# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2012
data_global
_journal_name_full Chem.Commun.
_journal_coden_cambridge 0182
#TrackingRef '9893_web_deposit_cif_file_0_MichaelHaindl_1330528584.h237_2.cif'
#==============================================================================
# 0. AUDIT DETAILS
_audit_creation_date 'Nov 10 09:02:39 2008'
_audit_creation_method 'PLATON
option'
_audit_update_record
;
;
#===============================================================================
# 1. SUBMISSION DETAILS
_publ_contact_author_name # Name of author for correspondence
'Ruth M. Gschwind'
_publ_contact_author_address # address of author for correspondence
;
;
_publ_contact_author_email ruth.gschwind@chemie.uni-regensburg.de
_publ_contact_author_fax ?
_publ_contact_author_phone ?
# Publication choise FI, CI or EI for Inorganic
# FM, CM or EM for Metal-organic
# FO, CO or EO for Organic
_publ_requested_category ?
_publ_requested_coeditor_name ?
_publ_contact_letter # Include date of submission
;
Date of submission ?
Please consider this CIF submission for publication as a
Regular Structural Paper in Acta Crystallographica C.
;
#===============================================================================
# 2. PROCESSING SUMMARY (JOURNAL OFFICE ONLY)
_journal_date_recd_electronic ?
_journal_date_to_coeditor ?
_journal_date_from_coeditor ?
_journal_date_accepted ?
_journal_date_printers_first ?
_journal_date_printers_final ?
_journal_date_proofs_out ?
_journal_date_proofs_in ?
_journal_coeditor_name ?
_journal_coeditor_code ?
_journal_coeditor_notes
;
;
_journal_techeditor_code ?
_journal_techeditor_notes
;
;
_journal_coden_ASTM ?
_journal_year ?
_journal_volume ?
_journal_issue ?
_journal_page_first ?
_journal_page_last ?
_journal_suppl_publ_number ?
_journal_suppl_publ_pages ?
#===============================================================================
# 3. TITLE AND AUTHOR LIST
_publ_section_title
;
;
_publ_section_title_footnote
;
;
# The loop structure below should contain the names and adresses of all
# authors, in the required order of publication. Repeat as necessary.
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
# author name
'Michael H. Haindl'
; # author related footnote
;
; # Address of this author
;
'Markus B. Schmid' '' ''
'Kirsten Zeitler' '' ''
'Ruth M.Gschwind' '' ''
#===============================================================================
# 4. TEXT
_publ_section_synopsis
;
?
;
_publ_section_abstract
;
?
;
# Insert blank lines between paragraphs
_publ_section_comment
;
;
_publ_section_exptl_prep
;
?
;
_publ_section_exptl_refinement
;
The data were collected at 123K using an Oxford Diffraction Cryojet
Cooler. The structure was solved by direct methods (SIR-97)
and refined by full-matrix anisotropic least squares (SHELXL97).
Most of the H-atoms were calculated geometrically and a riding model was
used during refinement process; the remaining ones were located by
difference Fourier syntheses and refined isotropically.
;
# Insert blank lines between references
_publ_section_references
;
Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C.
Guagliardi, A., Moliterni, A.G.G., Polidori, G. & Spagna, R.
(1999) J. Appl. Cryst. 32, 115-119.
Cosier, J. & Glazer, A.M. (1986). J. Appl. Cryst. 19, 105-107.
Flack, H.D. (1983). Acta Cryst. A39, 876-881.
L. J. Farrugia, J. Appl. Cryst (1997), 30, 565.
Sheldrick, G.M. SHELXL97 (1997). Program for crystal structure
refinement. University of G\\"ottingen, Germany.
Sheldrick, G.M. SHELXS97 (1997). Program for Crystal Structure
solution. University of G\\"ottingen, Germany.
Sluis, P. van der & Spek, A.L. (1990). Acta Cryst. A46, 194-201.
Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13.
Wilson, A.J.C. (1992) Ed. International Tables for Crystallography,
Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands.
;
_publ_section_acknowledgements
;
;
_publ_section_figure_captions
; View of the title compound with the atom numbering scheme.
Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
;
#===============================================================================
data_h237
_database_code_depnum_ccdc_archive 'CCDC 869742'
#TrackingRef '9893_web_deposit_cif_file_0_MichaelHaindl_1330528584.h237_2.cif'
#===============================================================================
# 5. CHEMICAL DATA
_chemical_name_systematic
;
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C17 H20 N O, C7 H5 O2'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural ?
_chemical_formula_sum 'C24 H25 N O3'
_chemical_formula_iupac ?
