#------------------------------------------------------------------------------
#$Date: 2019-11-17 13:10:10 +0100 (dom 17 de nov de 2019) $
#$Revision: 230396 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/73/7057378.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_7057378
loop_
_publ_author_name
'Gamekkanda, Janaka C.'
'Sinha, Abhijeet S.'
'Desper, John'
'Đaković, Marijana'
'Aakeröy, Christer B.'
_publ_section_title
;
 Competition between hydrogen bonds and halogen bonds: a structural study
;
_journal_issue                   13
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10539
_journal_paper_doi               10.1039/C8NJ00537K
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C10 H10 I2 O2, H2 O '
_chemical_formula_sum            'C10 H12 I2 O3'
_chemical_formula_weight         434.00
_space_group_crystal_system      tetragonal
_space_group_IT_number           84
_space_group_name_Hall           '-P 4c'
_space_group_name_H-M_alt        'P 42/m'
_symmetry_space_group_name_Hall  '-P 4c'
_symmetry_space_group_name_H-M   'P 42/m'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-01-29 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5167(5)
_cell_length_b                   8.5167(5)
_cell_length_c                   8.8404(9)
_cell_measurement_reflns_used    1458
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.4360
_cell_measurement_theta_min      5.1350
_cell_volume                     641.23(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35 
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35 
;
_computing_molecular_graphics
;
Mercury (Bruno et al., 2002)
;
_computing_publication_material
;
SHELXL-2014/7 (Sheldrick, 2013) and PLATON (Spek, 2003)
;
_computing_structure_refinement
;
SHELXL-2014/7 (Sheldrick, 2014)
;
_computing_structure_solution
;
SHELXS-2014/7 (Sheldrick, 2014)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5273
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.652
_diffrn_reflns_theta_min         4.611
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.891
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    2.248
_exptl_crystal_description       prizm
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.947
_refine_diff_density_min         -1.114
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       0.0162(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     49
_refine_ls_number_reflns         1152
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0294
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0300P)²+0.4460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0640
_refine_ls_wR_factor_ref         0.0741
_reflns_number_gt                891
_reflns_number_total             1239
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj00537k2.cif
_cod_data_source_block           D1
_cod_depositor_comments
'Adding full bibliography for 7057378--7057386.cif.'
_cod_original_cell_volume        641.23(10)
_cod_database_code               7057378
_diffrn_measurment_method        '\w scan'
_shelx_res_file
;

    shelx.res created by SHELXL-2014/7


TITL exp_941 in P4(2)                 New: P42/m
CELL  0.71073   8.5167   8.5167   8.8404   90.000   90.000   90.000
ZERR     2.00   0.0005   0.0005   0.0009    0.000    0.000    0.000
LATT   1
SYMM  - Y,   X, 1/2 + Z
SYMM  - X, - Y,   Z
SYMM    Y, - X, 1/2 + Z
SFAC  C    H    I    O
UNIT  20   24   4    6
MERG   2
DFIX  0.82 0.02 O1 H1O O2 H2O
FMAP   2
PLAN   20
ACTA
BOND   $H
HTAB
EQIV $1 x-1, y, z
HTAB C4 I1_$1
EQIV $2 y, -x, -z+1/2
HTAB O2 O1_$2
EQIV $3 -x, -y, -z+1
HTAB O1 O2_$3
BIND I1 O1_$4
EQIV $4 1+x, y, z
CONF
L.S.  10
TEMP    23.00
WGHT    0.030000    0.446000
EXTI    0.016163
FVAR       5.83571
I1    3    0.545150    0.251028    0.500000    10.50000    0.02620    0.03898 =
         0.04843    0.00000    0.00000   -0.00074
O1    4   -0.091334    0.185084    0.500000    10.50000    0.02856    0.03040 =
         0.04352    0.00000    0.00000   -0.00590
C1    1    0.310569    0.271392    0.500000    10.50000    0.03208    0.03639 =
         0.04350    0.00000    0.00000    0.00070
C2    1    0.172426    0.287374    0.500000    10.50000    0.03162    0.03259 =
         0.03585    0.00000    0.00000   -0.00026
C3    1    0.004746    0.326651    0.500000    10.50000    0.02902    0.02352 =
         0.02642    0.00000    0.00000    0.00338
C4    1   -0.039196    0.419710    0.358371    11.00000    0.03108    0.03401 =
         0.02657   -0.00028   -0.00073   -0.00146
AFIX  23
H4A   2   -0.006905    0.361772    0.269175    11.00000   -1.20000
H4B   2   -0.152264    0.432739    0.354310    11.00000   -1.20000
AFIX   0
O2    4    0.000000    0.000000    0.250000    10.25000    0.04008    0.04008 =
         0.04483    0.00000    0.00000    0.00000
H2O   2    0.070685    0.036100    0.201195    10.50000   -1.20000
H1O   2   -0.076831    0.141538    0.582215    10.50000   -1.20000
HKLF    4  1.0  1.00  0.00  0.00  0.00 -1.00  0.00  0.00  0.00 -1.00

REM  exp_941 in P4(2)                 New: P42/m
REM R1 =  0.0294 for     891 Fo > 4sig(Fo)  and  0.0446 for all    1152 data
REM     49 parameters refined using      2 restraints

END

WGHT      0.0288      0.4331

REM Instructions for potential hydrogen bonds
HTAB C4 I1_$1
HTAB O2 O1_$2
HTAB O1 O2_$3

