#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/48/2214826.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2214826
loop_
_publ_author_name
'D. Gayathri'
'R. M. Sethukkarasi'
'D. Velmurugan'
'K. Ravikumar'
'G. Periyasami'
_publ_section_title
1-(Benzylideneacetyl)-2-phenyl-1,2,3,5,10,10a-hexahydro-1H-pyrrolo[1,2-b]isoquinoline-3-spiro-3'(2'H)-1H-indol-3'-one
_journal_coeditor_code           PR2006
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3490
_journal_page_last               o3490
_journal_paper_doi               10.1107/S160053680703348X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C34 H28 N2 O2'
_chemical_formula_moiety         'C34 H28 N2 O2'
_chemical_formula_sum            'C34 H28 N2 O2'
_chemical_formula_weight         496.58
_chemical_name_systematic
;
1-(Benzylideneacetyl)-2-phenyl-1,2,3,5,10,10a-hexahydro-
1H-pyrrolo[1,2-b]isoquinoline-3-spiro-3'(2'H)-1H-
indol-3'-one
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.301(4)
_cell_length_b                   14.725(3)
_cell_length_c                   18.583(4)
_cell_measurement_reflns_used    3158
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.38
_cell_volume                     5281.4(19)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       'Bruker SMART APEX'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            44375
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.06
_diffrn_reflns_theta_min         1.38
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2096
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.127
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     685
_refine_ls_number_reflns         6482
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0723P)²+0.0694P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1221
_reflns_number_gt                5365
_reflns_number_total             6482
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pr2006.cif
_cod_data_source_block           I
_cod_original_cell_volume        5281(2)
_cod_database_code               2214826
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
N N1 0.46079(10) 0.50133(13) 0.42242(11) 0.0422(4) Uani d . 1
N N2 0.62533(12) 0.58129(15) 0.45090(14) 0.0587(6) Uani d . 1
H H2 0.6587 0.6178 0.4406 0.070 Uiso calc R 1
O O1 0.59608(10) 0.53639(13) 0.33659(12) 0.0601(5) Uani d . 1
O O2 0.54648(10) 0.24727(13) 0.49803(11) 0.0581(5) Uani d . 1
C C1 0.53286(12) 0.47841(16) 0.44209(13) 0.0403(5) Uani d . 1
C C2 0.53957(12) 0.37561(14) 0.42011(13) 0.0403(5) Uani d . 1
H H2A 0.5671 0.3732 0.3758 0.048 Uiso calc R 1
C C3 0.46564(12) 0.34610(15) 0.40080(13) 0.0402(5) Uani d . 1
H H3 0.4416 0.3289 0.4452 0.048 Uiso calc R 1
C C4 0.43374(12) 0.43268(15) 0.37264(13) 0.0432(5) Uani d . 1
H H4 0.4503 0.4449 0.3237 0.052 Uiso calc R 1
C C5 0.35535(13) 0.43692(18) 0.37494(16) 0.0526(6) Uani d . 1
H H5A 0.3364 0.3977 0.3379 0.063 Uiso calc R 1
H H5B 0.3392 0.4150 0.4212 0.063 Uiso calc R 1
C C6 0.32979(13) 0.53207(18) 0.36345(14) 0.0512(6) Uani d . 1
C C7 0.26194(15) 0.5487(2) 0.34094(17) 0.0632(7) Uani d . 1
H H7 0.2320 0.5000 0.3337 0.076 Uiso calc R 1
C C8 0.23858(17) 0.6352(3) 0.32928(19) 0.0743(9) Uani d . 1
H H8 0.1934 0.6447 0.3136 0.089 Uiso calc R 1
C C9 0.28120(18) 0.7074(3) 0.3405(2) 0.0788(10) Uani d . 1
