#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:48:54 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179541 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/10/4501091.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_4501091
loop_
_publ_author_name
'Roy, Sandipan'
'Biradha, Kumar'
_publ_section_title
;
 Two-Component Supramolecular Organic Hosts as Colorimetric Indicators for
 Aromatic Guests: Visual Molecular Recognition via Cation−π
 Interactions
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4120
_journal_paper_doi               10.1021/cg200690c
_journal_volume                  11
_journal_year                    2011
_chemical_formula_sum            'C48 H33 Cl N2 O16'
_chemical_formula_weight         929.21
_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                113.496(5)
_cell_angle_beta                 96.338(5)
_cell_angle_gamma                106.722(4)
_cell_formula_units_Z            1
_cell_length_a                   8.0922(10)
_cell_length_b                   12.4611(15)
_cell_length_c                   12.587(2)
_cell_measurement_reflns_used    4312
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      1.83
_cell_volume                     1077.5(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker CCD APEX 2'
_diffrn_measurement_method       hemisphere
_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  0.0614
_diffrn_reflns_av_sigmaI/netI    0.0743
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14040
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.1418
_refine_ls_R_factor_gt           0.0635
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0863P)²+0.3054P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1455
_refine_ls_wR_factor_ref         0.1871
_reflns_number_gt                2200
_reflns_number_total             4312
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200690c_si_002.cif
_cod_data_source_block           11
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4501091
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
O11 O 0.5060(3) 0.2814(2) 1.1186(2) 0.0581(7) Uani 1 1 d .
O12 O 0.2901(3) 0.3304(2) 1.0524(2) 0.0584(7) Uani 1 1 d .
H12O H 0.224(4) 0.330(3) 0.978(3) 0.050 Uiso 1 1 d .
O13 O 0.1464(4) -0.0800(3) 0.5896(2) 0.0972(12) Uani 1 1 d .
O14 O 0.2722(4) 0.0180(3) 0.4938(2) 0.0694(8) Uani 1 1 d .
H14O H 0.185(4) -0.051(3) 0.428(3) 0.050 Uiso 1 1 d .
C11 C 0.3370(4) 0.1441(3) 0.8139(3) 0.0394(8) Uani 1 1 d .
C12 C 0.4580(4) 0.2482(3) 0.9165(3) 0.0441(8) Uani 1 1 d .
C13 C 0.6180(4) 0.3205(3) 0.9086(3) 0.0558(10) Uani 1 1 d .
H13 H 0.6989 0.3878 0.9777 0.067 Uiso 1 1 calc R
C14 C 0.6583(5) 0.2937(3) 0.7998(3) 0.0592(10) Uani 1 1 d .
H14 H 0.7659 0.3425 0.7952 0.071 Uiso 1 1 calc R
C15 C 0.5387(4) 0.1947(3) 0.6983(3) 0.0513(9) Uani 1 1 d .
H15 H 0.5647 0.1778 0.6245 0.062 Uiso 1 1 calc R
C16 C 0.3784(4) 0.1187(3) 0.7036(3) 0.0398(8) Uani 1 1 d .
C17 C 0.4186(4) 0.2864(3) 1.0367(3) 0.0467(8) Uani 1 1 d .
C18 C 0.2541(4) 0.0102(3) 0.5919(3) 0.0453(8) Uani 1 1 d .
O21 O 0.4323(3) -0.0346(3) 0.8504(3) 0.0814(9) Uani 1 1 d .
O22 O 0.2454(3) -0.1724(2) 0.8906(2) 0.0649(7) Uani 1 1 d .
H22O H 0.349(4) -0.200(3) 0.896(3) 0.050 Uiso 1 1 d .
O23 O -0.0342(3) 0.1932(2) 0.6794(2) 0.0531(6) Uani 1 1 d .
O24 O 0.1370(3) 0.3244(2) 0.8624(2) 0.0557(7) Uani 1 1 d .
