# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is (c) The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2010
data_global
_journal_name_full 'New J.Chem.'
_journal_coden_Cambridge 0440
_publ_contact_author_name 'Roesler, Roland'
_publ_contact_author_email roesler@ucalgary.ca
_publ_section_title
;
The Influence of Electron Delocalization upon the Stability
and Structure of Potential N-Heterocyclic Carbene Precursors
with 1,3-Diaryl-imidazolidine-4,5-dione Skeletons
;
# Attachment '- 1a_final.cif'
_publ_section_references
;
Blessing, R. H. (1997). J. Appl. Cryst. 30, 421--426.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Fun, H-K., Goswami, S., Jana, S. & Chantrapromma, S. (2006).
Acta Cryst. E62, 05332--o5334.
Hooft, R. (1998). COLLECT. Nonius B V, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
Macromolecular Crystallography, Part A, edited by C. W. Carter Jr. and R. M.
Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122.
;
loop_
_publ_author_name
M.Hobbs
T.Forster
J.Borau-Garcia
C.Knapp
H.Tuononen
R.Roesler
#------------------------------------------------------------------------------
data_1a
_database_code_depnum_ccdc_archive 'CCDC 743953'
#TrackingRef '- 1a_final.cif'
#-----------------------------------------------------------------------------
_computing_data_collection 'COLLECT (Hooft, 1998)'
_computing_cell_refinement 'HKL DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)'
#-----------------------------------------------------------------------------
#data_shelxl
#TrackingRef '- 1a_final.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
2-chloro-1,3-bis(perfluorophenyl)imidazolidine-4,5-dione
;
_chemical_name_common
2-chloro-1,3-bis(perfluorophenyl)imidazolidine-4,5-dione
_chemical_melting_point ?
_chemical_formula_moiety 'C15 H1 Cl1 F10 N2 O2'
_chemical_formula_sum 'C15 H1 Cl1 F10 N2 O2'
_chemical_formula_weight 466.62
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_H-M 'C m c 21'
_symmetry_space_group_name_Hall 'C 2c -2'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
_cell_length_a 25.723(1)
_cell_length_b 10.273(2)
_cell_length_c 6.031(1)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1593.7(4)
_cell_formula_units_Z 4
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 1016
_cell_measurement_theta_min 3.09
_cell_measurement_theta_max 27.50
_exptl_crystal_description needles
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.08
_exptl_crystal_size_mid 0.03
_exptl_crystal_size_min 0.03
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.945
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 912
_exptl_absorpt_coefficient_mu 0.369
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_correction_T_min 0.9711
_exptl_absorpt_correction_T_max 0.9890
_exptl_absorpt_process_details 'SORTAV: (Blessing, 1997)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Nonius KappaCCD'
_diffrn_measurement_method ' \w and \f '
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 4697
_diffrn_reflns_av_R_equivalents 0.0562
_diffrn_reflns_av_sigmaI/netI 0.0429
_diffrn_reflns_limit_h_min -33
_diffrn_reflns_limit_h_max 29
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -7
_diffrn_reflns_limit_l_max 7
_diffrn_reflns_theta_min 3.09
_diffrn_reflns_theta_max 27.50
_reflns_number_total 1016
_reflns_number_gt 814
_reflns_threshold_expression >2sigma(I)
#_computing_data_collection ?
#_computing_cell_refinement ?
#_computing_data_reduction ?
#_computing_structure_solution ?
#_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
#_computing_molecular_graphics ?
#_computing_publication_material ?
_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^)+(0.0450P)^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 1016
_refine_ls_number_parameters 139
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0563
_refine_ls_R_factor_gt 0.0374
_refine_ls_wR_factor_ref 0.0835
_refine_ls_wR_factor_gt 0.0774
_refine_ls_goodness_of_fit_ref 1.098
_refine_ls_restrained_S_all 1.097
_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 0.0000 0.2484(4) 0.6460(8) 0.0261(10) Uani 1 2 d S . .
H1 H 0.0000 0.3151 0.5251 0.031 Uiso 1 2 calc SR . .
C2 C 0.02994(12) 0.2747(3) 1.0114(6) 0.0295(7) Uani 1 1 d . . .
C3 C 0.09545(11) 0.2571(3) 0.7134(5) 0.0277(7) Uani 1 1 d . . .
C4 C 0.11673(13) 0.3519(3) 0.5780(5) 0.0297(8) Uani 1 1 d . . .
C5 C 0.16611(13) 0.3397(3) 0.4937(6) 0.0338(8) Uani 1 1 d . . .
C6 C 0.19507(12) 0.2313(3) 0.5446(7) 0.0362(8) Uani 1 1 d . . .
C7 C 0.17520(13) 0.1361(3) 0.6806(6) 0.0331(8) Uani 1 1 d . . .
C8 C 0.12598(12) 0.1488(3) 0.7622(6) 0.0298(7) Uani 1 1 d . . .
F1 F 0.08860(8) 0.45749(15) 0.5289(4) 0.0396(5) Uani 1 1 d . . .
F2 F 0.18569(8) 0.4325(2) 0.3636(5) 0.0526(6) Uani 1 1 d . . .
F3 F 0.24358(8) 0.2192(2) 0.4661(4) 0.0503(6) Uani 1 1 d . . .
F4 F 0.20339(7) 0.0300(2) 0.7267(4) 0.0484(6) Uani 1 1 d . . .
F5 F 0.10638(7) 0.05452(19) 0.8904(4) 0.0436(5) Uani 1 1 d . . .
N1 N 0.04370(10) 0.2677(3) 0.7918(4) 0.0279(6) Uani 1 1 d . . .
O1 O 0.05755(9) 0.2819(3) 1.1710(4) 0.0375(6) Uani 1 1 d . . .
Cl1 Cl 0.0000 0.08740(10) 0.5315(2) 0.0340(3) Uani 1 2 d S . .
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 0.025(2) 0.030(2) 0.023(2) 0.0002(18) 0.000 0.000
C2 0.0366(17) 0.0282(14) 0.0238(17) 0.0023(16) -0.0024(15) -0.0022(13)
C3 0.0252(16) 0.0352(16) 0.0228(18) 0.0001(14) -0.0018(14) -0.0055(13)
C4 0.0340(17) 0.0324(17) 0.0228(19) 0.0021(14) -0.0041(14) -0.0035(15)
C5 0.0356(16) 0.0398(18) 0.0260(19) 0.0029(16) 0.0037(15) -0.0117(16)
C6 0.0260(16) 0.0498(19) 0.0329(19) -0.003(2) 0.0033(17) -0.0072(15)
C7 0.0299(16) 0.0394(18) 0.0300(18) 0.0032(16) -0.0060(14) 0.0035(15)
C8 0.0287(16) 0.0323(16) 0.0283(18) 0.0031(15) -0.0035(14) -0.0064(14)
F1 0.0483(10) 0.0329(9) 0.0376(11) 0.0050(11) 0.0043(11) 0.0009(8)
F2 0.0499(12) 0.0537(13) 0.0542(16) 0.0203(11) 0.0163(12) -0.0075(11)
F3 0.0295(10) 0.0707(15) 0.0508(15) 0.0050(12) 0.0118(10) -0.0002(10)
F4 0.0340(10) 0.0514(15) 0.0598(16) 0.0122(12) -0.0013(10) 0.0088(10)
F5 0.0356(10) 0.0468(11) 0.0483(13) 0.0200(11) 0.0032(10) -0.0031(9)
N1 0.0243(13) 0.0362(14) 0.0230(15) 0.0011(12) -0.0022(11) -0.0023(12)
O1 0.0390(13) 0.0493(16) 0.0243(13) 0.0017(12) -0.0048(12) -0.0063(11)
Cl1 0.0336(6) 0.0348(5) 0.0335(6) -0.0055(6) 0.000 0.000
_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 N1 1.441(4) . ?
C1 N1 1.441(4) 3 ?
C1 Cl1 1.793(4) . ?
C1 H1 1.0000 . ?
C2 O1 1.198(4) . ?
C2 N1 1.373(5) . ?
C2 C2 1.540(6) 3 ?
C3 C4 1.384(4) . ?
C3 C8 1.393(4) . ?
C3 N1 1.417(4) . ?
C4 F1 1.337(4) . ?
C4 C5 1.374(5) . ?
C5 F2 1.333(4) . ?
C5 C6 1.375(5) . ?
C6 F3 1.340(4) . ?
C6 C7 1.375(5) . ?
C7 F4 1.338(4) . ?
C7 C8 1.365(5) . ?
C8 F5 1.338(4) . ?
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
N1 C1 N1 102.5(4) . 3 ?
N1 C1 Cl1 111.2(2) . . ?
N1 C1 Cl1 111.2(2) 3 . ?
N1 C1 H1 110.5 . . ?
N1 C1 H1 110.5 3 . ?
Cl1 C1 H1 110.5 . . ?
O1 C2 N1 128.7(3) . . ?
O1 C2 C2 126.4(2) . 3 ?
N1 C2 C2 104.95(17) . 3 ?
C4 C3 C8 117.6(3) . . ?
C4 C3 N1 121.0(3) . . ?
C8 C3 N1 121.3(3) . . ?
F1 C4 C5 119.5(3) . . ?
F1 C4 C3 119.2(3) . . ?
C5 C4 C3 121.3(3) . . ?
F2 C5 C4 120.1(3) . . ?
F2 C5 C6 120.4(3) . . ?
C4 C5 C6 119.4(3) . . ?
F3 C6 C7 119.4(3) . . ?
F3 C6 C5 120.0(3) . . ?
C7 C6 C5 120.6(3) . . ?
F4 C7 C8 120.4(3) . . ?
F4 C7 C6 120.1(3) . . ?
C8 C7 C6 119.5(3) . . ?
F5 C8 C7 119.2(3) . . ?
F5 C8 C3 119.2(3) . . ?
C7 C8 C3 121.6(3) . . ?
C2 N1 C3 124.6(3) . . ?
C2 N1 C1 113.3(3) . . ?
C3 N1 C1 121.2(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
C8 C3 C4 F1 -179.6(3) . . . . ?
N1 C3 C4 F1 2.9(5) . . . . ?
C8 C3 C4 C5 0.3(5) . . . . ?
N1 C3 C4 C5 -177.2(3) . . . . ?
F1 C4 C5 F2 -0.1(5) . . . . ?
C3 C4 C5 F2 -180.0(3) . . . . ?
F1 C4 C5 C6 179.9(3) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
F2 C5 C6 F3 1.0(5) . . . . ?
C4 C5 C6 F3 -179.0(3) . . . . ?
F2 C5 C6 C7 179.3(3) . . . . ?
C4 C5 C6 C7 -0.7(5) . . . . ?
F3 C6 C7 F4 -2.6(5) . . . . ?
C5 C6 C7 F4 179.0(3) . . . . ?
F3 C6 C7 C8 179.4(3) . . . . ?
C5 C6 C7 C8 1.1(5) . . . . ?
F4 C7 C8 F5 0.5(5) . . . . ?
C6 C7 C8 F5 178.5(3) . . . . ?
F4 C7 C8 C3 -178.8(3) . . . . ?
C6 C7 C8 C3 -0.8(5) . . . . ?
C4 C3 C8 F5 -179.2(3) . . . . ?
N1 C3 C8 F5 -1.7(5) . . . . ?
C4 C3 C8 C7 0.2(5) . . . . ?
N1 C3 C8 C7 177.7(3) . . . . ?
O1 C2 N1 C3 5.4(5) . . . . ?
C2 C2 N1 C3 -175.9(2) 3 . . . ?
O1 C2 N1 C1 174.8(3) . . . . ?
C2 C2 N1 C1 -6.5(3) 3 . . . ?
C4 C3 N1 C2 -119.0(3) . . . . ?
C8 C3 N1 C2 63.6(4) . . . . ?
C4 C3 N1 C1 72.4(5) . . . . ?
C8 C3 N1 C1 -105.0(4) . . . . ?
N1 C1 N1 C2 10.1(5) 3 . . . ?
Cl1 C1 N1 C2 -108.9(3) . . . . ?
N1 C1 N1 C3 179.89(18) 3 . . . ?
Cl1 C1 N1 C3 60.9(4) . . . . ?
_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full 27.50
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max 0.220
_refine_diff_density_min -0.334
_refine_diff_density_rms 0.057
# Attachment '- 5a_final.cif'
_publ_section_references
;
Blessing, R. H. (1997). J. Appl. Cryst. 30, 421--426.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Fun, H-K., Goswami, S., Jana, S. & Chantrapromma, S. (2006).
Acta Cryst. E62, 05332--o5334.
Hooft, R. (1998). COLLECT. Nonius B V, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
Macromolecular Crystallography, Part A, edited by C. W. Carter Jr. and R. M.
Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122.
;
#------------------------------------------------------------------------------
data_shelxl2b
_database_code_depnum_ccdc_archive 'CCDC 743954'
#TrackingRef '- 2b.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C38 H38 N4 O4, C4 H8 O'
_chemical_formula_sum 'C42 H46 N4 O5'
_chemical_formula_weight 686.83
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 'C 1 2/c 1'
_symmetry_space_group_name_Hall '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 21.883(1)
_cell_length_b 14.616(1)
_cell_length_c 21.925(1)
_cell_angle_alpha 90.00
_cell_angle_beta 96.910(1)
_cell_angle_gamma 90.00
_cell_volume 6961.6(7)
_cell_formula_units_Z 8
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 7937
_cell_measurement_theta_min 1.87
_cell_measurement_theta_max 27.48
_exptl_crystal_description blocks
_exptl_crystal_colour Colorless
_exptl_crystal_size_max 0.10
_exptl_crystal_size_mid 0.10
_exptl_crystal_size_min 0.06
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.311
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 2928
_exptl_absorpt_coefficient_mu 0.086
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_correction_T_min 0.9914
_exptl_absorpt_correction_T_max 0.9948
_exptl_absorpt_process_details 'SORTAV: (Blessing, 1997)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Nonius KappaCCD'
_diffrn_measurement_method ' \w and \f '
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 40438
_diffrn_reflns_av_R_equivalents 0.1077
_diffrn_reflns_av_sigmaI/netI 0.0638
_diffrn_reflns_limit_h_min -28
_diffrn_reflns_limit_h_max 28
_diffrn_reflns_limit_k_min -18
_diffrn_reflns_limit_k_max 18
_diffrn_reflns_limit_l_min -28
_diffrn_reflns_limit_l_max 28
_diffrn_reflns_theta_min 1.87
_diffrn_reflns_theta_max 27.48
_reflns_number_total 7937
_reflns_number_gt 5490
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution ?
