#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/49/2224969.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_2224969
loop_
_publ_author_name
'Zhang, Xin'
'Huang, Meng'
'Du, Cong'
'Han, Junjing'
_publ_section_title
;Ethyl
 2-{[(1Z)-(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-ylidene)(p-tolyl)methyl]amino}-3-phenylpropanoate
;
_journal_coeditor_code           HB5268
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o273
_journal_paper_doi               10.1107/S1600536809054865
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C29 H29 N3 O3'
_chemical_formula_moiety         'C29 H29 N3 O3'
_chemical_formula_sum            'C29 H29 N3 O3'
_chemical_formula_weight         467.55
_chemical_name_systematic
;
Ethyl 2-{[(1Z)-(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-
4-ylidene)(p-tolyl)methyl]amino}-3-phenylpropanoate
;
_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                101.869(2)
_cell_angle_beta                 97.923(2)
_cell_angle_gamma                112.861(2)
_cell_formula_units_Z            4
_cell_length_a                   11.0637(11)
_cell_length_b                   13.2746(14)
_cell_length_c                   20.299(2)
_cell_measurement_reflns_used    2516
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.16
_cell_measurement_theta_min      2.27
_cell_volume                     2608.8(5)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART CCD'
_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  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13503
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1999)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.188
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     636
_refine_ls_number_reflns         9153
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0484
_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)+(0.0568P)²+0.1678P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1319
_reflns_number_gt                5450
_reflns_number_total             9153
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5268.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2224969
_cod_database_fobs_code          2224969
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.71923(17) 0.81845(14) 0.49334(9) 0.0766(5) Uani d . 1 . .
O O2 0.3638(2) 0.8629(2) 0.49767(10) 0.1062(7) Uani d . 1 . .
O O3 0.29842(17) 0.92431(15) 0.59120(9) 0.0799(5) Uani d . 1 . .
O O4 0.24307(14) 0.80519(12) 1.00473(7) 0.0631(4) Uani d . 1 . .
O O5 -0.08684(17) 0.87650(15) 1.01365(8) 0.0776(5) Uani d . 1 . .
O O6 -0.25145(15) 0.84962(13) 0.92501(7) 0.0649(4) Uani d . 1 . .
N N1 0.77524(18) 0.66606(16) 0.49565(9) 0.0609(5) Uani d . 1 . .
N N2 0.74399(19) 0.57817(16) 0.52761(9) 0.0616(5) Uani d . 1 . .
N N3 0.55387(18) 0.82573(16) 0.57946(9) 0.0617(5) Uani d . 1 . .
H H3A 0.5857 0.8429 0.5449 0.074 Uiso calc R 1 . .
N N4 0.29698(16) 0.65042(14) 0.99683(9) 0.0513(4) Uani d . 1 . .
N N5 0.23374(18) 0.53247(14) 0.96488(9) 0.0547(5) Uani d . 1 . .
N N6 -0.01134(18) 0.73294(15) 0.92980(9) 0.0598(5) Uani d . 1 . .
H H6 0.0499 0.7785 0.9666 0.072 Uiso calc R 1 . .
C C1 0.9533(3) 0.6259(2) 0.45793(15) 0.0834(8) Uani d . 1 . .
H H1 0.9543 0.5868 0.4910 0.100 Uiso calc R 1 . .
C C2 1.0407(3) 0.6352(3) 0.4136(2) 0.1111(11) Uani d . 1 . .
H H2 1.1001 0.6016 0.4171 0.133 Uiso calc R 1 . .
C C3 1.0397(4) 0.6932(3) 0.3653(2) 0.1202(13) Uani d . 1 . .
H H3 1.0988 0.6993 0.3364 0.144 Uiso calc R 1 . .
C C4 0.9522(3) 0.7420(3) 0.35953(17) 0.1045(10) Uani d . 1 . .
H H4 0.9515 0.7809 0.3263 0.125 Uiso calc R 1 . .
C C5 0.8643(3) 0.7342(2) 0.40263(14) 0.0801(8) Uani d . 1 . .
H H5 0.8050 0.7679 0.3987 0.096 Uiso calc R 1 . .
C C6 0.8655(2) 0.6759(2) 0.45169(13) 0.0667(7) Uani d . 1 . .
C C7 0.7118(2) 0.7346(2) 0.51423(11) 0.0591(6) Uani d . 1 . .
C C8 0.6389(2) 0.68835(18) 0.56273(10) 0.0520(5) Uani d . 1 . .
C C9 0.6635(2) 0.59172(19) 0.56667(11) 0.0551(6) Uani d . 1 . .
C C10 0.6086(3) 0.5064(2) 0.60524(12) 0.0732(7) Uani d . 1 . .
H H10A 0.6391 0.4479 0.5940 0.110 Uiso calc R 1 . .
H H10B 0.5116 0.4729 0.5923 0.110 Uiso calc R 1 . .
H H10C 0.6397 0.5435 0.6542 0.110 Uiso calc R 1 . .
