# Copyright The Royal Society of Chemistry, 1999
# CCDC Number: 188/159
# CIF-file generated for C14H11NO3 CP389
#==============================================================================
data_global
#==============================================================================
# 0. AUDIT DETAILS
_audit_creation_date 1998-07-06
_audit_creation_method 'PLATON
option'
_audit_update_record
;
?
;
#===============================================================================
# 1. SUBMISSION DETAILS
# Name and address of author for correspondence
_publ_contact_author_name
;
Drs. A. Meetsma
;
_publ_contact_author_address
;
Crystal Structure Center,
Chemical Physics,
Materials Science Center,
Groningen University,
Nijenborgh 4,
NL-9747 AG Groningen,
The Netherlands.
;
_publ_contact_author_email A.Meetsma@fwn.rug.nl
_publ_contact_author_fax '+31 50 3634441'
_publ_contact_author_phone '+31 50 3634368'
_publ_requested_journal 'J. Chem.Soc., Perkin Trans. 2'
# Publication choice FI FM FO CI CM CO AD
_publ_requested_category ?
_publ_requested_coeditor_name ?
_publ_contact_letter # Include date of submission
;
Date of first submission : 1998-07-06
Date of second submission : 1998-12-03
(Now included with a low temperatue (130 K) structure)
Consider this CIF submission for depostion of the
Xray-structure of a manuscript to be submitted to :
J. Chem.Soc., Perkin Trans. 2
Your paper code :: 8105506h Perkin2
(Our Code : CP389)
Title of manuscript ::
Hydrogen bonding properties of
N-(2-carboxyphenyl)salicylidenimine
Authors :
Alette G.J. Ligtenbarg, Ronald Hage,
Auke Meetsma, Ben L. Feringa
;
#===============================================================================
# 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_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
;
?
;
_publ_section_title_footnote
;
?
;
# The loop structure below should contain the names and addresses of all
# authors, in the required order of publication. Repeat as necessary.
loop_
_publ_author_name
_publ_author_address
'Meetsma, Auke'
;
Crystal Structure Center,
Chemical Physics,
Materials Science Center,
Groningen University,
Nijenborgh 4,
NL-9747 AG Groningen,
The Netherlands.
;
#===============================================================================
# 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
;
Boer, J.L. de & Duisenberg, A.J.M. (1984). Acta Cryst. A40, C-410.
Duisenberg, A.J.M. (1992). J. Appl. Cryst. 25, 92-96.
Enraf-Nonius (1994). CAD4-UNIX Software. Version 5.1
Utrecht modified version October 1994.
Enraf-Nonius, Delft, Scientific Instuments Division, Delft,
The Netherlands.
International Tables for Crystallography (1983). Vol. A.
Space-group symmetry, edited by T. Hahn. Dordrecht: Reidel.
(Present distributor Kluwer Academic Publishers, Dordrecht).
International Tables for Crystallography (1992). Vol. C.
Edited by A.J.C Wilson, 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. (1996). Extended version of the program PLUTO.
Groningen University, The Netherlands. (unpublished).
Motherwell, W.D.S & Clegg, W. (1978). PLUTO. Program for plotting
molecular and crystal structures. Univ. of Cambridge, England.
(unpublished).
Sheldrick, G.M. SHELXS86. Program for Crystal Structure
solution. University of G\\"ottingen, Germany, 1986.
Sheldrick, G.M. SHELXS93. Program for Crystal Structure
solution. University of G\\"ottingen, Germany, 1993.
Spek, A.L. (1990). Acta Cryst. A46, C-34.
Spek, A.L. (1997). HELENA, Program for Datareduction, Utrecht
University, The Netherlands.
Spek, A.L. (1994). Am. Crystallogr. Assoc.-Abstracts, 22, 66.
;
_publ_section_figure_captions
;
?
;
_publ_section_acknowledgements
;
?
;
#===============================================================================
data_c14h11no
#===============================================================================
# 5. CHEMICAL DATA
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety
'C14 H11 N O3'
_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
'C14 H11 N O3'
_chemical_formula_weight 241.25
_chemical_compound_source 'by syntheses'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O .0106 .0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C .0033 .0016
'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 '-I 2ya'
_symmetry_space_group_name_H-M 'I 2/a'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,y,-z
-x,-y,-z
1/2+x,-y,z
1/2+x,1/2+y,1/2+z
-x,1/2+y,1/2-z
1/2-x,1/2-y,1/2-z
x,1/2-y,1/2+z
_cell_length_a 14.840(1)
_cell_length_b 6.813(1)
_cell_length_c 22.680(1)
_cell_angle_alpha 90
_cell_angle_beta 97.796(6)
_cell_angle_gamma 90
_cell_volume 2271.9(4)
_cell_formula_units_Z 8
_cell_measurement_temperature 295
_cell_measurement_reflns_used 22
_cell_measurement_theta_min 17.14
_cell_measurement_theta_max 20.82
_cell_special_details
;
Unit cell parameters (Duisenberg, 1992) and orientation matrix were determined
from a least-squares treatment of SET4 (de Boer & Duisenberg, 1984) setting.
Reduced cell calculations did not indicate any higher metric lattice symmetry
and examination of the final atomic coordinates of the structure did not yield
extra symmetry elements (Spek, 1988; Le Page 1987, 1988)
;
_exptl_crystal_description 'block-shaped'
_exptl_crystal_colour 'orange-red'
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.15
_exptl_crystal_size_min 0.5
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas 'Not Measured'
_exptl_crystal_density_diffrn 1.411
_exptl_crystal_density_method ?
