#------------------------------------------------------------------------------
#$Date: 2025-08-19 21:30:04 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301811 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/18/4001841.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_4001841
loop_
_publ_author_name
'González, Lucía'
'Gimeno, Nélida'
'Tejedor, Rosa María'
'Polo, Víctor'
'Ros, M. Blanca'
'Uriel, Santiago'
'Serrano, José Luis'
_publ_section_title
;
 Halogen-Bonding Complexes Based on Bis(iodoethynyl)benzene Units: A New
 Versatile Route to Supramolecular Materials
;
_journal_issue                   22
_journal_name_full               'Chemistry of Materials'
_journal_page_first              4503
_journal_paper_doi               10.1021/cm401849f
_journal_volume                  25
_journal_year                    2013
_chemical_formula_sum            'C44 H54 I2 N2 O2'
_chemical_formula_weight         896.70
_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_date
;
'Wed Nov 09 00:28:52 2011'
;
_audit_creation_method
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_cell_angle_alpha                97.85(3)
_cell_angle_beta                 96.79(3)
_cell_angle_gamma                113.64(4)
_cell_formula_units_Z            1
_cell_length_a                   8.608(3)
_cell_length_b                   10.221(4)
_cell_length_c                   13.297(5)
_cell_measurement_reflns_used    306
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28.7403
_cell_measurement_theta_min      2.9659
_cell_volume                     1042.2(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      133(2)
_diffrn_detector_area_resol_mean 16.3990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -77.00   49.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9615   19.0000   90.0000 126

  2 omega  -40.00    1.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9615  -57.0000  150.0000 41

  3 omega  -21.00   24.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9615  -99.0000   60.0000 45

  4 omega  -77.00    3.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9615  -57.0000 -120.0000 80

  5 omega  -48.00   43.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       21.4302  -57.0000  120.0000 91

  6 omega   75.00  101.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       21.4302  179.0000  120.0000 26

