#------------------------------------------------------------------------------
#$Date: 2022-08-06 14:43:30 +0300 (Sat, 06 Aug 2022) $
#$Revision: 277103 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/70/1567048.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_1567048
loop_
_publ_author_name
'Gorai, Tumpa'
'Lovitt, June I.'
'Umadevi, Deivasigamani'
'McManus, Gavin'
'Gunnlaugsson, Thorfinnur'
_publ_section_title
;
 Hierarchical supramolecular co-assembly formation employing
 multi-component light-harvesting charge transfer interactions giving rise
 to long-wavelength emitting luminescent microspheres.
;
_journal_issue                   26
_journal_name_full               'Chemical science'
_journal_page_first              7805
_journal_page_last               7813
_journal_paper_doi               10.1039/d2sc02097a
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration syn
_chemical_formula_moiety         '2(C10 H2 N4), C31 H27 N3 O3, C2 H6 O'
_chemical_formula_sum            'C53 H37 N11 O4'
_chemical_formula_weight         891.93
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-02-28 deposited with the CCDC.	2022-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                93.3946(13)
_cell_angle_beta                 99.9779(14)
_cell_angle_gamma                107.9484(13)
_cell_formula_units_Z            1
_cell_length_a                   10.1334(4)
_cell_length_b                   10.2002(3)
_cell_length_c                   11.4807(4)
_cell_measurement_reflns_used    1362
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.56
_cell_measurement_theta_min      2.52
_cell_volume                     1103.79(7)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'APEX 3 (Bruker, 2017) '
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CMOS area detector'
_diffrn_detector_area_resol_mean 5.12
_diffrn_detector_type            'Bruker PHOTON 50'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Quest ECO'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_detector       'Bruker PHOTON 50'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            45138
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.755
_diffrn_reflns_theta_min         2.484
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_type              'Siemens, KFF Mo 2K -90 C'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0587 before and 0.0517 after correction.
The Ratio of minimum to maximum transmission is 0.9434.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 3658 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     621
_refine_ls_number_reflns         13673
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0551
_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)+(0.0540P)²+0.3529P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1315
_reflns_Friedel_coverage         0.990
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                9700
_reflns_number_total             13673
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc02097a2.cif
_cod_data_source_block           DPA-TCNB
_cod_depositor_comments          'Adding full bibliography for 1567048.cif.'
_cod_database_code               1567048
_shelx_shelxl_version_number     2016/4
_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   0.990
_shelx_estimated_absorpt_t_min   0.970
_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, All O(H) groups
2. Restrained distances
 O7-H7
 0.9 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C11(H11), C26(H26)
3.b Secondary CH2 refined with riding coordinates:
 C67(H67A,H67B)
3.c Aromatic/amide H refined with riding coordinates:
 C38(H38), C41(H41), C3(H3), C5(H5), N10(H10), C14(H14), C15(H15), C17(H17),
 C18(H18), C19(H19), C20(H20), C22(H22), N25(H25), C29(H29), C31(H31), C32(H32),
  C33(H33), C34(H34), C36(H36), C37(H37), C52(H52), C55(H55)
3.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C27(H27A,H27B,H27C), C68(H68A,H68B,H68C)
3.e Idealised tetrahedral OH refined as rotating group:
 O66(H66)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'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
C38 C 0.5521(3) 0.1683(3) 0.3918(3) 0.0181(6) Uani 1 1 d . . . . .
H38 H 0.575336 0.262527 0.423880 0.022 Uiso 1 1 calc R U . . .
C39 C 0.6433(3) 0.1267(3) 0.3325(3) 0.0182(7) Uani 1 1 d . . . . .
C40 C 0.6089(3) -0.0129(4) 0.2844(3) 0.0185(7) Uani 1 1 d . . . . .
C41 C 0.4838(4) -0.1092(4) 0.2960(3) 0.0196(7) Uani 1 1 d . . . . .
H41 H 0.460945 -0.203320 0.263802 0.024 Uiso 1 1 calc R U . . .
C42 C 0.3910(4) -0.0690(3) 0.3548(3) 0.0177(6) Uani 1 1 d . . . . .
