# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is (c) The Royal Society of Chemistry and
# The Centre National de la Recherche Scientifique, 2009
data_global
_journal_name_full 'New J.Chem.'
_journal_coden_Cambridge 0440
_publ_contact_author_name 'Iversen, Bo'
_publ_contact_author_email bo@chem.au.dk
_publ_section_title
;
Three new co-crystals of hydroquinone: Crystal
structures and Hirshfeld surface analysis of intermolecular interactions
;
loop_
_publ_author_name
B.Iversen
H.Clausen
M.Chevallier
M.Spackman
# Attachment '- Structure1.cif'
data_hq_isoprop
_database_code_depnum_ccdc_archive 'CCDC 692266'
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C6 H6 O2, C3 H8 O'
_chemical_formula_sum 'C9 H14 O3'
_chemical_formula_weight 170.2
#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_space_group_name_H-M 'P -1'
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_int_tables_number 2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 7.5561(5)
_cell_length_b 8.1977(8)
_cell_length_c 8.3331(6)
_cell_angle_alpha 88.322(7)
_cell_angle_beta 79.154(6)
_cell_angle_gamma 67.174(8)
_cell_volume 466.71(7)
_cell_formula_units_Z 2.00000
_cell_measurement_reflns_used 2549
_cell_measurement_theta_min 2.6925
_cell_measurement_theta_max 34.6999
_cell_measurement_temperature 100(2)
#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_density_diffrn 1.211
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 184
_exptl_special_details
;
?
;
#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_crystal_description rectangular
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.2284
_exptl_crystal_size_mid 0.1833
_exptl_crystal_size_min 0.1404
_exptl_absorpt_coefficient_mu 0.090
_exptl_absorpt_correction_T_min 0.986
_exptl_absorpt_correction_T_max 0.992
_exptl_absorpt_correction_type analytical
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May 8 2007,13:10:02)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.7107
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_source 'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator graphite
_diffrn_detector_area_resol_mean 16.0009
_diffrn_reflns_av_R_equivalents 0.031
_diffrn_reflns_av_unetI/netI 0.0585
_diffrn_reflns_number 8574
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_theta_min 2.7
_diffrn_reflns_theta_max 32.03
_diffrn_reflns_theta_full 32.03
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_reflns_number_total 3191
_reflns_number_gt 2117
_reflns_threshold_expression >2sigma(I)
_diffrn_reflns_reduction_process
;
Scaled and merged with SORTAV
R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_measurement_device_type 'Oxford diffraction Xcalibur S system'
_diffrn_measurement_method 'omega scans'
_diffrn_orient_matrix_UB_11 -0.0014276345
_diffrn_orient_matrix_UB_12 0.0868698133
_diffrn_orient_matrix_UB_13 0.0036536097
_diffrn_orient_matrix_UB_21 0.0166025704
_diffrn_orient_matrix_UB_22 0.0001867106
_diffrn_orient_matrix_UB_23 -0.0866519096
_diffrn_orient_matrix_UB_31 -0.1023551479
_diffrn_orient_matrix_UB_32 0.0358595283
_diffrn_orient_matrix_UB_33 0.0027476909
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
1 omega -55.00 -6.00 1.0000 33.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -28.9873 75.0000 120.0000 0.0000 0.0000 49
#__ type_ start__ end____ width___ exp.time_
2 omega -56.00 -11.00 1.0000 33.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -28.9873 -45.0000 240.0000 0.0000 0.0000 45
#__ type_ start__ end____ width___ exp.time_
3 omega -56.00 -11.00 1.0000 33.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -28.9873 -45.0000 120.0000 0.0000 0.0000 45
#__ type_ start__ end____ width___ exp.time_
4 omega -98.00 -52.00 1.0000 33.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -28.9873 -45.0000 120.0000 0.0000 0.0000 46
#__ type_ start__ end____ width___ exp.time_
5 omega -98.00 -52.00 1.0000 33.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -28.9873 -45.0000 240.0000 0.0000 0.0000 46
#__ type_ start__ end____ width___ exp.time_
