Reversible structural rearrangement of π-expanded cyclooctatetraene upon two-fold reduction with alkali metals
Zhou, Zheng; Zhu, Yikun; Wei, Zheng; Bergner, John; Neiß, Christian; Doloczki, Susanne; Görling, Andreas; Kivala, Milan; Petrukhina, Marina A.; Chemical Communications  (2022) –; doi:10.1039/D2CC00218C

data_7129725
_publ_section_title
;
 Reversible structural rearrangement of \p-expanded cyclooctatetraene upon
 two-fold reduction with alkali metals
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00218C
_journal_year                    2022
_chemical_formula_moiety         '2(C18 H36 Li N2 O6), C72 H48, 2[C4H8O]'
_chemical_formula_sum            'C116 H136 Li2 N4 O14'
_chemical_formula_weight         1824.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-04-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-10-21 deposited with the CCDC.	2022-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.384(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   31.5584(14)
_cell_length_b                   12.5876(6)
_cell_length_c                   25.8302(11)
_cell_measurement_reflns_used    5942
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.15
_cell_measurement_theta_min      2.97
_cell_volume                     9679.3(8)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'APEX3 v.2018.7-2 (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.42
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.2994
_diffrn_reflns_av_unetI/netI     0.2364
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            59724
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        66.992
_diffrn_reflns_theta_max         66.992
_diffrn_reflns_theta_min         2.969
_diffrn_source                   'INCOATEC ImuS micro-focus source'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker, 2016/2) was used for absorption correction.
wR2(int) was 0.1177 before and 0.0699 after correction.
The Ratio of minimum to maximum transmission is 0.7824.
The \l/2 correction factor is not present.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       plate
_exptl_crystal_F_000             3912
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.650
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1623
_refine_ls_number_reflns         16870
_refine_ls_number_restraints     4125
_refine_ls_restrained_S_all      0.930
_refine_ls_R_factor_all          0.2693
_refine_ls_R_factor_gt           0.1525
_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/[\s^2^(Fo^2^)+(0.1363P)^2^+52.9960P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3249
