# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_gj64
_database_code_depnum_ccdc_archive 'CCDC 1441683'
_audit_update_record             
;
2015-12-10 deposited with the CCDC.
2016-02-19 downloaded from the CCDC.
;
_audit_creation_date             2015-09-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H23 O5 Rh'
_chemical_formula_sum            'C14 H23 O5 Rh'
_chemical_formula_weight         374.23
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Rh Rh -1.1178 0.9187 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.2023(3)
_cell_length_b                   13.3209(4)
_cell_length_c                   16.1663(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.426(2)
_cell_angle_gamma                90
_cell_volume                     1548.24(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3053
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.18
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.118
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0844 before and 0.0620 after correction.
The Ratio of minimum to maximum transmission is 0.8281.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3802
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.991
_diffrn_reflns_theta_min         1.982
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3354
_reflns_number_total             3802
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.811
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3802
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0278
_refine_ls_restrained_S_all      1.037
_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)+(0.0149P)²+1.1910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0463
_refine_ls_wR_factor_ref         0.0487
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5276(6) 0.4724(6)
2. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 O5-H5B \\sim O5-H5A
 with sigma of 0.01
4.a Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,
 H10B,H10C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
Rh1 Rh 0.59554(3) 0.12507(2) 0.26825(2) 0.01391(5) Uani 1 1 d . . . . .
O1 O 0.4210(3) 0.07512(14) 0.36011(13) 0.0212(4) Uani 1 1 d . . . . .
O2 O 0.5097(3) -0.08543(14) 0.37714(12) 0.0236(5) Uani 1 1 d . . . . .
O3 O 0.3943(3) 0.06091(14) 0.18308(13) 0.0206(4) Uani 1 1 d . . . . .
O4 O 0.5758(3) -0.05377(16) 0.12679(13) 0.0292(5) Uani 1 1 d . . . . .
O5 O 0.7380(3) -0.01817(15) 0.27333(17) 0.0232(5) Uani 1 1 d D . . . .
C1 C 0.6611(4) 0.26161(19) 0.33245(17) 0.0123(5) Uani 1 1 d . . . . .
C2 C 0.8275(4) 0.2147(2) 0.30871(17) 0.0149(6) Uani 1 1 d . . . . .
C3 C 0.8169(4) 0.20679(19) 0.21927(18) 0.0161(6) Uani 1 1 d . . . . .
C4 C 0.6445(4) 0.24891(19) 0.18902(17) 0.0144(5) Uani 1 1 d . . . . .
C5 C 0.5443(4) 0.28136(18) 0.25884(17) 0.0139(6) Uani 1 1 d . . . . .
C6 C 0.6108(4) 0.2841(2) 0.41860(17) 0.0197(6) Uani 1 1 d . . . . .
H6A H 0.7070 0.2575 0.4581 0.030 Uiso 1 1 calc GR . . . .
H6B H 0.4911 0.2528 0.4286 0.030 Uiso 1 1 calc GR . . . .
H6C H 0.6012 0.3570 0.4258 0.030 Uiso 1 1 calc GR . . . .
C7 C 0.9866(4) 0.1823(2) 0.36632(19) 0.0234(7) Uani 1 1 d . . . . .
H7A H 1.0714 0.1402 0.3362 0.035 Uiso 1 1 calc GR . . . .
H7B H 0.9392 0.1439 0.4122 0.035 Uiso 1 1 calc GR . . . .
H7C H 1.0535 0.2416 0.3882 0.035 Uiso 1 1 calc GR . . . .
C8 C 0.9602(4) 0.1628(2) 0.16647(19) 0.0230(7) Uani 1 1 d . . . . .
H8A H 0.9000 0.1162 0.1263 0.034 Uiso 1 1 calc GR . . . .
H8B H 1.0533 0.1266 0.2016 0.034 Uiso 1 1 calc GR . . . .
H8C H 1.0209 0.2167 0.1369 0.034 Uiso 1 1 calc GR . . . .
C9 C 0.5774(4) 0.2562(2) 0.10014(17) 0.0216(6) Uani 1 1 d . . . . .
H9A H 0.4413 0.2525 0.0957 0.032 Uiso 1 1 calc GR . . . .
H9B H 0.6291 0.2007 0.0691 0.032 Uiso 1 1 calc GR . . . .
H9C H 0.6176 0.3202 0.0773 0.032 Uiso 1 1 calc GR . . . .
C10 C 0.3623(4) 0.3351(2) 0.25562(18) 0.0188(6) Uani 1 1 d . . . . .
H10A H 0.2952 0.3178 0.3046 0.028 Uiso 1 1 calc GR . . . .
H10B H 0.2880 0.3152 0.2055 0.028 Uiso 1 1 calc GR . . . .
H10C H 0.3840 0.4077 0.2546 0.028 Uiso 1 1 calc GR . . . .
C11 C 0.4089(4) -0.0126(2) 0.39156(18) 0.0182(6) Uani 1 1 d . . . . .
C12 C 0.2588(4) -0.0242(2) 0.45179(19) 0.0244(7) Uani 1 1 d . . . . .
H12A H 0.1393 -0.0362 0.4212 0.037 Uiso 1 1 calc GR . . . .
H12B H 0.2510 0.0371 0.4848 0.037 Uiso 1 1 calc GR . . . .
H12C H 0.2885 -0.0813 0.4885 0.037 Uiso 1 1 calc GR . . . .
C13 C 0.4292(4) -0.0052(2) 0.12895(18) 0.0186(7) Uani 1 1 d . . . . .
C14 C 0.2778(4) -0.0216(2) 0.06162(18) 0.0240(7) Uani 1 1 d . . . . .
H14A H 0.3092 0.0143 0.0114 0.036 Uiso 1 1 calc GR . . . .
H14B H 0.1595 0.0038 0.0802 0.036 Uiso 1 1 calc GR . . . .
H14C H 0.2663 -0.0935 0.0496 0.036 Uiso 1 1 calc GR . . . .
H5A H 0.665(5) -0.049(3) 0.306(2) 0.045(12) Uiso 1 1 d D . . . .
H5B H 0.705(5) -0.034(3) 0.2226(15) 0.042(13) Uiso 1 1 d 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
Rh1 O1 2.110(2) . ?
Rh1 O3 2.119(2) . ?
Rh1 O5 2.166(2) . ?
Rh1 C1 2.133(3) . ?
Rh1 C2 2.125(3) . ?
Rh1 C3 2.123(3) . ?
Rh1 C4 2.131(3) . ?
Rh1 C5 2.118(2) . ?
O1 C11 1.279(3) . ?
O2 C11 1.242(3) . ?
O3 C13 1.277(3) . ?
O4 C13 1.241(3) . ?
O5 H5A 0.87(2) . ?
O5 H5B 0.87(2) . ?
C1 C2 1.424(4) . ?
C1 C5 1.440(4) . ?
C1 C6 1.490(4) . ?
C2 C3 1.447(4) . ?
C2 C7 1.497(4) . ?
C3 C4 1.422(4) . ?
C3 C8 1.497(4) . ?
C4 C5 1.442(4) . ?
C4 C9 1.491(4) . ?
C5 C10 1.492(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.505(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.510(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
O1 Rh1 O3 85.24(8) . . ?
O1 Rh1 O5 89.79(8) . . ?
O1 Rh1 C1 92.89(9) . . ?
O1 Rh1 C2 116.81(10) . . ?
O1 Rh1 C3 156.46(10) . . ?
O1 Rh1 C4 142.59(9) . . ?
O1 Rh1 C5 104.60(9) . . ?
O3 Rh1 O5 88.48(8) . . ?
O3 Rh1 C1 141.55(9) . . ?
O3 Rh1 C2 157.16(9) . . ?
O3 Rh1 C3 117.68(10) . . ?
O3 Rh1 C4 93.04(9) . . ?
C1 Rh1 O5 129.95(10) . . ?
C2 Rh1 O5 96.98(10) . . ?
C2 Rh1 C1 39.07(10) . . ?
C2 Rh1 C4 66.07(11) . . ?
C3 Rh1 O5 95.80(9) . . ?
C3 Rh1 C1 66.10(10) . . ?
C3 Rh1 C2 39.85(10) . . ?
C3 Rh1 C4 39.07(11) . . ?
C4 Rh1 O5 127.57(10) . . ?
C4 Rh1 C1 65.96(10) . . ?
C5 Rh1 O3 103.91(9) . . ?
C5 Rh1 O5 161.57(9) . . ?
C5 Rh1 C1 39.59(10) . . ?
C5 Rh1 C2 66.42(10) . . ?
C5 Rh1 C3 66.47(10) . . ?
C5 Rh1 C4 39.68(10) . . ?
C11 O1 Rh1 128.7(2) . . ?
C13 O3 Rh1 124.63(19) . . ?
Rh1 O5 H5A 98(3) . . ?
Rh1 O5 H5B 95(3) . . ?
H5A O5 H5B 108(3) . . ?
C2 C1 Rh1 70.15(15) . . ?
C2 C1 C5 108.5(2) . . ?
C2 C1 C6 126.6(3) . . ?
C5 C1 Rh1 69.65(14) . . ?
C5 C1 C6 124.9(3) . . ?
C6 C1 Rh1 124.56(19) . . ?
C1 C2 Rh1 70.78(15) . . ?
C1 C2 C3 107.9(2) . . ?
C1 C2 C7 125.8(3) . . ?
C3 C2 Rh1 70.00(16) . . ?
C3 C2 C7 126.4(3) . . ?
C7 C2 Rh1 126.0(2) . . ?
C2 C3 Rh1 70.15(15) . . ?
C2 C3 C8 127.0(3) . . ?
C4 C3 Rh1 70.78(15) . . ?
C4 C3 C2 107.9(2) . . ?
C4 C3 C8 125.1(3) . . ?
C8 C3 Rh1 124.77(19) . . ?
C3 C4 Rh1 70.15(15) . . ?
C3 C4 C5 108.5(2) . . ?
C3 C4 C9 125.7(3) . . ?
C5 C4 Rh1 69.69(14) . . ?
C5 C4 C9 125.9(3) . . ?
C9 C4 Rh1 125.00(19) . . ?
C1 C5 Rh1 70.76(14) . . ?
C1 C5 C4 107.3(2) . . ?
C1 C5 C10 125.8(2) . . ?
C4 C5 Rh1 70.64(14) . . ?
C4 C5 C10 126.6(3) . . ?
C10 C5 Rh1 128.56(19) . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C11 C12 114.9(3) . . ?
O2 C11 O1 125.7(3) . . ?
O2 C11 C12 119.4(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 C14 115.5(3) . . ?
O4 C13 O3 125.6(3) . . ?
O4 C13 C14 118.9(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
O5 H5A O2 0.87(2) 1.72(2) 2.580(3) 168(4) .
O5 H5B O4 0.87(2) 1.78(2) 2.621(3) 164(4) .

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
Rh1 O1 C11 O2 5.1(4) . . . . ?
Rh1 O1 C11 C12 -175.71(19) . . . . ?
Rh1 O3 C13 O4 12.9(4) . . . . ?
Rh1 O3 C13 C14 -165.44(18) . . . . ?
Rh1 C1 C2 C3 60.47(18) . . . . ?
Rh1 C1 C2 C7 -121.1(3) . . . . ?
Rh1 C1 C5 C4 -61.55(17) . . . . ?
Rh1 C1 C5 C10 124.2(3) . . . . ?
Rh1 C2 C3 C4 61.04(18) . . . . ?
Rh1 C2 C3 C8 -119.2(3) . . . . ?
Rh1 C3 C4 C5 59.36(18) . . . . ?
Rh1 C3 C4 C9 -119.4(3) . . . . ?
Rh1 C4 C5 C1 61.63(17) . . . . ?
Rh1 C4 C5 C10 -124.2(3) . . . . ?
C1 C2 C3 Rh1 -60.96(18) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C1 C2 C3 C8 179.9(2) . . . . ?
C2 C1 C5 Rh1 59.62(18) . . . . ?
C2 C1 C5 C4 -1.9(3) . . . . ?
C2 C1 C5 C10 -176.2(2) . . . . ?
C2 C3 C4 Rh1 -60.64(18) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C2 C3 C4 C9 179.9(3) . . . . ?
C3 C4 C5 Rh1 -59.65(18) . . . . ?
C3 C4 C5 C1 2.0(3) . . . . ?
C3 C4 C5 C10 176.2(2) . . . . ?
C5 C1 C2 Rh1 -59.31(18) . . . . ?
C5 C1 C2 C3 1.2(3) . . . . ?
C5 C1 C2 C7 179.6(3) . . . . ?
C6 C1 C2 Rh1 118.9(3) . . . . ?
C6 C1 C2 C3 179.4(3) . . . . ?
C6 C1 C2 C7 -2.2(4) . . . . ?
C6 C1 C5 Rh1 -118.6(3) . . . . ?
C6 C1 C5 C4 179.8(2) . . . . ?
C6 C1 C5 C10 5.6(4) . . . . ?
C7 C2 C3 Rh1 120.6(3) . . . . ?
C7 C2 C3 C4 -178.4(3) . . . . ?
C7 C2 C3 C8 1.4(5) . . . . ?
C8 C3 C4 Rh1 119.5(3) . . . . ?
C8 C3 C4 C5 178.9(2) . . . . ?
C8 C3 C4 C9 0.1(4) . . . . ?
C9 C4 C5 Rh1 119.2(3) . . . . ?
C9 C4 C5 C1 -179.2(3) . . . . ?
C9 C4 C5 C10 -5.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.5276(6)
2 0.4724(6)