H H9 0.2650 0.7662 0.3335 0.095 Uiso calc R 1
C C10 0.34873(17) 0.6929(2) 0.36238(18) 0.0659(8) Uani d . 1
H H10 0.3781 0.7423 0.3688 0.079 Uiso calc R 1
C C11 0.37348(14) 0.60568(18) 0.37491(14) 0.0513(6) Uani d . 1
C C12 0.44767(14) 0.59353(17) 0.39869(18) 0.0550(6) Uani d . 1
H H12A 0.4784 0.6081 0.3590 0.066 Uiso calc R 1
H H12B 0.4576 0.6352 0.4378 0.066 Uiso calc R 1
C C13 0.58798(12) 0.53482(15) 0.40082(16) 0.0467(5) Uani d . 1
C C14 0.60314(14) 0.56264(18) 0.52101(16) 0.0542(6) Uani d . 1
C C15 0.62925(19) 0.5944(3) 0.5859(2) 0.0797(10) Uani d . 1
H H15 0.6656 0.6358 0.5873 0.096 Uiso calc R 1
C C16 0.5996(2) 0.5626(3) 0.6476(2) 0.0880(11) Uani d . 1
H H16 0.6165 0.5830 0.6916 0.106 Uiso calc R 1
C C17 0.54584(18) 0.5018(3) 0.64710(18) 0.0746(9) Uani d . 1
H H17 0.5273 0.4810 0.6902 0.090 Uiso calc R 1
C C18 0.51918(14) 0.47146(19) 0.58210(16) 0.0543(6) Uani d . 1
H H18 0.4822 0.4310 0.5811 0.065 Uiso calc R 1
C C19 0.54836(12) 0.50215(16) 0.51922(14) 0.0445(5) Uani d . 1
C C20 0.57527(12) 0.31515(16) 0.47504(13) 0.0434(5) Uani d . 1
C C21 0.64594(12) 0.33979(16) 0.49544(14) 0.0468(6) Uani d . 1
H H21 0.6688 0.3841 0.4688 0.056 Uiso calc R 1
C C22 0.67879(13) 0.30178(18) 0.55021(15) 0.0494(6) Uani d . 1
H H22 0.6552 0.2560 0.5745 0.059 Uiso calc R 1
C C23 0.74793(14) 0.32391(17) 0.57657(14) 0.0497(6) Uani d . 1
C C24 0.78893(15) 0.3894(2) 0.54376(17) 0.0622(7) Uani d . 1
H H24 0.7723 0.4202 0.5037 0.075 Uiso calc R 1
C C25 0.85405(16) 0.4092(2) 0.56991(19) 0.0698(8) Uani d . 1
H H25 0.8810 0.4531 0.5473 0.084 Uiso calc R 1
C C26 0.87937(17) 0.3645(2) 0.62915(19) 0.0689(8) Uani d . 1
H H26 0.9231 0.3784 0.6470 0.083 Uiso calc R 1
C C27 0.83963(17) 0.2994(2) 0.66163(18) 0.0705(8) Uani d . 1
H H27 0.8568 0.2686 0.7015 0.085 Uiso calc R 1
C C28 0.77457(15) 0.2788(2) 0.63601(17) 0.0626(7) Uani d . 1
H H28 0.7483 0.2342 0.6587 0.075 Uiso calc R 1
C C29 0.46236(12) 0.26695(15) 0.34907(13) 0.0419(5) Uani d . 1
C C30 0.49026(15) 0.27250(18) 0.28099(14) 0.0513(6) Uani d . 1
H H30 0.5118 0.3258 0.2663 0.062 Uiso calc R 1
C C31 0.48653(17) 0.1997(2) 0.23432(16) 0.0645(8) Uani d . 1
H H31 0.5053 0.2045 0.1884 0.077 Uiso calc R 1
C C32 0.45541(18) 0.1202(2) 0.2553(2) 0.0717(9) Uani d . 1
H H32 0.4529 0.0712 0.2238 0.086 Uiso calc R 1
C C33 0.42797(19) 0.1138(2) 0.3231(2) 0.0755(9) Uani d . 1
H H33 0.4072 0.0600 0.3380 0.091 Uiso calc R 1
C C34 0.43110(16) 0.18685(19) 0.36949(17) 0.0605(7) Uani d . 1
H H34 0.4118 0.1820 0.4152 0.073 Uiso calc R 1
N N3 0.30081(10) 0.01027(14) 0.48973(11) 0.0431(4) Uani d . 1
N N4 0.13746(12) -0.08201(15) 0.46957(14) 0.0538(5) Uani d . 1
H H4A 0.1044 -0.1181 0.4817 0.065 Uiso calc R 1
O O3 0.17250(10) -0.03839(14) 0.58196(11) 0.0622(5) Uani d . 1
O O4 0.22277(11) 0.26153(13) 0.42423(12) 0.0629(5) Uani d . 1
C C35 0.22770(12) 0.02546(15) 0.47260(13) 0.0404(5) Uani d . 1
C C36 0.21591(12) 0.12748(15) 0.49559(13) 0.0415(5) Uani d . 1
H H36 0.1801 0.1271 0.5330 0.050 Uiso calc R 1
C C37 0.28381(12) 0.15756(16) 0.53213(13) 0.0419(5) Uani d . 1
H H37 0.3125 0.1880 0.4959 0.050 Uiso calc R 1
C C38 0.31875(12) 0.06702(15) 0.55144(13) 0.0423(5) Uani d . 1
H H38 0.2978 0.0420 0.5952 0.051 Uiso calc R 1
C C39 0.39667(14) 0.07150(18) 0.56000(16) 0.0546(6) Uani d . 1
H H39A 0.4155 0.1128 0.5243 0.066 Uiso calc R 1
