#------------------------------------------------------------------------------
#$Date: 2019-11-04 09:09:41 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222320 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/37/4033745.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_4033745
loop_
_publ_author_name
'Církva, Vladimír'
'Jakubík, Pavel'
'Strašák, Tomáš'
'Hrbáč, Jan'
'Sýkora, Jan'
'Císařová, Ivana'
'Vacek, Jan'
'Žádný, Jaroslav'
'Storch, Jan'
_publ_section_title
;
 Preparation and Physicochemical Properties of [6]Helicenes Fluorinated at
 Terminal Rings.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1980
_journal_page_last               1993
_journal_paper_doi               10.1021/acs.joc.8b02870
_journal_volume                  84
_journal_year                    2019
_chemical_compound_source        synthetic
_chemical_formula_moiety         'C26 H13 F5'
_chemical_formula_sum            'C26 H13 F5'
_chemical_formula_weight         420.38
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 96.609(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.984(3)
_cell_length_b                   7.7036(14)
_cell_length_c                   15.893(2)
_cell_measurement_reflns_used    2030
_cell_measurement_temperature    150
_cell_measurement_theta_max      28
_cell_measurement_theta_min      2
_cell_volume                     1822.3(5)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9619
_diffrn_reflns_theta_full        27.491
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_min         1.769
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.441
_exptl_crystal_size_mid          0.301
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         2771
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          0.0002572
_refine_ls_shift/su_mean         0.0000153
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 1.67P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1099
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.0975
_reflns_limit_h_max              19
_reflns_limit_h_min              -19
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                2771
_reflns_number_total             4158
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.00
_oxford_diffrn_Wilson_scale      11.38
_oxford_refine_ls_r_factor_ref   0.0504
_oxford_refine_ls_scale          0.312
_oxford_reflns_number_all        4142
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_cod_data_source_file            jo8b02870_si_003.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               4033745
_iucr_refine_instructions_details_constraints
;
#
# Punched on 10/09/17 at 18:37:43
#
#LIST     12                                                                    
BLOCK F(1,X'S,U'S) UNTIL C(26), H(11,X'S,U[ISO]) UNTIL LAST 
END                                                                             
;
_iucr_refine_instructions_details_restraints
;
#
# Punched on 10/09/17 at 18:37:43
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2
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_occupancy