_refine_ls_wR_factor_ref         0.3945
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7039
_reflns_number_total             16870
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00218c2.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7129725
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.872
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C03Q-C03H
 1.54 with sigma of 0.02
 O00N-C02M = O00N-C032 = O001-C02P = O001-C02J = O003-C03A = O003-C033 = O007-
 C02T = O007-C039 = O029-C03Q = O029-C03E = O002-C02V = O002-C02K
 1.45 with sigma of 0.02
 C036-C032 = C02P-C02M = C02R-C02J = C02O-C02K = C03E-C02V = C03Q-C03H = C033-
 C02T = C03A-C02S = C039-C038
 1.54 with sigma of 0.02
 N01D-C036 = N01D-C03H = N01D-C02S = N01J-C02R = N01J-C02O = N01J-C038
 1.47 with sigma of 0.02
 O004-C02W \\sim O0-C1A
 with sigma of 0.02
 C02Y-Li03 \\sim C1E-Li
 with sigma of 0.04
 O00E-C02U \\sim O00F-C1F
 with sigma of 0.04
 O004-C030 \\sim O0-C0
 with sigma of 0.02
 O005-C03B \\sim O1-C03C
 with sigma of 0.02
 O004-Li03 \\sim O0-Li
 with sigma of 0.02
 N02G-C030 \\sim N02H-C0
 with sigma of 0.04
 C030-Li03 \\sim C0-Li
 with sigma of 0.04
 O008-C034 \\sim O2-C1C
 with sigma of 0.02
 O008-Li03 \\sim O2-Li
 with sigma of 0.02
 O005-C03D \\sim O1-C1B
 with sigma of 0.02
 C03B-C03D \\sim C03C-C1B
 with sigma of 0.04
 O005-Li03 \\sim O1-Li
 with sigma of 0.02
 O00D-C02Y \\sim O3-C1E
 with sigma of 0.02
 N01R-C02Y \\sim N01S-C1E
 with sigma of 0.04
 O00D-Li03 \\sim O3-Li
 with sigma of 0.02
 C02F-C034 \\sim C02G-C1C
 with sigma of 0.04
 O00E-C02Z \\sim O00F-C02{
 with sigma of 0.02
 O008-C02F \\sim O2-C02G
 with sigma of 0.02
 O00E-C03F \\sim O00F-C03G
 with sigma of 0.02
 C02X-C03N \\sim C65-C1I
 with sigma of 0.04
 O00E-Li03 \\sim O00F-Li
 with sigma of 0.02
 C02Z-Li03 \\sim C02{-Li
 with sigma of 0.04
 C031-C03O \\sim C1J-C03P
 with sigma of 0.04
 O01O-C031 \\sim O01P-C1J
 with sigma of 0.02
 O00D-C02L \\sim O3-C1D
 with sigma of 0.02
 N01R-C037 \\sim N01S-C1H
 with sigma of 0.02
 N01R-Li03 \\sim N01S-Li
 with sigma of 0.02
 O01O-C03N \\sim O01P-C1I
 with sigma of 0.04
 C02F-C02L \\sim C02G-C1D
 with sigma of 0.02
 N01R-C03D \\sim N01S-C1B
 with sigma of 0.04
 N02G-C02X \\sim N02H-C65
 with sigma of 0.02
 N02G-C03O \\sim N02H-C03P
 with sigma of 0.04
 N02G-C03I \\sim N02H-C03J
 with sigma of 0.02
 C02L-Li03 \\sim C1D-Li
 with sigma of 0.04
 N02G-C03N \\sim N02H-C1I
 with sigma of 0.02
 C02U-C037 \\sim C1F-C1H
 with sigma of 0.04
 C02U-C02Z \\sim C1F-C02{
 with sigma of 0.02
 C02W-C03B \\sim C1A-C03C
 with sigma of 0.02
 C02X-C034 \\sim C65-C1C
 with sigma of 0.02
