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#$Date: 2022-12-15 11:51:03 +0200 (Thu, 15 Dec 2022) $
#$Revision: 279911 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/64/8106408.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_8106408
loop_
_publ_author_name
'Zuo, Zhenyu'
'Lei, Fuhou'
'Song, Xiao'
'Wang, Lu'
_publ_section_title
;
 The crystal structure of
 N,N-diethyl-4,6-bis(naphthalen-2-yloxy)-1,3,5-triazin-2-amine, C27H24N4O2
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1083
_journal_page_last               1085
_journal_paper_doi               10.1515/ncrs-2018-0207
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C27 H24 N4 O2'
_chemical_formula_sum            'C27 H24 N4 O2'
_chemical_formula_weight         436.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90.13
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.8073(2)
_cell_length_b                   31.2564(9)
_cell_length_c                   24.8105(8)
_cell_measurement_reflns_used    5764
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      4.6200
_cell_measurement_theta_min      68.6860
_cell_volume                     4503.5(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  bruker-ccd
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0694
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13522
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        66.008
_diffrn_reflns_theta_max         66.008
_diffrn_reflns_theta_min         4.243
_exptl_absorpt_coefficient_mu    0.665
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       block
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     604
_refine_ls_number_reflns         6998
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0644
_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)+(0.0803P)²+0.7701P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1607
_refine_ls_wR_factor_ref         0.1854
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5443
_reflns_number_total             6998
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0207_suppl.cif
_cod_data_source_block           1
_cod_database_code               8106408
_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   0.895
_shelx_estimated_absorpt_t_min   0.884
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.586(2)
 0.414(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C27) = Uanis(C27A)
4. Others
 Fixed Sof: H26A(0.5) H26B(0.5) H26C(0.5) H26D(0.5) C27(0.5) H27A(0.5)
 H27B(0.5) H27C(0.5) C27A(0.5) H27D(0.5) H27E(0.5) H27F(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C26(H26A,H26B), C26(H26C,H26D), C51(H51A,H51B), C53(H53A,H53B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C14(H14), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C29(H29), C31(H31), C32(H32),
  C33(H33), C34(H34), C36(H36), C37(H37), C41(H41), C42(H42), C44(H44),
 C45(H45), C46(H46), C47(H47), C49(H49)
5.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C27A(H27D,H27E,H27F), C52(H52A,H52B,
 H52C), C54(H54A,H54B,H54C)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 1.5751(6) 0.07623(12) 0.34842(16) 0.0366(8) Uani 1 1 d . . . . .
H1 H 1.6264 0.0761 0.3121 0.044 Uiso 1 1 calc R . . . .
C2 C 1.7076(6) 0.05881(11) 0.38842(16) 0.0364(8) Uani 1 1 d . . . . .
H2 H 1.8522 0.0464 0.3798 0.044 Uiso 1 1 calc R . . . .
C3 C 1.6317(6) 0.05909(11) 0.44264(16) 0.0334(8) Uani 1 1 d . . . . .
C4 C 1.7662(7) 0.04089(12) 0.48427(17) 0.0406(9) Uani 1 1 d . . . . .
H4 H 1.9108 0.0283 0.4761 0.049 Uiso 1 1 calc R . . . .
C5 C 1.6897(8) 0.04135(14) 0.5358(2) 0.0532(12) Uani 1 1 d . . . . .
H5 H 1.7809 0.0287 0.5634 0.064 Uiso 1 1 calc R . . . .
C6 C 1.4750(8) 0.06052(13) 0.54948(18) 0.0469(10) Uani 1 1 d . . . . .
H6 H 1.4252 0.0610 0.5859 0.056 Uiso 1 1 calc R . . . .
C7 C 1.3397(7) 0.07839(12) 0.50970(17) 0.0417(9) Uani 1 1 d . . . . .
H7 H 1.1956 0.0909 0.5186 0.050 Uiso 1 1 calc R . . . .
C8 C 1.4162(6) 0.07808(10) 0.45559(16) 0.0322(8) Uani 1 1 d . . . . .
C9 C 1.2810(6) 0.09590(10) 0.41331(15) 0.0324(8) Uani 1 1 d . . . . .
H9 H 1.1364 0.1088 0.4208 0.039 Uiso 1 1 calc R . . . .
C10 C 1.3619(6) 0.09421(11) 0.36213(15) 0.0315(8) Uani 1 1 d . . . . .
C11 C 1.1321(6) 0.09058(10) 0.28290(15) 0.0320(8) Uani 1 1 d . . . . .
C12 C 0.9434(6) 0.08907(10) 0.20643(15) 0.0315(7) Uani 1 1 d . . . . .
C13 C 0.7102(6) 0.09100(11) 0.12761(16) 0.0347(8) Uani 1 1 d . . . . .
