#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:18:16 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179571 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/36/4503611.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_4503611
loop_
_publ_author_name
'Custelcean, Radu'
'Jiang, De-en'
'Hay, Benjamin P.'
'Luo, Wensui'
'Gu, Baohua'
_publ_section_title
;
 Hydrogen-Bonded Helices for Anion Binding and Separation
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1909
_journal_paper_doi               10.1021/cg800137e
_journal_volume                  8
_journal_year                    2008
_chemical_formula_sum            'C11 H11 Cl0.53 I0.47 N4 O3.12'
_chemical_formula_weight         327.59
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 102.853(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.309(2)
_cell_length_b                   7.7389(13)
_cell_length_c                   13.703(2)
_cell_measurement_temperature    173(2)
_cell_volume                     1272.6(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9756
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    1.353
_exptl_absorpt_correction_T_max  0.8879
_exptl_absorpt_correction_T_min  0.6790
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.048
_refine_diff_density_min         -1.635
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         3167
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0563
_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)+(0.0992P)²+0.9172P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1622
_reflns_number_gt                2321
_reflns_number_total             3167
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg800137e-file001.cif
_cod_data_source_block           comp-cryst
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4503611
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
I1 I 0.33051(3) -0.12445(6) -0.09747(3) 0.03041(18) Uani 0.468(5) 1 d P
Cl1 Cl 0.33051(3) -0.12445(6) -0.09747(3) 0.03041(18) Uani 0.532(5) 1 d P
N1 N 0.3193(3) 0.1193(5) 0.3811(3) 0.0387(9) Uani 1 1 d .
H1N H 0.2914 0.1357 0.4342 0.046 Uiso 1 1 calc R
O1 O 0.0696(3) -0.1137(4) 0.1739(2) 0.0385(8) Uani 1 1 d .
N4 N -0.1918(3) -0.3573(5) -0.0179(3) 0.0385(9) Uani 1 1 d .
C4 C 0.4675(4) 0.1447(6) 0.3027(4) 0.0463(12) Uani 1 1 d .
H4 H 0.5422 0.1784 0.3045 0.056 Uiso 1 1 calc R
C6 C 0.1255(4) -0.1142(5) 0.1112(3) 0.0312(9) Uani 1 1 d .
C5 C 0.4232(4) 0.1670(7) 0.3856(4) 0.0461(12) Uani 1 1 d .
H5 H 0.4668 0.2160 0.4452 0.055 Uiso 1 1 calc R
C8 C -0.0111(3) -0.2568(5) -0.0250(3) 0.0296(9) Uani 1 1 d .
N3 N 0.0897(3) -0.1735(5) 0.0151(2) 0.0326(8) Uani 1 1 d .
H3N H 0.1350 -0.1575 -0.0256 0.039 Uiso 1 1 calc R
C1 C 0.2537(4) 0.0471(6) 0.3000(3) 0.0349(10) Uani 1 1 d .
H1 H 0.1796 0.0139 0.3010 0.042 Uiso 1 1 calc R
N2 N 0.2332(3) -0.0533(5) 0.1277(3) 0.0369(9) Uani 1 1 d .
H2N H 0.2668 -0.0626 0.0775 0.044 Uiso 1 1 calc R
C7 C -0.0974(4) -0.2741(6) 0.0231(3) 0.0355(10) Uani 1 1 d .
H7 H -0.0896 -0.2251 0.0878 0.043 Uiso 1 1 calc R
C2 C 0.2947(3) 0.0213(5) 0.2148(3) 0.0316(9) Uani 1 1 d .
C3 C 0.4031(4) 0.0731(6) 0.2170(4) 0.0390(10) Uani 1 1 d .
H3 H 0.4330 0.0592 0.1593 0.047 Uiso 1 1 calc R
C11 C -0.2030(5) -0.4255(7) -0.1101(4) 0.0441(12) Uani 1 1 d .
H11 H -0.2694 -0.4865 -0.1391 0.053 Uiso 1 1 calc R
C9 C -0.0244(4) -0.3232(6) -0.1218(3) 0.0377(10) Uani 1 1 d .
H9 H 0.0323 -0.3089 -0.1581 0.045 Uiso 1 1 calc R
C10 C -0.1209(4) -0.4094(6) -0.1635(4) 0.0436(12) Uani 1 1 d .
H10 H -0.1311 -0.4577 -0.2286 0.052 Uiso 1 1 calc R
O2 O 0.2305(14) -0.1530(17) -0.1227(12) 0.137(5) Uiso 0.532(5) 1 d P
O4 O 0.4089(18) -0.230(3) -0.1010(17) 0.205(8) Uiso 0.532(5) 1 d P
O3 O 0.360(2) -0.041(4) -0.029(2) 0.270(12) Uiso 0.532(5) 1 d P
O5 O 0.351(2) -0.030(4) -0.189(2) 0.244(10) Uiso 0.532(5) 1 d P
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'
Cl Cl 0.1484 0.1585 '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
O3 I1 O2 117.1(16)
O3 I1 O4 107.0(17)
O2 I1 O4 126.6(12)
O3 I1 O5 109.3(18)
O2 I1 O5 101.1(12)
O4 I1 O5 90.8(14)
C5 N1 C1 123.6(4)
C7 N4 C11 118.7(4)
C5 C4 C3 119.7(5)
O1 C6 N3 124.7(4)
O1 C6 N2 124.0(4)
N3 C6 N2 111.3(4)
N1 C5 C4 119.0(4)
C7 C8 C9 118.6(4)
C7 C8 N3 124.7(4)
C9 C8 N3 116.7(4)
C6 N3 C8 126.8(4)
N1 C1 C2 119.6(4)
C6 N2 C2 127.1(4)
N4 C7 C8 122.5(4)
C1 C2 C3 117.9(4)
C1 C2 N2 123.6(4)
C3 C2 N2 118.4(4)
C4 C3 C2 120.2(4)
N4 C11 C10 121.8(5)
C10 C9 C8 118.8(4)
C9 C10 C11 119.5(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 O3 1.13(3)
I1 O2 1.223(16)
I1 O4 1.27(2)
I1 O5 1.52(3)
N1 C5 1.320(6)
N1 C1 1.341(5)
O1 C6 1.214(5)
N4 C7 1.338(6)
N4 C11 1.348(6)
C4 C5 1.377(8)
C4 C3 1.379(7)
C6 N3 1.373(5)
C6 N2 1.377(6)
C8 C7 1.376(6)
C8 C9 1.397(6)
C8 N3 1.398(5)
C1 C2 1.386(6)
N2 C2 1.388(5)
C2 C3 1.388(6)
C11 C10 1.379(8)
C9 C10 1.371(7)