C C11 0.5662(2) 0.73839(18) 0.59647(10) 0.0508(5) Uani d . 1 . .
C C12 0.5048(2) 0.69619(18) 0.65205(10) 0.0497(5) Uani d . 1 . .
C C13 0.3756(2) 0.6121(2) 0.63623(11) 0.0634(6) Uani d . 1 . .
H H13 0.3223 0.5857 0.5912 0.076 Uiso calc R 1 . .
C C14 0.3246(3) 0.5665(2) 0.68735(12) 0.0720(7) Uani d . 1 . .
H H14 0.2368 0.5095 0.6760 0.086 Uiso calc R 1 . .
C C15 0.3998(3) 0.6030(2) 0.75424(12) 0.0689(7) Uani d . 1 . .
C C16 0.5282(3) 0.6890(2) 0.76938(12) 0.0757(7) Uani d . 1 . .
H H16 0.5810 0.7159 0.8145 0.091 Uiso calc R 1 . .
C C17 0.5807(2) 0.7364(2) 0.71958(11) 0.0648(6) Uani d . 1 . .
H H17 0.6672 0.7954 0.7315 0.078 Uiso calc R 1 . .
C C18 0.3415(3) 0.5521(3) 0.80965(15) 0.1137(11) Uani d . 1 . .
H H18A 0.2749 0.5776 0.8210 0.170 Uiso d R 1 . .
H H18B 0.4126 0.5760 0.8504 0.170 Uiso d R 1 . .
H H18C 0.3003 0.4704 0.7925 0.170 Uiso d R 1 . .
C C19 0.4935(2) 0.89585(19) 0.61186(11) 0.0596(6) Uani d . 1 . .
H H19 0.4596 0.8685 0.6500 0.071 Uiso calc R 1 . .
C C20 0.5985(2) 1.0210(2) 0.64057(12) 0.0695(7) Uani d . 1 . .
H H20A 0.6400 1.0446 0.6039 0.083 Uiso calc R 1 . .
H H20B 0.5525 1.0681 0.6543 0.083 Uiso calc R 1 . .
C C21 0.7078(2) 1.04170(19) 0.70174(12) 0.0595(6) Uani d . 1 . .
C C22 0.8205(2) 1.0246(2) 0.69331(13) 0.0709(7) Uani d . 1 . .
H H22 0.8304 0.9999 0.6489 0.085 Uiso calc R 1 . .
C C23 0.9190(3) 1.0439(2) 0.75043(16) 0.0812(8) Uani d . 1 . .
H H23 0.9946 1.0320 0.7443 0.097 Uiso calc R 1 . .
C C24 0.9055(3) 1.0806(2) 0.81618(15) 0.0781(8) Uani d . 1 . .
H H24 0.9723 1.0943 0.8545 0.094 Uiso calc R 1 . .
C C25 0.7943(3) 1.0970(2) 0.82516(14) 0.0806(8) Uani d . 1 . .
H H25 0.7846 1.1215 0.8696 0.097 Uiso calc R 1 . .
C C26 0.6963(3) 1.0772(2) 0.76821(13) 0.0758(7) Uani d . 1 . .
H H26 0.6202 1.0880 0.7748 0.091 Uiso calc R 1 . .
C C27 0.3774(3) 0.8892(2) 0.55943(14) 0.0695(7) Uani d . 1 . .
C C28 0.1891(3) 0.9351(3) 0.54875(16) 0.0943(9) Uani d . 1 . .
H H28A 0.1342 0.8644 0.5125 0.113 Uiso calc R 1 . .
H H28B 0.2257 0.9955 0.5271 0.113 Uiso calc R 1 . .
C C29 0.1067(3) 0.9618(3) 0.59471(19) 0.1302(13) Uani d . 1 . .
H H29A 0.0646 0.8986 0.6126 0.195 Uiso calc R 1 . .
H H29B 0.0384 0.9759 0.5690 0.195 Uiso calc R 1 . .
H H29C 0.1636 1.0284 0.6325 0.195 Uiso calc R 1 . .
C C30 0.4752(2) 0.7986(2) 1.09284(12) 0.0640(6) Uani d . 1 . .
H H30 0.4203 0.8358 1.1002 0.077 Uiso calc R 1 . .
C C31 0.6034(3) 0.8419(2) 1.13540(14) 0.0793(7) Uani d . 1 . .
H H31 0.6349 0.9087 1.1714 0.095 Uiso calc R 1 . .
C C32 0.6846(3) 0.7867(3) 1.12470(16) 0.0868(8) Uani d . 1 . .
H H32 0.7700 0.8153 1.1541 0.104 Uiso calc R 1 . .
C C33 0.6400(3) 0.6900(3) 1.07104(16) 0.0837(8) Uani d . 1 . .
H H33 0.6958 0.6537 1.0633 0.100 Uiso calc R 1 . .
C C34 0.5129(2) 0.6461(2) 1.02831(13) 0.0667(6) Uani d . 1 . .
