#------------------------------------------------------------------------------
#$Date: 2016-03-21 01:21:50 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178377 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/11/4001131.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4001131
loop_
_publ_author_name
'See, Kevin C.'
'Landis, Chad'
'Sarjeant, Amy'
'Katz, Howard E.'
_publ_section_title
;
 Easily Synthesized Naphthalene Tetracarboxylic Diimide Semiconductors
 with High Electron Mobility in Air
;
_journal_issue                   11
_journal_name_full               'Chemistry of Materials'
_journal_page_first              3609
_journal_paper_doi               10.1021/cm7032614
_journal_volume                  20
_journal_year                    2008
_chemical_formula_moiety         'C32 H14 F12 N2 O4'
_chemical_formula_sum            'C32 H14 F12 N2 O4'
_chemical_formula_weight         718.45
_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_date
;
'Tue Sep 04 17:18:09 2007'
;
_audit_creation_method           SHELXL-97
_cell_angle_alpha                72.455(5)
_cell_angle_beta                 85.757(5)
_cell_angle_gamma                84.292(5)
_cell_formula_units_Z            1
_cell_length_a                   4.7402(3)
_cell_length_b                   11.6558(7)
_cell_length_c                   12.7944(7)
_cell_measurement_reflns_used    2717
_cell_measurement_temperature    110
_cell_measurement_theta_max      27.4959
_cell_measurement_theta_min      4.1674
_cell_volume                     669.95(7)
_computing_cell_refinement       'Oxford Diffraction CrysAlis RED'
_computing_data_collection       'Oxford Diffraction CrysAlis CCD'
_computing_data_reduction        'Oxford Diffraction CrysAlis RED'
_computing_molecular_graphics    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_publication_material  'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_structure_refinement  'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_structure_solution    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_diffrn_ambient_temperature      110
_diffrn_detector_area_resol_mean 15.9890
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      'see scan set'
_diffrn_measurement_device       Kappa
_diffrn_measurement_device_type  Xcalibur3
_diffrn_measurement_method       ' omega phi scans'
_diffrn_orient_matrix_UB_11      -0.0042486797
_diffrn_orient_matrix_UB_12      0.0568903329
_diffrn_orient_matrix_UB_13      0.0096825827
_diffrn_orient_matrix_UB_21      0.0273260422
_diffrn_orient_matrix_UB_22      0.0278360515
_diffrn_orient_matrix_UB_23      -0.0568971753
_diffrn_orient_matrix_UB_31      -0.1480281078
_diffrn_orient_matrix_UB_32      0.0089747761
_diffrn_orient_matrix_UB_33      -0.0082430397
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0754
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6725
_diffrn_reflns_resolution_max    0.77
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         4.18
_diffrn_source_current           40
_diffrn_source_power             2
_diffrn_source_voltage           50
_diffrn_standards_interval_count 2
_diffrn_standards_interval_time  50
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET)
(compiled Apr 27 2007,17:53:11)
Analytical numeric absorption correction using a multifaceted crystal
   model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.7925
_exptl_crystal_size_mid          0.1356
_exptl_crystal_size_min          0.0899
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0418
_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)+(0.0450P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0971
_reflns_number_gt                1734
_reflns_number_total             3049
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cm7032614-file001.cif
_cod_data_source_block           x0399
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               4001131
#BEGIN Tags that were not found in dictionaries:
_audit_creation_method_reference
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET)
(compiled Apr 27 2007,17:53:11)
;
_computing_data_collection_reference
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET)
(compiled Apr 27 2007,17:53:11)
;
_computing_cell_refinment_reference
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET)
(compiled Apr 27 2007,17:53:11)
;
_computing_data_reduction_reference
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET)
(compiled Apr 27 2007,17:53:11)
;
_cell_measurement_resolution_max 0.77
_jhu_your_name_here              'Dr. Amy A Sarjeant'
_jhu_your_lab_here               'NCB 240'
_jhu_your_phone_number_here      x6-8569
_jhu_your_email_here             xray@jhu.edu
_jhu_institutional_source        'Katz Lab'
_jhu_submitting_scientist        'Kevin See'
_jhu_scientist_phone             x6-0462
_jhu_scientist_email             kevsee@jhu.edu
_jhu_identifying_number          x0399
_jhu_xray_labbook                II-89
_jhu_crystalization_labbook      BCF3NTCDI
_jhu_crystalization_solvent      unknown
_jhu_crystalization_method       unknown
_jhu_diffraction_detector_distance 50
_jhu_quality_factor              2
#END Tags that were not found in dictionaries
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
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.519(2) -0.1302(10) 0.8365(8) 0.0405(16) Uani 0.57 1 d P A 1
F2 F 0.0886(9) -0.0574(4) 0.8359(4) 0.0652(16) Uani 0.57 1 d P A 1
F3 F 0.3832(9) -0.0134(3) 0.9338(2) 0.0738(11) Uani 0.57 1 d P A 1
F1' F 0.527(2) -0.1113(12) 0.8662(10) 0.049(3) Uani 0.43 1 d P A 2
F2' F 0.1290(13) -0.0920(5) 0.7952(4) 0.0374(13) Uani 0.43 1 d P A 2
F3' F 0.1921(9) -0.0001(4) 0.9094(3) 0.0438(10) Uani 0.43 1 d P A 2
F4 F 0.1445(2) 0.30771(11) 0.39854(9) 0.0359(3) Uani 1 1 d . . .
