#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:51:12 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180359 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/28/7202832.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_7202832
loop_
_publ_author_name
'Russo, Luca'
'Biella, Serena'
'Lahtinen, Manu'
'Liantonio, Rosalba'
'Metrangolo, Pierangelo'
'Resnati, Giuseppe'
'Rissanen, Kari'
_publ_section_title
;
 Solution stoichiometry determines crystal stoichiometry in
 halogen-bonded supramolecular complexes
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              341
_journal_paper_doi               10.1039/b702512m
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         '2 C7 H7 O2 N,C6 F4 I2'
_chemical_formula_sum            'C20 H14 F4 I2 N2 O4'
_chemical_formula_weight         676.13
_chemical_name_systematic
;
?
;
_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                91.102(11)
_cell_angle_beta                 97.913(12)
_cell_angle_gamma                90.912(8)
_cell_formula_units_Z            1
_cell_length_a                   4.1581(4)
_cell_length_b                   10.7974(8)
_cell_length_c                   12.7958(19)
_cell_measurement_reflns_used    2343
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.5
_cell_volume                     568.81(11)
_computing_cell_refinement       EvalCCD
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'Mercury 1.3, Diamond 3'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_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  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6429
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         5.15
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.826
_exptl_absorpt_correction_T_max  0.6765
_exptl_absorpt_correction_T_min  0.2819
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.974
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             322
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.179
_refine_ls_R_factor_all          0.0220
_refine_ls_R_factor_gt           0.0163
_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)+(0.0000P)²+0.3199P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0365
_refine_ls_wR_factor_ref         0.0404
_reflns_number_gt                1785
_reflns_number_total             1924
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b702512m.txt
_cod_data_source_block           lrs031
_cod_database_code               7202832
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
I1 I 0.74502(4) 0.417214(16) 0.241908(12) 0.02916(8) Uani 1 1 d . . .
F1 F 0.9982(5) 0.25628(14) 0.05427(13) 0.0481(5) Uani 1 1 d . . .
F2 F 0.7971(5) 0.68019(15) 0.12705(12) 0.0476(5) Uani 1 1 d . . .
C8 C 0.8907(6) 0.4660(2) 0.09631(18) 0.0250(6) Uani 1 1 d . . .
O1 O 0.5759(5) 0.11900(18) 0.78213(14) 0.0410(5) Uani 1 1 d . . .
N1 N 0.5707(6) 0.3299(2) 0.43841(17) 0.0334(5) Uani 1 1 d . . .
O2 O 0.1981(6) 0.00451(19) 0.67729(16) 0.0508(6) Uani 1 1 d . . .
C4 C 0.3878(7) 0.2254(2) 0.4211(2) 0.0328(6) Uani 1 1 d . . .
H4A H 0.2967 0.2044 0.3506 0.039 Uiso 1 1 calc R . .
C1 C 0.4607(6) 0.1760(2) 0.6043(2) 0.0267(6) Uani 1 1 d . . .
C10 C 0.8986(6) 0.5897(2) 0.06535(19) 0.0277(6) Uani 1 1 d . . .
C5 C 0.3255(7) 0.1467(2) 0.5009(2) 0.0333(6) Uani 1 1 d . . .
H5A H 0.1934 0.0744 0.4852 0.040 Uiso 1 1 calc R . .
C2 C 0.6511(7) 0.2839(2) 0.6236(2) 0.0326(6) Uani 1 1 d . . .
H2A H 0.7475 0.3065 0.6932 0.039 Uiso 1 1 calc R . .
C9 C 0.9953(6) 0.3786(2) 0.0286(2) 0.0279(6) Uani 1 1 d . . .
C6 C 0.3933(7) 0.0896(2) 0.6900(2) 0.0318(6) Uani 1 1 d . . .
C3 C 0.6963(7) 0.3577(3) 0.5382(2) 0.0360(7) Uani 1 1 d . . .
H3A H 0.8231 0.4317 0.5516 0.043 Uiso 1 1 calc R . .
C7 C 0.5243(9) 0.0398(3) 0.8697(2) 0.0551(9) Uani 1 1 d . . .
