#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:10:15 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180171 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/67/7106708.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_7106708
loop_
_publ_author_name
'Joshua Akhigbe'
'John Haskoor'
'Matthias Zeller'
'Christian Bruckner'
_publ_section_title
;
 Porpholactams and chlorolactams: Replacement of a b,b'-double bond in
 meso-tetraphenyl-porphyrin and -chlorin by a lactam moiety
;
_journal_name_full               Chem.Commun.
_journal_page_first              8599
_journal_paper_doi               10.1039/c1cc12955d
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         'C43 H32 N6 O, 2(C2 H6 O)'
_chemical_formula_sum            'C47 H44 N6 O3'
_chemical_formula_weight         740.88
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.192(2)
_cell_angle_beta                 95.593(2)
_cell_angle_gamma                90.383(3)
_cell_formula_units_Z            2
_cell_length_a                   11.805(2)
_cell_length_b                   12.627(2)
_cell_length_c                   13.460(2)
_cell_measurement_reflns_used    7477
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.95
_cell_measurement_theta_min      2.23
_cell_volume                     1906.3(5)
_computing_cell_refinement       'Apex2 v2009.7-0'
_computing_data_collection       'Apex2 v2009.7-0 (Bruker, 2009)'
_computing_data_reduction        'Apex2 v2009.7-0'
_computing_molecular_graphics    'SHELXTL 6.14'
_computing_publication_material  'SHELXTL 6.14'
_computing_structure_refinement  'SHELXTL 6.14'
_computing_structure_solution
'SHELXTL 6.14 (Bruker, 2000-2003; Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker AXS SMART APEX CCD diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25313
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         1.69
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.5968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Apex2 v2009.7-0 (Bruker, 2009)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     569
_refine_ls_number_reflns         9008
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0594
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0720P)²+1.1613P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1484
_refine_ls_wR_factor_ref         0.1640
_reflns_number_gt                7105
_reflns_number_total             9008
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c1cc12955d.txt
_cod_data_source_block           10mz469_0m
_cod_original_cell_volume        1906.2(6)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7106708
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.4831(4) 0.2400(4) 0.4588(3) 0.0507(9) Uani 0.753(7) 1 d PD A 1
H2A H 0.4598 0.2323 0.5134 0.076 Uiso 0.753(7) 1 calc PRD A 1
C45 C 0.5822(4) 0.1805(4) 0.4379(3) 0.0622(14) Uani 0.753(7) 1 d PD A 1
H45A H 0.5631 0.0999 0.4166 0.075 Uiso 0.753(7) 1 calc PR A 1
H45B H 0.6365 0.1986 0.5020 0.075 Uiso 0.753(7) 1 calc PR A 1
C46 C 0.6359(3) 0.2088(4) 0.3530(4) 0.0567(12) Uani 0.753(7) 1 d PD A 1
H46A H 0.6566 0.2882 0.3750 0.085 Uiso 0.753(7) 1 calc PR A 1
H46B H 0.5819 0.1909 0.2897 0.085 Uiso 0.753(7) 1 calc PR A 1