_chemical_formula_weight 375.45
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
# 6. CRYSTAL DATA
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_Hall 'P 2yb'
_symmetry_space_group_name_H-M 'P 21'
_symmetry_Int_Tables_number 4
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,-z
_cell_length_a 5.9196(3)
_cell_length_b 19.4951(9)
_cell_length_c 9.1303(5)
_cell_angle_alpha 90
_cell_angle_beta 107.906(5)
_cell_angle_gamma 90
_cell_volume 1002.63(9)
_cell_formula_units_Z 2
_cell_measurement_temperature 123
_cell_measurement_reflns_used 3543
_cell_measurement_theta_min 5.0794
_cell_measurement_theta_max 66.4670
_cell_special_details
;
;
_exptl_crystal_description rod
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.457
_exptl_crystal_size_mid 0.068
_exptl_crystal_size_min 0.048
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.244
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 400
_exptl_absorpt_coefficient_mu 0.650
_exptl_crystal_density_meas_temp ?
# Permitted for
# analytical 'analytical from crystal shape'
# Example: de Meulenaer&Tompa: ABST
# cylinder 'cylindrical'
# gaussian 'Gaussian from crystal shape'
# Example: PLATON/ABSG
# integration 'integration from crystal shape'
# multi-scan 'symmetry-related measurements'
# Example: SADABS, MULABS
# none 'no absorption corr. applied'
# numerical 'numerical from crystal shape'
# psi-scan 'psi-scan corrections'
# Example: PLATON/ABSP
# refdelf 'refined from delta-F'
# Example: SHELXA, DIFABS, DELABS
# sphere 'spherical'
# Example: PLATON/ABSS
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.30 (release 18-06-2008 CrysAlis171 .NET)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min 0.79562
_exptl_absorpt_correction_T_max 1.00000
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
;
;
_diffrn_ambient_temperature 123
_diffrn_radiation_wavelength 1.54184
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_source 'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator mirror
_diffrn_measurement_device_type 'Oxford Diffraction Gemini Ultra'
_diffrn_measurement_method omega-scan
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
1 omega 10.00 63.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -11.6137 45.0000 30.0000 0.0000 0.0000 53
#__ type_ start__ end____ width___ exp.time_
2 omega -58.00 -13.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 11.6137 -45.0000 0.0000 0.0000 0.0000 45
#__ type_ start__ end____ width___ exp.time_
3 omega 14.00 61.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -11.6137 45.0000 90.0000 0.0000 0.0000 47
#__ type_ start__ end____ width___ exp.time_
4 omega -123.00 -70.00 1.0000 23.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -90.0000 128.0000 38.0000 0.0000 0.0000 53
#__ type_ start__ end____ width___ exp.time_
5 omega -118.00 -65.00 1.0000 23.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -90.0000 45.0000 120.0000 0.0000 0.0000 53
#__ type_ start__ end____ width___ exp.time_
6 omega -148.00 -122.00 1.0000 23.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -90.0000 -142.0000 153.0000 0.0000 0.0000 26
#__ type_ start__ end____ width___ exp.time_
7 omega -165.00 -112.00 1.0000 23.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -90.0000 -45.0000 0.0000 0.0000 0.0000 53
#__ type_ start__ end____ width___ exp.time_
8 omega 66.00 119.00 1.0000 23.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 93.5000 45.0000 240.0000 0.0000 0.0000 53
#__ type_ start__ end____ width___ exp.time_
9 omega 80.00 133.00 1.0000 23.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 93.5000 -92.0000 296.0000 0.0000 0.0000 53
#__ type_ start__ end____ width___ exp.time_
10 omega 124.00 168.00 1.0000 23.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 93.5000 45.0000 210.0000 0.0000 0.0000 44
#__ type_ start__ end____ width___ exp.time_
11 omega 21.00 71.00 1.0000 23.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 93.5000 -45.0000 300.0000 0.0000 0.0000 50
#__ type_ start__ end____ width___ exp.time_
12 omega 117.00 162.00 1.0000 23.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 93.5000 130.0000 306.0000 0.0000 0.0000 45
#__ type_ start__ end____ width___ exp.time_
13 omega 15.00 73.00 1.0000 23.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 93.5000 -77.0000 120.0000 0.0000 0.0000 58
#__ type_ start__ end____ width___ exp.time_
14 omega 21.00 54.00 1.0000 23.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 93.5000 -139.0000 238.0000 0.0000 0.0000 33
#__ type_ start__ end____ width___ exp.time_
15 omega 117.00 167.00 1.0000 23.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 93.5000 45.0000 60.0000 0.0000 0.0000 50
#__ type_ start__ end____ width___ exp.time_
16 omega 84.00 113.00 1.0000 23.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 93.5000 -93.0000 133.0000 0.0000 0.0000 29
#__ type_ start__ end____ width___ exp.time_
