# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013
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# 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
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# data retrieval see:
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# from this site to visualise CIF-encoded structures and
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data_x1033a
#TrackingRef 'DBTX-312 Cis (final).cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C22 H22 N2 O2'
_chemical_formula_sum 'C22 H22 N2 O2'
_chemical_formula_weight 346.42
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 orthorhombic
_symmetry_space_group_name_H-M 'P b c n'
_symmetry_space_group_name_Hall '-P 2n 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
_cell_length_a 31.2908(12)
_cell_length_b 9.2585(3)
_cell_length_c 12.6610(5)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 3668.0(2)
_cell_formula_units_Z 8
_cell_measurement_temperature 110(2)
_cell_measurement_reflns_used 2661
_cell_measurement_theta_min 1.73
_cell_measurement_theta_max 24.05
_exptl_crystal_description lath
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.34
_exptl_crystal_size_mid 0.14
_exptl_crystal_size_min 0.08
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.255
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1472
_exptl_absorpt_coefficient_mu 0.081
_exptl_absorpt_correction_type analytical
_exptl_absorpt_correction_T_min 0.990
_exptl_absorpt_correction_T_max 0.998
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 110(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Goniometer KM4/Xcalibur, detector: Sapphire3'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean 15.989
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 8916
_diffrn_reflns_av_R_equivalents 0.0505
_diffrn_reflns_av_sigmaI/netI 0.0601
_diffrn_reflns_limit_h_min -27
_diffrn_reflns_limit_h_max 35
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 2.29
_diffrn_reflns_theta_max 24.00
_reflns_number_total 2867
_reflns_number_gt 2068
_reflns_threshold_expression I>2\s(I)
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_publication_material 'SHELXTL v6.10 (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^ > 2sigma(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^)+(0.0366P)^2^+0.9163P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens difmap
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2867
_refine_ls_number_parameters 238
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0730
_refine_ls_R_factor_gt 0.0434
_refine_ls_wR_factor_ref 0.0960
_refine_ls_wR_factor_gt 0.0870
_refine_ls_goodness_of_fit_ref 1.015
_refine_ls_restrained_S_all 1.015
_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
C1 C 0.59600(7) 0.0858(2) 0.65424(17) 0.0333(6) Uani 1 1 d . . .
H1A H 0.5987 0.1768 0.6931 0.050 Uiso 1 1 calc R . .
H1B H 0.6235 0.0350 0.6548 0.050 Uiso 1 1 calc R . .
H1C H 0.5742 0.0253 0.6879 0.050 Uiso 1 1 calc R . .
C2 C 0.54577(6) 0.1869(2) 0.53271(16) 0.0226(5) Uani 1 1 d . . .
C3 C 0.53439(7) 0.2139(3) 0.42887(17) 0.0367(6) Uani 1 1 d . . .
H3 H 0.5526 0.1828 0.3732 0.044 Uiso 1 1 calc R . .
C4 C 0.49703(7) 0.2855(2) 0.40546(17) 0.0357(6) Uani 1 1 d . . .
H4 H 0.4894 0.3028 0.3340 0.043 Uiso 1 1 calc R . .
C5 C 0.47062(6) 0.3323(2) 0.48650(15) 0.0199(5) Uani 1 1 d . . .
C6 C 0.48237(6) 0.3082(2) 0.58980(16) 0.0245(5) Uani 1 1 d . . .
H6 H 0.4647 0.3417 0.6456 0.029 Uiso 1 1 calc R . .
C7 C 0.51999(6) 0.2353(2) 0.61274(16) 0.0253(5) Uani 1 1 d . . .
H7 H 0.5279 0.2189 0.6842 0.030 Uiso 1 1 calc R . .
C8 C 0.39737(6) 0.4488(2) 0.53659(15) 0.0190(5) Uani 1 1 d . . .
H8 H 0.4081 0.5165 0.5922 0.023 Uiso 1 1 calc R . .
C9 C 0.36980(6) 0.3318(2) 0.58218(15) 0.0175(5) Uani 1 1 d . . .
C10 C 0.37752(6) 0.1858(2) 0.56641(15) 0.0212(5) Uani 1 1 d . . .
H10 H 0.4022 0.1560 0.5284 0.025 Uiso 1 1 calc R . .
C11 C 0.34945(7) 0.0830(2) 0.60590(16) 0.0253(5) Uani 1 1 d . . .
H11 H 0.3551 -0.0168 0.5955 0.030 Uiso 1 1 calc R . .
C12 C 0.31329(7) 0.1256(2) 0.66034(16) 0.0278(5) Uani 1 1 d . . .
H12 H 0.2937 0.0554 0.6857 0.033 Uiso 1 1 calc R . .
C13 C 0.30581(7) 0.2711(2) 0.67775(17) 0.0278(5) Uani 1 1 d . . .
H13 H 0.2812 0.3008 0.7160 0.033 Uiso 1 1 calc R . .
C14 C 0.33391(6) 0.3725(2) 0.63984(15) 0.0226(5) Uani 1 1 d . . .
H14 H 0.3288 0.4720 0.6532 0.027 Uiso 1 1 calc R . .
C15 C 0.37824(6) 0.5324(2) 0.43815(15) 0.0202(5) Uani 1 1 d . . .
H15 H 0.3835 0.6382 0.4471 0.024 Uiso 1 1 calc R . .
C16 C 0.41521(7) 0.4663(2) 0.37579(16) 0.0250(5) Uani 1 1 d . . .
C17 C 0.31696(7) 0.3901(2) 0.35897(15) 0.0233(5) Uani 1 1 d . . .
C18 C 0.27383(7) 0.4056(2) 0.36329(16) 0.0288(5) Uani 1 1 d . . .
H18 H 0.2535 0.3405 0.3343 0.035 Uiso 1 1 calc R . .
C19 C 0.26418(7) 0.5343(2) 0.41796(16) 0.0266(5) Uani 1 1 d . . .
H19 H 0.2364 0.5705 0.4325 0.032 Uiso 1 1 calc R . .
C20 C 0.30155(6) 0.5970(2) 0.44602(16) 0.0215(5) Uani 1 1 d . . .
C21 C 0.34269(7) 0.2730(2) 0.30915(17) 0.0329(6) Uani 1 1 d . . .
H21A H 0.3614 0.2293 0.3623 0.049 Uiso 1 1 calc R . .
H21B H 0.3601 0.3136 0.2520 0.049 Uiso 1 1 calc R . .
H21C H 0.3235 0.1992 0.2804 0.049 Uiso 1 1 calc R . .
C22 C 0.30958(7) 0.7341(2) 0.50430(17) 0.0285(5) Uani 1 1 d . . .
H22A H 0.2823 0.7749 0.5281 0.043 Uiso 1 1 calc R . .
H22B H 0.3239 0.8031 0.4575 0.043 Uiso 1 1 calc R . .
H22C H 0.3278 0.7146 0.5656 0.043 Uiso 1 1 calc R . .
N1 N 0.43180(5) 0.40273(17) 0.46425(12) 0.0201(4) Uani 1 1 d . . .
N2 N 0.33455(5) 0.50995(16) 0.40905(12) 0.0201(4) Uani 1 1 d . . .
O1 O 0.58380(4) 0.11525(15) 0.54763(11) 0.0298(4) Uani 1 1 d . . .
O2 O 0.42752(5) 0.47018(16) 0.28502(11) 0.0330(4) 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
C1 0.0294(13) 0.0340(13) 0.0366(14) 0.0075(12) -0.0024(11) 0.0080(10)
C2 0.0188(11) 0.0228(11) 0.0261(12) -0.0036(10) 0.0008(10) 0.0005(9)
C3 0.0320(14) 0.0578(16) 0.0203(12) -0.0072(12) 0.0065(11) 0.0117(12)
C4 0.0347(14) 0.0564(16) 0.0161(11) -0.0023(12) 0.0010(11) 0.0083(12)
C5 0.0198(11) 0.0232(11) 0.0167(11) 0.0011(9) 0.0026(9) -0.0013(9)
C6 0.0246(12) 0.0329(12) 0.0160(11) -0.0016(10) 0.0046(10) 0.0032(10)
C7 0.0250(12) 0.0327(12) 0.0182(11) 0.0019(10) -0.0013(10) 0.0029(10)
C8 0.0200(11) 0.0204(10) 0.0165(10) -0.0022(9) -0.0004(9) 0.0007(8)
C9 0.0220(11) 0.0198(11) 0.0106(10) -0.0013(9) -0.0037(9) -0.0009(9)
C10 0.0241(11) 0.0240(11) 0.0157(11) -0.0025(9) -0.0008(9) 0.0024(9)
C11 0.0320(13) 0.0159(10) 0.0280(12) -0.0027(10) -0.0019(10) -0.0021(10)
C12 0.0294(13) 0.0270(12) 0.0272(12) 0.0050(11) 0.0008(11) -0.0064(10)
C13 0.0286(12) 0.0298(12) 0.0249(12) 0.0030(11) 0.0098(10) 0.0008(10)
C14 0.0300(13) 0.0200(11) 0.0177(11) 0.0001(10) 0.0031(10) 0.0017(10)
C15 0.0223(11) 0.0190(10) 0.0192(11) 0.0029(9) -0.0044(9) -0.0028(9)
C16 0.0265(12) 0.0282(12) 0.0203(12) 0.0023(10) -0.0032(10) -0.0044(10)
C17 0.0352(13) 0.0162(10) 0.0185(11) 0.0016(10) -0.0068(10) -0.0036(9)
C18 0.0315(13) 0.0258(12) 0.0290(12) 0.0030(11) -0.0113(11) -0.0105(10)
C19 0.0231(12) 0.0251(12) 0.0315(12) 0.0047(11) -0.0031(10) -0.0017(9)
C20 0.0244(12) 0.0194(11) 0.0208(11) 0.0040(10) -0.0016(9) 0.0007(9)
C21 0.0462(15) 0.0262(12) 0.0262(12) -0.0034(11) -0.0107(11) 0.0010(11)
C22 0.0303(13) 0.0238(11) 0.0314(13) -0.0019(11) -0.0048(10) 0.0043(10)
N1 0.0224(9) 0.0253(9) 0.0126(8) 0.0029(8) 0.0006(8) 0.0001(8)
N2 0.0240(10) 0.0167(9) 0.0195(9) 0.0024(8) -0.0061(8) -0.0027(7)
O1 0.0256(8) 0.0345(8) 0.0294(8) -0.0047(7) -0.0007(7) 0.0088(7)
O2 0.0346(9) 0.0492(10) 0.0154(8) 0.0078(7) 0.0015(7) 0.0002(7)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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
C1 O1 1.429(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.370(3) . ?