_exptl_crystal_F_000 1008
_exptl_absorpt_coefficient_mu .10
_exptl_crystal_density_meas_temp 295
_exptl_absorpt_correction_type ?
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 295
_diffrn_radiation_wavelength .71073
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_source 'fine focus sealed Philips Mo tube '
_diffrn_radiation_monochromator 'perpendicular mounted graphite'
_diffrn_radiation_detector
;
scintillation NaI crystal with photomultiplier
;
_diffrn_measurement_device_type
;
Enraf Nonius CAD-4F diffractometer
;
_diffrn_measurement_method '\w/2\q'
_diffrn_special_details
;
Enraf-Nonius CAD-4F diffractometer.
Graphite-monochromated Mo K\a radiation,
\w/2\q scan, \D\w = (0.85 + 0.34 tg \q)\%.
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time 180
_diffrn_standards_decay_% 8.6
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-4 0 0
-4 -4 0
-2 0 6
# number of measured reflections (redundant set)
_diffrn_reflns_number 2484
_diffrn_reflns_av_R_equivalents 0.0000
_diffrn_reflns_av_sigmaI/netI 0.0120
_diffrn_reflns_limit_h_min -18
_diffrn_reflns_limit_h_max 18
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_k_max 0
_diffrn_reflns_limit_l_min -28
_diffrn_reflns_limit_l_max 28
_diffrn_reflns_theta_min 1.81
_diffrn_reflns_theta_max 26.98
_diffrn_reflns_reduction_process
;
Intensity data were corrected for Lorentz and polarization effects, scale
variation, but not for absorption and reduced to F~o~^2^
;
# number of unique reflections
_reflns_number_total 2484
_reflns_number_gt 1966
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CAD4-UNIX Software Version 5.1, 1994'
_computing_cell_refinement 'SET4 (de Boer & Duisenberg, 1984)'
_computing_data_reduction 'HELENA (Spek, 1993)'
_computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics
;
PLUTO (Meetsma, 1997)
ORTEP (Burnett et al., 1996)
PLATON (Spek, 1994, 1996)
;
_computing_publication_material 'PLATON (Spek, 1990)'
#===============================================================================
# 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 w=1/[\s^2^(Fo^2^)+(0.0777P)^2^+0.2129P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens difmap
_refine_ls_hydrogen_treatment isotropic
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_coef 0.0055(9)
_refine_ls_extinction_expression
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_number_reflns 2484
_refine_ls_number_parameters 208
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0500
_refine_ls_R_factor_gt 0.0388
_refine_ls_wR_factor_ref 0.1154
_refine_ls_wR_factor_gt 0.1102
_refine_ls_goodness_of_fit_ref 1.032
_refine_ls_restrained_S_all 1.032
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max .220
_refine_diff_density_min -.179
_refine_diff_density_rms .042
#===============================================================================
# 9. ATOMIC COORDINATES AND THERMAL PARAMETERS
loop_
_atom_site_label
_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 Uani .12921(6) .78696(15) -.01568(4) 1.000 .0454(3)
O2 Uani .26694(6) .80769(17) .09099(4) 1.000 .0527(3)
O3 Uani .34029(7) 1.0562(2) .13964(5) 1.000 .0674(4)
N1 Uani .08849(7) .83251(15) .09386(4) 1.000 .0350(3)
C1 Uani .04320(8) .74689(18) -.03407(5) 1.000 .0356(3)
C2 Uani .01094(10) .6974(2) -.09332(6) 1.000 .0443(4)
C3 Uani -.07955(11) .6571(2) -.10989(6) 1.000 .0492(4)
C4 Uani -.14186(10) .6656(2) -.06934(7) 1.000 .0514(4)
C5 Uani -.11250(9) .7167(2) -.01185(6) 1.000 .0453(4)
C6 Uani -.01997(8) .75670(18) .00749(5) 1.000 .0357(3)
C7 Uani .00554(8) .80782(18) .06811(5) 1.000 .0364(3)
