Supplementary Material for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2007
data_global
_journal_name_full Org.Biomol.Chem.
_journal_coden_cambridge 0177
_publ_contact_author_name 'Ben Feringa'
_publ_contact_author_address
;
Organic and Molecular Inorganic Chemistry
University of Groningen
Groningen
9747AG
NETHERLANDS
;
loop_
_publ_author_name
B.Feringa
'de Vries,Johannes G.'
'Robert M. Haak'
'Dick B. Janssen'
'Adriaan J. Minnaard'
'Chiara Tatabiono'
_publ_section_title
;
Synthesis of Enantiopure Chloroalcohols by Enzymatic
Kinetic Resolution
;
_publ_contact_letter # Include date of submission
;
Date of submission : 2006-04-27 07:34:18
Consider this CIF submission for deposition of the X-ray structure
of a manuscript which will probably be submitted to : Organic Letters
(Our Compound_Identification_Code : Q1080)
;
# 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 ?
#===============================================================================
# 3. TITLE AND AUTHOR LIST
data_Q1080
_database_code_depnum_ccdc_archive 'CCDC 605888'
#==============================================================================
# 0. AUDIT DETAILS
_audit_creation_date '2006-02-01 08:24:18'
_audit_creation_method
;
PLATON
option (version :: 300106)
SHELXL97-2 & Manual Editing
;
_audit_update_record
;
?
;
_publ_section_title_footnote
;
?
;
#===============================================================================
# 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 asymmetric unit consists of one molecule of the title compound;
the molecules are linked into an infinite one-dimensional chain by
O-H...O intermolecular bonds.
The chiral center of C9 showed the S-configuration.
;
# Insert blank lines between references
_publ_section_references
;
Allen, F.H. (2000). Acta Cryst. B58, 380-388.
Beurskens, P.T., Beurskens, G., Gelder, R. de, Garc\'ia-Granda, S.
Gould, R.O., Israel, & Smits, J.M.M. (1999).
The DIRDIF99 program system, Technical Report of the Crystallography
Laboratory, University of Nijmegen, The Netherlands.
Bondi, A. (1964). J. Phys. Chem. 68, 441-451.
Bruker, (2000). SMART, SAINTPLUS and XPREP.
Software Reference Manual Bruker AXS Inc. Madison, Wisconsin, USA.
Flack, H.D. & Bernardinelli, G. (1999). Acta Cryst. A55, 908-915.
Flack, H.D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143-1148.
Hahn, T. (1983) Ed. International Tables for Crystallography,
Volume A, Space-group symmetry, Kluwer Academic Publishers,
Dordrecht, The Netherlands.
Le Page, Y. (1987). J. Appl. Cryst. 20, 264-269.
Le Page, Y. (1988). J. Appl. Cryst. 21, 983-984.
Meetsma, A. (2005). Extended version of the program PLUTO.
Groningen University, The Netherlands. (unpublished).
Sheldrick, G.M. SHELXL97. Program for Crystal Structure
Refinement. University of Gottingen, Germany, 1997.
Sheldrick, G.M. SADABS. Version 2.03
Multi-Scan Absorption Correction Program.
University of Gottingen, Germany, 2001
Spek, A.L. (1987). Acta Cryst. C43, 1233-1235.
Spek, A.L. (1988). J. Appl. Cryst. 21, 578-579.
Spek, A.L. (1990). Acta Cryst. A46, C-34.
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_figure_captions
;
Fig. 1. Perspective PLUTO drawing of the moolecule illustrating the
configuration and the adopted numbering scheme.
Fig. 2. Molecular packing viewed down unit cell axes.
Fig. 3. Perspective ORTEP drawing of the title compound.
Displacement ellipsoids for non-H are represented at the 50%
probability level.
The H-atoms are drawn with an arbitrary radius.
;
#===============================================================================
# 5. CHEMICAL DATA
_chemical_name_systematic
;
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C10 H11 Cl O'
# 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 'C10 H11 Cl O'
_chemical_formula_iupac ?
_chemical_formula_weight 182.65
_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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
# 6. CRYSTAL DATA
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_Hall 'P 2ac 2ab'
_symmetry_space_group_name_H-M 'P 21 21 21'
_symmetry_Int_Tables_number 19
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z
_cell_length_a 4.9735(7)
_cell_length_b 10.531(2)
_cell_length_c 17.521(3)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 917.7(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(1)
_cell_measurement_reflns_used 3434
_cell_measurement_theta_min 2.26
_cell_measurement_theta_max 27.44
_cell_special_details
;
The final unit cell was obtained from the xyz centroids of
3434 reflections after integration using the SAINT software
package (Bruker, 2000).