C2 O1 1.376(2) . ?
C2 C3 1.385(3) . ?
C3 C4 1.376(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.377(3) . ?
C5 N1 1.407(2) . ?
C6 C7 1.388(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 N1 1.477(2) . ?
C8 C9 1.500(3) . ?
C8 C15 1.585(3) . ?
C8 H8 1.0000 . ?
C9 C10 1.388(3) . ?
C9 C14 1.391(3) . ?
C10 C11 1.388(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.373(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 N2 1.431(2) . ?
C15 C16 1.529(3) . ?
C15 H15 1.0000 . ?
C16 O2 1.213(2) . ?
C16 N1 1.368(2) . ?
C17 C18 1.358(3) . ?
C17 N2 1.392(2) . ?
C17 C21 1.490(3) . ?
C18 C19 1.411(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.353(3) . ?
C19 H19 0.9500 . ?
C20 N2 1.391(2) . ?
C20 C22 1.490(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 O1 124.43(19) . . ?
C7 C2 C3 119.44(19) . . ?
O1 C2 C3 116.10(18) . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 119.54(19) . . ?
C6 C5 N1 119.72(17) . . ?
C4 C5 N1 120.74(18) . . ?
C5 C6 C7 120.27(19) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C2 C7 C6 120.24(19) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
N1 C8 C9 116.72(15) . . ?
N1 C8 C15 85.92(13) . . ?
C9 C8 C15 115.96(16) . . ?
N1 C8 H8 112.0 . . ?
C9 C8 H8 112.0 . . ?
C15 C8 H8 112.0 . . ?
C10 C9 C14 118.66(18) . . ?
C10 C9 C8 123.21(17) . . ?
C14 C9 C8 118.09(17) . . ?
C9 C10 C11 120.38(19) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 120.13(18) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 119.7(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C9 121.03(19) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
N2 C15 C16 122.15(16) . . ?
N2 C15 C8 119.52(15) . . ?
C16 C15 C8 85.69(14) . . ?
N2 C15 H15 109.1 . . ?
C16 C15 H15 109.1 . . ?
C8 C15 H15 109.1 . . ?
O2 C16 N1 131.9(2) . . ?
O2 C16 C15 135.90(19) . . ?
N1 C16 C15 92.09(15) . . ?
C18 C17 N2 106.89(18) . . ?
C18 C17 C21 129.09(19) . . ?
N2 C17 C21 123.99(19) . . ?
C17 C18 C19 108.75(18) . . ?
C17 C18 H18 125.6 . . ?
C19 C18 H18 125.6 . . ?
C20 C19 C18 107.84(19) . . ?
C20 C19 H19 126.1 . . ?
C18 C19 H19 126.1 . . ?
C19 C20 N2 107.73(17) . . ?
C19 C20 C22 129.91(19) . . ?
N2 C20 C22 122.35(17) . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C16 N1 C5 133.71(16) . . ?
C16 N1 C8 96.13(15) . . ?
C5 N1 C8 129.74(15) . . ?
C20 N2 C17 108.76(16) . . ?
C20 N2 C15 122.58(16) . . ?
C17 N2 C15 127.66(17) . . ?
C2 O1 C1 116.94(16) . . ?
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
C7 C2 C3 C4 -1.7(3) . . . . ?
O1 C2 C3 C4 -179.7(2) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C3 C4 C5 N1 -178.5(2) . . . . ?
C4 C5 C6 C7 -1.2(3) . . . . ?
N1 C5 C6 C7 178.20(17) . . . . ?
O1 C2 C7 C6 179.21(18) . . . . ?
C3 C2 C7 C6 1.3(3) . . . . ?
C5 C6 C7 C2 0.1(3) . . . . ?
N1 C8 C9 C10 5.5(3) . . . . ?
C15 C8 C9 C10 104.5(2) . . . . ?
N1 C8 C9 C14 -172.11(16) . . . . ?
C15 C8 C9 C14 -73.1(2) . . . . ?
C14 C9 C10 C11 1.2(3) . . . . ?
C8 C9 C10 C11 -176.42(18) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C10 C11 C12 C13 -1.7(3) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C12 C13 C14 C9 1.1(3) . . . . ?
C10 C9 C14 C13 -2.1(3) . . . . ?
C8 C9 C14 C13 175.67(18) . . . . ?
N1 C8 C15 N2 127.66(18) . . . . ?
C9 C8 C15 N2 9.8(2) . . . . ?
N1 C8 C15 C16 2.87(13) . . . . ?
C9 C8 C15 C16 -114.95(17) . . . . ?
N2 C15 C16 O2 57.3(3) . . . . ?
C8 C15 C16 O2 179.7(3) . . . . ?
N2 C15 C16 N1 -125.52(18) . . . . ?
C8 C15 C16 N1 -3.09(14) . . . . ?
N2 C17 C18 C19 -1.0(2) . . . . ?
C21 C17 C18 C19 -179.5(2) . . . . ?
C17 C18 C19 C20 0.4(2) . . . . ?
C18 C19 C20 N2 0.4(2) . . . . ?
C18 C19 C20 C22 179.7(2) . . . . ?
O2 C16 N1 C5 7.9(4) . . . . ?
C15 C16 N1 C5 -169.5(2) . . . . ?
O2 C16 N1 C8 -179.3(2) . . . . ?
C15 C16 N1 C8 3.33(15) . . . . ?
C6 C5 N1 C16 165.0(2) . . . . ?
C4 C5 N1 C16 -15.6(3) . . . . ?
C6 C5 N1 C8 -5.7(3) . . . . ?
C4 C5 N1 C8 173.67(19) . . . . ?
C9 C8 N1 C16 113.87(18) . . . . ?
C15 C8 N1 C16 -3.22(15) . . . . ?
C9 C8 N1 C5 -72.8(2) . . . . ?
C15 C8 N1 C5 170.06(19) . . . . ?
C19 C20 N2 C17 -1.1(2) . . . . ?
C22 C20 N2 C17 179.59(18) . . . . ?
C19 C20 N2 C15 -170.46(17) . . . . ?
C22 C20 N2 C15 10.2(3) . . . . ?
C18 C17 N2 C20 1.3(2) . . . . ?
C21 C17 N2 C20 179.82(18) . . . . ?
C18 C17 N2 C15 170.00(18) . . . . ?
C21 C17 N2 C15 -11.5(3) . . . . ?
C16 C15 N2 C20 -162.67(17) . . . . ?
C8 C15 N2 C20 92.6(2) . . . . ?
C16 C15 N2 C17 30.1(3) . . . . ?
C8 C15 N2 C17 -74.6(2) . . . . ?
C7 C2 O1 C1 2.3(3) . . . . ?
C3 C2 O1 C1 -179.73(19) . . . . ?
