#------------------------------------------------------------------------------
#$Date: 2024-08-04 04:59:32 +0300 (Sun, 04 Aug 2024) $
#$Revision: 293665 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/34/7133450.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_7133450
loop_
_publ_author_name
'Song, Yuna'
'Song, Hayoung'
'Choi, Yunseop'
'Seo, Jongcheol'
'Lee, Eunsung'
_publ_section_title
;
 Synthesis of sterically congested unsymmetrical 1,2-dicarbonyl radicals
 through a stepwise approach.
;
_journal_issue                   62
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8043
_journal_page_last               8046
_journal_paper_doi               10.1039/d4cc02092h
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'Cl, H2 O, C51 H64 N4 O2'
_chemical_formula_sum            'C51 H66 Cl N4 O3'
_chemical_formula_weight         818.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-03
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6392)
;
_audit_update_record
;
2024-04-24 deposited with the CCDC.	2024-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 122.41(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.135(5)
_cell_length_b                   22.011(4)
_cell_length_c                   21.701(4)
_cell_measurement_reflns_used    24582
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.514
_cell_measurement_theta_min      1.850
_cell_volume                     9733(5)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.719
_diffrn_measurement_device_type  Synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.700000
_diffrn_reflns_av_R_equivalents  0.0838
_diffrn_reflns_av_unetI/netI     0.0923
_diffrn_reflns_Laue_measured_fraction_full 0.952
_diffrn_reflns_Laue_measured_fraction_max 0.719
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            24582
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.719
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.514
_diffrn_reflns_theta_min         1.850
_exptl_absorpt_coefficient_mu    0.122
_exptl_crystal_colour            'clear dark violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_description       block
_exptl_crystal_F_000             3528
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         8888
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0597
_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)+(0.0753P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1668
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4732
_reflns_number_total             8888
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc02092h2.cif
_cod_data_source_block           monoclinic-c2c
_cod_original_cell_volume        9733(4)
_cod_database_code               7133450
_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_max   0.994
_shelx_estimated_absorpt_t_min   0.964
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B)
2.b Ternary CH refined with riding coordinates:
 C17(H17), C20(H20), C32(H32), C29(H29)
2.c Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
2.d Aromatic/amide H refined with riding coordinates:
 C14(H14), C12(H12), C13(H13), C9(H9), C27(H27), C8(H8), C25(H25), C39(H39),
 C26(H26), C46(H46), C37(H37), C48(H48)
2.e Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C30(H30A,H30B,H30C), C41(H41A,H41B,H41C), C51(H51A,H51B,H51C), C42(H42A,
 H42B,H42C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C43(H43A,H43B,H43C),
 C31(H31A,H31B,H31C), C50(H50A,H50B,H50C), C52(H52A,H52B,H52C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.88647(4) 0.12333(3) 0.16790(3) 0.0614(2) Uani 1 1 d . . . . .
O3 O 0.98357(10) 0.14837(10) 0.33587(10) 0.0628(5) Uani 1 1 d . . . . .
H3A H 0.956107 0.140154 0.291242 0.094 Uiso 1 1 d G . . . .
H3B H 1.020849 0.143054 0.341325 0.094 Uiso 1 1 d G . . . .
O1 O 0.66975(10) 0.31812(10) 0.22295(10) 0.0660(6) Uani 1 1 d . . . . .
O2 O 0.79229(11) 0.42838(10) 0.27143(12) 0.0753(6) Uani 1 1 d . . . . .
N2 N 0.63679(10) 0.46608(10) 0.18528(10) 0.0459(6) Uani 1 1 d . . . . .
N1 N 0.65656(11) 0.43274(10) 0.29609(10) 0.0507(6) Uani 1 1 d . . . . .
N4 N 0.78344(12) 0.27319(11) 0.20596(13) 0.0633(7) Uani 1 1 d . . . . .
N3 N 0.85975(13) 0.30712(12) 0.31150(13) 0.0642(7) Uani 1 1 d . . . . .
C16 C 0.67868(13) 0.49670(13) 0.10913(13) 0.0493(7) Uani 1 1 d . . . . .
C10 C 0.63784(13) 0.45872(12) 0.11928(13) 0.0476(7) Uani 1 1 d . . . . .
C5 C 0.59442(13) 0.51525(12) 0.18396(14) 0.0500(7) Uani 1 1 d . . . . .
H5A H 0.563177 0.528251 0.132984 0.060 Uiso 1 1 calc R . . . .