C43 C 0.4254(3) 0.0699(4) 0.4039(3) 0.0178(6) Uani 1 1 d . . . . .
C44 C 0.7740(4) 0.2271(4) 0.3193(3) 0.0212(7) Uani 1 1 d . . . . .
N45 N 0.8784(3) 0.3060(3) 0.3090(3) 0.0267(7) Uani 1 1 d . . . . .
C46 C 0.7028(4) -0.0561(4) 0.2214(3) 0.0219(7) Uani 1 1 d . . . . .
N47 N 0.7744(3) -0.0934(4) 0.1706(3) 0.0311(7) Uani 1 1 d . . . . .
C48 C 0.2562(4) -0.1689(4) 0.3597(3) 0.0205(7) Uani 1 1 d . . . . .
N49 N 0.1481(3) -0.2505(3) 0.3570(3) 0.0259(6) Uani 1 1 d . . . . .
C50 C 0.3305(4) 0.1113(4) 0.4665(3) 0.0207(7) Uani 1 1 d . . . . .
N51 N 0.2555(3) 0.1435(3) 0.5169(3) 0.0270(7) Uani 1 1 d . . . . .
N1 N 0.1323(3) 0.5092(3) 0.5374(2) 0.0163(5) Uani 1 1 d . . . . .
C2 C 0.0768(3) 0.5324(3) 0.6310(3) 0.0171(6) Uani 1 1 d . . . . .
C3 C 0.1379(3) 0.5306(3) 0.7479(3) 0.0190(6) Uani 1 1 d . . . . .
H3 H 0.091761 0.543392 0.810869 0.023 Uiso 1 1 calc R U . . .
C4 C 0.2681(3) 0.5098(3) 0.7710(3) 0.0199(6) Uani 1 1 d . . . . .
C5 C 0.3326(3) 0.4915(3) 0.6765(3) 0.0200(6) Uani 1 1 d . . . . .
H5 H 0.424076 0.481612 0.689701 0.024 Uiso 1 1 calc R U . . .
C6 C 0.2582(3) 0.4883(3) 0.5617(3) 0.0173(6) Uani 1 1 d . . . . .
O7 O 0.3243(3) 0.5068(3) 0.8868(2) 0.0259(5) Uani 1 1 d D . . . .
C8 C 0.3190(3) 0.4593(3) 0.4550(3) 0.0186(6) Uani 1 1 d . . . . .
O9 O 0.4412(2) 0.4578(3) 0.4656(2) 0.0262(5) Uani 1 1 d . . . . .
N10 N 0.2280(3) 0.4374(3) 0.3507(2) 0.0188(5) Uani 1 1 d . . . . .
H10 H 0.139690 0.431572 0.351249 0.023 Uiso 1 1 calc R U . . .
C11 C 0.2690(4) 0.4228(4) 0.2358(3) 0.0195(7) Uani 1 1 d . . . . .
H11 H 0.369286 0.483661 0.243238 0.023 Uiso 1 1 calc R U . . .
C12 C 0.1744(4) 0.4743(4) 0.1432(3) 0.0260(7) Uani 1 1 d . . . . .
H12A H 0.075753 0.414569 0.133556 0.039 Uiso 1 1 calc R U . . .
H12B H 0.204620 0.471424 0.066827 0.039 Uiso 1 1 calc R U . . .
H12C H 0.182191 0.569897 0.170164 0.039 Uiso 1 1 calc R U . . .
C13 C 0.2593(3) 0.2746(4) 0.1959(3) 0.0192(7) Uani 1 1 d . . . . .
C14 C 0.1408(4) 0.1612(4) 0.2090(3) 0.0210(7) Uani 1 1 d . . . . .
H14 H 0.071309 0.178250 0.248056 0.025 Uiso 1 1 calc R U . . .
C15 C 0.1254(4) 0.0281(4) 0.1663(3) 0.0223(7) Uani 1 1 d . . . . .
H15 H 0.046085 -0.046114 0.176756 0.027 Uiso 1 1 calc R U . . .
C16 C 0.2263(4) -0.0001(4) 0.1067(3) 0.0212(7) Uani 1 1 d . . . . .