C14 C 0.7709(6) 0.09341(11) 0.07486(16) 0.0344(8) Uani 1 1 d . . . . .
H14 H 0.9132 0.1060 0.0647 0.041 Uiso 1 1 calc R . . . .
C15 C 0.6197(7) 0.07690(11) 0.03513(16) 0.0357(9) Uani 1 1 d . . . . .
C16 C 0.6779(8) 0.07841(13) -0.02049(17) 0.0462(10) Uani 1 1 d . . . . .
H16 H 0.8179 0.0912 -0.0319 0.055 Uiso 1 1 calc R . . . .
C17 C 0.5286(10) 0.06103(14) -0.0574(2) 0.0587(13) Uani 1 1 d . . . . .
H17 H 0.5672 0.0617 -0.0945 0.070 Uiso 1 1 calc R . . . .
C18 C 0.3182(10) 0.04211(14) -0.0413(2) 0.0601(14) Uani 1 1 d . . . . .
H18 H 0.2179 0.0303 -0.0676 0.072 Uiso 1 1 calc R . . . .
C19 C 0.2588(8) 0.04078(13) 0.01185(19) 0.0498(11) Uani 1 1 d . . . . .
H19 H 0.1169 0.0282 0.0224 0.060 Uiso 1 1 calc R . . . .
C20 C 0.3554(7) 0.05669(12) 0.10643(18) 0.0431(9) Uani 1 1 d . . . . .
H20 H 0.2137 0.0443 0.1175 0.052 Uiso 1 1 calc R . . . .
C21 C 0.4092(7) 0.05827(12) 0.05161(17) 0.0385(9) Uani 1 1 d . . . . .
C22 C 0.5038(7) 0.07274(12) 0.14474(17) 0.0392(9) Uani 1 1 d . . . . .
H22 H 0.4665 0.0714 0.1820 0.047 Uiso 1 1 calc R . . . .
C23 C 1.0287(6) 0.02736(11) 0.24803(14) 0.0304(8) Uani 1 1 d . . . . .
C24 C 1.1161(8) -0.03971(12) 0.29590(18) 0.0467(10) Uani 1 1 d . . . . .
H24A H 1.1979 -0.0652 0.2819 0.056 Uiso 1 1 calc R . . . .
H24B H 1.2300 -0.0217 0.3152 0.056 Uiso 1 1 calc R . . . .
C25 C 0.9380(10) -0.05380(15) 0.3344(2) 0.0658(14) Uani 1 1 d . . . . .
H25A H 0.8307 -0.0733 0.3162 0.099 Uiso 1 1 calc GR . . . .
H25B H 0.8536 -0.0288 0.3478 0.099 Uiso 1 1 calc GR . . . .
H25C H 1.0113 -0.0686 0.3647 0.099 Uiso 1 1 calc GR . . . .
C26 C 0.9123(8) -0.04028(13) 0.20664(19) 0.0478(10) Uani 1 1 d . . . . .
H26A H 0.8312 -0.0650 0.2227 0.057 Uiso 0.5 1 calc R . P A 1
H26B H 0.7960 -0.0223 0.1882 0.057 Uiso 0.5 1 calc R . P A 1
H26C H 0.9740 -0.0310 0.1714 0.057 Uiso 0.5 1 calc R . P B 2
H26D H 0.9500 -0.0709 0.2114 0.057 Uiso 0.5 1 calc R . P B 2
C27 C 1.076(2) -0.0557(3) 0.1673(4) 0.0594(18) Uani 0.5 1 d . . P C 1
H27A H 1.1447 -0.0313 0.1484 0.089 Uiso 0.5 1 calc GR . P C 1
H27B H 0.9969 -0.0741 0.1412 0.089 Uiso 0.5 1 calc GR . P C 1
H27C H 1.1972 -0.0720 0.1856 0.089 Uiso 0.5 1 calc GR . P C 1
C27A C 0.6726(18) -0.0350(3) 0.2070(4) 0.0594(18) Uani 0.5 1 d . . P C 2
H27D H 0.6130 -0.0418 0.2429 0.089 Uiso 0.5 1 calc GR . P C 2
H27E H 0.6026 -0.0542 0.1804 0.089 Uiso 0.5 1 calc GR . P C 2
H27F H 0.6346 -0.0053 0.1979 0.089 Uiso 0.5 1 calc GR . P C 2
N1 N 1.0425(5) 0.11384(9) 0.24328(13) 0.0351(7) Uani 1 1 d . . . . .
N2 N 1.1338(5) 0.04868(8) 0.28875(12) 0.0315(6) Uani 1 1 d . . . . .
N3 N 0.9303(5) 0.04699(9) 0.20495(12) 0.0324(6) Uani 1 1 d . . . . .
