#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/06/2200636.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2200636
loop_
_publ_author_name
'Batsanov, Andrei S.'
'Collings, Jonathan C.'
'Howard, Judith A. K.'
'Marder, Todd B.'
_publ_section_title
;
 Octafluoronaphthalene--1,8-diaminonaphthalene (1/1)
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o950
_journal_page_last               o952
_journal_paper_doi               10.1107/S1600536801015100
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C10 F8, C10 H10 N2'
_chemical_formula_moiety         'C10 F8, C10 H10 N2'
_chemical_formula_sum            'C20 H10 F8 N2'
_chemical_formula_weight         430.30
_chemical_name_systematic
;
octafluoronaphthalene : 1,8-diaminonaphthalene (1/1)
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.890(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.3090(10)
_cell_length_b                   8.5410(10)
_cell_length_c                   13.4120(10)
_cell_measurement_reflns_used    818
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      12.1
_cell_volume                     831.21(16)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full .996
_diffrn_measured_fraction_theta_max .996
_diffrn_measurement_device_type  'SMART 1K CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .037
_diffrn_reflns_av_sigmaI/netI    .024
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6791
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.53
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count none
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .165
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             432
_exptl_crystal_size_max          .44
_exptl_crystal_size_mid          .25
_exptl_crystal_size_min          .16
_refine_diff_density_max         .26
_refine_diff_density_min         -.25
_refine_ls_abs_structure_details
'undeterminable, Friedel pairs merged, all \Df" set to 0'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         2031
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          .036
_refine_ls_R_factor_gt           .030
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0612P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .083
_reflns_number_gt                1797
_reflns_number_total             2031
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6058.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 21'
_cod_database_code               2200636
_cod_database_fobs_code          2200636
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 .4880(3) .6679(2) .14591(15) .0191(4) Uani d . 1 . . C
C2 .5736(3) .7814(2) .20627(16) .0209(4) Uani d . 1 . . C
C3 .6344(3) .7500(2) .30716(16) .0209(4) Uani d . 1 . . C
C4 .6113(3) .6045(2) .34654(15) .0198(4) Uani d . 1 . . C
C5 .4895(3) .3325(2) .32491(15) .0207(4) Uani d . 1 . . C
C6 .4026(3) .2189(2) .26514(17) .0214(4) Uani d . 1 . . C
C7 .3439(3) .2495(2) .16366(16) .0210(4) Uani d . 1 . . C
C8 .3687(3) .3944(2) .12439(15) .0196(4) Uani d . 1 . . C
C9 .4582(3) .5159(2) .18366(14) .0174(4) Uani d . 1 . . C
C10 .5216(3) .4835(2) .28690(15) .0174(4) Uani d . 1 . . C
F1 .43168(17) .70269(16) .04966(9) .0276(3) Uani d . 1 . . F
F2 .60029(17) .92489(15) .17016(9) .0268(3) Uani d . 1 . . F
F3 .71630(17) .86499(15) .36456(9) .0278(3) Uani d . 1 . . F
F4 .67412(18) .57857(16) .44334(9) .0282(3) Uani d . 1 . . F
F5 .54090(18) .29900(15) .42232(9) .0282(3) Uani d . 1 . . F
F6 .37167(17) .07699(15) .30315(10) .0299(3) Uani d . 1 . . F
F7 .26213(17) .13435(15) .10652(10) .0287(3) Uani d . 1 . . F
F8 .30499(17) .41987(16) .02788(8) .0259(3) Uani d . 1 . . F
C11 -.0138(3) .3281(2) .32066(16) .0202(4) Uani d . 1 . . C