 C035-C037 \\sim C1G-C1H
 with sigma of 0.04
 C02Y-C035 \\sim C1E-C1G
 with sigma of 0.02
 N01R-C02U \\sim N01S-C1F
 with sigma of 0.02
 N01R-C035 \\sim N01S-C1G
 with sigma of 0.02
 O00D-C02F \\sim O3-C02G
 with sigma of 0.04
 O01O-C03O \\sim O01P-C03P
 with sigma of 0.02
 O00D-N01R \\sim O3-N01S
 with sigma of 0.04
 O00D-C035 \\sim O3-C1G
 with sigma of 0.04
 O00E-N01R \\sim O00F-N01S
 with sigma of 0.04
 O00E-C031 \\sim O00F-C1J
 with sigma of 0.04
 C037-C03D \\sim C1H-C1B
 with sigma of 0.02
 O01O-C03F \\sim O01P-C03G
 with sigma of 0.04
 N01R-C02Z \\sim N01S-C02{
 with sigma of 0.04
 C03N-C03O \\sim C1I-C03P
 with sigma of 0.02
 C02F-Li03 \\sim C02G-Li
 with sigma of 0.04
 N02G-C034 \\sim N02H-C1C
 with sigma of 0.04
 C02L-C02Y \\sim C1D-C1E
 with sigma of 0.04
 O004-O005 \\sim O0-O1
 with sigma of 0.04
 C02U-C035 \\sim C1F-C1G
 with sigma of 0.04
 O004-O008 \\sim O0-O2
 with sigma of 0.04
 C02U-Li03 \\sim C1F-Li
 with sigma of 0.04
 O004-O00D \\sim O0-O3
 with sigma of 0.04
 O004-O00E \\sim O0-O00F
 with sigma of 0.04
 C02W-C030 \\sim C1A-C0
 with sigma of 0.04
 O004-N01R \\sim O0-N01S
 with sigma of 0.04
 O004-C03B \\sim O0-C03C
 with sigma of 0.04
 C02X-C03I \\sim C65-C03J
 with sigma of 0.04
 O004-C03I \\sim O0-C03J
 with sigma of 0.04
 C02Z-C03F \\sim C02{-C03G
 with sigma of 0.04
 O005-O008 \\sim O1-O2
 with sigma of 0.04
 O005-O00D \\sim O1-O3
 with sigma of 0.04
 O005-O00E \\sim O1-O00F
 with sigma of 0.04
 O005-N01R \\sim O1-N01S
 with sigma of 0.04
 C034-Li03 \\sim C1C-Li
 with sigma of 0.04
 O005-C02W \\sim O1-C1A
 with sigma of 0.04
 O005-C037 \\sim O1-C1H
 with sigma of 0.04
 C035-Li03 \\sim C1G-Li
 with sigma of 0.04
 C037-Li03 \\sim C1H-Li
 with sigma of 0.04
 C03B-Li03 \\sim C03C-Li
 with sigma of 0.04
 C03D-Li03 \\sim C1B-Li
 with sigma of 0.04
 C03F-Li03 \\sim C03G-Li
 with sigma of 0.04
 O008-O00D \\sim O2-O3
 with sigma of 0.04
 O008-O00E \\sim O2-O00F
 with sigma of 0.04
 C03I-C03N \\sim C03J-C1I
 with sigma of 0.04
 O008-N01R \\sim O2-N01S
 with sigma of 0.04
 O008-C02L \\sim O2-C1D
 with sigma of 0.04
 O008-C02X \\sim O2-C65
 with sigma of 0.04
 C02W-Li03 \\sim C1A-Li
 with sigma of 0.04
 C030-C03I \\sim C0-C03J
 with sigma of 0.02
 C031-C03F \\sim C1J-C03G
 with sigma of 0.02
 O00D-O00E \\sim O3-O00F
 with sigma of 0.04
 O002-Li3R \\sim O5-Li3S
 with sigma of 0.02
 O003-C033 \\sim O6-C1N
 with sigma of 0.02
 O003-C03A \\sim O6-C1O
 with sigma of 0.02
 C02K-C02V \\sim C1L-C1M
 with sigma of 0.04
 C02T-Li3R \\sim C1P-Li3S
 with sigma of 0.04
 O003-Li3R \\sim O6-Li3S
 with sigma of 0.02
 C03E-C03Q \\sim C1R-C03R
 with sigma of 0.04