H7A H 0.6672 0.0677 0.9335 0.083 Uiso 1 1 calc R . .
H7B H 0.5737 -0.0460 0.8524 0.083 Uiso 1 1 calc R . .
H7C H 0.2975 0.0445 0.8822 0.083 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'
I I -0.4742 1.8119 '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
I1 C8 C10 121.42(18) . . ?
I1 C8 C9 121.94(18) . . ?
C10 C8 C9 116.6(2) . . ?
C6 O1 C7 115.0(2) . . ?
C4 N1 C3 117.3(2) . . ?
N1 C4 H4A 118.3 . . ?
N1 C4 C5 123.4(3) . . ?
H4A C4 C5 118.3 . . ?
C5 C1 C2 118.6(2) . . ?
C5 C1 C6 118.2(2) . . ?
C2 C1 C6 123.2(2) . . ?
F2 C10 C8 120.0(2) . . ?
F2 C10 C9 118.9(2) . 2_765 ?
C8 C10 C9 121.1(2) . 2_765 ?
C4 C5 C1 118.7(3) . . ?
C4 C5 H5A 120.7 . . ?
C1 C5 H5A 120.7 . . ?
C1 C2 H2A 120.8 . . ?
C1 C2 C3 118.3(3) . . ?
H2A C2 C3 120.8 . . ?
F1 C9 C8 119.8(2) . . ?
F1 C9 C10 117.8(2) . 2_765 ?
C8 C9 C10 122.3(2) . 2_765 ?
O1 C6 O2 124.3(2) . . ?
O1 C6 C1 111.6(2) . . ?
O2 C6 C1 124.2(3) . . ?
N1 C3 C2 123.6(3) . . ?
N1 C3 H3A 118.2 . . ?
C2 C3 H3A 118.2 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
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
I1 C8 2.111(2) . ?
F1 C9 1.368(3) . ?
F2 C10 1.354(3) . ?
C8 C10 1.401(4) . ?
C8 C9 1.384(4) . ?
O1 C6 1.342(3) . ?
O1 C7 1.460(3) . ?
N1 C4 1.349(4) . ?
N1 C3 1.337(4) . ?
O2 C6 1.210(4) . ?
C4 H4A 0.9500 . ?
C4 C5 1.389(4) . ?
C1 C5 1.393(4) . ?
C1 C2 1.396(4) . ?
C1 C6 1.506(3) . ?
C10 C9 1.383(4) 2_765 ?
C5 H5A 0.9500 . ?
C2 H2A 0.9500 . ?
C2 C3 1.397(4) . ?
C9 C10 1.383(4) 2_765 ?
C3 H3A 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C4 C5 -0.1(4) . . . . ?
I1 C8 C10 F2 -3.1(3) . . . . ?
I1 C8 C10 C9 177.8(2) . . . 2_765 ?
C9 C8 C10 F2 179.4(2) . . . . ?
C9 C8 C10 C9 0.3(4) . . . 2_765 ?
N1 C4 C5 C1 -0.6(4) . . . . ?
C2 C1 C5 C4 0.5(4) . . . . ?
C6 C1 C5 C4 -179.6(2) . . . . ?
C5 C1 C2 C3 0.2(4) . . . . ?
C6 C1 C2 C3 -179.7(2) . . . . ?
I1 C8 C9 F1 1.7(3) . . . . ?
I1 C8 C9 C10 -177.8(2) . . . 2_765 ?
C10 C8 C9 F1 179.2(2) . . . . ?
C10 C8 C9 C10 -0.3(4) . . . 2_765 ?
C7 O1 C6 O2 0.0(4) . . . . ?
C7 O1 C6 C1 179.8(2) . . . . ?
C5 C1 C6 O1 170.8(2) . . . . ?
C5 C1 C6 O2 -9.4(4) . . . . ?
C2 C1 C6 O1 -9.4(4) . . . . ?
C2 C1 C6 O2 170.4(3) . . . . ?
C4 N1 C3 C2 0.9(4) . . . . ?
C1 C2 C3 N1 -1.0(4) . . . . ?