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_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^)+(0.0661P)^2^+9.9799P] 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 SHELXL
_refine_ls_extinction_coef 0.0029(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 7937
_refine_ls_number_parameters 461
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0954
_refine_ls_R_factor_gt 0.0579
_refine_ls_wR_factor_ref 0.1570
_refine_ls_wR_factor_gt 0.1342
_refine_ls_goodness_of_fit_ref 1.018
_refine_ls_restrained_S_all 1.018
_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 0.29216(9) 0.94754(14) 0.13520(8) 0.0202(4) Uani 1 1 d . . .
H1 H 0.2930 0.8851 0.1539 0.024 Uiso 1 1 calc R . .
C2 C 0.19695(9) 1.02053(14) 0.11099(9) 0.0233(4) Uani 1 1 d . . .
C3 C 0.21592(9) 0.97936(14) 0.05228(9) 0.0236(4) Uani 1 1 d . . .
C4 C 0.22110(9) 0.98292(14) 0.21824(9) 0.0225(4) Uani 1 1 d . . .
C5 C 0.23452(9) 1.04418(14) 0.26699(9) 0.0239(4) Uani 1 1 d . . .
C6 C 0.21010(10) 1.02578(16) 0.32173(10) 0.0295(5) Uani 1 1 d . . .
H6 H 0.2198 1.0655 0.3558 0.035 Uiso 1 1 calc R . .
C7 C 0.17243(11) 0.95169(16) 0.32767(10) 0.0321(5) Uani 1 1 d . . .
H7 H 0.1560 0.9411 0.3652 0.038 Uiso 1 1 calc R . .
C8 C 0.15862(10) 0.89267(16) 0.27856(10) 0.0300(5) Uani 1 1 d . . .
H8 H 0.1326 0.8416 0.2827 0.036 Uiso 1 1 calc R . .
C9 C 0.18244(10) 0.90709(15) 0.22318(10) 0.0253(4) Uani 1 1 d . . .
C10 C 0.27381(11) 1.12772(16) 0.26441(10) 0.0309(5) Uani 1 1 d . . .
H10A H 0.2767 1.1598 0.3039 0.046 Uiso 0.50 1 calc PR . .
H10B H 0.2553 1.1683 0.2317 0.046 Uiso 0.50 1 calc PR . .
H10C H 0.3151 1.1096 0.2559 0.046 Uiso 0.50 1 calc PR . .
H10D H 0.2880 1.1320 0.2238 0.046 Uiso 0.50 1 calc PR . .
H10E H 0.3094 1.1235 0.2960 0.046 Uiso 0.50 1 calc PR . .
H10F H 0.2497 1.1822 0.2718 0.046 Uiso 0.50 1 calc PR . .
C11 C 0.16445(11) 0.84263(16) 0.17068(10) 0.0316(5) Uani 1 1 d . . .
H11A H 0.1847 0.8612 0.1351 0.047 Uiso 0.50 1 calc PR . .
H11B H 0.1197 0.8443 0.1598 0.047 Uiso 0.50 1 calc PR . .
H11C H 0.1772 0.7803 0.1829 0.047 Uiso 0.50 1 calc PR . .
H11D H 0.1364 0.7960 0.1834 0.047 Uiso 0.50 1 calc PR . .
H11E H 0.2014 0.8129 0.1588 0.047 Uiso 0.50 1 calc PR . .
H11F H 0.1439 0.8769 0.1356 0.047 Uiso 0.50 1 calc PR . .
C12 C 0.30711(9) 0.89261(14) 0.02691(9) 0.0224(4) Uani 1 1 d . . .
C13 C 0.32573(10) 0.94315(15) -0.02228(9) 0.0254(4) Uani 1 1 d . . .
C14 C 0.36300(10) 0.89837(17) -0.06043(10) 0.0321(5) Uani 1 1 d . . .
H14 H 0.3761 0.9306 -0.0942 0.039 Uiso 1 1 calc R . .
C15 C 0.38123(10) 0.80906(17) -0.05039(10) 0.0342(5) Uani 1 1 d . . .
H15 H 0.4080 0.7812 -0.0759 0.041 Uiso 1 1 calc R . .
C16 C 0.36049(10) 0.75982(16) -0.00295(10) 0.0311(5) Uani 1 1 d . . .
H16 H 0.3725 0.6977 0.0031 0.037 Uiso 1 1 calc R . .
C17 C 0.32224(10) 0.79994(15) 0.03611(9) 0.0253(4) Uani 1 1 d . . .
C18 C 0.30661(11) 1.04011(16) -0.03623(10) 0.0314(5) Uani 1 1 d . . .
H18A H 0.2808 1.0616 -0.0056 0.047 Uiso 0.50 1 calc PR . .
H18B H 0.2832 1.0432 -0.0772 0.047 Uiso 0.50 1 calc PR . .
H18C H 0.3433 1.0789 -0.0350 0.047 Uiso 0.50 1 calc PR . .
H18D H 0.3241 1.0609 -0.0730 0.047 Uiso 0.50 1 calc PR . .
H18E H 0.3217 1.0793 -0.0013 0.047 Uiso 0.50 1 calc PR . .
H18F H 0.2616 1.0436 -0.0435 0.047 Uiso 0.50 1 calc PR . .
C19 C 0.29706(11) 0.74062(15) 0.08355(10) 0.0291(5) Uani 1 1 d . . .
H19A H 0.3138 0.6786 0.0817 0.044 Uiso 0.50 1 calc PR . .
H19B H 0.2521 0.7384 0.0753 0.044 Uiso 0.50 1 calc PR . .
H19C H 0.3090 0.7663 0.1245 0.044 Uiso 0.50 1 calc PR . .
H19D H 0.2694 0.7769 0.1060 0.044 Uiso 0.50 1 calc PR . .
H19E H 0.3312 0.7172 0.1124 0.044 Uiso 0.50 1 calc PR . .
H19F H 0.2743 0.6892 0.0631 0.044 Uiso 0.50 1 calc PR . .
C21 C 0.40100(9) 1.11191(14) 0.20305(9) 0.0231(4) Uani 1 1 d . . .
C22 C 0.41580(9) 1.02471(14) 0.23997(9) 0.0216(4) Uani 1 1 d . . .
C23 C 0.37030(10) 1.14640(15) 0.09500(9) 0.0252(5) Uani 1 1 d . . .
C24 C 0.32558(10) 1.21418(15) 0.08130(9) 0.0283(5) Uani 1 1 d . . .
C25 C 0.33239(12) 1.27351(16) 0.03266(10) 0.0352(5) Uani 1 1 d . . .
H25 H 0.3023 1.3197 0.0224 0.042 Uiso 1 1 calc R . .
C26 C 0.38149(12) 1.26687(18) -0.00088(11) 0.0406(6) Uani 1 1 d . . .
H26 H 0.3850 1.3077 -0.0340 0.049 Uiso 1 1 calc R . .
C27 C 0.42553(11) 1.20053(18) 0.01394(10) 0.0379(6) Uani 1 1 d . . .
H27 H 0.4594 1.1962 -0.0092 0.045 Uiso 1 1 calc R . .
C28 C 0.42137(10) 1.13971(17) 0.06209(10) 0.0319(5) Uani 1 1 d . . .
C29 C 0.27172(11) 1.22717(16) 0.11649(10) 0.0343(5) Uani 1 1 d . . .
H29A H 0.2466 1.2784 0.0989 0.051 Uiso 0.50 1 calc PR . .
H29B H 0.2865 1.2404 0.1596 0.051 Uiso 0.50 1 calc PR . .
H29C H 0.2468 1.1713 0.1141 0.051 Uiso 0.50 1 calc PR . .
H29D H 0.2733 1.1816 0.1495 0.051 Uiso 0.50 1 calc PR . .
H29E H 0.2335 1.2196 0.0888 0.051 Uiso 0.50 1 calc PR . .
H29F H 0.2731 1.2888 0.1343 0.051 Uiso 0.50 1 calc PR . .
C30 C 0.47159(11) 1.0701(2) 0.07676(13) 0.0478(7) Uani 1 1 d . . .
H30A H 0.5026 1.0776 0.0484 0.072 Uiso 0.50 1 calc PR . .
H30B H 0.4540 1.0085 0.0724 0.072 Uiso 0.50 1 calc PR . .
H30C H 0.4909 1.0790 0.1190 0.072 Uiso 0.50 1 calc PR . .
H30D H 0.4624 1.0325 0.1115 0.072 Uiso 0.50 1 calc PR . .
H30E H 0.5110 1.1016 0.0875 0.072 Uiso 0.50 1 calc PR . .
H30F H 0.4741 1.0310 0.0408 0.072 Uiso 0.50 1 calc PR . .
C31 C 0.40085(9) 0.85813(14) 0.21757(9) 0.0219(4) Uani 1 1 d . . .
C32 C 0.37439(9) 0.82075(15) 0.26711(9) 0.0267(5) Uani 1 1 d . . .
C33 C 0.38030(11) 0.72672(16) 0.27753(11) 0.0353(5) Uani 1 1 d . . .
H33 H 0.3629 0.7002 0.3110 0.042 Uiso 1 1 calc R . .
C34 C 0.41095(11) 0.67155(16) 0.24005(12) 0.0394(6) Uani 1 1 d . . .
H34 H 0.4128 0.6073 0.2465 0.047 Uiso 1 1 calc R . .
C35 C 0.43888(11) 0.71026(16) 0.19324(11) 0.0349(5) Uani 1 1 d . . .
H35 H 0.4607 0.6721 0.1682 0.042 Uiso 1 1 calc R . .
C36 C 0.43596(9) 0.80397(15) 0.18162(9) 0.0263(5) Uani 1 1 d . . .
C37 C 0.34222(11) 0.87740(17) 0.31078(11) 0.0356(5) Uani 1 1 d . . .
H37A H 0.3272 0.8374 0.3416 0.053 Uiso 0.50 1 calc PR . .
H37B H 0.3074 0.9095 0.2879 0.053 Uiso 0.50 1 calc PR . .
H37C H 0.3711 0.9222 0.3312 0.053 Uiso 0.50 1 calc PR . .
H37D H 0.3433 0.9420 0.2989 0.053 Uiso 0.50 1 calc PR . .
H37E H 0.3631 0.8699 0.3526 0.053 Uiso 0.50 1 calc PR . .
H37F H 0.2994 0.8573 0.3093 0.053 Uiso 0.50 1 calc PR . .
C38 C 0.47194(10) 0.84296(17) 0.13323(10) 0.0320(5) Uani 1 1 d . . .
H38A H 0.4654 0.9092 0.1304 0.048 Uiso 0.50 1 calc PR . .
H38B H 0.4580 0.8146 0.0935 0.048 Uiso 0.50 1 calc PR . .
H38C H 0.5159 0.8304 0.1444 0.048 Uiso 0.50 1 calc PR . .
H38D H 0.4941 0.7936 0.1151 0.048 Uiso 0.50 1 calc PR . .
H38E H 0.5015 0.8882 0.1520 0.048 Uiso 0.50 1 calc PR . .
H38F H 0.4436 0.8724 0.1011 0.048 Uiso 0.50 1 calc PR . .
C53 C 0.00618(14) 0.8511(2) 0.35311(14) 0.0518(7) Uani 1 1 d . . .
H53A H -0.0138 0.8130 0.3191 0.062 Uiso 1 1 calc R . .
H53B H 0.0498 0.8325 0.3623 0.062 Uiso 1 1 calc R . .
C54 C 0.00108(15) 0.9518(2) 0.33697(14) 0.0581(8) Uani 1 1 d . . .
H54A H 0.0343 0.9710 0.3128 0.070 Uiso 1 1 calc R . .
H54B H -0.0393 0.9660 0.3134 0.070 Uiso 1 1 calc R . .
C55 C 0.00771(16) 0.9968(2) 0.39886(16) 0.0617(9) Uani 1 1 d . . .
H55A H -0.0187 1.0518 0.3986 0.074 Uiso 1 1 calc R . .
H55B H 0.0510 1.0147 0.4116 0.074 Uiso 1 1 calc R . .
C56 C -0.01284(14) 0.9240(2) 0.44131(13) 0.0518(7) Uani 1 1 d . . .
H56A H 0.0198 0.9126 0.4758 0.062 Uiso 1 1 calc R . .
H56B H -0.0505 0.9442 0.4585 0.062 Uiso 1 1 calc R . .
N1 N 0.24222(8) 0.99964(12) 0.15832(7) 0.0215(4) Uani 1 1 d . . .
N2 N 0.27110(8) 0.93854(12) 0.06893(7) 0.0212(4) Uani 1 1 d . . .
N3 N 0.36784(8) 1.08638(11) 0.14811(7) 0.0222(4) Uani 1 1 d . . .
N4 N 0.39236(8) 0.95469(11) 0.20334(7) 0.0205(4) Uani 1 1 d . . .
O1 O 0.14890(7) 1.05983(11) 0.11528(7) 0.0309(4) Uani 1 1 d . . .
O2 O 0.18569(7) 0.98112(11) 0.00202(6) 0.0313(4) Uani 1 1 d . . .
O3 O 0.41700(7) 1.18825(10) 0.21895(7) 0.0316(4) Uani 1 1 d . . .
O4 O 0.44413(7) 1.02014(10) 0.29104(6) 0.0296(4) Uani 1 1 d . . .
O5 O -0.02495(9) 0.84301(13) 0.40591(9) 0.0487(5) Uani 1 1 d . . .
C20 C 0.35969(9) 0.98715(13) 0.14476(8) 0.0197(4) Uani 1 1 d . . .