C12 -.0915(3) .2169(3) .25333(17) .0238(4) Uani d . 1 . . C
H12 -.115(4) .117(4) .282(2) .037(7) Uiso d . 1 . . H
C13 -.1409(3) .2532(3) .15134(17) .0258(5) Uani d . 1 . . C
H13 -.195(4) .178(4) .107(2) .042(8) Uiso d . 1 . . H
C14 -.1175(3) .4012(3) .11670(17) .0238(4) Uani d . 1 . . C
H14 -.149(4) .424(4) .049(2) .031(7) Uiso d . 1 . . H
C15 -.0126(3) .6747(3) .14585(18) .0253(5) Uani d . 1 . . C
H15 -.055(4) .698(4) .079(2) .037(8) Uiso d . 1 . . H
C16 .0673(3) .7881(3) .20902(19) .0283(5) Uani d . 1 . . C
H16 .074(4) .895(4) .183(2) .037(8) Uiso d . 1 . . H
C17 .1338(3) .7522(3) .30868(19) .0267(5) Uani d . 1 . . C
H17 .196(4) .827(4) .356(2) .037(8) Uiso d . 1 . . H
C18 .1183(3) .6029(2) .34760(16) .0213(4) Uani d . 1 . . C
C19 .0226(3) .4834(2) .28554(16) .0175(4) Uani d . 1 . . C
C20 -.0364(3) .5194(2) .18235(15) .0204(4) Uani d . 1 . . C
N11 .0334(3) .2868(2) .42147(15) .0286(4) Uani d . 1 . . N
H111 .003(4) .360(3) .468(2) .034(7) Uiso d . 1 . . H
H112 -.028(4) .193(4) .435(2) .050(8) Uiso d . 1 . . H
N18 .1944(3) .5725(3) .44685(15) .0270(4) Uani d . 1 . . N
H181 .232(4) .474(4) .454(3) .054(9) Uiso d . 1 . . H
H182 .286(4) .647(4) .470(2) .046(8) Uiso d . 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F .0171 .0000 '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
F1 C1 C2 118.64(18)
F1 C1 C9 120.26(17)
C2 C1 C9 121.10(18)
F2 C2 C1 120.73(19)
F2 C2 C3 118.78(18)
C1 C2 C3 120.49(19)
F3 C3 C4 120.64(18)
F3 C3 C2 118.84(18)
C4 C3 C2 120.52(18)
F4 C4 C3 118.65(18)
F4 C4 C10 120.42(17)
C3 C4 C10 120.92(18)
F5 C5 C6 118.36(18)
F5 C5 C10 120.23(17)
C6 C5 C10 121.39(18)
F6 C6 C5 120.36(19)
F6 C6 C7 119.34(19)
C5 C6 C7 120.30(19)
F7 C7 C8 120.96(19)
F7 C7 C6 118.78(19)
C8 C7 C6 120.26(18)
F8 C8 C7 118.23(17)
F8 C8 C9 120.39(17)
C7 C8 C9 121.37(18)
C8 C9 C1 123.32(17)
C8 C9 C10 118.28(16)
C1 C9 C10 118.39(16)
C5 C10 C4 123.08(17)
C5 C10 C9 118.36(16)
C4 C10 C9 118.56(16)
C12 C11 N11 119.5(2)
C12 C11 C19 119.67(19)
N11 C11 C19 120.85(18)
C11 C12 C13 121.4(2)
C11 C12 H12 115.1(18)
C13 C12 H12 123.5(18)
C14 C13 C12 120.5(2)
C14 C13 H13 119(2)
C12 C13 H13 121(2)
C13 C14 C20 120.5(2)
C13 C14 H14 120(2)
C20 C14 H14 120(2)
C16 C15 C20 120.2(2)
C16 C15 H15 121(2)
C20 C15 H15 119(2)
C15 C16 C17 120.5(2)
C15 C16 H16 118.0(17)
C17 C16 H16 121.5(17)
C18 C17 C16 121.7(2)
C18 C17 H17 114.3(18)
C16 C17 H17 123.9(18)
C17 C18 N18 119.1(2)
C17 C18 C19 119.2(2)
N18 C18 C19 121.69(18)
C20 C19 C11 117.84(16)
C20 C19 C18 118.27(16)
C11 C19 C18 123.88(18)
C14 C20 C15 120.34(19)
C14 C20 C19 120.01(17)
C15 C20 C19 119.65(17)
C11 N11 H111 115.5(17)
C11 N11 H112 109.3(19)
H111 N11 H112 106(2)
C18 N18 H181 111(2)
C18 N18 H182 112.0(19)
H181 N18 H182 114(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 F1 . 1.340(2) ?
C1 C2 . 1.366(3) ?
C1 C9 . 1.419(3) ?
C2 F2 . 1.341(2) ?
C2 C3 . 1.399(3) ?
C3 F3 . 1.344(2) ?
C3 C4 . 1.368(3) ?
C4 F4 . 1.343(2) ?
C4 C10 . 1.419(3) ?
C5 F5 . 1.346(2) ?
C5 C6 . 1.365(3) ?
C5 C10 . 1.417(3) ?
C6 F6 . 1.345(2) ?
C6 C7 . 1.402(3) ?
C7 F7 . 1.342(2) ?
C7 C8 . 1.365(3) ?
C8 F8 . 1.340(2) ?
C8 C9 . 1.419(3) ?
C9 C10 . 1.433(3) ?
C11 C12 . 1.385(3) ?
C11 N11 . 1.400(3) ?
C11 C19 . 1.443(3) ?
C12 C13 . 1.407(3) ?
C12 H12 . .96(3) ?
C13 C14 . 1.365(3) ?
C13 H13 . .93(3) ?
C14 C20 . 1.422(3) ?
C14 H14 . .93(3) ?
C15 C16 . 1.370(3) ?
C15 C20 . 1.432(3) ?
C15 H15 . .93(3) ?
C16 C17 . 1.400(4) ?
C16 H16 . .98(3) ?
C17 C18 . 1.387(3) ?
C17 H17 . .98(3) ?
C18 N18 . 1.404(3) ?
C18 C19 . 1.444(3) ?
C19 C20 . 1.433(3) ?
N11 H111 . .93(3) ?
N11 H112 . .95(3) ?
N18 H181 . .89(4) ?
N18 H182 . .95(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21132716
2 PubChem 139064980
