#------------------------------------------------------------------------------
#$Date: 2020-07-03 02:23:30 +0300 (Fri, 03 Jul 2020) $
#$Revision: 253675 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/84/1558472.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_1558472
loop_
_publ_author_name
'Ishizuka, Tomoya'
'Sakashita, Ryuichi'
'Iwanaga, Osamu'
'Morimoto, Tatsuki'
'Mori, Shigeki'
'Ishida, Masatoshi'
'Toganoh, Motoki'
'Takegoshi, Kiyonori'
'Osuka, Atsuhiro'
'Furuta, Hiroyuki'
_publ_section_title
;
 NH Tautomerism of N-Confused Porphyrin: Solvent/Substituent Effects and
 Isomerization Mechanism.
;
_journal_name_full               'The journal of physical chemistry. A'
_journal_paper_doi               10.1021/acs.jpca.0c04779
_journal_year                    2020
_chemical_formula_moiety         'C44 H30 N4, 2(C3 H7 N O)'
_chemical_formula_sum            'C50 H44 N6 O2'
_chemical_formula_weight         760.91
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                98.691(5)
_cell_angle_beta                 116.169(5)
_cell_angle_gamma                92.716(3)
_cell_formula_units_Z            2
_cell_length_a                   12.6211(12)
_cell_length_b                   13.1779(16)
_cell_length_c                   13.5455(18)
_cell_measurement_reflns_used    7922
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.42
_cell_volume                     1982.2(4)
_computing_molecular_graphics    'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_publication_material  'CrystalStructure 4.2.4'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.890
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measurement_device_type  'Rigaku RAXIS'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.1204
_diffrn_reflns_Laue_measured_fraction_full 0.890
_diffrn_reflns_Laue_measured_fraction_max 0.885
_diffrn_reflns_number            6894
_diffrn_reflns_point_group_measured_fraction_full 0.890
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.244
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            grey
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         6894
_refine_ls_number_restraints     242
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.1447
_refine_ls_R_factor_gt           0.0698
_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)+(0.1036P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1612
_refine_ls_wR_factor_ref         0.1923
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3582
_reflns_number_total             6894
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp0c04779_si_003.cif
_cod_data_source_block           shelxl
_cod_database_code               1558472
_shelx_shelxl_version_number     2016/6
_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_min   0.977
_shelx_estimated_absorpt_t_max   0.992
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
N1 N 0.7393(3) 0.2768(3) 0.6532(3) 0.0312(10) Uani 0.40(3) 1 d . . P A 1
H1 H 0.810811 0.312355 0.685911 0.037 Uiso 0.40(3) 1 calc R U P A 1
C102 C 0.7393(3) 0.2768(3) 0.6532(3) 0.0312(10) Uani 0.60(3) 1 d . . P A 2
H102 H 0.816499 0.315180 0.688514 0.037 Uiso 0.60(3) 1 calc R U P A 2
N2 N 0.3431(2) 0.0576(2) 0.4840(2) 0.0277(7) Uani 1 1 d . . . . .
N3 N 0.7785(3) 0.4806(2) 0.9082(3) 0.0265(9) Uani 0.39(3) 1 d . . P B 3
H3 H 0.828779 0.506227 0.886667 0.032 Uiso 0.39(3) 1 calc R U P B 3
C124 C 0.7785(3) 0.4806(2) 0.9082(3) 0.0265(9) Uani 0.61(3) 1 d . . P B 4
H124 H 0.832782 0.508265 0.884958 0.032 Uiso 0.61(3) 1 calc R U P B 4
N4 N 0.4817(2) 0.3481(2) 1.0243(2) 0.0237(6) Uani 1 1 d . . . . .
C1 C 0.7118(3) 0.1702(3) 0.6023(3) 0.0270(8) Uani 1 1 d . . . . .
C2 C 0.5897(3) 0.1456(2) 0.5592(3) 0.0290(9) Uani 0.40(3) 1 d . . P A 1
H2 H 0.545693 0.079732 0.519219 0.035 Uiso 0.40(3) 1 calc R U P A 1
N101 N 0.5897(3) 0.1456(2) 0.5592(3) 0.0290(9) Uani 0.60(3) 1 d . . P A 2
H101 H 0.548937 0.084587 0.522164 0.035 Uiso 0.60(3) 1 calc R U P A 2
C3 C 0.5427(3) 0.2326(3) 0.5838(3) 0.0268(8) Uani 1 1 d . . . . .
C4 C 0.6390(3) 0.3149(3) 0.6435(3) 0.0297(8) Uani 1 1 d . . . . .
H4 H 0.633078 0.383967 0.671209 0.036 Uiso 1 1 calc R U . A 1
C5 C 0.4240(3) 0.2417(3) 0.5656(3) 0.0250(8) Uani 1 1 d . . . . .
