# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011
data_global
_journal_name_full 'Chemical Science'
_journal_coden_cambridge 1475
_journal_year ?
_journal_volume ?
_journal_page_first ?
loop_
_publ_author_address
;
Department of Chemistry
University of Manchester
Manchester M13 9PL
England UK
;
_publ_contact_author_address
;
Department of Chemistry
University of Manchester
Manchester M13 9PL
England UK
;
_publ_contact_author_email jrtest@spec.ch.man.ac.uk
_publ_contact_author_fax 44(161)275-4734
_publ_contact_author_phone 44(161)275-4700
#TrackingRef 'S3167.cif'
#------------------ SUBMISSION DETAILS --------------------------------------#
# Name and address of author for correspondence
_publ_contact_author_name 'Raftery, James'
_publ_contact_letter # Include date of submission
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Date of submission ?
Please consider this CIF submission for publication as a
Regular Structural Paper in Acta Crystallographica C.
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_publ_requested_category ?
_publ_requested_coeditor_name ?
#------------------ TITLE AND AUTHOR LIST------------------------------------#
_publ_section_title
;
?
;
_publ_contact_author
;
Madeleine Helliwell
;
loop_
_publ_author_name
D.Procter
S.Coote
'Seidjolo Quenum'
data_s3167n
_database_code_depnum_ccdc_archive 'CCDC 780379'
_publ_section_title_footnote
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?
;
#------------------ TEXT ----------------------------------------------------#
_publ_section_synopsis
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# Insert blank lines between paragraphs
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_publ_section_abstract
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# Insert blank lines between paragraphs
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_publ_section_comment
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# Insert blank lines between paragraphs
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;
_publ_section_exptl_prep
;
?
;
_publ_section_exptl_refinement
;
The structure was solved by direct methods.
The non-hydrogen atoms were refined anisotropically. H atoms were included in
calculated positions with C-H lengths of 0.95(CH), 0.99(CH~2~) &
0.98(CH~3~)\%A; U\~iso(H) values were fixed at 1.2U~eq~(C) except for CH~3~
where it was 1.5U~eq~(C).
;
# Insert blank lines between references
_publ_section_references
;
#
# Put all your general crystallographic references here
# Delete as required from the document CIF
#
Bruker (2000). GEMINI (Version 1.02) and RLATT (Version 3.0).
Bruker AXS In=c., Madison, Wisconsin, USA.
Bruker (2001) SMART (Version 5.625), SADABS (Version 2.03a) and
SHELXTL (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2003). SMART (Version 5.630) and SAINT-Plus (Version 6.45A).
Bruker AXS Inc., Madison, Wisconsin, USA.
M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini,
G. L. Cascarano, L. De Caro,C. Giacovazzo, G. Polidori
and R. Spagna
SIR2004: an improved tool for crystal structure determination
and refinement
J. Appl. Cryst. (2005). 38, 381-388
Sheldrick, G.M. (1993) SHELXL93. Program for crystal structure
refinement. University of G\"ottingen, Germany.
Sheldrick, G.M. (1997) SHELXL97. Program for crystal structure
refinement. University of G\"ottingen, Germany.
Sheldrick, G.M. (1985). SHELXS86. In Crystallographic Computing 3,
edited by G. M. Sheldrick, C. Kruger & R. Goddard, pp. 175-189.
Oxford University Press.
Sheldrick, G.M. (1997) SHELXS97. Program for Crystal Structure solution.
University of G\"ottingen, Germany.
Sheldrick, G, M. (2005). CELL_NOW. University
of G\"ottingen, Germany.
Sheldrick, G, M. (2007). TWINABS. University
of G\"ottingen, Germany.
Sheldrick, G. M. (2008) A short history of SHELX . Acta Cryst. A64, 112-122.
Wilson, A.J.C. (1992) Ed. International Tables for Crystallography,
Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands.
;
_publ_section_figure_captions
;
Figure 1. View of (I) (50% probability displacement ellipsoids)
;
_publ_section_acknowledgements
;
?
;
_publ_section_table_legends
;
Table 1. Fractional atomic coordinates and equivalent
isotropic displacement parameters (\%A^2^)
Table 2. Selected geometric parameters (\%A ,\% )
;
#------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------#
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C25 H27 Br N2 O'
_chemical_formula_weight 451.40
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M P2(1)/c
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 16.0335(17)
_cell_length_b 9.3932(10)
_cell_length_c 15.1000(16)
_cell_angle_alpha 90.00
_cell_angle_beta 109.749(2)
_cell_angle_gamma 90.00
_cell_volume 2140.4(4)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 2362
_cell_measurement_theta_min 2.551
_cell_measurement_theta_max 22.763
_exptl_crystal_description block
_exptl_crystal_colour white
_exptl_crystal_size_max 0.20
_exptl_crystal_size_mid 0.16
_exptl_crystal_size_min 0.13
_exptl_crystal_density_diffrn 1.401
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 936
_exptl_absorpt_coefficient_mu 1.939
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 18153
_diffrn_reflns_av_R_equivalents 0.0662
_diffrn_reflns_av_sigmaI/netI 0.1066
_diffrn_reflns_limit_h_min -21
_diffrn_reflns_limit_h_max 21
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_theta_min 1.35
_diffrn_reflns_theta_max 28.29
_reflns_number_total 5107
_reflns_number_gt 3322
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker SMART'
_computing_cell_refinement 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0422P)^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 5107
_refine_ls_number_parameters 263
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0800
_refine_ls_R_factor_gt 0.0439
_refine_ls_wR_factor_ref 0.1093
_refine_ls_wR_factor_gt 0.0790
_refine_ls_goodness_of_fit_ref 0.905
_refine_ls_restrained_S_all 0.905
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.09798(3) -0.11414(4) 0.23196(3) 0.02311(12) Uani 1 1 d . . .
C1 C 0.2342(2) 0.2205(4) 0.5462(2) 0.0125(7) Uani 1 1 d . . .
C2 C 0.2335(2) 0.1394(4) 0.4596(2) 0.0131(7) Uani 1 1 d . . .
C3 C 0.1697(2) 0.0523(4) 0.3987(2) 0.0153(8) Uani 1 1 d . . .
H3 H 0.1168 0.0290 0.4104 0.018 Uiso 1 1 calc R . .
C4 C 0.1860(2) 0.0001(4) 0.3197(2) 0.0164(8) Uani 1 1 d . . .
C5 C 0.2628(2) 0.0309(4) 0.3016(2) 0.0187(8) Uani 1 1 d . . .
H5 H 0.2717 -0.0072 0.2473 0.022 Uiso 1 1 calc R . .
C6 C 0.3271(2) 0.1174(4) 0.3626(2) 0.0174(8) Uani 1 1 d . . .
H6 H 0.3802 0.1399 0.3509 0.021 Uiso 1 1 calc R . .
C7 C 0.3108(2) 0.1697(4) 0.4411(2) 0.0138(7) Uani 1 1 d . . .
C8 C 0.3211(2) 0.3017(4) 0.5714(2) 0.0146(8) Uani 1 1 d . . .
C9 C 0.4495(2) 0.3193(4) 0.5145(3) 0.0173(8) Uani 1 1 d . . .
H9A H 0.4641 0.4021 0.5575 0.021 Uiso 1 1 calc R . .
H9B H 0.4462 0.3530 0.4513 0.021 Uiso 1 1 calc R . .
C10 C 0.5233(2) 0.2102(4) 0.5485(3) 0.0212(9) Uani 1 1 d . . .
H10A H 0.5159 0.1367 0.4995 0.025 Uiso 1 1 calc R . .
H10B H 0.5200 0.1627 0.6058 0.025 Uiso 1 1 calc R . .
C11 C 0.6131(2) 0.2812(4) 0.5704(3) 0.0241(9) Uani 1 1 d . . .
H11A H 0.6140 0.3370 0.5159 0.036 Uiso 1 1 calc R . .
H11B H 0.6595 0.2081 0.5846 0.036 Uiso 1 1 calc R . .
H11C H 0.6240 0.3441 0.6249 0.036 Uiso 1 1 calc R . .
C12 C 0.2332(2) 0.1259(4) 0.6307(2) 0.0121(7) Uani 1 1 d . . .
H12 H 0.2547 0.1849 0.6892 0.014 Uiso 1 1 calc R . .
C13 C 0.0992(2) 0.2467(4) 0.5883(2) 0.0147(8) Uani 1 1 d . . .
H13 H 0.1118 0.2991 0.6491 0.018 Uiso 1 1 calc R . .
C14 C 0.1522(2) 0.3159(4) 0.5314(2) 0.0160(8) Uani 1 1 d . . .
H14A H 0.1705 0.4137 0.5543 0.019 Uiso 1 1 calc R . .
H14B H 0.1159 0.3206 0.4638 0.019 Uiso 1 1 calc R . .
C15 C 0.2896(2) -0.0063(4) 0.6460(2) 0.0131(7) Uani 1 1 d . . .
C16 C 0.3792(2) 0.0023(4) 0.6976(2) 0.0177(8) Uani 1 1 d . . .
H16 H 0.4039 0.0912 0.7237 0.021 Uiso 1 1 calc R . .
C17 C 0.4337(2) -0.1166(4) 0.7120(2) 0.0228(8) Uani 1 1 d . . .
H17 H 0.4952 -0.1083 0.7462 0.027 Uiso 1 1 calc R . .
C18 C 0.3980(3) -0.2473(4) 0.6763(3) 0.0225(9) Uani 1 1 d . . .
H18 H 0.4346 -0.3294 0.6870 0.027 Uiso 1 1 calc R . .
C19 C 0.3091(3) -0.2575(4) 0.6252(3) 0.0212(9) Uani 1 1 d . . .
H19 H 0.2845 -0.3472 0.6011 0.025 Uiso 1 1 calc R . .
C20 C 0.2548(2) -0.1379(4) 0.6085(2) 0.0174(8) Uani 1 1 d . . .
H20 H 0.1939 -0.1458 0.5715 0.021 Uiso 1 1 calc R . .
C21 C 0.1123(2) 0.0280(4) 0.6813(2) 0.0151(8) Uani 1 1 d . . .
H21A H 0.1248 -0.0748 0.6782 0.018 Uiso 1 1 calc R . .
H21B H 0.0475 0.0385 0.6663 0.018 Uiso 1 1 calc R . .
C22 C 0.1579(2) 0.0782(4) 0.7808(2) 0.0172(8) Uani 1 1 d . . .
H22 H 0.1523 0.1755 0.7951 0.021 Uiso 1 1 calc R . .
C23 C 0.2048(2) -0.0060(4) 0.8484(3) 0.0202(8) Uani 1 1 d . . .
H23A H 0.2113 -0.1037 0.8358 0.024 Uiso 1 1 calc R . .
H23B H 0.2323 0.0306 0.9101 0.024 Uiso 1 1 calc R . .
C24 C 0.0010(2) 0.2439(4) 0.5380(2) 0.0182(8) Uani 1 1 d . . .
H24 H -0.0212 0.1853 0.4838 0.022 Uiso 1 1 calc R . .
C25 C -0.0559(3) 0.3171(4) 0.5641(3) 0.0261(9) Uani 1 1 d . . .
H25A H -0.0359 0.3767 0.6180 0.031 Uiso 1 1 calc R . .
H25B H -0.1174 0.3107 0.5291 0.031 Uiso 1 1 calc R . .
N1 N 0.36326(19) 0.2643(3) 0.5094(2) 0.0146(6) Uani 1 1 d . . .
N2 N 0.13760(17) 0.1022(3) 0.60805(19) 0.0135(6) Uani 1 1 d . . .
O1 O 0.34962(15) 0.3862(3) 0.63636(16) 0.0193(6) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0289(2) 0.0202(2) 0.01645(19) -0.00432(18) 0.00260(15) -0.0017(2)
C1 0.0157(19) 0.0115(18) 0.0113(18) 0.0016(14) 0.0060(15) 0.0014(15)
C2 0.0157(18) 0.0133(19) 0.0103(17) 0.0025(14) 0.0047(14) 0.0035(15)
C3 0.0157(19) 0.0155(19) 0.0144(19) 0.0041(15) 0.0045(15) 0.0017(15)
C4 0.021(2) 0.0112(18) 0.0133(18) -0.0008(15) 0.0005(15) -0.0001(15)
C5 0.028(2) 0.017(2) 0.0112(19) -0.0004(15) 0.0066(16) 0.0039(17)
C6 0.0192(19) 0.0173(19) 0.0180(18) 0.0030(17) 0.0094(15) 0.0020(17)
C7 0.0165(19) 0.0122(18) 0.0114(17) 0.0030(14) 0.0030(15) 0.0011(15)
C8 0.0171(19) 0.0128(18) 0.0137(18) 0.0051(15) 0.0049(15) 0.0043(15)
C9 0.0143(19) 0.018(2) 0.020(2) 0.0007(16) 0.0070(16) -0.0040(16)
C10 0.019(2) 0.022(2) 0.024(2) 0.0013(17) 0.0090(17) 0.0000(17)
C11 0.019(2) 0.028(2) 0.027(2) -0.0014(18) 0.0097(18) 0.0004(18)
C12 0.0152(18) 0.0128(18) 0.0083(16) -0.0016(14) 0.0040(14) -0.0020(15)
C13 0.018(2) 0.0142(19) 0.0113(18) -0.0014(14) 0.0034(15) -0.0002(15)
C14 0.019(2) 0.0162(19) 0.0143(18) -0.0006(15) 0.0073(15) 0.0002(16)
C15 0.0179(19) 0.0147(19) 0.0092(17) 0.0028(14) 0.0082(15) 0.0014(15)
C16 0.020(2) 0.020(2) 0.0117(18) 0.0022(16) 0.0041(16) -0.0007(16)
C17 0.0180(19) 0.032(2) 0.0174(19) 0.0036(19) 0.0053(16) 0.0048(19)
C18 0.028(2) 0.022(2) 0.020(2) 0.0045(17) 0.0106(18) 0.0128(18)
C19 0.032(2) 0.016(2) 0.018(2) -0.0010(16) 0.0130(18) 0.0018(18)
C20 0.019(2) 0.021(2) 0.0127(18) 0.0015(15) 0.0062(15) -0.0018(16)
C21 0.0116(19) 0.0177(19) 0.0172(19) 0.0008(15) 0.0065(15) -0.0025(15)
C22 0.021(2) 0.018(2) 0.0171(19) -0.0039(15) 0.0121(16) -0.0051(16)
C23 0.023(2) 0.021(2) 0.0166(19) -0.0040(16) 0.0067(16) -0.0048(17)
C24 0.018(2) 0.018(2) 0.017(2) -0.0009(16) 0.0034(16) -0.0011(16)
C25 0.018(2) 0.025(2) 0.032(2) -0.0104(19) 0.0043(18) -0.0025(18)
N1 0.0154(16) 0.0151(16) 0.0146(15) 0.0003(13) 0.0067(13) -0.0013(13)
N2 0.0104(14) 0.0155(16) 0.0158(15) -0.0002(13) 0.0060(12) -0.0001(13)
O1 0.0213(14) 0.0179(13) 0.0191(13) -0.0043(12) 0.0073(11) -0.0034(12)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.906(3) . ?
C1 C2 1.511(4) . ?
C1 C8 1.520(5) . ?
C1 C14 1.544(5) . ?
