# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012
data_global
_journal_name_full Org.Biomol.Chem.
_journal_coden_cambridge 0177
_journal_year ?
_journal_volume ?
_journal_page_first ?
_publ_contact_author_name 'Viktor O. Iaroshenko'
_publ_contact_author_email iva108@googlemail.com
loop_
_publ_author_name
'Viktor O. Iaroshenko'
'Ingo Knepper'
'Muhammad Zahid'
'Sergii Dudkin'
'Rene Kuzora'
;
A.Villinger
;
'Peter Langer'
data_av_ikp193
_database_code_depnum_ccdc_archive 'CCDC 834862'
#TrackingRef 'Ingo-Knepper-av_ikp193.cif'
_audit_author_name 'Villinger, A.'
_audit_creation_method SHELXL-97
#==============================================================================
# CHEMICAL DATA
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C14 H10 N2 O'
_chemical_formula_sum 'C14 H10 N2 O'
_chemical_formula_weight 222.24
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'
#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/n'
_symmetry_space_group_name_Hall '-P 2yn'
_symmetry_Int_Tables_number 14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 3.78060(10)
_cell_length_b 24.0853(8)
_cell_length_c 11.7506(4)
_cell_angle_alpha 90.00
_cell_angle_beta 97.413(2)
_cell_angle_gamma 90.00
_cell_volume 1061.03(6)
_cell_formula_units_Z 4
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 5850
_cell_measurement_theta_min 6.163
_cell_measurement_theta_max 65.015
_exptl_crystal_description needle
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.75
_exptl_crystal_size_mid 0.25
_exptl_crystal_size_min 0.09
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.391
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 464
_exptl_absorpt_coefficient_mu 0.090
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9355
_exptl_absorpt_correction_T_max 0.9919
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)'
#==============================================================================
# EXPERIMENTAL DATA
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method 'phi and psi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 11312
_diffrn_reflns_av_R_equivalents 0.0280
_diffrn_reflns_av_sigmaI/netI 0.0238
_diffrn_reflns_limit_h_min -5
_diffrn_reflns_limit_h_max 4
_diffrn_reflns_limit_k_min -32
_diffrn_reflns_limit_k_max 32
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_theta_min 2.43
_diffrn_reflns_theta_max 28.49
_reflns_number_total 2658
_reflns_number_gt 2328
_reflns_threshold_expression >2\s(I)
_computing_data_collection 'Bruker Apex v2.0-2'
_computing_cell_refinement 'Bruker Apex v2.0-2'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material SHELXL-97
#==============================================================================
# REFINEMENT DATA
_refine_special_details
;
All H atoms (with exception of H1a) were positioned geometrically and
refined using a riding model , with C---H = 0.98 (methyl groups), 0.99\%A
(methylene groups), 1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with
U~iso~(H) = 1.5 times U~eq~(C) (methyl groups) or with
U~iso~(H) = 1.2 times U~eq~(C) (methylene groups, aryl CH,
methine groups). Torsion angles of all methyl groups were allowed to refine.
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0521P)^2^+1.0677P] 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 2658
_refine_ls_number_parameters 158
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0631
_refine_ls_R_factor_gt 0.0568
_refine_ls_wR_factor_ref 0.1405
_refine_ls_wR_factor_gt 0.1375
_refine_ls_goodness_of_fit_ref 1.065
_refine_ls_restrained_S_all 1.065
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
#==============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3750(4) 0.30201(5) 0.56182(10) 0.0264(3) Uani 1 1 d . . .
N1 N 0.0929(4) 0.24295(6) 0.86447(12) 0.0185(3) Uani 1 1 d . . .
N2 N 0.0114(4) 0.33159(6) 0.93322(12) 0.0223(3) Uani 1 1 d . . .
C1 C 0.2830(4) 0.28301(7) 0.65292(13) 0.0189(3) Uani 1 1 d . . .
C2 C 0.2530(4) 0.22541(7) 0.67770(14) 0.0199(3) Uani 1 1 d . . .
H2 H 0.2988 0.1990 0.6214 0.024 Uiso 1 1 calc R . .
C3 C 0.1601(4) 0.20686(7) 0.78026(13) 0.0177(3) Uani 1 1 d . . .
C4 C 0.1023(4) 0.29919(7) 0.84729(13) 0.0177(3) Uani 1 1 d . . .
C5 C 0.1956(4) 0.32058(7) 0.74360(13) 0.0181(3) Uani 1 1 d . . .
C6 C 0.0113(5) 0.38595(7) 0.91569(15) 0.0245(4) Uani 1 1 d . . .
H6 H -0.0552 0.4092 0.9747 0.029 Uiso 1 1 calc R . .
C7 C 0.1018(5) 0.41170(7) 0.81657(15) 0.0252(4) Uani 1 1 d . . .
H7 H 0.0982 0.4510 0.8092 0.030 Uiso 1 1 calc R . .
C8 C 0.1965(5) 0.37835(7) 0.73007(15) 0.0230(4) Uani 1 1 d . . .
H8 H 0.2617 0.3944 0.6619 0.028 Uiso 1 1 calc R . .
C9 C 0.1248(4) 0.14660(7) 0.80243(14) 0.0190(3) Uani 1 1 d . . .
C10 C -0.0365(5) 0.11272(7) 0.71349(15) 0.0248(4) Uani 1 1 d . . .
H10 H -0.1231 0.1286 0.6412 0.030 Uiso 1 1 calc R . .
C11 C -0.0701(5) 0.05608(8) 0.73067(17) 0.0295(4) Uani 1 1 d . . .
H11 H -0.1812 0.0333 0.6703 0.035 Uiso 1 1 calc R . .
C12 C 0.0583(5) 0.03259(7) 0.83579(18) 0.0302(4) Uani 1 1 d . . .
H12 H 0.0341 -0.0062 0.8476 0.036 Uiso 1 1 calc R . .
C13 C 0.2219(5) 0.06587(8) 0.92348(17) 0.0281(4) Uani 1 1 d . . .
H13 H 0.3121 0.0496 0.9951 0.034 Uiso 1 1 calc R . .
C14 C 0.2551(5) 0.12278(7) 0.90771(14) 0.0224(3) Uani 1 1 d . . .
H14 H 0.3662 0.1453 0.9684 0.027 Uiso 1 1 calc R . .
H1A H 0.021(7) 0.2310(11) 0.933(2) 0.045(7) 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
O1 0.0356(7) 0.0271(6) 0.0187(6) 0.0025(5) 0.0120(5) 0.0012(5)
N1 0.0205(7) 0.0230(7) 0.0131(6) 0.0006(5) 0.0057(5) 0.0003(5)
N2 0.0251(7) 0.0259(7) 0.0162(7) -0.0021(5) 0.0046(5) 0.0020(6)
C1 0.0172(7) 0.0251(8) 0.0148(7) 0.0002(6) 0.0031(5) 0.0012(6)
C2 0.0205(8) 0.0232(8) 0.0166(7) -0.0021(6) 0.0047(6) 0.0012(6)
C3 0.0152(7) 0.0219(7) 0.0162(7) -0.0004(6) 0.0023(5) -0.0001(6)
C4 0.0151(7) 0.0234(8) 0.0147(7) -0.0006(6) 0.0020(5) 0.0006(6)
C5 0.0153(7) 0.0235(8) 0.0154(7) 0.0003(6) 0.0017(5) -0.0002(6)
C6 0.0265(9) 0.0265(8) 0.0205(8) -0.0054(6) 0.0031(6) 0.0037(7)
C7 0.0280(9) 0.0209(8) 0.0266(9) 0.0008(6) 0.0033(7) 0.0021(6)
C8 0.0243(8) 0.0240(8) 0.0210(8) 0.0035(6) 0.0042(6) -0.0005(6)
C9 0.0171(7) 0.0210(7) 0.0196(7) -0.0006(6) 0.0053(6) 0.0009(6)
C10 0.0241(8) 0.0265(8) 0.0234(8) -0.0015(7) 0.0013(6) -0.0007(7)
C11 0.0304(10) 0.0260(9) 0.0322(10) -0.0063(7) 0.0044(8) -0.0042(7)
C12 0.0335(10) 0.0204(8) 0.0389(10) 0.0012(7) 0.0131(8) 0.0005(7)
C13 0.0302(9) 0.0273(9) 0.0280(9) 0.0057(7) 0.0076(7) 0.0057(7)
C14 0.0234(8) 0.0249(8) 0.0190(8) 0.0004(6) 0.0036(6) 0.0027(6)
#==============================================================================
# MOLECULAR GEOMETRY
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.254(2) . ?
N1 C3 1.365(2) . ?
N1 C4 1.371(2) . ?
N1 H1A 0.92(3) . ?
N2 C6 1.325(2) . ?
N2 C4 1.355(2) . ?
C1 C2 1.425(2) . ?
C1 C5 1.468(2) . ?
C2 C3 1.373(2) . ?
C2 H2 0.9500 . ?
C3 C9 1.484(2) . ?
C4 C5 1.409(2) . ?
C5 C8 1.401(2) . ?
C6 C7 1.401(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.378(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C14 1.395(2) . ?
C9 C10 1.402(2) . ?
C10 C11 1.387(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
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
C3 N1 C4 120.77(14) . . ?
C3 N1 H1A 122.1(16) . . ?
C4 N1 H1A 116.9(16) . . ?
C6 N2 C4 116.63(15) . . ?
O1 C1 C2 124.61(15) . . ?
O1 C1 C5 120.53(15) . . ?
C2 C1 C5 114.86(14) . . ?
C3 C2 C1 122.17(15) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
N1 C3 C2 121.44(15) . . ?
N1 C3 C9 117.78(14) . . ?
C2 C3 C9 120.77(14) . . ?
N2 C4 N1 116.46(14) . . ?
N2 C4 C5 123.34(15) . . ?
N1 C4 C5 120.19(14) . . ?
C8 C5 C4 117.77(15) . . ?
C8 C5 C1 121.74(15) . . ?
C4 C5 C1 120.49(14) . . ?
N2 C6 C7 124.85(16) . . ?
N2 C6 H6 117.6 . . ?
C7 C6 H6 117.6 . . ?
C8 C7 C6 118.02(16) . . ?
C8 C7 H7 121.0 . . ?
C6 C7 H7 121.0 . . ?
C7 C8 C5 119.38(16) . . ?
C7 C8 H8 120.3 . . ?
C5 C8 H8 120.3 . . ?
C14 C9 C10 119.46(16) . . ?
C14 C9 C3 121.92(15) . . ?
C10 C9 C3 118.60(15) . . ?
C11 C10 C9 120.20(17) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.15(17) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 119.80(17) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.66(17) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C9 119.72(16) . . ?
C13 C14 H14 120.1 . . ?
C9 C14 H14 120.1 . . ?
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 C1 C2 C3 178.24(16) . . . . ?
C5 C1 C2 C3 -2.0(2) . . . . ?
C4 N1 C3 C2 2.6(2) . . . . ?
C4 N1 C3 C9 -176.55(14) . . . . ?
C1 C2 C3 N1 -0.3(2) . . . . ?
C1 C2 C3 C9 178.87(15) . . . . ?
C6 N2 C4 N1 -178.31(15) . . . . ?
C6 N2 C4 C5 0.4(2) . . . . ?
C3 N1 C4 N2 176.22(14) . . . . ?
C3 N1 C4 C5 -2.5(2) . . . . ?
N2 C4 C5 C8 0.6(2) . . . . ?
N1 C4 C5 C8 179.20(15) . . . . ?
N2 C4 C5 C1 -178.52(14) . . . . ?
N1 C4 C5 C1 0.1(2) . . . . ?
O1 C1 C5 C8 2.8(2) . . . . ?
C2 C1 C5 C8 -177.04(15) . . . . ?
O1 C1 C5 C4 -178.15(15) . . . . ?
C2 C1 C5 C4 2.0(2) . . . . ?
C4 N2 C6 C7 -0.9(3) . . . . ?
N2 C6 C7 C8 0.4(3) . . . . ?
C6 C7 C8 C5 0.6(3) . . . . ?
C4 C5 C8 C7 -1.0(2) . . . . ?
C1 C5 C8 C7 178.05(15) . . . . ?
N1 C3 C9 C14 -42.9(2) . . . . ?
C2 C3 C9 C14 137.89(17) . . . . ?
N1 C3 C9 C10 138.74(16) . . . . ?
C2 C3 C9 C10 -40.5(2) . . . . ?
C14 C9 C10 C11 0.8(3) . . . . ?
C3 C9 C10 C11 179.20(16) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C12 C13 C14 0.8(3) . . . . ?
C12 C13 C14 C9 -0.4(3) . . . . ?
C10 C9 C14 C13 -0.4(3) . . . . ?
C3 C9 C14 C13 -178.70(16) . . . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 28.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.439
_refine_diff_density_min -0.264
_refine_diff_density_rms 0.058
# Attachment 'Ingo-Knepper-av_ikp194.cif'
#=============================================================================
data_av_ikp194
_database_code_depnum_ccdc_archive 'CCDC 834863'
#TrackingRef 'Ingo-Knepper-av_ikp194.cif'
_audit_author_name 'Villinger, A.'
_audit_creation_method SHELXL-97
#==============================================================================
# CHEMICAL DATA
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C21 H16 N2 O'
_chemical_formula_sum 'C21 H16 N2 O'
_chemical_formula_weight 312.36
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'
#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_Int_Tables_number 14
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 7.0872(2)
_cell_length_b 17.7874(5)
_cell_length_c 25.4096(6)
_cell_angle_alpha 90.00
_cell_angle_beta 91.4850(10)
_cell_angle_gamma 90.00
_cell_volume 3202.13(15)
_cell_formula_units_Z 8
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 8459
_cell_measurement_theta_min 4.853
_cell_measurement_theta_max 59.674
_exptl_crystal_description needle
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.82
_exptl_crystal_size_mid 0.21
_exptl_crystal_size_min 0.10
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.296
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1312
_exptl_absorpt_coefficient_mu 0.081
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9367
_exptl_absorpt_correction_T_max 0.9920
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)'
#==============================================================================
# EXPERIMENTAL DATA
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method 'phi and psi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 32931
_diffrn_reflns_av_R_equivalents 0.0380
_diffrn_reflns_av_sigmaI/netI 0.0553
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 4
_diffrn_reflns_limit_k_min -24
_diffrn_reflns_limit_k_max 23
_diffrn_reflns_limit_l_min -35
_diffrn_reflns_limit_l_max 35
_diffrn_reflns_theta_min 2.29
_diffrn_reflns_theta_max 30.00
_reflns_number_total 9203
_reflns_number_gt 6105
_reflns_threshold_expression >2\s(I)
_computing_data_collection 'Bruker Apex v2.0-2'
_computing_cell_refinement 'Bruker Apex v2.0-2'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material SHELXL-97
#==============================================================================
# REFINEMENT DATA
_refine_special_details
;
All H atoms were positioned geometrically and refined using a
riding model , with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups),
1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with U~iso~(H) =
1.5 times U~eq~(C) (methyl groups) or with U~iso~(H) = 1.2 times
U~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles
of all methyl groups were allowed to refine.
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+0.5689P] 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 9203
_refine_ls_number_parameters 433
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0951
_refine_ls_R_factor_gt 0.0546
_refine_ls_wR_factor_ref 0.1237
_refine_ls_wR_factor_gt 0.1094
_refine_ls_goodness_of_fit_ref 1.031
_refine_ls_restrained_S_all 1.031
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
#==============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.51129(17) 0.75353(6) 0.49805(4) 0.0331(3) Uani 1 1 d . . .