C6 C 0.3317(3) 0.1577(3) 0.5182(3) 0.0261(8) Uani 1 1 d . . . . .
C7 C 0.2092(3) 0.1664(3) 0.4953(3) 0.0294(8) Uani 1 1 d . . . . .
H7 H 0.177819 0.227478 0.511059 0.035 Uiso 1 1 calc R U . . .
C8 C 0.1488(3) 0.0711(3) 0.4473(3) 0.0299(8) Uani 1 1 d . . . . .
H8 H 0.066210 0.052517 0.422762 0.036 Uiso 1 1 calc R U . . .
C9 C 0.2313(3) 0.0021(3) 0.4396(3) 0.0271(8) Uani 1 1 d . . . . .
C10 C 0.2042(3) -0.1048(3) 0.3981(3) 0.0274(8) Uani 1 1 d . . . . .
C11 C 0.3995(3) 0.3454(3) 0.6039(3) 0.0272(8) Uani 1 1 d . . . . .
C12 C 0.4013(3) 0.4284(3) 0.5512(3) 0.0373(10) Uani 1 1 d . . . . .
H12 H 0.414281 0.417880 0.486617 0.045 Uiso 1 1 calc R U . . .
C13 C 0.3845(3) 0.5251(3) 0.5921(4) 0.0394(10) Uani 1 1 d . . . . .
H13 H 0.387646 0.580989 0.556239 0.047 Uiso 1 1 calc R U . . .
C14 C 0.3632(3) 0.5420(3) 0.6841(4) 0.0383(10) Uani 1 1 d . . . . .
H14 H 0.349681 0.608710 0.710547 0.046 Uiso 1 1 calc R U . . .
C15 C 0.3617(3) 0.4604(3) 0.7383(3) 0.0340(9) Uani 1 1 d . . . . .
H15 H 0.348298 0.471209 0.802541 0.041 Uiso 1 1 calc R U . . .
C16 C 0.3800(3) 0.3631(3) 0.6976(3) 0.0297(8) Uani 1 1 d . . . . .
H16 H 0.379142 0.307685 0.734701 0.036 Uiso 1 1 calc R U . . .
C17 C 0.0767(3) -0.1527(3) 0.3431(3) 0.0268(8) Uani 1 1 d . . . . .
C18 C -0.0028(3) -0.1285(3) 0.2427(3) 0.0310(9) Uani 1 1 d . . . . .
H18 H 0.022692 -0.077920 0.211907 0.037 Uiso 1 1 calc R U . . .
C19 C -0.1198(3) -0.1773(3) 0.1862(3) 0.0312(9) Uani 1 1 d . . . . .
H19 H -0.173607 -0.160035 0.117352 0.037 Uiso 1 1 calc R U . . .
C20 C -0.1574(3) -0.2512(3) 0.2306(3) 0.0332(9) Uani 1 1 d . . . . .
H20 H -0.236893 -0.284969 0.192251 0.040 Uiso 1 1 calc R U . . .
C21 C -0.0779(3) -0.2759(3) 0.3322(3) 0.0379(10) Uani 1 1 d . . . . .
H21 H -0.103517 -0.326683 0.362617 0.045 Uiso 1 1 calc R U . . .
C22 C 0.0383(3) -0.2267(3) 0.3888(3) 0.0341(9) Uani 1 1 d . . . . .
H22 H 0.091737 -0.243042 0.458271 0.041 Uiso 1 1 calc R U . . .
C23 C 0.6956(3) 0.5359(3) 0.9317(3) 0.0242(8) Uani 1 1 d . . . . .
C24 C 0.6341(3) 0.4663(2) 0.9605(3) 0.0244(9) Uani 0.39(3) 1 d . . P B 3
H24 H 0.572621 0.481616 0.980736 0.029 Uiso 0.39(3) 1 calc R U P B 3
N103 N 0.6341(3) 0.4663(2) 0.9605(3) 0.0244(9) Uani 0.61(3) 1 d . . P B 4
H103 H 0.577150 0.480491 0.979247 0.029 Uiso 0.61(3) 1 calc R U P B 4
C25 C 0.6752(3) 0.3708(3) 0.9557(3) 0.0225(8) Uani 1 1 d . . . . .
C26 C 0.7679(3) 0.3832(3) 0.9239(3) 0.0251(8) Uani 1 1 d . . . . .
H26 H 0.814443 0.331191 0.915273 0.030 Uiso 1 1 calc R U . B 3
C27 C 0.6350(3) 0.2785(3) 0.9768(3) 0.0244(8) Uani 1 1 d . . . . .
C28 C 0.5431(3) 0.2692(3) 1.0079(3) 0.0240(8) Uani 1 1 d . . . . .
