############################################################################## # # # This CIF contains the data in a paper accepted for publication in # # Acta Crystallographica Section E. It conforms to the requirements of # # Notes for Authors for Acta Crystallographica Section E, and has been # # peer reviewed under the auspices of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary is obtainable from # # ftp://ftp.iucr.org/pub/cif_core.dic. # # # # Software is freely available for graphical display of the structure(s) # # in this CIF. For information consult the CIF software page # # http://www.iucr.org/resources/cif/software. # # # # This file may be used for bona fide research purposes within the # # scientific community so long as proper attribution is given to the journal # # article from which it was obtained. # # # ############################################################################## data_global _audit_creation_method 'form.cif (version 2.0)' _journal_data_validation_number ? _journal_date_recd_electronic 2013-07-21 _journal_date_accepted 2013-07-29 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2013 _journal_volume 69 _journal_issue 9 _journal_page_first o1440 _journal_page_last o1440 _journal_paper_category QO _journal_paper_doi 10.1107/S1600536813021120 _journal_coeditor_code RZ5082 _publ_contact_author_name 'Yousuf, S.' _publ_contact_author_address ; H.E.J. Research Institute of Chemistry, International Cenetr for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan ; _publ_contact_author_email 'dr.sammer.yousuf@gmail.com' _publ_contact_author_fax '+92-21 34819018-9' _publ_contact_author_phone '+92-21 34824924' _publ_section_title ; 2,6-Difluoro-N-(prop-2-ynyl)benzamide ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Zahid Hussain' ? ; H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan ; 'Ejaz Hussain' ? ; H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan ; 'Hina Siddiqui' ? ; H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan ; 'M. Iqbal Choudhary' ? ; H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan Department of Biochemistry, Faculty of Science, King Abdulaziz University, Jaddhah Saudi Arabia ; 'Sammer Yousuf' ? ; H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan ; data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-Difluoro-N-(prop-2-ynyl)benzamide ; _chemical_name_common ? _chemical_formula_moiety 'C10 H7 F2 N O' _chemical_formula_sum 'C10 H7 F2 N O' _chemical_formula_iupac 'C10 H7 F2 N O' _chemical_formula_weight 195.17 _chemical_melting_point ? _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.0479(8) _cell_length_b 19.738(3) _cell_length_c 9.2428(15) _cell_angle_alpha 90.00 _cell_angle_beta 91.432(4) _cell_angle_gamma 90.00 _cell_volume 920.6(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1280 