#------------------------------------------------------------------------------
#$Date: 2016-03-21 01:21:50 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178377 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/18/4001842.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_4001842
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_moiety         '2(C15 H25 N O), C10 H4 I2'
_chemical_formula_sum            'C30 H54 I2 N2 O2'
_chemical_formula_weight         848.66
_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_date
;
'Wed Nov 16 01:08:27 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                75.71(3)
_cell_angle_beta                 84.00(3)
_cell_angle_gamma                66.93(4)
_cell_formula_units_Z            1
_cell_length_a                   7.728(3)
_cell_length_b                   9.453(4)
_cell_length_c                   14.800(5)
_cell_measurement_reflns_used    332
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.7966
_cell_measurement_theta_min      2.8348
_cell_volume                     963.9(7)
_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      150(2)
_diffrn_detector_area_resol_mean 16.3990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -91.00   -7.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.1177  -57.0000 -120.0000 84

  2 omega   -9.00   26.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       21.5865   77.0000    0.0000 35

  3 omega   55.00   92.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       21.5865   57.0000  150.0000 37

  4 omega  -22.00   59.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       21.5865  -99.0000  120.0000 81

  5 omega  -49.00   34.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       21.5865  -57.0000    0.0000 83

  6 omega  -25.00   65.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       21.5865  -99.0000 -120.0000 90

