# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
#######################################################################
data_5a
_database_code_depnum_ccdc_archive 'CCDC 894169'
_audit_update_record
;
2011-11-22 # Formatted by publCIF
;
_audit_creation_method SHELXL-97
_chemical_name_systematic
2-{(E)-5-[(E)-3-{4-(Diethylamino)phenyl}-1-{4-(dimethylamino)phenyl}allylidene]-4-phenylthiazol-2-ylidene}malononitrile
_chemical_name_common ?
_chemical_formula_moiety 'C33 H31 N5 S'
_chemical_formula_sum 'C33 H31 N5 S'
_exptl_crystal_recrystallization_method
'diffusion of hexane into a solution of AcOEt at r.t.'
_chemical_melting_point ?
_exptl_crystal_description block
_exptl_crystal_colour green
_diffrn_ambient_temperature 298(1)
_chemical_formula_weight 529.69
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_int_tables_number 2
_chemical_absolute_configuration ?
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.5856(3)
_cell_length_b 13.3808(10)
_cell_length_c 13.8389(9)
_cell_angle_alpha 66.612(7)
_cell_angle_beta 77.281(4)
_cell_angle_gamma 77.711(5)
_cell_volume 1409.37(15)
_cell_formula_units_Z 2
_cell_measurement_temperature 298(1)
_cell_measurement_reflns_used 3148
_cell_measurement_theta_min 2.6567
_cell_measurement_theta_max 28.7939
_exptl_crystal_size_max 0.37
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.06
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.248
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 560
_exptl_absorpt_coefficient_mu 0.146
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_special_details ?
_diffrn_radiation_probe ?
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator graphite
_diffrn_detector_area_resol_mean 16.3990
_diffrn_reflns_number 27453
_diffrn_measurement_device_type
;
CCD-based four-circle diffractometer
;
_diffrn_measurement_method \w-scans
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_av_R_equivalents 0.0973
_diffrn_reflns_av_sigmaI/netI 0.1691
_diffrn_reflns_limit_h_min -6
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_theta_min 2.67
_diffrn_reflns_theta_max 25.00
_reflns_number_total 4939
_reflns_number_gt 1804
_reflns_threshold_expression >2\s(I)
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
;
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
;
_computing_structure_solution SIR-92
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'Diamond 3.2g'
_computing_publication_material 'SHELXL-97 (Sheldrick, 2008)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0005P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 4939
_refine_ls_number_parameters 354
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1598
_refine_ls_R_factor_gt 0.0419
_refine_ls_wR_factor_ref 0.0424
_refine_ls_wR_factor_gt 0.0365
_refine_ls_goodness_of_fit_ref 0.805
_refine_ls_restrained_S_all 0.805
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
S1 S 0.29769(7) 0.60881(6) 0.37440(5) 0.0591(2) Uani 1 1 d . . .
C1 C 0.2345(3) 0.7489(2) 0.3196(2) 0.0519(7) Uani 1 1 d . . .
N1 N 0.3487(3) 0.80692(16) 0.24870(16) 0.0514(6) Uani 1 1 d . . .
C2 C 0.4876(3) 0.7421(2) 0.23852(19) 0.0436(7) Uani 1 1 d . . .
C3 C 0.4898(3) 0.6281(2) 0.29929(18) 0.0452(7) Uani 1 1 d . . .
C4 C 0.0820(3) 0.7954(3) 0.3503(2) 0.0618(9) Uani 1 1 d . . .
C5 C -0.0275(3) 0.7285(3) 0.4279(3) 0.0725(10) Uani 1 1 d . . .
N2 N -0.1140(3) 0.6702(2) 0.4908(2) 0.1020(10) Uani 1 1 d . . .
C6 C 0.0331(3) 0.9099(3) 0.3074(2) 0.0690(10) Uani 1 1 d . . .
N3 N -0.0102(3) 1.0018(2) 0.2732(2) 0.0946(10) Uani 1 1 d . . .
C7 C 0.6235(3) 0.7970(2) 0.1645(2) 0.0451(7) Uani 1 1 d . . .
C8 C 0.6010(3) 0.8624(2) 0.0619(2) 0.0586(8) Uani 1 1 d . . .
H8 H 0.5005 0.8728 0.0418 0.070 Uiso 1 1 calc R . .
C9 C 0.7242(4) 0.9129(2) -0.0123(2) 0.0657(8) Uani 1 1 d . . .
H9 H 0.7075 0.9557 -0.0819 0.079 Uiso 1 1 calc R . .
C10 C 0.8714(3) 0.8994(2) 0.0177(2) 0.0665(9) Uani 1 1 d . . .
H10 H 0.9561 0.9317 -0.0318 0.080 Uiso 1 1 calc R . .
C11 C 0.8931(3) 0.8381(2) 0.1213(3) 0.0633(9) Uani 1 1 d . . .
H11 H 0.9921 0.8314 0.1417 0.076 Uiso 1 1 calc R . .
C12 C 0.7714(3) 0.78602(19) 0.1959(2) 0.0536(7) Uani 1 1 d . . .
H12 H 0.7880 0.7444 0.2658 0.064 Uiso 1 1 calc R . .
C13 C 0.6065(3) 0.5369(2) 0.30465(19) 0.0430(7) Uani 1 1 d . . .
C14 C 0.5774(3) 0.4314(2) 0.37769(18) 0.0492(8) Uani 1 1 d . . .
H14 H 0.4818 0.4268 0.4255 0.059 Uiso 1 1 calc R . .
C15 C 0.6768(3) 0.3355(2) 0.38456(19) 0.0489(7) Uani 1 1 d . . .
H15 H 0.7726 0.3409 0.3369 0.059 Uiso 1 1 calc R . .
C16 C 0.7631(3) 0.54809(19) 0.2330(2) 0.0449(7) Uani 1 1 d . . .
C17 C 0.7719(3) 0.58879(18) 0.1244(2) 0.0484(7) Uani 1 1 d . . .
H17 H 0.6770 0.6067 0.0956 0.058 Uiso 1 1 calc R . .
C18 C 0.9161(3) 0.60427(18) 0.05609(19) 0.0562(8) Uani 1 1 d . . .
H18 H 0.9169 0.6317 -0.0172 0.067 Uiso 1 1 calc R . .
C19 C 1.0611(4) 0.5788(2) 0.0971(3) 0.0599(8) Uani 1 1 d . . .
C20 C 1.0530(3) 0.5360(2) 0.2060(3) 0.0635(9) Uani 1 1 d . . .
H20 H 1.1475 0.5175 0.2354 0.076 Uiso 1 1 calc R . .
C21 C 0.9078(3) 0.51985(18) 0.2727(2) 0.0573(8) Uani 1 1 d . . .
H21 H 0.9069 0.4893 0.3460 0.069 Uiso 1 1 calc R . .
N4 N 1.2056(3) 0.5961(2) 0.0291(2) 0.0849(9) Uani 1 1 d . . .
C22 C 1.2044(3) 0.6554(2) -0.0821(2) 0.1063(12) Uani 1 1 d . . .
H22B H 1.1449 0.6210 -0.1085 0.128 Uiso 1 1 calc R . .
H22C H 1.3131 0.6554 -0.1189 0.128 Uiso 1 1 calc R . .
H22A H 1.1543 0.7298 -0.0938 0.128 Uiso 1 1 calc R . .
C23 C 1.3451(3) 0.5944(2) 0.0699(2) 0.1471(16) Uani 1 1 d . . .
H23C H 1.3254 0.6505 0.0996 0.177 Uiso 1 1 calc R . .
H23A H 1.4350 0.6077 0.0134 0.177 Uiso 1 1 calc R . .
H23B H 1.3690 0.5238 0.1243 0.177 Uiso 1 1 calc R . .
C24 C 0.6494(3) 0.2287(2) 0.4566(2) 0.0436(7) Uani 1 1 d . . .
C25 C 0.7673(3) 0.1377(2) 0.4578(2) 0.0564(8) Uani 1 1 d . . .
H25 H 0.8634 0.1495 0.4110 0.068 Uiso 1 1 calc R . .
C26 C 0.7471(3) 0.0342(2) 0.5240(2) 0.0579(8) Uani 1 1 d . . .
H26 H 0.8300 -0.0228 0.5221 0.069 Uiso 1 1 calc R . .
C27 C 0.6026(3) 0.0096(2) 0.5966(2) 0.0495(7) Uani 1 1 d . . .
C28 C 0.4856(3) 0.1018(2) 0.59462(19) 0.0501(7) Uani 1 1 d . . .
H28 H 0.3890 0.0907 0.6410 0.060 Uiso 1 1 calc R . .
C29 C 0.5072(3) 0.2052(2) 0.5288(2) 0.0525(8) Uani 1 1 d . . .
H29 H 0.4255 0.2627 0.5312 0.063 Uiso 1 1 calc R . .
N5 N 0.5767(3) -0.09269(19) 0.66044(17) 0.0593(7) Uani 1 1 d . . .
C30 C 0.6962(3) -0.1905(2) 0.6645(2) 0.0818(9) Uani 1 1 d . . .
H30A H 0.6401 -0.2508 0.6757 0.098 Uiso 1 1 calc R . .
H30B H 0.7655 -0.1753 0.5961 0.098 Uiso 1 1 calc R . .
C31 C 0.7971(3) -0.2252(2) 0.7482(2) 0.1246(13) Uani 1 1 d . . .
H31B H 0.8740 -0.2879 0.7448 0.187 Uiso 1 1 calc R . .
H31C H 0.7303 -0.2445 0.8166 0.187 Uiso 1 1 calc R . .
H31A H 0.8532 -0.1661 0.7379 0.187 Uiso 1 1 calc R . .
C32 C 0.4245(3) -0.1139(2) 0.7319(2) 0.0647(8) Uani 1 1 d . . .
