# 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