_atom_site_adp_type
F1 F 0.50908(9) 0.85621(17) 0.04459(8) 0.0260 1.0000 Uani
F2 F 0.59306(10) 1.09054(17) 0.14902(10) 0.0341 1.0000 Uani
F3 F 0.68813(10) 0.9892(2) 0.29705(9) 0.0368 1.0000 Uani
F4 F 0.70086(10) 0.6461(2) 0.33673(8) 0.0383 1.0000 Uani
F5 F 0.62306(10) 0.40777(17) 0.22972(9) 0.0318 1.0000 Uani
C1 C 0.43002(17) 0.1142(4) 0.27401(15) 0.0267 1.0000 Uani
C2 C 0.48847(19) 0.1122(4) 0.34787(16) 0.0349 1.0000 Uani
C3 C 0.5103(2) -0.0441(5) 0.39016(18) 0.0427 1.0000 Uani
C4 C 0.4705(2) -0.1935(4) 0.35970(18) 0.0411 1.0000 Uani
C5 C 0.3639(2) -0.3521(4) 0.2578(2) 0.0410 1.0000 Uani
C6 C 0.2997(2) -0.3506(4) 0.1914(2) 0.0409 1.0000 Uani
C7 C 0.2060(2) -0.1978(4) 0.07639(18) 0.0397 1.0000 Uani
C8 C 0.18342(19) -0.0552(4) 0.03039(17) 0.0383 1.0000 Uani
C9 C 0.22119(17) 0.2405(4) -0.01518(17) 0.0339 1.0000 Uani
C10 C 0.28058(17) 0.3750(4) -0.01596(15) 0.0284 1.0000 Uani
C11 C 0.36404(15) 0.3674(3) 0.03615(14) 0.0207 1.0000 Uani
C12 C 0.37868(16) 0.2333(3) 0.09313(14) 0.0207 1.0000 Uani
C13 C 0.31630(16) 0.0987(3) 0.10000(14) 0.0233 1.0000 Uani
C14 C 0.23842(16) 0.0968(4) 0.03903(15) 0.0288 1.0000 Uani
C15 C 0.33024(16) -0.0450(3) 0.15986(15) 0.0247 1.0000 Uani
C16 C 0.27940(18) -0.1976(3) 0.14269(16) 0.0320 1.0000 Uani
C17 C 0.39218(16) -0.0405(3) 0.23743(15) 0.0254 1.0000 Uani
C18 C 0.40987(18) -0.1965(4) 0.28458(17) 0.0341 1.0000 Uani
C19 C 0.43224(15) 0.5055(3) 0.02263(13) 0.0191 1.0000 Uani
C20 C 0.52987(15) 0.4874(3) 0.06670(14) 0.0182 1.0000 Uani
C21 C 0.56469(15) 0.6222(3) 0.13145(13) 0.0174 1.0000 Uani
C22 C 0.55760(15) 0.7986(3) 0.11579(14) 0.0199 1.0000 Uani
C23 C 0.59961(16) 0.9210(3) 0.16926(16) 0.0228 1.0000 Uani
C24 C 0.64852(16) 0.8700(3) 0.24382(15) 0.0244 1.0000 Uani
C25 C 0.65417(16) 0.6973(3) 0.26349(14) 0.0250 1.0000 Uani
C26 C 0.61345(16) 0.5767(3) 0.20791(14) 0.0214 1.0000 Uani
H11 H 0.4117(16) 0.231(3) 0.2497(15) 0.022(6) 1.0000 Uiso
H21 H 0.5121(17) 0.225(4) 0.3710(16) 0.029(7) 1.0000 Uiso
H31 H 0.553(2) -0.044(4) 0.442(2) 0.053(9) 1.0000 Uiso
H41 H 0.4820(17) -0.307(3) 0.3885(15) 0.027(7) 1.0000 Uiso
H51 H 0.3813(19) -0.455(4) 0.2886(18) 0.042(8) 1.0000 Uiso
H61 H 0.269(2) -0.455(4) 0.1755(18) 0.046(9) 1.0000 Uiso
H71 H 0.1730(19) -0.305(4) 0.0688(17) 0.039(8) 1.0000 Uiso
H81 H 0.129(2) -0.044(4) -0.0143(18) 0.041(8) 1.0000 Uiso
H91 H 0.1682(19) 0.240(4) -0.0544(17) 0.038(8) 1.0000 Uiso
H101 H 0.2689(18) 0.473(4) -0.0554(17) 0.036(8) 1.0000 Uiso
H121 H 0.4360(16) 0.231(3) 0.1280(14) 0.018(6) 1.0000 Uiso
H191 H 0.4050(15) 0.622(3) 0.0306(14) 0.016(6) 1.0000 Uiso
H201 H 0.5390(14) 0.381(3) 0.0870(13) 0.008(5) 1.0000 Uiso
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 C17 . 121.6(3) yes
C2 . C1 H11 . 117.1(14) no
C17 . C1 H11 . 121.1(13) no
C1 . C2 C3 . 120.5(3) yes
C1 . C2 H21 . 118.0(15) no
C3 . C2 H21 . 121.4(15) no
C2 . C3 C4 . 119.3(3) yes
C2 . C3 H31 . 119.7(18) no
C4 . C3 H31 . 121.0(18) no
C3 . C4 C18 . 121.8(3) yes
C3 . C4 H41 . 122.3(14) no
C18 . C4 H41 . 115.9(15) no
C6 . C5 C18 . 120.4(3) yes
C6 . C5 H51 . 122.6(17) no
C18 . C5 H51 . 117.0(17) no
C5 . C6 C16 . 121.5(3) yes
C5 . C6 H61 . 118.9(18) no