C29 C 0.4959(3) 0.1736(3) 1.0245(3) 0.0246(8) Uani 1 1 d . . . . .
H29 H 0.521329 0.107555 1.016376 0.030 Uiso 1 1 calc R U . . .
C30 C 0.4094(3) 0.1966(3) 1.0536(3) 0.0253(8) Uani 1 1 d . . . . .
H30 H 0.362666 0.149936 1.070224 0.030 Uiso 1 1 calc R U . . .
C31 C 0.4011(3) 0.3063(3) 1.0546(3) 0.0256(8) Uani 1 1 d . . . . .
C32 C 0.3185(3) 0.3607(3) 1.0778(3) 0.0237(8) Uani 1 1 d . . . . .
C33 C 0.6976(3) 0.1862(3) 0.9689(3) 0.0261(8) Uani 1 1 d . . . . .
C34 C 0.7547(3) 0.1398(3) 1.0623(3) 0.0285(8) Uani 1 1 d . . . . .
H34 H 0.752589 0.166357 1.130531 0.034 Uiso 1 1 calc R U . . .
C35 C 0.8141(3) 0.0555(3) 1.0555(3) 0.0322(9) Uani 1 1 d . . . . .
H35 H 0.853379 0.025489 1.119796 0.039 Uiso 1 1 calc R U . . .
C36 C 0.8174(3) 0.0144(3) 0.9575(4) 0.0356(10) Uani 1 1 d . . . . .
H36 H 0.857621 -0.044000 0.953548 0.043 Uiso 1 1 calc R U . . .
C37 C 0.7609(3) 0.0596(3) 0.8643(4) 0.0384(10) Uani 1 1 d . . . . .
H37 H 0.763235 0.032053 0.796394 0.046 Uiso 1 1 calc R U . . .
C38 C 0.7008(3) 0.1450(3) 0.8693(3) 0.0322(9) Uani 1 1 d . . . . .
H38 H 0.662108 0.174942 0.804906 0.039 Uiso 1 1 calc R U . . .
C39 C 0.2424(3) 0.3049(2) 1.1161(3) 0.0236(8) Uani 1 1 d . . . . .
C40 C 0.2943(3) 0.2646(3) 1.2135(3) 0.0280(8) Uani 1 1 d . . . . .
H40 H 0.378570 0.272463 1.254809 0.034 Uiso 1 1 calc R U . . .
C41 C 0.2257(3) 0.2131(3) 1.2515(3) 0.0319(9) Uani 1 1 d . . . . .
H41 H 0.262755 0.185480 1.317819 0.038 Uiso 1 1 calc R U . . .
C42 C 0.1020(3) 0.2022(3) 1.1920(3) 0.0337(9) Uani 1 1 d . . . . .
H42 H 0.054386 0.167679 1.218115 0.040 Uiso 1 1 calc R U . . .
C43 C 0.0487(3) 0.2416(3) 1.0951(3) 0.0302(9) Uani 1 1 d . . . . .
H43 H -0.035623 0.234038 1.054674 0.036 Uiso 1 1 calc R U . . .
C44 C 0.1178(3) 0.2926(3) 1.0560(3) 0.0252(8) Uani 1 1 d . . . . .
H44 H 0.080402 0.318890 0.988836 0.030 Uiso 1 1 calc R U . . .
O1 O 0.9554(4) 0.4383(5) 0.8220(4) 0.142(2) Uani 1 1 d . . . . .
C45 C 1.0310(5) 0.4890(6) 0.8088(5) 0.0837(19) Uani 1 1 d . . . . .
H45 H 1.112275 0.490616 0.860379 0.100 Uiso 1 1 calc R U . . .
N5 N 1.0041(3) 0.5435(3) 0.7233(4) 0.0581(11) Uani 1 1 d . . . . .
C46 C 0.8842(4) 0.5377(4) 0.6426(5) 0.0772(17) Uani 1 1 d . . . . .
H46A H 0.869934 0.488382 0.574804 0.116 Uiso 1 1 calc R U . . .
H46B H 0.867710 0.606122 0.624059 0.116 Uiso 1 1 calc R U . . .
H46C H 0.831702 0.514400 0.672938 0.116 Uiso 1 1 calc R U . . .
C47 C 1.0970(5) 0.6013(4) 0.7176(5) 0.0853(19) Uani 1 1 d . . . . .
H47A H 1.170745 0.604994 0.786877 0.128 Uiso 1 1 calc R U . . .
H47B H 1.077194 0.671421 0.708476 0.128 Uiso 1 1 calc R U . . .
H47C H 1.107814 0.567865 0.653594 0.128 Uiso 1 1 calc R U . . .