 O007-C039 \\sim O7-C1Q
 with sigma of 0.02
 O007-Li3R \\sim O7-Li3S
 with sigma of 0.02
 O007-C02T \\sim O7-C1P
 with sigma of 0.02
 O00N-C02M \\sim O00O-C02N
 with sigma of 0.02
 C02O-C02R \\sim C1S-C1K
 with sigma of 0.04
 O00N-C032 \\sim O00O-C1U
 with sigma of 0.02
 C02S-C036 \\sim C1V-C1X
 with sigma of 0.04
 N01D-C02S \\sim N01E-C1V
 with sigma of 0.02
 C039-Li3R \\sim C1Q-Li3S
 with sigma of 0.04
 N01D-C036 \\sim N01E-C1X
 with sigma of 0.02
 N01D-C03H \\sim N01E-C1W
 with sigma of 0.02
 N01D-C03Q \\sim N01E-C03R
 with sigma of 0.04
 N01J-O029 \\sim N01K-O8
 with sigma of 0.04
 O029-C02V \\sim O8-C1M
 with sigma of 0.04
 N01J-C02O \\sim N01K-C1S
 with sigma of 0.02
 N01J-C02R \\sim N01K-C1K
 with sigma of 0.02
 C02M-C032 \\sim C02N-C1U
 with sigma of 0.04
 N01J-C038 \\sim N01K-C1T
 with sigma of 0.02
 N01J-Li3R \\sim N01K-Li3S
 with sigma of 0.02
 C02R-Li3R \\sim C1K-Li3S
 with sigma of 0.04
 C02V-Li3R \\sim C1M-Li3S
 with sigma of 0.04
 O029-C03E \\sim O8-C1R
 with sigma of 0.02
 C033-C03A \\sim C1N-C1O
 with sigma of 0.04
 O029-C03Q \\sim O8-C03R
 with sigma of 0.02
 O029-Li3R \\sim O8-Li3S
 with sigma of 0.02
 C02J-C02R \\sim C66-C1K
 with sigma of 0.02
 N01D-C032 \\sim N01E-C1U
 with sigma of 0.04
 C02K-C02O \\sim C1L-C1S
 with sigma of 0.02
 N01J-C02K \\sim N01K-C1L
 with sigma of 0.04
 C02M-C02P \\sim C02N-C02Q
 with sigma of 0.02
 C02J-Li3R \\sim C66-Li3S
 with sigma of 0.04
 C02O-Li3R \\sim C1S-Li3S
 with sigma of 0.04
 C02S-C03A \\sim C1V-C1O
 with sigma of 0.02
 C02P-Li3R \\sim C02Q-Li3S
 with sigma of 0.04
 C02T-C033 \\sim C1P-C1N
 with sigma of 0.02
 C02V-C03E \\sim C1M-C1R
 with sigma of 0.02
 C032-C036 \\sim C1U-C1X
 with sigma of 0.02
 C03Q-Li3R \\sim C03R-Li3S
 with sigma of 0.04
 C038-C039 \\sim C1T-C1Q
 with sigma of 0.02
 O001-C02P \\sim O4-C02Q
 with sigma of 0.02
 N01D-C03A \\sim N01E-C1O
 with sigma of 0.04
 C03H-C03Q \\sim C1W-C03R
 with sigma of 0.02
 N01J-C02J \\sim N01K-C66
 with sigma of 0.04
 N01J-C039 \\sim N01K-C1Q
 with sigma of 0.04
 O029-C03H \\sim O8-C1W
 with sigma of 0.04
 O001-C02J \\sim O4-C66
 with sigma of 0.02
 C02J-C02P \\sim C66-C02Q
 with sigma of 0.04
 O001-O002 \\sim O4-O5
 with sigma of 0.04
 O001-O003 \\sim O4-O6
 with sigma of 0.04
 C02K-Li3R \\sim C1L-Li3S
 with sigma of 0.04
 O001-O007 \\sim O4-O7
 with sigma of 0.04
 O001-N01J \\sim O4-N01K
 with sigma of 0.04
 O001-O029 \\sim O4-O8
 with sigma of 0.04
 O001-C02M \\sim O4-C02N
 with sigma of 0.04
 C02O-C038 \\sim C1S-C1T
 with sigma of 0.04
 O001-C02R \\sim O4-C1K
 with sigma of 0.04
 C02R-C038 \\sim C1K-C1T
 with sigma of 0.04
 O002-O003 \\sim O5-O6
 with sigma of 0.04