H H34 0.4828 0.5801 0.9918 0.080 Uiso calc R 1 . .
C C35 0.4297(2) 0.70014(18) 1.03960(11) 0.0527(5) Uani d . 1 . .
C C36 0.2138(2) 0.70135(18) 0.98212(10) 0.0486(5) Uani d . 1 . .
C C37 0.0921(2) 0.61086(17) 0.93655(10) 0.0472(5) Uani d . 1 . .
C C38 0.1131(2) 0.50964(17) 0.92975(10) 0.0503(5) Uani d . 1 . .
C C39 0.0195(2) 0.38911(18) 0.89275(12) 0.0700(7) Uani d . 1 . .
H H39A 0.0112 0.3770 0.8437 0.105 Uiso calc R 1 . .
H H39B -0.0676 0.3725 0.9024 0.105 Uiso calc R 1 . .
H H39C 0.0544 0.3399 0.9082 0.105 Uiso calc R 1 . .
C C40 -0.0169(2) 0.62915(18) 0.90837(10) 0.0486(5) Uani d . 1 . .
C C41 -0.1392(2) 0.54022(17) 0.85620(10) 0.0490(5) Uani d . 1 . .
C C42 -0.1335(2) 0.4956(2) 0.78968(11) 0.0642(6) Uani d . 1 . .
H H42 -0.0510 0.5193 0.7775 0.077 Uiso calc R 1 . .
C C43 -0.2494(3) 0.4158(2) 0.74106(12) 0.0730(7) Uani d . 1 . .
H H43 -0.2436 0.3865 0.6965 0.088 Uiso calc R 1 . .
C C44 -0.3731(3) 0.3787(2) 0.75699(13) 0.0706(7) Uani d . 1 . .
C C45 -0.3777(2) 0.4225(2) 0.82360(14) 0.0722(7) Uani d . 1 . .
H H45 -0.4601 0.3975 0.8358 0.087 Uiso calc R 1 . .
C C46 -0.2635(2) 0.5025(2) 0.87262(12) 0.0620(6) Uani d . 1 . .
H H46 -0.2698 0.5314 0.9171 0.074 Uiso calc R 1 . .
C C47 -0.5008(3) 0.2919(2) 0.70330(15) 0.1088(11) Uani d . 1 . .
H H47A -0.4778 0.2659 0.6612 0.163 Uiso calc R 1 . .
H H47B -0.5607 0.3265 0.6942 0.163 Uiso calc R 1 . .
H H47C -0.5448 0.2283 0.7206 0.163 Uiso calc R 1 . .
C C48 -0.0969(2) 0.77755(18) 0.89797(11) 0.0546(6) Uani d . 1 . .
H H48 -0.1760 0.7146 0.8644 0.065 Uiso calc R 1 . .
C C49 -0.0201(2) 0.86357(19) 0.86083(12) 0.0654(6) Uani d . 1 . .
H H49A -0.0807 0.8914 0.8401 0.078 Uiso calc R 1 . .
H H49B 0.0539 0.9282 0.8950 0.078 Uiso calc R 1 . .
C C50 0.0360(2) 0.81547(19) 0.80509(12) 0.0611(6) Uani d . 1 . .
C C51 0.1668(3) 0.8278(2) 0.81830(15) 0.0867(8) Uani d . 1 . .
H H51 0.2226 0.8663 0.8626 0.104 Uiso calc R 1 . .
C C52 0.2163(3) 0.7838(3) 0.76661(19) 0.1075(10) Uani d . 1 . .
H H52 0.3050 0.7924 0.7764 0.129 Uiso calc R 1 . .
C C53 0.1357(4) 0.7275(3) 0.70104(17) 0.1027(10) Uani d . 1 . .
H H53 0.1699 0.6993 0.6660 0.123 Uiso calc R 1 . .
C C54 0.0062(3) 0.7131(3) 0.68762(14) 0.0938(9) Uani d . 1 . .
H H54 -0.0496 0.6736 0.6434 0.113 Uiso calc R 1 . .
C C55 -0.0432(3) 0.7568(2) 0.73906(13) 0.0792(7) Uani d . 1 . .
H H55 -0.1326 0.7464 0.7290 0.095 Uiso calc R 1 . .
C C56 -0.1432(2) 0.83904(18) 0.95348(12) 0.0559(6) Uani d . 1 . .
C C57 -0.3000(2) 0.9187(2) 0.96945(12) 0.0712(7) Uani d . 1 . .
H H57A -0.2362 0.9984 0.9827 0.085 Uiso calc R 1 . .
H H57B -0.3104 0.8949 1.0112 0.085 Uiso calc R 1 . .
C C58 -0.4329(3) 0.9022(2) 0.92927(14) 0.0898(8) Uani d . 1 . .
H H58A -0.4228 0.9202 0.8863 0.135 Uiso calc R 1 . .
H H58B -0.4643 0.9516 0.9558 0.135 Uiso calc R 1 . .