H32A H 0.4104 -0.1895 0.7494 0.078 Uiso 1 1 calc R . .
H32B H 0.3369 -0.0668 0.6946 0.078 Uiso 1 1 calc R . .
C33 C 0.4132(3) -0.0953(2) 0.8336(2) 0.0851(9) Uani 1 1 d . . .
H33B H 0.3105 -0.1107 0.8763 0.128 Uiso 1 1 calc R . .
H33C H 0.4242 -0.0201 0.8172 0.128 Uiso 1 1 calc R . .
H33A H 0.4978 -0.1430 0.8721 0.128 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0553(4) 0.0609(6) 0.0532(5) -0.0194(4) -0.0014(4) -0.0018(4)
C1 0.0503(19) 0.062(2) 0.049(2) -0.0311(17) -0.0129(16) 0.0059(18)
N1 0.0507(15) 0.0511(17) 0.0528(16) -0.0219(13) -0.0118(13) 0.0016(14)
C2 0.0473(19) 0.047(2) 0.0395(19) -0.0195(16) -0.0117(15) -0.0007(17)
C3 0.0480(18) 0.045(2) 0.0397(18) -0.0157(16) -0.0041(14) -0.0023(16)
C4 0.052(2) 0.070(3) 0.058(2) -0.024(2) -0.0113(17) 0.007(2)
C5 0.056(3) 0.090(3) 0.068(3) -0.037(2) -0.0149(19) 0.0184(19)
N2 0.067(2) 0.112(3) 0.103(3) -0.032(2) 0.0017(16) 0.0097(16)
C6 0.054(2) 0.091(3) 0.064(3) -0.042(3) -0.0114(17) 0.013(2)
N3 0.0841(19) 0.084(2) 0.110(3) -0.042(2) -0.0216(16) 0.0188(18)
C7 0.052(2) 0.0399(19) 0.046(2) -0.0201(16) -0.0109(17) 0.0012(15)
C8 0.060(2) 0.056(2) 0.057(2) -0.0164(18) -0.0156(18) -0.0035(16)
C9 0.081(2) 0.054(2) 0.056(2) -0.0130(17) -0.011(2) -0.0087(18)
C10 0.073(2) 0.057(2) 0.069(3) -0.022(2) 0.0006(19) -0.0219(17)
C11 0.057(2) 0.068(2) 0.079(3) -0.036(2) -0.018(2) -0.0117(18)
C12 0.0630(19) 0.050(2) 0.051(2) -0.0200(16) -0.0121(17) -0.0068(16)
C13 0.0447(18) 0.047(2) 0.0374(18) -0.0159(16) -0.0034(15) -0.0075(16)
C14 0.0489(17) 0.049(2) 0.0423(19) -0.0145(17) 0.0024(14) -0.0060(16)
C15 0.0493(17) 0.051(2) 0.0435(19) -0.0159(17) -0.0034(14) -0.0065(16)
C16 0.0458(19) 0.0421(19) 0.043(2) -0.0120(15) -0.0128(17) 0.0005(14)
C17 0.0466(18) 0.0539(19) 0.047(2) -0.0202(16) -0.0080(16) -0.0084(14)
C18 0.067(2) 0.061(2) 0.044(2) -0.0252(16) 0.0038(19) -0.0181(17)
C19 0.056(2) 0.058(2) 0.074(3) -0.033(2) -0.001(2) -0.0143(17)
C20 0.048(2) 0.067(2) 0.073(2) -0.022(2) -0.0168(19) -0.0016(16)
C21 0.0591(19) 0.053(2) 0.054(2) -0.0134(16) -0.0102(18) -0.0063(16)
N4 0.0664(19) 0.117(2) 0.079(2) -0.0447(19) 0.0218(18) -0.0449(17)
C22 0.097(2) 0.097(3) 0.121(3) -0.052(3) 0.051(2) -0.052(2)
C23 0.055(2) 0.237(5) 0.164(4) -0.083(3) 0.007(2) -0.057(2)
C24 0.0425(18) 0.045(2) 0.0422(19) -0.0190(16) -0.0056(15) 0.0006(17)
C25 0.0446(18) 0.060(2) 0.055(2) -0.0156(18) 0.0020(15) -0.0072(18)
C26 0.0492(19) 0.046(2) 0.065(2) -0.0157(17) -0.0023(16) 0.0056(16)
C27 0.063(2) 0.041(2) 0.044(2) -0.0144(17) -0.0133(16) -0.0039(18)
C28 0.0494(18) 0.042(2) 0.052(2) -0.0154(17) -0.0019(14) -0.0020(17)
C29 0.0505(19) 0.041(2) 0.057(2) -0.0168(17) -0.0046(16) 0.0068(15)
N5 0.0696(18) 0.0430(18) 0.0589(17) -0.0160(14) -0.0056(14) -0.0042(14)
C30 0.093(2) 0.056(2) 0.083(3) -0.020(2) -0.0079(18) 0.0015(19)
C31 0.107(3) 0.111(3) 0.148(4) -0.041(3) -0.063(2) 0.033(2)
C32 0.080(2) 0.052(2) 0.062(2) -0.0163(17) -0.0084(18) -0.0200(16)
C33 0.112(2) 0.086(2) 0.062(2) -0.034(2) -0.0005(18) -0.0240(19)
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
S1 C1 1.733(2) . ?
S1 C3 1.755(2) . ?
C1 N1 1.350(2) . ?
C1 C4 1.379(3) . ?
N1 C2 1.333(2) . ?
C2 C3 1.418(3) . ?
C2 C7 1.481(3) . ?
C3 C13 1.392(3) . ?
C4 C5 1.410(3) . ?
C4 C6 1.411(3) . ?
C5 N2 1.158(3) . ?
C6 N3 1.138(3) . ?
C7 C8 1.372(3) . ?
C7 C12 1.391(3) . ?
C8 C9 1.381(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.370(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.371(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.408(3) . ?
C13 C16 1.481(3) . ?
C14 C15 1.362(3) . ?
C14 H14 0.9300 . ?
C15 C24 1.415(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(3) . ?
C16 C21 1.387(3) . ?
C17 C18 1.381(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.402(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.375(3) . ?
C19 N4 1.383(3) . ?
C20 C21 1.379(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
N4 C23 1.425(3) . ?
N4 C22 1.425(3) . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22 H22A 0.9600 . ?
C23 H23C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C24 C29 1.401(3) . ?
C24 C25 1.404(3) . ?
C25 C26 1.346(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.421(3) . ?
C26 H26 0.9300 . ?
C27 N5 1.337(3) . ?
C27 C28 1.411(3) . ?
C28 C29 1.347(3) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
N5 C32 1.460(2) . ?
N5 C30 1.471(3) . ?
C30 C31 1.467(3) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C31 H31A 0.9600 . ?
C32 C33 1.504(3) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C33 H33A 0.9600 . ?
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
C1 S1 C3 89.95(13) . . ?
N1 C1 C4 124.0(3) . . ?
N1 C1 S1 114.21(19) . . ?
C4 C1 S1 121.7(2) . . ?
C2 N1 C1 111.4(2) . . ?
N1 C2 C3 116.8(2) . . ?
N1 C2 C7 116.3(2) . . ?
C3 C2 C7 126.8(2) . . ?
C13 C3 C2 133.0(2) . . ?
C13 C3 S1 119.3(2) . . ?
C2 C3 S1 107.61(19) . . ?
C1 C4 C5 120.0(3) . . ?
C1 C4 C6 121.3(3) . . ?
C5 C4 C6 118.6(3) . . ?
N2 C5 C4 177.4(4) . . ?
N3 C6 C4 178.2(4) . . ?
C8 C7 C12 119.2(2) . . ?
C8 C7 C2 118.4(3) . . ?
C12 C7 C2 122.4(3) . . ?
C7 C8 C9 121.5(3) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C10 C9 C8 119.3(3) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 119.6(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 121.6(3) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C7 118.7(2) . . ?
C11 C12 H12 120.7 . . ?
C7 C12 H12 120.7 . . ?
C3 C13 C14 120.6(2) . . ?
C3 C13 C16 121.0(2) . . ?
C14 C13 C16 118.4(2) . . ?
C15 C14 C13 125.8(2) . . ?
C15 C14 H14 117.1 . . ?
C13 C14 H14 117.1 . . ?
C14 C15 C24 126.8(2) . . ?
C14 C15 H15 116.6 . . ?
C24 C15 H15 116.6 . . ?
C17 C16 C21 116.8(2) . . ?
C17 C16 C13 121.7(2) . . ?
C21 C16 C13 121.5(3) . . ?
C16 C17 C18 122.6(2) . . ?
C16 C17 H17 118.7 . . ?
C18 C17 H17 118.7 . . ?
C17 C18 C19 120.0(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C20 C19 N4 122.2(3) . . ?
C20 C19 C18 117.4(3) . . ?
N4 C19 C18 120.3(3) . . ?
C19 C20 C21 121.5(3) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C20 C21 C16 121.5(3) . . ?
C20 C21 H21 119.2 . . ?
C16 C21 H21 119.2 . . ?
C19 N4 C23 119.4(3) . . ?
C19 N4 C22 119.5(3) . . ?
C23 N4 C22 116.7(2) . . ?
N4 C22 H22B 109.5 . . ?
N4 C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N4 C22 H22A 109.5 . . ?
H22B C22 H22A 109.5 . . ?
H22C C22 H22A 109.5 . . ?
N4 C23 H23C 109.5 . . ?
N4 C23 H23A 109.5 . . ?
H23C C23 H23A 109.5 . . ?
N4 C23 H23B 109.5 . . ?
H23C C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C29 C24 C25 115.7(2) . . ?
C29 C24 C15 123.9(2) . . ?
C25 C24 C15 120.3(2) . . ?
C26 C25 C24 122.8(2) . . ?
C26 C25 H25 118.6 . . ?
C24 C25 H25 118.6 . . ?
