#------------------------------------------------------------------------------
#$Date: 2019-10-16 12:09:07 +0300 (Wed, 16 Oct 2019) $
#$Revision: 219385 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/46/7234660.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_7234660
loop_
_publ_author_name
'A. Punzi'
'M. A. M. Capozzi'
'V. Fino'
'C. Carlucci'
'M. Suriano'
'E. Mesto'
'E. Schingaro'
'E. Orgiu'
'S. Bonacchi'
'T. Leydecker'
'P. Samori'
'R. Musio'
'G. M. Farinola'
_publ_section_title
;
 Croconaines as molecular materials for organic electronics: synthesis,
 solid state structure and use in transistor devices
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              3138
_journal_page_last               3142
_journal_paper_doi               10.1039/C6TC00264A
_journal_volume                  4
_journal_year                    2016
_chemical_formula_moiety         'C27 H24 N2 O3'
_chemical_formula_sum            'C27 H24 N2 O3'
_chemical_formula_weight         424.50
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_cell_angle_alpha                66.188(2)
_cell_angle_beta                 81.891(2)
_cell_angle_gamma                72.294(2)
_cell_formula_units_Z            4
_cell_length_a                   11.0823(3)
_cell_length_b                   14.6505(5)
_cell_length_c                   18.1033(6)
_cell_measurement_reflns_used    4509
_cell_measurement_temperature    293
_cell_measurement_theta_max      32
_cell_measurement_theta_min      2
_cell_volume                     2561.12(15)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'Apex2 (Bruker AXS, 2010)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  CRYSTALS
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5370
_diffrn_reflns_theta_full        20.464
_diffrn_reflns_theta_max         20.882
_diffrn_reflns_theta_min         1.579
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.101
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platly
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         5331
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.1105
_refine_ls_R_factor_gt           0.0593
_refine_ls_shift/su_max          0.0001964
_refine_ls_shift/su_mean         0.0000176
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.09P)² + 1.34P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1601
_refine_ls_wR_factor_gt          0.1514
_refine_ls_wR_factor_ref         0.1601
_reflns_limit_h_max              11
_reflns_limit_h_min              -10
_reflns_limit_k_max              14
_reflns_limit_k_min              -13
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                3300
_reflns_number_total             5370
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   3.08
_oxford_diffrn_Wilson_scale      12.04
_oxford_refine_ls_r_factor_ref   0.1105
_oxford_refine_ls_scale          0.4039(8)
_oxford_reflns_number_all        5331
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-3138.cif
_cod_data_source_block           S41_4a
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               7234660
_iucr_refine_instruction_details_constraints
;
#
# Punched on 20/07/15 at 18:22:01
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 153,X'S) H   ( 152,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 163,X'S) H   ( 162,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 262,X'S) H   ( 261,X'S) H   ( 263,X'S) 
RIDE C   (  27,X'S) H   ( 272,X'S) H   ( 271,X'S) H   ( 273,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) 
RIDE C   (  40,X'S) H   ( 401,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) 
RIDE C   (  42,X'S) H   ( 423,X'S) H   ( 422,X'S) H   ( 421,X'S) 
RIDE C   (  43,X'S) H   ( 433,X'S) H   ( 432,X'S) H   ( 431,X'S) 
RIDE C   (  44,X'S) H   ( 441,X'S) 
RIDE C   (  49,X'S) H   ( 491,X'S) 
RIDE C   (  50,X'S) H   ( 501,X'S) 
RIDE C   (  51,X'S) H   ( 511,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) H   ( 533,X'S) H   ( 532,X'S) 
RIDE C   (  54,X'S) H   ( 541,X'S) H   ( 543,X'S) H   ( 542,X'S) 
RIDE N   (   1,X'S) H   (  11,X'S) 
RIDE N   (   2,X'S) H   (  21,X'S) 
RIDE N   (   3,X'S) H   (  31,X'S) 
RIDE N   (   4,X'S) H   (  41,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
#
# Punched on 20/07/15 at 18:22:01
#
#LIST     16                                                                    
SIMU  C(51)  C(50)  AND C(61)  C(60) 
DELU  C(51)  C(50)  AND C(61)  C(60) 
SIMU  0.005 C(36)  C(41)  AND C(47)  C(52) 
DELU  0.005 C(36)  C(41)  AND C(47)  C(52) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
loop_
_symmetry_equiv_pos_as_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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.7035(4) 0.6107(4) 0.5818(3) 0.0573 1.0000 Uani . . . . . .