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_testr1
_database_code_depnum_ccdc_archive 'CCDC 1441684'
_audit_update_record             
;
2015-12-10 deposited with the CCDC.
2016-02-19 downloaded from the CCDC.
;
_audit_creation_date             2015-06-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H24 Cl4 F6 Rh2'
_chemical_formula_sum            'C20 H24 Cl4 F6 Rh2'
_chemical_formula_weight         726.01
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Rh Rh -1.1178 0.9187 '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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   28.1638(9)
_cell_length_b                   28.1638(9)
_cell_length_c                   8.1635(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     5607.7(4)
_cell_formula_units_Z            9
_cell_measurement_reflns_used    2440
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.49
_cell_measurement_theta_min      2.50
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.805
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1418 before and 0.0785 after correction.
The Ratio of minimum to maximum transmission is 0.7677.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.935
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3204
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.098
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_av_unetI/netI     0.1233
_diffrn_reflns_Laue_measured_fraction_full 0.868
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13326
_diffrn_reflns_point_group_measured_fraction_full 0.868
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.949
_diffrn_reflns_theta_min         2.505
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.868
_diffrn_measured_fraction_theta_max 0.889
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1778
_reflns_number_total             2667
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.611
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2667
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      0.611
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0491
_refine_ls_wR_factor_ref         0.0532
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
Rh1 Rh 0.94033(2) 0.47647(2) 0.13046(3) 0.01354(8) Uani 1 1 d . . . . .
Cl1 Cl 1.03974(4) 0.53262(4) 0.15371(10) 0.0159(2) Uani 1 1 d . . . . .
Cl2 Cl 0.94502(4) 0.39711(4) 0.19822(12) 0.0230(2) Uani 1 1 d . . . . .
C7 C 0.87909(18) 0.52375(17) -0.1032(5) 0.0276(10) Uani 1 1 d . . . . .
H7A H 0.9145 0.5498 -0.1519 0.041 Uiso 1 1 calc GR . . . .
H7B H 0.8561 0.5407 -0.0962 0.041 Uiso 1 1 calc GR . . . .
H7C H 0.8608 0.4908 -0.1717 0.041 Uiso 1 1 calc GR . . . .
C2 C 0.88786(16) 0.50850(16) 0.0634(5) 0.0176(9) Uani 1 1 d . . . . .
C1 C 0.85851(16) 0.45539(17) 0.1438(5) 0.0228(10) Uani 1 1 d . . . . .
C4 C 0.92236(16) 0.51532(16) 0.3275(5) 0.0173(9) Uani 1 1 d . . . . .
C5 C 0.87841(17) 0.46067(16) 0.3110(5) 0.0222(10) Uani 1 1 d . . . . .
C3 C 0.92757(16) 0.54464(15) 0.1778(4) 0.0146(8) Uani 1 1 d . . . . .
F2 F 0.81519(12) 0.39984(12) -0.0862(4) 0.0670(10) Uani 1 1 d . . . . .
C9 C 0.95765(17) 0.54056(17) 0.4758(4) 0.0252(10) Uani 1 1 d . . . . .
H9A H 0.9541 0.5115 0.5495 0.038 Uiso 1 1 calc GR . . . .
H9B H 0.9459 0.5635 0.5328 0.038 Uiso 1 1 calc GR . . . .
H9C H 0.9960 0.5631 0.4419 0.038 Uiso 1 1 calc GR . . . .
C8 C 0.96869(16) 0.60366(16) 0.1484(5) 0.0211(9) Uani 1 1 d . . . . .
H8A H 1.0032 0.6128 0.2029 0.032 Uiso 1 1 calc GR . . . .
H8B H 0.9548 0.6267 0.1925 0.032 Uiso 1 1 calc GR . . . .
H8C H 0.9750 0.6102 0.0304 0.032 Uiso 1 1 calc GR . . . .
F1 F 0.80039(13) 0.35982(12) 0.1441(4) 0.0775(11) Uani 1 1 d . . . . .
C10 C 0.85807(18) 0.41763(17) 0.4410(5) 0.0347(12) Uani 1 1 d . . . . .
H10A H 0.8210 0.4086 0.4741 0.052 Uiso 1 1 calc GR . . . .
H10B H 0.8826 0.4313 0.5359 0.052 Uiso 1 1 calc GR . . . .
H10C H 0.8572 0.3847 0.3983 0.052 Uiso 1 1 calc GR . . . .
C6 C 0.80979(19) 0.4061(2) 0.0751(7) 0.0422(14) Uani 1 1 d . . . . .
F3 F 0.76518(11) 0.40900(13) 0.0843(5) 0.0816(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
Rh1 Cl1 2.4302(9) 10_765 ?
Rh1 Cl1 2.4387(10) . ?
Rh1 Cl2 2.3694(10) . ?
Rh1 C2 2.152(4) . ?
Rh1 C1 2.075(4) . ?
Rh1 C4 2.143(4) . ?
Rh1 C5 2.153(4) . ?
Rh1 C3 2.157(4) . ?
Cl1 Rh1 2.4302(9) 10_765 ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 C2 1.484(5) . ?
C2 C1 1.454(5) . ?
C2 C3 1.421(5) . ?
C1 C5 1.455(5) . ?
C1 C6 1.490(6) . ?
C4 C5 1.419(5) . ?
C4 C3 1.440(5) . ?
C4 C9 1.501(5) . ?
C5 C10 1.493(5) . ?
C3 C8 1.496(5) . ?
F2 C6 1.347(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
F1 C6 1.319(6) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C6 F3 1.302(5) . ?

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
Cl1 Rh1 Cl1 83.79(3) 10_765 . ?
Cl2 Rh1 Cl1 90.36(3) . . ?
Cl2 Rh1 Cl1 89.92(3) . 10_765 ?
C2 Rh1 Cl1 123.66(11) . . ?
C2 Rh1 Cl1 92.55(10) . 10_765 ?
C2 Rh1 Cl2 145.96(11) . . ?
C2 Rh1 C5 66.79(14) . . ?
C2 Rh1 C3 38.53(14) . . ?
C1 Rh1 Cl1 107.58(12) . 10_765 ?
C1 Rh1 Cl1 158.74(11) . . ?
C1 Rh1 Cl2 107.19(12) . . ?
C1 Rh1 C2 40.20(14) . . ?
C1 Rh1 C4 66.09(15) . . ?
C1 Rh1 C5 40.19(15) . . ?
C1 Rh1 C3 65.79(15) . . ?
C4 Rh1 Cl1 153.65(10) . 10_765 ?
C4 Rh1 Cl1 95.63(11) . . ?
C4 Rh1 Cl2 116.43(10) . . ?
C4 Rh1 C2 65.80(14) . . ?
C4 Rh1 C5 38.58(14) . . ?
C4 Rh1 C3 39.14(13) . . ?
C5 Rh1 Cl1 146.89(12) . 10_765 ?
C5 Rh1 Cl1 129.00(12) . . ?
C5 Rh1 Cl2 93.81(11) . . ?
C5 Rh1 C3 65.37(14) . . ?
C3 Rh1 Cl1 93.27(11) . . ?
C3 Rh1 Cl1 114.51(9) . 10_765 ?
C3 Rh1 Cl2 155.55(10) . . ?
Rh1 Cl1 Rh1 96.21(3) 10_765 . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
C7 C2 Rh1 127.1(3) . . ?
C1 C2 Rh1 67.1(2) . . ?
C1 C2 C7 128.3(4) . . ?
C3 C2 Rh1 70.9(2) . . ?
C3 C2 C7 125.5(4) . . ?
C3 C2 C1 106.2(3) . . ?
C2 C1 Rh1 72.7(2) . . ?
C2 C1 C6 125.0(4) . . ?
C5 C1 Rh1 72.8(2) . . ?
C5 C1 C2 109.1(4) . . ?
C5 C1 C6 125.2(4) . . ?
C6 C1 Rh1 128.3(3) . . ?
C5 C4 Rh1 71.1(2) . . ?
C5 C4 C3 109.0(3) . . ?
C5 C4 C9 127.0(4) . . ?
C3 C4 Rh1 71.0(2) . . ?
C3 C4 C9 124.0(3) . . ?
C9 C4 Rh1 125.3(3) . . ?
C1 C5 Rh1 67.0(2) . . ?
C1 C5 C10 127.7(4) . . ?
C4 C5 Rh1 70.3(2) . . ?
C4 C5 C1 106.4(3) . . ?
C4 C5 C10 125.9(4) . . ?
C10 C5 Rh1 126.6(3) . . ?
C2 C3 Rh1 70.5(2) . . ?
C2 C3 C4 109.2(3) . . ?
C2 C3 C8 125.8(3) . . ?
C4 C3 Rh1 69.9(2) . . ?
C4 C3 C8 125.0(3) . . ?
C8 C3 Rh1 125.4(3) . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
F2 C6 C1 112.2(4) . . ?
F1 C6 C1 113.4(5) . . ?
F1 C6 F2 105.6(4) . . ?
F3 C6 C1 112.8(4) . . ?
F3 C6 F2 103.9(5) . . ?
F3 C6 F1 108.3(4) . . ?

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
Rh1 C2 C1 C5 64.2(3) . . . . ?
Rh1 C2 C1 C6 -125.1(4) . . . . ?
Rh1 C2 C3 C4 -59.4(3) . . . . ?
Rh1 C2 C3 C8 120.2(4) . . . . ?
Rh1 C1 C5 C4 59.6(3) . . . . ?
Rh1 C1 C5 C10 -119.5(4) . . . . ?
Rh1 C1 C6 F2 -53.7(6) . . . . ?
Rh1 C1 C6 F1 65.8(6) . . . . ?
Rh1 C1 C6 F3 -170.6(3) . . . . ?
Rh1 C4 C5 C1 -57.5(3) . . . . ?
Rh1 C4 C5 C10 121.6(4) . . . . ?
Rh1 C4 C3 C2 59.8(3) . . . . ?
Rh1 C4 C3 C8 -119.8(4) . . . . ?
C7 C2 C1 Rh1 120.0(4) . . . . ?
C7 C2 C1 C5 -175.8(4) . . . . ?
C7 C2 C1 C6 -5.0(6) . . . . ?
C7 C2 C3 Rh1 -122.5(4) . . . . ?
C7 C2 C3 C4 178.1(3) . . . . ?
C7 C2 C3 C8 -2.3(6) . . . . ?
C2 C1 C5 Rh1 -64.1(3) . . . . ?
C2 C1 C5 C4 -4.5(4) . . . . ?
C2 C1 C5 C10 176.4(4) . . . . ?
C2 C1 C6 F2 41.5(6) . . . . ?
C2 C1 C6 F1 161.1(4) . . . . ?
C2 C1 C6 F3 -75.4(6) . . . . ?
C1 C2 C3 Rh1 58.0(2) . . . . ?
C1 C2 C3 C4 -1.4(4) . . . . ?
C1 C2 C3 C8 178.2(4) . . . . ?
C5 C1 C6 F2 -149.2(4) . . . . ?
C5 C1 C6 F1 -29.7(6) . . . . ?
C5 C1 C6 F3 93.9(6) . . . . ?
C5 C4 C3 Rh1 -61.2(3) . . . . ?
C5 C4 C3 C2 -1.4(4) . . . . ?
C5 C4 C3 C8 179.0(3) . . . . ?
C3 C2 C1 Rh1 -60.5(2) . . . . ?
C3 C2 C1 C5 3.6(4) . . . . ?
C3 C2 C1 C6 174.4(4) . . . . ?
C3 C4 C5 Rh1 61.1(3) . . . . ?
C3 C4 C5 C1 3.6(4) . . . . ?
C3 C4 C5 C10 -177.3(3) . . . . ?
C9 C4 C5 Rh1 -120.4(4) . . . . ?
C9 C4 C5 C1 -177.9(4) . . . . ?
C9 C4 C5 C10 1.2(6) . . . . ?
C9 C4 C3 Rh1 120.3(4) . . . . ?
C9 C4 C3 C2 -179.9(3) . . . . ?
C9 C4 C3 C8 0.5(6) . . . . ?
C6 C1 C5 Rh1 125.1(4) . . . . ?
C6 C1 C5 C4 -175.2(4) . . . . ?
C6 C1 C5 C10 5.7(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_testt1
_database_code_depnum_ccdc_archive 'CCDC 1441685'
_audit_update_record             
;
2015-12-10 deposited with the CCDC.
2016-02-19 downloaded from the CCDC.
;
_audit_creation_date             2015-06-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H38 Cl4 Rh2'
_chemical_formula_sum            'C24 H38 Cl4 Rh2'
_chemical_formula_weight         674.16
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Rh Rh -1.1178 0.9187 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2993(2)
_cell_length_b                   8.9088(2)
_cell_length_c                   9.3961(2)
_cell_angle_alpha                102.3346(11)
_cell_angle_beta                 106.6075(11)
_cell_angle_gamma                94.5603(11)
_cell_volume                     643.00(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    8108
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.94
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.709
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0457 before and 0.0312 after correction.
The Ratio of minimum to maximum transmission is 0.8629.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11847
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.962
_diffrn_reflns_theta_min         2.334
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2936
_reflns_number_total             3074
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         3074
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0176
_refine_ls_R_factor_gt           0.0163
_refine_ls_restrained_S_all      1.054
_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)+(0.0184P)²+0.3804P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0388
_refine_ls_wR_factor_ref         0.0393
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C),
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
Rh1 Rh 0.19866(2) 0.09135(2) 0.15304(2) 0.00807(4) Uani 1 1 d . . . . .
Cl1 Cl -0.10228(4) 0.02433(4) 0.12529(4) 0.01153(8) Uani 1 1 d . . . . .
Cl2 Cl 0.25194(5) -0.15513(4) 0.20593(5) 0.01411(8) Uani 1 1 d . . . . .
C1 C 0.31593(19) 0.25500(18) 0.36648(18) 0.0107(3) Uani 1 1 d . . . . .
C2 C 0.2029(2) 0.32971(18) 0.26361(18) 0.0113(3) Uani 1 1 d . . . . .
C3 C 0.25709(19) 0.32298(18) 0.13168(18) 0.0109(3) Uani 1 1 d . . . . .
C4 C 0.40801(19) 0.24777(18) 0.15222(18) 0.0107(3) Uani 1 1 d . . . . .
C5 C 0.44640(19) 0.21054(18) 0.29785(18) 0.0111(3) Uani 1 1 d . . . . .
C6 C 0.3189(2) 0.24181(19) 0.52456(18) 0.0136(3) Uani 1 1 d . . . . .
H6 H 0.4082 0.1762 0.5573 0.016 Uiso 1 1 calc R . . . .
C7 C 0.3785(3) 0.4018(2) 0.6360(2) 0.0286(4) Uani 1 1 d . . . . .
H7A H 0.4849 0.4481 0.6266 0.043 Uiso 1 1 calc GR . . . .
H7B H 0.3974 0.3914 0.7411 0.043 Uiso 1 1 calc GR . . . .
H7C H 0.2915 0.4687 0.6120 0.043 Uiso 1 1 calc GR . . . .
C8 C 0.1540(2) 0.1616(2) 0.5329(2) 0.0213(4) Uani 1 1 d . . . . .
H8A H 0.0653 0.2277 0.5127 0.032 Uiso 1 1 calc GR . . . .
H8B H 0.1721 0.1438 0.6353 0.032 Uiso 1 1 calc GR . . . .
H8C H 0.1185 0.0619 0.4561 0.032 Uiso 1 1 calc GR . . . .
C9 C 0.0550(2) 0.4070(2) 0.2859(2) 0.0169(3) Uani 1 1 d . . . . .
H9A H -0.0401 0.3769 0.1903 0.025 Uiso 1 1 calc GR . . . .
H9B H 0.0882 0.5201 0.3144 0.025 Uiso 1 1 calc GR . . . .
H9C H 0.0204 0.3748 0.3674 0.025 Uiso 1 1 calc GR . . . .
C10 C 0.1785(2) 0.3894(2) -0.0001(2) 0.0151(3) Uani 1 1 d . . . . .
H10A H 0.2222 0.3489 -0.0849 0.023 Uiso 1 1 calc GR . . . .
H10B H 0.2070 0.5029 0.0315 0.023 Uiso 1 1 calc GR . . . .
H10C H 0.0548 0.3600 -0.0335 0.023 Uiso 1 1 calc GR . . . .
C11 C 0.5083(2) 0.22369(19) 0.0427(2) 0.0146(3) Uani 1 1 d . . . . .
H11A H 0.5833 0.1467 0.0659 0.022 Uiso 1 1 calc GR . . . .
H11B H 0.5770 0.3223 0.0524 0.022 Uiso 1 1 calc GR . . . .
H11C H 0.4307 0.1863 -0.0622 0.022 Uiso 1 1 calc GR . . . .
C12 C 0.5980(2) 0.1405(2) 0.3671(2) 0.0157(3) Uani 1 1 d . . . . .
H12A H 0.5722 0.0824 0.4375 0.024 Uiso 1 1 calc GR . . . .
H12B H 0.6944 0.2232 0.4236 0.024 Uiso 1 1 calc GR . . . .
H12C H 0.6270 0.0700 0.2858 0.024 Uiso 1 1 calc GR . . . .