C25 C26 C27 121.8(2) . . ?
C25 C26 H26 119.1 . . ?
C27 C26 H26 119.1 . . ?
N5 C27 C28 122.1(3) . . ?
N5 C27 C26 123.1(3) . . ?
C28 C27 C26 114.7(2) . . ?
C29 C28 C27 123.1(2) . . ?
C29 C28 H28 118.4 . . ?
C27 C28 H28 118.4 . . ?
C28 C29 C24 121.8(2) . . ?
C28 C29 H29 119.1 . . ?
C24 C29 H29 119.1 . . ?
C27 N5 C32 121.1(2) . . ?
C27 N5 C30 123.4(2) . . ?
C32 N5 C30 115.5(2) . . ?
C31 C30 N5 114.0(2) . . ?
C31 C30 H30A 108.7 . . ?
N5 C30 H30A 108.7 . . ?
C31 C30 H30B 108.7 . . ?
N5 C30 H30B 108.7 . . ?
H30A C30 H30B 107.6 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C31 H31A 109.5 . . ?
H31B C31 H31A 109.5 . . ?
H31C C31 H31A 109.5 . . ?
N5 C32 C33 114.10(19) . . ?
N5 C32 H32A 108.7 . . ?
C33 C32 H32A 108.7 . . ?
N5 C32 H32B 108.7 . . ?
C33 C32 H32B 108.7 . . ?
H32A C32 H32B 107.6 . . ?
C32 C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C33 H33A 109.5 . . ?
H33B C33 H33A 109.5 . . ?
H33C C33 H33A 109.5 . . ?
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
C3 S1 C1 N1 0.6(2) . . . . ?
C3 S1 C1 C4 -177.1(2) . . . . ?
C4 C1 N1 C2 176.4(2) . . . . ?
S1 C1 N1 C2 -1.3(3) . . . . ?
C1 N1 C2 C3 1.5(3) . . . . ?
C1 N1 C2 C7 -178.6(2) . . . . ?
N1 C2 C3 C13 175.7(2) . . . . ?
C7 C2 C3 C13 -4.2(4) . . . . ?
N1 C2 C3 S1 -1.0(3) . . . . ?
C7 C2 C3 S1 179.1(2) . . . . ?
C1 S1 C3 C13 -177.0(2) . . . . ?
C1 S1 C3 C2 0.20(19) . . . . ?
N1 C1 C4 C5 -177.7(3) . . . . ?
S1 C1 C4 C5 -0.3(4) . . . . ?
N1 C1 C4 C6 0.8(4) . . . . ?
S1 C1 C4 C6 178.2(2) . . . . ?
N1 C2 C7 C8 -54.2(3) . . . . ?
C3 C2 C7 C8 125.7(3) . . . . ?
N1 C2 C7 C12 124.8(2) . . . . ?
C3 C2 C7 C12 -55.3(4) . . . . ?
C12 C7 C8 C9 3.3(4) . . . . ?
C2 C7 C8 C9 -177.7(2) . . . . ?
C7 C8 C9 C10 -1.3(4) . . . . ?
C8 C9 C10 C11 -1.4(4) . . . . ?
C9 C10 C11 C12 2.3(4) . . . . ?
C10 C11 C12 C7 -0.3(4) . . . . ?
C8 C7 C12 C11 -2.4(4) . . . . ?
C2 C7 C12 C11 178.6(2) . . . . ?
C2 C3 C13 C14 176.9(3) . . . . ?
S1 C3 C13 C14 -6.7(3) . . . . ?
C2 C3 C13 C16 -3.8(4) . . . . ?
S1 C3 C13 C16 172.52(19) . . . . ?
C3 C13 C14 C15 174.6(2) . . . . ?
C16 C13 C14 C15 -4.6(4) . . . . ?
C13 C14 C15 C24 -179.4(3) . . . . ?
C3 C13 C16 C17 -59.6(3) . . . . ?
C14 C13 C16 C17 119.7(3) . . . . ?
C3 C13 C16 C21 119.2(3) . . . . ?
C14 C13 C16 C21 -61.5(3) . . . . ?
C21 C16 C17 C18 -1.6(4) . . . . ?
C13 C16 C17 C18 177.2(2) . . . . ?
C16 C17 C18 C19 -0.4(4) . . . . ?
C17 C18 C19 C20 1.6(4) . . . . ?
C17 C18 C19 N4 -178.7(2) . . . . ?
N4 C19 C20 C21 179.6(2) . . . . ?
C18 C19 C20 C21 -0.8(4) . . . . ?
C19 C20 C21 C16 -1.3(4) . . . . ?
C17 C16 C21 C20 2.4(4) . . . . ?
C13 C16 C21 C20 -176.4(2) . . . . ?
C20 C19 N4 C23 -14.8(4) . . . . ?
C18 C19 N4 C23 165.5(3) . . . . ?
C20 C19 N4 C22 -170.7(3) . . . . ?
C18 C19 N4 C22 9.6(4) . . . . ?
C14 C15 C24 C29 4.2(4) . . . . ?
C14 C15 C24 C25 -176.7(2) . . . . ?
C29 C24 C25 C26 -0.3(4) . . . . ?
C15 C24 C25 C26 -179.4(3) . . . . ?
C24 C25 C26 C27 1.0(4) . . . . ?
C25 C26 C27 N5 177.5(3) . . . . ?
C25 C26 C27 C28 -1.1(4) . . . . ?
N5 C27 C28 C29 -178.0(3) . . . . ?
C26 C27 C28 C29 0.6(4) . . . . ?
C27 C28 C29 C24 0.0(4) . . . . ?
C25 C24 C29 C28 -0.2(4) . . . . ?
C15 C24 C29 C28 178.9(3) . . . . ?
C28 C27 N5 C32 0.0(4) . . . . ?
C26 C27 N5 C32 -178.5(2) . . . . ?
C28 C27 N5 C30 -179.9(2) . . . . ?
C26 C27 N5 C30 1.6(4) . . . . ?
C27 N5 C30 C31 94.5(3) . . . . ?
C32 N5 C30 C31 -85.5(3) . . . . ?
C27 N5 C32 C33 -80.9(3) . . . . ?
C30 N5 C32 C33 99.1(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max 0.130
_refine_diff_density_min -0.146
_refine_diff_density_rms 0.030
data_7c
_database_code_depnum_ccdc_archive 'CCDC 894170'
#TrackingRef '12922_web_deposit_cif_file_0_ElenaGalan_1343579398.5a, 7c, 10.cif'
_audit_update_record
;
2011-04-18 # Formatted by publCIF
;
_audit_creation_method SHELXL-97
_chemical_name_systematic
'(3E,5Z)-7-(2,6-Di-tert-butyl-4H-pyran-4-ylidene)-6-(4-(dimethylamino)phenyl)2-phenylhepta-1,3,5-triene-1,1,3-tricarbonitrile '
_chemical_name_common ?
_chemical_formula_moiety 'C37 H38 N4 O'
_chemical_formula_sum 'C37 H38 N4 O'
_exptl_crystal_recrystallization_method
'diffusion of hexane into a solution of CHCl3 at r.t.'
_chemical_melting_point ?
_exptl_crystal_description plate
_exptl_crystal_colour blue
_diffrn_ambient_temperature 150(1)
_chemical_formula_weight 554.71
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'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_int_tables_number 14
_chemical_absolute_configuration ?
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 9.8471(5)
_cell_length_b 28.4321(15)
_cell_length_c 11.7509(8)
_cell_angle_alpha 90.00
_cell_angle_beta 106.763(6)
_cell_angle_gamma 90.00
_cell_volume 3150.1(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 150(1)
_cell_measurement_reflns_used 3163
_cell_measurement_theta_min 3.0414
_cell_measurement_theta_max 28.8017
_exptl_crystal_size_max 0.29
_exptl_crystal_size_mid 0.24
_exptl_crystal_size_min 0.04
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.170
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1184
_exptl_absorpt_coefficient_mu 0.071
_exptl_absorpt_correction_T_min 0.97650
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Multi-scan absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details ?
_diffrn_radiation_probe ?
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 16.3990
_diffrn_measurement_method \w-scans
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 24720
_diffrn_reflns_av_R_equivalents 0.0914
_diffrn_reflns_av_sigmaI/netI 0.1404
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -38
_diffrn_reflns_limit_k_max 36
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_theta_min 3.05
_diffrn_reflns_theta_max 28.87
_reflns_number_total 7462
_reflns_number_gt 3573
_reflns_threshold_expression >2\s(I)
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_structure_solution
;
#INFO: [SHELX76, SHELXTL, SHELXS86, SHELXTL-Plus,
SHELXTL/PC, SHELXL93, SHELXL97, SHELXS97]#
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics Mercury
_computing_publication_material 'Shelxl-97 (Sheldrick, 2008)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0229P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 7462
_refine_ls_number_parameters 387
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1690
_refine_ls_R_factor_gt 0.0685
_refine_ls_wR_factor_ref 0.1209
_refine_ls_wR_factor_gt 0.0916
_refine_ls_goodness_of_fit_ref 0.984
_refine_ls_restrained_S_all 0.984
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
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
O1 O 0.42100(15) 0.72087(5) 0.30583(13) 0.0274(4) Uani 1 1 d . . .
C1 C 0.2818(2) 0.71088(8) 0.2887(2) 0.0236(6) Uani 1 1 d . . .
C2 C 0.2431(2) 0.67561(8) 0.3487(2) 0.0255(6) Uani 1 1 d . . .
H2 H 0.1449 0.6691 0.3345 0.031 Uiso 1 1 calc R . .
C3 C 0.3437(2) 0.64746(8) 0.43319(19) 0.0226(6) Uani 1 1 d . . .
C4 C 0.4881(2) 0.65981(8) 0.4464(2) 0.0251(6) Uani 1 1 d . . .
