# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2001
data_global
#==============================================================================
_journal_coden_Cambridge 188
# 0. AUDIT DETAILS
_audit_creation_date 'Wed Feb 14 09:36:25 2001'
_audit_creation_method 'PLATON
option'
_audit_update_record
;
?
;
#===============================================================================
# 1. SUBMISSION DETAILS
_publ_contact_author_name # Name of author for correspondence
;
Peter Luger
;
_publ_contact_author_address # address of author for correspondence
;
Institut f\"ur Chemie/Kristallographie
Freie Universit\"at Berlin
Takustrasse 6
D-14195 Berlin
Germany
;
_publ_contact_author_email 'luger@chemie.fu-berlin.de'
_publ_contact_author_fax ?
_publ_contact_author_phone ?
_publ_requested_journal
;
Journal of the Chemical Society Perkin Trans. 2'
;
# Publication choise FI FM FO CI CM CO AD
_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 Journal of the Chemical Society
Perkin Trans. 2.
;
#===============================================================================
# 2. PROCESSING SUMMARY (JOURNAL OFFICE ONLY)
_journal_coden_ASTM ?
_journal_name_full ?
_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
;
Experimental charge density and topological properties of
3-(tert-tutyloxycarbonylamino)bicyclo[1.1.1]pentanecarboxylic acid
;
_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_address
'Peter Luger' # author name
;
Institut f\"ur Chemie/Kristallographie # Address of this author
Freie Universit\"at Berlin
Takustrasse 6
D-14195 Berlin
Germany
;
'Manuela Weber' # author name
;
Institut f\"ur Chemie/Kristallographie # Address of this author
Freie Universit\"at Berlin
Takustrasse 6
D-14195 Berlin
Germany
;
'Gunter Szeimies' # author name
;
Institut f\"ur Organische und Bioorganische Chemie # Address of this author
Humboldt-Universit\"at zu Berlin
Hessische Str. 1-2
10115 Berlin
Germany
;
'Michael Patzel' # author name
;
Institut f\"ur Organische und Bioorganische Chemie
Humboldt-Universit\"at zu Berlin
Hessische Str. 1-2
10115 Berlin
Germany
;
#===============================================================================
# 4. TEXT
_publ_section_synopsis
;
?
;
_publ_section_abstract
;
?
;
# Insert blank lines between paragraphs
_publ_section_comment
;
?
;
_publ_section_exptl_prep
;
?
;
_publ_section_exptl_refinement
;
?
;
# Insert blank lines between references
_publ_section_references
;
?
;
_publ_section_figure_captions
;
?
;
_publ_section_acknowledgements
; View of the title compound with the atom numbering scheme
Displacement ellipsoids for non-H atoms are drawn at the 50% probability level
;
#===============================================================================
data_p08e
_database_code_CSD 163809
#===============================================================================
# 5. CHEMICAL DATA
_chemical_name_systematic
;
3-(tert-tutyloxycarbonylamino)bicyclo[1.1.1]pentane-carboxylic acid
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety
'C11 H17 N O4'
_chemical_formula_structural ?
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_sum
'C11 H17 N O4'
_chemical_formula_weight 227.26
_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 10.5109 0.3229
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 10.5109 0.3229
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 10.5109 0.3229
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 10.5109 0.3229
'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 'C -2yc'
_symmetry_space_group_name_H-M 'C c'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x,-y,1/2+z
1/2+x,1/2+y,z
1/2+x,1/2-y,1/2+z
_cell_length_a 6.0581
_cell_length_b 18.1774
_cell_length_c 11.2293
_cell_angle_alpha 90
_cell_angle_beta 92.9400
_cell_angle_gamma 90
_cell_volume 1234.95
_cell_formula_units_Z 4
_cell_measurement_temperature 110
_cell_measurement_reflns_used ?
_cell_measurement_theta_min ?
_cell_measurement_theta_max ?
_cell_special_details
; ?
;
_exptl_crystal_description prism
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.6
_exptl_crystal_size_mid 0.4
_exptl_crystal_size_min 0.3
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.222
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 488
_exptl_absorpt_coefficient_mu 0.09
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type no
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
; ?