H20 H 0.3821 0.9637 0.1108 0.024 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
C1 0.0235(10) 0.0186(10) 0.0179(9) -0.0017(7) 0.0006(7) -0.0006(8)
C2 0.0248(11) 0.0187(10) 0.0258(10) 0.0010(8) 0.0008(8) 0.0003(8)
C3 0.0241(10) 0.0222(11) 0.0236(10) 0.0020(8) -0.0005(8) 0.0014(8)
C4 0.0225(10) 0.0233(11) 0.0220(10) 0.0010(8) 0.0040(7) 0.0036(8)
C5 0.0241(10) 0.0233(11) 0.0243(10) -0.0006(8) 0.0023(8) 0.0050(8)
C6 0.0330(12) 0.0323(13) 0.0235(11) -0.0021(9) 0.0043(8) 0.0074(10)
C7 0.0329(12) 0.0369(13) 0.0281(11) 0.0074(9) 0.0106(9) 0.0074(10)
C8 0.0276(11) 0.0282(12) 0.0348(12) 0.0075(9) 0.0062(9) -0.0007(9)
C9 0.0229(10) 0.0234(11) 0.0295(11) 0.0016(8) 0.0025(8) 0.0038(8)
C10 0.0351(12) 0.0278(12) 0.0297(11) -0.0046(9) 0.0035(9) -0.0017(10)
C11 0.0319(12) 0.0253(12) 0.0373(12) -0.0019(9) 0.0034(9) -0.0059(9)
C12 0.0237(10) 0.0230(11) 0.0195(9) -0.0053(8) -0.0010(7) 0.0005(8)
C13 0.0270(11) 0.0269(11) 0.0212(10) -0.0045(8) -0.0009(8) -0.0032(9)
C14 0.0316(12) 0.0396(14) 0.0256(11) -0.0059(9) 0.0054(9) -0.0049(10)
C15 0.0284(12) 0.0397(14) 0.0352(12) -0.0158(10) 0.0063(9) -0.0010(10)
C16 0.0282(11) 0.0264(12) 0.0373(12) -0.0105(9) -0.0015(9) 0.0038(9)
C17 0.0247(10) 0.0235(11) 0.0259(10) -0.0050(8) -0.0039(8) -0.0008(8)
C18 0.0413(13) 0.0286(12) 0.0237(11) 0.0012(9) 0.0020(9) -0.0034(10)
C19 0.0353(12) 0.0202(11) 0.0303(11) -0.0019(8) -0.0030(9) -0.0009(9)
C21 0.0246(10) 0.0218(11) 0.0225(10) -0.0002(8) 0.0010(8) 0.0012(8)
C22 0.0206(10) 0.0216(10) 0.0225(10) -0.0015(8) 0.0022(7) 0.0001(8)
C23 0.0276(11) 0.0241(11) 0.0223(10) 0.0049(8) -0.0041(8) -0.0053(9)
C24 0.0339(12) 0.0209(11) 0.0279(11) 0.0015(8) -0.0057(9) -0.0038(9)
C25 0.0434(14) 0.0240(12) 0.0352(12) 0.0071(9) -0.0073(10) 0.0012(10)
C26 0.0481(15) 0.0387(14) 0.0329(12) 0.0152(10) -0.0045(11) -0.0100(12)
C27 0.0328(13) 0.0481(16) 0.0322(12) 0.0114(11) 0.0011(9) -0.0065(11)
C28 0.0264(11) 0.0374(13) 0.0305(12) 0.0083(9) -0.0029(9) -0.0047(10)
C29 0.0429(14) 0.0242(12) 0.0346(12) 0.0022(9) -0.0001(10) 0.0048(10)
C30 0.0276(13) 0.067(2) 0.0505(15) 0.0267(14) 0.0107(11) 0.0071(12)
C31 0.0213(10) 0.0174(10) 0.0250(10) 0.0002(7) -0.0048(7) 0.0020(8)
C32 0.0222(10) 0.0258(11) 0.0307(11) 0.0037(9) -0.0024(8) -0.0007(9)
C33 0.0329(12) 0.0284(13) 0.0425(13) 0.0107(10) -0.0036(10) -0.0059(10)
C34 0.0375(13) 0.0195(12) 0.0576(16) 0.0025(10) -0.0092(11) -0.0006(10)
C35 0.0317(12) 0.0254(12) 0.0447(13) -0.0077(10) -0.0067(10) 0.0068(10)
C36 0.0210(10) 0.0248(11) 0.0307(11) -0.0054(8) -0.0060(8) 0.0019(8)
C37 0.0366(13) 0.0385(14) 0.0327(12) 0.0071(10) 0.0087(10) 0.0030(11)
C38 0.0269(11) 0.0367(13) 0.0323(12) -0.0064(9) 0.0028(9) 0.0065(10)
C53 0.0437(16) 0.059(2) 0.0532(17) -0.0038(14) 0.0101(12) -0.0021(14)
C54 0.0469(17) 0.069(2) 0.0600(19) 0.0257(16) 0.0129(14) 0.0014(15)
C55 0.058(2) 0.0475(18) 0.083(2) 0.0025(16) 0.0241(17) -0.0077(15)
C56 0.0540(17) 0.0503(18) 0.0506(16) 0.0009(13) 0.0040(13) 0.0007(14)
N1 0.0226(9) 0.0214(9) 0.0203(8) -0.0016(6) 0.0019(6) 0.0017(7)
N2 0.0233(9) 0.0205(9) 0.0189(8) -0.0016(6) -0.0020(6) 0.0021(7)
N3 0.0251(9) 0.0193(9) 0.0214(8) 0.0024(6) -0.0003(6) -0.0014(7)
N4 0.0240(9) 0.0178(9) 0.0186(8) -0.0010(6) -0.0020(6) 0.0019(7)
O1 0.0271(8) 0.0309(9) 0.0344(8) 0.0007(6) 0.0016(6) 0.0086(7)
O2 0.0300(8) 0.0371(9) 0.0244(8) -0.0008(6) -0.0061(6) 0.0041(7)
O3 0.0403(9) 0.0206(8) 0.0323(8) -0.0021(6) -0.0019(6) -0.0031(7)
O4 0.0363(9) 0.0282(8) 0.0219(7) -0.0001(6) -0.0069(6) -0.0016(7)
O5 0.0458(11) 0.0440(12) 0.0564(12) 0.0088(9) 0.0069(9) -0.0088(9)
C20 0.0209(10) 0.0197(10) 0.0178(9) 0.0009(7) -0.0007(7) 0.0023(8)
_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 N1 1.471(3) . ?
C1 N2 1.476(2) . ?
C1 C20 1.577(3) . ?
C1 H1 1.0000 . ?
C2 O1 1.212(3) . ?
C2 N1 1.380(3) . ?
C2 C3 1.523(3) . ?
C3 O2 1.215(2) . ?
C3 N2 1.357(3) . ?
C4 C5 1.398(3) . ?
C4 C9 1.406(3) . ?
C4 N1 1.465(3) . ?
C5 C6 1.397(3) . ?
C5 C10 1.498(3) . ?
C6 C7 1.377(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.384(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(3) . ?
C8 H8 0.9500 . ?
C9 C11 1.503(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 H10D 0.9800 . ?
C10 H10E 0.9800 . ?
C10 H10F 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 H11D 0.9800 . ?
C11 H11E 0.9800 . ?
C11 H11F 0.9800 . ?
C12 C17 1.403(3) . ?
C12 C13 1.407(3) . ?
C12 N2 1.447(3) . ?
C13 C14 1.399(3) . ?
C13 C18 1.499(3) . ?
C14 C15 1.375(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.396(3) . ?
C16 H16 0.9500 . ?
C17 C19 1.508(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 H18D 0.9800 . ?
C18 H18E 0.9800 . ?
C18 H18F 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19 H19D 0.9800 . ?
C19 H19E 0.9800 . ?
C19 H19F 0.9800 . ?
C21 O3 1.208(3) . ?
C21 N3 1.381(2) . ?
C21 C22 1.524(3) . ?
C22 O4 1.215(2) . ?
C22 N4 1.362(3) . ?
C23 C24 1.400(3) . ?
C23 C28 1.405(3) . ?
C23 N3 1.464(2) . ?
C24 C25 1.396(3) . ?
C24 C29 1.496(3) . ?
C25 C26 1.377(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.378(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.391(3) . ?
C27 H27 0.9500 . ?
C28 C30 1.503(3) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C29 H29D 0.9800 . ?
C29 H29E 0.9800 . ?
C29 H29F 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C30 H30D 0.9800 . ?
C30 H30E 0.9800 . ?
C30 H30F 0.9800 . ?
C31 C32 1.402(3) . ?
C31 C36 1.408(3) . ?
C31 N4 1.453(3) . ?
C32 C33 1.397(3) . ?
C32 C37 1.503(3) . ?
C33 C34 1.381(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.378(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.393(3) . ?
C35 H35 0.9500 . ?
C36 C38 1.507(3) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C37 H37D 0.9800 . ?
C37 H37E 0.9800 . ?
C37 H37F 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C38 H38D 0.9800 . ?
C38 H38E 0.9800 . ?
C38 H38F 0.9800 . ?
C53 O5 1.417(3) . ?
C53 C54 1.514(4) . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C54 C55 1.499(5) . ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?
C55 C56 1.516(4) . ?
C55 H55A 0.9900 . ?
C55 H55B 0.9900 . ?
C56 O5 1.423(4) . ?
C56 H56A 0.9900 . ?
C56 H56B 0.9900 . ?
N3 C20 1.462(3) . ?
N4 C20 1.471(2) . ?
C20 H20 1.0000 . ?
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
N1 C1 N2 103.20(15) . . ?
N1 C1 C20 119.15(16) . . ?
N2 C1 C20 109.88(15) . . ?
N1 C1 H1 108.0 . . ?
N2 C1 H1 108.0 . . ?
C20 C1 H1 108.0 . . ?
O1 C2 N1 126.70(19) . . ?
O1 C2 C3 125.46(18) . . ?
N1 C2 C3 107.71(17) . . ?
O2 C3 N2 128.54(19) . . ?
O2 C3 C2 125.72(19) . . ?
N2 C3 C2 105.69(16) . . ?
C5 C4 C9 121.25(18) . . ?
C5 C4 N1 121.27(18) . . ?
C9 C4 N1 117.26(17) . . ?
C6 C5 C4 117.8(2) . . ?
C6 C5 C10 118.02(19) . . ?
C4 C5 C10 124.17(19) . . ?
C7 C6 C5 121.9(2) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C8 119.6(2) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 120.9(2) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C4 118.5(2) . . ?
C8 C9 C11 118.8(2) . . ?
C4 C9 C11 122.67(19) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C10 H10D 109.5 . . ?
H10A C10 H10D 141.1 . . ?
H10B C10 H10D 56.3 . . ?
H10C C10 H10D 56.3 . . ?
C5 C10 H10E 109.5 . . ?
H10A C10 H10E 56.3 . . ?
H10B C10 H10E 141.1 . . ?
H10C C10 H10E 56.3 . . ?
H10D C10 H10E 109.5 . . ?
C5 C10 H10F 109.5 . . ?
H10A C10 H10F 56.3 . . ?
H10B C10 H10F 56.3 . . ?
H10C C10 H10F 141.1 . . ?
H10D C10 H10F 109.5 . . ?
H10E C10 H10F 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C11 H11D 109.5 . . ?
H11A C11 H11D 141.1 . . ?
H11B C11 H11D 56.3 . . ?
H11C C11 H11D 56.3 . . ?
C9 C11 H11E 109.5 . . ?
H11A C11 H11E 56.3 . . ?
H11B C11 H11E 141.1 . . ?
H11C C11 H11E 56.3 . . ?
H11D C11 H11E 109.5 . . ?
C9 C11 H11F 109.5 . . ?
H11A C11 H11F 56.3 . . ?
H11B C11 H11F 56.3 . . ?
H11C C11 H11F 141.1 . . ?
H11D C11 H11F 109.5 . . ?
H11E C11 H11F 109.5 . . ?
C17 C12 C13 122.13(19) . . ?
C17 C12 N2 119.55(18) . . ?
C13 C12 N2 118.32(18) . . ?
C14 C13 C12 117.1(2) . . ?
C14 C13 C18 119.3(2) . . ?
C12 C13 C18 123.59(19) . . ?
C15 C14 C13 121.8(2) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C16 119.9(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 121.1(2) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C12 117.7(2) . . ?
C16 C17 C19 118.5(2) . . ?
C12 C17 C19 123.69(19) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C18 H18D 109.5 . . ?
H18A C18 H18D 141.1 . . ?
H18B C18 H18D 56.3 . . ?
H18C C18 H18D 56.3 . . ?
C13 C18 H18E 109.5 . . ?
H18A C18 H18E 56.3 . . ?
H18B C18 H18E 141.1 . . ?
H18C C18 H18E 56.3 . . ?
H18D C18 H18E 109.5 . . ?
C13 C18 H18F 109.5 . . ?
H18A C18 H18F 56.3 . . ?
H18B C18 H18F 56.3 . . ?
H18C C18 H18F 141.1 . . ?
H18D C18 H18F 109.5 . . ?
H18E C18 H18F 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C19 H19D 109.5 . . ?
H19A C19 H19D 141.1 . . ?
H19B C19 H19D 56.3 . . ?
H19C C19 H19D 56.3 . . ?
C17 C19 H19E 109.5 . . ?
H19A C19 H19E 56.3 . . ?
H19B C19 H19E 141.1 . . ?
H19C C19 H19E 56.3 . . ?
H19D C19 H19E 109.5 . . ?
C17 C19 H19F 109.5 . . ?
H19A C19 H19F 56.3 . . ?
H19B C19 H19F 56.3 . . ?
H19C C19 H19F 141.1 . . ?
H19D C19 H19F 109.5 . . ?
H19E C19 H19F 109.5 . . ?
O3 C21 N3 127.24(19) . . ?
O3 C21 C22 125.69(18) . . ?
N3 C21 C22 107.05(17) . . ?
O4 C22 N4 128.04(19) . . ?
O4 C22 C21 126.02(19) . . ?
N4 C22 C21 105.92(16) . . ?
C24 C23 C28 121.20(19) . . ?
C24 C23 N3 120.21(19) . . ?
C28 C23 N3 118.33(18) . . ?
C25 C24 C23 117.9(2) . . ?
C25 C24 C29 118.6(2) . . ?
C23 C24 C29 123.56(19) . . ?
C26 C25 C24 121.7(2) . . ?
C26 C25 H25 119.1 . . ?
C24 C25 H25 119.1 . . ?
C25 C26 C27 119.5(2) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C26 C27 C28 121.4(2) . . ?