6 omega 12.00 64.00 1.0000 33.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 29.7686 -90.0000 59.0000 0.0000 0.0000 52
#__ type_ start__ end____ width___ exp.time_
7 omega 7.00 55.00 1.0000 33.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 29.7686 -75.0000 240.0000 0.0000 0.0000 48
#__ type_ start__ end____ width___ exp.time_
8 omega 14.00 65.00 1.0000 33.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 29.7686 -92.0000 126.0000 0.0000 0.0000 51
#__ type_ start__ end____ width___ exp.time_
9 omega -38.00 11.00 1.0000 33.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 29.7686 -75.0000 240.0000 0.0000 0.0000 49
#__ type_ start__ end____ width___ exp.time_
10 omega 53.00 97.00 1.0000 33.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 29.7686 54.0000 34.0000 0.0000 0.0000 44
#__ type_ start__ end____ width___ exp.time_
11 omega 13.00 57.00 1.0000 33.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 29.7686 54.0000 34.0000 0.0000 0.0000 44
#__ type_ start__ end____ width___ exp.time_
12 omega 4.00 53.00 1.0000 33.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 29.7686 75.0000 240.0000 0.0000 0.0000 49
#__ type_ start__ end____ width___ exp.time_
13 omega 53.00 98.00 1.0000 33.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 29.7686 45.0000 120.0000 0.0000 0.0000 45
;
#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May 8 2007,13:10:02)
;
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May 8 2007,13:10:02) and
SORTAV (Blessing, 1987 & Blessing, 1989)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May 8 2007,13:10:02)
;
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
'XShell (Bruker, 2000)' and Crystal Explorer (Wolff et al., 2005)
;
_computing_publication_material
;
enCIFer (Allen et al., 2004) and WinGX (Farrugia, 1999)
;
#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#
_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^)+(0.0453P)^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_number_reflns 3191
_refine_ls_number_parameters 114
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.084
_refine_ls_R_factor_gt 0.0466
_refine_ls_wR_factor_ref 0.1287
_refine_ls_wR_factor_gt 0.1104
_refine_ls_goodness_of_fit_ref 1.413
_refine_ls_restrained_S_all 1.413
_refine_ls_shift/su_max 0
_refine_ls_shift/su_mean 0
_refine_diff_density_max 0.386
_refine_diff_density_min -0.251
_refine_diff_density_rms 0.056
#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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 0.20295(12) 0.72095(13) 0.47098(10) 0.0192(2) Uani 1 1 d . . .
H1 H 0.3052 0.6788 0.4036 0.029 Uiso 1 1 calc R . .
C1 C 0.10479(17) 0.60817(17) 0.48245(13) 0.0165(2) Uani 1 1 d . . .
C2 C 0.18307(18) 0.44423(18) 0.39904(14) 0.0194(3) Uani 1 1 d . . .
H2 H 0.3059 0.4066 0.3314 0.023 Uiso 1 1 calc R . .
C3 C -0.07814(17) 0.66371(18) 0.58356(14) 0.0188(3) Uani 1 1 d . . .
H3 H -0.1306 0.7735 0.6398 0.023 Uiso 1 1 calc R . .
O10 O 0.52665(13) 0.60930(13) 0.24630(11) 0.0214(2) Uani 1 1 d . . .
H10 H 0.5943 0.5033 0.2287 0.032 Uiso 1 1 calc R . .
C10 C 0.64939(17) 0.70963(18) 0.20943(14) 0.0192(3) Uani 1 1 d . . .
H10A H 0.7619 0.6585 0.2637 0.023 Uiso 1 1 calc R . .
C11 C 0.5266(2) 0.8952(2) 0.27862(18) 0.0296(3) Uani 1 1 d . . .
H11A H 0.484 0.8928 0.3944 0.044 Uiso 1 1 calc R . .
H11B H 0.4147 0.9447 0.2274 0.044 Uiso 1 1 calc R . .
H11C H 0.6029 0.9665 0.2582 0.044 Uiso 1 1 calc R . .
C12 C 0.7214(2) 0.7015(2) 0.02652(16) 0.0279(3) Uani 1 1 d . . .
H12A H 0.6114 0.7517 -0.027 0.042 Uiso 1 1 calc R . .
H12B H 0.7949 0.5803 -0.0118 0.042 Uiso 1 1 calc R . .
H12C H 0.8034 0.7673 0.0023 0.042 Uiso 1 1 calc R . .
O5 O 0.72030(12) 0.24785(13) 0.23042(10) 0.0204(2) Uani 1 1 d . . .
H5 H 0.7559 0.2382 0.3185 0.031 Uiso 1 1 calc R . .
C5 C 0.86204(16) 0.12317(17) 0.11818(14) 0.0157(2) Uani 1 1 d . . .
C6 C 1.00675(17) -0.02520(17) 0.16448(14) 0.0169(2) Uani 1 1 d . . .
H6 H 1.0113 -0.0423 0.2747 0.02 Uiso 1 1 calc R . .
C7 C 0.85542(17) 0.14800(17) -0.04683(14) 0.0176(2) Uani 1 1 d . . .
