# CIF-file generated for block_1 P 1 New: P6/m
#==============================================================================
data_global
#==============================================================================
# 0. AUDIT DETAILS
_audit_creation_date 'Jul 5 16:48:25 2012'
_audit_creation_method 'PLATON
option'
_audit_update_record
;
;
#===============================================================================
# 1. SUBMISSION DETAILS
_publ_contact_author_name # Name of author for correspondence
;
;
_publ_contact_author_address # address of author for correspondence
;
;
_publ_contact_author_email ?
_publ_contact_author_fax ?
_publ_contact_author_phone ?
_publ_requested_journal 'Acta Crystallographica C'
# Publication choise FI, CI or EI for Inorganic
# FM, CM or EM for Metal-organic
# FO, CO or EO for Organic
_publ_requested_category ?
_publ_requested_coeditor_name ?
_publ_contact_letter # Include date of submission
;
Date of submission ?
Please consider this CIF submission for publication as a
Regular Structural Paper in Acta Crystallographica C.
;
#===============================================================================
# 2. PROCESSING SUMMARY (JOURNAL OFFICE ONLY)
_journal_date_recd_electronic ?
_journal_date_to_coeditor ?
_journal_date_from_coeditor ?
_journal_date_accepted ?
_journal_date_printers_first ?
_journal_date_printers_final ?
_journal_date_proofs_out ?
_journal_date_proofs_in ?
_journal_coeditor_name ?
_journal_coeditor_code ?
_journal_coeditor_notes
;
;
_journal_techeditor_code ?
_journal_techeditor_notes
;
;
_journal_coden_ASTM ?
_journal_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 adresses of all
# authors, in the required order of publication. Repeat as necessary.
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
'?' # author name
; # author related footnote
;
; # Address of this author
;
#===============================================================================
# 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
;
Allen, F.H. (2002).
Acta Cryst. B58, 380-388.
Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C.
Guagliardi, A., Moliterni, A.G.G., Polidori, G. & Spagna, R.
(1999) J. Appl. Cryst. 32, 115-119.
Beurskens, P.T., Beurskens, G., de Gelder, R., Garc\'ia-Granda, S.,
Gould, R.O., Israel, R. & Smits, J.M.M. (1999) The DIRDIF99 Program System,
Technical Report of the Crystallography Laboratory,
University of Nijmegen, The Netherlands.
Boer, J.L. de & Duisenberg, A.J.M. (1984). Acta Cryst. A40, C-410.
Boeyens, J.C.A. (1978). J.Cryst.Mol.Struct. 8, 317-320.
Cremer, D. & Pople, J.A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Duisenberg, A.J.M. (1992). J. Appl. Cryst. 25, 92-96.
Duisenberg, A.J.M., Kroon-Batenburg, L.M.J. & Schreurs, A.M.M. (2003).
J. Appl. Cryst. 36, 220-229.
Enraf-Nonius (1989). CAD-4 Software. Version 5. Enraf-Nonius, Delft,
The Netherlands.
Flack, H.D. (1983). Acta Cryst. A39, 876-881.
Hooft, R.W.W. (1998). Collect Software, Nonius B.V., Delft, The Netherlands.
LePage, Y. (1987). J. Appl. Cryst. 20, 264-269.
Mackay, A.L. (1984). Acta Cryst. A40, 165-166.
Meulenaer, J. de & Tompa, H. (1965). Acta Cryst. 19, 1014-1018.
North, A.C.T., Phillips, D.C. & Mathews, F.S. (1968).
Acta Cryst. A24, 351-359.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
Macromolecular Crystallography, Part A, edited by C.W. Carter &
R.M. Sweet, pp. 307-326. London: Academic Press.
Sheldrick, G.M. (1986). SHELXS86. University of G\"ottingen, Germany.
Sheldrick, G.M. (1993). SHELXL93. University of G\"ottingen, Germany.
Sheldrick, G.M. (1997). SHELXS97. University of G\"ottingen, Germany.
Sheldrick, G.M. (1997). SHELXL97. University of G\"ottingen, Germany.
Sluis, P. van der & Spek, A.L. (1990). Acta Cryst. A46, 194-201.
Spek, A.L. (1987). Acta Cryst. C43, 1233-1235.
Spek, A.L. (1988). J. Appl. Cryst. 21, 578-579.
Spek, A.L. (1994). Am. Crystallogr. Assoc.-Abstracts, 22, 66.
Spek, A.L. (1997). HELENA, Program for Datareduction, Utrecht
University, The Netherlands.
Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13.
Wilson, A.J.C. (1992). Ed. International Tables for Crystallography,
Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands.
;
_publ_section_acknowledgements
;
;
_publ_section_figure_captions
; View of the title compound with the atom numbering scheme.
Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
;
#===============================================================================
data_block_1
#===============================================================================
# 5. CHEMICAL DATA
_chemical_name_systematic
;
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety
'C6 H4 N 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
'C6 H4 N O'
_chemical_formula_iupac ?
_chemical_formula_weight 106.10
_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'
N N 0.0061 0.0033
'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 Hexagonal
_symmetry_space_group_name_Hall '-P 6'
_symmetry_space_group_name_H-M 'P 6/m'
_symmetry_Int_Tables_number 175
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 x-y,x,z
3 -y,x-y,z
4 -x,-y,z
5 -x+y,-x,z
6 y,-x+y,z
7 -x,-y,-z
8 -x+y,-x,-z
9 y,-x+y,-z
10 x,y,-z
11 x-y,x,-z
12 -y,x-y,-z
_cell_length_a 22.55600
_cell_length_b 22.55600
_cell_length_c 3.40000
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 120
_cell_volume 1542.136
_cell_formula_units_Z 6
_cell_measurement_temperature ?
_cell_measurement_reflns_used ?
_cell_measurement_theta_min ?
_cell_measurement_theta_max ?
_cell_special_details
;
;
_exptl_crystal_description ' ?'
_exptl_crystal_colour ' ?'
_exptl_crystal_size_max ?
_exptl_crystal_size_mid ?
_exptl_crystal_size_min ?
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 0.685
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 330
_exptl_absorpt_coefficient_mu 0.048
_exptl_crystal_density_meas_temp ?
# Permitted for _exptl_absorpt_correction_type :
# analytical 'analytical from crystal shape'
# Example: de Meulenaer&Tompa: ABST
# cylinder 'cylindrical'
# gaussian 'Gaussian from crystal shape'
# Example: PLATON/ABSG
# integration 'integration from crystal shape'
# multi-scan 'symmetry-related measurements'
# Example: SADABS, MULABS
# none 'no absorption corr. applied'
# numerical 'numerical from crystal shape'
# psi-scan 'psi-scan corrections'
# Example: PLATON/ABSP
# refdelf 'refined from delta-F'
# Example: SHELXA,
# sphere 'spherical'
# Example: PLATON/ABSS
_exptl_absorpt_correction_type ' ?'
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
;
;
_diffrn_ambient_temperature ?
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_probe 'x-ray'
_diffrn_radiation_type 'MoK\a'
_diffrn_radiation_source ?
_diffrn_radiation_monochromator ?
_diffrn_measurement_device_type ?
_diffrn_measurement_method ?
_diffrn_detector_area_resol_mean ?
# number of measured reflections (redundant set)
_diffrn_reflns_number ?
_diffrn_reflns_av_R_equivalents ?
_diffrn_reflns_av_sigmaI/netI ?
_diffrn_reflns_limit_h_min ?
_diffrn_reflns_limit_h_max ?
_diffrn_reflns_limit_k_min ?
_diffrn_reflns_limit_k_max ?
_diffrn_reflns_limit_l_min ?
_diffrn_reflns_limit_l_max ?
_diffrn_reflns_theta_min ?
_diffrn_reflns_theta_max ?
_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 ?
# number of observed reflections (> n sig(I))
_reflns_number_gt ?
_reflns_threshold_expression ?
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution ?
_computing_structure_refinement ?
_computing_molecular_graphics ?
_computing_publication_material 'PLATON (Spek, 2003)'
#===============================================================================
# 8. REFINEMENT DATA
_refine_special_details ?
_refine_ls_structure_factor_coef ?
_refine_ls_matrix_type ?
_refine_ls_weighting_scheme ' ?'
_refine_ls_weighting_details
?
_atom_sites_solution_primary ' ?'
_atom_sites_solution_secondary ' ?'
_atom_sites_solution_hydrogens ' ?'
# Permitted for _refine_ls_hydrogen_treatment :
# refall - refined all H parameters
# refxyz - refined H coordinates only
# refU - refined H U only
# noref - no refinement of H parameters
# constr - H parameters constrained
# mixed - some constrained, some independent
# undef - H-atom parameters not defined
_refine_ls_hydrogen_treatment ' ?'
_refine_ls_extinction_method ' ?'
_refine_ls_extinction_coef ?
_refine_ls_extinction_expression
?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack .
_refine_ls_number_reflns ?
_refine_ls_number_parameters ?
_refine_ls_number_restraints 0
_refine_ls_number_constraints ?
_refine_ls_R_factor_all ?
_refine_ls_R_factor_gt ?
_refine_ls_wR_factor_ref ?
_refine_ls_wR_factor_gt ?
_refine_ls_goodness_of_fit_ref ?