_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
Rh1 Cl1 2.4467(4) . ?
Rh1 Cl1 2.4623(4) 2 ?
Rh1 Cl2 2.3999(4) . ?
Rh1 C1 2.1223(15) . ?
Rh1 C2 2.1481(15) . ?
Rh1 C3 2.1464(15) . ?
Rh1 C4 2.1420(15) . ?
Rh1 C5 2.1547(15) . ?
Cl1 Rh1 2.4623(4) 2 ?
C1 C2 1.454(2) . ?
C1 C5 1.450(2) . ?
C1 C6 1.508(2) . ?
C2 C3 1.426(2) . ?
C2 C9 1.498(2) . ?
C3 C4 1.451(2) . ?
C3 C10 1.490(2) . ?
C4 C5 1.430(2) . ?
C4 C11 1.491(2) . ?
C5 C12 1.492(2) . ?
C6 H6 1.0000 . ?
C6 C7 1.526(2) . ?
C6 C8 1.523(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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
Cl1 Rh1 Cl1 82.992(13) . 2 ?
Cl2 Rh1 Cl1 91.619(14) . 2 ?
Cl2 Rh1 Cl1 90.090(13) . . ?
C1 Rh1 Cl1 160.02(4) . 2 ?
C1 Rh1 Cl1 108.50(4) . . ?
C1 Rh1 Cl2 104.34(4) . . ?
C1 Rh1 C2 39.80(6) . . ?
C1 Rh1 C3 66.48(6) . . ?
C1 Rh1 C4 66.54(6) . . ?
C1 Rh1 C5 39.63(6) . . ?
C2 Rh1 Cl1 92.27(4) . . ?
C2 Rh1 Cl1 126.10(4) . 2 ?
C2 Rh1 Cl2 142.21(4) . . ?
C2 Rh1 C5 65.58(6) . . ?
C3 Rh1 Cl1 94.27(4) . 2 ?
C3 Rh1 Cl1 112.10(4) . . ?
C3 Rh1 Cl2 157.56(4) . . ?
C3 Rh1 C2 38.79(6) . . ?
C3 Rh1 C5 65.58(6) . . ?
C4 Rh1 Cl1 151.59(4) . . ?
C4 Rh1 Cl1 95.45(4) . 2 ?
C4 Rh1 Cl2 118.32(4) . . ?
C4 Rh1 C2 65.70(6) . . ?
C4 Rh1 C3 39.55(6) . . ?
C4 Rh1 C5 38.88(6) . . ?
C5 Rh1 Cl1 128.74(4) . 2 ?
C5 Rh1 Cl1 147.75(4) . . ?
C5 Rh1 Cl2 94.03(4) . . ?
Rh1 Cl1 Rh1 97.008(13) . 2 ?
C2 C1 Rh1 71.06(9) . . ?
C2 C1 C6 128.93(14) . . ?
C5 C1 Rh1 71.39(9) . . ?
C5 C1 C2 106.73(13) . . ?
C5 C1 C6 123.88(14) . . ?
C6 C1 Rh1 128.63(11) . . ?
C1 C2 Rh1 69.14(9) . . ?
C1 C2 C9 128.44(15) . . ?
C3 C2 Rh1 70.54(9) . . ?
C3 C2 C1 108.67(13) . . ?
C3 C2 C9 122.87(15) . . ?
C9 C2 Rh1 127.46(11) . . ?
C2 C3 Rh1 70.67(9) . . ?
C2 C3 C4 107.97(14) . . ?
C2 C3 C10 126.05(14) . . ?
C4 C3 Rh1 70.06(9) . . ?
C4 C3 C10 125.90(14) . . ?
C10 C3 Rh1 127.40(11) . . ?
C3 C4 Rh1 70.39(8) . . ?
C3 C4 C11 124.91(14) . . ?
C5 C4 Rh1 71.04(9) . . ?
C5 C4 C3 107.89(13) . . ?
C5 C4 C11 127.11(14) . . ?
C11 C4 Rh1 126.79(11) . . ?
C1 C5 Rh1 68.98(8) . . ?
C1 C5 C12 126.34(15) . . ?
C4 C5 Rh1 70.08(9) . . ?
C4 C5 C1 108.62(13) . . ?
C4 C5 C12 125.03(14) . . ?
C12 C5 Rh1 127.74(11) . . ?
C1 C6 H6 106.5 . . ?
C1 C6 C7 109.26(14) . . ?
C1 C6 C8 114.82(14) . . ?
C7 C6 H6 106.5 . . ?
C8 C6 H6 106.5 . . ?
C8 C6 C7 112.65(15) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
C5 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
Rh1 C1 C2 C3 -59.66(11) . . . . ?
Rh1 C1 C2 C9 121.91(17) . . . . ?
Rh1 C1 C5 C4 59.03(11) . . . . ?
Rh1 C1 C5 C12 -122.10(16) . . . . ?
Rh1 C1 C6 C7 -165.71(13) . . . . ?
Rh1 C1 C6 C8 -38.0(2) . . . . ?
Rh1 C2 C3 C4 -60.41(10) . . . . ?
Rh1 C2 C3 C10 122.74(16) . . . . ?
Rh1 C3 C4 C5 -61.48(11) . . . . ?
Rh1 C3 C4 C11 121.77(15) . . . . ?
Rh1 C4 C5 C1 -58.35(11) . . . . ?
Rh1 C4 C5 C12 122.76(16) . . . . ?
C1 C2 C3 Rh1 58.80(11) . . . . ?
C1 C2 C3 C4 -1.61(17) . . . . ?
C1 C2 C3 C10 -178.46(15) . . . . ?
C2 C1 C5 Rh1 -62.69(10) . . . . ?
C2 C1 C5 C4 -3.66(17) . . . . ?
C2 C1 C5 C12 175.21(15) . . . . ?
C2 C1 C6 C7 -69.3(2) . . . . ?
C2 C1 C6 C8 58.4(2) . . . . ?
C2 C3 C4 Rh1 60.80(11) . . . . ?
C2 C3 C4 C5 -0.68(17) . . . . ?
C2 C3 C4 C11 -177.43(15) . . . . ?
C3 C4 C5 Rh1 61.06(10) . . . . ?
C3 C4 C5 C1 2.71(17) . . . . ?
C3 C4 C5 C12 -176.18(15) . . . . ?
C5 C1 C2 Rh1 62.90(10) . . . . ?
C5 C1 C2 C3 3.24(17) . . . . ?
C5 C1 C2 C9 -175.19(16) . . . . ?
C5 C1 C6 C7 101.75(19) . . . . ?
C5 C1 C6 C8 -130.58(17) . . . . ?
C6 C1 C2 Rh1 -124.84(17) . . . . ?
C6 C1 C2 C3 175.50(15) . . . . ?
C6 C1 C2 C9 -2.9(3) . . . . ?
C6 C1 C5 Rh1 124.56(15) . . . . ?
C6 C1 C5 C4 -176.41(14) . . . . ?
C6 C1 C5 C12 2.5(3) . . . . ?
C9 C2 C3 Rh1 -122.66(15) . . . . ?
C9 C2 C3 C4 176.93(14) . . . . ?
C9 C2 C3 C10 0.1(2) . . . . ?
C10 C3 C4 Rh1 -122.34(16) . . . . ?
C10 C3 C4 C5 176.18(15) . . . . ?
C10 C3 C4 C11 -0.6(3) . . . . ?
C11 C4 C5 Rh1 -122.28(16) . . . . ?
C11 C4 C5 C1 179.37(15) . . . . ?
C11 C4 C5 C12 0.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_testt1
_database_code_depnum_ccdc_archive 'CCDC 1441686'
_audit_update_record             
;
2015-12-10 deposited with the CCDC.
2016-02-19 downloaded from the CCDC.
;
_audit_creation_date             2015-04-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H5 I O2'
_chemical_formula_sum            'C10 H5 I O2'
_chemical_formula_weight         284.04
_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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7536(3)
_cell_length_b                   8.2731(3)
_cell_length_c                   14.2858(5)
_cell_angle_alpha                73.2168(12)
_cell_angle_beta                 78.2230(15)
_cell_angle_gamma                85.3390(8)
_cell_volume                     858.64(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9940
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.94
_cell_measurement_theta_min      2.57
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.686
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0937 before and 0.0295 after correction.
The Ratio of minimum to maximum transmission is 0.6174.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.197
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15397
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.937
_diffrn_reflns_theta_min         1.516
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4005
_reflns_number_total             4116
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4116
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0164
_refine_ls_R_factor_gt           0.0159
_refine_ls_restrained_S_all      1.163
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0138P)²+1.0908P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0403
_refine_ls_wR_factor_ref         0.0407
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.28259(2) 0.14987(2) 0.61460(2) 0.01555(4) Uani 1 1 d . . . . .
O1 O 0.0956(2) 0.48056(19) 0.63548(11) 0.0225(3) Uani 1 1 d . . . . .
O2 O 0.26496(19) 0.91319(18) 0.28018(11) 0.0171(3) Uani 1 1 d . . . . .
C1 C 0.3226(2) 0.3450(2) 0.48072(14) 0.0138(3) Uani 1 1 d . . . . .
C2 C 0.4179(3) 0.2978(3) 0.39870(15) 0.0168(4) Uani 1 1 d . . . . .
H2 H 0.4580 0.1841 0.4060 0.020 Uiso 1 1 calc R . . . .
C3 C 0.4549(3) 0.4162(3) 0.30599(15) 0.0182(4) Uani 1 1 d . . . . .
H3 H 0.5197 0.3830 0.2502 0.022 Uiso 1 1 calc R . . . .
C4 C 0.3972(3) 0.5822(3) 0.29510(15) 0.0164(4) Uani 1 1 d . . . . .
H4 H 0.4206 0.6626 0.2316 0.020 Uiso 1 1 calc R . . . .
C5 C 0.3051(2) 0.6312(2) 0.37709(14) 0.0132(3) Uani 1 1 d . . . . .
C6 C 0.2655(2) 0.5131(2) 0.47175(14) 0.0121(3) Uani 1 1 d . . . . .
C7 C 0.1663(2) 0.5742(2) 0.55712(14) 0.0142(4) Uani 1 1 d . . . . .
C8 C 0.1509(3) 0.7594(3) 0.54252(15) 0.0178(4) Uani 1 1 d . . . . .
H8 H 0.1140 0.8008 0.5991 0.021 Uiso 1 1 calc R . . . .
C9 C 0.1869(3) 0.8696(3) 0.45269(16) 0.0178(4) Uani 1 1 d . . . . .
H9 H 0.1701 0.9870 0.4465 0.021 Uiso 1 1 calc R . . . .
C10 C 0.2521(2) 0.8128(2) 0.36297(15) 0.0139(3) Uani 1 1 d . . . . .
I2 I 0.58579(2) 0.07870(2) 0.13222(2) 0.01356(4) Uani 1 1 d . . . . .
O3 O 0.8543(2) 0.1976(2) 0.22547(11) 0.0221(3) Uani 1 1 d . . . . .
O4 O 1.38248(19) 0.4164(2) -0.07882(11) 0.0197(3) Uani 1 1 d . . . . .
C11 C 0.8143(2) 0.1705(2) 0.02956(14) 0.0117(3) Uani 1 1 d . . . . .
C12 C 0.8174(3) 0.1594(2) -0.06630(15) 0.0145(4) Uani 1 1 d . . . . .
H12 H 0.7205 0.1123 -0.0797 0.017 Uiso 1 1 calc R . . . .
C13 C 0.9601(3) 0.2162(2) -0.14231(15) 0.0153(4) Uani 1 1 d . . . . .
H13 H 0.9607 0.2079 -0.2073 0.018 Uiso 1 1 calc R . . . .
C14 C 1.1018(2) 0.2852(2) -0.12320(14) 0.0137(3) Uani 1 1 d . . . . .
H14 H 1.1997 0.3243 -0.1751 0.016 Uiso 1 1 calc R . . . .
C15 C 1.1003(2) 0.2970(2) -0.02813(14) 0.0114(3) Uani 1 1 d . . . . .
C16 C 0.9565(2) 0.2400(2) 0.05077(14) 0.0109(3) Uani 1 1 d . . . . .
C17 C 0.9644(2) 0.2559(2) 0.15159(14) 0.0132(3) Uani 1 1 d . . . . .
C18 C 1.1142(2) 0.3466(2) 0.16081(15) 0.0145(4) Uani 1 1 d . . . . .
H18 H 1.1139 0.3677 0.2228 0.017 Uiso 1 1 calc R . . . .
C19 C 1.2494(2) 0.4002(2) 0.08619(15) 0.0141(4) Uani 1 1 d . . . . .
H19 H 1.3432 0.4560 0.0966 0.017 Uiso 1 1 calc R . . . .
C20 C 1.2553(2) 0.3741(2) -0.01178(14) 0.0131(3) 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 C1 2.1017(19) . ?
O1 C7 1.213(2) . ?
O2 C10 1.223(2) . ?
C1 C2 1.391(3) . ?
C1 C6 1.402(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.392(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(3) . ?
C5 C6 1.412(3) . ?
C5 C10 1.492(3) . ?
C6 C7 1.498(3) . ?
C7 C8 1.484(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.332(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.471(3) . ?
I2 C11 2.0934(18) . ?
O3 C17 1.217(2) . ?
O4 C20 1.220(2) . ?
C11 C12 1.394(3) . ?
C11 C16 1.406(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(3) . ?
C15 C16 1.415(3) . ?
C15 C20 1.494(3) . ?
C16 C17 1.497(3) . ?
C17 C18 1.480(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.334(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.468(3) . ?

