#------------------------------------------------------------------------------
#$Date: 2017-07-11 14:26:40 +0300 (Tue, 11 Jul 2017) $
#$Revision: 198632 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/79/4027940.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_4027940
loop_
_publ_author_name
'Jan Vávra'
'Lukáš Severa'
'Ivana Císařová'
'Blanka Klepetářová'
'David Šaman'
'Dušan Koval'
'Václav Kašička'
'Filip Teplý'
_publ_section_title
;
 Search for Conglomerate in Set of [7]Helquat Salts: Multigram Resolution
 of Helicene-Viologen Hybrid by Preferential Crystallization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1329
_journal_page_last               1342
_journal_paper_doi               10.1021/jo301615k
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C30 H26 N2, 2(C2 F3 O2)'
_chemical_formula_sum            'C34 H26 F6 N2 O4'
_chemical_formula_weight         640.57
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           96
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3080(2)
_cell_length_b                   8.3080(2)
_cell_length_c                   40.7386(11)
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.50
_cell_volume                     2811.89(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0112
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            23633
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.9575
_exptl_absorpt_correction_T_min  0.9384
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_description       prism
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.8(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0652P)²+1.1936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1248
_reflns_number_gt                3151
_reflns_number_total             3221
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo301615k_2_CF3CO2.cif
_cod_data_source_block           jv1923_uochb
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multi-scans' was replaced
with the value 'multi-scan' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_cell_volume        2811.90(12)
_cod_database_code               4027940
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'x+1/2, -y+1/2, -z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'-x, -y, z+1/2'
'y, x, -z'
'-y, -x, -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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.3354(2) 0.0071(2) 1.00756(4) 0.0222(3) Uani 1 1 d .
H1 H 0.4102 0.0724 1.0191 0.027 Uiso 1 1 calc R
C2 C 0.2886(2) -0.1373(2) 1.02058(5) 0.0271(4) Uani 1 1 d .
H2 H 0.3284 -0.1704 1.0414 0.033 Uiso 1 1 calc R
C3 C 0.1805(2) -0.2375(2) 1.00295(5) 0.0309(4) Uani 1 1 d .
H3 H 0.1426 -0.3341 1.0128 0.037 Uiso 1 1 calc R
C4 C 0.1305(2) -0.1977(2) 0.97234(5) 0.0287(4) Uani 1 1 d .
H4 H 0.0658 -0.2705 0.9601 0.034 Uiso 1 1 calc R
C5 C 0.1749(2) -0.0467(2) 0.95855(5) 0.0247(4) Uani 1 1 d .
C6 C 0.1227(2) -0.0005(2) 0.92693(5) 0.0289(4) Uani 1 1 d .
H6 H 0.0555 -0.0699 0.9145 0.035 Uiso 1 1 calc R
C7 C 0.1691(3) 0.1438(3) 0.91441(4) 0.0301(4) Uani 1 1 d .
H7 H 0.1409 0.1712 0.8925 0.036 Uiso 1 1 calc R
N8 N 0.25602(19) 0.25013(19) 0.93300(4) 0.0243(3) Uani 1 1 d .
C9 C 0.3025(3) 0.4064(2) 0.91839(4) 0.0285(4) Uani 1 1 d .
H9A H 0.2269 0.4912 0.9257 0.034 Uiso 1 1 calc R
H9B H 0.2969 0.3995 0.8942 0.034 Uiso 1 1 calc R
C10 C 0.4708(3) 0.4489(2) 0.92879(4) 0.0294(4) Uani 1 1 d .
H10A H 0.5027 0.5535 0.9191 0.035 Uiso 1 1 calc R
H10B H 0.5472 0.3656 0.9211 0.035 Uiso 1 1 calc R
C11 C 0.4749(2) 0.4593(2) 0.96586(4) 0.0229(4) Uani 1 1 d .
C12 C 0.5709(2) 0.5707(2) 0.98286(4) 0.0230(4) Uani 1 1 d .
C13 C 0.6763(3) 0.6862(3) 0.96424(5) 0.0383(5) Uani 1 1 d .
H13A H 0.6242 0.7919 0.9634 0.057 Uiso 1 1 calc R
H13B H 0.6928 0.6460 0.9419 0.057 Uiso 1 1 calc R
H13C H 0.7804 0.6958 0.9754 0.057 Uiso 1 1 calc R
C14 C 0.3733(2) 0.3533(2) 0.98293(4) 0.0192(3) Uani 1 1 d .
C15 C 0.2999(2) 0.2178(2) 0.96430(4) 0.0199(3) Uani 1 1 d .
C16 C 0.2738(2) 0.0602(2) 0.97707(4) 0.0212(3) Uani 1 1 d .
C17 C 0.5329(2) 0.0703(2) 0.85913(5) 0.0309(4) Uani 1 1 d .
C18 C 0.6155(4) -0.0128(3) 0.88868(6) 0.0489(6) Uani 1 1 d .
F1 F 0.6207(14) 0.0662(11) 0.9163(2) 0.090(3) Uani 0.572(17) 1 d P
F2 F 0.5051(10) -0.1389(9) 0.89855(16) 0.078(2) Uani 0.572(17) 1 d P
F3 F 0.7453(9) -0.0822(12) 0.88554(13) 0.089(3) Uani 0.572(17) 1 d P
F1B F 0.5850(14) 0.0491(14) 0.91682(18) 0.073(3) Uani 0.428(17) 1 d P
F2B F 0.613(2) -0.1658(6) 0.8873(2) 0.094(5) Uani 0.428(17) 1 d P
F3B F 0.7846(8) 0.023(2) 0.8836(2) 0.103(4) Uani 0.428(17) 1 d P
O1 O 0.4435(2) 0.1823(2) 0.86624(4) 0.0400(4) Uani 1 1 d .
