#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:21:15 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179626 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/90/4509085.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4509085
loop_
_publ_author_name
'Fan, Yan'
'Zhao, Yunfeng'
'Ye, Ling'
'Li, Bao'
'Yang, Guangdi'
'Wang, Yue'
_publ_section_title
;
 Polymorphs and Pseudopolymorphs ofN,N-Di(n-butyl)Quinacridone: Structures
 and Solid-State Luminescence Properties
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1421
_journal_paper_doi               10.1021/cg800785u
_journal_volume                  9
_journal_year                    2009
_chemical_formula_sum            'C29 H29 Cl3 N2 O2'
_chemical_formula_weight         543.89
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.12(3)
_cell_angle_beta                 94.83(3)
_cell_angle_gamma                90.82(3)
_cell_formula_units_Z            2
_cell_length_a                   5.0722(10)
_cell_length_b                   15.926(3)
_cell_length_c                   17.571(4)
_cell_measurement_reflns_used    5987
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.61
_cell_measurement_theta_min      3
_cell_volume                     1335.0(5)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean none
_diffrn_measured_fraction_theta_full 0.933
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'Omega scan'
_diffrn_measurement_method       10.0
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1244
_diffrn_reflns_av_sigmaI/netI    0.2125
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12637
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.00
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_T_max  0.9658
_exptl_absorpt_correction_T_min  0.8737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;   
Higash,T(1995) Progrom for Absorption Correcttion.
Rigaku Corporation,Tokyo,Japan. 
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         5745
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.2579
_refine_ls_R_factor_gt           0.0935
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0933P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1928
_refine_ls_wR_factor_ref         0.2582
_reflns_number_gt                1851
_reflns_number_total             5745
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg800785usup1.cif
_cod_data_source_block           F
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               4509085
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.4786(10) 0.8800(3) 0.3392(3) 0.0514(13) Uani 1 1 d .
C2 C 0.3099(10) 0.8111(4) 0.2852(3) 0.0607(15) Uani 1 1 d .
H2 H 0.3416 0.7521 0.2794 0.073 Uiso 1 1 calc R
C3 C 0.1009(11) 0.8312(4) 0.2415(3) 0.0675(16) Uani 1 1 d .
H3 H -0.0100 0.7853 0.2065 0.081 Uiso 1 1 calc R
C4 C 0.0490(11) 0.9177(4) 0.2478(3) 0.0647(15) Uani 1 1 d .
H4 H -0.0951 0.9303 0.2175 0.078 Uiso 1 1 calc R
C5 C 0.2132(10) 0.9850(4) 0.2994(3) 0.0600(14) Uani 1 1 d .
H5 H 0.1804 1.0437 0.3038 0.072 Uiso 1 1 calc R
C6 C 0.4265(9) 0.9672(3) 0.3449(3) 0.0509(13) Uani 1 1 d .
C7 C 0.5954(10) 1.0415(3) 0.3991(3) 0.0532(13) Uani 1 1 d .
C8 C 0.8011(9) 1.0187(3) 0.4502(3) 0.0466(12) Uani 1 1 d .
C9 C 0.9597(9) 1.0860(3) 0.5046(3) 0.0483(12) Uani 1 1 d .
H9 H 0.9326 1.1443 0.5066 0.058 Uiso 1 1 calc R
C10 C 0.8431(10) 0.9296(3) 0.4437(3) 0.0479(12) Uani 1 1 d .
C11 C 0.7558(10) 0.7688(3) 0.3738(3) 0.0583(14) Uani 1 1 d .
H11A H 0.9459 0.7681 0.3857 0.070 Uiso 1 1 calc R
H11B H 0.7133 0.7341 0.3172 0.070 Uiso 1 1 calc R
C12 C 0.6223(11) 0.7244(3) 0.4241(4) 0.0697(16) Uani 1 1 d .
H12A H 0.4362 0.7129 0.4047 0.084 Uiso 1 1 calc R
H12B H 0.6350 0.7636 0.4798 0.084 Uiso 1 1 calc R
C13 C 0.7492(15) 0.6372(4) 0.4201(5) 0.094(2) Uani 1 1 d .
