#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/06/7150617.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_7150617
loop_
_publ_author_name
'Jarowski, Peter D.'
'Wu, Yi-Lin'
'Boudon, Corinne'
'Gisselbrecht, Jean-Paul'
'Gross, Maurice'
'Schweizer, W. Bernd'
'Diederich, François'
_publ_section_title
;
 New donor--acceptor chromophores by formal [2+2] cycloaddition of
 donor-substituted alkynes to dicyanovinyl derivatives
;
_journal_issue                   7
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              1312
_journal_page_last               1322
_journal_paper_doi               10.1039/b821230a
_journal_volume                  7
_journal_year                    2009
_chemical_compound_source        'LOC ETH Zurich'
_chemical_formula_moiety         'C21 H19 N3 O '
_chemical_formula_sum            'C21 H19 N3 O'
_chemical_formula_weight         329.403
_chemical_name_common
;2-(1-(4-(dimethylamino)phenyl)-3-(4-
methoxyphenyl)allylidene)propanedinitrile
;
_chemical_name_systematic
;
2-(1-(4-(dimethylamino)phenyl)-3-(4-methoxyphenyl)allylidene)propanedinitrile
;
_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_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                104.702(2)
_cell_angle_beta                 90.581(2)
_cell_angle_gamma                104.638(2)
_cell_formula_units_Z            4
_cell_length_a                   7.8176(2)
_cell_length_b                   15.0473(4)
_cell_length_c                   16.0532(5)
_cell_measurement_reflns_used    16543
_cell_measurement_temperature    203
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.425
_cell_volume                     1761.71(9)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction
'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'SIR97(Altomare et al., J. Appl. Cryst.,1999)'
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.09883
_diffrn_orient_matrix_UB_12      0.04275
_diffrn_orient_matrix_UB_13      0.07743
_diffrn_orient_matrix_UB_21      -0.00857
_diffrn_orient_matrix_UB_22      -0.03408
_diffrn_orient_matrix_UB_23      0.06196
_diffrn_orient_matrix_UB_31      0.03460
_diffrn_orient_matrix_UB_32      -0.05429
_diffrn_orient_matrix_UB_33      -0.00540
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10655
_diffrn_reflns_theta_full        25.19
_diffrn_reflns_theta_max         25.19
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Cinnabar
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             696.0
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .006
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.034(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     604
_refine_ls_number_reflns         6111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+ (0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1433
_reflns_number_gt                4731
_reflns_number_total             6111
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b821230a.txt
_cod_data_source_block           3g
_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 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C21 H19 N3 O '
_cod_database_code               7150617
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
O11 O 0.22312(19) 0.92393(10) 0.93357(10) 0.0538(4) Uani 1 1 d . . .
O36 O 0.71457(19) 0.91862(10) 0.77344(9) 0.0520(4) Uani 1 1 d . . .
N19 N -0.3336(2) 0.13079(11) 0.61061(10) 0.0474(4) Uani 1 1 d . . .
N23 N -0.5630(2) 0.20331(13) 1.00297(11) 0.0520(4) Uani 1 1 d . . .
N25 N -0.3597(3) 0.49646(13) 1.15168(11) 0.0572(5) Uani 1 1 d . . .
N44 N 0.1719(2) 0.13078(11) 0.71277(10) 0.0467(4) Uani 1 1 d . . .
N48 N -0.0698(2) 0.19885(13) 0.34938(12) 0.0555(5) Uani 1 1 d . . .
N50 N 0.1346(3) 0.49234(13) 0.34256(11) 0.0557(5) Uani 1 1 d . . .
C1 C -0.3828(2) 0.37288(13) 1.00451(11) 0.0383(4) Uani 1 1 d . . .
C2 C -0.3085(2) 0.40000(13) 0.93404(11) 0.0370(4) Uani 1 1 d . . .
C3 C -0.2260(2) 0.50010(13) 0.94320(12) 0.0397(4) Uani 1 1 d . . .
C4 C -0.1144(2) 0.53604(13) 0.88974(12) 0.0388(4) Uani 1 1 d . . .
C5 C -0.0306(2) 0.63646(13) 0.89977(11) 0.0370(4) Uani 1 1 d . . .
C6 C -0.0714(3) 0.70942(13) 0.96343(12) 0.0421(4) Uani 1 1 d . . .