C2 C 0.6028(4) 0.5596(4) 0.5857(3) 0.0520 1.0000 Uani . . . . . .
C3 C 0.4941(4) 0.6385(3) 0.5476(3) 0.0498 1.0000 Uani . . . . . .
C4 C 0.5287(4) 0.7378(4) 0.5117(3) 0.0524 1.0000 Uani . . . . . .
C5 C 0.6561(4) 0.7212(3) 0.5326(3) 0.0504 1.0000 Uani . . . . . .
C6 C 0.7288(4) 0.7885(4) 0.5150(3) 0.0596 1.0000 Uani . . . . . .
C7 C 0.7019(4) 0.8943(4) 0.4669(3) 0.0547 1.0000 Uani . . . . . .
C8 C 0.7906(4) 0.9625(4) 0.4512(3) 0.0587 1.0000 Uani . . . . . .
C9 C 0.7113(4) 1.0642(3) 0.3974(3) 0.0562 1.0000 Uani . . . . . .
C10 C 0.5958(4) 1.0559(4) 0.3862(3) 0.0545 1.0000 Uani . . . . . .
C11 C 0.5039(5) 1.1353(4) 0.3390(3) 0.0663 1.0000 Uani . . . . . .
C12 C 0.5282(5) 1.2325(4) 0.3025(3) 0.0796 1.0000 Uani . . . . . .
C13 C 0.6451(6) 1.2430(4) 0.3133(3) 0.0784 1.0000 Uani . . . . . .
C14 C 0.7356(5) 1.1597(4) 0.3601(3) 0.0715 1.0000 Uani . . . . . .
C15 C 0.9123(4) 0.9237(4) 0.4088(3) 0.0841 1.0000 Uani . . . . . .
C16 C 0.8187(5) 0.9660(4) 0.5319(3) 0.0875 1.0000 Uani . . . . . .
C17 C 0.3700(4) 0.6364(3) 0.5440(3) 0.0534 1.0000 Uani . . . . . .
C18 C 0.3215(4) 0.5517(4) 0.5742(3) 0.0510 1.0000 Uani . . . . . .
C19 C 0.1806(4) 0.5573(3) 0.5789(3) 0.0527 1.0000 Uani . . . . . .
C20 C 0.1868(4) 0.4428(3) 0.6157(3) 0.0549 1.0000 Uani . . . . . .
C21 C 0.3118(4) 0.3843(4) 0.6298(3) 0.0536 1.0000 Uani . . . . . .
C22 C 0.3472(5) 0.2769(4) 0.6634(3) 0.0637 1.0000 Uani . . . . . .
C23 C 0.2508(5) 0.2295(4) 0.6815(3) 0.0688 1.0000 Uani . . . . . .
C24 C 0.1258(5) 0.2861(4) 0.6679(3) 0.0719 1.0000 Uani . . . . . .
C25 C 0.0920(4) 0.3942(4) 0.6349(3) 0.0653 1.0000 Uani . . . . . .
C26 C 0.1113(4) 0.6121(4) 0.6356(3) 0.0700 1.0000 Uani . . . . . .
C27 C 0.1203(4) 0.6130(4) 0.4963(3) 0.0665 1.0000 Uani . . . . . .
C28 C 0.2996(5) 0.8030(4) 1.0683(3) 0.0713 1.0000 Uani . . . . . .
C29 C 0.3979(4) 0.8464(4) 1.0750(3) 0.0596 1.0000 Uani . . . . . .
C30 C 0.5097(4) 0.8099(3) 1.0336(3) 0.0524 1.0000 Uani . . . . . .
C31 C 0.4772(4) 0.7484(3) 0.9953(3) 0.0560 1.0000 Uani . . . . . .
C32 C 0.3494(4) 0.7444(3) 1.0160(3) 0.0582 1.0000 Uani . . . . . .
C33 C 0.2743(4) 0.6964(4) 0.9963(3) 0.0676 1.0000 Uani . . . . . .