H13A H 0.7589 0.6022 0.3638 0.113 Uiso 1 1 calc R
H13B H 0.9290 0.6503 0.4456 0.113 Uiso 1 1 calc R
C14 C 0.606(2) 0.5830(5) 0.4597(6) 0.142(3) Uani 1 1 d .
H14A H 0.5780 0.6191 0.5138 0.213 Uiso 1 1 calc R
H14B H 0.7096 0.5336 0.4614 0.213 Uiso 1 1 calc R
H14C H 0.4382 0.5614 0.4294 0.213 Uiso 1 1 calc R
C15 C 0.4847(9) 0.4073(3) 0.0920(3) 0.0529(13) Uani 1 1 d .
C16 C 0.3106(10) 0.3486(4) 0.1081(3) 0.0627(15) Uani 1 1 d .
H16 H 0.2929 0.2899 0.0738 0.075 Uiso 1 1 calc R
C17 C 0.1652(10) 0.3746(4) 0.1729(4) 0.0691(16) Uani 1 1 d .
H17 H 0.0488 0.3338 0.1818 0.083 Uiso 1 1 calc R
C18 C 0.1891(11) 0.4619(4) 0.2262(4) 0.0720(17) Uani 1 1 d .
H18 H 0.0885 0.4801 0.2701 0.086 Uiso 1 1 calc R
C19 C 0.3622(10) 0.5191(4) 0.2122(3) 0.0646(15) Uani 1 1 d .
H19 H 0.3805 0.5772 0.2480 0.077 Uiso 1 1 calc R
C20 C 0.5157(9) 0.4951(3) 0.1463(3) 0.0536(13) Uani 1 1 d .
C21 C 0.6989(9) 0.5590(3) 0.1355(3) 0.0522(13) Uani 1 1 d .
C22 C 0.8518(9) 0.5269(3) 0.0653(3) 0.0485(12) Uani 1 1 d .
C23 C 0.8111(9) 0.4403(3) 0.0115(3) 0.0463(12) Uani 1 1 d .
C24 C 0.9642(9) 0.4143(3) -0.0536(3) 0.0485(12) Uani 1 1 d .
H24 H 0.9430 0.3566 -0.0899 0.058 Uiso 1 1 calc R
C25 C 0.5629(9) 0.2940(3) -0.0367(3) 0.0593(14) Uani 1 1 d .
H25A H 0.6018 0.2966 -0.0891 0.071 Uiso 1 1 calc R
H25B H 0.3745 0.2803 -0.0398 0.071 Uiso 1 1 calc R
C26 C 0.7132(10) 0.2194(3) -0.0201(3) 0.0630(15) Uani 1 1 d .
H26A H 0.8930 0.2219 -0.0345 0.076 Uiso 1 1 calc R
H26B H 0.7219 0.2278 0.0373 0.076 Uiso 1 1 calc R
C27 C 0.5866(11) 0.1295(4) -0.0666(4) 0.0797(18) Uani 1 1 d .
H27A H 0.5706 0.1219 -0.1239 0.096 Uiso 1 1 calc R
H27B H 0.4098 0.1259 -0.0504 0.096 Uiso 1 1 calc R
C28 C 0.7460(15) 0.0548(4) -0.0524(5) 0.114(3) Uani 1 1 d .