H46C H 0.7044 0.1660 0.3382 0.085 Uiso 0.753(7) 1 calc PR A 1
O3 O 0.3986(7) 0.2232(9) 0.6192(5) 0.069(2) Uani 0.637(8) 1 d PD B 1
H3 H 0.3506 0.2650 0.6516 0.104 Uiso 0.637(8) 1 calc PRD A 1
C47 C 0.4683(5) 0.1803(5) 0.6905(5) 0.077(2) Uani 0.637(8) 1 d PD B 1
H47A H 0.5206 0.1258 0.6520 0.093 Uiso 0.637(8) 1 calc PR B 1
H47B H 0.4199 0.1423 0.7266 0.093 Uiso 0.637(8) 1 calc PR B 1
C48 C 0.5349(10) 0.2742(8) 0.7683(9) 0.141(6) Uani 0.637(8) 1 d PD B 1
H48A H 0.4828 0.3304 0.8022 0.212 Uiso 0.637(8) 1 calc PR B 1
H48B H 0.5877 0.3069 0.7328 0.212 Uiso 0.637(8) 1 calc PR B 1
H48C H 0.5780 0.2469 0.8212 0.212 Uiso 0.637(8) 1 calc PR B 1
O2B O 0.4741(14) 0.2598(14) 0.4336(12) 0.0507(9) Uani 0.247(7) 1 d P A 2
H2B H 0.4860 0.2294 0.4811 0.076 Uiso 0.247(7) 1 calc PRD A 2
C45B C 0.5742(8) 0.2628(7) 0.3869(8) 0.036(3) Uani 0.247(7) 1 d P A 2
H45C H 0.6102 0.3382 0.4152 0.044 Uiso 0.247(7) 1 calc PR A 2
H45D H 0.5545 0.2487 0.3108 0.044 Uiso 0.247(7) 1 calc PR A 2
C46B C 0.6567(12) 0.1820(9) 0.4035(12) 0.048(3) Uani 0.247(7) 1 d P A 2
H46D H 0.6224 0.1069 0.3744 0.072 Uiso 0.247(7) 1 calc PR A 2
H46E H 0.6785 0.1967 0.4786 0.072 Uiso 0.247(7) 1 calc PR A 2
H46F H 0.7245 0.1882 0.3686 0.072 Uiso 0.247(7) 1 calc PR A 2
O3B O 0.4037(9) 0.2449(12) 0.6537(8) 0.049(3) Uani 0.363(8) 1 d PD B 2
H3B H 0.3575 0.2952 0.6541 0.074 Uiso 0.363(8) 1 calc PR A 2
C47B C 0.4774(6) 0.2749(8) 0.7525(6) 0.045(3) Uani 0.363(8) 1 d PD B 2
H47C H 0.4430 0.2473 0.8048 0.054 Uiso 0.363(8) 1 calc PR B 2
H47D H 0.4883 0.3566 0.7806 0.054 Uiso 0.363(8) 1 calc PR B 2
C48B C 0.5888(6) 0.2227(8) 0.7301(7) 0.043(2) Uani 0.363(8) 1 d PD B 2
H48D H 0.6277 0.2593 0.6873 0.064 Uiso 0.363(8) 1 calc PR B 2
H48E H 0.5756 0.1438 0.6921 0.064 Uiso 0.363(8) 1 calc PR B 2
H48F H 0.6363 0.2308 0.7960 0.064 Uiso 0.363(8) 1 calc PR B 2
C1 C 0.21407(16) 0.46910(15) 0.62699(14) 0.0229(4) Uani 1 1 d . A .
C2 C 0.15007(15) 0.57003(15) 0.65690(13) 0.0211(4) Uani 1 1 d . . .
C3 C 0.12148(15) 0.61826(14) 0.75849(13) 0.0198(3) Uani 1 1 d . . .
C4 C 0.04843(15) 0.70714(14) 0.78654(13) 0.0198(3) Uani 1 1 d . . .
C5 C 0.01404(16) 0.75873(15) 0.88776(13) 0.0224(4) Uani 1 1 d . . .
H5 H 0.0405 0.7421 0.9502 0.027 Uiso 1 1 calc R . .
C6 C -0.06375(15) 0.83638(15) 0.87928(13) 0.0218(4) Uani 1 1 d . . .
H6 H -0.1010 0.8825 0.9349 0.026 Uiso 1 1 calc R . .
C7 C -0.07937(15) 0.83621(14) 0.77282(13) 0.0197(3) Uani 1 1 d . . .
C8 C -0.15338(15) 0.90262(14) 0.73019(13) 0.0200(3) Uani 1 1 d . . .
C9 C -0.16058(15) 0.91104(15) 0.62893(13) 0.0209(4) Uani 1 1 d . . .
C10 C -0.24260(18) 0.98702(17) 0.59305(14) 0.0287(4) Uani 1 1 d . . .
H10A H -0.2323 1.0640 0.6401 0.034 Uiso 1 1 calc R . .
H10B H -0.3226 0.9611 0.5900 0.034 Uiso 1 1 calc R . .
C11 C -0.21031(19) 0.97932(18) 0.48439(15) 0.0312(4) Uani 1 1 d . . .
H11A H -0.2775 0.9590 0.4315 0.037 Uiso 1 1 calc R . .
H11B H -0.1755 1.0502 0.4827 0.037 Uiso 1 1 calc R . .
C12 C -0.12510(16) 0.88853(15) 0.46619(14) 0.0223(4) Uani 1 1 d . . .
C13 C -0.08263(16) 0.84542(15) 0.36871(13) 0.0214(4) Uani 1 1 d . . .
C14 C 0.00160(16) 0.76676(15) 0.34652(13) 0.0226(4) Uani 1 1 d . . .
C15 C 0.05627(17) 0.73360(16) 0.25213(14) 0.0261(4) Uani 1 1 d . . .
H15 H 0.0405 0.7602 0.1934 0.031 Uiso 1 1 calc R . .