H7 H 0.7583 0.2472 -0.0782 0.021 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 0.0197(4) 0.0202(5) 0.0178(4) -0.0023(4) 0.0017(3) -0.0100(4)
C1 0.0180(5) 0.0175(6) 0.0140(5) 0.0007(4) -0.0036(4) -0.0066(5)
C2 0.0175(5) 0.0198(7) 0.0185(5) -0.0039(5) 0.0014(4) -0.0066(5)
C3 0.0191(5) 0.0161(7) 0.0193(5) -0.0034(5) 0.0015(4) -0.0067(5)
O10 0.0200(4) 0.0135(5) 0.0268(4) 0.0008(4) 0.0024(3) -0.0054(4)
C10 0.0182(5) 0.0244(7) 0.0176(5) 0.0035(5) -0.0021(4) -0.0120(5)
C11 0.0301(7) 0.0271(8) 0.0345(7) -0.0045(6) 0.0027(6) -0.0178(6)
C12 0.0292(7) 0.0358(9) 0.0220(6) 0.0014(6) -0.0012(5) -0.0179(7)
O5 0.0194(4) 0.0186(5) 0.0193(4) -0.0042(4) -0.0030(3) -0.0031(4)
C5 0.0141(5) 0.0136(6) 0.0194(5) -0.0010(5) -0.0018(4) -0.0059(5)
C6 0.0199(5) 0.0172(6) 0.0151(5) 0.0024(4) -0.0032(4) -0.0089(5)
C7 0.0162(5) 0.0141(6) 0.0210(5) 0.0005(5) -0.0056(4) -0.0035(5)
#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#
_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 C1 1.3836(14) . ?
O1 H1 0.82 . ?
C1 C2 1.3865(18) . ?
C1 C3 1.3869(16) . ?
C2 C3 1.3879(17) 2_566 ?
C2 H2 0.93 . ?
C3 H3 0.93 . ?
O10 C10 1.4495(14) . ?
O10 H10 0.82 . ?
C10 C11 1.504(2) . ?
C10 C12 1.5130(16) . ?
C10 H10A 0.98 . ?
C11 H11A 0.96 . ?
C11 H11B 0.96 . ?
C11 H11C 0.96 . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
O5 C5 1.3770(14) . ?
O5 H5 0.82 . ?
C5 C7 1.3916(16) . ?
C5 C6 1.3868(18) . ?
C6 C7 1.3854(17) 2_755 ?
C6 H6 0.93 . ?
C7 H7 0.93 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
O1 C1 C2 122.64(10) . . ?
O1 C1 C3 117.48(11) . . ?
C2 C1 C3 119.88(11) . . ?
C1 C2 C3 119.99(11) . 2_566 ?
C1 C2 H2 120 . . ?
C3 C2 H2 120 2_566 . ?
C2 C3 C1 120.13(12) 2_566 . ?
C2 C3 H3 119.9 2_566 . ?
C1 C3 H3 119.9 . . ?
C10 O10 H10 109.5 . . ?
O10 C10 C11 106.51(10) . . ?
O10 C10 C12 109.54(10) . . ?
C11 C10 C12 112.86(12) . . ?
O10 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C12 C10 H10A 109.3 . . ?
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 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 O5 H5 109.5 . . ?
O5 C5 C7 117.88(11) . . ?
O5 C5 C6 122.34(10) . . ?
C7 C5 C6 119.77(11) . . ?
C7 C6 C5 120.12(10) 2_755 . ?
C7 C6 H6 119.9 2_755 . ?
C5 C6 H6 119.9 . . ?
C6 C7 C5 120.11(12) 2_755 . ?
C6 C7 H7 119.9 2_755 . ?
C5 C7 H7 119.9 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 179.51(11) . . . 2_566 ?
C3 C1 C2 C3 0.2(2) . . . 2_566 ?
O1 C1 C3 C2 -179.54(11) . . . 2_566 ?
C2 C1 C3 C2 -0.2(2) . . . 2_566 ?
O5 C5 C6 C7 179.15(10) . . . 2_755 ?
C7 C5 C6 C7 0.19(18) . . . 2_755 ?
O5 C5 C7 C6 -179.20(10) . . . 2_755 ?
C6 C5 C7 C6 -0.19(18) . . . 2_755 ?