H5B H 0.621698 0.550689 0.211756 0.060 Uiso 1 1 calc R . . . .
C6 C 0.55729(13) 0.49299(13) 0.21718(13) 0.0485(7) Uani 1 1 d . . . . .
H6A H 0.528471 0.458638 0.188374 0.058 Uiso 1 1 calc R . . . .
H6B H 0.529587 0.525973 0.217560 0.058 Uiso 1 1 calc R . . . .
C11 C 0.59243(13) 0.41857(12) 0.06555(13) 0.0485(7) Uani 1 1 d . . . . .
C1 C 0.66621(13) 0.42845(13) 0.24167(14) 0.0514(7) Uani 1 1 d . . . . .
C23 C 0.69881(15) 0.40404(14) 0.36688(14) 0.0574(8) Uani 1 1 d . . . . .
C17 C 0.72400(14) 0.54386(13) 0.16467(14) 0.0524(7) Uani 1 1 d . . . . .
H17 H 0.725675 0.536174 0.211061 0.063 Uiso 1 1 calc R . . . .
C14 C 0.67387(14) 0.49251(13) 0.04241(14) 0.0550(7) Uani 1 1 d . . . . .
H14 H 0.700626 0.517863 0.033383 0.066 Uiso 1 1 calc R . . . .
C7 C 0.60663(14) 0.47273(13) 0.29410(14) 0.0535(7) Uani 1 1 d . . . . .
H7A H 0.628323 0.508768 0.325196 0.064 Uiso 1 1 calc R . . . .
H7B H 0.583761 0.450725 0.313968 0.064 Uiso 1 1 calc R . . . .
C12 C 0.59074(14) 0.41632(13) 0.00041(14) 0.0537(7) Uani 1 1 d . . . . .
H12 H 0.561106 0.389342 -0.037090 0.064 Uiso 1 1 calc R . . . .
C20 C 0.54200(14) 0.38305(12) 0.07224(14) 0.0519(7) Uani 1 1 d . . . . .
H20 H 0.554389 0.385261 0.124160 0.062 Uiso 1 1 calc R . . . .
C28 C 0.75489(15) 0.43635(15) 0.41909(15) 0.0602(8) Uani 1 1 d . . . . .
C13 C 0.63131(15) 0.45255(14) -0.01068(14) 0.0574(8) Uani 1 1 d . . . . .
H13 H 0.629802 0.449846 -0.055244 0.069 Uiso 1 1 calc R . . . .
C21 C 0.47465(14) 0.41300(15) 0.02431(15) 0.0657(8) Uani 1 1 d . . . . .
H21A H 0.461375 0.410943 -0.026956 0.099 Uiso 1 1 calc GR . . . .
H21B H 0.477167 0.455593 0.038737 0.099 Uiso 1 1 calc GR . . . .
H21C H 0.442324 0.391613 0.030491 0.099 Uiso 1 1 calc GR . . . .
C22 C 0.53905(16) 0.31586(13) 0.05183(16) 0.0671(9) Uani 1 1 d . . . . .
H22A H 0.506898 0.294700 0.058489 0.101 Uiso 1 1 calc GR . . . .
H22B H 0.582374 0.297325 0.083252 0.101 Uiso 1 1 calc GR . . . .
H22C H 0.526006 0.312654 0.000708 0.101 Uiso 1 1 calc GR . . . .
C35 C 0.72760(16) 0.26539(15) 0.13129(16) 0.0640(9) Uani 1 1 d . . . . .
C18 C 0.79397(14) 0.53976(15) 0.18152(15) 0.0658(8) Uani 1 1 d . . . . .
H18A H 0.810459 0.498263 0.196689 0.099 Uiso 1 1 calc GR . . . .
H18B H 0.822187 0.568115 0.220922 0.099 Uiso 1 1 calc GR . . . .
H18C H 0.794171 0.550256 0.137753 0.099 Uiso 1 1 calc GR . . . .
C24 C 0.67708(16) 0.35090(14) 0.38247(15) 0.0634(8) Uani 1 1 d . . . . .
C40 C 0.72474(16) 0.30163(15) 0.07746(17) 0.0659(9) Uani 1 1 d . . . . .
C19 C 0.69612(15) 0.60785(13) 0.13812(15) 0.0623(8) Uani 1 1 d . . . . .
H19A H 0.690135 0.615112 0.090356 0.094 Uiso 1 1 calc GR . . . .
H19B H 0.726688 0.637962 0.173163 0.094 Uiso 1 1 calc GR . . . .