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full 24.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max 0.174
_refine_diff_density_min -0.181
_refine_diff_density_rms 0.042
_iucr_refine_instructions_details
;
TITL x1033a
CELL 0.71073 31.2908 9.2585 12.6610 90.000 90.000 90.000
ZERR 8 0.0012 0.0003 0.0005 0.000 0.000 0.000
LATT 1
SYMM 1/2-X,1/2-Y,1/2+Z
SYMM 1/2+X,1/2-Y,-Z
SYMM -X,Y,1/2-Z
SFAC C H N O
UNIT 176 176 16 16
TEMP -163
ACTA
HTAB
BOND
BOND $H
CONF
WPDB
L.S. 6
FMAP 2
PLAN 10
OMIT -2 48
WGHT 0.036600 0.916300
FVAR 0.88048
C1 1 0.596005 0.085772 0.654243 11.00000 0.02938 0.03398 =
0.03661 0.00750 -0.00244 0.00799
AFIX 137
H1A 2 0.598706 0.176833 0.693135 11.00000 -1.50000
H1B 2 0.623480 0.034972 0.654841 11.00000 -1.50000
H1C 2 0.574196 0.025296 0.687864 11.00000 -1.50000
AFIX 0
C2 1 0.545766 0.186897 0.532711 11.00000 0.01883 0.02282 =
0.02607 -0.00363 0.00082 0.00049
C3 1 0.534393 0.213923 0.428872 11.00000 0.03199 0.05781 =
0.02028 -0.00725 0.00654 0.01173
AFIX 43
H3 2 0.552564 0.182754 0.373250 11.00000 -1.20000
AFIX 0
C4 1 0.497032 0.285476 0.405463 11.00000 0.03471 0.05642 =
0.01611 -0.00230 0.00102 0.00826
AFIX 43
H4 2 0.489350 0.302762 0.333981 11.00000 -1.20000
AFIX 0
C5 1 0.470619 0.332298 0.486498 11.00000 0.01979 0.02317 =
0.01666 0.00105 0.00263 -0.00125
C6 1 0.482371 0.308226 0.589800 11.00000 0.02456 0.03290 =
0.01599 -0.00161 0.00458 0.00321
AFIX 43
H6 2 0.464653 0.341671 0.645608 11.00000 -1.20000
AFIX 0
C7 1 0.519989 0.235312 0.612737 11.00000 0.02495 0.03274 =
0.01820 0.00189 -0.00129 0.00291
AFIX 43
H7 2 0.527903 0.218897 0.684175 11.00000 -1.20000
AFIX 0
C8 1 0.397374 0.448805 0.536590 11.00000 0.01999 0.02037 =
0.01649 -0.00216 -0.00039 0.00066
AFIX 13
H8 2 0.408051 0.516509 0.592184 11.00000 -1.20000
AFIX 0
C9 1 0.369795 0.331843 0.582177 11.00000 0.02198 0.01981 =
0.01064 -0.00134 -0.00369 -0.00088
C10 1 0.377524 0.185783 0.566412 11.00000 0.02411 0.02396 =
0.01566 -0.00246 -0.00082 0.00239
AFIX 43
H10 2 0.402167 0.155989 0.528385 11.00000 -1.20000
AFIX 0
C11 1 0.349446 0.082998 0.605901 11.00000 0.03202 0.01590 =
0.02797 -0.00273 -0.00188 -0.00213
AFIX 43
H11 2 0.355094 -0.016808 0.595483 11.00000 -1.20000
AFIX 0
C12 1 0.313290 0.125594 0.660345 11.00000 0.02936 0.02695 =
0.02722 0.00505 0.00077 -0.00639
AFIX 43
H12 2 0.293666 0.055398 0.685703 11.00000 -1.20000
AFIX 0
C13 1 0.305807 0.271095 0.677749 11.00000 0.02860 0.02981 =
0.02491 0.00297 0.00978 0.00081
AFIX 43
H13 2 0.281201 0.300773 0.715969 11.00000 -1.20000
AFIX 0
C14 1 0.333908 0.372494 0.639835 11.00000 0.02996 0.01999 =
0.01771 0.00007 0.00307 0.00172
AFIX 43
H14 2 0.328768 0.471961 0.653179 11.00000 -1.20000
AFIX 0
C15 1 0.378237 0.532372 0.438148 11.00000 0.02232 0.01901 =
0.01915 0.00286 -0.00438 -0.00282
AFIX 13
H15 2 0.383453 0.638223 0.447130 11.00000 -1.20000
AFIX 0
C16 1 0.415214 0.466304 0.375785 11.00000 0.02646 0.02825 =
0.02035 0.00225 -0.00321 -0.00441
C17 1 0.316961 0.390100 0.358967 11.00000 0.03524 0.01616 =
0.01849 0.00158 -0.00678 -0.00364
C18 1 0.273830 0.405576 0.363294 11.00000 0.03150 0.02580 =
0.02899 0.00295 -0.01127 -0.01048
AFIX 43
H18 2 0.253511 0.340457 0.334298 11.00000 -1.20000
AFIX 0
C19 1 0.264180 0.534322 0.417960 11.00000 0.02314 0.02508 =
0.03152 0.00472 -0.00305 -0.00169
AFIX 43
H19 2 0.236387 0.570532 0.432478 11.00000 -1.20000
AFIX 0
C20 1 0.301546 0.597026 0.446021 11.00000 0.02436 0.01938 =
0.02079 0.00396 -0.00158 0.00072
C21 1 0.342691 0.273021 0.309152 11.00000 0.04625 0.02615 =
0.02622 -0.00344 -0.01074 0.00096
AFIX 137
H21A 2 0.361436 0.229293 0.362280 11.00000 -1.50000
H21B 2 0.360062 0.313600 0.251988 11.00000 -1.50000
H21C 2 0.323496 0.199180 0.280429 11.00000 -1.50000
AFIX 0
C22 1 0.309582 0.734138 0.504296 11.00000 0.03028 0.02379 =
0.03144 -0.00192 -0.00479 0.00431
AFIX 137
H22A 2 0.282325 0.774886 0.528078 11.00000 -1.50000
H22B 2 0.323923 0.803132 0.457504 11.00000 -1.50000
H22C 2 0.327784 0.714598 0.565643 11.00000 -1.50000
AFIX 0
N1 3 0.431802 0.402734 0.464252 11.00000 0.02244 0.02528 =
0.01265 0.00291 0.00065 0.00012
N2 3 0.334554 0.509950 0.409052 11.00000 0.02402 0.01665 =
0.01950 0.00237 -0.00612 -0.00272
O1 4 0.583803 0.115249 0.547634 11.00000 0.02558 0.03448 =
0.02938 -0.00467 -0.00067 0.00877
O2 4 0.427520 0.470183 0.285018 11.00000 0.03457 0.04920 =
0.01537 0.00779 0.00148 0.00017
HKLF 4
REM x1033a
REM R1 = 0.0434 for 2068 Fo > 4sig(Fo) and 0.0730 for all 2867 data
REM 238 parameters refined using 0 restraints
END
WGHT 0.0366 0.9163
REM Highest difference peak 0.174, deepest hole -0.181, 1-sigma level 0.042
Q1 1 0.3778 0.3857 0.5494 11.00000 0.05 0.17
Q2 1 0.3547 0.5059 0.6980 11.00000 0.05 0.16
Q3 1 0.6096 0.0905 0.4955 11.00000 0.05 0.15
Q4 1 0.2705 0.3050 0.6372 11.00000 0.05 0.15
Q5 1 0.6358 0.0785 0.6376 11.00000 0.05 0.15
Q6 1 0.4688 0.5000 0.2959 11.00000 0.05 0.15
Q7 1 0.5678 0.2262 0.3788 11.00000 0.05 0.13
Q8 1 0.3829 0.4927 0.4936 11.00000 0.05 0.13
Q9 1 0.2914 0.7377 0.5949 11.00000 0.05 0.13
Q10 1 0.4878 0.1862 0.6006 11.00000 0.05 0.13
;
_database_code_depnum_ccdc_archive 'CCDC 932934'
#######################################################################
#
# 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_xs0040a
#TrackingRef 'DBTX-312(Trans) (final).cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C22 H22 N2 O2'
_chemical_formula_sum 'C22 H22 N2 O2'
_chemical_formula_weight 346.42
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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/n'
_symmetry_space_group_name_Hall '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 9.5368(2)
_cell_length_b 11.2841(3)
_cell_length_c 16.5037(5)
_cell_angle_alpha 90.00
_cell_angle_beta 90.689(2)
_cell_angle_gamma 90.00
_cell_volume 1775.90(8)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 9385
_cell_measurement_theta_min 3.8930
_cell_measurement_theta_max 67.01
_exptl_crystal_description 'very thin lath'
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.49
_exptl_crystal_size_mid 0.17
_exptl_crystal_size_min 0.03
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.296
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 736
_exptl_absorpt_coefficient_mu 0.664
_exptl_absorpt_correction_type analytical
_exptl_absorpt_correction_T_min 0.830
_exptl_absorpt_correction_T_max 0.981
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 1.54178
_diffrn_radiation_type CuK\a
_diffrn_radiation_source 'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator mirror
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean 10.3875
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 18253
_diffrn_reflns_av_R_equivalents 0.0284
_diffrn_reflns_av_sigmaI/netI 0.0139
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_theta_min 4.75
_diffrn_reflns_theta_max 67.24
_reflns_number_total 3194
_reflns_number_gt 3004
_reflns_threshold_expression I>2\s(I)
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
;
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
;
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_publication_material 'SHELXTL v6.10 (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^ > 2sigma(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^)+(0.0368P)^2^+0.8834P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens difmap
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3194
_refine_ls_number_parameters 238
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0415
_refine_ls_R_factor_gt 0.0392
_refine_ls_wR_factor_ref 0.0957
_refine_ls_wR_factor_gt 0.0941
_refine_ls_goodness_of_fit_ref 1.067
_refine_ls_restrained_S_all 1.067
_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
C1 C 0.67366(18) -0.04041(16) 0.43749(11) 0.0449(4) Uani 1 1 d . . .
H1A H 0.5928 0.0023 0.4591 0.067 Uiso 1 1 calc R . .
H1B H 0.6731 -0.1222 0.4574 0.067 Uiso 1 1 calc R . .
H1C H 0.6684 -0.0405 0.3782 0.067 Uiso 1 1 calc R . .