N4 N 1.0215(5) -0.01517(9) 0.25004(13) 0.0389(8) Uani 1 1 d . . . . .
O1 O 1.2335(5) 0.11476(8) 0.32150(11) 0.0403(6) Uani 1 1 d . . . . .
O2 O 0.8532(5) 0.11169(7) 0.16529(11) 0.0406(6) Uani 1 1 d . . . . .
C28 C 0.2088(6) 0.34473(11) 0.31667(16) 0.0351(8) Uani 1 1 d . . . . .
C29 C 0.2708(6) 0.34842(11) 0.36882(16) 0.0361(8) Uani 1 1 d . . . . .
H29 H 0.4130 0.3616 0.3781 0.043 Uiso 1 1 calc R . . . .
C30 C 0.1234(7) 0.33262(11) 0.41012(16) 0.0334(8) Uani 1 1 d . . . . .
C31 C 0.1821(7) 0.33443(12) 0.46515(16) 0.0403(9) Uani 1 1 d . . . . .
H31 H 0.3229 0.3473 0.4759 0.048 Uiso 1 1 calc R . . . .
C32 C 0.0373(8) 0.31770(13) 0.50331(18) 0.0502(12) Uani 1 1 d . . . . .
H32 H 0.0783 0.3192 0.5403 0.060 Uiso 1 1 calc R . . . .
C33 C -0.1677(8) 0.29871(13) 0.48833(19) 0.0485(11) Uani 1 1 d . . . . .
H33 H -0.2659 0.2869 0.5151 0.058 Uiso 1 1 calc R . . . .
C34 C -0.2295(7) 0.29683(12) 0.43564(19) 0.0450(10) Uani 1 1 d . . . . .
H34 H -0.3716 0.2838 0.4260 0.054 Uiso 1 1 calc R . . . .
C35 C -0.0875(6) 0.31378(11) 0.39474(16) 0.0355(9) Uani 1 1 d . . . . .
C36 C -0.1483(7) 0.31129(12) 0.33946(16) 0.0379(8) Uani 1 1 d . . . . .
H36 H -0.2907 0.2987 0.3292 0.046 Uiso 1 1 calc R . . . .
C37 C -0.0035(6) 0.32677(12) 0.30109(16) 0.0371(8) Uani 1 1 d . . . . .
H37 H -0.0453 0.3255 0.2641 0.045 Uiso 1 1 calc R . . . .
C38 C 0.4394(6) 0.33986(10) 0.23771(15) 0.0309(7) Uani 1 1 d . . . . .
C39 C 0.6280(6) 0.33865(11) 0.16087(15) 0.0312(7) Uani 1 1 d . . . . .
C40 C 0.8579(6) 0.33952(10) 0.08214(15) 0.0315(8) Uani 1 1 d . . . . .
C41 C 1.0685(6) 0.32137(11) 0.09718(16) 0.0367(9) Uani 1 1 d . . . . .
H41 H 1.1169 0.3216 0.1338 0.044 Uiso 1 1 calc R . . . .
C42 C 1.2034(6) 0.30331(11) 0.05835(16) 0.0359(8) Uani 1 1 d . . . . .
H42 H 1.3464 0.2908 0.0684 0.043 Uiso 1 1 calc R . . . .
C43 C 1.1358(6) 0.30275(11) 0.00397(16) 0.0325(8) Uani 1 1 d . . . . .
C44 C 1.2720(7) 0.28453(11) -0.03711(17) 0.0411(9) Uani 1 1 d . . . . .
H44 H 1.4157 0.2718 -0.0281 0.049 Uiso 1 1 calc R . . . .
C45 C 1.2006(7) 0.28486(13) -0.08966(18) 0.0481(10) Uani 1 1 d . . . . .
H45 H 1.2947 0.2723 -0.1166 0.058 Uiso 1 1 calc R . . . .
C46 C 0.9911(8) 0.30346(13) -0.10412(18) 0.0484(11) Uani 1 1 d . . . . .
H46 H 0.9425 0.3034 -0.1407 0.058 Uiso 1 1 calc R . . . .
C47 C 0.8562(6) 0.32180(12) -0.06549(16) 0.0376(8) Uani 1 1 d . . . . .
H47 H 0.7148 0.3349 -0.0756 0.045 Uiso 1 1 calc R . . . .
C48 C 0.9234(6) 0.32168(10) -0.01065(15) 0.0315(8) Uani 1 1 d . . . . .
C49 C 0.7856(6) 0.34034(11) 0.03025(15) 0.0321(8) Uani 1 1 d . . . . .
H49 H 0.6428 0.3534 0.0212 0.039 Uiso 1 1 calc R . . . .
