#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:22:36 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180075 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/21/7052133.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_7052133
loop_
_publ_author_name
'Arunkumar, Easwaran'
'Sudeep, Pallikkara K.'
'Kamat, Prashant V.'
'Noll, Bruce C.'
'Smith, Bradley D.'
_publ_section_title
;
 Singlet oxygen generation using iodinated squaraine and
 squaraine-rotaxane dyes.
;
_journal_issue                   5
_journal_name_full
'New journal of chemistry = Nouveau journal de chimie'
_journal_page_first              677
_journal_page_last               683
_journal_paper_doi               10.1039/b616224j
_journal_volume                  31
_journal_year                    2007
_chemical_compound_source        synthesized
_chemical_formula_moiety         'C44 H32 I4 N2 O2, 2(C H Cl3)'
_chemical_formula_sum            'C46 H34 Cl6 I4 N2 O2'
_chemical_formula_weight         1367.05
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            4
_cell_length_a                   14.2033(3)
_cell_length_b                   16.4470(4)
_cell_length_c                   20.4164(5)
_cell_measurement_reflns_used    6322
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.6811
_cell_measurement_theta_min      2.4767
_cell_volume                     4769.31(19)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004; Sheldrick, 2003)'
_computing_molecular_graphics    'XP (Sheldrick, 1998)'
_computing_publication_material  'XCIF (Sheldrick, 2001)/enCIFer (CCDC, 2004)'
_computing_structure_refinement  'XL (Sheldrick, 2001)'
_computing_structure_solution    'XS (Sheldrick, 2001)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker d8-ApexII CCD diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            56848
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         1.99
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Siemens KFFMO2K-90'
_exptl_absorpt_coefficient_mu    2.989
_exptl_absorpt_correction_T_max  0.8872
_exptl_absorpt_correction_T_min  0.6258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;Blessing, R. H. (1985) Acta Cryst. A51, 33-38.

Sheldrick, G. M. (2005) SADABS. University of G\:ottingen, Germany.
;
_exptl_crystal_colour            'translucent intense blue gold'
_exptl_crystal_density_diffrn    1.904
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2616
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4884
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0213
_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)+(0.0225P)²+4.0046P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0467
_refine_ls_wR_factor_ref         0.0512
_reflns_number_gt                4049
_reflns_number_total             4884
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b616224j.txt
_cod_data_source_block           bcn263_0m
_cod_database_code               7052133
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.304217(13) 0.297217(13) 0.704379(9) 0.03060(6) Uani 1 1 d . . .
I2 I 0.947998(13) -0.179831(10) 0.421415(9) 0.02560(6) Uani 1 1 d . . .
N1 N 0.73966(14) 0.17588(13) 0.56494(10) 0.0195(4) Uani 1 1 d . . .
O1 O 1.00142(13) 0.53398(11) 0.60775(9) 0.0225(4) Uani 1 1 d . . .
C1 C 1.00105(17) 0.51515(15) 0.54916(12) 0.0173(5) Uani 1 1 d . . .
C2 C 0.95798(16) 0.45005(15) 0.51050(12) 0.0164(5) Uani 1 1 d . . .
C3 C 0.90155(17) 0.38239(15) 0.52467(12) 0.0171(5) Uani 1 1 d . . .
C4 C 0.87205(17) 0.36483(15) 0.58911(12) 0.0188(5) Uani 1 1 d . . .
H4 H 0.8897 0.4002 0.6238 0.023 Uiso 1 1 calc R . .
C5 C 0.81849(17) 0.29789(16) 0.60255(13) 0.0199(5) Uani 1 1 d . . .
H5 H 0.7988 0.2876 0.6462 0.024 Uiso 1 1 calc R . .
C6 C 0.79186(16) 0.24330(15) 0.55162(12) 0.0173(5) Uani 1 1 d . . .
C7 C 0.82075(17) 0.26145(15) 0.48716(12) 0.0185(5) Uani 1 1 d . . .
H7 H 0.8036 0.2261 0.4524 0.022 Uiso 1 1 calc R . .
C8 C 0.87293(17) 0.32910(15) 0.47411(12) 0.0186(5) Uani 1 1 d . . .
H8 H 0.8904 0.3407 0.4302 0.022 Uiso 1 1 calc R . .
C9 C 0.70859(18) 0.15617(15) 0.63111(13) 0.0205(5) Uani 1 1 d . . .
H9A H 0.7585 0.1725 0.6623 0.025 Uiso 1 1 calc R . .
H9B H 0.7009 0.0965 0.6345 0.025 Uiso 1 1 calc R . .
C10 C 0.61689(18) 0.19658(15) 0.65146(13) 0.0193(5) Uani 1 1 d . . .
C11 C 0.57582(17) 0.25740(15) 0.61390(12) 0.0187(5) Uani 1 1 d . . .
H11 H 0.6080 0.2782 0.5767 0.022 Uiso 1 1 calc R . .
C12 C 0.48758(18) 0.28803(16) 0.63065(12) 0.0196(5) Uani 1 1 d . . .
H12 H 0.4597 0.3300 0.6053 0.024 Uiso 1 1 calc R . .
C13 C 0.44117(17) 0.25695(16) 0.68430(12) 0.0209(5) Uani 1 1 d . . .
C14 C 0.48261(19) 0.19862(16) 0.72396(13) 0.0220(6) Uani 1 1 d . . .
H14 H 0.4510 0.1792 0.7619 0.026 Uiso 1 1 calc R . .
C15 C 0.57081(19) 0.16912(15) 0.70744(13) 0.0216(5) Uani 1 1 d . . .
H15 H 0.6002 0.1297 0.7346 0.026 Uiso 1 1 calc R . .