17 omega 69.00 110.00 1.0000 23.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 93.5000 77.0000 60.0000 0.0000 0.0000 41
#__ type_ start__ end____ width___ exp.time_
18 omega 76.00 119.00 1.0000 23.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 93.5000 -37.0000 220.0000 0.0000 0.0000 43
#__ type_ start__ end____ width___ exp.time_
19 omega 70.00 96.00 1.0000 23.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 93.5000 -63.0000 176.0000 0.0000 0.0000 26
#__ type_ start__ end____ width___ exp.time_
20 omega 67.00 93.00 1.0000 23.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 93.5000 -34.0000 257.0000 0.0000 0.0000 26
#__ type_ start__ end____ width___ exp.time_
21 omega 74.00 101.00 1.0000 23.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 93.5000 -89.0000 255.0000 0.0000 0.0000 27
#__ type_ start__ end____ width___ exp.time_
22 omega 81.00 108.00 1.0000 23.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 93.5000 -92.0000 174.0000 0.0000 0.0000 27
#__ type_ start__ end____ width___ exp.time_
23 omega 19.00 45.00 1.0000 23.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 93.5000 -128.0000 321.0000 0.0000 0.0000 26
;
_diffrn_detector_area_resol_mean 10.5431
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% 0
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
# number of measured reflections (redundant set)
_diffrn_reflns_number 5354
_diffrn_reflns_av_R_equivalents 0.0464
_diffrn_reflns_av_sigmaI/netI 0.0368
_diffrn_reflns_limit_h_min -5
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_k_min -23
_diffrn_reflns_limit_k_max 22
_diffrn_reflns_limit_l_min -10
_diffrn_reflns_limit_l_max 10
_diffrn_reflns_theta_min 5.09
_diffrn_reflns_theta_max 66.65
_diffrn_reflns_theta_full 66.65
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_reduction_process
;
;
# number of unique reflections
_reflns_number_total 2855
# number of observed reflections (> n sig(I))
_reflns_number_gt 2584
_reflns_threshold_expression I>2\s(I)
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.30 (release 18-06-2008 CrysAlis171 .NET)
;
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.30 (release 18-06-2008 CrysAlis171 .NET)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.30 (release 18-06-2008 CrysAlis171 .NET)
;
_computing_structure_solution 'SIR-97 (Altomare, 1999)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'PLATON (Spek, 1990)'
_computing_publication_material 'PLATON (Spek, 2003)'
#===============================================================================
# 8. REFINEMENT DATA
_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^)+(0.0841P)^2^+0.1355P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
# Permitted for _refine_ls_hydrogen_treatment :
# refall - refined all H parameters
# refxyz - refined H coordinates only
# refU - refined H U only
# noref - no refinement of H parameters
# constr - H parameters constrained
# mixed - some constrained, some independent
# undef - H-atom parameters not defined
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method shelxl
_refine_ls_extinction_coef 0.0121(17)
_refine_ls_extinction_expression FC^*^=KFC[1+0.001XFC^2^\L^3^/SIN(2\Q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack -0.2(3)
# Permitted for _chemical_absolute_configuration:
# Absolute configuration details
# rm = Det. by chiral ref. mol. with known abs.conf
# ad = Det. by anomalous dispersion
# rmad = Det. by 'rm' and 'ad'
# syn = Det. with reference to synthesis
# unk = Unknown/Arbitrary
_chemical_absolute_configuration ?
_refine_ls_number_reflns 2855
_refine_ls_number_parameters 263
_refine_ls_number_restraints 1
_refine_ls_number_constraints ?
_refine_ls_R_factor_all 0.0513
_refine_ls_R_factor_gt 0.0455
_refine_ls_wR_factor_ref 0.1276
_refine_ls_wR_factor_gt 0.1208
_refine_ls_goodness_of_fit_ref 1.090
_refine_ls_restrained_S_all 1.090
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.186
_refine_diff_density_min -0.199
_refine_diff_density_rms 0.051
#===============================================================================
# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O Uani -0.3482(3) -0.52550(10) -0.9661(2) 1.000 0.0274(6) . .
N1 N Uani 0.0922(4) -0.60690(13) -0.9110(3) 1.000 0.0261(6) . .
C1 C Uani -0.1231(4) -0.49154(14) -0.9265(3) 1.000 0.0243(7) . .
C2 C Uani 0.0499(4) -0.53591(14) -0.9824(3) 1.000 0.0258(8) . .
C3 C Uani -0.0373(6) -0.55012(16) -1.1550(3) 1.000 0.0334(9) . .
C4 C Uani 0.0814(5) -0.61719(16) -1.1712(4) 1.000 0.0351(9) . .
C5 C Uani 0.0567(6) -0.65839(16) -1.0380(4) 1.000 0.0397(10) . .
C6 C Uani -0.0415(4) -0.47442(14) -0.7553(3) 1.000 0.0239(7) . .
C7 C Uani 0.1839(5) -0.48768(14) -0.6561(3) 1.000 0.0275(8) . .
C8 C Uani 0.2450(5) -0.46833(17) -0.5024(4) 1.000 0.0337(8) . .
C9 C Uani 0.0835(5) -0.43512(16) -0.4466(3) 1.000 0.0329(8) . .
C10 C Uani -0.1448(5) -0.42112(16) -0.5439(3) 1.000 0.0320(8) . .