C8 Uani .11521(8) .88493(18) .15454(5) 1.000 .0355(3)
C9 Uani .05234(9) .8893(2) .19481(6) 1.000 .0480(4)
C10 Uani .07955(11) .9493(3) .25240(6) 1.000 .0577(5)
C11 Uani .16761(12) 1.0044(3) .27080(6) 1.000 .0591(5)
C12 Uani .22986(11) 1.0010(2) .23076(6) 1.000 .0502(5)
C13 Uani .20539(8) .94030(19) .17252(5) 1.000 .0381(4)
C14 Uani .27762(8) .9385(2) .13150(5) 1.000 .0415(4)
H1 Uiso .1731(14) .803(3) -.0516(8) 1.000 .086(6)
H1' Uiso .1388(12) .818(2) .0709(8) 1.000 .061(5)
H2 Uiso .0558(11) .692(2) -.1217(7) 1.000 .054(4)
H3 Uiso -.1024(13) .620(3) -.1514(9) 1.000 .070(5)
H4 Uiso -.2032(14) .641(3) -.0813(9) 1.000 .074(5)
H5 Uiso -.1544(11) .725(2) .0199(8) 1.000 .057(4)
H7 Uiso -.0442(10) .826(2) .0914(7) 1.000 .050(4)
H9 Uiso -.0072(13) .851(3) .1826(8) 1.000 .061(5)
H10 Uiso .0332(12) .945(3) .2810(8) 1.000 .071(5)
H11 Uiso .1876(13) 1.046(3) .3090(10) 1.000 .079(6)
H12 Uiso .2884(13) 1.034(3) .2420(8) 1.000 .065(5)
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 .0334(5) .0687(6) .0352(5) -.0002(4) .0081(3) -.0067(4)
O2 .0361(5) .0801(7) .0439(5) -.0143(5) .0130(4) -.0059(5)
O3 .0428(6) .0910(9) .0713(7) -.0196(6) .0184(5) -.0223(6)
N1 .0309(5) .0411(6) .0339(5) .0019(4) .0077(4) -.0003(4)
C1 .0352(6) .0364(6) .0348(6) .0034(5) .0037(5) -.0016(5)
C2 .0482(8) .0457(7) .0385(7) -.0004(5) .0044(6) -.0017(6)
C3 .0542(8) .0474(8) .0426(7) -.0019(6) -.0055(6) -.0035(6)
C4 .0390(7) .0545(8) .0573(8) .0014(7) -.0062(6) -.0066(6)
C5 .0347(7) .0511(8) .0499(7) .0039(6) .0047(6) -.0038(6)
C6 .0330(6) .0362(6) .0379(6) .0037(5) .0048(5) -.0020(5)
C7 .0321(6) .0396(6) .0388(6) .0043(5) .0091(5) -.0006(5)
C8 .0349(6) .0400(6) .0321(6) .0040(5) .0065(5) .0023(5)
C9 .0389(7) .0680(9) .0389(7) .0074(6) .0117(6) .0016(6)
C10 .0540(8) .0843(11) .0381(7) .0034(7) .0178(6) .0073(8)
C11 .0648(10) .0800(11) .0330(7) -.0078(7) .0086(6) .0028(9)
C12 .0452(8) .0640(9) .0406(7) -.0042(6) .0024(6) -.0023(7)
C13 .0366(6) .0419(7) .0364(6) .0011(5) .0071(5) .0019(5)
C14 .0296(6) .0573(8) .0374(6) -.0002(6) .0036(5) -.0013(5)
#===============================================================================
# 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 C1 1.3165(15) . . yes
O2 C14 1.2744(16) . . yes
O3 C14 1.2229(18) . . yes
O1 H1 1.115(19) . . no
N1 C7 1.2999(16) . . yes
N1 C8 1.4250(15) . . yes
N1 H1' .972(18) . . no
C1 C2 1.4050(18) . . no
C1 C6 1.4183(17) . . no
C2 C3 1.372(2) . . no
C3 C4 1.391(2) . . no
C4 C5 1.363(2) . . no
C5 C6 1.4102(18) . . no
C6 C7 1.4190(16) . . no
C8 C13 1.3970(17) . . no
C8 C9 1.3917(18) . . no
C9 C10 1.376(2) . . no
C10 C11 1.369(2) . . no
C11 C12 1.381(2) . . no
C12 C13 1.3847(18) . . no
C13 C14 1.5117(17) . . no
C2 H2 .987(16) . . no
C3 H3 .99(2) . . no
C4 H4 .93(2) . . no
C5 H5 1.015(17) . . no
C7 H7 .972(15) . . no
C9 H9 .927(19) . . no
C10 H10 1.008(18) . . no
C11 H11 .92(2) . . no
C12 H12 .900(19) . . 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 H1 115.2(10) . . . no
C7 N1 C8 126.07(10) . . . yes
C7 N1 H1' 119.7(11) . . . no
C8 N1 H1' 114.2(11) . . . no
O1 C1 C2 122.87(11) . . . yes
O1 C1 C6 118.65(10) . . . yes
C2 C1 C6 118.47(11) . . . no
C1 C2 C3 120.25(13) . . . no
C2 C3 C4 121.61(13) . . . no
C3 C4 C5 119.23(14) . . . no
C4 C5 C6 121.23(12) . . . no
C1 C6 C5 119.19(11) . . . no
C1 C6 C7 122.82(11) . . . no
C5 C6 C7 117.99(11) . . . no
N1 C7 C6 125.38(11) . . . yes
C9 C8 C13 120.24(11) . . . no
N1 C8 C13 118.66(10) . . . yes
N1 C8 C9 121.04(11) . . . yes
C8 C9 C10 119.53(13) . . . no
C9 C10 C11 121.05(14) . . . no
C10 C11 C12 119.41(13) . . . no
C11 C12 C13 121.34(14) . . . no