F5 F 0.5179(2) 0.20489(11) 0.36213(9) 0.0352(3) Uani 1 1 d . . .
F6 F 0.1419(2) 0.11601(11) 0.43066(10) 0.0421(4) Uani 1 1 d . . .
O1 O 0.3849(2) 0.50287(12) 0.67730(10) 0.0209(3) Uani 1 1 d . . .
O2 O 1.0942(2) 0.27269(12) 0.88157(10) 0.0253(3) Uani 1 1 d . . .
N1 N 0.7439(3) 0.39068(14) 0.77835(12) 0.0171(4) Uani 1 1 d . . .
C1 C 0.5048(4) 0.47378(16) 0.76341(15) 0.0166(4) Uani 1 1 d . . .
C2 C 0.4106(3) 0.52225(16) 0.85573(14) 0.0151(4) Uani 1 1 d . . .
C3 C 0.5475(3) 0.47751(16) 0.95576(14) 0.0134(4) Uani 1 1 d . . .
C4 C 0.7802(3) 0.38982(16) 0.96913(15) 0.0152(4) Uani 1 1 d . . .
C5 C 0.8886(4) 0.34492(17) 0.87538(15) 0.0176(4) Uani 1 1 d . . .
C6 C 0.1872(4) 0.60916(16) 0.84417(15) 0.0168(4) Uani 1 1 d . . .
H6A H 0.0975 0.6396 0.7762 0.020 Uiso 1 1 calc R . .
C7 C 0.9095(3) 0.34675(16) 1.06729(15) 0.0165(4) Uani 1 1 d . . .
H7A H 1.0648 0.2870 1.0757 0.020 Uiso 1 1 calc R . .
C8 C 0.8434(4) 0.34815(17) 0.68387(15) 0.0187(4) Uani 1 1 d . . .
H8A H 1.0408 0.3116 0.6947 0.022 Uiso 1 1 calc R . .
H8B H 0.8446 0.4181 0.6168 0.022 Uiso 1 1 calc R . .
C9 C 0.6601(3) 0.25627(16) 0.66764(15) 0.0161(4) Uani 1 1 d . . .
C10 C 0.5861(4) 0.15779(17) 0.75458(15) 0.0195(4) Uani 1 1 d . . .
H10A H 0.6505 0.1475 0.8256 0.023 Uiso 1 1 calc R . .
C11 C 0.4183(4) 0.07432(16) 0.73803(16) 0.0207(5) Uani 1 1 d . A .
C12 C 0.3245(3) 0.08722(17) 0.63488(16) 0.0205(4) Uani 1 1 d . . .
H12A H 0.2101 0.0298 0.6238 0.025 Uiso 1 1 calc R . .
C13 C 0.3993(3) 0.18459(17) 0.54855(15) 0.0186(4) Uani 1 1 d . . .
C14 C 0.5644(3) 0.26922(17) 0.56474(15) 0.0168(4) Uani 1 1 d . . .
H14A H 0.6121 0.3365 0.5047 0.020 Uiso 1 1 calc R . .
C15 C 0.3363(5) -0.03124(19) 0.83196(19) 0.0318(5) Uani 1 1 d . . .
C16 C 0.3016(4) 0.20193(19) 0.43624(16) 0.0252(5) 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 16.00 3.00 0.0605
-6.00 -7.00 0.00 0.3503
0.00 -13.00 -14.00 0.0615
0.00 0.00 -17.00 0.0450
0.00 -3.00 16.00 0.0420
0.00 9.00 -11.00 0.0483
-6.00 7.00 -1.00 0.3413
0.00 -16.00 -1.00 0.0590
6.00 -3.00 2.00 0.3619
0.00 5.00 18.00 0.0479
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
C5 N1 C1 125.13(15) . .
C5 N1 C8 118.55(14) . .
C1 N1 C8 116.30(14) . .
O1 C1 N1 119.89(16) . .