H19C H 0.653731 0.611361 0.133888 0.094 Uiso 1 1 calc GR . . . .
C4 C 0.79753(17) 0.31727(15) 0.25520(17) 0.0678(9) Uani 1 1 d . . . . .
C9 C 0.83677(16) 0.23546(15) 0.23165(18) 0.0675(9) Uani 1 1 d . . . . .
H9 H 0.839566 0.200970 0.207124 0.081 Uiso 1 1 calc R . . . .
C36 C 0.68596(17) 0.21688(16) 0.11687(16) 0.0684(9) Uani 1 1 d . . . . .
C44 C 0.89647(16) 0.33853(14) 0.38080(17) 0.0644(8) Uani 1 1 d . . . . .
C27 C 0.79089(16) 0.41093(17) 0.48935(16) 0.0710(9) Uani 1 1 d . . . . .
H27 H 0.829771 0.430536 0.526253 0.085 Uiso 1 1 calc R . . . .
C38 C 0.63495(17) 0.23885(17) -0.01232(16) 0.0699(9) Uani 1 1 d . . . . .
C8 C 0.88417(17) 0.25588(15) 0.29742(18) 0.0692(9) Uani 1 1 d . . . . .
H8 H 0.926394 0.238471 0.328338 0.083 Uiso 1 1 calc R . . . .
C25 C 0.71525(18) 0.32832(16) 0.45355(16) 0.0721(10) Uani 1 1 d . . . . .
H25 H 0.702575 0.291784 0.466043 0.087 Uiso 1 1 calc R . . . .
C32 C 0.61368(17) 0.31909(14) 0.32806(16) 0.0664(9) Uani 1 1 d . . . . .
H32 H 0.594421 0.340444 0.280146 0.080 Uiso 1 1 calc R . . . .
C45 C 0.89046(16) 0.31795(14) 0.43729(17) 0.0634(8) Uani 1 1 d . . . . .
C29 C 0.77588(15) 0.49718(15) 0.40578(15) 0.0639(8) Uani 1 1 d . . . . .
H29 H 0.745484 0.507732 0.353097 0.077 Uiso 1 1 calc R . . . .
C39 C 0.67745(18) 0.28708(16) 0.00540(18) 0.0707(9) Uani 1 1 d . . . . .
H39 H 0.674329 0.311073 -0.032728 0.085 Uiso 1 1 calc R . . . .
C26 C 0.77093(18) 0.35829(17) 0.50568(17) 0.0753(10) Uani 1 1 d . . . . .
H26 H 0.795990 0.342289 0.553772 0.090 Uiso 1 1 calc R . . . .
C46 C 0.93116(17) 0.34451(15) 0.50547(18) 0.0710(9) Uani 1 1 d . . . . .
H46 H 0.927408 0.331734 0.544899 0.085 Uiso 1 1 calc R . . . .
C47 C 0.97670(18) 0.38862(17) 0.51816(19) 0.0781(10) Uani 1 1 d . . . . .
C37 C 0.63951(17) 0.20431(16) 0.04443(17) 0.0726(9) Uani 1 1 d . . . . .
H37 H 0.609993 0.171447 0.032915 0.087 Uiso 1 1 calc R . . . .
C30 C 0.77065(16) 0.54725(15) 0.45143(15) 0.0701(9) Uani 1 1 d . . . . .
H30A H 0.725305 0.549783 0.439232 0.105 Uiso 1 1 calc GR . . . .
H30B H 0.783447 0.586247 0.440872 0.105 Uiso 1 1 calc GR . . . .
H30C H 0.799860 0.537767 0.503409 0.105 Uiso 1 1 calc GR . . . .
C49 C 0.94254(18) 0.38218(16) 0.39058(19) 0.0730(9) Uani 1 1 d . . . . .
C2 C 0.7019(2) 0.3673(2) 0.23816(16) 0.0875(12) Uani 1 1 d . . . . .
C41 C 0.77214(18) 0.35272(16) 0.09493(18) 0.0801(10) Uani 1 1 d . . . . .
H41A H 0.761477 0.386647 0.116050 0.120 Uiso 1 1 calc GR . . . .
H41B H 0.769011 0.366210 0.050125 0.120 Uiso 1 1 calc GR . . . .
H41C H 0.816896 0.338679 0.130021 0.120 Uiso 1 1 calc GR . . . .
C51 C 0.84282(17) 0.26899(16) 0.42547(17) 0.0770(10) Uani 1 1 d . . . . .