C12 C13 C14 118.25(11) . . . no
C8 C13 C12 118.42(12) . . . no
C8 C13 C14 123.32(10) . . . no
O2 C14 O3 125.81(12) . . . yes
O2 C14 C13 114.84(11) . . . yes
O3 C14 C13 119.34(11) . . . yes
C1 C2 H2 117.4(9) . . . no
C3 C2 H2 122.4(9) . . . no
C2 C3 H3 120.5(11) . . . no
C4 C3 H3 117.8(11) . . . no
C3 C4 H4 120.8(13) . . . no
C5 C4 H4 119.9(13) . . . no
C4 C5 H5 123.1(10) . . . no
C6 C5 H5 115.7(10) . . . no
N1 C7 H7 118.8(9) . . . no
C6 C7 H7 115.8(9) . . . no
C8 C9 H9 119.6(11) . . . no
C10 C9 H9 120.8(11) . . . no
C9 C10 H10 117.7(11) . . . no
C11 C10 H10 121.2(10) . . . no
C10 C11 H11 122.9(12) . . . no
C12 C11 H11 117.7(12) . . . no
C11 C12 H12 121.0(12) . . . no
C13 C12 H12 117.6(12) . . . 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 N1 C8 C13 -168.51(12) . . . . no
C7 N1 C8 C9 8.80(19) . . . . no
C8 N1 C7 C6 179.61(11) . . . . no
C2 C1 C6 C5 .00(18) . . . . no
C2 C1 C6 C7 -179.16(12) . . . . no
O1 C1 C2 C3 -179.98(12) . . . . no
C6 C1 C2 C3 -.90(19) . . . . no
O1 C1 C6 C5 179.15(12) . . . . no
O1 C1 C6 C7 -.03(18) . . . . no
C1 C2 C3 C4 .6(2) . . . . no
C2 C3 C4 C5 .5(2) . . . . no
C3 C4 C5 C6 -1.4(2) . . . . no
C4 C5 C6 C1 1.2(2) . . . . no
C4 C5 C6 C7 -179.62(12) . . . . no
C1 C6 C7 N1 -7.0(2) . . . . no
C5 C6 C7 N1 173.85(12) . . . . no
N1 C8 C13 C12 176.65(11) . . . . no
N1 C8 C9 C10 -177.01(14) . . . . no
C13 C8 C9 C10 .3(2) . . . . no
C9 C8 C13 C14 179.69(12) . . . . no
N1 C8 C13 C14 -2.97(18) . . . . no
C9 C8 C13 C12 -.68(19) . . . . no
C8 C9 C10 C11 -.2(3) . . . . no
C9 C10 C11 C12 .5(3) . . . . no
C10 C11 C12 C13 -.9(3) . . . . no
C11 C12 C13 C8 1.0(2) . . . . no
C11 C12 C13 C14 -179.33(14) . . . . no
C8 C13 C14 O2 -30.90(18) . . . . no
C8 C13 C14 O3 149.99(13) . . . . no
C12 C13 C14 O2 149.48(12) . . . . no
C12 C13 C14 O3 -29.63(19) . . . . 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 2.9511(13) . . no
O1 N1 2.6535(13) . . no
O1 O2 2.4549(13) . 2_555 no
O1 C14 3.2959(16) . 2_555 no
O2 C1 3.2808(16) . 2_555 no
O2 O1 2.9511(13) . . no
O2 N1 2.6632(14) . . no
O2 C2 3.3742(18) . 2_555 no
O2 O1 2.4549(13) . 2_555 no
O3 C9 3.2462(18) . 4_575 no
O3 C7 3.2532(17) . 4_575 no
O1 H1' 1.961(18) . . no
O2 H1 1.34(2) . 2_555 no
O2 H1' 1.896(18) . . no
O2 H2 2.744(16) . 2_555 no
O3 H1 2.626(19) . 2_555 no
O3 H12 2.548(18) . . no
O3 H7 2.300(15) . 4_575 no
O3 H9 2.423(19) . 4_575 no
N1 O1 2.6535(13) . . no
N1 O2 2.6632(14) . . no
N1 C3 3.3600(18) . 3_565 no
C1 C6 3.5086(18) . 3_565 no
C1 O2 3.2807(16) . 2_555 no
C1 C5 3.4391(19) . 3_565 no
C1 C6 3.4608(18) . 3_575 no
C1 C7 3.1893(18) . 3_575 no
C2 C7 3.5032(19) . 3_565 no
C2 O2 3.3742(18) . 2_555 no
C2 C7 3.4333(19) . 3_575 no
C2 C8 3.5812(19) . 3_575 no
C3 C13 3.508(2) . 3_575 no
C3 C8 3.3008(19) . 3_575 no
C3 N1 3.3600(18) . 3_565 no
C3 C7 3.4431(19) . 3_565 no
C4 C14 3.543(2) . 3_575 no
C5 C1 3.4391(19) . 3_565 no
C6 C1 3.4608(18) . 3_575 no
C6 C1 3.5086(18) . 3_565 no
C6 C6 3.3929(18) . 3_575 no
C6 C7 3.4479(18) . 3_575 no
C6 C6 3.5715(18) . 3_565 no
C7 C2 3.4333(19) . 3_575 no
C7 C2 3.5032(19) . 3_565 no
C7 O3 3.2532(17) . 4_475 no
C7 C1 3.1893(18) . 3_575 no
C7 C6 3.4479(18) . 3_575 no
C7 C3 3.4431(19) . 3_565 no
C8 C2 3.5812(19) . 3_575 no
C8 C3 3.3008(19) . 3_575 no
C9 O3 3.2462(18) . 4_475 no
C12 C12 3.534(2) . 7_575 no
C12 C12 3.560(2) . 7_565 no
C13 C3 3.508(2) . 3_575 no
C14 O1 3.2959(16) . 2_555 no
C14 C4 3.543(2) . 3_575 no
C1 H1' 2.646(18) . . no
C2 H10 3.071(18) . 8_564 no
C7 H9 2.645(18) . . no
C9 H7 2.613(16) . . no
C10 H2 3.079(16) . 8_565 no
C14 H1' 2.457(18) . . no
C14 H1 2.243(19) . 2_555 no
C14 H2 3.022(16) . 2_555 no