C11 C Uani -0.2039(5) -0.44102(15) -0.6966(3) 1.000 0.0294(8) . .
C12 C Uani -0.1517(4) -0.42511(14) -1.0193(3) 1.000 0.0246(7) . .
C13 C Uani 0.0478(5) -0.38403(15) -1.0080(3) 1.000 0.0283(8) . .
C14 C Uani 0.0292(5) -0.32654(15) -1.0986(3) 1.000 0.0319(8) . .
C15 C Uani -0.1883(5) -0.30763(16) -1.2014(4) 1.000 0.0342(9) . .
C16 C Uani -0.3864(5) -0.34644(17) -1.2096(4) 1.000 0.0369(9) . .
C17 C Uani -0.3687(5) -0.40515(15) -1.1198(3) 1.000 0.0300(8) . .
O2 O Uani -0.4374(3) -0.60621(11) -0.7529(2) 1.000 0.0320(6) . .
O3 O Uani -0.1092(4) -0.66709(12) -0.7237(3) 1.000 0.0426(7) . .
C18 C Uani -0.3335(4) -0.69168(14) -0.5561(3) 1.000 0.0247(7) . .
C19 C Uani -0.5140(5) -0.67290(16) -0.4968(3) 1.000 0.0305(8) . .
C20 C Uani -0.5508(5) -0.71017(18) -0.3770(4) 1.000 0.0354(9) . .
C21 C Uani -0.4081(5) -0.76572(17) -0.3138(4) 1.000 0.0349(9) . .
C22 C Uani -0.2254(5) -0.78431(15) -0.3719(4) 1.000 0.0327(8) . .
C23 C Uani -0.1887(5) -0.74729(15) -0.4927(3) 1.000 0.0276(8) . .
C24 C Uani -0.2902(4) -0.65272(14) -0.6863(3) 1.000 0.0275(8) . .
H1M H Uiso 0.002(7) -0.615(2) -0.862(4) 1.000 0.0310 . .
H1N H Uiso 0.241(7) -0.6098(19) -0.841(4) 1.000 0.0310 . .
H1O H Uiso -0.356(6) -0.551(2) -0.889(4) 1.000 0.0330 . .
H2 H Uiso 0.20570 -0.51150 -0.95750 1.000 0.0310 calc R
H3A H Uiso -0.21230 -0.55460 -1.19250 1.000 0.0400 calc R
H3B H Uiso 0.01140 -0.51300 -1.21300 1.000 0.0400 calc R
H4A H Uiso -0.00040 -0.63980 -1.27050 1.000 0.0420 calc R
H4B H Uiso 0.25040 -0.61020 -1.16320 1.000 0.0420 calc R
H5A H Uiso -0.10260 -0.67960 -1.06330 1.000 0.0480 calc R
H5B H Uiso 0.17850 -0.69490 -1.00900 1.000 0.0480 calc R
H7 H Uiso 0.29750 -0.51020 -0.69360 1.000 0.0330 calc R
H8 H Uiso 0.39940 -0.47810 -0.43540 1.000 0.0400 calc R
H9 H Uiso 0.12740 -0.42170 -0.34160 1.000 0.0390 calc R
H10 H Uiso -0.25740 -0.39840 -0.50600 1.000 0.0380 calc R
H11 H Uiso -0.35900 -0.43170 -0.76330 1.000 0.0350 calc R
H13 H Uiso 0.19710 -0.39600 -0.93720 1.000 0.0340 calc R
H14 H Uiso 0.16610 -0.29960 -1.09070 1.000 0.0380 calc R
H15 H Uiso -0.20030 -0.26840 -1.26520 1.000 0.0410 calc R
H16 H Uiso -0.53660 -0.33300 -1.27720 1.000 0.0440 calc R
H17 H Uiso -0.50650 -0.43170 -1.12760 1.000 0.0360 calc R
H19 H Uiso -0.61210 -0.63460 -0.53830 1.000 0.0370 calc R
H20 H Uiso -0.67570 -0.69740 -0.33760 1.000 0.0420 calc R
H21 H Uiso -0.43480 -0.79090 -0.23160 1.000 0.0420 calc R
H22 H Uiso -0.12600 -0.82220 -0.32910 1.000 0.0390 calc R
H23 H Uiso -0.06380 -0.76000 -0.53230 1.000 0.0330 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 0.0174(8) 0.0284(10) 0.0318(11) 0.0024(9) 0.0010(7) -0.0051(7)
N1 0.0213(10) 0.0244(11) 0.0316(12) 0.0024(10) 0.0069(10) 0.0010(9)
C1 0.0192(11) 0.0251(13) 0.0261(14) 0.0006(11) 0.0033(10) -0.0024(10)
C2 0.0260(13) 0.0228(14) 0.0273(14) 0.0021(11) 0.0063(10) 0.0007(10)