# Attachment '- Structure2.cif'
#==============================================================================
data_hq_dma_mono2
_database_code_depnum_ccdc_archive 'CCDC 692267'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C4 H9 N O, C6 H6 O2'
_chemical_formula_sum 'C10 H15 N O3'
_chemical_formula_weight 197.23
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'C 2/c'
_symmetry_space_group_name_Hall '-C 2yc'
_symmetry_int_tables_number 15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 11.1325(6)
_cell_length_b 9.0410(5)
_cell_length_c 21.0854(11)
_cell_angle_alpha 90.00
_cell_angle_beta 100.098(4)
_cell_angle_gamma 90.00
_cell_volume 2089.35(19)
_cell_formula_units_Z 8
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 1500
_cell_measurement_theta_min 2.92
_cell_measurement_theta_max 23.99
_exptl_crystal_description plate
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.125
_exptl_crystal_size_min 0.125
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.254
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 848
_exptl_absorpt_coefficient_mu 0.092
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9930
_exptl_absorpt_correction_T_max 0.9939
_exptl_absorpt_process_details '(SORTAV; Blessing, 1997)'
_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 'Bruker SMART APEXII CCD-based diffractometer'
_diffrn_measurement_method '\f-scans and \w-scans'
_diffrn_detector_area_resol_mean 83.33
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 27651
_diffrn_reflns_av_R_equivalents 0.1378
_diffrn_reflns_av_sigmaI/netI 0.0917
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_k_min 0
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min 0
_diffrn_reflns_limit_l_max 30
_diffrn_reflns_theta_min 1.96
_diffrn_reflns_theta_max 30.51
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 30.51
_diffrn_measured_fraction_theta_full 0.999
_reflns_number_total 3185
_reflns_number_gt 1791
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'ApexII (Bruker, 2004)'
_computing_cell_refinement 'Saint+ (Bruker, 2004)'
_computing_data_reduction 'Saint+ (Bruker-Nonius, 2006)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
XShell (Bruker, 2000) and Crystal Explorer (Wolff et al., 2005)
;
_computing_publication_material
;
enCIFer (Allen et al., 2004) and WinGX (Farrugia, 1999)
;
_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^)+(0.0686P)^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 3185
_refine_ls_number_parameters 132
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1307
_refine_ls_R_factor_gt 0.0621
_refine_ls_wR_factor_ref 0.1623
_refine_ls_wR_factor_gt 0.1420
_refine_ls_goodness_of_fit_ref 1.078
_refine_ls_restrained_S_all 1.078
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.590
_refine_diff_density_min -0.331
_refine_diff_density_rms 0.065
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 1.11374(12) 0.92360(16) 0.06191(7) 0.0250(3) Uani 1 1 d . . .
H1 H 1.1512 0.9795 0.0906 0.037 Uiso 1 1 calc R . .
O4 O 0.74358(13) 0.61493(16) 0.14634(7) 0.0262(4) Uani 1 1 d . . .
H4 H 0.7363 0.6393 0.1839 0.039 Uiso 1 1 calc R . .
C4 C 0.83705(17) 0.6942(2) 0.12785(9) 0.0183(4) Uani 1 1 d . . .
C2 C 1.00307(16) 0.8678(2) 0.14811(9) 0.0178(4) Uani 1 1 d . . .
H2 H 1.0529 0.9332 0.1766 0.021 Uiso 1 1 calc R . .
C5 C 0.85770(17) 0.6760(2) 0.06521(9) 0.0194(4) Uani 1 1 d . . .
H5 H 0.8083 0.6099 0.0368 0.023 Uiso 1 1 calc R . .
C3 C 0.90994(16) 0.7905(2) 0.16918(9) 0.0175(4) Uani 1 1 d . . .
H3 H 0.8960 0.8035 0.2120 0.021 Uiso 1 1 calc R . .
C6 C 0.95019(18) 0.7540(2) 0.04428(9) 0.0204(4) Uani 1 1 d . . .
H6 H 0.9635 0.7420 0.0013 0.025 Uiso 1 1 calc R . .
C1 C 1.02386(16) 0.8501(2) 0.08552(9) 0.0180(4) Uani 1 1 d . . .
O10 O 0.69570(13) 0.67542(16) 0.25797(7) 0.0279(4) Uani 1 1 d . . .
C10 C 0.74362(18) 0.6190(2) 0.31101(10) 0.0247(5) Uani 1 1 d . A 1
N10 N 0.70080(16) 0.6512(2) 0.36401(8) 0.0269(4) Uani 1 1 d . A 1
C11 C 0.85048(19) 0.5143(2) 0.31579(10) 0.0268(5) Uani 1 1 d . A 1
H11A H 0.8718 0.5006 0.2730 0.040 Uiso 1 1 calc R A 1
H11B H 0.8284 0.4187 0.3324 0.040 Uiso 1 1 calc R A 1
H11C H 0.9205 0.5557 0.3451 0.040 Uiso 1 1 calc R A 1
C12 C 0.7483(2) 0.5872(3) 0.42702(9) 0.0290(5) Uani 1 1 d . A 1
H12A H 0.8085 0.5107 0.4224 0.044 Uiso 1 1 calc R A 1
H12B H 0.6811 0.5432 0.4450 0.044 Uiso 1 1 calc R A 1