H1 H2 2.32(3) . . no
H1 O2 1.34(2) . 2_555 no
H1 O3 2.626(19) . 2_555 no
H1 C14 2.243(19) . 2_555 no
H1' O1 1.961(18) . . no
H1' O2 1.896(18) . . no
H1' C1 2.646(18) . . no
H1' C14 2.457(18) . . no
H2 H1 2.32(3) . . no
H2 O2 2.744(16) . 2_555 no
H2 C14 3.022(16) . 2_555 no
H2 C10 3.079(16) . 8_564 no
H2 H10 2.38(2) . 8_564 no
H5 H7 2.25(2) . . no
H7 C9 2.613(16) . . no
H7 H5 2.25(2) . . no
H7 H9 2.07(2) . . no
H7 O3 2.300(15) . 4_475 no
H9 C7 2.645(18) . . no
H9 H7 2.07(2) . . no
H9 O3 2.423(19) . 4_475 no
H10 C2 3.071(18) . 8_565 no
H10 H2 2.38(2) . 8_565 no
H12 O3 2.548(18) . . 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)
#
O1 H1 O2 1.115(19) 1.34(2) 2.4549(13) 173.1(19) 2_555 yes
N1 H1' O1 .972(18) 1.961(18) 2.6535(13) 126.2(14) . yes
N1 H1' O2 .972(18) 1.896(18) 2.6632(14) 133.9(15) . yes
C7 H7 O3 .972(15) 2.300(15) 3.2532(17) 166.6(12) 4_475 yes
C9 H9 O3 .927(19) 2.423(19) 3.2462(18) 147.9(17) 4_475 yes
# End of Crystallographic Information File
# === END
# CIF-file generated for C14H11NO3 CP389B
data_c14h11no2
#===============================================================================
# 5. CHEMICAL DATA
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety
'C14 H11 N O3'
_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
'C14 H11 N O3'
_chemical_formula_weight 241.25
_chemical_compound_source 'by syntheses'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O .0106 .0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C .0033 .0016
'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 '-I 2ya'
_symmetry_space_group_name_H-M 'I 2/a'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,y,-z
-x,-y,-z
1/2+x,-y,z
1/2+x,1/2+y,1/2+z
-x,1/2+y,1/2-z
1/2-x,1/2-y,1/2-z
x,1/2-y,1/2+z
_cell_length_a 14.831(1)
_cell_length_b 6.718(1)
_cell_length_c 22.660(5)
_cell_angle_alpha 90
_cell_angle_beta 97.610(5)
_cell_angle_gamma 90
_cell_volume 2237.8(6)
_cell_formula_units_Z 8
_cell_measurement_temperature 130
_cell_measurement_reflns_used 22
_cell_measurement_theta_min 16.63
_cell_measurement_theta_max 21.46
_cell_special_details
;
Unit cell parameters (Duisenberg, 1992) and orientation matrix were determined
from a least-squares treatment of SET4 (de Boer & Duisenberg, 1984) setting.
Reduced cell calculations did not indicate any higher metric lattice symmetry
and examination of the final atomic coordinates of the structure did not yield
extra symmetry elements (Spek, 1988; Le Page 1987, 1988)
;
_exptl_crystal_description 'block-shaped'
_exptl_crystal_colour 'oranje-red'
_exptl_crystal_size_max 0.50
_exptl_crystal_size_mid 0.15
_exptl_crystal_size_min 0.10
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas 'Not Measured'
_exptl_crystal_density_diffrn 1.432
_exptl_crystal_density_method ?
_exptl_crystal_F_000 1008
_exptl_absorpt_coefficient_mu .10
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type ' none'
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 130
_diffrn_radiation_wavelength .71073
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_source 'fine focus sealed Philips Mo tube '
_diffrn_radiation_monochromator 'perpendicular mounted graphite'
_diffrn_radiation_detector
;
scintillation NaI crystal with photomultiplier
;
_diffrn_measurement_device_type
;
Enraf Nonius CAD-4F diffractometer
;
_diffrn_measurement_method '\w/2\q'
_diffrn_special_details
;
Crystal into the cold nitrogen stream of the low-temperature unit
(Bolhuis, 1971), on an Enraf-Nonius CAD-4F diffractometer.
Graphite-monochromated Mo K\a radiation,
\w/2\q scan, \D\w = (0.80 + 0.34 tg \q)\%.