C2 C 0.81927(16) 0.13166(13) 0.43858(9) 0.0298(3) Uani 1 1 d . . .
C3 C 0.71755(15) 0.20187(13) 0.40237(8) 0.0278(3) Uani 1 1 d . . .
H3 H 0.6265 0.1708 0.3919 0.033 Uiso 1 1 calc R . .
C4 C 0.74927(14) 0.31857(13) 0.38134(8) 0.0277(3) Uani 1 1 d . . .
H4 H 0.6797 0.3671 0.3564 0.033 Uiso 1 1 calc R . .
C5 C 0.88169(14) 0.36363(12) 0.39665(8) 0.0258(3) Uani 1 1 d . . .
C6 C 0.98451(15) 0.29168(13) 0.43201(9) 0.0314(3) Uani 1 1 d . . .
H6 H 1.0760 0.3221 0.4418 0.038 Uiso 1 1 calc R . .
C7 C 0.95316(16) 0.17657(14) 0.45268(9) 0.0334(3) Uani 1 1 d . . .
H7 H 1.0233 0.1276 0.4767 0.040 Uiso 1 1 calc R . .
C8 C 0.83929(14) 0.57051(12) 0.32539(8) 0.0267(3) Uani 1 1 d . . .
H8 H 0.8322 0.5438 0.2677 0.032 Uiso 1 1 calc R . .
C9 C 0.69980(14) 0.61383(12) 0.35513(8) 0.0257(3) Uani 1 1 d . . .
C10 C 0.66189(15) 0.60532(13) 0.43610(9) 0.0283(3) Uani 1 1 d . . .
H10 H 0.7253 0.5720 0.4746 0.034 Uiso 1 1 calc R . .
C11 C 0.53161(15) 0.64542(13) 0.46061(9) 0.0297(3) Uani 1 1 d . . .
H11 H 0.5065 0.6397 0.5160 0.036 Uiso 1 1 calc R . .
C12 C 0.43809(15) 0.69352(13) 0.40519(9) 0.0307(3) Uani 1 1 d . . .
H12 H 0.3487 0.7199 0.4224 0.037 Uiso 1 1 calc R . .
C13 C 0.47480(15) 0.70325(13) 0.32459(9) 0.0310(3) Uani 1 1 d . . .
H13 H 0.4107 0.7365 0.2864 0.037 Uiso 1 1 calc R . .
C14 C 0.60541(15) 0.66436(13) 0.29964(9) 0.0287(3) Uani 1 1 d . . .
H14 H 0.6309 0.6721 0.2444 0.034 Uiso 1 1 calc R . .
C15 C 0.97164(14) 0.65214(13) 0.33915(9) 0.0280(3) Uani 1 1 d . . .
H15 H 0.9496 0.7170 0.3783 0.034 Uiso 1 1 calc R . .
C16 C 1.03612(14) 0.54589(13) 0.38408(8) 0.0271(3) Uani 1 1 d . . .
C17 C 1.05735(16) 0.81927(14) 0.25404(10) 0.0355(4) Uani 1 1 d . . .
C18 C 1.12533(17) 0.82938(17) 0.18216(10) 0.0431(4) Uani 1 1 d . . .
H18 H 1.1476 0.9015 0.1555 0.052 Uiso 1 1 calc R . .
C19 C 1.15703(16) 0.71408(18) 0.15410(10) 0.0419(4) Uani 1 1 d . . .
H19 H 1.2046 0.6954 0.1055 0.050 Uiso 1 1 calc R . .
C20 C 1.10730(15) 0.63417(16) 0.20903(9) 0.0354(4) Uani 1 1 d . . .
C21 C 1.00552(19) 0.91155(15) 0.30998(11) 0.0444(4) Uani 1 1 d . . .
H21A H 1.0308 0.9900 0.2893 0.067 Uiso 1 1 calc R . .
H21B H 1.0481 0.9000 0.3637 0.067 Uiso 1 1 calc R . .
H21C H 0.9033 0.9057 0.3139 0.067 Uiso 1 1 calc R . .
C22 C 1.11698(17) 0.50297(16) 0.20824(10) 0.0418(4) Uani 1 1 d . . .
H22A H 1.1597 0.4769 0.1575 0.063 Uiso 1 1 calc R . .
H22B H 1.0228 0.4689 0.2124 0.063 Uiso 1 1 calc R . .
H22C H 1.1748 0.4764 0.2542 0.063 Uiso 1 1 calc R . .
N1 N 0.91463(12) 0.48183(11) 0.37587(7) 0.0268(3) Uani 1 1 d . . .
N2 N 1.04521(12) 0.69917(11) 0.27050(7) 0.0299(3) Uani 1 1 d . . .
O1 O 0.79898(12) 0.01630(9) 0.46324(7) 0.0387(3) Uani 1 1 d . . .
O2 O 1.14869(10) 0.52444(9) 0.41487(6) 0.0326(3) 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
C1 0.0382(9) 0.0404(10) 0.0560(11) 0.0129(8) -0.0006(8) -0.0085(7)
C2 0.0349(8) 0.0274(8) 0.0271(7) 0.0018(6) 0.0015(6) 0.0014(6)
C3 0.0248(7) 0.0304(8) 0.0284(7) -0.0014(6) 0.0018(5) -0.0020(6)
C4 0.0248(7) 0.0301(8) 0.0282(7) 0.0003(6) -0.0007(5) 0.0046(6)
C5 0.0254(7) 0.0252(7) 0.0269(7) -0.0005(6) -0.0002(5) 0.0024(5)
C6 0.0251(7) 0.0307(8) 0.0383(8) -0.0006(6) -0.0054(6) 0.0023(6)
C7 0.0332(8) 0.0295(8) 0.0372(8) 0.0016(6) -0.0081(6) 0.0062(6)
C8 0.0264(7) 0.0259(7) 0.0276(7) 0.0027(6) -0.0018(5) 0.0007(6)
C9 0.0245(7) 0.0208(7) 0.0318(7) 0.0010(5) -0.0013(6) -0.0018(5)
C10 0.0300(7) 0.0240(7) 0.0309(7) 0.0024(6) -0.0027(6) -0.0013(6)
C11 0.0319(7) 0.0254(7) 0.0320(7) -0.0009(6) 0.0049(6) -0.0034(6)
C12 0.0238(7) 0.0251(7) 0.0433(8) -0.0044(6) 0.0023(6) -0.0011(6)
C13 0.0279(7) 0.0264(7) 0.0387(8) 0.0003(6) -0.0070(6) 0.0031(6)
C14 0.0289(7) 0.0274(7) 0.0298(7) 0.0024(6) -0.0009(6) -0.0007(6)
C15 0.0259(7) 0.0293(8) 0.0289(7) 0.0016(6) 0.0001(6) -0.0006(6)
C16 0.0249(7) 0.0294(8) 0.0271(7) -0.0009(6) -0.0004(5) -0.0003(6)
C17 0.0283(8) 0.0380(9) 0.0402(8) 0.0099(7) -0.0046(6) -0.0068(6)
C18 0.0334(8) 0.0580(11) 0.0377(9) 0.0135(8) -0.0047(7) -0.0177(8)
C19 0.0277(8) 0.0677(12) 0.0303(8) 0.0034(8) 0.0000(6) -0.0109(8)
C20 0.0235(7) 0.0524(10) 0.0303(8) -0.0008(7) -0.0026(6) 0.0005(7)
C21 0.0450(10) 0.0321(9) 0.0563(11) 0.0098(8) 0.0021(8) -0.0019(7)
C22 0.0363(9) 0.0528(11) 0.0362(9) -0.0061(8) -0.0011(7) 0.0082(7)
N1 0.0230(6) 0.0263(6) 0.0310(6) 0.0026(5) -0.0031(5) 0.0019(5)
N2 0.0241(6) 0.0341(7) 0.0315(6) 0.0059(5) 0.0007(5) -0.0009(5)
O1 0.0433(6) 0.0281(6) 0.0446(6) 0.0082(5) -0.0073(5) -0.0049(5)
O2 0.0261(5) 0.0354(6) 0.0363(6) 0.0025(4) -0.0059(4) -0.0015(4)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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
C1 O1 1.416(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O1 1.3783(18) . ?
C2 C3 1.383(2) . ?
C2 C7 1.391(2) . ?
C3 C4 1.396(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(2) . ?
C5 N1 1.4134(18) . ?
C6 C7 1.377(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 N1 1.4824(17) . ?
C8 C9 1.5051(19) . ?
C8 C15 1.5768(19) . ?
C8 H8 1.0000 . ?
C9 C10 1.392(2) . ?
C9 C14 1.398(2) . ?
C10 C11 1.387(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 N2 1.4411(18) . ?
C15 C16 1.534(2) . ?
C15 H15 1.0000 . ?
C16 O2 1.2068(17) . ?
C16 N1 1.3710(18) . ?
C17 C18 1.364(2) . ?
C17 N2 1.387(2) . ?
C17 C21 1.480(2) . ?
C18 C19 1.415(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.368(2) . ?
C19 H19 0.9500 . ?
C20 N2 1.390(2) . ?
C20 C22 1.483(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 124.64(13) . . ?
O1 C2 C7 115.25(13) . . ?
C3 C2 C7 120.10(14) . . ?
C2 C3 C4 119.67(13) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.13(13) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.89(13) . . ?