C50 C 0.5183(6) 0.27707(10) 0.19906(15) 0.0307(8) Uani 1 1 d . . . . .
C51 C 0.4014(7) 0.21090(12) 0.24350(18) 0.0448(10) Uani 1 1 d . . . . .
H51A H 0.3243 0.1849 0.2296 0.054 Uiso 1 1 calc R . . . .
H51B H 0.2838 0.2291 0.2610 0.054 Uiso 1 1 calc R . . . .
C52 C 0.5881(9) 0.19825(14) 0.2850(2) 0.0581(12) Uani 1 1 d . . . . .
H52A H 0.7056 0.1807 0.2674 0.087 Uiso 1 1 calc GR . . . .
H52B H 0.5172 0.1819 0.3143 0.087 Uiso 1 1 calc GR . . . .
H52C H 0.6597 0.2241 0.2997 0.087 Uiso 1 1 calc GR . . . .
C53 C 0.6119(8) 0.20937(12) 0.15564(18) 0.0483(10) Uani 1 1 d . . . . .
H53A H 0.7001 0.1852 0.1711 0.058 Uiso 1 1 calc R . . . .
H53B H 0.7194 0.2275 0.1348 0.058 Uiso 1 1 calc R . . . .
C54 C 0.4187(12) 0.19216(17) 0.1181(2) 0.0810(18) Uani 1 1 d . . . . .
H54A H 0.4861 0.1733 0.0908 0.122 Uiso 1 1 calc GR . . . .
H54B H 0.3417 0.2162 0.1002 0.122 Uiso 1 1 calc GR . . . .
H54C H 0.3063 0.1761 0.1395 0.122 Uiso 1 1 calc GR . . . .
N5 N 0.5394(5) 0.36321(9) 0.19920(13) 0.0341(7) Uani 1 1 d . . . . .
N6 N 0.4232(5) 0.29812(8) 0.24128(12) 0.0317(6) Uani 1 1 d . . . . .
N7 N 0.6241(5) 0.29671(8) 0.15714(12) 0.0319(6) Uani 1 1 d . . . . .
N8 N 0.5073(6) 0.23435(9) 0.19873(13) 0.0390(8) Uani 1 1 d . . . . .
O3 O 0.3489(5) 0.36429(7) 0.27750(11) 0.0394(6) Uani 1 1 d . . . . .
O4 O 0.7292(5) 0.36153(8) 0.12125(11) 0.0399(6) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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
C2 C1 H1 120.7 . .
C2 C1 C10 118.6(4) . .
C10 C1 H1 120.7 . .
C1 C2 H2 119.6 . .
C1 C2 C3 120.7(3) . .
C3 C2 H2 119.6 . .
C2 C3 C8 119.5(3) . .
C4 C3 C2 121.2(3) . .
C4 C3 C8 119.2(4) . .
C3 C4 H4 119.9 . .
C5 C4 C3 120.3(4) . .
C5 C4 H4 119.9 . .
C4 C5 H5 119.4 . .
C4 C5 C6 121.2(4) . .
C6 C5 H5 119.4 . .
C5 C6 H6 120.1 . .
C7 C6 C5 119.9(4) . .
C7 C6 H6 120.1 . .
C6 C7 H7 120.1 . .
C6 C7 C8 119.8(4) . .
C8 C7 H7 120.1 . .
C3 C8 C9 118.8(3) . .
C7 C8 C3 119.7(4) . .
C7 C8 C9 121.5(3) . .
C8 C9 H9 120.5 . .
C10 C9 C8 118.9(3) . .
C10 C9 H9 120.5 . .
C1 C10 O1 118.4(3) . .
C9 C10 C1 123.4(4) . .
C9 C10 O1 117.9(3) . .
N1 C11 O1 112.8(3) . .
N2 C11 N1 129.0(3) . .
N2 C11 O1 118.3(3) . .
N1 C12 O2 112.5(3) . .
N3 C12 N1 128.7(3) . .
N3 C12 O2 118.7(3) . .
C14 C13 C22 122.8(4) . .
C14 C13 O2 117.4(3) . .
C22 C13 O2 119.5(4) . .
C13 C14 H14 120.4 . .
C13 C14 C15 119.2(3) . .
C15 C14 H14 120.4 . .
C14 C15 C16 121.0(4) . .
C21 C15 C14 118.9(4) . .
C21 C15 C16 120.1(4) . .
C15 C16 H16 120.6 . .
C17 C16 C15 118.9(4) . .
C17 C16 H16 120.6 . .
C16 C17 H17 119.3 . .
C16 C17 C18 121.5(5) . .
C18 C17 H17 119.3 . .
C17 C18 H18 119.8 . .
C19 C18 C17 120.4(4) . .
C19 C18 H18 119.8 . .
