Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Martin Schmidt' _publ_contact_author_address ; Institut fuer Anorganische und Analytische Chemie Goethe-Universitaet Frankfurt Max-von-Laue-Str. 7 D-60438 Frankfurt am Main D-60438 GERMANY ; _publ_contact_author_email M.SCHMIDT@CHEMIE.UNI-FRANKFURT.DE _publ_section_title ; Crystal structures of Quinacridones ; loop_ _publ_author_name 'Martin Schmidt' 'Frank J. J. Leusen' 'Erich F. Paulus' data_CHINACRIDON_publ _database_code_depnum_ccdc_archive 'CCDC 620257' _pd_block_id 2006-11-15T11:42|CHINACRIDON|Christian_Buchsbaum|inhouse _audit_creation_method 'from EXP file using GSAS2CIF' _audit_creation_date 2006-11-15T11:42 _audit_author_name 'Christian Buchsbaum' _audit_update_record ; 2006-11-15T11:42 Initial CIF as created by GSAS2CIF ; #============================================================================= # this information describes the project, paper etc. for the CIF # # Acta Cryst. Section C papers and editorial correspondence is generated # # from the information in this section # # # # (from) CIF submission form for Rietveld refinements (Acta Cryst. C) # # Version 14 December 1998 # #============================================================================= #============================================================================= # 5. OVERALL REFINEMENT & COMPUTING DETAILS _refine_special_details ; ? ; _pd_proc_ls_special_details ; ? ; # The following items are used to identify the programs used. _computing_molecular_graphics ? _computing_publication_material ? _refine_ls_weighting_scheme ? _refine_ls_weighting_details ? _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method ? _refine_ls_extinction_coef ? _refine_ls_number_constraints ? _refine_ls_restrained_S_all ? _refine_ls_restrained_S_obs ? #============================================================================== # 6. SAMPLE PREPARATION DATA # (In the unusual case where multiple samples are used in a single # Rietveld study, this information should be moved into the phase # blocks) # The following three fields describe the preparation of the material. # The cooling rate is in K/min. The pressure at which the sample was # prepared is in kPa. The temperature of preparation is in K. _pd_prep_cool_rate ? _pd_prep_pressure ? _pd_prep_temperature ? _pd_char_colour ? # use ICDD colour descriptions _refine_ls_shift/su_max 0.85 _refine_ls_shift/su_mean 0.24 _computing_structure_refinement GSAS _refine_ls_number_parameters 54 _refine_ls_goodness_of_fit_all 4.18 _refine_ls_number_restraints 47 _refine_ls_matrix_type full #============================================================================== # 7. CHEMICAL, STRUCTURAL AND CRYSTAL DATA _pd_char_particle_morphology powder _chemical_name_systematic 5,12-dihydro-quino[2,3-b]acridine-7,14-dione _chemical_name_common 5,12-dihydro-quino(2,3-b)acridine-7,14-dione _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_melting_point '> 600' _chemical_compound_source 'Industrial, different phase than CCDC QNACRD03' # for minerals and # natural products _symmetry_space_group_name_Hall ? _exptl_crystal_F_000 ? _exptl_crystal_density_diffrn ? _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _cell_measurement_temperature ? _cell_special_details ; ? ; _geom_special_details ? # The following item identifies the program(s) used (if appropriate). _computing_structure_solution ? #============================================================================== # 8. Phase information from GSAS _pd_phase_name \a^I^-phase _cell_length_a 3.8017(15) _cell_length_b 6.6115(32) _cell_length_c 14.485(6) _cell_angle_alpha 100.68(8) _cell_angle_beta 94.40(6) _cell_angle_gamma 102.11(5) _cell_volume 346.67(11) _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +x,+y,+z -1 -x,-y,-z # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_thermal_displace_type _atom_site_U_iso_or_equiv _atom_site_symmetry_multiplicity C C1 -0.1801(9) 0.2899(8) 0.00389(16) 1.0 Uiso 0.0 2 C C2 -0.0950(6) 0.93844(28) 0.32941(13) 1.0 Uiso 0.0 2 C C3 -0.2214(7) 0.88132(28) 0.40125(14) 1.0 Uiso 0.0 2 C C4 -0.4174(7) 0.67258(29) 0.39547(14) 1.0 Uiso 0.0 2 C C5 -0.4314(6) 0.52042(28) 0.31486(13) 1.0 Uiso 0.0 2 C C6 -0.2718(7) 0.57655(29) 0.24486(14) 1.0 Uiso 0.0 2 C C7 -0.0973(7) 0.78218(31) 0.24905(14) 1.0 Uiso 0.0 2 C C8 0.0479(9) 0.83258(33) 0.15817(17) 1.0 Uiso 0.0 2 C C9 0.0258(9) 0.6712(7) 0.07670(16) 1.0 Uiso 0.0 2 C C10 -0.1523(8) 0.46009(32) 0.08064(16) 1.0 Uiso 0.0 2 H H12 0.0137(9) 1.0795(16) 0.33201(19) 1.0 Uiso 0.0 2 H H13 -0.2016(22) 0.9878(6) 0.46162(28) 1.0 Uiso 0.0 2 H H14 -0.5250(19) 0.6310(4) 0.4523(8) 1.0 Uiso 0.0 2 H H15 -0.5273(9) 0.3772(13) 0.31664(20) 1.0 Uiso 0.0 2 H H16 -0.4150(9) 0.2832(13) 0.16182(18) 1.0 Uiso 0.0 2 H H17 -0.3004(13) 0.1535(15) 0.00789(29) 1.0 Uiso 0.0 2 N N18 -0.3104(6) 0.41632(29) 0.16158(13) 1.0 Uiso 0.0 2 O O19 0.2160(13) 1.0388(14) 0.16011(25) 1.0 Uiso 0.0 2 # If you change Z, be sure to change all 3 of the following _chemical_formula_sum 'C20 H12 N2 O2' _chemical_formula_weight 312.32 _cell_formula_units_Z 1 # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C9 1.388(4) . -1_565 N C1 C10 1.408(4) . 1_555 N C1 H17 0.936(10) . 1_555 N C2 C3 1.2660(30) . 1_555 N C2 C7 1.4040(29) . 1_555 N C2 H12 0.930(10) . 1_555 N C2 H13 1.970(5) . 1_555 N C3 C2 1.2660(30) . 1_555 N C3 C4 1.4080(27) . 1_555 N C3 H12 1.912(8) . 1_555 N C3 H13 1.003(4) . 1_555 N C3 H14 2.097(7) . 1_555 N C4 C3 1.4080(27) . 1_555 N C4 C5 1.3824(28) . 1_555 N C4 H13 2.087(4) . 1_555 N C4 H14 1.004(11) . 1_555 N C4 H15 2.013(8) . 1_555 N C5 C4 1.3824(28) . 1_555 N C5 C6 1.2935(31) . 1_555 N C5 H14 2.074(10) . 1_555 N C5 H15 0.946(9) . 1_555 N C6 C5 1.2935(31) . 1_555 N C6 C7 1.3701(29) . 1_555 N C6 H15 1.971(7) . 1_555 N C6 H16 2.024(7) . 1_555 N C6 N18 1.4259(28) . 1_555 N C7 C2 1.4040(29) . 1_555 N C7 C6 1.3701(29) . 1_555 N C7 C8 1.531(4) . 1_555 N C7 H12 2.046(9) . 1_555 N C8 C7 1.531(4) . 1_555 N C8 C9 1.421(4) . 1_555 N C8 O19 1.373(9) . 1_555 N C9 C1 1.388(4) . -1_565 N C9 C8 1.421(4) . 1_555 N C9 C10 1.431(5) . 1_555 N C9 H17 2.037(8) . -1_565 N C10 C1 1.408(4) . 1_555 N C10 C9 1.431(5) . 1_555 N C10 H16 1.987(6) . 1_555 N C10 H17 2.043(9) . 1_555 N C10 N18 1.4073(33) . 1_555 N H12 C2 0.930(10) . 1_555 N H12 C3 1.912(8) . 1_555 N H12 C7 2.046(9) . 1_555 N H13 C2 1.970(5) . 1_555 N H13 C3 1.003(4) . 