C3 0.0403(15) 0.0306(16) 0.0277(15) -0.0003(12) 0.0081(12) 0.0038(12)
C4 0.0373(14) 0.0325(16) 0.0334(15) -0.0069(13) 0.0079(12) 0.0021(12)
C5 0.0475(17) 0.0267(15) 0.0421(18) -0.0039(14) 0.0098(14) 0.0012(13)
C6 0.0243(12) 0.0227(12) 0.0242(13) 0.0014(11) 0.0068(11) -0.0036(10)
C7 0.0250(12) 0.0261(14) 0.0283(14) -0.0006(11) 0.0037(11) 0.0009(10)
C8 0.0325(14) 0.0338(15) 0.0276(15) 0.0015(12) -0.0012(12) -0.0022(12)
C9 0.0389(14) 0.0343(16) 0.0246(14) 0.0002(12) 0.0084(12) -0.0067(12)
C10 0.0313(13) 0.0335(15) 0.0340(16) -0.0049(13) 0.0143(11) -0.0049(12)
C11 0.0218(11) 0.0313(15) 0.0329(15) 0.0007(12) 0.0051(10) -0.0006(11)
C12 0.0244(12) 0.0238(13) 0.0238(13) -0.0035(11) 0.0048(10) 0.0010(10)
C13 0.0225(13) 0.0250(13) 0.0348(15) -0.0014(12) 0.0048(11) -0.0016(10)
C14 0.0330(14) 0.0278(14) 0.0351(15) -0.0017(12) 0.0107(11) -0.0013(12)
C15 0.0447(16) 0.0248(14) 0.0322(16) 0.0018(12) 0.0106(12) -0.0007(12)
C16 0.0339(14) 0.0349(17) 0.0341(16) 0.0033(14) -0.0008(12) 0.0003(12)
C17 0.0252(12) 0.0310(15) 0.0293(15) 0.0000(12) 0.0018(11) -0.0006(11)
O2 0.0228(8) 0.0324(10) 0.0384(11) 0.0078(10) 0.0058(7) 0.0026(8)
O3 0.0350(11) 0.0429(13) 0.0568(14) 0.0203(11) 0.0245(10) 0.0122(9)
C18 0.0204(12) 0.0230(13) 0.0285(13) -0.0033(11) 0.0043(10) -0.0024(9)
C19 0.0254(12) 0.0308(14) 0.0328(15) -0.0016(12) 0.0053(11) 0.0024(11)
C20 0.0313(14) 0.0428(18) 0.0322(15) -0.0036(13) 0.0100(12) 0.0010(13)
C21 0.0384(14) 0.0350(16) 0.0314(16) 0.0014(13) 0.0111(12) -0.0036(13)
C22 0.0360(14) 0.0267(14) 0.0323(16) 0.0004(12) 0.0060(12) 0.0003(12)
C23 0.0243(12) 0.0269(14) 0.0292(14) -0.0034(12) 0.0047(10) 0.0008(10)
C24 0.0225(12) 0.0238(13) 0.0325(14) 0.0025(11) 0.0029(11) 0.0016(10)
_geom_special_details
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.431(3) . . yes
O1 H1O 0.88(4) . . no
O2 C24 1.275(3) . . yes
O3 C24 1.252(4) . . yes
N1 C5 1.499(4) . . yes
N1 C2 1.517(4) . . yes
N1 H1N 0.92(4) . . no
N1 H1M 0.81(4) . . no
C1 C12 1.528(4) . . no
C1 C2 1.542(4) . . no
C1 C6 1.524(4) . . no
C2 C3 1.525(4) . . no
C3 C4 1.513(5) . . no
C4 C5 1.502(5) . . no
C6 C7 1.387(4) . . no
C6 C11 1.397(4) . . no
C7 C8 1.389(4) . . no
C8 C9 1.376(4) . . no
C9 C10 1.397(4) . . no
C10 C11 1.385(4) . . no
C12 C17 1.385(4) . . no
C12 C13 1.404(4) . . no
C13 C14 1.377(4) . . no
C14 C15 1.390(4) . . no
C15 C16 1.378(5) . . no
C16 C17 1.393(4) . . no
C2 H2 1.0000 . . no
C3 H3A 0.9900 . . no
C3 H3B 0.9900 . . no
C4 H4A 0.9900 . . no
C4 H4B 0.9900 . . no
C5 H5B 0.9900 . . no
C5 H5A 0.9900 . . no
C7 H7 0.9500 . . no
C8 H8 0.9500 . . no
C9 H9 0.9500 . . no
C10 H10 0.9500 . . no
C11 H11 0.9500 . . no
C13 H13 0.9500 . . no
C14 H14 0.9500 . . no
C15 H15 0.9500 . . no
C16 H16 0.9500 . . no
C17 H17 0.9500 . . no
C18 C19 1.387(4) . . no
C18 C23 1.393(4) . . no