C7 C 0.0132(3) 0.80341(14) 0.97184(12) 0.0444(4) Uani 1 1 d . . .
C8 C 0.1453(2) 0.82846(13) 0.91791(12) 0.0409(4) Uani 1 1 d . . .
C9 C 0.1855(2) 0.75797(14) 0.85287(12) 0.0417(4) Uani 1 1 d . . .
C10 C 0.0976(2) 0.66382(14) 0.84405(12) 0.0411(4) Uani 1 1 d . . .
C12 C 0.3728(3) 0.95162(18) 0.88642(18) 0.0598(6) Uani 1 1 d . . .
C13 C -0.3147(2) 0.32924(12) 0.85122(11) 0.0349(4) Uani 1 1 d . . .
C14 C -0.3535(2) 0.34906(13) 0.77349(11) 0.0380(4) Uani 1 1 d . . .
C15 C -0.3607(2) 0.28376(13) 0.69515(11) 0.0393(4) Uani 1 1 d . . .
C16 C -0.3279(2) 0.19534(12) 0.68965(11) 0.0370(4) Uani 1 1 d . . .
C17 C -0.2912(2) 0.17456(13) 0.76786(12) 0.0392(4) Uani 1 1 d . . .
C18 C -0.2843(2) 0.24033(13) 0.84595(12) 0.0383(4) Uani 1 1 d . . .
C20 C -0.3122(3) 0.16522(18) 0.53401(13) 0.0528(5) Uani 1 1 d . . .
C21 C -0.2892(4) 0.04234(16) 0.60594(16) 0.0561(5) Uani 1 1 d . . .
C22 C -0.4808(2) 0.27814(14) 1.00218(11) 0.0405(4) Uani 1 1 d . . .
C24 C -0.3695(3) 0.44129(14) 1.08640(12) 0.0433(4) Uani 1 1 d . . .
C26 C 0.1104(2) 0.36844(13) 0.43050(11) 0.0378(4) Uani 1 1 d . . .
C27 C 0.1843(2) 0.39546(12) 0.51449(11) 0.0358(4) Uani 1 1 d . . .
C28 C 0.2681(2) 0.49575(13) 0.55361(12) 0.0393(4) Uani 1 1 d . . .
C29 C 0.3820(2) 0.53115(13) 0.62381(12) 0.0377(4) Uani 1 1 d . . .
C30 C 0.4667(2) 0.63157(12) 0.66312(11) 0.0363(4) Uani 1 1 d . . .
C31 C 0.5888(2) 0.65801(13) 0.73433(12) 0.0400(4) Uani 1 1 d . . .
C32 C 0.6757(2) 0.75233(14) 0.77316(12) 0.0417(4) Uani 1 1 d . . .
C33 C 0.6381(2) 0.82313(13) 0.74083(12) 0.0396(4) Uani 1 1 d . . .
C34 C 0.5131(3) 0.79879(14) 0.67099(12) 0.0444(4) Uani 1 1 d . . .
C35 C 0.4301(3) 0.70503(13) 0.63256(12) 0.0422(4) Uani 1 1 d . . .
C37 C 0.8465(4) 0.94612(19) 0.84349(18) 0.0661(7) Uani 1 1 d . . .
C38 C 0.1791(2) 0.32574(12) 0.56415(11) 0.0351(4) Uani 1 1 d . . .
C39 C 0.2082(2) 0.23632(13) 0.52766(12) 0.0388(4) Uani 1 1 d . . .
C40 C 0.2045(2) 0.17217(13) 0.57589(12) 0.0402(4) Uani 1 1 d . . .
C41 C 0.1730(2) 0.19418(12) 0.66381(11) 0.0368(4) Uani 1 1 d . . .
C42 C 0.1405(2) 0.28297(13) 0.70004(12) 0.0381(4) Uani 1 1 d . . .
C43 C 0.1437(2) 0.34668(13) 0.65159(11) 0.0377(4) Uani 1 1 d . . .
C45 C 0.2045(3) 0.03942(16) 0.67415(17) 0.0559(6) Uani 1 1 d . . .
C46 C 0.1968(3) 0.16584(18) 0.80580(14) 0.0532(5) Uani 1 1 d . . .
