Electronic Supplementary MAterial for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Marcel Bouvet' ; Laboratoire de Chimie Inorganique et Materiaux Moleculaires, Universite Pierre et Marie Curie, CNRS-UMR 7071, 4 place Jussieu, case courrier 42 75252 Paris cedex 05, France. ; B. 'Patrick Herson' ; Laboratoire de Chimie Inorganique et Materiaux Moleculaires, Universite Pierre et Marie Curie, CNRS-UMR 7071, 4 place Jussieu, case courrier 42 75252 Pacris cedex 05, France. ; P. 'Bernard Malezieux' ; Laboratoire de Chimie Inorganique et Materiaux Moleculaires, Universite Pierre et Marie Curie, CNRS-UMR 7071, 4 place Jussieu, case courrier 42 75252 Paris cedex 05, France. ; O. 'Francoise Villain' Youchrett-Zallez ; Laboratoire de Thermodynamique et d'Electrochimie, Departement de Chimie Faculte des Sciences de Bizerte, 7021 Zarzouna, Bizerte, Tunisie. ; _publ_contact_author_name 'Marcel Bouvet' _publ_contact_author_address ; Chimie Inorganique et Materiaux Moleculaires UPMC-CNRS 4, Place Jussieu Paris 75252 FRANCE ; _publ_contact_author_email MARCEL.BOUVET@ESPCI.FR _publ_section_title ; Self-Organization of the 2-Methoxyquinhydrone Charge Transfer Complex in Polar Planes ; _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ? _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? # PROCESSING SUMMARY (IUCr Office Use Only): _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ? _journal_volume ? _journal_year ? _publ_contact_author_fax '+33 1 44 27 38 41' _publ_contact_author_phone '+33 1 44 27 30 83' # Check this file using the IUCr facility at: # http://checkcif.iucr.org/ # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica E. The figures have been sent by mail. ; _publ_requested_category CO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name 'Prof William Clegg' # Attachment 'MB-cif1.doc' data_1 _database_code_depnum_ccdc_archive 'CCDC 626640' _audit_creation_date 06-01-26 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title '1260941 Compound X' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 7.8386(10) _cell_length_b 12.791(3) _cell_length_c 13.187(2) _cell_angle_alpha 90 _cell_angle_beta 99.170(11) _cell_angle_gamma 90 _cell_volume 1305.3(4) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-p 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C14 H14 O6 # Dc = 1.42 Fooo = 584.00 Mu = 1.12 M = 278.26 # Found Formula = C14 H14 O6 # Dc = 1.42 FOOO = 584.00 Mu = 1.12 M = 278.26 _chemical_formula_sum 'C14 H14 O6' _chemical_formula_moiety 'C7 H8 O3, C7 H6 O3' _chemical_compound_source ? _chemical_formula_weight 278.26 _cell_measurement_reflns_used 45 _cell_measurement_theta_min 5 _cell_measurement_theta_max 19.8 _cell_measurement_temperature 295 _exptl_crystal_description parallelepiped _exptl_crystal_colour red _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_max 0.14 _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.112 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'COLLECT. Nonius (1997-2001).' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 295 _diffrn_reflns_number 11762 _reflns_number_total 3773 _diffrn_reflns_av_R_equivalents 0.039 # Number of reflections with Friedels Law is 3773 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3803 _diffrn_reflns_theta_min 2.232 _diffrn_reflns_theta_max 30.003 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.503 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -11 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 17 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.41 _refine_diff_density_max 0.33 _refine_ls_number_reflns 1213 _refine_ls_number_restraints 0 _refine_ls_number_parameters 183 #_refine_ls_R_factor_ref 0.0675 _refine_ls_wR_factor_ref 0.0570 _refine_ls_goodness_of_fit_ref 1.0526 #_reflns_number_all 3772 _refine_ls_R_factor_all 0.2296 _refine_ls_wR_factor_all 0.1282 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.50u(I) _reflns_number_gt 1213 _refine_ls_R_factor_gt 0.0675 _refine_ls_wR_factor_gt 0.0570 _refine_ls_shift/su_max 0.000121 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment refu _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.85 -0.490E-01 1.41 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # Some potentially useful phrases are: ; Because the data were collected with molybdenum radiation, there were no measurable anomalous differences, as a consequence of which it was admissible to merge Friedel pairs of reflections. All hydrogen atoms were found in difference density syntheses. Hydrogen atoms were placed geometrically after each cycle. Hydrogen atoms were placed geometrically after each cycle, the preferred orientations of those groups whose conformations could not be assigned unambiguously having been previously identified by examination of a difference Fourier map. Hydrogen atoms were seen in a difference density synthesis. Those attached to carbon atoms were repositioned geometrically. Hydrogen were initially refined with soft restraints on the bonds to regularise their geometry (bond lengths to accepted values, angles either set by symmetry or to accepted values, and U[iso] dependent upon the adjacent bonded atom), after which they were refined with riding constraints only. donated by Bill Clegg: The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93-98, O---N in the range 0.86-0.89 and O---H = 0.82 \%A) and isotropic adps (U(H) in the range 1.2-1.5 times U~equiv~ of the adjacent atom), after which they were refined with riding constraints. . ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin D.J. (1994). Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens C1 C 0.6827(7) 0.2124(4) 0.8822(5) 0.0349 1.0000 Uani . . . . . . C2 C 0.7385(7) 0.3232(4) 0.8667(4) 0.0261 1.0000 Uani . . . . . . C3 C 0.8439(6) 0.3740(4) 0.9405(4) 0.0283 1.0000 Uani . . . . . . C4 C 0.9056(7) 0.3233(4) 1.0399(5) 0.0308 1.0000 Uani . . . . . . C5 C 0.8494(8) 0.2141(5) 1.0554(5) 0.0396 1.0000 Uani . . . . . . C6 C 0.7422(7) 0.1638(4) 0.9819(5) 0.0358 1.0000 Uani . . . . . . C7 C 0.7137(8) 0.4650(4) 0.7492(5) 0.0471 1.0000 Uani . . . . . . C8 C 0.1705(7) 0.2104(4) 0.8913(4) 0.0265 1.0000 Uani . . . . . . C9 C 0.2356(6) 0.1659(5) 0.9865(5) 0.0366 1.0000 Uani . . . . . . C10 C 0.3556(7) 0.2169(4) 1.0582(5) 0.0318 1.0000 Uani . . . . . . C11 C 0.4094(7) 0.3158(4) 1.0346(5) 0.0292 1.0000 Uani . . . . . . C12 C 0.3471(7) 0.3638(4) 0.9406(5) 0.0308 1.0000 Uani . . . . . . C13 C 0.2271(6) 0.3097(4) 0.8694(4) 0.0252 1.0000 Uani . . . . . . C14 C 0.2102(7) 0.4527(4) 0.7488(4) 0.0312 1.0000 Uani . . . . . . O1 O 0.5887(5) 0.1643(3) 0.8138(3) 0.0454 1.0000 Uani . . . . . . O2 O 0.6694(4) 0.3585(3) 0.7723(3) 0.0356 1.0000 Uani . . . . . . O3 O 1.0017(5) 0.3691(3) 1.1090(3) 0.0420 1.0000 Uani . . . . . . O4 O 0.0499(5) 0.1561(3) 