C26 C27 H27 119.3 . . ?
C28 C27 H27 119.3 . . ?
C27 C28 C23 118.3(2) . . ?
C27 C28 C30 118.8(2) . . ?
C23 C28 C30 122.9(2) . . ?
C24 C29 H29A 109.5 . . ?
C24 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C24 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C24 C29 H29D 109.5 . . ?
H29A C29 H29D 141.1 . . ?
H29B C29 H29D 56.3 . . ?
H29C C29 H29D 56.3 . . ?
C24 C29 H29E 109.5 . . ?
H29A C29 H29E 56.3 . . ?
H29B C29 H29E 141.1 . . ?
H29C C29 H29E 56.3 . . ?
H29D C29 H29E 109.5 . . ?
C24 C29 H29F 109.5 . . ?
H29A C29 H29F 56.3 . . ?
H29B C29 H29F 56.3 . . ?
H29C C29 H29F 141.1 . . ?
H29D C29 H29F 109.5 . . ?
H29E C29 H29F 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C30 H30D 109.5 . . ?
H30A C30 H30D 141.1 . . ?
H30B C30 H30D 56.3 . . ?
H30C C30 H30D 56.3 . . ?
C28 C30 H30E 109.5 . . ?
H30A C30 H30E 56.3 . . ?
H30B C30 H30E 141.1 . . ?
H30C C30 H30E 56.3 . . ?
H30D C30 H30E 109.5 . . ?
C28 C30 H30F 109.5 . . ?
H30A C30 H30F 56.3 . . ?
H30B C30 H30F 56.3 . . ?
H30C C30 H30F 141.1 . . ?
H30D C30 H30F 109.5 . . ?
H30E C30 H30F 109.5 . . ?
C32 C31 C36 121.24(19) . . ?
C32 C31 N4 119.41(18) . . ?
C36 C31 N4 119.36(18) . . ?
C33 C32 C31 118.1(2) . . ?
C33 C32 C37 118.6(2) . . ?
C31 C32 C37 123.2(2) . . ?
C34 C33 C32 121.3(2) . . ?
C34 C33 H33 119.4 . . ?
C32 C33 H33 119.4 . . ?
C35 C34 C33 119.6(2) . . ?
C35 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
C34 C35 C36 121.7(2) . . ?
C34 C35 H35 119.2 . . ?
C36 C35 H35 119.2 . . ?
C35 C36 C31 117.8(2) . . ?
C35 C36 C38 119.0(2) . . ?
C31 C36 C38 123.21(19) . . ?
C32 C37 H37A 109.5 . . ?
C32 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C32 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C32 C37 H37D 109.5 . . ?
H37A C37 H37D 141.1 . . ?
H37B C37 H37D 56.3 . . ?
H37C C37 H37D 56.3 . . ?
C32 C37 H37E 109.5 . . ?
H37A C37 H37E 56.3 . . ?
H37B C37 H37E 141.1 . . ?
H37C C37 H37E 56.3 . . ?
H37D C37 H37E 109.5 . . ?
C32 C37 H37F 109.5 . . ?
H37A C37 H37F 56.3 . . ?
H37B C37 H37F 56.3 . . ?
H37C C37 H37F 141.1 . . ?
H37D C37 H37F 109.5 . . ?
H37E C37 H37F 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C36 C38 H38D 109.5 . . ?
H38A C38 H38D 141.1 . . ?
H38B C38 H38D 56.3 . . ?
H38C C38 H38D 56.3 . . ?
C36 C38 H38E 109.5 . . ?
H38A C38 H38E 56.3 . . ?
H38B C38 H38E 141.1 . . ?
H38C C38 H38E 56.3 . . ?
H38D C38 H38E 109.5 . . ?
C36 C38 H38F 109.5 . . ?
H38A C38 H38F 56.3 . . ?
H38B C38 H38F 56.3 . . ?
H38C C38 H38F 141.1 . . ?
H38D C38 H38F 109.5 . . ?
H38E C38 H38F 109.5 . . ?
O5 C53 C54 104.1(2) . . ?
O5 C53 H53A 110.9 . . ?
C54 C53 H53A 110.9 . . ?
O5 C53 H53B 110.9 . . ?
C54 C53 H53B 110.9 . . ?
H53A C53 H53B 109.0 . . ?
C55 C54 C53 102.6(2) . . ?
C55 C54 H54A 111.2 . . ?
C53 C54 H54A 111.2 . . ?
C55 C54 H54B 111.2 . . ?
C53 C54 H54B 111.2 . . ?
H54A C54 H54B 109.2 . . ?
C54 C55 C56 104.1(3) . . ?
C54 C55 H55A 110.9 . . ?
C56 C55 H55A 110.9 . . ?
C54 C55 H55B 110.9 . . ?
C56 C55 H55B 110.9 . . ?
H55A C55 H55B 108.9 . . ?
O5 C56 C55 107.4(2) . . ?
O5 C56 H56A 110.2 . . ?
C55 C56 H56A 110.2 . . ?
O5 C56 H56B 110.2 . . ?
C55 C56 H56B 110.2 . . ?
H56A C56 H56B 108.5 . . ?
C2 N1 C4 115.86(17) . . ?
C2 N1 C1 110.56(15) . . ?
C4 N1 C1 123.38(16) . . ?
C3 N2 C12 124.59(16) . . ?
C3 N2 C1 112.83(16) . . ?
C12 N2 C1 122.57(16) . . ?
C21 N3 C20 111.10(15) . . ?
C21 N3 C23 117.77(16) . . ?
C20 N3 C23 124.79(16) . . ?
C22 N4 C31 125.02(16) . . ?
C22 N4 C20 112.41(16) . . ?
C31 N4 C20 122.47(15) . . ?
C53 O5 C56 107.4(2) . . ?
N3 C20 N4 103.45(15) . . ?
N3 C20 C1 118.52(16) . . ?
N4 C20 C1 110.29(15) . . ?
N3 C20 H20 108.0 . . ?
N4 C20 H20 108.0 . . ?
C1 C20 H20 108.0 . . ?
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 O2 0.6(4) . . . . ?
N1 C2 C3 O2 176.8(2) . . . . ?
O1 C2 C3 N2 -177.0(2) . . . . ?
N1 C2 C3 N2 -0.8(2) . . . . ?
C9 C4 C5 C6 2.3(3) . . . . ?
N1 C4 C5 C6 176.81(18) . . . . ?
C9 C4 C5 C10 -178.2(2) . . . . ?
N1 C4 C5 C10 -3.7(3) . . . . ?
C4 C5 C6 C7 -2.0(3) . . . . ?
C10 C5 C6 C7 178.5(2) . . . . ?
C5 C6 C7 C8 0.8(3) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C7 C8 C9 C4 0.2(3) . . . . ?
C7 C8 C9 C11 -178.1(2) . . . . ?
C5 C4 C9 C8 -1.5(3) . . . . ?
N1 C4 C9 C8 -176.18(18) . . . . ?
C5 C4 C9 C11 176.8(2) . . . . ?
N1 C4 C9 C11 2.1(3) . . . . ?
C17 C12 C13 C14 -3.2(3) . . . . ?
N2 C12 C13 C14 176.96(18) . . . . ?
C17 C12 C13 C18 175.36(19) . . . . ?
N2 C12 C13 C18 -4.5(3) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C18 C13 C14 C15 -179.1(2) . . . . ?
C13 C14 C15 C16 2.7(3) . . . . ?
C14 C15 C16 C17 -1.5(3) . . . . ?
C15 C16 C17 C12 -2.0(3) . . . . ?
C15 C16 C17 C19 175.08(19) . . . . ?
C13 C12 C17 C16 4.4(3) . . . . ?
N2 C12 C17 C16 -175.77(18) . . . . ?
C13 C12 C17 C19 -172.53(19) . . . . ?
N2 C12 C17 C19 7.3(3) . . . . ?
O3 C21 C22 O4 2.2(3) . . . . ?
N3 C21 C22 O4 -179.5(2) . . . . ?
O3 C21 C22 N4 -176.2(2) . . . . ?
N3 C21 C22 N4 2.1(2) . . . . ?
C28 C23 C24 C25 1.8(3) . . . . ?
N3 C23 C24 C25 175.79(19) . . . . ?
C28 C23 C24 C29 -177.3(2) . . . . ?
N3 C23 C24 C29 -3.2(3) . . . . ?
C23 C24 C25 C26 -0.5(3) . . . . ?
C29 C24 C25 C26 178.6(2) . . . . ?
C24 C25 C26 C27 -0.5(4) . . . . ?
C25 C26 C27 C28 0.2(4) . . . . ?
C26 C27 C28 C23 1.0(4) . . . . ?
C26 C27 C28 C30 -178.8(2) . . . . ?
C24 C23 C28 C27 -2.0(3) . . . . ?
N3 C23 C28 C27 -176.2(2) . . . . ?
C24 C23 C28 C30 177.8(2) . . . . ?
N3 C23 C28 C30 3.6(3) . . . . ?
C36 C31 C32 C33 -4.2(3) . . . . ?
N4 C31 C32 C33 176.37(18) . . . . ?
C36 C31 C32 C37 173.4(2) . . . . ?
N4 C31 C32 C37 -6.1(3) . . . . ?
C31 C32 C33 C34 -0.4(3) . . . . ?
C37 C32 C33 C34 -178.1(2) . . . . ?
C32 C33 C34 C35 3.2(4) . . . . ?
C33 C34 C35 C36 -1.5(4) . . . . ?
C34 C35 C36 C31 -3.0(3) . . . . ?
C34 C35 C36 C38 174.9(2) . . . . ?
C32 C31 C36 C35 5.8(3) . . . . ?
N4 C31 C36 C35 -174.73(18) . . . . ?
C32 C31 C36 C38 -171.96(19) . . . . ?
N4 C31 C36 C38 7.5(3) . . . . ?
O5 C53 C54 C55 37.4(3) . . . . ?
C53 C54 C55 C56 -24.8(3) . . . . ?
C54 C55 C56 O5 4.3(3) . . . . ?
O1 C2 N1 C4 30.5(3) . . . . ?
C3 C2 N1 C4 -145.56(17) . . . . ?
O1 C2 N1 C1 177.1(2) . . . . ?
C3 C2 N1 C1 1.0(2) . . . . ?
C5 C4 N1 C2 -110.8(2) . . . . ?
C9 C4 N1 C2 63.9(2) . . . . ?
C5 C4 N1 C1 107.4(2) . . . . ?
C9 C4 N1 C1 -78.0(2) . . . . ?
N2 C1 N1 C2 -0.8(2) . . . . ?
C20 C1 N1 C2 121.23(18) . . . . ?
N2 C1 N1 C4 142.79(18) . . . . ?
C20 C1 N1 C4 -95.2(2) . . . . ?
O2 C3 N2 C12 4.3(4) . . . . ?
C2 C3 N2 C12 -178.21(18) . . . . ?
O2 C3 N2 C1 -177.2(2) . . . . ?
C2 C3 N2 C1 0.3(2) . . . . ?
C17 C12 N2 C3 -121.1(2) . . . . ?
C13 C12 N2 C3 58.7(3) . . . . ?
C17 C12 N2 C1 60.5(3) . . . . ?
C13 C12 N2 C1 -119.7(2) . . . . ?
N1 C1 N2 C3 0.3(2) . . . . ?
C20 C1 N2 C3 -127.82(18) . . . . ?
N1 C1 N2 C12 178.84(17) . . . . ?
C20 C1 N2 C12 50.8(2) . . . . ?
O3 C21 N3 C20 177.5(2) . . . . ?
C22 C21 N3 C20 -0.7(2) . . . . ?
O3 C21 N3 C23 24.1(3) . . . . ?
C22 C21 N3 C23 -154.17(17) . . . . ?
C24 C23 N3 C21 -93.1(2) . . . . ?
C28 C23 N3 C21 81.1(2) . . . . ?
C24 C23 N3 C20 117.4(2) . . . . ?
C28 C23 N3 C20 -68.4(3) . . . . ?
O4 C22 N4 C31 -4.5(3) . . . . ?
C21 C22 N4 C31 173.87(17) . . . . ?
O4 C22 N4 C20 178.9(2) . . . . ?
C21 C22 N4 C20 -2.8(2) . . . . ?
C32 C31 N4 C22 66.5(3) . . . . ?
C36 C31 N4 C22 -113.0(2) . . . . ?
C32 C31 N4 C20 -117.2(2) . . . . ?
C36 C31 N4 C20 63.3(3) . . . . ?
C54 C53 O5 C56 -35.8(3) . . . . ?
C55 C56 O5 C53 19.8(3) . . . . ?
C21 N3 C20 N4 -0.8(2) . . . . ?
C23 N3 C20 N4 150.36(17) . . . . ?
C21 N3 C20 C1 121.55(18) . . . . ?
C23 N3 C20 C1 -87.2(2) . . . . ?
C22 N4 C20 N3 2.3(2) . . . . ?
C31 N4 C20 N3 -174.40(16) . . . . ?
C22 N4 C20 C1 -125.38(17) . . . . ?
C31 N4 C20 C1 57.9(2) . . . . ?
N1 C1 C20 N3 -28.9(2) . . . . ?
N2 C1 C20 N3 89.80(19) . . . . ?
N1 C1 C20 N4 90.0(2) . . . . ?
N2 C1 C20 N4 -151.31(15) . . . . ?
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full 27.48
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max 0.459
_refine_diff_density_min -0.402
_refine_diff_density_rms 0.091
# Attachment '- 3c.cif'
_publ_section_references
;
Blessing, R. H. (1997). J. Appl. Cryst. 30, 421--426.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Fun, H-K., Goswami, S., Jana, S. & Chantrapromma, S. (2006).
Acta Cryst. E62, 05332--o5334.
Hooft, R. (1998). COLLECT. Nonius B V, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
Macromolecular Crystallography, Part A, edited by C. W. Carter Jr. and R. M.
Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122.