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time 180
_diffrn_standards_decay_% 0.2
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-3 2 -1
4 0 -2
-2 -1 -3
# number of measured reflections (redundant set)
_diffrn_reflns_number 2484
_diffrn_reflns_av_R_equivalents 0.0061
_diffrn_reflns_av_sigmaI/netI 0.0186
_diffrn_reflns_limit_h_min -18
_diffrn_reflns_limit_h_max 0
_diffrn_reflns_limit_k_min 0
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_l_min -27
_diffrn_reflns_limit_l_max 27
_diffrn_reflns_theta_min 1.55
_diffrn_reflns_theta_max 26.00
_diffrn_reflns_reduction_process
;
Intensity data were corrected for Lorentz and polarization effects, scale
variation, but not for absorption and reduced to F~o~^2^
;
# number of unique reflections
_reflns_number_total 2192
_reflns_number_gt 1783
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CAD4-UNIX Software Version 5.1, 1994'
_computing_cell_refinement 'SET4 (de Boer & Duisenberg, 1984)'
_computing_data_reduction 'HELENA (Spek, 1993)'
_computing_structure_solution
;
The coordinates of the room-temperature structure were used as starting
positions of the refinement
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
PLUTO (Meetsma, 1997)
ORTEP (Burnett et al., 1996)
PLATON (Spek, 1994, 1996)
;
_computing_publication_material 'PLATON (Spek, 1990)'
#===============================================================================
# 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 w=1/[\s^2^(Fo^2^)+(0.0636P)^2^+0.3190P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens difmap
_refine_ls_hydrogen_treatment isotropic
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2192
_refine_ls_number_parameters 207
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0482
_refine_ls_R_factor_gt 0.0359
_refine_ls_wR_factor_ref 0.1001
_refine_ls_wR_factor_gt 0.0951
_refine_ls_goodness_of_fit_ref 1.050
_refine_ls_restrained_S_all 1.050
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max .214
_refine_diff_density_min -.256
_refine_diff_density_rms .049
#===============================================================================
# 9. ATOMIC COORDINATES AND THERMAL PARAMETERS
loop_
_atom_site_label
_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 Uani .12980(6) .78538(15) -.01551(4) 1.000 .0248(3)
O2 Uani .26662(6) .80206(15) .09128(4) 1.000 .0280(3)
O3 Uani .33983(7) 1.05781(17) .13936(5) 1.000 .0346(3)
N1 Uani .08788(8) .83165(16) .09402(5) 1.000 .0200(3)
C1 Uani .04360(9) .74642(18) -.03433(6) 1.000 .0202(4)
C2 Uani .01177(10) .6979(2) -.09385(6) 1.000 .0247(4)
C3 Uani -.07892(10) .6580(2) -.11074(6) 1.000 .0268(4)
C4 Uani -.14234(10) .6674(2) -.07030(6) 1.000 .0280(4)
C5 Uani -.11313(10) .7184(2) -.01226(6) 1.000 .0251(4)
C6 Uani -.02015(9) .75678(19) .00711(6) 1.000 .0202(4)
C7 Uani .00482(9) .80837(19) .06808(6) 1.000 .0208(4)
C8 Uani .11423(9) .88418(19) .15485(5) 1.000 .0198(4)
C9 Uani .05096(10) .8894(2) .19506(6) 1.000 .0265(4)
C10 Uani .07777(10) .9499(2) .25296(6) 1.000 .0313(5)
C11 Uani .16672(11) 1.0065(2) .27150(6) 1.000 .0313(5)
C12 Uani .22920(10) 1.0016(2) .23128(6) 1.000 .0275(4)
C13 Uani .20474(9) .9394(2) .17287(6) 1.000 .0215(4)
C14 Uani .27718(9) .9368(2) .13160(6) 1.000 .0234(4)
H1 Uiso .1731(14) .801(3) -.0511(9) 1.000 .067(7)
H1' Uiso .1348(12) .813(3) .0699(8) 1.000 .041(5)
H2 Uiso .0572(11) .695(2) -.1231(7) 1.000 .031(4)
H3 Uiso -.1012(11) .620(2) -.1522(7) 1.000 .033(4)
H4 Uiso -.2039(13) .637(3) -.0824(8) 1.000 .042(5)
H5 Uiso -.1556(12) .725(3) .0185(8) 1.000 .037(4)
H7 Uiso -.0467(11) .826(2) .0917(7) 1.000 .036(4)
H9 Uiso -.0093(13) .855(3) .1822(8) 1.000 .041(5)
H10 Uiso .0309(11) .952(3) .2805(7) 1.000 .035(4)
