#------------------------------------------------------------------------------
#$Date: 2024-02-04 13:32:00 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289420 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/04/1570412.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_1570412
loop_
_publ_author_name
'Sudhakar, Pagidi'
'Gupta, Abhishek Kumar'
'Cordes, David B.'
'Zysman-Colman, Eli'
_publ_section_title
;
 Thermally activated delayed fluorescence emitters showing wide-range
 near-infrared piezochromism and their use in deep-red OLEDs.
;
_journal_issue                   2
_journal_name_full               'Chemical science'
_journal_page_first              545
_journal_page_last               554
_journal_paper_doi               10.1039/d3sc05188a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C52 H40 N4 O2'
_chemical_formula_sum            'C52 H40 N4 O2'
_chemical_formula_weight         752.88
_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     direct
_audit_creation_date             2023-09-07
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-09-21 deposited with the CCDC.	2023-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                109.639(3)
_cell_angle_beta                 95.666(2)
_cell_angle_gamma                108.274(3)
_cell_formula_units_Z            2
_cell_length_a                   10.0726(3)
_cell_length_b                   14.3581(4)
_cell_length_c                   15.3628(4)
_cell_measurement_reflns_used    12427
_cell_measurement_temperature    125
_cell_measurement_theta_max      75.2580
_cell_measurement_theta_min      3.1380
_cell_volume                     1934.60(11)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SIR2011  (Burla et al.,  2007)'
_diffrn_ambient_temperature      125
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Dectris PILATUS P200K'
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -125.00  55.00   0.50   10.00    --  -35.00  60.00 -45.00  360
  2  ω   -108.00 -48.00   0.50   10.00    --  -35.00  30.00  90.00  120
  3  ω   -173.50 -10.00   0.50   20.00    -- -100.00  60.00 -90.00  327
  4  ω   -187.00 -40.00   0.50   20.00    -- -100.00  30.00  45.00  294
  5  ω   -165.00 -10.00   0.50   20.00    -- -100.00  60.00-180.00  310
  6  ω   -190.00-127.50   0.50   20.00    -- -100.00  60.00 135.00  125
  7  ω   -165.00 -19.00   0.50   20.00    -- -100.00  60.00   0.00  292
  8  ω   -152.50 -44.50   0.50   20.00    -- -100.00  30.00 135.00  216
  9  ω   -174.00-114.00   0.50   20.00    -- -100.00  60.00  90.00  120
 10  ω    -70.00 -10.00   0.50   20.00    -- -100.00  30.00   0.00  120
 11  ω   -190.00 -10.00   0.50   20.00    -- -100.00  30.00 -90.00  360
 12  ω   -174.00 -10.00   0.50   20.00    -- -100.00  60.00  45.00  328
 13  ω   -190.00-120.00   0.50   20.00    -- -100.00  60.00-135.00  140
;
_diffrn_measurement_device       'AFC11: Quarter χ 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0804309000
_diffrn_orient_matrix_UB_12      -0.1165911000
_diffrn_orient_matrix_UB_13      -0.0143600000
_diffrn_orient_matrix_UB_21      0.0305843000
_diffrn_orient_matrix_UB_22      -0.0376426000
_diffrn_orient_matrix_UB_23      -0.0996803000
_diffrn_orient_matrix_UB_31      0.1412949000
_diffrn_orient_matrix_UB_32      -0.0051033000
_diffrn_orient_matrix_UB_33      0.0426249000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23164
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.547
_diffrn_reflns_theta_min         3.137
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane/hexane'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         7654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0416
_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)+(0.0654P)²+0.3712P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1179
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6439
_reflns_number_total             7654
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc05188a3.cif
_cod_data_source_block           MeTPA-BQ
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1570412--1570413.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1570412
_shelx_shelxl_version_number     2019/3
_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   0.865
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C16(H16), C17(H17), C19(H19), C20(H20),
 C23(H23), C24(H24), C26(H26), C27(H27), C30(H30), C31(H31), C33(H33), C34(H34),
  C37(H37), C38(H38), C40(H40), C41(H41), C44(H44), C45(H45), C47(H47),
 C48(H48), C51(H51), C52(H52), C54(H54), C55(H55)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C35(H35A,H35B,H35C), C49(H49A,H49B,H49C), C56(H56A,H56B,
 H56C)
;
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
O5 O 0.03104(14) 0.82632(9) 0.46560(7) 0.0475(3) Uani 1 1 d . . . . .
