#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/90/4509084.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_4509084
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 H30 N2 O3'
_chemical_formula_weight         442.54
_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                98.85(3)
_cell_angle_beta                 95.32(3)
_cell_angle_gamma                90.86(3)
_cell_formula_units_Z            2
_cell_length_a                   4.9927(10)
_cell_length_b                   14.153(3)
_cell_length_c                   16.101(3)
_cell_measurement_reflns_used    7088
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.00
_cell_volume                     1118.8(4)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        RAPID-AUTO
_computing_molecular_graphics    SHELXP97
_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 0.974
_diffrn_measured_fraction_theta_max 0.974
_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  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10980
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.00
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_correction_T_min  0.9670
_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    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         5011
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0665
_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)+(0.1360P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1981
_refine_ls_wR_factor_ref         0.2380
_reflns_number_gt                2973
_reflns_number_total             5011
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg800785usup1.cif
_cod_data_source_block           E
_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_cell_volume        1118.9(4)
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               4509084
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 0.1980(4) 0.96168(17) 0.05436(14) 0.0293(5) Uani 1 1 d .
C2 C 0.0289(5) 1.03307(18) 0.08577(15) 0.0311(5) Uani 1 1 d .
H2 H 0.0461 1.0559 0.1434 0.037 Uiso 1 1 calc R
C3 C 0.1651(4) 0.92847(17) -0.03386(14) 0.0295(5) Uani 1 1 d .
C4 C 0.3360(5) 0.85308(18) -0.07175(16) 0.0344(6) Uani 1 1 d .
C5 C 0.5278(5) 0.81479(18) -0.01331(16) 0.0345(6) Uani 1 1 d .
C6 C 0.7006(5) 0.7434(2) -0.0447(2) 0.0434(7) Uani 1 1 d .
H6 H 0.6906 0.7223 -0.1026 0.052 Uiso 1 1 calc R
C7 C 0.8846(6) 0.7040(2) 0.0081(2) 0.0504(8) Uani 1 1 d .
H7 H 1.0011 0.6579 -0.0136 0.060 Uiso 1 1 calc R
C8 C 0.8927(6) 0.7346(2) 0.0948(2) 0.0510(8) Uani 1 1 d .
H8 H 1.0131 0.7071 0.1310 0.061 Uiso 1 1 calc R
C9 C 0.7275(5) 0.8043(2) 0.12812(19) 0.0431(7) Uani 1 1 d .
H9 H 0.7340 0.8224 0.1863 0.052 Uiso 1 1 calc R
C10 C 0.5474(5) 0.84881(18) 0.07400(16) 0.0333(6) Uani 1 1 d .
C11 C 0.4546(5) 0.9687(2) 0.19563(15) 0.0362(6) Uani 1 1 d .
H11A H 0.4138 1.0360 0.2004 0.043 Uiso 1 1 calc R
H11B H 0.6460 0.9645 0.2111 0.043 Uiso 1 1 calc R
C12 C 0.3023(5) 0.9245(2) 0.25834(16) 0.0418(7) Uani 1 1 d .
H12A H 0.1168 0.9441 0.2538 0.050 Uiso 1 1 calc R
H12B H 0.3024 0.8554 0.2442 0.050 Uiso 1 1 calc R
C13 C 0.4250(6) 0.9540(2) 0.34870(18) 0.0511(8) Uani 1 1 d .
H13A H 0.6048 0.9293 0.3542 0.061 Uiso 1 1 calc R
H13B H 0.4410 1.0233 0.3608 0.061 Uiso 1 1 calc R
C14 C 0.2619(7) 0.9186(3) 0.4132(2) 0.0671(10) Uani 1 1 d .
H14A H 0.0917 0.9492 0.4132 0.101 Uiso 1 1 calc R
H14B H 0.3582 0.9334 0.4682 0.101 Uiso 1 1 calc R
H14C H 0.2325 0.8506 0.3990 0.101 Uiso 1 1 calc R
C15 C 0.8390(5) 0.44225(18) 0.43257(15) 0.0343(6) Uani 1 1 d .
