#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/15/2011560.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2011560 loop_ _publ_author_name 'Lynch, Daniel E.' 'McClenaghan, Ian' _publ_section_title ; 2-Chloro-3-morpholino-1,4-naphthoquinone ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first e537 _journal_page_last e537 _journal_paper_doi 10.1107/S0108270100014207 _journal_volume 56 _journal_year 2000 _chemical_formula_sum 'C14 H12 Cl N O3' _chemical_formula_weight 277.70 _chemical_melting_point 429.0(10) _chemical_name_systematic ; 2-Chloro-3-(4-morpholino)-1,4-naphthoquinone ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method SHELXL97 _cell_angle_alpha 67.2038(12) _cell_angle_beta 84.4066(10) _cell_angle_gamma 81.2678(12) _cell_formula_units_Z 2 _cell_length_a 5.03860(10) _cell_length_b 10.3948(2) _cell_length_c 12.7421(3) _cell_measurement_reflns_used 4135 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 2.91 _cell_volume 607.56(2) _computing_cell_refinement 'DENZO and COLLECT' _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO and COLLECT' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 9.091 _diffrn_measured_fraction_theta_full .984 _diffrn_measured_fraction_theta_max .984 _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .031 _diffrn_reflns_av_sigmaI/netI .0347 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 6621 _diffrn_reflns_theta_full 27.53 _diffrn_reflns_theta_max 27.53 _diffrn_reflns_theta_min 3.23 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .317 _exptl_absorpt_correction_T_max .977 _exptl_absorpt_correction_T_min .884 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.518 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 288 _exptl_crystal_size_max .40 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .08 _refine_diff_density_max .335 _refine_diff_density_min -.372 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.160 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 172 _refine_ls_number_reflns 2761 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.160 _refine_ls_R_factor_all .044 _refine_ls_R_factor_gt .039 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .142 _reflns_number_gt 2449 _reflns_number_total 2761 _reflns_threshold_expression I>2\s(I) _cod_data_source_file qa0432.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '428 - 430 K' was changed to '429.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '428 - 430 K' was changed to '429.0(10)' - the average value was taken and precision was estimated. '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2011560 _cod_database_fobs_code 2011560 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 C1 .5044(3) .20176(14) .10486(11) .0230(3) Uani d . 1 . . C O1 .4184(2) .28268(11) .01277(9) .0345(3) Uani d . 1 . . O C2 .4346(3) .05762(14) .15913(11) .0209(3) Uani d . 1 . . C Cl2 .20776(6) .01615(3) .08691(3) .02830(17) Uani d . 1 . . Cl C3 .5264(2) -.03813(13) .26084(11) .0203(3) Uani d . 