C16 C 0.13462(17) 0.65745(17) 0.26117(14) 0.0262(4) Uani 1 1 d . . .
H16 H 0.1841 0.6232 0.2104 0.031 Uiso 1 1 calc R . .
C17 C 0.12977(16) 0.63784(16) 0.36005(13) 0.0232(4) Uani 1 1 d . . .
C18 C 0.18983(16) 0.56049(15) 0.39679(13) 0.0227(4) Uani 1 1 d . . .
C19 C 0.17937(16) 0.54359(15) 0.49441(14) 0.0226(4) Uani 1 1 d . A .
C21 C 0.17779(16) 0.57881(14) 0.84494(13) 0.0208(4) Uani 1 1 d . . .
C22 C 0.29401(16) 0.60125(16) 0.87263(14) 0.0248(4) Uani 1 1 d . . .
H22 H 0.3352 0.6399 0.8360 0.030 Uiso 1 1 calc R . .
C23 C 0.35049(19) 0.56795(18) 0.95300(16) 0.0321(4) Uani 1 1 d . . .
H23 H 0.4298 0.5841 0.9714 0.038 Uiso 1 1 calc R . .
C24 C 0.29098(19) 0.51109(18) 1.00648(16) 0.0325(5) Uani 1 1 d . . .
H24 H 0.3294 0.4882 1.0616 0.039 Uiso 1 1 calc R . .
C25 C 0.1756(2) 0.48789(18) 0.97912(16) 0.0326(5) Uani 1 1 d . . .
H25 H 0.1349 0.4485 1.0154 0.039 Uiso 1 1 calc R . .
C26 C 0.11894(17) 0.52161(16) 0.89908(15) 0.0269(4) Uani 1 1 d . . .
H26 H 0.0395 0.5056 0.8811 0.032 Uiso 1 1 calc R . .
C27 C -0.23324(16) 0.96941(15) 0.80244(13) 0.0210(4) Uani 1 1 d . . .
C28 C -0.19466(17) 1.06496(16) 0.88256(14) 0.0260(4) Uani 1 1 d . . .
H28 H -0.1167 1.0885 0.8919 0.031 Uiso 1 1 calc R . .
C29 C -0.27042(19) 1.12585(17) 0.94875(15) 0.0313(4) Uani 1 1 d . . .
H29 H -0.2437 1.1906 1.0032 0.038 Uiso 1 1 calc R . .
C30 C -0.38380(19) 1.09286(18) 0.93575(16) 0.0323(5) Uani 1 1 d . . .
H30 H -0.4351 1.1350 0.9808 0.039 Uiso 1 1 calc R . .
C31 C -0.42287(18) 0.99792(18) 0.85662(16) 0.0311(4) Uani 1 1 d . . .
H31 H -0.5009 0.9747 0.8478 0.037 Uiso 1 1 calc R . .
C32 C -0.34788(17) 0.93670(16) 0.79027(15) 0.0263(4) Uani 1 1 d . . .
H32 H -0.3752 0.8719 0.7361 0.032 Uiso 1 1 calc R . .
C33 C -0.13773(16) 0.87654(15) 0.27665(13) 0.0223(4) Uani 1 1 d . . .
C34 C -0.12847(17) 0.98252(16) 0.26562(15) 0.0261(4) Uani 1 1 d . . .
H34 H -0.0850 1.0393 0.3182 0.031 Uiso 1 1 calc R . .
C35 C -0.18218(18) 1.00590(17) 0.17850(16) 0.0288(4) Uani 1 1 d . . .
H35 H -0.1746 1.0783 0.1716 0.035 Uiso 1 1 calc R . .
C36 C -0.24697(18) 0.92420(18) 0.10142(15) 0.0293(4) Uani 1 1 d . . .
H36 H -0.2845 0.9405 0.0423 0.035 Uiso 1 1 calc R . .
C37 C -0.25623(19) 0.81836(18) 0.11174(15) 0.0321(5) Uani 1 1 d . . .
H37 H -0.3002 0.7619 0.0592 0.039 Uiso 1 1 calc R . .
C38 C -0.20164(18) 0.79455(17) 0.19834(14) 0.0282(4) Uani 1 1 d . . .
H38 H -0.2079 0.7217 0.2043 0.034 Uiso 1 1 calc R . .
C39 C 0.27144(16) 0.49239(15) 0.32804(14) 0.0224(4) Uani 1 1 d . . .
C40 C 0.23173(16) 0.40651(15) 0.23926(13) 0.0232(4) Uani 1 1 d . . .
