data_2100366
_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'
_chemical_formula_sum          'C7 H3 Cl2 N O'
_chemical_formula_weight       188.00
_chemical_melting_point        ?
_chemical_name_common          Chloroxynil
_chemical_name_systematic
;
 3,5-dichloro-4-hydroxybenzonitrile
;
_symmetry_cell_setting         triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary   direct
_atom_sites_solution_secondary difmap
_audit_creation_method         SHELXTL
_cell_angle_alpha              78.650(10)
_cell_angle_beta               74.390(10)
_cell_angle_gamma              74.230(10)
_cell_formula_units_Z          '4 '
_cell_length_a                 7.3325(18)
_cell_length_b                 8.999(2)
_cell_length_c                 12.221(3)
_cell_measurement_reflns_used  1913
_cell_measurement_temperature  174(2)
_cell_measurement_theta_max    25.90
_cell_measurement_theta_min    2.75
_cell_volume                   740.7(3)
_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 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.070
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_l_max     15
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_number          8796
_diffrn_reflns_theta_full      27.50
_diffrn_reflns_theta_max       27.50
_diffrn_reflns_theta_min       1.75
_diffrn_standards_decay_%      'less than 1'
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number       0
_exptl_absorpt_coefficient_mu  0.805
_exptl_absorpt_correction_T_max 0.92
_exptl_absorpt_correction_T_min 0.80
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
 SADABS;  Sheldrick, 1996;  Blessing, 1995'
;
_exptl_crystal_colour          colorless
_exptl_crystal_density_diffrn  1.686
_exptl_crystal_density_meas    'not measured'
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     plate
_exptl_crystal_F_000           376
_exptl_crystal_size_max        0.40
_exptl_crystal_size_mid        0.25
_exptl_crystal_size_min        0.10
_refine_diff_density_max       0.34
_refine_diff_density_min       -0.28
_refine_ls_extinction_coef     ?
_refine_ls_extinction_method   none
_refine_ls_goodness_of_fit_ref 1.05
_refine_ls_hydrogen_treatment  constr
_refine_ls_matrix_type         full
_refine_ls_number_parameters   199
_refine_ls_number_reflns       3362
_refine_ls_number_restraints   0
_refine_ls_restrained_S_all    1.05
_refine_ls_R_factor_all        0.071
_refine_ls_R_factor_gt         0.040
_refine_ls_shift/su_max        0.003
_refine_ls_shift/su_mean       0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 calc w=1/[\s^2^(Fo^2^)+(0.029P)^2^+0.054P] where
P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.084
_refine_ls_wR_factor_ref       0.095
_reflns_number_gt              2309
_reflns_number_total           3362
_reflns_threshold_expression   '>2\s(I) '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cl13 0.44792(10) 0.47127(7) 0.27629(6) 0.03104(18) Uani d . 1 . . Cl
Cl15 0.04364(11) 0.56389(8) 0.70496(6) 0.0365(2) Uani d . 1 . . Cl
O14 0.2177(3) 0.38864(19) 0.51401(15) 0.0301(4) Uani d . 1 . . O
H14 0.2711 0.3403 0.4571 0.036 Uiso calc R 1 . . H