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
C2 C1 I1 114.95(14) . . ?
C2 C1 C6 120.57(18) . . ?
C6 C1 I1 124.44(14) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.45(18) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.94(19) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.99(19) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 121.01(18) . . ?
C4 C5 C10 118.24(17) . . ?
C6 C5 C10 120.74(17) . . ?
C1 C6 C5 118.03(17) . . ?
C1 C6 C7 123.62(17) . . ?
C5 C6 C7 118.35(17) . . ?
O1 C7 C6 123.39(18) . . ?
O1 C7 C8 119.17(18) . . ?
C8 C7 C6 117.42(17) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 C7 122.21(19) . . ?
C9 C8 H8 118.9 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.23(19) . . ?
C10 C9 H9 119.4 . . ?
O2 C10 C5 121.85(18) . . ?
O2 C10 C9 120.45(18) . . ?
C9 C10 C5 117.68(17) . . ?
C12 C11 I2 114.40(13) . . ?
C12 C11 C16 120.36(17) . . ?
C16 C11 I2 125.24(14) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.85(17) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.85(18) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.85(18) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 121.48(17) . . ?
C14 C15 C20 117.72(17) . . ?
C16 C15 C20 120.79(17) . . ?
C11 C16 C15 117.61(17) . . ?
C11 C16 C17 123.85(17) . . ?
C15 C16 C17 118.54(16) . . ?
O3 C17 C16 123.07(17) . . ?
O3 C17 C18 119.06(18) . . ?
C18 C17 C16 117.88(16) . . ?
C17 C18 H18 118.5 . . ?
C19 C18 C17 123.05(18) . . ?
C19 C18 H18 118.5 . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 120.92(17) . . ?
C20 C19 H19 119.5 . . ?
O4 C20 C15 120.65(18) . . ?
O4 C20 C19 120.97(17) . . ?
C19 C20 C15 118.37(16) . . ?

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
I1 C1 C2 C3 -179.27(15) . . . . ?
I1 C1 C6 C5 178.80(13) . . . . ?
I1 C1 C6 C7 -0.7(3) . . . . ?
O1 C7 C8 C9 -163.5(2) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C1 C6 C7 O1 -15.7(3) . . . . ?
C1 C6 C7 C8 166.08(18) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C2 C1 C6 C7 -178.46(18) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
C3 C4 C5 C10 177.37(18) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C4 C5 C6 C7 179.82(17) . . . . ?
C4 C5 C10 O2 10.6(3) . . . . ?
C4 C5 C10 C9 -168.09(18) . . . . ?
C5 C6 C7 O1 164.76(19) . . . . ?
C5 C6 C7 C8 -13.4(3) . . . . ?
C6 C1 C2 C3 -1.3(3) . . . . ?
C6 C5 C10 O2 -170.69(18) . . . . ?
C6 C5 C10 C9 10.7(3) . . . . ?
C6 C7 C8 C9 14.7(3) . . . . ?
C7 C8 C9 C10 -2.8(3) . . . . ?
C8 C9 C10 O2 171.4(2) . . . . ?
C8 C9 C10 C5 -10.0(3) . . . . ?
C10 C5 C6 C1 -178.43(17) . . . . ?
C10 C5 C6 C7 1.1(3) . . . . ?
I2 C11 C12 C13 179.63(15) . . . . ?
I2 C11 C16 C15 -179.58(13) . . . . ?
I2 C11 C16 C17 0.9(3) . . . . ?
O3 C17 C18 C19 173.3(2) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C11 C16 C17 O3 5.9(3) . . . . ?
C11 C16 C17 C18 -174.17(17) . . . . ?
C12 C11 C16 C15 -0.1(3) . . . . ?
C12 C11 C16 C17 -179.65(17) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C13 C14 C15 C20 -179.30(17) . . . . ?
C14 C15 C16 C11 0.1(3) . . . . ?
C14 C15 C16 C17 179.66(17) . . . . ?
C14 C15 C20 O4 -3.9(3) . . . . ?
C14 C15 C20 C19 175.09(17) . . . . ?
C15 C16 C17 O3 -173.61(19) . . . . ?
C15 C16 C17 C18 6.3(2) . . . . ?
C16 C11 C12 C13 0.1(3) . . . . ?
C16 C15 C20 O4 176.79(18) . . . . ?
C16 C15 C20 C19 -4.2(3) . . . . ?
C16 C17 C18 C19 -6.5(3) . . . . ?
C17 C18 C19 C20 1.2(3) . . . . ?
C18 C19 C20 O4 -176.76(19) . . . . ?
C18 C19 C20 C15 4.2(3) . . . . ?
C20 C15 C16 C11 179.31(16) . . . . ?
C20 C15 C16 C17 -1.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_testm1
_database_code_depnum_ccdc_archive 'CCDC 1441687'
_audit_update_record             
;
2015-12-10 deposited with the CCDC.
2016-02-19 downloaded from the CCDC.
;
_audit_creation_date             2015-08-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C11 H7 I O3'
_chemical_formula_sum            'C11 H7 I O3'
_chemical_formula_weight         314.07
_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'
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                   8.1168(3)
_cell_length_b                   7.9198(2)
_cell_length_c                   15.1553(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.0671(15)
_cell_angle_gamma                90
_cell_volume                     972.84(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6355
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.272
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0412 before and 0.0257 after correction.
The Ratio of minimum to maximum transmission is 0.8782.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.144
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8582
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.893
_diffrn_reflns_theta_min         2.513
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2222
_reflns_number_total             2319
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0145
_refine_ls_R_factor_gt           0.0135
_refine_ls_restrained_S_all      1.049
_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)+(0.0147P)²+0.9053P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0331
_refine_ls_wR_factor_ref         0.0335
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.49491(2) 0.29844(2) 0.35534(2) 0.01055(4) Uani 1 1 d . . . . .
O1 O 0.92133(15) -0.01078(15) 0.67180(7) 0.0133(2) Uani 1 1 d . . . . .
O2 O 0.98207(15) -0.27455(15) 0.57486(8) 0.0135(2) Uani 1 1 d . . . . .
O3 O 0.67402(15) -0.01098(16) 0.29512(8) 0.0146(2) Uani 1 1 d . . . . .
C1 C 0.9412(2) 0.0878(2) 0.75124(10) 0.0132(3) Uani 1 1 d . . . . .
H1A H 0.9860 0.1964 0.7376 0.020 Uiso 1 1 calc GR . . . .
H1B H 1.0150 0.0307 0.7929 0.020 Uiso 1 1 calc GR . . . .
H1C H 0.8360 0.1023 0.7763 0.020 Uiso 1 1 calc GR . . . .
C2 C 0.82616(19) 0.0531(2) 0.60416(10) 0.0101(3) Uani 1 1 d . . . . .
C3 C 0.7438(2) 0.2074(2) 0.60918(11) 0.0128(3) Uani 1 1 d . . . . .
H3 H 0.7510 0.2691 0.6614 0.015 Uiso 1 1 calc R . . . .
C4 C 0.6515(2) 0.2687(2) 0.53686(11) 0.0124(3) Uani 1 1 d . . . . .
H4 H 0.5963 0.3710 0.5414 0.015 Uiso 1 1 calc R . . . .
C5 C 0.63943(19) 0.1802(2) 0.45725(10) 0.0103(3) Uani 1 1 d . . . . .
C6 C 0.71730(19) 0.0238(2) 0.45094(10) 0.0089(3) Uani 1 1 d . . . . .
C7 C 0.80927(19) -0.0433(2) 0.52545(10) 0.0088(3) Uani 1 1 d . . . . .
C8 C 0.8822(2) -0.2159(2) 0.51996(11) 0.0097(3) Uani 1 1 d . . . . .
C9 C 0.8280(2) -0.3224(2) 0.44334(11) 0.0131(3) Uani 1 1 d . . . . .
H9 H 0.8518 -0.4373 0.4445 0.016 Uiso 1 1 calc R . . . .
C10 C 0.7456(2) -0.2569(2) 0.37266(11) 0.0137(3) Uani 1 1 d . . . . .
H10 H 0.7114 -0.3274 0.3261 0.016 Uiso 1 1 calc R . . . .
C11 C 0.70801(19) -0.0753(2) 0.36710(10) 0.0100(3) 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 C5 2.1080(16) . ?
O1 C1 1.4369(19) . ?
O1 C2 1.3487(19) . ?
O2 C8 1.222(2) . ?
O3 C11 1.222(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.397(2) . ?
C2 C7 1.417(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.394(2) . ?
C5 C6 1.397(2) . ?
C6 C7 1.423(2) . ?
C6 C11 1.492(2) . ?
C7 C8 1.493(2) . ?
C8 C9 1.483(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.337(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.472(2) . ?

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
C2 O1 C1 117.83(13) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 122.91(15) . . ?
O1 C2 C7 117.59(14) . . ?
C3 C2 C7 119.50(14) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.32(15) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.32(15) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 I1 114.93(12) . . ?
C4 C5 C6 119.60(15) . . ?
C6 C5 I1 125.45(12) . . ?
C5 C6 C7 119.82(14) . . ?
C5 C6 C11 121.50(14) . . ?
C7 C6 C11 118.68(14) . . ?
C2 C7 C6 119.32(14) . . ?
C2 C7 C8 121.30(14) . . ?
C6 C7 C8 119.35(14) . . ?
O2 C8 C7 124.09(15) . . ?
O2 C8 C9 118.37(15) . . ?
C9 C8 C7 117.55(14) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.44(15) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.21(15) . . ?
C11 C10 H10 119.4 . . ?
O3 C11 C6 122.67(15) . . ?
O3 C11 C10 119.64(15) . . ?
C10 C11 C6 117.67(14) . . ?