O12 O 0.18789(13) 0.85818(8) 0.82304(7) 0.0425(3) Uani 1 1 d . . . . .
N3 N 0.12214(12) 0.67441(8) 0.49170(7) 0.0270(2) Uani 1 1 d . . . . .
N14 N 0.21058(12) 0.69400(8) 0.67671(7) 0.0277(2) Uani 1 1 d . . . . .
N21 N 0.43581(14) 0.32250(9) 0.67644(8) 0.0342(3) Uani 1 1 d . . . . .
N42 N 0.15894(12) 0.28932(8) 0.15471(7) 0.0276(2) Uani 1 1 d . . . . .
C1 C 0.22224(13) 0.61739(10) 0.60314(8) 0.0257(3) Uani 1 1 d . . . . .
C2 C 0.17340(13) 0.60461(9) 0.50718(8) 0.0249(2) Uani 1 1 d . . . . .
C4 C 0.11553(14) 0.75309(10) 0.56628(9) 0.0270(3) Uani 1 1 d . . . . .
C5 C 0.05734(15) 0.82939(11) 0.54574(9) 0.0324(3) Uani 1 1 d . . . . .
C6 C 0.03236(15) 0.90854(10) 0.62826(9) 0.0310(3) Uani 1 1 d . . . . .
C7 C -0.03456(17) 0.97418(12) 0.61189(11) 0.0392(3) Uani 1 1 d . . . . .
H7 H -0.063289 0.968628 0.548986 0.047 Uiso 1 1 calc R U . . .
C8 C -0.05947(19) 1.04789(12) 0.68743(12) 0.0445(4) Uani 1 1 d . . . . .
H8 H -0.104758 1.092952 0.676065 0.053 Uiso 1 1 calc R U . . .
C9 C -0.01867(18) 1.05598(12) 0.77904(11) 0.0430(4) Uani 1 1 d . . . . .
H9 H -0.037202 1.105834 0.830377 0.052 Uiso 1 1 calc R U . . .
C10 C 0.04907(17) 0.99164(11) 0.79609(10) 0.0374(3) Uani 1 1 d . . . . .
H10 H 0.078340 0.998296 0.859305 0.045 Uiso 1 1 calc R U . . .
C11 C 0.07469(15) 0.91714(10) 0.72124(9) 0.0310(3) Uani 1 1 d . . . . .
C12 C 0.14384(15) 0.84714(10) 0.74230(9) 0.0305(3) Uani 1 1 d . . . . .
C13 C 0.15652(14) 0.76158(10) 0.65872(8) 0.0267(3) Uani 1 1 d . . . . .
C15 C 0.28603(14) 0.54719(10) 0.62810(8) 0.0267(3) Uani 1 1 d . . . . .
C16 C 0.40875(14) 0.53504(10) 0.59935(8) 0.0270(3) Uani 1 1 d . . . . .
H16 H 0.456361 0.575453 0.566022 0.032 Uiso 1 1 calc R U . . .
C17 C 0.46141(14) 0.46468(10) 0.61904(8) 0.0282(3) Uani 1 1 d . . . . .
H17 H 0.546822 0.458632 0.600987 0.034 Uiso 1 1 calc R U . . .
C18 C 0.39011(15) 0.40236(10) 0.66529(9) 0.0294(3) Uani 1 1 d . . . . .
C19 C 0.27151(16) 0.41746(12) 0.69772(10) 0.0371(3) Uani 1 1 d . . . . .
H19 H 0.224890 0.377706 0.731837 0.045 Uiso 1 1 calc R U . . .
C20 C 0.22113(16) 0.49035(11) 0.68042(10) 0.0349(3) Uani 1 1 d . . . . .
H20 H 0.141687 0.501791 0.704358 0.042 Uiso 1 1 calc R U . . .
C22 C 0.46480(15) 0.25197(10) 0.59775(9) 0.0305(3) Uani 1 1 d . . . . .
C23 C 0.38755(17) 0.22190(11) 0.50570(10) 0.0378(3) Uani 1 1 d . . . . .
H23 H 0.314747 0.248673 0.495835 0.045 Uiso 1 1 calc R U . . .