H12C H 0.7871 0.6649 0.4560 0.044 Uiso 1 1 calc R A 1
C13 C 0.5964(2) 0.7519(3) 0.36019(11) 0.0308(5) Uani 1 1 d . A 1
H13A H 0.6242 0.8472 0.3795 0.046 Uiso 1 1 calc R A 1
H13B H 0.5361 0.7090 0.3836 0.046 Uiso 1 1 calc R A 1
H13C H 0.5592 0.7666 0.3150 0.046 Uiso 1 1 calc R A 1
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 0.0250(7) 0.0278(8) 0.0236(8) -0.0020(6) 0.0080(6) -0.0122(6)
O4 0.0258(7) 0.0339(9) 0.0209(7) -0.0045(6) 0.0097(6) -0.0144(7)
C4 0.0174(9) 0.0183(9) 0.0200(10) 0.0002(8) 0.0058(7) -0.0017(8)
C2 0.0158(9) 0.0185(9) 0.0183(9) -0.0005(7) 0.0010(7) 0.0000(8)
C5 0.0192(9) 0.0202(10) 0.0188(10) -0.0029(8) 0.0036(7) -0.0046(8)
C3 0.0173(9) 0.0197(10) 0.0155(9) -0.0015(7) 0.0034(7) 0.0006(7)
C6 0.0224(9) 0.0238(10) 0.0160(9) -0.0025(8) 0.0058(7) -0.0022(8)
C1 0.0168(9) 0.0175(9) 0.0206(10) 0.0026(8) 0.0059(7) -0.0014(7)
O10 0.0319(8) 0.0326(9) 0.0204(8) 0.0056(6) 0.0081(6) 0.0026(7)
C10 0.0259(10) 0.0209(10) 0.0291(11) -0.0019(9) 0.0098(9) -0.0070(9)
N10 0.0300(10) 0.0257(10) 0.0260(10) 0.0008(7) 0.0075(8) -0.0014(8)
C11 0.0227(10) 0.0220(11) 0.0364(12) -0.0028(9) 0.0072(9) -0.0001(9)
C12 0.0369(12) 0.0326(12) 0.0176(10) 0.0025(9) 0.0046(9) -0.0055(10)
C13 0.0294(11) 0.0278(12) 0.0386(13) -0.0027(10) 0.0158(10) 0.0072(10)
_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 C1 1.366(2) . ?
O1 H1 0.8400 . ?
O4 C4 1.375(2) . ?
O4 H4 0.8400 . ?
C4 C3 1.388(3) . ?
C4 C5 1.390(3) . ?
C2 C3 1.386(3) . ?
C2 C1 1.389(2) . ?
C2 H2 0.9500 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9500 . ?
C3 H3 0.9500 . ?
C6 C1 1.390(3) . ?
C6 H6 0.9500 . ?
O10 C10 1.259(2) . ?
C10 N10 1.322(3) . ?
C10 C11 1.510(3) . ?
N10 C12 1.460(3) . ?
N10 C13 1.468(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C4 O4 H4 109.5 . . ?
O4 C4 C3 122.49(16) . . ?
O4 C4 C5 117.83(16) . . ?
C3 C4 C5 119.68(17) . . ?
C3 C2 C1 120.33(17) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C6 C5 C4 119.94(17) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C2 C3 C4 120.17(17) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C6 C1 120.65(17) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
O1 C1 C2 123.02(17) . . ?
O1 C1 C6 117.75(16) . . ?
C2 C1 C6 119.23(17) . . ?
O10 C10 N10 120.16(19) . . ?
O10 C10 C11 121.28(18) . . ?
N10 C10 C11 118.56(19) . . ?
C10 N10 C12 123.75(19) . . ?
C10 N10 C13 119.32(18) . . ?
C12 N10 C13 116.88(17) . . ?
# start Validation Reply Form
_vrf_PLAT380_hq_dma_mono2
;
PROBLEM: Check Incorrectly? Oriented X(sp2)-Methyl Moiety C11
RESPONSE: The group is modelled best with AFIX 137 of C11.
There is residual in the DMA group which might be due to unresolved disorder.
;
_vrf_RINTA01_hq_dma_mono2
;
PROBLEM: The value of Rint is greater than 0.10
Rint given 0.138
RESPONSE: The crystal quality is in general poor for this crystallization
;
_vrf_PLAT020_hq_dma_mono2
;
PROBLEM: The value of Rint is greater than 0.10 ......... 0.14
RESPONSE: The crystal quality is in general poor for this crystallization
;
# Attachment '- Structure3.cif'
#==============================================================================
data_hq_def_abs
_database_code_depnum_ccdc_archive 'CCDC 692268'
#==========================================================================
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C5 H11 N O, 2.5(C6 H6 O2)'
_chemical_formula_sum 'C20 H26 N O6'
_chemical_formula_weight 376.42
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 Triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
_symmetry_int_tables_number 2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 5.5742(1)
_cell_length_b 9.8776(3)
_cell_length_c 17.6573(4)
_cell_angle_alpha 101.171(1)
_cell_angle_beta 92.245(2)
_cell_angle_gamma 99.443(2)
_cell_volume 938.33(4)
_cell_formula_units_Z 2
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 5883
_cell_measurement_theta_min 2.358
_cell_measurement_theta_max 33.698
_exptl_crystal_description rectangular
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.14
_exptl_crystal_size_min 0.09
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.332
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 402
_exptl_absorpt_coefficient_mu 0.098
_exptl_absorpt_correction_type sphere
_exptl_absorpt_correction_T_min 0.896540
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_process_details
;
'SADABS; Sheldrick, 1996.'