O2 O 0.7684(4) 0.2299(3) 0.3400(4) 0.0468(14) Uani 0.657(6) 1 d D U P C 5
C48 C 0.6774(11) 0.1821(8) 0.3218(18) 0.039(2) Uani 0.657(6) 1 d D U P C 5
H48 H 0.618890 0.221529 0.328138 0.047 Uiso 0.657(6) 1 calc R U P C 5
N6 N 0.6473(5) 0.0789(6) 0.2933(8) 0.0337(15) Uani 0.657(6) 1 d D U P C 5
C49 C 0.7325(7) 0.0132(6) 0.2819(6) 0.0442(17) Uani 0.657(6) 1 d D U P C 5
H49A H 0.703227 -0.019156 0.202995 0.066 Uiso 0.657(6) 1 calc R U P C 5
H49B H 0.742104 -0.040643 0.326724 0.066 Uiso 0.657(6) 1 calc R U P C 5
H49C H 0.809384 0.055316 0.308384 0.066 Uiso 0.657(6) 1 calc R U P C 5
C50 C 0.5307(6) 0.0274(5) 0.2630(6) 0.0434(18) Uani 0.657(6) 1 d D U P C 5
H50A H 0.480616 0.078645 0.272883 0.065 Uiso 0.657(6) 1 calc R U P C 5
H50B H 0.537931 -0.023111 0.311129 0.065 Uiso 0.657(6) 1 calc R U P C 5
H50C H 0.494325 -0.008262 0.184529 0.065 Uiso 0.657(6) 1 calc R U P C 5
O102 O 0.8769(9) 0.1158(9) 0.3384(9) 0.081(4) Uani 0.343(6) 1 d D U P C 6
C148 C 0.7927(13) 0.0548(12) 0.3111(14) 0.052(3) Uani 0.343(6) 1 d D U P C 6
H148 H 0.803465 -0.015920 0.297463 0.062 Uiso 0.343(6) 1 calc R U P C 6
N106 N 0.6842(12) 0.0730(13) 0.2972(18) 0.046(3) Uani 0.343(6) 1 d D U P C 6
C149 C 0.656(2) 0.1771(15) 0.322(4) 0.054(5) Uani 0.343(6) 1 d D U P C 6
H14A H 0.715969 0.228382 0.324310 0.081 Uiso 0.343(6) 1 calc R U P C 6
H14B H 0.655154 0.187656 0.395067 0.081 Uiso 0.343(6) 1 calc R U P C 6
H14C H 0.577292 0.184925 0.263899 0.081 Uiso 0.343(6) 1 calc R U P C 6
C150 C 0.5870(14) -0.0085(12) 0.2557(13) 0.063(4) Uani 0.343(6) 1 d D U P C 6
H15A H 0.605403 -0.070082 0.218811 0.095 Uiso 0.343(6) 1 calc R U P C 6
H15B H 0.514550 0.014044 0.201636 0.095 Uiso 0.343(6) 1 calc R U P C 6
H15C H 0.574543 -0.025031 0.318241 0.095 Uiso 0.343(6) 1 calc R U P C 6
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
C4 N1 C1 109.3(3) . . ?
C4 N1 H1 125.3 . . ?
C1 N1 H1 125.3 . . ?
C4 C102 C1 109.3(3) . . ?
C4 C102 H102 125.3 . . ?
C1 C102 H102 125.3 . . ?
C6 N2 C9 106.5(3) . . ?
C26 N3 C23 109.3(3) . . ?
C26 N3 H3 125.3 . . ?
C23 N3 H3 125.3 . . ?
C26 C124 C23 109.3(3) . . ?
C26 C124 H124 125.3 . . ?
C23 C124 H124 125.3 . . ?
C28 N4 C31 106.3(3) . . ?
C2 C1 C10 128.4(3) . 2_656 ?
N101 C1 C102 106.8(3) . . ?
C10 C1 C102 124.8(3) 2_656 . ?
C2 C1 N1 106.8(3) . . ?
C10 C1 N1 124.8(3) 2_656 . ?
C3 C2 C1 108.8(3) . . ?
C3 C2 H2 125.6 . . ?
C1 C2 H2 125.6 . . ?
C3 N101 C1 108.8(3) . . ?
C3 N101 H101 125.6 . . ?
C1 N101 H101 125.6 . . ?
N101 C3 C5 128.6(3) . . ?
C2 C3 C5 128.6(3) . . ?
N101 C3 C4 107.5(3) . . ?
C2 C3 C4 107.5(3) . . ?
C5 C3 C4 123.6(3) . . ?
C102 C4 C3 107.6(3) . . ?
N1 C4 C3 107.6(3) . . ?
N1 C4 H4 126.2 . . ?
C3 C4 H4 126.2 . . ?
C6 C5 C3 123.8(3) . . ?
C6 C5 C11 119.4(3) . . ?