1_555 N H13 C4 2.087(4) . 1_555 N H13 H13 1.783(14) . -1_576 N H14 C3 2.097(7) . 1_555 N H14 C4 1.004(11) . 1_555 N H14 C5 2.074(10) . 1_555 N H15 C4 2.013(8) . 1_555 N H15 C5 0.946(9) . 1_555 N H15 C6 1.971(7) . 1_555 N H16 C6 2.024(7) . 1_555 N H16 C10 1.987(6) . 1_555 N H16 N18 0.887(8) . 1_555 N H16 O19 1.899(9) . 1_445 N H17 C1 0.936(10) . 1_555 N H17 C9 2.037(8) . -1_565 N H17 C10 2.043(9) . 1_555 N N18 C6 1.4259(28) . 1_555 N N18 C10 1.4073(33) . 1_555 N N18 H16 0.887(8) . 1_555 N O19 C8 1.373(9) . 1_555 N O19 H16 1.899(9) . 1_665 N loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 C1 C10 118.8(4) -1_565 . 1_555 N C9 C1 H17 121.2(5) -1_565 . 1_555 N C10 C1 H17 120.0(4) 1_555 . 1_555 N C3 C2 C7 118.43(18) 1_555 . 1_555 N C3 C2 H12 120.28(26) 1_555 . 1_555 N C7 C2 H12 121.09(28) 1_555 . 1_555 N C2 C3 C4 120.72(18) 1_555 . 1_555 N C2 C3 H13 120.10(33) 1_555 . 1_555 N C4 C3 H13 119.0(4) 1_555 . 1_555 N C3 C4 C5 119.96(21) 1_555 . 1_555 N C3 C4 H14 119.88(31) 1_555 . 1_555 N C5 C4 H14 119.87(29) 1_555 . 1_555 N C4 C5 C6 118.45(18) 1_555 . 1_555 N C4 C5 H15 118.38(28) 1_555 . 1_555 N C6 C5 H15 122.56(28) 1_555 . 1_555 N C5 C6 C7 121.31(19) 1_555 . 1_555 N C5 C6 N18 116.26(18) 1_555 . 1_555 N C7 C6 N18 122.29(20) 1_555 . 1_555 N C2 C7 C6 120.30(21) 1_555 . 1_555 N C2 C7 C8 123.02(18) 1_555 . 1_555 N C6 C7 C8 116.25(18) 1_555 . 1_555 N C7 C8 C9 121.44(23) 1_555 . 1_555 N C7 C8 O19 117.21(24) 1_555 . 1_555 N C9 C8 O19 121.28(30) 1_555 . 1_555 N C1 C9 C8 122.5(4) -1_565 . 1_555 N C1 C9 C10 119.65(33) -1_565 . 1_555 N C8 C9 C10 117.78(25) 1_555 . 1_555 N C1 C10 C9 121.57(26) 1_555 . 1_555 N C1 C10 N18 117.65(23) 1_555 . 1_555 N C9 C10 N18 120.77(20) 1_555 . 1_555 N C6 N18 C10 121.19(18) 1_555 . 1_555 N C6 N18 H16 120.29(28) 1_555 . 1_555 N C10 N18 H16 118.20(28) 1_555 . 1_555 N #--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--# #--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--# # Attachment 'beta_chin.CIF' data_0231 _database_code_depnum_ccdc_archive 'CCDC 620258' _audit_creation_method 'SHELXTL-plus (Sheldrick, 1997)' _chemical_name_systematic ; 7,14-dioxo-5,7,12,14-tetrahydro-chinolino-[2,3-b]-acridin ; _chemical_name_common 'beta-quinacridone (Pigment Violet 19, beta phase)' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H12 N2 O2' _chemical_formula_weight 312.32 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y+1/2, z+1/2' '-x, -y, -z' '-x, y-1/2, -z-1/2' _cell_length_a 5.692(1) _cell_length_b 3.975(1) _cell_length_c 30.02(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.76(6) _cell_angle_gamma 90.00 _cell_volume 674.5(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 18 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 11 _exptl_crystal_description 'very thin crystals' _exptl_crystal_colour red-violet _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 1.54 _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_method ; suspension in aqueous K(2)HgJ(4)-solution ; _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; The crystal was fixed in a Mark tube by a tiny bit of grease. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; computer controlled 4-circle diffractometer P3 (Nicolet) with a scintillation counter ; _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count '68 reflections' _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'no decay' _diffrn_reflns_number 2124 _diffrn_reflns_av_R_equivalents 0.1302 _diffrn_reflns_av_sigmaI/netI 0.1753 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 24.00 _reflns_number_total 1064 _reflns_number_gt 363 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nicolet software' _computing_cell_refinement 'Nicolet software' _computing_data_reduction 'Nicolet software' _computing_structure_solution 'SHELXTL-plus (Sheldrick, 1997)' _computing_structure_refinement 'SHELXTL-plus (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-plus (Sheldrick, 1997)' _computing_publication_material 'SHELXTL-plus (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1142P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1064 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1997 _refine_ls_R_factor_gt 0.0898 _refine_ls_wR_factor_ref 0.2728 _refine_ls_wR_factor_gt 0.2057 _refine_ls_goodness_of_fit_ref 0.908 _refine_ls_restrained_S_all 0.908 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2030(8) 0.4159(15) 0.08727(15) 0.0593(17) Uani 1 1 d . . . N1 N 0.7900(9) -0.1576(17) 0.07783(18) 0.0466(18) Uani 1 1 d . . . H1 H 0.9147 -0.2762 0.0758 0.046 Uiso 1 1 calc R . . C01 C 0.4916(13) 0.221(2) 0.1677(2) 0.057(2) Uani 1 1 d . . . H01 H 0.3580 0.3469 0.1717 0.059 Uiso 1 1 calc R . . C02 C 0.6420(13) 0.125(2) 0.2043(3) 0.059(2) Uani 1 1 d . . . H02 H 0.6062 0.1754 0.2330 0.077 Uiso 1 1 calc R . . C03 C 0.8501(12) -0.050(2) 0.1986(2) 0.056(2) Uani 1 1 d . . . H03 H 0.9560 -0.1030 0.2236 0.073 Uiso 1 1 calc R . . C04 C 0.9001(12) -0.143(2) 0.1572(2) 0.053(2) Uani 1 1 d . . . H04 H 1.0386 -0.2599 0.1539 0.065 Uiso 1 1 calc R . . C05 C 0.7430(10) -0.062(2) 0.1197(2) 0.046(2) Uani 1 1 d . . . C06 C 0.5353(11) 0.133(2) 0.1242(2) 0.046(2) Uani 1 1 d . . . C07 C 0.6497(10) -0.076(2) 0.0385(2) 0.0425(19) Uani 1 1 d . . . C08 C 0.4406(11) 0.110(2) 0.0414(2) 0.0411(18) Uani 1 1 d . . . C09 C 0.3805(12) 0.228(2) 0.0847(2) 0.0429(19) Uani 1 1 d . . . C10 C 0.2955(11) 0.181(2) 0.0021(2) 0.043(2) Uani 1 1 d . . . H10 H 0.1573 0.3033 0.0036 0.057 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.038(3) 0.084(4) 0.056(3) -0.006(3) 0.009(2) 0.015(3) N1 0.036(3) 0.056(5) 0.047(4) 0.010(3) 0.001(3) 0.010(3) C01 0.048(4) 0.083(7) 0.041(4) 0.002(5) 0.011(3) 0.004(5) C02 0.066(5) 0.063(6) 0.052(5) 0.004(5) 0.018(4) -0.008(5) C03 0.053(4) 0.052(6) 0.061(5) -0.004(5) 0.001(4) 0.014(5) C04 0.041(4) 0.064(6) 0.050(4) 0.003(5) -0.007(3) 0.009(4) C05 0.029(3) 0.076(7) 0.034(4) 0.001(4) 0.003(3) 0.001(4) C06 0.029(3) 0.064(6) 0.046(4) 0.009(5) 0.001(3) 0.002(4) C07 0.030(3) 0.047(5) 0.050(4) 0.013(4) 0.002(3) 0.002(4) C08 0.034(3) 0.051(5) 0.039(4) -0.005(4) 0.006(3) -0.004(4) C09 0.040(4) 0.043(5) 0.046(4) 0.001(4) 0.007(3) 0.000(4) C10 0.031(3) 0.052(6) 0.047(4) 0.000(4) 0.009(3) 0.008(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C09 1.265(8) . ? N1 C05 1.370(8) . ? N1 C07 1.384(8) . ? N1 H1 0.8600 . ? C01 C02 1.365(9) . ? C01 C06 1.401(9) . ? C01 H01 0.9300 . ? C02 C03 1.401(10) . ? C02 H02 0.9300 . ? C03 C04 1.359(8) . ? C03 H03 0.9300 . ? C04 C05 1.389(8) . ? C04 H04 0.9300 . ? C05 C06 1.433(10) . ? C06 C09 1.442(9) . ? C07 C10 1.360(9) 3_655 ? C07 C08 1.413(9) . ? C08 C10 1.387(9) . ? C08 C09 1.459(9) . ? C10 C07 1.360(9) 3_655 ? C10 H10 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C05 N1 C07 124.2(6) . . ? C05 N1 H1 117.9 . . ? C07 N1 H1 117.9 . . ? C02 C01 C06 121.1(7) . . ? C02 C01 H01 119.5 . . ? C06 C01 H01 119.5 . . ? C01 C02 C03 120.0(7) . . ? C01 C02 H02 120.0 . . ? C03 C02 H02 120.0 . . ? C04 C03 C02 121.2(7) . . ? C04 C03 H03 119.4 . . ? C02 C03 H03 119.4 . . ? C03 C04 C05 119.5(7) . . ? C03 C04 H04 120.2 . . ? C05 C04 H04 120.2 . . ? N1 C05 C04 120.1(7) . . ? N1 C05 C06 119.3(6) . . ? C04 C05 C06 120.6(6) . . ? C01 C06 C05 117.5(6) . . ? C01 C06 C09 122.8(7) . . ? C05 C06 C09 119.7(6) . . ? C10 C07 N1 121.5(7) 3_655 . ? C10 C07 C08 120.1(6) 3_655 . ? N1 C07 C08 118.4(6) . . ? C10 C08 C07 118.3(6) . . ? C10 C08 C09 120.9(7) . . ? C07 C08 C09 120.7(6) . . ? O1 C09 C06 121.3(7) . . ? O1 C09 C08 121.0(6) . . ? C06 C09 C08 117.6(7) . . ? C07 C10 C08 121.6(6) 3_655 . ? C07 C10 H10 119.2 3_655 . ? C08 C10 H10 119.2 . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C06 C01 C02 C03 3.3(13) . . . . ? C01 C02 C03 C04 -3.6(13) . . . . ? C02 C03 C04 C05 0.4(13) . . . . ? C07 N1 C05 C04 -177.0(8) . . . . ? C07 N1 C05 C06 0.6(11) . . . . ? C03 C04 C05 N1 -179.2(8) . . . . ? C03 C04 C05 C06 3.1(12) . . . . ? C02 C01 C06 C05 0.2(12) . . . . ? C02 C01 C06 C09 179.8(8) . . . . ? N1 C05 C06 C01 178.9(7) . . . . ? C04 C05 C06 C01 -3.4(12) . . . . ? N1 C05 C06 C09 -0.7(12) . . . . ? C04 C05 C06 C09 177.0(7) . . . . ? C05 N1 C07 C10 -179.4(8) . . . 3_655 ? C05 N1 C07 C08 -1.9(11) . . . . ? C10 C07 C08 C10 0.0(12) 3_655 . . . ? N1 C07 C08 C10 -177.6(7) . . . . ? C10 C07 C08 C09 -179.3(7) 3_655 . . . ? N1 C07 C08 C09 3.1(10) . . . . ? C01 C06 C09 O1 4.4(12) . . . . ? C05 C06 C09 O1 -176.0(7) . . . . ? C01 C06 C09 C08 -177.7(7) . . . . ? C05 C06 C09 C08 1.9(11) . . . . ? C10 C08 C09 O1 -4.5(11) . . . . ? C07 C08 C09 O1 174.7(7) . . . . ? C10 C08 C09 C06 177.6(7) . . . . ? C07 C08 C09 C06 -3.2(10) . . . . ? C07 C08 C10 C07 0.0(12) . . . 3_655 ? C09 C08 C10 C07 179.3(7) . . . 3_655 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.86 2.04 2.885(8) 165.9 1_645 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.276 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.077 # Attachment 'gamma_chin.cif' data_0188 _database_code_depnum_ccdc_archive 'CCDC 620259' _audit_creation_method 'SHELXTL-plus (Sheldrick, 1997)' _chemical_name_systematic ; 7,14-dioxo-5,7,12,14-tetrahydro-chinolino-[2,3-b]-acridin ; _chemical_name_common 'gamma-quinacridone (Pigment Violet 19, gamma phase)' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H12 N2 O2' _chemical_formula_weight 312.32 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2(1)/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y+1/2, z+1/2' '-x, -y, -z' '-x, y-1/2, -z-1/2' _cell_length_a 13.697(9) _cell_length_b 3.881(3) _cell_length_c 13.4020(10) _cell_angle_alpha 90.00 _cell_angle_beta 100.44(1) _cell_angle_gamma 90.00 _cell_volume 700.6(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 23 _cell_measurement_theta_min 3 _cell_measurement_theta_max 14 _exptl_crystal_description 'very thin plates' _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.65mm _exptl_crystal_size_mid 0.3mm _exptl_crystal_size_min 0.01mm _exptl_crystal_density_meas 1.47 _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method ; suspension in aqueous K(2)HgJ(4) solution ; _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; The crystal was fixed in a Mark tube by a very small amount of grease. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; computer controlled 4-circle diffractometer P3 (Nicolet) ; _diffrn_measurement_method ; two theta/theta scan, scintillation counter ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count 'every 20 reflections' _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'no decay' _diffrn_reflns_number 895 _diffrn_reflns_av_R_equivalents 0.0717 _diffrn_reflns_av_sigmaI/netI 0.1575 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 21.98 _reflns_number_total 846 _reflns_number_gt 330 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXTL-plus (Sheldrick, 1997)' _computing_structure_refinement 'SHELXTL-plus (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-plus (Sheldrick, 1997)' _computing_publication_material 'SHELXTL-plus (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method 'SHELXTL-plus (Sheldrick, 1997)' _refine_ls_extinction_coef 1.4(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 846 _refine_ls_number_parameters 98 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2742 _refine_ls_R_factor_gt 0.2090 _refine_ls_wR_factor_ref 0.4555 _refine_ls_wR_factor_gt 0.4250 _refine_ls_goodness_of_fit_ref 1.289 _refine_ls_restrained_S_all 1.289 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3291(10) 0.422(3) 0.1445(7) 0.113(5) Uani 1 1 d . . . N1 N 0.3499(9) 0.227(3) -0.1485(8) 0.066(4) Uani 1 1 d . . . H1 H 0.3542 0.1886 -0.2107 0.100 Uiso 1 1 calc R . . C01 C 0.1700(13) 0.618(5) -0.0122(11) 0.076(5) Uani 1 1 d . . . H01 H 0.1635 0.6664 0.0542 0.114 Uiso 1 1 calc R . . C02 C 0.0947(14) 0.716(5) -0.0889(11) 0.094(6) Uani 1 1 d . . . H02 H 0.0383 0.8260 -0.0751 0.141 Uiso 1 1 calc R . . C03 C 0.1060(15) 0.642(6) -0.1927(11) 0.089(6) Uani 1 1 d . . . H03 H 0.0552 0.6931 -0.2467 0.134 Uiso 1 1 calc R . . C04 C 0.1923(14) 0.496(5) -0.2097(11) 0.088(6) Uani 1 1 d . . . H04 H 0.2005 0.4629 -0.2764 0.132 Uiso 1 1 calc R . . C05 C 0.2676(13) 0.397(4) -0.1325(9) 0.061(5) Uani 1 1 d . . . C06 C 0.2561(11) 0.448(4) -0.0281(8) 0.056(4) Uani 1 1 d . . . C07 C 0.4262(11) 0.109(4) -0.0774(9) 0.054(4) Uani 1 1 d . . . C08 C 0.4189(12) 0.180(4) 0.0283(9) 0.055(4) Uani 1 1 d . . . C09 C 0.3344(12) 0.351(4) 0.0509(9) 0.063(5) Uani 1 1 d . . . C10 C 0.4939(14) 0.054(4) 0.0985(9) 0.068(5) Uani 1 1 d . . . H10 H 0.4897 0.0840 0.1664 0.103 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.199(13) 0.113(11) 0.043 -0.009(7) 0.059(6) 0.033(10) N1 0.099(10) 0.070(9) 0.035 0.012(6) 0.024(6) 0.019(9) C01 0.092(12) 0.086(13) 0.050 0.029(9) 0.012(9) 0.024(12) C02 0.124(15) 0.114(16) 0.051 0.001(11) 0.034(9) 