C1 C12 1.559(4) . ?
C2 C3 1.388(5) . ?
C2 C7 1.389(5) . ?
C3 C4 1.392(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(5) . ?
C5 C6 1.389(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(5) . ?
C6 H6 0.9500 . ?
C7 N1 1.405(4) . ?
C8 O1 1.224(4) . ?
C8 N1 1.373(4) . ?
C9 N1 1.453(4) . ?
C9 C10 1.518(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.519(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N2 1.470(4) . ?
C12 C15 1.508(5) . ?
C12 H12 1.0000 . ?
C13 N2 1.479(4) . ?
C13 C24 1.500(5) . ?
C13 C14 1.542(5) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.386(5) . ?
C15 C20 1.395(5) . ?
C16 C17 1.389(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.375(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.391(5) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 N2 1.476(4) . ?
C21 C22 1.507(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.310(5) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9500 . ?
C23 H23B 0.9500 . ?
C24 C25 1.305(5) . ?
C24 H24 0.9500 . ?
C25 H25A 0.9500 . ?
C25 H25B 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
C2 C1 C8 102.0(3) . . ?
C2 C1 C14 114.2(3) . . ?
C8 C1 C14 114.1(3) . . ?
C2 C1 C12 115.0(3) . . ?
C8 C1 C12 110.1(3) . . ?
C14 C1 C12 101.9(3) . . ?
C3 C2 C7 119.7(3) . . ?
C3 C2 C1 131.3(3) . . ?
C7 C2 C1 109.0(3) . . ?
C2 C3 C4 117.8(3) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C5 C4 C3 122.2(3) . . ?
C5 C4 Br1 118.7(3) . . ?
C3 C4 Br1 119.0(3) . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 117.5(3) . . ?
C7 C6 H6 121.3 . . ?
C5 C6 H6 121.3 . . ?
C6 C7 C2 122.5(3) . . ?
C6 C7 N1 127.8(3) . . ?
C2 C7 N1 109.6(3) . . ?
O1 C8 N1 125.1(3) . . ?
O1 C8 C1 126.1(3) . . ?
N1 C8 C1 108.8(3) . . ?
N1 C9 C10 113.4(3) . . ?
N1 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 C11 110.6(3) . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C11 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 . . ?
N2 C12 C15 115.8(3) . . ?
N2 C12 C1 101.2(3) . . ?
C15 C12 C1 115.0(3) . . ?
N2 C12 H12 108.1 . . ?
C15 C12 H12 108.1 . . ?
C1 C12 H12 108.1 . . ?
N2 C13 C24 112.4(3) . . ?
N2 C13 C14 103.3(3) . . ?
C24 C13 C14 114.0(3) . . ?
N2 C13 H13 109.0 . . ?
C24 C13 H13 109.0 . . ?
C14 C13 H13 109.0 . . ?
C13 C14 C1 106.0(3) . . ?
C13 C14 H14A 110.5 . . ?
C1 C14 H14A 110.5 . . ?
C13 C14 H14B 110.5 . . ?
C1 C14 H14B 110.5 . . ?
H14A C14 H14B 108.7 . . ?
C16 C15 C20 118.4(3) . . ?
C16 C15 C12 119.5(3) . . ?
C20 C15 C12 122.0(3) . . ?
C15 C16 C17 121.2(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 119.8(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 119.6(4) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 120.8(4) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C19 C20 C15 120.1(3) . . ?
C19 C20 H20 119.9 . . ?
C15 C20 H20 119.9 . . ?
N2 C21 C22 115.8(3) . . ?
N2 C21 H21A 108.3 . . ?
C22 C21 H21A 108.3 . . ?
N2 C21 H21B 108.3 . . ?
C22 C21 H21B 108.3 . . ?
H21A C21 H21B 107.4 . . ?
C23 C22 C21 123.1(3) . . ?
C23 C22 H22 118.5 . . ?
C21 C22 H22 118.5 . . ?
C22 C23 H23A 120.0 . . ?
C22 C23 H23B 120.0 . . ?
H23A C23 H23B 120.0 . . ?
C25 C24 C13 124.1(3) . . ?
C25 C24 H24 118.0 . . ?
C13 C24 H24 118.0 . . ?
C24 C25 H25A 120.0 . . ?
C24 C25 H25B 120.0 . . ?
H25A C25 H25B 120.0 . . ?
C8 N1 C7 110.6(3) . . ?
C8 N1 C9 123.5(3) . . ?
C7 N1 C9 125.9(3) . . ?
C12 N2 C21 115.2(3) . . ?
C12 N2 C13 103.8(3) . . ?
C21 N2 C13 112.5(3) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C1 C2 C3 -175.3(3) . . . . ?
C14 C1 C2 C3 -51.7(5) . . . . ?
C12 C1 C2 C3 65.6(5) . . . . ?
C8 C1 C2 C7 1.2(4) . . . . ?
C14 C1 C2 C7 124.8(3) . . . . ?
C12 C1 C2 C7 -117.9(3) . . . . ?
C7 C2 C3 C4 -0.9(5) . . . . ?
C1 C2 C3 C4 175.3(3) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C2 C3 C4 Br1 -177.7(2) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
Br1 C4 C5 C6 178.0(3) . . . . ?
C4 C5 C6 C7 0.2(5) . . . . ?
C5 C6 C7 C2 -0.4(5) . . . . ?
C5 C6 C7 N1 -176.4(3) . . . . ?
C3 C2 C7 C6 0.8(5) . . . . ?
C1 C2 C7 C6 -176.2(3) . . . . ?
C3 C2 C7 N1 177.4(3) . . . . ?
C1 C2 C7 N1 0.4(4) . . . . ?
C2 C1 C8 O1 177.9(3) . . . . ?
C14 C1 C8 O1 54.2(5) . . . . ?
C12 C1 C8 O1 -59.6(4) . . . . ?
C2 C1 C8 N1 -2.5(3) . . . . ?
C14 C1 C8 N1 -126.1(3) . . . . ?
C12 C1 C8 N1 120.1(3) . . . . ?
N1 C9 C10 C11 -168.9(3) . . . . ?
C2 C1 C12 N2 -86.0(3) . . . . ?
C8 C1 C12 N2 159.6(3) . . . . ?
C14 C1 C12 N2 38.1(3) . . . . ?
C2 C1 C12 C15 39.6(4) . . . . ?
C8 C1 C12 C15 -74.9(4) . . . . ?
C14 C1 C12 C15 163.7(3) . . . . ?
N2 C13 C14 C1 -15.3(3) . . . . ?
C24 C13 C14 C1 -137.6(3) . . . . ?
C2 C1 C14 C13 110.9(3) . . . . ?
C8 C1 C14 C13 -132.3(3) . . . . ?
C12 C1 C14 C13 -13.7(3) . . . . ?
N2 C12 C15 C16 -158.0(3) . . . . ?
C1 C12 C15 C16 84.4(4) . . . . ?
N2 C12 C15 C20 23.0(4) . . . . ?
C1 C12 C15 C20 -94.6(4) . . . . ?
C20 C15 C16 C17 0.1(5) . . . . ?
C12 C15 C16 C17 -179.0(3) . . . . ?
C15 C16 C17 C18 -1.6(5) . . . . ?
C16 C17 C18 C19 1.3(5) . . . . ?
C17 C18 C19 C20 0.4(5) . . . . ?
C18 C19 C20 C15 -2.0(5) . . . . ?
C16 C15 C20 C19 1.7(5) . . . . ?
C12 C15 C20 C19 -179.3(3) . . . . ?
N2 C21 C22 C23 -122.1(4) . . . . ?
N2 C13 C24 C25 130.3(4) . . . . ?
C14 C13 C24 C25 -112.6(4) . . . . ?
O1 C8 N1 C7 -177.5(3) . . . . ?
C1 C8 N1 C7 2.9(4) . . . . ?
O1 C8 N1 C9 1.3(5) . . . . ?
C1 C8 N1 C9 -178.4(3) . . . . ?
C6 C7 N1 C8 174.3(3) . . . . ?
C2 C7 N1 C8 -2.1(4) . . . . ?
C6 C7 N1 C9 -4.4(6) . . . . ?
C2 C7 N1 C9 179.2(3) . . . . ?
C10 C9 N1 C8 107.5(4) . . . . ?
C10 C9 N1 C7 -74.0(4) . . . . ?
C15 C12 N2 C21 61.7(4) . . . . ?
C1 C12 N2 C21 -173.3(3) . . . . ?
C15 C12 N2 C13 -174.8(3) . . . . ?
C1 C12 N2 C13 -49.8(3) . . . . ?
C22 C21 N2 C12 44.4(4) . . . . ?
C22 C21 N2 C13 -74.3(4) . . . . ?
C24 C13 N2 C12 164.1(3) . . . . ?
C14 C13 N2 C12 40.8(3) . . . . ?
C24 C13 N2 C21 -70.7(3) . . . . ?
C14 C13 N2 C21 166.0(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.522
_refine_diff_density_min -0.366
_refine_diff_density_rms 0.090
# Attachment 'S3219.cif'
data_z:\s3219\work\s3219abs
_database_code_depnum_ccdc_archive 'CCDC 780380'
#TrackingRef 'S3219.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_publ_section_abstract
;
ENTER ABSTRACT
;
_publ_section_exptl_prep
;
ENTER EXPERIMENTAL SECTION
;
_publ_section_exptl_refinement
;
The structure was solved by the direct methods.
All non-H atoms were refined anisotropically.
H atoms were included in calculated positions.
The atoms C22, C23 are disordered over two sites
whose occupancies were constrained to sum to 1.0.
;
_publ_section_comment
;
ENTER TEXT
;
_publ_section_references
;
Bruker (2001). SMART (Version 5.625), SADABS (Version 2.03a) and
SHELXTL (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2002). SAINT. Version 6.36a. Bruker AXS Inc., Madison,
Wisconsin, USA.
M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini,
G. L. Cascarano, L. De Caro,C. Giacovazzo, G. Polidori
and R. Spagna
SIR2004: an improved tool for crystal structure determination
and refinement
J. Appl. Cryst. (2005). 38, 381-388
Sheldrick, G. M. (1997). SHELXS-97 and SHELXL-97.
University of G\"ottingen, Germany.
Sheldrick, G, M. (2005). CELL_NOW. University
of G\"ottingen, Germany.
Sheldrick, G, M. (2007). TWINABS. University
of G\"ottingen, Germany.
Spek, A.L. (2003) J.Appl.Cryst. 36, 2003, 7-13.
;
_publ_section_acknowledgements
;
ENTER ACKNOWLEDGEMENTS
;
_publ_section_table_legends
;
ENTER TABLE LEGENDS
;
_publ_section_figure_captions
;
ENTER FIGURE CAPTIONS
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C25 H27 Br N2 O'
_chemical_formula_weight 451.40
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M P2(1)/c
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 8.197(2)
_cell_length_b 22.507(6)
_cell_length_c 12.208(3)
_cell_angle_alpha 90.00
_cell_angle_beta 101.368(4)
_cell_angle_gamma 90.00
_cell_volume 2208.0(10)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 914
_cell_measurement_theta_min 2.48
_cell_measurement_theta_max 26.30
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.25
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.358
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 936
_exptl_absorpt_coefficient_mu 1.880
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.693
_exptl_absorpt_correction_T_max 1.000
_exptl_absorpt_process_details SADABS
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 16610
_diffrn_reflns_av_R_equivalents 0.0303
_diffrn_reflns_av_sigmaI/netI 0.0300
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -27
_diffrn_reflns_limit_k_max 28
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_theta_min 1.81
_diffrn_reflns_theta_max 26.41
_reflns_number_total 4505
_reflns_number_gt 3808
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker SMART'
_computing_cell_refinement 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0316P)^2^+1.5037P] 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 4505
_refine_ls_number_parameters 282
_refine_ls_number_restraints 3
_refine_ls_R_factor_all 0.0461
_refine_ls_R_factor_gt 0.0354
_refine_ls_wR_factor_ref 0.0817
_refine_ls_wR_factor_gt 0.0782
_refine_ls_goodness_of_fit_ref 1.096
_refine_ls_restrained_S_all 1.099
_refine_ls_shift/su_max 0.002
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.47651(3) 0.600613(11) 1.30325(2) 0.03454(9) Uani 1 1 d . . .
O1 O 0.1707(2) 0.72240(7) 0.71191(13) 0.0297(4) Uani 1 1 d . . .
N1 N 0.3272(2) 0.64765(8) 0.80889(15) 0.0270(4) Uani 1 1 d . . .
N2 N -0.0942(2) 0.74552(8) 0.86533(15) 0.0255(4) Uani 1 1 d . . .
C1 C 0.3731(3) 0.62997(10) 0.92062(18) 0.0259(5) Uani 1 1 d . . .
C2 C 0.4848(3) 0.58597(11) 0.9656(2) 0.0322(5) Uani 1 1 d . . .
H2 H 0.5390 0.5621 0.9195 0.039 Uiso 1 1 calc R . .
C3 C 0.5145(3) 0.57813(11) 1.0807(2) 0.0343(6) Uani 1 1 d . . .
H3 H 0.5903 0.5484 1.1145 0.041 Uiso 1 1 calc R . .
C4 C 0.4344(3) 0.61329(10) 1.14621(19) 0.0285(5) Uani 1 1 d . . .
C5 C 0.3224(3) 0.65774(10) 1.10137(19) 0.0263(5) Uani 1 1 d . . .
H5 H 0.2684 0.6816 1.1477 0.032 Uiso 1 1 calc R . .
C6 C 0.2931(3) 0.66567(10) 0.98733(18) 0.0240(5) Uani 1 1 d . A .
C7 C 0.1776(3) 0.70746(10) 0.91326(18) 0.0235(5) Uani 1 1 d . . .
C8 C 0.2196(3) 0.69512(10) 0.79809(18) 0.0245(5) Uani 1 1 d . A .
C9 C -0.0082(3) 0.69295(10) 0.91546(18) 0.0247(5) Uani 1 1 d . A .
H9 H -0.0213 0.6904 0.9950 0.030 Uiso 1 1 calc R . .
C10 C 0.0055(3) 0.79762(11) 0.9089(2) 0.0323(5) Uani 1 1 d . A .
H10 H -0.0308 0.8124 0.9775 0.039 Uiso 1 1 calc R . .
C11 C 0.1860(3) 0.77414(10) 0.94045(19) 0.0266(5) Uani 1 1 d . A .
H11A H 0.2584 0.7949 0.8966 0.032 Uiso 1 1 calc R . .
H11B H 0.2313 0.7806 1.0209 0.032 Uiso 1 1 calc R . .
C12 C 0.3854(3) 0.62114(11) 0.71445(19) 0.0301(5) Uani 1 1 d . . .
H12A H 0.5038 0.6099 0.7383 0.036 Uiso 1 1 calc R . .
H12B H 0.3777 0.6510 0.6542 0.036 Uiso 1 1 calc R . .
C13 C 0.2858(3) 0.56671(12) 0.6691(2) 0.0362(6) Uani 1 1 d . . .
H13A H 0.1658 0.5766 0.6536 0.043 Uiso 1 1 calc R . .
H13B H 0.3047 0.5348 0.7260 0.043 Uiso 1 1 calc R . .
C14 C 0.3349(3) 0.54459(12) 0.5627(2) 0.0403(6) Uani 1 1 d . . .