;
_diffrn_ambient_temperature 110(2)
_diffrn_radiation_wavelength 0.7107
_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 '\w and \f'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time none
_diffrn_standards_decay_% none
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 29337
_diffrn_reflns_av_R_equivalents ?
_diffrn_reflns_av_sigmaI/netI ?
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_k_min -38
_diffrn_reflns_limit_k_max 39
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_limit_l_max 24
_diffrn_reflns_theta_min ?
_diffrn_reflns_theta_max 103.00
_diffrn_reflns_theta_full ?
_diffrn_measured_fraction_theta_max ?
_diffrn_measured_fraction_theta_full ?
_diffrn_reflns_reduction_process
;
?
;
# number of unique reflections
_reflns_number_total 6786
# number of observed reflections (> n sig(I))
_reflns_number_gt 6090
_reflns_threshold_expression >3sigma(I)
_computing_data_collection 'SMART (Bruker-AXS, 1996)'
_computing_cell_refinement 'SMART, SAINT (Bruker-AXS, 1996, 1994)'
_computing_data_reduction 'SHELXTL, SAINT (Bruker-AXS, 1996)'
_computing_structure_solution ?
_computing_structure_refinement 'XD (Koritsanszky et al, 1995)'
_computing_molecular_graphics
;
schakal88 (Keller, 1988), ortep (Johnson, 1976)
;
_computing_publication_material 'PLATON (Spek, 1990)'
#===============================================================================
# 8. REFINEMENT DATA
_refine_special_details none
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type full
_refine_ls_weighting_scheme 'sigma'
_refine_ls_weighting_details 'w=1/\S'
_refine_ls_hydrogen_treatment 'H-atom refinement: see text '
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_extinction_expression
?
_refine_ls_abs_structure_details
'Flack H.D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 999999
_refine_ls_number_reflns 6090
_refine_ls_number_parameters ?
_refine_ls_number_restraints 0
_refine_ls_number_constraints ?
_refine_ls_R_factor_all 0.027
_refine_ls_R_factor_gt 0.022
_refine_ls_wR_factor_ref ?
_refine_ls_wR_factor_gt 0.018
_refine_ls_goodness_of_fit_ref 3.39
_refine_ls_restrained_S_all ?
_refine_ls_shift/su_max ?
_refine_ls_shift/su_mean ?
_refine_diff_density_max ?
_refine_diff_density_min ?
_refine_diff_density_rms ?
#===============================================================================
# 9. ATOMIC COORDINATES AND THERMAL 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
O1 O Uani 0.83767(19) 0.59500(4) 1.17044(10) 1.000 0.0336(2)
O2 O Uani 0.98832(13) 0.48768(3) 1.23426(7) 1.000 0.0234(1)
O3 O Uani 0.45594 0.30815(3) 0.90111 1.000 0.0242(1)
O4 O Uani 0.16054(15) 0.33120(3) 0.77299(9) 1.000 0.0302(2)