H H58C -0.4973 0.8244 0.9199 0.135 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C27 O3 C28 . . 118.0(2) ?
C56 O6 C57 . . 117.64(17) ?
C7 N1 N2 . . 111.98(17) ?
C7 N1 C6 . . 128.7(2) ?
N2 N1 C6 . . 119.28(19) ?
C9 N2 N1 . . 106.36(17) ?
C11 N3 C19 . . 128.05(18) ?
C11 N3 H3A . . 116.0 ?
C19 N3 H3A . . 116.0 ?
C36 N4 N5 . . 111.77(16) ?
C36 N4 C35 . . 129.02(18) ?
N5 N4 C35 . . 119.18(16) ?
C38 N5 N4 . . 106.38(16) ?
C40 N6 C48 . . 127.15(18) ?
C40 N6 H6 . . 116.4 ?
C48 N6 H6 . . 116.4 ?
C6 C1 C2 . . 118.7(3) ?
C6 C1 H1 . . 120.7 ?
C2 C1 H1 . . 120.7 ?
C3 C2 C1 . . 120.7(3) ?
C3 C2 H2 . . 119.7 ?
C1 C2 H2 . . 119.7 ?
C4 C3 C2 . . 120.1(3) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C3 C4 C5 . . 120.5(3) ?
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
C6 C5 C4 . . 119.4(3) ?
C6 C5 H5 . . 120.3 ?
C4 C5 H5 . . 120.3 ?
C1 C6 C5 . . 120.6(2) ?
C1 C6 N1 . . 119.3(2) ?
C5 C6 N1 . . 120.1(2) ?
O1 C7 N1 . . 126.4(2) ?
O1 C7 C8 . . 129.1(2) ?
N1 C7 C8 . . 104.5(2) ?
C11 C8 C9 . . 132.3(2) ?
C11 C8 C7 . . 122.2(2) ?
C9 C8 C7 . . 105.55(18) ?
N2 C9 C8 . . 111.57(19) ?
N2 C9 C10 . . 118.3(2) ?
C8 C9 C10 . . 130.1(2) ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
N3 C11 C8 . . 119.18(19) ?
N3 C11 C12 . . 120.08(18) ?
C8 C11 C12 . . 120.7(2) ?
C13 C12 C17 . . 119.0(2) ?
C13 C12 C11 . . 120.66(18) ?
C17 C12 C11 . . 120.16(19) ?
C12 C13 C14 . . 119.9(2) ?
C12 C13 H13 . . 120.0 ?
C14 C13 H13 . . 120.0 ?
C15 C14 C13 . . 121.8(2) ?
C15 C14 H14 . . 119.1 ?
C13 C14 H14 . . 119.1 ?
C14 C15 C16 . . 117.4(2) ?
C14 C15 C18 . . 121.0(3) ?
C16 C15 C18 . . 121.7(2) ?
C15 C16 C17 . . 121.9(2) ?
C15 C16 H16 . . 119.1 ?
C17 C16 H16 . . 119.1 ?
C16 C17 C12 . . 119.9(2) ?
C16 C17 H17 . . 120.0 ?
C12 C17 H17 . . 120.0 ?
C15 C18 H18A . . 109.5 ?
C15 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C15 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
N3 C19 C27 . . 110.08(19) ?
N3 C19 C20 . . 110.38(19) ?
C27 C19 C20 . . 108.61(18) ?
N3 C19 H19 . . 109.2 ?
C27 C19 H19 . . 109.2 ?
C20 C19 H19 . . 109.2 ?
C21 C20 C19 . . 113.60(19) ?
C21 C20 H20A . . 108.8 ?
C19 C20 H20A . . 108.8 ?
C21 C20 H20B . . 108.8 ?
C19 C20 H20B . . 108.8 ?
H20A C20 H20B . . 107.7 ?
C26 C21 C22 . . 118.0(2) ?
C26 C21 C20 . . 120.3(2) ?
C22 C21 C20 . . 121.7(2) ?
C21 C22 C23 . . 120.4(2) ?
C21 C22 H22 . . 119.8 ?
C23 C22 H22 . . 119.8 ?
C24 C23 C22 . . 120.2(3) ?
C24 C23 H23 . . 119.9 ?
C22 C23 H23 . . 119.9 ?
C25 C24 C23 . . 119.9(3) ?
C25 C24 H24 . . 120.0 ?
C23 C24 H24 . . 120.0 ?
C24 C25 C26 . . 119.7(3) ?
C24 C25 H25 . . 120.2 ?
C26 C25 H25 . . 120.2 ?
C25 C26 C21 . . 121.8(2) ?
C25 C26 H26 . . 119.1 ?
C21 C26 H26 . . 119.1 ?
O2 C27 O3 . . 124.7(2) ?
O2 C27 C19 . . 124.7(2) ?
O3 C27 C19 . . 110.4(2) ?
O3 C28 C29 . . 107.6(2) ?
O3 C28 H28A . . 110.2 ?