N1 N 0.44141(18) 0.76632(6) 0.33692(4) 0.0248(3) Uani 1 1 d . . .
N2 N 0.38103(19) 0.89457(6) 0.34022(4) 0.0295(3) Uani 1 1 d . . .
C1 C 0.4937(2) 0.75744(8) 0.44925(5) 0.0250(3) Uani 1 1 d . . .
C2 C 0.5160(2) 0.69481(8) 0.41459(5) 0.0267(3) Uani 1 1 d . . .
H2 H 0.5518 0.6477 0.4293 0.032 Uiso 1 1 calc R . .
C3 C 0.4883(2) 0.69975(8) 0.36145(5) 0.0250(3) Uani 1 1 d . . .
C4 C 0.4234(2) 0.83110(7) 0.36697(5) 0.0235(3) Uani 1 1 d . . .
C5 C 0.4470(2) 0.82821(8) 0.42206(5) 0.0241(3) Uani 1 1 d . . .
C6 C 0.3579(2) 0.95662(8) 0.36846(6) 0.0332(4) Uani 1 1 d . . .
H6 H 0.3287 1.0018 0.3500 0.040 Uiso 1 1 calc R . .
C7 C 0.3736(2) 0.96007(8) 0.42307(6) 0.0336(4) Uani 1 1 d . . .
H7 H 0.3532 1.0059 0.4413 0.040 Uiso 1 1 calc R . .
C8 C 0.4193(2) 0.89526(8) 0.44986(5) 0.0293(3) Uani 1 1 d . . .
H8 H 0.4321 0.8958 0.4872 0.035 Uiso 1 1 calc R . .
C9 C 0.5087(3) 0.63086(8) 0.32838(5) 0.0297(3) Uani 1 1 d . . .
C10 C 0.3547(3) 0.58264(9) 0.32143(6) 0.0426(5) Uani 1 1 d . . .
H10 H 0.2366 0.5950 0.3361 0.051 Uiso 1 1 calc R . .
C11 C 0.3748(4) 0.51649(10) 0.29298(6) 0.0568(6) Uani 1 1 d . . .
H11 H 0.2704 0.4835 0.2882 0.068 Uiso 1 1 calc R . .
C12 C 0.5459(4) 0.49863(9) 0.27170(6) 0.0558(6) Uani 1 1 d . . .
H12 H 0.5593 0.4534 0.2523 0.067 Uiso 1 1 calc R . .
C13 C 0.6974(3) 0.54621(10) 0.27859(7) 0.0513(5) Uani 1 1 d . . .
H13 H 0.8150 0.5336 0.2638 0.062 Uiso 1 1 calc R . .
C14 C 0.6803(3) 0.61267(9) 0.30694(6) 0.0393(4) Uani 1 1 d . . .
H14 H 0.7855 0.6453 0.3115 0.047 Uiso 1 1 calc R . .
C15 C 0.3825(2) 0.76851(8) 0.28087(5) 0.0271(3) Uani 1 1 d . . .
H15A H 0.2752 0.8038 0.2767 0.033 Uiso 1 1 calc R . .
H15B H 0.3365 0.7180 0.2704 0.033 Uiso 1 1 calc R . .
C16 C 0.5346(2) 0.79181(7) 0.24370(5) 0.0236(3) Uani 1 1 d . . .
C17 C 0.4839(2) 0.80454(8) 0.19099(5) 0.0285(3) Uani 1 1 d . . .
H17 H 0.3560 0.7989 0.1795 0.034 Uiso 1 1 calc R . .
C18 C 0.6187(3) 0.82532(8) 0.15528(5) 0.0333(4) Uani 1 1 d . . .
H18 H 0.5828 0.8335 0.1195 0.040 Uiso 1 1 calc R . .
C19 C 0.8053(3) 0.83419(8) 0.17143(6) 0.0352(4) Uani 1 1 d . . .
H19 H 0.8975 0.8488 0.1470 0.042 Uiso 1 1 calc R . .
C20 C 0.8560(3) 0.82153(9) 0.22360(6) 0.0357(4) Uani 1 1 d . . .
H20 H 0.9839 0.8274 0.2350 0.043 Uiso 1 1 calc R . .
C21 C 0.7215(2) 0.80028(8) 0.25949(5) 0.0304(3) Uani 1 1 d . . .
H21 H 0.7582 0.7915 0.2952 0.037 Uiso 1 1 calc R . .
O2 O 0.02820(16) 0.73450(6) 0.34986(3) 0.0324(3) Uani 1 1 d . . .
N3 N -0.05940(18) 0.77767(6) 0.50668(4) 0.0229(3) Uani 1 1 d . . .
N4 N -0.12454(19) 0.90354(6) 0.48968(4) 0.0273(3) Uani 1 1 d . . .
C22 C 0.0041(2) 0.74765(7) 0.39735(5) 0.0240(3) Uani 1 1 d . . .
C23 C 0.0227(2) 0.69228(8) 0.43801(5) 0.0257(3) Uani 1 1 d . . .
H23 H 0.0595 0.6428 0.4286 0.031 Uiso 1 1 calc R . .
C24 C -0.0099(2) 0.70726(7) 0.48959(5) 0.0230(3) Uani 1 1 d . . .
C25 C -0.0770(2) 0.83585(7) 0.47016(5) 0.0212(3) Uani 1 1 d . . .
C26 C -0.0475(2) 0.82248(7) 0.41651(5) 0.0221(3) Uani 1 1 d . . .
C27 C -0.1446(2) 0.95938(8) 0.45530(6) 0.0308(3) Uani 1 1 d . . .
H27 H -0.1783 1.0074 0.4685 0.037 Uiso 1 1 calc R . .
C28 C -0.1198(2) 0.95263(8) 0.40129(6) 0.0310(3) Uani 1 1 d . . .
H28 H -0.1368 0.9946 0.3785 0.037 Uiso 1 1 calc R . .
C29 C -0.0702(2) 0.88359(8) 0.38207(5) 0.0273(3) Uani 1 1 d . . .
H29 H -0.0512 0.8772 0.3455 0.033 Uiso 1 1 calc R . .
C30 C 0.0089(2) 0.64414(7) 0.52843(5) 0.0258(3) Uani 1 1 d . . .
C31 C 0.1798(3) 0.63089(8) 0.55491(6) 0.0350(4) Uani 1 1 d . . .
H31 H 0.2827 0.6644 0.5508 0.042 Uiso 1 1 calc R . .
C32 C 0.1992(3) 0.56810(9) 0.58750(6) 0.0419(4) Uani 1 1 d . . .
H32 H 0.3157 0.5590 0.6057 0.050 Uiso 1 1 calc R . .
C33 C 0.0501(3) 0.51917(9) 0.59343(6) 0.0401(4) Uani 1 1 d . . .
H33 H 0.0639 0.4766 0.6158 0.048 Uiso 1 1 calc R . .
C34 C -0.1184(3) 0.53210(9) 0.56699(6) 0.0405(4) Uani 1 1 d . . .
H34 H -0.2205 0.4981 0.5709 0.049 Uiso 1 1 calc R . .
C35 C -0.1400(3) 0.59449(8) 0.53466(6) 0.0339(4) Uani 1 1 d . . .
H35 H -0.2572 0.6033 0.5167 0.041 Uiso 1 1 calc R . .
C36 C -0.1175(2) 0.79103(8) 0.56107(5) 0.0253(3) Uani 1 1 d . . .
H36A H -0.1616 0.7429 0.5759 0.030 Uiso 1 1 calc R . .
H36B H -0.2260 0.8261 0.5602 0.030 Uiso 1 1 calc R . .
C37 C 0.0341(2) 0.82286(7) 0.59747(5) 0.0239(3) Uani 1 1 d . . .
C38 C -0.0159(2) 0.84339(8) 0.64844(5) 0.0305(3) Uani 1 1 d . . .
H38 H -0.1436 0.8393 0.6585 0.037 Uiso 1 1 calc R . .
C39 C 0.1194(3) 0.86967(8) 0.68429(5) 0.0353(4) Uani 1 1 d . . .
H39 H 0.0839 0.8830 0.7189 0.042 Uiso 1 1 calc R . .
C40 C 0.3053(3) 0.87666(8) 0.67005(6) 0.0355(4) Uani 1 1 d . . .
H40 H 0.3977 0.8948 0.6946 0.043 Uiso 1 1 calc R . .
C41 C 0.3556(2) 0.85689(8) 0.61956(6) 0.0326(3) Uani 1 1 d . . .
H41 H 0.4831 0.8619 0.6095 0.039 Uiso 1 1 calc R . .
C42 C 0.2210(2) 0.82982(8) 0.58359(5) 0.0273(3) Uani 1 1 d . . .
H42 H 0.2575 0.8160 0.5492 0.033 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
O1 0.0351(7) 0.0445(6) 0.0195(4) -0.0004(4) -0.0002(5) -0.0052(5)
N1 0.0289(7) 0.0258(6) 0.0195(5) 0.0007(4) -0.0006(5) -0.0024(5)
N2 0.0316(8) 0.0277(6) 0.0293(6) 0.0028(5) 0.0017(6) -0.0023(6)
C1 0.0189(8) 0.0333(7) 0.0229(6) 0.0009(5) 0.0019(6) -0.0059(6)
C2 0.0275(9) 0.0284(7) 0.0242(6) 0.0029(5) -0.0003(6) -0.0027(6)
C3 0.0258(8) 0.0266(7) 0.0225(6) 0.0008(5) 0.0014(6) -0.0033(6)
C4 0.0193(7) 0.0267(6) 0.0246(6) 0.0000(5) 0.0034(6) -0.0030(6)
C5 0.0175(7) 0.0315(7) 0.0234(6) -0.0023(5) 0.0029(6) -0.0059(6)
C6 0.0323(10) 0.0278(7) 0.0395(8) 0.0017(6) 0.0027(7) -0.0027(7)
C7 0.0317(10) 0.0295(7) 0.0399(8) -0.0071(6) 0.0066(7) -0.0050(7)
C8 0.0246(8) 0.0356(8) 0.0278(7) -0.0056(6) 0.0051(6) -0.0083(7)
C9 0.0435(10) 0.0248(7) 0.0207(6) 0.0024(5) -0.0035(7) -0.0024(7)
C10 0.0616(13) 0.0360(8) 0.0304(7) 0.0004(6) 0.0035(8) -0.0174(9)
C11 0.103(2) 0.0318(9) 0.0352(8) 0.0012(7) -0.0026(11) -0.0278(11)
C12 0.114(2) 0.0239(8) 0.0290(8) -0.0001(6) -0.0036(11) 0.0061(10)
C13 0.0779(17) 0.0374(9) 0.0384(9) -0.0052(7) -0.0002(10) 0.0191(10)
C14 0.0493(12) 0.0328(8) 0.0359(8) -0.0038(6) -0.0006(8) 0.0060(8)
C15 0.0321(9) 0.0288(7) 0.0200(6) 0.0009(5) -0.0046(6) -0.0022(6)
C16 0.0297(9) 0.0196(6) 0.0214(6) -0.0016(5) -0.0004(6) 0.0014(6)
C17 0.0333(9) 0.0284(7) 0.0235(6) -0.0011(5) -0.0023(7) 0.0031(7)
C18 0.0438(11) 0.0347(8) 0.0215(6) 0.0006(6) 0.0017(7) 0.0054(8)
C19 0.0391(10) 0.0361(8) 0.0308(7) -0.0012(6) 0.0107(8) 0.0015(8)
C20 0.0287(9) 0.0433(9) 0.0352(8) -0.0033(7) 0.0010(7) 0.0028(7)
C21 0.0325(9) 0.0345(7) 0.0241(6) -0.0003(6) -0.0027(7) 0.0016(7)
O2 0.0371(7) 0.0393(6) 0.0208(4) -0.0025(4) 0.0014(5) -0.0013(5)
N3 0.0247(7) 0.0251(5) 0.0189(5) 0.0006(4) 0.0013(5) -0.0024(5)
N4 0.0265(7) 0.0256(6) 0.0298(6) -0.0020(5) -0.0004(5) -0.0013(5)
C22 0.0203(8) 0.0288(7) 0.0229(6) -0.0017(5) -0.0008(6) -0.0032(6)
C23 0.0277(8) 0.0242(6) 0.0254(6) -0.0015(5) 0.0012(6) -0.0003(6)
C24 0.0221(8) 0.0230(6) 0.0240(6) 0.0013(5) -0.0006(6) -0.0032(6)
C25 0.0171(7) 0.0235(6) 0.0230(6) 0.0005(5) -0.0007(6) -0.0030(6)
C26 0.0169(7) 0.0261(6) 0.0232(6) 0.0019(5) -0.0001(6) -0.0038(6)
C27 0.0275(9) 0.0233(7) 0.0414(8) 0.0007(6) 0.0003(7) -0.0002(6)
C28 0.0282(9) 0.0275(7) 0.0371(8) 0.0092(6) -0.0022(7) -0.0024(6)
C29 0.0232(8) 0.0329(7) 0.0257(6) 0.0045(5) -0.0007(6) -0.0051(6)
C30 0.0325(9) 0.0239(6) 0.0209(6) 0.0007(5) -0.0004(6) -0.0012(6)
C31 0.0345(10) 0.0304(7) 0.0398(8) 0.0069(6) -0.0056(8) -0.0040(7)
C32 0.0454(12) 0.0366(9) 0.0431(9) 0.0085(7) -0.0122(9) 0.0028(8)
C33 0.0602(13) 0.0271(7) 0.0327(7) 0.0074(6) -0.0056(9) -0.0017(8)
C34 0.0523(12) 0.0320(8) 0.0371(8) 0.0074(6) -0.0023(9) -0.0140(8)
C35 0.0351(10) 0.0360(8) 0.0303(7) 0.0060(6) -0.0047(7) -0.0071(7)
C36 0.0251(8) 0.0296(7) 0.0213(6) 0.0001(5) 0.0053(6) -0.0028(6)
C37 0.0295(9) 0.0212(6) 0.0210(6) 0.0022(5) 0.0010(6) 0.0001(6)
C38 0.0362(10) 0.0302(7) 0.0253(6) -0.0021(5) 0.0054(7) 0.0001(7)
C39 0.0500(12) 0.0327(8) 0.0232(6) -0.0038(6) -0.0012(7) 0.0024(8)
C40 0.0435(11) 0.0300(7) 0.0324(7) -0.0002(6) -0.0110(8) -0.0002(7)
C41 0.0292(9) 0.0312(7) 0.0371(7) 0.0016(6) -0.0032(7) -0.0010(7)
C42 0.0309(9) 0.0264(7) 0.0247(6) 0.0007(5) 0.0025(6) -0.0001(6)
#==============================================================================
# MOLECULAR GEOMETRY
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2449(15) . ?
N1 C3 1.3750(17) . ?
N1 C4 1.3900(17) . ?
N1 C15 1.4743(16) . ?
N2 C6 1.3289(18) . ?
N2 C4 1.3476(17) . ?
C1 C2 1.4315(19) . ?
C1 C5 1.4695(19) . ?
C2 C3 1.3623(17) . ?
C2 H2 0.9500 . ?
C3 C9 1.4949(19) . ?
C4 C5 1.4066(17) . ?
C5 C8 1.4027(19) . ?
C6 C7 1.391(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.373(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C14 1.384(2) . ?
C9 C10 1.396(2) . ?
C10 C11 1.390(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.509(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C21 1.383(2) . ?