;
_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 'Bruker X8 APEX-II diffractometer'
_diffrn_measurement_method '\f-scans and \w-scans'
_diffrn_detector_area_resol_mean 83.33
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 28368
_diffrn_reflns_av_R_equivalents 0.0445
_diffrn_reflns_av_sigmaI/netI 0.0575
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_l_min -27
_diffrn_reflns_limit_l_max 27
_diffrn_reflns_theta_min 2.13
_diffrn_reflns_theta_max 33.14
_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full 33.14
_diffrn_measured_fraction_theta_full 0.986
_reflns_number_total 7063
_reflns_number_gt 5086
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'ApexII (Bruker, 2004)'
_computing_cell_refinement 'Saint+ (Bruker, 2004)'
_computing_data_reduction 'Saint+ (Bruker-Nonius, 2006)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
XShell (Bruker, 2000) and Crystal Explorer (Wolff et al., 2005)
;
_computing_publication_material
;
enCIFer (Allen et al., 2004) and WinGX (Farrugia, 1999)
;
_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^)+(0.0473P)^2^+0.2105P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_coef 0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 7063
_refine_ls_number_parameters 252
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0838
_refine_ls_R_factor_gt 0.0542
_refine_ls_wR_factor_ref 0.1211
_refine_ls_wR_factor_gt 0.1092
_refine_ls_goodness_of_fit_ref 1.034
_refine_ls_restrained_S_all 1.034
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.396
_refine_diff_density_min -0.283
_refine_diff_density_rms 0.058
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 0.31711(17) -0.05779(9) 0.26014(5) 0.01858(19) Uani 1 1 d . . .
H1 H 0.3289 -0.1250 0.2240 0.028 Uiso 1 1 calc R . .
C1 C 0.5087(2) 0.05105(12) 0.26095(6) 0.0146(2) Uani 1 1 d . . .
C2 C 0.6900(2) 0.04178(12) 0.20929(7) 0.0164(2) Uani 1 1 d . . .
H2 H 0.6829 -0.0407 0.1707 0.020 Uiso 1 1 calc R . .
C3 C 0.8810(2) 0.15285(13) 0.21414(7) 0.0175(2) Uani 1 1 d . . .
H3 H 1.0047 0.1464 0.1787 0.021 Uiso 1 1 calc R . .
C4 C 0.8928(2) 0.27398(12) 0.27066(7) 0.0162(2) Uani 1 1 d . . .
C5 C 0.7100(2) 0.28347(12) 0.32177(7) 0.0163(2) Uani 1 1 d . . .
H5 H 0.7166 0.3661 0.3602 0.020 Uiso 1 1 calc R . .
C6 C 0.5180(2) 0.17251(12) 0.31677(7) 0.0160(2) Uani 1 1 d . . .
H6 H 0.3927 0.1796 0.3516 0.019 Uiso 1 1 calc R . .
O4 O 1.08455(17) 0.38070(9) 0.27173(5) 0.0217(2) Uani 1 1 d . . .
H4 H 1.0915 0.4403 0.3131 0.033 Uiso 1 1 calc R . .
O11 O 0.17756(16) 0.58584(9) 0.40370(5) 0.01778(18) Uani 1 1 d . . .
H11 H 0.2235 0.6701 0.4011 0.027 Uiso 1 1 calc R . .
C11 C 0.3416(2) 0.54627(12) 0.45223(6) 0.0149(2) Uani 1 1 d . . .
C12 C 0.2749(2) 0.41806(12) 0.47328(7) 0.0166(2) Uani 1 1 d . . .
H12 H 0.1207 0.3621 0.4549 0.020 Uiso 1 1 calc R . .
C13 C 0.4329(2) 0.37087(12) 0.52120(7) 0.0158(2) Uani 1 1 d . . .
H13 H 0.3872 0.2829 0.5356 0.019 Uiso 1 1 calc R . .
O21 O 0.28021(16) 0.86069(9) 0.39612(5) 0.01753(19) Uani 1 1 d . . .
H21 H 0.2765 0.8880 0.3540 0.026 Uiso 1 1 calc R . .
C21 C 0.1397(2) 0.93271(12) 0.44678(6) 0.0141(2) Uani 1 1 d . . .
C22 C -0.0225(2) 1.01138(12) 0.42267(7) 0.0160(2) Uani 1 1 d . . .
H22 H -0.0378 1.0191 0.3700 0.019 Uiso 1 1 calc R . .
C23 C -0.1619(2) 1.07867(12) 0.47645(7) 0.0165(2) Uani 1 1 d . . .
H23 H -0.2730 1.1328 0.4604 0.020 Uiso 1 1 calc R . .
O31 O 0.87579(17) 0.76270(9) 1.06161(5) 0.0211(2) Uani 1 1 d . . .
H31 H 0.9958 0.7489 1.0875 0.032 Uiso 1 1 calc R . .
C31 C 0.9419(2) 0.88082(12) 1.03167(7) 0.0155(2) Uani 1 1 d . . .