C3 C5 C11 116.8(3) . . ?
N2 C6 C5 125.6(3) . . ?
N2 C6 C7 109.9(3) . . ?
C5 C6 C7 124.5(3) . . ?
C8 C7 C6 106.5(3) . . ?
C8 C7 H7 126.7 . . ?
C6 C7 H7 126.7 . . ?
C7 C8 C9 108.0(3) . . ?
C7 C8 H8 126.0 . . ?
C9 C8 H8 126.0 . . ?
N2 C9 C10 125.2(3) . . ?
N2 C9 C8 109.0(3) . . ?
C10 C9 C8 125.8(3) . . ?
C1 C10 C9 124.1(3) 2_656 . ?
C1 C10 C17 116.8(3) 2_656 . ?
C9 C10 C17 119.0(3) . . ?
C16 C11 C12 118.3(3) . . ?
C16 C11 C5 119.9(3) . . ?
C12 C11 C5 121.7(3) . . ?
C13 C12 C11 120.5(4) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 121.0(4) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C15 119.3(4) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 119.5(4) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C11 C16 C15 121.3(4) . . ?
C11 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C18 C17 C22 119.4(3) . . ?
C18 C17 C10 119.8(3) . . ?
C22 C17 C10 120.7(3) . . ?
C17 C18 C19 120.8(4) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C20 C19 C18 119.8(4) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 119.8(3) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C22 C21 C20 120.4(4) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C17 119.9(4) . . ?
C21 C22 H22 120.1 . . ?
C17 C22 H22 120.1 . . ?
N103 C23 C32 129.6(3) . 2_667 ?
C24 C23 C32 129.6(3) . 2_667 ?
N103 C23 C124 106.0(3) . . ?
C32 C23 C124 124.4(3) 2_667 . ?
C24 C23 N3 106.0(3) . . ?
C32 C23 N3 124.4(3) 2_667 . ?
C23 C24 C25 110.0(3) . . ?
C23 C24 H24 125.0 . . ?
C25 C24 H24 125.0 . . ?
C23 N103 C25 110.0(3) . . ?
C23 N103 H103 125.0 . . ?
C25 N103 H103 125.0 . . ?
N103 C25 C27 128.2(3) . . ?
C24 C25 C27 128.2(3) . . ?
N103 C25 C26 106.1(3) . . ?
C24 C25 C26 106.1(3) . . ?
C27 C25 C26 125.7(3) . . ?
C124 C26 C25 108.6(3) . . ?
N3 C26 C25 108.6(3) . . ?
N3 C26 H26 125.7 . . ?
C25 C26 H26 125.7 . . ?
C28 C27 C25 124.1(3) . . ?
C28 C27 C33 118.4(3) . . ?
C25 C27 C33 117.4(3) . . ?
N4 C28 C27 125.2(3) . . ?
N4 C28 C29 109.6(3) . . ?
C27 C28 C29 125.1(3) . . ?
C30 C29 C28 107.1(3) . . ?
C30 C29 H29 126.4 . . ?
C28 C29 H29 126.4 . . ?
C29 C30 C31 107.0(3) . . ?
C29 C30 H30 126.5 . . ?
C31 C30 H30 126.5 . . ?
N4 C31 C32 125.0(3) . . ?
N4 C31 C30 109.9(3) . . ?
C32 C31 C30 125.0(3) . . ?
C23 C32 C31 124.2(3) 2_667 . ?
C23 C32 C39 118.0(3) 2_667 . ?
C31 C32 C39 117.8(3) . . ?
C38 C33 C34 118.7(3) . . ?
C38 C33 C27 121.0(3) . . ?
C34 C33 C27 120.3(3) . . ?
C35 C34 C33 120.3(4) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C36 C35 C34 121.2(4) . . ?
C36 C35 H35 119.4 . . ?
C34 C35 H35 119.4 . . ?
C35 C36 C37 119.0(3) . . ?
C35 C36 H36 120.5 . . ?
C37 C36 H36 120.5 . . ?
C36 C37 C38 120.7(4) . . ?
C36 C37 H37 119.6 . . ?
C38 C37 H37 119.6 . . ?
C33 C38 C37 120.0(4) . . ?
C33 C38 H38 120.0 . . ?
C37 C38 H38 120.0 . . ?
C40 C39 C44 118.6(3) . . ?
C40 C39 C32 120.2(3) . . ?
C44 C39 C32 121.2(3) . . ?
C41 C40 C39 121.4(3) . . ?
C41 C40 H40 119.3 . . ?
C39 C40 H40 119.3 . . ?
C40 C41 C42 119.6(4) . . ?
C40 C41 H41 120.2 . . ?
C42 C41 H41 120.2 . . ?
C43 C42 C41 119.9(3) . . ?
C43 C42 H42 120.1 . . ?
