#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/32/1513257.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_1513257
loop_
_publ_author_name
'Zhao, Yunfeng'
'Mu, Xiaoyue'
'Bao, Chunxiao'
'Fan, Yan'
'Zhang, Jingying'
'Wang, Yue'
_publ_section_title
;
 Alkyl Chain Length Dependent Morphology and Emission Properties of the
 Organic Micromaterials Based on Fluorinated Quinacridone Derivatives
;
_journal_issue                   5
_journal_name_full               Langmuir
_journal_page_first              3264
_journal_page_last               3270
_journal_paper_doi               10.1021/la804182d
_journal_volume                  25
_journal_year                    2009
_chemical_formula_sum            'C36 H42 F2 N2 O2'
_chemical_formula_weight         572.72
_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                110.82(3)
_cell_angle_beta                 101.89(3)
_cell_angle_gamma                99.42(3)
_cell_formula_units_Z            1
_cell_length_a                   8.0930(16)
_cell_length_b                   8.8966(18)
_cell_length_c                   12.017(2)
_cell_measurement_reflns_used    5319
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      3.17
_cell_volume                     764.4(4)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7612
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.17
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_correction_T_min  0.9721
_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    1.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             306
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.709
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3474
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.709
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0516
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1705
_refine_ls_wR_factor_ref         0.2084
_reflns_number_gt                2023
_reflns_number_total             3474
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            la804182dsup1.cif
_cod_data_source_block           C8-DFQA
_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_cell_volume        764.3(3)
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               1513257
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 0.0704(2) 0.1979(2) 0.14110(15) 0.0431(4) Uani 1 1 d .
C2 C 0.1525(2) 0.1154(2) 0.20832(18) 0.0533(5) Uani 1 1 d .
H2 H 0.2736 0.1472 0.2406 0.064 Uiso 1 1 calc R
C3 C 0.0565(3) -0.0106(2) 0.22666(19) 0.0586(5) Uani 1 1 d .
H3 H 0.1119 -0.0656 0.2698 0.070 Uiso 1 1 calc R
C4 C -0.1241(3) -0.0555(2) 0.18043(18) 0.0546(5) Uani 1 1 d .
C5 C -0.2104(2) 0.0225(2) 0.11856(16) 0.0484(4) Uani 1 1 d .
H5 H -0.3319 -0.0084 0.0904 0.058 Uiso 1 1 calc R
C6 C -0.1141(2) 0.15073(19) 0.09745(15) 0.0419(4) Uani 1 1 d .
C7 C -0.20737(19) 0.2275(2) 0.02494(15) 0.0432(4) Uani 1 1 d .
C8 C -0.09845(19) 0.36801(19) 0.01358(15) 0.0402(4) Uani 1 1 d .
C9 C 0.08615(19) 0.41027(19) 0.06040(15) 0.0404(4) Uani 1 1 d .
C10 C 0.18049(19) 0.5446(2) 0.04524(15) 0.0432(4) Uani 1 1 d .
H10 H 0.3018 0.5760 0.0756 0.052 Uiso 1 1 calc R
C11 C 0.35841(19) 0.3428(2) 0.13940(16) 0.0447(4) Uani 1 1 d .
H11A H 0.3922 0.3724 0.0755 0.054 Uiso 1 1 calc R
H11B H 0.3839 0.2370 0.1305 0.054 Uiso 1 1 calc R
C12 C 0.4695(2) 0.4738(2) 0.26547(16) 0.0485(4) Uani 1 1 d .
H12A H 0.4407 0.4438 0.3306 0.058 Uiso 1 1 calc R
H12B H 0.4452 0.5805 0.2762 0.058 Uiso 1 1 calc R
C13 C 0.6623(2) 0.4877(2) 0.27566(16) 0.0499(4) Uani 1 1 d .
H13A H 0.6851 0.3814 0.2685 0.060 Uiso 1 1 calc R
H13B H 0.6864 0.5084 0.2059 0.060 Uiso 1 1 calc R
C14 C 0.7884(2) 0.6225(2) 0.39470(17) 0.0537(5) Uani 1 1 d .