;
#------------------------------------------------------------------------------
data_shelxl3c
_database_code_depnum_ccdc_archive 'CCDC 743955'
#TrackingRef '- 3c.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C29 H38 N2 O4'
_chemical_formula_sum 'C29 H38 N2 O4'
_chemical_formula_weight 478.61
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 n a 21'
_symmetry_space_group_name_Hall 'P 2c -2n'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
_cell_length_a 19.300(2)
_cell_length_b 12.239(2)
_cell_length_c 11.804(1)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 2788.3(4)
_cell_formula_units_Z 4
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 1896
_cell_measurement_theta_min 4.86
_cell_measurement_theta_max 22.48
_exptl_crystal_description blocks
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.08
_exptl_crystal_size_mid 0.07
_exptl_crystal_size_min 0.06
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.140
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1032
_exptl_absorpt_coefficient_mu 0.076
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_correction_T_min 0.9940
_exptl_absorpt_correction_T_max 0.9955
_exptl_absorpt_process_details 'SORTAV: (Blessing, 1997)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Nonius KappaCCD'
_diffrn_measurement_method ' \w and \f '
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 6812
_diffrn_reflns_av_R_equivalents 0.1060
_diffrn_reflns_av_sigmaI/netI 0.1121
_diffrn_reflns_limit_h_min -20
_diffrn_reflns_limit_h_max 18
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 4.86
_diffrn_reflns_theta_max 22.48
_reflns_number_total 1896
_reflns_number_gt 1398
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution ?
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_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^)+(0.0440P)^2^+0.7371P] 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 1896
_refine_ls_number_parameters 325
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0887
_refine_ls_R_factor_gt 0.0551
_refine_ls_wR_factor_ref 0.1275
_refine_ls_wR_factor_gt 0.1098
_refine_ls_goodness_of_fit_ref 1.078
_refine_ls_restrained_S_all 1.078
_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 0.0900(3) 0.4604(4) 0.9487(5) 0.0339(15) Uani 1 1 d . . .
H1 H 0.1042 0.4572 1.0301 0.041 Uiso 1 1 calc R . .
C2 C 0.1347(3) 0.3624(5) 0.7964(6) 0.0390(16) Uani 1 1 d . . .
C3 C 0.1617(4) 0.4780(5) 0.7905(6) 0.0398(16) Uani 1 1 d . . .
C4 C -0.0188(4) 0.5160(5) 1.0305(6) 0.0470(17) Uani 1 1 d . . .
C5 C -0.0895(4) 0.5544(6) 0.9995(7) 0.062(2) Uani 1 1 d . . .
H5A H -0.1241 0.5111 1.0405 0.093 Uiso 1 1 calc R . .
H5B H -0.0965 0.5456 0.9178 0.093 Uiso 1 1 calc R . .
H5C H -0.0945 0.6316 1.0199 0.093 Uiso 1 1 calc R . .
C6 C 0.0690(3) 0.2537(4) 0.9354(5) 0.0382(15) Uani 1 1 d . . .
C7 C 0.0091(3) 0.2108(5) 0.8852(6) 0.0407(16) Uani 1 1 d . . .
C8 C -0.0128(4) 0.1098(5) 0.9236(6) 0.0476(18) Uani 1 1 d . . .
H8 H -0.0524 0.0767 0.8905 0.057 Uiso 1 1 calc R . .
C9 C 0.0220(4) 0.0561(5) 1.0093(7) 0.0501(19) Uani 1 1 d . . .
H9 H 0.0052 -0.0122 1.0356 0.060 Uiso 1 1 calc R . .
C10 C 0.0799(4) 0.0996(5) 1.0566(6) 0.0493(19) Uani 1 1 d . . .
H10 H 0.1031 0.0607 1.1150 0.059 Uiso 1 1 calc R . .
C11 C 0.1059(3) 0.1997(5) 1.0211(5) 0.0380(16) Uani 1 1 d . . .
C12 C -0.0301(4) 0.2686(5) 0.7917(5) 0.0442(17) Uani 1 1 d . . .
H12 H -0.0089 0.3425 0.7817 0.053 Uiso 1 1 calc R . .
C13 C -0.1061(4) 0.2846(7) 0.8221(7) 0.066(2) Uani 1 1 d . . .
H13A H -0.1285 0.2132 0.8305 0.098 Uiso 1 1 calc R . .
H13B H -0.1292 0.3259 0.7617 0.098 Uiso 1 1 calc R . .
H13C H -0.1096 0.3251 0.8935 0.098 Uiso 1 1 calc R . .
C14 C -0.0223(4) 0.2069(6) 0.6798(7) 0.066(2) Uani 1 1 d . . .
H14A H 0.0263 0.2080 0.6562 0.099 Uiso 1 1 calc R . .
H14B H -0.0509 0.2421 0.6217 0.099 Uiso 1 1 calc R . .
H14C H -0.0375 0.1311 0.6899 0.099 Uiso 1 1 calc R . .
C15 C 0.1746(3) 0.2423(6) 1.0657(6) 0.0494(18) Uani 1 1 d . . .
H15 H 0.1749 0.3228 1.0516 0.059 Uiso 1 1 calc R . .
C16 C 0.2345(4) 0.1948(8) 0.9983(8) 0.083(3) Uani 1 1 d . . .
H16A H 0.2385 0.1165 1.0142 0.124 Uiso 1 1 calc R . .
H16B H 0.2776 0.2316 1.0199 0.124 Uiso 1 1 calc R . .
H16C H 0.2260 0.2056 0.9172 0.124 Uiso 1 1 calc R . .
C17 C 0.1864(4) 0.2269(7) 1.1909(6) 0.075(2) Uani 1 1 d . . .
H17A H 0.1903 0.1488 1.2078 0.113 Uiso 1 1 calc R . .
H17B H 0.1474 0.2580 1.2330 0.113 Uiso 1 1 calc R . .
H17C H 0.2293 0.2640 1.2132 0.113 Uiso 1 1 calc R . .
C18 C 0.1557(3) 0.6374(5) 0.9222(5) 0.0344(15) Uani 1 1 d . . .
C19 C 0.1215(3) 0.7296(5) 0.8785(5) 0.0380(16) Uani 1 1 d . . .
C20 C 0.1433(4) 0.8315(5) 0.9172(6) 0.0442(17) Uani 1 1 d . . .
H20 H 0.1209 0.8958 0.8907 0.053 Uiso 1 1 calc R . .
C21 C 0.1971(4) 0.8398(5) 0.9941(7) 0.054(2) Uani 1 1 d . . .
H21 H 0.2117 0.9101 1.0183 0.065 Uiso 1 1 calc R . .
C22 C 0.2298(4) 0.7486(5) 1.0363(6) 0.0509(18) Uani 1 1 d . . .
H22 H 0.2654 0.7564 1.0912 0.061 Uiso 1 1 calc R . .
C23 C 0.2109(3) 0.6447(5) 0.9987(6) 0.0386(16) Uani 1 1 d . . .
C24 C 0.0634(4) 0.7210(5) 0.7926(5) 0.0435(17) Uani 1 1 d . . .
H24 H 0.0483 0.6430 0.7896 0.052 Uiso 1 1 calc R . .
C25 C 0.0011(4) 0.7895(7) 0.8251(7) 0.063(2) Uani 1 1 d . . .
H25A H -0.0134 0.7708 0.9023 0.094 Uiso 1 1 calc R . .
H25B H -0.0370 0.7749 0.7724 0.094 Uiso 1 1 calc R . .
H25C H 0.0135 0.8672 0.8218 0.094 Uiso 1 1 calc R . .
C26 C 0.0898(4) 0.7520(6) 0.6760(6) 0.058(2) Uani 1 1 d . . .
H26A H 0.1058 0.8280 0.6769 0.088 Uiso 1 1 calc R . .
H26B H 0.0523 0.7441 0.6206 0.088 Uiso 1 1 calc R . .
H26C H 0.1283 0.7039 0.6551 0.088 Uiso 1 1 calc R . .
C27 C 0.2520(4) 0.5458(5) 1.0397(6) 0.0452(17) Uani 1 1 d . . .
H27 H 0.2316 0.4792 1.0038 0.054 Uiso 1 1 calc R . .
C28 C 0.3277(4) 0.5539(8) 1.0023(8) 0.084(3) Uani 1 1 d . . .
H28A H 0.3492 0.6179 1.0378 0.125 Uiso 1 1 calc R . .
H28B H 0.3298 0.5614 0.9197 0.125 Uiso 1 1 calc R . .
H28C H 0.3526 0.4878 1.0254 0.125 Uiso 1 1 calc R . .
C29 C 0.2470(5) 0.5323(6) 1.1663(7) 0.073(2) Uani 1 1 d . . .
H29A H 0.2705 0.4647 1.1889 0.110 Uiso 1 1 calc R . .
H29B H 0.1982 0.5287 1.1886 0.110 Uiso 1 1 calc R . .
H29C H 0.2692 0.5946 1.2037 0.110 Uiso 1 1 calc R . .
N1 N 0.0971(3) 0.3549(4) 0.8934(4) 0.0333(12) Uani 1 1 d . . .
N2 N 0.1352(3) 0.5301(3) 0.8835(4) 0.0330(12) Uani 1 1 d . . .
O1 O 0.1473(2) 0.2896(3) 0.7292(4) 0.0499(12) Uani 1 1 d . . .
O2 O 0.2012(2) 0.5150(3) 0.7206(4) 0.0543(13) Uani 1 1 d . . .
O3 O 0.0200(2) 0.4967(3) 0.9361(4) 0.0377(10) Uani 1 1 d . . .
O4 O 0.0034(3) 0.4998(5) 1.1242(5) 0.0741(16) 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 0.035(4) 0.032(3) 0.035(3) -0.008(3) -0.002(3) -0.002(3)
C2 0.038(4) 0.041(4) 0.039(4) -0.006(4) 0.005(3) -0.001(3)
C3 0.035(4) 0.041(4) 0.044(4) -0.002(3) 0.006(3) -0.005(3)
C4 0.060(5) 0.040(4) 0.041(4) -0.006(3) 0.013(4) -0.002(3)
C5 0.040(5) 0.070(5) 0.076(5) -0.006(4) 0.016(4) 0.009(4)
C6 0.037(4) 0.032(3) 0.045(4) -0.003(3) 0.012(3) 0.003(3)
C7 0.032(4) 0.044(4) 0.045(4) -0.004(3) 0.005(3) 0.000(3)
C8 0.049(4) 0.038(4) 0.056(5) -0.002(4) 0.007(4) -0.011(3)
C9 0.051(5) 0.036(3) 0.064(5) 0.008(4) 0.012(4) 0.000(4)
C10 0.043(5) 0.043(4) 0.062(5) 0.015(4) 0.003(4) 0.008(4)
C11 0.041(4) 0.029(3) 0.044(4) -0.003(3) 0.005(3) 0.005(3)
C12 0.055(5) 0.040(4) 0.037(3) -0.007(3) -0.007(3) -0.010(3)
C13 0.052(5) 0.079(6) 0.066(5) 0.011(4) -0.001(4) 0.003(4)
C14 0.077(6) 0.071(5) 0.050(4) -0.010(4) -0.001(4) -0.024(5)
C15 0.029(4) 0.049(4) 0.071(5) 0.017(4) 0.001(3) 0.009(3)
C16 0.049(5) 0.130(8) 0.070(5) -0.001(6) 0.000(5) 0.002(5)
C17 0.050(5) 0.116(7) 0.059(5) -0.001(5) -0.002(4) -0.004(5)
C18 0.028(4) 0.034(3) 0.041(4) 0.001(3) -0.004(3) -0.004(3)
C19 0.031(4) 0.039(4) 0.044(4) -0.002(3) 0.000(3) -0.002(3)
C20 0.045(4) 0.035(4) 0.053(4) 0.003(3) -0.002(4) 0.000(3)
C21 0.046(5) 0.044(4) 0.072(5) -0.003(4) -0.007(4) -0.005(4)
C22 0.045(4) 0.046(4) 0.061(5) -0.014(4) -0.023(4) -0.006(3)
C23 0.033(4) 0.040(4) 0.043(4) -0.003(3) 0.001(3) 0.004(3)
C24 0.045(4) 0.044(4) 0.041(4) 0.007(3) -0.012(4) 0.002(3)
C25 0.035(5) 0.086(6) 0.067(5) 0.002(4) -0.007(4) 0.006(4)
C26 0.063(5) 0.065(5) 0.047(4) 0.012(4) -0.004(4) -0.005(4)
C27 0.045(4) 0.043(4) 0.048(4) 0.000(3) -0.012(4) 0.008(3)
C28 0.049(5) 0.106(6) 0.096(7) 0.017(6) 0.007(5) 0.028(5)
C29 0.098(7) 0.058(5) 0.063(5) 0.006(4) -0.010(5) 0.017(5)
N1 0.032(3) 0.034(3) 0.034(3) -0.003(3) 0.002(3) -0.002(2)
N2 0.037(3) 0.026(3) 0.035(3) -0.002(2) 0.003(3) -0.006(2)
O1 0.052(3) 0.049(3) 0.048(3) -0.009(3) 0.012(3) -0.001(2)
O2 0.059(3) 0.046(3) 0.058(3) -0.003(3) 0.018(3) -0.011(2)
O3 0.036(3) 0.043(2) 0.034(2) -0.003(2) 0.005(2) 0.001(2)
O4 0.079(4) 0.097(4) 0.046(3) -0.004(3) 0.020(3) 0.004(3)
_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 O3 1.430(7) . ?
C1 N2 1.442(8) . ?
C1 N1 1.454(7) . ?
C1 H1 1.0000 . ?
C2 O1 1.217(7) . ?
C2 N1 1.359(8) . ?
C2 C3 1.510(9) . ?
C3 O2 1.212(7) . ?
C3 N2 1.368(8) . ?
C4 O4 1.203(9) . ?
C4 O3 1.362(8) . ?
C4 C5 1.490(10) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.401(8) . ?
C6 C11 1.403(8) . ?
C6 N1 1.440(7) . ?
C7 C8 1.383(8) . ?
C7 C12 1.512(9) . ?
C8 C9 1.380(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.358(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(8) . ?
C10 H10 0.9500 . ?
C11 C15 1.518(9) . ?
C12 C13 1.523(10) . ?
C12 C14 1.528(9) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C17 1.506(9) . ?
C15 C16 1.519(10) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C23 1.399(8) . ?
C18 C19 1.406(8) . ?
C18 N2 1.445(7) . ?
C19 C20 1.393(9) . ?
C19 C24 1.515(9) . ?
C20 C21 1.382(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.376(9) . ?