C18 C19 H19 120.0 . .
C18 C19 C21 120.1(5) . .
C21 C19 H19 120.0 . .
C21 C20 H20 119.4 . .
C22 C20 H20 119.4 . .
C22 C20 C21 121.2(4) . .
C15 C21 C19 119.1(4) . .
C20 C21 C15 119.4(4) . .
C20 C21 C19 121.5(4) . .
C13 C22 H22 120.8 . .
C20 C22 C13 118.4(4) . .
C20 C22 H22 120.8 . .
N2 C23 N3 123.6(3) . .
N4 C23 N2 118.5(3) . .
N4 C23 N3 117.9(3) . .
H24A C24 H24B 107.8 . .
C25 C24 H24A 109.0 . .
C25 C24 H24B 109.0 . .
C25 C24 N4 113.1(4) . .
N4 C24 H24A 109.0 . .
N4 C24 H24B 109.0 . .
C24 C25 H25A 109.5 . .
C24 C25 H25B 109.5 . .
C24 C25 H25C 109.5 . .
H25A C25 H25B 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
H26A C26 H26B 107.8 . .
H26C C26 H26D 108.0 . .
C27 C26 H26A 109.0 . .
C27 C26 H26B 109.0 . .
C27 C26 N4 112.8(5) . .
C27A C26 H26C 109.4 . .
C27A C26 H26D 109.4 . .
C27A C26 N4 111.0(5) . .
N4 C26 H26A 109.0 . .
N4 C26 H26B 109.0 . .
N4 C26 H26C 109.4 . .
N4 C26 H26D 109.4 . .
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 . .
C26 C27A H27D 109.5 . .
C26 C27A H27E 109.5 . .
C26 C27A H27F 109.5 . .
H27D C27A H27E 109.5 . .
H27D C27A H27F 109.5 . .
H27E C27A H27F 109.5 . .
C11 N1 C12 111.0(3) . .
C11 N2 C23 113.8(3) . .
C12 N3 C23 113.9(3) . .
C23 N4 C24 122.4(3) . .
C23 N4 C26 121.2(3) . .
C26 N4 C24 116.4(3) . .
C11 O1 C10 118.7(3) . .
C12 O2 C13 119.4(3) . .
C29 C28 C37 122.0(4) . .
C29 C28 O3 118.2(3) . .
C37 C28 O3 119.4(4) . .
C28 C29 H29 120.0 . .
C28 C29 C30 120.1(4) . .
C30 C29 H29 120.0 . .
C31 C30 C29 122.6(4) . .
C31 C30 C35 119.2(4) . .
C35 C30 C29 118.2(4) . .
C30 C31 H31 119.8 . .
C32 C31 C30 120.4(4) . .
C32 C31 H31 119.8 . .
C31 C32 H32 119.7 . .
C31 C32 C33 120.5(4) . .
C33 C32 H32 119.7 . .
C32 C33 H33 119.8 . .
C34 C33 C32 120.3(4) . .
C34 C33 H33 119.8 . .
C33 C34 H34 119.3 . .
C33 C34 C35 121.5(4) . .
C35 C34 H34 119.3 . .
C30 C35 C34 118.1(4) . .
C30 C35 C36 119.9(4) . .
C34 C35 C36 122.0(4) . .
C35 C36 H36 119.8 . .
C37 C36 C35 120.3(4) . .
C37 C36 H36 119.8 . .
C28 C37 H37 120.3 . .
C36 C37 C28 119.4(4) . .
C36 C37 H37 120.3 . .
N5 C38 O3 112.5(3) . .
N6 C38 N5 128.6(3) . .
N6 C38 O3 118.9(3) . .
N5 C39 O4 112.7(3) . .
N7 C39 N5 128.4(3) . .
N7 C39 O4 118.9(3) . .
C41 C40 O4 118.7(3) . .
C49 C40 C41 122.1(3) . .
C49 C40 O4 118.9(3) . .
C40 C41 H41 120.6 . .
C42 C41 C40 118.8(4) . .
C42 C41 H41 120.6 . .
C41 C42 H42 119.2 . .
C41 C42 C43 121.6(3) . .
C43 C42 H42 119.2 . .
C42 C43 C44 122.9(4) . .
C42 C43 C48 118.9(3) . .
C44 C43 C48 118.3(4) . .
C43 C44 H44 119.5 . .
C45 C44 C43 121.1(4) . .
C45 C44 H44 119.5 . .
C44 C45 H45 119.6 . .
C44 C45 C46 120.7(4) . .
C46 C45 H45 119.6 . .
C45 C46 H46 120.1 . .
C47 C46 C45 119.7(4) . .
C47 C46 H46 120.1 . .
C46 C47 H47 119.5 . .
C46 C47 C48 121.1(4) . .