H40 H 0.1521 0.3940 0.2199 0.028 Uiso 1 1 calc R . .
C41 C 0.30727(17) 0.33922(16) 0.17901(14) 0.0262(4) Uani 1 1 d . . .
H41 H 0.2793 0.2795 0.1199 0.031 Uiso 1 1 calc R . .
C42 C 0.42261(19) 0.35869(18) 0.20459(18) 0.0351(5) Uani 1 1 d . . .
H42 H 0.4744 0.3130 0.1629 0.042 Uiso 1 1 calc R . .
C43 C 0.4631(2) 0.4455(2) 0.2917(2) 0.0497(7) Uani 1 1 d . . .
H43 H 0.5428 0.4596 0.3090 0.060 Uiso 1 1 calc R . .
C44 C 0.38771(18) 0.5120(2) 0.35372(19) 0.0396(5) Uani 1 1 d . . .
H44 H 0.4160 0.5707 0.4136 0.047 Uiso 1 1 calc R . .
N1 N 0.12743(13) 0.61017(13) 0.57359(11) 0.0210(3) Uani 1 1 d . . .
N2 N -0.00901(13) 0.75812(12) 0.71995(11) 0.0199(3) Uani 1 1 d . . .
H2 H -0.0015 0.7426 0.6528 0.024 Uiso 1 1 calc R . .
N3 N -0.09634(13) 0.85532(12) 0.55188(11) 0.0209(3) Uani 1 1 d . . .
N4 N 0.05004(13) 0.70838(13) 0.40962(11) 0.0225(3) Uani 1 1 d . . .
H4 H 0.0327 0.7149 0.4732 0.027 Uiso 1 1 calc R . .
O1 O 0.23978(14) 0.39798(12) 0.67493(11) 0.0341(3) Uani 1 1 d D . .
N6 N 0.2664(2) 0.35965(17) 0.45994(14) 0.0421(5) Uani 1 1 d D A .
H6A H 0.3391(15) 0.367(3) 0.474(3) 0.063 Uiso 1 1 d D . .
H6B H 0.251(2) 0.303(2) 0.485(2) 0.063 Uiso 1 1 d D . .
N5 N 0.23183(15) 0.45548(14) 0.52524(12) 0.0280(4) 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 0.0033 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
O2 C45 C46 110.1(4) . . ?
O2 C45 H45A 109.6 . . ?
C46 C45 H45A 109.6 . . ?
O2 C45 H45B 109.6 . . ?
C46 C45 H45B 109.6 . . ?
H45A C45 H45B 108.1 . . ?
O3 C47 C48 108.6(6) . . ?
O3 C47 H47A 110.0 . . ?
C48 C47 H47A 110.0 . . ?
O3 C47 H47B 110.0 . . ?
C48 C47 H47B 110.0 . . ?
H47A C47 H47B 108.4 . . ?
C45B O2B H2B 109.5 . . ?
O2B C45B C46B 113.7(10) . . ?
O2B C45B H45C 108.8 . . ?
C46B C45B H45C 108.8 . . ?
O2B C45B H45D 108.8 . . ?
C46B C45B H45D 108.8 . . ?
H45C C45B H45D 107.7 . . ?
C45B C46B H46D 109.5 . . ?
C45B C46B H46E 109.5 . . ?
H46D C46B H46E 109.5 . . ?
C45B C46B H46F 109.5 . . ?
H46D C46B H46F 109.5 . . ?
H46E C46B H46F 109.5 . . ?
C47B O3B H3B 109.5 . . ?
O3B C47B C48B 107.1(7) . . ?
O3B C47B H47C 110.3 . . ?
C48B C47B H47C 110.3 . . ?
O3B C47B H47D 110.3 . . ?
C48B C47B H47D 110.3 . . ?
H47C C47B H47D 108.6 . . ?
C47B C48B H48D 109.5 . . ?
C47B C48B H48E 109.5 . . ?
H48D C48B H48E 109.5 . . ?
C47B C48B H48F 109.5 . . ?
H48D C48B H48F 109.5 . . ?
H48E C48B H48F 109.5 . . ?
O1 C1 N5 123.77(17) . . ?
O1 C1 C2 131.13(17) . . ?
N5 C1 C2 104.67(16) . . ?
N1 C2 C3 126.53(16) . . ?
N1 C2 C1 110.31(15) . . ?
C3 C2 C1 123.12(16) . . ?
C2 C3 C4 124.16(16) . . ?
C2 C3 C21 118.58(16) . . ?
C4 C3 C21 117.12(15) . . ?
N2 C4 C3 126.49(15) . . ?