C24 C 0.41659(18) 0.15319(11) 0.42867(10) 0.0397(3) Uani 1 1 d . . . . .
H24 H 0.364405 0.134866 0.366514 0.048 Uiso 1 1 calc R U . . .
C25 C 0.51997(17) 0.11054(10) 0.44010(10) 0.0356(3) Uani 1 1 d . . . . .
C26 C 0.59546(16) 0.14039(11) 0.53186(10) 0.0344(3) Uani 1 1 d . . . . .
H26 H 0.666673 0.112211 0.541678 0.041 Uiso 1 1 calc R U . . .
C27 C 0.56938(15) 0.21048(10) 0.60970(9) 0.0318(3) Uani 1 1 d . . . . .
H27 H 0.623573 0.230170 0.671610 0.038 Uiso 1 1 calc R U . . .
C28 C 0.5474(2) 0.03319(12) 0.35570(11) 0.0442(4) Uani 1 1 d . . . . .
H28A H 0.623267 0.011542 0.377457 0.066 Uiso 1 1 calc R U . . .
H28B H 0.577617 0.067570 0.311820 0.066 Uiso 1 1 calc R U . . .
H28C H 0.459183 -0.029653 0.323108 0.066 Uiso 1 1 calc R U . . .
C29 C 0.45928(15) 0.31741(11) 0.76738(9) 0.0298(3) Uani 1 1 d . . . . .
C30 C 0.40281(16) 0.22131(11) 0.77821(10) 0.0352(3) Uani 1 1 d . . . . .
H30 H 0.343723 0.158835 0.725065 0.042 Uiso 1 1 calc R U . . .
C31 C 0.43249(17) 0.21640(12) 0.86636(10) 0.0377(3) Uani 1 1 d . . . . .
H31 H 0.393879 0.150113 0.872577 0.045 Uiso 1 1 calc R U . . .
C32 C 0.51758(16) 0.30650(12) 0.94577(10) 0.0361(3) Uani 1 1 d . . . . .
C33 C 0.56941(16) 0.40244(12) 0.93431(10) 0.0366(3) Uani 1 1 d . . . . .
H33 H 0.625589 0.465411 0.987919 0.044 Uiso 1 1 calc R U . . .
C34 C 0.54121(16) 0.40864(11) 0.84659(9) 0.0336(3) Uani 1 1 d . . . . .
H34 H 0.577922 0.475245 0.840705 0.040 Uiso 1 1 calc R U . . .
C35 C 0.5517(2) 0.30018(16) 1.04115(11) 0.0498(4) Uani 1 1 d . . . . .
H35A H 0.642300 0.288630 1.048770 0.075 Uiso 1 1 calc R U . . .
H35B H 0.474317 0.240919 1.044849 0.075 Uiso 1 1 calc R U . . .
H35C H 0.560705 0.366895 1.091684 0.075 Uiso 1 1 calc R U . . .
C36 C 0.17341(13) 0.51942(9) 0.41959(8) 0.0246(2) Uani 1 1 d . . . . .
C37 C 0.16773(14) 0.53888(10) 0.33579(9) 0.0269(3) Uani 1 1 d . . . . .
H37 H 0.165921 0.605459 0.338230 0.032 Uiso 1 1 calc R U . . .
C38 C 0.16470(14) 0.46451(10) 0.25031(8) 0.0270(3) Uani 1 1 d . . . . .
H38 H 0.161306 0.480855 0.195322 0.032 Uiso 1 1 calc R U . . .
C39 C 0.16656(13) 0.36496(9) 0.24319(8) 0.0253(2) Uani 1 1 d . . . . .
C40 C 0.17313(13) 0.34453(9) 0.32631(8) 0.0258(3) Uani 1 1 d . . . . .
H40 H 0.176258 0.278272 0.323864 0.031 Uiso 1 1 calc R U . . .
C41 C 0.17512(13) 0.41975(9) 0.41211(8) 0.0251(2) Uani 1 1 d . . . . .
H41 H 0.177713 0.403298 0.467049 0.030 Uiso 1 1 calc R U . . .
C43 C 0.10115(14) 0.29933(9) 0.07041(8) 0.0265(3) Uani 1 1 d . . . . .
C44 C -0.03888(15) 0.29438(11) 0.05254(9) 0.0335(3) Uani 1 1 d . . . . .