C16 . C6 H61 . 119.5(18) no
C8 . C7 C16 . 121.6(3) yes
C8 . C7 H71 . 122.6(17) no
C16 . C7 H71 . 115.7(17) no
C7 . C8 C14 . 120.8(3) yes
C7 . C8 H81 . 125.5(16) no
C14 . C8 H81 . 113.7(16) no
C10 . C9 C14 . 121.9(2) yes
C10 . C9 H91 . 119.4(17) no
C14 . C9 H91 . 118.6(17) no
C9 . C10 C11 . 119.6(3) yes
C9 . C10 H101 . 121.3(16) no
C11 . C10 H101 . 118.9(16) no
C10 . C11 C12 . 118.6(2) yes
C10 . C11 C19 . 117.0(2) yes
C12 . C11 C19 . 124.4(2) yes
C11 . C12 C13 . 123.2(2) yes
C11 . C12 H121 . 117.2(14) no
C13 . C12 H121 . 119.6(14) no
C12 . C13 C14 . 116.9(2) yes
C12 . C13 C15 . 124.2(2) yes
C14 . C13 C15 . 118.6(2) yes
C8 . C14 C13 . 119.4(3) yes
C8 . C14 C9 . 121.5(2) yes
C13 . C14 C9 . 119.0(2) yes
C13 . C15 C16 . 118.2(2) yes
C13 . C15 C17 . 124.3(2) yes
C16 . C15 C17 . 117.4(2) yes
C7 . C16 C6 . 119.8(3) yes
C7 . C16 C15 . 119.6(3) yes
C6 . C16 C15 . 120.5(3) yes
C15 . C17 C1 . 123.6(2) yes
C15 . C17 C18 . 119.2(2) yes
C1 . C17 C18 . 116.9(2) yes
C17 . C18 C5 . 119.9(3) yes
C17 . C18 C4 . 119.5(3) yes
C5 . C18 C4 . 120.5(3) yes
C11 . C19 C20 2_665 118.00(19) yes
C11 . C19 C20 . 119.40(19) yes
C20 2_665 C19 C20 . 89.49(17) yes
C11 . C19 H191 . 108.8(13) no
C20 2_665 C19 H191 . 105.9(13) no
C20 . C19 H191 . 113.6(13) no
C19 . C20 C19 2_665 90.51(17) yes
C19 . C20 C21 . 118.58(19) yes
C19 2_665 C20 C21 . 116.96(19) yes
C19 . C20 H201 . 110.2(14) no
C19 2_665 C20 H201 . 107.5(14) no
C21 . C20 H201 . 111.2(14) no
C20 . C21 C22 . 122.6(2) yes
C20 . C21 C26 . 121.8(2) yes
C22 . C21 C26 . 115.3(2) yes
F1 . C22 C21 . 119.8(2) yes
F1 . C22 C23 . 117.3(2) yes
C21 . C22 C23 . 122.9(2) yes
F2 . C23 C22 . 120.2(2) yes
F2 . C23 C24 . 120.0(2) yes
C22 . C23 C24 . 119.8(2) yes
F3 . C24 C23 . 120.0(2) yes
F3 . C24 C25 . 120.8(2) yes
C23 . C24 C25 . 119.2(2) yes
F4 . C25 C24 . 119.7(2) yes
F4 . C25 C26 . 120.4(2) yes
C24 . C25 C26 . 119.9(2) yes
F5 . C26 C21 . 119.9(2) yes
F5 . C26 C25 . 117.4(2) yes
C21 . C26 C25 . 122.8(2) yes
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
F1 C22 . 1.348(2) yes
F2 C23 . 1.346(3) yes
F3 C24 . 1.341(3) yes
F4 C25 . 1.346(3) yes
F5 C26 . 1.350(3) yes
C1 C2 . 1.381(4) yes
C1 C17 . 1.416(4) yes
C1 H11 . 1.00(2) no
C2 C3 . 1.399(4) yes
C2 H21 . 0.99(3) no
C3 C4 . 1.359(5) yes
C3 H31 . 0.98(3) no
C4 C18 . 1.415(4) yes
C4 H41 . 0.99(3) no
C5 C6 . 1.343(4) yes
C5 C18 . 1.423(4) yes
C5 H51 . 0.96(3) no
C6 C16 . 1.424(4) yes
C6 H61 . 0.95(3) no
C7 C8 . 1.341(4) yes
C7 C16 . 1.432(4) yes
C7 H71 . 0.96(3) no
C8 C14 . 1.429(4) yes
C8 H81 . 1.02(3) no
C9 C10 . 1.367(4) yes
C9 C14 . 1.408(4) yes
C9 H91 . 0.95(3) no
C10 C11 . 1.419(3) yes
C10 H101 . 0.98(3) no
C11 C12 . 1.375(3) yes
C11 C19 . 1.508(3) yes
C12 C13 . 1.409(3) yes
C12 H121 . 0.97(2) no
C13 C14 . 1.429(3) yes
C13 C15 . 1.459(3) yes
C15 C16 . 1.411(3) yes
C15 C17 . 1.456(3) yes
C17 C18 . 1.425(4) yes
C19 C20 2_665 1.589(3) yes
C19 C20 . 1.554(3) yes
C19 H191 . 1.00(2) no
C20 C21 . 1.512(3) yes
C20 H201 . 0.88(2) no
C21 C22 . 1.383(3) yes
C21 C26 . 1.389(3) yes
C22 C23 . 1.373(3) yes
C23 C24 . 1.377(3) yes
C24 C25 . 1.367(4) yes
C25 C26 . 1.375(3) yes