C47 C 0.0117(3) 0.27337(14) 0.38657(12) 0.0416(4) Uani 1 1 d . . .
C49 C 0.1239(3) 0.43681(13) 0.38109(12) 0.0418(4) Uani 1 1 d . . .
H29 H 0.416(3) 0.4894(15) 0.6545(12) 0.044(5) Uiso 1 1 d . . .
H39 H 0.237(3) 0.2217(14) 0.4673(13) 0.043(5) Uiso 1 1 d . . .
H31 H 0.609(3) 0.6082(15) 0.7560(13) 0.050(6) Uiso 1 1 d . . .
H18 H -0.251(3) 0.2252(14) 0.8992(13) 0.043(5) Uiso 1 1 d . . .
H4 H -0.085(3) 0.4905(15) 0.8404(14) 0.049(5) Uiso 1 1 d . . .
H6 H -0.161(3) 0.6934(14) 1.0036(13) 0.042(5) Uiso 1 1 d . . .
H15 H -0.390(2) 0.3014(13) 0.6426(12) 0.037(5) Uiso 1 1 d . . .
H42 H 0.118(3) 0.3007(14) 0.7594(13) 0.043(5) Uiso 1 1 d . . .
H43 H 0.116(2) 0.4060(15) 0.6794(12) 0.040(5) Uiso 1 1 d . . .
H14 H -0.387(3) 0.4089(15) 0.7744(12) 0.043(5) Uiso 1 1 d . . .
H28 H 0.240(3) 0.5369(15) 0.5207(13) 0.047(5) Uiso 1 1 d . . .
H10 H 0.126(2) 0.6130(14) 0.7988(12) 0.036(5) Uiso 1 1 d . . .
H3 H -0.248(3) 0.5443(16) 0.9965(14) 0.053(6) Uiso 1 1 d . . .
H35 H 0.347(3) 0.6904(15) 0.5805(15) 0.054(6) Uiso 1 1 d . . .
H32 H 0.758(3) 0.7682(14) 0.8238(13) 0.041(5) Uiso 1 1 d . . .
H46 H 0.208(3) 0.1141(19) 0.8313(16) 0.073(7) Uiso 1 1 d . . .
H34 H 0.490(3) 0.8507(18) 0.6470(15) 0.068(7) Uiso 1 1 d . . .
H20 H -0.209(4) 0.220(2) 0.5416(17) 0.083(8) Uiso 1 1 d . . .
H7 H -0.021(3) 0.8571(17) 1.0162(16) 0.064(6) Uiso 1 1 d . . .
H17 H -0.270(2) 0.1136(14) 0.7669(12) 0.037(5) Uiso 1 1 d . . .
H40 H 0.225(3) 0.1090(16) 0.5475(14) 0.050(5) Uiso 1 1 d . . .
H20B H -0.418(4) 0.1889(18) 0.5177(16) 0.070(7) Uiso 1 1 d . . .
H45A H 0.125(4) 0.004(2) 0.6187(19) 0.079(8) Uiso 1 1 d . . .
H46B H 0.090(3) 0.1868(17) 0.8310(15) 0.065(7) Uiso 1 1 d . . .
H9 H 0.271(3) 0.7751(15) 0.8138(14) 0.052(6) Uiso 1 1 d . . .
H20C H -0.301(4) 0.114(2) 0.4840(19) 0.081(8) Uiso 1 1 d . . .
H37A H 0.804(4) 0.929(2) 0.8953(18) 0.077(8) Uiso 1 1 d . . .
H12A H 0.409(3) 1.0205(18) 0.9075(15) 0.060(6) Uiso 1 1 d . . .
H21A H -0.341(4) -0.0019(19) 0.5480(18) 0.076(7) Uiso 1 1 d . . .
H21B H -0.355(4) 0.009(2) 0.6487(18) 0.083(8) Uiso 1 1 d . . .
H12B H 0.345(4) 0.9358(19) 0.8231(19) 0.081(8) Uiso 1 1 d . . .
H46C H 0.285(4) 0.2284(19) 0.8250(16) 0.070(7) Uiso 1 1 d . . .
H45B H 0.183(4) 0.003(2) 0.714(2) 0.096(9) Uiso 1 1 d . . .