C21 H21 0.9500 . ?
C22 C23 1.396(8) . ?
C22 H22 0.9500 . ?
C23 C27 1.527(8) . ?
C24 C26 1.515(9) . ?
C24 C25 1.516(10) . ?
C24 H24 1.0000 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C29 1.506(10) . ?
C27 C28 1.529(10) . ?
C27 H27 1.0000 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 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
O3 C1 N2 109.5(5) . . ?
O3 C1 N1 108.6(5) . . ?
N2 C1 N1 103.2(5) . . ?
O3 C1 H1 111.7 . . ?
N2 C1 H1 111.7 . . ?
N1 C1 H1 111.7 . . ?
O1 C2 N1 127.3(6) . . ?
O1 C2 C3 126.0(6) . . ?
N1 C2 C3 106.6(5) . . ?
O2 C3 N2 127.4(6) . . ?
O2 C3 C2 126.8(6) . . ?
N2 C3 C2 105.8(5) . . ?
O4 C4 O3 121.9(6) . . ?
O4 C4 C5 127.2(7) . . ?
O3 C4 C5 110.9(6) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C11 123.2(6) . . ?
C7 C6 N1 119.1(6) . . ?
C11 C6 N1 117.5(5) . . ?
C8 C7 C6 116.6(6) . . ?
C8 C7 C12 120.3(6) . . ?
C6 C7 C12 123.1(6) . . ?
C9 C8 C7 121.2(6) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C10 C9 C8 121.0(6) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 121.3(6) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C6 116.7(6) . . ?
C10 C11 C15 120.9(6) . . ?
C6 C11 C15 122.1(5) . . ?
C7 C12 C13 111.7(6) . . ?
C7 C12 C14 110.5(6) . . ?
C13 C12 C14 111.2(6) . . ?
C7 C12 H12 107.7 . . ?
C13 C12 H12 107.7 . . ?
C14 C12 H12 107.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C17 C15 C11 115.4(6) . . ?
C17 C15 C16 110.6(6) . . ?
C11 C15 C16 110.5(6) . . ?
C17 C15 H15 106.6 . . ?
C11 C15 H15 106.6 . . ?
C16 C15 H15 106.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 122.9(5) . . ?
C23 C18 N2 118.1(5) . . ?
C19 C18 N2 119.0(5) . . ?
C20 C19 C18 117.2(6) . . ?
C20 C19 C24 120.3(6) . . ?
C18 C19 C24 122.5(5) . . ?
C21 C20 C19 120.5(6) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C20 121.5(6) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C23 120.3(6) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C18 117.6(5) . . ?
C22 C23 C27 119.1(6) . . ?
C18 C23 C27 123.3(5) . . ?
C26 C24 C25 111.0(6) . . ?
C26 C24 C19 110.0(6) . . ?
C25 C24 C19 112.3(6) . . ?
C26 C24 H24 107.8 . . ?
C25 C24 H24 107.8 . . ?
C19 C24 H24 107.8 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C29 C27 C23 111.6(6) . . ?
C29 C27 C28 110.8(7) . . ?
C23 C27 C28 110.7(6) . . ?
C29 C27 H27 107.8 . . ?
C23 C27 H27 107.8 . . ?
C28 C27 H27 107.8 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C2 N1 C6 123.3(5) . . ?
C2 N1 C1 111.6(5) . . ?
C6 N1 C1 125.1(5) . . ?
C3 N2 C1 112.2(4) . . ?
C3 N2 C18 125.1(5) . . ?
C1 N2 C18 122.3(5) . . ?
C4 O3 C1 119.2(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
O1 C2 C3 O2 -2.3(12) . . . . ?
N1 C2 C3 O2 174.7(7) . . . . ?
O1 C2 C3 N2 -179.1(7) . . . . ?
N1 C2 C3 N2 -2.1(7) . . . . ?
C11 C6 C7 C8 -0.5(9) . . . . ?
N1 C6 C7 C8 175.6(5) . . . . ?
C11 C6 C7 C12 -179.2(6) . . . . ?
N1 C6 C7 C12 -3.0(9) . . . . ?
C6 C7 C8 C9 1.7(9) . . . . ?
C12 C7 C8 C9 -179.5(6) . . . . ?
C7 C8 C9 C10 -1.8(10) . . . . ?
C8 C9 C10 C11 0.5(10) . . . . ?
C9 C10 C11 C6 0.7(9) . . . . ?
C9 C10 C11 C15 -173.7(6) . . . . ?
C7 C6 C11 C10 -0.6(9) . . . . ?
N1 C6 C11 C10 -176.9(5) . . . . ?
C7 C6 C11 C15 173.7(6) . . . . ?
N1 C6 C11 C15 -2.6(8) . . . . ?
C8 C7 C12 C13 56.5(8) . . . . ?
C6 C7 C12 C13 -124.9(7) . . . . ?
C8 C7 C12 C14 -67.9(8) . . . . ?
C6 C7 C12 C14 110.8(7) . . . . ?
C10 C11 C15 C17 -42.5(9) . . . . ?
C6 C11 C15 C17 143.5(7) . . . . ?
C10 C11 C15 C16 83.9(8) . . . . ?
C6 C11 C15 C16 -90.1(7) . . . . ?
C23 C18 C19 C20 -2.0(9) . . . . ?
N2 C18 C19 C20 -179.5(6) . . . . ?
C23 C18 C19 C24 177.9(6) . . . . ?
N2 C18 C19 C24 0.4(9) . . . . ?
C18 C19 C20 C21 1.0(10) . . . . ?
C24 C19 C20 C21 -178.8(6) . . . . ?
C19 C20 C21 C22 -1.3(11) . . . . ?
C20 C21 C22 C23 2.4(11) . . . . ?
C21 C22 C23 C18 -3.2(10) . . . . ?
C21 C22 C23 C27 175.0(6) . . . . ?
C19 C18 C23 C22 3.0(9) . . . . ?
N2 C18 C23 C22 -179.4(6) . . . . ?
C19 C18 C23 C27 -175.1(6) . . . . ?
N2 C18 C23 C27 2.4(9) . . . . ?
C20 C19 C24 C26 75.8(8) . . . . ?
C18 C19 C24 C26 -104.1(7) . . . . ?
C20 C19 C24 C25 -48.4(9) . . . . ?
C18 C19 C24 C25 131.8(7) . . . . ?
C22 C23 C27 C29 62.4(9) . . . . ?
C18 C23 C27 C29 -119.5(7) . . . . ?
C22 C23 C27 C28 -61.5(9) . . . . ?
C18 C23 C27 C28 116.6(8) . . . . ?
O1 C2 N1 C6 3.9(10) . . . . ?
C3 C2 N1 C6 -173.0(5) . . . . ?
O1 C2 N1 C1 -176.9(7) . . . . ?
C3 C2 N1 C1 6.2(7) . . . . ?
C7 C6 N1 C2 -77.6(8) . . . . ?
C11 C6 N1 C2 98.8(7) . . . . ?
C7 C6 N1 C1 103.4(7) . . . . ?
C11 C6 N1 C1 -80.2(7) . . . . ?
O3 C1 N1 C2 108.5(6) . . . . ?
N2 C1 N1 C2 -7.6(6) . . . . ?
O3 C1 N1 C6 -72.3(7) . . . . ?
N2 C1 N1 C6 171.6(5) . . . . ?
O2 C3 N2 C1 -179.6(6) . . . . ?
C2 C3 N2 C1 -2.8(7) . . . . ?
O2 C3 N2 C18 -6.8(11) . . . . ?
C2 C3 N2 C18 170.0(5) . . . . ?
O3 C1 N2 C3 -109.3(6) . . . . ?
N1 C1 N2 C3 6.2(7) . . . . ?
O3 C1 N2 C18 77.7(6) . . . . ?
N1 C1 N2 C18 -166.8(5) . . . . ?
C23 C18 N2 C3 -89.5(8) . . . . ?
C19 C18 N2 C3 88.1(7) . . . . ?
C23 C18 N2 C1 82.5(7) . . . . ?
C19 C18 N2 C1 -99.9(7) . . . . ?
O4 C4 O3 C1 -2.6(9) . . . . ?
C5 C4 O3 C1 179.3(5) . . . . ?
N2 C1 O3 C4 -127.7(5) . . . . ?
N1 C1 O3 C4 120.3(5) . . . . ?
_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full 22.48
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max 0.164
_refine_diff_density_min -0.176
_refine_diff_density_rms 0.044
# Attachment '- 5a.cif'
_publ_section_references
;
Blessing, R. H. (1997). J. Appl. Cryst. 30, 421--426.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Fun, H-K., Goswami, S., Jana, S. & Chantrapromma, S. (2006).
Acta Cryst. E62, 05332--o5334.
Hooft, R. (1998). COLLECT. Nonius B V, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
Macromolecular Crystallography, Part A, edited by C. W. Carter Jr. and R. M.
Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122.
;
#------------------------------------------------------------------------------
data_5a
_database_code_depnum_ccdc_archive 'CCDC 743956'
#TrackingRef '- 5a_final.cif'
#-----------------------------------------------------------------------------
_computing_data_collection 'COLLECT (Hooft, 1998)'
_computing_cell_refinement 'HKL DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)'
#-----------------------------------------------------------------------------
#data_shelxl
#TrackingRef '- 5a_final.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
2-fluoro-1,3-bis(perfluorophenyl)imidazolidine-4,5-dione
;
_chemical_name_common
2-fluoro-1,3-bis(perfluorophenyl)imidazolidine-4,5-dione
_chemical_melting_point ?
_chemical_formula_moiety 'C15 H F11 N2 O2'
_chemical_formula_sum 'C15 H F11 N2 O2'
_chemical_formula_weight 450.18
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'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_H-M 'C m c 21'
_symmetry_space_group_name_Hall 'C 2c -2'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
_cell_length_a 25.917(2)
_cell_length_b 9.789(1)
_cell_length_c 6.040(1)
_cell_angle_alpha 90.000
_cell_angle_beta 90.000
_cell_angle_gamma 90.000
_cell_volume 1532.4(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 969
_cell_measurement_theta_min 1.57
_cell_measurement_theta_max 27.61
_exptl_crystal_description needle
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.08
_exptl_crystal_size_mid 0.06
_exptl_crystal_size_min 0.02
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.951
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 880
_exptl_absorpt_coefficient_mu 0.220
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_correction_T_min 0.9826
_exptl_absorpt_correction_T_max 0.9956
_exptl_absorpt_process_details 'SORTAV: (Blessing, 1997)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Nonius KappaCCD'
_diffrn_measurement_method ' \w and \f '
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 9614
_diffrn_reflns_av_R_equivalents 0.1430
_diffrn_reflns_av_sigmaI/netI 0.0573
_diffrn_reflns_limit_h_min -33
_diffrn_reflns_limit_h_max 33
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -7
_diffrn_reflns_limit_l_max 7
_diffrn_reflns_theta_min 1.57
_diffrn_reflns_theta_max 27.61
_reflns_number_total 969
_reflns_number_gt 723
_reflns_threshold_expression >2sigma(I)
#_computing_data_collection ?
#_computing_cell_refinement ?
#_computing_data_reduction ?
#_computing_structure_solution ?
#_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
#_computing_molecular_graphics ?
#_computing_publication_material ?
_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^)+(0.0267P)^2^+2.2147P] 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 969
_refine_ls_number_parameters 139
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0856
_refine_ls_R_factor_gt 0.0587
_refine_ls_wR_factor_ref 0.1080
_refine_ls_wR_factor_gt 0.0985
_refine_ls_goodness_of_fit_ref 1.185
_refine_ls_restrained_S_all 1.184
_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 0.0000 0.2252(8) 0.6285(12) 0.0298(17) Uani 1 2 d S . .
H1 H 0.0000 0.2914 0.5025 0.036 Uiso 1 2 calc SR . .
C2 C 0.02978(18) 0.2502(5) 0.9950(9) 0.0280(11) Uani 1 1 d . . .
C3 C 0.09532(17) 0.2437(5) 0.6992(7) 0.0253(11) Uani 1 1 d . . .
C4 C 0.1155(2) 0.3488(5) 0.5745(9) 0.0310(12) Uani 1 1 d . . .
C5 C 0.16558(19) 0.3451(5) 0.4971(10) 0.0314(12) Uani 1 1 d . . .
C6 C 0.19636(19) 0.2361(5) 0.5525(9) 0.0338(13) Uani 1 1 d . . .
C7 C 0.17734(19) 0.1288(5) 0.6755(10) 0.0322(12) Uani 1 1 d . . .
C8 C 0.12657(19) 0.1331(5) 0.7471(9) 0.0306(12) Uani 1 1 d . . .
F1 F 0.08544(12) 0.4572(3) 0.5253(6) 0.0441(9) Uani 1 1 d . . .
F2 F 0.18450(13) 0.4489(3) 0.3808(7) 0.0534(10) Uani 1 1 d . . .
F3 F 0.24523(12) 0.2316(3) 0.4815(6) 0.0469(9) Uani 1 1 d . . .
F4 F 0.20659(10) 0.0203(3) 0.7198(6) 0.0452(9) Uani 1 1 d . . .
F5 F 0.10751(11) 0.0274(3) 0.8597(7) 0.0417(8) Uani 1 1 d . . .
F6 F 0.0000 0.0922(4) 0.5557(8) 0.0422(12) Uani 1 2 d S . .
N1 N 0.04352(15) 0.2465(4) 0.7749(7) 0.0296(10) Uani 1 1 d . . .