N2 C4 C5 106.34(15) . . ?
C3 C4 C5 127.09(17) . . ?
C6 C5 C4 108.12(16) . . ?
C6 C5 H5 125.9 . . ?
C4 C5 H5 125.9 . . ?
C5 C6 C7 108.41(15) . . ?
C5 C6 H6 125.8 . . ?
C7 C6 H6 125.8 . . ?
N2 C7 C8 126.82(15) . . ?
N2 C7 C6 106.41(15) . . ?
C8 C7 C6 126.77(16) . . ?
C9 C8 C7 126.95(16) . . ?
C9 C8 C27 117.43(16) . . ?
C7 C8 C27 115.61(15) . . ?
N3 C9 C8 125.77(17) . . ?
N3 C9 C10 112.32(15) . . ?
C8 C9 C10 121.90(16) . . ?
C9 C10 C11 103.10(15) . . ?
C9 C10 H10A 111.1 . . ?
C11 C10 H10A 111.1 . . ?
C9 C10 H10B 111.1 . . ?
C11 C10 H10B 111.1 . . ?
H10A C10 H10B 109.1 . . ?
C12 C11 C10 102.72(16) . . ?
C12 C11 H11A 111.2 . . ?
C10 C11 H11A 111.2 . . ?
C12 C11 H11B 111.2 . . ?
C10 C11 H11B 111.2 . . ?
H11A C11 H11B 109.1 . . ?
N3 C12 C13 125.35(17) . . ?
N3 C12 C11 113.04(15) . . ?
C13 C12 C11 121.61(16) . . ?
C14 C13 C12 125.61(17) . . ?
C14 C13 C33 115.44(15) . . ?
C12 C13 C33 118.69(16) . . ?
N4 C14 C13 127.80(16) . . ?
N4 C14 C15 106.31(16) . . ?
C13 C14 C15 125.88(17) . . ?
C16 C15 C14 108.29(16) . . ?
C16 C15 H15 125.9 . . ?
C14 C15 H15 125.9 . . ?
C15 C16 C17 108.44(16) . . ?
C15 C16 H16 125.8 . . ?
C17 C16 H16 125.8 . . ?
N4 C17 C18 127.08(16) . . ?
N4 C17 C16 106.00(16) . . ?
C18 C17 C16 126.87(17) . . ?
C17 C18 C19 124.11(16) . . ?
C17 C18 C39 117.27(16) . . ?
C19 C18 C39 118.62(17) . . ?
N1 C19 C18 126.39(17) . . ?
N1 C19 N5 110.50(16) . . ?
C18 C19 N5 122.94(16) . . ?
C22 C21 C26 118.76(17) . . ?
C22 C21 C3 118.26(16) . . ?
C26 C21 C3 122.97(17) . . ?
C23 C22 C21 120.82(18) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 119.9(2) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 119.66(19) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 120.48(19) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.36(19) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
C32 C27 C28 118.86(17) . . ?
C32 C27 C8 120.06(16) . . ?
C28 C27 C8 121.08(16) . . ?
C29 C28 C27 120.10(18) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C30 C29 C28 120.51(19) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C29 C30 C31 119.82(18) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C30 C31 C32 120.03(19) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C31 C32 C27 120.66(18) . . ?
C31 C32 H32 119.7 . . ?
C27 C32 H32 119.7 . . ?
C38 C33 C34 118.68(17) . . ?
C38 C33 C13 117.76(16) . . ?
C34 C33 C13 123.57(16) . . ?
C35 C34 C33 120.61(18) . . ?
C35 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C34 C35 C36 120.42(18) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C35 C36 C37 119.26(18) . . ?
C35 C36 H36 120.4 . . ?
C37 C36 H36 120.4 . . ?
C38 C37 C36 120.39(19) . . ?
C38 C37 H37 119.8 . . ?
C36 C37 H37 119.8 . . ?
C37 C38 C33 120.63(18) . . ?
C37 C38 H38 119.7 . . ?
C33 C38 H38 119.7 . . ?
C44 C39 C40 119.16(17) . . ?
C44 C39 C18 120.23(17) . . ?
C40 C39 C18 120.58(16) . . ?
C41 C40 C39 120.62(18) . . ?
C41 C40 H40 119.7 . . ?
C39 C40 H40 119.7 . . ?
C42 C41 C40 120.14(18) . . ?
C42 C41 H41 119.9 . . ?
C40 C41 H41 119.9 . . ?
C41 C42 C43 119.68(19) . . ?
C41 C42 H42 120.2 . . ?