;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0209596000
_diffrn_orient_matrix_UB_12      -0.0535701000
_diffrn_orient_matrix_UB_13      0.0190812000
_diffrn_orient_matrix_UB_21      -0.0634865000
_diffrn_orient_matrix_UB_22      -0.0110473000
_diffrn_orient_matrix_UB_23      0.0314071000
_diffrn_orient_matrix_UB_31      -0.0626609000
_diffrn_orient_matrix_UB_32      -0.0546921000
_diffrn_orient_matrix_UB_33      -0.0407251000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1884
_diffrn_reflns_av_sigmaI/netI    0.4255
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7425
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.97
_exptl_absorpt_coefficient_mu    1.545
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             454
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.746
_refine_diff_density_min         -1.552
_refine_diff_density_rms         0.182
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         4262
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.2913
_refine_ls_R_factor_gt           0.1092
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.016
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1476
_refine_ls_wR_factor_ref         0.2204
_reflns_number_gt                1413
_reflns_number_total             4262
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cm401849f_si_002.cif
_cod_data_source_block           xcalibur
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1042.2(7)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4001841
#BEGIN Tags that were not found in dictionaries:
_cell_oxdiff_length_a            8.608(3)
_cell_oxdiff_length_b            10.221(4)
_cell_oxdiff_length_c            13.297(5)
_cell_oxdiff_angle_alpha         97.85(3)
_cell_oxdiff_angle_beta          96.79(3)
_cell_oxdiff_angle_gamma         113.64(4)
_cell_oxdiff_volume              1042.2(7)
_cell_oxdiff_measurement_reflns_used 306
#END Tags that were not found in dictionaries
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
I1 I 0.66417(15) 0.42374(13) -0.28643(10) 0.0409(4) Uani 1 1 d .
O1 O 0.9194(13) 0.9852(11) -0.2214(8) 0.034(3) Uani 1 1 d .
C1 C 0.6066(18) 0.2838(17) -0.1879(13) 0.031(4) Uani 1 1 d .
N1 N 1.2298(19) 1.3644(17) -0.5774(12) 0.054(5) Uani 1 1 d .
C2 C 0.5723(18) 0.1974(19) -0.1384(14) 0.037(5) Uani 1 1 d .
C3 C 0.5368(17) 0.0981(17) -0.0673(13) 0.026(4) Uani 1 1 d .
C4 C 0.467(2) 0.1216(18) 0.0182(13) 0.041(5) Uani 1 1 d .
H4 H 0.4423 0.2042 0.0311 0.049 Uiso 1 1 calc R
C5 C 0.4326(18) 0.0239(18) 0.0861(12) 0.034(5) Uani 1 1 d .
H5 H 0.3877 0.0425 0.1456 0.041 Uiso 1 1 calc R
C6 C 1.180(2) 1.302(2) -0.5175(15) 0.042(5) Uani 1 1 d .
C7 C 1.114(2) 1.2186(17) -0.4420(12) 0.032(4) Uani 1 1 d .
C8 C 1.1945(19) 1.1350(17) -0.4062(12) 0.035(5) Uani 1 1 d .
H8 H 1.2916 1.1332 -0.4327 0.042 Uiso 1 1 calc R
C9 C 1.133(2) 1.0540(16) -0.3315(13) 0.034(5) Uani 1 1 d .
H9 H 1.1871 0.9965 -0.3075 0.041 Uiso 1 1 calc R
C10 C 0.993(2) 1.0578(17) -0.2927(12) 0.029(4) Uani 1 1 d .
C11 C 0.9128(19) 1.1394(15) -0.3309(12) 0.028(4) Uani 1 1 d .
H11 H 0.8133 1.1391 -0.3066 0.034 Uiso 1 1 calc R
C12 C 0.9738(19) 1.2190(15) -0.4021(12) 0.028(4) Uani 1 1 d .
H12 H 0.9189 1.2766 -0.4251 0.034 Uiso 1 1 calc R
C13 C 0.9941(19) 0.8979(16) -0.1795(13) 0.038(5) Uani 1 1 d .
H13A H 1.1152 0.9589 -0.1439 0.046 Uiso 1 1 calc R
H13B H 0.9926 0.8220 -0.2350 0.046 Uiso 1 1 calc R
C14 C 0.8825(19) 0.8276(16) -0.1023(12) 0.035(5) Uani 1 1 d .
H14A H 0.8753 0.9062 -0.0533 0.042 Uiso 1 1 calc R
H14B H 0.7641 0.7643 -0.1412 0.042 Uiso 1 1 calc R
C15 C 0.9428(19) 0.7377(16) -0.0399(12) 0.031(4) Uani 1 1 d .
H15A H 1.0579 0.8006 0.0034 0.037 Uiso 1 1 calc R
H15B H 0.9538 0.6598 -0.0874 0.037 Uiso 1 1 calc R
C16 C 0.8162(19) 0.6697(16) 0.0289(12) 0.030(4) Uani 1 1 d .
H16A H 0.8091 0.7484 0.0778 0.036 Uiso 1 1 calc R
H16B H 0.7002 0.6112 -0.0146 0.036 Uiso 1 1 calc R
C17 C 0.865(2) 0.5745(17) 0.0888(12) 0.033(4) Uani 1 1 d .
H17A H 0.9841 0.6312 0.1293 0.040 Uiso 1 1 calc R
H17B H 0.8652 0.4921 0.0401 0.040 Uiso 1 1 calc R
C18 C 0.7442(19) 0.5156(16) 0.1612(12) 0.033(4) Uani 1 1 d .
H18A H 0.6256 0.4636 0.1198 0.039 Uiso 1 1 calc R
H18B H 0.7472 0.5995 0.2097 0.039 Uiso 1 1 calc R
C19 C 0.7771(18) 0.4130(16) 0.2249(12) 0.031(4) Uani 1 1 d .
H19A H 0.7778 0.3305 0.1767 0.037 Uiso 1 1 calc R
H19B H 0.8941 0.4660 0.2683 0.037 Uiso 1 1 calc R
C20 C 0.6538(19) 0.3523(16) 0.2932(12) 0.027(4) Uiso 1 1 d .
H20A H 0.5351 0.3060 0.2516 0.032 Uiso 1 1 calc R
H20B H 0.6609 0.4333 0.3465 0.032 Uiso 1 1 calc R
C21 C 0.685(2) 0.2429(18) 0.3456(14) 0.051(5) Uani 1 1 d .
H21A H 0.8012 0.2901 0.3900 0.061 Uiso 1 1 calc R
H21B H 0.6826 0.1638 0.2926 0.061 Uiso 1 1 calc R
C22 C 0.550(2) 0.1764(19) 0.4123(14) 0.062(6) Uani 1 1 d .
H22A H 0.5374 0.2546 0.4569 0.093 Uiso 1 1 calc R
H22B H 0.5886 0.1202 0.4552 0.093 Uiso 1 1 calc R
H22C H 0.4389 0.1119 0.3673 0.093 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'
I I -0.4742 1.8119 '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'
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
C10 O1 C13 117.7(13) .
C2 C1 I1 175.1(18) .
C1 C2 C3 175(2) .
C5 C3 C4 118.9(17) 2_655
C5 C3 C2 119.9(18) 2_655
C4 C3 C2 121.1(18) .
C3 C4 C5 120.4(18) .
C3 C5 C4 120.7(17) 2_655
N1 C6 C7 179(2) .
C12 C7 C8 118.5(16) .
C12 C7 C6 122.0(17) .
C8 C7 C6 119.4(16) .
C7 C8 C9 120.2(16) .
C10 C9 C8 119.7(16) .
O1 C10 C9 126.2(16) .
O1 C10 C11 114.7(15) .
C9 C10 C11 119.0(16) .
C12 C11 C10 121.1(16) .
C11 C12 C7 121.3(16) .
O1 C13 C14 105.9(13) .
C15 C14 C13 116.8(14) .
C14 C15 C16 110.9(13) .
C17 C16 C15 113.2(14) .
C16 C17 C18 112.3(14) .
C17 C18 C19 117.6(14) .
C20 C19 C18 117.0(14) .
C19 C20 C21 113.8(14) .
C20 C21 C22 112.9(15) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C1 2.025(17) .
O1 C10 1.345(17) .
O1 C13 1.425(16) .
C1 C2 1.14(2) .
N1 C6 1.10(2) .
C2 C3 1.45(2) .
C3 C5 1.37(2) 2_655
C3 C4 1.38(2) .
C4 C5 1.40(2) .
C5 C3 1.37(2) 2_655
C6 C7 1.43(2) .
C7 C12 1.38(2) .
C7 C8 1.39(2) .
C8 C9 1.40(2) .
C9 C10 1.38(2) .
C10 C11 1.39(2) .
C11 C12 1.35(2) .
C13 C14 1.54(2) .
C14 C15 1.512(18) .
C15 C16 1.52(2) .
C16 C17 1.491(18) .
C17 C18 1.51(2) .
C18 C19 1.523(18) .
C19 C20 1.48(2) .
C20 C21 1.488(19) .
C21 C22 1.54(2) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139089314