H51A H 0.798110 0.282656 0.389592 0.116 Uiso 1 1 calc GR . . . .
H51B H 0.846493 0.259849 0.471720 0.116 Uiso 1 1 calc GR . . . .
H51C H 0.852609 0.232359 0.407338 0.116 Uiso 1 1 calc GR . . . .
C48 C 0.98161(18) 0.40653(17) 0.4603(2) 0.0833(10) Uani 1 1 d . . . . .
H48 H 1.012961 0.436734 0.468446 0.100 Uiso 1 1 calc R . . . .
C42 C 0.58410(17) 0.22294(17) -0.09095(16) 0.0851(11) Uani 1 1 d . . . . .
H42A H 0.540761 0.236613 -0.102962 0.128 Uiso 1 1 calc GR . . . .
H42B H 0.583418 0.178840 -0.097542 0.128 Uiso 1 1 calc GR . . . .
H42C H 0.595229 0.243075 -0.123218 0.128 Uiso 1 1 calc GR . . . .
C33 C 0.56432(17) 0.32282(17) 0.35100(18) 0.0792(10) Uani 1 1 d . . . . .
H33A H 0.583176 0.304460 0.399378 0.119 Uiso 1 1 calc GR . . . .
H33B H 0.524294 0.300911 0.315609 0.119 Uiso 1 1 calc GR . . . .
H33C H 0.553675 0.365484 0.352812 0.119 Uiso 1 1 calc GR . . . .
C3 C 0.7615(2) 0.3778(2) 0.25337(17) 0.0899(12) Uani 1 1 d . . . . .
C34 C 0.62483(19) 0.25207(15) 0.31664(18) 0.0851(11) Uani 1 1 d . . . . .
H34A H 0.658846 0.249743 0.305072 0.128 Uiso 1 1 calc GR . . . .
H34B H 0.583848 0.234883 0.276258 0.128 Uiso 1 1 calc GR . . . .
H34C H 0.638891 0.229035 0.361339 0.128 Uiso 1 1 calc GR . . . .
C43 C 0.69110(18) 0.17785(16) 0.17679(17) 0.0849(11) Uani 1 1 d . . . . .
H43A H 0.730182 0.152068 0.197156 0.127 Uiso 1 1 calc GR . . . .
H43B H 0.651933 0.152233 0.156860 0.127 Uiso 1 1 calc GR . . . .
H43C H 0.694522 0.203886 0.215328 0.127 Uiso 1 1 calc GR . . . .
C31 C 0.84571(17) 0.49667(19) 0.42200(19) 0.0891(11) Uani 1 1 d . . . . .
H31A H 0.876539 0.486951 0.473611 0.134 Uiso 1 1 calc GR . . . .
H31B H 0.856237 0.536756 0.411280 0.134 Uiso 1 1 calc GR . . . .
H31C H 0.849213 0.465984 0.391537 0.134 Uiso 1 1 calc GR . . . .
C50 C 0.94768(19) 0.40269(19) 0.3274(2) 0.0929(12) Uani 1 1 d . . . . .
H50A H 0.907747 0.424755 0.292076 0.139 Uiso 1 1 calc GR . . . .
H50B H 0.952844 0.367163 0.303696 0.139 Uiso 1 1 calc GR . . . .
H50C H 0.985785 0.429465 0.345431 0.139 Uiso 1 1 calc GR . . . .
C52 C 1.01888(19) 0.4172(2) 0.5925(2) 0.1024(13) Uani 1 1 d . . . . .
H52A H 0.991931 0.444166 0.601915 0.154 Uiso 1 1 calc GR . . . .
H52B H 1.054072 0.440749 0.593992 0.154 Uiso 1 1 calc GR . . . .
H52C H 1.038058 0.385322 0.629740 0.154 Uiso 1 1 calc GR . . . .
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'
Cl Cl 0.1484 0.1585 '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
H3A O3 H3B 104.5 . . ?
C10 N2 C5 116.05(19) . . ?
C1 N2 C10 123.8(2) . . ?
C1 N2 C5 119.9(2) . . ?
C1 N1 C23 123.5(2) . . ?
C1 N1 C7 123.3(2) . . ?
C23 N1 C7 112.9(2) . . ?
C4 N4 C35 131.0(3) . . ?
C4 N4 C9 109.3(3) . . ?
C9 N4 C35 119.1(3) . . ?
C4 N3 C44 128.6(3) . . ?
