.20911(18) 0.56977(14) 0.0244(4) Uani 1 1 d . . . . .
H3 H -0.214828 0.156542 0.578747 0.029 Uiso 1 1 calc R U . . .
C4 C -0.04443(19) 0.15476(17) 0.49017(13) 0.0213(4) Uani 1 1 d . . . . .
C5 C 0.10214(19) 0.23325(17) 0.47731(13) 0.0203(4) Uani 1 1 d . . . . .
H5 H 0.151414 0.197250 0.424333 0.024 Uiso 1 1 calc R U . . .
C6 C 0.17474(19) 0.36570(17) 0.54392(13) 0.0204(4) Uani 1 1 d . . . . .
H6 H 0.273247 0.417910 0.535141 0.024 Uiso 1 1 calc R U . . .
C7 C 0.18194(18) 0.56923(16) 0.69115(13) 0.0188(4) Uani 1 1 d . . . . .
H7 H 0.127212 0.587803 0.751066 0.023 Uiso 1 1 calc R U . . .
C8 C 0.17751(19) 0.65625(17) 0.62802(13) 0.0212(4) Uani 1 1 d . . . . .
H8A H 0.216650 0.627591 0.563134 0.025 Uiso 1 1 calc R U . . .
H8B H 0.070648 0.643427 0.610913 0.025 Uiso 1 1 calc R U . . .
C9 C 0.27355(19) 0.80428(16) 0.68692(13) 0.0198(4) Uani 1 1 d . . . . .
H9A H 0.234038 0.834450 0.751347 0.024 Uiso 1 1 calc R U . . .
H9B H 0.266732 0.856623 0.645073 0.024 Uiso 1 1 calc R U . . .
C10 C 0.44435(18) 0.82488(16) 0.71129(12) 0.0182(4) Uani 1 1 d . . . . .
C11 C 0.45379(18) 0.73925(16) 0.77927(12) 0.0169(4) Uani 1 1 d . . . . .
C12 C 0.41807(19) 0.80727(16) 0.89016(12) 0.0190(4) Uani 1 1 d . . . . .
C13 C 0.66933(19) 0.82543(16) 0.91210(13) 0.0203(4) Uani 1 1 d . . . . .
C14 C 0.61847(18) 0.75156(16) 0.80644(13) 0.0180(4) Uani 1 1 d . . . . .
C15 C 0.7159(2) 0.70318(17) 0.74687(14) 0.0241(4) Uani 1 1 d . . . . .
H15 H 0.683833 0.652565 0.676163 0.029 Uiso 1 1 calc R U . . .
C16 C 0.8635(2) 0.7315(2) 0.79448(16) 0.0319(5) Uani 1 1 d . . . . .
H16 H 0.929633 0.698855 0.754953 0.038 Uiso 1 1 calc R U . . .
C17 C 0.9126(2) 0.80672(19) 0.89889(16) 0.0327(5) Uani 1 1 d . . . . .
H17 H 1.011871 0.825257 0.928829 0.039 Uiso 1 1 calc R U . . .
C18 C 0.8157(2) 0.85522(18) 0.95991(15) 0.0288(4) Uani 1 1 d . . . . .
H18 H 0.847960 0.906024 1.030575 0.035 Uiso 1 1 calc R U . . .
C19 C 0.35445(19) 0.51389(16) 0.78667(13) 0.0206(4) Uani 1 1 d . . . . .
C20 C 0.4377(2) 0.43473(17) 0.75267(14) 0.0267(4) Uani 1 1 d . . . . .
H20 H 0.486311 0.436595 0.694114 0.032 Uiso 1 1 calc R U . . .
C21 C 0.4498(2) 0.35227(19) 0.80491(16) 0.0372(5) Uani 1 1 d . . . . .
H21 H 0.507960 0.300604 0.782218 0.045 Uiso 1 1 calc R U . . .
C22 C 0.3755(3) 0.3473(2) 0.89040(16) 0.0424(6) Uani 1 1 d . . . . .
H22 H 0.383366 0.292081 0.925498 0.051 Uiso 1 1 calc R U . . .
C23 C 0.2896(3) 0.4236(2) 0.92396(16) 0.0413(5) Uani 1 1 d . . . . .
H23 H 0.238697 0.419267 0.981286 0.050 Uiso 1 1 calc R U . . .