C29 C28 H28A . . 110.2 ?
O3 C28 H28B . . 110.2 ?
C29 C28 H28B . . 110.2 ?
H28A C28 H28B . . 108.5 ?
C28 C29 H29A . . 109.5 ?
C28 C29 H29B . . 109.5 ?
H29A C29 H29B . . 109.5 ?
C28 C29 H29C . . 109.5 ?
H29A C29 H29C . . 109.5 ?
H29B C29 H29C . . 109.5 ?
C35 C30 C31 . . 119.5(2) ?
C35 C30 H30 . . 120.2 ?
C31 C30 H30 . . 120.2 ?
C32 C31 C30 . . 120.3(3) ?
C32 C31 H31 . . 119.9 ?
C30 C31 H31 . . 119.9 ?
C33 C32 C31 . . 120.0(3) ?
C33 C32 H32 . . 120.0 ?
C31 C32 H32 . . 120.0 ?
C32 C33 C34 . . 120.3(3) ?
C32 C33 H33 . . 119.9 ?
C34 C33 H33 . . 119.9 ?
C33 C34 C35 . . 120.0(2) ?
C33 C34 H34 . . 120.0 ?
C35 C34 H34 . . 120.0 ?
C30 C35 C34 . . 119.9(2) ?
C30 C35 N4 . . 121.19(19) ?
C34 C35 N4 . . 118.9(2) ?
O4 C36 N4 . . 125.45(19) ?
O4 C36 C37 . . 129.52(18) ?
N4 C36 C37 . . 105.02(17) ?
C40 C37 C38 . . 132.1(2) ?
C40 C37 C36 . . 122.48(18) ?
C38 C37 C36 . . 105.47(17) ?
N5 C38 C37 . . 111.32(19) ?
N5 C38 C39 . . 118.58(19) ?
C37 C38 C39 . . 130.0(2) ?
C38 C39 H39A . . 109.5 ?
C38 C39 H39B . . 109.5 ?
H39A C39 H39B . . 109.5 ?
C38 C39 H39C . . 109.5 ?
H39A C39 H39C . . 109.5 ?
H39B C39 H39C . . 109.5 ?
N6 C40 C37 . . 118.00(19) ?
N6 C40 C41 . . 117.83(18) ?
C37 C40 C41 . . 124.17(18) ?
C42 C41 C46 . . 118.2(2) ?
C42 C41 C40 . . 121.3(2) ?
C46 C41 C40 . . 120.46(19) ?
C41 C42 C43 . . 120.4(2) ?
C41 C42 H42 . . 119.8 ?
C43 C42 H42 . . 119.8 ?
C44 C43 C42 . . 121.5(2) ?
C44 C43 H43 . . 119.2 ?
C42 C43 H43 . . 119.2 ?
C43 C44 C45 . . 117.6(2) ?
C43 C44 C47 . . 121.5(3) ?
C45 C44 C47 . . 120.9(3) ?
C44 C45 C46 . . 121.7(2) ?
C44 C45 H45 . . 119.2 ?
C46 C45 H45 . . 119.2 ?
C45 C46 C41 . . 120.5(2) ?
C45 C46 H46 . . 119.8 ?
C41 C46 H46 . . 119.8 ?
C44 C47 H47A . . 109.5 ?
C44 C47 H47B . . 109.5 ?
H47A C47 H47B . . 109.5 ?
C44 C47 H47C . . 109.5 ?
H47A C47 H47C . . 109.5 ?
H47B C47 H47C . . 109.5 ?
N6 C48 C56 . . 109.45(17) ?
N6 C48 C49 . . 111.18(18) ?
C56 C48 C49 . . 107.89(17) ?
N6 C48 H48 . . 109.4 ?
C56 C48 H48 . . 109.4 ?
C49 C48 H48 . . 109.4 ?
C50 C49 C48 . . 114.14(18) ?
C50 C49 H49A . . 108.7 ?
C48 C49 H49A . . 108.7 ?
C50 C49 H49B . . 108.7 ?
C48 C49 H49B . . 108.7 ?
H49A C49 H49B . . 107.6 ?
C51 C50 C55 . . 117.6(2) ?
C51 C50 C49 . . 121.6(2) ?
C55 C50 C49 . . 120.8(2) ?
C50 C51 C52 . . 120.7(3) ?
C50 C51 H51 . . 119.6 ?
C52 C51 H51 . . 119.6 ?
C53 C52 C51 . . 120.3(3) ?
C53 C52 H52 . . 119.8 ?
C51 C52 H52 . . 119.8 ?
C54 C53 C52 . . 119.5(3) ?
C54 C53 H53 . . 120.2 ?
C52 C53 H53 . . 120.2 ?
C53 C54 C55 . . 120.2(3) ?
C53 C54 H54 . . 119.9 ?
C55 C54 H54 . . 119.9 ?
C54 C55 C50 . . 121.6(2) ?
C54 C55 H55 . . 119.2 ?