H44 H -0.099230 0.280681 0.094117 0.040 Uiso 1 1 calc R U . . .
C45 C -0.09018(16) 0.30970(12) -0.02694(10) 0.0364(3) Uani 1 1 d . . . . .
H45 H -0.185708 0.307608 -0.038373 0.044 Uiso 1 1 calc R U . . .
C46 C -0.00550(16) 0.32799(11) -0.09018(9) 0.0336(3) Uani 1 1 d . . . . .
C47 C 0.13302(16) 0.32953(11) -0.07217(9) 0.0337(3) Uani 1 1 d . . . . .
H47 H 0.192234 0.340069 -0.115134 0.040 Uiso 1 1 calc R U . . .
C48 C 0.18647(15) 0.31593(10) 0.00749(9) 0.0306(3) Uani 1 1 d . . . . .
H48 H 0.281978 0.317998 0.018992 0.037 Uiso 1 1 calc R U . . .
C49 C -0.0613(2) 0.34609(14) -0.17537(11) 0.0475(4) Uani 1 1 d . . . . .
H49A H -0.003705 0.417708 -0.170030 0.071 Uiso 1 1 calc R U . . .
H49B H -0.161750 0.339131 -0.178265 0.071 Uiso 1 1 calc R U . . .
H49C H -0.054729 0.293204 -0.233226 0.071 Uiso 1 1 calc R U . . .
C50 C 0.22401(14) 0.21254(9) 0.14393(8) 0.0258(3) Uani 1 1 d . . . . .
C51 C 0.16243(15) 0.11434(10) 0.06735(9) 0.0307(3) Uani 1 1 d . . . . .
H51 H 0.075406 0.098267 0.025138 0.037 Uiso 1 1 calc R U . . .
C52 C 0.22753(15) 0.04025(10) 0.05260(9) 0.0319(3) Uani 1 1 d . . . . .
H52 H 0.184556 -0.025840 -0.000276 0.038 Uiso 1 1 calc R U . . .
C53 C 0.35398(15) 0.06005(10) 0.11307(9) 0.0300(3) Uani 1 1 d . . . . .
C54 C 0.41504(15) 0.15886(10) 0.18881(9) 0.0318(3) Uani 1 1 d . . . . .
H54 H 0.502077 0.174975 0.231025 0.038 Uiso 1 1 calc R U . . .
C55 C 0.35154(14) 0.23411(10) 0.20386(9) 0.0294(3) Uani 1 1 d . . . . .
H55 H 0.395876 0.300983 0.255701 0.035 Uiso 1 1 calc R U . . .
C56 C 0.42135(18) -0.02253(12) 0.09654(10) 0.0399(3) Uani 1 1 d . . . . .
H56A H 0.389178 -0.064716 0.134372 0.060 Uiso 1 1 calc R U . . .
H56B H 0.526140 0.012776 0.115393 0.060 Uiso 1 1 calc R U . . .
H56C H 0.392573 -0.069415 0.029085 0.060 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 N3 C2 118.73(11) . . ?
C1 N14 C13 117.84(11) . . ?
C18 N21 C22 119.35(10) . . ?
C18 N21 C29 119.83(10) . . ?
C22 N21 C29 120.74(10) . . ?
C39 N42 C43 118.42(9) . . ?
C39 N42 C50 123.14(10) . . ?
C50 N42 C43 117.81(9) . . ?
N14 C1 C2 121.31(11) . . ?
N14 C1 C15 115.08(10) . . ?
C2 C1 C15 123.61(10) . . ?
N3 C2 C1 119.30(10) . . ?
N3 C2 C36 114.32(10) . . ?
C1 C2 C36 126.38(11) . . ?
N3 C4 C5 116.98(11) . . ?
N3 C4 C13 121.44(11) . . ?
C13 C4 C5 121.55(11) . . ?
O5 C5 C4 121.34(11) . . ?
O5 C5 C6 121.93(12) . . ?
C6 C5 C4 116.73(11) . . ?
C7 C6 C5 119.05(12) . . ?
C7 C6 C11 119.75(12) . . ?
C11 C6 C5 121.19(12) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.03(14) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.29(14) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.08(13) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.43(13) . . ?
C11 C10 H10 119.8 . . ?
C6 C11 C12 121.82(11) . . ?
C10 C11 C6 119.41(12) . . ?