C41 C42 H42 120.1 . . ?
C42 C43 C44 120.6(3) . . ?
C42 C43 H43 119.7 . . ?
C44 C43 H43 119.7 . . ?
C43 C44 C39 119.9(3) . . ?
C43 C44 H44 120.0 . . ?
C39 C44 H44 120.0 . . ?
O1 C45 N5 123.6(5) . . ?
O1 C45 H45 118.2 . . ?
N5 C45 H45 118.2 . . ?
C45 N5 C47 119.1(5) . . ?
C45 N5 C46 118.9(5) . . ?
C47 N5 C46 122.0(5) . . ?
N5 C46 H46A 109.5 . . ?
N5 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
N5 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
N5 C47 H47A 109.5 . . ?
N5 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
N5 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
O2 C48 N6 127.9(10) . . ?
O2 C48 H48 116.1 . . ?
N6 C48 H48 116.1 . . ?
C48 N6 C50 124.2(7) . . ?
C48 N6 C49 119.2(8) . . ?
C50 N6 C49 116.3(6) . . ?
N6 C49 H49A 109.5 . . ?
N6 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
N6 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
N6 C50 H50A 109.5 . . ?
N6 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
N6 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
O102 C148 N106 127.9(16) . . ?
O102 C148 H148 116.0 . . ?
N106 C148 H148 116.0 . . ?
C148 N106 C150 122.2(16) . . ?
C148 N106 C149 122.6(14) . . ?
C150 N106 C149 115.3(15) . . ?
N106 C149 H14A 109.5 . . ?
N106 C149 H14B 109.5 . . ?
H14A C149 H14B 109.5 . . ?
N106 C149 H14C 109.5 . . ?
H14A C149 H14C 109.5 . . ?
H14B C149 H14C 109.5 . . ?
N106 C150 H15A 109.5 . . ?
N106 C150 H15B 109.5 . . ?
H15A C150 H15B 109.5 . . ?
N106 C150 H15C 109.5 . . ?
H15A C150 H15C 109.5 . . ?
H15B C150 H15C 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
N1 C4 1.343(5) . ?
N1 C1 1.422(5) . ?
N1 H1 0.8800 . ?
C102 C4 1.343(5) . ?
C102 C1 1.422(5) . ?
C102 H102 0.9500 . ?
N2 C6 1.367(4) . ?
N2 C9 1.382(4) . ?
N3 C26 1.343(5) . ?
N3 C23 1.422(4) . ?
N3 H3 0.8800 . ?
C124 C26 1.343(5) . ?
C124 C23 1.422(4) . ?
C124 H124 0.9500 . ?
N4 C28 1.375(4) . ?
N4 C31 1.375(4) . ?
C1 N101 1.387(4) . ?
C1 C2 1.387(4) . ?
C1 C10 1.399(5) 2_656 ?
C2 C3 1.379(5) . ?
C2 H2 0.9500 . ?
N101 C3 1.379(5) . ?
N101 H101 0.8800 . ?
C3 C5 1.422(5) . ?
C3 C4 1.432(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.413(5) . ?
C5 C11 1.482(5) . ?
C6 C7 1.451(5) . ?
C7 C8 1.344(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.443(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.400(5) . ?
C10 C17 1.498(5) . ?
C11 C16 1.385(5) . ?
C11 C12 1.397(5) . ?
C12 C13 1.376(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.376(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.395(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.384(5) . ?
C17 C22 1.404(5) . ?
C18 C19 1.395(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.397(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(5) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 N103 1.380(4) . ?
C23 C24 1.380(4) . ?
C23 C32 1.400(5) 2_667 ?
C24 C25 1.387(4) . ?
C24 H24 0.9500 . ?
N103 C25 1.387(4) . ?
N103 H103 0.8800 . ?
C25 C27 1.412(5) . ?
C25 C26 1.424(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.403(5) . ?
C27 C33 1.497(5) . ?
C28 C29 1.458(5) . ?
C29 C30 1.346(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.452(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.412(5) . ?
C32 C39 1.489(5) . ?
C33 C38 1.395(5) . ?
C33 C34 1.402(5) . ?
C34 C35 1.383(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.376(5) . ?
C35 H35 0.9500 . ?
C36 C37 1.389(5) . ?
C36 H36 0.9500 . ?
C37 C38 1.396(5) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 C40 1.391(5) . ?
C39 C44 1.404(5) . ?
C40 C41 1.385(5) . ?
C40 H40 0.9500 . ?
C41 C42 1.393(5) . ?
C41 H41 0.9500 . ?
C42 C43 1.381(5) . ?
C42 H42 0.9500 . ?
C43 C44 1.396(5) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
O1 C45 1.230(7) . ?
C45 N5 1.379(7) . ?