0.8247(3) 0.0399 1.0000 Uani . . . . . . O5 O 0.1548(4) 0.3495(3) 0.7749(3) 0.0357 1.0000 Uani . . . . . . O6 O 0.5291(5) 0.3726(3) 1.1016(3) 0.0444 1.0000 Uani . . . . . . H4 H 0.0412 0.1787 0.7516 0.055(3) 1.0000 Uiso . . . . . . H6 H 0.5796 0.3420 1.1614 0.055(3) 1.0000 Uiso . . . . . . H31 H 0.8811 0.4470 0.9281 0.055(3) 1.0000 Uiso . . . . . . H51 H 0.8922 0.1776 1.1216 0.055(3) 1.0000 Uiso . . . . . . H61 H 0.7021 0.0917 0.9955 0.055(3) 1.0000 Uiso . . . . . . H71 H 0.6564 0.4834 0.6782 0.055(3) 1.0000 Uiso . . . . . . H72 H 0.6730 0.5137 0.7996 0.055(3) 1.0000 Uiso . . . . . . H73 H 0.8417 0.4711 0.7537 0.055(3) 1.0000 Uiso . . . . . . H91 H 0.1945 0.0949 1.0034 0.055(3) 1.0000 Uiso . . . . . . H101 H 0.4021 0.1833 1.1255 0.055(3) 1.0000 Uiso . . . . . . H121 H 0.3876 0.4352 0.9245 0.055(3) 1.0000 Uiso . . . . . . H141 H 0.1492 0.4725 0.6790 0.055(3) 1.0000 Uiso . . . . . . H142 H 0.3377 0.4523 0.7489 0.055(3) 1.0000 Uiso . . . . . . H143 H 0.1817 0.5043 0.8005 0.055(3) 1.0000 Uiso . . . . . . 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 C1 0.028(3) 0.043(3) 0.032(3) -0.013(3) -0.002(3) -0.003(2) C2 0.031(2) 0.024(3) 0.024(3) 0.004(2) 0.007(2) 0.000(2) C3 0.031(2) 0.034(3) 0.016(3) -0.003(2) -0.008(2) -0.005(2) C4 0.029(3) 0.033(3) 0.031(3) -0.003(3) 0.007(3) -0.004(2) C5 0.039(3) 0.043(4) 0.036(4) 0.005(3) 0.002(3) 0.002(3) C6 0.043(3) 0.022(3) 0.041(4) 0.002(3) 0.003(3) -0.002(3) C7 0.051(3) 0.039(4) 0.050(5) 0.008(3) 0.004(3) 0.002(3) C8 0.029(3) 0.017(2) 0.034(3) 0.000(2) 0.006(3) -0.002(2) C9 0.037(3) 0.035(4) 0.037(4) 0.004(3) 0.002(3) -0.004(3) C10 0.036(3) 0.031(3) 0.024(3) 0.010(3) -0.008(3) 0.002(2) C11 0.030(3) 0.036(3) 0.019(3) -0.006(2) -0.005(2) 0.005(2) C12 0.031(3) 0.024(3) 0.040(4) -0.003(2) 0.013(3) -0.003(2) C13 0.024(2) 0.028(3) 0.022(3) -0.005(2) -0.003(2) -0.001(2) C14 0.039(3) 0.030(3) 0.024(3) 0.005(2) 0.003(2) 0.001(2) O1 0.059(2) 0.032(2) 0.041(2) -0.0080(17) -0.0047(19) -0.0111(18) O2 0.039(2) 0.040(2) 0.024(2) 0.0027(19) -0.0044(17) -0.0061(18) O3 0.047(2) 0.043(2) 0.030(2) -0.0073(19) -0.0103(18) -0.0077(18) O4 0.0484(19) 0.037(2) 0.030(2) -0.0049(16) -0.0054(16) -0.0182(17) O5 0.041(2) 0.034(2) 0.029(2) 0.0013(18) -0.0046(18) -0.0023(17) O6 0.048(2) 0.054(3) 0.026(2) -0.0003(19) -0.0084(18) -0.0070(19) _refine_ls_extinction_coef 90 _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.507(8) yes C1 . C6 . 1.461(9) yes C1 . O1 . 1.234(7) yes C2 . C3 . 1.341(7) yes C2 . O2 . 1.353(7) yes C3 . C4 . 1.472(8) yes C3 . H31 . 1.000 no C4 . C5 . 1.488(8) yes C4 . O3 . 1.234(7) yes C5 . C6 . 1.342(9) yes C5 . H51 . 1.000 no C6 . H61 . 1.000 no C7 . O2 . 1.450(6) yes C7 . H71 . 1.000 no C7 . H72 . 1.000 no C7 . H73 . 0.999 no C8 . C9 . 1.399(8) yes C8 . C13 . 1.392(7) yes C8 . O4 . 1.372(7) yes C9 . C10 . 1.386(9) yes C9 . H91 . 1.000 no C10 . C11 . 1.385(8) yes C10 . H101 . 1.000 no C11 . C12 . 1.399(8) yes C11 . O6 . 1.387(7) yes C12 . C13 . 1.401(8) yes C12 . H121 . 1.001 no C13 . O5 . 1.380(6) yes C14 . O5 . 1.449(6) yes C14 . H141 . 1.000 no C14 . H142 . 1.000 no C14 . H143 . 1.000 no O4 . H4 . 0.998 no O6 . H6 . 0.912 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . C6 . 117.7(5) yes C2 . C1 . O1 . 121.4(6) yes C6 . C1 . O1 . 120.9(6) yes C1 . C2 . C3 . 121.0(6) yes C1 . C2 . O2 . 110.9(5) yes C3 . C2 . O2 . 128.1(5) yes C2 . C3 . C4 . 120.7(5) yes C2 . C3 . H31 . 119.7 no C4 . C3 . H31 . 