H4 H 0.5615 0.6427 0.5010 0.030 Uiso 1 1 calc R . .
C5 C 0.5227(2) 0.69493(8) 0.3835(2) 0.0236(6) Uani 1 1 d . . .
C6 C 0.1882(2) 0.74165(9) 0.1942(2) 0.0294(6) Uani 1 1 d . . .
C7 C 0.1940(3) 0.72311(11) 0.0739(2) 0.0626(10) Uani 1 1 d . . .
H7A H 0.2922 0.7237 0.0704 0.094 Uiso 1 1 calc R . .
H7B H 0.1351 0.7430 0.0105 0.094 Uiso 1 1 calc R . .
H7C H 0.1584 0.6907 0.0634 0.094 Uiso 1 1 calc R . .
C8 C 0.2417(3) 0.79242(8) 0.2100(2) 0.0426(8) Uani 1 1 d . . .
H8A H 0.2475 0.8032 0.2905 0.064 Uiso 1 1 calc R . .
H8B H 0.1760 0.8126 0.1518 0.064 Uiso 1 1 calc R . .
H8C H 0.3359 0.7940 0.1977 0.064 Uiso 1 1 calc R . .
C9 C 0.0363(2) 0.74034(9) 0.2015(2) 0.0485(8) Uani 1 1 d . . .
H9A H -0.0020 0.7085 0.1836 0.073 Uiso 1 1 calc R . .
H9B H -0.0219 0.7625 0.1439 0.073 Uiso 1 1 calc R . .
H9C H 0.0350 0.7492 0.2818 0.073 Uiso 1 1 calc R . .
C10 C 0.6683(2) 0.71203(8) 0.3859(2) 0.0254(6) Uani 1 1 d . . .
C11 C 0.7821(2) 0.67713(9) 0.4505(3) 0.0471(8) Uani 1 1 d . . .
H11A H 0.7807 0.6740 0.5332 0.071 Uiso 1 1 calc R . .
H11B H 0.8754 0.6885 0.4486 0.071 Uiso 1 1 calc R . .
H11C H 0.7633 0.6464 0.4112 0.071 Uiso 1 1 calc R . .
C12 C 0.6751(3) 0.71889(11) 0.2585(2) 0.0523(8) Uani 1 1 d . . .
H12A H 0.6524 0.6891 0.2150 0.079 Uiso 1 1 calc R . .
H12B H 0.7707 0.7289 0.2600 0.079 Uiso 1 1 calc R . .
H12C H 0.6064 0.7430 0.2191 0.079 Uiso 1 1 calc R . .
C13 C 0.6938(3) 0.75957(8) 0.4487(2) 0.0391(7) Uani 1 1 d . . .
H13A H 0.6186 0.7815 0.4082 0.059 Uiso 1 1 calc R . .
H13B H 0.7859 0.7720 0.4466 0.059 Uiso 1 1 calc R . .
H13C H 0.6934 0.7557 0.5314 0.059 Uiso 1 1 calc R . .
C14 C 0.2950(2) 0.61009(8) 0.4877(2) 0.0249(6) Uani 1 1 d . . .
H14 H 0.1949 0.6061 0.4646 0.030 Uiso 1 1 calc R . .
C15 C 0.3715(2) 0.57755(8) 0.5714(2) 0.0208(5) Uani 1 1 d . . .
C16 C 0.3026(2) 0.53860(8) 0.6026(2) 0.0239(6) Uani 1 1 d . . .
H16 H 0.2055 0.5333 0.5619 0.029 Uiso 1 1 calc R . .
C17 C 0.3719(2) 0.50781(8) 0.6906(2) 0.0227(6) Uani 1 1 d . . .
H17 H 0.4686 0.5149 0.7288 0.027 Uiso 1 1 calc R . .
C18 C 0.3194(2) 0.46736(8) 0.7318(2) 0.0221(5) Uani 1 1 d . . .
C19 C 0.4081(2) 0.43949(8) 0.8237(2) 0.0229(6) Uani 1 1 d . . .
C20 C 0.3644(2) 0.40394(8) 0.8848(2) 0.0267(6) Uani 1 1 d . . .
C21 C 0.5263(2) 0.58273(8) 0.6286(2) 0.0206(5) Uani 1 1 d . . .
C22 C 0.6233(2) 0.55663(8) 0.5890(2) 0.0273(6) Uani 1 1 d . . .
H22 H 0.5894 0.5344 0.5268 0.033 Uiso 1 1 calc R . .
C23 C 0.7669(2) 0.56218(8) 0.6377(2) 0.0282(6) Uani 1 1 d . . .
H23 H 0.8303 0.5445 0.6071 0.034 Uiso 1 1 calc R . .
C24 C 0.8214(2) 0.59349(8) 0.7318(2) 0.0270(6) Uani 1 1 d . . .
C25 C 0.7231(2) 0.61860(8) 0.7733(2) 0.0297(6) Uani 1 1 d . . .
H25 H 0.7563 0.6397 0.8381 0.036 Uiso 1 1 calc R . .
C26 C 0.5790(2) 0.61352(8) 0.7222(2) 0.0284(6) Uani 1 1 d . . .
H26 H 0.5150 0.6314 0.7517 0.034 Uiso 1 1 calc R . .
N1 N 0.9658(2) 0.59910(8) 0.78104(18) 0.0364(6) Uani 1 1 d . . .
C27 C 1.0604(2) 0.58293(10) 0.7156(2) 0.0409(7) Uani 1 1 d . . .
H27A H 1.0531 0.5487 0.7069 0.061 Uiso 1 1 calc R . .
H27B H 1.1581 0.5915 0.7587 0.061 Uiso 1 1 calc R . .
H27C H 1.0342 0.5976 0.6368 0.061 Uiso 1 1 calc R . .
C28 C 1.0185(2) 0.63434(9) 0.8719(2) 0.0373(7) Uani 1 1 d . . .
H28A H 0.9888 0.6656 0.8389 0.056 Uiso 1 1 calc R . .
H28B H 1.1223 0.6329 0.8996 0.056 Uiso 1 1 calc R . .
H28C H 0.9800 0.6284 0.9387 0.056 Uiso 1 1 calc R . .
C29 C 0.1734(3) 0.45546(8) 0.6745(2) 0.0272(6) Uani 1 1 d . . .
N2 N 0.0579(2) 0.44777(8) 0.6241(2) 0.0456(7) Uani 1 1 d . . .
C30 C 0.5643(2) 0.44791(8) 0.8560(2) 0.0244(6) Uani 1 1 d . . .
C31 C 0.6371(2) 0.44015(8) 0.7725(2) 0.0302(6) Uani 1 1 d . . .
H31 H 0.5867 0.4305 0.6944 0.036 Uiso 1 1 calc R . .
C32 C 0.7816(3) 0.44635(9) 0.8023(2) 0.0385(7) Uani 1 1 d . . .
H32 H 0.8310 0.4402 0.7453 0.046 Uiso 1 1 calc R . .
C33 C 0.8547(3) 0.46145(9) 0.9147(3) 0.0417(7) Uani 1 1 d . . .
H33 H 0.9545 0.4658 0.9350 0.050 Uiso 1 1 calc R . .
C34 C 0.7837(3) 0.47019(9) 0.9978(2) 0.0389(7) Uani 1 1 d . . .
H34 H 0.8342 0.4812 1.0747 0.047 Uiso 1 1 calc R . .
C35 C 0.6384(2) 0.46292(8) 0.9689(2) 0.0318(6) Uani 1 1 d . . .
H35 H 0.5898 0.4683 1.0268 0.038 Uiso 1 1 calc R . .
C36 C 0.2201(3) 0.39164(9) 0.8729(2) 0.0342(7) Uani 1 1 d . . .
N3 N 0.1064(2) 0.37981(8) 0.8665(2) 0.0517(7) Uani 1 1 d . . .
C37 C 0.4662(3) 0.37481(9) 0.9671(2) 0.0335(7) Uani 1 1 d . . .