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
I1 C5 C6 C7 -178.92(11) . . . . ?
I1 C5 C6 C11 1.7(2) . . . . ?
O1 C2 C3 C4 178.25(15) . . . . ?
O1 C2 C7 C6 -176.62(14) . . . . ?
O1 C2 C7 C8 5.1(2) . . . . ?
O2 C8 C9 C10 -166.66(16) . . . . ?
C1 O1 C2 C3 -1.8(2) . . . . ?
C1 O1 C2 C7 178.94(14) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C2 C7 C8 O2 -12.8(2) . . . . ?
C2 C7 C8 C9 166.60(15) . . . . ?
C3 C2 C7 C6 4.0(2) . . . . ?
C3 C2 C7 C8 -174.25(15) . . . . ?
C3 C4 C5 I1 -179.24(13) . . . . ?
C3 C4 C5 C6 2.2(2) . . . . ?
C4 C5 C6 C7 -0.5(2) . . . . ?
C4 C5 C6 C11 -179.91(15) . . . . ?
C5 C6 C7 C2 -2.6(2) . . . . ?
C5 C6 C7 C8 175.76(14) . . . . ?
C5 C6 C11 O3 20.5(2) . . . . ?
C5 C6 C11 C10 -160.93(15) . . . . ?
C6 C7 C8 O2 168.92(15) . . . . ?
C6 C7 C8 C9 -11.7(2) . . . . ?
C7 C2 C3 C4 -2.5(2) . . . . ?
C7 C6 C11 O3 -158.86(15) . . . . ?
C7 C6 C11 C10 19.7(2) . . . . ?
C7 C8 C9 C10 13.9(2) . . . . ?
C8 C9 C10 C11 1.2(3) . . . . ?
C9 C10 C11 O3 160.37(17) . . . . ?
C9 C10 C11 C6 -18.2(2) . . . . ?
C11 C6 C7 C2 176.84(14) . . . . ?
C11 C6 C7 C8 -4.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_gj107
_database_code_depnum_ccdc_archive 'CCDC 1441688'
_audit_update_record             
;
2015-12-10 deposited with the CCDC.
2016-02-19 downloaded from the CCDC.
;
_audit_creation_date             2015-08-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H9 I O3'
_chemical_formula_sum            'C12 H9 I O3'
_chemical_formula_weight         328.09
_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'
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                   17.2465(4)
_cell_length_b                   16.7627(3)
_cell_length_c                   7.5137(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.9216(12)
_cell_angle_gamma                90
_cell_volume                     2170.97(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.92
_cell_measurement_theta_min      2.363
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.937
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0582 before and 0.0448 after correction.
The Ratio of minimum to maximum transmission is 0.8420.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.008
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.379
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            38215
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.943
_diffrn_reflns_theta_min         1.181
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Pt135 CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker Mircostar Rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus rotating anode'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4674
_reflns_number_total             5196
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.181
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0202
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0270P)²+1.1381P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0472
_refine_ls_wR_factor_ref         0.0492
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C9(H9), C14(H14), C15(H15), C21(H21)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
C1 C 1.01282(12) 0.27014(13) 0.2320(3) 0.0122(4) Uani 1 1 d . . . . .
C2 C 1.01829(13) 0.18761(13) 0.2176(3) 0.0148(4) Uani 1 1 d . . . . .
H2 H 1.0639 0.1649 0.1714 0.018 Uiso 1 1 calc R . . . .
C3 C 0.95939(13) 0.13786(13) 0.2686(3) 0.0155(4) Uani 1 1 d . . . . .
H3 H 0.9645 0.0817 0.2573 0.019 Uiso 1 1 calc R . . . .
C4 C 0.89210(13) 0.17053(13) 0.3370(3) 0.0135(4) Uani 1 1 d . . . . .
C5 C 0.88351(12) 0.25433(13) 0.3478(3) 0.0124(4) Uani 1 1 d . . . . .
C6 C 0.94503(12) 0.30449(12) 0.2947(3) 0.0114(4) Uani 1 1 d . . . . .
C7 C 0.93644(13) 0.39299(13) 0.3086(3) 0.0144(4) Uani 1 1 d . . . . .
C8 C 0.86156(13) 0.42714(13) 0.3660(3) 0.0138(4) Uani 1 1 d . . . . .
C9 C 0.80528(13) 0.37789(13) 0.4146(3) 0.0157(4) Uani 1 1 d . . . . .
H9 H 0.7580 0.4008 0.4514 0.019 Uiso 1 1 calc R . . . .
C10 C 0.81178(13) 0.29041(13) 0.4148(3) 0.0143(4) Uani 1 1 d . . . . .
C11 C 0.84302(15) 0.03956(13) 0.3833(3) 0.0208(5) Uani 1 1 d . . . . .
H11A H 0.8474 0.0240 0.2584 0.031 Uiso 1 1 calc GR . . . .
H11B H 0.7981 0.0129 0.4334 0.031 Uiso 1 1 calc GR . . . .
H11C H 0.8902 0.0239 0.4506 0.031 Uiso 1 1 calc GR . . . .
C12 C 0.85564(14) 0.51592(13) 0.3719(3) 0.0189(5) Uani 1 1 d . . . . .
H12A H 0.8047 0.5312 0.4148 0.028 Uiso 1 1 calc GR . . . .
H12B H 0.8620 0.5377 0.2522 0.028 Uiso 1 1 calc GR . . . .
H12C H 0.8964 0.5372 0.4527 0.028 Uiso 1 1 calc GR . . . .
I1 I 1.11417(2) 0.32837(2) 0.15237(2) 0.01482(5) Uani 1 1 d . . . . .
O1 O 0.83329(10) 0.12394(9) 0.3944(2) 0.0201(4) Uani 1 1 d . . . . .
O2 O 0.98879(10) 0.43853(10) 0.2750(3) 0.0297(5) Uani 1 1 d . . . . .
O3 O 0.75824(10) 0.25132(10) 0.4713(3) 0.0233(4) Uani 1 1 d . . . . .
C13 C 0.50902(13) 0.36489(13) 0.7088(3) 0.0128(4) Uani 1 1 d . . . . .
C14 C 0.51738(13) 0.44762(13) 0.7119(3) 0.0149(4) Uani 1 1 d . . . . .
H14 H 0.5637 0.4705 0.6699 0.018 Uiso 1 1 calc R . . . .
C15 C 0.46059(13) 0.49716(13) 0.7742(3) 0.0152(4) Uani 1 1 d . . . . .
H15 H 0.4681 0.5533 0.7748 0.018 Uiso 1 1 calc R . . . .
C16 C 0.39201(12) 0.46463(13) 0.8363(3) 0.0129(4) Uani 1 1 d . . . . .
C17 C 0.38162(12) 0.38094(13) 0.8345(3) 0.0117(4) Uani 1 1 d . . . . .
C18 C 0.44119(13) 0.33064(12) 0.7706(3) 0.0116(4) Uani 1 1 d . . . . .
C19 C 0.42933(12) 0.24203(12) 0.7687(3) 0.0122(4) Uani 1 1 d . . . . .
C20 C 0.35876(13) 0.20802(13) 0.8482(3) 0.0131(4) Uani 1 1 d . . . . .
C21 C 0.30402(13) 0.25685(13) 0.9061(3) 0.0143(4) Uani 1 1 d . . . . .
H21 H 0.2588 0.2338 0.9535 0.017 Uiso 1 1 calc R . . . .
C22 C 0.30968(13) 0.34449(13) 0.9008(3) 0.0133(4) Uani 1 1 d . . . . .
C23 C 0.34757(14) 0.59564(13) 0.9037(3) 0.0178(5) Uani 1 1 d . . . . .
H23A H 0.3534 0.6151 0.7820 0.027 Uiso 1 1 calc GR . . . .
H23B H 0.3947 0.6076 0.9751 0.027 Uiso 1 1 calc GR . . . .
H23C H 0.3031 0.6220 0.9564 0.027 Uiso 1 1 calc GR . . . .
C24 C 0.35242(14) 0.11895(13) 0.8544(3) 0.0180(5) Uani 1 1 d . . . . .
H24A H 0.3928 0.0975 0.9358 0.027 Uiso 1 1 calc GR . . . .
H24B H 0.3590 0.0971 0.7349 0.027 Uiso 1 1 calc GR . . . .
H24C H 0.3013 0.1039 0.8965 0.027 Uiso 1 1 calc GR . . . .
I2 I 0.60698(2) 0.30705(2) 0.61029(2) 0.01412(5) Uani 1 1 d . . . . .
O4 O 0.33493(9) 0.51050(9) 0.9004(2) 0.0173(3) Uani 1 1 d . . . . .
O5 O 0.47534(10) 0.19664(9) 0.7023(2) 0.0200(4) Uani 1 1 d . . . . .
O6 O 0.25524(10) 0.38369(10) 0.9537(2) 0.0220(4) 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
C1 C2 1.391(3) . ?
C1 C6 1.399(3) . ?
C1 I1 2.106(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.397(3) . ?
C4 C5 1.415(3) . ?
C4 O1 1.362(3) . ?
C5 C6 1.421(3) . ?
C5 C10 1.480(3) . ?
C6 C7 1.495(3) . ?
C7 C8 1.490(3) . ?
C7 O2 1.215(3) . ?
C8 C9 1.335(3) . ?
C8 C12 1.492(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.471(3) . ?
C10 O3 1.220(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 O1 1.427(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.394(3) . ?
C13 C18 1.396(3) . ?
C13 I2 2.104(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.378(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.397(3) . ?
C16 C17 1.414(3) . ?
C16 O4 1.351(3) . ?
C17 C18 1.425(3) . ?
C17 C22 1.484(3) . ?
C18 C19 1.499(3) . ?
C19 C20 1.487(3) . ?
C19 O5 1.218(3) . ?
C20 C21 1.333(3) . ?
C20 C24 1.498(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.473(3) . ?
C22 O6 1.223(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C23 O4 1.444(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
C2 C1 C6 119.7(2) . . ?
C2 C1 I1 112.32(15) . . ?
C6 C1 I1 128.00(16) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.8(2) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.0(2) . . ?
O1 C4 C3 121.92(19) . . ?
O1 C4 C5 118.07(19) . . ?
C4 C5 C6 119.38(19) . . ?
C4 C5 C10 121.02(19) . . ?
C6 C5 C10 119.60(19) . . ?
C1 C6 C5 119.41(19) . . ?
C1 C6 C7 121.19(19) . . ?
C5 C6 C7 119.40(19) . . ?
C8 C7 C6 119.37(19) . . ?
O2 C7 C6 122.2(2) . . ?
O2 C7 C8 118.4(2) . . ?
C7 C8 C12 116.92(19) . . ?
C9 C8 C7 119.2(2) . . ?
C9 C8 C12 123.9(2) . . ?
C8 C9 H9 117.9 . . ?
C8 C9 C10 124.1(2) . . ?
C10 C9 H9 117.9 . . ?
C9 C10 C5 118.14(19) . . ?
O3 C10 C5 123.4(2) . . ?
O3 C10 C9 118.5(2) . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C4 O1 C11 117.36(18) . . ?
C14 C13 C18 119.38(19) . . ?
C14 C13 I2 112.36(16) . . ?
C18 C13 I2 128.25(16) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 C13 122.1(2) . . ?
C15 C14 H14 119.0 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 119.51(19) . . ?
O4 C16 C15 122.17(19) . . ?
O4 C16 C17 118.32(19) . . ?
C16 C17 C18 119.84(19) . . ?
C16 C17 C22 120.83(19) . . ?
C18 C17 C22 119.33(19) . . ?
C13 C18 C17 119.36(19) . . ?
C13 C18 C19 121.32(19) . . ?
C17 C18 C19 119.32(19) . . ?
C20 C19 C18 119.30(18) . . ?
O5 C19 C18 122.1(2) . . ?
O5 C19 C20 118.57(19) . . ?
C19 C20 C24 117.14(19) . . ?
C21 C20 C19 119.6(2) . . ?
C21 C20 C24 123.3(2) . . ?
C20 C21 H21 118.1 . . ?
C20 C21 C22 123.7(2) . . ?
C22 C21 H21 118.1 . . ?
C21 C22 C17 118.47(19) . . ?
O6 C22 C17 123.2(2) . . ?
O6 C22 C21 118.35(19) . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C16 O4 C23 117.23(17) . . ?

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
C1 C2 C3 C4 -0.1(4) . . . . ?
C1 C6 C7 C8 176.5(2) . . . . ?
C1 C6 C7 O2 -3.8(4) . . . . ?
C2 C1 C6 C5 1.8(3) . . . . ?
C2 C1 C6 C7 -178.8(2) . . . . ?
C2 C3 C4 C5 2.2(3) . . . . ?
C2 C3 C4 O1 -177.9(2) . . . . ?
C3 C4 C5 C6 -2.3(3) . . . . ?
C3 C4 C5 C10 178.2(2) . . . . ?
C3 C4 O1 C11 0.4(3) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C4 C5 C6 C7 -179.1(2) . . . . ?
C4 C5 C10 C9 -177.2(2) . . . . ?
C4 C5 C10 O3 3.4(4) . . . . ?
C5 C4 O1 C11 -179.7(2) . . . . ?
C5 C6 C7 C8 -4.2(3) . . . . ?
C5 C6 C7 O2 175.6(2) . . . . ?
C6 C1 C2 C3 -2.0(4) . . . . ?
C6 C5 C10 C9 3.3(3) . . . . ?
C6 C5 C10 O3 -176.1(2) . . . . ?
C6 C7 C8 C9 4.2(3) . . . . ?
C6 C7 C8 C12 -178.2(2) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
C8 C9 C10 C5 -3.4(3) . . . . ?
C8 C9 C10 O3 176.0(2) . . . . ?
C10 C5 C6 C1 179.8(2) . . . . ?
C10 C5 C6 C7 0.4(3) . . . . ?
C12 C8 C9 C10 -177.8(2) . . . . ?
I1 C1 C2 C3 177.77(18) . . . . ?
I1 C1 C6 C5 -177.86(16) . . . . ?
I1 C1 C6 C7 1.5(3) . . . . ?
O1 C4 C5 C6 177.8(2) . . . . ?
O1 C4 C5 C10 -1.7(3) . . . . ?
O2 C7 C8 C9 -175.6(2) . . . . ?
O2 C7 C8 C12 2.0(3) . . . . ?
C13 C14 C15 C16 -0.1(4) . . . . ?
C13 C18 C19 C20 175.5(2) . . . . ?
C13 C18 C19 O5 -5.3(3) . . . . ?
C14 C13 C18 C17 0.4(3) . . . . ?
C14 C13 C18 C19 179.6(2) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C14 C15 C16 O4 179.3(2) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C15 C16 C17 C22 179.6(2) . . . . ?
C15 C16 O4 C23 -0.4(3) . . . . ?
C16 C17 C18 C13 -0.6(3) . . . . ?
C16 C17 C18 C19 -179.8(2) . . . . ?
C16 C17 C22 C21 -176.3(2) . . . . ?
C16 C17 C22 O6 2.6(4) . . . . ?
C17 C16 O4 C23 178.9(2) . . . . ?
C17 C18 C19 C20 -5.3(3) . . . . ?
C17 C18 C19 O5 173.9(2) . . . . ?
C18 C13 C14 C15 -0.1(4) . . . . ?
C18 C17 C22 C21 2.9(3) . . . . ?
C18 C17 C22 O6 -178.2(2) . . . . ?
C18 C19 C20 C21 5.7(3) . . . . ?
C18 C19 C20 C24 -175.8(2) . . . . ?
C19 C20 C21 C22 -1.6(3) . . . . ?
C20 C21 C22 C17 -2.7(3) . . . . ?
C20 C21 C22 O6 178.3(2) . . . . ?
C22 C17 C18 C13 -179.8(2) . . . . ?
C22 C17 C18 C19 1.0(3) . . . . ?
C24 C20 C21 C22 179.9(2) . . . . ?
I2 C13 C14 C15 -178.99(18) . . . . ?
I2 C13 C18 C17 179.15(16) . . . . ?
I2 C13 C18 C19 -1.7(3) . . . . ?
O4 C16 C17 C18 -178.97(19) . . . . ?
O4 C16 C17 C22 0.2(3) . . . . ?
O5 C19 C20 C21 -173.6(2) . . . . ?
O5 C19 C20 C24 4.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_testm1
_database_code_depnum_ccdc_archive 'CCDC 1441689'
_audit_update_record             
;
2015-12-10 deposited with the CCDC.
2016-02-19 downloaded from the CCDC.
;
_audit_creation_date             2015-10-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H4 I N O4'
_chemical_formula_sum            'C10 H4 I N O4'
_chemical_formula_weight         329.04
_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'
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'