C10 C11 C12 118.76(12) . . ?
O12 C12 C11 122.03(11) . . ?
O12 C12 C13 121.28(12) . . ?
C11 C12 C13 116.68(11) . . ?
N14 C13 C4 121.25(11) . . ?
N14 C13 C12 117.14(11) . . ?
C4 C13 C12 121.60(11) . . ?
C16 C15 C1 121.55(11) . . ?
C16 C15 C20 118.90(11) . . ?
C20 C15 C1 119.55(11) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.37(12) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.47(12) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 N21 120.20(12) . . ?
C19 C18 N21 120.46(12) . . ?
C19 C18 C17 119.31(12) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.11(13) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 119.7 . . ?
C19 C20 C15 120.60(12) . . ?
C19 C20 H20 119.7 . . ?
C23 C22 N21 120.46(12) . . ?
C27 C22 N21 121.23(12) . . ?
C27 C22 C23 118.31(12) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.37(13) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 119.2 . . ?
C23 C24 C25 121.66(13) . . ?
C25 C24 H24 119.2 . . ?
C24 C25 C26 117.50(12) . . ?
C24 C25 C28 121.07(14) . . ?
C26 C25 C28 121.41(14) . . ?
C25 C26 H26 119.2 . . ?
C25 C26 C27 121.59(13) . . ?
C27 C26 H26 119.2 . . ?
C22 C27 C26 120.56(13) . . ?
C22 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 N21 120.81(12) . . ?
C34 C29 N21 120.16(12) . . ?
C34 C29 C30 119.02(12) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 C29 120.24(13) . . ?
C31 C30 H30 119.9 . . ?
C30 C31 H31 119.3 . . ?
C30 C31 C32 121.36(13) . . ?
C32 C31 H31 119.3 . . ?
C31 C32 C35 121.08(14) . . ?
C33 C32 C31 117.64(12) . . ?
C33 C32 C35 121.28(15) . . ?
C32 C33 H33 119.2 . . ?
C34 C33 C32 121.70(14) . . ?
C34 C33 H33 119.2 . . ?
C29 C34 H34 120.0 . . ?
C33 C34 C29 119.98(13) . . ?
C33 C34 H34 120.0 . . ?
C32 C35 H35A 109.5 . . ?
C32 C35 H35B 109.5 . . ?
C32 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C37 C36 C2 117.36(10) . . ?
C41 C36 C2 125.89(11) . . ?
C41 C36 C37 116.74(10) . . ?
C36 C37 H37 119.0 . . ?
C38 C37 C36 122.08(11) . . ?
C38 C37 H37 119.0 . . ?
C37 C38 H38 119.5 . . ?
C37 C38 C39 120.98(11) . . ?
C39 C38 H38 119.5 . . ?
N42 C39 C40 122.46(11) . . ?
C38 C39 N42 119.88(11) . . ?
C38 C39 C40 117.65(11) . . ?
C39 C40 H40 119.5 . . ?
C41 C40 C39 120.96(11) . . ?
C41 C40 H40 119.5 . . ?
C36 C41 H41 119.2 . . ?
C40 C41 C36 121.58(11) . . ?
C40 C41 H41 119.2 . . ?
C44 C43 N42 120.28(11) . . ?
C44 C43 C48 119.73(12) . . ?
C48 C43 N42 119.98(11) . . ?
C43 C44 H44 120.4 . . ?
C43 C44 C45 119.27(13) . . ?
C45 C44 H44 120.4 . . ?
C44 C45 H45 119.1 . . ?
C44 C45 C46 121.82(13) . . ?
C46 C45 H45 119.1 . . ?
C45 C46 C49 121.45(14) . . ?
C47 C46 C45 117.79(12) . . ?
C47 C46 C49 120.75(13) . . ?
C46 C47 H47 119.5 . . ?
C48 C47 C46 121.08(13) . . ?
C48 C47 H47 119.5 . . ?
C43 C48 C47 120.27(12) . . ?
C43 C48 H48 119.9 . . ?
C47 C48 H48 119.9 . . ?
C46 C49 H49A 109.5 . . ?
C46 C49 H49B 109.5 . . ?
C46 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C51 C50 N42 119.21(11) . . ?
C55 C50 N42 122.14(11) . . ?
C55 C50 C51 118.54(11) . . ?