C45 H45 0.9500 . ?
N5 C47 1.404(6) . ?
N5 C46 1.413(6) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
O2 C48 1.189(12) . ?
C48 N6 1.343(12) . ?
C48 H48 0.9500 . ?
N6 C50 1.443(8) . ?
N6 C49 1.457(10) . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
O102 C148 1.182(14) . ?
C148 N106 1.336(16) . ?
C148 H148 0.9500 . ?
N106 C150 1.435(14) . ?
N106 C149 1.46(2) . ?
C149 H14A 0.9800 . ?
C149 H14B 0.9800 . ?
C149 H14C 0.9800 . ?
C150 H15A 0.9800 . ?
C150 H15B 0.9800 . ?
C150 H15C 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
C4 C102 C1 N101 1.2(4) . . . . ?
C4 C102 C1 C10 -176.6(3) . . . 2_656 ?
C4 N1 C1 C2 1.2(4) . . . . ?
C4 N1 C1 C10 -176.6(3) . . . 2_656 ?
C10 C1 C2 C3 176.6(4) 2_656 . . . ?
N1 C1 C2 C3 -1.1(4) . . . . ?
C10 C1 N101 C3 176.6(4) 2_656 . . . ?
C102 C1 N101 C3 -1.1(4) . . . . ?
C1 N101 C3 C5 -173.6(4) . . . . ?
C1 N101 C3 C4 0.7(4) . . . . ?
C1 C2 C3 C5 -173.6(4) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
C1 C102 C4 C3 -0.8(4) . . . . ?
C1 N1 C4 C3 -0.8(4) . . . . ?
N101 C3 C4 C102 0.1(4) . . . . ?
C5 C3 C4 C102 174.7(3) . . . . ?
C2 C3 C4 N1 0.1(4) . . . . ?
C5 C3 C4 N1 174.7(3) . . . . ?
N101 C3 C5 C6 1.0(6) . . . . ?
C2 C3 C5 C6 1.0(6) . . . . ?
C4 C3 C5 C6 -172.5(3) . . . . ?
N101 C3 C5 C11 178.3(3) . . . . ?
C2 C3 C5 C11 178.3(3) . . . . ?
C4 C3 C5 C11 4.8(5) . . . . ?
C9 N2 C6 C5 -177.9(3) . . . . ?
C9 N2 C6 C7 0.2(4) . . . . ?
C3 C5 C6 N2 0.1(5) . . . . ?
C11 C5 C6 N2 -177.0(3) . . . . ?
C3 C5 C6 C7 -177.6(3) . . . . ?
C11 C5 C6 C7 5.2(5) . . . . ?
N2 C6 C7 C8 -0.1(4) . . . . ?
C5 C6 C7 C8 177.9(3) . . . . ?
C6 C7 C8 C9 0.1(4) . . . . ?
C6 N2 C9 C10 -177.8(3) . . . . ?
C6 N2 C9 C8 -0.1(4) . . . . ?
C7 C8 C9 N2 0.0(4) . . . . ?
C7 C8 C9 C10 177.7(3) . . . . ?
N2 C9 C10 C1 1.0(6) . . . 2_656 ?
C8 C9 C10 C1 -176.3(3) . . . 2_656 ?
N2 C9 C10 C17 -174.6(3) . . . . ?
C8 C9 C10 C17 8.1(6) . . . . ?
C6 C5 C11 C16 69.9(4) . . . . ?
C3 C5 C11 C16 -107.5(4) . . . . ?
C6 C5 C11 C12 -113.4(4) . . . . ?
C3 C5 C11 C12 69.2(5) . . . . ?
C16 C11 C12 C13 0.2(5) . . . . ?
C5 C11 C12 C13 -176.5(3) . . . . ?
C11 C12 C13 C14 -1.3(6) . . . . ?
C12 C13 C14 C15 1.6(6) . . . . ?
C13 C14 C15 C16 -0.9(6) . . . . ?
C12 C11 C16 C15 0.5(5) . . . . ?
C5 C11 C16 C15 177.3(3) . . . . ?
C14 C15 C16 C11 -0.2(5) . . . . ?
C1 C10 C17 C18 -109.4(4) 2_656 . . . ?
C9 C10 C17 C18 66.5(5) . . . . ?
C1 C10 C17 C22 66.8(5) 2_656 . . . ?
C9 C10 C17 C22 -117.3(4) . . . . ?
C22 C17 C18 C19 -0.6(5) . . . . ?
C10 C17 C18 C19 175.6(3) . . . . ?
C17 C18 C19 C20 -0.1(5) . . . . ?
C18 C19 C20 C21 0.3(5) . . . . ?
C19 C20 C21 C22 0.2(6) . . . . ?
C20 C21 C22 C17 -0.9(6) . . . . ?
