#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/35/1503564.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_1503564
loop_
_publ_author_name
'Mahanta, Sanjeev P.'
'Kumar, B. Sathish'
'Baskaran, Sambath'
'Sivasankar, Chinnappan'
'Panda, Pradeepta K.'
_publ_section_title
;
 Colorimetric sensing of fluoride ion by new expanded calix[4]pyrrole
 through anion-π interaction.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              548
_journal_page_last               551
_journal_paper_doi               10.1021/ol203165x
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C18 H22 N2'
_chemical_formula_weight         266.38
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :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            16
_cell_length_a                   13.9875(18)
_cell_length_b                   13.9875(18)
_cell_length_c                   31.440(7)
_cell_measurement_reflns_used    1072
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8774
_cell_measurement_theta_min      2.9067
_cell_volume                     6151.2(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.897
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_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  0.1398
_diffrn_reflns_av_sigmaI/netI    0.1779
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            13670
_diffrn_reflns_theta_full        28.94
_diffrn_reflns_theta_max         28.94
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_correction_T_min  0.9899
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             2304
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3649
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.2735
_refine_ls_R_factor_gt           0.0933
_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)+(0.0326P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1742
_reflns_number_gt                1287
_reflns_number_total             3649
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol203165x_si_001.cif
_cod_data_source_block           2
_cod_original_cell_volume        6151.2(17)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               1503564
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'
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
C1 C 1.0248(3) 0.9792(3) 0.10078(16) 0.0653(11) Uani 1 1 d .
C2 C 1.0333(3) 0.9967(3) 0.14288(16) 0.0887(15) Uani 1 1 d .
H2 H 1.0767 1.0387 0.1552 0.106 Uiso 1 1 calc R
C3 C 0.9657(3) 0.9410(3) 0.16498(14) 0.0850(14) Uani 1 1 d .
H3 H 0.9578 0.9391 0.1943 0.102 Uiso 1 1 calc R
C4 C 0.9139(3) 0.8905(2) 0.13618(13) 0.0546(10) Uani 1 1 d .
C5 C 0.8262(2) 0.8286(2) 0.13981(10) 0.0474(9) Uani 1 1 d .
C6 C 0.8143(2) 0.7709(2) 0.09986(10) 0.0437(9) Uani 1 1 d .
C7 C 0.7729(2) 0.7918(3) 0.06165(11) 0.0614(11) Uani 1 1 d .
H7 H 0.7397 0.8474 0.0551 0.074 Uiso 1 1 calc R
C8 C 0.7890(3) 0.7145(3) 0.03401(11) 0.0718(12) Uani 1 1 d .
H8 H 0.7680 0.7106 0.0060 0.086 Uiso 1 1 calc R
C9 C 0.8401(3) 0.6467(3) 0.05473(11) 0.0551(10) Uani 1 1 d .
C10 C 1.0782(3) 1.0095(3) 0.06248(16) 0.0777(14) Uani 1 1 d .
C12 C 0.7388(2) 0.8948(2) 0.14575(11) 0.0623(11) Uani 1 1 d .
H12A H 0.7514 0.9384 0.1691 0.075 Uiso 1 1 calc R
H12B H 0.7304 0.9328 0.1202 0.075 Uiso 1 1 calc R
C13 C 0.6467(2) 0.8411(3) 0.15477(12) 0.0713(12) Uani 1 1 d .
H13A H 0.5956 0.8866 0.1599 0.086 Uiso 1 1 calc R
H13B H 0.6296 0.8031 0.1301 0.086 Uiso 1 1 calc R
C14 C 0.6571(3) 0.7764(3) 0.19308(12) 0.0808(13) Uani 1 1 d .
H14A H 0.5996 0.7384 0.1964 0.097 Uiso 1 1 calc R
H14B H 0.6648 0.8150 0.2185 0.097 Uiso 1 1 calc R
C15 C 0.7427(3) 0.7105(3) 0.18832(10) 0.0679(11) Uani 1 1 d .
H15A H 0.7503 0.6733 0.2141 0.081 Uiso 1 1 calc R
H15B H 0.7311 0.6664 0.1651 0.081 Uiso 1 1 calc R
C16 C 0.8340(2) 0.7656(2) 0.17973(10) 0.0585(10) Uani 1 1 d .
H16A H 0.8863 0.7209 0.1761 0.070 Uiso 1 1 calc R
H16B H 0.8484 0.8056 0.2041 0.070 Uiso 1 1 calc R
C17 C 0.8660(3) 0.5498(3) 0.04142(13) 0.0693(12) Uani 1 1 d .
H1A H 0.934(2) 0.891(2) 0.0732(9) 0.050(11) Uiso 1 1 d .
H2A H 0.893(2) 0.650(2) 0.1139(9) 0.061(12) Uiso 1 1 d .
N1 N 0.9509(2) 0.9152(2) 0.09751(12) 0.0589(9) Uani 1 1 d .
N2 N 0.8550(2) 0.6826(2) 0.09543(9) 0.0478(8) Uani 1 1 d .
C11 C 1.0626(3) 1.1147(3) 0.05064(16) 0.130(2) Uani 1 1 d .