C24 C 0.2786(2) 0.50741(19) 0.87260(14) 0.0308(4) Uani 1 1 d . . . . .
H24 H 0.220624 0.559095 0.895650 0.037 Uiso 1 1 calc R U . . .
C25 C 0.5415(2) 0.97388(17) 0.77223(13) 0.0202(4) Uani 1 1 d . . . . .
C26 C 0.7945(2) 1.14276(19) 0.83283(16) 0.0382(5) Uani 1 1 d . . . . .
H26A H 0.771295 1.204195 0.808023 0.057 Uiso 1 1 calc R U . . .
H26B H 0.900773 1.154807 0.827750 0.057 Uiso 1 1 calc R U . . .
H26C H 0.778433 1.159895 0.904310 0.057 Uiso 1 1 calc R U . . .
C27 C 0.49924(18) 0.78322(17) 0.60539(13) 0.0187(4) Uani 1 1 d . . . . .
C28 C 0.5367(2) 0.83704(18) 0.45321(13) 0.0253(4) Uani 1 1 d . . . . .
H28A H 0.451110 0.756111 0.411777 0.038 Uiso 1 1 calc R U . . .
H28B H 0.631128 0.822072 0.448577 0.038 Uiso 1 1 calc R U . . .
H28C H 0.544884 0.907958 0.427859 0.038 Uiso 1 1 calc R U . . .
C29 C -0.0650(2) -0.03108(19) 0.33830(15) 0.0338(5) Uani 1 1 d . . . . .
H29A H -0.055530 0.020462 0.293854 0.051 Uiso 1 1 calc R U . . .
H29B H -0.133506 -0.122923 0.301178 0.051 Uiso 1 1 calc R U . . .
H29C H 0.035444 -0.027122 0.359078 0.051 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
C4 O1 C29 117.32(13) . . ?
C25 O4 C26 115.71(14) . . ?
C27 O5 C28 114.81(13) . . ?
C11 N1 C7 118.29(12) . . ?
C19 N1 C7 112.41(12) . . ?
C19 N1 C11 112.42(12) . . ?
C12 N2 H2 123.8 . . ?
C12 N2 C13 112.30(14) . . ?
C13 N2 H2 123.8 . . ?
C2 C1 C7 121.47(15) . . ?
C6 C1 C2 118.12(15) . . ?
C6 C1 C7 120.37(14) . . ?
C1 C2 H2A 119.5 . . ?
C3 C2 C1 120.98(16) . . ?
C3 C2 H2A 119.5 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.01(16) . . ?
C4 C3 H3 120.0 . . ?
O1 C4 C3 115.90(15) . . ?
O1 C4 C5 124.28(16) . . ?
C5 C4 C3 119.82(16) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.53(16) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 H6 119.2 . . ?
C5 C6 C1 121.53(15) . . ?
C5 C6 H6 119.2 . . ?
N1 C7 C1 108.27(13) . . ?
N1 C7 H7 109.4 . . ?
N1 C7 C8 110.65(13) . . ?
C1 C7 H7 109.4 . . ?
C1 C7 C8 109.71(13) . . ?
C8 C7 H7 109.4 . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 C7 112.10(13) . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C8 C9 H9A 109.9 . . ?
C8 C9 H9B 109.9 . . ?
C8 C9 C10 109.05(13) . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 H9A 109.9 . . ?
C10 C9 H9B 109.9 . . ?
C9 C10 C11 109.35(13) . . ?
C25 C10 C9 109.31(13) . . ?
C25 C10 C11 109.32(13) . . ?
C25 C10 C27 109.37(13) . . ?
C27 C10 C9 106.01(13) . . ?
C27 C10 C11 113.38(13) . . ?
N1 C11 C10 110.59(12) . . ?
N1 C11 C12 112.58(13) . . ?
N1 C11 C14 111.80(13) . . ?
C12 C11 C10 107.08(12) . . ?
C14 C11 C10 113.37(13) . . ?
C14 C11 C12 101.02(12) . . ?
O2 C12 N2 125.65(15) . . ?
O2 C12 C11 126.89(14) . . ?
N2 C12 C11 107.46(14) . . ?
C14 C13 N2 109.89(14) . . ?
C18 C13 N2 127.54(16) . . ?
C18 C13 C14 122.55(17) . . ?