C34 C 0.3063(5) 0.6347(4) 0.9521(3) 0.0622 1.0000 Uani . . . . . .
C35 C 0.2185(5) 0.5864(4) 0.9340(3) 0.0732 1.0000 Uani . . . . . .
C36 C 0.3044(5) 0.5291(4) 0.8849(3) 0.0740 1.0000 Uani D . . . . .
C37 C 0.4241(5) 0.5438(4) 0.8789(3) 0.0644 1.0000 Uani . . . . . .
C38 C 0.5242(5) 0.5006(4) 0.8382(3) 0.0774 1.0000 Uani . . . . . .
C39 C 0.5034(7) 0.4393(4) 0.8020(3) 0.0953 1.0000 Uani . . . . . .
C40 C 0.3816(8) 0.4256(5) 0.8070(4) 0.0995 1.0000 Uani . . . . . .
C41 C 0.2818(6) 0.4706(4) 0.8480(3) 0.0855 1.0000 Uani D . . . . .
C42 C 0.1062(5) 0.6700(5) 0.8859(4) 0.1112 1.0000 Uani . . . . . .
C43 C 0.1741(5) 0.5107(4) 1.0123(3) 0.0950 1.0000 Uani . . . . . .
C44 C 0.6316(4) 0.8166(3) 1.0297(3) 0.0611 1.0000 Uani . . . . . .
C45 C 0.6793(4) 0.8684(3) 1.0629(3) 0.0531 1.0000 Uani . . . . . .
C46 C 0.8196(4) 0.8584(3) 1.0680(3) 0.0561 1.0000 Uani . . . . . .
C47 C 0.8121(4) 0.9301(3) 1.1100(3) 0.0571 1.0000 Uani D . . . . .
C48 C 0.6880(4) 0.9715(3) 1.1272(3) 0.0541 1.0000 Uani . . . . . .
C49 C 0.6493(5) 1.0397(4) 1.1657(3) 0.0626 1.0000 Uani . . . . . .
C50 C 0.7426(5) 1.0660(4) 1.1885(3) 0.0714 1.0000 Uani D . . . . .
C51 C 0.8689(5) 1.0253(4) 1.1740(3) 0.0749 1.0000 Uani D . . . . .
C52 C 0.9064(4) 0.9547(4) 1.1338(3) 0.0673 1.0000 Uani D . . . . .
C53 C 0.8905(4) 0.7461(4) 1.1169(3) 0.0706 1.0000 Uani . . . . . .
C54 C 0.8818(4) 0.8947(4) 0.9833(3) 0.0742 1.0000 Uani . . . . . .
N1 N 0.5948(3) 0.9513(3) 0.4293(2) 0.0587 1.0000 Uani . . . . . .
N2 N 0.3886(3) 0.4527(3) 0.6045(2) 0.0543 1.0000 Uani . . . . . .
N3 N 0.4209(4) 0.6079(3) 0.9191(2) 0.0641 1.0000 Uani . . . . . .
N4 N 0.6105(3) 0.9317(3) 1.0991(2) 0.0587 1.0000 Uani . . . . . .
O1 O 0.8068(3) 0.5673(2) 0.6145(2) 0.0806 1.0000 Uani . . . . . .
O2 O 0.6209(3) 0.4643(2) 0.61701(19) 0.0643 1.0000 Uani . . . . . .
O3 O 0.4534(3) 0.8220(2) 0.46993(19) 0.0636 1.0000 Uani . . . . . .
O4 O 0.1938(3) 0.8126(3) 1.1022(3) 0.1037 1.0000 Uani . . . . . .
O5 O 0.3803(3) 0.9062(3) 1.1109(2) 0.0828 1.0000 Uani . . . . . .
O6 O 0.5557(3) 0.7067(3) 0.9533(2) 0.0713 1.0000 Uani . . . . . .
H61 H 0.8074 0.7590 0.5394 0.0692 1.0000 Uiso R . . . . .
H111 H 0.4249 1.1268 0.3325 0.0787 1.0000 Uiso R . . . . .
H121 H 0.4657 1.2898 0.2710 0.0930 1.0000 Uiso R . . . . .
H131 H 0.6629 1.3076 0.2880 0.0933 1.0000 Uiso R . . . . .