C32 C 0.7662(2) 0.92274(12) 0.98790(7) 0.0163(2) Uani 1 1 d . . .
H32 H 0.6053 0.8702 0.9797 0.020 Uiso 1 1 calc R . .
C33 C 0.8236(2) 1.04077(12) 0.95607(7) 0.0166(2) Uani 1 1 d . . .
H33 H 0.7025 1.0682 0.9258 0.020 Uiso 1 1 calc R . .
O41 O 0.28385(17) 0.72175(9) 0.14297(5) 0.01966(19) Uani 1 1 d . . .
C41 C 0.3489(2) 0.60671(13) 0.12018(7) 0.0173(2) Uani 1 1 d . . .
H41 H 0.3098 0.5638 0.0672 0.021 Uiso 1 1 calc R . .
N41 N 0.46627(19) 0.53912(10) 0.16242(6) 0.0161(2) Uani 1 1 d . . .
C42 C 0.5336(2) 0.59636(13) 0.24500(7) 0.0177(2) Uani 1 1 d . . .
H42A H 0.5338 0.5176 0.2721 0.021 Uiso 1 1 calc R . .
H42B H 0.4078 0.6498 0.2666 0.021 Uiso 1 1 calc R . .
C43 C 0.5193(2) 0.40064(13) 0.12701(8) 0.0222(3) Uani 1 1 d . . .
H43A H 0.4051 0.3603 0.0808 0.027 Uiso 1 1 calc R . .
H43B H 0.4903 0.3377 0.1643 0.027 Uiso 1 1 calc R . .
C44 C 0.7807(3) 0.69134(14) 0.26141(8) 0.0227(3) Uani 1 1 d . . .
H44A H 0.9081 0.6375 0.2439 0.034 Uiso 1 1 calc R . .
H44B H 0.8098 0.7293 0.3172 0.034 Uiso 1 1 calc R . .
H44C H 0.7839 0.7686 0.2338 0.034 Uiso 1 1 calc R . .
C45 C 0.7789(2) 0.40531(14) 0.10321(7) 0.0222(3) Uani 1 1 d . . .
H45A H 0.8150 0.4750 0.0707 0.033 Uiso 1 1 calc R . .
H45B H 0.7968 0.3129 0.0740 0.033 Uiso 1 1 calc R . .
H45C H 0.8924 0.4310 0.1495 0.033 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0221(5) 0.0150(4) 0.0165(4) 0.0011(3) 0.0039(3) -0.0008(3)
C1 0.0162(6) 0.0136(5) 0.0145(5) 0.0046(4) 0.0003(4) 0.0017(4)
C2 0.0202(6) 0.0148(5) 0.0139(5) 0.0014(4) 0.0026(4) 0.0040(5)
C3 0.0181(6) 0.0192(6) 0.0155(5) 0.0034(4) 0.0041(4) 0.0040(5)
C4 0.0172(6) 0.0154(5) 0.0158(5) 0.0044(4) -0.0009(4) 0.0017(4)
C5 0.0208(6) 0.0140(5) 0.0142(5) 0.0015(4) -0.0008(4) 0.0050(5)
C6 0.0184(6) 0.0167(5) 0.0137(5) 0.0032(4) 0.0028(4) 0.0048(5)
O4 0.0227(5) 0.0183(4) 0.0206(4) 0.0010(3) 0.0016(4) -0.0035(4)
O11 0.0202(5) 0.0147(4) 0.0188(4) 0.0050(3) -0.0014(3) 0.0027(3)
C11 0.0175(6) 0.0145(5) 0.0129(5) 0.0016(4) 0.0019(4) 0.0042(4)
C12 0.0167(6) 0.0148(5) 0.0173(5) 0.0021(4) 0.0019(4) 0.0015(4)
C13 0.0198(6) 0.0115(5) 0.0163(5) 0.0030(4) 0.0036(4) 0.0026(4)
O21 0.0225(5) 0.0168(4) 0.0148(4) 0.0041(3) 0.0044(3) 0.0063(3)
C21 0.0159(6) 0.0111(5) 0.0146(5) 0.0017(4) 0.0024(4) 0.0007(4)
C22 0.0198(6) 0.0150(5) 0.0131(5) 0.0037(4) -0.0001(4) 0.0019(4)
C23 0.0184(6) 0.0155(5) 0.0164(5) 0.0049(4) -0.0006(4) 0.0035(5)
O31 0.0191(5) 0.0194(4) 0.0272(5) 0.0108(4) 0.0007(4) 0.0030(4)
C31 0.0182(6) 0.0141(5) 0.0148(5) 0.0020(4) 0.0036(4) 0.0055(4)
C32 0.0143(6) 0.0168(5) 0.0169(5) 0.0011(4) 0.0010(4) 0.0030(4)
C33 0.0162(6) 0.0175(6) 0.0165(5) 0.0025(4) -0.0007(4) 0.0055(5)
O41 0.0228(5) 0.0170(4) 0.0196(4) 0.0030(3) -0.0014(3) 0.0063(4)
C41 0.0164(6) 0.0188(6) 0.0156(5) 0.0020(4) -0.0007(4) 0.0023(5)
N41 0.0168(5) 0.0130(5) 0.0175(5) 0.0011(4) -0.0007(4) 0.0022(4)
C42 0.0191(6) 0.0187(6) 0.0156(5) 0.0048(4) -0.0002(4) 0.0027(5)
C43 0.0210(6) 0.0139(6) 0.0299(7) -0.0005(5) -0.0006(5) 0.0042(5)
C44 0.0231(7) 0.0204(6) 0.0217(6) 0.0012(5) -0.0022(5) -0.0002(5)
C45 0.0252(7) 0.0219(6) 0.0196(6) 0.0018(5) 0.0013(5) 0.0077(5)
_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 C1 1.3829(16) . ?
