data_2100368 _journal_coeditor_code DE5020 _journal_date_accepted 2005-11-19 _journal_date_recd_electronic 2005-04-29 _journal_issue 1 _journal_name_full 'Acta Crystallographica, Section B' _journal_page_first 109 _journal_page_last 117 _journal_paper_category FA _journal_volume 62 _journal_year 2006 _chemical_formula_moiety 'C7 H3 Cl2 N O, 0.25(C8 H10)' _chemical_formula_sum 'C9 H5.5 Cl2 N O' _chemical_formula_weight 214.55 _chemical_melting_point ? _chemical_name_common ? _chemical_name_systematic ; 3,5-dichloro-4-hydroxybenzonitrile / 1/4 p-xylene ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXTL _cell_angle_alpha 90.00 _cell_angle_beta 98.000(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.5522(11) _cell_length_b 15.067(4) _cell_length_c 13.636(3) _cell_measurement_reflns_used 3547 _cell_measurement_temperature 174(2) _cell_measurement_theta_max 27.20 _cell_measurement_theta_min 2.70 _cell_volume 926.2(4) _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_collection 'SMART (Bruker, 2002)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 174(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type ; Siemens area detector diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.054 _diffrn_reflns_av_sigmaI/netI 0.041 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 8934 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.03 _diffrn_standards_decay_% 'less than 1' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.654 _exptl_absorpt_correction_T_max 0.94 _exptl_absorpt_correction_T_min 0.88 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS; Sheldrick, 1996; Blessing, 1995' ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.539 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 434 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.22 _refine_diff_density_min -0.19 _refine_ls_extinction_coef 0.0043(16) _refine_ls_extinction_expression ; Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ ; _refine_ls_extinction_method SHELXTL _refine_ls_goodness_of_fit_ref 1.22 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 151 _refine_ls_number_reflns 1636 _refine_ls_number_restraints 67 _refine_ls_restrained_S_all 1.20 _refine_ls_R_factor_all 0.070 _refine_ls_R_factor_gt 0.048 _refine_ls_shift/su_max 0.023 _refine_ls_shift/su_mean 0.002 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.022P)^2^+0.43P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.075 _refine_ls_wR_factor_ref 0.079 _reflns_number_gt 1317 _reflns_number_total 1636 _reflns_threshold_expression '>2\s(I) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol 04 1.2136(4) 0.84495(12) 0.74697(13) 0.0351(5) Uani d . 1 . . O H4 1.2799 0.8003 0.7797 0.042 Uiso calc R 1 . . H C4 0.9847(5) 0.82074(17) 0.67956(18) 0.0249(6) Uani d . 1 . . C Cl3 1.04842(16) 0.65090(4) 0.74032(5) 0.0376(2) Uani d . 1 . . Cl C3 0.8767(5) 0.73432(17) 0.66611(18) 0.0245(6) Uani d . 1 . . C C2 0.6421(6) 0.71394(17) 0.59419(18) 0.0276(6) Uani d . 1 . . C H2 0.5706 0.6548 0.5865 0.033 Uiso calc R 1 . . H C1 0.5117(5) 0.78098(17) 0.53313(18) 0.0257(6) Uani d . 1 . . C N7 0.0819(5) 0.74320(16) 0.39527(18) 0.0423(6) Uani d . 1 . . N C6 0.6128(6) 0.86740(17) 0.54498(19) 0.0277(6) Uani d . 1 . . C H6 0.5228 0.9131 0.5031 0.033 Uiso calc R 1 . . H Cl5 0.96867(17) 0.99512(5) 0.63438(6) 0.0432(3) Uani d . 1 . . Cl C5 0.8453(6) 0.88677(17) 0.61796(18) 0.0260(6) Uani d . 1 . . C C7 0.2710(6) 0.76007(18) 0.4564(2) 0.0307(7) Uani d . 