N1 N Uani 0.29876(11) 0.41928(3) 0.90118(6) 1.000 0.0230(1)
C1 C Uani 0.67232(11) 0.48727(2) 1.09510(6) 1.000 0.0176(1)
C2 C Uani 0.51734(12) 0.42061(3) 1.11750(6) 1.000 0.0267(1)
C3 C Uani 0.46386(10) 0.44603(2) 0.98637(6) 1.000 0.0182(1)
C4 C Uani 0.46937(11) 0.52631(3) 1.03274(6) 1.000 0.0272(1)
C5 C Uani 0.71729(11) 0.45220(3) 0.97236(6) 1.000 0.0268(1)
C6 C Uani 0.29721(10) 0.35081(3) 0.85277(6) 1.000 0.0226(1)
C7 C Uani 0.49026(11) 0.23184(3) 0.85876(6) 1.000 0.0228(1)
C8 C Uani 0.68245(13) 0.20644(3) 0.94118(7) 1.000 0.0371(1)
C9 C Uani 0.28674(13) 0.18491(3) 0.87717(7) 1.000 0.0300(1)
C10 C Uani 0.55530(14) 0.23267(3) 0.72943(7) 1.000 0.0354(2)
C11 C Uani 0.84830(11) 0.52219(3) 1.17438(6) 1.000 0.0189(1)
H1 H Uiso 0.18741 0.45580 0.85943 1.000 0.016(4)
H10 H Uiso 0.96599 0.61601 1.20918 1.000 0.018(4)
H21 H Uiso 0.59693 0.36709 1.13003 1.000 0.037(4)
H22 H Uiso 0.38756 0.43070 1.17930 1.000 0.032(3)
H41 H Uiso 0.51142 0.56726 0.96655 1.000 0.028(3)
H42 H Uiso 0.33307 0.54045 1.08828 1.000 0.025(3)
H51 H Uiso 0.76682 0.49046 0.90374 1.000 0.043(4)
H52 H Uiso 0.80737 0.40021 0.97658 1.000 0.036(3)
H81 H Uiso 0.82480 0.24241 0.93274 1.000 0.034(4)
H82 H Uiso 0.72655 0.15044 0.91703 1.000 0.031(3)
H83 H Uiso 0.63089 0.20718 1.03294 1.000 0.033(3)
H91 H Uiso 0.23233 0.18665 0.96824 1.000 0.052(4)
H92 H Uiso 0.32357 0.12753 0.85773 1.000 0.037(3)
H93 H Uiso 0.14792 0.20129 0.81745 1.000 0.036(3)
H101 H Uiso 0.41876 0.25321 0.67157 1.000 0.039(4)
H102 H Uiso 0.59446 0.17619 0.70543 1.000 0.034(4)
H103 H Uiso 0.69765 0.26835 0.71846 1.000 0.046(4)
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 0.0373(3) 0.0184(2) 0.0424(3) 0.0022(2) -0.0236(3) -0.0046(2)
O2 0.0219(2) 0.0216(2) 0.0259(2) -0.0012(2) -0.0071(2) 0.0012(2)
O3 0.0245(2) 0.0177(2) 0.0290(2) -0.0028(1) -0.0127(2) 0.0046(1)
O4 0.0318(3) 0.0195(2) 0.0369(3) -0.0060(2) -0.0210(2) 0.0058(2)
N1 0.0215(2) 0.0168(2) 0.0294(2) -0.0031(1) -0.0112(1) 0.0031(1)
C1 0.0168(1) 0.0183(2) 0.0175(1) -0.0010(1) -0.0015(1) -0.0015(1)
C2 0.0296(2) 0.0277(2) 0.0222(2) 0.0053(1) -0.0040(1) -0.0102(2)
C3 0.0169(2) 0.0166(2) 0.0207(2) -0.0012(1) -0.0037(1) 0.0004(1)
C4 0.0245(2) 0.0182(2) 0.0377(2) -0.0042(1) -0.0102(2) 0.0030(1)
C5 0.0194(2) 0.0393(3) 0.0217(2) -0.0089(2) 0.0017(1) -0.0018(2)
C6 0.0227(2) 0.0166(2) 0.0271(2) -0.0025(1) -0.0119(1) 0.0032(1)
C7 0.0232(2) 0.0183(2) 0.0264(2) 0.0005(1) -0.0047(1) 0.0041(1)
C8 0.0327(2) 0.0300(2) 0.0469(3) 0.0020(2) -0.0142(2) 0.0119(2)
C9 0.0312(2) 0.0225(2) 0.0359(2) -0.0003(2) -0.0017(2) -0.0019(2)
C10 0.0420(3) 0.0332(3) 0.0315(2) -0.0001(2) 0.0056(2) 0.0051(2)
C11 0.0189(2) 0.0190(2) 0.0184(2) -0.0007(1) -0.0035(1) -0.0013(1)
#===============================================================================