C17 C 0.2115(4) -0.1383(4) 0.0596(3) 0.0251(8) Uani 1 1 d . . . . .
H17 H 0.132540 -0.214209 0.067975 0.030 Uiso 1 1 calc R U . . .
C18 C 0.3128(4) -0.1598(4) 0.0023(3) 0.0273(8) Uani 1 1 d . . . . .
H18 H 0.303128 -0.251329 -0.029175 0.033 Uiso 1 1 calc R U . . .
C19 C 0.4303(4) -0.0486(4) -0.0105(3) 0.0280(8) Uani 1 1 d . . . . .
H19 H 0.498660 -0.065657 -0.050932 0.034 Uiso 1 1 calc R U . . .
C20 C 0.4472(4) 0.0834(4) 0.0344(3) 0.0247(8) Uani 1 1 d . . . . .
H20 H 0.527896 0.157341 0.026104 0.030 Uiso 1 1 calc R U . . .
C21 C 0.3461(3) 0.1113(4) 0.0931(3) 0.0189(7) Uani 1 1 d . . . . .
C22 C 0.3579(4) 0.2486(4) 0.1391(3) 0.0197(7) Uani 1 1 d . . . . .
H22 H 0.436782 0.324025 0.129907 0.024 Uiso 1 1 calc R U . . .
C23 C -0.0602(3) 0.5640(3) 0.6055(3) 0.0172(6) Uani 1 1 d . . . . .
O24 O -0.1279(2) 0.5684(2) 0.6847(2) 0.0233(5) Uani 1 1 d . . . . .
N25 N -0.0999(3) 0.5877(3) 0.4940(2) 0.0181(5) Uani 1 1 d . . . . .
H25 H -0.045386 0.584041 0.442827 0.022 Uiso 1 1 calc R U . . .
C26 C -0.2303(3) 0.6196(4) 0.4532(3) 0.0191(7) Uani 1 1 d . . . . .
H26 H -0.307891 0.556064 0.486180 0.023 Uiso 1 1 calc R U . . .
C27 C -0.2697(4) 0.5932(4) 0.3185(3) 0.0269(7) Uani 1 1 d . . . . .
H27A H -0.195117 0.655453 0.284722 0.040 Uiso 1 1 calc R U . . .
H27B H -0.359364 0.610383 0.291048 0.040 Uiso 1 1 calc R U . . .
H27C H -0.280275 0.496580 0.292545 0.040 Uiso 1 1 calc R U . . .
C28 C -0.2138(3) 0.7691(4) 0.4972(3) 0.0197(7) Uani 1 1 d . . . . .
C29 C -0.3139(3) 0.7970(4) 0.5524(3) 0.0184(6) Uani 1 1 d . . . . .
H29 H -0.392743 0.722651 0.563382 0.022 Uiso 1 1 calc R U . . .
C30 C -0.3011(3) 0.9363(4) 0.5934(3) 0.0188(7) Uani 1 1 d . . . . .
C31 C -0.4001(4) 0.9672(4) 0.6535(3) 0.0231(7) Uani 1 1 d . . . . .
H31 H -0.479737 0.894490 0.665719 0.028 Uiso 1 1 calc R U . . .
C32 C -0.3817(4) 1.1015(4) 0.6942(3) 0.0297(9) Uani 1 1 d . . . . .
H32 H -0.448632 1.121023 0.735025 0.036 Uiso 1 1 calc R U . . .
C33 C -0.2656(4) 1.2112(4) 0.6768(3) 0.0270(8) Uani 1 1 d . . . . .
H33 H -0.255116 1.303897 0.705505 0.032 Uiso 1 1 calc R U . . .
C34 C -0.1676(4) 1.1852(4) 0.6188(3) 0.0255(8) Uani 1 1 d . . . . .
H34 H -0.089134 1.259898 0.607521 0.031 Uiso 1 1 calc R U . . .
C35 C -0.1828(4) 1.0462(4) 0.5750(3) 0.0199(7) Uani 1 1 d . . . . .
C36 C -0.0837(4) 1.0151(4) 0.5154(3) 0.0225(7) Uani 1 1 d . . . . .