C16 C17 1.3962(18) . ?
C17 C18 1.385(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.389(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
O2 C22 1.2453(15) . ?
N3 C24 1.3741(17) . ?
N3 C25 1.3934(16) . ?
N3 C36 1.4716(16) . ?
N4 C27 1.3281(17) . ?
N4 C25 1.3484(17) . ?
C22 C23 1.4310(18) . ?
C22 C26 1.4667(18) . ?
C23 C24 1.3629(18) . ?
C23 H23 0.9500 . ?
C24 C30 1.4987(18) . ?
C25 C26 1.4050(17) . ?
C26 C29 1.4022(18) . ?
C27 C28 1.393(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.371(2) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 C35 1.388(2) . ?
C30 C31 1.390(2) . ?
C31 C32 1.395(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.380(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.374(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.387(2) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 C37 1.509(2) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C42 1.385(2) . ?
C37 C38 1.3998(18) . ?
C38 C39 1.386(2) . ?
C38 H38 0.9500 . ?
C39 C40 1.381(3) . ?
C39 H39 0.9500 . ?
C40 C41 1.386(2) . ?
C40 H40 0.9500 . ?
C41 C42 1.390(2) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
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
C3 N1 C4 119.32(11) . . ?
C3 N1 C15 121.31(11) . . ?
C4 N1 C15 118.75(11) . . ?
C6 N2 C4 116.90(12) . . ?
O1 C1 C2 124.02(13) . . ?
O1 C1 C5 122.12(12) . . ?
C2 C1 C5 113.86(11) . . ?
C3 C2 C1 122.98(13) . . ?
C3 C2 H2 118.5 . . ?
C1 C2 H2 118.5 . . ?
C2 C3 N1 122.12(12) . . ?
C2 C3 C9 119.40(12) . . ?
N1 C3 C9 118.48(11) . . ?
N2 C4 N1 116.10(11) . . ?
N2 C4 C5 123.50(12) . . ?
N1 C4 C5 120.40(12) . . ?
C8 C5 C4 117.09(13) . . ?
C8 C5 C1 121.63(12) . . ?
C4 C5 C1 121.26(12) . . ?
N2 C6 C7 124.60(14) . . ?
N2 C6 H6 117.7 . . ?
C7 C6 H6 117.7 . . ?
C8 C7 C6 117.98(13) . . ?
C8 C7 H7 121.0 . . ?
C6 C7 H7 121.0 . . ?
C7 C8 C5 119.91(13) . . ?
C7 C8 H8 120.0 . . ?
C5 C8 H8 120.0 . . ?
C14 C9 C10 119.93(15) . . ?
C14 C9 C3 120.76(14) . . ?
C10 C9 C3 119.23(16) . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C12 C11 C10 120.19(19) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 120.02(16) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.7(2) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C9 C14 C13 119.45(18) . . ?
C9 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
N1 C15 C16 115.03(13) . . ?
N1 C15 H15A 108.5 . . ?
C16 C15 H15A 108.5 . . ?
N1 C15 H15B 108.5 . . ?
C16 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
C21 C16 C17 118.79(14) . . ?
C21 C16 C15 122.86(12) . . ?
C17 C16 C15 118.34(14) . . ?
C18 C17 C16 120.46(15) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 120.45(14) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 119.23(16) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C19 C20 C21 120.54(16) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C16 C21 C20 120.53(13) . . ?
C16 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C24 N3 C25 119.05(10) . . ?
C24 N3 C36 121.60(11) . . ?
C25 N3 C36 118.89(11) . . ?
C27 N4 C25 116.70(12) . . ?
O2 C22 C23 123.91(12) . . ?
O2 C22 C26 122.25(12) . . ?
C23 C22 C26 113.83(11) . . ?
C24 C23 C22 123.02(12) . . ?
C24 C23 H23 118.5 . . ?
C22 C23 H23 118.5 . . ?
C23 C24 N3 122.22(12) . . ?
C23 C24 C30 118.19(12) . . ?
N3 C24 C30 119.58(11) . . ?
N4 C25 N3 115.92(11) . . ?
N4 C25 C26 123.58(12) . . ?
N3 C25 C26 120.50(11) . . ?
C29 C26 C25 117.17(12) . . ?
C29 C26 C22 121.47(12) . . ?
C25 C26 C22 121.35(11) . . ?
N4 C27 C28 124.72(13) . . ?
N4 C27 H27 117.6 . . ?
C28 C27 H27 117.6 . . ?
C29 C28 C27 117.92(13) . . ?
C29 C28 H28 121.0 . . ?
C27 C28 H28 121.0 . . ?
C28 C29 C26 119.91(13) . . ?
C28 C29 H29 120.0 . . ?
C26 C29 H29 120.0 . . ?
C35 C30 C31 119.49(13) . . ?
C35 C30 C24 119.78(14) . . ?
C31 C30 C24 120.48(14) . . ?
C30 C31 C32 119.61(16) . . ?
C30 C31 H31 120.2 . . ?
C32 C31 H31 120.2 . . ?
C33 C32 C31 120.38(17) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C34 C33 C32 119.94(14) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C33 C34 C35 120.32(16) . . ?
C33 C34 H34 119.8 . . ?
C35 C34 H34 119.8 . . ?
C34 C35 C30 120.26(16) . . ?
C34 C35 H35 119.9 . . ?
C30 C35 H35 119.9 . . ?
N3 C36 C37 115.08(12) . . ?
N3 C36 H36A 108.5 . . ?
C37 C36 H36A 108.5 . . ?
N3 C36 H36B 108.5 . . ?
C37 C36 H36B 108.5 . . ?
H36A C36 H36B 107.5 . . ?
C42 C37 C38 118.59(14) . . ?
C42 C37 C36 123.21(12) . . ?
C38 C37 C36 118.15(14) . . ?
C39 C38 C37 120.58(16) . . ?
C39 C38 H38 119.7 . . ?
C37 C38 H38 119.7 . . ?
C40 C39 C38 120.43(14) . . ?
C40 C39 H39 119.8 . . ?
C38 C39 H39 119.8 . . ?
C39 C40 C41 119.33(15) . . ?
C39 C40 H40 120.3 . . ?
C41 C40 H40 120.3 . . ?
C40 C41 C42 120.53(16) . . ?
C40 C41 H41 119.7 . . ?
C42 C41 H41 119.7 . . ?
C37 C42 C41 120.54(13) . . ?
C37 C42 H42 119.7 . . ?
C41 C42 H42 119.7 . . ?
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 C1 C2 C3 177.15(15) . . . . ?
C5 C1 C2 C3 -2.7(2) . . . . ?
C1 C2 C3 N1 1.8(2) . . . . ?
C1 C2 C3 C9 -178.02(15) . . . . ?
C4 N1 C3 C2 0.7(2) . . . . ?
C15 N1 C3 C2 -170.14(15) . . . . ?
C4 N1 C3 C9 -179.47(14) . . . . ?
C15 N1 C3 C9 9.7(2) . . . . ?
C6 N2 C4 N1 178.12(14) . . . . ?
C6 N2 C4 C5 -1.2(2) . . . . ?
C3 N1 C4 N2 178.66(13) . . . . ?
C15 N1 C4 N2 -10.2(2) . . . . ?
C3 N1 C4 C5 -2.0(2) . . . . ?
C15 N1 C4 C5 169.10(13) . . . . ?
N2 C4 C5 C8 1.8(2) . . . . ?
N1 C4 C5 C8 -177.51(14) . . . . ?
N2 C4 C5 C1 -179.85(14) . . . . ?
N1 C4 C5 C1 0.9(2) . . . . ?
O1 C1 C5 C8 -0.2(2) . . . . ?
C2 C1 C5 C8 179.72(14) . . . . ?
O1 C1 C5 C4 -178.48(14) . . . . ?
C2 C1 C5 C4 1.4(2) . . . . ?
C4 N2 C6 C7 -0.4(2) . . . . ?
N2 C6 C7 C8 1.2(3) . . . . ?
C6 C7 C8 C5 -0.5(2) . . . . ?
C4 C5 C8 C7 -0.8(2) . . . . ?
C1 C5 C8 C7 -179.21(14) . . . . ?
C2 C3 C9 C14 -91.42(18) . . . . ?
N1 C3 C9 C14 88.77(18) . . . . ?
C2 C3 C9 C10 85.34(19) . . . . ?
N1 C3 C9 C10 -94.47(17) . . . . ?
C14 C9 C10 C11 0.0(2) . . . . ?
C3 C9 C10 C11 -176.74(14) . . . . ?
C9 C10 C11 C12 -0.1(2) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C10 C9 C14 C13 0.0(2) . . . . ?
C3 C9 C14 C13 176.72(13) . . . . ?
C12 C13 C14 C9 0.0(2) . . . . ?
C3 N1 C15 C16 -99.82(16) . . . . ?
C4 N1 C15 C16 89.26(16) . . . . ?
N1 C15 C16 C21 8.75(19) . . . . ?
N1 C15 C16 C17 -171.93(12) . . . . ?
C21 C16 C17 C18 0.0(2) . . . . ?
C15 C16 C17 C18 -179.39(13) . . . . ?
C16 C17 C18 C19 -0.4(2) . . . . ?
C17 C18 C19 C20 0.5(2) . . . . ?
C18 C19 C20 C21 -0.1(2) . . . . ?
C17 C16 C21 C20 0.4(2) . . . . ?
C15 C16 C21 C20 179.72(13) . . . . ?
C19 C20 C21 C16 -0.3(2) . . . . ?
O2 C22 C23 C24 -177.94(15) . . . . ?
C26 C22 C23 C24 1.8(2) . . . . ?
C22 C23 C24 N3 -1.5(2) . . . . ?
C22 C23 C24 C30 178.32(14) . . . . ?
C25 N3 C24 C23 0.0(2) . . . . ?
C36 N3 C24 C23 172.14(14) . . . . ?
C25 N3 C24 C30 -179.82(13) . . . . ?
C36 N3 C24 C30 -7.7(2) . . . . ?
C27 N4 C25 N3 -179.04(13) . . . . ?
C27 N4 C25 C26 0.4(2) . . . . ?
C24 N3 C25 N4 -179.54(13) . . . . ?
C36 N3 C25 N4 8.14(19) . . . . ?
C24 N3 C25 C26 1.0(2) . . . . ?
C36 N3 C25 C26 -171.34(13) . . . . ?
N4 C25 C26 C29 -0.3(2) . . . . ?
N3 C25 C26 C29 179.17(13) . . . . ?
N4 C25 C26 C22 -179.99(14) . . . . ?
N3 C25 C26 C22 -0.5(2) . . . . ?
O2 C22 C26 C29 -0.7(2) . . . . ?
C23 C22 C26 C29 179.49(14) . . . . ?
O2 C22 C26 C25 178.98(14) . . . . ?
C23 C22 C26 C25 -0.8(2) . . . . ?
C25 N4 C27 C28 -0.1(2) . . . . ?
N4 C27 C28 C29 -0.3(2) . . . . ?
C27 C28 C29 C26 0.5(2) . . . . ?
C25 C26 C29 C28 -0.2(2) . . . . ?
C22 C26 C29 C28 179.51(14) . . . . ?
C23 C24 C30 C35 -82.41(19) . . . . ?
N3 C24 C30 C35 97.44(17) . . . . ?
C23 C24 C30 C31 91.89(17) . . . . ?
N3 C24 C30 C31 -88.26(18) . . . . ?
C35 C30 C31 C32 -0.2(2) . . . . ?
C24 C30 C31 C32 -174.55(14) . . . . ?
C30 C31 C32 C33 0.2(2) . . . . ?
C31 C32 C33 C34 0.2(3) . . . . ?
C32 C33 C34 C35 -0.5(3) . . . . ?
C33 C34 C35 C30 0.5(2) . . . . ?
C31 C30 C35 C34 -0.1(2) . . . . ?
C24 C30 C35 C34 174.28(14) . . . . ?
C24 N3 C36 C37 99.71(15) . . . . ?
C25 N3 C36 C37 -88.17(16) . . . . ?
N3 C36 C37 C42 -8.44(19) . . . . ?
N3 C36 C37 C38 174.27(12) . . . . ?
C42 C37 C38 C39 -0.4(2) . . . . ?
C36 C37 C38 C39 177.02(13) . . . . ?
C37 C38 C39 C40 0.6(2) . . . . ?
C38 C39 C40 C41 -0.2(2) . . . . ?
C39 C40 C41 C42 -0.4(2) . . . . ?
C38 C37 C42 C41 -0.2(2) . . . . ?
C36 C37 C42 C41 -177.50(13) . . . . ?
C40 C41 C42 C37 0.6(2) . . . . ?
_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full 30.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max 0.229
_refine_diff_density_min -0.228
_refine_diff_density_rms 0.047
# Attachment 'Ingo-Knepper-is_ikp207.cif'
#=============================================================================
data_is_ikp207
_database_code_depnum_ccdc_archive 'CCDC 834864'
#TrackingRef 'Ingo-Knepper-is_ikp207.cif'
_audit_author_name 'Villinger, A.'
_audit_creation_method SHELXL-97
#==============================================================================
# CHEMICAL DATA
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C17 H22 N2 O'
_chemical_formula_sum 'C17 H22 N2 O'
_chemical_formula_weight 270.37
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'
#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'C 2/m'
_symmetry_space_group_name_Hall '-C 2y'
_symmetry_Int_Tables_number 12
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
_cell_length_a 18.4597(18)
_cell_length_b 7.1537(7)
_cell_length_c 11.0986(12)
_cell_angle_alpha 90.00
_cell_angle_beta 98.355(6)
_cell_angle_gamma 90.00
_cell_volume 1450.1(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 6329
_cell_measurement_theta_min 5.371
_cell_measurement_theta_max 61.168
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.67
_exptl_crystal_size_mid 0.28
_exptl_crystal_size_min 0.21
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.238
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 584
_exptl_absorpt_coefficient_mu 0.077
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9499
_exptl_absorpt_correction_T_max 0.9839
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)'
#==============================================================================
# EXPERIMENTAL DATA
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method 'phi and psi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 15903
_diffrn_reflns_av_R_equivalents 0.0282
_diffrn_reflns_av_sigmaI/netI 0.0167
_diffrn_reflns_limit_h_min -25
_diffrn_reflns_limit_h_max 25
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_theta_min 2.23
_diffrn_reflns_theta_max 30.00
_reflns_number_total 2273
_reflns_number_gt 1920
_reflns_threshold_expression >2\s(I)
_computing_data_collection 'Bruker Apex v2.0-2'
_computing_cell_refinement 'Bruker Apex v2.0-2'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material SHELXL-97
#==============================================================================
# REFINEMENT DATA
_refine_special_details
;
All H atoms were positioned geometrically and
refined using a riding model , with C---H = 0.98 (methyl groups), 0.99\%A
(methylene groups), 1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with
U~iso~(H) = 1.5 times U~eq~(C) (methyl groups) or with
U~iso~(H) = 1.2 times U~eq~(C) (methylene groups, aryl CH,
methine groups). Torsion angles of all methyl groups were allowed to refine.
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0830P)^2^+0.2720P] 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 2273
_refine_ls_number_parameters 116
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0492
_refine_ls_R_factor_gt 0.0419
_refine_ls_wR_factor_ref 0.1332
_refine_ls_wR_factor_gt 0.1267
_refine_ls_goodness_of_fit_ref 1.099
_refine_ls_restrained_S_all 1.099
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
#==============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
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 0.24608(5) 0.0000 0.65617(8) 0.0199(2) Uani 1 2 d S . .
