#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/38/1503847.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_1503847
loop_
_publ_author_name
'Ueki, Hisanori'
'Soloshonok, Vadim A.'
_publ_section_title
;
 New sterically driven mode for generation of helical chirality.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1797
_journal_page_last               1800
_journal_paper_doi               10.1021/ol900357d
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C13 H13 F6 N O'
_chemical_formula_sum            'C13 H13 F6 N O'
_chemical_formula_weight         313.24
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           92
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 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            8
_cell_length_a                   11.865(2)
_cell_length_b                   11.865(2)
_cell_length_c                   19.328(4)
_cell_measurement_reflns_used    6506
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.84
_cell_measurement_theta_min      2.65
_cell_volume                     2721.0(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2000)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2000)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       '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  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21550
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.01
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_T_max  0.9804
_exptl_absorpt_correction_T_min  0.9557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2673
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0282
_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)+(0.0490P)²+0.4487P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0740
_reflns_number_gt                2579
_reflns_number_total             2673
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ol900357d_si_001.cif
_cod_data_source_block           06113
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               1503847
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'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
F1 F 0.73882(8) 0.42495(8) 0.88476(5) 0.0296(2) Uani 1 1 d .
F2 F 0.78681(8) 0.28251(8) 0.82230(4) 0.0244(2) Uani 1 1 d .
F3 F 0.69871(8) 0.25641(9) 0.91732(5) 0.0295(2) Uani 1 1 d .
F4 F 0.97345(8) 0.16927(8) 0.86117(5) 0.0279(2) Uani 1 1 d .
F5 F 0.86852(9) 0.11747(8) 0.94573(5) 0.0319(2) Uani 1 1 d .
F6 F 1.03139(9) 0.19043(9) 0.96548(5) 0.0365(3) Uani 1 1 d .
O1 O 0.96431(9) 0.42326(9) 0.83267(5) 0.0220(2) Uani 1 1 d .
N1 N 1.05666(11) 0.43810(10) 0.93330(6) 0.0180(3) Uani 1 1 d .
H1NA H 1.0605(15) 0.4266(15) 0.9744(10) 0.022 Uiso 1 1 d .
C1 C 0.86205(14) 0.34450(15) 1.00452(8) 0.0279(4) Uani 1 1 d .
H1A H 0.9313 0.3411 1.0321 0.042 Uiso 1 1 calc R
H1B H 0.8075 0.2899 1.0226 0.042 Uiso 1 1 calc R
H1C H 0.8301 0.4205 1.0072 0.042 Uiso 1 1 calc R
C2 C 0.88916(12) 0.31610(13) 0.92860(7) 0.0184(3) Uani 1 1 d .
C3 C 0.77827(12) 0.31952(13) 0.88708(8) 0.0202(3) Uani 1 1 d .
C4 C 0.94080(13) 0.19733(13) 0.92496(8) 0.0224(3) Uani 1 1 d .
C5 C 0.97381(12) 0.39919(12) 0.89390(7) 0.0163(3) Uani 1 1 d .
C6 C 1.14293(13) 0.51204(13) 0.90336(7) 0.0177(3) Uani 1 1 d .
H6 H 1.1637 0.4817 0.8568 0.021 Uiso 1 1 calc R
C7 C 1.24797(13) 0.50912(13) 0.94905(7) 0.0218(3) Uani 1 1 d .
H7A H 1.2753 0.4314 0.9527 0.033 Uiso 1 1 calc R
H7B H 1.2292 0.5376 0.9952 0.033 Uiso 1 1 calc R
H7C H 1.3068 0.5565 0.9285 0.033 Uiso 1 1 calc R
C8 C 1.10153(13) 0.63247(13) 0.89412(7) 0.0188(3) Uani 1 1 d .
C9 C 1.01367(15) 0.67731(15) 0.93230(9) 0.0278(4) Uani 1 1 d .
H9 H 0.9730 0.6308 0.9636 0.033 Uiso 1 1 calc R
C10 C 0.98474(16) 0.79001(16) 0.92501(10) 0.0379(4) Uani 1 1 d .
H10 H 0.9239 0.8197 0.9512 0.045 Uiso 1 1 calc R
C11 C 1.04275(17) 0.85954(15) 0.88033(10) 0.0369(4) Uani 1 1 d .
H11 H 1.0225 0.9367 0.8760 0.044 Uiso 1 1 calc R
C12 C 1.13008(19) 0.81595(16) 0.84220(9) 0.0372(4) Uani 1 1 d .
H12 H 1.1709 0.8632 0.8114 0.045 Uiso 1 1 calc R
C13 C 1.15917(15) 0.70232(14) 0.84844(8) 0.0276(4) Uani 1 1 d .
