data_2003520 _journal_name_full 'Acta Crystallographica' _journal_year 1995 _journal_volume C51 _journal_page_first 1173 _journal_page_last 1175 _publ_section_title ; 10-Hydroxybenzo[h]quinoline ; _chemical_formula_moiety 'C13 H9 N O' _chemical_formula_sum 'C13 H9 N O' _chemical_formula_weight 195.21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, z' 'x, -y+1/2, z+1/2' '-x, -y, z+1/2' _symmetry_space_group_name_H-M 'P b c 21' _cell_length_a 4.6530(4) _cell_length_b 15.1910(10) _cell_length_c 26.902(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1901.5(2) _cell_formula_units_Z 8 _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _cell_measurement_reflns_used 15 _cell_measurement_theta_min 19.35 _cell_measurement_theta_max 37.54 _exptl_absorpt_coefficient_mu 0.695 _cell_measurement_temperature 293(2) _exptl_crystal_description prism _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_colour colorless _chemical_compound_source ; synthesized from CH~2~Cl~2~--benzene system ; _diffrn_measurement_device 'Syntex P2~1~' _diffrn_measurement_method \w/2\q _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_reflns_number 1312 _reflns_number_total 1312 _reflns_number_observed 1076 _reflns_observed_criterion >2sigma(I) _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_theta_max 57.34 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 29 _diffrn_standards_number 2 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1.5 _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_obs 0.0383 _refine_ls_wR_factor_obs 0.0767 _refine_ls_wR_factor_all 0.1128 _refine_ls_goodness_of_fit_obs 1.260 _refine_ls_goodness_of_fit_all 1.213 _refine_ls_number_reflns 1306 _refine_ls_number_parameters 280 _refine_ls_hydrogen_treatment ;noref except H10A and H10B, which were refined isotropically ; _refine_ls_weighting_scheme ; calc w=1/[\s~2~(F~o~^2^) + (0.0150P)^2^ + 0.9500P] where P=(F~o~^2^ + 2F~c~^2^)/3 ; _refine_ls_shift/esd_max 0.000 _refine_diff_density_max 0.117 _refine_diff_density_min -0.131 _refine_ls_extinction_method 'SHELXL93 (Sheldrick, 1994)' _refine_ls_extinction_coef 0.0048(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag 'C' 'C' 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0181 0.009 'H' 'H' 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0000 0.000 'N' 'N' 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0311 0.018 'O' 'O' 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0492 0.032 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881 _refine_ls_abs_structure_Flack -0.32(56) loop_ _atom_site_label _atom_site_occupancy _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv N1A 1 1.0034(9) 1.0843(2) 0.19974(14) 0.0568(10) C2A 1 1.1949(11) 1.0912(3) 0.2364(2) 0.0637(13) H2A 1 1.2638 1.1468 0.2446 0.076 C3A 1 1.2955(11) 1.0195(4) 0.2626(2) 0.0684(14) H3A 1 1.4292 1.0273 0.2880 0.082 C4A 1 1.1979(10) 0.9372(3) 0.2512(2) 0.0624(13) H4A 1 1.2642 0.8884 0.2687 0.075 C4aA 1 0.9963(10) 0.9272(3) 0.2129(2) 0.0516(11) C5A 1 0.8866(11) 0.8426(3) 0.1987(2) 0.0636(13) H5A 1 0.9511 0.7921 0.2148 0.076 C6A 1 0.6899(11) 0.8364(3) 0.1622(2) 0.0656(14) H6A 1 0.6204 0.7810 0.1537 0.079 C6aA 1 0.5831(10) 0.9113(3) 0.1357(2) 0.0558(12) C7A 1 0.3734(11) 0.9023(4) 0.0990(2) 0.0671(14) H7A 1 0.3014 0.8469 0.0912 0.081 C8A 1 