H36 H -0.005672 1.088242 0.501495 0.027 Uiso 1 1 calc R U . . .
C37 C -0.0987(4) 0.8803(4) 0.4773(3) 0.0222(7) Uani 1 1 d . . . . .
H37 H -0.030941 0.861232 0.437168 0.027 Uiso 1 1 calc R U . . .
C52 C -0.0300(3) -0.1196(4) 0.7968(3) 0.0191(7) Uani 1 1 d . . . . .
H52 H -0.065811 -0.215852 0.768581 0.023 Uiso 1 1 calc R U . . .
C53 C -0.1074(4) -0.0576(4) 0.8577(3) 0.0200(7) Uani 1 1 d . . . . .
C54 C -0.0557(4) 0.0847(4) 0.8988(3) 0.0204(7) Uani 1 1 d . . . . .
C55 C 0.0753(4) 0.1654(4) 0.8803(3) 0.0211(7) Uani 1 1 d . . . . .
H55 H 0.110937 0.261783 0.908058 0.025 Uiso 1 1 calc R U . . .
C56 C 0.1539(4) 0.1044(3) 0.8210(3) 0.0192(7) Uani 1 1 d . . . . .
C57 C 0.1005(3) -0.0378(4) 0.7783(3) 0.0179(7) Uani 1 1 d . . . . .
C58 C -0.2433(4) -0.1429(4) 0.8762(3) 0.0238(7) Uani 1 1 d . . . . .
N59 N -0.3507(4) -0.2125(4) 0.8902(3) 0.0335(8) Uani 1 1 d . . . . .
C60 C -0.1381(4) 0.1474(4) 0.9612(3) 0.0224(7) Uani 1 1 d . . . . .
N61 N -0.2022(3) 0.1975(4) 1.0109(3) 0.0289(7) Uani 1 1 d . . . . .
C62 C 0.2918(4) 0.1862(4) 0.8053(3) 0.0206(7) Uani 1 1 d . . . . .
N63 N 0.4018(3) 0.2505(3) 0.7960(3) 0.0269(7) Uani 1 1 d . . . . .
C64 C 0.1822(4) -0.0990(4) 0.7154(3) 0.0209(7) Uani 1 1 d . . . . .
N65 N 0.2486(3) -0.1460(3) 0.6652(3) 0.0273(7) Uani 1 1 d . . . . .
O66 O 0.5877(3) 0.5182(3) 0.9809(3) 0.0373(6) Uani 1 1 d . . . . .
H66 H 0.609885 0.604796 0.995717 0.056 Uiso 1 1 calc R U . . .
C67 C 0.6953(4) 0.4846(4) 0.9269(4) 0.0368(9) Uani 1 1 d . . . . .
H67A H 0.693477 0.518155 0.847673 0.044 Uiso 1 1 calc R U . . .
H67B H 0.672366 0.382506 0.915094 0.044 Uiso 1 1 calc R U . . .
C68 C 0.8410(4) 0.5480(5) 1.0016(4) 0.0404(10) Uani 1 1 d . . . . .
H68A H 0.909953 0.526820 0.960021 0.061 Uiso 1 1 calc R U . . .
H68B H 0.845267 0.509836 1.078038 0.061 Uiso 1 1 calc R U . . .
H68C H 0.863030 0.648846 1.015783 0.061 Uiso 1 1 calc R U . . .
H7 H 0.414(2) 0.521(5) 0.877(4) 0.038(12) Uiso 1 1 d D . . . .
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
C39 C38 H38 120.4 . . ?
C39 C38 C43 119.2(3) . . ?
C43 C38 H38 120.4 . . ?
C38 C39 C40 120.6(3) . . ?
C38 C39 C44 119.8(3) . . ?
C40 C39 C44 119.6(3) . . ?
C39 C40 C46 120.7(3) . . ?
C41 C40 C39 120.0(3) . . ?
C41 C40 C46 119.3(3) . . ?
C40 C41 H41 119.9 . . ?
C40 C41 C42 120.1(3) . . ?
C42 C41 H41 119.9 . . ?