C16 C 0.70087(17) 0.12549(15) 0.51255(13) 0.0205(5) Uani 1 1 d . . .
H16A H 0.6868 0.1607 0.4744 0.025 Uiso 1 1 calc R . .
H16B H 0.6406 0.1018 0.5277 0.025 Uiso 1 1 calc R . .
C17 C 0.76501(17) 0.05682(15) 0.49026(12) 0.0184(5) Uani 1 1 d . . .
C18 C 0.83530(19) 0.02528(16) 0.53020(13) 0.0237(6) Uani 1 1 d . . .
H18 H 0.8475 0.0499 0.5714 0.028 Uiso 1 1 calc R . .
C19 C 0.88806(19) -0.04164(16) 0.51085(13) 0.0237(6) Uani 1 1 d . . .
H19 H 0.9359 -0.0628 0.5386 0.028 Uiso 1 1 calc R . .
C20 C 0.86987(18) -0.07732(15) 0.45010(13) 0.0202(5) Uani 1 1 d . . .
C21 C 0.80120(18) -0.04579(16) 0.40927(13) 0.0223(5) Uani 1 1 d . . .
H21 H 0.7897 -0.0697 0.3677 0.027 Uiso 1 1 calc R . .
C22 C 0.74925(18) 0.02104(16) 0.42962(13) 0.0225(6) Uani 1 1 d . . .
H22 H 0.7021 0.0427 0.4016 0.027 Uiso 1 1 calc R . .
C23 C 0.0718(2) 0.47857(17) 0.73872(14) 0.0267(6) Uani 1 1 d . . .
H23 H 0.0481 0.5132 0.7020 0.032 Uiso 1 1 calc R . .
Cl1 Cl 0.18649(6) 0.51073(5) 0.75931(5) 0.0476(2) Uani 1 1 d . . .
Cl2 Cl -0.00408(6) 0.49064(5) 0.80622(4) 0.0413(2) Uani 1 1 d . . .
Cl3 Cl 0.07347(5) 0.37668(4) 0.71235(3) 0.02712(14) 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C9 122.1(2) . . ?
C6 N1 C16 121.4(2) . . ?
C9 N1 C16 116.0(2) . . ?
O1 C1 C2 135.0(2) . . ?
O1 C1 C2 134.8(2) . 5_766 ?
C2 C1 C2 90.2(2) . 5_766 ?
C3 C2 C1 135.1(2) . . ?
C3 C2 C1 135.1(2) . 5_766 ?
C1 C2 C1 89.8(2) . 5_766 ?
C2 C3 C4 121.7(2) . . ?
C2 C3 C8 120.4(2) . . ?
C4 C3 C8 117.9(2) . . ?
C5 C4 C3 121.2(2) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
N1 C6 C7 121.1(2) . . ?
N1 C6 C5 120.8(2) . . ?
C7 C6 C5 118.1(2) . . ?
C8 C7 C6 120.9(2) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C3 121.3(2) . . ?
C7 C8 H8 119.3 . . ?
C3 C8 H8 119.3 . . ?
N1 C9 C10 114.5(2) . . ?
N1 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
N1 C9 H9B 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C15 119.3(2) . . ?
C11 C10 C9 121.6(2) . . ?
C15 C10 C9 119.0(2) . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 119.4(2) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 121.2(2) . . ?
C12 C13 I1 118.86(19) . . ?
C14 C13 I1 119.90(19) . . ?
C15 C14 C13 119.0(2) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C10 120.8(2) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
N1 C16 C17 114.5(2) . . ?
N1 C16 H16A 108.6 . . ?
C17 C16 H16A 108.6 . . ?
N1 C16 H16B 108.6 . . ?
C17 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C22 C17 C18 118.7(2) . . ?
C22 C17 C16 119.0(2) . . ?
C18 C17 C16 122.1(2) . . ?
C19 C18 C17 121.1(3) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 119.1(2) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C21 C20 C19 120.5(2) . . ?
C21 C20 I2 120.32(19) . . ?
C19 C20 I2 119.14(19) . . ?
C20 C21 C22 119.4(2) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C21 C22 C17 121.1(2) . . ?
C21 C22 H22 119.4 . . ?
C17 C22 H22 119.4 . . ?
Cl3 C23 Cl2 110.81(15) . . ?
Cl3 C23 Cl1 110.22(16) . . ?
Cl2 C23 Cl1 110.18(15) . . ?
Cl3 C23 H23 108.5 . . ?
Cl2 C23 H23 108.5 . . ?
Cl1 C23 H23 108.5 . . ?
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 C13 2.095(3) . ?
I2 C20 2.102(3) . ?
N1 C6 1.361(3) . ?
N1 C9 1.458(3) . ?
N1 C16 1.461(3) . ?
O1 C1 1.236(3) . ?
C1 C2 1.464(3) . ?
C1 C2 1.466(3) 5_766 ?
C2 C3 1.401(3) . ?
C2 C1 1.466(3) 5_766 ?
C3 C4 1.411(3) . ?
C3 C8 1.414(4) . ?
C4 C5 1.366(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.425(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.410(4) . ?
C7 C8 1.363(4) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.520(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.389(4) . ?
C10 C15 1.392(4) . ?
C11 C12 1.393(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(4) . ?
C14 C15 1.385(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.521(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C22 1.389(4) . ?
C17 C18 1.389(4) . ?
C18 C19 1.389(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.396(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.384(4) . ?
C21 C22 1.388(4) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 Cl3 1.760(3) . ?
C23 Cl2 1.760(3) . ?
C23 Cl1 1.764(3) . ?
C23 H23 1.0000 . ?