1 . . C N31 .4885(2) -.17681(12) .30333(10) .0247(3) Uani d . 1 . . N C32 .4332(3) -.26062(15) .42384(12) .0280(3) Uani d . 1 . . C H111 .3748 -.1981 .4661 .035 Uiso calc R 1 . . H H112 .5974 -.3226 .4581 .035 Uiso calc R 1 . . H C33 .2117(3) -.34858(15) .43056(13) .0329(3) Uani d . 1 . . C H121 .1748 -.4083 .5112 .041 Uiso calc R 1 . . H H122 .0451 -.2853 .4012 .041 Uiso calc R 1 . . H O34 .2832(2) -.43609(10) .36633(9) .0344(3) Uani d . 1 . . O C35 .3313(3) -.35325(15) .24931(13) .0303(3) Uani d . 1 . . C H131 .1645 -.2919 .2177 .038 Uiso calc R 1 . . H H132 .3831 -.4156 .2065 .038 Uiso calc R 1 . . H C36 .5524(3) -.26367(14) .23482(12) .0244(3) Uani d . 1 . . C H141 .7240 -.3250 .2586 .030 Uiso calc R 1 . . H H142 .5746 -.2023 .1535 .030 Uiso calc R 1 . . H C4 .6912(3) .01070(14) .32853(12) .0230(3) Uani d . 1 . . C O4 .7648(3) -.06883(11) .42194(10) .0419(3) Uani d . 1 . . O C5 .9383(3) .19717(14) .33317(12) .0242(3) Uani d . 1 . . C H5 .9982 .1350 .4061 .030 Uiso calc R 1 . . H C6 1.0187(3) .33047(15) .28378(13) .0293(3) Uani d . 1 . . C H6 1.1341 .3596 .3227 .037 Uiso calc R 1 . . H C7 .9300(3) .42136(14) .17709(13) .0304(3) Uani d . 1 . . C H7 .9838 .5129 .1438 .038 Uiso calc R 1 . . H C8 .7641(3) .37966(14) .11893(12) .0274(3) Uani d . 1 . . C H8 .7053 .4422 .0459 .034 Uiso calc R 1 . . H C9 .6838(3) .24580(13) .16766(11) .0203(3) Uani d . 1 . . C C10 .7691(3) .15463(13) .27548(11) .0206(3) Uani d . 1 . . C 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 C1 .0255(7) .0223(7) .0224(7) .0005(5) -.0045(5) -.0100(5) O1 .0511(7) .0251(5) .0262(6) -.0009(5) -.0165(5) -.0064(4) C2 .0199(6) .0245(6) .0225(7) -.0037(5) -.0035(5) -.0124(5) Cl2 .0250(2) .0357(3) .0301(3) -.00578(16) -.00844(16) -.01645(18) C3 .0202(6) .0223(6) .0212(7) -.0059(5) -.0001(5) -.0103(5) N31 .0335(7) .0221(6) .0221(6) -.0111(5) .0015(5) -.0101(5) C32 .0349(8) .0251(7) .0240(7) -.0115(6) .0004(6) -.0070(6) C33 .0363(8) .0305(8) .0325(8) -.0139(6) .0072(6) -.0109(6) O34 .0421(6) .0267(5) .0379(6) -.0167(5) .0042(5) -.0129(5) C35 .0319(7) .0291(7) .0357(8) -.0140(6) .0003(6) -.0152(6) C36 .0248(7) .0241(6) .0290(7) -.0080(5) .0010(5) -.0138(6) C4 .0274(7) .0198(6) .0229(7) -.0038(5) -.0065(5) -.0078(5) O4 .0642(8) .0265(6) .0332(6) -.0144(5) -.0259(6) -.0006(5) C5 .0280(7) .0243(6) .0239(7) -.0047(5) -.0044(5) -.0119(6) C6 .0313(7) .0303(7) .0335(8) -.0102(6) -.0014(6) -.0176(6) C7 .0372(8) .0225(7) .0355(8) -.0117(6) .0024(6) -.0135(6) C8 .0327(7) .0228(7) .0253(7) -.0032(6) -.0019(6) -.0075(6) C9 .0230(6) .0185(6) .0213(6) -.0013(5) -.0021(5) -.0097(5) C10 .0229(7) .0187(6) .0219(7) -.0016(5) -.0027(5) -.0094(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl .1484 .