H141 H 0.8144 1.1664 0.3668 0.0844 1.0000 Uiso R . . . . .
H151 H 0.9671 0.9689 0.3963 0.1239 1.0000 Uiso R . . . . .
H153 H 0.9575 0.8553 0.4431 0.1239 1.0000 Uiso R . . . . .
H152 H 0.8929 0.9220 0.3582 0.1237 1.0000 Uiso R . . . . .
H161 H 0.8696 1.0124 0.5216 0.1291 1.0000 Uiso R . . . . .
H163 H 0.7400 0.9883 0.5598 0.1289 1.0000 Uiso R . . . . .
H162 H 0.8646 0.8976 0.5678 0.1287 1.0000 Uiso R . . . . .
H171 H 0.3119 0.7009 0.5184 0.0621 1.0000 Uiso R . . . . .
H221 H 0.4325 0.2391 0.6724 0.0762 1.0000 Uiso R . . . . .
H231 H 0.2709 0.1574 0.7034 0.0816 1.0000 Uiso R . . . . .
H241 H 0.0620 0.2521 0.6800 0.0847 1.0000 Uiso R . . . . .
H251 H 0.0075 0.4326 0.6254 0.0777 1.0000 Uiso R . . . . .
H262 H 0.0250 0.6075 0.6424 0.1004 1.0000 Uiso R . . . . .
H261 H 0.1110 0.6834 0.6131 0.1008 1.0000 Uiso R . . . . .
H263 H 0.1520 0.5764 0.6881 0.1009 1.0000 Uiso R . . . . .
H272 H 0.0331 0.6135 0.5025 0.0967 1.0000 Uiso R . . . . .
H271 H 0.1255 0.6843 0.4735 0.0964 1.0000 Uiso R . . . . .
H273 H 0.1628 0.5772 0.4615 0.0965 1.0000 Uiso R . . . . .
H331 H 0.1899 0.7078 1.0157 0.0786 1.0000 Uiso R . . . . .
H381 H 0.6041 0.5118 0.8347 0.0910 1.0000 Uiso R . . . . .
H391 H 0.5707 0.4084 0.7753 0.1125 1.0000 Uiso R . . . . .
H401 H 0.3672 0.3862 0.7806 0.1178 1.0000 Uiso R . . . . .
H411 H 0.2001 0.4615 0.8507 0.1091 1.0000 Uiso R . . . . .
H423 H 0.0500 0.6399 0.8746 0.1639 1.0000 Uiso R . . . . .
H422 H 0.0589 0.7109 0.9152 0.1640 1.0000 Uiso R . . . . .
H421 H 0.1358 0.7142 0.8358 0.1638 1.0000 Uiso R . . . . .
H433 H 0.1313 0.4712 0.9997 0.1410 1.0000 Uiso R . . . . .
H432 H 0.1166 0.5484 1.0421 0.1408 1.0000 Uiso R . . . . .
H431 H 0.2464 0.4642 1.0447 0.1409 1.0000 Uiso R . . . . .
H441 H 0.6893 0.7826 0.9991 0.0726 1.0000 Uiso R . . . . .
H491 H 0.5644 1.0666 1.1753 0.0748 1.0000 Uiso R . . . . .
H501 H 0.7190 1.1118 1.2147 0.0840 1.0000 Uiso R . . . . .
H511 H 0.9323 1.0440 1.1894 0.0868 1.0000 Uiso R . . . . .
H521 H 0.9932 0.9256 1.1234 0.0807 1.0000 Uiso R . . . . .
H531 H 0.9764 0.7427 1.1252 0.1048 1.0000 Uiso R . . . . .
H533 H 0.8464 0.7225 1.1689 0.1047 1.0000 Uiso R . . . . .
H532 H 0.8916 0.7019 1.0890 0.1046 1.0000 Uiso R . . . . .
H541 H 0.9704 0.8864 0.9899 0.1096 1.0000 Uiso R . . . . .
H543 H 0.8394 0.9664 0.9520 0.1098 1.0000 Uiso R . . . . .
H542 H 0.8768 0.8522 0.9549 0.1097 1.0000 Uiso R . . . . .
H31 H 0.4817 0.6348 0.9172 0.0756 1.0000 Uiso R . . . . .
