data_tw4
_audit_creation_date              2017-07-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number      '2017/1'
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_id_orcid     ?
_publ_contact_author_name
;

;
_publ_contact_author_phone        ?
_publ_section_references
;
?

Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.
;
_chemical_name_common             ?
_chemical_name_systematic         ?
_chemical_formula_moiety          'C11 H8 Br I O3'
_chemical_formula_sum             'C11 H8 Br I O3'
_chemical_formula_weight          394.98
_chemical_melting_point           ?
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'
 'Br' 'Br' -0.2901 2.4595
 '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'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system       'monoclinic'
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 1 21/c 1'
_space_group_name_Hall            '-P 2ybc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'

_cell_length_a                    10.8432(7)
_cell_length_b                    9.2630(6)
_cell_length_c                    11.9112(8)
_cell_angle_alpha                 90
_cell_angle_beta                  108.277(2)
_cell_angle_gamma                 90
_cell_volume                      1136.01(13)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     7971
_cell_measurement_temperature     100(2)
_cell_measurement_theta_max       26.91
_cell_measurement_theta_min       2.84
_shelx_estimated_absorpt_T_max    0.632
_shelx_estimated_absorpt_T_min    0.396
_exptl_absorpt_coefficient_mu     6.324
_exptl_absorpt_correction_T_max   0.745
_exptl_absorpt_correction_T_min   0.608
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0832 before and 0.0514 after correction.

For component 2:
 wR2(int) was 0.0835 before and 0.0512 after correction.

Final HKLF 4 output contains 25787 reflections, Rint = 0.0547
 (15006 with I > 3sig(I), Rint = 0.0391)
;
_exptl_absorpt_special_details    ?
_exptl_crystal_colour             colourless
_exptl_crystal_colour_primary     colourless
_exptl_crystal_density_diffrn     2.309
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        block
_exptl_crystal_F_000              744
_exptl_crystal_size_max           0.18
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.08
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0547
_diffrn_reflns_av_unetI/netI      0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.742
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_k_min        0
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_limit_l_min        0
_diffrn_reflns_number             3906
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.742
_diffrn_reflns_theta_full         25.242
_diffrn_reflns_theta_max          30.104
_diffrn_reflns_theta_min          2.842
_diffrn_ambient_temperature       100(2)
_diffrn_detector                  'Bruker PHOTON 100'
_diffrn_detector_area_resol_mean  10.4167
_diffrn_detector_type             CMOS
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.742
_diffrn_measurement_device        'three-circle diffractometer'
_diffrn_measurement_device_type   D8Venture
_diffrn_measurement_method        'φ and ω scans'
_diffrn_radiation_monochromator   mirrors
_diffrn_radiation_probe           x-ray
_diffrn_radiation_type            MoK\a
_diffrn_radiation_wavelength      0.71073
_diffrn_source                    'micro-focus X-ray tube'
_diffrn_source_type               'INCOATEC ImuS'
_diffrn_standards_number          0
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_full     .
_reflns_Friedel_fraction_max      .
_reflns_number_gt                 3331
_reflns_number_total              3906
_reflns_special_details
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression      'I > 2σ(I)'
_computing_cell_refinement        'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection        'APEX3 v.2015.9-0 (Bruker AXS Inc., 2015)'
_computing_data_reduction         'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics
;
OLEX2: a complete structure solution, refinement and analysis program 
Dolomanov et al., 2009

Mercury: visualization and analysis of crystal structures
Macrae, et al., 2006

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann.
J. Appl. Cryst. (2009). 42, 339-341;