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 22.93 _cell_measurement_temperature 273(2) _exptl_crystal_description 'block' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5388 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0210 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.50 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_max 0.977 _diffrn_measured_fraction_theta_full 0.977 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^ > \s(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. ; _reflns_number_total 1669 _reflns_number_gt 1283 _reflns_threshold_expression I>2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0547 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_gt 0.0895 _refine_ls_wR_factor_ref 0.0994 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_number_reflns 1669 _refine_ls_number_parameters 135 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0397P)^2^+0.1720P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.132 _refine_diff_density_min -0.154 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 '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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_disorder_assembly _atom_site_disorder_group F F1 0.4706(2) 0.66642(6) 0.01184(13) 0.0784(4) Uani d . 1 1 . . F F2 1.1590(2) 0.68247(6) -0.31627(13) 0.0808(4) Uani d . 1 1 . . O O1 1.0617(2) 0.56728(6) -0.15774(16) 0.0689(4) Uani d . 1 1 . . N N1 0.6219(3) 0.55850(7) -0.17077(17) 0.0520(4) Uani d . 1 1 . . C C1 0.6337(3) 0.70378(9) -0.06950(19) 0.0533(5) Uani d . 1 1 . . C C2 0.6133(4) 0.77291(10) -0.0635(2) 0.0670(6) Uani d . 1 1 . . H H2A 0.4884 0.7934 -0.0055 0.080 Uiso calc R 1 1 . . C C3 0.7807(4) 0.81150(10) -0.1445(2) 0.0690(6) Uani d . 1 1 . . H H3A 0.7685 0.8585 -0.1419 0.083 Uiso calc R 1 1 . . C C4 0.9655(4) 0.78117(10) -0.2290(2) 0.0664(5) Uani d . 1 1 . . H H4A 1.0802 0.8071 -0.2835 0.080 Uiso calc R 1 1 . . C C5 0.9778(3) 0.71209(9) -0.2314(2) 0.0546(5) Uani d . 1 1 . . C C6 0.8147(3) 0.66992(8) -0.15372(17) 0.0453(4) Uani d . 1 1 . . C C7 0.8430(3) 0.59431(9) -0.16021(17) 0.0475(4) Uani d . 1 1 . . C C8 0.6276(4) 0.48497(9) -0.1809(2) 0.0607(5) Uani d . 1 1 . . H H8A 0.4535 0.4673 -0.1599 0.073 Uiso calc R 1 1 . . H H8B 0.7519 0.4674 -0.1085 0.073 Uiso calc R 1 1 . . C C9 0.7041(4) 0.46128(9) -0.3233(2) 0.0621(5) Uani d . 1 1 . . C C10 0.7642(5) 0.44382(12) -0.4380(3) 0.0880(7) Uani d . 1 1 . . H H1 0.475(4) 0.5775(9) -0.1715(19) 0.061(6) Uiso d . 1 1 . . H H2 0.817(5) 0.4327(13) -0.524(3) 0.120(10) Uiso d . 