# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_2015565
_database_code_depnum_ccdc_archive 'CCDC 1471065'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-07-06 downloaded from the CCDC.
;
_audit_creation_date             2016-01-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Br C3 F2), C11 H8 O2'
_chemical_formula_sum            'C17 H8 Br2 F4 O2'
_chemical_formula_weight         480.05
_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'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 '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                   3.8981(3)
_cell_length_b                   13.3018(10)
_cell_length_c                   15.2307(11)
_cell_angle_alpha                93.626(3)
_cell_angle_beta                 96.888(3)
_cell_angle_gamma                93.357(4)
_cell_volume                     780.72(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8377
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.70
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.244
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1183 before and 0.0410 after correction.
The Ratio of minimum to maximum transmission is 0.5268.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'yellowish yellow'
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.042
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12713
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.558
_diffrn_reflns_theta_min         1.537
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.980
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3170
_reflns_number_total             3519
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3519
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0209
_refine_ls_restrained_S_all      1.031
_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+0.4292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0511
_refine_ls_wR_factor_ref         0.0529
_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:
 C6(H6), C8(H8), C7(H7), C5(H5), C3(H3)
2.b Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c)
;
_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 0.11532(5) 0.44333(2) 0.79418(2) 0.01838(6) Uani 1 1 d . . . . .
Br2 Br 0.81159(5) 0.08647(2) 0.19305(2) 0.01971(6) Uani 1 1 d . . . . .
F2 F 0.2356(3) 0.68439(8) 1.07766(7) 0.0238(2) Uani 1 1 d . . . . .
F3 F 1.1493(3) 0.19752(8) 0.05328(7) 0.0248(2) Uani 1 1 d . . . . .
F1 F 0.3234(3) 0.63762(8) 0.90838(7) 0.0240(2) Uani 1 1 d . . . . .
F4 F 0.7036(3) -0.12787(9) 0.10549(7) 0.0254(3) Uani 1 1 d . . . . .
O2 O 0.2287(4) 0.41389(10) 0.60855(9) 0.0243(3) Uani 1 1 d . . . . .
O1 O 0.6756(4) 0.16149(11) 0.36658(9) 0.0268(3) Uani 1 1 d . . . . .
C15 C 0.9206(5) 0.03674(14) 0.08290(11) 0.0167(4) Uani 1 1 d . . . . .
C14 C 0.1167(5) 0.59341(13) 1.03996(12) 0.0168(4) Uani 1 1 d . . . . .
C9 C 0.6010(5) 0.19314(14) 0.51704(12) 0.0177(4) Uani 1 1 d . . . . .
C16 C 1.0722(5) 0.10030(14) 0.02764(12) 0.0174(4) Uani 1 1 d . . . . .
C12 C 0.0462(5) 0.47576(14) 0.91176(11) 0.0157(3) Uani 1 1 d . . . . .
C6 C 0.6634(5) 0.14552(16) 0.69270(13) 0.0252(4) Uani 1 1 d . . . . .
H6 H 0.6864 0.1298 0.7517 0.030 Uiso 1 1 calc R . . . .
C17 C 0.8514(5) -0.06376(14) 0.05412(12) 0.0178(4) Uani 1 1 d . . . . .
C8 C 0.7372(5) 0.10350(15) 0.54025(13) 0.0218(4) Uani 1 1 d . . . . .
H8 H 0.8093 0.0596 0.4972 0.026 Uiso 1 1 calc R . . . .
C13 C 0.1614(5) 0.56934(13) 0.95279(12) 0.0168(4) Uani 1 1 d . . . . .
C7 C 0.7659(5) 0.07914(15) 0.62853(13) 0.0249(4) Uani 1 1 d . . . . .
H7 H 0.8538 0.0184 0.6443 0.030 Uiso 1 1 calc R . . . .
C10 C 0.4914(5) 0.26031(14) 0.58169(12) 0.0186(4) Uani 1 1 d . . . . .
C2 C 0.4237(5) 0.31451(14) 0.39805(12) 0.0196(4) Uani 1 1 d . . . . .
C11 C 0.4056(5) 0.33623(16) 0.30277(13) 0.0257(4) Uani 1 1 d . . . . .