C43 C42 H42 120.2 . . ?
C42 C43 C44 120.5(2) . . ?
C42 C43 H43 119.8 . . ?
C44 C43 H43 119.8 . . ?
C39 C44 C43 119.9(2) . . ?
C39 C44 H44 120.0 . . ?
C43 C44 H44 120.0 . . ?
C19 N1 C2 106.44(15) . . ?
C7 N2 C4 110.68(14) . . ?
C7 N2 H2 124.7 . . ?
C4 N2 H2 124.7 . . ?
C12 N3 C9 108.22(15) . . ?
C14 N4 C17 110.88(15) . . ?
C14 N4 H4 124.6 . . ?
C17 N4 H4 124.6 . . ?
C1 O1 H3B 128.8 . . ?
C1 O1 H3 134.5 . . ?
C1 O1 H2A 102.1 . . ?
C1 O1 H2B 97.9 . . ?
N5 N6 H6A 101(2) . . ?
N5 N6 H6B 109(2) . . ?
H6A N6 H6B 101(2) . . ?
N6 N5 C1 123.93(17) . . ?
N6 N5 C19 126.01(16) . . ?
C1 N5 C19 107.97(15) . . ?
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
O2 C45 1.402(6) . ?
O2 H2A 0.8400 . ?
C45 C46 1.489(7) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
O3 C47 1.432(8) . ?
O3 H3 0.8400 . ?
C47 C48 1.487(9) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
O2B C45B 1.397(19) . ?
O2B H2B 0.8400 . ?
C45B C46B 1.466(15) . ?
C45B H45C 0.9900 . ?
C45B H45D 0.9900 . ?
C46B H46D 0.9800 . ?
C46B H46E 0.9800 . ?
C46B H46F 0.9800 . ?
O3B C47B 1.463(11) . ?
O3B H3B 0.8400 . ?
C47B C48B 1.492(8) . ?
C47B H47C 0.9900 . ?
C47B H47D 0.9900 . ?
C48B H48D 0.9800 . ?
C48B H48E 0.9800 . ?
C48B H48F 0.9800 . ?
C1 O1 1.274(2) . ?
C1 N5 1.366(2) . ?
C1 C2 1.458(3) . ?
C2 N1 1.366(2) . ?
C2 C3 1.398(2) . ?
C3 C4 1.404(2) . ?
C3 C21 1.497(2) . ?
C4 N2 1.381(2) . ?
C4 C5 1.425(2) . ?
C5 C6 1.369(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.426(2) . ?
C6 H6 0.9500 . ?
C7 N2 1.371(2) . ?
C7 C8 1.411(3) . ?
C8 C9 1.393(2) . ?
C8 C27 1.500(2) . ?
C9 N3 1.369(2) . ?
C9 C10 1.512(3) . ?
C10 C11 1.523(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.511(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N3 1.354(2) . ?
C12 C13 1.407(2) . ?
C13 C14 1.400(3) . ?
C13 C33 1.499(2) . ?
C14 N4 1.369(2) . ?
C14 C15 1.433(2) . ?
C15 C16 1.362(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.430(2) . ?
C16 H16 0.9500 . ?
C17 N4 1.381(2) . ?
C17 C18 1.388(3) . ?
C18 C19 1.409(3) . ?
C18 C39 1.496(2) . ?
C19 N1 1.350(2) . ?
C19 N5 1.423(2) . ?
C21 C22 1.391(3) . ?
C21 C26 1.392(3) . ?
C22 C23 1.387(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.387(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.381(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.387(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C32 1.392(3) . ?
C27 C28 1.398(2) . ?
C28 C29 1.394(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.378(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.388(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.391(3) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C38 1.393(3) . ?
C33 C34 1.394(3) . ?
C34 C35 1.388(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.388(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.389(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.388(3) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 C44 1.385(3) . ?
C39 C40 1.393(2) . ?
C40 C41 1.385(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.374(3) . ?
C41 H41 0.9500 . ?
C42 C43 1.389(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.391(3) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
N2 H2 0.8800 . ?
N4 H4 0.8800 . ?
N6 N5 1.361(2) . ?
N6 H6A 0.859(17) . ?
N6 H6B 0.906(17) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H6B N3 0.906(17) 2.60(2) 3.322(3) 137(2) 2_566
N6 H6A O2 0.859(17) 2.33(3) 2.978(5) 133(3) .
N6 H6A O2B 0.859(17) 2.11(3) 2.769(15) 134(3) .
N4 H4 N3 0.88 2.41 2.947(2) 119.4 .
