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