O1 O 0.05744(14) 0.2566(4) 1.1542(6) 0.0361(9) 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 0.032(4) 0.035(4) 0.023(4) 0.000(3) 0.000 0.000
C2 0.027(2) 0.034(3) 0.022(3) 0.002(2) 0.003(2) -0.001(2)
C3 0.022(2) 0.038(3) 0.016(3) -0.006(2) -0.003(2) -0.001(2)
C4 0.036(3) 0.037(3) 0.021(3) -0.003(2) -0.004(2) 0.000(2)
C5 0.030(3) 0.040(3) 0.024(3) 0.003(2) 0.001(3) -0.007(2)
C6 0.026(3) 0.046(3) 0.029(3) -0.002(3) -0.002(2) -0.004(2)
C7 0.028(3) 0.040(3) 0.029(3) -0.005(3) -0.005(2) 0.005(2)
C8 0.035(3) 0.032(3) 0.025(3) 0.006(2) -0.001(3) -0.008(2)
F1 0.0481(19) 0.0372(17) 0.047(2) 0.0046(15) 0.0043(18) 0.0088(14)
F2 0.0513(19) 0.0502(19) 0.059(2) 0.0177(18) 0.013(2) -0.0089(15)
F3 0.0254(16) 0.067(2) 0.049(2) 0.0034(19) 0.0126(18) -0.0021(14)
F4 0.0368(17) 0.050(2) 0.049(2) 0.0081(18) -0.0015(18) 0.0097(16)
F5 0.0384(16) 0.0453(17) 0.0414(19) 0.0141(17) 0.0043(16) -0.0012(15)
F6 0.038(2) 0.049(3) 0.039(3) -0.017(2) 0.000 0.000
N1 0.024(2) 0.047(3) 0.018(2) -0.001(2) -0.0018(19) -0.002(2)
O1 0.035(2) 0.051(2) 0.0222(19) 0.0016(17) -0.0070(19) -0.0050(19)
_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 F6 1.374(8) . ?
C1 N1 1.448(6) 3 ?
C1 N1 1.448(6) . ?
C1 H1 1.0000 . ?
C2 O1 1.201(6) . ?
C2 N1 1.377(7) . ?
C2 C2 1.544(9) 3 ?
C3 C4 1.378(7) . ?
C3 C8 1.383(7) . ?
C3 N1 1.418(6) . ?
C4 F1 1.350(6) . ?
C4 C5 1.380(7) . ?
C5 F2 1.330(6) . ?
C5 C6 1.373(7) . ?
C6 F3 1.338(6) . ?
C6 C7 1.378(7) . ?
C7 F4 1.333(6) . ?
C7 C8 1.386(7) . ?
C8 F5 1.333(6) . ?
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
F6 C1 N1 109.4(4) . 3 ?
F6 C1 N1 109.4(4) . . ?
N1 C1 N1 102.3(5) 3 . ?
F6 C1 H1 111.8 . . ?
N1 C1 H1 111.8 3 . ?
N1 C1 H1 111.8 . . ?
O1 C2 N1 128.3(4) . . ?
O1 C2 C2 126.6(3) . 3 ?
N1 C2 C2 105.0(3) . 3 ?
C4 C3 C8 118.5(4) . . ?
C4 C3 N1 121.4(5) . . ?
C8 C3 N1 120.1(5) . . ?
F1 C4 C3 119.2(4) . . ?
F1 C4 C5 119.3(5) . . ?
C3 C4 C5 121.5(5) . . ?
F2 C5 C6 120.6(4) . . ?
F2 C5 C4 120.4(4) . . ?
C6 C5 C4 119.0(5) . . ?
F3 C6 C5 119.8(5) . . ?
F3 C6 C7 119.1(5) . . ?
C5 C6 C7 121.0(5) . . ?
F4 C7 C6 120.8(5) . . ?
F4 C7 C8 120.1(5) . . ?
C6 C7 C8 119.0(5) . . ?
F5 C8 C3 119.8(4) . . ?
F5 C8 C7 119.2(4) . . ?
C3 C8 C7 120.9(5) . . ?
C2 N1 C3 123.8(4) . . ?
C2 N1 C1 113.1(4) . . ?
C3 N1 C1 122.5(4) . . ?
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
C8 C3 C4 F1 179.7(5) . . . . ?
N1 C3 C4 F1 0.7(7) . . . . ?
C8 C3 C4 C5 0.3(7) . . . . ?
N1 C3 C4 C5 -178.7(5) . . . . ?
F1 C4 C5 F2 1.9(8) . . . . ?
C3 C4 C5 F2 -178.7(5) . . . . ?
F1 C4 C5 C6 178.3(5) . . . . ?
C3 C4 C5 C6 -2.3(8) . . . . ?
F2 C5 C6 F3 -2.7(8) . . . . ?
C4 C5 C6 F3 -179.1(5) . . . . ?
F2 C5 C6 C7 179.1(5) . . . . ?
C4 C5 C6 C7 2.7(8) . . . . ?
F3 C6 C7 F4 -1.5(8) . . . . ?
C5 C6 C7 F4 176.7(5) . . . . ?
F3 C6 C7 C8 -179.4(5) . . . . ?
C5 C6 C7 C8 -1.2(8) . . . . ?
C4 C3 C8 F5 -177.3(5) . . . . ?
N1 C3 C8 F5 1.7(8) . . . . ?
C4 C3 C8 C7 1.3(8) . . . . ?
N1 C3 C8 C7 -179.7(5) . . . . ?
F4 C7 C8 F5 -0.2(8) . . . . ?
C6 C7 C8 F5 177.7(5) . . . . ?
F4 C7 C8 C3 -178.8(5) . . . . ?
C6 C7 C8 C3 -0.9(8) . . . . ?
O1 C2 N1 C3 2.9(9) . . . . ?
C2 C2 N1 C3 -179.3(4) 3 . . . ?
O1 C2 N1 C1 174.2(6) . . . . ?
C2 C2 N1 C1 -8.0(5) 3 . . . ?
C4 C3 N1 C2 -116.5(6) . . . . ?
C8 C3 N1 C2 64.5(7) . . . . ?
C4 C3 N1 C1 73.0(7) . . . . ?
C8 C3 N1 C1 -106.0(6) . . . . ?
F6 C1 N1 C2 -103.6(5) . . . . ?
N1 C1 N1 C2 12.3(8) 3 . . . ?
F6 C1 N1 C3 67.9(7) . . . . ?
N1 C1 N1 C3 -176.2(3) 3 . . . ?
_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full 27.61
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max 0.285
_refine_diff_density_min -0.342
_refine_diff_density_rms 0.070
# Attachment '- 6b.cif'
data_shelxl6b
_database_code_depnum_ccdc_archive 'CCDC 743957'
#TrackingRef '- 6b.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
2-methoxy-1,3-bis(2,6-dimethylphenyl)imidazolidine-4,5-dione
;
_chemical_name_common
2-methoxy-1,3-bis(2,6-dimethylphenyl)imidazolidine-4,5-dione
_chemical_melting_point ?
_chemical_formula_moiety 'C20 H22 N2 O3'
_chemical_formula_sum 'C20 H22 N2 O3'
_chemical_formula_weight 338.40
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_space_group_name_Hall -P2ybc
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 13.9920(9)
_cell_length_b 10.1520(14)
_cell_length_c 12.9910(15)
_cell_angle_alpha 90.00
_cell_angle_beta 102.895(6)
_cell_angle_gamma 90.00
_cell_volume 1798.8(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 17110
_cell_measurement_theta_min 2.50
_cell_measurement_theta_max 24.02
_exptl_crystal_description plates
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.10
_exptl_crystal_size_mid 0.08
_exptl_crystal_size_min 0.02
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.250
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 720
_exptl_absorpt_coefficient_mu 0.085
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_correction_T_min 0.9916
_exptl_absorpt_correction_T_max 0.9983
_exptl_absorpt_process_details 'SORTAV: (Blessing, 1997)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Nonius KappaCCD'
_diffrn_measurement_method ' \w and \f'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 17110
_diffrn_reflns_av_R_equivalents 0.1112
_diffrn_reflns_av_sigmaI/netI 0.0535
_diffrn_reflns_limit_h_min -16
_diffrn_reflns_limit_h_max 16
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_theta_min 2.50
_diffrn_reflns_theta_max 24.02
_reflns_number_total 2811
_reflns_number_gt 2077
_reflns_threshold_expression >2sigma(I)
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution ?
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_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^)+(0.0525P)^2^+4.9368P] 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 mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2811
_refine_ls_number_parameters 230
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1031
_refine_ls_R_factor_gt 0.0697
_refine_ls_wR_factor_ref 0.1944
_refine_ls_wR_factor_gt 0.1638
_refine_ls_goodness_of_fit_ref 1.081
_refine_ls_restrained_S_all 1.081
_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 0.7533(3) -0.1964(4) 0.0742(3) 0.0288(9) Uani 1 1 d . . .
C2 C 0.8095(3) -0.2045(4) 0.2571(3) 0.0300(9) Uani 1 1 d . . .
C3 C 0.7783(3) -0.0649(4) 0.2245(3) 0.0299(9) Uani 1 1 d . . .
C4 C 0.6518(3) -0.3381(5) -0.0514(4) 0.0425(11) Uani 1 1 d . . .
H4A H 0.5829 -0.3594 -0.0813 0.064 Uiso 0.50 1 calc PR . .
H4B H 0.6857 -0.4165 -0.0174 0.064 Uiso 0.50 1 calc PR . .
H4C H 0.6830 -0.3086 -0.1078 0.064 Uiso 0.50 1 calc PR . .
H4D H 0.7182 -0.3636 -0.0564 0.064 Uiso 0.50 1 calc PR . .
H4E H 0.6154 -0.3065 -0.1203 0.064 Uiso 0.50 1 calc PR . .
H4F H 0.6181 -0.4144 -0.0299 0.064 Uiso 0.50 1 calc PR . .
C5 C 0.8269(3) -0.4095(4) 0.1629(3) 0.0320(9) Uani 1 1 d . . .
C6 C 0.9165(3) -0.4327(4) 0.1354(3) 0.0353(10) Uani 1 1 d . . .
C7 C 0.9478(3) -0.5608(5) 0.1356(3) 0.0437(12) Uani 1 1 d . . .
H7 H 1.0090 -0.5792 0.1183 0.052 Uiso 1 1 calc R . .
C8 C 0.8928(4) -0.6629(5) 0.1602(4) 0.0514(13) Uani 1 1 d . . .
H8 H 0.9158 -0.7508 0.1593 0.062 Uiso 1 1 calc R . .
C9 C 0.8035(4) -0.6381(5) 0.1865(3) 0.0500(13) Uani 1 1 d . . .
H9 H 0.7654 -0.7095 0.2027 0.060 Uiso 1 1 calc R . .
C10 C 0.7695(3) -0.5099(4) 0.1894(3) 0.0387(10) Uani 1 1 d . . .
C11 C 0.7166(3) 0.0469(4) 0.0543(3) 0.0301(9) Uani 1 1 d . . .
C12 C 0.6261(3) 0.1050(4) 0.0582(3) 0.0342(10) Uani 1 1 d . . .
C13 C 0.5978(3) 0.2162(4) -0.0025(3) 0.0398(11) Uani 1 1 d . . .
H13 H 0.5368 0.2568 -0.0017 0.048 Uiso 1 1 calc R . .
C14 C 0.6570(3) 0.2695(4) -0.0644(3) 0.0400(10) Uani 1 1 d . . .
H14 H 0.6359 0.3457 -0.1057 0.048 Uiso 1 1 calc R . .
C15 C 0.7456(3) 0.2135(4) -0.0666(3) 0.0374(10) Uani 1 1 d . . .
H15 H 0.7856 0.2515 -0.1089 0.045 Uiso 1 1 calc R . .
C16 C 0.7776(3) 0.1003(4) -0.0068(3) 0.0337(10) Uani 1 1 d . . .
C17 C 0.9770(3) -0.3212(5) 0.1066(4) 0.0429(11) Uani 1 1 d . . .
H17A H 0.9433 -0.2374 0.1108 0.064 Uiso 0.50 1 calc PR . .
H17B H 0.9858 -0.3341 0.0345 0.064 Uiso 0.50 1 calc PR . .
H17C H 1.0412 -0.3197 0.1558 0.064 Uiso 0.50 1 calc PR . .
H17D H 1.0369 -0.3567 0.0900 0.064 Uiso 0.50 1 calc PR . .
H17E H 0.9944 -0.2600 0.1662 0.064 Uiso 0.50 1 calc PR . .
H17F H 0.9389 -0.2744 0.0449 0.064 Uiso 0.50 1 calc PR . .
C18 C 0.6733(3) -0.4818(5) 0.2202(4) 0.0477(12) Uani 1 1 d . . .
H18A H 0.6438 -0.5648 0.2359 0.072 Uiso 0.50 1 calc PR . .
H18B H 0.6286 -0.4372 0.1618 0.072 Uiso 0.50 1 calc PR . .
H18C H 0.6852 -0.4252 0.2829 0.072 Uiso 0.50 1 calc PR . .
H18D H 0.6613 -0.3866 0.2178 0.072 Uiso 0.50 1 calc PR . .
H18E H 0.6765 -0.5143 0.2920 0.072 Uiso 0.50 1 calc PR . .
H18F H 0.6199 -0.5263 0.1709 0.072 Uiso 0.50 1 calc PR . .
C19 C 0.5634(3) 0.0505(5) 0.1273(4) 0.0412(11) Uani 1 1 d . . .
H19A H 0.5948 -0.0278 0.1642 0.062 Uiso 0.50 1 calc PR . .
H19B H 0.4991 0.0264 0.0839 0.062 Uiso 0.50 1 calc PR . .
H19C H 0.5550 0.1171 0.1792 0.062 Uiso 0.50 1 calc PR . .
H19D H 0.5045 0.1049 0.1207 0.062 Uiso 0.50 1 calc PR . .
H19E H 0.6002 0.0507 0.2010 0.062 Uiso 0.50 1 calc PR . .
H19F H 0.5443 -0.0400 0.1057 0.062 Uiso 0.50 1 calc PR . .
C20 C 0.8771(3) 0.0413(4) -0.0073(4) 0.0394(10) Uani 1 1 d . . .
H20A H 0.9083 0.0922 -0.0549 0.059 Uiso 0.50 1 calc PR . .
H20B H 0.8688 -0.0502 -0.0317 0.059 Uiso 0.50 1 calc PR . .
H20C H 0.9184 0.0438 0.0643 0.059 Uiso 0.50 1 calc PR . .
H20D H 0.8887 -0.0350 0.0400 0.059 Uiso 0.50 1 calc PR . .
H20E H 0.9282 0.1074 0.0169 0.059 Uiso 0.50 1 calc PR . .
H20F H 0.8786 0.0134 -0.0791 0.059 Uiso 0.50 1 calc PR . .
N1 N 0.7949(2) -0.2752(3) 0.1672(2) 0.0287(8) Uani 1 1 d . . .