N4 H4 N1 0.88 2.37 2.913(2) 120.3 .
N2 H2 N3 0.88 2.45 2.982(2) 119.6 .
N2 H2 N1 0.88 2.36 2.907(2) 120.9 .
O3B H3B O1 0.84 1.89 2.719(12) 168.4 .
O3 H3 O1 0.84 2.10 2.881(8) 153.6 .
O2B H2B O3 0.84 2.23 2.892(16) 135.5 .
O2 H2A O3B 0.84 2.02 2.854(12) 169.4 .
O2B H2B O3B 0.84 2.56 3.212(18) 135.3 .
O2 H2A O3 0.84 1.69 2.527(9) 173.3 .
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
O1 C1 C2 N1 -169.8(2) . . . . ?
N5 C1 C2 N1 2.6(2) . . . . ?
O1 C1 C2 C3 12.4(3) . . . . ?
N5 C1 C2 C3 -175.15(17) . . . . ?
N1 C2 C3 C4 10.7(3) . . . . ?
C1 C2 C3 C4 -171.86(17) . . . . ?
N1 C2 C3 C21 -164.87(17) . . . . ?
C1 C2 C3 C21 12.6(3) . . . . ?
C2 C3 C4 N2 2.3(3) . . . . ?
C21 C3 C4 N2 177.95(16) . . . . ?
C2 C3 C4 C5 178.70(18) . . . . ?
C21 C3 C4 C5 -5.7(3) . . . . ?
N2 C4 C5 C6 1.3(2) . . . . ?
C3 C4 C5 C6 -175.69(17) . . . . ?
C4 C5 C6 C7 -0.5(2) . . . . ?
C5 C6 C7 N2 -0.5(2) . . . . ?
C5 C6 C7 C8 179.04(17) . . . . ?
N2 C7 C8 C9 -7.7(3) . . . . ?
C6 C7 C8 C9 172.92(18) . . . . ?
N2 C7 C8 C27 171.39(16) . . . . ?
C6 C7 C8 C27 -8.0(3) . . . . ?
C7 C8 C9 N3 0.2(3) . . . . ?
C27 C8 C9 N3 -178.90(16) . . . . ?
C7 C8 C9 C10 -178.98(18) . . . . ?
C27 C8 C9 C10 2.0(3) . . . . ?
N3 C9 C10 C11 -5.9(2) . . . . ?
C8 C9 C10 C11 173.35(17) . . . . ?
C9 C10 C11 C12 7.3(2) . . . . ?
C10 C11 C12 N3 -7.3(2) . . . . ?
C10 C11 C12 C13 172.56(18) . . . . ?
N3 C12 C13 C14 -4.5(3) . . . . ?
C11 C12 C13 C14 175.61(18) . . . . ?
N3 C12 C13 C33 169.40(17) . . . . ?
C11 C12 C13 C33 -10.5(3) . . . . ?
C12 C13 C14 N4 7.4(3) . . . . ?
C33 C13 C14 N4 -166.67(17) . . . . ?
C12 C13 C14 C15 -170.96(19) . . . . ?
C33 C13 C14 C15 14.9(3) . . . . ?
N4 C14 C15 C16 0.0(2) . . . . ?
C13 C14 C15 C16 178.72(18) . . . . ?
C14 C15 C16 C17 1.6(2) . . . . ?
C15 C16 C17 N4 -2.6(2) . . . . ?
C15 C16 C17 C18 175.15(19) . . . . ?
N4 C17 C18 C19 -1.3(3) . . . . ?
C16 C17 C18 C19 -178.57(19) . . . . ?
N4 C17 C18 C39 179.43(17) . . . . ?
C16 C17 C18 C39 2.2(3) . . . . ?
C17 C18 C19 N1 -12.5(3) . . . . ?
C39 C18 C19 N1 166.71(17) . . . . ?
C17 C18 C19 N5 172.60(18) . . . . ?
C39 C18 C19 N5 -8.2(3) . . . . ?
C2 C3 C21 C22 67.4(2) . . . . ?
C4 C3 C21 C22 -108.51(19) . . . . ?
C2 C3 C21 C26 -113.1(2) . . . . ?
C4 C3 C21 C26 71.0(2) . . . . ?
C26 C21 C22 C23 -0.3(3) . . . . ?
C3 C21 C22 C23 179.19(17) . . . . ?
C21 C22 C23 C24 0.3(3) . . . . ?
C22 C23 C24 C25 0.1(3) . . . . ?
C23 C24 C25 C26 -0.4(3) . . . . ?