O1 C1 C2 123.10(16) . .
N1 C1 C2 117.01(15) . .
C6 C2 C3 120.33(16) . .
C6 C2 C1 119.93(16) . .
C3 C2 C1 119.74(15) . .
C2 C3 C4 121.44(15) . .
C2 C3 C3 119.41(19) . 2_667
C4 C3 C3 119.15(19) . 2_667
C7 C4 C3 120.62(16) . .
C7 C4 C5 119.70(16) . .
C3 C4 C5 119.67(15) . .
O2 C5 N1 120.97(16) . .
O2 C5 C4 122.19(16) . .
N1 C5 C4 116.84(15) . .
C2 C6 C7 120.32(17) . 2_667
C2 C6 H6A 119.8 . .
C7 C6 H6A 119.8 2_667 .
C4 C7 C6 120.15(17) . 2_667
C4 C7 H7A 119.9 . .
C6 C7 H7A 119.9 2_667 .
N1 C8 C9 112.64(14) . .
N1 C8 H8A 109.1 . .
C9 C8 H8A 109.1 . .
N1 C8 H8B 109.1 . .
C9 C8 H8B 109.1 . .
H8A C8 H8B 107.8 . .
C14 C9 C10 118.88(17) . .
C14 C9 C8 120.01(17) . .
C10 C9 C8 121.11(16) . .
C11 C10 C9 120.27(17) . .
C11 C10 H10A 119.9 . .
C9 C10 H10A 119.9 . .
C12 C11 C10 120.67(18) . .
C12 C11 C15 119.04(17) . .
C10 C11 C15 120.28(18) . .
C13 C12 C11 119.02(17) . .
C13 C12 H12A 120.5 . .
C11 C12 H12A 120.5 . .
C12 C13 C14 120.63(17) . .
C12 C13 C16 120.65(16) . .
C14 C13 C16 118.72(17) . .
C9 C14 C13 120.53(18) . .
C9 C14 H14A 119.7 . .
C13 C14 H14A 119.7 . .
F1' C15 F3' 112.8(6) . .
F2 C15 F1 110.2(5) . .
F2 C15 F3 107.2(3) . .
F1 C15 F3 100.2(4) . .
F1' C15 F2' 103.9(6) . .
F3' C15 F2' 100.9(3) . .
F1' C15 C11 116.2(6) . .
F2 C15 C11 116.0(3) . .
F3' C15 C11 113.1(2) . .
F1 C15 C11 110.8(5) . .
F3 C15 C11 111.1(2) . .
F2' C15 C11 108.3(3) . .
F6 C16 F5 106.71(16) . .
F6 C16 F4 106.31(14) . .
F5 C16 F4 105.48(16) . .
F6 C16 C13 113.50(17) . .
F5 C16 C13 112.48(14) . .
F4 C16 C13 111.81(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C15 1.362(11) .
F2 C15 1.235(4) .
F3 C15 1.416(4) .
F1' C15 1.234(13) .
F2' C15 1.447(6) .
F3' C15 1.284(4) .
F4 C16 1.349(2) .
F5 C16 1.340(2) .
F6 C16 1.335(2) .
O1 C1 1.217(2) .
O2 C5 1.214(2) .
N1 C5 1.396(2) .
N1 C1 1.400(2) .
N1 C8 1.470(2) .
C1 C2 1.479(2) .
C2 C6 1.374(2) .
C2 C3 1.409(2) .
C3 C4 1.410(2) .
C3 C3 1.412(3) 2_667
C4 C7 1.370(2) .
C4 C5 1.487(2) .
C6 C7 1.409(2) 2_667
C6 H6A 0.9500 .
C7 C6 1.409(2) 2_667
C7 H7A 0.9500 .
C8 C9 1.514(2) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C14 1.384(2) .
C9 C10 1.390(3) .
C10 C11 1.388(3) .
C10 H10A 0.9500 .
C11 C12 1.384(3) .
C11 C15 1.498(3) .
C12 C13 1.379(3) .
C12 H12A 0.9500 .
C13 C14 1.389(2) .
C13 C16 1.492(3) .
C14 H14A 0.9500 .
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_4
C5 N1 C1 O1 -175.91(16) . .
C8 N1 C1 O1 3.0(2) . .
C5 N1 C1 C2 4.1(2) . .
C8 N1 C1 C2 -176.97(14) . .
O1 C1 C2 C6 -3.6(3) . .
N1 C1 C2 C6 176.36(16) . .
O1 C1 C2 C3 175.28(17) . .
N1 C1 C2 C3 -4.7(2) . .
C6 C2 C3 C4 -178.92(16) . .
C1 C2 C3 C4 2.2(2) . .