1 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F1 0.0691(7) 0.0792(8) 0.0889(9) -0.0091(6) 0.0395(6) -0.0161(6) F2 0.0727(7) 0.0810(8) 0.0907(9) -0.0041(6) 0.0418(7) -0.0052(6) O1 0.0315(6) 0.0655(8) 0.1096(11) 0.0057(5) 0.0013(6) -0.0028(7) N1 0.0316(7) 0.0521(9) 0.0726(11) 0.0022(6) 0.0071(7) -0.0047(7) C1 0.0412(9) 0.0628(11) 0.0559(11) -0.0019(8) 0.0054(8) -0.0104(9) C2 0.0543(10) 0.0674(13) 0.0794(14) 0.0088(9) 0.0033(10) -0.0230(10) C3 0.0648(12) 0.0532(11) 0.0885(16) 0.0037(9) -0.0073(11) -0.0048(10) C4 0.0604(11) 0.0634(12) 0.0753(14) -0.0065(9) 0.0039(10) 0.0069(10) C5 0.0432(9) 0.0629(11) 0.0579(11) -0.0003(8) 0.0070(8) -0.0048(9) C6 0.0320(8) 0.0553(10) 0.0484(10) 0.0000(7) -0.0021(7) -0.0053(8) C7 0.0328(8) 0.0571(10) 0.0527(10) 0.0014(7) 0.0052(7) -0.0023(8) C8 0.0503(10) 0.0529(11) 0.0794(14) -0.0025(8) 0.0094(9) 0.0042(9) C9 0.0579(11) 0.0451(10) 0.0835(16) 0.0055(8) 0.0048(11) -0.0031(10) C10 0.1032(19) 0.0689(15) 0.092(2) 0.0121(12) 0.0132(16) -0.0128(14) _geom_special_details ; All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag F1 C1 . 1.3482(19) ? F2 C5 . 1.3530(18) ? O1 C7 . 1.2256(17) ? N1 C7 . 1.323(2) ? N1 C8 . 1.455(2) ? N1 H1 . 0.830(19) ? C1 C2 . 1.370(3) ? C1 C6 . 1.387(2) ? C2 C3 . 1.374(3) ? C2 H2A . 0.9300 ? C3 C4 . 1.369(3) ? C3 H3A . 0.9300 ? C4 C5 . 1.365(3) ? C4 H4A . 0.9300 ? C5 C6 . 1.384(2) ? C6 C7 . 1.501(2) ? C8 C9 . 1.458(3) ? C8 H8A . 0.9700 ? C8 H8B . 0.9700 ? C9 C10 . 1.162(3) ? C10 H2 . 0.87(3) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C7 N1 C8 . . 121.31(15) ? C7 N1 H1 . . 120.7(13) ? C8 N1 H1 . . 118.0(13) ? F1 C1 C2 . . 118.34(15) ? F1 C1 C6 . . 118.01(16) ? C2 C1 C6 . . 123.65(17) ? C1 C2 C3 . . 118.85(17) ? C1 C2 H2A . . 120.6 ? C3 C2 H2A . . 120.6 ? C4 C3 C2 . . 120.37(18) ? C4 C3 H3A . . 119.8 ? C2 C3 H3A . . 119.8 ? C5 C4 C3 . . 118.53(18) ? C5 C4 H4A . . 120.7 ? C3 C4 H4A . . 120.7 ? F2 C5 C4 . . 118.19(16) ? F2 C5 C6 . . 117.42(16) ? C4 C5 C6 . . 124.38(16) ? C5 C6 C1 . . 114.22(16) ? C5 C6 C7 . . 121.27(14) ? C1 C6 C7 . . 124.49(15) ? O1 C7 N1 . . 121.78(16) ? O1 C7 C6 . . 121.24(14) ? N1 C7 C6 . . 116.97(13) ? N1 C8 C9 . . 112.60(15) ? N1 C8 H8A . . 109.1 ? C9 C8 H8A . . 109.1 ? N1 C8 H8B . . 109.1 ? C9 C8 H8B . . 109.1 ? H8A C8 H8B . . 107.8 ? C10 C9 C8 . . 178.5(2) ? C9 C10 H2 . . 176.4(19) ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag F1 C1 C2 C3 . . . . 179.19(17) ? C6 C1 C2 C3 . . . . -0.2(3) ? C1 C2 C3 C4 . . . . -0.4(3) ? C2 C3 C4 C5 . . . . 0.4(3) ? C3 C4 C5 F2 . . . . 179.33(17) ? C3 C4 C5 C6 . . . . 0.1(3) ? F2 C5 C6 C1 . . . . -179.83(15) ? C4 C5 C6 C1 . . . . -0.6(3) ? F2 C5 C6 C7 . . . . 1.7(2) ? C4 C5 C6 C7 . . . . -179.07(18) ? F1 C1 C6 C5 . . . . -178.74(15) ? C2 C1 C6 C5 . . . . 0.6(3) ? F1 C1 C6 C7 . . . . -0.3(2) ? C2 C1 C6 C7 . . . . 179.05(18) ? C8 N1 C7 O1 . . . . -0.4(3) ? C8 N1 C7 C6 . . . . 178.68(15) ? C5 C6 C7 O1 . . . . 41.8(2) ? C1 C6 C7 O1 . . . . -136.53(18) ? C5 C6 C7 N1 . . . . -137.26(17) ? C1 C6 C7 N1 . . . . 