H14A H 0.3124 0.5756 0.5053 0.060 Uiso 1 1 calc R . .
H14B H 0.2702 0.5090 0.5362 0.060 Uiso 1 1 calc R . .
H14C H 0.4538 0.5349 0.5778 0.060 Uiso 1 1 calc R . .
C15 C -0.0724(3) 0.63625(10) 0.8564(2) 0.0295(5) Uani 1 1 d . . .
C16 C -0.0801(3) 0.58435(12) 0.9163(3) 0.0430(7) Uani 1 1 d . A .
H16 H -0.0480 0.5846 0.9954 0.052 Uiso 1 1 calc R . .
C17 C -0.1353(4) 0.53134(13) 0.8603(3) 0.0573(9) Uani 1 1 d . . .
H17 H -0.1403 0.4958 0.9017 0.069 Uiso 1 1 calc R A .
C18 C -0.1821(3) 0.53077(13) 0.7457(3) 0.0549(9) Uani 1 1 d . A .
H18 H -0.2182 0.4948 0.7078 0.066 Uiso 1 1 calc R . .
C19 C -0.1766(3) 0.58188(13) 0.6866(3) 0.0440(7) Uani 1 1 d . . .
H19 H -0.2102 0.5814 0.6075 0.053 Uiso 1 1 calc R A .
C20 C -0.1228(3) 0.63452(11) 0.7405(2) 0.0324(5) Uani 1 1 d . A .
H20 H -0.1201 0.6698 0.6981 0.039 Uiso 1 1 calc R . .
C21 C -0.2712(3) 0.74913(11) 0.8729(2) 0.0309(5) Uani 0.684(7) 1 d PD A 1
H21A H -0.3334 0.7189 0.8223 0.037 Uiso 0.684(7) 1 calc PR A 1
H21B H -0.3140 0.7886 0.8453 0.037 Uiso 0.684(7) 1 calc PR A 1
C22 C -0.3089(6) 0.7399(2) 0.9902(4) 0.0303(12) Uani 0.684(7) 1 d PD A 1
H22 H -0.2811 0.7028 1.0263 0.036 Uiso 0.684(7) 1 calc PR A 1
C23 C -0.3775(4) 0.78079(18) 1.0426(3) 0.0364(12) Uani 0.684(7) 1 d PD A 1
H23A H -0.4063 0.8182 1.0081 0.044 Uiso 0.684(7) 1 calc PR A 1
H23B H -0.3985 0.7730 1.1151 0.044 Uiso 0.684(7) 1 calc PR A 1
C21A C -0.2712(3) 0.74913(11) 0.8729(2) 0.0309(5) Uani 0.316(7) 1 d PD A 2
H21C H -0.3224 0.7095 0.8560 0.037 Uiso 0.316(7) 1 calc PR A 2
H21D H -0.3279 0.7770 0.8150 0.037 Uiso 0.316(7) 1 calc PR A 2
C22A C -0.3014(11) 0.7689(4) 0.9834(7) 0.025(2) Uani 0.316(7) 1 d PD A 2
H22A H -0.3021 0.8100 1.0012 0.029 Uiso 0.316(7) 1 calc PR A 2
C23A C -0.3272(10) 0.7287(4) 1.0560(8) 0.038(3) Uani 0.316(7) 1 d PD A 2
H23C H -0.3263 0.6877 1.0375 0.045 Uiso 0.316(7) 1 calc PR A 2
H23D H -0.3467 0.7406 1.1270 0.045 Uiso 0.316(7) 1 calc PR A 2
C24 C -0.0165(3) 0.84568(13) 0.8229(3) 0.0520(8) Uani 1 1 d . . .
H24 H 0.0021 0.8359 0.7507 0.062 Uiso 1 1 calc R A .
C25 C -0.0601(4) 0.90089(14) 0.8404(4) 0.0838(14) Uani 1 1 d . A .
H25A H -0.0798 0.9122 0.9116 0.101 Uiso 1 1 calc R . .
H25B H -0.0719 0.9292 0.7817 0.101 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 0.03512(14) 0.03494(15) 0.03066(13) 0.00482(11) -0.00058(9) -0.00337(11)
O1 0.0322(9) 0.0297(9) 0.0291(9) 0.0027(7) 0.0107(7) 0.0017(7)
N1 0.0263(10) 0.0296(11) 0.0268(10) -0.0019(8) 0.0090(8) 0.0034(8)
N2 0.0225(9) 0.0254(10) 0.0293(10) -0.0023(8) 0.0067(8) 0.0028(8)
C1 0.0222(11) 0.0275(12) 0.0285(12) -0.0024(9) 0.0062(9) -0.0017(9)
C2 0.0281(12) 0.0315(13) 0.0365(13) -0.0048(10) 0.0055(10) 0.0080(10)
C3 0.0286(13) 0.0266(12) 0.0444(14) -0.0003(11) -0.0006(11) 0.0058(10)
C4 0.0268(12) 0.0280(13) 0.0294(12) 0.0030(9) 0.0026(9) -0.0035(9)
C5 0.0225(11) 0.0254(12) 0.0308(12) -0.0021(9) 0.0050(9) -0.0024(9)
C6 0.0177(10) 0.0240(12) 0.0305(12) -0.0005(9) 0.0058(9) -0.0011(8)
C7 0.0218(11) 0.0239(11) 0.0254(11) 0.0007(9) 0.0063(9) 0.0001(9)
C8 0.0201(11) 0.0250(12) 0.0295(12) -0.0029(9) 0.0075(9) -0.0023(9)
C9 0.0205(11) 0.0286(12) 0.0263(11) 0.0005(9) 0.0076(9) 0.0028(9)
C10 0.0265(12) 0.0279(13) 0.0432(14) -0.0064(11) 0.0083(10) 0.0029(10)
C11 0.0267(12) 0.0246(12) 0.0285(12) -0.0023(9) 0.0056(9) 0.0003(9)
C12 0.0306(12) 0.0328(13) 0.0296(12) -0.0038(10) 0.0125(10) 0.0048(10)
C13 0.0347(13) 0.0423(15) 0.0342(13) -0.0092(11) 0.0133(11) -0.0008(11)
C14 0.0457(16) 0.0429(16) 0.0331(14) -0.0071(12) 0.0096(12) 0.0042(12)
C15 0.0180(11) 0.0266(12) 0.0450(14) 0.0010(10) 0.0091(10) 0.0012(9)
C16 0.0296(13) 0.0337(15) 0.0639(18) 0.0107(13) 0.0046(12) 0.0005(11)
C17 0.0329(15) 0.0260(15) 0.111(3) 0.0140(16) 0.0096(17) 0.0008(11)
C18 0.0256(14) 0.0368(17) 0.099(3) -0.0202(17) 0.0039(15) -0.0013(12)
C19 0.0240(13) 0.0454(17) 0.0626(18) -0.0220(14) 0.0083(12) -0.0022(11)
C20 0.0229(12) 0.0340(14) 0.0409(14) -0.0092(11) 0.0082(10) -0.0006(10)
C21 0.0237(12) 0.0354(13) 0.0329(12) -0.0063(10) 0.0039(10) 0.0042(10)
C22 0.023(2) 0.028(3) 0.039(3) -0.002(3) 0.0053(17) 0.002(2)
C23 0.028(2) 0.045(3) 0.035(2) -0.0003(17) 0.0058(16) 0.0017(17)
C21A 0.0237(12) 0.0354(13) 0.0329(12) -0.0063(10) 0.0039(10) 0.0042(10)
C22A 0.016(4) 0.021(5) 0.037(5) -0.007(5) 0.005(3) 0.001(4)
C23A 0.033(5) 0.050(6) 0.029(5) -0.005(4) 0.005(4) -0.004(4)
C24 0.0281(14) 0.0349(16) 0.090(2) 0.0174(15) 0.0041(14) 0.0010(12)
C25 0.0362(17) 0.0339(17) 0.174(4) 0.020(2) 0.003(2) 0.0032(14)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.901(2) . ?
O1 C8 1.216(3) . ?
N1 C8 1.375(3) . ?
N1 C1 1.399(3) . ?
N1 C12 1.459(3) . ?
N2 C9 1.450(3) . ?
N2 C10 1.468(3) . ?
N2 C21 1.474(3) . ?
C1 C2 1.387(3) . ?
C1 C6 1.396(3) . ?
C2 C3 1.389(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(3) . ?
C5 C6 1.377(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.504(3) . ?
C7 C11 1.536(3) . ?
C7 C8 1.537(3) . ?
C7 C9 1.563(3) . ?
C9 C15 1.508(3) . ?
C9 H9 1.0000 . ?
C10 C24 1.493(4) . ?
C10 C11 1.547(3) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.515(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.518(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.386(3) . ?
C15 C20 1.395(3) . ?
C16 C17 1.404(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.377(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.363(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.385(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.537(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.309(6) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9500 . ?
C23 H23B 0.9500 . ?
C22A C23A 1.312(11) . ?
C22A H22A 0.9500 . ?
C23A H23C 0.9500 . ?
C23A H23D 0.9500 . ?
C24 C25 1.322(4) . ?
C24 H24 0.9500 . ?
C25 H25A 0.9500 . ?
C25 H25B 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
C8 N1 C1 111.03(18) . . ?
C8 N1 C12 123.04(19) . . ?
C1 N1 C12 125.92(19) . . ?
C9 N2 C10 108.02(17) . . ?
C9 N2 C21 114.93(18) . . ?
C10 N2 C21 114.70(18) . . ?
C2 C1 C6 122.0(2) . . ?
C2 C1 N1 128.3(2) . . ?
C6 C1 N1 109.74(19) . . ?
C1 C2 C3 117.5(2) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 122.4(2) . . ?
C3 C4 Br1 119.07(18) . . ?
C5 C4 Br1 118.55(17) . . ?
C6 C5 C4 117.4(2) . . ?
C6 C5 H5 121.3 . . ?
C4 C5 H5 121.3 . . ?
C5 C6 C1 120.5(2) . . ?
C5 C6 C7 130.7(2) . . ?
C1 C6 C7 108.76(19) . . ?
C6 C7 C11 119.02(18) . . ?
C6 C7 C8 102.06(17) . . ?
C11 C7 C8 111.44(18) . . ?
C6 C7 C9 111.05(18) . . ?
C11 C7 C9 101.71(17) . . ?
C8 C7 C9 111.88(18) . . ?
O1 C8 N1 124.8(2) . . ?
O1 C8 C7 127.2(2) . . ?
N1 C8 C7 107.91(18) . . ?
N2 C9 C15 113.19(18) . . ?
N2 C9 C7 102.52(17) . . ?
C15 C9 C7 114.71(18) . . ?
N2 C9 H9 108.7 . . ?
C15 C9 H9 108.7 . . ?
C7 C9 H9 108.7 . . ?
N2 C10 C24 110.0(2) . . ?
N2 C10 C11 104.73(18) . . ?
C24 C10 C11 113.6(2) . . ?
N2 C10 H10 109.5 . . ?
C24 C10 H10 109.5 . . ?
C11 C10 H10 109.5 . . ?
C7 C11 C10 106.26(18) . . ?
C7 C11 H11A 110.5 . . ?
C10 C11 H11A 110.5 . . ?
C7 C11 H11B 110.5 . . ?
C10 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
N1 C12 C13 112.52(19) . . ?
N1 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
N1 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 C14 111.3(2) . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 118.4(2) . . ?
C16 C15 C9 120.6(2) . . ?
C20 C15 C9 120.9(2) . . ?
C15 C16 C17 120.2(3) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 120.1(3) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.8(3) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C19 C20 C15 120.6(3) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?
N2 C21 C22 115.6(2) . . ?
N2 C21 H21A 108.4 . . ?
C22 C21 H21A 108.4 . . ?
N2 C21 H21B 108.4 . . ?
C22 C21 H21B 108.4 . . ?
H21A C21 H21B 107.4 . . ?
C23 C22 C21 123.0(5) . . ?
C23 C22 H22 118.5 . . ?
C21 C22 H22 118.5 . . ?
C22 C23 H23A 120.0 . . ?
C22 C23 H23B 120.0 . . ?
H23A C23 H23B 120.0 . . ?
C23A C22A H22A 120.5 . . ?
C22A C23A H23C 120.0 . . ?
C22A C23A H23D 120.0 . . ?
H23C C23A H23D 120.0 . . ?
C25 C24 C10 124.5(4) . . ?
C25 C24 H24 117.7 . . ?
C10 C24 H24 117.7 . . ?
C24 C25 H25A 120.0 . . ?
C24 C25 H25B 120.0 . . ?
H25A C25 H25B 120.0 . . ?
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 -176.6(2) . . . . ?
C12 N1 C1 C2 2.2(4) . . . . ?
C8 N1 C1 C6 0.9(3) . . . . ?
C12 N1 C1 C6 179.8(2) . . . . ?
C6 C1 C2 C3 0.4(4) . . . . ?
N1 C1 C2 C3 177.6(2) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C2 C3 C4 Br1 179.32(19) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
Br1 C4 C5 C6 -179.49(16) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C4 C5 C6 C7 177.7(2) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
N1 C1 C6 C5 -178.2(2) . . . . ?
C2 C1 C6 C7 -178.5(2) . . . . ?
N1 C1 C6 C7 3.8(2) . . . . ?
C5 C6 C7 C11 52.9(3) . . . . ?
C1 C6 C7 C11 -129.5(2) . . . . ?
C5 C6 C7 C8 176.0(2) . . . . ?
C1 C6 C7 C8 -6.4(2) . . . . ?
C5 C6 C7 C9 -64.6(3) . . . . ?
C1 C6 C7 C9 113.0(2) . . . . ?
C1 N1 C8 O1 173.8(2) . . . . ?
C12 N1 C8 O1 -5.2(3) . . . . ?
C1 N1 C8 C7 -5.1(2) . . . . ?
C12 N1 C8 C7 176.01(19) . . . . ?
C6 C7 C8 O1 -171.9(2) . . . . ?
C11 C7 C8 O1 -43.8(3) . . . . ?
C9 C7 C8 O1 69.3(3) . . . . ?
C6 C7 C8 N1 6.9(2) . . . . ?
C11 C7 C8 N1 134.95(19) . . . . ?
C9 C7 C8 N1 -111.9(2) . . . . ?
C10 N2 C9 C15 -164.94(19) . . . . ?
C21 N2 C9 C15 65.6(2) . . . . ?
C10 N2 C9 C7 -40.8(2) . . . . ?
C21 N2 C9 C7 -170.29(17) . . . . ?
C6 C7 C9 N2 165.66(17) . . . . ?
C11 C7 C9 N2 38.0(2) . . . . ?
C8 C7 C9 N2 -81.0(2) . . . . ?
C6 C7 C9 C15 -71.2(2) . . . . ?
C11 C7 C9 C15 161.14(19) . . . . ?
C8 C7 C9 C15 42.1(3) . . . . ?
C9 N2 C10 C24 148.7(2) . . . . ?
C21 N2 C10 C24 -81.7(3) . . . . ?
C9 N2 C10 C11 26.3(2) . . . . ?
C21 N2 C10 C11 155.89(19) . . . . ?
C6 C7 C11 C10 -144.8(2) . . . . ?
C8 C7 C11 C10 96.9(2) . . . . ?
C9 C7 C11 C10 -22.5(2) . . . . ?