H11A H 1.0688 1.1536 0.0756 0.195 Uiso 1 1 calc R
H11B H 0.9997 1.1225 0.0389 0.195 Uiso 1 1 calc R
H11C H 1.1094 1.1337 0.0300 0.195 Uiso 1 1 calc R
C18 C 0.8187(3) 0.5198(3) -0.00023(12) 0.1104(18) Uani 1 1 d .
H18A H 0.8473 0.4616 -0.0102 0.166 Uiso 1 1 calc R
H18B H 0.8275 0.5692 -0.0211 0.166 Uiso 1 1 calc R
H18C H 0.7516 0.5099 0.0044 0.166 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'
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
C2 C1 N1 105.0(4) .
C2 C1 C10 134.5(4) .
N1 C1 C10 120.4(4) .
C1 C2 C3 108.9(4) .
C1 C2 H2 125.6 .
C3 C2 H2 125.6 .
C4 C3 C2 108.5(4) .
C4 C3 H3 125.7 .
C2 C3 H3 125.7 .
C3 C4 N1 105.0(4) .
C3 C4 C5 133.1(4) .
N1 C4 C5 121.5(3) .
C6 C5 C4 109.6(3) .
C6 C5 C16 112.5(3) .
C4 C5 C16 109.5(3) .
C6 C5 C12 109.6(3) .
C4 C5 C12 108.0(3) .
C16 C5 C12 107.5(3) .
C7 C6 N2 106.2(3) .
C7 C6 C5 131.9(3) .
N2 C6 C5 121.7(3) .
C6 C7 C8 108.2(3) .
C6 C7 H7 125.9 .
C8 C7 H7 125.9 .
C9 C8 C7 109.0(3) .
C9 C8 H8 125.5 .
C7 C8 H8 125.5 .
C8 C9 N2 105.6(3) .
C8 C9 C17 129.9(4) .
N2 C9 C17 124.1(4) .
C17 C10 C1 121.8(4) 6_664
C17 C10 C11 124.5(4) 6_664
C1 C10 C11 113.6(4) .
C13 C12 C5 113.4(3) .
C13 C12 H12A 108.9 .
C5 C12 H12A 108.9 .
C13 C12 H12B 108.9 .
C5 C12 H12B 108.9 .
H12A C12 H12B 107.7 .
C14 C13 C12 111.3(3) .
C14 C13 H13A 109.4 .
C12 C13 H13A 109.4 .
C14 C13 H13B 109.4 .
C12 C13 H13B 109.4 .
H13A C13 H13B 108.0 .
C13 C14 C15 111.1(3) .
C13 C14 H14A 109.4 .
C15 C14 H14A 109.4 .
C13 C14 H14B 109.4 .
C15 C14 H14B 109.4 .
H14A C14 H14B 108.0 .
C16 C15 C14 111.9(3) .
C16 C15 H15A 109.2 .
C14 C15 H15A 109.2 .
C16 C15 H15B 109.2 .
C14 C15 H15B 109.2 .
H15A C15 H15B 107.9 .
C15 C16 C5 112.2(3) .
C15 C16 H16A 109.2 .
C5 C16 H16A 109.2 .
C15 C16 H16B 109.2 .
C5 C16 H16B 109.2 .
H16A C16 H16B 107.9 .
C10 C17 C9 125.9(4) 6_664
C10 C17 C18 121.0(4) 6_664
C9 C17 C18 113.1(4) .
C4 N1 C1 112.6(4) .
C4 N1 H1A 125(2) .
C1 N1 H1A 122(2) .
C6 N2 C9 111.0(3) .
C6 N2 H2A 129.0(19) .
C9 N2 H2A 119.7(19) .
C10 C11 H11A 109.5 .
C10 C11 H11B 109.5 .
H11A C11 H11B 109.5 .
C10 C11 H11C 109.5 .
H11A C11 H11C 109.5 .
H11B C11 H11C 109.5 .
C17 C18 H18A 109.5 .
C17 C18 H18B 109.5 .
H18A C18 H18B 109.5 .
C17 C18 H18C 109.5 .
H18A C18 H18C 109.5 .
H18B C18 H18C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.351(5) .
C1 N1 1.371(4) .
C1 C10 1.479(5) .
C2 C3 1.410(5) .
C2 H2 0.9300 .
C3 C4 1.358(4) .
C3 H3 0.9300 .
C4 N1 1.366(4) .
C4 C5 1.505(4) .
C5 C6 1.502(4) .
C5 C16 1.537(4) .
C5 C12 1.545(4) .
C6 C7 1.365(4) .
C6 N2 1.367(4) .
C7 C8 1.405(4) .
C7 H7 0.9300 .
C8 C9 1.354(5) .
C8 H8 0.9300 .
C9 N2 1.390(4) .
C9 C17 1.464(5) .
C10 C17 1.318(5) 6_664
C10 C11 1.532(5) .
C12 C13 1.518(4) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C14 1.514(4) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 C15 1.517(4) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 C16 1.516(4) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 C10 1.318(5) 6_664
C17 C18 1.526(5) .
N1 H1A 0.87(3) .
N2 H2A 0.91(3) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