_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                   7.7794(3)
_cell_length_b                   9.0897(3)
_cell_length_c                   13.9834(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.5625(14)
_cell_angle_gamma                90
_cell_volume                     975.06(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6582
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.281
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6200
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0650 before and 0.0266 after correction.
The Ratio of minimum to maximum transmission is 0.8315.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.241
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8574
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.921
_diffrn_reflns_theta_min         2.655
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2252
_reflns_number_total             2322
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0153
_refine_ls_R_factor_gt           0.0145
_refine_ls_restrained_S_all      1.109
_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)+(0.0123P)²+0.9842P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0341
_refine_ls_wR_factor_ref         0.0344
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.46394(2) 0.32037(2) 0.63337(2) 0.01333(4) Uani 1 1 d . . . . .
O1 O 0.11999(17) -0.05159(15) 0.20509(9) 0.0190(3) Uani 1 1 d . . . . .
O2 O -0.11253(16) 0.04387(15) 0.24664(9) 0.0175(3) Uani 1 1 d . . . . .
O3 O 0.44675(17) -0.00426(14) 0.67419(9) 0.0168(3) Uani 1 1 d . . . . .
O4 O 0.01075(17) -0.21258(15) 0.37038(9) 0.0175(3) Uani 1 1 d . . . . .
N1 N 0.04325(19) 0.01491(16) 0.26085(10) 0.0116(3) Uani 1 1 d . . . . .
C1 C 0.3392(2) 0.19929(18) 0.51415(12) 0.0110(3) Uani 1 1 d . . . . .
C2 C 0.2940(2) 0.28094(19) 0.42923(12) 0.0126(3) Uani 1 1 d . . . . .
H2 H 0.3277 0.3813 0.4281 0.015 Uiso 1 1 calc R . . . .
C3 C 0.2007(2) 0.21760(19) 0.34642(12) 0.0122(3) Uani 1 1 d . . . . .
H3 H 0.1737 0.2724 0.2880 0.015 Uiso 1 1 calc R . . . .
C4 C 0.1479(2) 0.07350(18) 0.35065(11) 0.0103(3) Uani 1 1 d . . . . .
C5 C 0.1899(2) -0.01266(18) 0.43334(11) 0.0097(3) Uani 1 1 d . . . . .
C6 C 0.2921(2) 0.04998(18) 0.51619(11) 0.0095(3) Uani 1 1 d . . . . .
C7 C 0.3484(2) -0.04704(19) 0.60256(12) 0.0112(3) Uani 1 1 d . . . . .
C8 C 0.2863(2) -0.20099(19) 0.59827(13) 0.0142(3) Uani 1 1 d . . . . .
H8 H 0.3217 -0.2628 0.6527 0.017 Uiso 1 1 calc R . . . .
C9 C 0.1830(2) -0.25662(19) 0.52145(13) 0.0143(3) Uani 1 1 d . . . . .
H9 H 0.1489 -0.3569 0.5221 0.017 Uiso 1 1 calc R . . . .
C10 C 0.1205(2) -0.16642(18) 0.43567(12) 0.0113(3) 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 C1 2.0964(16) . ?
O1 N1 1.2183(19) . ?
O2 N1 1.2237(19) . ?
O3 C7 1.219(2) . ?
O4 C10 1.216(2) . ?
N1 C4 1.478(2) . ?
C1 C2 1.395(2) . ?
C1 C6 1.407(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.377(2) . ?
C4 C5 1.390(2) . ?
C5 C6 1.412(2) . ?
C5 C10 1.501(2) . ?
C6 C7 1.501(2) . ?
C7 C8 1.478(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.330(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.467(2) . ?

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
O1 N1 O2 125.46(14) . . ?
O1 N1 C4 117.60(14) . . ?
O2 N1 C4 116.84(13) . . ?
C2 C1 I1 114.55(12) . . ?
C2 C1 C6 120.05(15) . . ?
C6 C1 I1 125.30(12) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.88(16) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.7 . . ?
C4 C3 C2 118.55(15) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 N1 115.63(14) . . ?
C3 C4 C5 122.77(15) . . ?
C5 C4 N1 121.61(15) . . ?
C4 C5 C6 118.56(15) . . ?
C4 C5 C10 120.48(15) . . ?
C6 C5 C10 120.90(15) . . ?
C1 C6 C5 119.04(15) . . ?
C1 C6 C7 122.74(15) . . ?
C5 C6 C7 118.21(15) . . ?
O3 C7 C6 122.23(15) . . ?
O3 C7 C8 119.46(15) . . ?
C8 C7 C6 118.28(14) . . ?
C7 C8 H8 118.6 . . ?
C9 C8 C7 122.84(16) . . ?
C9 C8 H8 118.6 . . ?
C8 C9 H9 119.3 . . ?
C8 C9 C10 121.43(16) . . ?
C10 C9 H9 119.3 . . ?
O4 C10 C5 121.01(15) . . ?
O4 C10 C9 121.11(16) . . ?
C9 C10 C5 117.81(15) . . ?

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
I1 C1 C2 C3 -175.70(13) . . . . ?
I1 C1 C6 C5 172.33(12) . . . . ?
I1 C1 C6 C7 -8.7(2) . . . . ?
O1 N1 C4 C3 94.52(18) . . . . ?
O1 N1 C4 C5 -85.3(2) . . . . ?
O2 N1 C4 C3 -81.96(19) . . . . ?
O2 N1 C4 C5 98.27(19) . . . . ?
O3 C7 C8 C9 -177.99(17) . . . . ?
N1 C4 C5 C6 179.25(14) . . . . ?
N1 C4 C5 C10 -3.7(2) . . . . ?
C1 C2 C3 C4 2.3(3) . . . . ?
C1 C6 C7 O3 -4.3(2) . . . . ?
C1 C6 C7 C8 177.84(15) . . . . ?
C2 C1 C6 C5 -3.9(2) . . . . ?
C2 C1 C6 C7 175.14(15) . . . . ?
C2 C3 C4 N1 177.76(15) . . . . ?
C2 C3 C4 C5 -2.5(3) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C3 C4 C5 C10 176.55(15) . . . . ?
C4 C5 C6 C1 3.7(2) . . . . ?
C4 C5 C6 C7 -175.39(14) . . . . ?
C4 C5 C10 O4 -8.7(2) . . . . ?
C4 C5 C10 C9 174.20(15) . . . . ?
C5 C6 C7 O3 174.72(16) . . . . ?
C5 C6 C7 C8 -3.1(2) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C6 C5 C10 O4 168.26(16) . . . . ?
C6 C5 C10 C9 -8.8(2) . . . . ?
C6 C7 C8 C9 -0.1(2) . . . . ?
C7 C8 C9 C10 -1.3(3) . . . . ?
C8 C9 C10 O4 -171.55(17) . . . . ?
C8 C9 C10 C5 5.5(2) . . . . ?
C10 C5 C6 C1 -173.38(15) . . . . ?
C10 C5 C6 C7 7.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_testo1
_database_code_depnum_ccdc_archive 'CCDC 1441690'
_audit_update_record             
;
2015-12-10 deposited with the CCDC.
2016-02-19 downloaded from the CCDC.
;
_audit_creation_date             2015-09-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H4 Br I O2'
_chemical_formula_sum            'C10 H4 Br I O2'
_chemical_formula_weight         362.94
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.07520(10)
_cell_length_b                   6.1752(2)
_cell_length_c                   30.9217(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     969.10(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3455
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.86
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.393
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1086 before and 0.0544 after correction.
The Ratio of minimum to maximum transmission is 0.5486.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.488
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7320
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.923
_diffrn_reflns_theta_min         1.317
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.652
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2194
_reflns_number_total             2329
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.969
_refine_diff_density_min         -1.133
_refine_diff_density_rms         0.140
_refine_ls_abs_structure_details 
;
 Flack x determined using 827 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.038(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0278
_refine_ls_restrained_S_all      1.127
_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)+(0.0101P)²+0.5125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0486
_refine_ls_wR_factor_ref         0.0493
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 1.06028(7) 0.35787(7) 0.46176(2) 0.01228(10) Uani 1 1 d . . . . .
Br1 Br 0.23589(11) 0.15148(13) 0.26022(2) 0.01696(15) Uani 1 1 d . . . . .
O1 O 0.1340(9) 0.5579(8) 0.31165(14) 0.0197(11) Uani 1 1 d . . . . .
O2 O 0.9777(7) 0.1467(8) 0.37416(12) 0.0142(9) Uani 1 1 d . . . . .
C1 C 0.3262(12) 0.4670(11) 0.32620(18) 0.0113(13) Uani 1 1 d . . . . .
C2 C 0.4237(13) 0.2584(10) 0.30785(18) 0.0130(13) Uani 1 1 d . . . . .
C3 C 0.6311(10) 0.1563(12) 0.32432(17) 0.0132(12) Uani 1 1 d . . . . .
H3 H 0.6872 0.0282 0.3115 0.016 Uiso 1 1 calc R . . . .
C4 C 0.7756(12) 0.2391(11) 0.36233(19) 0.0127(13) Uani 1 1 d . . . . .
C5 C 0.6768(11) 0.4374(10) 0.38415(19) 0.0101(13) Uani 1 1 d . . . . .
C6 C 0.4674(12) 0.5543(11) 0.36508(18) 0.0125(13) Uani 1 1 d . . . . .
C7 C 0.3781(12) 0.7471(11) 0.3817(2) 0.0130(14) Uani 1 1 d . . . . .
H7 H 0.2433 0.8229 0.3680 0.016 Uiso 1 1 calc R . . . .
C8 C 0.4924(11) 0.8263(11) 0.41903(19) 0.0166(14) Uani 1 1 d . . . . .
H8 H 0.4358 0.9583 0.4301 0.020 Uiso 1 1 calc R . . . .
C9 C 0.6892(12) 0.7135(11) 0.4403(2) 0.0151(14) Uani 1 1 d . . . . .
H9 H 0.7606 0.7670 0.4658 0.018 Uiso 1 1 calc R . . . .
C10 C 0.7792(11) 0.5185(10) 0.42294(19) 0.0100(13) 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 C10 2.112(6) . ?
Br1 C2 1.875(6) . ?
O1 C1 1.212(7) . ?
O2 C4 1.229(7) . ?
C1 C2 1.492(9) . ?
C1 C6 1.500(8) . ?
C2 C3 1.329(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.477(8) . ?
C4 C5 1.485(9) . ?
C5 C6 1.414(9) . ?
C5 C10 1.400(8) . ?
C6 C7 1.373(9) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(9) . ?
C8 H8 0.9300 . ?
C8 C9 1.384(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.395(9) . ?

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
O1 C1 C2 121.7(6) . . ?
O1 C1 C6 121.0(6) . . ?
C2 C1 C6 117.2(5) . . ?
C1 C2 Br1 115.7(4) . . ?
C3 C2 Br1 122.5(5) . . ?
C3 C2 C1 121.8(5) . . ?
C2 C3 H3 118.9 . . ?
C2 C3 C4 122.3(6) . . ?
C4 C3 H3 118.9 . . ?
O2 C4 C3 119.4(6) . . ?
O2 C4 C5 121.9(5) . . ?
C3 C4 C5 118.6(6) . . ?
C6 C5 C4 119.0(5) . . ?
C10 C5 C4 124.0(5) . . ?
C10 C5 C6 117.0(6) . . ?
C5 C6 C1 120.7(6) . . ?
C7 C6 C1 116.9(6) . . ?
C7 C6 C5 122.3(6) . . ?
C6 C7 H7 120.6 . . ?
C6 C7 C8 118.7(6) . . ?
C8 C7 H7 120.6 . . ?
C7 C8 H8 119.3 . . ?
C7 C8 C9 121.5(6) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.2(6) . . ?
C10 C9 H9 120.4 . . ?
C5 C10 I1 124.7(5) . . ?
C9 C10 I1 114.1(4) . . ?
C9 C10 C5 121.1(6) . . ?

