data_k1039a
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C26 H20 N2'
_chemical_formula_sum
'C26 H20 N2'
_chemical_formula_weight 360.44
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'
_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 18.6734(5)
_cell_length_b 8.9202(7)
_cell_length_c 11.2248(6)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1869.72(18)
_cell_formula_units_Z 4
_cell_measurement_temperature 150(1)
_cell_measurement_reflns_used 11923
_cell_measurement_theta_min 2.8
_cell_measurement_theta_max 27.4
_exptl_crystal_description 'block'
_exptl_crystal_colour 'colourless'
_exptl_crystal_size_max 0.18
_exptl_crystal_size_mid 0.15
_exptl_crystal_size_min 0.12
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.280
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 760
_exptl_absorpt_coefficient_mu 0.075
# Absorption correction
_exptl_absorpt_correction_type 'multi-scan'
_exptl_absorpt_correction_T_min 0.873
_exptl_absorpt_correction_T_max 0.991
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 150(1)
_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 '\f scans and \w scans with \k offsets'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number 11923
_diffrn_reflns_av_R_equivalents 0.0845
_diffrn_reflns_av_sigmaI/netI 0.0712
_diffrn_reflns_limit_h_min -22
_diffrn_reflns_limit_h_max 24
_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 2.84
_diffrn_reflns_theta_max 27.37
_reflns_number_total 2217
_reflns_number_gt 1456
_reflns_threshold_expression 'I>2\s(I)'
_computing_data_collection 'Collect (Nonius B.V., 1997-2002)'
_computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction 'Denzo-SMN'
_computing_structure_solution 'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_molecular_graphics 'PLATON (Spek, 2009)'
_computing_publication_material 'SHELXTL V6.1'
_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A.,
Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst.
27, 435.
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.
Nonius B.V (1997-2002). Collect. Data collection software, Delft,
The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
Macromolecular Crystallography, Part A edited by C. W. Carter &
R. M. Sweet pp. 307-326. London: Academic press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148--155.
;
_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^)+(0.0619P)^2^] 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 0.012(2)
_refine_ls_extinction_expression
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
#_refine_ls_abs_structure_details
# 'Flack H D (1983), Acta Cryst. A39, 876-881'
#_refine_ls_abs_structure_Flack 3(5)
_refine_ls_number_reflns 2217
_refine_ls_number_parameters 254
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0966
_refine_ls_R_factor_gt 0.0479
_refine_ls_wR_factor_ref 0.1204
_refine_ls_wR_factor_gt 0.1000
_refine_ls_goodness_of_fit_ref 1.036
_refine_ls_restrained_S_all 1.035
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.63877(13) 0.2450(3) 0.4084(3) 0.0298(7) Uani 1 1 d . . .
N2 N 0.76398(13) 0.2263(3) 0.3679(3) 0.0288(7) Uani 1 1 d . . .
C1 C 0.70898(15) 0.2989(3) 0.4480(3) 0.0262(7) Uani 1 1 d . . .
C2 C 0.72662(16) 0.2455(4) 0.5762(3) 0.0310(8) Uani 1 1 d . . .
H2A H 0.7356 0.3318 0.6297 0.037 Uiso 1 1 calc R . .
H2B H 0.6871 0.1845 0.6094 0.037 Uiso 1 1 calc R . .
C3 C 0.79292(16) 0.1532(4) 0.5604(3) 0.0289(8) Uani 1 1 d . . .
C4 C 0.83369(17) 0.0798(4) 0.6476(3) 0.0335(8) Uani 1 1 d . . .
H4A H 0.8227 0.0925 0.7297 0.040 Uiso 1 1 calc R . .
C5 C 0.88898(17) -0.0097(4) 0.6140(4) 0.0359(9) Uani 1 1 d . . .
H5A H 0.9163 -0.0598 0.6732 0.043 Uiso 1 1 calc R . .
C6 C 0.90678(17) -0.0297(4) 0.4921(3) 0.0316(8) Uani 1 1 d . . .
C7 C 0.96196(16) -0.1294(4) 0.4556(4) 0.0383(9) Uani 1 1 d . . .
H7A H 0.9885 -0.1827 0.5141 0.046 Uiso 1 1 calc R . .
C8 C 0.97745(17) -0.1498(4) 0.3381(4) 0.0416(10) Uani 1 1 d . . .
H8A H 1.0138 -0.2186 0.3155 0.050 Uiso 1 1 calc R . .
C9 C 0.94001(17) -0.0697(4) 0.2501(3) 0.0375(9) Uani 1 1 d . . .
H9A H 0.9516 -0.0838 0.1685 0.045 Uiso 1 1 calc R . .
C10 C 0.88688(15) 0.0285(4) 0.2814(3) 0.0328(9) Uani 1 1 d . . .
H10A H 0.8627 0.0835 0.2211 0.039 Uiso 1 1 calc R . .
C11 C 0.86756(16) 0.0491(4) 0.4022(3) 0.0296(8) Uani 1 1 d . . .
C12 C 0.80945(16) 0.1399(3) 0.4420(3) 0.0271(8) Uani 1 1 d . . .