 C02S-C03H \\sim C1V-C1W
 with sigma of 0.04
 O002-O007 \\sim O5-O7
 with sigma of 0.04
 O002-N01J \\sim O5-N01K
 with sigma of 0.04
 O002-O029 \\sim O5-O8
 with sigma of 0.04
 C02T-C039 \\sim C1P-C1Q
 with sigma of 0.04
 O002-C02O \\sim O5-C1S
 with sigma of 0.04
 O002-C03E \\sim O5-C1R
 with sigma of 0.04
 C033-Li3R \\sim C1N-Li3S
 with sigma of 0.04
 C036-C03H \\sim C1X-C1W
 with sigma of 0.04
 O003-O007 \\sim O6-O7
 with sigma of 0.04
 O003-N01J \\sim O6-N01K
 with sigma of 0.04
 O003-O029 \\sim O6-O8
 with sigma of 0.04
 C038-Li3R \\sim C1T-Li3S
 with sigma of 0.04
 O003-C02S \\sim O6-C1V
 with sigma of 0.04
 O003-C02T \\sim O6-C1P
 with sigma of 0.04
 C03A-Li3R \\sim C1O-Li3S
 with sigma of 0.04
 C03E-Li3R \\sim C1R-Li3S
 with sigma of 0.04
 O007-N01J \\sim O7-N01K
 with sigma of 0.04
 O007-O029 \\sim O7-O8
 with sigma of 0.04
 O007-C033 \\sim O7-C1N
 with sigma of 0.04
 O007-C038 \\sim O7-C1T
 with sigma of 0.04
 O00N-C02P \\sim O00O-C02Q
 with sigma of 0.04
 O00N-C036 \\sim O00O-C1X
 with sigma of 0.04
 O001-Li3R \\sim O4-Li3S
 with sigma of 0.02
 O002-C02K \\sim O5-C1L
 with sigma of 0.02
 O002-C02V \\sim O5-C1M
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C03Q \\sim O001 \\sim C02J \\sim C02P \\sim Li3R \\sim C02R \\sim C02M \\sim
O002 \\sim O003 \\sim O007 \\sim O029 \\sim N01J \\sim O00N \\sim C02K \\sim
C02V \\sim C033 \\sim C03A \\sim C02T \\sim C039 \\sim C03E \\sim C02O \\sim
C038 \\sim C032 \\sim C02S \\sim C03H \\sim C036 \\sim N01D: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C47 \\sim C006 \\sim C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7
\\sim C8 \\sim C9 \\sim C00M \\sim C11 \\sim C10 \\sim C12 \\sim C13 \\sim C14
\\sim C15 \\sim C18 \\sim C16 \\sim C17 \\sim C21 \\sim C19 \\sim C20 \\sim
C00B \\sim C22 \\sim C23 \\sim C24 \\sim C25 \\sim C26 \\sim C29 \\sim C00I
\\sim C28 \\sim C27 \\sim C32 \\sim C30 \\sim C31 \\sim C35 \\sim C36 \\sim C33
\\sim C34 \\sim C37 \\sim C40 \\sim C38 \\sim C39 \\sim C00C \\sim C00J \\sim
C00L \\sim C42 \\sim C41 \\sim C44 \\sim C45 \\sim C43 \\sim C00O \\sim C46
\\sim C50 \\sim C51 \\sim C48 \\sim C49 \\sim C52 \\sim C53 \\sim C54 \\sim C55
\\sim C56 \\sim C59 \\sim C57 \\sim C58 \\sim C60 \\sim C61 \\sim C62 \\sim C63
\\sim C64: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
O001 \\sim C02J \\sim C02P \\sim Li3R \\sim C02R \\sim C02M \\sim O003 \\sim
O002 \\sim N01J \\sim O029 \\sim O007 \\sim O00N \\sim C033 \\sim C03A \\sim
C02K \\sim C02V \\sim C02O \\sim C038 \\sim C03E \\sim C03Q \\sim C02T \\sim