C18 C24 1.498(4) . . no
C19 C20 1.385(4) . . no
C20 C21 1.386(5) . . no
C21 C22 1.391(5) . . no
C22 C23 1.390(4) . . no
C19 H19 0.9500 . . no
C20 H20 0.9500 . . no
C21 H21 0.9500 . . no
C22 H22 0.9500 . . no
C23 H23 0.9500 . . no
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1O 110(2) . . . no
C2 N1 C5 108.3(2) . . . yes
C5 N1 H1N 112(2) . . . no
H1M N1 H1N 105(4) . . . no
C5 N1 H1M 110(3) . . . no
C2 N1 H1M 111(3) . . . no
C2 N1 H1N 111(2) . . . no
C2 C1 C6 115.4(2) . . . no
C2 C1 C12 105.3(2) . . . no
C6 C1 C12 109.2(2) . . . no
O1 C1 C2 108.6(2) . . . yes
O1 C1 C6 109.7(2) . . . yes
O1 C1 C12 108.4(2) . . . yes
C1 C2 C3 113.3(2) . . . no
N1 C2 C1 114.1(2) . . . yes
N1 C2 C3 103.7(2) . . . yes
C2 C3 C4 103.8(2) . . . no
C3 C4 C5 102.7(3) . . . no
N1 C5 C4 104.1(2) . . . yes
C1 C6 C7 124.5(2) . . . no
C7 C6 C11 118.3(2) . . . no
C1 C6 C11 117.2(2) . . . no
C6 C7 C8 120.6(3) . . . no
C7 C8 C9 120.5(3) . . . no
C8 C9 C10 120.2(3) . . . no
C9 C10 C11 118.8(3) . . . no
C6 C11 C10 121.8(3) . . . no
C1 C12 C13 119.7(2) . . . no
C1 C12 C17 121.8(2) . . . no
C13 C12 C17 118.4(3) . . . no
C12 C13 C14 120.7(3) . . . no
C13 C14 C15 120.5(3) . . . no
C14 C15 C16 119.2(3) . . . no
C15 C16 C17 120.7(3) . . . no
C12 C17 C16 120.5(3) . . . no
N1 C2 H2 109.00 . . . no
C1 C2 H2 109.00 . . . no
C3 C2 H2 108.00 . . . no
C2 C3 H3A 111.00 . . . no
C2 C3 H3B 111.00 . . . no
C4 C3 H3A 111.00 . . . no
C4 C3 H3B 111.00 . . . no
H3A C3 H3B 109.00 . . . no
C3 C4 H4A 111.00 . . . no
C3 C4 H4B 111.00 . . . no
C5 C4 H4A 111.00 . . . no
C5 C4 H4B 111.00 . . . no
H4A C4 H4B 109.00 . . . no
N1 C5 H5A 111.00 . . . no
N1 C5 H5B 111.00 . . . no
C4 C5 H5A 111.00 . . . no
C4 C5 H5B 111.00 . . . no
H5A C5 H5B 109.00 . . . no
C6 C7 H7 120.00 . . . no
C8 C7 H7 120.00 . . . no
C7 C8 H8 120.00 . . . no
C9 C8 H8 120.00 . . . no
C8 C9 H9 120.00 . . . no
C10 C9 H9 120.00 . . . no
C9 C10 H10 121.00 . . . no
C11 C10 H10 121.00 . . . no
C6 C11 H11 119.00 . . . no
C10 C11 H11 119.00 . . . no
C12 C13 H13 120.00 . . . no
C14 C13 H13 120.00 . . . no
C13 C14 H14 120.00 . . . no
C15 C14 H14 120.00 . . . no
C14 C15 H15 120.00 . . . no
C16 C15 H15 120.00 . . . no
C15 C16 H16 120.00 . . . no
C17 C16 H16 120.00 . . . no
C12 C17 H17 120.00 . . . no
C16 C17 H17 120.00 . . . no
C19 C18 C23 119.5(3) . . . no
C19 C18 C24 121.1(2) . . . no
C23 C18 C24 119.4(2) . . . no
C18 C19 C20 119.8(3) . . . no
C19 C20 C21 121.0(3) . . . no
C20 C21 C22 119.4(3) . . . no
C21 C22 C23 119.8(3) . . . no
C18 C23 C22 120.5(3) . . . no
O2 C24 O3 123.1(3) . . . yes
O2 C24 C18 118.7(2) . . . yes
O3 C24 C18 118.2(2) . . . yes
C18 C19 H19 120.00 . . . no
C20 C19 H19 120.00 . . . no
C19 C20 H20 119.00 . . . no
C21 C20 H20 120.00 . . . no
C20 C21 H21 120.00 . . . no
C22 C21 H21 120.00 . . . no
C21 C22 H22 120.00 . . . no