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 O1 C1 C2 121.87(12) O1 C1 C9 121.24(12) C2 C1 C9 116.88(11) C3 C2 C1 124.69(11) C3 C2 Cl2 120.44(10) C1 C2 Cl2 114.82(10) C2 C3 N31 124.03(11) C2 C3 C4 118.06(11) N31 C3 C4 117.85(12) C3 N31 C32 124.81(11) C3 N31 C36 121.78(11) C32 N31 C36 112.39(11) N31 C32 C33 107.81(12) N31 C32 H111 110.1 C33 C32 H111 110.1 N31 C32 H112 110.1 C33 C32 H112 110.1 H111 C32 H112 108.5 O34 C33 C32 111.99(11) O34 C33 H121 109.2 C32 C33 H121 109.2 O34 C33 H122 109.2 C32 C33 H122 109.2 H121 C33 H122 107.9 C35 O34 C33 110.69(10) O34 C35 C36 110.76(11) O34 C35 H131 109.5 C36 C35 H131 109.5 O34 C35 H132 109.5 C36 C35 H132 109.5 H131 C35 H132 108.1 N31 C36 C35 110.60(10) N31 C36 H141 109.5 C35 C36 H141 109.5 N31 C36 H142 109.5 C35 C36 H142 109.5 H141 C36 H142 108.1 O4 C4 C10 121.35(12) O4 C4 C3 120.22(12) C10 C4 C3 118.37(12) C6 C5 C10 119.88(13) C6 C5 H5 120.1 C10 C5 H5 120.1 C5 C6 C7 119.87(12) C5 C6 H6 120.1 C7 C6 H6 120.1 C8 C7 C6 120.63(12) C8 C7 H7 119.7 C6 C7 H7 119.7 C7 C8 C9 119.83(13) C7 C8 H8 120.1 C9 C8 H8 120.1 C8 C9 C10 119.84(12) C8 C9 C1 119.58(12) C10 C9 C1 120.57(12) C5 C10 C9 119.93(12) C5 C10 C4 118.96(12) C9 C10 C4 121.07(11) 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 C1 O1 . 1.2229(17) ? C1 C2 . 1.4685(19) ? C1 C9 . 1.4892(17) ? C2 C3 . 1.3645(19) ? C2 Cl2 . 1.7322(12) ? C3 N31 . 1.3661(16) ? C3 C4 . 1.5160(17) ? N31 C32 . 1.4657(18) ? N31 C36 . 1.4658(15) ? C32 C33 . 1.5230(18) ? C32 H111 . .9900 ? C32 H112 . .9900 ? C33 O34 . 1.4307(16) ? C33 H121 . .9900 ? C33 H122 . .9900 ? O34 C35 . 1.4218(18) ? C35 C36 . 1.5110(17) ? C35 H131 . .9900 ? C35 H132 . .9900 ? C36 H141 . .9900 ? C36 H142 . .9900 ? C4 O4 . 1.2116(18) ? C4 C10 . 1.4806(18) ? C5 C6 . 1.3875(19) ? C5 C10 . 1.3968(17) ? C5 H5 . .9500 ? C6 C7 . 1.391(2) ? C6 H6 . .9500 ? C7 C8 . 1.384(2) ? C7 H7 . .9500 ? C8 C9 . 1.3922(19) ? C8 H8 . .9500 ? C9 C10 . 1.3975(18) ? 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 C5 H5 O4 2_756 .95 2.41 3.2914(18) 154.8 yes C33 H122 O4 1_455 .99 2.56 3.3692(19) 139.0 yes C36 H142 Cl2 . .99 2.61 3.1439(14) 113.6 yes C36 H142 O1 2_655 .99 2.56 3.2246(17) 124.7 yes 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 O1 C1 C2 C3 179.13(13) C9 C1 C2 C3 -1.4(2) O1 C1 C2 Cl2 -3.65(18) C9 C1 C2 Cl2 175.86(8) C1 C2 C3 N31 -171.18(12) Cl2 C2 C3 N31 11.74(19) C1 C2 C3 C4 6.0(2) Cl2 C2 C3 C4 -171.09(9) C2 C3 N31 C32 -142.17(14) C4 C3 N31 C32 40.65(19) C2 C3 N31 C36 50.26(19) C4 C3 N31 C36 -126.92(13) C3 N31 C32 C33 136.77(13) C36 N31 C32 C33 -54.65(15) N31 C32 C33 O34 57.20(16) C32 C33 O34 C35 -60.29(16) C33 O34 C35 C36 58.29(15) C3 N31 C36 C35 -136.06(13) C32 N31 C36 C35 54.96(16) O34 C35 C36 N31 -55.48(15) C2 C3 C4 O4 176.14(13) N31 C3 C4 O4 -6.5(2) C2 C3 C4 C10 -6.58(19) N31 C3 C4 C10 170.77(11) C10 C5 C6 C7 .2(2) C5 C6 C7 C8 -.7(2) C6 C7 C8 C9 .3(2) C7 C8 C9 C10 .5(2) C7 C8 C9 C1 179.75(11) O1 C1 C9 C8 -2.6(2) C2 C1 C9 C8 177.94(11) O1 C1 C9 C10 176.66(12) C2 C1 C9 C10 -2.85(19) C6 C5 C10 C9 .7(2) C6 C5 C10 C4 178.52(12) C8 C9 C10 C5 -1.1(2) C1 C9 C10 C5 179.73(11) C8 C9 C10 C4 -178.81(12) C1 C9 C10 C4 2.0(2) O4 C4 C10 C5 2.2(2) C3 C4 C10 C5 -175.08(11) O4 C4 C10 C9 179.94(14) C3 C4 C10 C9 2.69(19) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 206576 2 PubChem 236652