C50 C55 H55 . . 119.2 ?
O5 C56 O6 . . 125.0(2) ?
O5 C56 C48 . . 124.8(2) ?
O6 C56 C48 . . 110.16(18) ?
O6 C57 C58 . . 107.41(19) ?
O6 C57 H57A . . 110.2 ?
C58 C57 H57A . . 110.2 ?
O6 C57 H57B . . 110.2 ?
C58 C57 H57B . . 110.2 ?
H57A C57 H57B . . 108.5 ?
C57 C58 H58A . . 109.5 ?
C57 C58 H58B . . 109.5 ?
H58A C58 H58B . . 109.5 ?
C57 C58 H58C . . 109.5 ?
H58A C58 H58C . . 109.5 ?
H58B C58 H58C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . 1.248(3) ?
O2 C27 . 1.201(3) ?
O3 C27 . 1.320(3) ?
O3 C28 . 1.457(3) ?
O4 C36 . 1.252(2) ?
O5 C56 . 1.195(2) ?
O6 C56 . 1.327(2) ?
O6 C57 . 1.456(2) ?
N1 C7 . 1.375(3) ?
N1 N2 . 1.401(2) ?
N1 C6 . 1.415(3) ?
N2 C9 . 1.309(3) ?
N3 C11 . 1.325(3) ?
N3 C19 . 1.449(3) ?
N3 H3A . 0.8600 ?
N4 C36 . 1.373(2) ?
N4 N5 . 1.403(2) ?
N4 C35 . 1.416(3) ?
N5 C38 . 1.310(2) ?
N6 C40 . 1.331(2) ?
N6 C48 . 1.445(2) ?
N6 H6 . 0.8600 ?
C1 C6 . 1.378(3) ?
C1 C2 . 1.396(4) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.366(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.364(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.383(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.383(3) ?
C5 H5 . 0.9300 ?
C7 C8 . 1.443(3) ?
C8 C11 . 1.392(3) ?
C8 C9 . 1.426(3) ?
C9 C10 . 1.492(3) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 C12 . 1.491(3) ?
C12 C13 . 1.371(3) ?
C12 C17 . 1.379(3) ?
C13 C14 . 1.384(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.370(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.375(3) ?
C15 C18 . 1.521(3) ?
C16 C17 . 1.377(3) ?
C16 H16 . 0.9300 ?
C17 H17 . 0.9300 ?
C18 H18A . 0.9599 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 C27 . 1.512(3) ?
C19 C20 . 1.538(3) ?
C19 H19 . 0.9800 ?
C20 C21 . 1.506(3) ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
C21 C26 . 1.375(3) ?
C21 C22 . 1.378(3) ?
C22 C23 . 1.382(3) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.373(3) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.358(4) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.374(3) ?
C25 H25 . 0.9300 ?
C26 H26 . 0.9300 ?
C28 C29 . 1.475(4) ?
C28 H28A . 0.9700 ?
C28 H28B . 0.9700 ?
C29 H29A . 0.9600 ?
C29 H29B . 0.9600 ?
C29 H29C . 0.9600 ?
C30 C35 . 1.374(3) ?
C30 C31 . 1.383(3) ?
C30 H30 . 0.9300 ?
C31 C32 . 1.376(4) ?
C31 H31 . 0.9300 ?
C32 C33 . 1.364(4) ?
C32 H32 . 0.9300 ?
C33 C34 . 1.374(3) ?
C33 H33 . 0.9300 ?
C34 C35 . 1.385(3) ?
C34 H34 . 0.9300 ?
C36 C37 . 1.433(3) ?
C37 C40 . 1.390(3) ?
C37 C38 . 1.433(3) ?
C38 C39 . 1.483(3) ?
C39 H39A . 0.9600 ?
C39 H39B . 0.9600 ?
C39 H39C . 0.9600 ?
C40 C41 . 1.482(3) ?
C41 C42 . 1.379(3) ?
C41 C46 . 1.383(3) ?
C42 C43 . 1.381(3) ?
C42 H42 . 0.9300 ?
C43 C44 . 1.373(3) ?
C43 H43 . 0.9300 ?
C44 C45 . 1.374(3) ?
C44 C47 . 1.518(3) ?
C45 C46 . 1.375(3) ?
C45 H45 . 0.9300 ?
C46 H46 . 0.9300 ?
C47 H47A . 0.9600 ?
C47 H47B . 0.9600 ?
C47 H47C . 0.9600 ?
C48 C56 . 1.518(3) ?
C48 C49 . 1.540(3) ?
C48 H48 . 0.9800 ?
C49 C50 . 1.510(3) ?
C49 H49A . 0.9700 ?
C49 H49B . 0.9700 ?
C50 C51 . 1.372(3) ?
C50 C55 . 1.374(3) ?
C51 C52 . 1.378(4) ?
C51 H51 . 0.9300 ?
C52 C53 . 1.368(4) ?
C52 H52 . 0.9300 ?