H12C H 0.465(3) 0.9186(18) 0.8957(16) 0.068(7) Uiso 1 1 d . . .
H37B H 0.884(4) 1.017(2) 0.8570(18) 0.088(8) Uiso 1 1 d . . .
H45C H 0.333(4) 0.0464(18) 0.6572(16) 0.072(7) Uiso 1 1 d . . .
H37C H 0.950(4) 0.919(2) 0.824(2) 0.098(10) Uiso 1 1 d . . .
H21C H -0.163(5) 0.045(2) 0.614(2) 0.099(10) Uiso 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_
_diffrn_radiation_wavelength
0.71073
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
C8 O11 C12 116.82(16) . . ?
C33 O36 C37 117.04(17) . . ?
C16 N19 C21 120.13(17) . . ?
C16 N19 C20 118.79(17) . . ?
C21 N19 C20 116.46(17) . . ?
C41 N44 C45 120.20(17) . . ?
C41 N44 C46 119.16(17) . . ?
C45 N44 C46 117.57(18) . . ?
C2 C1 C22 124.20(17) . . ?
C2 C1 C24 120.83(17) . . ?
C22 C1 C24 114.95(15) . . ?
C1 C2 C3 118.59(16) . . ?
C1 C2 C13 120.87(16) . . ?
C3 C2 C13 120.53(15) . . ?
C4 C3 C2 125.96(17) . . ?
C3 C4 C5 125.71(17) . . ?
C6 C5 C10 117.13(17) . . ?
C6 C5 C4 123.06(16) . . ?
C10 C5 C4 119.81(16) . . ?
C7 C6 C5 121.28(17) . . ?
C6 C7 C8 120.42(18) . . ?
O11 C8 C9 125.13(16) . . ?
O11 C8 C7 115.26(16) . . ?
C9 C8 C7 119.59(17) . . ?
C10 C9 C8 119.47(17) . . ?
C9 C10 C5 122.01(17) . . ?
C18 C13 C14 117.33(16) . . ?
C18 C13 C2 122.44(15) . . ?
C14 C13 C2 120.23(16) . . ?
C15 C14 C13 121.29(17) . . ?
C14 C15 C16 121.47(17) . . ?
N19 C16 C15 120.96(16) . . ?
N19 C16 C17 121.62(17) . . ?
C15 C16 C17 117.41(16) . . ?
C18 C17 C16 120.69(17) . . ?
C17 C18 C13 121.79(17) . . ?
N23 C22 C1 177.36(19) . . ?
N25 C24 C1 179.4(2) . . ?
C27 C26 C47 124.22(15) . . ?
C27 C26 C49 120.93(17) . . ?
C47 C26 C49 114.82(16) . . ?
C26 C27 C28 118.52(15) . . ?
C26 C27 C38 121.48(16) . . ?
C28 C27 C38 120.00(16) . . ?
C29 C28 C27 125.89(17) . . ?
C28 C29 C30 126.10(17) . . ?
C31 C30 C35 117.27(17) . . ?
C31 C30 C29 119.86(16) . . ?
C35 C30 C29 122.87(17) . . ?
C32 C31 C30 122.23(17) . . ?
C31 C32 C33 119.09(18) . . ?
O36 C33 C32 124.70(17) . . ?
O36 C33 C34 115.43(16) . . ?
C32 C33 C34 119.86(17) . . ?
C35 C34 C33 120.31(18) . . ?
C34 C35 C30 121.21(18) . . ?
C39 C38 C43 117.21(15) . . ?
C39 C38 C27 122.32(15) . . ?
C43 C38 C27 120.47(15) . . ?
C40 C39 C38 121.32(17) . . ?
C39 C40 C41 121.31(17) . . ?
N44 C41 C42 121.01(16) . . ?
N44 C41 C40 121.55(16) . . ?
C42 C41 C40 117.44(15) . . ?
C43 C42 C41 121.05(16) . . ?
C42 C43 C38 121.64(17) . . ?
N48 C47 C26 177.4(2) . . ?
N50 C49 C26 179.1(2) . . ?
C4 C3 H3 118.3(12) . . ?
C2 C3 H3 115.6(12) . . ?
C3 C4 H4 117.0(12) . . ?
C5 C4 H4 117.3(12) . . ?