C23 C22 H22 120.00 . . . no
C18 C23 H23 120.00 . . . no
C22 C23 H23 120.00 . . . no
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 C2 C1 129.8(3) . . . . no
C5 N1 C2 C3 6.0(3) . . . . no
C2 N1 C5 C4 19.7(3) . . . . no
O1 C1 C2 N1 -60.6(3) . . . . no
O1 C1 C2 C3 57.8(3) . . . . no
C12 C1 C2 C3 -58.1(3) . . . . no
O1 C1 C6 C7 132.3(3) . . . . no
O1 C1 C6 C11 -50.0(3) . . . . no
C2 C1 C6 C7 9.3(4) . . . . no
C6 C1 C2 N1 63.0(3) . . . . no
C12 C1 C6 C7 -109.0(3) . . . . no
C12 C1 C6 C11 68.7(3) . . . . no
O1 C1 C12 C13 -176.3(2) . . . . no
O1 C1 C12 C17 1.1(3) . . . . no
C2 C1 C12 C13 -60.3(3) . . . . no
C2 C1 C12 C17 117.2(3) . . . . no
C6 C1 C12 C13 64.2(3) . . . . no
C6 C1 C12 C17 -118.4(3) . . . . no
C6 C1 C2 C3 -178.6(2) . . . . no
C12 C1 C2 N1 -176.5(2) . . . . no
C2 C1 C6 C11 -173.0(2) . . . . no
N1 C2 C3 C4 -29.3(3) . . . . no
C1 C2 C3 C4 -153.5(2) . . . . no
C2 C3 C4 C5 41.9(3) . . . . no
C3 C4 C5 N1 -37.7(3) . . . . no
C1 C6 C7 C8 178.0(3) . . . . no
C11 C6 C7 C8 0.2(4) . . . . no
C1 C6 C11 C10 -177.8(3) . . . . no
C7 C6 C11 C10 0.1(4) . . . . no
C6 C7 C8 C9 -0.6(5) . . . . no
C7 C8 C9 C10 0.6(5) . . . . no
C8 C9 C10 C11 -0.3(5) . . . . no
C9 C10 C11 C6 -0.1(5) . . . . no
C1 C12 C13 C14 175.4(3) . . . . no
C17 C12 C13 C14 -2.2(4) . . . . no
C1 C12 C17 C16 -176.2(3) . . . . no
C13 C12 C17 C16 1.3(4) . . . . no
C12 C13 C14 C15 0.9(4) . . . . no
C13 C14 C15 C16 1.2(5) . . . . no
C14 C15 C16 C17 -2.0(5) . . . . no
C15 C16 C17 C12 0.7(5) . . . . no
C23 C18 C19 C20 -1.0(4) . . . . no
C24 C18 C19 C20 179.6(3) . . . . no
C19 C18 C23 C22 0.6(4) . . . . no
C24 C18 C23 C22 -179.9(3) . . . . no
C19 C18 C24 O2 -7.2(4) . . . . no
C19 C18 C24 O3 172.2(3) . . . . no
C23 C18 C24 O2 173.4(2) . . . . no
C23 C18 C24 O3 -7.2(4) . . . . no
C18 C19 C20 C21 0.7(5) . . . . no
C19 C20 C21 C22 -0.1(5) . . . . no
C20 C21 C22 C23 -0.3(5) . . . . no
C21 C22 C23 C18 0.0(5) . . . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 O2 2.679(3) . . no
O1 N1 2.960(3) . . no
O2 N1 2.714(3) . 1_455 no
O2 C2 3.401(3) . 1_455 no
O2 O1 2.679(3) . . no
O3 C5 3.311(4) . . no
O3 N1 2.641(4) . . no
O1 H17 2.3600 . . no
O1 H1M 2.65(4) . . no
O1 H11 2.6200 . . no
O1 H3A 2.5000 . . no
O1 H2 2.6800 . 1_455 no
O2 H1O 1.82(4) . . no
O2 H1N 1.83(4) . 1_455 no
O2 H7 2.6000 . 1_455 no
O2 H19 2.5400 . . no
O3 H1O 2.86(4) . . no
O3 H1M 1.89(4) . . no
O3 H23 2.4700 . . no
O3 H15 2.7200 . 2_543 no
O3 H1N 2.84(4) . . no
N1 C7 3.215(4) . . no
N1 O1 2.960(3) . . no
N1 O2 2.714(3) . 1_655 no
N1 O3 2.641(4) . . no
N1 H7 2.7400 . . no
N1 H1O 2.93(4) . . no
C2 O2 3.401(3) . 1_655 no
C3 C13 3.482(4) . . no
C3 C17 3.511(4) . . no
C5 C15 3.578(5) . 2_543 no
C5 O3 3.311(4) . . no
C5 C14 3.599(4) . 2_543 no
C7 N1 3.215(4) . . no
C9 C22 3.599(4) . 2_554 no
C13 C3 3.482(4) . . no