C039 \\sim C032 \\sim C02S \\sim C03H \\sim C036 \\sim N01D: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C03G \\sim C65 \\sim N02H \\sim C1C \\sim C03J \\sim C1I \\sim O2 \\sim C0
\\sim C03P \\sim Li \\sim C02G \\sim O0 \\sim O01P \\sim O1 \\sim O3 \\sim O00F
\\sim N01S \\sim C1D \\sim C1A \\sim C1J \\sim C03C \\sim C1B \\sim C1E \\sim
C02{ \\sim C1F \\sim C1G \\sim C1H \\sim C031 \\sim O004 \\sim C02W \\sim C030
\\sim Li03 \\sim C03B \\sim C03I \\sim O005 \\sim O008 \\sim N01R \\sim O00D
\\sim O00E \\sim N02G \\sim C03D \\sim C02F \\sim C034 \\sim C02U \\sim C035
\\sim C037 \\sim C02L \\sim C02Y \\sim C02Z \\sim C03F \\sim C02X \\sim C03N
\\sim C03O \\sim O01O: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
O00N \\sim O001 \\sim C02J \\sim C02P \\sim Li3R \\sim C02R \\sim C02M \\sim
O003 \\sim O029 \\sim O002 \\sim O007 \\sim N01J \\sim C033 \\sim C03A \\sim
C03E \\sim C03Q \\sim C02K \\sim C02V \\sim C02T \\sim C039 \\sim C02O \\sim
C038 \\sim C032 \\sim C02S \\sim C03H \\sim C036 \\sim N01D: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C1N \\sim C02N \\sim C02Q \\sim O00O \\sim O4 \\sim C1U \\sim C66 \\sim Li3S
\\sim C1X \\sim C1K \\sim O5 \\sim O6 \\sim O7 \\sim O8 \\sim N01K \\sim N01E
\\sim C1L \\sim C1M \\sim C1O \\sim C1P \\sim C1Q \\sim C1R \\sim C03R \\sim
C1S \\sim C1T \\sim C1V \\sim C1W \\sim C033 \\sim O001 \\sim C02J \\sim C02P
\\sim Li3R \\sim C02R \\sim C02M \\sim O002 \\sim O003 \\sim O007 \\sim N01J
\\sim O029 \\sim O00N \\sim C02K \\sim C02V \\sim C03A \\sim C02T \\sim C039
\\sim C02O \\sim C038 \\sim C03E \\sim C03Q \\sim C032 \\sim C02S \\sim C03H
\\sim C036 \\sim N01D: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 C037, O004, C02W, C030, Li03, C03B, C03I, N01R, O005, O008, O00D, O00E, N02G,
 C02U, C035, C03D, C02F, C034, C02L, C02Y, C02Z, C03F, C02X, C03N, C031, C03O,
 O01O
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C40, C006, C1, C2, C3, C4, C5, C6, C7, C8, C9, C00M, C11, C10, C12, C13, C14,
 C15, C18, C16, C17, C21, C19, C20, C00B, C22, C23, C24, C25, C26, C29, C00I,
 C28, C27, C32, C30, C31, C35, C36, C33, C34, C37, C38, C39, C00C, C00J, C00L,
 C42, C41, C44, C45, C43, C00O, C46, C47, C50, C51, C48, C49, C52, C53, C54,
 C55, C56, C59, C57, C58, C60, C61, C62, C63, C64
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O001, C02J, C02P, Li3R, C02R, C02M, O003, O002, N01J, O029, O007, O00N, C033,
 C03A, C02K, C02V, C02O, C038, C03E, C03Q, C02T, C039, C032, C02S, C03H, C036,
 N01D
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C031, O004, C02W, C030, Li03, C03B, C03I, O005, O008, N01R, O00D, O00E, N02G,
 C03D, C02F, C034, C02U, C035, C037, C02L, C02Y, C02Z, C03F, C02X, C03N, C03O,