N17 0.3350(4) 1.1216(3) 0.4097(2) 0.0372(6) Uani d . 1 . . N
C17 0.3216(4) 0.9954(3) 0.4245(2) 0.0287(6) Uani d . 1 . . C
C11 0.2982(4) 0.8376(3) 0.4456(2) 0.0251(6) Uani d . 1 . . C
C12 0.3819(4) 0.7403(3) 0.3608(2) 0.0234(6) Uani d . 1 . . C
H12 0.4580 0.7758 0.2892 0.028 Uiso calc R 1 . . H
C13 0.3519(4) 0.5911(3) 0.3828(2) 0.0219(6) Uani d . 1 . . C
C14 0.2479(4) 0.5332(3) 0.4884(2) 0.0223(6) Uani d . 1 . . C
C15 0.1700(4) 0.6329(3) 0.5724(2) 0.0234(6) Uani d . 1 . . C
C16 0.1923(4) 0.7835(3) 0.5512(2) 0.0265(6) Uani d . 1 . . C
H16 0.1353 0.8504 0.6087 0.032 Uiso calc R 1 . . H
Cl23 0.26550(10) 1.08330(7) 1.14836(5) 0.02751(17) Uani d . 1 . . Cl
Cl25 0.18386(10) 1.09927(7) 0.72286(5) 0.03108(18) Uani d . 1 . . Cl
O24 0.2355(3) 1.22312(18) 0.90769(15) 0.0291(4) Uani d . 1 . . O
H24 0.2479 1.2578 0.9636 0.035 Uiso calc R 1 . . H
N27 0.2523(3) 0.4597(3) 1.0168(2) 0.0349(6) Uani d . 1 . . N
C27 0.2504(4) 0.5887(3) 1.0014(2) 0.0267(6) Uani d . 1 . . C
C21 0.2481(4) 0.7533(3) 0.9794(2) 0.0214(5) Uani d . 1 . . C
C22 0.2609(3) 0.8279(3) 1.0652(2) 0.0228(6) Uani d . 1 . . C
H22 0.2730 0.7719 1.1384 0.027 Uiso calc R 1 . . H
C23 0.2557(3) 0.9854(3) 1.0420(2) 0.0209(5) Uani d . 1 . . C
C24 0.2380(3) 1.0709(3) 0.9358(2) 0.0207(5) Uani d . 1 . . C
C25 0.2188(3) 0.9925(3) 0.8520(2) 0.0215(5) Uani d . 1 . . C
C26 0.2255(3) 0.8356(3) 0.8729(2) 0.0229(6) Uani d . 1 . . C
H26 0.2148 0.7836 0.8152 0.027 Uiso calc R 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
Cl13 0.0393(4) 0.0233(3) 0.0302(4) -0.0077(3) -0.0021(3) -0.0106(3)
Cl15 0.0483(5) 0.0360(4) 0.0256(4) -0.0190(3) 0.0002(3) -0.0039(3)
O14 0.0452(12) 0.0186(9) 0.0287(10) -0.0137(8) -0.0055(9) -0.0033(8)
N17 0.0551(17) 0.0206(12) 0.0396(15) -0.0118(11) -0.0139(13) -0.0041(11)
C17 0.0371(16) 0.0232(15) 0.0291(15) -0.0088(12) -0.0106(12) -0.0044(12)
C11 0.0321(15) 0.0183(13) 0.0289(15) -0.0085(11) -0.0117(12) -0.0021(11)
C12 0.0282(14) 0.0195(13) 0.0243(14) -0.0060(11) -0.0085(11) -0.0028(11)
C13 0.0251(14) 0.0172(13) 0.0249(14) -0.0033(11) -0.0073(11) -0.0063(10)
C14 0.0270(14) 0.0158(12) 0.0259(14) -0.0067(11) -0.0086(11) -0.0011(11)
C15 0.0306(15) 0.0210(13) 0.0185(13) -0.0079(11) -0.0044(11) -0.0015(10)
C16 0.0339(16) 0.0211(13) 0.0273(14) -0.0055(12) -0.0085(12) -0.0086(11)
Cl23 0.0384(4) 0.0216(3) 0.0270(3) -0.0093(3) -0.0092(3) -0.0079(3)
Cl25 0.0456(4) 0.0270(4) 0.0231(3) -0.0130(3) -0.0093(3) -0.0008(3)
O24 0.0482(12) 0.0173(9) 0.0265(10) -0.0138(8) -0.0100(9) -0.0029(8)
N27 0.0494(16) 0.0202(12) 0.0380(14) -0.0111(11) -0.0112(12) -0.0050(11)
C27 0.0299(15) 0.0233(14) 0.0275(15) -0.0046(12) -0.0073(12) -0.0061(12)
C21 0.0225(14) 0.0128(12) 0.0284(14) -0.0042(10) -0.0037(11) -0.0041(10)
C22 0.0265(14) 0.0194(13) 0.0225(13) -0.0055(11) -0.0055(11) -0.0028(11)
C23 0.0224(13) 0.0186(13) 0.0237(13) -0.0054(10) -0.0039(11) -0.0087(11)
C24 0.0237(13) 0.0143(12) 0.0248(14) -0.0083(10) -0.0019(11) -0.0034(10)
C25 0.0217(13) 0.0222(13) 0.0193(13) -0.0064(11) -0.0023(11) -0.0010(10)
C26 0.0240(14) 0.0224(14) 0.0250(14) -0.0065(11) -0.0049(11) -0.0086(11)
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
C14 O14 H14 . . 109.5 ?