C18 C17 C22 C21 1.1(5) . . . . ?
C10 C17 C22 C21 -175.1(3) . . . . ?
C26 C124 C23 N103 -0.8(4) . . . . ?
C26 C124 C23 C32 -179.0(3) . . . 2_667 ?
C26 N3 C23 C24 -0.8(4) . . . . ?
C26 N3 C23 C32 -179.0(3) . . . 2_667 ?
C32 C23 C24 C25 178.0(3) 2_667 . . . ?
N3 C23 C24 C25 -0.1(4) . . . . ?
C32 C23 N103 C25 178.0(3) 2_667 . . . ?
C124 C23 N103 C25 -0.1(4) . . . . ?
C23 N103 C25 C27 -178.7(3) . . . . ?
C23 N103 C25 C26 0.9(4) . . . . ?
C23 C24 C25 C27 -178.7(3) . . . . ?
C23 C24 C25 C26 0.9(4) . . . . ?
C23 C124 C26 C25 1.4(4) . . . . ?
C23 N3 C26 C25 1.4(4) . . . . ?
N103 C25 C26 C124 -1.5(4) . . . . ?
C27 C25 C26 C124 178.2(3) . . . . ?
C24 C25 C26 N3 -1.5(4) . . . . ?
C27 C25 C26 N3 178.2(3) . . . . ?
N103 C25 C27 C28 -0.3(6) . . . . ?
C24 C25 C27 C28 -0.3(6) . . . . ?
C26 C25 C27 C28 -179.9(3) . . . . ?
N103 C25 C27 C33 -178.2(3) . . . . ?
C24 C25 C27 C33 -178.2(3) . . . . ?
C26 C25 C27 C33 2.2(5) . . . . ?
C31 N4 C28 C27 -179.4(3) . . . . ?
C31 N4 C28 C29 2.2(4) . . . . ?
C25 C27 C28 N4 -1.5(5) . . . . ?
C33 C27 C28 N4 176.4(3) . . . . ?
C25 C27 C28 C29 176.7(3) . . . . ?
C33 C27 C28 C29 -5.4(5) . . . . ?
N4 C28 C29 C30 -1.6(4) . . . . ?
C27 C28 C29 C30 180.0(3) . . . . ?
C28 C29 C30 C31 0.4(4) . . . . ?
C28 N4 C31 C32 -179.0(3) . . . . ?
C28 N4 C31 C30 -1.9(4) . . . . ?
C29 C30 C31 N4 0.9(4) . . . . ?
C29 C30 C31 C32 178.0(3) . . . . ?
N4 C31 C32 C23 2.9(5) . . . 2_667 ?
C30 C31 C32 C23 -173.8(3) . . . 2_667 ?
N4 C31 C32 C39 -176.4(3) . . . . ?
C30 C31 C32 C39 6.9(5) . . . . ?
C28 C27 C33 C38 122.2(4) . . . . ?
C25 C27 C33 C38 -59.8(4) . . . . ?
C28 C27 C33 C34 -58.0(4) . . . . ?
C25 C27 C33 C34 120.0(4) . . . . ?
C38 C33 C34 C35 0.8(5) . . . . ?
C27 C33 C34 C35 -179.0(3) . . . . ?
C33 C34 C35 C36 -0.9(5) . . . . ?
C34 C35 C36 C37 0.8(5) . . . . ?
C35 C36 C37 C38 -0.5(6) . . . . ?
C34 C33 C38 C37 -0.5(5) . . . . ?
C27 C33 C38 C37 179.3(3) . . . . ?
C36 C37 C38 C33 0.4(5) . . . . ?
C23 C32 C39 C40 -119.8(4) 2_667 . . . ?
C31 C32 C39 C40 59.6(4) . . . . ?
C23 C32 C39 C44 59.5(4) 2_667 . . . ?
C31 C32 C39 C44 -121.1(3) . . . . ?
C44 C39 C40 C41 0.0(5) . . . . ?
C32 C39 C40 C41 179.4(3) . . . . ?
C39 C40 C41 C42 -0.7(5) . . . . ?
C40 C41 C42 C43 0.7(6) . . . . ?
C41 C42 C43 C44 0.0(5) . . . . ?
C42 C43 C44 C39 -0.6(5) . . . . ?
C40 C39 C44 C43 0.6(5) . . . . ?
C32 C39 C44 C43 -178.7(3) . . . . ?
O1 C45 N5 C47 178.2(6) . . . . ?
O1 C45 N5 C46 -3.2(9) . . . . ?
O2 C48 N6 C50 -174.3(14) . . . . ?
O2 C48 N6 C49 0(3) . . . . ?
O102 C148 N106 C150 175.4(18) . . . . ?
O102 C148 N106 C149 -4(4) . . . . ?