C13 C14 C11 108.92(14) . . ?
C15 C14 C11 132.00(15) . . ?
C15 C14 C13 119.07(15) . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 118.92(17) . . ?
C16 C15 H15 120.5 . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.12(18) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.63(17) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 C17 117.70(17) . . ?
C13 C18 H18 121.2 . . ?
C17 C18 H18 121.2 . . ?
C20 C19 N1 118.39(15) . . ?
C20 C19 C24 119.10(16) . . ?
C24 C19 N1 122.47(16) . . ?
C19 C20 H20 119.6 . . ?
C19 C20 C21 120.74(18) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.8(2) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.11(19) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.3(2) . . ?
C24 C23 H23 119.9 . . ?
C19 C24 H24 120.0 . . ?
C23 C24 C19 119.96(19) . . ?
C23 C24 H24 120.0 . . ?
O3 C25 O4 123.84(16) . . ?
O3 C25 C10 123.95(15) . . ?
O4 C25 C10 112.20(14) . . ?
O4 C26 H26A 109.5 . . ?
O4 C26 H26B 109.5 . . ?
O4 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O5 C27 C10 108.84(13) . . ?
O6 C27 O5 123.44(16) . . ?
O6 C27 C10 127.52(15) . . ?
O5 C28 H28A 109.5 . . ?
O5 C28 H28B 109.5 . . ?
O5 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O1 C29 H29A 109.5 . . ?
O1 C29 H29B 109.5 . . ?
O1 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
O1 C4 1.372(2) . ?
O1 C29 1.425(2) . ?
O2 C12 1.220(2) . ?
O3 C25 1.210(2) . ?
O4 C25 1.330(2) . ?
O4 C26 1.455(2) . ?
O5 C27 1.3448(19) . ?
O5 C28 1.449(2) . ?
O6 C27 1.195(2) . ?
N1 C7 1.485(2) . ?
N1 C11 1.476(2) . ?
N1 C19 1.452(2) . ?
N2 H2 0.8600 . ?
N2 C12 1.358(2) . ?
N2 C13 1.400(2) . ?
C1 C2 1.391(2) . ?
C1 C6 1.388(2) . ?
C1 C7 1.511(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.385(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(2) . ?
C4 C5 1.386(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C7 C8 1.526(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.516(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.543(2) . ?
C10 C11 1.577(2) . ?
C10 C25 1.531(2) . ?
C10 C27 1.533(2) . ?
C11 C12 1.570(2) . ?
C11 C14 1.525(2) . ?
C13 C14 1.389(2) . ?
C13 C18 1.382(2) . ?
C14 C15 1.380(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.396(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.376(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.379(2) . ?
C19 C24 1.391(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.389(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.377(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.374(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.390(3) . ?
C24 H24 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
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
O1 C4 C5 C6 179.81(14) . . . . ?
N1 C7 C8 C9 -52.61(18) . . . . ?
N1 C11 C12 O2 -54.3(2) . . . . ?
N1 C11 C12 N2 125.63(14) . . . . ?
N1 C11 C14 C13 -125.06(14) . . . . ?
N1 C11 C14 C15 54.3(2) . . . . ?
N1 C19 C20 C21 -179.67(16) . . . . ?
N1 C19 C24 C23 178.86(16) . . . . ?
N2 C13 C14 C11 2.37(18) . . . . ?
N2 C13 C14 C15 -177.06(14) . . . . ?
N2 C13 C18 C17 177.25(16) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C1 C7 C8 C9 -172.01(13) . . . . ?
C2 C1 C6 C5 0.9(2) . . . . ?
C2 C1 C7 N1 132.98(15) . . . . ?
C2 C1 C7 C8 -106.18(17) . . . . ?
C2 C3 C4 O1 -179.90(14) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
C6 C1 C2 C3 -1.0(2) . . . . ?
C6 C1 C7 N1 -49.67(19) . . . . ?
C6 C1 C7 C8 71.17(18) . . . . ?
C7 N1 C11 C10 -48.69(18) . . . . ?
C7 N1 C11 C12 71.05(17) . . . . ?
C7 N1 C11 C14 -176.03(13) . . . . ?
C7 N1 C19 C20 122.93(16) . . . . ?
C7 N1 C19 C24 -54.9(2) . . . . ?
C7 C1 C2 C3 176.44(15) . . . . ?