H11 Uiso .1864(11) 1.053(2) .3110(8) 1.000 .035(4)
H12 Uiso .2899(12) 1.039(2) .2435(7) 1.000 .032(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 .0184(5) .0354(6) .0209(5) .0005(4) .0034(4) -.0034(4)
O2 .0206(5) .0399(6) .0243(5) -.0068(4) .0061(4) -.0026(4)
O3 .0228(5) .0445(7) .0376(6) -.0085(5) .0084(4) -.0102(5)
N1 .0178(6) .0226(6) .0198(5) .0016(5) .0035(4) .0004(5)
C1 .0197(7) .0179(6) .0225(6) .0030(5) .0007(5) -.0010(5)
C2 .0269(7) .0239(7) .0232(7) -.0003(5) .0026(6) -.0001(6)
C3 .0310(8) .0236(7) .0241(7) -.0010(6) -.0031(6) -.0012(6)
C4 .0227(7) .0277(8) .0319(8) .0009(6) -.0026(6) -.0035(6)
C5 .0208(7) .0260(7) .0286(7) .0038(6) .0031(6) -.0017(6)
C6 .0202(7) .0182(6) .0224(6) .0021(5) .0033(5) -.0001(5)
C7 .0189(6) .0202(7) .0235(7) .0041(5) .0038(5) .0007(5)
C8 .0209(7) .0202(6) .0185(6) .0032(5) .0030(5) .0013(5)
C9 .0219(7) .0341(8) .0239(7) .0040(6) .0045(6) .0005(6)
C10 .0300(8) .0422(9) .0230(7) .0030(6) .0087(6) .0041(7)
C11 .0360(9) .0383(8) .0192(7) -.0034(6) .0027(6) .0019(7)
C12 .0245(7) .0323(8) .0247(7) -.0015(6) .0000(6) -.0007(6)
C13 .0205(7) .0223(7) .0219(6) .0018(5) .0041(5) .0015(5)
C14 .0167(6) .0314(7) .0219(6) .0012(6) .0013(5) .0002(6)
#===============================================================================
# 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 C1 1.3192(16) . . yes
O2 C14 1.2809(17) . . yes
O3 C14 1.2296(18) . . yes
O1 H1 1.10(2) . . no
N1 C7 1.3022(18) . . yes
N1 C8 1.4264(16) . . yes
N1 H1' .948(18) . . no
C1 C2 1.4070(19) . . no
C1 C6 1.4198(19) . . no
C2 C3 1.375(2) . . no
C3 C4 1.399(2) . . no
C4 C5 1.3725(19) . . no
C5 C6 1.414(2) . . no
C6 C7 1.4250(19) . . no
C8 C13 1.4004(19) . . no
C8 C9 1.3923(19) . . no
C9 C10 1.3808(19) . . no
C10 C11 1.384(2) . . no
C11 C12 1.383(2) . . no
C12 C13 1.3896(19) . . no
C13 C14 1.5150(19) . . no
C2 H2 1.006(16) . . no
C3 H3 .987(16) . . no
C4 H4 .940(19) . . no
C5 H5 1.000(18) . . no
C7 H7 .996(16) . . no
C9 H9 .932(19) . . no
C10 H10 .994(16) . . no
C11 H11 .956(18) . . no
C12 H12 .940(18) . . 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 H1 114.6(11) . . . no
C7 N1 C8 125.99(12) . . . yes
C7 N1 H1' 116.5(11) . . . no
C8 N1 H1' 117.5(11) . . . no
O1 C1 C2 122.93(12) . . . yes
O1 C1 C6 118.57(12) . . . yes
C2 C1 C6 118.50(12) . . . no
C1 C2 C3 120.24(13) . . . no
C2 C3 C4 121.78(13) . . . no
C3 C4 C5 118.99(14) . . . no
C4 C5 C6 120.92(13) . . . no
C1 C6 C5 119.55(12) . . . no
C1 C6 C7 122.88(12) . . . no
C5 C6 C7 117.56(12) . . . no
N1 C7 C6 125.15(12) . . . yes
C9 C8 C13 120.37(11) . . . no
N1 C8 C13 118.47(11) . . . yes
N1 C8 C9 121.10(12) . . . yes
C8 C9 C10 119.67(13) . . . no
C9 C10 C11 120.82(13) . . . no
C10 C11 C12 119.23(13) . . . no
C11 C12 C13 121.43(13) . . . no
C12 C13 C14 118.32(12) . . . no
C8 C13 C12 118.47(12) . . . no
C8 C13 C14 123.21(12) . . . no
O2 C14 O3 126.01(13) . . . yes
O2 C14 C13 114.75(11) . . . yes
O3 C14 C13 119.23(12) . . . yes
C1 C2 H2 117.8(9) . . . no
C3 C2 H2 121.9(9) . . . no
C2 C3 H3 120.5(10) . . . no
C4 C3 H3 117.8(10) . . . no
C3 C4 H4 120.7(11) . . . no
C5 C4 H4 120.3(11) . . . no
C4 C5 H5 122.1(10) . . . no
C6 C5 H5 117.0(10) . . . no
N1 C7 H7 119.4(9) . . . no
C6 C7 H7 115.5(9) . . . no
C8 C9 H9 119.4(11) . . . no
C10 C9 H9 120.9(11) . . . no
C9 C10 H10 117.6(10) . . . no
C11 C10 H10 121.6(10) . . . no
C10 C11 H11 122.3(10) . . . no
C12 C11 H11 118.4(10) . . . no
C11 C12 H12 119.9(10) . . . no
C13 C12 H12 118.7(10) . . . 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 N1 C8 C13 -168.22(13) . . . . no
C7 N1 C8 C9 9.0(2) . . . . no
C8 N1 C7 C6 179.67(12) . . . . no
C2 C1 C6 C5 .03(18) . . . . no
C2 C1 C6 C7 -178.76(12) . . . . no
O1 C1 C2 C3 179.75(15) . . . . no