C50 C51 H51 119.8 . . ?
C52 C51 C50 120.36(12) . . ?
C52 C51 H51 119.8 . . ?
C51 C52 H52 119.1 . . ?
C51 C52 C53 121.71(12) . . ?
C53 C52 H52 119.1 . . ?
C52 C53 C54 117.33(11) . . ?
C52 C53 C56 120.73(12) . . ?
C54 C53 C56 121.94(12) . . ?
C53 C54 H54 119.2 . . ?
C55 C54 C53 121.50(12) . . ?
C55 C54 H54 119.2 . . ?
C50 C55 C54 120.55(11) . . ?
C50 C55 H55 119.7 . . ?
C54 C55 H55 119.7 . . ?
C53 C56 H56A 109.5 . . ?
C53 C56 H56B 109.5 . . ?
C53 C56 H56C 109.5 . . ?
H56A C56 H56B 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 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
O5 C5 1.2165(16) . ?
O12 C12 1.2147(17) . ?
N3 C2 1.3372(16) . ?
N3 C4 1.3362(15) . ?
N14 C1 1.3315(15) . ?
N14 C13 1.3403(16) . ?
N21 C18 1.4154(16) . ?
N21 C22 1.4157(16) . ?
N21 C29 1.4239(16) . ?
N42 C39 1.4029(15) . ?
N42 C43 1.4371(15) . ?
N42 C50 1.4228(15) . ?
C1 C2 1.4378(17) . ?
C1 C15 1.4809(17) . ?
C2 C36 1.4835(16) . ?
C4 C5 1.4973(17) . ?
C4 C13 1.3922(18) . ?
C5 C6 1.4952(17) . ?
C6 C7 1.3893(19) . ?
C6 C11 1.4020(19) . ?
C7 H7 0.9500 . ?
C7 C8 1.389(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.382(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.382(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.3921(18) . ?
C11 C12 1.4876(18) . ?
C12 C13 1.4983(16) . ?
C15 C16 1.3945(18) . ?
C15 C20 1.3963(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.3796(17) . ?
C17 H17 0.9500 . ?
C17 C18 1.3951(19) . ?
C18 C19 1.3892(19) . ?
C19 H19 0.9500 . ?
C19 C20 1.3845(19) . ?
C20 H20 0.9500 . ?
C22 C23 1.3977(19) . ?
C22 C27 1.3882(19) . ?
C23 H23 0.9500 . ?
C23 C24 1.387(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.388(2) . ?
C25 C26 1.388(2) . ?
C25 C28 1.5121(18) . ?
C26 H26 0.9500 . ?
C26 C27 1.3895(18) . ?
C27 H27 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.3913(19) . ?
C29 C34 1.3892(19) . ?
C30 H30 0.9500 . ?
C30 C31 1.388(2) . ?
C31 H31 0.9500 . ?
C31 C32 1.391(2) . ?
C32 C33 1.390(2) . ?
C32 C35 1.5109(19) . ?
C33 H33 0.9500 . ?
C33 C34 1.3877(19) . ?
C34 H34 0.9500 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 C37 1.4057(17) . ?
C36 C41 1.4024(17) . ?
C37 H37 0.9500 . ?
C37 C38 1.3765(16) . ?
C38 H38 0.9500 . ?
C38 C39 1.4027(17) . ?
C39 C40 1.4029(17) . ?
C40 H40 0.9500 . ?
C40 C41 1.3887(16) . ?
C41 H41 0.9500 . ?
C43 C44 1.3847(19) . ?
C43 C48 1.3857(18) . ?
C44 H44 0.9500 . ?
C44 C45 1.3905(19) . ?
C45 H45 0.9500 . ?
C45 C46 1.391(2) . ?
C46 C47 1.387(2) . ?
C46 C49 1.5072(19) . ?
C47 H47 0.9500 . ?
C47 C48 1.3865(19) . ?
C48 H48 0.9500 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 C51 1.3962(17) . ?
C50 C55 1.3853(19) . ?
C51 H51 0.9500 . ?
C51 C52 1.3848(18) . ?
C52 H52 0.9500 . ?
C52 C53 1.388(2) . ?
C53 C54 1.3952(18) . ?
C53 C56 1.5058(18) . ?
C54 H54 0.9500 . ?
C54 C55 1.3873(18) . ?