N2 N 0.34503(5) 0.0000 0.81289(9) 0.0279(2) Uani 1 2 d S . .
O1 O 0.38584(5) 0.0000 0.39795(8) 0.0357(2) Uani 1 2 d S . .
C1 C 0.21990(6) 0.0000 0.53344(9) 0.0185(2) Uani 1 2 d S . .
C2 C 0.26576(6) 0.0000 0.44715(10) 0.0217(2) Uani 1 2 d S . .
H2 H 0.2446 0.0000 0.3638 0.026 Uiso 1 2 calc SR . .
C3 C 0.34341(6) 0.0000 0.47557(10) 0.0238(2) Uani 1 2 d S . .
C4 C 0.37034(6) 0.0000 0.60590(10) 0.0220(2) Uani 1 2 d S . .
C5 C 0.44525(6) 0.0000 0.64846(11) 0.0276(3) Uani 1 2 d S . .
H5 H 0.4795 0.0000 0.5923 0.033 Uiso 1 2 calc SR . .
C6 C 0.46964(6) 0.0000 0.77121(12) 0.0309(3) Uani 1 2 d S . .
H6 H 0.5204 0.0000 0.8019 0.037 Uiso 1 2 calc SR . .
C7 C 0.41677(6) 0.0000 0.84901(11) 0.0319(3) Uani 1 2 d S . .
H7 H 0.4333 0.0000 0.9342 0.038 Uiso 1 2 calc SR . .
C8 C 0.32148(6) 0.0000 0.69255(9) 0.0210(2) Uani 1 2 d S . .
C9 C 0.13804(6) 0.0000 0.49460(9) 0.0212(2) Uani 1 2 d S . .
H9A H 0.1174 0.1115 0.5300 0.025 Uiso 0.50 1 calc PR . .
H9B H 0.1174 -0.1115 0.5300 0.025 Uiso 0.50 1 calc PR . .
C10 C 0.11243(6) 0.0000 0.35774(10) 0.0260(2) Uani 1 2 d S . .
H10A H 0.1318 0.1120 0.3208 0.031 Uiso 0.50 1 calc PR . .
H10B H 0.1318 -0.1120 0.3208 0.031 Uiso 0.50 1 calc PR . .
C11 C 0.02914(7) 0.0000 0.33109(13) 0.0372(3) Uani 1 2 d S . .
H11A H 0.0137 0.0093 0.2430 0.056 Uiso 0.50 1 calc PR . .
H11B H 0.0099 0.1069 0.3717 0.056 Uiso 0.50 1 calc PR . .
H11C H 0.0102 -0.1162 0.3614 0.056 Uiso 0.50 1 calc PR . .
C12 C 0.19502(5) 0.0000 0.74929(9) 0.0203(2) Uani 1 2 d S . .
H12 H 0.1446 0.0000 0.7021 0.024 Uiso 1 2 calc SR . .
C13 C 0.20031(4) 0.17784(12) 0.82578(7) 0.0263(2) Uani 1 1 d . . .
H13A H 0.1932 0.2884 0.7717 0.032 Uiso 1 1 calc R . .
H13B H 0.2495 0.1866 0.8747 0.032 Uiso 1 1 calc R . .
C14 C 0.14189(5) 0.17520(14) 0.91022(8) 0.0321(2) Uani 1 1 d . . .
H14A H 0.1478 0.2868 0.9635 0.039 Uiso 1 1 calc R . .
H14B H 0.0928 0.1812 0.8608 0.039 Uiso 1 1 calc R . .
C15 C 0.14713(8) 0.0000 0.98865(11) 0.0370(3) Uani 1 2 d S . .
H15A H 0.1943 0.0000 1.0441 0.044 Uiso 1 2 calc SR . .
H15B H 0.1071 0.0000 1.0391 0.044 Uiso 1 2 calc SR . .
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 0.0179(4) 0.0257(4) 0.0167(4) 0.000 0.0043(3) 0.000
N2 0.0204(4) 0.0434(6) 0.0199(4) 0.000 0.0027(3) 0.000
O1 0.0276(4) 0.0574(6) 0.0249(4) 0.000 0.0131(3) 0.000
C1 0.0210(5) 0.0174(4) 0.0172(4) 0.000 0.0032(3) 0.000
C2 0.0239(5) 0.0236(5) 0.0183(5) 0.000 0.0053(4) 0.000
C3 0.0251(5) 0.0258(5) 0.0221(5) 0.000 0.0089(4) 0.000
C4 0.0201(5) 0.0249(5) 0.0219(5) 0.000 0.0063(4) 0.000
C5 0.0210(5) 0.0348(6) 0.0283(6) 0.000 0.0082(4) 0.000
C6 0.0183(5) 0.0436(7) 0.0304(6) 0.000 0.0026(4) 0.000
C7 0.0213(5) 0.0505(8) 0.0234(5) 0.000 0.0013(4) 0.000
C8 0.0187(5) 0.0253(5) 0.0195(5) 0.000 0.0043(4) 0.000
C9 0.0202(5) 0.0239(5) 0.0195(5) 0.000 0.0026(4) 0.000
C10 0.0263(5) 0.0305(6) 0.0206(5) 0.000 0.0009(4) 0.000
C11 0.0279(6) 0.0495(8) 0.0317(6) 0.000 -0.0045(5) 0.000
C12 0.0179(4) 0.0271(5) 0.0164(4) 0.000 0.0043(3) 0.000
C13 0.0289(4) 0.0263(4) 0.0244(4) -0.0016(3) 0.0065(3) 0.0024(3)
C14 0.0294(4) 0.0431(5) 0.0246(4) -0.0060(3) 0.0064(3) 0.0092(3)
C15 0.0368(7) 0.0544(8) 0.0220(5) 0.000 0.0115(5) 0.000
#==============================================================================
# MOLECULAR GEOMETRY
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.3777(13) . ?
N1 C8 1.3917(13) . ?
N1 C12 1.4965(12) . ?
N2 C7 1.3266(14) . ?
N2 C8 1.3432(14) . ?
O1 C3 1.2456(13) . ?
C1 C2 1.3673(14) . ?
C1 C9 1.5099(14) . ?
C2 C3 1.4224(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.4596(15) . ?
C4 C5 1.3947(15) . ?
C4 C8 1.4110(14) . ?
C5 C6 1.3714(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.3939(16) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C9 C10 1.5239(15) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5228(17) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.5247(10) . ?
C12 C13 1.5247(10) 6 ?
C12 H12 1.0000 . ?
C13 C14 1.5282(11) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5210(12) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C14 1.5210(12) 6 ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 118.64(9) . . ?
C1 N1 C12 121.14(8) . . ?
C8 N1 C12 120.22(8) . . ?
C7 N2 C8 117.72(10) . . ?
C2 C1 N1 121.91(10) . . ?
C2 C1 C9 119.73(9) . . ?
N1 C1 C9 118.36(9) . . ?
C1 C2 C3 123.46(10) . . ?
C1 C2 H2 118.3 . . ?
C3 C2 H2 118.3 . . ?
O1 C3 C2 124.15(11) . . ?
O1 C3 C4 121.84(10) . . ?
C2 C3 C4 114.01(9) . . ?
C5 C4 C8 118.02(10) . . ?
C5 C4 C3 120.92(9) . . ?
C8 C4 C3 121.07(10) . . ?
C6 C5 C4 120.18(10) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 117.20(11) . . ?
C5 C6 H6 121.4 . . ?
C7 C6 H6 121.4 . . ?
N2 C7 C6 124.81(11) . . ?
N2 C7 H7 117.6 . . ?
C6 C7 H7 117.6 . . ?
N2 C8 N1 117.01(9) . . ?
N2 C8 C4 122.08(10) . . ?
N1 C8 C4 120.91(9) . . ?
C1 C9 C10 115.93(9) . . ?
C1 C9 H9A 108.3 . . ?
C10 C9 H9A 108.3 . . ?
C1 C9 H9B 108.3 . . ?
C10 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
C11 C10 C9 110.60(10) . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C13 112.88(5) . . ?
N1 C12 C13 112.88(5) . 6 ?
C13 C12 C13 113.12(9) . 6 ?
N1 C12 H12 105.7 . . ?
C13 C12 H12 105.7 . . ?
C13 C12 H12 105.7 6 . ?
C12 C13 C14 109.72(7) . . ?
C12 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
C12 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C15 C14 C13 111.67(8) . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 C14 110.98(10) 6 . ?
C14 C15 H15A 109.4 6 . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 6 . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 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
C8 N1 C1 C2 0.0 . . . . ?
C12 N1 C1 C2 180.0 . . . . ?
C8 N1 C1 C9 180.0 . . . . ?
C12 N1 C1 C9 0.0 . . . . ?
N1 C1 C2 C3 0.0 . . . . ?
C9 C1 C2 C3 180.0 . . . . ?
C1 C2 C3 O1 180.0 . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
O1 C3 C4 C5 0.0 . . . . ?
C2 C3 C4 C5 180.0 . . . . ?
O1 C3 C4 C8 180.0 . . . . ?
C2 C3 C4 C8 0.0 . . . . ?
C8 C4 C5 C6 0.0 . . . . ?
C3 C4 C5 C6 180.0 . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C8 N2 C7 C6 0.0 . . . . ?
C5 C6 C7 N2 0.0 . . . . ?
C7 N2 C8 N1 180.0 . . . . ?
C7 N2 C8 C4 0.0 . . . . ?
C1 N1 C8 N2 180.0 . . . . ?
C12 N1 C8 N2 0.0 . . . . ?
C1 N1 C8 C4 0.0 . . . . ?
C12 N1 C8 C4 180.0 . . . . ?
C5 C4 C8 N2 0.0 . . . . ?
C3 C4 C8 N2 180.0 . . . . ?
C5 C4 C8 N1 180.0 . . . . ?
C3 C4 C8 N1 0.0 . . . . ?
C2 C1 C9 C10 0.0 . . . . ?
N1 C1 C9 C10 180.0 . . . . ?
C1 C9 C10 C11 180.0 . . . . ?
C1 N1 C12 C13 -115.08(6) . . . . ?
C8 N1 C12 C13 64.92(6) . . . . ?
C1 N1 C12 C13 115.08(6) . . . 6 ?
C8 N1 C12 C13 -64.92(6) . . . 6 ?
N1 C12 C13 C14 174.80(7) . . . . ?
C13 C12 C13 C14 -55.49(11) 6 . . . ?
C12 C13 C14 C15 55.15(10) . . . . ?
C13 C14 C15 C14 -56.32(13) . . . 6 ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full 30.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.370
_refine_diff_density_min -0.251
_refine_diff_density_rms 0.050
# Attachment 'Ingo-Knepper-is_ikp272.cif'
#=============================================================================
data_is_ikp272
_database_code_depnum_ccdc_archive 'CCDC 834865'
#TrackingRef 'Ingo-Knepper-is_ikp272.cif'
_audit_author_name 'Villinger, A.'
_audit_creation_method SHELXL-97
#==============================================================================
# CHEMICAL DATA
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C20 H19 Br N2 O'
_chemical_formula_sum 'C20 H19 Br N2 O'
_chemical_formula_weight 383.28
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/n'
_symmetry_space_group_name_Hall '-P 2yn'
_symmetry_Int_Tables_number 14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 9.2174(3)
_cell_length_b 19.7268(7)
_cell_length_c 10.0151(3)
_cell_angle_alpha 90.00
_cell_angle_beta 110.322(2)
_cell_angle_gamma 90.00
_cell_volume 1707.69(10)
_cell_formula_units_Z 4
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 5267
_cell_measurement_theta_min 4.804
_cell_measurement_theta_max 59.184
_exptl_crystal_description needle
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.95
_exptl_crystal_size_mid 0.14
_exptl_crystal_size_min 0.04
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.491
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 784
_exptl_absorpt_coefficient_mu 2.416
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.2074
_exptl_absorpt_correction_T_max 0.9096
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)'
#==============================================================================
# EXPERIMENTAL DATA
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method 'phi and psi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 20001
_diffrn_reflns_av_R_equivalents 0.0352
_diffrn_reflns_av_sigmaI/netI 0.0384
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -27
_diffrn_reflns_limit_k_max 27
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_theta_min 2.79
_diffrn_reflns_theta_max 30.00
_reflns_number_total 4968
_reflns_number_gt 3720
_reflns_threshold_expression >2\s(I)
_computing_data_collection 'Bruker Apex v2.0-2'
_computing_cell_refinement 'Bruker Apex v2.0-2'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material SHELXL-97
#==============================================================================
# REFINEMENT DATA
_refine_special_details
;
All H atoms were positioned geometrically and
refined using a riding model , with C---H = 0.98 (methyl groups), 0.99\%A
(methylene groups), 1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with
U~iso~(H) = 1.5 times U~eq~(C) (methyl groups) or with
U~iso~(H) = 1.2 times U~eq~(C) (methylene groups, aryl CH,
methine groups). Torsion angles of all methyl groups were allowed to refine.
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0367P)^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 4968
_refine_ls_number_parameters 217
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0556
_refine_ls_R_factor_gt 0.0335
_refine_ls_wR_factor_ref 0.0781
_refine_ls_wR_factor_gt 0.0724
_refine_ls_goodness_of_fit_ref 1.077
_refine_ls_restrained_S_all 1.077
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
#==============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
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
Br1 Br 0.18278(2) 0.017574(10) 0.28576(2) 0.03043(7) Uani 1 1 d . . .
N1 N 0.61331(16) 0.03922(7) 0.24764(14) 0.0182(3) Uani 1 1 d . . .
N2 N 0.82905(17) -0.03049(7) 0.29436(15) 0.0231(3) Uani 1 1 d . . .
O1 O 0.38214(15) -0.10787(7) 0.38824(13) 0.0311(3) Uani 1 1 d . . .
C1 C 0.46490(18) 0.05023(9) 0.24662(16) 0.0177(3) Uani 1 1 d . . .
C2 C 0.3867(2) 0.00146(9) 0.29222(17) 0.0202(3) Uani 1 1 d . . .
C3 C 0.45062(19) -0.06380(9) 0.34462(16) 0.0214(4) Uani 1 1 d . . .
C4 C 0.60585(19) -0.07374(9) 0.34033(16) 0.0196(3) Uani 1 1 d . . .
C5 C 0.68446(19) -0.02294(9) 0.29557(16) 0.0191(3) Uani 1 1 d . . .
C6 C 0.6824(2) -0.13580(9) 0.38269(17) 0.0245(4) Uani 1 1 d . . .
H6 H 0.6322 -0.1720 0.4118 0.029 Uiso 1 1 calc R . .
C7 C 0.8293(2) -0.14394(9) 0.38195(18) 0.0267(4) Uani 1 1 d . . .
H7 H 0.8831 -0.1855 0.4110 0.032 Uiso 1 1 calc R . .
C8 C 0.8980(2) -0.08969(10) 0.33743(18) 0.0266(4) Uani 1 1 d . . .
H8 H 1.0005 -0.0954 0.3379 0.032 Uiso 1 1 calc R . .
C9 C 0.39270(18) 0.11727(9) 0.19374(16) 0.0182(3) Uani 1 1 d . . .
C10 C 0.4134(2) 0.17095(9) 0.28805(18) 0.0243(4) Uani 1 1 d . . .
H10 H 0.4692 0.1644 0.3866 0.029 Uiso 1 1 calc R . .
C11 C 0.3525(2) 0.23423(10) 0.23818(19) 0.0296(4) Uani 1 1 d . . .