N4 N 0.5452(2) 0.35111(8) 1.0324(2) 0.0476(7) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0229(10) 0.0288(10) 0.0283(10) 0.0042(8) 0.0038(7) -0.0014(8)
C1 0.0191(13) 0.0249(14) 0.0245(14) -0.0020(11) 0.0025(11) -0.0018(11)
C2 0.0188(13) 0.0301(14) 0.0264(15) 0.0014(12) 0.0047(11) -0.0027(11)
C3 0.0216(14) 0.0266(14) 0.0189(14) -0.0020(11) 0.0045(10) -0.0003(11)
C4 0.0232(14) 0.0243(14) 0.0261(15) 0.0036(12) 0.0040(11) 0.0003(11)
C5 0.0219(14) 0.0249(14) 0.0238(14) -0.0021(12) 0.0060(11) 0.0028(11)
C6 0.0284(15) 0.0289(15) 0.0273(15) 0.0040(12) 0.0020(12) -0.0028(12)
C7 0.088(2) 0.061(2) 0.0285(18) 0.0008(17) 0.0016(17) 0.0134(19)
C8 0.0374(17) 0.0315(16) 0.0515(19) 0.0096(14) 0.0009(14) 0.0025(13)
C9 0.0282(16) 0.0469(18) 0.059(2) 0.0176(16) -0.0053(14) -0.0006(13)
C10 0.0221(14) 0.0277(14) 0.0278(15) -0.0018(12) 0.0096(11) -0.0032(11)
C11 0.0246(15) 0.0347(16) 0.082(2) 0.0074(16) 0.0147(15) -0.0006(13)
C12 0.0369(18) 0.086(2) 0.0398(18) -0.0103(17) 0.0195(14) -0.0130(16)
C13 0.0365(16) 0.0317(15) 0.0480(19) -0.0059(14) 0.0105(13) -0.0056(13)
C14 0.0179(13) 0.0274(14) 0.0289(15) 0.0027(12) 0.0061(11) -0.0009(11)
C15 0.0207(13) 0.0242(13) 0.0190(13) -0.0044(11) 0.0080(10) 0.0007(11)
C16 0.0189(13) 0.0246(14) 0.0282(15) -0.0027(12) 0.0066(11) -0.0008(11)
C17 0.0203(13) 0.0266(14) 0.0228(14) -0.0034(11) 0.0087(10) 0.0022(11)
C18 0.0201(13) 0.0221(13) 0.0236(14) -0.0006(11) 0.0055(10) -0.0006(10)
C19 0.0262(14) 0.0225(13) 0.0209(14) -0.0041(11) 0.0083(11) 0.0005(11)
C20 0.0261(15) 0.0270(14) 0.0282(15) 0.0025(12) 0.0095(11) 0.0007(11)
C21 0.0200(13) 0.0210(13) 0.0219(14) 0.0038(11) 0.0079(10) 0.0003(10)
C22 0.0245(14) 0.0271(14) 0.0298(15) -0.0055(12) 0.0073(11) -0.0013(11)
C23 0.0237(14) 0.0288(14) 0.0348(16) -0.0073(13) 0.0130(12) 0.0027(11)
C24 0.0199(14) 0.0314(15) 0.0294(15) -0.0024(12) 0.0069(11) -0.0002(11)
C25 0.0282(15) 0.0319(15) 0.0285(15) -0.0119(12) 0.0077(12) -0.0011(12)
C26 0.0244(14) 0.0341(15) 0.0275(15) -0.0058(12) 0.0086(11) 0.0059(12)
N1 0.0189(12) 0.0503(15) 0.0393(14) -0.0167(12) 0.0071(10) -0.0042(10)
C27 0.0245(15) 0.0544(19) 0.0459(19) -0.0095(15) 0.0132(13) 0.0001(13)
C28 0.0253(15) 0.0440(17) 0.0409(18) -0.0101(14) 0.0068(12) -0.0061(13)
C29 0.0284(15) 0.0248(14) 0.0308(16) 0.0027(12) 0.0122(12) -0.0009(12)
N2 0.0290(14) 0.0524(16) 0.0493(16) 0.0091(13) 0.0018(12) -0.0092(12)
C30 0.0220(14) 0.0214(13) 0.0289(15) -0.0003(12) 0.0059(11) 0.0004(11)
C31 0.0252(15) 0.0323(15) 0.0322(16) -0.0040(13) 0.0068(12) -0.0012(12)
C32 0.0276(16) 0.0447(18) 0.0471(19) -0.0095(15) 0.0170(13) -0.0010(13)
C33 0.0241(15) 0.0418(18) 0.055(2) -0.0058(16) 0.0047(14) -0.0029(13)
C34 0.0322(16) 0.0432(17) 0.0354(17) -0.0062(14) 0.0005(13) -0.0050(13)
C35 0.0302(15) 0.0334(15) 0.0304(16) -0.0028(13) 0.0068(12) -0.0003(12)
C36 0.0357(17) 0.0321(16) 0.0375(17) 0.0082(13) 0.0149(13) -0.0013(13)
N3 0.0408(15) 0.0535(17) 0.0684(19) 0.0150(14) 0.0278(13) -0.0017(13)
C37 0.0347(16) 0.0356(16) 0.0316(17) 0.0013(14) 0.0117(13) -0.0050(13)
N4 0.0467(15) 0.0479(16) 0.0465(16) 0.0156(13) 0.0105(12) 0.0041(12)
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
O1 C1 1.357(2) . ?
O1 C5 1.361(2) . ?
C1 C2 1.343(3) . ?
C1 C6 1.502(3) . ?
C2 C3 1.428(3) . ?
C2 H2 0.9500 . ?
C3 C14 1.395(3) . ?
C3 C4 1.429(3) . ?
C4 C5 1.343(3) . ?
C4 H4 0.9500 . ?
C5 C10 1.507(3) . ?
C6 C9 1.524(3) . ?
C6 C7 1.526(3) . ?
C6 C8 1.529(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.525(3) . ?
C10 C13 1.525(3) . ?
C10 C12 1.529(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.401(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.401(3) . ?
C15 C21 1.485(3) . ?
C16 C17 1.377(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.403(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.419(3) . ?
C18 C29 1.442(3) . ?
C19 C20 1.378(3) . ?
C19 C30 1.493(3) . ?
C20 C36 1.430(3) . ?
C20 C37 1.438(3) . ?
C21 C26 1.385(3) . ?
C21 C22 1.391(3) . ?
C22 C23 1.372(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.400(3) . ?
C23 H23 0.9500 . ?
C24 N1 1.381(3) . ?
C24 C25 1.399(3) . ?
C25 C26 1.379(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
N1 C27 1.443(3) . ?
N1 C28 1.447(3) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 N2 1.141(3) . ?
C30 C35 1.385(3) . ?
C30 C31 1.389(3) . ?
C31 C32 1.375(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.378(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.377(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.387(3) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 N3 1.151(3) . ?
C37 N4 1.142(3) . ?
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
C1 O1 C5 120.15(18) . . ?
C2 C1 O1 120.4(2) . . ?
C2 C1 C6 128.1(2) . . ?
O1 C1 C6 111.4(2) . . ?
C1 C2 C3 122.6(2) . . ?
C1 C2 H2 118.7 . . ?
C3 C2 H2 118.7 . . ?
C14 C3 C2 119.0(2) . . ?
C14 C3 C4 126.9(2) . . ?
C2 C3 C4 114.0(2) . . ?
C5 C4 C3 121.7(2) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 O1 121.2(2) . . ?
C4 C5 C10 128.3(2) . . ?
O1 C5 C10 110.5(2) . . ?
C1 C6 C9 110.3(2) . . ?
C1 C6 C7 107.8(2) . . ?
C9 C6 C7 110.1(2) . . ?
C1 C6 C8 110.12(19) . . ?
C9 C6 C8 109.0(2) . . ?
C7 C6 C8 109.6(2) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 C11 111.0(2) . . ?
C5 C10 C13 108.5(2) . . ?
C11 C10 C13 109.9(2) . . ?
C5 C10 C12 109.42(19) . . ?
C11 C10 C12 109.7(2) . . ?
C13 C10 C12 108.2(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C14 C15 129.7(2) . . ?
C3 C14 H14 115.2 . . ?
C15 C14 H14 115.2 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 C21 118.1(2) . . ?
C14 C15 C21 121.7(2) . . ?
C17 C16 C15 121.8(2) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C16 C17 C18 128.9(2) . . ?
C16 C17 H17 115.5 . . ?
C18 C17 H17 115.5 . . ?
C17 C18 C19 120.9(2) . . ?
C17 C18 C29 116.6(2) . . ?
C19 C18 C29 122.4(2) . . ?
C20 C19 C18 126.1(2) . . ?
C20 C19 C30 116.0(2) . . ?
C18 C19 C30 117.8(2) . . ?
C19 C20 C36 125.4(2) . . ?
C19 C20 C37 120.7(2) . . ?
C36 C20 C37 113.9(2) . . ?
C26 C21 C22 117.8(2) . . ?
C26 C21 C15 121.5(2) . . ?
C22 C21 C15 120.7(2) . . ?
C23 C22 C21 121.5(2) . . ?
C23 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C22 C23 C24 121.1(2) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
N1 C24 C25 121.8(2) . . ?
N1 C24 C23 121.2(2) . . ?
C25 C24 C23 117.0(2) . . ?
C26 C25 C24 121.5(2) . . ?
C26 C25 H25 119.2 . . ?
C24 C25 H25 119.2 . . ?
C25 C26 C21 121.0(2) . . ?
C25 C26 H26 119.5 . . ?
C21 C26 H26 119.5 . . ?
C24 N1 C27 119.0(2) . . ?
C24 N1 C28 119.7(2) . . ?
C27 N1 C28 117.7(2) . . ?
N1 C27 H27A 109.5 . . ?
N1 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N1 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N1 C28 H28A 109.5 . . ?
N1 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N1 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N2 C29 C18 176.1(3) . . ?
C35 C30 C31 119.2(2) . . ?
C35 C30 C19 120.8(2) . . ?
C31 C30 C19 119.9(2) . . ?
C32 C31 C30 120.5(2) . . ?
C32 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C31 C32 C33 120.0(2) . . ?
C31 C32 H32 120.0 . . ?
C33 C32 H32 120.0 . . ?
C34 C33 C32 120.3(2) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C33 C34 C35 119.9(2) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C30 C35 C34 120.1(2) . . ?
C30 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
N3 C36 C20 176.7(3) . . ?
N4 C37 C20 178.8(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
C5 O1 C1 C2 0.5(3) . . . . ?
C5 O1 C1 C6 -176.46(19) . . . . ?
O1 C1 C2 C3 0.7(4) . . . . ?
C6 C1 C2 C3 177.1(2) . . . . ?
C1 C2 C3 C14 -177.1(2) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C14 C3 C4 C5 175.8(2) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 O1 1.2(3) . . . . ?
C3 C4 C5 C10 -179.4(2) . . . . ?
C1 O1 C5 C4 -1.4(3) . . . . ?
C1 O1 C5 C10 179.08(19) . . . . ?
C2 C1 C6 C9 20.0(4) . . . . ?
O1 C1 C6 C9 -163.4(2) . . . . ?
C2 C1 C6 C7 -100.2(3) . . . . ?
O1 C1 C6 C7 76.4(2) . . . . ?
C2 C1 C6 C8 140.4(3) . . . . ?
O1 C1 C6 C8 -43.0(3) . . . . ?
C4 C5 C10 C11 13.1(3) . . . . ?
O1 C5 C10 C11 -167.47(19) . . . . ?
C4 C5 C10 C13 -107.9(3) . . . . ?
O1 C5 C10 C13 71.6(2) . . . . ?