H11 H 0.5317 0.9270 0.4287 0.0690 1.0000 Uiso R . . . . .
H21 H 0.4700 0.4328 0.6038 0.0650 1.0000 Uiso R . . . . .
H41 H 0.5284 0.9510 1.1005 0.0690 1.0000 Uiso R . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . C5 . 107.8(4) yes
C2 . C1 . O1 . 125.9(4) yes
C5 . C1 . O1 . 126.3(4) yes
C1 . C2 . C3 . 107.8(4) yes
C1 . C2 . O2 . 122.3(4) yes
C3 . C2 . O2 . 130.0(4) yes
C2 . C3 . C4 . 107.6(4) yes
C2 . C3 . C17 . 131.7(4) yes
C4 . C3 . C17 . 120.5(4) yes
C3 . C4 . C5 . 109.6(4) yes
C3 . C4 . O3 . 122.7(4) yes
C5 . C4 . O3 . 127.7(4) yes
C1 . C5 . C4 . 106.9(4) yes
C1 . C5 . C6 . 121.8(4) yes
C4 . C5 . C6 . 131.3(4) yes
C5 . C6 . C7 . 129.7(4) yes
C5 . C6 . H61 . 114.7 no
C7 . C6 . H61 . 115.6 no
C6 . C7 . C8 . 125.4(4) yes
C6 . C7 . N1 . 125.2(4) yes
C8 . C7 . N1 . 109.4(4) yes
C7 . C8 . C9 . 100.5(4) yes
C7 . C8 . C15 . 110.4(4) yes
C9 . C8 . C15 . 112.0(4) yes
C7 . C8 . C16 . 110.3(4) yes
C9 . C8 . C16 . 111.7(4) yes
C15 . C8 . C16 . 111.5(4) yes
C8 . C9 . C10 . 110.7(4) yes
C8 . C9 . C14 . 130.9(4) yes
C10 . C9 . C14 . 118.4(5) yes
C9 . C10 . C11 . 124.3(4) yes
C9 . C10 . N1 . 107.6(4) yes
C11 . C10 . N1 . 128.1(4) yes
C10 . C11 . C12 . 117.1(5) yes
C10 . C11 . H111 . 122.1 no
C12 . C11 . H111 . 120.8 no
C11 . C12 . C13 . 119.7(5) yes
C11 . C12 . H121 . 119.5 no
C13 . C12 . H121 . 120.9 no
C12 . C13 . C14 . 120.8(5) yes
C12 . C13 . H131 . 120.2 no
C14 . C13 . H131 . 118.9 no
C9 . C14 . C13 . 119.7(5) yes
C9 . C14 . H141 . 119.3 no
C13 . C14 . H141 . 121.0 no
C8 . C15 . H151 . 110.5 no
C8 . C15 . H153 . 110.1 no
H151 . C15 . H153 . 108.2 no
C8 . C15 . H152 . 110.4 no
H151 . C15 . H152 . 108.5 no
H153 . C15 . H152 . 109.1 no
C8 . C16 . H161 . 110.2 no
C8 . C16 . H163 . 111.0 no
H161 . C16 . H163 . 109.4 no
C8 . C16 . H162 . 110.3 no
H161 . C16 . H162 . 108.2 no
H163 . C16 . H162 . 107.6 no
C3 . C17 . C18 . 128.2(4) yes
C3 . C17 . H171 . 115.9 no
C18 . C17 . H171 . 115.9 no
C17 . C18 . C19 . 124.9(4) yes
C17 . C18 . N2 . 125.9(4) yes
C19 . C18 . N2 . 109.1(3) yes
C18 . C19 . C20 . 100.7(3) yes
C18 . C19 . C26 . 109.3(3) yes
C20 . C19 . C26 . 111.3(4) yes
C18 . C19 . C27 . 112.2(4) yes
C20 . C19 . C27 . 112.9(3) yes
C26 . C19 . C27 . 110.1(4) yes
C19 . C20 . C21 . 109.7(4) yes
C19 . C20 . C25 . 130.5(4) yes
C21 . C20 . C25 . 119.8(4) yes
C20 . C21 . C22 . 122.9(4) yes
C20 . C21 . N2 . 108.1(4) yes
C22 . C21 . N2 . 129.0(4) yes
C21 . C22 . C23 . 116.4(4) yes
