#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/18/7201809.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_7201809
loop_
_publ_author_name
'Schollmeyer, Dieter'
'Shishkin, Oleg V.'
'Rühl, Thomas'
'Vysotsky, Myroslav O.'
_publ_section_title
;
 OH--π and halogen--π interactions as driving forces in the crystal
 organisations of tri-bromo and tri-iodo trityl alcohols
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              715
_journal_paper_doi               10.1039/b716442d
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C19 H13 I3 O, C H2 Cl2'
_chemical_formula_sum            'C20 H15 Cl2 I3 O'
_chemical_formula_weight         722.92
_chemical_name_systematic
;
?
;
_space_group_IT_number           39
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'A 2 -2b'
_symmetry_space_group_name_H-M   'A b m 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            4
_cell_length_a                   12.2182(4)
_cell_length_b                   20.4790(5)
_cell_length_c                   8.5939(2)
_cell_measurement_reflns_used    6423
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      2.5
_cell_volume                     2150.34(10)
_computing_cell_refinement       'APEX2 V2.0 (Bruker, 2006)'
_computing_data_collection       'APEX2 V2.0 (Bruker, 2006)'
_computing_data_reduction        'APEX2 V2.0 (Bruker, 2006)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Altomare, 1997)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SMART CCD'
_diffrn_measurement_method       'CCD scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9554
_diffrn_reflns_theta_full        27.86
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         1.67
_diffrn_source                   'sealed Tube'
_exptl_absorpt_coefficient_mu    4.617
_exptl_absorpt_correction_T_max  0.7692
_exptl_absorpt_correction_T_min  0.2596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Blessing
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.920
_refine_diff_density_min         -1.217
_refine_diff_density_rms         0.134
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         2546
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0273
_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)+(0.0462P)²+7.6243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0751
_refine_ls_wR_factor_ref         0.0756
_reflns_number_gt                2462
_reflns_number_total             2546
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b716442d.txt
_cod_data_source_block           2C
_cod_original_sg_symbol_Hall     'A 2 -2c'
_cod_original_sg_symbol_H-M      'A bm2'
_cod_database_code               7201809
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x, y, z+1/2'
'x, -y, z+1/2'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, z+1'
'x, -y+1/2, z+1'
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
I2 I 0.17893(3) 0.014137(13) 0.39999(5) 0.03665(11) Uani 1 1 d . . .
I1 I 0.46537(4) 0.2500 1.45267(6) 0.03611(13) Uani 1 2 d S . .
O20 O 0.0128(3) 0.2500 0.9429(6) 0.0236(8) Uani 1 2 d S . .
H20 H -0.0085 0.2500 1.0352 0.028 Uiso 1 2 d SR . .
C1 C 0.1230(5) 0.2500 0.8859(8) 0.0220(11) Uani 1 2 d S . .
C8 C 0.1362(4) 0.18985(19) 0.7812(5) 0.0190(8) Uani 1 1 d . . .
C13 C 0.2397(4) 0.1716(2) 0.7266(6) 0.0268(9) Uani 1 1 d . . .
H13 H 0.3026 0.1941 0.7631 0.032 Uiso 1 1 calc R . .
C12 C 0.2520(4) 0.1212(2) 0.6202(6) 0.0297(10) Uani 1 1 d . . .
H12 H 0.3227 0.1094 0.5838 0.036 Uiso 1 1 calc R . .
C11 C 0.1597(4) 0.0881(2) 0.5673(5) 0.0240(9) Uani 1 1 d . . .
C10 C 0.0576(4) 0.1038(2) 0.6225(6) 0.0263(9) Uani 1 1 d . . .
H10 H -0.0049 0.0804 0.5878 0.032 Uiso 1 1 calc R . .
C9 C 0.0461(4) 0.15453(19) 0.7303(6) 0.0222(8) Uani 1 1 d . . .
H9 H -0.0245 0.1650 0.7693 0.027 Uiso 1 1 calc R . .
C2 C 0.2030(5) 0.2500 1.0224(7) 0.0186(11) Uani 1 2 d S . .
C3 C 0.2368(4) 0.1914(2) 1.0894(5) 0.0256(9) Uani 1 1 d . . .
H3 H 0.2104 0.1512 1.0490 0.031 Uiso 1 1 calc R . .
C4 C 0.3096(4) 0.1912(2) 1.2164(6) 0.0280(10) Uani 1 1 d . . .
H4 H 0.3331 0.1512 1.2610 0.034 Uiso 1 1 calc R . .