C41 C42 C43 120.1(3) . . ?
C41 C42 C48 119.6(3) . . ?
C43 C42 C48 120.3(3) . . ?
C38 C43 C42 120.0(3) . . ?
C38 C43 C50 119.8(3) . . ?
C42 C43 C50 120.2(3) . . ?
N45 C44 C39 179.4(4) . . ?
N47 C46 C40 178.3(4) . . ?
N49 C48 C42 176.2(4) . . ?
N51 C50 C43 179.5(4) . . ?
C2 N1 C6 116.4(3) . . ?
N1 C2 C3 124.2(3) . . ?
N1 C2 C23 117.0(3) . . ?
C3 C2 C23 118.8(3) . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.4(3) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 C5 119.2(3) . . ?
O7 C4 C3 116.8(3) . . ?
O7 C4 C5 124.0(3) . . ?
C4 C5 H5 121.2 . . ?
C4 C5 C6 117.5(3) . . ?
C6 C5 H5 121.2 . . ?
N1 C6 C5 124.1(3) . . ?
N1 C6 C8 116.1(3) . . ?
C5 C6 C8 119.9(3) . . ?
C4 O7 H7 96(3) . . ?
O9 C8 C6 121.9(3) . . ?
O9 C8 N10 124.3(3) . . ?
N10 C8 C6 113.8(3) . . ?
C8 N10 H10 118.5 . . ?
C8 N10 C11 122.9(3) . . ?
C11 N10 H10 118.5 . . ?
N10 C11 H11 108.3 . . ?
N10 C11 C12 108.3(3) . . ?
N10 C11 C13 112.9(3) . . ?
C12 C11 H11 108.3 . . ?
C13 C11 H11 108.3 . . ?
C13 C11 C12 110.5(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C11 120.3(3) . . ?
C22 C13 C11 120.8(3) . . ?
C22 C13 C14 118.8(3) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.1(3) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.7(3) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C17 121.7(3) . . ?
C15 C16 C21 119.4(3) . . ?
C21 C16 C17 118.9(3) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 C16 119.3(4) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 121.0(4) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.7(3) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.6(4) . . ?
C21 C20 H20 119.7 . . ?
C16 C21 C22 118.1(3) . . ?
C20 C21 C16 119.5(3) . . ?
C20 C21 C22 122.4(3) . . ?
C13 C22 C21 122.0(3) . . ?
C13 C22 H22 119.0 . . ?
C21 C22 H22 119.0 . . ?
O24 C23 C2 120.9(3) . . ?
O24 C23 N25 123.9(3) . . ?
N25 C23 C2 115.2(3) . . ?
C23 N25 H25 118.6 . . ?
C23 N25 C26 122.7(3) . . ?
C26 N25 H25 118.6 . . ?
N25 C26 H26 108.4 . . ?
N25 C26 C27 109.3(3) . . ?
N25 C26 C28 111.1(3) . . ?
C27 C26 H26 108.4 . . ?
C27 C26 C28 111.0(3) . . ?
C28 C26 H26 108.4 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C26 120.1(3) . . ?
C29 C28 C37 119.5(3) . . ?
C37 C28 C26 120.4(3) . . ?
C28 C29 H29 119.5 . . ?
C28 C29 C30 121.0(3) . . ?
C30 C29 H29 119.5 . . ?
C31 C30 C29 122.0(3) . . ?
C31 C30 C35 119.5(3) . . ?
C35 C30 C29 118.5(3) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 C30 120.0(3) . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 119.4 . . ?
C31 C32 C33 121.3(4) . . ?
C33 C32 H32 119.4 . . ?
C32 C33 H33 119.9 . . ?
C34 C33 C32 120.3(3) . . ?
C34 C33 H33 119.9 . . ?
C33 C34 H34 119.9 . . ?
C33 C34 C35 120.2(4) . . ?
C35 C34 H34 119.9 . . ?
C30 C35 C34 118.7(3) . . ?
C36 C35 C30 119.4(3) . . ?
C36 C35 C34 121.9(3) . . ?
C35 C36 H36 119.6 . . ?
C37 C36 C35 120.7(3) . . ?
