#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:53:33 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180361 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/30/7203076.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_7203076
loop_
_publ_author_name
'Piotrkowska, Barbara'
'Gdaniec, Maria'
'Milewska, Maria J.'
'Połoński, Tadeusz'
_publ_section_title
;
 Aryl--perfluoroaryl stacking interactions, hydrogen bonding and steric
 effects in controlling the structure of supramolecular assemblies of
 N,N′-diaryloxalamides
;
_journal_issue                   10
_journal_name_full               CrystEngComm
_journal_page_first              868
_journal_paper_doi               10.1039/b709654b
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C18 H20 N2 O2, 2(C6 H F5 O)'
_chemical_formula_sum            'C30 H22 F10 N2 O4'
_chemical_formula_weight         664.50
_chemical_name_systematic
;
N,N'-bis(3,5-dimethylphenyl)ethanediamide
bis-2,3,4,5,6-pentafluorophenol
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.511(5)
_cell_angle_beta                 101.938(6)
_cell_angle_gamma                92.892(6)
_cell_formula_units_Z            1
_cell_length_a                   7.0285(5)
_cell_length_b                   7.5525(5)
_cell_length_c                   13.6546(9)
_cell_measurement_reflns_used    4271
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      4
_cell_volume                     707.74(8)
_computing_cell_refinement
;
Oxford Diffraction, CrysAlis Software, Version 1.171, 2003
;
_computing_data_collection
;
Oxford Diffraction, CrysAlis Software, Version 1.171, 2003
;
_computing_data_reduction
;
Oxford Diffraction, CrysAlis Software, Version 1.171, 2003
;
_computing_molecular_graphics
; 'Stereochemical Workstation (Siemens
Analytical X-Ray Instruments, Inc., 1989)'
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'KumaCCD diffractometer'
_diffrn_measurement_method       'ο scan'
_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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7436
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         4.58
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 50
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             338
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2883
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0382
_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)+(0.0620P)²+0.1966P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1112
_reflns_number_gt                2393
_reflns_number_total             2883
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b709654b.txt
_cod_data_source_block           4pfp
_cod_depositor_comments
;
The following automatic conversions were performed:
'_refine_ls_hydrogen_treatment' value 'refu' changed to 'refU' 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 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7203076
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.02035(17) 0.40420(14) 1.11353(8) 0.0298(3) Uani 1 1 d . . .
N1 N 0.11224(17) 0.67557(15) 1.08501(9) 0.0211(3) Uani 1 1 d . . .
H1N H 0.1339 0.7416 1.0341 0.031(5) Uiso 1 1 d R . .
C1 C 0.0232(2) 0.51637(18) 1.05725(10) 0.0207(3) Uani 1 1 d . . .
C2 C 0.17293(19) 0.75371(17) 1.18293(10) 0.0192(3) Uani 1 1 d . . .
C3 C 0.24233(19) 0.93144(18) 1.18858(11) 0.0206(3) Uani 1 1 d . . .
H3 H 0.2489 0.9879 1.1271 0.019(4) Uiso 1 1 d R . .
C4 C 0.30267(19) 1.01909(18) 1.28148(11) 0.0225(3) Uani 1 1 d . . .
C5 C 0.2937(2) 0.92662(19) 1.36746(11) 0.0237(3) Uani 1 1 d . . .
H5 H 0.3335 0.9914 1.4305 0.026(4) Uiso 1 1 d R . .
C6 C 0.2264(2) 0.74979(19) 1.36275(10) 0.0232(3) Uani 1 1 d . . .
C7 C 0.1646(2) 0.66298(18) 1.26914(10) 0.0209(3) Uani 1 1 d . . .
H7 H 0.1135 0.5423 1.2669 0.024(4) Uiso 1 1 d R . .
C8 C 0.3751(2) 1.2110(2) 1.28849(13) 0.0318(4) Uani 1 1 d . . .
H81 H 0.3209 1.2722 1.3379 0.070(7) Uiso 1 1 d R . .
H82 H 0.3413 1.2724 1.2272 0.082(8) Uiso 1 1 d R . .
H83 H 0.5124 1.2290 1.3152 0.062(7) Uiso 1 1 d R . .
C9 C 0.2187(3) 0.6510(2) 1.45611(12) 0.0366(4) Uani 1 1 d . . .
H91 H 0.1943 0.7239 1.5104 0.085(8) Uiso 1 1 d R . .
H92 H 0.1295 0.5485 1.4458 0.080(8) Uiso 1 1 d R . .
H93 H 0.3428 0.6067 1.4849 0.088(9) Uiso 1 1 d R . .
O1A O 0.21081(17) 0.91276(15) 0.91877(8) 0.0348(3) Uani 1 1 d . . .
H1O H 0.1620 0.8159 0.8886 0.075(8) Uiso 1 1 d R . .
F2A F 0.36264(15) 1.23988(13) 0.98767(7) 0.0383(3) Uani 1 1 d . . .
F3A F 0.43650(14) 1.49146(12) 0.86077(8) 0.0400(3) Uani 1 1 d . . .
F4A F 0.34817(15) 1.42170(13) 0.65902(8) 0.0431(3) Uani 1 1 d . . .
F5A F 0.19718(15) 1.09472(14) 0.58658(7) 0.0397(3) Uani 1 1 d . . .
F6A F 0.12899(13) 0.84002(12) 0.71401(7) 0.0333(2) Uani 1 1 d . . .