N2 N 0.7491(2) -0.0661(3) 0.1177(2) 0.0289(8) Uani 1 1 d . . .
O1 O 0.8422(2) -0.2433(3) 0.3470(2) 0.0363(7) Uani 1 1 d . . .
O2 O 0.7808(2) 0.0290(3) 0.2837(2) 0.0373(7) Uani 1 1 d . . .
O3 O 0.65741(19) -0.2353(3) 0.0252(2) 0.0328(7) Uani 1 1 d . . .
H1 H 0.794(3) -0.203(4) 0.022(3) 0.023(10) Uiso 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 0.027(2) 0.028(2) 0.031(2) 0.0000(17) 0.0054(17) 0.0004(16)
C2 0.027(2) 0.034(2) 0.028(2) 0.0006(18) 0.0047(17) -0.0040(17)
C3 0.030(2) 0.030(2) 0.031(2) -0.0041(19) 0.0085(17) -0.0023(17)
C4 0.040(2) 0.042(3) 0.045(3) -0.015(2) 0.007(2) -0.002(2)
C5 0.039(2) 0.025(2) 0.029(2) -0.0023(17) 0.0003(17) 0.0028(17)
C6 0.037(2) 0.041(2) 0.024(2) -0.0057(18) -0.0018(17) 0.0023(19)
C7 0.047(3) 0.047(3) 0.032(2) -0.006(2) -0.002(2) 0.017(2)
C8 0.071(3) 0.037(3) 0.036(3) -0.008(2) -0.009(2) 0.017(2)
C9 0.073(3) 0.037(3) 0.032(2) 0.000(2) -0.006(2) -0.005(2)
C10 0.046(3) 0.029(2) 0.036(2) 0.0004(19) -0.0001(19) -0.0003(19)
C11 0.035(2) 0.025(2) 0.028(2) -0.0005(17) 0.0038(17) 0.0003(17)
C12 0.032(2) 0.036(2) 0.033(2) -0.0037(19) 0.0019(17) 0.0012(18)
C13 0.036(2) 0.038(2) 0.041(2) -0.003(2) 0.000(2) 0.0087(19)
C14 0.048(3) 0.030(2) 0.037(2) 0.0017(19) 0.001(2) 0.004(2)
C15 0.047(3) 0.032(2) 0.032(2) 0.0016(19) 0.0059(19) -0.0049(19)
C16 0.035(2) 0.032(2) 0.033(2) -0.0048(18) 0.0067(18) -0.0011(18)
C17 0.034(2) 0.055(3) 0.040(2) 0.000(2) 0.0089(19) 0.006(2)
C18 0.044(3) 0.048(3) 0.052(3) 0.008(2) 0.010(2) -0.008(2)
C19 0.034(2) 0.045(3) 0.045(3) -0.003(2) 0.0106(19) 0.0015(19)
C20 0.040(2) 0.035(2) 0.046(3) -0.003(2) 0.017(2) -0.0012(19)
N1 0.0324(17) 0.0262(17) 0.0276(17) 0.0017(14) 0.0071(14) 0.0008(14)
N2 0.0300(17) 0.0275(18) 0.0292(18) -0.0045(14) 0.0068(14) 0.0003(14)
O1 0.0406(16) 0.0357(16) 0.0314(16) 0.0005(13) 0.0057(13) -0.0023(13)
O2 0.0421(17) 0.0331(16) 0.0364(16) -0.0043(14) 0.0082(13) 0.0009(13)
O3 0.0296(14) 0.0339(16) 0.0341(15) -0.0087(13) 0.0052(12) -0.0011(12)
_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 O3 1.407(5) . ?
C1 N2 1.445(5) . ?
C1 N1 1.457(5) . ?
C1 H1 0.98(4) . ?
C2 O1 1.220(5) . ?
C2 N1 1.348(5) . ?
C2 C3 1.515(6) . ?
C3 O2 1.220(5) . ?
C3 N2 1.356(5) . ?
C4 O3 1.432(5) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 H4D 0.9800 . ?
C4 H4E 0.9800 . ?
C4 H4F 0.9800 . ?
C5 C10 1.387(6) . ?
C5 C6 1.398(6) . ?
C5 N1 1.439(5) . ?
C6 C7 1.372(6) . ?
C6 C17 1.510(6) . ?
C7 C8 1.370(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(6) . ?
C9 H9 0.9500 . ?
C10 C18 1.515(6) . ?
C11 C16 1.398(6) . ?
C11 C12 1.408(6) . ?
C11 N2 1.426(5) . ?
C12 C13 1.384(6) . ?
C12 C19 1.495(6) . ?
C13 C14 1.386(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.370(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.403(6) . ?
C15 H15 0.9500 . ?
C16 C20 1.516(6) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 H17D 0.9800 . ?
C17 H17E 0.9800 . ?
C17 H17F 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 H18D 0.9800 . ?
C18 H18E 0.9800 . ?
C18 H18F 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19 H19D 0.9800 . ?
C19 H19E 0.9800 . ?
C19 H19F 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 H20D 0.9800 . ?
C20 H20E 0.9800 . ?
C20 H20F 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
O3 C1 N2 108.3(3) . . ?
O3 C1 N1 112.7(3) . . ?
N2 C1 N1 102.9(3) . . ?
O3 C1 H1 108(2) . . ?
N2 C1 H1 114(2) . . ?
N1 C1 H1 110(2) . . ?
O1 C2 N1 127.5(4) . . ?
O1 C2 C3 126.3(4) . . ?
N1 C2 C3 106.1(3) . . ?
O2 C3 N2 127.7(4) . . ?
O2 C3 C2 126.0(4) . . ?
N2 C3 C2 106.3(3) . . ?
O3 C4 H4A 109.5 . . ?
O3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O3 C4 H4D 109.5 . . ?
H4A C4 H4D 141.1 . . ?
H4B C4 H4D 56.3 . . ?
H4C C4 H4D 56.3 . . ?
O3 C4 H4E 109.5 . . ?
H4A C4 H4E 56.3 . . ?
H4B C4 H4E 141.1 . . ?
H4C C4 H4E 56.3 . . ?
H4D C4 H4E 109.5 . . ?
O3 C4 H4F 109.5 . . ?
H4A C4 H4F 56.3 . . ?
H4B C4 H4F 56.3 . . ?
H4C C4 H4F 141.1 . . ?
H4D C4 H4F 109.5 . . ?
H4E C4 H4F 109.5 . . ?
C10 C5 C6 122.8(4) . . ?
C10 C5 N1 119.0(4) . . ?
C6 C5 N1 118.2(4) . . ?
C7 C6 C5 117.6(4) . . ?
C7 C6 C17 121.0(4) . . ?
C5 C6 C17 121.4(4) . . ?
C8 C7 C6 121.4(4) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 120.2(4) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 120.5(5) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C5 C10 C9 117.5(4) . . ?
C5 C10 C18 121.7(4) . . ?
C9 C10 C18 120.9(4) . . ?
C16 C11 C12 121.7(4) . . ?
C16 C11 N2 118.9(3) . . ?
C12 C11 N2 119.3(4) . . ?
C13 C12 C11 117.8(4) . . ?
C13 C12 C19 120.9(4) . . ?
C11 C12 C19 121.4(4) . . ?
C12 C13 C14 121.1(4) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 120.7(4) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 120.5(4) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 118.2(4) . . ?
C11 C16 C20 121.8(4) . . ?
C15 C16 C20 120.1(4) . . ?
C6 C17 H17A 109.5 . . ?
C6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C6 C17 H17D 109.5 . . ?
H17A C17 H17D 141.1 . . ?
H17B C17 H17D 56.3 . . ?
H17C C17 H17D 56.3 . . ?
C6 C17 H17E 109.5 . . ?
H17A C17 H17E 56.3 . . ?
H17B C17 H17E 141.1 . . ?
H17C C17 H17E 56.3 . . ?
H17D C17 H17E 109.5 . . ?
C6 C17 H17F 109.5 . . ?
H17A C17 H17F 56.3 . . ?
H17B C17 H17F 56.3 . . ?
H17C C17 H17F 141.1 . . ?
H17D C17 H17F 109.5 . . ?
H17E C17 H17F 109.5 . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C18 H18D 109.5 . . ?
H18A C18 H18D 141.1 . . ?
H18B C18 H18D 56.3 . . ?
H18C C18 H18D 56.3 . . ?
C10 C18 H18E 109.5 . . ?
H18A C18 H18E 56.3 . . ?
H18B C18 H18E 141.1 . . ?
H18C C18 H18E 56.3 . . ?
H18D C18 H18E 109.5 . . ?
C10 C18 H18F 109.5 . . ?
H18A C18 H18F 56.3 . . ?
H18B C18 H18F 56.3 . . ?
H18C C18 H18F 141.1 . . ?
H18D C18 H18F 109.5 . . ?
H18E C18 H18F 109.5 . . ?
C12 C19 H19A 109.5 . . ?
C12 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C12 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 C19 H19D 109.5 . . ?
H19A C19 H19D 141.1 . . ?
H19B C19 H19D 56.3 . . ?
H19C C19 H19D 56.3 . . ?
C12 C19 H19E 109.5 . . ?
H19A C19 H19E 56.3 . . ?
H19B C19 H19E 141.1 . . ?
H19C C19 H19E 56.3 . . ?
H19D C19 H19E 109.5 . . ?
C12 C19 H19F 109.5 . . ?
H19A C19 H19F 56.3 . . ?
H19B C19 H19F 56.3 . . ?
H19C C19 H19F 141.1 . . ?
H19D C19 H19F 109.5 . . ?
H19E C19 H19F 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C20 H20D 109.5 . . ?
H20A C20 H20D 141.1 . . ?
H20B C20 H20D 56.3 . . ?
H20C C20 H20D 56.3 . . ?
C16 C20 H20E 109.5 . . ?
H20A C20 H20E 56.3 . . ?
H20B C20 H20E 141.1 . . ?
H20C C20 H20E 56.3 . . ?
H20D C20 H20E 109.5 . . ?
C16 C20 H20F 109.5 . . ?
H20A C20 H20F 56.3 . . ?
H20B C20 H20F 56.3 . . ?
H20C C20 H20F 141.1 . . ?
H20D C20 H20F 109.5 . . ?
H20E C20 H20F 109.5 . . ?
C2 N1 C5 123.4(3) . . ?
C2 N1 C1 112.4(3) . . ?
C5 N1 C1 123.9(3) . . ?
C3 N2 C11 124.7(3) . . ?
C3 N2 C1 112.2(3) . . ?
C11 N2 C1 123.1(3) . . ?
C1 O3 C4 114.7(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
O1 C2 C3 O2 -0.5(7) . . . . ?
N1 C2 C3 O2 -179.7(4) . . . . ?
O1 C2 C3 N2 178.6(4) . . . . ?
N1 C2 C3 N2 -0.7(4) . . . . ?
C10 C5 C6 C7 -0.3(6) . . . . ?
N1 C5 C6 C7 177.5(3) . . . . ?
C10 C5 C6 C17 179.8(4) . . . . ?
N1 C5 C6 C17 -2.4(6) . . . . ?
C5 C6 C7 C8 1.0(6) . . . . ?
C17 C6 C7 C8 -179.1(4) . . . . ?
C6 C7 C8 C9 -0.5(7) . . . . ?
C7 C8 C9 C10 -0.7(7) . . . . ?
C6 C5 C10 C9 -0.9(6) . . . . ?
N1 C5 C10 C9 -178.7(4) . . . . ?
C6 C5 C10 C18 179.2(4) . . . . ?
N1 C5 C10 C18 1.4(6) . . . . ?
C8 C9 C10 C5 1.4(6) . . . . ?
C8 C9 C10 C18 -178.7(4) . . . . ?
C16 C11 C12 C13 1.3(6) . . . . ?
N2 C11 C12 C13 178.6(3) . . . . ?
C16 C11 C12 C19 -177.4(4) . . . . ?
N2 C11 C12 C19 -0.2(6) . . . . ?
C11 C12 C13 C14 -0.6(6) . . . . ?
C19 C12 C13 C14 178.1(4) . . . . ?
C12 C13 C14 C15 -0.3(6) . . . . ?
C13 C14 C15 C16 0.6(6) . . . . ?
C12 C11 C16 C15 -1.1(6) . . . . ?
N2 C11 C16 C15 -178.3(3) . . . . ?
C12 C11 C16 C20 177.2(4) . . . . ?
N2 C11 C16 C20 0.0(6) . . . . ?
C14 C15 C16 C11 0.2(6) . . . . ?
C14 C15 C16 C20 -178.2(4) . . . . ?
O1 C2 N1 C5 -7.1(6) . . . . ?
C3 C2 N1 C5 172.1(3) . . . . ?
O1 C2 N1 C1 179.2(4) . . . . ?
C3 C2 N1 C1 -1.6(4) . . . . ?
C10 C5 N1 C2 81.6(5) . . . . ?
C6 C5 N1 C2 -96.3(5) . . . . ?
C10 C5 N1 C1 -105.4(4) . . . . ?
C6 C5 N1 C1 76.7(5) . . . . ?
O3 C1 N1 C2 -113.4(4) . . . . ?
N2 C1 N1 C2 3.0(4) . . . . ?
O3 C1 N1 C5 72.9(5) . . . . ?
N2 C1 N1 C5 -170.6(3) . . . . ?
O2 C3 N2 C11 1.0(6) . . . . ?
C2 C3 N2 C11 -178.0(3) . . . . ?
O2 C3 N2 C1 -178.3(4) . . . . ?
C2 C3 N2 C1 2.7(4) . . . . ?
C16 C11 N2 C3 107.8(4) . . . . ?
C12 C11 N2 C3 -69.5(5) . . . . ?
C16 C11 N2 C1 -73.0(5) . . . . ?
C12 C11 N2 C1 109.8(4) . . . . ?
O3 C1 N2 C3 116.0(3) . . . . ?
N1 C1 N2 C3 -3.5(4) . . . . ?
O3 C1 N2 C11 -63.4(4) . . . . ?
N1 C1 N2 C11 177.2(3) . . . . ?
N2 C1 O3 C4 159.3(3) . . . . ?
N1 C1 O3 C4 -87.6(4) . . . . ?
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full 24.02
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max 0.372
_refine_diff_density_min -0.293
_refine_diff_density_rms 0.073