N2 C10 C11 C7 -0.7(2) . . . . ?
C24 C10 C11 C7 -120.8(2) . . . . ?
C8 N1 C12 C13 -97.1(3) . . . . ?
C1 N1 C12 C13 84.1(3) . . . . ?
N1 C12 C13 C14 173.0(2) . . . . ?
N2 C9 C15 C16 -144.1(2) . . . . ?
C7 C9 C15 C16 98.7(3) . . . . ?
N2 C9 C15 C20 36.9(3) . . . . ?
C7 C9 C15 C20 -80.2(3) . . . . ?
C20 C15 C16 C17 0.9(4) . . . . ?
C9 C15 C16 C17 -178.0(2) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C16 C17 C18 C19 -0.7(4) . . . . ?
C17 C18 C19 C20 0.7(4) . . . . ?
C18 C19 C20 C15 0.2(4) . . . . ?
C16 C15 C20 C19 -1.0(3) . . . . ?
C9 C15 C20 C19 178.0(2) . . . . ?
C9 N2 C21 C22 51.0(3) . . . . ?
C10 N2 C21 C22 -75.1(3) . . . . ?
N2 C21 C22 C23 118.2(4) . . . . ?
N2 C10 C24 C25 127.0(3) . . . . ?
C11 C10 C24 C25 -115.9(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full 26.41
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max 0.328
_refine_diff_density_min -0.325
_refine_diff_density_rms 0.054
# Attachment 'S3242.cif'
data_s3242m
_database_code_depnum_ccdc_archive 'CCDC 780381'
_publ_section_title_footnote
;
?
;
#------------------ TEXT ----------------------------------------------------#
_publ_section_synopsis
;
# Insert blank lines between paragraphs
?
;
_publ_section_abstract
;
# Insert blank lines between paragraphs
?
;
_publ_section_comment
;
# Insert blank lines between paragraphs
?
;
_publ_section_exptl_prep
;
?
;
_publ_section_exptl_refinement
;
The structure was solved by direct methods.
The non-hydrogen atoms were refined anisotropically. H atoms were included in
calculated positions with C-H lengths of 0.95(CH), 0.99(CH~2~) &
0.98(CH~3~)\%A; U\~iso(H) values were fixed at 1.2U~eq~(C) except for CH~3~
where it was 1.5U~eq~(C).
;
# Insert blank lines between references
_publ_section_references
;
#
# Put all your general crystallographic references here
# Delete as required from the document CIF
#
Bruker (2000). GEMINI (Version 1.02) and RLATT (Version 3.0).
Bruker AXS In=c., Madison, Wisconsin, USA.
Bruker (2001) SMART (Version 5.625), SADABS (Version 2.03a) and
SHELXTL (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2003). SMART (Version 5.630) and SAINT-Plus (Version 6.45A).
Bruker AXS Inc., Madison, Wisconsin, USA.
M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini,
G. L. Cascarano, L. De Caro,C. Giacovazzo, G. Polidori
and R. Spagna
SIR2004: an improved tool for crystal structure determination
and refinement
J. Appl. Cryst. (2005). 38, 381-388
Sheldrick, G.M. (1993) SHELXL93. Program for crystal structure
refinement. University of G\"ottingen, Germany.
Sheldrick, G.M. (1997) SHELXL97. Program for crystal structure
refinement. University of G\"ottingen, Germany.
Sheldrick, G.M. (1985). SHELXS86. In Crystallographic Computing 3,
edited by G. M. Sheldrick, C. Kruger & R. Goddard, pp. 175-189.
Oxford University Press.
Sheldrick, G.M. (1997) SHELXS97. Program for Crystal Structure solution.
University of G\"ottingen, Germany.
Sheldrick, G, M. (2005). CELL_NOW. University
of G\"ottingen, Germany.
Sheldrick, G, M. (2007). TWINABS. University
of G\"ottingen, Germany.
Sheldrick, G. M. (2008) A short history of SHELX . Acta Cryst. A64, 112-122.
Wilson, A.J.C. (1992) Ed. International Tables for Crystallography,
Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands.
;
_publ_section_figure_captions
;
Figure 1. View of (I) (50% probability displacement ellipsoids)
;
_publ_section_acknowledgements
;
?
;
_publ_section_table_legends
;
Table 1. Fractional atomic coordinates and equivalent
isotropic displacement parameters (\%A^2^)
Table 2. Selected geometric parameters (\%A ,\% )
;
#------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------#
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C27 H27 Br N2 O2 S'
_chemical_formula_weight 523.48
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M P2(1)/c
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 13.9702(9)
_cell_length_b 9.4045(6)
_cell_length_c 18.4052(12)
_cell_angle_alpha 90.00
_cell_angle_beta 94.4320(10)
_cell_angle_gamma 90.00
_cell_volume 2410.9(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 5155
_cell_measurement_theta_min 2.2205
_cell_measurement_theta_max 28.196
_exptl_crystal_description block
_exptl_crystal_colour white
_exptl_crystal_size_max 0.32
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_min 0.20
_exptl_crystal_density_diffrn 1.442
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1080
_exptl_absorpt_coefficient_mu 1.819
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 20289
_diffrn_reflns_av_R_equivalents 0.0530
_diffrn_reflns_av_sigmaI/netI 0.0599
_diffrn_reflns_limit_h_min -18
_diffrn_reflns_limit_h_max 18
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_limit_l_max 23
_diffrn_reflns_theta_min 1.46
_diffrn_reflns_theta_max 28.26
_reflns_number_total 5721
_reflns_number_gt 4170
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker SMART'
_computing_cell_refinement 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0446P)^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 5721
_refine_ls_number_parameters 300
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0533
_refine_ls_R_factor_gt 0.0356
_refine_ls_wR_factor_ref 0.0928
_refine_ls_wR_factor_gt 0.0772
_refine_ls_goodness_of_fit_ref 0.958
_refine_ls_restrained_S_all 0.958
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.399292(19) 0.15232(3) 0.061289(15) 0.03391(10) Uani 1 1 d . . .
C1 C 0.74552(15) 0.2388(2) 0.21681(12) 0.0138(5) Uani 1 1 d . . .
C2 C 0.66873(16) 0.2563(2) 0.15526(12) 0.0141(5) Uani 1 1 d . . .
C3 C 0.57910(17) 0.1943(2) 0.14248(13) 0.0177(5) Uani 1 1 d . . .
H3 H 0.5558 0.1286 0.1761 0.021 Uiso 1 1 calc R . .
C4 C 0.52422(16) 0.2310(3) 0.07897(13) 0.0193(5) Uani 1 1 d . . .
C5 C 0.55697(17) 0.3245(2) 0.02814(13) 0.0197(5) Uani 1 1 d . . .
H5 H 0.5180 0.3461 -0.0150 0.024 Uiso 1 1 calc R . .
C6 C 0.64736(17) 0.3867(2) 0.04068(12) 0.0171(5) Uani 1 1 d . . .
H6 H 0.6710 0.4514 0.0067 0.021 Uiso 1 1 calc R . .
C7 C 0.70157(16) 0.3510(2) 0.10427(12) 0.0141(5) Uani 1 1 d . . .
C8 C 0.82476(16) 0.3394(2) 0.19328(12) 0.0152(5) Uani 1 1 d . . .
C9 C 0.84978(16) 0.5013(2) 0.08869(13) 0.0171(5) Uani 1 1 d . . .
H9A H 0.8442 0.4772 0.0362 0.021 Uiso 1 1 calc R . .
H9B H 0.9183 0.4932 0.1065 0.021 Uiso 1 1 calc R . .
C10 C 0.81685(18) 0.6536(2) 0.09827(14) 0.0221(5) Uani 1 1 d . . .
H10A H 0.7481 0.6611 0.0811 0.027 Uiso 1 1 calc R . .
H10B H 0.8534 0.7167 0.0675 0.027 Uiso 1 1 calc R . .
C11 C 0.8301(2) 0.7045(3) 0.17674(15) 0.0326(7) Uani 1 1 d . . .
H11A H 0.7912 0.6457 0.2072 0.049 Uiso 1 1 calc R . .
H11B H 0.8096 0.8039 0.1794 0.049 Uiso 1 1 calc R . .
H11C H 0.8979 0.6967 0.1943 0.049 Uiso 1 1 calc R . .
C12 C 0.71940(15) 0.2777(2) 0.29579(11) 0.0132(5) Uani 1 1 d . . .
H12 H 0.7325 0.3810 0.3047 0.016 Uiso 1 1 calc R . .
C13 C 0.61671(16) 0.2467(2) 0.30960(12) 0.0149(5) Uani 1 1 d . . .
C14 C 0.53919(17) 0.3368(2) 0.30236(12) 0.0175(5) Uani 1 1 d . . .
H14 H 0.5436 0.4345 0.2900 0.021 Uiso 1 1 calc R . .
C15 C 0.45192(17) 0.2678(3) 0.31535(14) 0.0258(6) Uani 1 1 d . . .
H15 H 0.3914 0.3142 0.3122 0.031 Uiso 1 1 calc R . .
C16 C 0.46398(17) 0.1293(3) 0.33259(13) 0.0232(6) Uani 1 1 d . . .
H16 H 0.4130 0.0671 0.3426 0.028 Uiso 1 1 calc R . .
C17 C 0.82568(16) 0.2591(2) 0.40803(12) 0.0138(5) Uani 1 1 d . . .
C18 C 0.77004(16) 0.3567(2) 0.44424(12) 0.0156(5) Uani 1 1 d . . .
H18 H 0.7062 0.3765 0.4255 0.019 Uiso 1 1 calc R . .
C19 C 0.80721(16) 0.4243(2) 0.50687(12) 0.0162(5) Uani 1 1 d . . .
H19 H 0.7690 0.4915 0.5301 0.019 Uiso 1 1 calc R . .
C20 C 0.89967(16) 0.3951(2) 0.53628(12) 0.0145(5) Uani 1 1 d . . .
C21 C 0.95452(16) 0.2957(2) 0.50252(12) 0.0161(5) Uani 1 1 d . . .
H21 H 1.0173 0.2733 0.5227 0.019 Uiso 1 1 calc R . .
C22 C 0.91754(16) 0.2286(2) 0.43894(12) 0.0149(5) Uani 1 1 d . . .
H22 H 0.9557 0.1606 0.4162 0.018 Uiso 1 1 calc R . .
C23 C 1.02108(17) 0.4343(3) 0.63328(13) 0.0208(5) Uani 1 1 d . . .
H23A H 1.0220 0.3336 0.6471 0.031 Uiso 1 1 calc R . .
H23B H 1.0333 0.4929 0.6770 0.031 Uiso 1 1 calc R . .
H23C H 1.0710 0.4522 0.5998 0.031 Uiso 1 1 calc R . .
C24 C 0.84555(16) 0.0975(2) 0.30209(12) 0.0147(5) Uani 1 1 d . . .
H24 H 0.9091 0.1430 0.2957 0.018 Uiso 1 1 calc R . .
C25 C 0.78699(16) 0.0889(2) 0.22810(12) 0.0151(5) Uani 1 1 d . . .
H25A H 0.8285 0.0637 0.1888 0.018 Uiso 1 1 calc R . .
H25B H 0.7351 0.0174 0.2292 0.018 Uiso 1 1 calc R . .
C26 C 0.86111(16) -0.0476(2) 0.33518(12) 0.0167(5) Uani 1 1 d . . .
H26 H 0.9103 -0.1042 0.3170 0.020 Uiso 1 1 calc R . .
C27 C 0.81335(18) -0.1038(3) 0.38681(13) 0.0219(5) Uani 1 1 d . . .
H27A H 0.7635 -0.0515 0.4068 0.026 Uiso 1 1 calc R . .
H27B H 0.8287 -0.1968 0.4042 0.026 Uiso 1 1 calc R . .
N1 N 0.79354(13) 0.39961(19) 0.12798(10) 0.0142(4) Uani 1 1 d . . .
N2 N 0.78676(13) 0.19346(19) 0.34363(10) 0.0135(4) Uani 1 1 d . . .
O1 O 0.90272(11) 0.36179(17) 0.22593(8) 0.0189(4) Uani 1 1 d . . .
O2 O 0.92915(11) 0.46945(17) 0.59821(8) 0.0182(4) Uani 1 1 d . . .
S2 S 0.58202(4) 0.07852(7) 0.33436(3) 0.01977(14) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.02240(15) 0.04255(19) 0.03435(17) 0.01245(13) -0.01347(11) -0.01463(12)
C1 0.0138(11) 0.0152(11) 0.0123(11) -0.0008(9) -0.0002(9) -0.0021(9)
C2 0.0156(11) 0.0138(11) 0.0126(11) -0.0034(9) 0.0003(9) 0.0008(9)
C3 0.0183(12) 0.0174(12) 0.0171(12) 0.0008(9) 0.0005(10) -0.0034(9)
C4 0.0143(12) 0.0218(13) 0.0213(12) -0.0011(10) -0.0024(10) -0.0051(10)
C5 0.0225(13) 0.0206(13) 0.0151(12) 0.0004(10) -0.0036(10) 0.0008(10)
C6 0.0190(12) 0.0178(12) 0.0146(11) 0.0015(9) 0.0021(9) -0.0008(9)
C7 0.0150(11) 0.0134(11) 0.0141(11) -0.0048(9) 0.0020(9) 0.0004(9)
C8 0.0165(12) 0.0146(11) 0.0146(11) -0.0038(9) 0.0024(9) 0.0007(9)
C9 0.0166(12) 0.0183(12) 0.0169(12) 0.0015(9) 0.0035(10) -0.0035(9)
C10 0.0192(12) 0.0182(12) 0.0291(14) 0.0041(11) 0.0028(10) -0.0031(10)
C11 0.0390(17) 0.0200(14) 0.0389(17) -0.0081(12) 0.0040(13) 0.0014(12)
C12 0.0139(11) 0.0127(11) 0.0125(11) 0.0005(9) -0.0028(9) 0.0008(9)
C13 0.0158(11) 0.0179(12) 0.0104(11) 0.0000(9) -0.0021(9) -0.0017(9)
C14 0.0163(11) 0.0185(12) 0.0176(12) 0.0006(10) 0.0005(9) 0.0005(10)
C15 0.0141(12) 0.0368(16) 0.0263(14) -0.0016(12) 0.0000(10) 0.0037(11)
C16 0.0137(12) 0.0370(16) 0.0189(12) -0.0009(11) 0.0013(10) -0.0082(11)
C17 0.0154(11) 0.0135(11) 0.0124(11) 0.0015(9) 0.0013(9) -0.0016(9)
C18 0.0127(11) 0.0175(12) 0.0163(11) 0.0017(10) 0.0003(9) 0.0017(9)
C19 0.0176(12) 0.0147(12) 0.0166(12) -0.0023(9) 0.0036(9) 0.0024(9)
C20 0.0166(11) 0.0161(11) 0.0105(10) 0.0007(9) 0.0002(9) -0.0047(9)
C21 0.0140(11) 0.0184(12) 0.0156(11) 0.0012(9) -0.0012(9) -0.0007(9)
C22 0.0136(11) 0.0157(12) 0.0154(11) -0.0009(9) 0.0015(9) 0.0020(9)
C23 0.0199(12) 0.0252(14) 0.0165(12) -0.0010(10) -0.0037(10) -0.0016(10)
C24 0.0138(11) 0.0160(11) 0.0144(11) -0.0024(9) 0.0007(9) 0.0008(9)
C25 0.0157(11) 0.0154(12) 0.0141(11) -0.0022(9) 0.0007(9) -0.0008(9)
C26 0.0156(11) 0.0156(12) 0.0180(12) -0.0051(10) -0.0034(9) 0.0035(9)
C27 0.0243(13) 0.0195(13) 0.0212(13) 0.0016(10) -0.0022(11) 0.0044(10)
N1 0.0135(9) 0.0148(10) 0.0142(10) 0.0002(8) 0.0011(8) -0.0026(7)
N2 0.0139(9) 0.0142(9) 0.0121(9) -0.0019(7) -0.0015(8) 0.0037(7)
O1 0.0151(8) 0.0219(9) 0.0191(9) -0.0006(7) -0.0014(7) -0.0042(7)
O2 0.0165(8) 0.0233(9) 0.0142(8) -0.0050(7) -0.0029(7) -0.0005(7)
S2 0.0184(3) 0.0216(3) 0.0193(3) 0.0023(3) 0.0012(2) -0.0028(2)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.900(2) . ?