C37 C36 H36 119.6 . . ?
C28 C37 H37 119.6 . . ?
C36 C37 C28 120.8(3) . . ?
C36 C37 H37 119.6 . . ?
C53 C52 H52 120.7 . . ?
C57 C52 H52 120.7 . . ?
C57 C52 C53 118.7(3) . . ?
C52 C53 C54 121.0(3) . . ?
C52 C53 C58 118.5(3) . . ?
C54 C53 C58 120.5(3) . . ?
C53 C54 C60 120.2(3) . . ?
C55 C54 C53 119.8(3) . . ?
C55 C54 C60 120.0(3) . . ?
C54 C55 H55 120.2 . . ?
C56 C55 C54 119.6(3) . . ?
C56 C55 H55 120.2 . . ?
C55 C56 C57 120.3(3) . . ?
C55 C56 C62 120.0(3) . . ?
C57 C56 C62 119.7(3) . . ?
C52 C57 C56 120.6(3) . . ?
C52 C57 C64 119.8(3) . . ?
C56 C57 C64 119.6(3) . . ?
N59 C58 C53 178.9(4) . . ?
N61 C60 C54 179.5(4) . . ?
N63 C62 C56 178.2(4) . . ?
N65 C64 C57 179.1(4) . . ?
C67 O66 H66 109.5 . . ?
O66 C67 H67A 109.1 . . ?
O66 C67 H67B 109.1 . . ?
O66 C67 C68 112.4(4) . . ?
H67A C67 H67B 107.9 . . ?
C68 C67 H67A 109.1 . . ?
C68 C67 H67B 109.1 . . ?
C67 C68 H68A 109.5 . . ?
C67 C68 H68B 109.5 . . ?
C67 C68 H68C 109.5 . . ?
H68A C68 H68B 109.5 . . ?
H68A C68 H68C 109.5 . . ?
H68B C68 H68C 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
C38 H38 0.9500 . ?
C38 C39 1.386(5) . ?
C38 C43 1.400(5) . ?
C39 C40 1.410(5) . ?
C39 C44 1.442(5) . ?
C40 C41 1.377(5) . ?
C40 C46 1.443(5) . ?
C41 H41 0.9500 . ?
C41 C42 1.391(5) . ?
C42 C43 1.407(5) . ?
C42 C48 1.442(5) . ?
C43 C50 1.441(5) . ?
C44 N45 1.145(4) . ?
C46 N47 1.141(5) . ?
C48 N49 1.148(4) . ?
C50 N51 1.142(4) . ?
N1 C2 1.337(4) . ?
N1 C6 1.343(4) . ?
C2 C3 1.381(4) . ?
C2 C23 1.505(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(4) . ?
C4 C5 1.392(4) . ?
C4 O7 1.359(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(4) . ?
C6 C8 1.516(4) . ?
O7 H7 0.900(14) . ?
C8 O9 1.228(4) . ?
C8 N10 1.339(4) . ?
N10 H10 0.8800 . ?
N10 C11 1.462(4) . ?
C11 H11 1.0000 . ?
C11 C12 1.533(5) . ?
C11 C13 1.521(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.425(5) . ?
C13 C22 1.365(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.369(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.413(5) . ?
C16 C17 1.432(5) . ?
C16 C21 1.423(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.375(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.405(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.361(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.406(5) . ?
C21 C22 1.429(5) . ?
C22 H22 0.9500 . ?
C23 O24 1.237(4) . ?
C23 N25 1.333(4) . ?
N25 H25 0.8800 . ?
N25 C26 1.463(4) . ?
C26 H26 1.0000 . ?
C26 C27 1.515(5) . ?
C26 C28 1.526(5) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.375(4) . ?
C28 C37 1.417(5) . ?
C29 H29 0.9500 . ?
C29 C30 1.429(5) . ?
C30 C31 1.412(5) . ?
C30 C35 1.423(5) . ?
C31 H31 0.9500 . ?
C31 C32 1.366(5) . ?
C32 H32 0.9500 . ?
C32 C33 1.405(6) . ?
C33 H33 0.9500 . ?