C13 C 0.72353(15) 0.1510(4) 0.2723(3) 0.0316(8) Uani 1 1 d . . .
H13A H 0.7376 0.0445 0.2650 0.038 Uiso 1 1 calc R . .
H13B H 0.7309 0.2016 0.1948 0.038 Uiso 1 1 calc R . .
C14 C 0.64676(16) 0.1658(4) 0.3137(3) 0.0293(8) Uani 1 1 d . . .
C15 C 0.58610(16) 0.0976(4) 0.2486(3) 0.0328(9) Uani 1 1 d . . .
C16 C 0.59817(19) -0.0094(4) 0.1619(4) 0.0414(10) Uani 1 1 d . . .
H16A H 0.6458 -0.0404 0.1451 0.050 Uiso 1 1 calc R . .
C17 C 0.5415(2) -0.0723(4) 0.0988(4) 0.0478(11) Uani 1 1 d . . .
H17A H 0.5503 -0.1464 0.0398 0.057 Uiso 1 1 calc R . .
C18 C 0.47221(19) -0.0263(5) 0.1223(4) 0.0454(11) Uani 1 1 d . . .
H18A H 0.4334 -0.0682 0.0790 0.054 Uiso 1 1 calc R . .
C19 C 0.45951(18) 0.0800(4) 0.2085(4) 0.0432(10) Uani 1 1 d . . .
H19A H 0.4118 0.1104 0.2251 0.052 Uiso 1 1 calc R . .
C20 C 0.51581(16) 0.1431(4) 0.2712(4) 0.0375(9) Uani 1 1 d . . .
H20A H 0.5066 0.2176 0.3297 0.045 Uiso 1 1 calc R . .
C21 C 0.71260(16) 0.4688(3) 0.4410(3) 0.0266(7) Uani 1 1 d . . .
C22 C 0.65295(18) 0.5555(4) 0.4671(3) 0.0319(8) Uani 1 1 d . . .
H22A H 0.6085 0.5080 0.4837 0.038 Uiso 1 1 calc R . .
C23 C 0.65744(19) 0.7113(4) 0.4690(3) 0.0361(9) Uani 1 1 d . . .
H23A H 0.6164 0.7696 0.4878 0.043 Uiso 1 1 calc R . .
C24 C 0.72173(18) 0.7808(4) 0.4437(4) 0.0393(9) Uani 1 1 d . . .
H24A H 0.7250 0.8871 0.4451 0.047 Uiso 1 1 calc R . .
C25 C 0.78110(18) 0.6961(4) 0.4164(4) 0.0397(9) Uani 1 1 d . . .
H25A H 0.8253 0.7440 0.3986 0.048 Uiso 1 1 calc R . .
C26 C 0.77654(17) 0.5410(4) 0.4148(3) 0.0346(9) Uani 1 1 d . . .
H26A H 0.8177 0.4834 0.3955 0.042 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
N1 0.0306(14) 0.0277(15) 0.0311(17) 0.0010(15) 0.0003(12) -0.0041(11)
N2 0.0278(14) 0.0304(15) 0.0283(16) -0.0011(13) -0.0008(12) 0.0009(12)
C1 0.0242(16) 0.0288(17) 0.0255(19) 0.0008(17) -0.0002(13) -0.0023(13)
C2 0.0372(19) 0.031(2) 0.024(2) 0.0020(16) 0.0004(15) -0.0008(15)
C3 0.0315(17) 0.0261(19) 0.029(2) -0.0016(16) -0.0020(15) -0.0059(13)
C4 0.0352(19) 0.036(2) 0.029(2) 0.0013(17) -0.0027(16) -0.0015(16)
C5 0.0337(17) 0.041(2) 0.033(2) 0.0060(18) -0.0057(15) -0.0002(15)
C6 0.0322(17) 0.0297(18) 0.033(2) 0.0009(17) -0.0015(16) -0.0034(14)
C7 0.0304(18) 0.044(2) 0.041(3) 0.0005(19) -0.0053(17) 0.0034(15)
C8 0.0331(18) 0.046(2) 0.045(3) -0.004(2) -0.0003(17) 0.0038(16)
C9 0.0320(18) 0.052(2) 0.029(2) -0.0019(19) 0.0042(16) 0.0021(16)
C10 0.0295(18) 0.037(2) 0.032(2) 0.0006(18) -0.0039(14) -0.0039(14)
C11 0.0283(16) 0.0263(18) 0.034(2) -0.0008(17) -0.0002(15) -0.0034(13)
C12 0.0303(16) 0.0245(17) 0.027(2) 0.0040(16) -0.0021(15) -0.0066(13)
C13 0.0321(17) 0.036(2) 0.027(2) 0.0001(17) -0.0012(15) -0.0006(14)
C14 0.0334(17) 0.0273(17) 0.027(2) 0.0032(17) -0.0017(15) -0.0013(13)
C15 0.0318(18) 0.033(2) 0.033(2) 0.0002(18) -0.0020(15) -0.0047(14)
C16 0.037(2) 0.042(2) 0.045(3) -0.004(2) -0.0049(17) -0.0004(16)
C17 0.051(3) 0.044(2) 0.048(3) -0.011(2) -0.0092(19) -0.0048(18)
C18 0.042(2) 0.047(2) 0.046(3) 0.005(2) -0.0126(19) -0.0152(18)
C19 0.030(2) 0.050(2) 0.050(3) 0.007(2) -0.0034(17) -0.0067(16)
C20 0.0331(19) 0.041(2) 0.038(2) 0.0038(19) -0.0007(16) -0.0027(15)
C21 0.0337(16) 0.0253(16) 0.0207(18) 0.0000(16) -0.0003(13) -0.0034(13)
C22 0.0346(18) 0.035(2) 0.026(2) -0.0021(17) 0.0014(15) -0.0015(15)
C23 0.043(2) 0.034(2) 0.031(2) -0.0007(17) 0.0031(16) 0.0038(16)
C24 0.050(2) 0.0277(18) 0.040(2) 0.0006(19) -0.0051(18) -0.0075(16)
C25 0.0417(19) 0.038(2) 0.039(2) 0.0001(19) -0.0032(17) -0.0133(16)
C26 0.0328(17) 0.039(2) 0.032(2) -0.0021(18) -0.0012(15) -0.0031(14)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C14 1.285(4) . ?
