#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:42:19 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178439 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/60/4026059.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_4026059
loop_
_publ_author_name
'Daniela Vuluga'
'Julien Legros'
'Benoit Crousse'
'Alexandra M. Z. Slawin'
'Christian Laurence'
'Pierre Nicolet'
'Danièle Bonnet-Delpon'
_publ_section_title
;
 Influence of the Structure of Polyfluorinated Alcohols on Brønsted
 Acidity/Hydrogen-Bond Donor Ability and Consequences on the Promoter
 Effect
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1126
_journal_page_last               1133
_journal_paper_doi               10.1021/jo1023816
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C4 H10 N2,2(C6 H6 F6 O1)'
_chemical_formula_sum            'C16 H22 F12 N2 O2'
_chemical_formula_weight         502.36
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.055(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.9943(9)
_cell_length_b                   16.750(2)
_cell_length_c                   9.4455(13)
_cell_measurement_reflns_used    8531
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.1
_cell_volume                     1032.7(2)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2004)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'graphite monochromator'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0888
_diffrn_reflns_av_sigmaI/netI    0.0669
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8764
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.15
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  0.9780
_exptl_absorpt_correction_T_min  0.9600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1896
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0563
_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)+(0.0385P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1123
_reflns_number_gt                1394
_reflns_number_total             1896
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1023816_si_002.cif
_cod_data_source_block           legros4
_cod_database_code               4026059
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.8102(3) 0.01873(13) 0.5258(2) 0.0203(5) Uani 1 1 d D
H1N H 0.722(3) -0.0172(12) 0.464(2) 0.016(7) Uiso 1 1 d D
C2 C 0.8912(4) 0.07093(15) 0.4353(3) 0.0217(6) Uani 1 1 d .
H2A H 0.9737 0.1139 0.5013 0.026 Uiso 1 1 calc R
H2B H 0.7750 0.0964 0.3543 0.026 Uiso 1 1 calc R
C3 C 1.0226(4) 0.02696(16) 0.3635(3) 0.0221(6) Uani 1 1 d .
H3A H 0.9350 -0.0100 0.2852 0.026 Uiso 1 1 calc R
H3B H 1.0820 0.0661 0.3122 0.026 Uiso 1 1 calc R
O11 O 0.5474(3) 0.09638(10) 0.61484(18) 0.0194(4) Uani 1 1 d D
H11O H 0.658(4) 0.0707(16) 0.592(3) 0.050(10) Uiso 1 1 d D
C11 C 0.6197(4) 0.13519(15) 0.7553(3) 0.0154(6) Uani 1 1 d .
C12 C 0.6531(4) 0.07165(16) 0.8795(3) 0.0212(6) Uani 1 1 d .
F1 F 0.8149(2) 0.02618(9) 0.89184(18) 0.0352(5) Uani 1 1 d .
F2 F 0.4946(2) 0.02214(9) 0.85083(17) 0.0322(4) Uani 1 1 d .
F3 F 0.6880(2) 0.10382(9) 1.01683(16) 0.0314(4) Uani 1 1 d .
C13 C 0.4485(4) 0.19166(15) 0.7566(3) 0.0195(6) Uani 1 1 d .
F4 F 0.2835(2) 0.15312(9) 0.76266(19) 0.0341(4) Uani 1 1 d .
F5 F 0.5072(2) 0.24189(9) 0.87354(17) 0.0321(4) Uani 1 1 d .
F6 F 0.3813(3) 0.23612(9) 0.63135(18) 0.0348(5) Uani 1 1 d .
C14 C 0.8205(4) 0.18084(15) 0.7849(3) 0.0200(6) Uani 1 1 d .
H14A H 0.8648 0.2040 0.8882 0.024 Uiso 1 1 calc R
H14B H 0.9269 0.1424 0.7831 0.024 Uiso 1 1 calc R
C15 C 0.8092(4) 0.24635(16) 0.6748(3) 0.0265(7) Uani 1 1 d .
H15A H 0.7621 0.2335 0.5699 0.032 Uiso 1 1 calc R
C16 C 0.8610(4) 0.32096(17) 0.7152(4) 0.0389(8) Uani 1 1 d .
H16A H 0.9086 0.3355 0.8193 0.047 Uiso 1 1 calc R
H16B H 0.8507 0.3602 0.6401 0.047 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 N1 C3 110.39(19) . 3_756
C2 N1 H1N 109.8(16) . .