C6 C2 C3 C3 0.2(3) . 2_667
C1 C2 C3 C3 -178.73(19) . 2_667
C2 C3 C4 C7 -179.56(16) . .
C3 C3 C4 C7 1.3(3) 2_667 .
C2 C3 C4 C5 1.3(2) . .
C3 C3 C4 C5 -177.85(19) 2_667 .
C1 N1 C5 O2 179.79(17) . .
C8 N1 C5 O2 0.9(3) . .
C1 N1 C5 C4 -0.8(2) . .
C8 N1 C5 C4 -179.70(15) . .
C7 C4 C5 O2 -1.8(3) . .
C3 C4 C5 O2 177.39(17) . .
C7 C4 C5 N1 178.79(16) . .
C3 C4 C5 N1 -2.0(2) . .
C3 C2 C6 C7 -0.8(3) . 2_667
C1 C2 C6 C7 178.10(15) . 2_667
C3 C4 C7 C6 -0.7(3) . 2_667
C5 C4 C7 C6 178.46(16) . 2_667
C5 N1 C8 C9 102.75(18) . .
C1 N1 C8 C9 -76.3(2) . .
N1 C8 C9 C14 131.47(17) . .
N1 C8 C9 C10 -48.9(2) . .
C14 C9 C10 C11 -0.2(2) . .
C8 C9 C10 C11 -179.85(16) . .
C9 C10 C11 C12 0.5(3) . .
C9 C10 C11 C15 -179.44(16) . .
C10 C11 C12 C13 -0.2(3) . .
C15 C11 C12 C13 179.80(16) . .
C11 C12 C13 C14 -0.5(3) . .
C11 C12 C13 C16 -179.78(16) . .
C10 C9 C14 C13 -0.6(2) . .
C8 C9 C14 C13 179.12(15) . .
C12 C13 C14 C9 0.9(3) . .
C16 C13 C14 C9 -179.82(16) . .
C12 C11 C15 F1' 107.8(5) . .
C10 C11 C15 F1' -72.2(5) . .
C12 C11 C15 F2 -41.4(4) . .
C10 C11 C15 F2 138.6(3) . .
C12 C11 C15 F3' -119.4(3) . .
C10 C11 C15 F3' 60.5(3) . .
C12 C11 C15 F1 85.2(4) . .
C10 C11 C15 F1 -94.8(4) . .
C12 C11 C15 F3 -164.3(3) . .
C10 C11 C15 F3 15.7(3) . .
C12 C11 C15 F2' -8.5(3) . .
C10 C11 C15 F2' 171.4(3) . .
C12 C13 C16 F6 0.0(2) . .
C14 C13 C16 F6 -179.27(15) . .
C12 C13 C16 F5 -121.30(18) . .
C14 C13 C16 F5 59.5(2) . .
C12 C13 C16 F4 120.24(18) . .
C14 C13 C16 F4 -59.0(2) . .
#BEGIN Loops that were not found in dictionaries:
loop_
_diffrn_scan_number
_diffrn_scan_type
_diffrn_scan_start
_diffrn_scan_end
_diffrn_scan_width
_diffrn_scan_exptime
_diffrn_scan_omega
_diffrn_scan_theta
_diffrn_scan_kappa
_diffrn_scan_phi
_diffrn_scan_omega1
_diffrn_scan_theta1
_diffrn_scan_frames
1 omega 44.00 94.00 1.00 15.00 - 22.84 45.00 0.00 0.00 0.00 50
2 omega 1.00 55.00 1.00 15.00 - 22.84 -75.00 240.00 0.00 0.00 54
3 omega 40.00 85.00 1.00 15.00 - 22.84 -128.00 84.00 0.00 0.00 45
4 omega 45.00 95.00 1.00 15.00 - 22.84 45.00 240.00 0.00 0.00 50
5 omega 0.00 51.00 1.00 15.00 - 22.84 -70.00 134.00 0.00 0.00 51
6 omega 44.00 94.00 1.00 15.00 - 22.84 45.00 120.00 0.00 0.00 50
7 omega -4.00 46.00 1.00 15.00 - 22.84 45.00 120.00 0.00 0.00 50
8 omega -55.00 -1.00 1.00 15.00 - -23.46 75.00 0.00 0.00 0.00 54
9 phi -147.00 -107.00 1.00 15.00 -40.00 -23.46 0.00 - 0.00 0.00 40
10 omega -55.00 -2.00 1.00 15.00 - -23.46 75.00 240.00 0.00 0.00 53
11 phi 96.00 149.00 1.00 15.00 -40.00 -23.46 0.00 - 0.00 0.00 53
#END Loops that were not found in dictionaries