H H39B 0.4076 0.0957 0.6072 0.066 Uiso calc R 1
C C40 0.43057(12) -0.02032(19) 0.55155(14) 0.0514(6) Uani d . 1
C C41 0.49887(14) -0.0325(2) 0.57275(16) 0.0615(7) Uani d . 1
H H41 0.5236 0.0162 0.5917 0.074 Uiso calc R 1
C C42 0.53040(15) -0.1157(3) 0.56606(17) 0.0717(9) Uani d . 1
H H42 0.5763 -0.1229 0.5803 0.086 Uiso calc R 1
C C43 0.49443(17) -0.1884(3) 0.53838(19) 0.0723(9) Uani d . 1
H H43 0.5158 -0.2448 0.5344 0.087 Uiso calc R 1
C C44 0.42672(16) -0.1777(2) 0.51665(17) 0.0646(8) Uani d . 1
H H44 0.4024 -0.2268 0.4979 0.078 Uiso calc R 1
C C45 0.39465(14) -0.09327(19) 0.52270(14) 0.0517(6) Uani d . 1
C C46 0.31998(14) -0.08480(18) 0.49940(17) 0.0564(7) Uani d . 1
H H46A 0.3133 -0.1173 0.4545 0.068 Uiso calc R 1
H H46B 0.2902 -0.1121 0.5354 0.068 Uiso calc R 1
C C47 0.17671(12) -0.03513(16) 0.51703(15) 0.0459(5) Uani d . 1
C C48 0.15689(13) -0.06487(17) 0.39832(16) 0.0503(6) Uani d . 1
C C49 0.12964(18) -0.1014(2) 0.3361(2) 0.0708(9) Uani d . 1
H H49 0.0932 -0.1426 0.3375 0.085 Uiso calc R 1
C C50 0.1583(2) -0.0746(3) 0.2723(2) 0.0866(11) Uani d . 1
H H50 0.1403 -0.0974 0.2295 0.104 Uiso calc R 1
C C51 0.2136(2) -0.0145(3) 0.26936(19) 0.0803(10) Uani d . 1
H H51 0.2331 0.0010 0.2253 0.096 Uiso calc R 1
C C52 0.23952(17) 0.02232(19) 0.33228(16) 0.0598(7) Uani d . 1
H H52 0.2761 0.0635 0.3308 0.072 Uiso calc R 1
C C53 0.21077(13) -0.00253(16) 0.39683(14) 0.0452(5) Uani d . 1
C C54 0.19103(13) 0.19223(16) 0.43715(14) 0.0446(5) Uani d . 1
C C55 0.12545(13) 0.17004(17) 0.40118(15) 0.0487(6) Uani d . 1
H H55 0.0979 0.1239 0.4199 0.058 Uiso calc R 1
C C56 0.10429(14) 0.21369(19) 0.34293(16) 0.0547(6) Uani d . 1
H H56 0.1323 0.2612 0.3275 0.066 Uiso calc R 1
C C57 0.04232(16) 0.1963(2) 0.29999(16) 0.0574(7) Uani d . 1
C C58 -0.00864(18) 0.1359(2) 0.3203(2) 0.0738(9) Uani d . 1
H H58 -0.0046 0.1045 0.3635 0.089 Uiso calc R 1
C C59 -0.0659(2) 0.1219(2) 0.2767(3) 0.0885(12) Uani d . 1
H H59 -0.1006 0.0821 0.2913 0.106 Uiso calc R 1
C C60 -0.0717(2) 0.1664(3) 0.2121(2) 0.0898(13) Uani d . 1
H H60 -0.1091 0.1548 0.1819 0.108 Uiso calc R 1
C C61 -0.0228(3) 0.2269(4) 0.1927(2) 0.1200(18) Uani d . 1
H H61 -0.0274 0.2585 0.1497 0.144 Uiso calc R 1
C C62 0.0339(2) 0.2423(3) 0.2362(2) 0.0962(13) Uani d . 1
H H62 0.0670 0.2847 0.2221 0.115 Uiso calc R 1
C C63 0.27609(13) 0.22087(17) 0.59528(15) 0.0483(6) Uani d . 1
C C64 0.23529(16) 0.1990(2) 0.65397(16) 0.0600(7) Uani d . 1
H H64 0.2100 0.1452 0.6535 0.072 Uiso calc R 1
C C65 0.2313(2) 0.2548(3) 0.71295(19) 0.0781(10) Uani d . 1
H H65 0.2038 0.2385 0.7519 0.094 Uiso calc R 1
C C66 0.2676(2) 0.3339(3) 0.7146(2) 0.0886(12) Uani d . 1
H H66 0.2651 0.3714 0.7548 0.106 Uiso calc R 1
C C67 0.3075(2) 0.3580(2) 0.6576(3) 0.0885(12) Uani d . 1
H H67 0.3320 0.4124 0.6587 0.106 Uiso calc R 1
C C68 0.31184(16) 0.3019(2) 0.5973(2) 0.0668(8) Uani d . 1
H H68 0.3390 0.3192 0.5584 0.080 Uiso calc R 1
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_publ_flag
C12 N1 C4 113.0(2) n
C12 N1 C1 117.0(2) n
C4 N1 C1 109.5(2) n
C13 N2 C14 112.1(2) ?
C13 N2 H2 124.0 ?
C14 N2 H2 124.0 ?
N1 C1 C19 111.70(19) ?
N1 C1 C13 113.62(19) ?
C19 C1 C13 102.1(2) ?
N1 C1 C2 103.47(17) ?
C19 C1 C2 117.0(2) ?
C13 C1 C2 109.28(19) ?
C20 C2 C3 114.39(19) ?
C20 C2 C1 115.25(19) ?
C3 C2 C1 104.88(18) ?