C1 C2 1.508(3) . ?
C1 C25 1.532(3) . ?
C1 C8 1.543(3) . ?
C1 C12 1.569(3) . ?
C2 C3 1.385(3) . ?
C2 C7 1.397(3) . ?
C3 C4 1.391(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(3) . ?
C5 C6 1.395(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(3) . ?
C6 H6 0.9500 . ?
C7 N1 1.401(3) . ?
C8 O1 1.221(3) . ?
C8 N1 1.369(3) . ?
C9 N1 1.464(3) . ?
C9 C10 1.519(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.519(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N2 1.470(3) . ?
C12 C13 1.505(3) . ?
C12 H12 1.0000 . ?
C13 C14 1.373(3) . ?
C13 S2 1.726(2) . ?
C14 C15 1.418(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.348(4) . ?
C15 H15 0.9500 . ?
C16 S2 1.715(3) . ?
C16 H16 0.9500 . ?
C17 C22 1.393(3) . ?
C17 C18 1.404(3) . ?
C17 N2 1.408(3) . ?
C18 C19 1.382(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.389(3) . ?
C19 H19 0.9500 . ?
C20 O2 1.373(3) . ?
C20 C21 1.386(3) . ?
C21 C22 1.393(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 O2 1.431(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 N2 1.473(3) . ?
C24 C26 1.503(3) . ?
C24 C25 1.536(3) . ?
C24 H24 1.0000 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.314(3) . ?
C26 H26 0.9500 . ?
C27 H27A 0.9500 . ?
C27 H27B 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
C2 C1 C25 116.24(18) . . ?
C2 C1 C8 101.90(18) . . ?
C25 C1 C8 109.28(18) . . ?
C2 C1 C12 117.88(18) . . ?
C25 C1 C12 101.62(17) . . ?
C8 C1 C12 109.90(17) . . ?
C3 C2 C7 119.6(2) . . ?
C3 C2 C1 131.5(2) . . ?
C7 C2 C1 108.85(19) . . ?
C2 C3 C4 118.1(2) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C5 C4 C3 122.3(2) . . ?
C5 C4 Br1 118.53(17) . . ?
C3 C4 Br1 119.13(18) . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 117.9(2) . . ?
C7 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C6 C7 C2 122.4(2) . . ?
C6 C7 N1 127.8(2) . . ?
C2 C7 N1 109.85(19) . . ?
O1 C8 N1 124.9(2) . . ?
O1 C8 C1 126.8(2) . . ?
N1 C8 C1 108.25(18) . . ?
N1 C9 C10 112.32(19) . . ?
N1 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 C11 113.1(2) . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
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 . . ?
N2 C12 C13 111.67(18) . . ?
N2 C12 C1 104.21(17) . . ?
C13 C12 C1 113.86(18) . . ?
N2 C12 H12 109.0 . . ?
C13 C12 H12 109.0 . . ?
C1 C12 H12 109.0 . . ?
C14 C13 C12 128.3(2) . . ?
C14 C13 S2 110.82(17) . . ?
C12 C13 S2 120.86(17) . . ?
C13 C14 C15 112.5(2) . . ?
C13 C14 H14 123.7 . . ?
C15 C14 H14 123.7 . . ?
C16 C15 C14 112.9(2) . . ?
C16 C15 H15 123.6 . . ?
C14 C15 H15 123.6 . . ?
C15 C16 S2 112.09(19) . . ?
C15 C16 H16 124.0 . . ?
S2 C16 H16 124.0 . . ?
C22 C17 C18 117.9(2) . . ?
C22 C17 N2 122.5(2) . . ?
C18 C17 N2 119.63(19) . . ?
C19 C18 C17 120.7(2) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 120.8(2) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
O2 C20 C21 125.1(2) . . ?
O2 C20 C19 115.7(2) . . ?
C21 C20 C19 119.2(2) . . ?
C20 C21 C22 120.0(2) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C21 121.3(2) . . ?
C17 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C24 C26 114.51(19) . . ?
N2 C24 C25 102.25(17) . . ?
C26 C24 C25 111.22(18) . . ?
N2 C24 H24 109.5 . . ?
C26 C24 H24 109.5 . . ?
C25 C24 H24 109.5 . . ?
C1 C25 C24 103.99(17) . . ?
C1 C25 H25A 111.0 . . ?
C24 C25 H25A 111.0 . . ?
C1 C25 H25B 111.0 . . ?
C24 C25 H25B 111.0 . . ?
H25A C25 H25B 109.0 . . ?
C27 C26 C24 126.4(2) . . ?
C27 C26 H26 116.8 . . ?
C24 C26 H26 116.8 . . ?
C26 C27 H27A 120.0 . . ?
C26 C27 H27B 120.0 . . ?
H27A C27 H27B 120.0 . . ?
C8 N1 C7 111.14(18) . . ?
C8 N1 C9 123.87(18) . . ?
C7 N1 C9 124.99(18) . . ?
C17 N2 C12 117.12(17) . . ?
C17 N2 C24 120.73(18) . . ?
C12 N2 C24 112.09(17) . . ?
C20 O2 C23 117.25(17) . . ?
C16 S2 C13 91.67(12) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C25 C1 C2 C3 60.6(3) . . . . ?
C8 C1 C2 C3 179.2(2) . . . . ?
C12 C1 C2 C3 -60.4(3) . . . . ?
C25 C1 C2 C7 -117.7(2) . . . . ?
C8 C1 C2 C7 1.0(2) . . . . ?
C12 C1 C2 C7 121.3(2) . . . . ?
C7 C2 C3 C4 -0.9(3) . . . . ?
C1 C2 C3 C4 -179.0(2) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C2 C3 C4 Br1 -178.06(17) . . . . ?
C3 C4 C5 C6 -1.0(4) . . . . ?
Br1 C4 C5 C6 178.31(18) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C5 C6 C7 C2 -0.1(3) . . . . ?
C5 C6 C7 N1 179.8(2) . . . . ?
C3 C2 C7 C6 0.3(3) . . . . ?
C1 C2 C7 C6 178.8(2) . . . . ?
C3 C2 C7 N1 -179.6(2) . . . . ?
C1 C2 C7 N1 -1.1(2) . . . . ?
C2 C1 C8 O1 -179.8(2) . . . . ?
C25 C1 C8 O1 -56.3(3) . . . . ?
C12 C1 C8 O1 54.4(3) . . . . ?
C2 C1 C8 N1 -0.6(2) . . . . ?
C25 C1 C8 N1 122.96(19) . . . . ?
C12 C1 C8 N1 -126.34(19) . . . . ?
N1 C9 C10 C11 63.3(3) . . . . ?
C2 C1 C12 N2 155.50(18) . . . . ?
C25 C1 C12 N2 27.2(2) . . . . ?
C8 C1 C12 N2 -88.4(2) . . . . ?
C2 C1 C12 C13 33.6(3) . . . . ?
C25 C1 C12 C13 -94.7(2) . . . . ?
C8 C1 C12 C13 149.68(19) . . . . ?
N2 C12 C13 C14 149.0(2) . . . . ?
C1 C12 C13 C14 -93.3(3) . . . . ?
N2 C12 C13 S2 -34.0(2) . . . . ?
C1 C12 C13 S2 83.7(2) . . . . ?
C12 C13 C14 C15 175.9(2) . . . . ?
S2 C13 C14 C15 -1.3(3) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C14 C15 C16 S2 0.5(3) . . . . ?
C22 C17 C18 C19 2.6(3) . . . . ?
N2 C17 C18 C19 -178.9(2) . . . . ?
C17 C18 C19 C20 -1.4(3) . . . . ?
C18 C19 C20 O2 179.5(2) . . . . ?
C18 C19 C20 C21 -0.7(3) . . . . ?
O2 C20 C21 C22 -178.8(2) . . . . ?
C19 C20 C21 C22 1.4(3) . . . . ?
C18 C17 C22 C21 -2.0(3) . . . . ?
N2 C17 C22 C21 179.6(2) . . . . ?
C20 C21 C22 C17 0.0(3) . . . . ?
C2 C1 C25 C24 -168.53(19) . . . . ?
C8 C1 C25 C24 76.9(2) . . . . ?
C12 C1 C25 C24 -39.2(2) . . . . ?
N2 C24 C25 C1 36.2(2) . . . . ?
C26 C24 C25 C1 158.91(18) . . . . ?
N2 C24 C26 C27 14.5(3) . . . . ?
C25 C24 C26 C27 -100.8(3) . . . . ?
O1 C8 N1 C7 179.2(2) . . . . ?
C1 C8 N1 C7 -0.1(2) . . . . ?
O1 C8 N1 C9 -0.8(4) . . . . ?
C1 C8 N1 C9 179.98(19) . . . . ?
C6 C7 N1 C8 -179.2(2) . . . . ?
C2 C7 N1 C8 0.7(3) . . . . ?
C6 C7 N1 C9 0.8(4) . . . . ?
C2 C7 N1 C9 -179.31(19) . . . . ?
C10 C9 N1 C8 -101.7(2) . . . . ?
C10 C9 N1 C7 78.4(3) . . . . ?
C22 C17 N2 C12 -148.2(2) . . . . ?
C18 C17 N2 C12 33.4(3) . . . . ?
C22 C17 N2 C24 -5.4(3) . . . . ?
C18 C17 N2 C24 176.18(19) . . . . ?
C13 C12 N2 C17 -95.9(2) . . . . ?
C1 C12 N2 C17 140.73(18) . . . . ?
C13 C12 N2 C24 118.2(2) . . . . ?
C1 C12 N2 C24 -5.1(2) . . . . ?
C26 C24 N2 C17 76.0(3) . . . . ?
C25 C24 N2 C17 -163.61(19) . . . . ?
C26 C24 N2 C12 -139.56(19) . . . . ?
C25 C24 N2 C12 -19.2(2) . . . . ?
C21 C20 O2 C23 -4.6(3) . . . . ?
C19 C20 O2 C23 175.26(19) . . . . ?
C15 C16 S2 C13 -1.1(2) . . . . ?
C14 C13 S2 C16 1.38(18) . . . . ?
C12 C13 S2 C16 -176.11(18) . . . . ?
_diffrn_measured_fraction_theta_max 0.956
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.872
_refine_diff_density_min -0.560
_refine_diff_density_rms 0.081
# Attachment 'S3327.cif'
data_s3327m
_database_code_depnum_ccdc_archive 'CCDC 780382'
_publ_section_title_footnote
;
?
;
#------------------ TEXT ----------------------------------------------------#
_publ_section_synopsis
;
# Insert blank lines between paragraphs
?
;
_publ_section_abstract
;
# Insert blank lines between paragraphs
?
;
_publ_section_comment
;
# Insert blank lines between paragraphs
?
;
_publ_section_exptl_prep
;
?
;
_publ_section_exptl_refinement
;
The structure was solved by direct methods.
The Et2O is positioned close to a special position but
doesn't conform to its symmetry and so is disordered.
This was modelled using the PART -3 command.
The non-hydrogen atoms were refined anisotropically. H atoms were included in
calculated positions with C-H lengths of 0.95(CH), 0.99(CH~2~) &
0.98(CH~3~)\%A; U\~iso(H) values were fixed at 1.2U~eq~(C) except for CH~3~
where it was 1.5U~eq~(C).
;
# Insert blank lines between references
_publ_section_references
;
#
# Put all your general crystallographic references here
# Delete as required from the document CIF
#
Bruker (2000). GEMINI (Version 1.02) and RLATT (Version 3.0).
Bruker AXS In=c., Madison, Wisconsin, USA.
Bruker (2001) SMART (Version 5.625), SADABS (Version 2.03a) and
SHELXTL (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2003). SMART (Version 5.630) and SAINT-Plus (Version 6.45A).
Bruker AXS Inc., Madison, Wisconsin, USA.
M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini,
G. L. Cascarano, L. De Caro,C. Giacovazzo, G. Polidori
and R. Spagna
SIR2004: an improved tool for crystal structure determination
and refinement
J. Appl. Cryst. (2005). 38, 381-388
Sheldrick, G.M. (1993) SHELXL93. Program for crystal structure
refinement. University of G\"ottingen, Germany.
Sheldrick, G.M. (1997) SHELXL97. Program for crystal structure
refinement. University of G\"ottingen, Germany.
Sheldrick, G.M. (1985). SHELXS86. In Crystallographic Computing 3,
edited by G. M. Sheldrick, C. Kruger & R. Goddard, pp. 175-189.
Oxford University Press.
Sheldrick, G.M. (1997) SHELXS97. Program for Crystal Structure solution.
University of G\"ottingen, Germany.
Sheldrick, G, M. (2005). CELL_NOW. University
of G\"ottingen, Germany.
Sheldrick, G, M. (2007). TWINABS. University
of G\"ottingen, Germany.
Sheldrick, G. M. (2008) A short history of SHELX . Acta Cryst. A64, 112-122.
Wilson, A.J.C. (1992) Ed. International Tables for Crystallography,
Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands.
;
_publ_section_figure_captions
;
Figure 1. View of (I) (50% probability displacement ellipsoids)
;
_publ_section_acknowledgements
;
?
;
_publ_section_table_legends
;
Table 1. Fractional atomic coordinates and equivalent
isotropic displacement parameters (\%A^2^)
Table 2. Selected geometric parameters (\%A ,\% )
;
#------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------#
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C50 H62 N4 O9'
_chemical_formula_weight 863.04
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M P2/n
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'
_cell_length_a 13.7253(11)
_cell_length_b 10.4969(8)
_cell_length_c 16.7159(13)
_cell_angle_alpha 90.00
_cell_angle_beta 102.557(2)
_cell_angle_gamma 90.00
_cell_volume 2350.7(3)
_cell_formula_units_Z 2
_cell_measurement_temperature 180(2)
_cell_measurement_reflns_used 2201
_cell_measurement_theta_min 2.306
_cell_measurement_theta_max 20.1655
_exptl_crystal_description cuboid
_exptl_crystal_colour white
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.25
_exptl_crystal_size_min 0.18
_exptl_crystal_density_diffrn 1.219
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 924
_exptl_absorpt_coefficient_mu 0.084
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 180(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega 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 0.0528
_diffrn_reflns_av_sigmaI/netI 0.0872
_diffrn_reflns_limit_h_min -18
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -21
_diffrn_reflns_limit_l_max 21
_diffrn_reflns_theta_min 1.74
_diffrn_reflns_theta_max 28.28
_reflns_number_total 5586
_reflns_number_gt 2294
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker SMART'
_computing_cell_refinement 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1161P)^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 mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 5586
_refine_ls_number_parameters 282
_refine_ls_number_restraints 3
_refine_ls_R_factor_all 0.1423
_refine_ls_R_factor_gt 0.0661
_refine_ls_wR_factor_ref 0.2116
_refine_ls_wR_factor_gt 0.1864
_refine_ls_goodness_of_fit_ref 0.845
_refine_ls_restrained_S_all 0.848
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.24144(19) 0.4679(3) 1.05248(16) 0.0417(7) Uani 1 1 d . . .