H11 H 0.3661 0.2708 0.3030 0.035 Uiso 1 1 calc R . .
C12 C 0.2722(2) 0.24433(10) 0.09458(19) 0.0290(4) Uani 1 1 d . . .
H12 H 0.2320 0.2878 0.0606 0.035 Uiso 1 1 calc R . .
C13 C 0.2509(2) 0.19076(10) 0.00131(19) 0.0292(4) Uani 1 1 d . . .
H13 H 0.1954 0.1975 -0.0972 0.035 Uiso 1 1 calc R . .
C14 C 0.3098(2) 0.12705(10) 0.04975(17) 0.0248(4) Uani 1 1 d . . .
H14 H 0.2935 0.0903 -0.0151 0.030 Uiso 1 1 calc R . .
C15 C 0.69361(19) 0.09335(9) 0.19522(16) 0.0200(3) Uani 1 1 d . . .
H15 H 0.6186 0.1319 0.1678 0.024 Uiso 1 1 calc R . .
C16 C 0.8369(2) 0.12210(9) 0.30881(17) 0.0242(4) Uani 1 1 d . . .
H16A H 0.9206 0.0878 0.3359 0.029 Uiso 1 1 calc R . .
H16B H 0.8129 0.1342 0.3948 0.029 Uiso 1 1 calc R . .
C17 C 0.8888(2) 0.18508(10) 0.2485(2) 0.0310(4) Uani 1 1 d . . .
H17A H 0.8090 0.2208 0.2315 0.037 Uiso 1 1 calc R . .
H17B H 0.9860 0.2026 0.3191 0.037 Uiso 1 1 calc R . .
C18 C 0.9151(2) 0.16946(10) 0.10974(19) 0.0307(4) Uani 1 1 d . . .
H18A H 0.9412 0.2119 0.0705 0.037 Uiso 1 1 calc R . .
H18B H 1.0041 0.1382 0.1294 0.037 Uiso 1 1 calc R . .
C19 C 0.7739(2) 0.13750(11) -0.00041(19) 0.0325(4) Uani 1 1 d . . .
H19A H 0.7988 0.1251 -0.0858 0.039 Uiso 1 1 calc R . .
H19B H 0.6883 0.1708 -0.0295 0.039 Uiso 1 1 calc R . .
C20 C 0.7222(2) 0.07430(10) 0.05895(17) 0.0275(4) Uani 1 1 d . . .
H20A H 0.6262 0.0560 -0.0118 0.033 Uiso 1 1 calc R . .
H20B H 0.8033 0.0389 0.0794 0.033 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
Br1 0.02329(10) 0.02870(12) 0.04389(12) 0.00376(9) 0.01748(8) 0.00007(8)
N1 0.0202(7) 0.0150(7) 0.0205(7) 0.0031(6) 0.0083(5) -0.0002(6)
N2 0.0218(7) 0.0197(8) 0.0280(8) 0.0034(6) 0.0089(6) 0.0012(6)
O1 0.0309(7) 0.0255(7) 0.0392(7) 0.0088(6) 0.0151(6) -0.0053(6)
C1 0.0186(8) 0.0177(9) 0.0163(7) -0.0007(6) 0.0055(6) 0.0002(7)
C2 0.0201(8) 0.0199(9) 0.0209(8) -0.0005(6) 0.0076(6) -0.0015(6)
C3 0.0237(9) 0.0201(9) 0.0203(8) 0.0010(7) 0.0074(7) -0.0042(7)
C4 0.0225(8) 0.0166(8) 0.0183(7) 0.0002(6) 0.0054(6) -0.0014(7)
C5 0.0222(8) 0.0180(8) 0.0160(7) 0.0006(6) 0.0052(6) 0.0018(7)
C6 0.0325(10) 0.0163(9) 0.0243(8) 0.0029(7) 0.0094(7) -0.0011(7)
C7 0.0310(10) 0.0168(9) 0.0298(9) 0.0033(7) 0.0073(8) 0.0051(8)
C8 0.0245(9) 0.0232(10) 0.0307(9) 0.0010(8) 0.0079(7) 0.0033(8)
C9 0.0179(8) 0.0171(8) 0.0216(8) 0.0022(6) 0.0095(6) -0.0002(6)
C10 0.0294(9) 0.0236(10) 0.0209(8) -0.0012(7) 0.0102(7) 0.0003(8)
C11 0.0364(11) 0.0199(10) 0.0369(10) -0.0059(8) 0.0185(8) 0.0021(8)
C12 0.0320(10) 0.0209(10) 0.0396(10) 0.0069(8) 0.0192(8) 0.0072(8)
C13 0.0322(10) 0.0283(11) 0.0265(9) 0.0072(8) 0.0093(8) 0.0061(8)
C14 0.0284(10) 0.0220(9) 0.0222(8) -0.0005(7) 0.0067(7) 0.0026(8)
C15 0.0227(9) 0.0154(8) 0.0230(8) 0.0048(7) 0.0094(7) 0.0001(7)
C16 0.0287(9) 0.0214(9) 0.0226(8) -0.0003(7) 0.0088(7) -0.0033(8)
C17 0.0322(11) 0.0220(10) 0.0367(10) 0.0002(8) 0.0094(8) -0.0075(8)
C18 0.0315(10) 0.0238(10) 0.0423(11) 0.0089(9) 0.0198(9) -0.0023(8)
C19 0.0420(12) 0.0320(12) 0.0285(9) 0.0057(8) 0.0185(9) -0.0037(9)
C20 0.0361(11) 0.0258(10) 0.0224(8) -0.0013(7) 0.0125(8) -0.0074(8)
#==============================================================================
# MOLECULAR GEOMETRY
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.8852(17) . ?
N1 C1 1.382(2) . ?
N1 C5 1.395(2) . ?
N1 C15 1.495(2) . ?
N2 C8 1.328(2) . ?
N2 C5 1.345(2) . ?
O1 C3 1.240(2) . ?
C1 C2 1.372(2) . ?
C1 C9 1.493(2) . ?
C2 C3 1.437(2) . ?
C3 C4 1.460(2) . ?
C4 C5 1.399(2) . ?
C4 C6 1.403(2) . ?
C6 C7 1.366(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.393(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.387(2) . ?
C9 C14 1.391(2) . ?
C10 C11 1.389(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.522(2) . ?
C15 C20 1.524(2) . ?
C15 H15 1.0000 . ?
C16 C17 1.529(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.523(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.520(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.527(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 119.13(14) . . ?
C1 N1 C15 119.66(14) . . ?
C5 N1 C15 121.20(13) . . ?
C8 N2 C5 117.26(15) . . ?
C2 C1 N1 121.37(16) . . ?
C2 C1 C9 121.23(15) . . ?
N1 C1 C9 117.41(14) . . ?
C1 C2 C3 123.62(16) . . ?
C1 C2 Br1 120.21(13) . . ?
C3 C2 Br1 116.17(12) . . ?
O1 C3 C2 124.24(16) . . ?
O1 C3 C4 122.71(17) . . ?
C2 C3 C4 113.04(15) . . ?
C5 C4 C6 117.39(16) . . ?
C5 C4 C3 122.37(16) . . ?
C6 C4 C3 120.23(16) . . ?
N2 C5 N1 116.30(15) . . ?
N2 C5 C4 123.28(15) . . ?
N1 C5 C4 120.41(15) . . ?
C7 C6 C4 119.75(17) . . ?
C7 C6 H6 120.1 . . ?
C4 C6 H6 120.1 . . ?
C6 C7 C8 118.23(17) . . ?
C6 C7 H7 120.9 . . ?
C8 C7 H7 120.9 . . ?
N2 C8 C7 124.07(18) . . ?
N2 C8 H8 118.0 . . ?
C7 C8 H8 118.0 . . ?
C10 C9 C14 119.74(16) . . ?
C10 C9 C1 119.72(14) . . ?
C14 C9 C1 120.50(15) . . ?
C9 C10 C11 119.89(16) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 120.44(17) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 119.50(18) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 120.73(17) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C9 119.69(17) . . ?
C13 C14 H14 120.2 . . ?
C9 C14 H14 120.2 . . ?
N1 C15 C16 114.25(13) . . ?
N1 C15 C20 113.52(14) . . ?
C16 C15 C20 112.70(14) . . ?
N1 C15 H15 105.1 . . ?
C16 C15 H15 105.1 . . ?
C20 C15 H15 105.1 . . ?
C15 C16 C17 108.48(14) . . ?
C15 C16 H16A 110.0 . . ?
C17 C16 H16A 110.0 . . ?
C15 C16 H16B 110.0 . . ?
C17 C16 H16B 110.0 . . ?
H16A C16 H16B 108.4 . . ?
C18 C17 C16 111.52(16) . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C19 C18 C17 112.27(15) . . ?
C19 C18 H18A 109.1 . . ?
C17 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
C17 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 C20 111.11(15) . . ?
C18 C19 H19A 109.4 . . ?
C20 C19 H19A 109.4 . . ?
C18 C19 H19B 109.4 . . ?
C20 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
C15 C20 C19 108.76(15) . . ?
C15 C20 H20A 109.9 . . ?
C19 C20 H20A 109.9 . . ?
C15 C20 H20B 109.9 . . ?
C19 C20 H20B 109.9 . . ?
H20A C20 H20B 108.3 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.3(2) . . . . ?
C15 N1 C1 C2 179.18(14) . . . . ?
C5 N1 C1 C9 -179.66(13) . . . . ?
C15 N1 C1 C9 -0.7(2) . . . . ?
N1 C1 C2 C3 0.3(2) . . . . ?
C9 C1 C2 C3 -179.76(15) . . . . ?
N1 C1 C2 Br1 -178.73(11) . . . . ?
C9 C1 C2 Br1 1.2(2) . . . . ?
C1 C2 C3 O1 178.79(16) . . . . ?
Br1 C2 C3 O1 -2.1(2) . . . . ?
C1 C2 C3 C4 -1.8(2) . . . . ?
Br1 C2 C3 C4 177.33(11) . . . . ?
O1 C3 C4 C5 -177.75(15) . . . . ?
C2 C3 C4 C5 2.8(2) . . . . ?
O1 C3 C4 C6 1.9(3) . . . . ?
C2 C3 C4 C6 -177.56(15) . . . . ?
C8 N2 C5 N1 -178.94(14) . . . . ?
C8 N2 C5 C4 0.4(2) . . . . ?
C1 N1 C5 N2 -179.82(14) . . . . ?
C15 N1 C5 N2 1.3(2) . . . . ?
C1 N1 C5 C4 0.8(2) . . . . ?
C15 N1 C5 C4 -178.12(14) . . . . ?
C6 C4 C5 N2 -1.4(2) . . . . ?
C3 C4 C5 N2 178.21(15) . . . . ?
C6 C4 C5 N1 177.90(15) . . . . ?
C3 C4 C5 N1 -2.4(2) . . . . ?
C5 C4 C6 C7 1.4(2) . . . . ?
C3 C4 C6 C7 -178.22(15) . . . . ?
C4 C6 C7 C8 -0.5(3) . . . . ?
C5 N2 C8 C7 0.6(3) . . . . ?
C6 C7 C8 N2 -0.6(3) . . . . ?
C2 C1 C9 C10 91.2(2) . . . . ?
N1 C1 C9 C10 -88.89(19) . . . . ?
C2 C1 C9 C14 -91.3(2) . . . . ?
N1 C1 C9 C14 88.66(19) . . . . ?
C14 C9 C10 C11 -0.6(3) . . . . ?
C1 C9 C10 C11 177.00(16) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 C9 -0.8(3) . . . . ?
C10 C9 C14 C13 1.2(3) . . . . ?
C1 C9 C14 C13 -176.35(16) . . . . ?
C1 N1 C15 C16 115.70(16) . . . . ?
C5 N1 C15 C16 -65.39(19) . . . . ?
C1 N1 C15 C20 -113.17(17) . . . . ?
C5 N1 C15 C20 65.74(19) . . . . ?
N1 C15 C16 C17 -169.49(14) . . . . ?
C20 C15 C16 C17 59.0(2) . . . . ?
C15 C16 C17 C18 -55.3(2) . . . . ?
C16 C17 C18 C19 54.8(2) . . . . ?
C17 C18 C19 C20 -54.9(2) . . . . ?
N1 C15 C20 C19 168.69(15) . . . . ?
C16 C15 C20 C19 -59.4(2) . . . . ?
C18 C19 C20 C15 55.8(2) . . . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 30.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.662
_refine_diff_density_min -0.445
_refine_diff_density_rms 0.068
# Attachment 'Ingo-Knepper-rk_ikp165.cif'
#=============================================================================
data_rk_1kp165
_database_code_depnum_ccdc_archive 'CCDC 834866'
#TrackingRef 'Ingo-Knepper-rk_ikp165.cif'
_audit_author_name 'Villinger, A., Kuzora, R.'
_audit_creation_method SHELXL-97
#==============================================================================
# CHEMICAL DATA
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C14 H8 Cl N O'
_chemical_formula_sum 'C14 H8 Cl N O'
_chemical_formula_weight 241.66
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_Int_Tables_number 14
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 11.4766(8)
_cell_length_b 3.8102(2)
_cell_length_c 25.7302(16)
_cell_angle_alpha 90.00
_cell_angle_beta 94.941(4)
_cell_angle_gamma 90.00
_cell_volume 1120.95(12)
_cell_formula_units_Z 4
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 4896
_cell_measurement_theta_min 4.565
_cell_measurement_theta_max 64.805
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.28
_exptl_crystal_size_mid 0.15
_exptl_crystal_size_min 0.11
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.432
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 496
_exptl_absorpt_coefficient_mu 0.320
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9158
_exptl_absorpt_correction_T_max 0.9657
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)'
#==============================================================================
# EXPERIMENTAL DATA
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method 'phi and psi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 14319
_diffrn_reflns_av_R_equivalents 0.0275
_diffrn_reflns_av_sigmaI/netI 0.0268
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_h_max 16
_diffrn_reflns_limit_k_min -4
_diffrn_reflns_limit_k_max 5
_diffrn_reflns_limit_l_min -35
_diffrn_reflns_limit_l_max 36
_diffrn_reflns_theta_min 1.78
_diffrn_reflns_theta_max 30.00
_reflns_number_total 3266
_reflns_number_gt 2521
_reflns_threshold_expression >2\s(I)
_computing_data_collection 'Bruker Apex v2.0-2'
_computing_cell_refinement 'Bruker Apex v2.0-2'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material SHELXL-97
#==============================================================================
# REFINEMENT DATA
_refine_special_details
;
All H atoms were positioned geometrically and refined using a
riding model , with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups),
1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with U~iso~(H) =
1.5 times U~eq~(C) (methyl groups) or with U~iso~(H) = 1.2 times
U~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles
of all methyl groups were allowed to refine.
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0522P)^2^+0.1515P] 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 3266
_refine_ls_number_parameters 154
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0532
_refine_ls_R_factor_gt 0.0364
_refine_ls_wR_factor_ref 0.0991
_refine_ls_wR_factor_gt 0.0936
_refine_ls_goodness_of_fit_ref 1.070
_refine_ls_restrained_S_all 1.070
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
#==============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
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
Cl1 Cl 0.11521(3) 0.63207(9) 0.122634(13) 0.03213(11) Uani 1 1 d . . .
N1 N 0.10479(9) 0.3597(3) 0.21377(4) 0.0298(3) Uani 1 1 d . . .
O1 O 0.48040(8) 0.5888(3) 0.16196(4) 0.0399(3) Uani 1 1 d . . .