C4 N3 C8 109.5(3) . . ?
C8 N3 C44 121.6(3) . . ?
C10 C16 C17 123.5(2) . . ?
C14 C16 C10 116.8(3) . . ?
C14 C16 C17 119.6(3) . . ?
C16 C10 N2 118.3(2) . . ?
C16 C10 C11 123.3(2) . . ?
C11 C10 N2 118.0(2) . . ?
N2 C5 H5A 109.7 . . ?
N2 C5 H5B 109.7 . . ?
N2 C5 C6 109.7(2) . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
C5 C6 H6A 110.1 . . ?
C5 C6 H6B 110.1 . . ?
C5 C6 C7 107.9(2) . . ?
H6A C6 H6B 108.4 . . ?
C7 C6 H6A 110.1 . . ?
C7 C6 H6B 110.1 . . ?
C10 C11 C20 123.6(2) . . ?
C12 C11 C10 116.8(3) . . ?
C12 C11 C20 119.3(2) . . ?
N2 C1 C2 120.7(2) . . ?
N1 C1 N2 121.0(2) . . ?
N1 C1 C2 117.0(2) . . ?
C28 C23 N1 117.3(3) . . ?
C24 C23 N1 118.5(3) . . ?
C24 C23 C28 123.6(3) . . ?
C16 C17 H17 107.8 . . ?
C16 C17 C18 112.5(2) . . ?
C16 C17 C19 110.2(2) . . ?
C18 C17 H17 107.8 . . ?
C18 C17 C19 110.5(2) . . ?
C19 C17 H17 107.8 . . ?
C16 C14 H14 119.2 . . ?
C13 C14 C16 121.5(3) . . ?
C13 C14 H14 119.2 . . ?
N1 C7 C6 110.9(2) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.0 . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.2(3) . . ?
C13 C12 H12 119.4 . . ?
C11 C20 H20 108.2 . . ?
C11 C20 C21 109.1(2) . . ?
C11 C20 C22 112.6(2) . . ?
C21 C20 H20 108.2 . . ?
C21 C20 C22 110.5(2) . . ?
C22 C20 H20 108.2 . . ?
C23 C28 C29 124.7(2) . . ?
C27 C28 C23 116.2(3) . . ?
C27 C28 C29 119.0(3) . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C40 C35 N4 117.9(3) . . ?
C36 C35 N4 118.0(3) . . ?
C36 C35 C40 123.5(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C23 C24 C25 117.0(3) . . ?
C23 C24 C32 123.6(3) . . ?
C25 C24 C32 119.3(3) . . ?
C35 C40 C39 117.1(3) . . ?
C35 C40 C41 122.1(3) . . ?
C39 C40 C41 120.8(3) . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N4 C4 N3 106.5(3) . . ?
N4 C4 C3 133.4(3) . . ?
N3 C4 C3 119.4(3) . . ?
N4 C9 H9 126.0 . . ?
C8 C9 N4 108.0(3) . . ?
C8 C9 H9 126.0 . . ?
C35 C36 C37 117.4(3) . . ?
C35 C36 C43 122.1(3) . . ?
C37 C36 C43 120.5(3) . . ?
C45 C44 N3 117.8(3) . . ?
C45 C44 C49 122.9(3) . . ?
C49 C44 N3 118.7(3) . . ?
C28 C27 H27 119.4 . . ?
C26 C27 C28 121.2(3) . . ?
C26 C27 H27 119.4 . . ?
C39 C38 C37 118.4(3) . . ?
C39 C38 C42 121.6(3) . . ?
C37 C38 C42 120.0(4) . . ?
N3 C8 H8 126.6 . . ?
C9 C8 N3 106.7(3) . . ?
C9 C8 H8 126.6 . . ?
C24 C25 H25 119.6 . . ?
C26 C25 C24 120.9(3) . . ?
C26 C25 H25 119.6 . . ?
C24 C32 H32 107.8 . . ?
C24 C32 C33 111.2(3) . . ?
C24 C32 C34 112.2(3) . . ?
C33 C32 H32 107.8 . . ?
C33 C32 C34 109.8(3) . . ?
C34 C32 H32 107.8 . . ?
C44 C45 C46 117.0(3) . . ?
C44 C45 C51 121.3(3) . . ?
C46 C45 C51 121.7(3) . . ?
C28 C29 H29 107.9 . . ?
C28 C29 C30 111.2(3) . . ?
C28 C29 C31 113.0(3) . . ?
