#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:21:15 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179626 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/90/4509083.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_4509083
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            'C28 H28 N2 O2'
_chemical_formula_weight         424.52
_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                94.67(3)
_cell_angle_beta                 90.58(3)
_cell_angle_gamma                101.87(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1938(14)
_cell_length_b                   10.337(2)
_cell_length_c                   15.022(3)
_cell_measurement_reflns_used    5713
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.17
_cell_volume                     1089.1(4)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        RAPID-AUTO
_computing_molecular_graphics    SHELXL97
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_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  0.0838
_diffrn_reflns_av_sigmaI/netI    0.1254
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10764
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.16
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_correction_T_min  0.9694
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;   
Higash,T(1995) Progrom for Absorption Correcttion.
Rigaku Corporation,Tokyo,Japan. 
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.1967
_refine_ls_R_factor_gt           0.0746
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0850P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1585
_refine_ls_wR_factor_ref         0.2055
_reflns_number_gt                2016
_reflns_number_total             4939
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg800785usup1.cif
_cod_data_source_block           D
_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 
;
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               4509083
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 0.1257(5) 0.9169(3) 0.9696(2) 0.0327(8) Uani 1 1 d .
C2 C 0.1439(5) 0.9824(3) 1.0563(2) 0.0349(8) Uani 1 1 d .
C3 C 0.0209(5) 1.0623(3) 1.0855(2) 0.0373(8) Uani 1 1 d .
H3 H 0.0361 1.1032 1.1433 0.045 Uiso 1 1 calc R
C4 C 0.2993(5) 0.9709(3) 1.1175(2) 0.0364(8) Uani 1 1 d .
C5 C 0.4169(5) 0.8794(3) 1.0860(2) 0.0347(8) Uani 1 1 d .
C6 C 0.5607(5) 0.8568(4) 1.1424(2) 0.0442(9) Uani 1 1 d .
H6 H 0.5777 0.9005 1.1995 0.053 Uiso 1 1 calc R
C7 C 0.6775(6) 0.7720(4) 1.1161(3) 0.0517(10) Uani 1 1 d .
H7 H 0.7731 0.7584 1.1542 0.062 Uiso 1 1 calc R
C8 C 0.6490(5) 0.7072(4) 1.0313(2) 0.0518(10) Uani 1 1 d .
H8 H 0.7274 0.6494 1.0129 0.062 Uiso 1 1 calc R
C9 C 0.5099(5) 0.7248(4) 0.9735(2) 0.0449(9) Uani 1 1 d .
H9 H 0.4935 0.6784 0.9173 0.054 Uiso 1 1 calc R
C10 C 0.3915(5) 0.8135(3) 0.9994(2) 0.0356(8) Uani 1 1 d .
C11 C 0.2370(5) 0.7807(3) 0.8470(2) 0.0427(9) Uani 1 1 d .
H11A H 0.3577 0.7588 0.8307 0.051 Uiso 1 1 calc R
H11B H 0.2143 0.8481 0.8094 0.051 Uiso 1 1 calc R
C12 C 0.0781(7) 0.6557(4) 0.8281(3) 0.0679(14) Uani 1 1 d .
H12A H -0.0425 0.6805 0.8408 0.082 Uiso 1 1 calc R
H12B H 0.0766 0.6282 0.7648 0.082 Uiso 1 1 calc R
C13 C 0.0889(7) 0.5414(4) 0.8771(3) 0.0720(14) Uani 1 1 d .
H13A H 0.0997 0.5689 0.9405 0.086 Uiso 1 1 calc R
H13B H 0.2028 0.5099 0.8604 0.086 Uiso 1 1 calc R
C14 C -0.0836(7) 0.4274(4) 0.8594(3) 0.0757(14) Uani 1 1 d .
H14A H -0.1973 0.4585 0.8742 0.114 Uiso 1 1 calc R
H14B H -0.0721 0.3568 0.8956 0.114 Uiso 1 1 calc R
H14C H -0.0897 0.3952 0.7975 0.114 Uiso 1 1 calc R
C15 C 0.1151(5) 0.1905(3) 0.5188(2) 0.0370(8) Uani 1 1 d .
C16 C 0.0024(5) 0.2845(4) 0.5045(2) 0.0472(10) Uani 1 1 d .
H16 H 0.0238 0.3344 0.4554 0.057 Uiso 1 1 calc R
C17 C -0.1366(6) 0.3026(4) 0.5618(3) 0.0523(10) Uani 1 1 d .
H17 H -0.2078 0.3658 0.5515 0.063 Uiso 1 1 calc R
C18 C -0.1752(6) 0.2291(4) 0.6355(3) 0.0550(11) Uani 1 1 d .
H18 H -0.2736 0.2405 0.6731 0.066 Uiso 1 1 calc R
C19 C -0.0664(5) 0.1405(4) 0.6514(2) 0.0432(9) Uani 1 1 d .
H19 H -0.0894 0.0927 0.7014 0.052 Uiso 1 1 calc R
C20 C 0.0803(5) 0.1186(3) 0.5946(2) 0.0365(8) Uani 1 1 d .
C21 C 0.1929(5) 0.0229(3) 0.6152(2) 0.0371(8) Uani 1 1 d .
C22 C 0.3508(5) 0.0133(3) 0.5556(2) 0.0342(8) Uani 1 1 d .
C23 C 0.3767(5) 0.0856(3) 0.4796(2) 0.0346(8) Uani 1 1 d .
C24 C 0.5270(5) 0.0687(3) 0.4247(2) 0.0359(8) Uani 1 1 d .
H24 H 0.5456 0.1139 0.3734 0.043 Uiso 1 1 calc R
C25 C 0.2788(5) 0.2357(3) 0.3768(2) 0.0400(9) Uani 1 1 d .