C9 C 0.29132(11) 0.1307(3) -0.00037(5) 0.0229(2) Uani 1 1 d . . .
C5 C 0.29964(10) 0.3824(3) 0.18592(4) 0.0200(2) Uani 1 1 d . . .
C8 C 0.33112(11) 0.2544(4) 0.05037(5) 0.0254(3) Uani 1 1 d . . .
C10 C 0.36319(12) 0.1357(3) -0.04133(5) 0.0274(3) Uani 1 1 d . . .
H10 H 0.4408 0.2227 -0.0359 0.033 Uiso 1 1 calc R . .
C13 C 0.13564(12) -0.1150(4) -0.05796(5) 0.0316(3) Uani 1 1 d . . .
H13 H 0.0577 -0.1996 -0.0638 0.038 Uiso 1 1 calc R . .
C1 C 0.17892(10) 0.4350(3) 0.17902(5) 0.0226(2) Uani 1 1 d . . .
C4 C 0.34320(10) 0.2490(3) 0.23410(5) 0.0223(2) Uani 1 1 d . . .
H4 H 0.4249 0.2143 0.2414 0.027 Uiso 1 1 calc R . .
C7 C 0.35730(11) 0.3565(3) 0.09394(5) 0.0264(3) Uani 1 1 d . . .
C3 C 0.26746(12) 0.1670(4) 0.27122(5) 0.0279(3) Uani 1 1 d . . .
H3 H 0.2959 0.0747 0.3042 0.034 Uiso 1 1 calc R . .
C12 C 0.20754(14) -0.1100(4) -0.09833(5) 0.0334(3) Uani 1 1 d . . .
H12 H 0.1789 -0.1915 -0.1319 0.040 Uiso 1 1 calc R . .
C6 C 0.38650(10) 0.4604(3) 0.14723(5) 0.0241(3) Uani 1 1 d . . .
C11 C 0.32103(13) 0.0132(4) -0.09011(5) 0.0334(3) Uani 1 1 d . . .
H11 H 0.3702 0.0138 -0.1180 0.040 Uiso 1 1 calc R . .
C14 C 0.17702(11) 0.0030(4) -0.00901(5) 0.0280(3) Uani 1 1 d . . .
H14 H 0.1277 -0.0026 0.0188 0.034 Uiso 1 1 calc R . .
C2 C 0.14927(12) 0.2226(4) 0.25914(5) 0.0320(3) Uani 1 1 d . . .
H2 H 0.0969 0.1605 0.2843 0.038 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
Cl1 0.02924(17) 0.03251(19) 0.03220(18) 0.00104(13) -0.01142(12) 0.00468(13)
N1 0.0203(5) 0.0359(6) 0.0332(6) -0.0052(5) 0.0022(4) -0.0020(4)
O1 0.0277(5) 0.0638(7) 0.0277(5) -0.0036(5) 0.0004(4) -0.0181(5)
C9 0.0278(6) 0.0206(6) 0.0199(6) 0.0018(4) -0.0003(5) 0.0025(5)
C5 0.0196(5) 0.0194(5) 0.0203(5) -0.0036(4) -0.0019(4) -0.0022(4)
C8 0.0269(6) 0.0248(6) 0.0244(6) 0.0012(5) 0.0015(5) -0.0001(5)
C10 0.0281(6) 0.0291(7) 0.0251(6) 0.0023(5) 0.0033(5) 0.0005(5)
C13 0.0303(6) 0.0296(7) 0.0332(7) -0.0007(6) -0.0065(5) -0.0033(5)
C1 0.0216(5) 0.0207(6) 0.0246(6) -0.0038(5) -0.0038(4) -0.0004(4)
C4 0.0200(5) 0.0243(6) 0.0219(6) -0.0011(5) -0.0024(4) -0.0006(5)
C7 0.0259(6) 0.0295(7) 0.0239(6) -0.0003(5) 0.0026(5) -0.0036(5)
C3 0.0313(6) 0.0311(7) 0.0212(6) 0.0014(5) 0.0007(5) -0.0045(5)
C12 0.0474(8) 0.0289(7) 0.0222(6) -0.0039(5) -0.0063(6) 0.0055(6)
C6 0.0224(6) 0.0278(6) 0.0216(6) -0.0010(5) -0.0007(4) -0.0028(5)
C11 0.0426(8) 0.0369(8) 0.0216(6) 0.0011(6) 0.0072(5) 0.0055(6)
C14 0.0284(6) 0.0307(7) 0.0250(6) 0.0000(5) 0.0030(5) -0.0001(5)
C2 0.0287(6) 0.0388(8) 0.0293(7) -0.0014(6) 0.0072(5) -0.0064(6)
#==============================================================================
# MOLECULAR GEOMETRY
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.7380(12) . ?
N1 C1 1.3178(17) . ?
N1 C2 1.3393(18) . ?
O1 C6 1.2140(15) . ?
C9 C10 1.3934(18) . ?
C9 C14 1.3989(18) . ?
C9 C8 1.4256(17) . ?
C5 C4 1.3923(16) . ?
C5 C1 1.3960(16) . ?
C5 C6 1.4980(17) . ?
C8 C7 1.2001(18) . ?
C10 C11 1.3865(19) . ?
C10 H10 0.9500 . ?
C13 C12 1.381(2) . ?
C13 C14 1.3824(18) . ?
C13 H13 0.9500 . ?
C4 C3 1.3816(17) . ?
C4 H4 0.9500 . ?
C7 C6 1.4387(17) . ?
C3 C2 1.3816(19) . ?
C3 H3 0.9500 . ?
C12 C11 1.383(2) . ?
C12 H12 0.9500 . ?
C11 H11 0.9500 . ?
C14 H14 0.9500 . ?
C2 H2 0.9500 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 117.16(11) . . ?
C10 C9 C14 119.51(11) . . ?
C10 C9 C8 121.63(12) . . ?
C14 C9 C8 118.86(11) . . ?
C4 C5 C1 116.23(11) . . ?
C4 C5 C6 117.11(10) . . ?
C1 C5 C6 126.66(11) . . ?
C7 C8 C9 175.75(13) . . ?
C11 C10 C9 119.80(12) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C12 C13 C14 120.00(13) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
N1 C1 C5 125.04(11) . . ?
N1 C1 Cl1 114.25(9) . . ?
C5 C1 Cl1 120.64(10) . . ?
C3 C4 C5 119.94(11) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C8 C7 C6 176.79(14) . . ?
C2 C3 C4 118.28(12) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C13 C12 C11 120.35(12) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
O1 C6 C7 122.42(11) . . ?
O1 C6 C5 119.74(11) . . ?
C7 C6 C5 117.71(10) . . ?
C12 C11 C10 120.22(13) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C14 C9 120.13(12) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
N1 C2 C3 123.30(12) . . ?
N1 C2 H2 118.4 . . ?
C3 C2 H2 118.4 . . ?
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
C10 C9 C8 C7 171.1(19) . . . . ?
C14 C9 C8 C7 -9(2) . . . . ?
C14 C9 C10 C11 -0.23(19) . . . . ?
C8 C9 C10 C11 -179.94(13) . . . . ?
C2 N1 C1 C5 0.1(2) . . . . ?
C2 N1 C1 Cl1 -176.92(10) . . . . ?
C4 C5 C1 N1 -1.86(19) . . . . ?
C6 C5 C1 N1 179.24(12) . . . . ?
C4 C5 C1 Cl1 174.95(9) . . . . ?
C6 C5 C1 Cl1 -3.96(18) . . . . ?
C1 C5 C4 C3 1.89(18) . . . . ?
C6 C5 C4 C3 -179.10(11) . . . . ?
C9 C8 C7 C6 61(4) . . . . ?
C5 C4 C3 C2 -0.29(19) . . . . ?
C14 C13 C12 C11 -0.1(2) . . . . ?
C8 C7 C6 O1 131(2) . . . . ?
C8 C7 C6 C5 -44(3) . . . . ?
C4 C5 C6 O1 -39.33(18) . . . . ?
C1 C5 C6 O1 139.57(14) . . . . ?
C4 C5 C6 C7 136.59(12) . . . . ?
C1 C5 C6 C7 -44.51(18) . . . . ?
C13 C12 C11 C10 -0.6(2) . . . . ?
C9 C10 C11 C12 0.7(2) . . . . ?
C12 C13 C14 C9 0.6(2) . . . . ?
C10 C9 C14 C13 -0.4(2) . . . . ?
C8 C9 C14 C13 179.28(12) . . . . ?
C1 N1 C2 C3 1.8(2) . . . . ?
C4 C3 C2 N1 -1.6(2) . . . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 30.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.363
_refine_diff_density_min -0.199
_refine_diff_density_rms 0.047
#===================== End of CIF submission =================================
# Attachment 'Ingo-Knepper-rk_ikp169.cif'
#=============================================================================
data_rk_ikp169
_database_code_depnum_ccdc_archive 'CCDC 834867'
#TrackingRef 'Ingo-Knepper-rk_ikp169.cif'
_audit_author_name 'Villinger, A., Kuzora, R.'
_audit_creation_method SHELXL-97
#==============================================================================
# CHEMICAL DATA
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C22 H18 N2 O1, H1 O0.5'
_chemical_formula_sum 'C22 H19 N2 O1.50'
_chemical_formula_weight 335.39
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'
#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_Int_Tables_number 14
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 8.6083(6)
_cell_length_b 26.5181(19)
_cell_length_c 7.4938(6)
_cell_angle_alpha 90.00
_cell_angle_beta 98.838(4)
_cell_angle_gamma 90.00
_cell_volume 1690.3(2)
_cell_formula_units_Z 4
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 5309
_cell_measurement_theta_min 5.690
_cell_measurement_theta_max 62.150
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.45
_exptl_crystal_size_mid 0.16
_exptl_crystal_size_min 0.09
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.318
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 708
_exptl_absorpt_coefficient_mu 0.083
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9634
_exptl_absorpt_correction_T_max 0.9925
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)'
#==============================================================================
# EXPERIMENTAL DATA
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method 'phi and psi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 20776
_diffrn_reflns_av_R_equivalents 0.0278
_diffrn_reflns_av_sigmaI/netI 0.0300
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -37
_diffrn_reflns_limit_k_max 37
_diffrn_reflns_limit_l_min -10
_diffrn_reflns_limit_l_max 7
_diffrn_reflns_theta_min 2.39
_diffrn_reflns_theta_max 30.00
_reflns_number_total 4921
_reflns_number_gt 3391
_reflns_threshold_expression >2\s(I)
_computing_data_collection 'Bruker Apex v2.0-2'
_computing_cell_refinement 'Bruker Apex v2.0-2'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material SHELXL-97
#==============================================================================
# REFINEMENT DATA
_refine_special_details
;
All H atoms were positioned geometrically and refined using a
riding model , with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups),
1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with U~iso~(H) =
1.5 times U~eq~(C) (methyl groups) or with U~iso~(H) = 1.2 times
U~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles
of all methyl groups were allowed to refine.
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0601P)^2^+0.2215P] 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 4921
_refine_ls_number_parameters 243
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0779
_refine_ls_R_factor_gt 0.0475
_refine_ls_wR_factor_ref 0.1286
_refine_ls_wR_factor_gt 0.1177
_refine_ls_goodness_of_fit_ref 1.069
_refine_ls_restrained_S_all 1.069
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
#==============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
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 0.70589(13) 0.42436(4) 0.56691(14) 0.0352(2) Uani 1 1 d . . .
N2 N 0.45988(11) 0.39038(3) 0.57037(12) 0.0265(2) Uani 1 1 d . . .
O1 O 0.27638(12) 0.46853(4) 0.11458(13) 0.0511(3) Uani 1 1 d . . .
C1 C 0.55627(14) 0.42204(4) 0.48863(14) 0.0270(2) Uani 1 1 d . . .
C2 C 0.80114(18) 0.45323(5) 0.48804(19) 0.0429(3) Uani 1 1 d . . .
H2 H 0.9080 0.4554 0.5429 0.051 Uiso 1 1 calc R . .
C3 C 0.75523(18) 0.48047(5) 0.33070(18) 0.0424(3) Uani 1 1 d . . .
H3 H 0.8292 0.4997 0.2776 0.051 Uiso 1 1 calc R . .
C4 C 0.60167(17) 0.47886(4) 0.25484(16) 0.0357(3) Uani 1 1 d . . .
H4 H 0.5663 0.4978 0.1488 0.043 Uiso 1 1 calc R . .
C5 C 0.49558(15) 0.44926(4) 0.33282(15) 0.0294(3) Uani 1 1 d . . .
C6 C 0.33070(16) 0.44541(5) 0.25533(15) 0.0347(3) Uani 1 1 d . . .
C7 C 0.23969(15) 0.41372(5) 0.35314(16) 0.0343(3) Uani 1 1 d . . .
H7 H 0.1301 0.4107 0.3122 0.041 Uiso 1 1 calc R . .
C8 C 0.30414(14) 0.38756(4) 0.50358(15) 0.0287(2) Uani 1 1 d . . .
C9 C 0.20159(14) 0.35626(5) 0.60290(16) 0.0331(3) Uani 1 1 d . . .
C10 C 0.12035(19) 0.37896(6) 0.7251(2) 0.0525(4) Uani 1 1 d . . .
H10 H 0.1350 0.4139 0.7503 0.063 Uiso 1 1 calc R . .
C11 C 0.0173(2) 0.35146(7) 0.8121(3) 0.0655(5) Uani 1 1 d . . .
H11 H -0.0396 0.3677 0.8947 0.079 Uiso 1 1 calc R . .
C12 C -0.00256(18) 0.30116(7) 0.7792(2) 0.0575(5) Uani 1 1 d . . .
H12 H -0.0738 0.2824 0.8382 0.069 Uiso 1 1 calc R . .
C13 C 0.08031(19) 0.27770(6) 0.6611(2) 0.0531(4) Uani 1 1 d . . .
H13 H 0.0688 0.2424 0.6410 0.064 Uiso 1 1 calc R . .
C14 C 0.18086(17) 0.30510(6) 0.57058(18) 0.0427(3) Uani 1 1 d . . .
H14 H 0.2357 0.2888 0.4862 0.051 Uiso 1 1 calc R . .
C15 C 0.52963(14) 0.36030(4) 0.72790(14) 0.0264(2) Uani 1 1 d . . .
H15A H 0.6372 0.3500 0.7120 0.032 Uiso 1 1 calc R . .
H15B H 0.4666 0.3293 0.7338 0.032 Uiso 1 1 calc R . .
C16 C 0.53724(16) 0.38895(4) 0.90507(15) 0.0330(3) Uani 1 1 d . . .
H16A H 0.6163 0.4162 0.9102 0.040 Uiso 1 1 calc R . .
H16B H 0.4338 0.4045 0.9120 0.040 Uiso 1 1 calc R . .
C17 C 0.58084(14) 0.35374(4) 1.06268(14) 0.0275(2) Uani 1 1 d . . .
C18 C 0.47067(15) 0.32023(5) 1.11186(16) 0.0328(3) Uani 1 1 d . . .
H18 H 0.3672 0.3197 1.0458 0.039 Uiso 1 1 calc R . .
C19 C 0.51020(16) 0.28759(5) 1.25638(17) 0.0365(3) Uani 1 1 d . . .
H19 H 0.4341 0.2647 1.2880 0.044 Uiso 1 1 calc R . .
C20 C 0.65860(17) 0.28829(5) 1.35369(17) 0.0388(3) Uani 1 1 d . . .