C2 C 0.1997(2) 0.3313(3) 1.04854(17) 0.0453(7) Uani 1 1 d . . .
C3 C 0.09679(19) 0.4447(3) 0.94750(16) 0.0420(7) Uani 1 1 d . . .
C4 C 0.0193(2) 0.4764(3) 0.88337(16) 0.0462(7) Uani 1 1 d . . .
H4 H -0.0277 0.4144 0.8579 0.055 Uiso 1 1 calc R . .
C5 C 0.0124(2) 0.6013(3) 0.85741(16) 0.0481(8) Uani 1 1 d . . .
C6 C 0.0821(2) 0.6914(3) 0.89362(17) 0.0506(8) Uani 1 1 d . . .
H6 H 0.0768 0.7768 0.8744 0.061 Uiso 1 1 calc R . .
C7 C 0.1601(2) 0.6561(3) 0.95853(16) 0.0475(7) Uani 1 1 d . . .
H7 H 0.2078 0.7177 0.9835 0.057 Uiso 1 1 calc R . .
C8 C 0.16778(19) 0.5333(3) 0.98597(16) 0.0399(7) Uani 1 1 d . . .
C9 C 0.0590(2) 0.2116(3) 0.96346(18) 0.0555(8) Uani 1 1 d D . .
H9A H -0.0128 0.2336 0.9480 0.067 Uiso 1 1 calc R A 1
H9B H 0.0694 0.1521 1.0105 0.067 Uiso 1 1 calc R A 1
C12 C -0.0817(3) 0.7565(3) 0.7663(2) 0.0714(10) Uani 1 1 d . . .
H12A H -0.0926 0.8106 0.8114 0.107 Uiso 1 1 calc R . .
H12B H -0.1400 0.7613 0.7207 0.107 Uiso 1 1 calc R . .
H12C H -0.0224 0.7860 0.7480 0.107 Uiso 1 1 calc R . .
C13 C 0.35045(18) 0.4680(3) 1.03969(16) 0.0413(7) Uani 1 1 d . . .
H13 H 0.3895 0.4016 1.0760 0.050 Uiso 1 1 calc R . .
C14 C 0.3562(2) 0.6018(3) 1.15055(17) 0.0454(7) Uani 1 1 d . . .
H14 H 0.4073 0.5553 1.1921 0.054 Uiso 1 1 calc R . .
C15 C 0.2562(2) 0.5284(3) 1.13851(16) 0.0483(7) Uani 1 1 d . . .
H15A H 0.2597 0.4618 1.1810 0.058 Uiso 1 1 calc R . .
H15B H 0.2006 0.5871 1.1414 0.058 Uiso 1 1 calc R . .
C16 C 0.36088(19) 0.4445(3) 0.95264(17) 0.0450(7) Uani 1 1 d . . .
C17 C 0.3628(2) 0.3221(3) 0.92423(19) 0.0546(8) Uani 1 1 d . . .
H17 H 0.3598 0.2525 0.9599 0.065 Uiso 1 1 calc R . .
C18 C 0.3692(2) 0.2991(4) 0.8428(2) 0.0661(10) Uani 1 1 d . . .
H18 H 0.3696 0.2142 0.8232 0.079 Uiso 1 1 calc R . .
C19 C 0.3748(2) 0.4004(4) 0.7912(2) 0.0657(10) Uani 1 1 d . . .
H19 H 0.3787 0.3855 0.7359 0.079 Uiso 1 1 calc R . .
C20 C 0.3746(2) 0.5205(4) 0.81972(19) 0.0605(9) Uani 1 1 d . . .
H20 H 0.3796 0.5898 0.7843 0.073 Uiso 1 1 calc R . .
C21 C 0.3672(2) 0.5451(3) 0.89983(18) 0.0552(8) Uani 1 1 d . . .
H21 H 0.3665 0.6305 0.9185 0.066 Uiso 1 1 calc R . .
C22 C 0.3489(2) 0.7352(3) 1.1800(2) 0.0571(8) Uani 1 1 d . . .
C23 C 0.2947(4) 0.9449(4) 1.1449(3) 0.1075(15) Uani 1 1 d . . .
H23A H 0.2506 0.9432 1.1838 0.161 Uiso 1 1 calc R . .
H23B H 0.2630 0.9938 1.0962 0.161 Uiso 1 1 calc R . .
H23C H 0.3583 0.9849 1.1707 0.161 Uiso 1 1 calc R . .
N1 N 0.11775(16) 0.3246(2) 0.98504(13) 0.0449(6) Uani 1 1 d . C .
N2 N 0.38391(19) 0.5926(2) 1.07163(14) 0.0464(6) Uani 1 1 d . . .
O1 O 0.23400(15) 0.2426(2) 1.09239(13) 0.0580(6) Uani 1 1 d . . .
O2 O -0.06716(15) 0.6278(2) 0.79401(12) 0.0628(6) Uani 1 1 d . . .
O3 O 0.37071(18) 0.7650(2) 1.25166(15) 0.0773(7) Uani 1 1 d . . .
O4 O 0.3126(2) 0.8164(2) 1.12109(14) 0.0795(8) Uani 1 1 d . . .
O5 O 0.4565(4) 0.9943(5) 0.9707(4) 0.114(2) Uiso 0.50 1 d PG B -3
C25 C 0.3418(7) 0.9077(10) 0.8578(5) 0.188(6) Uiso 0.50 1 d PG B -3
H25A H 0.2827 0.9623 0.8437 0.282 Uiso 0.50 1 calc PR B -3
H25B H 0.3245 0.8211 0.8377 0.282 Uiso 0.50 1 calc PR B -3
H25C H 0.3944 0.9415 0.8324 0.282 Uiso 0.50 1 calc PR B -3
C26 C 0.3782(9) 0.9048(14) 0.9487(5) 0.56(4) Uiso 0.50 1 d PG B -3
H26A H 0.3230 0.9266 0.9758 0.669 Uiso 0.50 1 calc PR B -3
H26B H 0.4026 0.8184 0.9666 0.669 Uiso 0.50 1 calc PR B -3
C27 C 0.4913(10) 1.0039(16) 1.0566(3) 0.275(11) Uiso 0.50 1 d PG B -3
H27A H 0.5115 0.9189 1.0801 0.330 Uiso 0.50 1 calc PR B -3
H27B H 0.4376 1.0369 1.0820 0.330 Uiso 0.50 1 calc PR B -3
C28 C 0.5795(7) 1.0934(8) 1.0737(5) 0.159(5) Uiso 0.50 1 d PG B -3
H28A H 0.6375 1.0512 1.0601 0.238 Uiso 0.50 1 calc PR B -3
H28B H 0.5947 1.1169 1.1318 0.238 Uiso 0.50 1 calc PR B -3
H28C H 0.5634 1.1703 1.0401 0.238 Uiso 0.50 1 calc PR B -3
H2 H 0.448(2) 0.591(3) 1.0787(18) 0.056(9) Uiso 1 1 d . . .
C10 C 0.0930(4) 0.1489(4) 0.8898(3) 0.1216(17) Uani 0.680(6) 1 d PD C 1
H10A H 0.0788 0.2070 0.8421 0.146 Uiso 0.680(6) 1 calc PR C 1
H10B H 0.1658 0.1332 0.9044 0.146 Uiso 0.680(6) 1 calc PR C 1
C11 C 0.0379(5) 0.0231(5) 0.8675(5) 0.127(2) Uiso 0.680(6) 1 d PD C 1
H11A H 0.0511 -0.0337 0.9152 0.191 Uiso 0.680(6) 1 calc PR C 1
H11B H 0.0612 -0.0170 0.8222 0.191 Uiso 0.680(6) 1 calc PR C 1
H11C H -0.0340 0.0394 0.8509 0.191 Uiso 0.680(6) 1 calc PR C 1
C10S C 0.0930(4) 0.1489(4) 0.8898(3) 0.1216(17) Uani 0.320(6) 1 d PD C 2
H10C H 0.0320 0.1149 0.8532 0.146 Uiso 0.320(6) 1 calc PR C 2
H10D H 0.1172 0.2188 0.8595 0.146 Uiso 0.320(6) 1 calc PR C 2
C11S C 0.1710(9) 0.0436(12) 0.8990(10) 0.127(2) Uiso 0.320(6) 1 d PD C 2
H11D H 0.2376 0.0801 0.9191 0.191 Uiso 0.320(6) 1 calc PR C 2
H11E H 0.1680 0.0031 0.8457 0.191 Uiso 0.320(6) 1 calc PR C 2
H11F H 0.1577 -0.0202 0.9381 0.191 Uiso 0.320(6) 1 calc PR C 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0361(14) 0.0551(18) 0.0346(15) 0.0023(13) 0.0092(12) -0.0002(13)
C2 0.0415(16) 0.060(2) 0.0369(15) 0.0009(15) 0.0133(13) -0.0012(15)
C3 0.0332(14) 0.062(2) 0.0345(15) -0.0010(14) 0.0148(12) 0.0031(14)
C4 0.0347(15) 0.065(2) 0.0397(16) -0.0083(15) 0.0092(13) 0.0003(14)
C5 0.0386(16) 0.070(2) 0.0350(15) -0.0029(15) 0.0058(13) 0.0097(15)
C6 0.0450(17) 0.065(2) 0.0420(16) 0.0040(15) 0.0106(14) 0.0097(16)
C7 0.0369(16) 0.064(2) 0.0412(16) 0.0012(14) 0.0080(13) -0.0011(14)
C8 0.0332(14) 0.0536(19) 0.0348(15) 0.0011(13) 0.0118(12) 0.0009(13)
C9 0.0576(19) 0.057(2) 0.0512(19) -0.0136(15) 0.0108(15) -0.0035(16)
C12 0.061(2) 0.088(3) 0.055(2) 0.0092(19) -0.0090(17) 0.0138(19)
C13 0.0312(14) 0.0551(19) 0.0368(15) 0.0019(13) 0.0054(12) 0.0033(13)
C14 0.0436(16) 0.0532(19) 0.0385(15) 0.0028(14) 0.0069(13) -0.0039(14)
C15 0.0453(16) 0.063(2) 0.0366(16) -0.0007(14) 0.0098(13) -0.0021(15)
C16 0.0296(14) 0.064(2) 0.0422(16) 0.0012(15) 0.0087(12) 0.0005(14)
C17 0.0493(18) 0.066(2) 0.0514(19) -0.0071(16) 0.0172(15) -0.0064(16)
C18 0.057(2) 0.087(3) 0.058(2) -0.0194(19) 0.0197(17) -0.0138(18)
C19 0.052(2) 0.105(3) 0.0439(19) -0.012(2) 0.0177(15) -0.009(2)
C20 0.0501(19) 0.088(3) 0.0466(19) 0.0102(18) 0.0185(15) 0.0033(18)
C21 0.0466(18) 0.071(2) 0.0509(19) 0.0066(16) 0.0161(15) 0.0060(16)
C22 0.0528(19) 0.068(2) 0.052(2) -0.0023(18) 0.0148(16) -0.0057(17)
C23 0.167(5) 0.052(2) 0.109(3) 0.006(2) 0.042(3) 0.020(3)
N1 0.0368(13) 0.0599(17) 0.0384(13) -0.0005(12) 0.0091(11) -0.0035(12)
N2 0.0350(14) 0.0618(18) 0.0423(14) -0.0004(12) 0.0082(11) -0.0023(12)
O1 0.0628(14) 0.0607(14) 0.0468(12) 0.0078(11) 0.0037(10) -0.0002(11)
O2 0.0530(13) 0.0786(17) 0.0486(13) 0.0000(11) -0.0072(10) 0.0108(12)
O3 0.0893(18) 0.0812(18) 0.0590(15) -0.0144(13) 0.0107(13) 0.0012(14)
O4 0.115(2) 0.0584(16) 0.0629(16) 0.0091(12) 0.0150(14) 0.0144(14)
C10 0.121(4) 0.097(4) 0.136(4) -0.029(3) 0.005(3) -0.004(3)
C10S 0.121(4) 0.097(4) 0.136(4) -0.029(3) 0.005(3) -0.004(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C8 1.497(4) . ?
C1 C2 1.540(4) . ?
C1 C15 1.544(4) . ?
C1 C13 1.557(4) . ?
C2 O1 1.215(3) . ?
C2 N1 1.371(3) . ?
C3 C4 1.376(4) . ?
C3 C8 1.398(4) . ?
C3 N1 1.410(4) . ?
C4 C5 1.378(4) . ?
C4 H4 0.9500 . ?
C5 O2 1.375(3) . ?
C5 C6 1.387(4) . ?
C6 C7 1.399(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.365(4) . ?
C7 H7 0.9500 . ?
C9 N1 1.436(4) . ?
C9 C10 1.554(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C12 O2 1.428(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N2 1.449(4) . ?
C13 C16 1.513(4) . ?
C13 H13 1.0000 . ?
C14 N2 1.453(3) . ?
C14 C22 1.495(4) . ?
C14 C15 1.549(4) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.372(4) . ?
C16 C21 1.391(4) . ?
C17 C18 1.404(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.348(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.389(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 O3 1.211(3) . ?
C22 O4 1.315(4) . ?
C23 O4 1.443(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
N2 H2 0.87(3) . ?
O5 C26 1.4145 . ?
O5 C27 1.4152 . ?
C25 C26 1.4932 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.5091 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C10 C11 1.526(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11S H11D 0.9800 . ?
C11S H11E 0.9800 . ?
C11S H11F 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
C8 C1 C2 102.1(2) . . ?
C8 C1 C15 115.7(2) . . ?
C2 C1 C15 113.3(2) . . ?
C8 C1 C13 114.3(2) . . ?
C2 C1 C13 110.7(2) . . ?
C15 C1 C13 101.1(2) . . ?
O1 C2 N1 124.9(3) . . ?
O1 C2 C1 126.6(3) . . ?
N1 C2 C1 108.4(2) . . ?
C4 C3 C8 122.7(3) . . ?
C4 C3 N1 127.7(3) . . ?
C8 C3 N1 109.6(2) . . ?
C3 C4 C5 117.7(3) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
O2 C5 C4 115.1(3) . . ?
O2 C5 C6 123.7(3) . . ?
C4 C5 C6 121.2(3) . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 120.0(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C3 118.6(3) . . ?
C7 C8 C1 132.3(3) . . ?
C3 C8 C1 109.1(2) . . ?
N1 C9 C10 107.5(3) . . ?
N1 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
N1 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C16 114.4(2) . . ?
N2 C13 C1 100.8(2) . . ?