C21 C 0.1629(4) 0.0704(3) 0.8255(3) 0.0375(7) Uani 1 1 d .
C22 C 0.1390(4) -0.0327(3) 0.8500(2) 0.0388(8) Uani 1 1 d .
C23 C -0.0273(4) -0.0949(3) 0.8597(3) 0.0442(8) Uani 1 1 d .
H23 H -0.0429 -0.1626 0.8769 0.053 Uiso 1 1 calc R
C24 C -0.1696(4) -0.0577(3) 0.8444(3) 0.0466(9) Uani 1 1 d .
H24 H -0.2798 -0.1002 0.8512 0.056 Uiso 1 1 calc R
C25 C -0.1478(4) 0.0421(3) 0.8190(3) 0.0463(8) Uani 1 1 d .
H25 H -0.2440 0.0665 0.8075 0.056 Uiso 1 1 calc R
C26 C 0.0172(4) 0.1069(3) 0.8103(3) 0.0403(8) Uani 1 1 d .
C27 C 0.2885(4) -0.0776(3) 0.8628(3) 0.0450(8) Uani 1 1 d .
C28 C 0.0410(4) 0.2163(3) 0.7831(3) 0.0430(8) Uani 1 1 d .
N1 N 0.1941(4) 0.2952(4) 0.5680(4) 0.0673(10) Uani 1 1 d .
H1N H 0.111(4) 0.251(3) 0.588(3) 0.050 Uiso 1 1 d .
C1 C 0.2954(6) 0.4056(4) 0.6542(4) 0.0836(14) Uani 1 1 d .
H1 H 0.2846 0.4283 0.7322 0.100 Uiso 1 1 calc R
C2 C 0.4168(6) 0.4870(4) 0.6290(4) 0.0845(15) Uani 1 1 d .
H2 H 0.4879 0.5658 0.6904 0.101 Uiso 1 1 calc R
C3 C 0.4368(4) 0.4552(3) 0.5148(3) 0.0524(9) Uani 1 1 d .
C4 C 0.3318(6) 0.3370(4) 0.4300(4) 0.0835(15) Uani 1 1 d .
H4 H 0.3417 0.3099 0.3515 0.100 Uiso 1 1 calc R
C5 C 0.2125(6) 0.2580(4) 0.4592(4) 0.0919(16) Uani 1 1 d .
H5 H 0.1436 0.1769 0.4009 0.110 Uiso 1 1 calc R
Cl Cl 0.853(2) 0.431(2) 0.6079(18) 0.277(9) Uani 0.50 1 d P
C101 C 0.837(9) 0.362(7) 0.443(5) 0.28(4) Uani 0.50 1 d P
C102 C 1.049(8) 0.587(6) 0.633(4) 0.22(3) Uani 0.50 1 d P
C103 C 0.958(5) 0.544(3) 0.675(6) 0.26(3) Uani 0.50 1 d P
C104 C 0.814(2) 0.369(3) 0.527(6) 0.19(2) Uani 0.50 1 d P
C105 C 0.961(3) 0.470(4) 0.521(3) 0.138(10) Uani 0.50 1 d P
C106 C 1.067(3) 0.595(3) 0.5867(17) 0.089(5) Uani 0.50 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'
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
C16 C11 C12 118.3(3) . .
C16 C11 C21 122.7(3) . .
C12 C11 C21 118.8(3) . .
C13 C12 C11 120.4(3) . .
C13 C12 C17 117.9(3) . .
C11 C12 C17 121.6(3) . .
C14 C13 C12 120.8(3) . .
C15 C14 C13 119.4(3) . .
C14 C15 C16 121.2(3) . .
C15 C16 C11 119.9(3) . .
C15 C16 C18 119.6(3) . .
C11 C16 C18 120.5(3) . .
O11 C17 O12 120.7(3) . .
O11 C17 C12 121.9(3) . .
O12 C17 C12 117.4(3) . .
O13 C18 O14 121.1(3) . .
O13 C18 C16 123.8(3) . .