H20 H 0.6854 0.2661 1.4533 0.047 Uiso 1 1 calc R . .
C21 C 0.76849(16) 0.32130(5) 1.30605(17) 0.0391(3) Uani 1 1 d . . .
H21 H 0.8716 0.3219 1.3730 0.047 Uiso 1 1 calc R . .
C22 C 0.72970(15) 0.35371(5) 1.16103(16) 0.0322(3) Uani 1 1 d . . .
H22 H 0.8068 0.3762 1.1291 0.039 Uiso 1 1 calc R . .
O2 O -0.0273(4) 0.46046(13) -0.0369(5) 0.0803(10) Uani 0.50 1 d P . .
H1A H -0.073(6) 0.485(2) -0.060(7) 0.089(17) Uiso 0.50 1 d P . .
H1B H 0.063(7) 0.470(2) 0.033(8) 0.101(16) Uiso 0.50 1 d P . .
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 0.0398(6) 0.0360(6) 0.0285(5) 0.0023(4) 0.0013(4) -0.0055(4)
N2 0.0321(5) 0.0277(5) 0.0195(4) 0.0046(4) 0.0032(4) 0.0048(4)
O1 0.0537(6) 0.0663(7) 0.0341(5) 0.0250(5) 0.0088(5) 0.0222(5)
C1 0.0370(6) 0.0241(5) 0.0206(5) -0.0001(4) 0.0065(4) 0.0034(4)
C2 0.0468(8) 0.0426(7) 0.0380(7) 0.0008(6) 0.0023(6) -0.0145(6)
C3 0.0591(9) 0.0337(7) 0.0358(7) -0.0004(5) 0.0120(6) -0.0149(6)
C4 0.0603(9) 0.0239(6) 0.0244(6) 0.0020(4) 0.0110(6) 0.0014(5)
C5 0.0442(7) 0.0246(5) 0.0203(5) 0.0011(4) 0.0083(5) 0.0080(5)
C6 0.0438(7) 0.0382(7) 0.0231(5) 0.0066(5) 0.0086(5) 0.0169(5)
C7 0.0329(6) 0.0435(7) 0.0262(6) 0.0060(5) 0.0035(5) 0.0120(5)
C8 0.0320(6) 0.0321(6) 0.0224(5) 0.0017(4) 0.0055(4) 0.0090(5)
C9 0.0286(6) 0.0408(7) 0.0291(6) 0.0100(5) 0.0023(5) 0.0067(5)
C10 0.0578(10) 0.0448(8) 0.0625(10) 0.0169(7) 0.0330(8) 0.0162(7)
C11 0.0588(11) 0.0751(12) 0.0720(12) 0.0281(9) 0.0396(9) 0.0196(9)
C12 0.0382(8) 0.0778(12) 0.0548(10) 0.0339(9) 0.0022(7) -0.0081(8)
C13 0.0544(9) 0.0565(9) 0.0429(8) 0.0119(7) -0.0100(7) -0.0185(7)
C14 0.0454(8) 0.0486(8) 0.0317(7) 0.0007(6) -0.0018(6) -0.0074(6)
C15 0.0335(6) 0.0250(5) 0.0199(5) 0.0040(4) 0.0013(4) 0.0048(4)
C16 0.0505(8) 0.0270(6) 0.0212(5) 0.0026(4) 0.0046(5) 0.0063(5)
C17 0.0399(7) 0.0253(5) 0.0182(5) -0.0007(4) 0.0068(4) 0.0061(5)
C18 0.0355(7) 0.0332(6) 0.0294(6) 0.0007(5) 0.0040(5) 0.0038(5)
C19 0.0479(8) 0.0305(6) 0.0341(6) 0.0048(5) 0.0161(6) 0.0035(5)
C20 0.0552(9) 0.0368(7) 0.0255(6) 0.0082(5) 0.0098(6) 0.0147(6)
C21 0.0383(7) 0.0475(8) 0.0301(6) 0.0023(5) 0.0009(5) 0.0119(6)
C22 0.0361(7) 0.0346(6) 0.0269(6) -0.0010(5) 0.0085(5) 0.0023(5)
O2 0.0499(17) 0.083(2) 0.099(2) -0.0259(17) -0.0153(15) 0.0290(15)
#==============================================================================
# MOLECULAR GEOMETRY
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.3253(17) . ?
N1 C1 1.3322(16) . ?
N2 C8 1.3592(15) . ?
N2 C1 1.3873(15) . ?
N2 C15 1.4739(13) . ?
O1 C6 1.2472(14) . ?
C1 C5 1.4035(15) . ?
C2 C3 1.387(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.357(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3985(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.4522(19) . ?
C6 C7 1.4260(18) . ?
C7 C8 1.3667(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.4914(17) . ?
C9 C10 1.3737(18) . ?
C9 C14 1.385(2) . ?
C10 C11 1.386(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.362(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.369(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.5223(15) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5070(15) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C22 1.3766(17) . ?
C17 C18 1.3900(17) . ?
C18 C19 1.3873(17) . ?
C18 H18 0.9500 . ?
C19 C20 1.370(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.376(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.3856(17) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
O2 H1A 0.77(6) . ?
O2 H1B 0.90(7) . ?
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
C2 N1 C1 116.93(11) . . ?
C8 N2 C1 119.58(9) . . ?
C8 N2 C15 121.50(9) . . ?
C1 N2 C15 118.91(9) . . ?
N1 C1 N2 115.91(10) . . ?
N1 C1 C5 123.62(11) . . ?
N2 C1 C5 120.47(11) . . ?
N1 C2 C3 124.39(13) . . ?
N1 C2 H2 117.8 . . ?
C3 C2 H2 117.8 . . ?
C4 C3 C2 118.13(12) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 119.96(12) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C1 116.92(12) . . ?
C4 C5 C6 122.23(11) . . ?
C1 C5 C6 120.83(11) . . ?
O1 C6 C7 124.07(13) . . ?
O1 C6 C5 121.33(12) . . ?
C7 C6 C5 114.60(10) . . ?
C8 C7 C6 122.53(12) . . ?
C8 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
N2 C8 C7 121.89(11) . . ?
N2 C8 C9 118.22(10) . . ?
C7 C8 C9 119.86(11) . . ?
C10 C9 C14 118.74(13) . . ?
C10 C9 C8 119.33(12) . . ?
C14 C9 C8 121.89(11) . . ?
C9 C10 C11 120.74(15) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 120.12(16) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 119.89(14) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 120.36(15) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 120.12(14) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
N2 C15 C16 112.71(9) . . ?
N2 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
N2 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C15 110.28(9) . . ?
C17 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 . . ?
C17 C16 H16B 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C22 C17 C18 118.33(10) . . ?
C22 C17 C16 121.28(11) . . ?
C18 C17 C16 120.39(11) . . ?
C19 C18 C17 120.69(12) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 120.25(12) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 119.50(11) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C20 C21 C22 120.39(12) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 120.84(12) . . ?
C17 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
H1A O2 H1B 105(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
C2 N1 C1 N2 178.07(11) . . . . ?
C2 N1 C1 C5 -1.80(17) . . . . ?
C8 N2 C1 N1 177.12(10) . . . . ?
C15 N2 C1 N1 -3.17(14) . . . . ?
C8 N2 C1 C5 -3.02(15) . . . . ?
C15 N2 C1 C5 176.70(9) . . . . ?
C1 N1 C2 C3 -0.4(2) . . . . ?
N1 C2 C3 C4 2.1(2) . . . . ?
C2 C3 C4 C5 -1.62(19) . . . . ?
C3 C4 C5 C1 -0.36(17) . . . . ?
C3 C4 C5 C6 -178.81(11) . . . . ?
N1 C1 C5 C4 2.18(16) . . . . ?
N2 C1 C5 C4 -177.67(10) . . . . ?
N1 C1 C5 C6 -179.34(11) . . . . ?
N2 C1 C5 C6 0.80(16) . . . . ?
C4 C5 C6 O1 0.07(18) . . . . ?
C1 C5 C6 O1 -178.32(11) . . . . ?
C4 C5 C6 C7 -179.76(11) . . . . ?
C1 C5 C6 C7 1.85(16) . . . . ?
O1 C6 C7 C8 177.70(12) . . . . ?
C5 C6 C7 C8 -2.48(17) . . . . ?
C1 N2 C8 C7 2.46(16) . . . . ?
C15 N2 C8 C7 -177.25(10) . . . . ?
C1 N2 C8 C9 -175.36(10) . . . . ?
C15 N2 C8 C9 4.93(15) . . . . ?
C6 C7 C8 N2 0.40(19) . . . . ?
C6 C7 C8 C9 178.19(11) . . . . ?
N2 C8 C9 C10 95.47(15) . . . . ?
C7 C8 C9 C10 -82.40(17) . . . . ?
N2 C8 C9 C14 -87.07(15) . . . . ?
C7 C8 C9 C14 95.06(15) . . . . ?
C14 C9 C10 C11 -1.2(2) . . . . ?
C8 C9 C10 C11 176.34(15) . . . . ?
C9 C10 C11 C12 1.1(3) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C11 C12 C13 C14 -1.9(2) . . . . ?
C12 C13 C14 C9 1.8(2) . . . . ?
C10 C9 C14 C13 -0.2(2) . . . . ?
C8 C9 C14 C13 -177.72(12) . . . . ?
C8 N2 C15 C16 -93.99(13) . . . . ?
C1 N2 C15 C16 86.30(12) . . . . ?
N2 C15 C16 C17 169.52(10) . . . . ?
C15 C16 C17 C22 104.34(13) . . . . ?
C15 C16 C17 C18 -75.49(14) . . . . ?
C22 C17 C18 C19 -0.07(17) . . . . ?
C16 C17 C18 C19 179.76(10) . . . . ?
C17 C18 C19 C20 0.54(18) . . . . ?
C18 C19 C20 C21 -0.55(19) . . . . ?
C19 C20 C21 C22 0.12(19) . . . . ?
C18 C17 C22 C21 -0.36(17) . . . . ?
C16 C17 C22 C21 179.81(11) . . . . ?
C20 C21 C22 C17 0.35(18) . . . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 30.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.251
_refine_diff_density_min -0.209
_refine_diff_density_rms 0.043
#===================== End of CIF submission =================================
# Attachment 'Sergii-Dudkin-rk_sd120.cif'
#=============================================================================
data_is_ag045
_database_code_depnum_ccdc_archive 'CCDC 834868'
#TrackingRef 'Sergii-Dudkin-rk_sd120.cif'
_audit_author_name 'Villinger, A., Kuzora, R.'
_audit_creation_method SHELXL-97
#==============================================================================
# CHEMICAL DATA
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C27 H24 Cl N3 O2'
_chemical_formula_sum 'C27 H24 Cl N3 O2'
_chemical_formula_weight 457.94
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
_symmetry_Int_Tables_number 2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 9.9870(4)
_cell_length_b 10.6502(4)
_cell_length_c 11.9022(5)
_cell_angle_alpha 94.557(2)
_cell_angle_beta 114.488(2)
_cell_angle_gamma 93.883(2)
_cell_volume 1141.35(8)
_cell_formula_units_Z 2
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 5389
_cell_measurement_theta_min 4.501
_cell_measurement_theta_max 60.422
_exptl_crystal_description block
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.17
_exptl_crystal_size_mid 0.15
_exptl_crystal_size_min 0.11
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.333
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 480
_exptl_absorpt_coefficient_mu 0.198
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9672
_exptl_absorpt_correction_T_max 0.9786
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)'
#==============================================================================
# EXPERIMENTAL DATA
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method 'phi and psi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 25092
_diffrn_reflns_av_R_equivalents 0.0407
_diffrn_reflns_av_sigmaI/netI 0.0461
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_theta_min 2.25
_diffrn_reflns_theta_max 30.00
_reflns_number_total 6633
_reflns_number_gt 4591
_reflns_threshold_expression >2\s(I)
_computing_data_collection 'Bruker Apex v2.0-2'
_computing_cell_refinement 'Bruker Apex v2.0-2'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material SHELXL-97
#==============================================================================
# REFINEMENT DATA
_refine_special_details
;
All H atoms were positioned geometrically and refined using a
riding model , with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups),
1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with U~iso~(H) =
1.5 times U~eq~(C) (methyl groups) or with U~iso~(H) = 1.2 times
U~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles
of all methyl groups were allowed to refine.
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0614P)^2^+0.0052P] 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 6633
_refine_ls_number_parameters 304
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0757
_refine_ls_R_factor_gt 0.0437
_refine_ls_wR_factor_ref 0.1160
_refine_ls_wR_factor_gt 0.1074
_refine_ls_goodness_of_fit_ref 1.043
_refine_ls_restrained_S_all 1.043
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
#==============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
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
Cl1 Cl -0.00750(4) 0.16378(3) 0.45378(3) 0.03123(10) Uani 1 1 d . . .
N1 N -0.13337(13) 0.11552(11) 0.20875(11) 0.0262(3) Uani 1 1 d . . .
N2 N -0.15679(14) 0.16307(11) 0.09929(11) 0.0322(3) Uani 1 1 d . . .
N3 N 0.25292(14) 0.65695(11) 0.47380(13) 0.0300(3) Uani 1 1 d . . .
O1 O 0.05267(12) 0.52337(9) 0.27220(10) 0.0352(3) Uani 1 1 d . . .
O2 O 0.25392(13) 1.15845(10) 0.21145(11) 0.0386(3) Uani 1 1 d . . .
C1 C -0.04533(15) 0.19878(13) 0.30739(13) 0.0232(3) Uani 1 1 d . . .
C2 C -0.00870(15) 0.30641(12) 0.26427(13) 0.0238(3) Uani 1 1 d . . .
C3 C -0.08151(16) 0.27758(13) 0.13361(13) 0.0288(3) Uani 1 1 d . . .
C4 C -0.0778(2) 0.35576(16) 0.03590(15) 0.0452(4) Uani 1 1 d . . .
H4A H -0.1376 0.3093 -0.0465 0.068 Uiso 1 1 calc R . .
H4B H 0.0247 0.3734 0.0466 0.068 Uiso 1 1 calc R . .
H4C H -0.1180 0.4358 0.0435 0.068 Uiso 1 1 calc R . .
C5 C -0.20177(16) -0.00821(13) 0.20605(13) 0.0261(3) Uani 1 1 d . . .
C6 C -0.35343(17) -0.02748(15) 0.16212(15) 0.0347(3) Uani 1 1 d . . .
H6 H -0.4118 0.0404 0.1355 0.042 Uiso 1 1 calc R . .
C7 C -0.41946(19) -0.14753(16) 0.15741(17) 0.0424(4) Uani 1 1 d . . .
H7 H -0.5240 -0.1624 0.1273 0.051 Uiso 1 1 calc R . .
C8 C -0.3339(2) -0.24615(16) 0.19639(15) 0.0423(4) Uani 1 1 d . . .
H8 H -0.3798 -0.3281 0.1938 0.051 Uiso 1 1 calc R . .
C9 C -0.1829(2) -0.22557(15) 0.23870(15) 0.0394(4) Uani 1 1 d . . .
H9 H -0.1246 -0.2936 0.2646 0.047 Uiso 1 1 calc R . .
C10 C -0.11510(17) -0.10601(14) 0.24387(15) 0.0337(3) Uani 1 1 d . . .
H10 H -0.0106 -0.0915 0.2730 0.040 Uiso 1 1 calc R . .
