#------------------------------------------------------------------------------ #$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $ #$Revision: 26029 $ #$URL: svn://www.crystallography.net/cod/cif/2/2002923.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_2002923 _journal_name_full 'Acta Crystallographica, Section B' _journal_volume 54 _journal_year 1998 _journal_page_first 695 _journal_page_last 704 _chemical_name_systematic ; (1,4-diaminobenzene).2(4-chloro,1-hydroxybenzene) ; _chemical_name_common '1,4-phenylenediamine.2p-chlorophenol' _chemical_formula_moiety 'C6 H8 N2 , 2C6 H5 O Cl ' _chemical_formula_sum 'C18 H18 Cl2 N2 O2' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_weight 365.24 _chemical_melting_point 91 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.4878(7) _cell_length_b 8.785(2) _cell_length_c 11.9870(10) _cell_angle_alpha 70.000(10) _cell_angle_beta 86.670(10) _cell_angle_gamma 82.180(10) _cell_volume 439.95(12) _cell_formula_units_Z 1 _cell_measurement_reflns_used 50 _cell_measurement_theta_min 4.45 _cell_measurement_theta_max 12.43 _cell_measurement_temperature 295(2) _exptl_crystal_description cut-plate _exptl_crystal_colour colorless _exptl_crystal_size_max .58 _exptl_crystal_size_mid .42 _exptl_crystal_size_min .30 _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method ? _exptl_crystal_F_000 190 _exptl_absorpt_coefficient_mu 0.381 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 295(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 'Siemens P4' _diffrn_measurement_method \w _diffrn_reflns_number 2005 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 24.25 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1.2 _reflns_number_total 1410 _reflns_number_observed 1025 _reflns_observed_criterion >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0624 _refine_ls_R_factor_obs 0.0401 _refine_ls_wR_factor_all 0.1082 _refine_ls_wR_factor_obs 0.0952 _refine_ls_goodness_of_fit_all 1.040 _refine_ls_goodness_of_fit_obs 1.090 _refine_ls_restrained_S_all 1.040 _refine_ls_restrained_S_obs 1.090 _refine_ls_number_reflns 1025 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment ; phenyl hydrogens calculated; riding model .96A, U = 1.2 times U attached C. amine and hydroxyl hydrogens positions refined, U~iso~ = 1.2 times U of O or N. ; _refine_ls_weighting_scheme ;w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+0.0889P] where P = (Fo^2^+2Fc^2^)/3 ; _refine_ls_shift/esd_max 0.002 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.144 _refine_diff_density_min -0.195 _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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' ## 'XTAL3.4 CRYLSQ (Hall et al., 1995), SHELXL-93 (Sheldrick, 1993)' ## 'XTAL3.4 (Hall et al., 1995), ORTEPIII (Burnett & Johnson, 1996)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol N1 0.2267(6) 0.2791(3) 0.9280(2) 0.0714(7) Uani d . 1 . N H2 0.159(7) 0.204(4) 0.986(3) 0.086 Uiso d . 1 . H H1 0.105(7) 0.325(3) 0.878(3) 0.086 Uiso d . 1 . H C2 0.3550(5) 0.3926(3) 0.9653(2) 0.0526(6) Uani d . 1 . C C3 0.6019(6) 0.4551(3) 1.1136(2) 0.0589(6) Uani d . 1 . C H3 0.6721(6) 0.4226(3) 1.1935(2) 0.071 Uiso calc R 1 . H C4 0.5406(6) 0.6512(3) 0.9207(2) 0.0584(6) Uani d . 1 . C H4 0.5673(6) 0.7567(3) 0.8645(2) 0.070 Uiso calc R 1 . H Cl 0.1857(2) 0.28383(9) 0.38541(6) 0.0877(3) Uani d . 1 . Cl O5 -0.2962(5) 0.0755(2) 0.8720(2) 0.0756(6) Uani d . 1 . O H5 -0.445(7) 0.134(4) 0.881(3) 0.091 Uiso d . 1 . H C6 -0.1914(6) 0.1292(3) 0.7581(2) 0.0557(6) Uani d . 1 . C C7 0.0323(6) 0.0301(3) 0.7244(2) 0.0738(8) Uani d . 1 . C H7 0.1080(6) -0.0732(3) 0.7811(2) 0.089 Uiso calc R 1 . H C8 0.1496(7) 0.0762(3) 0.6109(3) 0.0765(8) Uani d . 1 . C H8 0.3074(7) 0.0062(3) 0.5887(3) 0.092 Uiso calc R 1 . H C9 0.0396(6) 0.2227(3) 0.5297(2) 0.0604(6) Uani d . 1 . C C10 -0.1809(6) 0.3226(3) 0.5622(2) 0.0709(7) Uani d . 1 . C H10 -0.2557(6) 0.4260(3) 0.5054(2) 0.085 Uiso calc R 1 . H C11 -0.2971(6) 0.2761(3) 0.6759(2) 0.0703(7) Uani d . 1 . C H11 -0.4534(6) 0.3470(3) 0.6979(2) 0.084 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 N1 0.075(2) 0.078(2) 0.073(2) -0.0226(13) 0.0081(12) -0.0365(13) C2 0.0483(14) 0.0572(13) 0.0561(14) -0.0046(11) 0.0081(11) -0.0260(11) C3 0.064(2) 0.0628(15) 0.0469(13) -0.0019(13) -0.0014(11) -0.0170(11) C4 0.067(2) 0.0489(13) 0.0530(14) -0.0046(12) 0.0082(12) -0.0111(11) Cl 0.1093(7) 0.0912(6) 0.0674(5) -0.0197(5) 0.0203(4) -0.0334(4) O5 0.0908(15) 0.0677(12) 0.0632(11) -0.0059(10) 0.0109(11) -0.0187(9) C6 0.062(2) 0.0516(14) 0.0569(14) -0.0114(12) 0.0010(12) -0.0212(11) C7 0.083(2) 0.0525(14) 0.075(2) 0.0064(14) 0.0020(15) -0.0130(13) C8 0.082(2) 0.060(2) 0.083(2) 0.0042(15) 0.017(2) -0.0267(15) C9 0.065(2) 0.062(2) 0.0610(15) -0.0124(13) 0.0048(12) -0.0287(13) C10 0.073(2) 0.061(2) 0.065(2) 0.0057(14) 0.0001(14) -0.0097(13) C11 0.073(2) 0.0593(15) 0.070(2) 0.0075(13) 0.0106(14) -0.0190(13) _cod_database_code 2002923