 O01O, C03G, C65, N02H, C1C, C03J, C1I, O2, C0, C03P, Li, C02G, O0, O01P, O1,
 O3, O00F, N01S, C1D, C1A, C1J, C03C, C1B, C1E, C02{, C1F, C1G, C1H
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C032, O001, C02J, C02P, Li3R, C02R, C02M, O003, O029, O002, O007, N01J, O00N,
 C033, C03A, C03E, C03Q, C02K, C02V, C02T, C039, C02O, C038, C02S, C03H, C036,
 N01D
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C033, O001, C02J, C02P, Li3R, C02R, C02M, O002, O003, O007, N01J, O029, O00N,
 C02K, C02V, C03A, C02T, C039, C02O, C038, C03E, C03Q, C032, C02S, C03H, C036,
 N01D, C1N, C02N, C02Q, O00O, O4, C1U, C66, Li3S, C1X, C1K, O5, O6, O7, O8,
 N01K, N01E, C1L, C1M, C1O, C1P, C1Q, C1R, C03R, C1S, C1T, C1V, C1W
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C65)=Sof(H65A)=Sof(H65B)=Sof(O0)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(C0)=
 Sof(H0A)=Sof(H0B)=Sof(Li)=Sof(C03C)=Sof(H9)=Sof(HL)=Sof(C03J)=Sof(H10)=Sof(HM)=
 Sof(O1)=Sof(O2)=Sof(O3)=Sof(O00F)=Sof(N01S)=Sof(N02H)=Sof(C1B)=Sof(H1BA)=
 Sof(H1BB)=Sof(C02G)=Sof(H11)=Sof(HN)=Sof(C1C)=Sof(H1CA)=Sof(H1CB)=Sof(C1D)=
 Sof(H1DA)=Sof(H1DB)=Sof(C1E)=Sof(H1EA)=Sof(H1EB)=Sof(C02{)=Sof(H16)=Sof(HO)=
 Sof(C03G)=Sof(H17)=Sof(HP)=Sof(C1F)=Sof(H1FA)=Sof(H1FB)=Sof(C1G)=Sof(H1GA)=
 Sof(H1GB)=Sof(C1H)=Sof(H1HA)=Sof(H1HB)=Sof(C1I)=Sof(H1IA)=Sof(H1IB)=Sof(C1J)=
 Sof(H1JA)=Sof(H1JB)=Sof(C03P)=Sof(H18)=Sof(HQ)=Sof(O01P)=1-FVAR(1)
 Sof(O004)=Sof(O005)=Sof(O008)=Sof(O00D)=Sof(O00E)=Sof(O01O)=Sof(N01R)=
 Sof(C02F)=Sof(H02S)=Sof(H02T)=Sof(N02G)=Sof(C02L)=Sof(H02U)=Sof(H02V)=
 Sof(C02U)=Sof(H02W)=Sof(H02X)=Sof(C02W)=Sof(H02Y)=Sof(H)=Sof(C02X)=Sof(H02Z)=
 Sof(HA)=Sof(C02Y)=Sof(H02)=Sof(HB)=Sof(C02Z)=Sof(H1)=Sof(HC)=Sof(C030)=
 Sof(H03S)=Sof(H03T)=Sof(C031)=Sof(H03U)=Sof(H03V)=Sof(C034)=Sof(H03W)=
 Sof(H03X)=Sof(C035)=Sof(H03Y)=Sof(HD)=Sof(C037)=Sof(H03Z)=Sof(HE)=Sof(C03B)=
 Sof(H03)=Sof(HF)=Sof(C03D)=Sof(H2)=Sof(HG)=Sof(C03F)=Sof(H3)=Sof(HH)=Sof(C03I)=
 Sof(H4)=Sof(HI)=Sof(C03N)=Sof(H5)=Sof(HJ)=Sof(C03O)=Sof(H8)=Sof(HK)=Sof(Li03)=
 FVAR(1)
 Sof(C02N)=Sof(H19)=Sof(HR)=Sof(O4)=Sof(C66)=Sof(H66A)=Sof(H66B)=Sof(C02Q)=
 Sof(H21)=Sof(HS)=Sof(Li3S)=Sof(C1K)=Sof(H1KA)=Sof(H1KB)=Sof(O5)=Sof(O6)=
 Sof(O7)=Sof(O8)=Sof(N01K)=Sof(O00O)=Sof(C1L)=Sof(H1LA)=Sof(H1LB)=Sof(C1M)=
 Sof(H1MA)=Sof(H1MB)=Sof(C1N)=Sof(H1NA)=Sof(H1NB)=Sof(C1O)=Sof(H1OA)=Sof(H1OB)=
 Sof(C1P)=Sof(H1PA)=Sof(H1PB)=Sof(C1Q)=Sof(H1QA)=Sof(H1QB)=Sof(C1R)=Sof(H1RA)=
 Sof(H1RB)=Sof(C03R)=Sof(H27)=Sof(HT)=Sof(C1S)=Sof(H1SA)=Sof(H1SB)=Sof(C1T)=
 Sof(H1TA)=Sof(H1TB)=Sof(C1U)=Sof(H1UA)=Sof(H1UB)=Sof(C1V)=Sof(H1VA)=Sof(H1VB)=