C6 C1 C2 C3 -1.22(19) . . . . no
O1 C1 C6 C5 179.10(12) . . . . no
O1 C1 C6 C7 .3(2) . . . . no
C1 C2 C3 C4 1.1(2) . . . . no
C2 C3 C4 C5 .2(2) . . . . no
C3 C4 C5 C6 -1.4(2) . . . . no
C4 C5 C6 C1 1.3(2) . . . . no
C4 C5 C6 C7 -179.85(12) . . . . no
C1 C6 C7 N1 -7.3(2) . . . . no
C5 C6 C7 N1 173.91(13) . . . . no
N1 C8 C13 C12 176.34(12) . . . . no
N1 C8 C9 C10 -176.95(12) . . . . no
C13 C8 C9 C10 .2(2) . . . . no
C9 C8 C13 C14 179.83(13) . . . . no
N1 C8 C13 C14 -2.98(19) . . . . no
C9 C8 C13 C12 -.8(2) . . . . no
C8 C9 C10 C11 .3(2) . . . . no
C9 C10 C11 C12 -.1(2) . . . . no
C10 C11 C12 C13 -.6(2) . . . . no
C11 C12 C13 C8 1.1(2) . . . . no
C11 C12 C13 C14 -179.58(12) . . . . no
C8 C13 C14 O2 -31.70(19) . . . . no
C8 C13 C14 O3 149.09(14) . . . . no
C12 C13 C14 O2 148.98(13) . . . . no
C12 C13 C14 O3 -30.23(19) . . . . 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 2.9471(14) . . no
O1 N1 2.6555(16) . . no
O1 C5 3.4075(18) . 3_575 no
O1 O2 2.4534(14) . 2_555 no
O1 C14 3.2893(18) . 2_555 no
O2 O1 2.4534(14) . 2_555 no
O2 O1 2.9471(14) . . no
O2 N1 2.6672(16) . . no
O2 C2 3.3533(19) . 2_555 no
O2 C1 3.2694(18) . 2_555 no
O3 C9 3.237(2) . 4_575 no
O3 C7 3.2329(19) . 4_575 no
O1 H1' 1.936(18) . . no
O2 H1 1.36(2) . 2_555 no
O2 H1' 1.952(18) . . no
O2 H2 2.714(16) . 2_555 no
O3 H1 2.63(2) . 2_555 no
O3 H12 2.568(16) . . no
O3 H7 2.256(16) . 4_575 no
O3 H9 2.391(19) . 4_575 no
O3 H11 2.893(14) . 7_575 no
N1 O1 2.6555(16) . . no
N1 O2 2.6672(16) . . no
N1 C3 3.3159(19) . 3_565 no
C1 C6 3.4621(19) . 3_565 no
C1 O2 3.2694(18) . 2_555 no
C1 C5 3.412(2) . 3_565 no
C1 C6 3.4201(19) . 3_575 no
C1 C7 3.1465(19) . 3_575 no
C2 C7 3.465(2) . 3_565 no
C2 O2 3.3533(19) . 2_555 no
C2 C7 3.382(2) . 3_575 no
C2 C8 3.550(2) . 3_575 no
C3 C13 3.476(2) . 3_575 no
C3 C8 3.255(2) . 3_575 no
C3 N1 3.3159(19) . 3_565 no
C3 C7 3.417(2) . 3_565 no
C4 C14 3.502(2) . 3_575 no
C4 C13 3.559(2) . 3_575 no
C5 C1 3.412(2) . 3_565 no
C5 O1 3.4075(18) . 3_575 no
C6 C1 3.4201(19) . 3_575 no
C6 C6 3.345(2) . 3_575 no
C6 C1 3.4621(19) . 3_565 no
C6 C7 3.405(2) . 3_575 no
C6 C6 3.524(2) . 3_565 no
C7 O3 3.2329(19) . 4_475 no
C7 C1 3.1465(19) . 3_575 no
C7 C2 3.382(2) . 3_575 no
C7 C3 3.417(2) . 3_565 no
C7 C2 3.465(2) . 3_565 no
C7 C6 3.405(2) . 3_575 no
C8 C2 3.550(2) . 3_575 no
C8 C3 3.255(2) . 3_575 no
C9 O3 3.237(2) . 4_475 no
C12 C12 3.520(2) . 7_565 no
C12 C12 3.479(2) . 7_575 no
C13 C4 3.559(2) . 3_575 no
C13 C3 3.476(2) . 3_575 no
C14 O1 3.2893(18) . 2_555 no
C14 C4 3.502(2) . 3_575 no
C1 H1' 2.600(18) . . no
C2 H10 3.068(16) . 8_564 no
C7 H9 2.641(18) . . no
C9 H7 2.620(16) . . no
C10 H2 3.026(16) . 8_565 no
C14 H1' 2.515(18) . . no
C14 H1 2.25(2) . 2_555 no
C14 H2 2.972(16) . 2_555 no
H1 H2 2.32(3) . . no
H1 O2 1.36(2) . 2_555 no
H1 O3 2.63(2) . 2_555 no
H1 C14 2.25(2) . 2_555 no
H1' O1 1.936(18) . . no
H1' O2 1.952(18) . . no
H1' C1 2.600(18) . . no
H1' C14 2.515(18) . . no
H2 H1 2.32(3) . . no
H2 O2 2.714(16) . 2_555 no
H2 C14 2.972(16) . 2_555 no
H2 C10 3.026(16) . 8_564 no
H2 H10 2.38(2) . 8_564 no
H5 H7 2.26(2) . . no
H7 C9 2.620(16) . . no
H7 H5 2.26(2) . . no
H7 H9 2.06(2) . . no
H7 O3 2.256(16) . 4_475 no
H9 C7 2.641(18) . . no
H9 H7 2.06(2) . . no
H9 O3 2.391(19) . 4_475 no
H10 C2 3.068(16) . 8_565 no
H10 H2 2.38(2) . 8_565 no
H11 O3 2.893(14) . 7_575 no
H12 O3 2.568(16) . . 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)
#
O1 H1 O2 1.10(2) 1.36(2) 2.4534(14) 172.7(19) 2_555 yes
N1 H1' O1 .948(18) 1.936(18) 2.6555(16) 130.9(15) . yes
N1 H1' O2 .948(18) 1.952(18) 2.6672(16) 130.5(15) . yes
C7 H7 O3 .996(16) 2.256(16) 3.2329(19) 166.4(11) 4_475 yes
C9 H9 O3 .932(19) 2.391(19) 3.237(2) 150.9(17) 4_475 yes
# End of Crystallographic Information File