44.4(2) ? C7 N1 C8 C9 . . . . -75.0(2) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 O1 1_455 0.83(2) 2.10(2) 2.8387(19) 147.4(17) yes C2 H2A F2 4_476 0.93 2.49 3.394(2) 164.3 yes _iucr_refine_instructions_details ; TITL a in P2(1)/c CELL 0.71073 5.0479 19.7384 9.2428 90.000 91.432 90.000 ZERR 4.00 0.0008 0.0032 0.0015 0.000 0.004 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O F UNIT 40 28 4 4 8 TEMP 0 ACTA CONF OMIT -3 51 SIZE 0.38 0.17 0.1 EQIV $1 -1+X,3/2-Y,1/2+Z HTAB C2 F2_$1 L.S. 20 BOND $H FMAP 2 1 60 PLAN 10 WGHT 0.039700 0.172000 FVAR 0.70828 F1 5 0.470584 0.666423 0.011839 11.00000 0.06909 0.07917 = 0.08886 -0.01608 0.03948 -0.00913 F2 5 1.159022 0.682466 -0.316273 11.00000 0.07267 0.08101 = 0.09066 -0.00518 0.04179 -0.00415 O1 4 1.061654 0.567281 -0.157740 11.00000 0.03150 0.06547 = 0.10956 -0.00276 0.00133 0.00575 N1 3 0.621861 0.558497 -0.170774 11.00000 0.03159 0.05212 = 0.07258 -0.00470 0.00713 0.00224 C1 1 0.633676 0.703780 -0.069499 11.00000 0.04120 0.06285 = 0.05593 -0.01042 0.00537 -0.00191 C2 1 0.613343 0.772905 -0.063458 11.00000 0.05432 0.06736 = 0.07938 -0.02304 0.00331 0.00885 AFIX 43 H2A 2 0.488356 0.793362 -0.005505 11.00000 -1.20000 AFIX 0 C3 1 0.780742 0.811498 -0.144472 11.00000 0.06483 0.05318 = 0.08845 -0.00481 -0.00730 0.00367 AFIX 43 H3A 2 0.768509 0.858493 -0.141917 11.00000 -1.20000 AFIX 0 C4 1 0.965542 0.781166 -0.228983 11.00000 0.06042 0.06342 = 0.07535 0.00686 0.00388 -0.00650 AFIX 43 H4A 2 1.080177 0.807055 -0.283546 11.00000 -1.20000 AFIX 0 C5 1 0.977776 0.712086 -0.231365 11.00000 0.04325 0.06286 = 0.05785 -0.00485 0.00698 -0.00033 C6 1 0.814744 0.669924 -0.153716 11.00000 0.03199 0.05533 = 0.04841 -0.00532 -0.00211 0.00002 C7 1 0.842993 0.594307 -0.160212 11.00000 0.03283 0.05708 = 0.05269 -0.00229 0.00516 0.00142 C8 1 0.627630 0.484974 -0.180879 11.00000 0.05027 0.05292 = 0.07940 0.00416 0.00944 -0.00252 AFIX 23 H8A 2 0.453507 0.467273 -0.159864 11.00000 -1.20000 H8B 2 0.751851 0.467366 -0.108474 11.00000 -1.20000 AFIX 0 C9 1 0.704053 0.461283 -0.323256 11.00000 0.05793 0.04515 = 0.08345 -0.00306 0.00484 0.00547 C10 1 0.764233 0.443817 -0.437966 11.00000 0.10324 0.06893 = 0.09223 -0.01278 0.01320 0.01212 H1 2 0.475090 0.577498 -0.171547 11.00000 0.06143 H2 2 0.817041 0.432712 -0.524044 11.00000 0.11963 HKLF 4 REM a in P2(1)/c REM R1 = 0.0402 for 1283 Fo > 4sig(Fo) and 0.0547 for all 1669 data REM 135 parameters refined using 0 restraints END WGHT 0.0397 0.1720 REM Highest difference peak 0.132, deepest hole -0.154, 1-sigma level 0.029 Q1 1 0.7976 0.6813 -0.0734 11.00000 0.05 0.13 Q2 1 0.7144 0.7392 -0.0171 11.00000 0.05 0.12 Q3 1 0.6863 0.6831 -0.1587 11.00000 0.05 0.12 Q4 1 0.8018 0.6840 -0.2402 11.00000 0.05 0.11 Q5 1 1.0670 0.5972 -0.2240 11.00000 0.05 0.11 Q6 1 0.9660 0.6788 -0.1386 11.00000 0.05 0.11 Q7 1 1.2189 0.5993 -0.1585 11.00000 0.05 0.11 Q8 1 0.6302 0.6446 0.0628 11.00000 0.05 0.10 Q9 1 0.9095 0.4587 -0.3415 11.00000 0.05 0.09 Q10 1 0.7673 0.4862 -0.3828 11.00000 0.05 0.09 ;