O14 C18 C16 115.1(3) . .
C26 C21 C22 118.7(3) . .
C26 C21 C11 117.8(3) . .
C22 C21 C11 123.5(3) . .
C23 C22 C21 119.4(3) . .
C23 C22 C27 120.0(3) . .
C21 C22 C27 120.6(3) . .
C24 C23 C22 121.1(3) . .
C25 C24 C23 119.8(3) . .
C24 C25 C26 120.3(3) . .
C25 C26 C21 120.7(3) . .
C25 C26 C28 120.2(3) . .
C21 C26 C28 119.1(3) . .
O21 C27 O22 122.3(3) . .
O21 C27 C22 124.9(3) . .
O22 C27 C22 112.8(3) . .
O24 C28 O23 123.4(3) . .
O24 C28 C26 119.2(3) . .
O23 C28 C26 117.4(3) . .
C5 N1 C1 121.7(4) . .
N1 C1 C2 119.5(4) . .
C1 C2 C3 121.4(4) . .
C4 C3 C2 116.1(3) . .
C4 C3 C3 122.0(4) . 2_666
C2 C3 C3 121.9(4) . 2_666
C5 C4 C3 120.7(4) . .
N1 C5 C4 120.5(4) . .
C104 Cl C103 142(3) . .
C104 Cl C105 66(2) . .
C103 Cl C105 76(3) . .
C104 Cl C101 23(2) . .
C103 Cl C101 119(3) . .
C105 Cl C101 43(3) . .
C104 Cl C102 113(2) . .
C103 Cl C102 29(4) . .
C105 Cl C102 47(2) . .
C101 Cl C102 90(3) . .
C106 C101 C104 137(9) 2_766 .
C106 C101 C105 62(5) 2_766 .
C104 C101 C105 77(4) . .
C106 C101 C102 14(2) 2_766 2_766
C104 C101 C102 151(9) . 2_766
C105 C101 C102 74(5) . 2_766
C106 C101 Cl 119(6) 2_766 .
C104 C101 Cl 20(3) . .
C105 C101 Cl 57(2) . .
C102 C101 Cl 131(6) 2_766 .
C106 C102 C103 151(10) . .
C106 C102 C105 68(7) . .
C103 C102 C105 87(6) . .
C106 C102 C101 22(5) . 2_766
C103 C102 C101 173(8) . 2_766
C105 C102 C101 86(4) . 2_766
C106 C102 C105 27(6) . 2_766
C103 C102 C105 127(7) . 2_766
C105 C102 C105 41(2) . 2_766
C101 C102 C105 46(3) 2_766 2_766
C106 C102 Cl 119(8) . .
C103 C102 Cl 35(4) . .
C105 C102 Cl 52(2) . .
C101 C102 Cl 139(5) 2_766 .
C105 C102 Cl 93(3) 2_766 .
C102 C103 Cl 116(8) . .
C102 C103 C106 11(4) . .
Cl C103 C106 107(4) . .
C102 C103 C105 55(5) . .
Cl C103 C105 60(3) . .
C106 C103 C105 46(2) . .
Cl C104 C101 136(4) . .
Cl C104 C105 78.5(18) . .
C101 C104 C105 59(4) . .
Cl C104 C106 117(2) . 2_766
C101 C104 C106 21(4) . 2_766
C105 C104 C106 39(2) . 2_766
C105 C105 C106 71(3) 2_766 2_766
C105 C105 C101 115(5) 2_766 .
C106 C105 C101 47(3) 2_766 .
C105 C105 C106 57(3) 2_766 .
C106 C105 C106 127.2(18) 2_766 .
C101 C105 C106 165(3) . .
C105 C105 C102 83(5) 2_766 .
C106 C105 C102 153(4) 2_766 .
C101 C105 C102 158(3) . .
C106 C105 C102 26(2) . .
C105 C105 C104 158(5) 2_766 .
C106 C105 C104 91(4) 2_766 .