C20 C2 H2A 107.3 ?
C3 C2 H2A 107.3 ?
C1 C2 H2A 107.3 ?
C4 C3 C29 114.4(2) ?
C4 C3 C2 102.78(18) ?
C29 C3 C2 113.96(19) ?
C4 C3 H3 108.5 ?
C29 C3 H3 108.5 ?
C2 C3 H3 108.5 ?
N1 C4 C3 102.61(18) ?
N1 C4 C5 108.03(19) ?
C3 C4 C5 115.6(2) ?
N1 C4 H4 110.1 ?
C3 C4 H4 110.1 ?
C5 C4 H4 110.1 ?
C6 C5 C4 111.3(2) ?
C6 C5 H5A 109.4 ?
C4 C5 H5A 109.4 ?
C6 C5 H5B 109.4 ?
C4 C5 H5B 109.4 ?
H5A C5 H5B 108.0 ?
C11 C6 C7 118.6(3) ?
C11 C6 C5 120.5(2) ?
C7 C6 C5 121.0(3) ?
C8 C7 C6 121.3(3) ?
C8 C7 H7 119.3 ?
C6 C7 H7 119.3 ?
C9 C8 C7 120.3(3) ?
C9 C8 H8 119.9 ?
C7 C8 H8 119.9 ?
C8 C9 C10 119.6(3) ?
C8 C9 H9 120.2 ?
C10 C9 H9 120.2 ?
C9 C10 C11 121.1(3) ?
C9 C10 H10 119.4 ?
C11 C10 H10 119.4 ?
C10 C11 C6 119.1(3) ?
C10 C11 C12 119.0(3) ?
C6 C11 C12 121.9(2) ?
N1 C12 C11 111.5(2) ?
N1 C12 H12A 109.3 ?
C11 C12 H12A 109.3 ?
N1 C12 H12B 109.3 ?
C11 C12 H12B 109.3 ?
H12A C12 H12B 108.0 ?
O1 C13 N2 126.8(3) ?
O1 C13 C1 126.1(2) ?
N2 C13 C1 107.1(2) ?
C19 C14 C15 121.0(3) ?
C19 C14 N2 109.8(2) ?
C15 C14 N2 129.2(3) ?
C16 C15 C14 117.6(3) ?
C16 C15 H15 121.2 ?
C14 C15 H15 121.2 ?
C15 C16 C17 122.4(3) ?
C15 C16 H16 118.8 ?
C17 C16 H16 118.8 ?
C16 C17 C18 119.8(3) ?
C16 C17 H17 120.1 ?
C18 C17 H17 120.1 ?
C19 C18 C17 118.8(3) ?
C19 C18 H18 120.6 ?
C17 C18 H18 120.6 ?
C18 C19 C14 120.3(2) ?
C18 C19 C1 130.7(2) ?
C14 C19 C1 108.9(2) ?
O2 C20 C21 122.5(2) ?
O2 C20 C2 120.6(2) ?
C21 C20 C2 116.9(2) ?
C22 C21 C20 122.8(2) ?
C22 C21 H21 118.6 ?
C20 C21 H21 118.6 ?
C21 C22 C23 127.0(2) ?
C21 C22 H22 116.5 ?
C23 C22 H22 116.5 ?
C28 C23 C24 118.1(3) ?
C28 C23 C22 119.9(2) ?
C24 C23 C22 122.0(2) ?
C25 C24 C23 120.8(3) ?
C25 C24 H24 119.6 ?
C23 C24 H24 119.6 ?
C26 C25 C24 120.4(3) ?
C26 C25 H25 119.8 ?
C24 C25 H25 119.8 ?
C27 C26 C25 119.4(3) ?
C27 C26 H26 120.3 ?
C25 C26 H26 120.3 ?
C26 C27 C28 120.9(3) ?
C26 C27 H27 119.6 ?
C28 C27 H27 119.6 ?
C27 C28 C23 120.5(3) ?
C27 C28 H28 119.8 ?
C23 C28 H28 119.8 ?
C30 C29 C34 118.3(2) ?
C30 C29 C3 121.5(2) ?
C34 C29 C3 120.2(2) ?
C29 C30 C31 120.7(3) ?
C29 C30 H30 119.7 ?
C31 C30 H30 119.7 ?
C32 C31 C30 120.4(3) ?
C32 C31 H31 119.8 ?
C30 C31 H31 119.8 ?
C33 C32 C31 119.3(3) ?
C33 C32 H32 120.3 ?
C31 C32 H32 120.3 ?
C32 C33 C34 120.2(3) ?
C32 C33 H33 119.9 ?
C34 C33 H33 119.9 ?
C29 C34 C33 121.0(3) ?
C29 C34 H34 119.5 ?
C33 C34 H34 119.5 ?
C46 N3 C38 113.1(2) n
C46 N3 C35 114.7(2) n
C38 N3 C35 108.2(2) n
C47 N4 C48 112.0(2) ?
C47 N4 H4A 124.0 ?
C48 N4 H4A 124.0 ?
N3 C35 C53 111.8(2) ?
N3 C35 C47 113.88(19) ?