C4 C5 N1 120.54(12) . . ?
C6 C5 N1 119.56(12) . . ?
C7 C6 C5 119.93(14) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 120.26(13) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
N1 C8 C9 117.41(11) . . ?
N1 C8 C15 86.08(10) . . ?
C9 C8 C15 118.20(12) . . ?
N1 C8 H8 111.0 . . ?
C9 C8 H8 111.0 . . ?
C15 C8 H8 111.0 . . ?
C10 C9 C14 118.97(13) . . ?
C10 C9 C8 122.11(12) . . ?
C14 C9 C8 118.92(12) . . ?
C11 C10 C9 120.09(13) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 120.58(14) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 119.93(13) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 119.89(13) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C9 120.52(14) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
N2 C15 C16 118.14(12) . . ?
N2 C15 C8 119.89(12) . . ?
C16 C15 C8 85.91(10) . . ?
N2 C15 H15 110.3 . . ?
C16 C15 H15 110.3 . . ?
C8 C15 H15 110.3 . . ?
O2 C16 N1 133.03(14) . . ?
O2 C16 C15 135.20(13) . . ?
N1 C16 C15 91.77(11) . . ?
C18 C17 N2 107.08(15) . . ?
C18 C17 C21 130.50(16) . . ?
N2 C17 C21 122.39(14) . . ?
C17 C18 C19 108.28(15) . . ?
C17 C18 H18 125.9 . . ?
C19 C18 H18 125.9 . . ?
C20 C19 C18 108.19(15) . . ?
C20 C19 H19 125.9 . . ?
C18 C19 H19 125.9 . . ?
C19 C20 N2 106.86(15) . . ?
C19 C20 C22 129.06(16) . . ?
N2 C20 C22 124.06(14) . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C16 N1 C5 131.58(12) . . ?
C16 N1 C8 95.91(11) . . ?
C5 N1 C8 131.74(11) . . ?
C17 N2 C20 109.59(13) . . ?
C17 N2 C15 123.80(13) . . ?
C20 N2 C15 126.52(13) . . ?
C2 O1 C1 117.33(12) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 178.71(13) . . . . ?
C7 C2 C3 C4 -1.1(2) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C3 C4 C5 C6 1.0(2) . . . . ?
C3 C4 C5 N1 -179.74(12) . . . . ?
C4 C5 C6 C7 -1.0(2) . . . . ?
N1 C5 C6 C7 179.79(13) . . . . ?
C5 C6 C7 C2 -0.1(2) . . . . ?
O1 C2 C7 C6 -178.67(14) . . . . ?
C3 C2 C7 C6 1.1(2) . . . . ?
N1 C8 C9 C10 21.2(2) . . . . ?
C15 C8 C9 C10 -79.78(17) . . . . ?
N1 C8 C9 C14 -158.89(12) . . . . ?
C15 C8 C9 C14 100.13(15) . . . . ?
C14 C9 C10 C11 0.7(2) . . . . ?
C8 C9 C10 C11 -179.39(13) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
C10 C11 C12 C13 -0.7(2) . . . . ?
C11 C12 C13 C14 0.2(2) . . . . ?
C12 C13 C14 C9 0.9(2) . . . . ?
C10 C9 C14 C13 -1.3(2) . . . . ?
C8 C9 C14 C13 178.79(13) . . . . ?
N1 C8 C15 N2 124.29(13) . . . . ?
C9 C8 C15 N2 -116.58(15) . . . . ?
N1 C8 C15 C16 4.00(10) . . . . ?
C9 C8 C15 C16 123.13(13) . . . . ?
N2 C15 C16 O2 53.6(2) . . . . ?
C8 C15 C16 O2 175.48(17) . . . . ?
N2 C15 C16 N1 -126.21(13) . . . . ?
C8 C15 C16 N1 -4.32(11) . . . . ?
N2 C17 C18 C19 -0.60(17) . . . . ?
C21 C17 C18 C19 177.72(16) . . . . ?
C17 C18 C19 C20 0.33(18) . . . . ?
C18 C19 C20 N2 0.08(17) . . . . ?
C18 C19 C20 C22 -178.50(15) . . . . ?
O2 C16 N1 C5 -4.6(3) . . . . ?
C15 C16 N1 C5 175.19(14) . . . . ?
O2 C16 N1 C8 -175.20(16) . . . . ?
C15 C16 N1 C8 4.61(11) . . . . ?
C4 C5 N1 C16 -179.49(14) . . . . ?
C6 C5 N1 C16 -0.3(2) . . . . ?
C4 C5 N1 C8 -12.1(2) . . . . ?
C6 C5 N1 C8 167.13(14) . . . . ?
C9 C8 N1 C16 -124.36(13) . . . . ?
C15 C8 N1 C16 -4.49(11) . . . . ?
C9 C8 N1 C5 65.09(19) . . . . ?
C15 C8 N1 C5 -175.05(14) . . . . ?
C18 C17 N2 C20 0.66(17) . . . . ?
C21 C17 N2 C20 -177.83(14) . . . . ?
C18 C17 N2 C15 -176.13(13) . . . . ?
C21 C17 N2 C15 5.4(2) . . . . ?
C19 C20 N2 C17 -0.45(16) . . . . ?
C22 C20 N2 C17 178.21(14) . . . . ?
C19 C20 N2 C15 176.22(13) . . . . ?
C22 C20 N2 C15 -5.1(2) . . . . ?
C16 C15 N2 C17 -140.03(14) . . . . ?
C8 C15 N2 C17 117.60(15) . . . . ?
C16 C15 N2 C20 43.74(19) . . . . ?
C8 C15 N2 C20 -58.63(19) . . . . ?
C3 C2 O1 C1 11.2(2) . . . . ?
C7 C2 O1 C1 -168.97(14) . . . . ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full 67.24
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.207
_refine_diff_density_min -0.197
_refine_diff_density_rms 0.034
_iucr_refine_instructions_details
;
TITL xs0040a
CELL 1.54178 9.5368 11.2841 16.5037 90.000 90.689 90.000
ZERR 4 0.0002 0.0003 0.0005 0.000 0.002 0.000
LATT 1
SYMM 1/2-X,1/2+Y,1/2-Z
SFAC C H N O
UNIT 88 88 8 8
TEMP -173
ACTA
HTAB
BOND
BOND $H
CONF
WPDB
L.S. 6
FMAP 2
PLAN 10
OMIT -2 134.5
WGHT 0.036800 0.883400
FVAR 6.80116
C1 1 0.673663 -0.040413 0.437491 11.00000 0.03817 0.04040 =
0.05601 0.01291 -0.00061 -0.00850
AFIX 137
H1A 2 0.592821 0.002280 0.459110 11.00000 -1.50000
H1B 2 0.673069 -0.122232 0.457397 11.00000 -1.50000
H1C 2 0.668394 -0.040526 0.378152 11.00000 -1.50000
AFIX 0
C2 1 0.819273 0.131665 0.438580 11.00000 0.03495 0.02740 =
0.02715 0.00180 0.00147 0.00141
C3 1 0.717552 0.201866 0.402373 11.00000 0.02479 0.03037 =
0.02839 -0.00137 0.00185 -0.00203
AFIX 43
H3 2 0.626534 0.170838 0.391863 11.00000 -1.20000
AFIX 0
C4 1 0.749273 0.318571 0.381338 11.00000 0.02476 0.03011 =
0.02820 0.00029 -0.00068 0.00456
AFIX 43
H4 2 0.679688 0.367107 0.356450 11.00000 -1.20000
AFIX 0
C5 1 0.881687 0.363630 0.396647 11.00000 0.02545 0.02524 =
0.02685 -0.00046 -0.00018 0.00241
C6 1 0.984507 0.291680 0.432010 11.00000 0.02509 0.03073 =
0.03831 -0.00065 -0.00537 0.00234
AFIX 43
H6 2 1.076035 0.322100 0.441808 11.00000 -1.20000
AFIX 0
C7 1 0.953162 0.176573 0.452679 11.00000 0.03317 0.02951 =
0.03723 0.00164 -0.00812 0.00616
AFIX 43
H7 2 1.023268 0.127624 0.476670 11.00000 -1.20000
AFIX 0
C8 1 0.839290 0.570512 0.325387 11.00000 0.02642 0.02586 =
0.02764 0.00271 -0.00179 0.00065
AFIX 13
H8 2 0.832179 0.543790 0.267712 11.00000 -1.20000
AFIX 0
C9 1 0.699799 0.613826 0.355129 11.00000 0.02450 0.02085 =
0.03183 0.00102 -0.00129 -0.00182
C10 1 0.661887 0.605320 0.436105 11.00000 0.02999 0.02397 =
0.03089 0.00237 -0.00272 -0.00133
AFIX 43
H10 2 0.725326 0.572007 0.474638 11.00000 -1.20000
AFIX 0
C11 1 0.531613 0.645416 0.460614 11.00000 0.03189 0.02536 =
0.03200 -0.00088 0.00491 -0.00344
AFIX 43
H11 2 0.506505 0.639737 0.516009 11.00000 -1.20000
AFIX 0
C12 1 0.438094 0.693520 0.405193 11.00000 0.02383 0.02512 =
0.04327 -0.00437 0.00227 -0.00114
AFIX 43
H12 2 0.348653 0.719907 0.422378 11.00000 -1.20000
AFIX 0
C13 1 0.474804 0.703247 0.324589 11.00000 0.02786 0.02642 =
0.03869 0.00034 -0.00700 0.00308
AFIX 43
H13 2 0.410696 0.736492 0.286399 11.00000 -1.20000
AFIX 0
C14 1 0.605409 0.664362 0.299643 11.00000 0.02892 0.02741 =
0.02979 0.00245 -0.00094 -0.00068
AFIX 43
H14 2 0.630873 0.672146 0.244425 11.00000 -1.20000
AFIX 0
C15 1 0.971643 0.652135 0.339150 11.00000 0.02587 0.02934 =
0.02891 0.00165 0.00013 -0.00060
AFIX 13
H15 2 0.949569 0.717001 0.378262 11.00000 -1.20000