H25A H 0.1572 0.2511 0.3569 0.048 Uiso 1 1 calc R
H25B H 0.3227 0.1788 0.3307 0.048 Uiso 1 1 calc R
C26 C 0.4207(5) 0.3678(4) 0.3896(2) 0.0461(9) Uani 1 1 d .
H26A H 0.3838 0.4203 0.4402 0.055 Uiso 1 1 calc R
H26B H 0.5450 0.3509 0.4037 0.055 Uiso 1 1 calc R
C27 C 0.4353(6) 0.4465(4) 0.3096(2) 0.0568(11) Uani 1 1 d .
H27A H 0.3123 0.4663 0.2967 0.068 Uiso 1 1 calc R
H27B H 0.4687 0.3932 0.2584 0.068 Uiso 1 1 calc R
C28 C 0.5818(7) 0.5751(5) 0.3230(3) 0.0750(14) Uani 1 1 d .
H28A H 0.5528 0.6265 0.3752 0.113 Uiso 1 1 calc R
H28B H 0.5796 0.6245 0.2717 0.113 Uiso 1 1 calc R
H28C H 0.7057 0.5559 0.3305 0.113 Uiso 1 1 calc R
N1 N 0.2504(4) 0.8358(3) 0.94078(16) 0.0360(7) Uani 1 1 d .
N2 N 0.2535(4) 0.1678(3) 0.45940(16) 0.0357(7) Uani 1 1 d .
O1 O 0.3270(4) 1.0351(3) 1.19155(15) 0.0534(7) Uani 1 1 d .
O2 O 0.1589(4) -0.0461(3) 0.67883(15) 0.0528(7) Uani 1 1 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'
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
C3 C1 N1 122.1(3) 2_577 .
C3 C1 C2 117.0(3) 2_577 .
N1 C1 C2 121.0(3) . .
C3 C2 C1 121.4(3) . .
C3 C2 C4 117.9(3) . .
C1 C2 C4 120.7(3) . .
C2 C3 C1 121.6(3) . 2_577
O1 C4 C5 122.2(3) . .
O1 C4 C2 122.0(3) . .
C5 C4 C2 115.8(3) . .
C6 C5 C10 119.1(3) . .
C6 C5 C4 119.3(3) . .
C10 C5 C4 121.6(3) . .
C7 C6 C5 121.9(3) . .
C6 C7 C8 118.1(3) . .
C9 C8 C7 122.5(4) . .
C8 C9 C10 119.7(3) . .
N1 C10 C5 120.4(3) . .
N1 C10 C9 121.0(3) . .
C5 C10 C9 118.6(3) . .
N1 C11 C12 113.6(3) . .
C13 C12 C11 117.3(3) . .
C12 C13 C14 113.1(4) . .
N2 C15 C20 120.8(3) . .
N2 C15 C16 121.3(3) . .
C20 C15 C16 117.9(3) . .
C17 C16 C15 120.6(4) . .
C16 C17 C18 121.7(4) . .
C19 C18 C17 118.6(4) . .
C18 C19 C20 122.0(4) . .
C15 C20 C19 119.1(3) . .
C15 C20 C21 121.3(3) . .
C19 C20 C21 119.6(3) . .
O2 C21 C20 122.4(3) . .
O2 C21 C22 121.9(3) . .
C20 C21 C22 115.7(3) . .
C24 C22 C23 120.7(3) 2_656 .
C24 C22 C21 118.8(3) 2_656 .
C23 C22 C21 120.5(3) . .
N2 C23 C24 121.8(3) . .
N2 C23 C22 120.9(3) . .
C24 C23 C22 117.3(3) . .
C22 C24 C23 122.0(3) 2_656 .
N2 C25 C26 112.2(3) . .
C27 C26 C25 113.8(3) . .
C26 C27 C28 112.7(3) . .
C1 N1 C10 120.2(3) . .
C1 N1 C11 118.6(2) . .
C10 N1 C11 121.0(3) . .
C15 N2 C23 120.3(3) . .
C15 N2 C25 120.4(3) . .
C23 N2 C25 119.2(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C3 1.395(4) 2_577
C1 N1 1.398(4) .
C1 C2 1.410(4) .
C2 C3 1.381(5) .
C2 C4 1.470(4) .
C3 C1 1.395(4) 2_577
C4 O1 1.241(4) .
C4 C5 1.449(5) .
C5 C6 1.399(4) .
C5 C10 1.410(4) .
C6 C7 1.373(5) .
C7 C8 1.383(5) .
C8 C9 1.369(5) .
C9 C10 1.410(5) .
C10 N1 1.403(4) .
C11 N1 1.471(4) .
C11 C12 1.543(6) .
C12 C13 1.456(6) .
C13 C14 1.530(6) .
C15 N2 1.386(4) .
C15 C20 1.406(5) .
C15 C16 1.415(5) .
C16 C17 1.358(5) .
C17 C18 1.392(6) .
C18 C19 1.354(5) .
C19 C20 1.407(5) .
C20 C21 1.452(5) .
C21 O2 1.235(4) .
C21 C22 1.467(5) .
C22 C24 1.386(4) 2_656
C22 C23 1.408(4) .
C23 N2 1.395(4) .
C23 C24 1.397(5) .
C24 C22 1.386(4) 2_656
C25 N2 1.468(4) .
C25 C26 1.524(5) .
C26 C27 1.497(5) .
C27 C28 1.515(6) .
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
C19 H19 O1 0.93 2.59 3.430(5) 149.9 2_567
C25 H25B O1 0.97 2.47 3.397(4) 160.5 1_544
C11 H11B O2 0.97 2.39 3.320(4) 160.5 1_565