;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0517250000
_diffrn_orient_matrix_UB_12      -0.0575451000
_diffrn_orient_matrix_UB_13      0.0383984000
_diffrn_orient_matrix_UB_21      -0.0851721000
_diffrn_orient_matrix_UB_22      -0.0012167000
_diffrn_orient_matrix_UB_23      0.0225819000
_diffrn_orient_matrix_UB_31      0.0049227000
_diffrn_orient_matrix_UB_32      -0.0607763000
_diffrn_orient_matrix_UB_33      -0.0214854000
_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  0.1458
_diffrn_reflns_av_sigmaI/netI    0.3072
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5810
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         2.84
_exptl_absorpt_coefficient_mu    1.666
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49554
_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    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Neddle
_exptl_crystal_F_000             430
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.081
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.184
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3282
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.2226
_refine_ls_R_factor_gt           0.1115
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0384P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1637
_refine_ls_wR_factor_ref         0.2118
_reflns_number_gt                1528
_reflns_number_total             3282
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cm401849f_si_003.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        963.8(6)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4001842
#BEGIN Tags that were not found in dictionaries:
_cell_oxdiff_length_a            7.728(2)
_cell_oxdiff_length_b            9.453(4)
_cell_oxdiff_length_c            14.800(5)
_cell_oxdiff_angle_alpha         75.71(3)
_cell_oxdiff_angle_beta          84.00(3)
_cell_oxdiff_angle_gamma         66.93(3)
_cell_oxdiff_volume              963.8(6)
_cell_oxdiff_measurement_reflns_used 332
#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 0.43240(18) 0.74628(15) 0.17099(9) 0.0392(4) Uani 1 1 d .
O1 O 0.9656(15) 0.5877(13) -0.2212(7) 0.039(3) Uani 1 1 d .
N1 N 0.6593(19) 0.6576(18) 0.0219(10) 0.040(4) Uani 1 1 d .
C1 C 0.284(2) 0.829(2) 0.2794(12) 0.038(5) Uiso 1 1 d .
C2 C 0.201(2) 0.8792(19) 0.3442(12) 0.033(4) Uani 1 1 d .
C3 C 0.096(2) 0.9426(19) 0.4221(12) 0.031(4) Uani 1 1 d .
C4 C 0.097(2) 0.8398(19) 0.5086(11) 0.039(5) Uani 1 1 d .
H4 H 0.1610 0.7317 0.5149 0.047 Uiso 1 1 calc R
C5 C -0.004(2) 1.1032(18) 0.4158(10) 0.030(4) Uani 1 1 d .
H5 H -0.0080 1.1736 0.3590 0.036 Uiso 1 1 calc R
C6 C 0.696(2) 0.766(2) -0.0393(11) 0.039(5) Uani 1 1 d .
H6 H 0.6515 0.8665 -0.0268 0.047 Uiso 1 1 calc R
C7 C 0.796(2) 0.748(2) -0.1215(11) 0.033(5) Uani 1 1 d .
H7 H 0.8166 0.8319 -0.1623 0.040 Uiso 1 1 calc R
C8 C 0.866(2) 0.600(2) -0.1413(12) 0.038(5) Uani 1 1 d .
C9 C 0.831(2) 0.4800(19) -0.0757(10) 0.030(4) Uani 1 1 d .
H9 H 0.8779 0.3778 -0.0851 0.036 Uiso 1 1 calc R
C10 C 0.729(2) 0.514(2) 0.0021(11) 0.038(5) Uani 1 1 d .
H10 H 0.7045 0.4322 0.0442 0.045 Uiso 1 1 calc R
C11 C 1.036(2) 0.439(2) -0.2482(11) 0.041(5) Uani 1 1 d .
H11A H 0.9338 0.4053 -0.2532 0.049 Uiso 1 1 calc R
H11B H 1.1263 0.3575 -0.2036 0.049 Uiso 1 1 calc R
C12 C 1.129(2) 0.4710(19) -0.3431(10) 0.034(5) Uani 1 1 d .
H12A H 1.0351 0.5552 -0.3851 0.041 Uiso 1 1 calc R
H12B H 1.2258 0.5082 -0.3359 0.041 Uiso 1 1 calc R
C13 C 1.216(2) 0.3298(17) -0.3877(9) 0.026(4) Uani 1 1 d .
H13A H 1.3126 0.2463 -0.3471 0.031 Uiso 1 1 calc R
H13B H 1.1201 0.2907 -0.3942 0.031 Uiso 1 1 calc R
C14 C 1.301(2) 0.3700(18) -0.4822(10) 0.032(4) Uani 1 1 d .
H14A H 1.3965 0.4089 -0.4747 0.038 Uiso 1 1 calc R
H14B H 1.2038 0.4554 -0.5216 0.038 Uiso 1 1 calc R
C15 C 1.390(2) 0.2356(19) -0.5329(11) 0.039(5) Uani 1 1 d .
H15A H 1.4911 0.1517 -0.4949 0.047 Uiso 1 1 calc R
H15B H 1.2963 0.1939 -0.5385 0.047 Uiso 1 1 calc R
C16 C 1.468(2) 0.2802(19) -0.6285(11) 0.034(4) Uani 1 1 d .
H16A H 1.5600 0.3241 -0.6237 0.041 Uiso 1 1 calc R
H16B H 1.3667 0.3613 -0.6677 0.041 Uiso 1 1 calc R
C17 C 1.559(2) 0.1414(18) -0.6739(10) 0.031(4) Uani 1 1 d .
H17A H 1.4643 0.1016 -0.6813 0.037 Uiso 1 1 calc R
H17B H 1.6541 0.0581 -0.6323 0.037 Uiso 1 1 calc R
C18 C 1.650(2) 0.178(2) -0.7687(11) 0.038(5) Uani 1 1 d .
H18A H 1.7447 0.2179 -0.7619 0.046 Uiso 1 1 calc R
H18B H 1.5551 0.2598 -0.8110 0.046 Uiso 1 1 calc R
C19 C 1.742(2) 0.031(2) -0.8113(12) 0.042(5) Uani 1 1 d .
H19A H 1.8368 -0.0505 -0.7687 0.050 Uiso 1 1 calc R
H19B H 1.6472 -0.0089 -0.8175 0.050 Uiso 1 1 calc R
C20 C 1.833(2) 0.063(2) -0.9050(11) 0.054(6) Uani 1 1 d .
H20A H 1.7393 0.1390 -0.9488 0.082 Uiso 1 1 calc R
H20B H 1.8909 -0.0335 -0.9264 0.082 Uiso 1 1 calc R
H20C H 1.9270 0.1031 -0.8998 0.082 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
C8 O1 C11 118.6(13) .
C6 N1 C10 115.4(15) .
C2 C1 I1 177.3(15) .
C1 C2 C3 178.5(18) .
C5 C3 C4 117.5(15) .
C5 C3 C2 122.9(16) .
C4 C3 C2 119.6(15) .
C5 C4 C3 120.8(15) 2_576
C4 C5 C3 121.6(16) 2_576
N1 C6 C7 126.0(17) .
C8 C7 C6 118.1(17) .
O1 C8 C7 115.7(16) .
O1 C8 C9 127.2(15) .
C7 C8 C9 117.1(16) .
C10 C9 C8 119.4(15) .
N1 C10 C9 124.0(16) .
O1 C11 C12 104.1(13) .
C13 C12 C11 114.8(13) .
C14 C13 C12 112.4(12) .
C13 C14 C15 116.0(13) .
C16 C15 C14 115.0(13) .
C15 C16 C17 112.5(13) .
C16 C17 C18 114.7(13) .
C17 C18 C19 112.4(13) .
C20 C19 C18 113.9(14) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C1 2.008(16) .
O1 C8 1.348(18) .
O1 C11 1.440(16) .
N1 C6 1.29(2) .
N1 C10 1.349(19) .
C1 C2 1.190(19) .
C2 C3 1.45(2) .
C3 C5 1.392(19) .
C3 C4 1.40(2) .
C4 C5 1.372(18) 2_576
C5 C4 1.372(18) 2_576
C6 C7 1.38(2) .
C7 C8 1.38(2) .
C8 C9 1.39(2) .
C9 C10 1.359(19) .
C11 C12 1.527(19) .
C12 C13 1.519(18) .
C13 C14 1.508(18) .
C14 C15 1.526(19) .
C15 C16 1.506(19) .
C16 C17 1.510(18) .
C17 C18 1.526(19) .
C18 C19 1.55(2) .
C19 C20 1.50(2) .