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
Br1 C2 C3 C4 -178.9(4) . . . . ?
O1 C1 C2 Br1 1.6(8) . . . . ?
O1 C1 C2 C3 -178.6(6) . . . . ?
O1 C1 C6 C5 174.4(6) . . . . ?
O1 C1 C6 C7 -3.6(9) . . . . ?
O2 C4 C5 C6 170.4(6) . . . . ?
O2 C4 C5 C10 -9.3(9) . . . . ?
C1 C2 C3 C4 1.3(9) . . . . ?
C1 C6 C7 C8 176.1(5) . . . . ?
C2 C1 C6 C5 -2.5(8) . . . . ?
C2 C1 C6 C7 179.5(5) . . . . ?
C2 C3 C4 O2 -174.5(6) . . . . ?
C2 C3 C4 C5 3.2(9) . . . . ?
C3 C4 C5 C6 -7.3(8) . . . . ?
C3 C4 C5 C10 173.0(6) . . . . ?
C4 C5 C6 C1 6.9(8) . . . . ?
C4 C5 C6 C7 -175.3(5) . . . . ?
C4 C5 C10 I1 -7.6(8) . . . . ?
C4 C5 C10 C9 175.7(6) . . . . ?
C5 C6 C7 C8 -1.9(9) . . . . ?
C6 C1 C2 Br1 178.4(4) . . . . ?
C6 C1 C2 C3 -1.8(8) . . . . ?
C6 C5 C10 I1 172.6(4) . . . . ?
C6 C5 C10 C9 -4.0(9) . . . . ?
C6 C7 C8 C9 -1.4(9) . . . . ?
C7 C8 C9 C10 1.8(9) . . . . ?
C8 C9 C10 I1 -176.0(5) . . . . ?
C8 C9 C10 C5 1.0(9) . . . . ?
C10 C5 C6 C1 -173.4(5) . . . . ?
C10 C5 C6 C7 4.5(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_testt1
_database_code_depnum_ccdc_archive 'CCDC 1441691'
_audit_update_record             
;
2015-12-10 deposited with the CCDC.
2016-02-19 downloaded from the CCDC.
;
_audit_creation_date             2015-09-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H3 Br2 I O2'
_chemical_formula_sum            'C10 H3 Br2 I O2'
_chemical_formula_weight         441.84
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1805(2)
_cell_length_b                   8.2069(3)
_cell_length_c                   10.2503(3)
_cell_angle_alpha                67.006(2)
_cell_angle_beta                 88.761(2)
_cell_angle_gamma                69.374(2)
_cell_volume                     515.67(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3903
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      2.83
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    10.825
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4539
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0834 before and 0.0374 after correction.
The Ratio of minimum to maximum transmission is 0.6088.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.846
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8930
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.028
_diffrn_reflns_theta_min         2.178
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2214
_reflns_number_total             2508
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.890
_refine_diff_density_min         -0.808
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2508
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0212
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0257P)²+0.2385P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0489
_refine_ls_wR_factor_ref         0.0510
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.24019(3) 0.51390(3) 0.60445(2) 0.01379(7) Uani 1 1 d . . . . .
Br1 Br 0.28464(5) -0.04062(4) 1.41084(3) 0.01569(8) Uani 1 1 d . . . . .
Br2 Br 0.28779(5) 0.39861(4) 1.21666(3) 0.01420(8) Uani 1 1 d . . . . .
O1 O 0.2556(3) -0.2217(3) 1.2148(2) 0.0143(5) Uani 1 1 d . . . . .
O2 O 0.2196(4) 0.4887(3) 0.9091(2) 0.0204(5) Uani 1 1 d . . . . .
C1 C 0.2423(4) 0.0119(4) 0.9841(3) 0.0094(6) Uani 1 1 d . . . . .
C2 C 0.2539(4) -0.0633(4) 1.1437(3) 0.0108(6) Uani 1 1 d . . . . .
C3 C 0.2649(5) 0.0636(4) 1.2116(3) 0.0115(6) Uani 1 1 d . . . . .
C4 C 0.2647(4) 0.2377(4) 1.1348(3) 0.0109(6) Uani 1 1 d . . . . .
C5 C 0.2391(5) 0.3233(4) 0.9735(3) 0.0114(6) Uani 1 1 d . . . . .
C6 C 0.2368(4) 0.1971(4) 0.9010(3) 0.0095(6) Uani 1 1 d . . . . .
C7 C 0.2275(4) 0.2552(4) 0.7521(3) 0.0109(6) Uani 1 1 d . . . . .
C8 C 0.2185(4) 0.1342(4) 0.6911(3) 0.0126(6) Uani 1 1 d . . . . .
H8 H 0.2099 0.1754 0.5922 0.015 Uiso 1 1 calc R . . . .
C9 C 0.2218(5) -0.0473(4) 0.7739(3) 0.0125(6) Uani 1 1 d . . . . .
H9 H 0.2137 -0.1261 0.7310 0.015 Uiso 1 1 calc R . . . .
C10 C 0.2373(4) -0.1098(4) 0.9216(3) 0.0116(6) Uani 1 1 d . . . . .
H10 H 0.2443 -0.2326 0.9786 0.014 Uiso 1 1 calc R . . . .


_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 C7 2.104(3) . ?
Br1 C3 1.867(3) . ?
Br2 C4 1.872(3) . ?
O1 C2 1.213(4) . ?
O2 C5 1.212(4) . ?
C1 C2 1.498(4) . ?
C1 C6 1.409(4) . ?
C1 C10 1.391(4) . ?
C2 C3 1.484(4) . ?
C3 C4 1.334(4) . ?
C4 C5 1.508(4) . ?
C5 C6 1.496(4) . ?
C6 C7 1.405(4) . ?
C7 C8 1.384(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.389(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.389(4) . ?
C10 H10 0.9300 . ?

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
C6 C1 C2 121.6(3) . . ?
C10 C1 C2 116.8(3) . . ?
C10 C1 C6 121.5(3) . . ?
O1 C2 C1 121.5(3) . . ?
O1 C2 C3 121.2(3) . . ?
C3 C2 C1 117.2(2) . . ?
C2 C3 Br1 115.1(2) . . ?
C4 C3 Br1 123.0(2) . . ?
C4 C3 C2 121.9(3) . . ?
C3 C4 Br2 123.2(2) . . ?
C3 C4 C5 122.4(3) . . ?
C5 C4 Br2 114.4(2) . . ?
O2 C5 C4 119.4(3) . . ?
O2 C5 C6 123.2(3) . . ?
C6 C5 C4 117.3(2) . . ?
C1 C6 C5 119.3(3) . . ?
C7 C6 C1 117.8(3) . . ?
C7 C6 C5 123.0(3) . . ?
C6 C7 I1 125.9(2) . . ?
C8 C7 I1 113.9(2) . . ?
C8 C7 C6 120.2(3) . . ?
C7 C8 H8 119.2 . . ?
C7 C8 C9 121.6(3) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 120.4 . . ?
C10 C9 C8 119.2(3) . . ?
C10 C9 H9 120.4 . . ?
C1 C10 H10 120.1 . . ?
C9 C10 C1 119.8(3) . . ?
C9 C10 H10 120.1 . . ?

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
I1 C7 C8 C9 176.0(2) . . . . ?
Br1 C3 C4 Br2 0.9(4) . . . . ?
Br1 C3 C4 C5 -177.1(2) . . . . ?
Br2 C4 C5 O2 -5.7(4) . . . . ?
Br2 C4 C5 C6 175.0(2) . . . . ?
O1 C2 C3 Br1 0.8(4) . . . . ?
O1 C2 C3 C4 179.5(3) . . . . ?
O2 C5 C6 C1 -174.3(3) . . . . ?
O2 C5 C6 C7 5.1(5) . . . . ?
C1 C2 C3 Br1 -178.7(2) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C1 C6 C7 I1 -175.0(2) . . . . ?
C1 C6 C7 C8 1.8(4) . . . . ?
C2 C1 C6 C5 -1.0(4) . . . . ?
C2 C1 C6 C7 179.5(3) . . . . ?
C2 C1 C10 C9 178.5(3) . . . . ?
C2 C3 C4 Br2 -177.7(2) . . . . ?
C2 C3 C4 C5 4.3(5) . . . . ?
C3 C4 C5 O2 172.5(3) . . . . ?
C3 C4 C5 C6 -6.7(4) . . . . ?
C4 C5 C6 C1 5.0(4) . . . . ?
C4 C5 C6 C7 -175.6(3) . . . . ?
C5 C6 C7 I1 5.6(4) . . . . ?
C5 C6 C7 C8 -177.6(3) . . . . ?
C6 C1 C2 O1 178.9(3) . . . . ?
C6 C1 C2 C3 -1.6(4) . . . . ?
C6 C1 C10 C9 -1.5(4) . . . . ?
C6 C7 C8 C9 -1.2(5) . . . . ?
C7 C8 C9 C10 -0.9(5) . . . . ?
C8 C9 C10 C1 2.2(4) . . . . ?
C10 C1 C2 O1 -1.2(4) . . . . ?
C10 C1 C2 C3 178.4(3) . . . . ?
C10 C1 C6 C5 179.0(3) . . . . ?
C10 C1 C6 C7 -0.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_testm1
_database_code_depnum_ccdc_archive 'CCDC 1441692'
_audit_update_record             
;
2015-12-10 deposited with the CCDC.
2016-02-19 downloaded from the CCDC.
;
_audit_creation_date             2015-04-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H5 I O2'
_chemical_formula_sum            'C10 H5 I O2'
_chemical_formula_weight         284.04
_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'
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                   14.1706(8)
_cell_length_b                   4.1298(2)
_cell_length_c                   15.9165(10)
_cell_angle_alpha                90
_cell_angle_beta                 106.661(4)
_cell_angle_gamma                90
_cell_volume                     892.36(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1850
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.52
_cell_measurement_theta_min      2.67
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.547
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0733 before and 0.0527 after correction.
The Ratio of minimum to maximum transmission is 0.8138.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.114
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7669
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.027
_diffrn_reflns_theta_min         2.663
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1644
_reflns_number_total             2160
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         2.220
_refine_diff_density_min         -1.084
_refine_diff_density_rms         0.184
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.004
_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)+(0.0549P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.1009
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.85978(3) -0.34134(8) 0.46750(3) 0.02716(14) Uani 1 1 d . . . . .
O1 O 0.6547(3) -0.0362(11) 0.4679(3) 0.0309(9) Uani 1 1 d . . . . .
O2 O 0.8981(3) 0.0800(10) 0.7933(3) 0.0322(10) Uani 1 1 d . . . . .
C1 C 0.8133(4) -0.1240(12) 0.5671(4) 0.0224(11) Uani 1 1 d . . . . .
C2 C 0.7099(4) -0.0008(13) 0.5420(4) 0.0233(11) Uani 1 1 d . . . . .
C3 C 0.6767(4) 0.1640(12) 0.6120(4) 0.0210(11) Uani 1 1 d . . . . .
C4 C 0.5822(4) 0.2869(13) 0.5922(4) 0.0255(12) Uani 1 1 d . . . . .
H4 H 0.5389 0.2633 0.5347 0.031 Uiso 1 1 calc R . . . .
C5 C 0.5509(4) 0.4423(13) 0.6551(4) 0.0278(13) Uani 1 1 d . . . . .
H5 H 0.4865 0.5319 0.6402 0.033 Uiso 1 1 calc R . . . .
C6 C 0.6120(4) 0.4719(14) 0.7409(4) 0.0307(13) Uani 1 1 d . . . . .
H6 H 0.5889 0.5763 0.7844 0.037 Uiso 1 1 calc R . . . .
C7 C 0.7062(4) 0.3474(13) 0.7616(4) 0.0264(12) Uani 1 1 d . . . . .
H7 H 0.7485 0.3662 0.8197 0.032 Uiso 1 1 calc R . . . .
C8 C 0.7396(4) 0.1942(12) 0.6974(4) 0.0206(11) Uani 1 1 d . . . . .
C9 C 0.8415(4) 0.0609(13) 0.7195(4) 0.0261(12) Uani 1 1 d . . . . .
C10 C 0.8733(4) -0.0933(13) 0.6483(4) 0.0262(12) Uani 1 1 d . . . . .
H10 H 0.9387 -0.1733 0.6608 0.031 Uiso 1 1 calc R . . . .


_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 C1 2.087(5) . ?
O1 C2 1.223(7) . ?
O2 C9 1.221(7) . ?
C1 C2 1.494(7) . ?
C1 C10 1.333(8) . ?
C2 C3 1.492(7) . ?
C3 C4 1.381(7) . ?
C3 C8 1.402(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.366(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.397(9) . ?
C6 H6 0.9500 . ?
C6 C7 1.380(8) . ?
C7 H7 0.9500 . ?
C7 C8 1.395(7) . ?
C8 C9 1.491(8) . ?
C9 C10 1.478(8) . ?
C10 H10 0.9500 . ?

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
C2 C1 I1 116.2(4) . . ?
C10 C1 I1 121.7(4) . . ?
C10 C1 C2 122.1(5) . . ?
O1 C2 C1 121.7(5) . . ?
O1 C2 C3 121.6(5) . . ?
C3 C2 C1 116.7(5) . . ?
C4 C3 C2 119.3(5) . . ?
C4 C3 C8 119.6(5) . . ?
C8 C3 C2 121.1(5) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(6) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.1(5) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.2(5) . . ?
C7 C6 H6 120.4 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.1(6) . . ?
C8 C7 H7 119.9 . . ?
C3 C8 C9 119.9(5) . . ?
C7 C8 C3 119.8(5) . . ?
C7 C8 C9 120.3(5) . . ?
O2 C9 C8 121.8(5) . . ?
O2 C9 C10 120.4(5) . . ?
C10 C9 C8 117.8(5) . . ?
C1 C10 C9 122.3(5) . . ?
C1 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?