C48 C47 H47 119.5 . .
C43 C48 C49 118.8(3) . .
C47 C48 C43 119.1(3) . .
C47 C48 C49 122.1(3) . .
C40 C49 C48 119.9(3) . .
C40 C49 H49 120.1 . .
C48 C49 H49 120.1 . .
N6 C50 N7 124.0(3) . .
N8 C50 N6 118.0(3) . .
N8 C50 N7 118.0(3) . .
H51A C51 H51B 108.2 . .
C52 C51 H51A 109.7 . .
C52 C51 H51B 109.7 . .
N8 C51 H51A 109.7 . .
N8 C51 H51B 109.7 . .
N8 C51 C52 109.8(3) . .
C51 C52 H52A 109.5 . .
C51 C52 H52B 109.5 . .
C51 C52 H52C 109.5 . .
H52A C52 H52B 109.5 . .
H52A C52 H52C 109.5 . .
H52B C52 H52C 109.5 . .
H53A C53 H53B 108.3 . .
C54 C53 H53A 109.9 . .
C54 C53 H53B 109.9 . .
N8 C53 H53A 109.9 . .
N8 C53 H53B 109.9 . .
N8 C53 C54 108.9(4) . .
C53 C54 H54A 109.5 . .
C53 C54 H54B 109.5 . .
C53 C54 H54C 109.5 . .
H54A C54 H54B 109.5 . .
H54A C54 H54C 109.5 . .
H54B C54 H54C 109.5 . .
C39 N5 C38 111.5(3) . .
C38 N6 C50 113.7(3) . .
C39 N7 C50 113.9(3) . .
C50 N8 C51 121.0(3) . .
C50 N8 C53 121.3(3) . .
C53 N8 C51 117.6(3) . .
C38 O3 C28 118.9(3) . .
C39 O4 C40 118.4(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 H1 0.9500 .
C1 C2 1.368(6) .
C1 C10 1.402(5) .
C2 H2 0.9500 .
C2 C3 1.417(6) .
C3 C4 1.413(5) .
C3 C8 1.422(5) .
C4 H4 0.9500 .
C4 C5 1.355(6) .
C5 H5 0.9500 .
C5 C6 1.425(7) .
C6 H6 0.9500 .
C6 C7 1.378(6) .
C7 H7 0.9500 .
C7 C8 1.415(6) .
C8 C9 1.423(5) .
C9 H9 0.9500 .
C9 C10 1.356(5) .
C10 O1 1.408(4) .
C11 N1 1.328(5) .
C11 N2 1.318(4) .
C11 O1 1.354(4) .
C12 N1 1.328(5) .
C12 N3 1.318(4) .
C12 O2 1.347(4) .
C13 C14 1.358(6) .
C13 C22 1.395(6) .
C13 O2 1.406(4) .
C14 H14 0.9500 .
C14 C15 1.416(5) .
C15 C16 1.422(6) .
C15 C21 1.415(6) .
C16 H16 0.9500 .
C16 C17 1.371(7) .
C17 H17 0.9500 .
C17 C18 1.415(8) .
C18 H18 0.9500 .
C18 C19 1.364(7) .
C19 H19 0.9500 .
C19 C21 1.425(6) .
C20 H20 0.9500 .
C20 C21 1.397(6) .
C20 C22 1.376(6) .
C22 H22 0.9500 .
C23 N2 1.355(4) .
C23 N3 1.357(5) .
C23 N4 1.331(4) .
C24 H24A 0.9900 .
C24 H24B 0.9900 .
C24 C25 1.476(7) .
C24 N4 1.477(5) .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
C26 H26A 0.9900 .
C26 H26B 0.9900 .
C26 H26C 0.9900 .
C26 H26D 0.9900 .
C26 C27 1.446(11) .
C26 C27A 1.402(12) .
C26 N4 1.475(5) .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
C27A H27D 0.9800 .
C27A H27E 0.9800 .
C27A H27F 0.9800 .
C28 C29 1.347(6) .
C28 C37 1.408(5) .
C28 O3 1.408(4) .
C29 H29 0.9500 .
C29 C30 1.425(5) .
C30 C31 1.408(6) .
C30 C35 1.410(6) .
C31 H31 0.9500 .
C31 C32 1.371(6) .
C32 H32 0.9500 .
C32 C33 1.380(7) .
C33 H33 0.9500 .
C33 C34 1.356(7) .
C34 H34 0.9500 .
C34 C35 1.412(5) .
C35 C36 1.418(6) .
C36 H36 0.9500 .
C36 C37 1.360(5) .
C37 H37 0.9500 .
C38 N5 1.336(5) .
C38 N6 1.311(4) .
C38 O3 1.355(4) .
C39 N5 1.327(5) .