C21 . C22 . H221 . 121.1 no
C23 . C22 . H221 . 122.4 no
C22 . C23 . C24 . 121.7(5) yes
C22 . C23 . H231 . 119.0 no
C24 . C23 . H231 . 119.3 no
C23 . C24 . C25 . 121.1(5) yes
C23 . C24 . H241 . 120.1 no
C25 . C24 . H241 . 118.8 no
C24 . C25 . C20 . 118.1(4) yes
C24 . C25 . H251 . 121.1 no
C20 . C25 . H251 . 120.8 no
C19 . C26 . H262 . 107.6 no
C19 . C26 . H261 . 110.9 no
H262 . C26 . H261 . 109.3 no
C19 . C26 . H263 . 109.2 no
H262 . C26 . H263 . 109.1 no
H261 . C26 . H263 . 110.8 no
C19 . C27 . H272 . 108.8 no
C19 . C27 . H271 . 109.5 no
H272 . C27 . H271 . 108.7 no
C19 . C27 . H273 . 109.6 no
H272 . C27 . H273 . 109.5 no
H271 . C27 . H273 . 110.7 no
C29 . C28 . C32 . 107.9(4) yes
C29 . C28 . O4 . 125.7(5) yes
C32 . C28 . O4 . 126.4(4) yes
C28 . C29 . C30 . 108.7(4) yes
C28 . C29 . O5 . 122.8(4) yes
C30 . C29 . O5 . 128.5(4) yes
C29 . C30 . C31 . 106.9(4) yes
C29 . C30 . C44 . 132.3(4) yes
C31 . C30 . C44 . 120.6(4) yes
C30 . C31 . C32 . 109.3(4) yes
C30 . C31 . O6 . 122.4(4) yes
C32 . C31 . O6 . 128.3(4) yes
C28 . C32 . C31 . 107.1(4) yes
C28 . C32 . C33 . 121.0(4) yes
C31 . C32 . C33 . 131.9(5) yes
C32 . C33 . C34 . 129.1(4) yes
C32 . C33 . H331 . 115.9 no
C34 . C33 . H331 . 115.0 no
C33 . C34 . C35 . 125.2(5) yes
C33 . C34 . N3 . 125.2(4) yes
C35 . C34 . N3 . 109.6(4) yes
C34 . C35 . C36 . 101.3(4) yes
C34 . C35 . C42 . 110.4(4) yes
C36 . C35 . C42 . 112.2(5) yes
C34 . C35 . C43 . 110.5(4) yes
C36 . C35 . C43 . 110.8(4) yes
C42 . C35 . C43 . 111.1(5) yes
C35 . C36 . C37 . 108.9(4) yes
C35 . C36 . C41 . 131.3(5) yes
C37 . C36 . C41 . 119.8(6) yes
C36 . C37 . C38 . 123.1(5) yes
C36 . C37 . N3 . 108.4(5) yes
C38 . C37 . N3 . 128.5(5) yes
C37 . C38 . C39 . 117.8(5) yes
C37 . C38 . H381 . 121.6 no
C39 . C38 . H381 . 120.6 no
C38 . C39 . C40 . 119.3(6) yes
C38 . C39 . H391 . 118.7 no
C40 . C39 . H391 . 122.0 no
C39 . C40 . C41 . 121.9(6) yes
C39 . C40 . H401 . 118.9 no
C41 . C40 . H401 . 119.3 no
C40 . C41 . C36 . 118.3(6) yes
C40 . C41 . H411 . 121.3 no
C36 . C41 . H411 . 120.4 no
C35 . C42 . H423 . 110.8 no
C35 . C42 . H422 . 111.3 no
H423 . C42 . H422 . 107.1 no
C35 . C42 . H421 . 109.8 no
H423 . C42 . H421 . 108.8 no
H422 . C42 . H421 . 109.0 no
C35 . C43 . H433 . 109.6 no
C35 . C43 . H432 . 110.0 no
H433 . C43 . H432 . 109.0 no
C35 . C43 . H431 . 109.4 no
H433 . C43 . H431 . 109.2 no
H432 . C43 . H431 . 109.6 no
C30 . C44 . C45 . 128.5(4) yes