C11 C 0.07746(15) 0.42895(13) 0.33166(14) 0.0258(3) Uani 1 1 d . . .
C12 C 0.18406(15) 0.43579(12) 0.45665(13) 0.0253(3) Uani 1 1 d . . .
H12 H 0.1976 0.3610 0.4968 0.030 Uiso 1 1 calc R . .
C13 C 0.26897(15) 0.54747(13) 0.52216(13) 0.0237(3) Uani 1 1 d . . .
C14 C 0.38404(15) 0.54912(12) 0.65175(13) 0.0237(3) Uani 1 1 d . . .
C15 C 0.51680(16) 0.50045(14) 0.67449(14) 0.0301(3) Uani 1 1 d . . .
H15 H 0.5337 0.4625 0.6072 0.036 Uiso 1 1 calc R . .
C16 C 0.62527(17) 0.50694(16) 0.79521(15) 0.0359(4) Uani 1 1 d . . .
H16 H 0.7168 0.4745 0.8103 0.043 Uiso 1 1 calc R . .
C17 C 0.60025(18) 0.56051(15) 0.89339(14) 0.0361(4) Uani 1 1 d . . .
H17 H 0.6743 0.5646 0.9761 0.043 Uiso 1 1 calc R . .
C18 C 0.4676(2) 0.60805(16) 0.87107(15) 0.0402(4) Uani 1 1 d . . .
H18 H 0.4500 0.6442 0.9386 0.048 Uiso 1 1 calc R . .
C19 C 0.36047(18) 0.60322(15) 0.75120(15) 0.0351(4) Uani 1 1 d . . .
H19 H 0.2699 0.6371 0.7364 0.042 Uiso 1 1 calc R . .
C20 C 0.34336(17) 0.77727(13) 0.53317(15) 0.0343(3) Uani 1 1 d . . .
H20A H 0.4494 0.7637 0.5672 0.041 Uiso 1 1 calc R . .
H20B H 0.3213 0.8098 0.6032 0.041 Uiso 1 1 calc R . .
C21 C 0.31401(15) 0.87372(13) 0.44224(14) 0.0278(3) Uani 1 1 d . . .
C22 C 0.31675(16) 1.00045(13) 0.48310(14) 0.0294(3) Uani 1 1 d . . .
H22 H 0.3327 1.0239 0.5667 0.035 Uiso 1 1 calc R . .
C23 C 0.29669(16) 1.09235(13) 0.40420(15) 0.0301(3) Uani 1 1 d . . .
H23 H 0.2999 1.1784 0.4341 0.036 Uiso 1 1 calc R . .
C24 C 0.27185(16) 1.06035(13) 0.28172(15) 0.0283(3) Uani 1 1 d . . .
C25 C 0.26655(17) 0.93413(13) 0.23778(15) 0.0322(3) Uani 1 1 d . . .
H25 H 0.2479 0.9106 0.1535 0.039 Uiso 1 1 calc R . .
C26 C 0.28914(17) 0.84300(13) 0.31962(15) 0.0329(3) Uani 1 1 d . . .
H26 H 0.2874 0.7570 0.2903 0.039 Uiso 1 1 calc R . .
C27 C 0.2188(2) 1.12798(16) 0.08300(16) 0.0442(4) Uani 1 1 d . . .
H27A H 0.2998 1.0875 0.0743 0.066 Uiso 1 1 calc R . .
H27B H 0.2052 1.2057 0.0425 0.066 Uiso 1 1 calc R . .
H27C H 0.1274 1.0698 0.0438 0.066 Uiso 1 1 calc R . .
H28 H 0.183(2) 0.6514(18) 0.3991(19) 0.048(5) 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
Cl1 0.0377(2) 0.03178(19) 0.02423(18) 0.00402(14) 0.01394(15) -0.00239(15)
N1 0.0294(6) 0.0221(6) 0.0210(6) 0.0049(5) 0.0049(5) -0.0024(5)
N2 0.0391(7) 0.0270(6) 0.0211(6) 0.0071(5) 0.0039(5) -0.0040(5)
N3 0.0283(7) 0.0217(6) 0.0297(7) 0.0037(5) 0.0027(6) -0.0031(5)
O1 0.0383(6) 0.0229(5) 0.0320(6) 0.0078(4) 0.0024(5) -0.0013(4)
O2 0.0575(7) 0.0230(5) 0.0422(7) 0.0072(5) 0.0275(6) 0.0023(5)
C1 0.0222(6) 0.0238(6) 0.0228(7) 0.0038(5) 0.0083(6) 0.0029(5)
C2 0.0221(6) 0.0218(6) 0.0250(7) 0.0062(5) 0.0067(6) 0.0032(5)
C3 0.0303(7) 0.0250(7) 0.0248(7) 0.0072(6) 0.0051(6) -0.0006(6)
C4 0.0628(12) 0.0328(8) 0.0271(8) 0.0101(7) 0.0073(8) -0.0087(8)
C5 0.0308(7) 0.0239(7) 0.0206(7) 0.0014(5) 0.0091(6) -0.0047(6)
C6 0.0305(8) 0.0331(8) 0.0381(9) -0.0016(7) 0.0138(7) 0.0000(6)
C7 0.0358(9) 0.0439(10) 0.0459(10) -0.0101(8) 0.0215(8) -0.0155(7)
C8 0.0586(11) 0.0325(8) 0.0327(9) -0.0018(7) 0.0210(8) -0.0196(8)
C9 0.0506(10) 0.0261(7) 0.0315(8) 0.0085(7) 0.0076(8) -0.0012(7)
C10 0.0310(8) 0.0287(7) 0.0333(8) 0.0082(6) 0.0056(7) -0.0013(6)
C11 0.0254(7) 0.0208(6) 0.0292(7) 0.0046(6) 0.0095(6) 0.0016(5)
C12 0.0275(7) 0.0191(6) 0.0265(7) 0.0050(5) 0.0080(6) 0.0032(5)
C13 0.0213(6) 0.0233(6) 0.0263(7) 0.0029(5) 0.0096(6) 0.0035(5)
C14 0.0248(7) 0.0201(6) 0.0242(7) 0.0024(5) 0.0089(6) -0.0007(5)
C15 0.0321(8) 0.0343(8) 0.0253(7) 0.0049(6) 0.0128(6) 0.0063(6)
C16 0.0281(8) 0.0414(9) 0.0350(9) 0.0109(7) 0.0090(7) 0.0057(7)
C17 0.0402(9) 0.0333(8) 0.0227(7) 0.0030(6) 0.0024(7) -0.0036(7)
C18 0.0540(11) 0.0391(9) 0.0279(8) -0.0009(7) 0.0182(8) 0.0069(8)
C19 0.0380(9) 0.0376(8) 0.0320(8) 0.0021(7) 0.0165(7) 0.0107(7)
C20 0.0327(8) 0.0235(7) 0.0342(8) 0.0018(6) 0.0035(7) -0.0064(6)
C21 0.0243(7) 0.0229(7) 0.0329(8) 0.0026(6) 0.0097(6) -0.0024(5)
C22 0.0286(7) 0.0261(7) 0.0319(8) -0.0019(6) 0.0131(6) -0.0027(6)
C23 0.0322(8) 0.0189(6) 0.0420(9) -0.0009(6) 0.0195(7) 0.0006(6)
C24 0.0282(7) 0.0212(6) 0.0402(8) 0.0055(6) 0.0187(7) 0.0016(5)
C25 0.0399(9) 0.0250(7) 0.0343(8) 0.0004(6) 0.0190(7) 0.0014(6)
C26 0.0385(8) 0.0196(7) 0.0377(9) -0.0011(6) 0.0144(7) 0.0014(6)
C27 0.0607(12) 0.0339(9) 0.0420(10) 0.0103(7) 0.0252(9) -0.0001(8)
#==============================================================================
# MOLECULAR GEOMETRY
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.7012(14) . ?
N1 C1 1.3457(18) . ?
N1 N2 1.3699(16) . ?
N1 C5 1.4344(17) . ?
N2 C3 1.3272(18) . ?
N3 C13 1.3312(18) . ?
N3 C20 1.4586(18) . ?
N3 H28 0.87(2) . ?
O1 C11 1.2549(17) . ?
O2 C24 1.3650(17) . ?
O2 C27 1.424(2) . ?
C1 C2 1.3797(18) . ?
C2 C3 1.413(2) . ?
C2 C11 1.4820(19) . ?
C3 C4 1.494(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.376(2) . ?
C5 C10 1.382(2) . ?
C6 C7 1.384(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.385(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.372(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.418(2) . ?
C12 C13 1.3818(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.4911(19) . ?
C14 C15 1.3849(19) . ?
C14 C19 1.389(2) . ?
C15 C16 1.388(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.378(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.506(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C26 1.383(2) . ?
C21 C22 1.392(2) . ?
C22 C23 1.377(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.383(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.393(2) . ?
C25 C26 1.393(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 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
C1 N1 N2 111.28(11) . . ?
C1 N1 C5 129.13(12) . . ?
N2 N1 C5 119.59(11) . . ?
C3 N2 N1 104.61(12) . . ?
C13 N3 C20 125.98(13) . . ?
C13 N3 H28 113.7(13) . . ?
C20 N3 H28 120.3(13) . . ?
C24 O2 C27 117.37(12) . . ?
N1 C1 C2 108.32(12) . . ?
N1 C1 Cl1 119.86(10) . . ?
C2 C1 Cl1 131.69(11) . . ?
C1 C2 C3 103.48(12) . . ?
C1 C2 C11 131.00(13) . . ?
C3 C2 C11 125.43(12) . . ?
N2 C3 C2 112.31(12) . . ?
N2 C3 C4 119.11(13) . . ?
C2 C3 C4 128.53(13) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 121.48(14) . . ?
C6 C5 N1 118.90(13) . . ?
C10 C5 N1 119.60(13) . . ?
C5 C6 C7 118.81(15) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C6 C7 C8 120.37(16) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 120.05(15) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.31(15) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C5 C10 C9 118.98(15) . . ?
C5 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
O1 C11 C12 122.80(13) . . ?
O1 C11 C2 116.82(13) . . ?
C12 C11 C2 120.37(12) . . ?
C13 C12 C11 122.31(13) . . ?
C13 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
N3 C13 C12 122.35(13) . . ?
N3 C13 C14 117.21(12) . . ?
C12 C13 C14 120.44(12) . . ?
C15 C14 C19 119.19(14) . . ?
C15 C14 C13 120.79(12) . . ?
C19 C14 C13 119.99(12) . . ?
C14 C15 C16 120.22(14) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 120.03(14) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 119.85(15) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 120.23(15) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C14 120.46(14) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
N3 C20 C21 111.17(13) . . ?
N3 C20 H20A 109.4 . . ?
C21 C20 H20A 109.4 . . ?
N3 C20 H20B 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C26 C21 C22 117.84(14) . . ?
C26 C21 C20 122.85(13) . . ?
C22 C21 C20 119.27(14) . . ?
C23 C22 C21 121.06(14) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 120.52(13) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
O2 C24 C23 115.92(12) . . ?
O2 C24 C25 124.38(14) . . ?
C23 C24 C25 119.70(14) . . ?
C24 C25 C26 118.80(15) . . ?
C24 C25 H25 120.6 . . ?
C26 C25 H25 120.6 . . ?
C21 C26 C25 122.06(13) . . ?
C21 C26 H26 119.0 . . ?
C25 C26 H26 119.0 . . ?
O2 C27 H27A 109.5 . . ?
O2 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O2 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C3 -0.30(16) . . . . ?
C5 N1 N2 C3 179.05(13) . . . . ?
N2 N1 C1 C2 0.53(16) . . . . ?
C5 N1 C1 C2 -178.74(13) . . . . ?
N2 N1 C1 Cl1 176.91(10) . . . . ?
C5 N1 C1 Cl1 -2.4(2) . . . . ?
N1 C1 C2 C3 -0.50(15) . . . . ?
Cl1 C1 C2 C3 -176.30(11) . . . . ?
N1 C1 C2 C11 176.12(13) . . . . ?
Cl1 C1 C2 C11 0.3(2) . . . . ?
N1 N2 C3 C2 -0.03(17) . . . . ?
N1 N2 C3 C4 177.63(14) . . . . ?
C1 C2 C3 N2 0.34(17) . . . . ?
C11 C2 C3 N2 -176.54(13) . . . . ?
C1 C2 C3 C4 -177.05(15) . . . . ?
C11 C2 C3 C4 6.1(2) . . . . ?
C1 N1 C5 C6 112.24(17) . . . . ?
N2 N1 C5 C6 -66.98(18) . . . . ?
C1 N1 C5 C10 -69.7(2) . . . . ?
N2 N1 C5 C10 111.12(16) . . . . ?
C10 C5 C6 C7 0.7(2) . . . . ?
N1 C5 C6 C7 178.80(14) . . . . ?
C5 C6 C7 C8 0.0(2) . . . . ?
C6 C7 C8 C9 -0.7(3) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C6 C5 C10 C9 -0.8(2) . . . . ?
N1 C5 C10 C9 -178.87(14) . . . . ?
C8 C9 C10 C5 0.1(2) . . . . ?
C1 C2 C11 O1 -156.24(14) . . . . ?
C3 C2 C11 O1 19.7(2) . . . . ?
C1 C2 C11 C12 24.9(2) . . . . ?
C3 C2 C11 C12 -159.14(14) . . . . ?
O1 C11 C12 C13 -0.2(2) . . . . ?
C2 C11 C12 C13 178.64(13) . . . . ?
C20 N3 C13 C12 -176.03(14) . . . . ?
C20 N3 C13 C14 3.8(2) . . . . ?
C11 C12 C13 N3 2.3(2) . . . . ?
C11 C12 C13 C14 -177.51(12) . . . . ?
N3 C13 C14 C15 -105.06(16) . . . . ?
C12 C13 C14 C15 74.80(19) . . . . ?
N3 C13 C14 C19 73.07(18) . . . . ?
C12 C13 C14 C19 -107.07(16) . . . . ?
C19 C14 C15 C16 -0.6(2) . . . . ?
C13 C14 C15 C16 177.53(13) . . . . ?
C14 C15 C16 C17 0.9(2) . . . . ?
C15 C16 C17 C18 -0.3(2) . . . . ?
C16 C17 C18 C19 -0.5(3) . . . . ?
C17 C18 C19 C14 0.8(3) . . . . ?
C15 C14 C19 C18 -0.2(2) . . . . ?
C13 C14 C19 C18 -178.40(14) . . . . ?
C13 N3 C20 C21 168.53(14) . . . . ?
N3 C20 C21 C26 -38.1(2) . . . . ?
N3 C20 C21 C22 144.15(14) . . . . ?
C26 C21 C22 C23 -0.6(2) . . . . ?
C20 C21 C22 C23 177.23(13) . . . . ?
C21 C22 C23 C24 0.6(2) . . . . ?
C27 O2 C24 C23 -176.11(14) . . . . ?
C27 O2 C24 C25 3.9(2) . . . . ?
C22 C23 C24 O2 -179.76(13) . . . . ?
C22 C23 C24 C25 0.2(2) . . . . ?
O2 C24 C25 C26 178.90(14) . . . . ?
C23 C24 C25 C26 -1.1(2) . . . . ?
C22 C21 C26 C25 -0.3(2) . . . . ?
C20 C21 C26 C25 -178.04(14) . . . . ?
C24 C25 C26 C21 1.2(2) . . . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 30.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.321
_refine_diff_density_min -0.344
_refine_diff_density_rms 0.049
#===================== End of CIF submission =================================