0.038(14) C03 0.102(13) 0.113(16) 0.054 0.013(11) 0.016(9) -0.003(14) C04 0.113(15) 0.104(17) 0.045 0.010(10) 0.005(9) 0.014(13) C05 0.099(12) 0.058(10) 0.028 0.011(7) 0.017(7) 0.024(10) C06 0.063(10) 0.078(11) 0.028 -0.019(7) 0.015(6) -0.008(10) C07 0.066(10) 0.066(11) 0.030 0.018(8) 0.006(7) -0.007(10) C08 0.093(11) 0.047(10) 0.027 0.018(7) 0.012(7) 0.002(9) C09 0.068(10) 0.085(13) 0.038 -0.019(9) 0.011(7) -0.002(10) C10 0.133(14) 0.047(10) 0.036 0.009(8) 0.046(8) -0.001(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C09 1.300(15) . ? N1 C05 1.355(17) . ? N1 C07 1.359(16) . ? N1 H1 0.8600 . ? C01 C02 1.37(2) . ? C01 C06 1.400(19) . ? C01 H01 0.9300 . ? C02 C03 1.46(2) . ? C02 H02 0.9300 . ? C03 C04 1.37(2) . ? C03 H03 0.9300 . ? C04 C05 1.38(2) . ? C04 H04 0.9300 . ? C05 C06 1.450(17) . ? C06 C09 1.415(19) . ? C07 C10 1.339(18) 3_655 ? C07 C08 1.464(18) . ? C08 C10 1.351(19) . ? C08 C09 1.413(19) . ? C10 C07 1.339(18) 3_655 ? C10 H10 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C05 N1 C07 127.5(12) . . ? C05 N1 H1 116.3 . . ? C07 N1 H1 116.3 . . ? C02 C01 C06 123.8(15) . . ? C02 C01 H01 118.1 . . ? C06 C01 H01 118.1 . . ? C01 C02 C03 117.7(18) . . ? C01 C02 H02 121.1 . . ? C03 C02 H02 121.1 . . ? C04 C03 C02 119.1(17) . . ? C04 C03 H03 120.4 . . ? C02 C03 H03 120.4 . . ? C03 C04 C05 122.9(16) . . ? C03 C04 H04 118.5 . . ? C05 C04 H04 118.5 . . ? N1 C05 C04 123.3(14) . . ? N1 C05 C06 117.3(13) . . ? C04 C05 C06 119.2(17) . . ? C01 C06 C09 123.9(12) . . ? C01 C06 C05 117.0(14) . . ? C09 C06 C05 119.0(14) . . ? C10 C07 N1 124.5(13) 3_655 . ? C10 C07 C08 119.6(12) 3_655 . ? N1 C07 C08 115.9(15) . . ? C10 C08 C09 124.7(12) . . ? C10 C08 C07 115.4(13) . . ? C09 C08 C07 119.8(13) . . ? O1 C09 C08 119.9(13) . . ? O1 C09 C06 119.8(15) . . ? C08 C09 C06 120.3(12) . . ? C07 C10 C08 124.9(12) 3_655 . ? C07 C10 H10 117.6 3_655 . ? C08 C10 H10 117.6 . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C06 C01 C02 C03 -1(3) . . . . ? C01 C02 C03 C04 -3(3) . . . . ? C02 C03 C04 C05 4(3) . . . . ? C07 N1 C05 C04 -177.8(16) . . . . ? C07 N1 C05 C06 -3(2) . . . . ? C03 C04 C05 N1 174.4(17) . . . . ? C03 C04 C05 C06 0(3) . . . . ? C02 C01 C06 C09 179.2(19) . . . . ? C02 C01 C06 C05 4(3) . . . . ? N1 C05 C06 C01 -178.7(14) . . . . ? C04 C05 C06 C01 -4(2) . . . . ? N1 C05 C06 C09 6(2) . . . . ? C04 C05 C06 C09 -179.0(15) . . . . ? C05 N1 C07 C10 -179.3(15) . . . 3_655 ? C05 N1 C07 C08 -1(2) . . . . ? C10 C07 C08 C10 -3(2) 3_655 . . . ? N1 C07 C08 C10 178.4(13) . . . . ? C10 C07 C08 C09 -179.6(14) 3_655 . . . ? N1 C07 C08 C09 2(2) . . . . ? C10 C08 C09 O1 6(2) . . . . ? C07 C08 C09 O1 -178.0(14) . . . . ? C10 C08 C09 C06 -174.9(16) . . . . ? C07 C08 C09 C06 1(2) . . . . ? C01 C06 C09 O1 -1(3) . . . . ? C05 C06 C09 O1 174.0(15) . . . . ? C01 C06 C09 C08 180.0(15) . . . . ? C05 C06 C09 C08 -5(2) . . . . ? C09 C08 C10 C07 179.6(15) . . . 3_655 ? C07 C08 C10 C07 3(2) . . . 3_655 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.86 1.96 2.797(14) 165.8 2_554 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 21.98 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.874 _refine_diff_density_min -0.745 _refine_diff_density_rms 0.291