N17 C17 C11 . . 178.1(3) ?
C16 C11 C12 . . 120.4(2) ?
C16 C11 C17 . . 119.3(2) ?
C12 C11 C17 . . 120.2(2) ?
C13 C12 C11 . . 118.7(2) ?
C13 C12 H12 . . 120.7 ?
C11 C12 H12 . . 120.7 ?
C12 C13 C14 . . 122.1(2) ?
C12 C13 Cl13 . . 119.14(19) ?
C14 C13 Cl13 . . 118.77(19) ?
O14 C14 C13 . . 124.1(2) ?
O14 C14 C15 . . 118.3(2) ?
C13 C14 C15 . . 117.6(2) ?
C16 C15 C14 . . 121.3(2) ?
C16 C15 Cl15 . . 119.87(19) ?
C14 C15 Cl15 . . 118.79(19) ?
C15 C16 C11 . . 119.8(2) ?
C15 C16 H16 . . 120.1 ?
C11 C16 H16 . . 120.1 ?
C24 O24 H24 . . 109.5 ?
N27 C27 C21 . . 178.9(3) ?
C22 C21 C26 . . 120.9(2) ?
C22 C21 C27 . . 120.0(2) ?
C26 C21 C27 . . 119.0(2) ?
C23 C22 C21 . . 118.6(2) ?
C23 C22 H22 . . 120.7 ?
C21 C22 H22 . . 120.7 ?
C22 C23 C24 . . 122.2(2) ?
C22 C23 Cl23 . . 119.8(2) ?
C24 C23 Cl23 . . 118.04(18) ?
O24 C24 C23 . . 124.8(2) ?
O24 C24 C25 . . 117.5(2) ?
C23 C24 C25 . . 117.7(2) ?
C26 C25 C24 . . 121.0(2) ?
C26 C25 Cl25 . . 120.85(19) ?
C24 C25 Cl25 . . 118.11(18) ?
C25 C26 C21 . . 119.5(2) ?
C25 C26 H26 . . 120.2 ?
C21 C26 H26 . . 120.2 ?
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
Cl13 C13 . 1.731(2) ?
Cl15 C15 . 1.726(3) ?
O14 C14 . 1.341(3) ?
O14 H14 . 0.8400 ?
N17 C17 . 1.141(3) ?
C17 C11 . 1.442(3) ?
C11 C16 . 1.387(4) ?
C11 C12 . 1.393(3) ?
C12 C13 . 1.382(3) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.394(3) ?
C14 C15 . 1.397(3) ?
C15 C16 . 1.375(3) ?
C16 H16 . 0.9500 ?
Cl23 C23 . 1.734(2) ?
Cl25 C25 . 1.722(2) ?
O24 C24 . 1.341(3) ?
O24 H24 . 0.8400 ?
N27 C27 . 1.135(3) ?
C27 C21 . 1.449(3) ?
C21 C22 . 1.387(3) ?
C21 C26 . 1.393(3) ?
C22 C23 . 1.382(3) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.392(3) ?
C24 C25 . 1.408(3) ?
C25 C26 . 1.375(3) ?
C26 H26 . 0.9500 ?