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
I1 C1 C2 O1 2.5(7) . . . . ?
I1 C1 C2 C3 -178.2(3) . . . . ?
I1 C1 C10 C9 179.8(4) . . . . ?
O1 C2 C3 C4 -1.6(8) . . . . ?
O1 C2 C3 C8 178.0(5) . . . . ?
O2 C9 C10 C1 178.8(5) . . . . ?
C1 C2 C3 C4 179.1(5) . . . . ?
C1 C2 C3 C8 -1.3(7) . . . . ?
C2 C1 C10 C9 0.8(8) . . . . ?
C2 C3 C4 C5 -179.1(5) . . . . ?
C2 C3 C8 C7 -179.5(5) . . . . ?
C2 C3 C8 C9 0.1(7) . . . . ?
C3 C4 C5 C6 -2.0(8) . . . . ?
C3 C8 C9 O2 -179.3(5) . . . . ?
C3 C8 C9 C10 1.5(7) . . . . ?
C4 C3 C8 C7 0.1(7) . . . . ?
C4 C3 C8 C9 179.7(5) . . . . ?
C4 C5 C6 C7 1.4(8) . . . . ?
C5 C6 C7 C8 0.0(8) . . . . ?
C6 C7 C8 C3 -0.7(8) . . . . ?
C6 C7 C8 C9 179.7(5) . . . . ?
C7 C8 C9 O2 0.3(8) . . . . ?
C7 C8 C9 C10 -178.9(5) . . . . ?
C8 C3 C4 C5 1.2(8) . . . . ?
C8 C9 C10 C1 -2.0(8) . . . . ?
C10 C1 C2 O1 -178.4(5) . . . . ?
C10 C1 C2 C3 0.8(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_testm1
_database_code_depnum_ccdc_archive 'CCDC 1441693'
_audit_update_record             
;
2015-12-10 deposited with the CCDC.
2016-02-19 downloaded from the CCDC.
;
_audit_creation_date             2015-09-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H4 I2 O2'
_chemical_formula_sum            'C10 H4 I2 O2'
_chemical_formula_weight         409.93
_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'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.9652(6)
_cell_length_b                   4.4527(2)
_cell_length_c                   16.4351(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.327(3)
_cell_angle_gamma                90
_cell_volume                     998.42(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3366
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.78
_cell_measurement_theta_min      2.54
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.267
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0638 before and 0.0406 after correction.
The Ratio of minimum to maximum transmission is 0.6947.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.727
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8503
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.859
_diffrn_reflns_theta_min         1.740
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2061
_reflns_number_total             2370
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.134
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0220
_refine_ls_restrained_S_all      1.029
_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)+(0.0180P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0408
_refine_ls_wR_factor_ref         0.0426
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.70080(2) 0.77724(4) 0.85624(2) 0.01831(7) Uani 1 1 d . . . . .
I2 I 0.33652(2) 0.17033(4) 0.54120(2) 0.01600(6) Uani 1 1 d . . . . .
O1 O 0.57265(18) 0.4125(5) 0.94129(14) 0.0246(6) Uani 1 1 d . . . . .
O2 O 0.31650(17) -0.1195(5) 0.70024(14) 0.0212(5) Uani 1 1 d . . . . .
C1 C 0.5105(2) 0.3205(7) 0.8838(2) 0.0148(7) Uani 1 1 d . . . . .
C2 C 0.4291(3) 0.1402(7) 0.9007(2) 0.0196(7) Uani 1 1 d . . . . .
H2 H 0.4215 0.1216 0.9554 0.023 Uiso 1 1 calc R . . . .
C3 C 0.3658(2) 0.0022(7) 0.8404(2) 0.0175(7) Uani 1 1 d . . . . .
H3 H 0.3175 -0.1190 0.8544 0.021 Uiso 1 1 calc R . . . .
C4 C 0.3697(2) 0.0351(7) 0.7523(2) 0.0147(7) Uani 1 1 d . . . . .
C5 C 0.4403(2) 0.2552(6) 0.72912(19) 0.0121(6) Uani 1 1 d . . . . .
C6 C 0.5121(2) 0.3876(6) 0.79405(19) 0.0117(6) Uani 1 1 d . . . . .
C7 C 0.5822(2) 0.5780(6) 0.7726(2) 0.0135(6) Uani 1 1 d . . . . .
C8 C 0.5783(2) 0.6516(7) 0.6899(2) 0.0160(7) Uani 1 1 d . . . . .
H8 H 0.6245 0.7823 0.6764 0.019 Uiso 1 1 calc R . . . .
C9 C 0.5063(2) 0.5322(7) 0.62735(19) 0.0150(7) Uani 1 1 d . . . . .
H9 H 0.5032 0.5873 0.5723 0.018 Uiso 1 1 calc R . . . .
C10 C 0.4387(2) 0.3308(6) 0.64627(19) 0.0127(6) 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 C7 2.109(3) . ?
I2 C10 2.116(3) . ?
O1 C1 1.210(4) . ?
O2 C4 1.219(4) . ?
C1 C2 1.466(5) . ?
C1 C6 1.510(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.330(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.467(4) . ?
C4 C5 1.496(4) . ?
C5 C6 1.427(4) . ?
C5 C10 1.398(4) . ?
C6 C7 1.395(4) . ?
C7 C8 1.388(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.381(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(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
O1 C1 C2 119.6(3) . . ?
O1 C1 C6 122.5(3) . . ?
C2 C1 C6 117.9(3) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 C1 122.0(3) . . ?
C3 C2 H2 119.0 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.1(3) . . ?
C4 C3 H3 119.0 . . ?
O2 C4 C3 119.4(3) . . ?
O2 C4 C5 121.8(3) . . ?
C3 C4 C5 118.8(3) . . ?
C6 C5 C4 118.5(3) . . ?
C10 C5 C4 122.1(3) . . ?
C10 C5 C6 119.4(3) . . ?
C5 C6 C1 119.6(3) . . ?
C7 C6 C1 121.7(3) . . ?
C7 C6 C5 118.8(3) . . ?
C6 C7 I1 125.9(2) . . ?
C8 C7 I1 113.6(2) . . ?
C8 C7 C6 120.5(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.3(3) . . ?
C10 C9 H9 119.8 . . ?
C5 C10 I2 125.5(2) . . ?
C9 C10 I2 114.1(2) . . ?
C9 C10 C5 120.3(3) . . ?

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
I1 C7 C8 C9 178.2(2) . . . . ?
O1 C1 C2 C3 -171.4(3) . . . . ?
O1 C1 C6 C5 175.7(3) . . . . ?
O1 C1 C6 C7 -4.6(5) . . . . ?
O2 C4 C5 C6 -168.8(3) . . . . ?
O2 C4 C5 C10 10.4(5) . . . . ?
C1 C2 C3 C4 -3.6(5) . . . . ?
C1 C6 C7 I1 4.6(4) . . . . ?
C1 C6 C7 C8 -175.8(3) . . . . ?
C2 C1 C6 C5 -5.1(4) . . . . ?
C2 C1 C6 C7 174.6(3) . . . . ?
C2 C3 C4 O2 172.6(3) . . . . ?
C2 C3 C4 C5 -6.5(5) . . . . ?
C3 C4 C5 C6 10.3(4) . . . . ?
C3 C4 C5 C10 -170.6(3) . . . . ?
C4 C5 C6 C1 -4.4(4) . . . . ?
C4 C5 C6 C7 175.9(3) . . . . ?
C4 C5 C10 I2 2.6(4) . . . . ?
C4 C5 C10 C9 -179.0(3) . . . . ?
C5 C6 C7 I1 -175.7(2) . . . . ?
C5 C6 C7 C8 3.9(4) . . . . ?
C6 C1 C2 C3 9.4(5) . . . . ?
C6 C5 C10 I2 -178.3(2) . . . . ?
C6 C5 C10 C9 0.1(4) . . . . ?
C6 C7 C8 C9 -1.4(5) . . . . ?
C7 C8 C9 C10 -1.8(5) . . . . ?
C8 C9 C10 I2 -179.0(2) . . . . ?
C8 C9 C10 C5 2.4(5) . . . . ?
C10 C5 C6 C1 176.5(3) . . . . ?
C10 C5 C6 C7 -3.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_testm1
_database_code_depnum_ccdc_archive 'CCDC 1441694'
_audit_update_record             
;
2015-12-10 deposited with the CCDC.
2016-02-19 downloaded from the CCDC.
;
_audit_creation_date             2015-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H5 Br O2'
_chemical_formula_sum            'C10 H5 Br O2'
_chemical_formula_weight         237.05
_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'
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                   7.7808(5)
_cell_length_b                   8.1027(5)
_cell_length_c                   12.8379(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.413(5)
_cell_angle_gamma                90
_cell_volume                     806.97(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2514
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.048
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0519 before and 0.0396 after correction.
The Ratio of minimum to maximum transmission is 0.8679.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.951
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7204
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.019
_diffrn_reflns_theta_min         2.626
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1671
_reflns_number_total             1953
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.208
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1953
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0248
_refine_ls_restrained_S_all      1.040
_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)+(0.0291P)²+0.4476P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0569
_refine_ls_wR_factor_ref         0.0600
_refine_special_details          
'Multiple datasets collected similar residuals.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Br1 Br 0.54293(3) 0.18912(3) 0.38587(2) 0.01400(8) Uani 1 1 d . . . . .
O1 O 0.9635(2) 0.8056(2) 0.61063(14) 0.0240(4) Uani 1 1 d . . . . .
O2 O 0.6377(2) 0.4993(2) 0.28804(13) 0.0231(4) Uani 1 1 d . . . . .
C1 C 0.7235(3) 0.4799(3) 0.47054(18) 0.0125(5) Uani 1 1 d . . . . .
C2 C 0.6713(3) 0.3173(3) 0.48776(17) 0.0128(4) Uani 1 1 d . . . . .
C3 C 0.7098(3) 0.2407(3) 0.58349(18) 0.0149(5) Uani 1 1 d . . . . .
H3 H 0.6712 0.1339 0.5942 0.018 Uiso 1 1 calc R . . . .
C4 C 0.8055(3) 0.3226(3) 0.66318(18) 0.0164(5) Uani 1 1 d . . . . .
H4 H 0.8333 0.2701 0.7267 0.020 Uiso 1 1 calc R . . . .
C5 C 0.8592(3) 0.4820(3) 0.64787(18) 0.0162(5) Uani 1 1 d . . . . .
H5 H 0.9239 0.5367 0.7012 0.019 Uiso 1 1 calc R . . . .
C6 C 0.8176(3) 0.5622(3) 0.55328(18) 0.0131(4) Uani 1 1 d . . . . .
C7 C 0.8736(3) 0.7364(3) 0.54172(19) 0.0161(5) Uani 1 1 d . . . . .
C8 C 0.8161(3) 0.8239(3) 0.4448(2) 0.0174(5) Uani 1 1 d . . . . .
H8 H 0.8426 0.9351 0.4380 0.021 Uiso 1 1 calc R . . . .
C9 C 0.7272(3) 0.7471(3) 0.36679(19) 0.0165(5) Uani 1 1 d . . . . .
H9 H 0.6872 0.8081 0.3085 0.020 Uiso 1 1 calc R . . . .
C10 C 0.6892(3) 0.5687(3) 0.36889(18) 0.0138(5) 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
Br1 C2 1.894(2) . ?
O1 C7 1.221(3) . ?
O2 C10 1.221(3) . ?
C1 C2 1.401(3) . ?
C1 C6 1.410(3) . ?
C1 C10 1.496(3) . ?
C2 C3 1.389(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.393(3) . ?
C6 C7 1.488(3) . ?
C7 C8 1.472(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.327(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.476(3) . ?

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
C2 C1 C6 117.8(2) . . ?
C2 C1 C10 123.7(2) . . ?
C6 C1 C10 118.5(2) . . ?
C1 C2 Br1 123.41(17) . . ?
C3 C2 Br1 115.63(18) . . ?
C3 C2 C1 120.9(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C7 120.8(2) . . ?
C5 C6 C1 120.6(2) . . ?
C5 C6 C7 118.6(2) . . ?
O1 C7 C6 121.3(2) . . ?
O1 C7 C8 120.8(2) . . ?
C8 C7 C6 118.0(2) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.3(2) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 118.7 . . ?
C8 C9 C10 122.6(2) . . ?
C10 C9 H9 118.7 . . ?
O2 C10 C1 123.0(2) . . ?
O2 C10 C9 119.2(2) . . ?
C9 C10 C1 117.7(2) . . ?

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
Br1 C2 C3 C4 179.03(17) . . . . ?
O1 C7 C8 C9 175.9(2) . . . . ?
C1 C2 C3 C4 -1.9(3) . . . . ?
C1 C6 C7 O1 -175.7(2) . . . . ?
C1 C6 C7 C8 4.8(3) . . . . ?
C2 C1 C6 C5 1.2(3) . . . . ?
C2 C1 C6 C7 -178.5(2) . . . . ?
C2 C1 C10 O2 -12.1(3) . . . . ?
C2 C1 C10 C9 170.6(2) . . . . ?
C2 C3 C4 C5 1.4(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 C1 -1.7(3) . . . . ?
C4 C5 C6 C7 178.0(2) . . . . ?
C5 C6 C7 O1 4.6(3) . . . . ?
C5 C6 C7 C8 -174.9(2) . . . . ?
C6 C1 C2 Br1 179.56(16) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C6 C1 C10 O2 166.2(2) . . . . ?
C6 C1 C10 C9 -11.1(3) . . . . ?
C6 C7 C8 C9 -4.6(3) . . . . ?
C7 C8 C9 C10 -3.8(4) . . . . ?
C8 C9 C10 O2 -165.6(2) . . . . ?
C8 C9 C10 C1 11.8(3) . . . . ?
C10 C1 C2 Br1 -2.2(3) . . . . ?
C10 C1 C2 C3 178.8(2) . . . . ?
C10 C1 C6 C5 -177.2(2) . . . . ?
C10 C1 C6 C7 3.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