C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst. (2006). 39, 453-457.
;
_computing_publication_material
;
 APEX3 v.2015.5-2 (Bruker AXS Inc., 2015)
 OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement   'XL-2014/7 (Sheldrick, 2015b)'
_computing_structure_solution     'XT 2014/5 (Sheldrick, 2015a)'
_refine_diff_density_max          0.818
_refine_diff_density_min          -0.718
_refine_diff_density_rms          0.171
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.037
_refine_ls_hydrogen_treatment     mixed
_refine_ls_matrix_type            full
_refine_ls_number_parameters      149
_refine_ls_number_reflns          3906
_refine_ls_number_restraints      7
_refine_ls_R_factor_all           0.0506
_refine_ls_R_factor_gt            0.0357
_refine_ls_restrained_S_all       1.037
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0238P)²+3.0665P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.0627
_refine_ls_wR_factor_ref          0.0666
_refine_special_details
;
 Refined as a 2-component twin.
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5611(8)
 0.4389(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
3. Restrained distances
 O2-H2
 0.84 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C3) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
5.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C9(H9)
5.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C7(H7)
;
_atom_sites_solution_hydrogens    mixed
_atom_sites_solution_primary      dual
_atom_sites_solution_secondary    difmap
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
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 I1 I 0.95131(3) 0.32736(4) 0.24657(3) 0.02326(11) Uani 1 1 d . . . . .
 Br1 Br 0.83205(5) 0.93856(5) 0.45238(5) 0.02170(14) Uani 1 1 d . . . . .
 O1 O 0.5891(3) 0.6647(4) 0.0417(3) 0.0196(8) Uani 1 1 d . . . . .
 O2 O 0.4942(3) 0.4891(4) 0.1913(3) 0.0184(8) Uani 1 1 d D . . . .
 H2 H 0.482(6) 0.467(6) 0.120(3) 0.028 Uiso 1 1 d DR . . . .
 O3 O 0.6495(3) 0.3809(4) 0.5453(4) 0.0233(9) Uani 1 1 d . . . . .
 C1 C 0.7481(4) 0.7826(5) 0.3545(5) 0.0145(11) Uani 1 1 d . . . . .
 C2 C 0.6863(4) 0.7947(5) 0.2300(5) 0.0144(11) Uani 1 1 d . . . . .
 H2A H 0.682093 0.885666 0.192181 0.017 Uiso 1 1 calc R . . . .
 C3 C 0.6290(4) 0.6659(5) 0.1597(4) 0.0115(10) Uani 1 1 d . U . . .
 C4 C 0.6143(4) 0.5336(5) 0.2377(5) 0.0156(11) Uani 1 1 d . . . . .
 C5 C 0.6434(4) 0.5616(5) 0.3818(5) 0.0152(11) Uani 1 1 d . . . . .
 H5 H 0.570921 0.617872 0.395945 0.018 Uiso 1 1 calc R . . . .
 C6 C 0.7632(4) 0.6397(5) 0.4246(5) 0.0144(11) Uani 1 1 d . . . . .
 H6 H 0.791927 0.654484 0.512148 0.017 Uiso 1 1 calc R . . . .
 C7 C 0.8563(4) 0.5541(5) 0.3845(5) 0.0176(12) Uani 1 1 d . . . . .
 H7 H 0.946058 0.570865 0.423296 0.021 Uiso 1 1 calc R . . . .
 C8 C 0.8250(4) 0.4524(5) 0.2962(5) 0.0169(11) Uani 1 1 d . . . . .
 C9 C 0.6967(4) 0.4042(5) 0.2378(5) 0.0161(11) Uani 1 1 d . . . . .
 H9 H 0.682672 0.356924 0.159322 0.019 Uiso 1 1 calc R . . . .
 C10 C 0.6699(5) 0.3037(5) 0.3391(5) 0.0216(13) Uani 1 1 d . . . . .
 H10A H 0.590105 0.245792 0.305384 0.026 Uiso 1 1 calc R . . . .
 H10B H 0.743698 0.236991 0.372531 0.026 Uiso 1 1 calc R . . . .
 C11 C 0.6536(4) 0.4094(5) 0.4392(5) 0.0174(12) Uani 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C8 2.018(5) . ?
 Br1 C1 1.899(5) . ?
 O1 C3 1.335(6) . ?
 O2 H2 0.85(2) . ?
 O2 C4 1.311(5) . ?
 O3 C11 1.306(7) . ?
 C1 C2 1.428(7) . ?
 C1 C6 1.546(7) . ?
 C2 H2A 0.9500 . ?
 C2 C3 1.478(7) . ?
 C3 C4 1.575(7) . ?
 C4 C5 1.666(7) . ?
 C4 C9 1.495(6) . ?
 C5 H5 1.0000 . ?
 C5 C6 1.434(6) . ?
 C5 C11 1.555(7) . ?
 C6 H6 1.0000 . ?
 C6 C7 1.476(7) . ?
 C7 H7 0.9500 . ?
 C7 C8 1.373(7) . ?
 C8 C9 1.418(6) . ?
 C9 H9 1.0000 . ?
 C9 C10 1.620(7) . ?
 C10 H10A 0.9900 . ?
 C10 H10B 0.9900 . ?
 C10 C11 1.595(8) . ?