C30 C29 H29 108.0 . . ?
C31 C29 H29 108.0 . . ?
C31 C29 C30 108.6(3) . . ?
C40 C39 H39 119.0 . . ?
C38 C39 C40 122.0(3) . . ?
C38 C39 H39 119.0 . . ?
C27 C26 C25 121.1(3) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C45 C46 H46 118.6 . . ?
C47 C46 C45 122.7(3) . . ?
C47 C46 H46 118.6 . . ?
C46 C47 C48 117.9(3) . . ?
C46 C47 C52 121.1(4) . . ?
C48 C47 C52 121.0(4) . . ?
C36 C37 C38 121.6(3) . . ?
C36 C37 H37 119.2 . . ?
C38 C37 H37 119.2 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C44 C49 C50 120.9(3) . . ?
C48 C49 C44 116.8(3) . . ?
C48 C49 C50 122.3(3) . . ?
O1 C2 C1 117.0(3) . . ?
O1 C2 C3 130.7(4) . . ?
C3 C2 C1 112.3(4) . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C45 C51 H51A 109.5 . . ?
C45 C51 H51B 109.5 . . ?
C45 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C47 C48 C49 122.7(4) . . ?
C47 C48 H48 118.6 . . ?
C49 C48 H48 118.6 . . ?
C38 C42 H42A 109.5 . . ?
C38 C42 H42B 109.5 . . ?
C38 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O2 C3 C4 120.3(4) . . ?
O2 C3 C2 127.7(5) . . ?
C2 C3 C4 111.8(4) . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C36 C43 H43A 109.5 . . ?
C36 C43 H43B 109.5 . . ?
C36 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C49 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
C49 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C47 C52 H52A 109.5 . . ?
C47 C52 H52B 109.5 . . ?
C47 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 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
O3 H3A 0.8497 . ?
O3 H3B 0.8503 . ?
O1 C2 1.269(4) . ?
O2 C3 1.278(4) . ?
N2 C10 1.455(3) . ?
N2 C5 1.479(3) . ?
N2 C1 1.325(3) . ?
N1 C1 1.324(3) . ?
N1 C23 1.456(3) . ?
N1 C7 1.474(3) . ?
N4 C35 1.460(4) . ?
N4 C4 1.345(4) . ?
N4 C9 1.374(4) . ?
N3 C4 1.353(4) . ?
N3 C44 1.448(4) . ?
N3 C8 1.381(4) . ?
C16 C10 1.397(4) . ?
C16 C17 1.521(4) . ?
C16 C14 1.392(3) . ?
C10 C11 1.404(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.502(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.507(3) . ?
C11 C12 1.393(4) . ?
C11 C20 1.518(4) . ?
C1 C2 1.622(5) . ?
C23 C28 1.406(4) . ?
C23 C24 1.396(4) . ?
C17 H17 1.0000 . ?
C17 C18 1.527(4) . ?
C17 C19 1.534(4) . ?
C14 H14 0.9500 . ?
C14 C13 1.374(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C12 H12 0.9500 . ?
C12 C13 1.380(4) . ?
C20 H20 1.0000 . ?
C20 C21 1.532(4) . ?
C20 C22 1.534(4) . ?
C28 C27 1.405(4) . ?
C28 C29 1.513(4) . ?
C13 H13 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C35 C40 1.385(4) . ?
C35 C36 1.382(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C24 C25 1.397(4) . ?
C24 C32 1.513(4) . ?
C40 C39 1.392(4) . ?
C40 C41 1.501(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C4 C3 1.581(5) . ?
C9 H9 0.9500 . ?
C9 C8 1.341(4) . ?
C36 C37 1.384(4) . ?
C36 C43 1.507(4) . ?
C44 C45 1.386(4) . ?
C44 C49 1.397(5) . ?
C27 H27 0.9500 . ?
C27 C26 1.372(5) . ?
C38 C39 1.380(5) . ?
C38 C37 1.401(4) . ?
C38 C42 1.515(4) . ?
C8 H8 0.9500 . ?
C25 H25 0.9500 . ?
C25 C26 1.375(5) . ?
C32 H32 1.0000 . ?
C32 C33 1.520(4) . ?
C32 C34 1.543(4) . ?
C45 C46 1.392(4) . ?
C45 C51 1.494(4) . ?
C29 H29 1.0000 . ?
C29 C30 1.532(4) . ?
C29 C31 1.526(4) . ?
C39 H39 0.9500 . ?