C4 C5 C10 C12 134.2(3) . . . . ?
O1 C5 C10 C12 -46.3(3) . . . . ?
C2 C3 C14 C15 179.3(2) . . . . ?
C4 C3 C14 C15 3.7(4) . . . . ?
C3 C14 C15 C16 -171.1(2) . . . . ?
C3 C14 C15 C21 8.3(4) . . . . ?
C14 C15 C16 C17 -175.2(2) . . . . ?
C21 C15 C16 C17 5.4(3) . . . . ?
C15 C16 C17 C18 -179.5(2) . . . . ?
C16 C17 C18 C19 179.5(2) . . . . ?
C16 C17 C18 C29 0.7(4) . . . . ?
C17 C18 C19 C20 168.6(2) . . . . ?
C29 C18 C19 C20 -12.7(4) . . . . ?
C17 C18 C19 C30 -13.5(3) . . . . ?
C29 C18 C19 C30 165.2(2) . . . . ?
C18 C19 C20 C36 -5.7(4) . . . . ?
C30 C19 C20 C36 176.4(2) . . . . ?
C18 C19 C20 C37 173.1(2) . . . . ?
C30 C19 C20 C37 -4.9(3) . . . . ?
C16 C15 C21 C26 -101.1(3) . . . . ?
C14 C15 C21 C26 79.5(3) . . . . ?
C16 C15 C21 C22 79.1(3) . . . . ?
C14 C15 C21 C22 -100.3(3) . . . . ?
C26 C21 C22 C23 -2.3(3) . . . . ?
C15 C21 C22 C23 177.6(2) . . . . ?
C21 C22 C23 C24 1.9(4) . . . . ?
C22 C23 C24 N1 180.0(2) . . . . ?
C22 C23 C24 C25 0.0(4) . . . . ?
N1 C24 C25 C26 178.7(2) . . . . ?
C23 C24 C25 C26 -1.3(4) . . . . ?
C24 C25 C26 C21 0.9(4) . . . . ?
C22 C21 C26 C25 0.9(3) . . . . ?
C15 C21 C26 C25 -178.9(2) . . . . ?
C25 C24 N1 C27 -162.9(2) . . . . ?
C23 C24 N1 C27 17.1(4) . . . . ?
C25 C24 N1 C28 -4.8(4) . . . . ?
C23 C24 N1 C28 175.2(2) . . . . ?
C20 C19 C30 C35 -63.8(3) . . . . ?
C18 C19 C30 C35 118.0(3) . . . . ?
C20 C19 C30 C31 115.4(3) . . . . ?
C18 C19 C30 C31 -62.7(3) . . . . ?
C35 C30 C31 C32 1.3(4) . . . . ?
C19 C30 C31 C32 -178.0(2) . . . . ?
C30 C31 C32 C33 -1.6(4) . . . . ?
C31 C32 C33 C34 0.3(4) . . . . ?
C32 C33 C34 C35 1.2(4) . . . . ?
C31 C30 C35 C34 0.2(4) . . . . ?
C19 C30 C35 C34 179.4(2) . . . . ?
C33 C34 C35 C30 -1.4(4) . . . . ?
_diffrn_measured_fraction_theta_max 0.903
_diffrn_reflns_theta_full 27.50
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max 0.218
_refine_diff_density_min -0.221
_refine_diff_density_rms 0.050
data_10
_database_code_depnum_ccdc_archive 'CCDC 894171'
#TrackingRef '12922_web_deposit_cif_file_0_ElenaGalan_1343579398.5a, 7c, 10.cif'
_audit_update_record
;
2011-04-14 # Formatted by publCIF
;
_audit_creation_method SHELXL-97
_chemical_name_systematic
"4-Dimethylamino-[1,1': 3',1''-terphenyl]-2',4'-dicarbonitrile-5'-[2, 6-di-tert-butyl-4H-pyran-4-ylidene] "
_chemical_name_common ?
_chemical_formula_moiety 'C36 H37 N3 O'
_chemical_formula_sum 'C36 H37 N3 O'
_exptl_crystal_recrystallization_method
'diffusion of hexane into a solution of CH2Cl2 at r.t.'
_chemical_melting_point ?
_exptl_crystal_description needle
_exptl_crystal_colour orange
_diffrn_ambient_temperature 150(1)
_chemical_formula_weight 527.69
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'
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_int_tables_number 2
_chemical_absolute_configuration ?
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 5.9702(5)
_cell_length_b 12.9502(14)
_cell_length_c 20.426(2)
_cell_angle_alpha 104.108(9)
_cell_angle_beta 92.797(8)
_cell_angle_gamma 95.045(8)
_cell_volume 1521.6(3)
_cell_formula_units_Z 2
_cell_measurement_temperature 150(1)
_cell_measurement_reflns_used 1038
_cell_measurement_theta_min 2.9244
_cell_measurement_theta_max 28.8735
_exptl_crystal_size_max 0.34
_exptl_crystal_size_mid 0.05
_exptl_crystal_size_min 0.04
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.152
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 564
_exptl_absorpt_coefficient_mu 0.069
_exptl_absorpt_correction_T_min 0.86157
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Multi-scan absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details ?
_diffrn_radiation_probe ?
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 16.3990
_diffrn_measurement_method \w-scans
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 9971
_diffrn_reflns_av_R_equivalents 0.0851
_diffrn_reflns_av_sigmaI/netI 0.2091
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_limit_l_max 24
_diffrn_reflns_theta_min 2.93
_diffrn_reflns_theta_max 25.00
_reflns_number_total 5343
_reflns_number_gt 2142
_reflns_threshold_expression >2\s(I)
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_structure_solution SIR-92
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics Mercury
_computing_publication_material 'SHELXL-97 (Sheldrick, 2008)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0164P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 5343
_refine_ls_number_parameters 361
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.2233
_refine_ls_R_factor_gt 0.0804
_refine_ls_wR_factor_ref 0.1405
_refine_ls_wR_factor_gt 0.0971
_refine_ls_goodness_of_fit_ref 0.968
_refine_ls_restrained_S_all 0.968
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
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
O1 O 0.2548(4) 0.2239(2) 0.57390(15) 0.0350(8) Uani 1 1 d . . .
C1 C 0.3849(7) 0.2521(4) 0.6343(2) 0.0299(11) Uani 1 1 d . . .
C2 C 0.4778(7) 0.3526(3) 0.6603(2) 0.0321(11) Uani 1 1 d . . .
H2 H 0.5661 0.3692 0.7021 0.039 Uiso 1 1 calc R . .
C3 C 0.4468(7) 0.4371(4) 0.6258(2) 0.0364(12) Uani 1 1 d . . .
C4 C 0.2937(7) 0.4018(4) 0.5658(2) 0.0423(13) Uani 1 1 d . . .
H4 H 0.2552 0.4537 0.5425 0.051 Uiso 1 1 calc R . .
C5 C 0.2032(7) 0.3012(4) 0.5412(2) 0.0342(12) Uani 1 1 d . . .
C6 C 0.3979(7) 0.1566(4) 0.6642(2) 0.0347(12) Uani 1 1 d . . .
C7 C 0.4916(7) 0.0672(3) 0.6135(2) 0.0445(14) Uani 1 1 d . . .
H7A H 0.4995 0.0050 0.6326 0.067 Uiso 1 1 calc R . .
H7B H 0.6429 0.0920 0.6034 0.067 Uiso 1 1 calc R . .
H7C H 0.3926 0.0469 0.5717 0.067 Uiso 1 1 calc R . .
C8 C 0.1594(6) 0.1185(4) 0.6784(2) 0.0510(15) Uani 1 1 d . . .
H8A H 0.1645 0.0565 0.6978 0.076 Uiso 1 1 calc R . .
H8B H 0.0633 0.0982 0.6361 0.076 Uiso 1 1 calc R . .
H8C H 0.0977 0.1765 0.7105 0.076 Uiso 1 1 calc R . .
C9 C 0.5487(7) 0.1855(3) 0.7295(2) 0.0407(13) Uani 1 1 d . . .
H9A H 0.5536 0.1224 0.7478 0.061 Uiso 1 1 calc R . .
H9B H 0.4884 0.2428 0.7625 0.061 Uiso 1 1 calc R . .
H9C H 0.7013 0.2099 0.7203 0.061 Uiso 1 1 calc R . .
C10 C 0.0462(7) 0.2552(4) 0.4798(2) 0.0335(12) Uani 1 1 d . . .
C11 C -0.0152(8) 0.3419(4) 0.4462(3) 0.0731(18) Uani 1 1 d . . .
H11A H -0.1185 0.3103 0.4061 0.110 Uiso 1 1 calc R . .
H11B H 0.1217 0.3761 0.4326 0.110 Uiso 1 1 calc R . .
H11C H -0.0887 0.3956 0.4781 0.110 Uiso 1 1 calc R . .
C12 C 0.1586(7) 0.1711(4) 0.4302(2) 0.0630(16) Uani 1 1 d . . .
H12A H 0.0566 0.1413 0.3896 0.094 Uiso 1 1 calc R . .
H12B H 0.1930 0.1137 0.4515 0.094 Uiso 1 1 calc R . .
H12C H 0.2985 0.2042 0.4175 0.094 Uiso 1 1 calc R . .
C13 C -0.1681(7) 0.2022(4) 0.5001(2) 0.0679(18) Uani 1 1 d . . .
H13A H -0.2722 0.1729 0.4599 0.102 Uiso 1 1 calc R . .
H13B H -0.2396 0.2554 0.5329 0.102 Uiso 1 1 calc R . .
H13C H -0.1306 0.1443 0.5205 0.102 Uiso 1 1 calc R . .
C14 C 0.5363(7) 0.5407(4) 0.6463(2) 0.0392(13) Uani 1 1 d . . .
H14 H 0.4868 0.5867 0.6200 0.047 Uiso 1 1 calc R . .