C53 C35 C47 101.61(19) ?
N3 C35 C36 103.04(18) ?
C53 C35 C36 118.90(19) ?
C47 C35 C36 108.01(18) ?
C54 C36 C37 113.74(19) ?
C54 C36 C35 116.6(2) ?
C37 C36 C35 105.67(18) ?
C54 C36 H36 106.7 ?
C37 C36 H36 106.7 ?
C35 C36 H36 106.7 ?
C63 C37 C38 113.5(2) ?
C63 C37 C36 115.9(2) ?
C38 C37 C36 103.11(18) ?
C63 C37 H37 108.0 ?
C38 C37 H37 108.0 ?
C36 C37 H37 108.0 ?
N3 C38 C39 110.1(2) ?
N3 C38 C37 102.06(18) ?
C39 C38 C37 115.0(2) ?
N3 C38 H38 109.8 ?
C39 C38 H38 109.8 ?
C37 C38 H38 109.8 ?
C40 C39 C38 112.4(2) ?
C40 C39 H39A 109.1 ?
C38 C39 H39A 109.1 ?
C40 C39 H39B 109.1 ?
C38 C39 H39B 109.1 ?
H39A C39 H39B 107.9 ?
C45 C40 C41 119.0(3) ?
C45 C40 C39 121.1(2) ?
C41 C40 C39 119.8(3) ?
C42 C41 C40 120.7(3) ?
C42 C41 H41 119.7 ?
C40 C41 H41 119.7 ?
C41 C42 C43 120.3(3) ?
C41 C42 H42 119.9 ?
C43 C42 H42 119.9 ?
C42 C43 C44 119.9(3) ?
C42 C43 H43 120.0 ?
C44 C43 H43 120.0 ?
C43 C44 C45 120.0(3) ?
C43 C44 H44 120.0 ?
C45 C44 H44 120.0 ?
C40 C45 C44 120.0(3) ?
C40 C45 C46 121.6(2) ?
C44 C45 C46 118.3(3) ?
N3 C46 C45 110.9(2) ?
N3 C46 H46A 109.5 ?
C45 C46 H46A 109.5 ?
N3 C46 H46B 109.5 ?
C45 C46 H46B 109.5 ?
H46A C46 H46B 108.0 ?
O3 C47 N4 126.3(2) ?
O3 C47 C35 126.2(2) ?
N4 C47 C35 107.4(2) ?
C49 C48 C53 121.8(3) ?
C49 C48 N4 128.4(3) ?
C53 C48 N4 109.8(2) ?
C50 C49 C48 117.4(3) ?
C50 C49 H49 121.3 ?
C48 C49 H49 121.3 ?
C49 C50 C51 121.9(3) ?
C49 C50 H50 119.0 ?
C51 C50 H50 119.0 ?
C52 C51 C50 119.7(3) ?
C52 C51 H51 120.1 ?
C50 C51 H51 120.1 ?
C53 C52 C51 119.2(3) ?
C53 C52 H52 120.4 ?
C51 C52 H52 120.4 ?
C52 C53 C48 119.8(2) ?
C52 C53 C35 131.2(2) ?
C48 C53 C35 109.0(2) ?
O4 C54 C55 122.1(2) ?
O4 C54 C36 120.5(2) ?
C55 C54 C36 117.2(2) ?
C56 C55 C54 122.0(2) ?
C56 C55 H55 119.0 ?
C54 C55 H55 119.0 ?
C55 C56 C57 127.9(3) ?
C55 C56 H56 116.0 ?
C57 C56 H56 116.0 ?
C62 C57 C58 118.0(3) ?
C62 C57 C56 118.8(3) ?
C58 C57 C56 123.2(3) ?
C57 C58 C59 120.4(3) ?
C57 C58 H58 119.8 ?
C59 C58 H58 119.8 ?
C60 C59 C58 120.3(4) ?
C60 C59 H59 119.8 ?
C58 C59 H59 119.8 ?
C61 C60 C59 119.5(4) ?
C61 C60 H60 120.3 ?
C59 C60 H60 120.3 ?
C60 C61 C62 120.6(4) ?
C60 C61 H61 119.7 ?
C62 C61 H61 119.7 ?
C57 C62 C61 121.1(4) ?
C57 C62 H62 119.4 ?
C61 C62 H62 119.4 ?
C68 C63 C64 117.7(3) ?
C68 C63 C37 120.5(3) ?
C64 C63 C37 121.7(2) ?
C65 C64 C63 121.4(3) ?
C65 C64 H64 119.3 ?
C63 C64 H64 119.3 ?
C66 C65 C64 120.2(4) ?
C66 C65 H65 119.9 ?
C64 C65 H65 119.9 ?
C67 C66 C65 119.9(3) ?
C67 C66 H66 120.1 ?
C65 C66 H66 120.1 ?
C66 C67 C68 120.4(3) ?
C66 C67 H67 119.8 ?
C68 C67 H67 119.8 ?
C63 C68 C67 120.3(4) ?
C63 C68 H68 119.8 ?