AFIX 0
C16 1 1.036117 0.545895 0.384084 11.00000 0.02485 0.02936 =
0.02713 -0.00093 -0.00040 -0.00032
C17 1 1.057353 0.819271 0.254043 11.00000 0.02830 0.03801 =
0.04021 0.00989 -0.00460 -0.00678
C18 1 1.125334 0.829378 0.182161 11.00000 0.03344 0.05798 =
0.03766 0.01347 -0.00474 -0.01766
AFIX 43
H18 2 1.147597 0.901460 0.155501 11.00000 -1.20000
AFIX 0
C19 1 1.157026 0.714082 0.154095 11.00000 0.02770 0.06769 =
0.03035 0.00342 0.00003 -0.01091
AFIX 43
H19 2 1.204618 0.695408 0.105495 11.00000 -1.20000
AFIX 0
C20 1 1.107298 0.634174 0.209029 11.00000 0.02354 0.05239 =
0.03032 -0.00080 -0.00260 0.00054
C21 1 1.005523 0.911546 0.309977 11.00000 0.04498 0.03206 =
0.05632 0.00982 0.00212 -0.00193
AFIX 137
H21A 2 1.030821 0.990022 0.289334 11.00000 -1.50000
H21B 2 1.048133 0.900035 0.363732 11.00000 -1.50000
H21C 2 0.903304 0.905666 0.313890 11.00000 -1.50000
AFIX 0
C22 1 1.116976 0.502969 0.208241 11.00000 0.03633 0.05277 =
0.03622 -0.00606 -0.00111 0.00820
AFIX 137
H22A 2 1.159672 0.476923 0.157545 11.00000 -1.50000
H22B 2 1.022803 0.468933 0.212437 11.00000 -1.50000
H22C 2 1.174847 0.476376 0.254220 11.00000 -1.50000
AFIX 0
N1 3 0.914634 0.481827 0.375868 11.00000 0.02300 0.02632 =
0.03095 0.00256 -0.00311 0.00194
N2 3 1.045214 0.699171 0.270499 11.00000 0.02412 0.03408 =
0.03146 0.00586 0.00073 -0.00089
O1 4 0.798983 0.016300 0.463240 11.00000 0.04329 0.02808 =
0.04457 0.00822 -0.00729 -0.00492
O2 4 1.148691 0.524444 0.414874 11.00000 0.02608 0.03541 =
0.03630 0.00253 -0.00587 -0.00145
HKLF 4
REM xs0040a
REM R1 = 0.0392 for 3004 Fo > 4sig(Fo) and 0.0415 for all 3194 data
REM 238 parameters refined using 0 restraints
END
WGHT 0.0367 0.8834
REM Highest difference peak 0.207, deepest hole -0.197, 1-sigma level 0.034
Q1 1 0.9253 0.9047 0.3672 11.00000 0.05 0.21
Q2 1 1.1415 0.8305 0.2372 11.00000 0.05 0.18
Q3 1 0.5781 0.7334 0.3140 11.00000 0.05 0.18
Q4 1 0.7831 0.1552 0.3977 11.00000 0.05 0.18
Q5 1 0.7710 0.5945 0.3417 11.00000 0.05 0.16
Q6 1 0.8970 0.3515 0.4436 11.00000 0.05 0.16
Q7 1 0.4908 0.6458 0.4199 11.00000 0.05 0.16
Q8 1 0.9728 0.7361 0.3341 11.00000 0.05 0.16
Q9 1 1.1167 0.6644 0.2611 11.00000 0.05 0.16
Q10 1 0.9026 0.6221 0.3238 11.00000 0.05 0.15
;
_database_code_depnum_ccdc_archive 'CCDC 932935'
#######################################################################
#
# 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_cdptao
#TrackingRef '19316_web_deposit_cif_file_0_HadiD.Arman_1365539920.tcdptaa.CIF'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
(+/-)N-(chrysen-6-yl)-3-(2,5-dimethyl-1H-pyrrol-1-yl)-4-
(thiophene-2-yl)azetidin-2-one acetone solvate
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C31 H24 N2 O S, C3 H6 O'
_chemical_formula_sum 'C34 H30 N2 O2 S'
_chemical_formula_weight 529.65
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M P2(1)/n
_symmetry_space_group_name_Hall '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 15.6995(12)
_cell_length_b 10.4795(9)
_cell_length_c 17.7531(16)
_cell_angle_alpha 90.00
_cell_angle_beta 111.535(8)
_cell_angle_gamma 90.00
_cell_volume 2716.9(4)
_cell_formula_units_Z 4
_cell_measurement_temperature 98(2)
_cell_measurement_reflns_used 13267
_cell_measurement_theta_min 3.0
_cell_measurement_theta_max 27.6
_exptl_crystal_description chunk
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.22
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.12
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.295
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1116
_exptl_absorpt_coefficient_mu 0.154
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.509
_exptl_absorpt_correction_T_max 1.000
_exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 98(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type
;
Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method \w
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number 0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% <1
_diffrn_reflns_number 16810
_diffrn_reflns_av_R_equivalents 0.0418
_diffrn_reflns_av_sigmaI/netI 0.0466
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_h_max 18
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -21
_diffrn_reflns_limit_l_max 21
_diffrn_reflns_theta_min 3.05
_diffrn_reflns_theta_max 25.05
_diffrn_reflns_reduction_process 'Lp corrections applied'
_reflns_number_total 4817
_reflns_number_gt 3812
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_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^ > 2sigma(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^)+(0.0300P)^2^+2.0000P] 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 4817
_refine_ls_number_parameters 370
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0580
_refine_ls_R_factor_gt 0.0436
_refine_ls_wR_factor_ref 0.1044
_refine_ls_wR_factor_gt 0.0968
_refine_ls_goodness_of_fit_ref 0.991
_refine_ls_restrained_S_all 0.991
_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
N1 N 0.66130(9) 0.83690(14) -0.05266(8) 0.0228(3) Uani 1 1 d . . .
O1 O 0.52927(8) 0.74658(12) -0.14946(7) 0.0287(3) Uani 1 1 d . . .
N2 N 0.62748(9) 0.55472(13) 0.00842(9) 0.0230(3) Uani 1 1 d . . .
C1 C 0.58863(12) 0.75530(16) -0.08332(11) 0.0232(4) Uani 1 1 d . . .
C4 C 0.70484(12) 0.92207(17) -0.08991(10) 0.0260(4) Uani 1 1 d . . .
C5 C 0.79292(13) 0.89851(18) -0.08121(11) 0.0292(4) Uani 1 1 d . . .
H5A H 0.8228 0.8281 -0.0512 0.035 Uiso 1 1 calc R . .
C20 C 0.56601(14) 1.05828(18) -0.13908(11) 0.0339(5) Uani 1 1 d . . .
H20A H 0.5366 1.0042 -0.1149 0.041 Uiso 1 1 calc R . .
C2 C 0.61237(11) 0.68948(16) -0.00040(10) 0.0226(4) Uani 1 1 d . . .
H2A H 0.5686 0.7154 0.0244 0.027 Uiso 1 1 calc R . .
C21 C 0.65570(13) 1.03038(18) -0.13338(11) 0.0302(4) Uani 1 1 d . . .
C29 C 0.66879(12) 0.47769(17) -0.03220(11) 0.0269(4) Uani 1 1 d . . .
C27 C 0.63553(13) 0.36138(18) 0.06000(11) 0.0304(4) Uani 1 1 d . . .
H27A H 0.6304 0.2923 0.0910 0.036 Uiso 1 1 calc R . .
C6 C 0.84055(14) 0.9791(2) -0.11703(11) 0.0345(5) Uani 1 1 d . . .
C15 C 0.79457(16) 1.0843(2) -0.16237(12) 0.0406(5) Uani 1 1 d . . .
C26 C 0.60815(12) 0.48291(17) 0.06593(10) 0.0249(4) Uani 1 1 d . . .
C16 C 0.70124(15) 1.11158(19) -0.17054(11) 0.0375(5) Uani 1 1 d . . .
C19 C 0.52140(16) 1.16435(19) -0.17991(13) 0.0444(6) Uani 1 1 d . . .
H19A H 0.4625 1.1831 -0.1826 0.053 Uiso 1 1 calc R . .
C8 C 0.98497(14) 0.8481(2) -0.06183(14) 0.0458(6) Uani 1 1 d . . .
H8A H 0.9578 0.7947 -0.0353 0.055 Uiso 1 1 calc R . .