C16 C 1.0187(5) 0.51287(19) 0.41736(16) 0.0369(6) Uani 1 1 d .
H16 H 1.0321 0.5225 0.3620 0.044 Uiso 1 1 calc R
C17 C 0.8217(5) 0.43081(18) 0.51755(15) 0.0345(6) Uani 1 1 d .
C18 C 0.6355(5) 0.35851(19) 0.53912(16) 0.0376(6) Uani 1 1 d .
C19 C 0.4620(5) 0.30703(19) 0.46842(17) 0.0370(6) Uani 1 1 d .
C20 C 0.2612(6) 0.2426(2) 0.48465(19) 0.0441(7) Uani 1 1 d .
H20 H 0.2425 0.2343 0.5400 0.053 Uiso 1 1 calc R
C21 C 0.0924(6) 0.1919(2) 0.4197(2) 0.0486(7) Uani 1 1 d .
H21 H -0.0408 0.1503 0.4309 0.058 Uiso 1 1 calc R
C22 C 0.1258(6) 0.2045(2) 0.33718(19) 0.0475(7) Uani 1 1 d .
H22 H 0.0123 0.1708 0.2931 0.057 Uiso 1 1 calc R
C23 C 0.3207(6) 0.2649(2) 0.31904(18) 0.0444(7) Uani 1 1 d .
H23 H 0.3403 0.2702 0.2630 0.053 Uiso 1 1 calc R
C24 C 0.4933(5) 0.31984(19) 0.38431(16) 0.0351(6) Uani 1 1 d .
C25 C 0.7254(5) 0.39116(19) 0.27886(15) 0.0364(6) Uani 1 1 d .
H25A H 0.6943 0.3286 0.2446 0.044 Uiso 1 1 calc R
H25B H 0.9111 0.4106 0.2761 0.044 Uiso 1 1 calc R
C26 C 0.5422(5) 0.4618(2) 0.24177(17) 0.0414(6) Uani 1 1 d .
H26A H 0.5437 0.5204 0.2820 0.050 Uiso 1 1 calc R
H26B H 0.3595 0.4354 0.2330 0.050 Uiso 1 1 calc R
C27 C 0.6237(6) 0.4857(2) 0.15837(19) 0.0493(7) Uani 1 1 d .
H27A H 0.7995 0.5177 0.1679 0.059 Uiso 1 1 calc R
H27B H 0.6373 0.4268 0.1194 0.059 Uiso 1 1 calc R
C28 C 0.4223(7) 0.5496(3) 0.1190(3) 0.0711(11) Uani 1 1 d .
H28A H 0.2488 0.5177 0.1084 0.107 Uiso 1 1 calc R
H28B H 0.4806 0.5631 0.0667 0.107 Uiso 1 1 calc R
H28C H 0.4107 0.6085 0.1569 0.107 Uiso 1 1 calc R
N1 N 0.3937(4) 0.92407(15) 0.10660(12) 0.0327(5) Uani 1 1 d .
N2 N 0.6854(4) 0.38335(16) 0.36676(13) 0.0359(5) Uani 1 1 d .
O1 O 0.3138(4) 0.82459(15) -0.14899(12) 0.0480(5) Uani 1 1 d .
O2 O 0.6287(4) 0.34398(15) 0.61270(12) 0.0540(6) Uani 1 1 d .
O3 O 0.1492(12) 0.2928(5) 0.7033(3) 0.1599(19) Uani 1 1 d D
H3A H 0.232(14) 0.292(8) 0.658(3) 0.240 Uiso 1 1 d D
H3B H -0.016(6) 0.277(7) 0.681(5) 0.240 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'
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
C2 C1 N1 122.0(2) . .
C2 C1 C3 117.2(2) . .
N1 C1 C3 120.8(2) . .
C1 C2 C3 122.3(2) . 2_575
C2 C3 C1 120.5(2) 2_575 .