C67 C68 H68 119.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C12 1.450(3) n
N1 C4 1.466(3) n
N1 C1 1.477(3) n
N2 C13 1.362(4) n
N2 C14 1.399(4) n
N2 H2 0.8600 ?
O1 C13 1.204(3) n
O2 C20 1.221(3) n
C1 C19 1.505(3) n
C1 C13 1.552(4) n
C1 C2 1.573(3) n
C2 C20 1.520(3) n
C2 C3 1.534(3) n
C2 H2A 0.9800 ?
C3 C4 1.510(3) n
C3 C29 1.512(3) n
C3 H3 0.9800 ?
C4 C5 1.515(4) n
C4 H4 0.9800 ?
C5 C6 1.501(4) ?
C5 H5A 0.9700 ?
C5 H5B 0.9700 ?
C6 C11 1.390(4) ?
C6 C7 1.397(4) ?
C7 C8 1.368(4) ?
C7 H7 0.9300 ?
C8 C9 1.361(5) ?
C8 H8 0.9300 ?
C9 C10 1.382(4) ?
C9 H9 0.9300 ?
C10 C11 1.390(4) ?
C10 H10 0.9300 ?
C11 C12 1.509(4) ?
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C14 C19 1.383(4) ?
C14 C15 1.388(4) ?
C15 C16 1.364(6) ?
C15 H15 0.9300 ?
C16 C17 1.371(6) ?
C16 H16 0.9300 ?
C17 C18 1.387(4) ?
C17 H17 0.9300 ?
C18 C19 1.374(4) ?
C18 H18 0.9300 ?
C20 C21 1.462(3) ?
C21 C22 1.323(4) ?
C21 H21 0.9300 ?
C22 C23 1.459(4) ?
C22 H22 0.9300 ?
C23 C28 1.388(4) ?
C23 C24 1.388(4) ?
C24 C25 1.379(4) ?
C24 H24 0.9300 ?
C25 C26 1.372(5) ?
C25 H25 0.9300 ?
C26 C27 1.369(5) ?
C26 H26 0.9300 ?
C27 C28 1.377(4) ?
C27 H27 0.9300 ?
C28 H28 0.9300 ?
C29 C30 1.377(4) ?
C29 C34 1.378(4) ?
C30 C31 1.381(4) ?
C30 H30 0.9300 ?
C31 C32 1.371(5) ?
C31 H31 0.9300 ?
C32 C33 1.371(5) ?
C32 H32 0.9300 ?
C33 C34 1.379(4) ?
C33 H33 0.9300 ?
C34 H34 0.9300 ?
N3 C46 1.459(3) n
N3 C38 1.461(3) n
N3 C35 1.464(3) n
N4 C47 1.352(4) n
N4 C48 1.399(4) n
N4 H4A 0.8600 ?
O3 C47 1.210(3) n
O4 C54 1.214(3) n
C35 C53 1.503(4) n
C35 C47 1.564(3) n
C35 C36 1.578(3) n
C36 C54 1.523(3) n
C36 C37 1.541(3) n
C36 H36 0.9800 ?
C37 C63 1.506(3) n
C37 C38 1.537(3) n
C37 H37 0.9800 ?
C38 C39 1.514(3) n
C38 H38 0.9800 ?
C39 C40 1.510(4) ?
C39 H39A 0.9700 ?
C39 H39B 0.9700 ?
C40 C45 1.386(4) ?
C40 C41 1.387(4) ?
C41 C42 1.374(5) ?
C41 H41 0.9300 ?
C42 C43 1.376(5) ?
C42 H42 0.9300 ?
C43 C44 1.377(5) ?
C43 H43 0.9300 ?
C44 C45 1.393(4) ?
C44 H44 0.9300 ?
C45 C46 1.510(4) ?
C46 H46A 0.9700 ?
C46 H46B 0.9700 ?
C48 C49 1.380(4) ?
C48 C53 1.388(4) ?
C49 C50 1.367(6) ?
C49 H49 0.9300 ?
C50 C51 1.387(6) ?
C50 H50 0.9300 ?
C51 C52 1.383(5) ?
C51 H51 0.9300 ?
C52 C53 1.371(4) ?
C52 H52 0.9300 ?
C54 C55 1.468(4) ?
C55 C56 1.323(4) ?
C55 H55 0.9300 ?
C56 C57 1.460(4) ?
C56 H56 0.9300 ?
C57 C62 1.375(5) ?
C57 C58 1.378(5) ?
C58 C59 1.386(5) ?
C58 H58 0.9300 ?
C59 C60 1.373(6) ?
C59 H59 0.9300 ?
C60 C61 1.346(7) ?
C60 H60 0.9300 ?
C61 C62 1.379(6) ?
C61 H61 0.9300 ?
C62 H62 0.9300 ?
C63 C68 1.379(4) ?
C63 C64 1.383(4) ?
C64 C65 1.372(5) ?
C64 H64 0.9300 ?
C65 C66 1.359(6) ?
C65 H65 0.9300 ?
C66 C67 1.357(6) ?
C66 H66 0.9300 ?
C67 C68 1.395(5) ?
C67 H67 0.9300 ?