C7 C6 H6 118.9(11) . . ?
C5 C6 H6 119.8(11) . . ?
C6 C7 H7 121.4(13) . . ?
C8 C7 H7 118.1(13) . . ?
C10 C9 H9 120.7(13) . . ?
C8 C9 H9 119.8(13) . . ?
C9 C10 H10 120.3(10) . . ?
C5 C10 H10 117.6(11) . . ?
O11 C12 H12A 103.8(13) . . ?
O11 C12 H12B 114.0(16) . . ?
H12A C12 H12B 107(2) . . ?
O11 C12 H12C 109.8(14) . . ?
H12A C12 H12C 115(2) . . ?
H12B C12 H12C 107(2) . . ?
C15 C14 H14 118.5(11) . . ?
C13 C14 H14 120.0(11) . . ?
C14 C15 H15 117.6(11) . . ?
C16 C15 H15 120.9(11) . . ?
C18 C17 H17 119.4(11) . . ?
C16 C17 H17 119.9(11) . . ?
C17 C18 H18 118.6(12) . . ?
C13 C18 H18 119.5(12) . . ?
N19 C20 H20 111.7(16) . . ?
N19 C20 H20B 113.5(13) . . ?
H20 C20 H20B 105(2) . . ?
N19 C20 H20C 110.4(16) . . ?
H20 C20 H20C 110(2) . . ?
H20B C20 H20C 106(2) . . ?
N19 C21 H21A 106.6(15) . . ?
N19 C21 H21B 110.7(15) . . ?
H21A C21 H21B 104(2) . . ?
N19 C21 H21C 117.7(18) . . ?
H21A C21 H21C 110(2) . . ?
H21B C21 H21C 108(2) . . ?
C29 C28 H28 121.0(13) . . ?
C27 C28 H28 113.0(13) . . ?
C28 C29 H29 120.9(12) . . ?
C30 C29 H29 113.0(12) . . ?
C32 C31 H31 121.0(13) . . ?
C30 C31 H31 116.7(13) . . ?
C31 C32 H32 119.9(12) . . ?
C33 C32 H32 121.0(12) . . ?
C35 C34 H34 120.5(15) . . ?
C33 C34 H34 119.1(15) . . ?
C34 C35 H35 117.8(12) . . ?
C30 C35 H35 120.9(12) . . ?
O36 C37 H37A 114.4(17) . . ?
O36 C37 H37B 104.1(17) . . ?
H37A C37 H37B 108(2) . . ?
O36 C37 H37C 109.5(19) . . ?
H37A C37 H37C 111(2) . . ?
H37B C37 H37C 110(2) . . ?
C40 C39 H39 120.6(11) . . ?
C38 C39 H39 118.1(11) . . ?
C39 C40 H40 118.9(12) . . ?
C41 C40 H40 119.8(12) . . ?
C43 C42 H42 118.8(12) . . ?
C41 C42 H42 120.2(12) . . ?
C42 C43 H43 117.5(11) . . ?
C38 C43 H43 120.8(11) . . ?
N44 C45 H45A 111.5(15) . . ?
N44 C45 H45B 108.2(19) . . ?
H45A C45 H45B 110(2) . . ?
N44 C45 H45C 111.8(14) . . ?
H45A C45 H45C 106(2) . . ?
H45B C45 H45C 109(2) . . ?
N44 C46 H46 109.7(15) . . ?
N44 C46 H46B 111.6(14) . . ?
H46 C46 H46B 105.9(19) . . ?
N44 C46 H46C 112.4(14) . . ?
H46 C46 H46C 119(2) . . ?
H46B C46 H46C 97.6(19) . . ?
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
O11 C8 1.367(2) . ?
O11 C12 1.431(3) . ?
O36 C33 1.369(2) . ?
O36 C37 1.423(3) . ?
N19 C16 1.381(2) . ?
N19 C21 1.442(3) . ?
N19 C20 1.446(3) . ?
N23 C22 1.150(2) . ?
N25 C24 1.148(2) . ?
N44 C41 1.380(2) . ?
N44 C45 1.445(3) . ?
N44 C46 1.445(3) . ?
N48 C47 1.145(2) . ?
N50 C49 1.147(2) . ?
C1 C2 1.383(2) . ?
C1 C22 1.429(3) . ?