C26 H26 0.9500 . ?
C46 H46 0.9500 . ?
C46 C47 1.379(5) . ?
C47 C48 1.380(5) . ?
C47 C52 1.508(5) . ?
C37 H37 0.9500 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C49 C48 1.392(5) . ?
C49 C50 1.511(5) . ?
C2 C3 1.311(5) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C48 H48 0.9500 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
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 C2 C3 O2 -176.7(3) . . . . ?
O1 C2 C3 C4 -2.6(5) . . . . ?
N2 C10 C11 C12 174.7(2) . . . . ?
N2 C10 C11 C20 0.7(4) . . . . ?
N2 C5 C6 C7 58.4(3) . . . . ?
N2 C1 C2 O1 -98.4(3) . . . . ?
N2 C1 C2 C3 82.8(4) . . . . ?
N1 C1 C2 O1 68.7(3) . . . . ?
N1 C1 C2 C3 -110.1(3) . . . . ?
N1 C23 C28 C27 173.2(2) . . . . ?
N1 C23 C28 C29 -2.9(4) . . . . ?
N1 C23 C24 C25 -173.0(3) . . . . ?
N1 C23 C24 C32 3.9(4) . . . . ?
N4 C35 C40 C39 169.8(3) . . . . ?
N4 C35 C40 C41 -7.5(4) . . . . ?
N4 C35 C36 C37 -170.1(3) . . . . ?
N4 C35 C36 C43 8.6(5) . . . . ?
N4 C4 C3 O2 -127.6(4) . . . . ?
N4 C4 C3 C2 57.8(5) . . . . ?
N4 C9 C8 N3 -0.8(4) . . . . ?
N3 C4 C3 O2 41.5(4) . . . . ?
N3 C4 C3 C2 -133.0(3) . . . . ?
N3 C44 C45 C46 173.5(3) . . . . ?
N3 C44 C45 C51 -5.9(4) . . . . ?
N3 C44 C49 C48 -173.3(3) . . . . ?
N3 C44 C49 C50 8.4(5) . . . . ?
C16 C10 C11 C12 2.0(4) . . . . ?
C16 C10 C11 C20 -172.0(2) . . . . ?
C16 C14 C13 C12 1.6(4) . . . . ?
C10 N2 C5 C6 136.9(2) . . . . ?
C10 N2 C1 N1 -171.1(3) . . . . ?
C10 N2 C1 C2 -4.6(4) . . . . ?
C10 C16 C17 C18 130.4(3) . . . . ?
C10 C16 C17 C19 -105.9(3) . . . . ?
C10 C16 C14 C13 -0.5(4) . . . . ?
C10 C11 C12 C13 -0.8(4) . . . . ?
C10 C11 C20 C21 103.5(3) . . . . ?
C10 C11 C20 C22 -133.4(3) . . . . ?
C5 N2 C10 C16 82.0(3) . . . . ?
C5 N2 C10 C11 -91.0(3) . . . . ?
C5 N2 C1 N1 2.4(4) . . . . ?
C5 N2 C1 C2 168.9(3) . . . . ?
C5 C6 C7 N1 -48.4(3) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
C1 N2 C10 C16 -104.4(3) . . . . ?
C1 N2 C10 C11 82.6(3) . . . . ?
C1 N2 C5 C6 -37.0(3) . . . . ?
C1 N1 C23 C28 86.0(3) . . . . ?
C1 N1 C23 C24 -102.7(3) . . . . ?
C1 N1 C7 C6 16.1(4) . . . . ?
C1 C2 C3 O2 1.9(5) . . . . ?
C1 C2 C3 C4 176.0(2) . . . . ?
C23 N1 C1 N2 -163.9(3) . . . . ?
C23 N1 C1 C2 29.1(4) . . . . ?
C23 N1 C7 C6 -170.5(2) . . . . ?
C23 C28 C27 C26 -1.5(4) . . . . ?
C23 C28 C29 C30 113.2(3) . . . . ?
C23 C28 C29 C31 -124.3(3) . . . . ?
C23 C24 C25 C26 1.3(5) . . . . ?
C23 C24 C32 C33 -112.4(3) . . . . ?
C23 C24 C32 C34 124.1(3) . . . . ?
C17 C16 C10 N2 2.3(4) . . . . ?
C17 C16 C10 C11 174.9(2) . . . . ?
C17 C16 C14 C13 -176.9(3) . . . . ?
C14 C16 C10 N2 -174.0(2) . . . . ?