C16 C13 C1 115.3(2) . . ?
N2 C13 H13 108.7 . . ?
C16 C13 H13 108.7 . . ?
C1 C13 H13 108.7 . . ?
N2 C14 C22 114.2(2) . . ?
N2 C14 C15 104.4(2) . . ?
C22 C14 C15 112.8(2) . . ?
N2 C14 H14 108.4 . . ?
C22 C14 H14 108.4 . . ?
C15 C14 H14 108.4 . . ?
C1 C15 C14 105.0(2) . . ?
C1 C15 H15A 110.7 . . ?
C14 C15 H15A 110.7 . . ?
C1 C15 H15B 110.7 . . ?
C14 C15 H15B 110.7 . . ?
H15A C15 H15B 108.8 . . ?
C17 C16 C21 118.8(3) . . ?
C17 C16 C13 119.9(3) . . ?
C21 C16 C13 121.3(3) . . ?
C16 C17 C18 120.5(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 119.7(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C20 C19 C18 119.6(3) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 121.4(3) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C20 C21 C16 119.9(3) . . ?
C20 C21 H21 120.0 . . ?
C16 C21 H21 120.0 . . ?
O3 C22 O4 123.0(3) . . ?
O3 C22 C14 123.2(3) . . ?
O4 C22 C14 113.7(3) . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C2 N1 C3 110.6(2) . . ?
C2 N1 C9 124.0(3) . . ?
C3 N1 C9 125.3(2) . . ?
C13 N2 C14 105.7(2) . . ?
C13 N2 H2 105(2) . . ?
C14 N2 H2 110(2) . . ?
C5 O2 C12 118.2(3) . . ?
C22 O4 C23 117.3(3) . . ?
C26 O5 C27 112.4 . . ?
O5 C26 C25 108.6 . . ?
O5 C26 H26A 110.0 . . ?
C25 C26 H26A 110.0 . . ?
O5 C26 H26B 110.0 . . ?
C25 C26 H26B 110.0 . . ?
H26A C26 H26B 108.4 . . ?
O5 C27 C28 108.4 . . ?
O5 C27 H27A 110.0 . . ?
C28 C27 H27A 110.0 . . ?
O5 C27 H27B 110.0 . . ?
C28 C27 H27B 110.0 . . ?
H27A C27 H27B 108.4 . . ?
C11 C10 C9 110.0(5) . . ?
C11 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
C11 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
H11D C11S H11E 109.5 . . ?
H11D C11S H11F 109.5 . . ?
H11E C11S H11F 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
C8 C1 C2 O1 -178.8(3) . . . . ?
C15 C1 C2 O1 -53.6(4) . . . . ?
C13 C1 C2 O1 59.1(3) . . . . ?
C8 C1 C2 N1 2.9(3) . . . . ?
C15 C1 C2 N1 128.0(2) . . . . ?
C13 C1 C2 N1 -119.3(2) . . . . ?
C8 C3 C4 C5 -0.5(4) . . . . ?
N1 C3 C4 C5 178.8(2) . . . . ?
C3 C4 C5 O2 -179.1(2) . . . . ?
C3 C4 C5 C6 1.2(4) . . . . ?
O2 C5 C6 C7 179.3(2) . . . . ?
C4 C5 C6 C7 -1.0(4) . . . . ?
C5 C6 C7 C8 0.2(4) . . . . ?
C6 C7 C8 C3 0.4(4) . . . . ?
C6 C7 C8 C1 179.7(3) . . . . ?
C4 C3 C8 C7 -0.3(4) . . . . ?
N1 C3 C8 C7 -179.7(2) . . . . ?
C4 C3 C8 C1 -179.7(2) . . . . ?
N1 C3 C8 C1 0.8(3) . . . . ?
C2 C1 C8 C7 178.5(3) . . . . ?
C15 C1 C8 C7 55.0(4) . . . . ?
C13 C1 C8 C7 -61.9(4) . . . . ?
C2 C1 C8 C3 -2.2(3) . . . . ?
C15 C1 C8 C3 -125.7(3) . . . . ?
C13 C1 C8 C3 117.4(3) . . . . ?
C8 C1 C13 N2 83.1(3) . . . . ?
C2 C1 C13 N2 -162.3(2) . . . . ?
C15 C1 C13 N2 -42.0(3) . . . . ?
C8 C1 C13 C16 -40.6(3) . . . . ?
C2 C1 C13 C16 74.1(3) . . . . ?
C15 C1 C13 C16 -165.6(2) . . . . ?
C8 C1 C15 C14 -102.8(3) . . . . ?
C2 C1 C15 C14 139.8(2) . . . . ?
C13 C1 C15 C14 21.3(3) . . . . ?
N2 C14 C15 C1 6.6(3) . . . . ?
C22 C14 C15 C1 131.2(3) . . . . ?
N2 C13 C16 C17 159.3(3) . . . . ?
C1 C13 C16 C17 -84.6(3) . . . . ?
N2 C13 C16 C21 -21.7(3) . . . . ?
C1 C13 C16 C21 94.5(3) . . . . ?
C21 C16 C17 C18 -1.2(4) . . . . ?
C13 C16 C17 C18 177.9(2) . . . . ?
C16 C17 C18 C19 0.8(5) . . . . ?
C17 C18 C19 C20 0.4(5) . . . . ?
C18 C19 C20 C21 -1.1(5) . . . . ?
C19 C20 C21 C16 0.7(5) . . . . ?
C17 C16 C21 C20 0.4(4) . . . . ?
C13 C16 C21 C20 -178.6(2) . . . . ?
N2 C14 C22 O3 -146.1(3) . . . . ?
C15 C14 C22 O3 94.9(4) . . . . ?
N2 C14 C22 O4 36.6(4) . . . . ?
C15 C14 C22 O4 -82.4(3) . . . . ?
O1 C2 N1 C3 179.0(3) . . . . ?
C1 C2 N1 C3 -2.6(3) . . . . ?
O1 C2 N1 C9 2.2(4) . . . . ?
C1 C2 N1 C9 -179.4(2) . . . . ?
C4 C3 N1 C2 -178.3(2) . . . . ?
C8 C3 N1 C2 1.2(3) . . . . ?
C4 C3 N1 C9 -1.5(4) . . . . ?
C8 C3 N1 C9 178.0(2) . . . . ?
C10 C9 N1 C2 -99.5(3) . . . . ?
C10 C9 N1 C3 84.1(4) . . . . ?
C16 C13 N2 C14 173.0(2) . . . . ?
C1 C13 N2 C14 48.7(3) . . . . ?
C22 C14 N2 C13 -158.6(2) . . . . ?
C15 C14 N2 C13 -34.9(3) . . . . ?
C4 C5 O2 C12 177.2(3) . . . . ?
C6 C5 O2 C12 -3.1(4) . . . . ?
O3 C22 O4 C23 -2.7(5) . . . . ?
C14 C22 O4 C23 174.6(3) . . . . ?
C27 O5 C26 C25 176.1 . . . . ?
C26 O5 C27 C28 175.7 . . . . ?
N1 C9 C10 C11 176.3(4) . . . . ?
_diffrn_measured_fraction_theta_max 0.957
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.610
_refine_diff_density_min -0.466
_refine_diff_density_rms 0.052
data_s3410m
_database_code_depnum_ccdc_archive 'CCDC 791298'
#TrackingRef 's3410m.cif.txt'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_publ_section_abstract
;
ENTER ABSTRACT
;
_publ_section_exptl_prep
;
ENTER EXPERIMENTAL SECTION
;
_publ_section_exptl_refinement
;
The structure was solved by the direct methods.
All non-H atoms were refined anisotropically.
H atoms were included in calculated positions,
except H3n which was found by difference Fourier methods and
refined isotropically. The absolute configuration was input.
;
_publ_section_comment
;
ENTER TEXT
;
_publ_section_references
;
Bruker (2001). SMART (Version 5.625), SADABS (Version 2.03a) and
SHELXTL (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2002). SAINT. Version 6.36a. Bruker AXS Inc., Madison,
Wisconsin, USA.
M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini,
G. L. Cascarano, L. De Caro,C. Giacovazzo, G. Polidori
and R. Spagna
SIR2004: an improved tool for crystal structure determination
and refinement
J. Appl. Cryst. (2005). 38, 381-388
Sheldrick, G. M. (1997). SHELXS-97 and SHELXL-97.
University of G\"ottingen, Germany.
Sheldrick, G, M. (2005). CELL_NOW. University
of G\"ottingen, Germany.
Sheldrick, G, M. (2007). TWINABS. University
of G\"ottingen, Germany.
Spek, A.L. (2003) J.Appl.Cryst. 36, 2003, 7-13.
;
_publ_section_acknowledgements
;
ENTER ACKNOWLEDGEMENTS
;
_publ_section_table_legends
;
ENTER TABLE LEGENDS
;
_publ_section_figure_captions
;
ENTER FIGURE CAPTIONS
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C24 H23 N3 O4'
_chemical_formula_sum 'C24 H23 N3 O4'
_chemical_formula_weight 417.45
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_H-M P2(1)2(1)2(1)
_symmetry_space_group_name_Hall P2ac2ab
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 9.9030(13)
_cell_length_b 10.8311(14)
_cell_length_c 19.231(2)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 2062.7(5)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 1001
_cell_measurement_theta_min 2.79
_cell_measurement_theta_max 20.55
_exptl_crystal_description plate
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.35
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.15
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.344
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 880
_exptl_absorpt_coefficient_mu 0.093
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 11643
_diffrn_reflns_av_R_equivalents 0.0685
_diffrn_reflns_av_sigmaI/netI 0.0608
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -21
_diffrn_reflns_limit_l_max 24
_diffrn_reflns_theta_min 2.12
_diffrn_reflns_theta_max 26.40
_reflns_number_total 2401
_reflns_number_gt 2096
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker SMART'
_computing_cell_refinement 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0309P)^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 mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_chemical_absolute_configuration syn
_refine_ls_number_reflns 2401
_refine_ls_number_parameters 285
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0554
_refine_ls_R_factor_gt 0.0445
_refine_ls_wR_factor_ref 0.0817
_refine_ls_wR_factor_gt 0.0786
_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
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 0.13977(19) 0.51366(17) 0.88569(10) 0.0201(5) Uani 1 1 d . . .
O2 O 0.4323(2) 0.90646(18) 0.94207(10) 0.0230(5) Uani 1 1 d . . .
O3 O 0.0540(2) 0.95111(18) 0.79341(10) 0.0230(5) Uani 1 1 d . . .
O4 O 0.3249(2) 0.86572(19) 0.46023(10) 0.0293(5) Uani 1 1 d . . .
N1 N 0.2289(2) 0.6401(2) 0.96661(11) 0.0171(5) Uani 1 1 d . . .
N2 N 0.2847(2) 0.8132(2) 0.86856(11) 0.0153(5) Uani 1 1 d . . .
N3 N 0.0962(2) 0.9381(2) 0.67650(12) 0.0184(6) Uani 1 1 d . . .
H3N H 0.021(3) 0.976(3) 0.6600(16) 0.032(9) Uiso 1 1 d . . .
C1 C 0.2698(3) 0.7640(3) 0.98972(13) 0.0184(6) Uani 1 1 d . . .
H1 H 0.1885 0.8101 1.0063 0.022 Uiso 1 1 calc R . .
C2 C 0.3607(3) 0.7346(3) 1.05161(14) 0.0220(7) Uani 1 1 d . . .
H2A H 0.3609 0.8033 1.0856 0.026 Uiso 1 1 calc R . .
H2B H 0.4546 0.7186 1.0364 0.026 Uiso 1 1 calc R . .
C3 C 0.2969(3) 0.6183(3) 1.08289(14) 0.0248(7) Uani 1 1 d . . .
H3A H 0.3637 0.5712 1.1105 0.030 Uiso 1 1 calc R . .
H3B H 0.2192 0.6396 1.1130 0.030 Uiso 1 1 calc R . .
C4 C 0.2510(3) 0.5446(3) 1.01951(14) 0.0215(7) Uani 1 1 d . . .
H4A H 0.3216 0.4855 1.0046 0.026 Uiso 1 1 calc R . .
H4B H 0.1667 0.4988 1.0294 0.026 Uiso 1 1 calc R . .
C5 C 0.1782(3) 0.6171(3) 0.90409(14) 0.0158(6) Uani 1 1 d . . .
C6 C 0.1718(3) 0.7276(3) 0.85623(13) 0.0162(6) Uani 1 1 d . . .
H6 H 0.0846 0.7721 0.8640 0.019 Uiso 1 1 calc R . .
C7 C 0.3371(3) 0.8362(3) 0.93144(14) 0.0171(6) Uani 1 1 d . . .
C8 C 0.1855(3) 0.6966(2) 0.77904(13) 0.0168(6) Uani 1 1 d . . .
H8A H 0.0973 0.6738 0.7586 0.020 Uiso 1 1 calc R . .
H8B H 0.2504 0.6283 0.7716 0.020 Uiso 1 1 calc R . .
C9 C 0.2391(3) 0.8191(2) 0.74791(13) 0.0166(6) Uani 1 1 d . . .
C10 C 0.3437(3) 0.8626(3) 0.80411(13) 0.0164(6) Uani 1 1 d . . .
H10 H 0.3454 0.9548 0.8061 0.020 Uiso 1 1 calc R . .
C11 C 0.4845(3) 0.8141(2) 0.79142(13) 0.0150(6) Uani 1 1 d . . .
C12 C 0.5742(3) 0.8801(3) 0.75034(14) 0.0199(6) Uani 1 1 d . . .
H12 H 0.5483 0.9587 0.7330 0.024 Uiso 1 1 calc R . .
C13 C 0.7010(3) 0.8338(3) 0.73408(14) 0.0227(7) Uani 1 1 d . . .
H13 H 0.7610 0.8801 0.7057 0.027 Uiso 1 1 calc R . .
C14 C 0.7393(3) 0.7197(3) 0.75958(14) 0.0216(7) Uani 1 1 d . . .
H14 H 0.8254 0.6868 0.7483 0.026 Uiso 1 1 calc R . .
C15 C 0.6526(3) 0.6539(3) 0.80129(14) 0.0200(7) Uani 1 1 d . . .
H15 H 0.6798 0.5760 0.8191 0.024 Uiso 1 1 calc R . .
C16 C 0.5258(3) 0.7001(2) 0.81767(14) 0.0171(6) Uani 1 1 d . . .
H16 H 0.4669 0.6540 0.8468 0.021 Uiso 1 1 calc R . .
C17 C 0.1182(3) 0.9114(2) 0.74440(14) 0.0167(6) Uani 1 1 d . . .
C18 C 0.2816(3) 0.8115(3) 0.67265(14) 0.0170(6) Uani 1 1 d . . .
C19 C 0.1936(3) 0.8840(2) 0.63270(14) 0.0157(6) Uani 1 1 d . . .
C20 C 0.2066(3) 0.9005(3) 0.56235(14) 0.0198(6) Uani 1 1 d . . .
H20 H 0.1450 0.9505 0.5370 0.024 Uiso 1 1 calc R . .
C21 C 0.3138(3) 0.8412(3) 0.52955(14) 0.0216(7) Uani 1 1 d . . .
C22 C 0.4002(3) 0.7636(3) 0.56677(14) 0.0217(7) Uani 1 1 d . . .