;
_exptl_crystal_description needle
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.52
_exptl_crystal_size_mid 0.11
_exptl_crystal_size_min 0.09
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.322
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 384
_exptl_absorpt_coefficient_mu 0.363
_exptl_absorpt_correction_type Multi-Scan
_exptl_absorpt_process_details '(SADABS, Sheldrick, Bruker, 2001))'
_exptl_absorpt_correction_T_min 0.9098
_exptl_absorpt_correction_T_max 0.9681
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
;
;
_diffrn_ambient_temperature 100(1)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine focus sealed Siemens Mo tube '
_diffrn_radiation_monochromator 'parallel mounted graphite'
_diffrn_radiation_detector
;
CCD area-detector
;
_diffrn_measurement_device_type
;
Bruker Smart Apex; CCD area detector
;
_diffrn_measurement_method '\f and \w scans'
_diffrn_special_details
;
Crystal into the cold nitrogen stream of the low-temparature unit
(KRYOFLEX, (Bruker, 2000)).
;
_diffrn_detector_area_resol_mean '4096x4096 / 62x62 (binned 512)'
_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 7911
_diffrn_reflns_av_R_equivalents 0.0278
_diffrn_reflns_av_sigmaI/netI 0.0302
_diffrn_reflns_limit_h_min -5
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -22
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_theta_min 2.32
_diffrn_reflns_theta_max 27.52
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_reduction_process
;
Intensity data were corrected for Lorentz and polarization
effects, decay and absorption and reduced to F~o~^2^
using SAINT (Bruker, 2000) and SADABS (Sheldrick, 2001)
;
# number of unique reflections
_reflns_number_total 2109
_reflns_number_gt 1994
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'SMART, Version 5.624, (Bruker, 2001)'
_computing_cell_refinement 'SAINTPLUS, Version 6.02A, (Bruker, 2000)'
_computing_data_reduction 'XPREP, Version 5.1/NT, (Bruker, 2000)'
_computing_structure_solution
;
DIRDIF-99 (Beurskens et al., 1999)
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
PLUTO (Meetsma, 2005)
PLATON (Spek, 2003)
;
_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^)+(0.0301P)^2^+0.2279P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary heavy
_atom_sites_solution_secondary direct
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment refall
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details
;
Flack, H.D. & Bernardinelli, G. (1999, 2000)
;
_chemical_absolute_configuration ad
_refine_ls_abs_structure_Flack 0.01(6)
_refine_ls_number_reflns 2109
_refine_ls_number_parameters 153
_refine_ls_number_restraints 0
_refine_ls_number_constraints ?
_refine_ls_R_factor_all 0.0337
_refine_ls_R_factor_gt 0.0311
_refine_ls_wR_factor_ref 0.0698
_refine_ls_wR_factor_gt 0.0687
_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 0.230
_refine_diff_density_min -0.225
_refine_diff_density_rms 0.043
_vrn_publ_code_squeezed_elec 0.0
_vrn_publ_code_void_volume 0.0
_vrn_publ_code_frame_time_sec 10.0
_vrn_publ_code_meas_time_hour 8.0
#===============================================================================
# 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
Cl Cl Uani 0.92114(9) -0.04147(4) -0.03098(2) 1.000 0.0263(1) . .
O O Uani 0.8067(3) 0.23205(11) 0.03509(7) 1.000 0.0213(3) . .
C1 C Uani 0.1000(4) 0.36388(16) 0.22969(9) 1.000 0.0219(5) . .
C2 C Uani -0.0816(4) 0.38140(16) 0.28913(10) 1.000 0.0252(5) . .
C3 C Uani -0.0855(4) 0.29944(17) 0.34995(10) 1.000 0.0250(5) . .
C4 C Uani 0.0988(4) 0.20058(17) 0.35287(10) 1.000 0.0252(5) . .
C5 C Uani 0.2817(4) 0.18317(17) 0.29443(10) 1.000 0.0218(5) . .
C6 C Uani 0.2811(3) 0.26325(15) 0.23074(9) 1.000 0.0183(4) . .
C7 C Uani 0.4613(3) 0.24410(16) 0.16477(9) 1.000 0.0188(4) . .
C8 C Uani 0.6194(3) 0.14516(16) 0.15303(9) 1.000 0.0187(5) . .
C9 C Uani 0.7946(3) 0.12461(16) 0.08427(9) 1.000 0.0181(5) . .
C10 C Uani 0.6923(3) 0.00791(16) 0.04267(10) 1.000 0.0213(5) . .
H1 H Uiso 0.093(5) 0.4194(18) 0.1862(11) 1.000 0.026(5) . .
H2 H Uiso -0.197(4) 0.4511(19) 0.2872(10) 1.000 0.025(5) . .
H3 H Uiso -0.214(4) 0.3056(18) 0.3870(10) 1.000 0.021(5) . .
H4 H Uiso 0.104(5) 0.149(2) 0.3949(12) 1.000 0.039(6) . .