O2 O 0.5632(2) 0.0072(3) 0.83249(4) 0.0507(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_
_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 C16 120.77(17) . .
C2 C1 H1 119.6 . .
C16 C1 H1 119.6 . .
C1 C2 C3 119.85(18) . .
C1 C2 H2 120.1 . .
C3 C2 H2 120.1 . .
C4 C3 C2 121.08(18) . .
C4 C3 H3 119.5 . .
C2 C3 H3 119.5 . .
C3 C4 C5 119.92(17) . .
C3 C4 H4 120.0 . .
C5 C4 H4 120.0 . .
C6 C5 C4 121.33(17) . .
C6 C5 C16 119.36(17) . .
C4 C5 C16 119.30(17) . .
C7 C6 C5 119.70(17) . .
C7 C6 H6 120.2 . .
C5 C6 H6 120.2 . .
C6 C7 N8 120.73(17) . .
C6 C7 H7 119.6 . .
N8 C7 H7 119.6 . .
C15 N8 C7 122.34(16) . .
C15 N8 C9 118.89(15) . .
C7 N8 C9 118.77(16) . .
N8 C9 C10 109.60(15) . .
N8 C9 H9A 109.8 . .
C10 C9 H9A 109.8 . .
N8 C9 H9B 109.8 . .
C10 C9 H9B 109.8 . .
H9A C9 H9B 108.2 . .
C9 C10 C11 108.39(15) . .
C9 C10 H10A 110.0 . .
C11 C10 H10A 110.0 . .
C9 C10 H10B 110.0 . .
C11 C10 H10B 110.0 . .
H10A C10 H10B 108.4 . .
C14 C11 C12 120.70(16) . .
C14 C11 C10 116.44(15) . .
C12 C11 C10 122.84(16) . .
C12 C12 C11 119.54(10) 7_557 .
C12 C12 C13 120.28(11) 7_557 .
C11 C12 C13 120.16(17) . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C11 C14 C14 119.03(10) . 7_557
C11 C14 C15 117.90(14) . .
C14 C14 C15 122.94(9) 7_557 .
N8 C15 C16 119.04(16) . .
N8 C15 C14 116.14(15) . .
C16 C15 C14 124.82(15) . .
C1 C16 C15 123.52(16) . .
C1 C16 C5 118.63(17) . .
C15 C16 C5 117.81(16) . .
O1 C17 O2 130.9(2) . .
O1 C17 C18 115.04(19) . .
O2 C17 C18 113.9(2) . .
F3 C18 F2B 62.6(6) . .
F3 C18 F1B 117.0(5) . .
F2B C18 F1B 115.9(7) . .
F3 C18 F1 107.3(6) . .
F2B C18 F1 122.8(6) . .
F1B C18 F1 14.6(9) . .
F3 C18 F2 104.2(4) . .
F2B C18 F2 44.0(6) . .
F1B C18 F2 85.2(6) . .
F1 C18 F2 98.4(5) . .
F3 C18 F3B 39.8(4) . .
F2B C18 F3B 102.2(6) . .
F1B C18 F3B 103.8(7) . .
F1 C18 F3B 89.4(6) . .
F2 C18 F3B 143.2(5) . .
F3 C18 C17 121.1(4) . .
F2B C18 C17 113.9(3) . .
F1B C18 C17 115.4(5) . .
F1 C18 C17 117.5(5) . .
F2 C18 C17 104.9(3) . .
F3B C18 C17 103.1(5) . .
F2B F2 C18 58.8(4) . .
F3B F3 C18 82.9(7) . .
F3B F3 F2B 142.9(8) . .
C18 F3 F2B 60.3(4) . .
F2 F2B C18 77.1(6) . .
F2 F2B F3 130.0(7) . .
C18 F2B F3 57.1(4) . .
F3 F3B C18 57.3(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.368(3) .
C1 C16 1.414(2) .
C1 H1 0.9500 .
C2 C3 1.420(3) .
C2 H2 0.9500 .
C3 C4 1.355(3) .
C3 H3 0.9500 .
C4 C5 1.424(3) .
C4 H4 0.9500 .
C5 C6 1.412(3) .
C5 C16 1.426(2) .
C6 C7 1.358(3) .
C6 H6 0.9500 .
C7 N8 1.370(2) .
C7 H7 0.9500 .
N8 C15 1.353(2) .
N8 C9 1.480(2) .
C9 C10 1.503(3) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.513(2) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C14 1.404(2) .
C11 C12 1.404(3) .
C12 C12 1.397(4) 7_557
C12 C13 1.504(3) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 C14 1.410(3) 7_557
C14 C15 1.489(2) .
C15 C16 1.425(2) .
C17 O1 1.225(3) .
C17 O2 1.231(3) .
C17 C18 1.548(3) .
C18 F3 1.229(5) .
C18 F2B 1.273(6) .
C18 F1B 1.282(8) .
C18 F1 1.302(8) .
C18 F2 1.450(5) .
C18 F3B 1.451(8) .
F2 F2B 1.034(11) .
F3 F3B 0.936(10) .
F3 F2B 1.300(11) .