C33 C34 1.368(5) . ?
C34 H34 0.9500 . ?
C34 C35 1.429(5) . ?
C35 C36 1.409(5) . ?
C36 H36 0.9500 . ?
C36 C37 1.372(5) . ?
C37 H37 0.9500 . ?
C52 H52 0.9500 . ?
C52 C53 1.396(5) . ?
C52 C57 1.388(5) . ?
C53 C54 1.403(5) . ?
C53 C58 1.443(5) . ?
C54 C55 1.390(5) . ?
C54 C60 1.450(5) . ?
C55 H55 0.9500 . ?
C55 C56 1.388(5) . ?
C56 C57 1.407(5) . ?
C56 C62 1.438(5) . ?
C57 C64 1.438(5) . ?
C58 N59 1.145(5) . ?
C60 N61 1.143(5) . ?
C62 N63 1.133(5) . ?
C64 N65 1.147(4) . ?
O66 H66 0.8400 . ?
O66 C67 1.459(5) . ?
C67 H67A 0.9900 . ?
C67 H67B 0.9900 . ?
C67 C68 1.497(6) . ?
C68 H68A 0.9800 . ?
C68 H68B 0.9800 . ?
C68 H68C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7 O66 0.900(14) 1.96(3) 2.665(4) 134(4) .
C26 H26 O9_$1 1.00 2.39 3.261(4) 144.9 1_455
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
C38 C39 C40 C41 0.0(5) . . . . ?
C38 C39 C40 C46 179.3(3) . . . . ?
C39 C38 C43 C42 -0.8(4) . . . . ?
C39 C38 C43 C50 179.2(3) . . . . ?
C39 C40 C41 C42 0.2(5) . . . . ?
C40 C41 C42 C43 -0.8(5) . . . . ?
C40 C41 C42 C48 176.0(3) . . . . ?
C41 C42 C43 C38 1.1(5) . . . . ?
C41 C42 C43 C50 -179.0(3) . . . . ?
C43 C38 C39 C40 0.2(5) . . . . ?
C43 C38 C39 C44 179.9(3) . . . . ?
C44 C39 C40 C41 -179.6(3) . . . . ?
C44 C39 C40 C46 -0.4(5) . . . . ?
C46 C40 C41 C42 -179.0(3) . . . . ?
C48 C42 C43 C38 -175.7(3) . . . . ?
C48 C42 C43 C50 4.3(5) . . . . ?
N1 C2 C3 C4 3.1(5) . . . . ?
N1 C2 C23 O24 170.3(3) . . . . ?
N1 C2 C23 N25 -10.5(4) . . . . ?
N1 C6 C8 O9 169.6(3) . . . . ?
N1 C6 C8 N10 -9.8(4) . . . . ?
C2 N1 C6 C5 -0.9(4) . . . . ?
C2 N1 C6 C8 178.9(3) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C2 C3 C4 O7 -179.2(3) . . . . ?
C2 C23 N25 C26 179.8(3) . . . . ?
C3 C2 C23 O24 -10.4(4) . . . . ?
C3 C2 C23 N25 168.8(3) . . . . ?
C3 C4 C5 C6 -3.2(5) . . . . ?
C4 C5 C6 N1 3.8(5) . . . . ?
C4 C5 C6 C8 -176.0(3) . . . . ?
C5 C6 C8 O9 -10.5(5) . . . . ?
C5 C6 C8 N10 170.0(3) . . . . ?
C6 N1 C2 C3 -2.6(4) . . . . ?
C6 N1 C2 C23 176.6(3) . . . . ?
C6 C8 N10 C11 173.1(3) . . . . ?
O7 C4 C5 C6 175.9(3) . . . . ?
C8 N10 C11 C12 -150.8(3) . . . . ?
C8 N10 C11 C13 86.5(4) . . . . ?
O9 C8 N10 C11 -6.3(5) . . . . ?
N10 C11 C13 C14 42.9(4) . . . . ?
N10 C11 C13 C22 -142.0(3) . . . . ?
C11 C13 C14 C15 175.5(3) . . . . ?
C11 C13 C22 C21 -175.5(3) . . . . ?