C30 . C44 . H441 . 115.1 no
C45 . C44 . H441 . 116.4 no
C44 . C45 . C46 . 125.6(4) yes
C44 . C45 . N4 . 125.6(4) yes
C46 . C45 . N4 . 108.7(4) yes
C45 . C46 . C47 . 101.2(3) yes
C45 . C46 . C53 . 110.5(3) yes
C47 . C46 . C53 . 112.6(4) yes
C45 . C46 . C54 . 111.3(4) yes
C47 . C46 . C54 . 111.7(4) yes
C53 . C46 . C54 . 109.4(4) yes
C46 . C47 . C48 . 109.8(4) yes
C46 . C47 . C52 . 130.5(4) yes
C48 . C47 . C52 . 119.7(4) yes
C47 . C48 . C49 . 124.1(4) yes
C47 . C48 . N4 . 108.7(4) yes
C49 . C48 . N4 . 127.2(4) yes
C48 . C49 . C50 . 116.7(4) yes
C48 . C49 . H491 . 121.3 no
C50 . C49 . H491 . 122.0 no
C49 . C50 . C51 . 121.5(5) yes
C49 . C50 . H501 . 118.4 no
C51 . C50 . H501 . 120.0 no
C50 . C51 . C52 . 120.6(5) yes
C50 . C51 . H511 . 121.1 no
C52 . C51 . H511 . 118.3 no
C51 . C52 . C47 . 117.4(4) yes
C51 . C52 . H521 . 121.8 no
C47 . C52 . H521 . 120.9 no
C46 . C53 . H531 . 109.4 no
C46 . C53 . H533 . 108.5 no
H531 . C53 . H533 . 110.0 no
C46 . C53 . H532 . 110.5 no
H531 . C53 . H532 . 109.7 no
H533 . C53 . H532 . 108.7 no
C46 . C54 . H541 . 108.0 no
C46 . C54 . H543 . 110.5 no
H541 . C54 . H543 . 110.8 no
C46 . C54 . H542 . 110.2 no
H541 . C54 . H542 . 108.7 no
H543 . C54 . H542 . 108.7 no
C10 . N1 . C7 . 111.8(4) yes
C10 . N1 . H11 . 123.7 no
C7 . N1 . H11 . 124.4 no
C21 . N2 . C18 . 112.4(3) yes
C21 . N2 . H21 . 123.7 no
C18 . N2 . H21 . 123.6 no
C37 . N3 . C34 . 111.7(4) yes
C37 . N3 . H31 . 124.3 no
C34 . N3 . H31 . 123.4 no
C48 . N4 . C45 . 111.6(4) yes
C48 . N4 . H41 . 124.3 no
C45 . N4 . H41 . 123.8 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.501(6) yes
C1 . C5 . 1.463(6) yes
C1 . O1 . 1.229(5) yes
C2 . C3 . 1.417(6) yes
C2 . O2 . 1.238(5) yes
C3 . C4 . 1.481(6) yes
C3 . C17 . 1.397(5) yes
C4 . C5 . 1.436(6) yes
C4 . O3 . 1.260(5) yes
C5 . C6 . 1.371(6) yes
C6 . C7 . 1.397(6) yes
C6 . H61 . 0.930 no
C7 . C8 . 1.528(6) yes
C7 . N1 . 1.317(5) yes
C8 . C9 . 1.488(6) yes
C8 . C15 . 1.525(6) yes
C8 . C16 . 1.559(6) yes
C9 . C10 . 1.372(6) yes
C9 . C14 . 1.379(6) yes
C10 . C11 . 1.358(6) yes
C10 . N1 . 1.414(5) yes
C11 . C12 . 1.399(6) yes
C11 . H111 . 0.951 no
C12 . C13 . 1.400(7) yes
C12 . H121 . 0.938 no
C13 . C14 . 1.369(7) yes
C13 . H131 . 0.939 no
C14 . H141 . 0.936 no
C15 . H151 . 0.971 no
C15 . H153 . 0.959 no
C15 . H152 . 0.981 no
C16 . H161 . 0.958 no
C16 . H163 . 0.979 no
C16 . H162 . 0.971 no
C17 . C18 . 1.378(6) yes
C17 . H171 . 0.939 no