C3 N1 H1N 107.2(15) 3_756 .
N1 C2 C3 113.2(2) . .
N1 C2 H2A 108.9 . .
C3 C2 H2A 108.9 . .
N1 C2 H2B 108.9 . .
C3 C2 H2B 108.9 . .
H2A C2 H2B 107.8 . .
N1 C3 C2 112.9(2) 3_756 .
N1 C3 H3A 109.0 3_756 .
C2 C3 H3A 109.0 . .
N1 C3 H3B 109.0 3_756 .
C2 C3 H3B 109.0 . .
H3A C3 H3B 107.8 . .
C11 O11 H11O 111.8(17) . .
O11 C11 C13 106.12(19) . .
O11 C11 C14 113.6(2) . .
C13 C11 C14 111.0(2) . .
O11 C11 C12 107.8(2) . .
C13 C11 C12 109.1(2) . .
C14 C11 C12 109.1(2) . .
F2 C12 F1 106.3(2) . .
F2 C12 F3 107.2(2) . .
F1 C12 F3 106.9(2) . .
F2 C12 C11 112.9(2) . .
F1 C12 C11 110.7(2) . .
F3 C12 C11 112.6(2) . .
F5 C13 F6 106.8(2) . .
F5 C13 F4 106.4(2) . .
F6 C13 F4 105.8(2) . .
F5 C13 C11 112.8(2) . .
F6 C13 C11 111.5(2) . .
F4 C13 C11 113.0(2) . .
C15 C14 C11 115.0(2) . .
C15 C14 H14A 108.5 . .
C11 C14 H14A 108.5 . .
C15 C14 H14B 108.5 . .
C11 C14 H14B 108.5 . .
H14A C14 H14B 107.5 . .
C16 C15 C14 123.6(3) . .
C16 C15 H15A 118.2 . .
C14 C15 H15A 118.2 . .
C15 C16 H16A 120.0 . .
C15 C16 H16B 120.0 . .
H16A C16 H16B 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.471(3) .
N1 C3 1.473(3) 3_756
N1 H1N 0.908(16) .
C2 C3 1.515(3) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 N1 1.473(3) 3_756
C3 H3A 0.9900 .
C3 H3B 0.9900 .
O11 C11 1.399(3) .
O11 H11O 0.978(18) .
C11 C13 1.530(3) .
C11 C14 1.534(3) .
C11 C12 1.538(4) .
C12 F2 1.332(3) .
C12 F1 1.334(3) .
C12 F3 1.343(3) .
C13 F5 1.331(3) .
C13 F6 1.333(3) .
C13 F4 1.341(3) .
C14 C15 1.494(4) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.319(4) .
C15 H15A 0.9500 .
C16 H16A 0.9500 .
C16 H16B 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 H1N O11 0.908(16) 2.202(18) 3.058(3) 157(2) 3_656
O11 H11O N1 0.978(18) 1.658(19) 2.624(3) 169(3) .
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
C3 N1 C2 C3 52.3(3) 3_756 .
N1 C2 C3 N1 -53.7(3) . 3_756
O11 C11 C12 F2 -47.6(3) . .
C13 C11 C12 F2 67.2(3) . .
C14 C11 C12 F2 -171.4(2) . .
O11 C11 C12 F1 71.4(2) . .
C13 C11 C12 F1 -173.8(2) . .
C14 C11 C12 F1 -52.4(3) . .
O11 C11 C12 F3 -169.07(19) . .
C13 C11 C12 F3 -54.3(3) . .
C14 C11 C12 F3 67.1(3) . .
O11 C11 C13 F5 -170.04(19) . .
C14 C11 C13 F5 -46.2(3) . .
C12 C11 C13 F5 74.1(3) . .
O11 C11 C13 F6 -49.9(3) . .
C14 C11 C13 F6 73.9(3) . .
C12 C11 C13 F6 -165.8(2) . .
O11 C11 C13 F4 69.1(2) . .
C14 C11 C13 F4 -167.0(2) . .
C12 C11 C13 F4 -46.8(3) . .
O11 C11 C14 C15 61.3(3) . .
C13 C11 C14 C15 -58.2(3) . .
C12 C11 C14 C15 -178.4(2) . .
C11 C14 C15 C16 124.7(3) . .