H5 H Uiso 0.410(4) 0.1218(18) 0.2967(10) 1.000 0.022(5) . .
H7 H Uiso 0.460(4) 0.3098(17) 0.1286(10) 1.000 0.016(4) . .
H8 H Uiso 0.626(4) 0.0854(17) 0.1886(10) 1.000 0.020(5) . .
H9 H Uiso 0.974(4) 0.1092(17) 0.0995(10) 1.000 0.022(5) . .
H10 H Uiso 0.522(4) 0.0270(18) 0.0173(10) 1.000 0.022(5) . .
H10' H Uiso 0.676(4) -0.0650(19) 0.0753(11) 1.000 0.023(5) . .
H11 H Uiso 0.685(6) 0.246(3) 0.0163(15) 1.000 0.052(9) . .
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
Cl 0.0264(2) 0.0300(2) 0.0225(2) -0.0044(2) 0.0009(2) 0.0031(2)
O 0.0194(6) 0.0233(6) 0.0211(6) 0.0056(5) -0.0001(5) 0.0006(5)
C1 0.0210(9) 0.0204(8) 0.0244(8) -0.0020(7) -0.0031(7) -0.0006(8)
C2 0.0200(8) 0.0243(9) 0.0314(8) -0.0082(7) -0.0029(8) 0.0046(9)
C3 0.0179(8) 0.0332(9) 0.0240(8) -0.0090(7) 0.0032(8) -0.0035(8)
C4 0.0249(9) 0.0311(9) 0.0196(7) 0.0000(7) -0.0003(8) -0.0025(8)
C5 0.0186(9) 0.0246(9) 0.0221(8) -0.0005(7) -0.0015(7) 0.0018(8)
C6 0.0144(8) 0.0204(8) 0.0200(7) -0.0035(6) -0.0010(6) -0.0039(7)
C7 0.0172(8) 0.0212(8) 0.0181(7) 0.0027(6) -0.0011(6) -0.0039(7)
C8 0.0150(9) 0.0227(8) 0.0184(7) 0.0048(6) -0.0004(6) -0.0015(7)
C9 0.0109(8) 0.0231(9) 0.0204(8) 0.0026(6) -0.0013(6) 0.0014(7)
C10 0.0162(8) 0.0235(8) 0.0241(8) 0.0004(7) 0.0017(7) 0.0009(7)
#===============================================================================
# 10. MOLECULAR GEOMETRY
_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
Cl C10 1.7975(17) . . yes
O C9 1.424(2) . . yes
O H11 0.71(3) . . no
C1 C6 1.391(2) . . no
C1 C2 1.391(3) . . no
C2 C3 1.372(2) . . no
C3 C4 1.388(3) . . no
C4 C5 1.382(3) . . no
C5 C6 1.399(2) . . no
C6 C7 1.477(2) . . no
C7 C8 1.322(2) . . no
C8 C9 1.503(2) . . no
C9 C10 1.517(2) . . no
C1 H1 0.961(19) . . no
C2 H2 0.93(2) . . no
C3 H3 0.913(19) . . no
C4 H4 0.92(2) . . no
C5 H5 0.91(2) . . no
C7 H7 0.938(18) . . no
C8 H8 0.886(18) . . no
C9 H9 0.95(2) . . no
C10 H10 0.977(19) . . no
C10 H10' 0.96(2) . . 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
C9 O H11 114(2) . . . no
C2 C1 C6 120.78(15) . . . no
C1 C2 C3 120.50(17) . . . no
C2 C3 C4 119.43(17) . . . no
C3 C4 C5 120.46(16) . . . no
C4 C5 C6 120.65(17) . . . no
C1 C6 C5 118.12(15) . . . no
C1 C6 C7 119.13(14) . . . no
C5 C6 C7 122.75(15) . . . no
C6 C7 C8 126.21(15) . . . no
C7 C8 C9 125.70(15) . . . no
O C9 C8 113.29(14) . . . yes
C8 C9 C10 107.91(13) . . . no
O C9 C10 111.55(13) . . . yes
Cl C10 C9 111.53(11) . . . yes
C2 C1 H1 119.3(14) . . . no
C6 C1 H1 119.8(13) . . . no
C1 C2 H2 118.5(11) . . . no
C3 C2 H2 121.0(11) . . . no
C2 C3 H3 121.2(12) . . . no
C4 C3 H3 119.3(12) . . . no
C3 C4 H4 119.6(15) . . . no
C5 C4 H4 119.9(15) . . . no
C4 C5 H5 121.6(11) . . . no
C6 C5 H5 117.7(11) . . . no
C6 C7 H7 115.1(12) . . . no
C8 C7 H7 118.7(12) . . . no
C7 C8 H8 118.2(12) . . . no
C9 C8 H8 116.1(12) . . . no
O C9 H9 105.5(11) . . . no
C8 C9 H9 110.2(11) . . . no