C18 . C19 . 1.531(5) yes
C18 . N2 . 1.333(5) yes
C19 . C20 . 1.517(6) yes
C19 . C26 . 1.536(6) yes
C19 . C27 . 1.521(6) yes
C20 . C21 . 1.386(6) yes
C20 . C25 . 1.373(6) yes
C21 . C22 . 1.386(6) yes
C21 . N2 . 1.406(5) yes
C22 . C23 . 1.377(6) yes
C22 . H221 . 0.938 no
C23 . C24 . 1.378(6) yes
C23 . H231 . 0.930 no
C24 . C25 . 1.394(6) yes
C24 . H241 . 0.938 no
C25 . H251 . 0.933 no
C26 . H262 . 0.966 no
C26 . H261 . 0.954 no
C26 . H263 . 0.978 no
C27 . H272 . 0.955 no
C27 . H271 . 0.973 no
C27 . H273 . 0.963 no
C28 . C29 . 1.458(6) yes
C28 . C32 . 1.470(6) yes
C28 . O4 . 1.240(5) yes
C29 . C30 . 1.430(6) yes
C29 . O5 . 1.244(5) yes
C30 . C31 . 1.480(6) yes
C30 . C44 . 1.374(6) yes
C31 . C32 . 1.426(6) yes
C31 . O6 . 1.254(5) yes
C32 . C33 . 1.399(6) yes
C33 . C34 . 1.376(6) yes
C33 . H331 . 0.942 no
C34 . C35 . 1.500(6) yes
C34 . N3 . 1.340(5) yes
C35 . C36 . 1.509(7) yes
C35 . C42 . 1.525(7) yes
C35 . C43 . 1.532(7) yes
C36 . C37 . 1.390(6) yes
C36 . C41 . 1.373(7) yes
C37 . C38 . 1.376(7) yes
C37 . N3 . 1.392(6) yes
C38 . C39 . 1.392(7) yes
C38 . H381 . 0.937 no
C39 . C40 . 1.410(8) yes
C39 . H391 . 0.930 no
C40 . C41 . 1.389(8) yes
C40 . H401 . 0.942 no
C41 . H411 . 0.946 no
C42 . H423 . 0.948 no
C42 . H422 . 0.950 no
C42 . H421 . 0.960 no
C43 . H433 . 0.956 no
C43 . H432 . 0.965 no
C43 . H431 . 0.964 no
C44 . C45 . 1.386(6) yes
C44 . H441 . 0.944 no
C45 . C46 . 1.530(6) yes
C45 . N4 . 1.339(5) yes
C46 . C47 . 1.505(6) yes
C46 . C53 . 1.531(6) yes
C46 . C54 . 1.541(6) yes
C47 . C48 . 1.370(6) yes
C47 . C52 . 1.374(6) yes
C48 . C49 . 1.374(6) yes
C48 . N4 . 1.414(5) yes
C49 . C50 . 1.371(6) yes
C49 . H491 . 0.924 no
C50 . C51 . 1.379(6) yes
C50 . H501 . 0.927 no
C51 . C52 . 1.426(6) yes
C51 . H511 . 0.939 no
C52 . H521 . 0.951 no
C53 . H531 . 0.968 no
C53 . H533 . 0.977 no
C53 . H532 . 0.966 no
C54 . H541 . 0.970 no
C54 . H543 . 0.970 no
C54 . H542 . 0.971 no
N1 . H11 . 0.880 no
N2 . H21 . 0.859 no
N3 . H31 . 0.868 no
N4 . H41 . 0.867 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C25 . H251 . O1 1_455 162.5 0.933 2.453 3.355(8) no
C52 . H521 . O4 1_655 164.8 0.951 2.422 3.349(8) no
N3 . H31 . C31 . 123.9 0.868 2.570 3.138(8) no
N3 . H31 . O6 . 150.8 0.868 1.856 2.648(8) yes
N1 . H11 . C4 . 123.1 0.880 2.572 3.140(8) yes
N1 . H11 . O3 . 149.7 0.880 1.837 2.634(8) yes
N2 . H21 . O2 . 144.1 0.859 1.934 2.677(8) yes
N4 . H41 . O5 . 144.1 0.867 1.905 2.656(8) yes