C15 C 0.6970(7) 0.5905(4) 0.7028(2) 0.0331(12) Uani 1 1 d . . .
C16 C 0.8615(7) 0.5372(4) 0.7279(2) 0.0338(12) Uani 1 1 d . . .
H16 H 0.8764 0.4654 0.7046 0.041 Uiso 1 1 calc R . .
C17 C 1.0048(7) 0.5838(4) 0.7851(2) 0.0294(12) Uani 1 1 d . . .
C18 C 0.9893(7) 0.6926(3) 0.8171(2) 0.0284(11) Uani 1 1 d . . .
C19 C 0.8395(7) 0.7522(4) 0.7912(2) 0.0306(12) Uani 1 1 d . . .
C20 C 0.6942(7) 0.7017(3) 0.7353(2) 0.0287(11) Uani 1 1 d . . .
C21 C 1.1587(7) 0.5206(3) 0.8133(2) 0.0287(11) Uani 1 1 d . . .
C22 C 1.0808(7) 0.4190(3) 0.8200(2) 0.0336(12) Uani 1 1 d . . .
H22 H 0.9353 0.3878 0.8005 0.040 Uiso 1 1 calc R . .
C23 C 1.2094(7) 0.3629(4) 0.8542(2) 0.0360(12) Uani 1 1 d . . .
H23 H 1.1512 0.2937 0.8572 0.043 Uiso 1 1 calc R . .
C24 C 1.4234(7) 0.4054(4) 0.8846(2) 0.0341(12) Uani 1 1 d . . .
C25 C 1.5116(7) 0.5033(4) 0.8733(2) 0.0385(13) Uani 1 1 d . . .
H25 H 1.6626 0.5312 0.8887 0.046 Uiso 1 1 calc R . .
C26 C 1.3795(7) 0.5587(4) 0.8398(2) 0.0343(12) Uani 1 1 d . . .
H26 H 1.4410 0.6260 0.8343 0.041 Uiso 1 1 calc R . .
N1 N 1.5452(6) 0.3535(3) 0.92356(19) 0.0424(11) Uani 1 1 d . . .
C27 C 1.4243(7) 0.2663(4) 0.9460(3) 0.0616(16) Uani 1 1 d . . .
H27A H 1.5290 0.2363 0.9731 0.092 Uiso 1 1 calc R . .
H27B H 1.3605 0.2102 0.9064 0.092 Uiso 1 1 calc R . .
H27C H 1.3025 0.2940 0.9735 0.092 Uiso 1 1 calc R . .
C28 C 1.7433(7) 0.4091(4) 0.9645(2) 0.0447(14) Uani 1 1 d . . .
H28A H 1.8096 0.3612 0.9888 0.067 Uiso 1 1 calc R . .
H28B H 1.7015 0.4721 0.9972 0.067 Uiso 1 1 calc R . .
H28C H 1.8534 0.4317 0.9354 0.067 Uiso 1 1 calc R . .
C29 C 1.1158(8) 0.7435(4) 0.8805(3) 0.0357(12) Uani 1 1 d . . .
N2 N 1.2076(7) 0.7842(3) 0.9316(2) 0.0524(12) Uani 1 1 d . . .
C30 C 0.8357(7) 0.8678(3) 0.8249(2) 0.0315(12) Uani 1 1 d . . .
C31 C 0.7127(9) 0.9008(4) 0.8792(3) 0.080(2) Uani 1 1 d . . .
H31 H 0.6198 0.8493 0.8944 0.096 Uiso 1 1 calc R . .
C32 C 0.7200(9) 1.0068(5) 0.9123(3) 0.096(3) Uani 1 1 d . . .
H32 H 0.6347 1.0278 0.9506 0.115 Uiso 1 1 calc R . .
C33 C 0.8484(9) 1.0815(4) 0.8907(3) 0.0603(16) Uani 1 1 d . . .
H33 H 0.8533 1.1551 0.9133 0.072 Uiso 1 1 calc R . .
C34 C 0.9697(9) 1.0497(4) 0.8365(3) 0.076(2) Uani 1 1 d . . .
H34 H 1.0595 1.1016 0.8207 0.091 Uiso 1 1 calc R . .
C35 C 0.9645(9) 0.9432(4) 0.8041(3) 0.0634(18) Uani 1 1 d . . .
H35 H 1.0526 0.9222 0.7665 0.076 Uiso 1 1 calc R . .
C36 C 0.5305(8) 0.7624(4) 0.7120(2) 0.0357(12) Uani 1 1 d . . .
N3 N 0.3959(6) 0.8098(3) 0.6935(2) 0.0491(12) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.045(2) 0.0233(19) 0.035(2) 0.0069(17) -0.0045(16) 0.0021(15)
C1 0.029(3) 0.026(3) 0.033(3) 0.003(3) 0.002(2) 0.007(2)
C2 0.037(3) 0.027(3) 0.032(3) 0.008(3) -0.007(2) 0.005(2)
C3 0.050(3) 0.020(3) 0.035(3) 0.002(3) -0.010(2) 0.002(2)
C4 0.058(3) 0.028(3) 0.041(3) 0.012(3) -0.018(3) 0.004(3)
C5 0.039(3) 0.028(3) 0.038(3) 0.012(3) -0.002(2) 0.007(2)
C6 0.037(3) 0.028(3) 0.042(3) 0.011(3) 0.007(2) 0.002(2)
C7 0.062(3) 0.026(3) 0.049(4) 0.013(3) 0.001(3) 0.013(3)
C8 0.045(3) 0.060(4) 0.057(4) 0.034(3) 0.006(3) 0.004(3)
C9 0.047(3) 0.034(3) 0.043(3) 0.014(3) -0.002(3) 0.006(2)
C10 0.038(3) 0.026(3) 0.033(3) 0.004(3) -0.007(2) 0.002(2)
C11 0.094(4) 0.045(4) 0.073(4) 0.017(4) -0.053(3) -0.004(3)
C12 0.072(4) 0.070(5) 0.039(4) -0.001(3) -0.008(3) 0.011(3)
C13 0.049(4) 0.090(5) 0.057(4) 0.010(4) -0.004(3) -0.010(3)
C14 0.052(3) 0.021(3) 0.045(3) 0.011(3) -0.013(3) 0.007(2)
C15 0.045(3) 0.026(3) 0.031(3) 0.014(3) -0.003(2) -0.001(2)
C16 0.047(3) 0.022(3) 0.031(3) 0.006(2) -0.001(2) 0.001(2)
C17 0.033(3) 0.026(3) 0.029(3) 0.010(2) 0.001(2) -0.005(2)
C18 0.038(3) 0.018(3) 0.029(3) 0.007(2) -0.002(2) -0.005(2)
C19 0.041(3) 0.028(3) 0.024(3) 0.010(2) 0.005(2) -0.002(2)
C20 0.040(3) 0.018(3) 0.029(3) 0.009(2) -0.001(2) 0.001(2)
C21 0.033(3) 0.024(3) 0.029(3) 0.008(2) 0.001(2) 0.003(2)
C22 0.033(3) 0.026(3) 0.038(3) 0.005(3) -0.003(2) -0.001(2)
C23 0.045(3) 0.023(3) 0.039(3) 0.005(3) -0.001(2) 0.009(2)
C24 0.037(3) 0.032(3) 0.033(3) 0.005(3) 0.002(2) 0.012(2)
C25 0.030(3) 0.044(3) 0.041(3) 0.009(3) 0.003(2) 0.006(2)
C26 0.035(3) 0.035(3) 0.034(3) 0.010(3) 0.010(2) 0.000(2)
N1 0.042(3) 0.036(3) 0.048(3) 0.008(2) -0.006(2) 0.010(2)
C27 0.065(4) 0.048(4) 0.077(4) 0.027(4) -0.016(3) 0.015(3)
C28 0.046(3) 0.051(4) 0.041(3) 0.016(3) -0.001(3) 0.016(3)
C29 0.045(3) 0.025(3) 0.040(3) 0.013(3) -0.003(3) 0.005(2)
N2 0.070(3) 0.043(3) 0.042(3) 0.009(3) -0.015(2) 0.012(2)
C30 0.046(3) 0.019(3) 0.026(3) 0.001(2) -0.002(2) 0.000(2)
C31 0.101(5) 0.023(4) 0.109(5) -0.004(4) 0.066(4) -0.009(3)
C32 0.115(5) 0.041(4) 0.124(6) -0.003(4) 0.084(5) -0.003(4)
C33 0.084(4) 0.026(3) 0.065(4) 0.000(3) 0.017(3) 0.003(3)
C34 0.125(5) 0.028(4) 0.072(5) 0.009(3) 0.042(4) -0.009(3)
C35 0.109(5) 0.026(3) 0.052(4) 0.005(3) 0.034(3) -0.008(3)
C36 0.049(3) 0.021(3) 0.034(3) 0.005(3) -0.003(3) -0.004(2)
N3 0.056(3) 0.037(3) 0.053(3) 0.012(2) -0.010(2) 0.005(2)
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
O1 C1 1.377(5) . ?
O1 C5 1.380(5) . ?
C1 C2 1.338(5) . ?
C1 C6 1.514(5) . ?
C2 C3 1.458(5) . ?
C2 H2 0.9500 . ?
C3 C14 1.356(5) . ?
C3 C4 1.446(6) . ?
C4 C5 1.331(6) . ?
C4 H4 0.9500 . ?
C5 C10 1.494(6) . ?
C6 C9 1.520(5) . ?
C6 C7 1.521(5) . ?
C6 C8 1.530(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.513(5) . ?
C10 C13 1.522(5) . ?
C10 C12 1.523(6) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.445(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.395(5) . ?
C15 C20 1.433(6) . ?
C16 C17 1.390(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.414(6) . ?
C17 C21 1.469(6) . ?
C18 C19 1.398(6) . ?