0.2742(12) 0.9748(4) 0.0746(2) 0.0745(15) H8A 1 0.1324 0.9683 0.0505 0.089 C9A 1 0.3794(11) 1.0571(4) 0.0849(2) 0.0690(15) H9A 1 0.3092 1.1056 0.0676 0.083 C10A 1 0.5907(10) 1.0688(3) 0.1210(2) 0.0571(12) O10A 1 0.6961(8) 1.1515(2) 0.12983(14) 0.0762(10) H10A 1 0.8552(119) 1.1531(33) 0.1723(21) 0.106(18) C10aA 1 0.6929(9) 0.9956(3) 0.1483(2) 0.0486(11) C10bA 1 0.9016(9) 1.0025(3) 0.1878(2) 0.0480(11) N1B 1 0.0295(9) 0.3704(2) 0.39230(15) 0.0621(10) C2B 1 -0.1629(11) 0.4246(3) 0.4131(2) 0.0723(15) H2B 1 -0.2410 0.4691 0.3936 0.087 C3B 1 -0.2514(12) 0.4181(4) 0.4617(2) 0.077(2) H3B 1 -0.3860 0.4573 0.4745 0.092 C4B 1 -0.1385(11) 0.3533(3) 0.4909(2) 0.0669(13) H4B 1 -0.1956 0.3482 0.5239 0.080 C4aB 1 0.0618(10) 0.2947(3) 0.4714(2) 0.0541(12) C5B 1 0.1861(11) 0.2256(3) 0.4993(2) 0.0634(13) H5B 1 0.1328 0.2183 0.5324 0.076 C6B 1 0.3795(12) 0.1703(3) 0.4792(2) 0.0634(13) H6B 1 0.4564 0.1256 0.4988 0.076 C6aB 1 0.4708(10) 0.1782(3) 0.4284(2) 0.0533(12) C7B 1 0.6763(11) 0.1209(3) 0.4080(2) 0.0643(13) H7B 1 0.7542 0.0759 0.4272 0.077 C8B 1 0.7608(11) 0.1317(3) 0.3596(2) 0.0715(15) H8B 1 0.8982 0.0941 0.3463 0.086 C9B 1 0.6460(11) 0.1974(3) 0.3305(2) 0.0658(13) H9B 1 0.7054 0.2029 0.2976 0.079 C10B 1 0.4467(10) 0.2542(3) 0.3490(2) 0.0576(12) O10B 1 0.3330(8) 0.3175(3) 0.31866(13) 0.0848(11) H10B 1 0.1501(87) 0.3681(24) 0.3442(15) 0.053(11) C10aB 1 0.3530(9) 0.2464(3) 0.3991(2) 0.0491(10) C10bB 1 0.1455(10) 0.3050(3) 0.4211(2) 0.0494(11) loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 N1A 0.062(2) -0.002(2) 0.002(2) 0.049(2) -0.006(2) 0.059(2) C2A 0.067(3) -0.004(3) -0.002(3) 0.063(3) -0.015(2) 0.062(3) C3A 0.067(3) -0.002(3) -0.006(3) 0.086(4) -0.008(3) 0.052(3) C4A 0.066(3) 0.008(3) -0.003(3) 0.068(3) 0.009(2) 0.052(3) C4aA 0.057(3) 0.003(2) 0.009(2) 0.050(3) 0.003(2) 0.047(2) C5A 0.075(3) -0.003(3) 0.002(3) 0.048(2) 0.008(2) 0.067(3) C6A 0.081(4) -0.013(3) 0.006(3) 0.049(3) -0.002(2) 0.066(3) C6aA 0.057(3) -0.004(2) 0.008(2) 0.064(3) -0.005(2) 0.046(3) C7A 0.060(3) -0.010(3) 0.004(3) 0.089(4) -0.010(3) 0.052(3) C8A 0.060(3) -0.006(3) 0.000(3) 0.115(4) -0.015(3) 0.049(3) C9A 0.061(3) 0.024(3) 0.002(2) 0.102(4) 0.011(3) 0.044(3) C10A 0.055(3) 0.008(2) 0.008(2) 0.061(3) 0.003(2) 0.056(3) O10A 0.089(3) 0.013(2) -0.004(2) 0.056(2) 0.009(2) 0.084(2) C10aA 0.048(3) 0.004(2) 0.008(2) 0.054(3) -0.001(2) 0.044(2) C10bA 0.051(3) -0.001(2) 0.008(2) 0.052(3) 0.001(2) 0.040(2) N1B 0.059(3) -0.005(2) -0.007(2) 0.058(2) 0.008(2) 0.070(2) C2B 0.066(3) -0.002(3) -0.006(3) 0.051(3) 0.001(3) 0.100(4) C3B 0.065(3) -0.003(3) 0.008(3) 0.069(3) -0.027(3) 0.096(4) C4B 0.062(3) -0.011(3) 0.004(3) 0.072(3) -0.022(3) 0.067(3) C4aB 0.050(3) -0.013(2) 0.004(2) 0.057(3) -0.007(2) 0.055(3) C5B 0.073(3) -0.011(3) 0.000(3) 0.068(3) 0.001(2) 0.049(3) C6B 0.075(3) -0.004(3) -0.012(3) 0.063(3) 0.007(2) 0.052(3) C6aB 0.054(3) -0.011(2) -0.009(2) 0.050(2) 0.000(2) 0.055(3) C7B 0.057(3) 0.000(3) -0.005(3) 0.054(3) -0.011(3) 0.082(4) C8B 0.054(3) -0.001(3) 0.003(3) 0.074(3) -0.030(3) 0.087(4) C9B 0.060(3) -0.013(3) 0.005(3) 0.082(3) -0.014(3) 0.055(3) C10B 0.059(3) -0.012(3) 0.001(2) 0.066(3) -0.002(2) 0.047(3) O10B 0.083(3) -0.007(2) 0.002(2) 0.108(3) 0.020(2) 0.063(2) C10aB 0.043(2) -0.010(2) 0.000(2) 0.054(2) -0.005(2) 0.050(2) C10bB 0.048(3) -0.012(2) -0.005(2) 0.047(2) -0.001(2) 0.053(3)