C68 H68 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2 O4 3_565 0.86 2.19 3.023(3) 164.2
N4 H4A O2 3_455 0.86 2.23 3.047(3) 159.3
C2 H2A O1 . 0.98 2.57 3.034(3) 108.8
C12 H12A O1 . 0.97 2.54 3.201(3) 125.4
C37 H37 O4 . 0.98 2.44 2.784(3) 100.2
C56 H56 O4 . 0.93 2.51 2.830(4) 100.7
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
C12 N1 C1 C19 85.8(3)
C4 N1 C1 C19 -143.9(2)
C12 N1 C1 C13 -29.1(3)
C4 N1 C1 C13 101.2(2)
C12 N1 C1 C2 -147.5(2)
C4 N1 C1 C2 -17.2(2)
N1 C1 C2 C20 -135.5(2)
C19 C1 C2 C20 -12.2(3)
C13 C1 C2 C20 103.1(2)
N1 C1 C2 C3 -8.8(2)
C19 C1 C2 C3 114.5(2)
C13 C1 C2 C3 -130.2(2)
C20 C2 C3 C4 157.62(19)
C1 C2 C3 C4 30.4(2)
C20 C2 C3 C29 -78.0(3)
C1 C2 C3 C29 154.8(2)
C12 N1 C4 C3 169.2(2)
C1 N1 C4 C3 36.9(2)
C12 N1 C4 C5 -68.2(3)
C1 N1 C4 C5 159.5(2)
C29 C3 C4 N1 -164.70(19)
C2 C3 C4 N1 -40.6(2)
C29 C3 C4 C5 78.0(3)
C2 C3 C4 C5 -157.9(2)
N1 C4 C5 C6 51.7(3)
C3 C4 C5 C6 166.0(2)
C4 C5 C6 C11 -20.3(4)
C4 C5 C6 C7 159.6(3)
C11 C6 C7 C8 0.9(5)
C5 C6 C7 C8 -179.0(3)
C6 C7 C8 C9 -0.9(5)
C7 C8 C9 C10 1.3(6)
C8 C9 C10 C11 -1.6(5)
C9 C10 C11 C6 1.6(5)
C9 C10 C11 C12 180.0(3)
C7 C6 C11 C10 -1.2(4)
C5 C6 C11 C10 178.7(3)
C7 C6 C11 C12 -179.5(3)
C5 C6 C11 C12 0.3(4)
C4 N1 C12 C11 47.0(3)
C1 N1 C12 C11 175.6(2)
C10 C11 C12 N1 169.0(3)
C6 C11 C12 N1 -12.7(4)
C14 N2 C13 O1 -178.8(3)
C14 N2 C13 C1 0.8(3)
N1 C1 C13 O1 -60.6(3)
C19 C1 C13 O1 179.0(2)
C2 C1 C13 O1 54.4(3)
N1 C1 C13 N2 119.8(2)
C19 C1 C13 N2 -0.6(2)
C2 C1 C13 N2 -125.2(2)
C13 N2 C14 C19 -0.6(3)
C13 N2 C14 C15 178.0(3)
C19 C14 C15 C16 1.0(5)
N2 C14 C15 C16 -177.4(3)
C14 C15 C16 C17 -0.2(6)
C15 C16 C17 C18 -0.8(6)
C16 C17 C18 C19 1.1(5)
C17 C18 C19 C14 -0.3(4)
C17 C18 C19 C1 177.0(3)
C15 C14 C19 C18 -0.7(4)
N2 C14 C19 C18 178.0(2)
C15 C14 C19 C1 -178.6(3)
N2 C14 C19 C1 0.1(3)
N1 C1 C19 C18 61.0(3)
C13 C1 C19 C18 -177.2(3)
C2 C1 C19 C18 -58.0(3)
N1 C1 C19 C14 -121.5(2)
C13 C1 C19 C14 0.3(2)
C2 C1 C19 C14 119.6(2)
C3 C2 C20 O2 2.9(3)
C1 C2 C20 O2 124.6(2)
C3 C2 C20 C21 179.9(2)
C1 C2 C20 C21 -58.4(3)
O2 C20 C21 C22 -13.8(4)
C2 C20 C21 C22 169.3(2)
C20 C21 C22 C23 -177.4(2)
C21 C22 C23 C28 178.6(3)
C21 C22 C23 C24 -1.6(5)
C28 C23 C24 C25 -0.4(5)
C22 C23 C24 C25 179.8(3)
C23 C24 C25 C26 -0.2(5)
C24 C25 C26 C27 0.7(5)
C25 C26 C27 C28 -0.5(5)
C26 C27 C28 C23 -0.1(5)
C24 C23 C28 C27 0.5(5)
C22 C23 C28 C27 -179.7(3)
C4 C3 C29 C30 56.8(3)
C2 C3 C29 C30 -61.0(3)
C4 C3 C29 C34 -123.3(3)
C2 C3 C29 C34 118.8(3)
C34 C29 C30 C31 0.4(4)
C3 C29 C30 C31 -179.7(3)
C29 C30 C31 C32 -0.5(5)
C30 C31 C32 C33 0.0(5)