C14 C16 C10 C11 -1.4(4) . . . . ?
C14 C16 C17 C18 -53.5(3) . . . . ?
C14 C16 C17 C19 70.3(3) . . . . ?
C7 N1 C1 N2 8.8(4) . . . . ?
C7 N1 C1 C2 -158.2(3) . . . . ?
C7 N1 C23 C28 -87.4(3) . . . . ?
C7 N1 C23 C24 83.9(3) . . . . ?
C12 C11 C20 C21 -70.3(3) . . . . ?
C12 C11 C20 C22 52.7(3) . . . . ?
C20 C11 C12 C13 173.4(3) . . . . ?
C28 C23 C24 C25 -2.3(4) . . . . ?
C28 C23 C24 C32 174.6(3) . . . . ?
C28 C27 C26 C25 0.6(5) . . . . ?
C35 N4 C4 N3 -170.9(3) . . . . ?
C35 N4 C4 C3 -0.7(6) . . . . ?
C35 N4 C9 C8 172.7(3) . . . . ?
C35 C40 C39 C38 0.1(5) . . . . ?
C35 C36 C37 C38 0.5(5) . . . . ?
C24 C23 C28 C27 2.4(4) . . . . ?
C24 C23 C28 C29 -173.7(3) . . . . ?
C24 C25 C26 C27 -0.5(5) . . . . ?
C40 C35 C36 C37 0.4(5) . . . . ?
C40 C35 C36 C43 179.1(3) . . . . ?
C4 N4 C35 C40 74.8(4) . . . . ?
C4 N4 C35 C36 -114.2(4) . . . . ?
C4 N4 C9 C8 0.4(4) . . . . ?
C4 N3 C44 C45 87.5(4) . . . . ?
C4 N3 C44 C49 -101.1(4) . . . . ?
C4 N3 C8 C9 1.0(4) . . . . ?
C9 N4 C35 C40 -95.6(3) . . . . ?
C9 N4 C35 C36 75.5(4) . . . . ?
C9 N4 C4 N3 0.2(4) . . . . ?
C9 N4 C4 C3 170.3(4) . . . . ?
C36 C35 C40 C39 -0.7(5) . . . . ?
C36 C35 C40 C41 -178.0(3) . . . . ?
C44 N3 C4 N4 -174.6(3) . . . . ?
C44 N3 C4 C3 13.6(5) . . . . ?
C44 N3 C8 C9 175.3(3) . . . . ?
C44 C45 C46 C47 -1.2(5) . . . . ?
C44 C49 C48 C47 0.9(5) . . . . ?
C27 C28 C29 C30 -62.8(4) . . . . ?
C27 C28 C29 C31 59.7(4) . . . . ?
C8 N3 C4 N4 -0.7(4) . . . . ?
C8 N3 C4 C3 -172.5(3) . . . . ?
C8 N3 C44 C45 -85.7(4) . . . . ?
C8 N3 C44 C49 85.7(4) . . . . ?
C25 C24 C32 C33 64.4(4) . . . . ?
C25 C24 C32 C34 -59.0(4) . . . . ?
C32 C24 C25 C26 -175.8(3) . . . . ?
C45 C44 C49 C48 -2.3(5) . . . . ?
C45 C44 C49 C50 179.4(3) . . . . ?
C45 C46 C47 C48 -0.2(5) . . . . ?
C45 C46 C47 C52 178.7(3) . . . . ?
C29 C28 C27 C26 174.8(3) . . . . ?
C39 C38 C37 C36 -1.1(5) . . . . ?
C46 C47 C48 C49 0.3(5) . . . . ?
C37 C38 C39 C40 0.8(5) . . . . ?
C49 C44 C45 C46 2.5(5) . . . . ?
C49 C44 C45 C51 -177.0(3) . . . . ?
C41 C40 C39 C38 177.4(3) . . . . ?
C51 C45 C46 C47 178.2(3) . . . . ?
C42 C38 C39 C40 -179.3(3) . . . . ?
C42 C38 C37 C36 179.0(3) . . . . ?
C43 C36 C37 C38 -178.2(3) . . . . ?
C50 C49 C48 C47 179.2(3) . . . . ?
C52 C47 C48 C49 -178.5(3) . . . . ?
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 0.533 0.250 243.4 35.2 ?
2 0.000 0.467 0.750 243.4 35.3 ?
3 0.500 -0.033 0.750 243.4 35.3 ?
4 0.500 0.033 0.250 243.4 35.2 ?