C55 H55 0.9500 . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 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
O5 C5 C6 C7 5.8(2) . . . . ?
O5 C5 C6 C11 -174.42(14) . . . . ?
O12 C12 C13 N14 3.9(2) . . . . ?
O12 C12 C13 C4 -175.43(13) . . . . ?
N3 C2 C36 C37 20.63(16) . . . . ?
N3 C2 C36 C41 -157.75(12) . . . . ?
N3 C4 C5 O5 -7.2(2) . . . . ?
N3 C4 C5 C6 172.32(12) . . . . ?
N3 C4 C13 N14 3.2(2) . . . . ?
N3 C4 C13 C12 -177.56(12) . . . . ?
N14 C1 C2 N3 3.52(19) . . . . ?
N14 C1 C2 C36 -176.56(12) . . . . ?
N14 C1 C15 C16 -122.53(13) . . . . ?
N14 C1 C15 C20 58.44(16) . . . . ?
N21 C18 C19 C20 -175.27(13) . . . . ?
N21 C22 C23 C24 179.69(13) . . . . ?
N21 C22 C27 C26 179.26(13) . . . . ?
N21 C29 C30 C31 176.73(12) . . . . ?
N21 C29 C34 C33 -177.00(12) . . . . ?
N42 C39 C40 C41 -177.54(11) . . . . ?
N42 C43 C44 C45 176.73(12) . . . . ?
N42 C43 C48 C47 -177.64(11) . . . . ?
N42 C50 C51 C52 176.81(12) . . . . ?
N42 C50 C55 C54 -177.27(12) . . . . ?
C1 N14 C13 C4 -0.84(18) . . . . ?
C1 N14 C13 C12 179.86(11) . . . . ?
C1 C2 C36 C37 -159.29(12) . . . . ?
C1 C2 C36 C41 22.3(2) . . . . ?
C1 C15 C16 C17 -176.40(11) . . . . ?
C1 C15 C20 C19 174.50(13) . . . . ?
C2 N3 C4 C5 -179.94(11) . . . . ?
C2 N3 C4 C13 -2.00(19) . . . . ?
C2 C1 C15 C16 58.45(17) . . . . ?
C2 C1 C15 C20 -120.58(14) . . . . ?
C2 C36 C37 C38 -178.85(12) . . . . ?
C2 C36 C41 C40 179.17(12) . . . . ?
C4 N3 C2 C1 -1.20(18) . . . . ?
C4 N3 C2 C36 178.87(11) . . . . ?
C4 C5 C6 C7 -173.73(13) . . . . ?
C4 C5 C6 C11 6.0(2) . . . . ?
C5 C4 C13 N14 -178.97(12) . . . . ?
C5 C4 C13 C12 0.29(19) . . . . ?
C5 C6 C7 C8 179.68(14) . . . . ?
C5 C6 C11 C10 -179.80(13) . . . . ?
C5 C6 C11 C12 -1.1(2) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
C6 C11 C12 O12 175.84(14) . . . . ?
C6 C11 C12 C13 -4.29(19) . . . . ?
C7 C6 C11 C10 0.0(2) . . . . ?
C7 C6 C11 C12 178.66(13) . . . . ?
C7 C8 C9 C10 0.9(3) . . . . ?
C8 C9 C10 C11 -1.0(2) . . . . ?
C9 C10 C11 C6 0.6(2) . . . . ?
C9 C10 C11 C12 -178.15(14) . . . . ?
C10 C11 C12 O12 -5.4(2) . . . . ?
C10 C11 C12 C13 174.42(12) . . . . ?
C11 C6 C7 C8 -0.1(2) . . . . ?
C11 C12 C13 N14 -176.01(11) . . . . ?
C11 C12 C13 C4 4.70(19) . . . . ?
C13 N14 C1 C2 -2.39(18) . . . . ?
C13 N14 C1 C15 178.57(11) . . . . ?
C13 C4 C5 O5 174.82(14) . . . . ?
C13 C4 C5 C6 -5.62(19) . . . . ?
C15 C1 C2 N3 -177.52(11) . . . . ?
C15 C1 C2 C36 2.4(2) . . . . ?
C15 C16 C17 C18 2.03(18) . . . . ?
C16 C15 C20 C19 -4.6(2) . . . . ?
C16 C17 C18 N21 173.35(11) . . . . ?