H28A H 0.9188 0.0567 -0.0704 0.172 Uiso 1 1 calc R
H28B H 0.6569 -0.0014 -0.0820 0.172 Uiso 1 1 calc R
H28C H 0.7629 0.0622 0.0043 0.172 Uiso 1 1 calc R
C29 C 0.7436(14) 0.2273(5) 0.3036(4) 0.118(3) Uani 1 1 d D
Cl1 Cl 0.656(2) 0.3326(5) 0.3056(8) 0.133(3) Uani 0.60 1 d PD
Cl2 Cl 1.0510(9) 0.2315(4) 0.3559(5) 0.1234(19) Uani 0.60 1 d PD
Cl3 Cl 0.739(4) 0.1517(12) 0.2073(7) 0.261(9) Uani 0.60 1 d PD
Cl4 Cl 0.708(8) 0.3418(9) 0.336(2) 0.21(2) Uani 0.20 1 d PD
Cl5 Cl 0.572(4) 0.275(2) 0.2402(17) 0.234(15) Uani 0.20 1 d PD
Cl6 Cl 0.595(7) 0.1770(16) 0.2044(10) 0.28(3) Uani 0.20 1 d PD
Cl7 Cl 0.848(8) 0.1582(15) 0.2133(10) 0.178(17) Uani 0.20 1 d PD
Cl8 Cl 1.039(4) 0.189(2) 0.262(2) 0.37(3) Uani 0.20 1 d PD
Cl9 Cl 1.023(4) 0.2814(17) 0.366(2) 0.222(15) Uani 0.20 1 d PD
N1 N 0.6847(8) 0.8608(2) 0.3858(3) 0.0523(11) Uani 1 1 d .
N2 N 0.6247(7) 0.3818(2) 0.0241(2) 0.0507(11) Uani 1 1 d .
O1 O 0.5619(7) 1.1185(2) 0.4012(2) 0.0696(11) Uani 1 1 d .
O2 O 0.7229(7) 0.6369(2) 0.1815(2) 0.0732(11) Uani 1 1 d .
H29 H 0.621(12) 0.215(6) 0.329(5) 0.17(4) Uiso 1 1 d D
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'
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
N1 C1 C6 121.4(5) .
N1 C1 C2 120.5(5) .
C6 C1 C2 118.1(5) .
C3 C2 C1 119.9(5) .
C2 C3 C4 121.8(5) .
C5 C4 C3 118.8(5) .
C4 C5 C6 121.1(5) .
C5 C6 C1 120.3(5) .
C5 C6 C7 118.9(5) .
C1 C6 C7 120.8(5) .
O1 C7 C8 122.5(5) .
O1 C7 C6 121.7(5) .
C8 C7 C6 115.9(5) .
C9 C8 C10 120.1(4) .
C9 C8 C7 118.6(4) .
C10 C8 C7 121.2(4) .
C10 C9 C8 122.4(5) 2_776
C9 C10 C8 117.4(4) 2_776
C9 C10 N1 122.9(4) 2_776
C8 C10 N1 119.7(5) .
N1 C11 C12 115.2(4) .
C11 C12 C13 110.9(5) .
C14 C13 C12 114.3(6) .
C16 C15 N2 121.7(5) .
C16 C15 C20 118.3(5) .
N2 C15 C20 119.9(5) .
C17 C16 C15 121.7(5) .
C16 C17 C18 120.6(6) .
C19 C18 C17 118.2(5) .
C18 C19 C20 123.0(5) .
C19 C20 C15 118.0(5) .
C19 C20 C21 120.2(5) .
C15 C20 C21 121.8(5) .
O2 C21 C20 122.3(5) .
O2 C21 C22 121.8(5) .
C20 C21 C22 115.8(4) .
C24 C22 C23 121.2(4) 2_765
C24 C22 C21 117.9(4) 2_765
C23 C22 C21 121.0(5) .
C24 C23 C22 117.8(4) .
C24 C23 N2 121.7(4) .
C22 C23 N2 120.5(4) .
C22 C24 C23 121.0(4) 2_765
N2 C25 C26 114.3(4) .
C27 C26 C25 112.4(4) .
C26 C27 C28 111.9(5) .
Cl3 C29 Cl1 113.6(9) .
Cl3 C29 Cl5 73.8(13) .
Cl1 C29 Cl5 42.3(12) .
Cl3 C29 Cl2 110.0(9) .
Cl1 C29 Cl2 110.8(7) .
Cl5 C29 Cl2 141.4(12) .
Cl3 C29 Cl4 130.3(17) .