1 . . C C11 0.176(3) 0.508(2) 0.4806(19) 0.0328(17) Uani d PDU 0.25 A -1 C C12 0.357(3) 0.528(2) 0.4094(19) 0.0324(16) Uani d PDU 0.25 A -1 C H12A 0.2690 0.5491 0.3462 0.039 Uiso calc PR 0.25 A -1 H C13 0.663(3) 0.520(2) 0.4292(19) 0.0325(17) Uani d PDU 0.25 A -1 C H13A 0.7814 0.5346 0.3794 0.039 Uiso calc PR 0.25 A -1 H C14 0.800(3) 0.490(2) 0.5209(19) 0.0328(17) Uani d PDU 0.25 A -1 C C15 0.619(3) 0.469(2) 0.5921(19) 0.0324(16) Uani d PDU 0.25 A -1 C H15A 0.7072 0.4477 0.6551 0.039 Uiso calc PR 0.25 A -1 H C16 0.313(3) 0.478(2) 0.5724(19) 0.0325(17) Uani d PDU 0.25 A -1 C H16A 0.1950 0.4634 0.6224 0.039 Uiso calc PR 0.25 A -1 H C17 -0.156(4) 0.517(3) 0.460(6) 0.046(3) Uani d PDU 0.25 A -1 C H17A -0.2069 0.5760 0.4338 0.069 Uiso calc PR 0.25 A -1 H H17B -0.2404 0.5077 0.5215 0.069 Uiso calc PR 0.25 A -1 H H17C -0.2354 0.4719 0.4112 0.069 Uiso calc PR 0.25 A -1 H C18 1.132(4) 0.480(3) 0.543(6) 0.046(3) Uani d PDU 0.25 A -1 C H18A 1.2013 0.5051 0.6081 0.069 Uiso calc PR 0.25 A -1 H H18B 1.2237 0.5126 0.4923 0.069 Uiso calc PR 0.25 A -1 H H18C 1.1858 0.4175 0.5412 0.069 Uiso calc PR 0.25 A -1 H 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 04 0.0359(11) 0.0308(11) 0.0326(11) 0.0019(9) -0.0170(9) -0.0008(9) C4 0.0239(15) 0.0279(15) 0.0213(14) 0.0023(11) -0.0028(12) -0.0033(11) Cl3 0.0454(5) 0.0297(4) 0.0346(4) 0.0070(3) -0.0050(3) 0.0058(3) C3 0.0244(15) 0.0267(15) 0.0220(14) 0.0050(12) 0.0017(12) 0.0025(11) C2 0.0278(15) 0.0260(15) 0.0288(15) -0.0025(12) 0.0035(12) -0.0067(12) C1 0.0204(14) 0.0328(16) 0.0229(14) -0.0006(12) -0.0011(11) -0.0039(12) N7 0.0375(15) 0.0475(16) 0.0375(14) -0.0058(12) -0.0097(13) -0.0027(12) C6 0.0263(15) 0.0290(15) 0.0263(15) 0.0038(12) -0.0016(12) 0.0031(12) Cl5 0.0510(5) 0.0253(4) 0.0469(5) -0.0051(4) -0.0162(4) -0.0002(3) C5 0.0271(15) 0.0244(14) 0.0251(15) -0.0012(11) -0.0010(12) -0.0012(11) C7 0.0302(17) 0.0318(16) 0.0290(15) -0.0010(13) 0.0003(14) -0.0007(13) C11 0.038(4) 0.021(3) 0.041(4) 0.001(3) 0.009(3) -0.003(3) C12 0.043(4) 0.027(3) 0.027(3) -0.001(3) 0.005(3) 0.001(2) C13 0.048(5) 0.022(3) 0.031(4) -0.003(4) 0.017(3) -0.003(3) C14 0.038(4) 0.021(3) 0.041(4) 0.001(3) 0.009(3) -0.003(3) C15 0.043(4) 0.027(3) 0.027(3) -0.001(3) 0.005(3) 0.001(2) C16 0.048(5) 0.022(3) 0.031(4) -0.003(4) 0.017(3) -0.003(3) C17 0.043(5) 0.044(5) 0.051(5) 0.001(5) 0.006(6) -0.007(5) C18 0.043(5) 0.044(5) 0.051(5) 0.001(5) 0.006(6) -0.007(5) 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C4 04 H4 . . 109.5 ? 04 C4 C3 . . 124.8(2) ? 04 C4 C5 . . 117.6(2) ? C3 C4 C5 . . 117.6(2) ? C2 C3 C4 . . 121.6(2) ? C2 C3 Cl3 . . 119.7(2) ? C4 C3 Cl3 . . 118.61(19) ? C3 C2 C1 . . 119.2(2) ? C3 C2 H2 . . 120.4 ? C1 C2 H2 . . 120.4 ? C6 C1 C2 . . 120.5(2) ? C6 C1 C7 . . 119.9(2) ? C2 C1 C7 . . 119.7(2) ? C5 C6 C1 . . 119.5(2) ? C5 C6 H6 . . 120.2 ? C1 C6 H6 . . 120.2 ? C6 C5 C4 . . 121.5(2) ? C6 C5 Cl5 . . 119.7(2) ? C4 C5 Cl5 . . 118.82(19) ? N7 C7 C1 . . 179.5(3) ? C12 C11 C16 . . 117.77(13) ? C12 C11 C17 . . 122(4) ? C16 C11 C17 . . 121(4) ? C13 C12 C11 . . 121.12(13) ? C13 C12 H12A . . 119.4 ? C11 C12 H12A . . 119.4 ? C12 C13 C14 . . 121.10(13) ? C12 C13 H13A . . 119.4 ? C14 C13 H13A . . 119.4 ? C15 C14 C13 . . 117.77(13) ? C15 C14 C18 . . 121(4) ? C13 C14 C18 . . 121(4) ? C16 C15 C14 . . 121.12(13) ? C16 C15 H15A . . 119.4 ? C14 C15 H15A . . 119.4 ? C15 C16 C11 . . 121.10(13) ? C15 C16 H16A . . 119.5 ? C11 C16 H16A . . 119.5 ? 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 04 C4 . 1.341(3) ? 04 H4 . 0.8400 ? C4 C3 . 1.395(4) ? C4 C5 . 1.396(3) ? Cl3 C3 . 1.730(2) ? C3 C2 . 1.380(3) ? C2 C1 . 1.388(3) ? C2 H2 . 0.9500 ? C1 C6 . 1.383(4) ? C1 C7 . 1.441(4) ? N7 C7 . 1.140(3) ? C6 C5 . 1.379(3) ? C6 H6 . 0.9500 ? Cl5 C5 . 1.731(3) ? C11 C12 . 1.3929(10) ? C11 C16 . 1.3930(10) ? C11 C17 . 1.5032(11) ? C12 C13 . 1.3899(10) ? C12 H12A . 0.9500 ? C13 C14 . 1.3930(10) ? C13 H13A . 0.9500 ? C14 C15 . 1.3929(10) ? C14 C18 . 1.5032(12) ? C15 C16 . 1.3899(10) ? C15 H15A . 0.9500 ? C16 H16A . 0.9500 ? C17 H17A . 0.9800 ? C17 H17B . 0.9800 ? C17 H17C . 0.9800 ? C18 H18A . 0.9800 ? C18 H18B . 0.9800 ? C18 H18C . 0.9800 ?