C7 C1 C6 C5 -176.57(14) . . . . ?
C7 C8 C9 C10 60.46(18) . . . . ?
C8 C9 C10 C11 -59.50(17) . . . . ?
C8 C9 C10 C25 -179.14(13) . . . . ?
C8 C9 C10 C27 63.08(16) . . . . ?
C9 C10 C11 N1 52.80(17) . . . . ?
C9 C10 C11 C12 -70.19(16) . . . . ?
C9 C10 C11 C14 179.28(13) . . . . ?
C9 C10 C25 O3 19.3(2) . . . . ?
C9 C10 C25 O4 -161.87(13) . . . . ?
C9 C10 C27 O5 69.93(16) . . . . ?
C9 C10 C27 O6 -104.99(19) . . . . ?
C10 C11 C12 O2 67.4(2) . . . . ?
C10 C11 C12 N2 -112.62(14) . . . . ?
C10 C11 C14 C13 109.11(15) . . . . ?
C10 C11 C14 C15 -71.6(2) . . . . ?
C11 N1 C7 C1 168.29(13) . . . . ?
C11 N1 C7 C8 48.03(18) . . . . ?
C11 N1 C19 C20 -100.61(17) . . . . ?
C11 N1 C19 C24 81.60(19) . . . . ?
C11 C10 C25 O3 -100.37(18) . . . . ?
C11 C10 C25 O4 78.47(16) . . . . ?
C11 C10 C27 O5 -170.10(13) . . . . ?
C11 C10 C27 O6 15.0(2) . . . . ?
C11 C14 C15 C16 179.94(16) . . . . ?
C12 N2 C13 C14 2.05(19) . . . . ?
C12 N2 C13 C18 -176.39(17) . . . . ?
C12 C11 C14 C13 -5.10(16) . . . . ?
C12 C11 C14 C15 174.23(17) . . . . ?
C13 N2 C12 O2 174.58(15) . . . . ?
C13 N2 C12 C11 -5.38(18) . . . . ?
C13 C14 C15 C16 -0.8(2) . . . . ?
C14 C11 C12 O2 -173.73(16) . . . . ?
C14 C11 C12 N2 6.23(16) . . . . ?
C14 C13 C18 C17 -1.0(3) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
C16 C17 C18 C13 -0.1(3) . . . . ?
C18 C13 C14 C11 -179.10(15) . . . . ?
C18 C13 C14 C15 1.5(3) . . . . ?
C19 N1 C7 C1 -58.04(17) . . . . ?
C19 N1 C7 C8 -178.30(13) . . . . ?
C19 N1 C11 C10 177.64(13) . . . . ?
C19 N1 C11 C12 -62.62(17) . . . . ?
C19 N1 C11 C14 50.30(18) . . . . ?
C19 C20 C21 C22 1.3(3) . . . . ?
C20 C19 C24 C23 1.1(3) . . . . ?
C20 C21 C22 C23 0.0(3) . . . . ?
C21 C22 C23 C24 -0.7(3) . . . . ?
C22 C23 C24 C19 0.1(3) . . . . ?
C24 C19 C20 C21 -1.8(3) . . . . ?
C25 C10 C11 N1 172.44(13) . . . . ?
C25 C10 C11 C12 49.45(16) . . . . ?
C25 C10 C11 C14 -61.08(17) . . . . ?
C25 C10 C27 O5 -47.81(17) . . . . ?
C25 C10 C27 O6 137.27(17) . . . . ?
C26 O4 C25 O3 3.6(2) . . . . ?
C26 O4 C25 C10 -175.22(14) . . . . ?
C27 C10 C11 N1 -65.25(17) . . . . ?
C27 C10 C11 C12 171.76(13) . . . . ?
C27 C10 C11 C14 61.23(18) . . . . ?
C27 C10 C25 O3 134.95(16) . . . . ?
C27 C10 C25 O4 -46.21(17) . . . . ?
C28 O5 C27 O6 5.0(2) . . . . ?
C28 O5 C27 C10 -170.21(13) . . . . ?
C29 O1 C4 C3 172.26(15) . . . . ?
C29 O1 C4 C5 -7.9(2) . . . . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 0.000 68.7 4.3 ?
2 0.278 0.547 0.400 7.3 0.2 ?
3 0.722 0.453 0.600 7.3 0.2 ?