C14 C5 3.599(4) . 2_553 no
C15 C5 3.578(5) . 2_553 no
C17 C3 3.511(4) . . no
C22 C9 3.599(4) . 2_544 no
C2 H13 2.8500 . . no
C2 H7 2.6400 . . no
C4 H20 2.8600 . 1_654 no
C6 H13 2.9200 . . no
C6 H1M 2.95(4) . . no
C7 H2 2.8300 . . no
C7 H1M 3.10(4) . . no
C7 H1N 3.00(4) . . no
C9 H16 3.0500 . 1_656 no
C9 H3B 2.7600 . 1_556 no
C9 H22 3.0700 . 2_554 no
C10 H22 2.9600 . 2_554 no
C11 H22 2.9900 . 2_554 no
C11 H1O 2.74(4) . . no
C12 H3A 2.9400 . . no
C12 H11 2.9600 . . no
C12 H3B 2.8400 . . no
C13 H2 2.6500 . . no
C14 H9 3.0800 . 1_554 no
C15 H5B 2.9100 . 2_553 no
C17 H9 3.0600 . 1_454 no
C18 H4A 2.9200 . 1_556 no
C19 H15 2.9600 . 2_443 no
C20 H23 3.0900 . 1_455 no
C21 H5A 2.9600 . 1_556 no
C23 H16 2.7800 . 2_443 no
C23 H4A 2.8900 . 1_556 no
C23 H20 3.0900 . 1_655 no
C24 H1N 2.83(4) . 1_455 no
C24 H1O 2.66(4) . . no
C24 H1M 2.80(4) . . no
H1M O1 2.65(4) . . no
H1M O3 1.89(4) . . no
H1M C6 2.95(4) . . no
H1M C24 2.80(4) . . no
H1M H1O 2.41(6) . . no
H1M C7 3.10(4) . . no
H1N O2 1.83(4) . 1_655 no
H1N O3 2.84(4) . . no
H1N C24 2.83(4) . 1_655 no
H1N H7 2.3300 . . no
H1N C7 3.00(4) . . no
H1O O2 1.82(4) . . no
H1O O3 2.86(4) . . no
H1O N1 2.93(4) . . no
H1O C11 2.74(4) . . no
H1O C24 2.66(4) . . no
H1O H1M 2.41(6) . . no
H1O H2 2.5900 . 1_455 no
H1O H11 2.6000 . . no
H2 H1O 2.5900 . 1_655 no
H2 H7 2.3000 . . no
H2 H13 2.2600 . . no
H2 C13 2.6500 . . no
H2 O1 2.6800 . 1_655 no
H2 C7 2.8300 . . no
H3A O1 2.5000 . . no
H3A C12 2.9400 . . no
H3B C9 2.7600 . 1_554 no
H3B H9 2.3500 . 1_554 no
H3B C12 2.8400 . . no
H4A C18 2.9200 . 1_554 no
H4A C23 2.8900 . 1_554 no
H4A H20 2.4600 . 1_654 no
H4B H20 2.4600 . 1_654 no
H5A C21 2.9600 . 1_554 no
H5B C15 2.9100 . 2_543 no
H7 C2 2.6400 . . no
H7 H1N 2.3300 . . no
H7 N1 2.7400 . . no
H7 O2 2.6000 . 1_655 no
H7 H2 2.3000 . . no
H9 C17 3.0600 . 1_656 no
H9 C14 3.0800 . 1_556 no
H9 H16 2.5600 . 1_656 no
H9 H17 2.4400 . 1_656 no
H9 H3B 2.3500 . 1_556 no
H11 O1 2.6200 . . no
H11 H1O 2.6000 . . no
H11 C12 2.9600 . . no
H13 C2 2.8500 . . no
H13 H2 2.2600 . . no
H13 C6 2.9200 . . no
H15 O3 2.7200 . 2_553 no
H15 C19 2.9600 . 2_453 no
H16 H9 2.5600 . 1_454 no
H16 C9 3.0500 . 1_454 no
H16 C23 2.7800 . 2_453 no
H17 O1 2.3600 . . no
H17 H9 2.4400 . 1_454 no
H19 O2 2.5400 . . no
H20 C4 2.8600 . 1_456 no
H20 C23 3.0900 . 1_455 no
H20 H4A 2.4600 . 1_456 no
H20 H4B 2.4600 . 1_456 no
H22 C9 3.0700 . 2_544 no
H22 C10 2.9600 . 2_544 no
H22 C11 2.9900 . 2_544 no
H23 O3 2.4700 . . no
H23 C20 3.0900 . 1_655 no
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
_geom_hbond_publ_flag
N1 H1M O3 0.81(4) 1.89(4) 2.641(4) 154(4) . yes
N1 H1N O2 0.92(4) 1.83(4) 2.714(3) 162(3) 1_655 yes
O1 H1O O2 0.88(4) 1.82(4) 2.679(3) 168(4) . yes
C3 H3A O1 0.9900 2.5000 2.923(4) 105.00 . yes
C17 H17 O1 0.9500 2.3600 2.717(3) 102.00 . yes
#===END