C53 C54 . 1.350(4) ?
C53 H53 . 0.9300 ?
C54 C55 . 1.371(3) ?
C54 H54 . 0.9300 ?
C55 H55 . 0.9300 ?
C57 C58 . 1.491(3) ?
C57 H57A . 0.9700 ?
C57 H57B . 0.9700 ?
C58 H58A . 0.9600 ?
C58 H58B . 0.9600 ?
C58 H58C . 0.9600 ?
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
N3 H3A O1 . 0.86 2.01 2.713(2) 138
N6 H6 O4 . 0.86 2.03 2.698(2) 133
C16 H16 O6 1_655 0.93 2.51 3.397(3) 161
C28 H28B O1 2_676 0.97 2.44 3.357(3) 157
C45 H45 Cg6 2_567 0.93 2.77 3.449(3) 130
C57 H57B Cg6 1_455 0.96 2.78 3.663(3) 152
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 N2 C9 . . . . -0.9(2) ?
C6 N1 N2 C9 . . . . 177.74(19) ?
C36 N4 N5 C38 . . . . 0.9(2) ?
C35 N4 N5 C38 . . . . 179.14(17) ?
C6 C1 C2 C3 . . . . 0.3(5) ?
C1 C2 C3 C4 . . . . -0.5(5) ?
C2 C3 C4 C5 . . . . 0.5(5) ?
C3 C4 C5 C6 . . . . -0.3(5) ?
C2 C1 C6 C5 . . . . -0.1(4) ?
C2 C1 C6 N1 . . . . 179.3(2) ?
C4 C5 C6 C1 . . . . 0.1(4) ?
C4 C5 C6 N1 . . . . -179.3(2) ?
C7 N1 C6 C1 . . . . 157.5(2) ?
N2 N1 C6 C1 . . . . -20.9(3) ?
C7 N1 C6 C5 . . . . -23.1(4) ?
N2 N1 C6 C5 . . . . 158.5(2) ?
N2 N1 C7 O1 . . . . -179.0(2) ?
C6 N1 C7 O1 . . . . 2.5(4) ?
N2 N1 C7 C8 . . . . 1.7(2) ?
C6 N1 C7 C8 . . . . -176.8(2) ?
O1 C7 C8 C11 . . . . -2.5(4) ?
N1 C7 C8 C11 . . . . 176.71(19) ?
O1 C7 C8 C9 . . . . 179.0(2) ?
N1 C7 C8 C9 . . . . -1.8(2) ?
N1 N2 C9 C8 . . . . -0.4(2) ?
N1 N2 C9 C10 . . . . 177.50(18) ?
C11 C8 C9 N2 . . . . -176.9(2) ?
C7 C8 C9 N2 . . . . 1.4(2) ?
C11 C8 C9 C10 . . . . 5.5(4) ?
C7 C8 C9 C10 . . . . -176.2(2) ?
C19 N3 C11 C8 . . . . -174.1(2) ?
C19 N3 C11 C12 . . . . 4.7(3) ?
C9 C8 C11 N3 . . . . -176.2(2) ?
C7 C8 C11 N3 . . . . 5.8(3) ?
C9 C8 C11 C12 . . . . 5.0(4) ?
C7 C8 C11 C12 . . . . -173.09(19) ?
N3 C11 C12 C13 . . . . 90.7(3) ?
C8 C11 C12 C13 . . . . -90.5(3) ?
N3 C11 C12 C17 . . . . -93.4(3) ?
C8 C11 C12 C17 . . . . 85.4(3) ?
C17 C12 C13 C14 . . . . -1.9(3) ?
C11 C12 C13 C14 . . . . 174.0(2) ?
C12 C13 C14 C15 . . . . 0.0(4) ?
C13 C14 C15 C16 . . . . 1.3(4) ?
C13 C14 C15 C18 . . . . 179.7(2) ?
C14 C15 C16 C17 . . . . -0.7(4) ?
C18 C15 C16 C17 . . . . -179.1(3) ?
C15 C16 C17 C12 . . . . -1.2(4) ?
C13 C12 C17 C16 . . . . 2.5(3) ?
C11 C12 C17 C16 . . . . -173.5(2) ?
C11 N3 C19 C27 . . . . -120.7(2) ?
C11 N3 C19 C20 . . . . 119.4(2) ?
N3 C19 C20 C21 . . . . -68.9(2) ?
C27 C19 C20 C21 . . . . 170.4(2) ?
C19 C20 C21 C26 . . . . -94.8(3) ?
C19 C20 C21 C22 . . . . 84.4(3) ?
C26 C21 C22 C23 . . . . -0.6(4) ?
C20 C21 C22 C23 . . . . -179.8(2) ?
C21 C22 C23 C24 . . . . -0.2(4) ?
C22 C23 C24 C25 . . . . 0.6(4) ?
C23 C24 C25 C26 . . . . -0.3(4) ?
C24 C25 C26 C21 . . . . -0.5(4) ?