H14A H 0.7706 0.5990 0.4649 0.064 Uiso 1 1 calc R
H14B H 0.7635 0.7288 0.4046 0.064 Uiso 1 1 calc R
C15 C 0.9777(2) 0.6345(2) 0.39497(18) 0.0564(5) Uani 1 1 d .
H15A H 1.0032 0.5297 0.3895 0.068 Uiso 1 1 calc R
H15B H 0.9925 0.6502 0.3214 0.068 Uiso 1 1 calc R
C16 C 1.1093(2) 0.7739(2) 0.50829(18) 0.0587(5) Uani 1 1 d .
H16A H 1.0831 0.8788 0.5149 0.070 Uiso 1 1 calc R
H16B H 1.0969 0.7572 0.5819 0.070 Uiso 1 1 calc R
C17 C 1.2968(3) 0.7852(3) 0.5049(2) 0.0688(6) Uani 1 1 d .
H17A H 1.3245 0.6820 0.5019 0.083 Uiso 1 1 calc R
H17B H 1.3080 0.7971 0.4294 0.083 Uiso 1 1 calc R
C18 C 1.4278(3) 0.9288(3) 0.6153(2) 0.0842(8) Uani 1 1 d .
H18A H 1.3997 1.0313 0.6203 0.126 Uiso 1 1 calc R
H18B H 1.5431 0.9326 0.6057 0.126 Uiso 1 1 calc R
H18C H 1.4238 0.9137 0.6900 0.126 Uiso 1 1 calc R
F1 F -0.21572(17) -0.18255(15) 0.19914(13) 0.0781(4) Uani 1 1 d .
N1 N 0.16834(16) 0.32098(16) 0.11777(13) 0.0434(4) Uani 1 1 d .
O1 O -0.36659(14) 0.18089(15) -0.02210(13) 0.0589(4) 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'
F F 0.0171 0.0103 '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 C2 120.94(15) .
N1 C1 C6 121.04(15) .
C2 C1 C6 118.03(16) .
C3 C2 C1 120.90(17) .
C2 C3 C4 119.41(18) .
C5 C4 F1 119.76(17) .
C5 C4 C3 122.31(18) .
F1 C4 C3 117.93(18) .
C4 C5 C6 119.15(17) .
C5 C6 C1 120.16(16) .
C5 C6 C7 118.75(15) .
C1 C6 C7 121.02(15) .
O1 C7 C6 122.61(15) .
O1 C7 C8 121.91(16) .
C6 C7 C8 115.47(14) .
C10 C8 C9 121.13(16) 2_565
C10 C8 C7 118.40(14) 2_565
C9 C8 C7 120.47(16) .
N1 C9 C10 121.93(14) .
N1 C9 C8 121.05(15) .
C10 C9 C8 117.02(16) .
C8 C10 C9 121.85(15) 2_565
N1 C11 C12 114.86(14) .
C11 C12 C13 110.00(14) .
C14 C13 C12 115.32(15) .
C13 C14 C15 112.16(16) .
C16 C15 C14 114.51(17) .
C17 C16 C15 113.38(17) .
C18 C17 C16 113.48(19) .
C9 N1 C1 120.36(13) .
C9 N1 C11 119.25(14) .
C1 N1 C11 119.94(14) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.389(2) .
C1 C2 1.412(3) .
C1 C6 1.414(2) .
C2 C3 1.368(3) .
C3 C4 1.386(3) .
C4 C5 1.355(3) .
C4 F1 1.361(2) .
C5 C6 1.403(2) .
C6 C7 1.455(2) .
C7 O1 1.2289(18) .
C7 C8 1.472(2) .
C8 C10 1.382(3) 2_565
C8 C9 1.417(2) .
C9 N1 1.386(2) .
C9 C10 1.399(2) .
C10 C8 1.382(3) 2_565
C11 N1 1.4741(19) .
C11 C12 1.517(2) .
C12 C13 1.521(2) .
C13 C14 1.518(2) .
C14 C15 1.518(3) .
C15 C16 1.515(3) .
C16 C17 1.515(3) .
C17 C18 1.513(3) .
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
C5 H5 O1 0.93 2.46 3.344(2) 159.6 2_455