O1 H1 0.8400 . ?
C1 C6 1.3896(16) . ?
C1 C2 1.3901(17) . ?
C2 C3 1.3849(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3921(16) . ?
C3 H3 0.9500 . ?
C4 O4 1.3691(16) . ?
C4 C5 1.3902(18) . ?
C5 C6 1.3874(18) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
O4 H4 0.8400 . ?
O11 C11 1.3816(15) . ?
O11 H11 0.8400 . ?
C11 C12 1.3851(17) . ?
C11 C13 1.3922(18) 2_666 ?
C12 C13 1.3921(17) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
O21 C21 1.3824(14) . ?
O21 H21 0.8400 . ?
C21 C23 1.3843(16) 2_576 ?
C21 C22 1.3893(17) . ?
C22 C23 1.3894(17) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
O31 C31 1.3747(15) . ?
O31 H31 0.8400 . ?
C31 C32 1.3878(17) . ?
C31 C33 1.3912(18) 2_777 ?
C32 C33 1.3867(18) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
O41 C41 1.2465(14) . ?
C41 N41 1.3147(16) . ?
C41 H41 0.9500 . ?
N41 C42 1.4679(16) . ?
N41 C43 1.4715(15) . ?
C42 C44 1.5172(19) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C45 1.5185(19) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
O1 C1 C6 117.60(11) . . ?
O1 C1 C2 122.52(10) . . ?
C6 C1 C2 119.88(11) . . ?
C3 C2 C1 119.97(11) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.33(11) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
O4 C4 C5 122.94(11) . . ?
O4 C4 C3 117.47(11) . . ?
C5 C4 C3 119.57(12) . . ?
C6 C5 C4 120.16(11) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.08(11) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C4 O4 H4 109.5 . . ?
C11 O11 H11 109.5 . . ?
O11 C11 C12 117.29(11) . . ?
O11 C11 C13 122.37(11) . 2_666 ?
C12 C11 C13 120.33(11) . 2_666 ?
C11 C12 C13 120.29(12) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C11 119.38(11) . 2_666 ?
C12 C13 H13 120.3 . . ?
C11 C13 H13 120.3 2_666 . ?
C21 O21 H21 109.5 . . ?
O21 C21 C23 117.26(10) . 2_576 ?
O21 C21 C22 122.36(10) . . ?
C23 C21 C22 120.36(11) 2_576 . ?
C21 C22 C23 119.31(11) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C21 C23 C22 120.33(11) 2_576 . ?
C21 C23 H23 119.8 2_576 . ?
C22 C23 H23 119.8 . . ?
C31 O31 H31 109.5 . . ?
O31 C31 C32 118.19(11) . . ?
O31 C31 C33 122.53(11) . 2_777 ?
C32 C31 C33 119.28(11) . 2_777 ?
C33 C32 C31 120.51(12) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C32 C33 C31 120.21(11) . 2_777 ?
C32 C33 H33 119.9 . . ?
C31 C33 H33 119.9 2_777 . ?
O41 C41 N41 126.26(11) . . ?
O41 C41 H41 116.9 . . ?
N41 C41 H41 116.9 . . ?
C41 N41 C42 121.01(10) . . ?
C41 N41 C43 119.21(10) . . ?
C42 N41 C43 119.70(10) . . ?
N41 C42 C44 113.96(11) . . ?
N41 C42 H42A 108.8 . . ?
C44 C42 H42A 108.8 . . ?
N41 C42 H42B 108.8 . . ?
C44 C42 H42B 108.8 . . ?
H42A C42 H42B 107.7 . . ?
N41 C43 C45 113.32(11) . . ?
N41 C43 H43A 108.9 . . ?
C45 C43 H43A 108.9 . . ?
N41 C43 H43B 108.9 . . ?
C45 C43 H43B 108.9 . . ?
H43A C43 H43B 107.7 . . ?
C42 C44 H44A 109.5 . . ?
C42 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C42 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C43 C45 H45A 109.5 . . ?
C43 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C43 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?