C1 C24 1.434(3) . ?
C2 C3 1.450(3) . ?
C2 C13 1.469(2) . ?
C3 C4 1.343(3) . ?
C4 C5 1.453(3) . ?
C5 C6 1.402(3) . ?
C5 C10 1.404(2) . ?
C6 C7 1.373(3) . ?
C7 C8 1.395(3) . ?
C8 C9 1.388(3) . ?
C9 C10 1.380(3) . ?
C13 C18 1.399(3) . ?
C13 C14 1.402(2) . ?
C14 C15 1.376(3) . ?
C15 C16 1.399(3) . ?
C16 C17 1.412(3) . ?
C17 C18 1.377(3) . ?
C26 C27 1.380(3) . ?
C26 C47 1.435(3) . ?
C26 C49 1.435(2) . ?
C27 C28 1.453(3) . ?
C27 C38 1.463(2) . ?
C28 C29 1.335(3) . ?
C29 C30 1.457(3) . ?
C30 C31 1.389(3) . ?
C30 C35 1.406(3) . ?
C31 C32 1.385(3) . ?
C32 C33 1.388(3) . ?
C33 C34 1.391(3) . ?
C34 C35 1.371(3) . ?
C38 C39 1.401(2) . ?
C38 C43 1.405(2) . ?
C39 C40 1.378(3) . ?
C40 C41 1.405(3) . ?
C41 C42 1.403(3) . ?
C42 C43 1.375(3) . ?
C3 H3 0.99(2) . ?
C4 H4 0.98(2) . ?
C6 H6 0.98(2) . ?
C7 H7 1.03(2) . ?
C9 H9 0.96(2) . ?
C10 H10 0.986(19) . ?
C12 H12A 0.97(3) . ?
C12 H12B 0.99(3) . ?
C12 H12C 1.00(3) . ?
C14 H14 1.00(2) . ?
C15 H15 0.989(19) . ?
C17 H17 0.97(2) . ?
C18 H18 0.99(2) . ?
C20 H20 0.98(3) . ?
C20 H20B 1.04(3) . ?
C20 H20C 0.98(3) . ?
C21 H21A 1.01(3) . ?
C21 H21B 1.02(3) . ?
C21 H21C 0.98(3) . ?
C28 H28 0.97(2) . ?
C29 H29 0.97(2) . ?
C31 H31 0.95(2) . ?
C32 H32 0.97(2) . ?
C34 H34 1.01(2) . ?
C35 H35 1.00(2) . ?
C37 H37A 0.97(3) . ?
C37 H37B 1.00(3) . ?
C37 H37C 1.01(3) . ?
C39 H39 0.98(2) . ?
C40 H40 1.00(2) . ?
C42 H42 0.95(2) . ?
C43 H43 0.97(2) . ?
C45 H45A 1.02(3) . ?
C45 H45B 0.94(3) . ?
C45 H45C 1.03(3) . ?
C46 H46 0.99(3) . ?
C46 H46B 1.02(3) . ?
C46 H46C 0.99(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
C22 C1 C2 C3 174.54(17) . . . . ?
C24 C1 C2 C3 -3.7(3) . . . . ?
C22 C1 C2 C13 -4.7(3) . . . . ?
C24 C1 C2 C13 177.07(16) . . . . ?
C1 C2 C3 C4 163.72(18) . . . . ?
C13 C2 C3 C4 -17.0(3) . . . . ?
C2 C3 C4 C5 -179.32(17) . . . . ?
C3 C4 C5 C6 -6.5(3) . . . . ?
C3 C4 C5 C10 173.51(18) . . . . ?
C10 C5 C6 C7 -1.3(3) . . . . ?
C4 C5 C6 C7 178.73(17) . . . . ?
C5 C6 C7 C8 -1.3(3) . . . . ?
C12 O11 C8 C9 -8.5(3) . . . . ?
C12 O11 C8 C7 172.94(19) . . . . ?
C6 C7 C8 O11 -178.49(17) . . . . ?
C6 C7 C8 C9 2.9(3) . . . . ?
O11 C8 C9 C10 179.75(17) . . . . ?
C7 C8 C9 C10 -1.8(3) . . . . ?
C8 C9 C10 C5 -0.9(3) . . . . ?