# 10. MOLECULAR GEOMETRY
_geom_special_details
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All esds 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 C11 1.3257(9) . . yes
O2 C11 1.2275(10) . . yes
O3 C6 1.3293(7) . . yes
O3 C7 1.4845(8) . . yes
O4 C6 1.2406(11) . . yes
O1 H10 0.9512 . . no
N1 C3 1.4331(9) . . yes
N1 C6 1.3580(8) . . yes
N1 H1 1.0407 . . no
C1 C5 1.5552(9) . . no
C1 C2 1.5612(8) . . no
C1 C4 1.5548(9) . . no
C1 C11 1.4949(9) . . no
C2 C3 1.5613(9) . . no
C3 C5 1.5554(9) . . no
C3 C4 1.5492(7) . . no
C7 C10 1.5242(10) . . no
C7 C8 1.5215(10) . . no
C7 C9 1.5221(10) . . no
C2 H21 1.0917 . . no
C2 H22 1.0906 . . no
C4 H41 1.0913 . . no
C4 H42 1.0907 . . no
C5 H51 1.0914 . . no
C5 H52 1.0911 . . no
C8 H81 1.0902 . . no
C8 H82 1.0902 . . no
C8 H83 1.0920 . . no
C9 H91 1.0909 . . no
C9 H92 1.0910 . . no
C9 H93 1.0899 . . no
C10 H101 1.0912 . . no
C10 H102 1.0906 . . no
C10 H103 1.0911 . . 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
C6 O3 C7 121.64(4) . . . yes
C11 O1 H10 110.39 . . . no
C3 N1 C6 124.64(6) . . . yes
C6 N1 H1 114.41 . . . no
C3 N1 H1 119.89 . . . no
C2 C1 C5 87.64(4) . . . no
C4 C1 C11 126.71(4) . . . no
C2 C1 C11 130.54(6) . . . no
C4 C1 C5 87.61(5) . . . no
C2 C1 C4 87.63(5) . . . no
C5 C1 C11 123.36(6) . . . no
C1 C2 C3 73.49(4) . . . no
N1 C3 C4 123.11(5) . . . yes
C2 C3 C5 87.63(5) . . . no
N1 C3 C5 128.00(6) . . . yes
C2 C3 C4 87.82(5) . . . no
N1 C3 C2 129.28(5) . . . yes
C4 C3 C5 87.81(4) . . . no
C1 C4 C3 74.00(4) . . . no
C1 C5 C3 73.81(4) . . . no
O3 C6 N1 112.41(6) . . . yes
O3 C6 O4 124.70(6) . . . yes
O4 C6 N1 122.89(6) . . . yes
O3 C7 C8 101.78(4) . . . yes
O3 C7 C9 110.64(5) . . . yes
C9 C7 C10 112.69(6) . . . no
O3 C7 C10 110.08(4) . . . yes
C8 C7 C9 110.32(5) . . . no
C8 C7 C10 110.82(6) . . . no
O1 C11 O2 124.02(8) . . . yes
O1 C11 C1 111.85(7) . . . yes
O2 C11 C1 124.12(5) . . . yes
C1 C2 H21 116.56 . . . no
C1 C2 H22 115.54 . . . no
C3 C2 H21 117.01 . . . no
C3 C2 H22 115.40 . . . no
H21 C2 H22 113.32 . . . no
C1 C4 H41 114.28 . . . no
C1 C4 H42 117.03 . . . no
C3 C4 H41 114.54 . . . no
C3 C4 H42 114.22 . . . no
H41 C4 H42 116.02 . . . no
C1 C5 H51 115.56 . . . no
C1 C5 H52 115.24 . . . no
C3 C5 H51 115.21 . . . no
C3 C5 H52 115.29 . . . no
H51 C5 H52 115.31 . . . no
C7 C8 H81 110.44 . . . no
C7 C8 H82 108.76 . . . no
C7 C8 H83 108.86 . . . no
H81 C8 H82 109.47 . . . no
H81 C8 H83 109.90 . . . no
H82 C8 H83 109.38 . . . no
C7 C9 H91 113.38 . . . no
C7 C9 H92 109.46 . . . no
C7 C9 H93 111.60 . . . no
H91 C9 H92 106.86 . . . no
H91 C9 H93 107.95 . . . no
H92 C9 H93 107.30 . . . no
C7 C10 H101 110.22 . . . no
C7 C10 H102 107.23 . . . no