C22 C21 C26 C25 . . . . 1.0(4) ?
C20 C21 C26 C25 . . . . -179.9(2) ?
C28 O3 C27 O2 . . . . -1.8(4) ?
C28 O3 C27 C19 . . . . 173.7(2) ?
N3 C19 C27 O2 . . . . -22.5(3) ?
C20 C19 C27 O2 . . . . 98.5(3) ?
N3 C19 C27 O3 . . . . 162.01(19) ?
C20 C19 C27 O3 . . . . -77.0(2) ?
C27 O3 C28 C29 . . . . 173.4(2) ?
C35 C30 C31 C32 . . . . -0.2(4) ?
C30 C31 C32 C33 . . . . 1.4(4) ?
C31 C32 C33 C34 . . . . -1.3(4) ?
C32 C33 C34 C35 . . . . 0.1(4) ?
C31 C30 C35 C34 . . . . -1.0(3) ?
C31 C30 C35 N4 . . . . 177.2(2) ?
C33 C34 C35 C30 . . . . 1.0(3) ?
C33 C34 C35 N4 . . . . -177.2(2) ?
C36 N4 C35 C30 . . . . 25.2(3) ?
N5 N4 C35 C30 . . . . -152.77(19) ?
C36 N4 C35 C34 . . . . -156.7(2) ?
N5 N4 C35 C34 . . . . 25.4(3) ?
N5 N4 C36 O4 . . . . 178.62(19) ?
C35 N4 C36 O4 . . . . 0.6(3) ?
N5 N4 C36 C37 . . . . -1.7(2) ?
C35 N4 C36 C37 . . . . -179.78(19) ?
O4 C36 C37 C40 . . . . 1.4(3) ?
N4 C36 C37 C40 . . . . -178.28(18) ?
O4 C36 C37 C38 . . . . -178.5(2) ?
N4 C36 C37 C38 . . . . 1.9(2) ?
N4 N5 C38 C37 . . . . 0.4(2) ?
N4 N5 C38 C39 . . . . -177.18(18) ?
C40 C37 C38 N5 . . . . 178.7(2) ?
C36 C37 C38 N5 . . . . -1.4(2) ?
C40 C37 C38 C39 . . . . -4.1(4) ?
C36 C37 C38 C39 . . . . 175.8(2) ?
C48 N6 C40 C37 . . . . 165.84(19) ?
C48 N6 C40 C41 . . . . -14.5(3) ?
C38 C37 C40 N6 . . . . 173.7(2) ?
C36 C37 C40 N6 . . . . -6.1(3) ?
C38 C37 C40 C41 . . . . -6.0(4) ?
C36 C37 C40 C41 . . . . 174.20(18) ?
N6 C40 C41 C42 . . . . 112.5(2) ?
C37 C40 C41 C42 . . . . -67.8(3) ?
N6 C40 C41 C46 . . . . -65.4(3) ?
C37 C40 C41 C46 . . . . 114.3(2) ?
C46 C41 C42 C43 . . . . 0.4(3) ?
C40 C41 C42 C43 . . . . -177.6(2) ?
C41 C42 C43 C44 . . . . 0.1(4) ?
C42 C43 C44 C45 . . . . -0.9(4) ?
C42 C43 C44 C47 . . . . 179.4(2) ?
C43 C44 C45 C46 . . . . 1.3(4) ?
C47 C44 C45 C46 . . . . -179.0(2) ?
C44 C45 C46 C41 . . . . -0.9(4) ?
C42 C41 C46 C45 . . . . 0.0(3) ?
C40 C41 C46 C45 . . . . 178.0(2) ?
C40 N6 C48 C56 . . . . 134.3(2) ?
C40 N6 C48 C49 . . . . -106.6(2) ?
N6 C48 C49 C50 . . . . 58.3(2) ?
C56 C48 C49 C50 . . . . 178.36(19) ?
C48 C49 C50 C51 . . . . -95.1(3) ?
C48 C49 C50 C55 . . . . 84.4(3) ?
C55 C50 C51 C52 . . . . 0.8(4) ?
C49 C50 C51 C52 . . . . -179.7(3) ?
C50 C51 C52 C53 . . . . 0.4(5) ?
C51 C52 C53 C54 . . . . -1.4(5) ?
C52 C53 C54 C55 . . . . 1.3(5) ?
C53 C54 C55 C50 . . . . -0.2(5) ?
C51 C50 C55 C54 . . . . -0.9(4) ?
C49 C50 C55 C54 . . . . 179.5(2) ?
C57 O6 C56 O5 . . . . 4.4(3) ?
C57 O6 C56 C48 . . . . -172.72(19) ?
N6 C48 C56 O5 . . . . 21.9(3) ?
C49 C48 C56 O5 . . . . -99.2(3) ?
N6 C48 C56 O6 . . . . -160.91(17) ?
C49 C48 C56 O6 . . . . 78.0(2) ?
C56 O6 C57 C58 . . . . -171.0(2) ?