C5 C 0.3465(5) 0.2500 1.2752(7) 0.0267(13) Uani 1 2 d S . .
C1L C 0.5000 0.0000 0.7668(19) 0.076(3) Uani 1 2 d S . .
H1L1 H 0.5641 0.0055 0.7007 0.092 Uiso 1 1 d R . .
Cl1 Cl 0.48285(19) 0.07045(10) 0.8815(4) 0.0785(6) 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'
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'
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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O20 C1 C2 109.8(5) . . ?
O20 C1 C8 107.4(3) . . ?
C2 C1 C8 112.6(3) . . ?
O20 C1 C8 107.4(3) . 8_554 ?
C2 C1 C8 112.6(3) . 8_554 ?
C8 C1 C8 106.8(5) . 8_554 ?
C9 C8 C13 118.1(4) . . ?
C9 C8 C1 121.3(4) . . ?
C13 C8 C1 120.5(4) . . ?
C12 C13 C8 121.2(4) . . ?
C13 C12 C11 119.3(5) . . ?
C10 C11 C12 120.6(4) . . ?
C10 C11 I2 120.4(3) . . ?
C12 C11 I2 119.0(4) . . ?
C11 C10 C9 119.6(4) . . ?
C8 C9 C10 121.1(4) . . ?
C3 C2 C3 118.9(6) 8_554 . ?
C3 C2 C1 120.5(3) 8_554 . ?
C3 C2 C1 120.5(3) . . ?
C2 C3 C4 120.7(4) . . ?
C5 C4 C3 119.2(4) . . ?
C4 C5 C4 121.3(6) . 8_554 ?
C4 C5 I1 119.3(3) . . ?
C4 C5 I1 119.3(3) 8_554 . ?
Cl1 C1L Cl1 111.9(9) . 2_655 ?
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
I2 C11 2.102(4) . ?
I1 C5 2.106(7) . ?
O20 C1 1.433(7) . ?
C1 C2 1.527(9) . ?
C1 C8 1.534(6) . ?
C1 C8 1.534(6) 8_554 ?
C8 C9 1.388(6) . ?
C8 C13 1.399(6) . ?
C13 C12 1.386(7) . ?
C12 C11 1.392(7) . ?
C11 C10 1.373(7) . ?
C10 C9 1.398(7) . ?
C2 C3 1.393(5) 8_554 ?
C2 C3 1.393(5) . ?
C3 C4 1.408(7) . ?
C4 C5 1.381(6) . ?
C5 C4 1.381(6) 8_554 ?
C1L Cl1 1.760(9) . ?
C1L Cl1 1.760(9) 2_655 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O20 C1 C8 C9 13.3(6) . . . . ?
C2 C1 C8 C9 134.2(5) . . . . ?
C8 C1 C8 C9 -101.7(5) 8_554 . . . ?
O20 C1 C8 C13 -170.7(4) . . . . ?
C2 C1 C8 C13 -49.7(6) . . . . ?
C8 C1 C8 C13 74.3(6) 8_554 . . . ?
C9 C8 C13 C12 2.4(7) . . . . ?
C1 C8 C13 C12 -173.8(5) . . . . ?
C8 C13 C12 C11 -0.3(8) . . . . ?
C13 C12 C11 C10 -1.7(7) . . . . ?
C13 C12 C11 I2 177.8(4) . . . . ?
C12 C11 C10 C9 1.5(7) . . . . ?
I2 C11 C10 C9 -178.1(3) . . . . ?
C13 C8 C9 C10 -2.6(6) . . . . ?
C1 C8 C9 C10 173.5(4) . . . . ?
C11 C10 C9 C8 0.7(7) . . . . ?
O20 C1 C2 C3 -87.6(5) . . . 8_554 ?
C8 C1 C2 C3 152.8(5) . . . 8_554 ?
C8 C1 C2 C3 32.0(7) 8_554 . . 8_554 ?
O20 C1 C2 C3 87.6(5) . . . . ?
C8 C1 C2 C3 -32.0(7) . . . . ?
C8 C1 C2 C3 -152.8(5) 8_554 . . . ?
C3 C2 C3 C4 -4.1(9) 8_554 . . . ?
C1 C2 C3 C4 -179.4(5) . . . . ?
C2 C3 C4 C5 0.7(8) . . . . ?
C3 C4 C5 C4 2.9(10) . . . 8_554 ?
C3 C4 C5 I1 -175.0(4) . . . . ?