C31 C32 C33 C34 0.6(6)
C30 C29 C34 C33 0.2(5)
C3 C29 C34 C33 -179.6(3)
C32 C33 C34 C29 -0.8(6)
C46 N3 C35 C53 -72.9(3)
C38 N3 C35 C53 159.84(19)
C46 N3 C35 C47 41.5(3)
C38 N3 C35 C47 -85.7(2)
C46 N3 C35 C36 158.3(2)
C38 N3 C35 C36 31.0(2)
N3 C35 C36 C54 121.4(2)
C53 C35 C36 C54 -2.9(3)
C47 C35 C36 C54 -117.8(2)
N3 C35 C36 C37 -6.1(2)
C53 C35 C36 C37 -130.4(2)
C47 C35 C36 C37 114.7(2)
C54 C36 C37 C63 87.3(2)
C35 C36 C37 C63 -143.5(2)
C54 C36 C37 C38 -148.1(2)
C35 C36 C37 C38 -18.9(2)
C46 N3 C38 C39 65.6(3)
C35 N3 C38 C39 -166.3(2)
C46 N3 C38 C37 -171.9(2)
C35 N3 C38 C37 -43.7(2)
C63 C37 C38 N3 163.32(19)
C36 C37 C38 N3 37.1(2)
C63 C37 C38 C39 -77.6(3)
C36 C37 C38 C39 156.2(2)
N3 C38 C39 C40 -44.3(3)
C37 C38 C39 C40 -158.9(2)
C38 C39 C40 C45 14.0(4)
C38 C39 C40 C41 -166.2(2)
C45 C40 C41 C42 -0.7(4)
C39 C40 C41 C42 179.4(3)
C40 C41 C42 C43 -0.2(5)
C41 C42 C43 C44 0.6(5)
C42 C43 C44 C45 0.0(5)
C41 C40 C45 C44 1.3(4)
C39 C40 C45 C44 -178.9(3)
C41 C40 C45 C46 179.3(3)
C39 C40 C45 C46 -0.9(4)
C43 C44 C45 C40 -0.9(4)
C43 C44 C45 C46 -179.0(3)
C38 N3 C46 C45 -50.7(3)
C35 N3 C46 C45 -175.4(2)
C40 C45 C46 N3 18.2(4)
C44 C45 C46 N3 -163.8(3)
C48 N4 C47 O3 -178.2(3)
C48 N4 C47 C35 2.8(3)
N3 C35 C47 O3 57.4(3)
C53 C35 C47 O3 177.8(3)
C36 C35 C47 O3 -56.4(3)
N3 C35 C47 N4 -123.6(2)
C53 C35 C47 N4 -3.2(2)
C36 C35 C47 N4 122.6(2)
C47 N4 C48 C49 178.8(3)
C47 N4 C48 C53 -1.1(3)
C53 C48 C49 C50 0.7(5)
N4 C48 C49 C50 -179.1(3)
C48 C49 C50 C51 1.2(6)
C49 C50 C51 C52 -2.2(6)
C50 C51 C52 C53 1.1(5)
C51 C52 C53 C48 0.8(4)
C51 C52 C53 C35 179.9(3)
C49 C48 C53 C52 -1.8(4)
N4 C48 C53 C52 178.1(2)
C49 C48 C53 C35 179.0(3)
N4 C48 C53 C35 -1.2(3)
N3 C35 C53 C52 -54.7(3)
C47 C35 C53 C52 -176.6(3)
C36 C35 C53 C52 65.2(4)
N3 C35 C53 C48 124.4(2)
C47 C35 C53 C48 2.6(2)
C36 C35 C53 C48 -115.7(2)
C37 C36 C54 O4 -2.0(3)
C35 C36 C54 O4 -125.4(3)
C37 C36 C54 C55 -178.1(2)
C35 C36 C54 C55 58.5(3)
O4 C54 C55 C56 14.1(4)
C36 C54 C55 C56 -169.8(2)
C54 C55 C56 C57 177.0(3)
C55 C56 C57 C62 -172.2(3)
C55 C56 C57 C58 8.0(5)
C62 C57 C58 C59 0.8(5)
C56 C57 C58 C59 -179.4(3)
C57 C58 C59 C60 1.5(6)
C58 C59 C60 C61 -2.9(7)
C59 C60 C61 C62 2.0(8)
C58 C57 C62 C61 -1.8(7)
C56 C57 C62 C61 178.4(4)
C60 C61 C62 C57 0.4(9)
C38 C37 C63 C68 114.1(3)
C36 C37 C63 C68 -126.8(3)
C38 C37 C63 C64 -63.6(3)
C36 C37 C63 C64 55.4(3)
C68 C63 C64 C65 -1.2(4)
C37 C63 C64 C65 176.6(3)
C63 C64 C65 C66 0.4(5)
C64 C65 C66 C67 0.5(6)
C65 C66 C67 C68 -0.4(6)
C64 C63 C68 C67 1.2(4)
C37 C63 C68 C67 -176.6(3)
C66 C67 C68 C63 -0.4(6)