C101 C105 C104 44(3) . .
C106 C105 C104 141(4) . .
C102 C105 C104 116(3) . .
C105 C105 Cl 161(5) 2_766 .
C106 C105 Cl 126(4) 2_766 .
C101 C105 Cl 79(3) . .
C106 C105 Cl 106(3) . .
C102 C105 Cl 81(3) . .
C104 C105 Cl 35(2) . .
C105 C105 C102 56(3) 2_766 2_766
C106 C105 C102 14(3) 2_766 2_766
C101 C105 C102 60(3) . 2_766
C106 C105 C102 113(3) . 2_766
C102 C105 C102 139(2) . 2_766
C104 C105 C102 104(4) . 2_766
Cl C105 C102 139(4) . 2_766
C105 C105 C103 119(5) 2_766 .
C106 C105 C103 169(3) 2_766 .
C101 C105 C103 122(3) . .
C106 C105 C103 63(2) . .
C102 C105 C103 37(2) . .
C104 C105 C103 79(2) . .
Cl C105 C103 43.5(11) . .
C102 C105 C103 171(3) 2_766 .
C102 C106 C101 144(7) . 2_766
C102 C106 C105 138(9) . 2_766
C101 C106 C105 72(4) 2_766 2_766
C102 C106 C105 86(8) . .
C101 C106 C105 122(4) 2_766 .
C105 C106 C105 52.8(18) 2_766 .
C102 C106 C103 18(8) . .
C101 C106 C103 162(4) 2_766 .
C105 C106 C103 123(2) 2_766 .
C105 C106 C103 70.7(15) . .
C102 C106 C104 165(7) . 2_766
C101 C106 C104 22(4) 2_766 2_766
C105 C106 C104 51(2) 2_766 2_766
C105 C106 C104 102.7(18) . 2_766
C103 C106 C104 173(2) . 2_766
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O11 C17 1.218(4) .
O12 C17 1.306(4) .
O13 C18 1.195(4) .
O14 C18 1.298(4) .
C11 C16 1.398(4) .
C11 C12 1.401(4) .
C11 C21 1.502(4) .
C12 C13 1.389(5) .
C12 C17 1.495(5) .
C13 C14 1.375(5) .
C14 C15 1.369(5) .
C15 C16 1.395(4) .
C16 C18 1.485(4) .
O21 C27 1.189(4) .
O22 C27 1.326(4) .
O23 C28 1.258(4) .
O24 C28 1.252(4) .
C21 C26 1.400(4) .
C21 C22 1.404(4) .
C22 C23 1.393(4) .
C22 C27 1.490(4) .
C23 C24 1.381(4) .
C24 C25 1.373(5) .
C25 C26 1.389(4) .
C26 C28 1.499(5) .
N1 C5 1.300(5) .
N1 C1 1.306(5) .
C1 C2 1.359(5) .
C2 C3 1.372(5) .
C3 C4 1.363(5) .
C3 C3 1.480(6) 2_666
C4 C5 1.362(6) .
Cl C104 0.95(5) .
Cl C103 1.27(4) .
Cl C105 1.606(17) .
Cl C101 1.88(6) .
Cl C102 2.00(7) .
C101 C106 1.01(8) 2_766
C101 C104 1.08(6) .
C101 C105 1.32(8) .
C101 C102 1.58(7) 2_766
C102 C106 0.66(5) .
C102 C103 1.09(7) .
C102 C105 1.48(7) .
C102 C101 1.58(7) 2_766
C102 C105 1.76(6) 2_766
C103 C106 1.69(7) .
C103 C105 1.79(7) .
C104 C105 1.50(4) .
C104 C106 1.94(6) 2_766
C105 C105 1.16(4) 2_766
C105 C106 1.22(4) 2_766
C105 C106 1.38(5) .
C105 C102 1.76(6) 2_766
C106 C101 1.01(8) 2_766
C106 C105 1.22(4) 2_766
C106 C104 1.94(6) 2_766