C7 C10 H103 110.97 . . . no
H101 C10 H102 110.05 . . . no
H101 C10 H103 107.99 . . . no
H102 C10 H103 110.39 . . . 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
C7 O3 C6 O4 2.72(10) . . . . no
C7 O3 C6 N1 -177.76(5) . . . . no
C6 O3 C7 C8 -179.03(5) . . . . no
C6 O3 C7 C9 -61.80(7) . . . . no
C6 O3 C7 C10 63.41(7) . . . . no
C6 N1 C3 C5 58.60(9) . . . . no
C3 N1 C6 O3 5.74(9) . . . . no
C6 N1 C3 C4 175.44(6) . . . . no
C6 N1 C3 C2 -66.23(10) . . . . no
C3 N1 C6 O4 -174.72(8) . . . . no
C5 C1 C2 C3 -44.02(4) . . . . no
C11 C1 C5 C3 -177.12(5) . . . . no
C11 C1 C2 C3 -177.56(6) . . . . no
C2 C1 C4 C3 -43.98(4) . . . . no
C5 C1 C4 C3 43.75(4) . . . . no
C11 C1 C4 C3 174.70(7) . . . . no
C2 C1 C5 C3 44.14(4) . . . . no
C4 C1 C5 C3 -43.59(4) . . . . no
C4 C1 C2 C3 43.69(4) . . . . no
C4 C1 C11 O1 -11.54(10) . . . . no
C2 C1 C11 O1 -136.28(8) . . . . no
C2 C1 C11 O2 44.96(11) . . . . no
C5 C1 C11 O2 -74.92(9) . . . . no
C4 C1 C11 O2 169.70(7) . . . . no
C5 C1 C11 O1 103.84(8) . . . . no
C1 C2 C3 C4 -43.88(4) . . . . no
C1 C2 C3 N1 -176.34(6) . . . . no
C1 C2 C3 C5 44.01(4) . . . . no
N1 C3 C4 C1 -179.02(7) . . . . no
C2 C3 C4 C1 43.96(4) . . . . no
C5 C3 C4 C1 -43.74(4) . . . . no
N1 C3 C5 C1 175.36(5) . . . . no
C2 C3 C5 C1 -44.13(3) . . . . no
C4 C3 C5 C1 43.78(4) . . . . 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 O4 2.5924(14) . 2_665 no
O2 N1 3.0901(10) . 2_665 no
O2 C5 3.3896(10) . 2_565 no
O3 C5 3.1422(7) . . no
O3 C2 3.1826(7) . . no
O4 C10 3.0473(11) . . no
O4 C11 3.4193(9) . 2_464 no
O4 C9 2.9887(9) . . no
O4 O1 2.5924(14) . 2_464 no
O1 H91 2.8617 . 3_555 no
O1 H103 2.6883 . 2_565 no
O2 H92 2.7288 . 4_555 no
O2 H42 2.8845 . 1_655 no
O2 H1 2.0765 . 2_665 no
O2 H51 2.4171 . 2_565 no
O2 H22 2.7307 . 1_655 no
O3 H52 2.8047 . . no
O3 H21 2.8741 . . no
O4 H101 2.4365 . . no
O4 H93 2.4156 . . no
O4 H10 1.6543 . 2_464 no
O4 H83 2.7813 . 4_454 no
N1 O2 3.0901(10) . 2_464 no
N1 H10 2.9459 . 2_464 no
C2 O3 3.1826(7) . . no
C5 C11 3.5093(9) . 2_564 no
C5 O3 3.1422(7) . . no
C5 O2 3.3896(10) . 2_564 no
C9 O4 2.9887(9) . . no
C10 O4 3.0473(11) . . no
C11 C5 3.5093(9) . 2_565 no
C11 O4 3.4193(9) . 2_665 no
C4 H82 2.9576 . 3_455 no
C6 H93 2.8854 . . no
C6 H101 2.8255 . . no
C6 H10 2.5803 . 2_464 no
C8 H101 2.9834 . 4_555 no
C9 H81 3.0810 . 1_455 no
C9 H41 2.9214 . 3_445 no
C9 H21 3.0968 . 4_454 no
C11 H1 2.8741 . 2_665 no
C11 H51 2.6571 . 2_565 no
H1 O2 2.0765 . 2_464 no
H1 C11 2.8741 . 2_464 no
H1 H10 2.4734 . 2_464 no
H10 O4 1.6543 . 2_665 no
H10 N1 2.9459 . 2_665 no
H10 C6 2.5803 . 2_665 no
H10 H1 2.4734 . 2_665 no
H21 O3 2.8741 . . no
H21 H52 2.2765 . . no
H21 C9 3.0968 . 4_555 no
H21 H93 2.4501 . 4_555 no
H22 O2 2.7307 . 1_455 no