C10 C9 H9 108.3(11) . . . no
Cl C10 H10 106.4(11) . . . no
Cl C10 H10' 104.4(12) . . . no
C9 C10 H10 110.0(11) . . . no
C9 C10 H10' 113.0(12) . . . no
H10 C10 H10' 111.2(16) . . . 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
C6 C1 C2 C3 -0.1(3) . . . . no
C2 C1 C6 C5 -2.3(3) . . . . no
C2 C1 C6 C7 176.94(16) . . . . no
C1 C2 C3 C4 1.8(3) . . . . no
C2 C3 C4 C5 -1.2(3) . . . . no
C3 C4 C5 C6 -1.2(3) . . . . no
C4 C5 C6 C1 2.9(3) . . . . no
C4 C5 C6 C7 -176.28(16) . . . . no
C1 C6 C7 C8 -171.16(16) . . . . no
C5 C6 C7 C8 8.0(3) . . . . no
C6 C7 C8 C9 177.69(15) . . . . no
C7 C8 C9 O 8.4(2) . . . . no
C7 C8 C9 C10 -115.66(18) . . . . no
O C9 C10 Cl 64.96(15) . . . . no
C8 C9 C10 Cl -169.98(11) . . . . 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
Cl O 3.1561(14) . . no
Cl C4 3.557(2) . 2_654 no
Cl H4 3.13(2) . 2_554 no
Cl H4 2.92(2) . 2_654 no
Cl H7 2.986(18) . 3_555 no
O Cl 3.1561(14) . . no
O O 2.800(2) . 3_455 no
O O 2.800(2) . 3_555 no
O H7 2.516(19) . . no
O H10 2.903(19) . 3_555 no
O H11 2.10(3) . 3_555 no
C1 C8 3.581(3) . 1_455 no
C2 C6 3.555(3) . 1_455 no
C2 C7 3.465(3) . 1_455 no
C3 C5 3.514(3) . 1_455 no
C3 C10 3.491(3) . 4_655 no
C4 Cl 3.557(2) . 2_655 no
C5 C3 3.514(3) . 1_655 no
C6 C2 3.555(3) . 1_655 no
C7 C2 3.465(3) . 1_655 no
C8 C1 3.581(3) . 1_655 no
C10 C3 3.491(3) . 4_645 no
C1 H8 3.058(18) . 4_655 no
C3 H10' 2.81(2) . 4_655 no
C4 H10' 2.99(2) . 4_655 no
C5 H2 2.863(19) . 4_545 no
C5 H8 2.726(19) . . no
C7 H9 3.033(19) . 1_455 no
C7 H11 2.83(3) . . no
C8 H5 2.735(18) . . no
C9 H11 2.96(3) . 3_555 no
H1 H7 2.38(3) . . no
H2 C5 2.86(2) . 4_555 no
H2 H5 2.55(3) . 4_555 no
H2 H8 2.60(3) . 4_555 no
H4 Cl 3.13(2) . 2_555 no
H4 Cl 2.92(2) . 2_655 no
H5 C8 2.735(18) . . no
H5 H8 2.21(3) . . no
H5 H2 2.55(3) . 4_545 no
H7 O 2.516(19) . . no
H7 H1 2.38(3) . . no
H7 H11 2.36(3) . . no
H7 Cl 2.986(18) . 3_455 no
H8 C5 2.726(19) . . no
H8 H5 2.21(3) . . no
H8 H10' 2.55(3) . . no
H8 C1 3.058(18) . 4_645 no
H8 H2 2.60(3) . 4_545 no
H9 C7 3.033(19) . 1_655 no
H10 H11 2.45(4) . . no
H10 O 2.903(19) . 3_455 no
H10' H8 2.55(3) . . no
H10' C3 2.81(2) . 4_645 no
H10' C4 2.99(2) . 4_645 no
H11 C7 2.83(3) . . no
H11 H7 2.36(3) . . no
H11 H10 2.45(4) . . no
H11 O 2.10(3) . 3_455 no
H11 C9 2.96(3) . 3_455 no
H11 H11 2.55(4) . 3_455 no
H11 H11 2.55(4) . 3_555 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)
#
O H11 O 0.71(3) 2.10(3) 2.800(2) 174(3) 3_455 yes
C7 H7 O 0.938(18) 2.516(19) 2.851(2) 101.3(13) . yes
# Loop Mechanism for Extra Tables(s)
#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'
#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?
#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?
#
#_geom_table_footnote_A
#;
# ?
#;
#
#_geom_table_footnote_B
#;
# ?
#;
#
#_geom_table_footnote_A
#;
# ?
#;
#
#_geom_table_footnote_B
#;
# ?
#;
#===END of Crystallographic Information File