C39 N7 1.314(4) .
C39 O4 1.351(4) .
C40 C41 1.398(5) .
C40 C49 1.354(5) .
C40 O4 1.406(4) .
C41 H41 0.9500 .
C41 C42 1.365(5) .
C42 H42 0.9500 .
C42 C43 1.404(6) .
C43 C44 1.412(5) .
C43 C48 1.415(5) .
C44 H44 0.9500 .
C44 C45 1.367(6) .
C45 H45 0.9500 .
C45 C46 1.395(7) .
C46 H46 0.9500 .
C46 C47 1.365(6) .
C47 H47 0.9500 .
C47 C48 1.415(5) .
C48 C49 1.419(5) .
C49 H49 0.9500 .
C50 N6 1.356(5) .
C50 N7 1.356(5) .
C50 N8 1.337(4) .
C51 H51A 0.9900 .
C51 H51B 0.9900 .
C51 C52 1.546(7) .
C51 N8 1.467(5) .
C52 H52A 0.9800 .
C52 H52B 0.9800 .
C52 H52C 0.9800 .
C53 H53A 0.9900 .
C53 H53B 0.9900 .
C53 C54 1.553(7) .
C53 N8 1.458(5) .
C54 H54A 0.9800 .
C54 H54B 0.9800 .
C54 H54C 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
C1 C2 C3 C4 179.5(3) . . . .
C1 C2 C3 C8 -0.6(5) . . . .
C1 C10 O1 C11 71.8(4) . . . .
C2 C1 C10 C9 1.1(5) . . . .
C2 C1 C10 O1 175.6(3) . . . .
C2 C3 C4 C5 -179.7(4) . . . .
C2 C3 C8 C7 180.0(3) . . . .
C2 C3 C8 C9 0.8(5) . . . .
C3 C4 C5 C6 -0.8(6) . . . .
C3 C8 C9 C10 0.0(5) . . . .
C4 C3 C8 C7 -0.1(5) . . . .
C4 C3 C8 C9 -179.3(3) . . . .
C4 C5 C6 C7 1.1(6) . . . .
C5 C6 C7 C8 -0.8(5) . . . .
C6 C7 C8 C3 0.4(5) . . . .
C6 C7 C8 C9 179.5(3) . . . .
C7 C8 C9 C10 -179.2(3) . . . .
C8 C3 C4 C5 0.4(5) . . . .
C8 C9 C10 C1 -0.9(5) . . . .
C8 C9 C10 O1 -175.5(3) . . . .
C9 C10 O1 C11 -113.4(4) . . . .
C10 C1 C2 C3 -0.3(5) . . . .
C13 C14 C15 C16 -179.4(3) . . . .
C13 C14 C15 C21 -0.1(5) . . . .
C14 C13 C22 C20 -0.3(5) . . . .
C14 C13 O2 C12 -124.0(4) . . . .
C14 C15 C16 C17 178.3(4) . . . .
C14 C15 C21 C19 -178.6(3) . . . .
C14 C15 C21 C20 0.2(5) . . . .
C15 C16 C17 C18 0.6(6) . . . .
C16 C15 C21 C19 0.6(5) . . . .
C16 C15 C21 C20 179.5(4) . . . .
C16 C17 C18 C19 0.1(6) . . . .
C17 C18 C19 C21 -0.4(6) . . . .
C18 C19 C21 C15 0.0(6) . . . .
C18 C19 C21 C20 -178.8(4) . . . .
C21 C15 C16 C17 -0.9(5) . . . .
C21 C20 C22 C13 0.4(5) . . . .
C22 C13 C14 C15 0.1(5) . . . .
C22 C13 O2 C12 62.2(5) . . . .
C22 C20 C21 C15 -0.3(5) . . . .
C22 C20 C21 C19 178.5(3) . . . .
C25 C24 N4 C23 99.9(4) . . . .
C25 C24 N4 C26 -78.6(5) . . . .
C27 C26 N4 C23 96.2(6) . . . .
C27 C26 N4 C24 -85.2(6) . . . .
C27A C26 N4 C23 -70.1(6) . . . .
C27A C26 N4 C24 108.4(6) . . . .
N1 C11 N2 C23 0.1(6) . . . .
N1 C11 O1 C10 -171.6(3) . . . .
N1 C12 N3 C23 1.6(6) . . . .
N1 C12 O2 C13 -169.7(3) . . . .
N2 C11 N1 C12 0.5(6) . . . .
N2 C11 O1 C10 8.3(5) . . . .
N2 C23 N3 C12 -0.8(5) . . . .
N2 C23 N4 C24 2.3(5) . . . .
N2 C23 N4 C26 -179.2(3) . . . .
N3 C12 N1 C11 -1.4(6) . . . .