REM Highest difference peak  0.947,  deepest hole -1.114,  1-sigma level  0.129
Q1    1   0.0416  0.1598  0.5000  10.50000  0.05    0.95
Q2    1   0.5389  0.2949  0.5601  11.00000  0.05    0.87
Q3    1   0.5647  0.4732  0.5000  10.50000  0.05    0.68
Q4    1   0.0000  0.5000  0.3617  10.50000  0.05    0.59
Q5    1   0.5260  0.1289  0.5000  10.50000  0.05    0.49
Q6    1   0.5000  0.0000  0.5000  10.25000  0.05    0.43
Q7    1  -0.0212  0.3407  0.5658  11.00000  0.05    0.42
Q8    1   0.5247  0.3526  0.5000  10.50000  0.05    0.37
Q9    1  -0.3997  0.4863  0.3024  11.00000  0.05    0.34
Q10   1   0.2787  0.1740  0.3498  11.00000  0.05    0.34
Q11   1  -0.0123  0.2743  0.5000  10.50000  0.05    0.33
Q12   1   0.0616  0.3398  0.5000  10.50000  0.05    0.33
Q13   1  -0.0637  0.2099  0.6813  11.00000  0.05    0.31
Q14   1  -0.0270  0.0506  0.2269  11.00000  0.05    0.30
Q15   1  -0.0183  0.2573  0.2172  11.00000  0.05    0.30
Q16   1  -0.0972  0.2201  0.1769  11.00000  0.05    0.30
Q17   1  -0.2125  0.2552  0.6391  11.00000  0.05    0.29
Q18   1   0.2329  0.2236  0.4524  11.00000  0.05    0.29
Q19   1  -0.3518  0.5600  0.3139  11.00000  0.05    0.29
Q20   1   0.3729  0.2234  0.5000  10.50000  0.05    0.29
;
_shelx_res_checksum              85422
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x, z+1/2'
'-x, -y, z'
'y, -x, z+1/2'
'-x, -y, -z'
'y, -x, -z-1/2'
'x, y, -z'
'-y, x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
I1 I 0.54515(3) 0.25103(4) 0.5000 0.03787(15) Uani 1 2 d S T P
O1 O -0.0913(4) 0.1851(4) 0.5000 0.0342(7) Uani 1 2 d DS T P
C1 C 0.3106(5) 0.2714(5) 0.5000 0.0373(10) Uani 1 2 d S T P
C2 C 0.1724(5) 0.2874(5) 0.5000 0.0334(9) Uani 1 2 d S T P
C3 C 0.0047(5) 0.3267(5) 0.5000 0.0263(8) Uani 1 2 d S T P
C4 C -0.0392(3) 0.4197(3) 0.3584(3) 0.0306(6) Uani 1 1 d . . .
H4A H -0.0069 0.3618 0.2692 0.037 Uiso 1 1 calc R U .
H4B H -0.1523 0.4327 0.3543 0.037 Uiso 1 1 calc R U .
O2 O 0.0000 0.0000 0.2500 0.0417(11) Uani 1 4 d DS T P
H2O H 0.071(7) 0.036(10) 0.201(8) 0.050 Uiso 0.5 1 d D U P
H1O H -0.077(9) 0.142(9) 0.582(5) 0.050 Uiso 0.5 1 d D U P
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.02620(17) 0.0390(2) 0.0484(2) 0.000 0.000 -0.00074(11)
O1 0.0286(15) 0.0304(15) 0.0435(19) 0.000 0.000 -0.0059(13)
C1 0.032(2) 0.036(2) 0.043(2) 0.000 0.000 0.0007(18)
C2 0.032(2) 0.033(2) 0.036(2) 0.000 0.000 -0.0003(16)
C3 0.0290(18) 0.0235(17) 0.0264(19) 0.000 0.000 0.0034(15)
C4 0.0311(14) 0.0340(14) 0.0266(13) -0.0003(12) -0.0007(11) -0.0015(11)
O2 0.0401(16) 0.0401(16) 0.045(3) 0.000 0.000 0.000
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'
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
C1 I1 O1 174.68(15) . 1_655
C3 O1 H1O 107(6) . .
C2 C1 I1 178.4(4) . .
C1 C2 C3 173.4(5) . .
O1 C3 C2 111.0(3) . .
O1 C3 C4 107.0(2) . .
C2 C3 C4 110.9(2) . .
O1 C3 C4 107.0(2) . 7_556
C2 C3 C4 110.9(2) . 7_556
C4 C3 C4 110.0(3) . 7_556
C4 C4 C3 111.0(2) 3_565 .
C4 C4 H4A 109.4 3_565 .
C3 C4 H4A 109.4 . .
C4 C4 H4B 109.4 3_565 .
C3 C4 H4B 109.4 . .
H4A C4 H4B 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C1 2.005(5) .
I1 O1 3.146(3) 1_655
O1 C3 1.457(5) .
O1 H1O 0.83(2) .
C1 C2 1.184(6) .
C2 C3 1.467(6) .
C3 C4 1.528(4) .
C3 C4 1.528(4) 7_556
C4 C4 1.522(6) 3_565
C4 H4A 0.9700 .
C4 H4B 0.9700 .
O2 H2O 0.802(19) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4B I1 0.97 3.27 4.020(3) 135.5 1_455
O2 H2O O1 0.802(19) 2.08(4) 2.8239(19) 154(8) 6_556
O1 H1O O2 0.83(2) 2.02(3) 2.8239(19) 164(8) 5_556
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_4
O1 C3 C4 C4 172.5(3) . 3_565
C2 C3 C4 C4 -66.3(4) . 3_565
C4 C3 C4 C4 56.7(4) 7_556 3_565