119.6 no C3 . C4 . C5 . 118.2(6) yes C3 . C4 . O3 . 121.6(5) yes C5 . C4 . O3 . 120.2(6) yes C4 . C5 . C6 . 121.1(6) yes C4 . C5 . H51 . 119.6 no C6 . C5 . H51 . 119.4 no C1 . C6 . C5 . 121.3(5) yes C1 . C6 . H61 . 119.3 no C5 . C6 . H61 . 119.4 no O2 . C7 . H71 . 109.3 no O2 . C7 . H72 . 109.4 no H71 . C7 . H72 . 109.5 no O2 . C7 . H73 . 109.5 no H71 . C7 . H73 . 109.6 no H72 . C7 . H73 . 109.6 no C9 . C8 . C13 . 118.4(5) yes C9 . C8 . O4 . 119.0(5) yes C13 . C8 . O4 . 122.6(5) yes C8 . C9 . C10 . 122.1(5) yes C8 . C9 . H91 . 119.0 no C10 . C9 . H91 . 118.9 no C9 . C10 . C11 . 118.3(5) yes C9 . C10 . H101 . 120.9 no C11 . C10 . H101 . 120.7 no C10 . C11 . C12 . 121.6(5) yes C10 . C11 . O6 . 122.3(5) yes C12 . C11 . O6 . 116.1(5) yes C11 . C12 . C13 . 118.7(5) yes C11 . C12 . H121 . 120.7 no C13 . C12 . H121 . 120.6 no C12 . C13 . C8 . 120.9(6) yes C12 . C13 . O5 . 124.0(5) yes C8 . C13 . O5 . 115.1(5) yes O5 . C14 . H141 . 109.4 no O5 . C14 . H142 . 109.5 no H141 . C14 . H142 . 109.5 no O5 . C14 . H143 . 109.4 no H141 . C14 . H143 . 109.5 no H142 . C14 . H143 . 109.5 no C7 . O2 . C2 . 115.7(4) yes C8 . O4 . H4 . 113.9 no C14 . O5 . C13 . 117.0(4) yes C11 . O6 . H6 . 118.8 no # Attachment 'MB-cif2.doc' data_2 _database_code_depnum_ccdc_archive 'CCDC 626643' _audit_creation_date 06-10-23 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title '10230942 Compound X' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 4.9678(7) _cell_length_b 10.533(4) _cell_length_c 13.094(2) _cell_angle_alpha 90 _cell_angle_beta 91.194(13) _cell_angle_gamma 90 _cell_volume 685.0(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C7 H8 O3 # Dc = 1.36 Fooo = 296.00 Mu = 1.07 M = 140.14 # Found Formula = C7 H8 O3 # Dc = 1.36 FOOO = 296.00 Mu = 1.07 M = 140.14 _chemical_formula_sum 'C7 H8 O3' _chemical_formula_moiety 'C7 H8 O3' _chemical_compound_source ? _chemical_formula_weight 140.14 _cell_measurement_reflns_used 35 _cell_measurement_theta_min 3 _cell_measurement_theta_max 22 _cell_measurement_temperature 295 _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_min 0.06 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.12 _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.107 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 0.99 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 295 _diffrn_reflns_number 3578 _reflns_number_total 1564 _diffrn_reflns_av_R_equivalents 0.039 # Number of reflections with Friedels Law is 1564 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1574 _diffrn_reflns_theta_min 3.665 _diffrn_reflns_theta_max 27.505 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.679 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -6 _reflns_limit_h_max 6 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 16 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.28 _refine_diff_density_max 0.25 _refine_ls_number_reflns 978 _refine_ls_number_restraints 0 _refine_ls_number_parameters 93 #_refine_ls_R_factor_ref 0.0473 _refine_ls_wR_factor_ref 0.0595 _refine_ls_goodness_of_fit_ref 1.0549 #_reflns_number_all 1564 _refine_ls_R_factor_all 0.0706 _refine_ls_wR_factor_all 0.0756 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.0\s(I) _reflns_number_gt 978 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_gt 0.0595 _refine_ls_shift/su_max 0.000562 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment refu _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.71 0.783 1.20 ; _publ_section_abstract # Text of the abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fih. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens C1 C 0.5213(3) 0.18888(18) 0.83841(13) 0.0330 1.0000 Uani . . . . . . C2 C 0.5188(4) 0.2276(2) 0.94060(14) 0.0377 1.0000 Uani . . . . . . C3 C 0.3345(4) 0.3187(2) 0.97086(13) 0.0382 1.0000 Uani . . . . . . C4 C 0.1492(4) 0.3708(2) 0.90171(15) 0.0416 1.0000 Uani . . . . . . C5 C 0.1543(4) 0.3324(2) 0.79941(14) 0.0390 1.0000 Uani . . . . . . C6 C 0.3379(4) 0.24378(18) 0.76718(13) 0.0345 1.0000 Uani . . . . . . C7 C 0.8640(4) 0.0317(2) 0.86903(18) 0.0522 1.0000 Uani . . . . . . O1 O 0.6905(3) 0.09955(14) 0.79896(10) 0.0452 1.0000 Uani . . . . . . O2 O 0.3245(3) 0.35967(17) 1.07213(10) 0.0538 1.0000 Uani . . . . . . O3 O 0.3345(3) 0.20655(16) 0.66538(10) 0.0488 1.0000 Uani . . . . . . H2 H 0.6600 0.1863 0.9861 0.069(3) 1.0000 Uiso . . . . . . H4 H 0.0006 0.4228 0.9289 0.069(3) 1.0000 Uiso . . . . . . H5 H 0.0225 0.3678 0.7527 0.069(3) 1.0000 Uiso . . . . . . H6 H 0.4944 0.3434 1.1011 0.069(3) 1.0000 Uiso . . . . . . H7 H 0.4988 0.1794 0.6509 0.069(3) 1.0000 Uiso . . . . . . H72 H 0.9869 0.0913 0.9045 0.069(3) 1.0000 Uiso . . . . . . H73 H 0.9700 -0.0300 0.8277 0.069(3) 1.0000 Uiso . . . . . . H71 H 0.7513 -0.0137 0.9214 0.069(3) 1.0000 Uiso . . . . . . 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 C1 0.0259(8) 0.0415(10) 0.0314(8) 0.0017(7) -0.0018(6) -0.0010(7) C2 0.0301(9) 0.0527(11) 0.0300(9) 0.0036(7) -0.0062(7) 0.0007(7) C3 0.0333(9) 0.0540(11) 0.0273(8) -0.0018(8) 0.0006(6) -0.0038(8) C4 0.0365(10) 0.0493(12) 0.0390(10) -0.0013(8) 0.0014(7) 0.0047(8) C5 0.0350(10) 0.0475(11) 0.0341(9) 0.0046(8) -0.0072(7) 0.0045(8) C6 0.0331(9) 0.0446(10) 0.0256(8) 0.0013(7) -0.0037(7) -0.0042(7) C7 0.0433(11) 0.0530(12) 0.0600(13) 0.0026(11) -0.0062(9) 0.0121(10) O1 0.0421(8) 0.0565(9) 0.0367(7) -0.0058(6) -0.0056(5) 0.0117(6) O2 0.0452(8) 0.0865(13) 0.0295(7) -0.0133(7) -0.0013(5) 0.0049(7) O3 0.0443(8) 0.0763(11) 0.0256(7) -0.0058(7) -0.0074(5) 0.0080(7) _refine_ls_extinction_coef 110 _refine_ls_extinction_method 'Larson (1970), Equation 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.399(3) yes C1 . C6 . 1.414(2) yes C1 . O1 . 1.370(2) yes C2 . C3 . 1.390(3) yes C2 . H2 . 1.010 no C3 . C4 . 1.391(3) yes C3 . O2 . 1.396(2) yes C4 . C5 . 1.400(3) yes C4 . H4 . 0.991 no C5 . C6 . 1.377(3) yes C5 . H5 . 0.962 no C6 . O3 . 1.389(2) yes C7 . O1 . 1.436(2) yes C7 . H72 . 0.985 no C7 . H73 . 1.002 no C7 . H71 . 1.014 no O2 . H6 . 0.934 no O3 . H7 . 0.889 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . C6 . 119.56(17) yes C2 . C1 . O1 . 125.34(15) yes C6 . C1 . O1 . 115.10(15) yes C1 . C2 . C3 . 119.53(16) yes C1 . C2 . H2 . 114.8 no C3 . C2 . H2 . 125.7 no C2 . C3 . C4 . 121.20(17) yes C2 . C3 . O2 . 121.39(17) yes C4 . C3 . O2 . 117.40(18) yes C3 . C4 . C5 . 118.94(17) yes C3 . C4 . H4 . 118.2 no C5 . C4 . H4 . 122.1 no C4 . C5 . C6 . 120.96(16) yes C4 . C5 . H5 . 118.0 no C6 . C5 . H5 . 121.0 no C1 . C6 . C5 . 119.78(16) yes C1 . C6 . O3 . 120.82(17) yes C5 . C6 . O3 . 119.37(16) yes O1 . C7 . H72 . 110.0 no O1 . C7 . H73 . 107.0 no H72 . C7 . H73 . 109.9 no O1 . C7 . H71 . 109.5 no H72 . C7 . H71 . 109.1 no H73 . C7 . H71 . 111.2 no C7 . O1 . C1 . 117.75(14) yes C3 . O2 . H6 . 106.2 no C6 . O3 . H7 . 107.6 no