C28 C 0.67311(13) 0.35791(18) -0.00136(12) 0.0304(4) Uani 1 1 d . . .
H28A H 0.6967 0.2862 -0.0177 0.036 Uiso 1 1 calc R . .
C3 C 0.69769(11) 0.77955(16) 0.02874(10) 0.0228(4) Uani 1 1 d . C .
H3A H 0.7552 0.7335 0.0391 0.027 Uiso 1 1 calc R . .
C22 C 0.70230(12) 0.86741(17) 0.09573(11) 0.0232(4) Uani 1 1 d . . .
C24 C 0.72397(13) 0.9516(2) 0.22693(12) 0.0363(5) Uani 1 1 d . . .
H24A H 0.7434 0.9567 0.2830 0.044 Uiso 1 1 calc R A 1
C23 C 0.67006(15) 1.0341(2) 0.17246(12) 0.0383(5) Uani 1 1 d . C .
H23A H 0.6521 1.1097 0.1898 0.046 Uiso 1 1 calc R B 1
C7 C 0.93488(15) 0.9512(2) -0.10740(13) 0.0433(6) Uani 1 1 d . . .
C18 C 0.56512(19) 1.2440(2) -0.21741(13) 0.0540(7) Uani 1 1 d . . .
H18A H 0.5347 1.3154 -0.2457 0.065 Uiso 1 1 calc R . .
C14 C 0.8432(2) 1.1630(2) -0.19961(13) 0.0565(7) Uani 1 1 d . . .
H14A H 0.8140 1.2334 -0.2301 0.068 Uiso 1 1 calc R . .
C17 C 0.65191(19) 1.2185(2) -0.21316(13) 0.0507(6) Uani 1 1 d . . .
H17A H 0.6794 1.2728 -0.2390 0.061 Uiso 1 1 calc R . .
C12 C 0.97895(18) 1.0307(3) -0.14564(15) 0.0557(7) Uani 1 1 d . . .
C13 C 0.9309(2) 1.1362(3) -0.19095(15) 0.0667(9) Uani 1 1 d . . .
H13A H 0.9603 1.1891 -0.2157 0.080 Uiso 1 1 calc R . .
C9 C 1.07352(16) 0.8248(3) -0.05578(16) 0.0620(8) Uani 1 1 d . . .
H9A H 1.1053 0.7561 -0.0251 0.074 Uiso 1 1 calc R . .
C11 C 1.0700(2) 1.0034(4) -0.13849(19) 0.0758(11) Uani 1 1 d . . .
H11A H 1.0987 1.0558 -0.1643 0.091 Uiso 1 1 calc R . .
C10 C 1.1161(2) 0.9022(4) -0.0947(2) 0.0799(11) Uani 1 1 d . . .
H10A H 1.1757 0.8849 -0.0908 0.096 Uiso 1 1 calc R . .
O4 O 0.90611(10) 0.64130(16) 0.04008(9) 0.0488(4) Uani 1 1 d . . .
C30 C 0.56813(12) 0.53958(18) 0.12267(11) 0.0286(4) Uani 1 1 d . . .
H30A H 0.5602 0.4740 0.1573 0.043 Uiso 1 1 calc R . .
H30B H 0.5099 0.5772 0.0922 0.043 Uiso 1 1 calc R . .
H30C H 0.6086 0.6040 0.1550 0.043 Uiso 1 1 calc R . .
C31 C 0.69800(13) 0.52443(19) -0.09810(12) 0.0327(4) Uani 1 1 d . . .
H31A H 0.7247 0.4554 -0.1173 0.049 Uiso 1 1 calc R . .
H31B H 0.7423 0.5913 -0.0777 0.049 Uiso 1 1 calc R . .
H31C H 0.6458 0.5567 -0.1418 0.049 Uiso 1 1 calc R . .
C32 C 0.94473(14) 0.5693(2) 0.09535(13) 0.0395(5) Uani 1 1 d . . .
C33 C 1.04268(15) 0.5311(2) 0.11549(15) 0.0525(6) Uani 1 1 d . . .
H33A H 1.0661 0.5722 0.0787 0.079 Uiso 1 1 calc R . .
H33B H 1.0464 0.4403 0.1107 0.079 Uiso 1 1 calc R . .
H33C H 1.0783 0.5566 0.1700 0.079 Uiso 1 1 calc R . .
C34 C 0.89673(18) 0.5156(3) 0.14546(16) 0.0641(8) Uani 1 1 d . . .
H34A H 0.8350 0.5471 0.1266 0.096 Uiso 1 1 calc R . .
H34B H 0.9279 0.5406 0.2009 0.096 Uiso 1 1 calc R . .
H34C H 0.8960 0.4242 0.1416 0.096 Uiso 1 1 calc R . .
C25A C 0.7467(9) 0.8472(12) 0.1768(7) 0.025(2) Uani 0.50 1 d P C 1
S1A S 0.63553(12) 1.00252(16) 0.07518(10) 0.0304(3) Uani 0.50 1 d P C 1
S1B S 0.7577(3) 0.8185(3) 0.1954(2) 0.0266(5) Uani 0.50 1 d P C 2
C25B C 0.6670(5) 0.9791(9) 0.0962(5) 0.056(3) Uani 0.50 1 d P C 2
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
N1 0.0250(8) 0.0209(8) 0.0218(8) 0.0024(6) 0.0080(6) -0.0033(6)
O1 0.0324(7) 0.0251(7) 0.0242(7) -0.0002(5) 0.0055(6) -0.0020(5)
N2 0.0254(8) 0.0175(7) 0.0256(8) 0.0009(6) 0.0087(6) -0.0014(6)
C1 0.0272(9) 0.0170(9) 0.0262(10) -0.0007(7) 0.0108(8) 0.0013(7)
C4 0.0361(10) 0.0216(9) 0.0208(9) -0.0026(7) 0.0110(7) -0.0072(8)
C5 0.0373(11) 0.0281(10) 0.0246(10) -0.0063(8) 0.0141(8) -0.0105(8)
C20 0.0428(11) 0.0232(10) 0.0270(10) -0.0013(8) 0.0025(8) -0.0032(8)
C2 0.0238(9) 0.0185(9) 0.0253(9) -0.0002(7) 0.0088(7) -0.0010(7)
C21 0.0436(11) 0.0222(10) 0.0209(9) -0.0029(7) 0.0072(8) -0.0088(8)
C29 0.0243(9) 0.0244(10) 0.0298(10) -0.0024(8) 0.0073(7) 0.0006(7)
C27 0.0356(10) 0.0205(10) 0.0298(10) 0.0047(8) 0.0058(8) -0.0027(8)
C6 0.0458(12) 0.0372(12) 0.0242(10) -0.0119(8) 0.0173(9) -0.0217(9)
C15 0.0620(14) 0.0390(12) 0.0243(11) -0.0102(9) 0.0198(9) -0.0285(11)
C26 0.0253(9) 0.0226(9) 0.0231(9) 0.0019(7) 0.0047(7) -0.0047(7)
C16 0.0612(14) 0.0256(10) 0.0203(10) -0.0032(8) 0.0086(9) -0.0176(9)
C19 0.0526(13) 0.0240(11) 0.0387(12) -0.0022(9) -0.0046(10) 0.0015(9)
C8 0.0376(12) 0.0613(16) 0.0452(13) -0.0235(12) 0.0230(10) -0.0202(11)
C28 0.0326(10) 0.0193(9) 0.0356(11) -0.0019(8) 0.0081(8) 0.0023(8)
C3 0.0215(8) 0.0220(9) 0.0237(9) 0.0038(7) 0.0070(7) -0.0015(7)
C22 0.0236(9) 0.0205(9) 0.0255(10) 0.0020(7) 0.0092(7) -0.0052(7)
C24 0.0364(11) 0.0403(12) 0.0293(11) -0.0003(9) 0.0087(8) -0.0100(9)
C23 0.0528(13) 0.0271(11) 0.0318(11) -0.0045(8) 0.0117(9) -0.0067(9)
C7 0.0481(13) 0.0561(15) 0.0362(12) -0.0286(11) 0.0278(10) -0.0334(11)
C18 0.0831(19) 0.0209(11) 0.0341(13) 0.0052(9) -0.0066(12) -0.0034(11)
C14 0.092(2) 0.0506(15) 0.0296(12) -0.0093(10) 0.0259(12) -0.0444(14)
C17 0.0841(19) 0.0295(12) 0.0268(12) 0.0028(9) 0.0068(11) -0.0195(12)
C12 0.0692(17) 0.0723(19) 0.0378(13) -0.0296(13) 0.0340(12) -0.0489(15)
C13 0.091(2) 0.084(2) 0.0394(14) -0.0284(14) 0.0410(14) -0.0672(18)
C9 0.0377(13) 0.094(2) 0.0595(16) -0.0395(15) 0.0244(12) -0.0258(13)
C11 0.0673(19) 0.122(3) 0.0581(18) -0.0556(19) 0.0467(16) -0.072(2)
C10 0.0492(17) 0.131(3) 0.072(2) -0.054(2) 0.0381(16) -0.0471(19)
O4 0.0448(9) 0.0531(10) 0.0466(10) 0.0122(8) 0.0146(7) 0.0068(8)
C30 0.0309(10) 0.0268(10) 0.0266(10) 0.0020(8) 0.0089(8) -0.0059(8)
C31 0.0369(11) 0.0270(10) 0.0381(11) -0.0042(8) 0.0184(9) 0.0007(8)
C32 0.0427(12) 0.0381(12) 0.0329(12) -0.0009(9) 0.0083(9) 0.0054(10)
C33 0.0456(13) 0.0459(15) 0.0580(16) -0.0035(11) 0.0097(11) 0.0083(11)
C34 0.0584(16) 0.083(2) 0.0530(16) 0.0262(14) 0.0234(13) 0.0198(14)
C25A 0.025(4) 0.030(5) 0.024(6) 0.005(3) 0.012(4) -0.005(3)
S1A 0.0399(10) 0.0230(6) 0.0304(9) -0.0060(6) 0.0155(7) -0.0034(6)
S1B 0.0265(8) 0.0313(13) 0.0180(12) 0.0055(7) 0.0033(8) -0.0063(8)
C25B 0.048(5) 0.064(6) 0.046(4) 0.012(3) 0.006(3) -0.011(4)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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
N1 C1 1.369(2) . ?