H22 H42 2.2581 . . no
H41 H51 2.2254 . . no
H41 C9 2.9214 . 3_555 no
H41 H82 2.3399 . 3_455 no
H41 H91 2.5492 . 3_555 no
H41 H92 2.5508 . 3_555 no
H42 O2 2.8845 . 1_455 no
H42 H22 2.2581 . . no
H51 H41 2.2254 . . no
H51 O2 2.4171 . 2_564 no
H51 C11 2.6571 . 2_564 no
H51 H92 2.5712 . 3_555 no
H52 O3 2.8047 . . no
H52 H21 2.2765 . . no
H81 C9 3.0810 . 1_655 no
H81 H93 2.5153 . 1_655 no
H81 H103 2.5329 . . no
H82 H92 2.5318 . . no
H82 H102 2.5120 . . no
H82 C4 2.9576 . 3_545 no
H82 H41 2.3399 . 3_545 no
H83 H91 2.5134 . . no
H83 O4 2.7813 . 4_555 no
H83 H101 2.3884 . 4_555 no
H91 H83 2.5134 . . no
H91 O1 2.8617 . 3_445 no
H91 H41 2.5492 . 3_445 no
H92 H82 2.5318 . . no
H92 H102 2.5862 . . no
H92 H41 2.5508 . 3_445 no
H92 H51 2.5712 . 3_445 no
H92 O2 2.7288 . 4_454 no
H93 O4 2.4156 . . no
H93 C6 2.8854 . . no
H93 H81 2.5153 . 1_455 no
H93 H101 2.5577 . . no
H93 H21 2.4501 . 4_454 no
H101 O4 2.4365 . . no
H101 C6 2.8255 . . no
H101 H93 2.5577 . . no
H101 C8 2.9834 . 4_454 no
H101 H83 2.3884 . 4_454 no
H102 H82 2.5120 . . no
H102 H92 2.5862 . . no
H103 H81 2.5329 . . no
H103 O1 2.6883 . 2_564 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
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N1 H1 O2 1.0407 2.0765 3.0901(10) 163.96 2_464 yes
O1 H10 O4 0.9512 1.6543 2.5924(14) 168.07 2_665 yes
C5 H51 O2 1.0914 2.4171 3.3896(10) 147.62 2_564 yes
C9 H93 O4 1.0899 2.4156 2.9887(9) 111.26 . yes
C10 H101 O4 1.0912 2.4365 3.0473(11) 113.96 . yes
loop_
_publ_manuscript_incl_extra_item
'_geom_extra_tableA_col_1'
'_geom_extra_tableA_col_2'
'_geom_extra_tableA_col_3'
'_geom_extra_tableA_col_4'
'_geom_extra_tableA_col_5'
'_geom_extra_table_head_A'
_geom_extra_table_head_A
;
Summary of topological data at the bond critical
points (BCP, located at r~b~ where nabla \r(r~b~)=0).
The quantities given are
\r(r~b~) and nabla^2^ \r(r~b~))
and the ellipticity
\e (defined by \e= \l~1~/\l~2~^-1^, with
\l~1~, \l~2~
being the two principal curvatures of \r(r) at a BCP), a measure
for the charge
asphericity. First row experimental results after multipole refinement,
second an third
subsequent rows:
single point ab initio calculations at the experimental geometry,
fourth and
fifth row: single point
ab initio calculations after geometry optimization at the HF/6-311+G(d,p)
level. Bond length are
experimental (first row) and optimized theoretically (second row).
;
loop_
_geom_extra_tableA_col_1
_geom_extra_tableA_col_2
_geom_extra_tableA_col_3
_geom_extra_tableA_col_4
_geom_extra_tableA_col_5
bond/bond length[\%A] \r[e\%A^-3^] nabla^2^\r[e\%A^-5^] ellipticity method
C(1)--C(2) 1.60(2) -10.66(8) 0.10 multipole
1.5612(7) 1.59 -13.2 0.02 HF/6-311+G(d,p)(exp. geo.)