C1A C 0.2466(2) 1.03462(19) 0.85313(11) 0.0233(3) Uani 1 1 d . . .
C2A C 0.3243(2) 1.2022(2) 0.88844(11) 0.0248(3) Uani 1 1 d . . .
C3A C 0.3601(2) 1.33116(19) 0.82397(12) 0.0258(3) Uani 1 1 d . . .
C4A C 0.3171(2) 1.2959(2) 0.72218(12) 0.0272(3) Uani 1 1 d . . .
C5A C 0.2398(2) 1.1296(2) 0.68557(11) 0.0261(3) Uani 1 1 d . . .
C6A C 0.2054(2) 1.00149(19) 0.75040(11) 0.0238(3) 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'
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'
N N 0.0061 0.0033 '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
_geom_angle_publ_flag
C1 N1 C2 128.66(12) . . ?
C1 N1 H1N 114.7 . . ?
C2 N1 H1N 116.7 . . ?
O1 C1 N1 126.06(13) . . ?
O1 C1 C1 121.45(15) . 2_567 ?
N1 C1 C1 112.49(15) . 2_567 ?
C7 C2 C3 120.81(12) . . ?
C7 C2 N1 123.22(12) . . ?
C3 C2 N1 115.97(12) . . ?
C4 C3 C2 119.82(13) . . ?
C4 C3 H3 122.2 . . ?
C2 C3 H3 118.0 . . ?
C3 C4 C5 118.84(13) . . ?
C3 C4 C8 120.32(14) . . ?
C5 C4 C8 120.83(13) . . ?
C6 C5 C4 121.82(13) . . ?
C6 C5 H5 121.2 . . ?
C4 C5 H5 117.0 . . ?
C5 C6 C7 119.03(13) . . ?
C5 C6 C9 121.34(13) . . ?
C7 C6 C9 119.64(13) . . ?
C2 C7 C6 119.68(13) . . ?
C2 C7 H7 122.2 . . ?
C6 C7 H7 118.1 . . ?
C4 C8 H81 108.8 . . ?
C4 C8 H82 114.5 . . ?
H81 C8 H82 107.5 . . ?
C4 C8 H83 113.5 . . ?
H81 C8 H83 102.0 . . ?
H82 C8 H83 109.6 . . ?
C6 C9 H91 114.0 . . ?
C6 C9 H92 114.3 . . ?
H91 C9 H92 109.3 . . ?
C6 C9 H93 111.5 . . ?
H91 C9 H93 101.8 . . ?
H92 C9 H93 104.9 . . ?
C1A O1A H1O 111.1 . . ?
O1A C1A C6A 122.93(13) . . ?
O1A C1A C2A 119.51(13) . . ?
C6A C1A C2A 117.55(14) . . ?
F2A C2A C3A 119.53(13) . . ?
F2A C2A C1A 119.10(14) . . ?
C3A C2A C1A 121.36(14) . . ?
F3A C3A C4A 120.06(14) . . ?
F3A C3A C2A 119.76(14) . . ?
C4A C3A C2A 120.18(13) . . ?
F4A C4A C3A 120.48(14) . . ?
F4A C4A C5A 120.22(14) . . ?
C3A C4A C5A 119.30(14) . . ?
F5A C5A C6A 120.30(14) . . ?
F5A C5A C4A 119.55(14) . . ?
C6A C5A C4A 120.15(14) . . ?
F6A C6A C5A 119.74(13) . . ?
F6A C6A C1A 118.79(13) . . ?
C5A C6A C1A 121.46(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2279(18) . ?
N1 C1 1.3351(18) . ?
N1 C2 1.4195(17) . ?
N1 H1N 0.9000 . ?
C1 C1 1.540(3) 2_567 ?
C2 C7 1.388(2) . ?
C2 C3 1.3995(19) . ?
C3 C4 1.390(2) . ?
C3 H3 0.9600 . ?
C4 C5 1.393(2) . ?
C4 C8 1.5057(19) . ?
C5 C6 1.389(2) . ?
C5 H5 0.9600 . ?
C6 C7 1.3963(19) . ?
C6 C9 1.503(2) . ?
C7 H7 0.9600 . ?
C8 H81 0.9600 . ?
C8 H82 0.9600 . ?
C8 H83 0.9600 . ?
C9 H91 0.9600 . ?
C9 H92 0.9600 . ?
C9 H93 0.9600 . ?
O1A C1A 1.3518(18) . ?
O1A H1O 0.8500 . ?
F2A C2A 1.3456(17) . ?
F3A C3A 1.3406(16) . ?
F4A C4A 1.3395(17) . ?
F5A C5A 1.3385(17) . ?
F6A C6A 1.3469(16) . ?
C1A C6A 1.386(2) . ?
C1A C2A 1.386(2) . ?
C2A C3A 1.378(2) . ?
C3A C4A 1.376(2) . ?
C4A C5A 1.381(2) . ?
C5A C6A 1.374(2) . ?
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 O1A 0.90 2.20 3.0953(16) 174.8 .
N1 H1N O1 0.90 2.24 2.6981(15) 110.7 2_567
O1A H1O O1 0.85 1.89 2.6634(16) 150.5 2_567
C7 H7 O1 0.96 2.31 2.8994(17) 119.1 .
N1 H1N O1 0.90 2.24 2.6981(15) 110.7 2_567