C2 C3 C4 119.1(2) 2_575 .
C1 C3 C4 120.4(2) . .
O1 C4 C5 122.9(2) . .
O1 C4 C3 121.3(2) . .
C5 C4 C3 115.8(2) . .
C6 C5 C10 119.4(3) . .
C6 C5 C4 119.2(2) . .
C10 C5 C4 121.4(2) . .
C7 C6 C5 121.5(3) . .
C6 C7 C8 118.6(3) . .
C9 C8 C7 121.7(3) . .
C8 C9 C10 120.1(3) . .
N1 C10 C5 121.0(2) . .
N1 C10 C9 120.5(2) . .
C5 C10 C9 118.5(2) . .
N1 C11 C12 114.9(2) . .
C13 C12 C11 112.2(2) . .
C14 C13 C12 113.3(2) . .
C16 C15 N2 122.0(2) . .
C16 C15 C17 117.2(2) . .
N2 C15 C17 120.8(2) . .
C17 C16 C15 122.0(2) 2_766 .
C16 C17 C15 120.7(2) 2_766 .
C16 C17 C18 118.6(2) 2_766 .
C15 C17 C18 120.7(2) . .
O2 C18 C19 123.1(3) . .
O2 C18 C17 121.4(2) . .
C19 C18 C17 115.4(2) . .
C20 C19 C24 119.9(2) . .
C20 C19 C18 119.0(3) . .
C24 C19 C18 121.1(2) . .
C21 C20 C19 121.1(3) . .
C20 C21 C22 118.6(3) . .
C23 C22 C21 121.9(3) . .
C22 C23 C24 121.0(3) . .
N2 C24 C19 121.1(2) . .
N2 C24 C23 121.5(2) . .
C19 C24 C23 117.5(2) . .
N2 C25 C26 113.6(2) . .
C25 C26 C27 113.2(2) . .
C28 C27 C26 111.9(3) . .
C10 N1 C1 120.4(2) . .
C10 N1 C11 119.1(2) . .
C1 N1 C11 120.4(2) . .
C24 N2 C15 120.3(2) . .
C24 N2 C25 120.1(2) . .
C15 N2 C25 119.5(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.392(3) .
C1 N1 1.395(3) .
C1 C3 1.419(3) .
C2 C3 1.392(3) 2_575
C3 C2 1.392(3) 2_575
C3 C4 1.470(3) .
C4 O1 1.241(3) .
C4 C5 1.450(4) .
C5 C6 1.404(4) .
C5 C10 1.408(4) .
C6 C7 1.377(4) .
C7 C8 1.392(4) .
C8 C9 1.373(4) .
C9 C10 1.416(4) .
C10 N1 1.388(3) .
C11 N1 1.477(3) .
C11 C12 1.520(4) .
C12 C13 1.519(4) .
C13 C14 1.515(5) .
C15 C16 1.397(4) .
C15 N2 1.402(3) .
C15 C17 1.412(4) .
C16 C17 1.392(3) 2_766
C17 C16 1.392(3) 2_766
C17 C18 1.474(4) .
C18 O2 1.237(3) .
C18 C19 1.456(4) .
C19 C20 1.414(4) .
C19 C24 1.416(4) .
C20 C21 1.381(4) .
C21 C22 1.392(4) .
C22 C23 1.367(4) .
C23 C24 1.418(4) .
C24 N2 1.382(3) .
C25 N2 1.468(3) .
C25 C26 1.518(4) .
C26 C27 1.523(4) .
C27 C28 1.523(5) .
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
C9 H9 O3 0.93 2.62 3.241(6) 124.3 2_666
C26 H26A O2 0.97 2.57 3.497(4) 159.5 2_666
C25 H25A O1 0.97 2.46 3.417(3) 170.6 2_665
C22 H22 O1 0.93 2.72 3.539(4) 147.6 2_565
C11 H11A O1 0.97 2.66 3.346(4) 128.3 2_675
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146836