N1 C1 1.466(4) . ?
N2 C12 1.416(4) . ?
N2 C13 1.474(4) . ?
N2 C1 1.511(4) . ?
C1 C21 1.519(4) . ?
C1 C2 1.551(5) . ?
C2 C3 1.497(4) . ?
C3 C12 1.370(5) . ?
C3 C4 1.402(5) . ?
C4 C5 1.359(5) . ?
C5 C6 1.419(5) . ?
C6 C7 1.422(5) . ?
C6 C11 1.432(5) . ?
C7 C8 1.362(6) . ?
C8 C9 1.405(6) . ?
C9 C10 1.369(5) . ?
C10 C11 1.415(5) . ?
C11 C12 1.426(4) . ?
C13 C14 1.513(4) . ?
C14 C15 1.479(5) . ?
C15 C16 1.382(5) . ?
C15 C20 1.397(5) . ?
C16 C17 1.392(5) . ?
C17 C18 1.382(5) . ?
C18 C19 1.375(6) . ?
C19 C20 1.385(5) . ?
C21 C22 1.387(4) . ?
C21 C26 1.388(4) . ?
C22 C23 1.392(5) . ?
C23 C24 1.381(5) . ?
C24 C25 1.376(5) . ?
C25 C26 1.386(5) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 N1 C1 109.1(3) . . ?
C12 N2 C13 119.2(3) . . ?
C12 N2 C1 106.9(3) . . ?
C13 N2 C1 106.3(2) . . ?
N1 C1 N2 106.7(3) . . ?
N1 C1 C21 110.6(2) . . ?
N2 C1 C21 111.5(2) . . ?
N1 C1 C2 111.8(3) . . ?
N2 C1 C2 106.0(2) . . ?
C21 C1 C2 110.2(3) . . ?
C3 C2 C1 103.6(3) . . ?
C12 C3 C4 121.0(3) . . ?
C12 C3 C2 110.4(3) . . ?
C4 C3 C2 128.5(3) . . ?
C5 C4 C3 119.5(3) . . ?
C4 C5 C6 121.3(3) . . ?
C5 C6 C7 121.8(3) . . ?
C5 C6 C11 119.9(3) . . ?
C7 C6 C11 118.3(3) . . ?
C8 C7 C6 121.1(3) . . ?
C7 C8 C9 120.5(3) . . ?
C10 C9 C8 120.4(4) . . ?
C9 C10 C11 120.9(3) . . ?
C10 C11 C12 124.6(3) . . ?
C10 C11 C6 118.8(3) . . ?
C12 C11 C6 116.6(3) . . ?
C3 C12 N2 112.8(3) . . ?
C3 C12 C11 121.7(3) . . ?
N2 C12 C11 125.5(3) . . ?
N2 C13 C14 102.9(3) . . ?
N1 C14 C15 123.1(3) . . ?
N1 C14 C13 114.3(3) . . ?
C15 C14 C13 122.6(3) . . ?
C16 C15 C20 118.8(3) . . ?
C16 C15 C14 120.5(3) . . ?
C20 C15 C14 120.7(3) . . ?
C15 C16 C17 120.9(3) . . ?
C18 C17 C16 119.6(4) . . ?
C19 C18 C17 120.0(3) . . ?
C18 C19 C20 120.5(3) . . ?
C19 C20 C15 120.2(4) . . ?
C22 C21 C26 118.5(3) . . ?
C22 C21 C1 120.6(3) . . ?
C26 C21 C1 120.8(3) . . ?
C21 C22 C23 120.7(3) . . ?
C24 C23 C22 119.8(3) . . ?
C25 C24 C23 120.0(3) . . ?
C24 C25 C26 120.1(3) . . ?
C25 C26 C21 120.9(3) . . ?
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full 27.37
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max 0.204
_refine_diff_density_min -0.210
_refine_diff_density_rms 0.051