N3 C12 O2 C13 12.2(5) . . . .
N3 C23 N2 C11 0.1(5) . . . .
N3 C23 N4 C24 -177.9(3) . . . .
N3 C23 N4 C26 0.6(5) . . . .
N4 C23 N2 C11 179.9(3) . . . .
N4 C23 N3 C12 179.4(3) . . . .
O1 C11 N1 C12 -179.6(3) . . . .
O1 C11 N2 C23 -179.9(3) . . . .
O2 C12 N1 C11 -179.2(3) . . . .
O2 C12 N3 C23 179.3(3) . . . .
O2 C13 C14 C15 -173.5(3) . . . .
O2 C13 C22 C20 173.2(3) . . . .
C28 C29 C30 C31 178.1(3) . . . .
C28 C29 C30 C35 -0.7(5) . . . .
C29 C28 C37 C36 -2.3(5) . . . .
C29 C28 O3 C38 122.6(4) . . . .
C29 C30 C31 C32 -178.1(3) . . . .
C29 C30 C35 C34 177.9(3) . . . .
C29 C30 C35 C36 -0.5(5) . . . .
C30 C31 C32 C33 0.2(6) . . . .
C30 C35 C36 C37 0.4(5) . . . .
C31 C30 C35 C34 -1.0(5) . . . .
C31 C30 C35 C36 -179.4(3) . . . .
C31 C32 C33 C34 -0.8(6) . . . .
C32 C33 C34 C35 0.4(6) . . . .
C33 C34 C35 C30 0.5(5) . . . .
C33 C34 C35 C36 178.8(4) . . . .
C34 C35 C36 C37 -177.9(3) . . . .
C35 C30 C31 C32 0.7(5) . . . .
C35 C36 C37 C28 0.9(5) . . . .
C37 C28 C29 C30 2.1(5) . . . .
C37 C28 O3 C38 -65.1(4) . . . .
C40 C41 C42 C43 0.3(5) . . . .
C41 C40 C49 C48 1.2(5) . . . .
C41 C40 O4 C39 -70.6(4) . . . .
C41 C42 C43 C44 179.6(3) . . . .
C41 C42 C43 C48 0.4(5) . . . .
C42 C43 C44 C45 -179.6(4) . . . .
C42 C43 C48 C47 179.0(3) . . . .
C42 C43 C48 C49 -0.4(5) . . . .
C43 C44 C45 C46 0.3(6) . . . .
C43 C48 C49 C40 -0.4(5) . . . .
C44 C43 C48 C47 -0.2(5) . . . .
C44 C43 C48 C49 -179.6(3) . . . .
C44 C45 C46 C47 0.4(6) . . . .
C45 C46 C47 C48 -1.0(6) . . . .
C46 C47 C48 C43 1.0(5) . . . .
C46 C47 C48 C49 -179.7(3) . . . .
C47 C48 C49 C40 -179.8(3) . . . .
C48 C43 C44 C45 -0.4(5) . . . .
C49 C40 C41 C42 -1.1(5) . . . .
C49 C40 O4 C39 116.0(4) . . . .
C52 C51 N8 C50 -93.1(4) . . . .
C52 C51 N8 C53 83.2(5) . . . .
C54 C53 N8 C50 -105.5(4) . . . .
C54 C53 N8 C51 78.1(5) . . . .
N5 C38 N6 C50 -1.4(6) . . . .
N5 C38 O3 C28 170.7(3) . . . .
N5 C39 N7 C50 -1.3(6) . . . .
N5 C39 O4 C40 171.2(3) . . . .
N6 C38 N5 C39 0.6(6) . . . .
N6 C38 O3 C28 -10.1(5) . . . .
N6 C50 N7 C39 0.2(5) . . . .
N6 C50 N8 C51 -1.8(5) . . . .
N6 C50 N8 C53 -178.0(4) . . . .
N7 C39 N5 C38 1.0(6) . . . .
N7 C39 O4 C40 -10.0(5) . . . .
N7 C50 N6 C38 1.0(5) . . . .
N7 C50 N8 C51 178.2(3) . . . .
N7 C50 N8 C53 2.0(6) . . . .
N8 C50 N6 C38 -179.1(3) . . . .
N8 C50 N7 C39 -179.7(3) . . . .
O3 C28 C29 C30 174.1(3) . . . .
O3 C28 C37 C36 -174.2(3) . . . .
O3 C38 N5 C39 179.6(3) . . . .
O3 C38 N6 C50 179.6(3) . . . .
O4 C39 N5 C38 179.7(3) . . . .
O4 C39 N7 C50 -180.0(3) . . . .
O4 C40 C41 C42 -174.3(3) . . . .
O4 C40 C49 C48 174.3(3) . . . .