 Sof(C1W)=Sof(H1WA)=Sof(H1WB)=Sof(C1X)=Sof(H1XA)=Sof(H1XB)=Sof(N01E)=1-FVAR(2)
 Sof(O001)=Sof(O002)=Sof(O003)=Sof(O007)=Sof(O00N)=Sof(N01D)=Sof(N01J)=
 Sof(O029)=Sof(C02J)=Sof(H02A)=Sof(H02B)=Sof(C02K)=Sof(H02C)=Sof(H02D)=
 Sof(C02M)=Sof(H02E)=Sof(H02F)=Sof(C02O)=Sof(H02G)=Sof(H02H)=Sof(C02P)=
 Sof(H02I)=Sof(H02J)=Sof(C02R)=Sof(H02K)=Sof(H02L)=Sof(C02S)=Sof(H02M)=
 Sof(H02N)=Sof(C02T)=Sof(H02O)=Sof(H02P)=Sof(C02V)=Sof(H02Q)=Sof(H02R)=
 Sof(C032)=Sof(H03A)=Sof(H03B)=Sof(C033)=Sof(H03C)=Sof(H03D)=Sof(C036)=
 Sof(H03E)=Sof(H03F)=Sof(C038)=Sof(H03G)=Sof(H03H)=Sof(C039)=Sof(H03I)=
 Sof(H03J)=Sof(C03A)=Sof(H03K)=Sof(H03L)=Sof(C03E)=Sof(H03M)=Sof(H03N)=
 Sof(C03H)=Sof(H03O)=Sof(H03P)=Sof(C03Q)=Sof(H03Q)=Sof(H03R)=Sof(Li3R)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C02F(H02S,H02T), C02J(H02A,H02B), C02K(H02C,H02D), C02L(H02U,H02V), C02M(H02E,
 H02F), C02O(H02G,H02H), C02P(H02I,H02J), C02R(H02K,H02L), C02S(H02M,H02N),
 C02T(H02O,H02P), C02U(H02W,H02X), C02V(H02Q,H02R), C02W(H02Y,H), C02X(H02Z,HA),
  C02Y(H02,HB), C02Z(H1,HC), C030(H03S,H03T), C031(H03U,H03V), C032(H03A,H03B),
 C033(H03C,H03D), C034(H03W,H03X), C035(H03Y,HD), C036(H03E,H03F), C037(H03Z,
 HE), C038(H03G,H03H), C039(H03I,H03J), C03A(H03K,H03L), C03B(H03,HF), C03D(H2,
 HG), C03E(H03M,H03N), C03F(H3,HH), C03H(H03O,H03P), C03I(H4,HI), C03N(H5,HJ),
 C03O(H8,HK), C03Q(H03Q,H03R), C65(H65A,H65B), C1A(H1AA,H1AB), C0(H0A,H0B),
 C03C(H9,HL), C03J(H10,HM), C1B(H1BA,H1BB), C02G(H11,HN), C1C(H1CA,H1CB),
 C1D(H1DA,H1DB), C1E(H1EA,H1EB), C02{(H16,HO), C03G(H17,HP), C1F(H1FA,H1FB),
 C1G(H1GA,H1GB), C1H(H1HA,H1HB), C1I(H1IA,H1IB), C1J(H1JA,H1JB), C03P(H18,HQ),
 C02N(H19,HR), C66(H66A,H66B), C02Q(H21,HS), C1K(H1KA,H1KB), C1L(H1LA,H1LB),
 C1M(H1MA,H1MB), C1N(H1NA,H1NB), C1O(H1OA,H1OB), C1P(H1PA,H1PB), C1Q(H1QA,H1QB),
  C1R(H1RA,H1RB), C03R(H27,HT), C1S(H1SA,H1SB), C1T(H1TA,H1TB), C1U(H1UA,H1UB),
 C1V(H1VA,H1VB), C1W(H1WA,H1WB), C1X(H1XA,H1XB)
6.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00J(H00J), C31(H31), C48(H48), C51(H51), C49(H49), C30(H30),
 C41(H41), C40(H40), C59(H59), C20(H20), C6(H6), C35(H35), C29(H29), C7(H7),
 C12(H12), C14(H14), C32(H32), C50(H50), C53(H53), C22(H22), C13(H13), C23(H23),
  C57(H57), C46(H46), C61(H61), C43(H43), C34(H34), C64(H64), C58(H58),
 C44(H44), C60(H60), C26(H26), C25(H25), C36(H36), C33(H33), C54(H54), C47(H47),
  C42(H42), C63(H63), C56(H56), C37(H37), C15(H15), C52(H52), C24(H24),
 C45(H45), C55(H55), C62(H62)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              67457
_shelx_fab_checksum              34531
_olex2_submission_special_instructions 'No special instructions were received'