H13 H 1.2188 0.6725 0.8212 0.033 Uiso 1 1 calc R
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
C5 N1 C6 119.92(12)
C5 N1 H1NA 123.2(13)
C6 N1 H1NA 116.7(13)
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C4 C2 C1 109.11(12)
C4 C2 C3 109.89(12)
C1 C2 C3 108.18(12)
C4 C2 C5 107.64(12)
C1 C2 C5 113.96(12)
C3 C2 C5 108.02(11)
F2 C3 F1 107.70(12)
F2 C3 F3 106.25(12)
F1 C3 F3 106.93(12)
F2 C3 C2 114.59(12)
F1 C3 C2 109.94(12)
F3 C3 C2 111.08(12)
F6 C4 F4 107.07(13)
F6 C4 F5 107.27(12)
F4 C4 F5 106.63(13)
F6 C4 C2 110.53(13)
F4 C4 C2 112.73(12)
F5 C4 C2 112.29(13)
O1 C5 N1 122.87(13)
O1 C5 C2 120.31(13)
N1 C5 C2 116.79(12)
N1 C6 C8 112.50(12)
N1 C6 C7 109.13(12)
C8 C6 C7 110.64(12)
N1 C6 H6 108.1
C8 C6 H6 108.1
C7 C6 H6 108.1
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C9 C8 C13 118.68(15)
C9 C8 C6 122.80(14)
C13 C8 C6 118.39(14)
C8 C9 C10 120.18(17)
C8 C9 H9 119.9
C10 C9 H9 119.9
C11 C10 C9 121.12(17)
C11 C10 H10 119.4
C9 C10 H10 119.4
C12 C11 C10 119.19(16)
C12 C11 H11 120.4
C10 C11 H11 120.4
C11 C12 C13 120.25(17)
C11 C12 H12 119.9
C13 C12 H12 119.9
C8 C13 C12 120.56(17)
C8 C13 H13 119.7
C12 C13 H13 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C3 1.3364(19)
F2 C3 1.3308(18)
F3 C3 1.3391(17)
F4 C4 1.3345(19)
F5 C4 1.3396(19)
F6 C4 1.3325(18)
O1 C5 1.2227(17)
N1 C5 1.3263(19)
N1 C6 1.4670(19)
N1 H1NA 0.807(19)
C1 C2 1.540(2)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C4 1.538(2)
C2 C3 1.542(2)
C2 C5 1.559(2)
C6 C8 1.522(2)
C6 C7 1.528(2)
C6 H6 1.0000
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 C9 1.384(2)
C8 C13 1.391(2)
C9 C10 1.388(3)
C9 H9 0.9500
C10 C11 1.378(3)
C10 H10 0.9500
C11 C12 1.373(3)
C11 H11 0.9500
C12 C13 1.397(3)
C12 H12 0.9500
C13 H13 0.9500
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
N1 H1NA O1 0.807(19) 2.149(19) 2.9135(17) 158.1(17) 3_645
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
C4 C2 C3 F2 -52.78(16)
C1 C2 C3 F2 -171.81(13)
C5 C2 C3 F2 64.39(16)
C4 C2 C3 F1 -174.21(12)
C1 C2 C3 F1 66.76(15)
C5 C2 C3 F1 -57.05(16)
C4 C2 C3 F3 67.64(16)
C1 C2 C3 F3 -51.39(17)
C5 C2 C3 F3 -175.20(12)
C1 C2 C4 F6 -56.13(16)
C3 C2 C4 F6 -174.60(12)
C5 C2 C4 F6 68.00(15)
C1 C2 C4 F4 -175.93(12)
C3 C2 C4 F4 65.61(15)
C5 C2 C4 F4 -51.79(15)
C1 C2 C4 F5 63.60(16)
C3 C2 C4 F5 -54.86(16)
C5 C2 C4 F5 -172.26(12)
C6 N1 C5 O1 -1.0(2)
C6 N1 C5 C2 176.86(13)
C4 C2 C5 O1 93.73(16)
C1 C2 C5 O1 -145.13(15)
C3 C2 C5 O1 -24.89(19)
C4 C2 C5 N1 -84.15(15)
C1 C2 C5 N1 37.00(19)
C3 C2 C5 N1 157.24(13)
C5 N1 C6 C8 77.69(16)
C5 N1 C6 C7 -159.12(13)
N1 C6 C8 C9 23.3(2)
C7 C6 C8 C9 -99.08(16)
N1 C6 C8 C13 -160.87(13)
C7 C6 C8 C13 76.78(16)
C13 C8 C9 C10 -0.3(2)
C6 C8 C9 C10 175.52(15)
C8 C9 C10 C11 -0.4(3)
C9 C10 C11 C12 0.4(3)
C10 C11 C12 C13 0.3(3)
C9 C8 C13 C12 1.1(2)
C6 C8 C13 C12 -174.92(15)
C11 C12 C13 C8 -1.1(3)