C6 C5 C10 C9 2.4(3) . . . . ?
C4 C5 C10 C9 -177.60(17) . . . . ?
C1 C2 C13 C18 -41.8(3) . . . . ?
C3 C2 C13 C18 138.96(18) . . . . ?
C1 C2 C13 C14 137.69(18) . . . . ?
C3 C2 C13 C14 -41.6(2) . . . . ?
C18 C13 C14 C15 -0.2(3) . . . . ?
C2 C13 C14 C15 -179.72(16) . . . . ?
C13 C14 C15 C16 -0.7(3) . . . . ?
C21 N19 C16 C15 176.35(19) . . . . ?
C20 N19 C16 C15 21.3(3) . . . . ?
C21 N19 C16 C17 -4.5(3) . . . . ?
C20 N19 C16 C17 -159.52(18) . . . . ?
C14 C15 C16 N19 -179.27(16) . . . . ?
C14 C15 C16 C17 1.5(3) . . . . ?
N19 C16 C17 C18 179.31(17) . . . . ?
C15 C16 C17 C18 -1.5(3) . . . . ?
C16 C17 C18 C13 0.6(3) . . . . ?
C14 C13 C18 C17 0.2(3) . . . . ?
C2 C13 C18 C17 179.73(16) . . . . ?
C2 C1 C22 N23 -155(4) . . . . ?
C24 C1 C22 N23 23(5) . . . . ?
C2 C1 C24 N25 6E1(3) . . . . ?
C22 C1 C24 N25 -12E1(3) . . . . ?
C47 C26 C27 C28 -174.83(16) . . . . ?
C49 C26 C27 C28 3.3(3) . . . . ?
C47 C26 C27 C38 4.9(3) . . . . ?
C49 C26 C27 C38 -176.95(15) . . . . ?
C26 C27 C28 C29 -162.14(18) . . . . ?
C38 C27 C28 C29 18.1(3) . . . . ?
C27 C28 C29 C30 179.80(15) . . . . ?
C28 C29 C30 C31 -177.31(17) . . . . ?
C28 C29 C30 C35 3.1(3) . . . . ?
C35 C30 C31 C32 -1.7(2) . . . . ?
C29 C30 C31 C32 178.73(15) . . . . ?
C30 C31 C32 C33 0.9(3) . . . . ?
C37 O36 C33 C32 2.4(3) . . . . ?
C37 O36 C33 C34 -178.4(2) . . . . ?
C31 C32 C33 O36 179.90(16) . . . . ?
C31 C32 C33 C34 0.7(3) . . . . ?
O36 C33 C34 C35 179.13(16) . . . . ?
C32 C33 C34 C35 -1.6(3) . . . . ?
C33 C34 C35 C30 0.9(3) . . . . ?
C31 C30 C35 C34 0.7(3) . . . . ?
C29 C30 C35 C34 -179.67(16) . . . . ?
C26 C27 C38 C39 41.0(3) . . . . ?
C28 C27 C38 C39 -139.22(18) . . . . ?
C26 C27 C38 C43 -138.87(18) . . . . ?
C28 C27 C38 C43 40.9(2) . . . . ?
C43 C38 C39 C40 -0.8(3) . . . . ?
C27 C38 C39 C40 179.31(17) . . . . ?
C38 C39 C40 C41 -0.6(3) . . . . ?
C45 N44 C41 C42 179.61(19) . . . . ?
C46 N44 C41 C42 -20.7(3) . . . . ?
C45 N44 C41 C40 0.3(3) . . . . ?
C46 N44 C41 C40 160.02(19) . . . . ?
C39 C40 C41 N44 -178.95(18) . . . . ?
C39 C40 C41 C42 1.7(3) . . . . ?
N44 C41 C42 C43 179.17(17) . . . . ?
C40 C41 C42 C43 -1.5(3) . . . . ?
C41 C42 C43 C38 0.1(3) . . . . ?
C39 C38 C43 C42 1.0(3) . . . . ?
C27 C38 C43 C42 -179.08(17) . . . . ?
C27 C26 C47 N48 160(4) . . . . ?
C49 C26 C47 N48 -18(5) . . . . ?
C27 C26 C49 N50 -35(14) . . . . ?
C47 C26 C49 N50 144(14) . . . . ?