H22 H 0.4705 0.7208 0.5434 0.026 Uiso 1 1 calc R . .
C23 C 0.3833(3) 0.7489(3) 0.63851(14) 0.0203(7) Uani 1 1 d . . .
H23 H 0.4418 0.6958 0.6637 0.024 Uiso 1 1 calc R . .
C24 C 0.4309(3) 0.8070(3) 0.42227(15) 0.0291(8) Uani 1 1 d . . .
H24A H 0.4160 0.7176 0.4219 0.044 Uiso 1 1 calc R . .
H24B H 0.5177 0.8252 0.4444 0.044 Uiso 1 1 calc R . .
H24C H 0.4316 0.8380 0.3744 0.044 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 0.0186(11) 0.0210(11) 0.0205(11) -0.0015(9) -0.0033(9) -0.0031(9)
O2 0.0198(12) 0.0253(12) 0.0239(11) -0.0053(9) -0.0004(9) -0.0065(9)
O3 0.0197(12) 0.0270(11) 0.0221(11) -0.0017(9) 0.0034(9) 0.0065(9)
O4 0.0362(14) 0.0358(13) 0.0159(11) 0.0011(9) 0.0036(9) 0.0093(11)
N1 0.0152(13) 0.0188(13) 0.0172(12) -0.0003(10) -0.0005(10) -0.0009(10)
N2 0.0111(12) 0.0182(12) 0.0167(12) -0.0010(10) 0.0013(10) -0.0021(10)
N3 0.0131(14) 0.0213(14) 0.0206(14) 0.0001(11) -0.0034(11) 0.0028(10)
C1 0.0134(15) 0.0232(16) 0.0187(15) -0.0051(12) 0.0008(12) 0.0011(12)
C2 0.0175(16) 0.0311(17) 0.0173(15) -0.0028(13) -0.0029(12) 0.0000(13)
C3 0.0222(17) 0.0328(18) 0.0195(16) 0.0019(13) -0.0015(13) 0.0027(15)
C4 0.0206(17) 0.0255(16) 0.0183(16) 0.0041(12) -0.0010(13) 0.0032(14)
C5 0.0115(14) 0.0195(15) 0.0166(14) -0.0014(12) 0.0038(12) 0.0012(12)
C6 0.0097(14) 0.0196(15) 0.0193(15) -0.0012(12) -0.0007(11) -0.0013(11)
C7 0.0153(15) 0.0171(15) 0.0188(15) -0.0056(12) 0.0014(12) 0.0021(12)
C8 0.0134(15) 0.0171(14) 0.0199(15) 0.0021(12) -0.0023(12) -0.0009(12)
C9 0.0147(15) 0.0162(14) 0.0189(15) 0.0008(11) 0.0007(12) 0.0008(12)
C10 0.0169(15) 0.0159(14) 0.0165(14) 0.0005(12) -0.0005(11) -0.0003(12)
C11 0.0136(15) 0.0205(15) 0.0110(13) -0.0029(11) -0.0022(11) -0.0008(12)
C12 0.0204(16) 0.0200(15) 0.0192(15) 0.0024(12) 0.0005(12) 0.0020(13)
C13 0.0214(17) 0.0263(16) 0.0205(15) 0.0034(13) 0.0061(13) -0.0047(14)
C14 0.0120(16) 0.0279(16) 0.0250(16) -0.0054(13) 0.0017(13) 0.0029(13)
C15 0.0227(17) 0.0145(14) 0.0227(16) 0.0001(13) -0.0026(12) 0.0022(12)
C16 0.0161(15) 0.0204(15) 0.0148(14) 0.0005(12) 0.0008(12) -0.0030(12)
C17 0.0156(16) 0.0173(15) 0.0172(15) -0.0014(12) -0.0014(12) -0.0023(12)
C18 0.0164(16) 0.0184(15) 0.0163(14) 0.0016(12) -0.0014(12) -0.0047(12)
C19 0.0140(15) 0.0131(14) 0.0201(15) -0.0012(12) -0.0011(12) -0.0024(12)
C20 0.0200(16) 0.0190(15) 0.0203(15) 0.0023(12) -0.0046(13) -0.0021(13)
C21 0.0256(17) 0.0213(16) 0.0179(15) -0.0017(13) -0.0012(13) -0.0029(14)
C22 0.0210(17) 0.0234(16) 0.0209(16) -0.0057(13) 0.0029(13) 0.0012(13)
C23 0.0197(16) 0.0172(15) 0.0239(16) -0.0010(13) -0.0039(13) 0.0025(12)
C24 0.034(2) 0.0334(19) 0.0194(16) -0.0036(14) 0.0047(14) 0.0022(16)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.235(3) . ?
O2 C7 1.228(3) . ?
O3 C17 1.215(3) . ?
O4 C21 1.364(3) . ?
O4 C24 1.428(4) . ?
N1 C5 1.327(3) . ?
N1 C4 1.467(3) . ?
N1 C1 1.470(4) . ?
N2 C7 1.339(3) . ?
N2 C10 1.471(3) . ?
N2 C6 1.472(3) . ?
N3 C17 1.355(3) . ?
N3 C19 1.408(4) . ?
N3 H3N 0.91(3) . ?
C1 C7 1.521(4) . ?
C1 C2 1.526(4) . ?
C1 H1 1.0000 . ?
C2 C3 1.533(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.526(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.511(4) . ?
C6 C8 1.528(4) . ?
C6 H6 1.0000 . ?
C8 C9 1.549(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C18 1.510(3) . ?
C9 C17 1.561(4) . ?
C9 C10 1.569(4) . ?
C10 C11 1.510(4) . ?
C10 H10 1.0000 . ?
C11 C12 1.387(4) . ?
C11 C16 1.395(4) . ?
C12 C13 1.388(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.374(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C23 1.380(4) . ?
C18 C19 1.402(4) . ?
C19 C20 1.371(4) . ?
C20 C21 1.393(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.396(4) . ?
C22 C23 1.399(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C21 O4 C24 118.2(2) . . ?
C5 N1 C4 123.5(2) . . ?
C5 N1 C1 123.3(2) . . ?
C4 N1 C1 113.1(2) . . ?
C7 N2 C10 122.6(2) . . ?
C7 N2 C6 123.8(2) . . ?
C10 N2 C6 113.3(2) . . ?
C17 N3 C19 112.2(2) . . ?
C17 N3 H3N 124(2) . . ?
C19 N3 H3N 123(2) . . ?
N1 C1 C7 111.6(2) . . ?
N1 C1 C2 102.0(2) . . ?
C7 C1 C2 115.1(2) . . ?
N1 C1 H1 109.3 . . ?
C7 C1 H1 109.3 . . ?
C2 C1 H1 109.3 . . ?
C1 C2 C3 103.5(2) . . ?
C1 C2 H2A 111.1 . . ?
C3 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
C3 C2 H2B 111.1 . . ?
H2A C2 H2B 109.0 . . ?
C4 C3 C2 103.8(2) . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
C2 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
N1 C4 C3 103.3(2) . . ?
N1 C4 H4A 111.1 . . ?
C3 C4 H4A 111.1 . . ?
N1 C4 H4B 111.1 . . ?
C3 C4 H4B 111.1 . . ?
H4A C4 H4B 109.1 . . ?
O1 C5 N1 123.1(3) . . ?
O1 C5 C6 122.1(2) . . ?
N1 C5 C6 114.8(2) . . ?
N2 C6 C5 111.7(2) . . ?
N2 C6 C8 103.1(2) . . ?
C5 C6 C8 114.5(2) . . ?
N2 C6 H6 109.1 . . ?
C5 C6 H6 109.1 . . ?
C8 C6 H6 109.1 . . ?
O2 C7 N2 124.2(3) . . ?
O2 C7 C1 122.2(2) . . ?
N2 C7 C1 113.6(2) . . ?
C6 C8 C9 102.6(2) . . ?
C6 C8 H8A 111.2 . . ?
C9 C8 H8A 111.2 . . ?
C6 C8 H8B 111.2 . . ?
C9 C8 H8B 111.2 . . ?
H8A C8 H8B 109.2 . . ?
C18 C9 C8 114.8(2) . . ?
C18 C9 C17 102.0(2) . . ?
C8 C9 C17 107.6(2) . . ?
C18 C9 C10 119.5(2) . . ?
C8 C9 C10 102.5(2) . . ?
C17 C9 C10 110.1(2) . . ?
N2 C10 C11 112.1(2) . . ?
N2 C10 C9 102.1(2) . . ?
C11 C10 C9 113.2(2) . . ?
N2 C10 H10 109.7 . . ?
C11 C10 H10 109.7 . . ?
C9 C10 H10 109.7 . . ?
C12 C11 C16 118.3(3) . . ?
C12 C11 C10 120.3(2) . . ?
C16 C11 C10 121.3(3) . . ?
C13 C12 C11 121.4(3) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C12 119.4(3) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.7(3) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C11 120.1(3) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
O3 C17 N3 126.0(3) . . ?
O3 C17 C9 126.4(2) . . ?
N3 C17 C9 107.5(2) . . ?
C23 C18 C19 117.9(2) . . ?
C23 C18 C9 133.3(3) . . ?
C19 C18 C9 108.8(2) . . ?
C20 C19 C18 123.8(3) . . ?
C20 C19 N3 126.9(3) . . ?
C18 C19 N3 109.3(2) . . ?
C19 C20 C21 117.3(3) . . ?
C19 C20 H20 121.4 . . ?
C21 C20 H20 121.4 . . ?
O4 C21 C20 114.4(3) . . ?
O4 C21 C22 124.7(3) . . ?
C20 C21 C22 120.9(3) . . ?
C21 C22 C23 120.0(3) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C18 C23 C22 120.0(3) . . ?
C18 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
O4 C24 H24A 109.5 . . ?
O4 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O4 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C5 N1 C1 C7 -38.6(4) . . . . ?
C4 N1 C1 C7 140.9(2) . . . . ?
C5 N1 C1 C2 -161.9(2) . . . . ?
C4 N1 C1 C2 17.6(3) . . . . ?
N1 C1 C2 C3 -33.4(3) . . . . ?
C7 C1 C2 C3 -154.3(2) . . . . ?
C1 C2 C3 C4 37.8(3) . . . . ?
C5 N1 C4 C3 -174.8(2) . . . . ?
C1 N1 C4 C3 5.7(3) . . . . ?
C2 C3 C4 N1 -26.6(3) . . . . ?
C4 N1 C5 O1 3.0(4) . . . . ?
C1 N1 C5 O1 -177.5(3) . . . . ?
C4 N1 C5 C6 -176.5(2) . . . . ?
C1 N1 C5 C6 3.0(4) . . . . ?
C7 N2 C6 C5 -35.9(3) . . . . ?
C10 N2 C6 C5 138.4(2) . . . . ?
C7 N2 C6 C8 -159.3(2) . . . . ?
C10 N2 C6 C8 15.0(3) . . . . ?
O1 C5 C6 N2 -146.4(2) . . . . ?
N1 C5 C6 N2 33.1(3) . . . . ?
O1 C5 C6 C8 -29.7(4) . . . . ?
N1 C5 C6 C8 149.8(2) . . . . ?
C10 N2 C7 O2 5.3(4) . . . . ?
C6 N2 C7 O2 179.1(3) . . . . ?
C10 N2 C7 C1 -173.2(2) . . . . ?
C6 N2 C7 C1 0.6(4) . . . . ?
N1 C1 C7 O2 -143.3(3) . . . . ?
C2 C1 C7 O2 -27.7(4) . . . . ?
N1 C1 C7 N2 35.3(3) . . . . ?
C2 C1 C7 N2 150.9(2) . . . . ?
N2 C6 C8 C9 -34.1(3) . . . . ?
C5 C6 C8 C9 -155.6(2) . . . . ?
C6 C8 C9 C18 171.8(2) . . . . ?
C6 C8 C9 C17 -75.5(3) . . . . ?
C6 C8 C9 C10 40.6(3) . . . . ?
C7 N2 C10 C11 63.3(3) . . . . ?
C6 N2 C10 C11 -111.1(3) . . . . ?
C7 N2 C10 C9 -175.3(2) . . . . ?
C6 N2 C10 C9 10.3(3) . . . . ?
C18 C9 C10 N2 -159.3(2) . . . . ?
C8 C9 C10 N2 -31.0(3) . . . . ?
C17 C9 C10 N2 83.3(2) . . . . ?
C18 C9 C10 C11 -38.6(3) . . . . ?
C8 C9 C10 C11 89.7(3) . . . . ?
C17 C9 C10 C11 -156.0(2) . . . . ?
N2 C10 C11 C12 -156.1(2) . . . . ?
C9 C10 C11 C12 89.1(3) . . . . ?
N2 C10 C11 C16 26.8(3) . . . . ?
C9 C10 C11 C16 -88.0(3) . . . . ?
C16 C11 C12 C13 1.4(4) . . . . ?
C10 C11 C12 C13 -175.7(2) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C12 C13 C14 C15 -0.8(4) . . . . ?
C13 C14 C15 C16 0.7(4) . . . . ?
C14 C15 C16 C11 0.4(4) . . . . ?
C12 C11 C16 C15 -1.5(4) . . . . ?
C10 C11 C16 C15 175.6(2) . . . . ?
C19 N3 C17 O3 175.9(3) . . . . ?
C19 N3 C17 C9 -4.9(3) . . . . ?
C18 C9 C17 O3 -176.4(3) . . . . ?
C8 C9 C17 O3 62.4(4) . . . . ?
C10 C9 C17 O3 -48.6(4) . . . . ?
C18 C9 C17 N3 4.4(3) . . . . ?
C8 C9 C17 N3 -116.7(2) . . . . ?
C10 C9 C17 N3 132.3(2) . . . . ?
C8 C9 C18 C23 -65.3(4) . . . . ?
C17 C9 C18 C23 178.6(3) . . . . ?
C10 C9 C18 C23 57.1(4) . . . . ?
C8 C9 C18 C19 113.5(3) . . . . ?
C17 C9 C18 C19 -2.5(3) . . . . ?
C10 C9 C18 C19 -124.0(3) . . . . ?
C23 C18 C19 C20 -3.1(4) . . . . ?
C9 C18 C19 C20 177.8(3) . . . . ?
C23 C18 C19 N3 178.9(2) . . . . ?
C9 C18 C19 N3 -0.2(3) . . . . ?
C17 N3 C19 C20 -174.6(3) . . . . ?
C17 N3 C19 C18 3.4(3) . . . . ?
C18 C19 C20 C21 0.1(4) . . . . ?
N3 C19 C20 C21 177.7(3) . . . . ?
C24 O4 C21 C20 -179.0(3) . . . . ?
C24 O4 C21 C22 0.9(4) . . . . ?
C19 C20 C21 O4 -177.2(3) . . . . ?
C19 C20 C21 C22 2.9(4) . . . . ?
O4 C21 C22 C23 177.3(3) . . . . ?
C20 C21 C22 C23 -2.8(4) . . . . ?
C19 C18 C23 C22 3.1(4) . . . . ?
C9 C18 C23 C22 -178.1(3) . . . . ?
C21 C22 C23 C18 -0.3(4) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3N O1 0.91(3) 1.86(3) 2.750(3) 164(3) 3_556
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full 26.40
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max 0.257
_refine_diff_density_min -0.176
_refine_diff_density_rms 0.047