1.5386 1.52 -10.4 0.02 B3LYP/6-311+G(d,p)(exp. geo.)
1.67 -14.8 0.02 HF/6-311+G(d,p)(opt. geo.)
1.54 -11.8 0.02 B3LYP/6-311+G(d,p)(opt. geo.)
C(1)--C(4) 1.53(3) -9.69(9) 0.15 multipole
1.5548(7) 1.62 -13.9 0.02 HF/6-311+G(d,p)(exp. geo.)
1.5472 1.55 -10.9 0.02 B3LYP/6-311+G(d,p)(exp. geo.)
1.63 -14.0 0.02 HF/6-311+G(d,p)(opt. geo.)
1.56 -11.0 0.02 B3LYP/6-311+G(d,p)(opt. geo.)
C(1)--C(5) 1.59(3) -11.39(8) 0.09 multipole
1.5553(6) 1.60 -13.5 0.03 HF/6-311+G(d,p)(exp. geo.)
1.5510 1.53 -10.6 0.02 B3LYP/6-311+G(d,p)(exp. geo.)
1.61 -13.6 0.03 HF/6-311+G(d,p)(opt. geo.)
1.54 -10.7 0.03 B3LYP/6-311+G(d,p)(opt. geo.)
C(3)--C(2) 1.65(2) -13.07(7) 0.15 multipole
1.5613(6) 1.63 -14.0 0.02 HF/6-311+G(d,p)(exp. geo.)
1.5476 1.54 -10.9 0.02 B3LYP/6-311+G(d,p)(exp. geo.)
1.67 -14.7 0.02 HF/6-311+G(d,p)(opt. geo.)
1.59 -11.5 0.01 B3LYP/6-311+G(d,p)(opt. geo.)
C(3)--C(4) 1.63(3) -12.63(9) 0.08 multipole
1.5493(7) 1.66 -14.6 0.00 HF/6-311+G(d,p)(exp. geo.)
1.5409 1.58 -11.5 0.00 B3LYP/6-311+G(d,p)(exp. geo.)
1.69 -15.1 0.01 HF/6-311+G(d,p)(opt. geo.)
1.60 -11.9 0.00 B3LYP/6-311+G(d,p)(opt. geo.)
C(3)--C(5) 1.67(3) -13.07(7) 0.10 multipole
1.5554(7) 1.65 -14.3 0.02 HF/6-311+G(d,p)(exp. geo.)
1.5475 1.56 -11.2 0.02 B3LYP/6-311+G(d,p)(exp. geo.)
1.67 -14.7 0.02 HF/6-311+G(d,p)(opt. geo.)
1.59 -11.5 0.01 B3LYP/6-311+G(d,p)(opt. geo.)
C(1)--C(11) 1.94(3) -21.3(10) 0.03 multipole
1.4949(6) 1.88 -20.6 0.07 HF/6-311+G(d,p)(exp. geo.)
1.4913 1.79 -16.2 0.07 B3LYP/6-311+G(d,p)(exp. geo.)
1.90 -20.8 0.07 HF/6-311+G(d,p)(opt. geo.)
1.80 -16.5 0.07 B3LYP/6-311+G(d,p)(opt. geo.)
C(11)--O(1) 2.49(4) -32.5(3) 0.23 multipole
1.3257(8) 2.10 -2.2 0.14 HF/6-311+G(d,p)(exp. geo.)
1.3295 2.10 -9.0 0.03 B3LYP/6-311+G(d,p)(exp. geo.)
2.08 -2.2 0.14 HF/6-311+G(d,p)(opt. geo.)
2.09 -9.3 0.03 B3LYP/6-311+G(d,p)(opt. geo.)
C(11)--O(2) 3.09(5) -36.1(4) 0.10 multipole
1.2274(7) 2.75 -5.8 0.07 HF/6-311+G(d,p)(exp. geo.)
1.1826 2.72 -9.9 0.09 B3LYP/6-311+G(d,p)(exp. geo.)
2.99 +3.5 0.08 HF/6-311+G(d,p)(opt. geo.)
2.98 -1.9 0.08 B3LYP/6-311+G(d,p)(opt. geo.)
N(1)--C(3) 1.99(4) -27.3(2) 0.09 multipole
1.4331(6) 1.83 -15.1 0.03 HF/6-311+G(d,p)(exp. geo.)