C24 C25 C26 C21 0.3(3) . . . . ?
C22 C21 C26 C25 0.0(3) . . . . ?
C3 C21 C26 C25 -179.48(17) . . . . ?
C9 C8 C27 C32 74.4(2) . . . . ?
C7 C8 C27 C32 -104.8(2) . . . . ?
C9 C8 C27 C28 -105.5(2) . . . . ?
C7 C8 C27 C28 75.3(2) . . . . ?
C32 C27 C28 C29 0.0(3) . . . . ?
C8 C27 C28 C29 179.93(18) . . . . ?
C27 C28 C29 C30 -0.2(3) . . . . ?
C28 C29 C30 C31 0.4(3) . . . . ?
C29 C30 C31 C32 -0.4(3) . . . . ?
C30 C31 C32 C27 0.2(3) . . . . ?
C28 C27 C32 C31 0.0(3) . . . . ?
C8 C27 C32 C31 -179.93(17) . . . . ?
C14 C13 C33 C38 64.8(2) . . . . ?
C12 C13 C33 C38 -109.8(2) . . . . ?
C14 C13 C33 C34 -115.3(2) . . . . ?
C12 C13 C33 C34 70.1(2) . . . . ?
C38 C33 C34 C35 0.2(3) . . . . ?
C13 C33 C34 C35 -179.69(18) . . . . ?
C33 C34 C35 C36 0.6(3) . . . . ?
C34 C35 C36 C37 -0.8(3) . . . . ?
C35 C36 C37 C38 0.2(3) . . . . ?
C36 C37 C38 C33 0.6(3) . . . . ?
C34 C33 C38 C37 -0.8(3) . . . . ?
C13 C33 C38 C37 179.07(18) . . . . ?
C17 C18 C39 C44 107.4(2) . . . . ?
C19 C18 C39 C44 -71.9(3) . . . . ?
C17 C18 C39 C40 -74.6(2) . . . . ?
C19 C18 C39 C40 106.1(2) . . . . ?
C44 C39 C40 C41 2.0(3) . . . . ?
C18 C39 C40 C41 -176.15(17) . . . . ?
C39 C40 C41 C42 -1.9(3) . . . . ?
C40 C41 C42 C43 0.6(3) . . . . ?
C41 C42 C43 C44 0.7(4) . . . . ?
C40 C39 C44 C43 -0.6(4) . . . . ?
C18 C39 C44 C43 177.5(2) . . . . ?
C42 C43 C44 C39 -0.7(4) . . . . ?
C18 C19 N1 C2 -172.45(18) . . . . ?
N5 C19 N1 C2 2.9(2) . . . . ?
C3 C2 N1 C19 174.25(18) . . . . ?
C1 C2 N1 C19 -3.5(2) . . . . ?
C8 C7 N2 C4 -178.19(17) . . . . ?
C6 C7 N2 C4 1.31(19) . . . . ?
C3 C4 N2 C7 175.39(17) . . . . ?
C5 C4 N2 C7 -1.62(19) . . . . ?
C13 C12 N3 C9 -176.04(18) . . . . ?
C11 C12 N3 C9 3.8(2) . . . . ?
C8 C9 N3 C12 -177.71(17) . . . . ?
C10 C9 N3 C12 1.5(2) . . . . ?
C13 C14 N4 C17 179.63(18) . . . . ?
C15 C14 N4 C17 -1.7(2) . . . . ?
C18 C17 N4 C14 -175.06(18) . . . . ?
C16 C17 N4 C14 2.7(2) . . . . ?
N5 C1 O1 H3B 29.6 . . . . ?
C2 C1 O1 H3B -159.2 . . . . ?
N5 C1 O1 H3 20.1 . . . . ?
C2 C1 O1 H3 -168.7 . . . . ?
N5 C1 O1 H2A 21.2 . . . . ?
C2 C1 O1 H2A -167.7 . . . . ?
N5 C1 O1 H2B 21.7 . . . . ?
C2 C1 O1 H2B -167.1 . . . . ?
O1 C1 N5 N6 8.0(3) . . . . ?
C2 C1 N5 N6 -165.2(2) . . . . ?
O1 C1 N5 C19 172.36(18) . . . . ?
C2 C1 N5 C19 -0.8(2) . . . . ?
N1 C19 N5 N6 162.7(2) . . . . ?
C18 C19 N5 N6 -21.8(3) . . . . ?
N1 C19 N5 C1 -1.3(2) . . . . ?
C18 C19 N5 C1 174.27(18) . . . . ?