C18 C29 1.442(6) . ?
C19 C20 1.387(6) . ?
C19 C30 1.490(6) . ?
C20 C36 1.439(6) . ?
C21 C22 1.398(5) . ?
C21 C26 1.400(5) . ?
C22 C23 1.377(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.398(5) . ?
C23 H23 0.9500 . ?
C24 N1 1.380(5) . ?
C24 C25 1.406(6) . ?
C25 C26 1.375(5) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
N1 C28 1.441(5) . ?
N1 C27 1.465(5) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 N2 1.137(5) . ?
C30 C35 1.352(5) . ?
C30 C31 1.363(6) . ?
C31 C32 1.370(7) . ?
C31 H31 0.9500 . ?
C32 C33 1.352(6) . ?
C32 H32 0.9500 . ?
C33 C34 1.353(6) . ?
C33 H33 0.9500 . ?
C34 C35 1.374(6) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 N3 1.155(5) . ?
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
C1 O1 C5 120.1(3) . . ?
C2 C1 O1 121.5(4) . . ?
C2 C1 C6 127.9(4) . . ?
O1 C1 C6 110.6(4) . . ?
C1 C2 C3 121.6(4) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C14 C3 C4 120.3(4) . . ?
C14 C3 C2 126.8(4) . . ?
C4 C3 C2 112.8(4) . . ?
C5 C4 C3 124.1(4) . . ?
C5 C4 H4 117.9 . . ?
C3 C4 H4 117.9 . . ?
C4 C5 O1 119.5(4) . . ?
C4 C5 C10 129.0(4) . . ?
O1 C5 C10 111.5(4) . . ?
C1 C6 C9 111.2(4) . . ?
C1 C6 C7 109.3(3) . . ?
C9 C6 C7 109.2(4) . . ?
C1 C6 C8 108.3(4) . . ?
C9 C6 C8 109.6(3) . . ?
C7 C6 C8 109.3(4) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 C11 110.7(4) . . ?
C5 C10 C13 109.4(4) . . ?
C11 C10 C13 108.9(4) . . ?
C5 C10 C12 109.3(4) . . ?
C11 C10 C12 109.7(4) . . ?
C13 C10 C12 108.9(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C14 C15 128.8(4) . . ?
C3 C14 H14 115.6 . . ?
C15 C14 H14 115.6 . . ?
C16 C15 C20 116.7(4) . . ?
C16 C15 C14 123.9(4) . . ?
C20 C15 C14 119.5(4) . . ?
C17 C16 C15 123.3(4) . . ?
C17 C16 H16 118.3 . . ?
C15 C16 H16 118.3 . . ?
C16 C17 C18 117.8(4) . . ?
C16 C17 C21 121.0(4) . . ?
C18 C17 C21 121.2(4) . . ?
C19 C18 C17 121.3(4) . . ?
C19 C18 C29 117.6(4) . . ?
C17 C18 C29 121.0(4) . . ?
C20 C19 C18 119.1(4) . . ?
C20 C19 C30 121.4(4) . . ?
C18 C19 C30 119.5(4) . . ?
C19 C20 C15 121.6(4) . . ?
C19 C20 C36 118.4(4) . . ?
C15 C20 C36 120.0(4) . . ?
C22 C21 C26 115.9(4) . . ?
C22 C21 C17 119.8(4) . . ?
C26 C21 C17 124.0(4) . . ?
C23 C22 C21 121.7(4) . . ?
C23 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
C22 C23 C24 121.6(4) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
N1 C24 C23 121.8(4) . . ?
N1 C24 C25 121.0(4) . . ?
C23 C24 C25 117.1(4) . . ?
C26 C25 C24 120.0(4) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C21 123.1(4) . . ?
C25 C26 H26 118.4 . . ?
C21 C26 H26 118.4 . . ?
C24 N1 C28 119.8(4) . . ?
C24 N1 C27 117.5(4) . . ?
C28 N1 C27 117.3(4) . . ?
N1 C27 H27A 109.5 . . ?
N1 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N1 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N1 C28 H28A 109.5 . . ?
N1 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N1 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N2 C29 C18 177.2(6) . . ?
C35 C30 C31 117.8(5) . . ?
C35 C30 C19 120.3(4) . . ?
C31 C30 C19 121.8(4) . . ?
C30 C31 C32 121.4(5) . . ?
C30 C31 H31 119.3 . . ?
C32 C31 H31 119.3 . . ?
C33 C32 C31 120.1(5) . . ?
C33 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
C32 C33 C34 119.0(5) . . ?
C32 C33 H33 120.5 . . ?
C34 C33 H33 120.5 . . ?
C33 C34 C35 120.7(5) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 H34 119.7 . . ?
C30 C35 C34 120.9(5) . . ?
C30 C35 H35 119.5 . . ?
C34 C35 H35 119.5 . . ?
N3 C36 C20 178.7(5) . . ?
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
C5 O1 C1 C2 -5.0(6) . . . . ?
C5 O1 C1 C6 173.9(3) . . . . ?
O1 C1 C2 C3 -0.2(6) . . . . ?
C6 C1 C2 C3 -178.9(4) . . . . ?
C1 C2 C3 C14 -178.4(4) . . . . ?
C1 C2 C3 C4 4.9(6) . . . . ?
C14 C3 C4 C5 178.1(5) . . . . ?
C2 C3 C4 C5 -4.9(7) . . . . ?
C3 C4 C5 O1 0.2(7) . . . . ?
C3 C4 C5 C10 -179.2(4) . . . . ?
C1 O1 C5 C4 5.0(6) . . . . ?
C1 O1 C5 C10 -175.5(3) . . . . ?
C2 C1 C6 C9 -3.5(6) . . . . ?
O1 C1 C6 C9 177.7(3) . . . . ?
C2 C1 C6 C7 -124.1(5) . . . . ?
O1 C1 C6 C7 57.2(4) . . . . ?
C2 C1 C6 C8 116.9(5) . . . . ?
O1 C1 C6 C8 -61.8(4) . . . . ?
C4 C5 C10 C11 -2.7(7) . . . . ?
O1 C5 C10 C11 177.9(3) . . . . ?
C4 C5 C10 C13 -122.6(5) . . . . ?
O1 C5 C10 C13 57.9(5) . . . . ?
C4 C5 C10 C12 118.2(5) . . . . ?
O1 C5 C10 C12 -61.2(5) . . . . ?
C4 C3 C14 C15 -177.6(4) . . . . ?
C2 C3 C14 C15 5.9(8) . . . . ?
C3 C14 C15 C16 30.1(7) . . . . ?
C3 C14 C15 C20 -151.2(5) . . . . ?
C20 C15 C16 C17 5.9(6) . . . . ?
C14 C15 C16 C17 -175.3(4) . . . . ?
C15 C16 C17 C18 -3.4(6) . . . . ?
C15 C16 C17 C21 173.5(4) . . . . ?
C16 C17 C18 C19 -1.7(6) . . . . ?
C21 C17 C18 C19 -178.6(4) . . . . ?
C16 C17 C18 C29 173.7(4) . . . . ?
C21 C17 C18 C29 -3.2(6) . . . . ?
C17 C18 C19 C20 3.9(6) . . . . ?
C29 C18 C19 C20 -171.7(4) . . . . ?
C17 C18 C19 C30 -177.4(4) . . . . ?
C29 C18 C19 C30 7.0(6) . . . . ?
C18 C19 C20 C15 -1.2(6) . . . . ?
C30 C19 C20 C15 -179.8(4) . . . . ?
C18 C19 C20 C36 175.8(4) . . . . ?
C30 C19 C20 C36 -2.8(6) . . . . ?
C16 C15 C20 C19 -3.5(6) . . . . ?
C14 C15 C20 C19 177.7(4) . . . . ?
C16 C15 C20 C36 179.5(4) . . . . ?
C14 C15 C20 C36 0.7(6) . . . . ?
C16 C17 C21 C22 -44.6(6) . . . . ?
C18 C17 C21 C22 132.2(4) . . . . ?
C16 C17 C21 C26 140.9(4) . . . . ?
C18 C17 C21 C26 -42.3(6) . . . . ?
C26 C21 C22 C23 3.7(6) . . . . ?
C17 C21 C22 C23 -171.3(4) . . . . ?
C21 C22 C23 C24 0.8(7) . . . . ?
C22 C23 C24 N1 174.6(4) . . . . ?
C22 C23 C24 C25 -6.1(6) . . . . ?
N1 C24 C25 C26 -173.8(4) . . . . ?
C23 C24 C25 C26 6.8(6) . . . . ?
C24 C25 C26 C21 -2.5(7) . . . . ?
C22 C21 C26 C25 -2.9(6) . . . . ?
C17 C21 C26 C25 171.9(4) . . . . ?
C23 C24 N1 C28 -167.8(4) . . . . ?
C25 C24 N1 C28 12.9(6) . . . . ?
C23 C24 N1 C27 -14.6(6) . . . . ?
C25 C24 N1 C27 166.1(4) . . . . ?
C20 C19 C30 C35 -89.2(6) . . . . ?
C18 C19 C30 C35 92.2(6) . . . . ?
C20 C19 C30 C31 94.1(6) . . . . ?
C18 C19 C30 C31 -84.5(6) . . . . ?
C35 C30 C31 C32 -0.6(9) . . . . ?
C19 C30 C31 C32 176.2(6) . . . . ?
C30 C31 C32 C33 1.0(11) . . . . ?
C31 C32 C33 C34 -0.5(10) . . . . ?
C32 C33 C34 C35 -0.5(9) . . . . ?
C31 C30 C35 C34 -0.4(8) . . . . ?
C19 C30 C35 C34 -177.3(5) . . . . ?
C33 C34 C35 C30 1.0(9) . . . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.194
_refine_diff_density_min -0.207
_refine_diff_density_rms 0.049
#===END