_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 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
O O Uiso 0.28355 0.52709 0.50000 1.000 0.0500 . .
N N Uiso 0.41129 0.55212 0.50000 1.000 0.0500 . .
C C Uiso 0.30695 0.59146 0.50000 1.000 0.0500 . .
C1 C Uiso 0.38113 0.64063 0.50000 1.000 0.0500 . .
C5 C Uiso 0.42797 0.61784 0.50000 1.000 0.0500 . .
C6 C Uiso 0.45481 0.52704 0.50000 1.000 0.0500 . .
C7 C Uiso 0.42936 0.45590 0.50000 1.000 0.0500 . .
C8 C Uiso 0.52674 0.57065 0.50000 1.000 0.0500 . .
H H Uiso 0.37353 0.42043 0.50000 1.000 0.0600 . .
H1 H Uiso 0.48370 0.65597 0.50000 1.000 0.0600 . .
H1# H Uiso 0.54893 0.62685 0.50000 1.000 0.0600 . .
H17 H Uiso 0.35757 0.51744 0.50000 1.000 0.0600 . .
#===============================================================================
# 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
O C 1.2729 . . yes
N C5 1.3346 . . yes
N C6 1.3561 . . yes
N H17 1.0600 . . no
C C1 1.4797 . 5_565 no
C C1 1.4744 . . no
C1 C5 1.3869 . . no
C6 C8 1.4156 . . no
C6 C7 1.4083 . . no
C7 C8 1.3900 . 4_665 no
C5 H1 1.1100 . . no
C7 H 1.1000 . . no
C8 H1# 1.1100 . . 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
C5 N C6 127.05 . . . yes
C6 N H17 119.00 . . . no
C5 N H17 114.00 . . . no
O C C1 120.17 . . 5_565 yes
O C C1 121.69 . . . yes
C1 C C1 118.14 . . 5_565 no
C C1 C 121.86 . . 3_665 no
C C1 C5 120.63 . . . no
C C1 C5 117.51 3_665 . . no
N C5 C1 124.59 . . . yes
N C6 C8 121.82 . . . yes
N C6 C7 120.51 . . . yes
C7 C6 C8 117.67 . . . no
C6 C7 C8 121.24 . . 4_665 no
C6 C8 C7 121.10 . . 4_665 no
N C5 H1 116.00 . . . no
C1 C5 H1 119.00 . . . no
C6 C7 H 120.00 . . . no
C8 C7 H 119.00 4_665 . . no
C6 C8 H1# 120.00 . . . no
C7 C8 H1# 119.00 4_665 . . no
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N C6 C7 180.00 . . . . no
C5 N C6 C8 0.00 . . . . no
C6 N C5 C1 180.00 . . . . no
O C C1 C5 0.00 . . . . no
C C1 C5 N 0.00 . . . . 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
O N 2.6446 . . no
O H17 1.7900 . . no
O H1 2.4000 . 5_565 no
O H1 2.4000 . 5_565 no
N O 2.6446 . . no
C C 3.5000 . 1_554 no
C C 3.5000 . 1_556 no
C C 3.5000 . 10_555 no
C C 3.5000 . 10_557 no
C1 C1 3.5000 . 1_554 no
C1 C1 3.5000 . 10_557 no
C1 C1 3.5000 . 1_556 no
C1 C1 3.5000 . 10_555 no
C5 C5 3.5000 . 1_554 no
C5 C5 3.5000 . 10_555 no
C5 C5 3.5000 . 1_556 no
C5 C5 3.5000 . 10_557 no
C6 C6 3.5000 . 1_554 no
C6 C6 3.5000 . 10_557 no
C6 C6 3.5000 . 1_556 no
C6 C6 3.5000 . 10_555 no
C7 C7 3.5000 . 1_554 no
C7 C7 3.5000 . 10_555 no
C7 C7 3.5000 . 10_557 no
C7 C7 3.5000 . 1_556 no
C8 C8 3.5000 . 1_556 no
C8 C8 3.5000 . 10_557 no
C8 C8 3.5000 . 1_554 no
C8 C8 3.5000 . 10_555 no
C H17 2.4500 . . no
C5 H1# 2.6300 . . no
C8 H1 2.5500 . . no
H H17 2.3900 . . no
H1 C8 2.5500 . . no
H1 H1# 1.8900 . . no
H1 O 2.4000 . 3_665 no
H1 O 2.4000 . 3_665 no
H1# C5 2.6300 . . no
H1# H1 1.8900 . . no
H17 O 1.7900 . . no
H17 C 2.4500 . . no
H17 H 2.3900 . . 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)
#
N H17 O 1.0600 1.7900 2.6446 134.00 . 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