1.4219 1.83 -17.8 0.06 B3LYP/6-311+G(d,p)(exp. geo.)
1.87 -15.2 0.04 HF/6-311+G(d,p)(opt. geo.)
1.87 -18.5 0.06 B3LYP/6-311+G(d,p)(opt. geo.)
N(1)--C(6) 2.52(4) -26.7(2) 0.26 multipole
1.3579(6) 2.26 -26.0 0.11 HF/6-311+G(d,p)(exp. geo.)
1.3577 2.21 -24.4 0.19 B3LYP/6-311+G(d,p)(exp. geo.)
2.25 -25.1 0.10 HF/6-311+G(d,p)(opt. geo.)
2.21 -24.1 0.19 B3LYP/6-311+G(d,p)(opt. geo.)
C(6)--O(3) 2.60(4) -33.4(2) 0.02 multipole
1.3294(6) 2.13 -7.4 0.05 HF/6-311+G(d,p)(exp. geo.)
1.3180 2.12 -12.4 0.05 B3LYP/6-311+G(d,p)(exp. geo.)
2.16 -5.1 0.05 HF/6-311+G(d,p)(opt. geo.)
2.16 -10.8 0.04 B3LYP/6-311+G(d,p)(opt. geo.)
C(6)--O(4) 3.11(5) -42.0(3) 0.05 multipole
1.2406(7) 2.72 -12.5 0.07 HF/6-311+G(d,p)(exp. geo.)
1.1922 2.68 -14.7 0.11 B3LYP/6-311+G(d,p)(exp. geo.)
2.97 -3.1 0.08 HF/6-311+G(d,p)(opt. geo.)
2.94 -6.8 0.10 B3LYP/6-311+G(d,p)(opt. geo.)
O(3)--C(7) 1.81(4) -19.4(2) 0.01 multipole
1.4845(7) 1.36 +1.5 0.05 HF/6-311+G(d,p)(exp. geo.)
1.4528 1.43 -7.2 0.01 B3LYP/6-311+G(d,p)(exp. geo.)
1.45 +3.4 0.02 HF/6-311+G(d,p)(opt. geo.)
1.52 -6.8 0.00 B3LYP/6-311+G(d,p)(opt. geo.)
C(7)--C(8) 1.89(2) -20.02(6) 0.08 multipole
1.5215(7) 1.79 -18.0 0.04 HF/6-311+G(d,p)(exp. geo.)
1.5252 1.70 -14.5 0.03 B3LYP/6-311+G(d,p)(exp. geo.)
1.78 -17.8 0.04 HF/6-311+G(d,p)(opt. geo.)
1.69 -14.3 0.04 B3LYP/6-311+G(d,p)(opt. geo.)
C(7)--C(9) 1.86(2) -18.87(7) 0.07 multipole
1.5220(7) 1.78 -17.7 0.03 HF/6-311+G(d,p)(exp. geo.)
1.5269 1.69 -14.2 0.03 B3LYP/6-311+G(d,p)(exp. geo.)
1.76 -17.4 0.03 HF/6-311+G(d,p)(opt. geo.)
1.67 -13.9 0.03 B3LYP/6-311+G(d,p)(opt. geo.)
C(7)--C(10) 1.86(2) -18.85(7) 0.07 multipole
1.5242(8) 1.77 -17.6 0.03 HF/6-311+G(d,p)(exp. geo.)
1.5269 1.68 -14.0 0.03 B3LYP/6-311+G(d,p)(exp. geo.)
1.76 -17.4 0.03 HF/6-311+G(d,p)(opt. geo.)
1.67 -13.9 0.03 B3LYP/6-311+G(d,p)(opt. geo.)
C(1)--C(3) 0.68(2) 11.09(6) -- multipole
1.8680(6) 0.66 11.85 -- HF/6-311+G(d,p)(exp. geo.)
1.8538 0.67 11.09 -- B3LYP/6-311+G(d,p)(exp. geo.)
0.68 12.21 -- HF/6-311+G(d,p)(opt. geo.)
0.69 11.42 -- B3LYP/6-311+G(d,p)(opt. geo.)
# End of Crystallographic Information File