C16 C17 C18 C19 -4.79(19) . . . . ?
C17 C18 C19 C20 2.9(2) . . . . ?
C18 N21 C22 C23 -32.2(2) . . . . ?
C18 N21 C22 C27 148.13(13) . . . . ?
C18 N21 C29 C30 132.29(14) . . . . ?
C18 N21 C29 C34 -48.71(18) . . . . ?
C18 C19 C20 C15 1.8(2) . . . . ?
C20 C15 C16 C17 2.63(18) . . . . ?
C22 N21 C18 C17 -46.55(18) . . . . ?
C22 N21 C18 C19 131.57(14) . . . . ?
C22 N21 C29 C30 -51.01(19) . . . . ?
C22 N21 C29 C34 127.98(14) . . . . ?
C22 C23 C24 C25 1.4(2) . . . . ?
C23 C22 C27 C26 -0.4(2) . . . . ?
C23 C24 C25 C26 -0.9(2) . . . . ?
C23 C24 C25 C28 178.18(14) . . . . ?
C24 C25 C26 C27 -0.1(2) . . . . ?
C25 C26 C27 C22 0.8(2) . . . . ?
C27 C22 C23 C24 -0.7(2) . . . . ?
C28 C25 C26 C27 -179.24(13) . . . . ?
C29 N21 C18 C17 130.19(13) . . . . ?
C29 N21 C18 C19 -51.69(19) . . . . ?
C29 N21 C22 C23 151.04(14) . . . . ?
C29 N21 C22 C27 -28.6(2) . . . . ?
C29 C30 C31 C32 0.5(2) . . . . ?
C30 C29 C34 C33 2.0(2) . . . . ?
C30 C31 C32 C33 1.4(2) . . . . ?
C30 C31 C32 C35 -178.85(13) . . . . ?
C31 C32 C33 C34 -1.7(2) . . . . ?
C32 C33 C34 C29 0.0(2) . . . . ?
C34 C29 C30 C31 -2.3(2) . . . . ?
C35 C32 C33 C34 178.58(13) . . . . ?
C36 C37 C38 C39 0.3(2) . . . . ?
C37 C36 C41 C40 0.78(18) . . . . ?
C37 C38 C39 N42 178.04(12) . . . . ?
C37 C38 C39 C40 -0.66(19) . . . . ?
C38 C39 C40 C41 1.12(19) . . . . ?
C39 N42 C43 C44 -61.08(16) . . . . ?
C39 N42 C43 C48 117.74(13) . . . . ?
C39 N42 C50 C51 150.40(12) . . . . ?
C39 N42 C50 C55 -33.43(18) . . . . ?
C39 C40 C41 C36 -1.22(19) . . . . ?
C41 C36 C37 C38 -0.32(19) . . . . ?
C43 N42 C39 C38 -21.02(17) . . . . ?
C43 N42 C39 C40 157.61(12) . . . . ?
C43 N42 C50 C51 -38.88(17) . . . . ?
C43 N42 C50 C55 137.28(13) . . . . ?
C43 C44 C45 C46 1.2(2) . . . . ?
C44 C43 C48 C47 1.19(19) . . . . ?
C44 C45 C46 C47 0.6(2) . . . . ?
C44 C45 C46 C49 -179.10(14) . . . . ?
C45 C46 C47 C48 -1.6(2) . . . . ?
C46 C47 C48 C43 0.7(2) . . . . ?
C48 C43 C44 C45 -2.10(19) . . . . ?
C49 C46 C47 C48 178.17(13) . . . . ?
C50 N42 C39 C38 149.64(12) . . . . ?
C50 N42 C39 C40 -31.73(19) . . . . ?
C50 N42 C43 C44 127.75(13) . . . . ?
C50 N42 C43 C48 -53.42(16) . . . . ?
C50 C51 C52 C53 0.7(2) . . . . ?
C51 C50 C55 C54 -1.08(19) . . . . ?
C51 C52 C53 C54 -1.2(2) . . . . ?
C51 C52 C53 C56 178.91(13) . . . . ?
C52 C53 C54 C55 0.6(2) . . . . ?
C53 C54 C55 C50 0.5(2) . . . . ?
C55 C50 C51 C52 0.5(2) . . . . ?
C56 C53 C54 C55 -179.49(13) . . . . ?