N1 C4 1.426(2) . ?
N1 C3 1.473(2) . ?
O1 C1 1.205(2) . ?
N2 C26 1.389(2) . ?
N2 C29 1.391(2) . ?
N2 C2 1.431(2) . ?
C1 C2 1.542(2) . ?
C4 C5 1.357(3) . ?
C4 C21 1.429(3) . ?
C5 C6 1.423(3) . ?
C5 H5A 0.9300 . ?
C20 C19 1.371(3) . ?
C20 C21 1.405(3) . ?
C20 H20A 0.9300 . ?
C2 C3 1.563(2) . ?
C2 H2A 0.9800 . ?
C21 C16 1.420(3) . ?
C29 C28 1.361(3) . ?
C29 C31 1.487(3) . ?
C27 C26 1.360(3) . ?
C27 C28 1.417(3) . ?
C27 H27A 0.9300 . ?
C6 C15 1.399(3) . ?
C6 C7 1.457(3) . ?
C15 C14 1.439(3) . ?
C15 C16 1.447(3) . ?
C26 C30 1.492(3) . ?
C16 C17 1.413(3) . ?
C19 C18 1.395(3) . ?
C19 H19A 0.9300 . ?
C8 C9 1.376(3) . ?
C8 C7 1.405(3) . ?
C8 H8A 0.9300 . ?
C28 H28A 0.9300 . ?
C3 C22 1.485(2) . ?
C3 H3A 0.9800 . ?
C22 C25B 1.296(9) . ?
C22 C25A 1.366(11) . ?
C22 S1A 1.719(2) . ?
C22 S1B 1.738(3) . ?
C24 C23 1.341(3) . ?
C24 C25A 1.533(16) . ?
C24 S1B 1.660(5) . ?
C24 H24A 0.9300 . ?
C23 C25B 1.457(10) . ?
C23 S1A 1.643(3) . ?
C23 H23A 0.9300 . ?
C7 C12 1.406(3) . ?
C18 C17 1.363(4) . ?
C18 H18A 0.9300 . ?
C14 C13 1.357(4) . ?
C14 H14A 0.9300 . ?
C17 H17A 0.9300 . ?
C12 C13 1.412(4) . ?
C12 C11 1.417(4) . ?
C13 H13A 0.9300 . ?
C9 C10 1.386(4) . ?
C9 H9A 0.9300 . ?
C11 C10 1.357(5) . ?
C11 H11A 0.9300 . ?
C10 H10A 0.9300 . ?
O4 C32 1.209(2) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C34 1.472(3) . ?
C32 C33 1.500(3) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 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 N1 C4 132.71(15) . . ?
C1 N1 C3 95.84(13) . . ?
C4 N1 C3 129.13(14) . . ?
C26 N2 C29 109.63(15) . . ?
C26 N2 C2 122.90(15) . . ?
C29 N2 C2 127.29(15) . . ?
O1 C1 N1 131.95(16) . . ?
O1 C1 C2 136.51(16) . . ?
N1 C1 C2 91.48(13) . . ?
C5 C4 N1 118.38(16) . . ?
C5 C4 C21 122.12(17) . . ?
N1 C4 C21 119.48(16) . . ?
C4 C5 C6 121.46(19) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C19 C20 C21 120.7(2) . . ?
C19 C20 H20A 119.6 . . ?
C21 C20 H20A 119.6 . . ?
N2 C2 C1 121.21(15) . . ?
N2 C2 C3 118.18(14) . . ?
C1 C2 C3 85.61(12) . . ?
N2 C2 H2A 109.9 . . ?
C1 C2 H2A 109.9 . . ?
C3 C2 H2A 109.9 . . ?
C20 C21 C16 120.27(18) . . ?
C20 C21 C4 122.16(17) . . ?
C16 C21 C4 117.57(18) . . ?
C28 C29 N2 106.89(16) . . ?
C28 C29 C31 129.48(17) . . ?
N2 C29 C31 123.61(16) . . ?
C26 C27 C28 108.43(16) . . ?
C26 C27 H27A 125.8 . . ?
C28 C27 H27A 125.8 . . ?
C15 C6 C5 118.67(19) . . ?
C15 C6 C7 120.87(19) . . ?
C5 C6 C7 120.5(2) . . ?
C6 C15 C14 117.9(2) . . ?
C6 C15 C16 120.20(18) . . ?
C14 C15 C16 121.9(2) . . ?
C27 C26 N2 106.85(16) . . ?
C27 C26 C30 130.40(17) . . ?
N2 C26 C30 122.71(16) . . ?
C17 C16 C21 117.0(2) . . ?
C17 C16 C15 123.1(2) . . ?
C21 C16 C15 119.93(19) . . ?
C20 C19 C18 119.5(2) . . ?
C20 C19 H19A 120.3 . . ?
C18 C19 H19A 120.3 . . ?
C9 C8 C7 121.2(2) . . ?
C9 C8 H8A 119.4 . . ?
C7 C8 H8A 119.4 . . ?
C29 C28 C27 108.19(17) . . ?
C29 C28 H28A 125.9 . . ?
C27 C28 H28A 125.9 . . ?
N1 C3 C22 114.84(15) . . ?
N1 C3 C2 86.85(12) . . ?
C22 C3 C2 115.06(14) . . ?
N1 C3 H3A 112.6 . . ?
C22 C3 H3A 112.6 . . ?
C2 C3 H3A 112.6 . . ?
C25B C22 C25A 100.8(7) . . ?
C25B C22 C3 132.0(4) . . ?
C25A C22 C3 127.1(6) . . ?
C25B C22 S1A 13.8(4) . . ?
C25A C22 S1A 112.8(6) . . ?
C3 C22 S1A 119.61(14) . . ?
C25B C22 S1B 108.4(4) . . ?
C25A C22 S1B 8.2(7) . . ?
C3 C22 S1B 119.46(19) . . ?
S1A C22 S1B 119.80(18) . . ?
C23 C24 C25A 105.1(3) . . ?
C23 C24 S1B 119.58(19) . . ?
C25A C24 S1B 14.9(3) . . ?
C23 C24 H24A 127.4 . . ?
C25A C24 H24A 127.4 . . ?
S1B C24 H24A 112.9 . . ?
C24 C23 C25B 102.2(3) . . ?
C24 C23 S1A 120.36(18) . . ?
C25B C23 S1A 19.5(3) . . ?
C24 C23 H23A 119.8 . . ?
C25B C23 H23A 137.3 . . ?
S1A C23 H23A 119.8 . . ?
C8 C7 C12 117.6(2) . . ?
C8 C7 C6 123.50(19) . . ?
C12 C7 C6 118.9(2) . . ?
C17 C18 C19 120.9(2) . . ?
C17 C18 H18A 119.6 . . ?
C19 C18 H18A 119.6 . . ?
C13 C14 C15 121.1(3) . . ?
C13 C14 H14A 119.5 . . ?
C15 C14 H14A 119.5 . . ?
C18 C17 C16 121.7(2) . . ?
C18 C17 H17A 119.2 . . ?
C16 C17 H17A 119.2 . . ?
C7 C12 C13 118.9(2) . . ?
C7 C12 C11 119.8(3) . . ?
C13 C12 C11 121.3(3) . . ?
C14 C13 C12 122.3(2) . . ?
C14 C13 H13A 118.8 . . ?
C12 C13 H13A 118.8 . . ?
C8 C9 C10 121.0(3) . . ?
C8 C9 H9A 119.5 . . ?
C10 C9 H9A 119.5 . . ?
C10 C11 C12 121.1(3) . . ?
C10 C11 H11A 119.4 . . ?
C12 C11 H11A 119.4 . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H10A 120.3 . . ?
C9 C10 H10A 120.3 . . ?
C26 C30 H30A 109.5 . . ?
C26 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C26 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O4 C32 C34 120.9(2) . . ?
O4 C32 C33 121.6(2) . . ?
C34 C32 C33 117.5(2) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C22 C25A C24 111.3(7) . . ?
C23 S1A C22 90.16(13) . . ?
C24 S1B C22 89.61(15) . . ?
C22 C25B C23 119.7(6) . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 25.05
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.378
_refine_diff_density_min -0.277
_refine_diff_density_rms 0.042
_database_code_depnum_ccdc_archive 'CCDC 933213'