Cl1 C29 Cl4 18.0(18) .
Cl5 C29 Cl4 60.3(19) .
Cl2 C29 Cl4 95.8(15) .
Cl3 C29 Cl7 18.5(19) .
Cl1 C29 Cl7 116.4(10) .
Cl5 C29 Cl7 82.9(16) .
Cl2 C29 Cl7 92.8(14) .
Cl4 C29 Cl7 129.2(17) .
Cl3 C29 Cl9 126.3(15) .
Cl1 C29 Cl9 85.2(11) .
Cl5 C29 Cl9 120.8(18) .
Cl2 C29 Cl9 25.8(9) .
Cl4 C29 Cl9 70.1(17) .
Cl7 C29 Cl9 107.8(18) .
Cl3 C29 Cl8 59.2(17) .
Cl1 C29 Cl8 116.9(10) .
Cl5 C29 Cl8 107.7(11) .
Cl2 C29 Cl8 53.3(14) .
Cl4 C29 Cl8 116.6(18) .
Cl7 C29 Cl8 40.8(17) .
Cl9 C29 Cl8 67.4(17) .
Cl3 C29 Cl6 28.0(14) .
Cl1 C29 Cl6 92.9(10) .
Cl5 C29 Cl6 50.6(16) .
Cl2 C29 Cl6 137.5(12) .
Cl4 C29 Cl6 110.9(18) .
Cl7 C29 Cl6 44.7(19) .
Cl9 C29 Cl6 147(2) .
Cl8 C29 Cl6 84.7(18) .
C1 N1 C10 120.7(4) .
C1 N1 C11 121.2(4) .
C10 N1 C11 118.0(4) .
C15 N2 C23 120.8(4) .
C15 N2 C25 118.7(4) .
C23 N2 C25 120.4(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.372(6) .
C1 C6 1.392(7) .
C1 C2 1.411(7) .
C2 C3 1.359(7) .
C3 C4 1.377(7) .
C4 C5 1.369(7) .
C5 C6 1.379(7) .
C6 C7 1.462(7) .
C7 O1 1.229(6) .
C7 C8 1.447(7) .
C8 C9 1.373(6) .
C8 C10 1.408(6) .
C9 C10 1.374(6) 2_776
C10 C9 1.374(6) 2_776
C10 N1 1.411(6) .
C11 N1 1.465(6) .
C11 C12 1.495(7) .
C12 C13 1.522(7) .
C13 C14 1.489(10) .
C15 C16 1.388(7) .
C15 N2 1.388(6) .
C15 C20 1.409(7) .
C16 C17 1.361(7) .
C17 C18 1.395(8) .
C18 C19 1.350(8) .
C19 C20 1.402(7) .
C20 C21 1.436(7) .
C21 O2 1.236(6) .
C21 C22 1.464(6) .
C22 C24 1.387(7) 2_765
C22 C23 1.395(6) .
C23 C24 1.390(6) .
C23 N2 1.399(6) .
C24 C22 1.387(6) 2_765
C25 N2 1.465(6) .
C25 C26 1.515(7) .
C26 C27 1.499(7) .
C27 C28 1.522(8) .
C29 Cl3 1.724(9) .
C29 Cl1 1.731(8) .
C29 Cl5 1.727(9) .
C29 Cl2 1.731(8) .
C29 Cl4 1.741(10) .
C29 Cl7 1.739(10) .
C29 Cl9 1.741(10) .
C29 Cl8 1.750(10) .
C29 Cl6 1.758(10) .
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
C29 H29 O1 0.855(10) 2.32(6) 2.994(9) 136(8) 1_545
C25 H25A O2 0.97 2.68 3.323(7) 123.8 2_665
C5 H5 Cl8 0.93 2.74 3.63(2) 160.6 1_465
C5 H5 Cl7 0.93 3.20 3.96(3) 141.1 1_465
C5 H5 Cl2 0.93 2.93 3.840(9) 166.6 1_465
C3 H3 O2 0.93 2.60 3.423(7) 148.3 1_455