C12 C11 C13 C14 -78.6(4) . . . . ?
C12 C11 C13 C22 96.5(4) . . . . ?
C13 C14 C15 C16 -0.7(5) . . . . ?
C14 C13 C22 C21 -0.3(5) . . . . ?
C14 C15 C16 C17 -179.1(3) . . . . ?
C14 C15 C16 C21 1.1(5) . . . . ?
C15 C16 C17 C18 179.9(3) . . . . ?
C15 C16 C21 C20 179.6(3) . . . . ?
C15 C16 C21 C22 -1.1(5) . . . . ?
C16 C17 C18 C19 0.1(5) . . . . ?
C16 C21 C22 C13 0.7(5) . . . . ?
C17 C16 C21 C20 -0.2(5) . . . . ?
C17 C16 C21 C22 179.1(3) . . . . ?
C17 C18 C19 C20 0.5(5) . . . . ?
C18 C19 C20 C21 -0.9(5) . . . . ?
C19 C20 C21 C16 0.8(5) . . . . ?
C19 C20 C21 C22 -178.5(3) . . . . ?
C20 C21 C22 C13 180.0(3) . . . . ?
C21 C16 C17 C18 -0.2(5) . . . . ?
C22 C13 C14 C15 0.3(5) . . . . ?
C23 C2 C3 C4 -176.2(3) . . . . ?
C23 N25 C26 C27 -161.0(3) . . . . ?
C23 N25 C26 C28 76.1(4) . . . . ?
O24 C23 N25 C26 -1.0(5) . . . . ?
N25 C26 C28 C29 -130.2(3) . . . . ?
N25 C26 C28 C37 52.2(4) . . . . ?
C26 C28 C29 C30 -179.5(3) . . . . ?
C26 C28 C37 C36 179.3(3) . . . . ?
C27 C26 C28 C29 107.9(4) . . . . ?
C27 C26 C28 C37 -69.6(4) . . . . ?
C28 C29 C30 C31 -178.0(3) . . . . ?
C28 C29 C30 C35 0.6(5) . . . . ?
C29 C28 C37 C36 1.8(5) . . . . ?
C29 C30 C31 C32 178.2(3) . . . . ?
C29 C30 C35 C34 -178.3(3) . . . . ?
C29 C30 C35 C36 1.1(5) . . . . ?
C30 C31 C32 C33 0.4(5) . . . . ?
C30 C35 C36 C37 -1.3(5) . . . . ?
C31 C30 C35 C34 0.3(5) . . . . ?
C31 C30 C35 C36 179.7(3) . . . . ?
C31 C32 C33 C34 -0.3(6) . . . . ?
C32 C33 C34 C35 0.2(5) . . . . ?
C33 C34 C35 C30 -0.2(5) . . . . ?
C33 C34 C35 C36 -179.6(3) . . . . ?
C34 C35 C36 C37 178.1(3) . . . . ?
C35 C30 C31 C32 -0.4(5) . . . . ?
C35 C36 C37 C28 -0.1(5) . . . . ?
C37 C28 C29 C30 -2.0(5) . . . . ?
C52 C53 C54 C55 -0.8(5) . . . . ?
C52 C53 C54 C60 179.6(3) . . . . ?
C53 C52 C57 C56 0.5(5) . . . . ?
C53 C52 C57 C64 -179.7(3) . . . . ?
C53 C54 C55 C56 0.1(5) . . . . ?
C54 C55 C56 C57 0.9(5) . . . . ?
C54 C55 C56 C62 -177.8(3) . . . . ?
C55 C56 C57 C52 -1.3(5) . . . . ?
C55 C56 C57 C64 179.0(3) . . . . ?
C57 C52 C53 C54 0.5(5) . . . . ?
C57 C52 C53 C58 179.7(3) . . . . ?
C58 C53 C54 C55 180.0(3) . . . . ?
C58 C53 C54 C60 0.4(5) . . . . ?
C60 C54 C55 C56 179.6(3) . . . . ?
C62 C56 C57 C52 177.5(3) . . . . ?
C62 C56 C57 C64 -2.3(5) . . . . ?