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
 C4 O2 H2 108(4) . . ?
 C2 C1 Br1 123.8(4) . . ?
 C2 C1 C6 124.3(4) . . ?
 C6 C1 Br1 111.8(4) . . ?
 C1 C2 H2A 119.9 . . ?
 C1 C2 C3 120.2(4) . . ?
 C3 C2 H2A 119.9 . . ?
 O1 C3 C2 122.9(4) . . ?
 O1 C3 C4 123.7(4) . . ?
 C2 C3 C4 113.4(4) . . ?
 O2 C4 C3 105.5(4) . . ?
 O2 C4 C5 109.0(4) . . ?
 O2 C4 C9 105.2(4) . . ?
 C3 C4 C5 117.7(4) . . ?
 C9 C4 C3 117.0(4) . . ?
 C9 C4 C5 101.8(4) . . ?
 C4 C5 H5 110.5 . . ?
 C6 C5 C4 107.6(4) . . ?
 C6 C5 H5 110.5 . . ?
 C6 C5 C11 111.7(4) . . ?
 C11 C5 C4 106.0(4) . . ?
 C11 C5 H5 110.5 . . ?
 C1 C6 H6 113.0 . . ?
 C5 C6 C1 108.0(4) . . ?
 C5 C6 H6 113.0 . . ?
 C5 C6 C7 104.5(4) . . ?
 C7 C6 C1 104.7(4) . . ?
 C7 C6 H6 113.0 . . ?
 C6 C7 H7 117.0 . . ?
 C8 C7 C6 125.9(4) . . ?
 C8 C7 H7 117.0 . . ?
 C7 C8 I1 126.2(3) . . ?
 C7 C8 C9 124.1(5) . . ?
 C9 C8 I1 109.1(4) . . ?
 C4 C9 H9 115.7 . . ?
 C4 C9 C10 102.4(4) . . ?
 C8 C9 C4 104.0(4) . . ?
 C8 C9 H9 115.7 . . ?
 C8 C9 C10 101.2(4) . . ?
 C10 C9 H9 115.7 . . ?
 C9 C10 H10A 110.3 . . ?
 C9 C10 H10B 110.3 . . ?
 H10A C10 H10B 108.6 . . ?
 C11 C10 C9 106.9(4) . . ?
 C11 C10 H10A 110.3 . . ?
 C11 C10 H10B 110.3 . . ?
 O3 C11 C5 126.1(5) . . ?
 O3 C11 C10 130.1(4) . . ?
 C5 C11 C10 103.8(4) . . ?

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
  _geom_hbond_publ_flag
 O2 H2 O1 0.85(2) 2.20(3) 2.996(5) 156(6) 3_665 yes

_olex2_submission_special_instructions 'No special instructions were received'
loop_
  _twin_individual_id
  _twin_individual_mass_fraction_refined
 1 0.5611(8)
 2 0.4389(8)