H11A H 0.3138 0.4009 0.2948 0.038 Uiso 1 1 calc GR . . . .
H11B H 0.2577 0.2850 0.2673 0.038 Uiso 1 1 calc GR . . . .
H11C H 0.6336 0.3368 0.2849 0.038 Uiso 1 1 calc GR . . . .
C1 C 0.5732(5) 0.21832(14) 0.42263(13) 0.0189(4) Uani 1 1 d . . . . .
C4 C 0.3380(5) 0.35429(14) 0.55546(13) 0.0192(4) Uani 1 1 d . . . . .
C5 C 0.5257(5) 0.23596(15) 0.66913(13) 0.0222(4) Uani 1 1 d . . . . .
H5 H 0.4566 0.2801 0.7125 0.027 Uiso 1 1 calc R . . . .
C3 C 0.3133(5) 0.37629(14) 0.45997(13) 0.0201(4) Uani 1 1 d . . . . .
H3 H 0.2170 0.4354 0.4428 0.024 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
Br1 C12 1.8702(17) . ?
Br2 C15 1.8699(17) . ?
F2 C14 1.339(2) . ?
F3 C16 1.333(2) . ?
F1 C13 1.340(2) . ?
F4 C17 1.344(2) . ?
O2 C4 1.227(2) . ?
O1 C1 1.223(2) . ?
C15 C16 1.387(2) . ?
C15 C17 1.381(3) . ?
C14 C12 1.386(3) 2_567 ?
C14 C13 1.380(2) . ?
C9 C8 1.382(3) . ?
C9 C10 1.409(2) . ?
C9 C1 1.490(3) . ?
C16 C17 1.380(2) 2_755 ?
C12 C14 1.385(3) 2_567 ?
C12 C13 1.382(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.386(3) . ?
C6 C5 1.396(3) . ?
C17 C16 1.380(2) 2_755 ?
C8 H8 0.9300 . ?
C8 C7 1.396(3) . ?
C7 H7 0.9300 . ?
C10 C4 1.474(3) . ?
C10 C5 1.383(3) . ?
C2 C11 1.492(3) . ?
C2 C1 1.487(3) . ?
C2 C3 1.338(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C4 C3 1.495(3) . ?
C5 H5 0.9300 . ?
C3 H3 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
C16 C15 Br2 120.65(14) . . ?
C17 C15 Br2 121.16(14) . . ?
C17 C15 C16 118.19(16) . . ?
F2 C14 C12 120.30(16) . 2_567 ?
F2 C14 C13 119.09(16) . . ?
C13 C14 C12 120.61(16) . 2_567 ?
C8 C9 C10 120.62(17) . . ?
C8 C9 C1 119.14(16) . . ?
C10 C9 C1 120.24(17) . . ?
F3 C16 C15 120.32(16) . . ?
F3 C16 C17 119.09(16) . 2_755 ?
C17 C16 C15 120.59(17) 2_755 . ?
C14 C12 Br1 121.06(13) 2_567 . ?
C13 C12 Br1 120.43(14) . . ?
C13 C12 C14 118.51(16) . 2_567 ?
C7 C6 H6 119.9 . . ?
C7 C6 C5 120.21(18) . . ?
C5 C6 H6 119.9 . . ?
F4 C17 C15 120.11(16) . . ?
F4 C17 C16 118.67(16) . 2_755 ?
C16 C17 C15 121.21(17) 2_755 . ?
C9 C8 H8 120.1 . . ?
C9 C8 C7 119.75(18) . . ?
C7 C8 H8 120.1 . . ?
F1 C13 C14 119.03(16) . . ?
F1 C13 C12 120.08(16) . . ?
C14 C13 C12 120.88(17) . . ?
C6 C7 C8 119.96(19) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C10 C4 119.93(17) . . ?
C5 C10 C9 119.08(18) . . ?
C5 C10 C4 120.98(17) . . ?
C1 C2 C11 116.47(16) . . ?
C3 C2 C11 123.39(19) . . ?
C3 C2 C1 120.13(18) . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C1 C9 120.54(17) . . ?
O1 C1 C2 120.62(17) . . ?
C2 C1 C9 118.83(16) . . ?
O2 C4 C10 122.63(18) . . ?
O2 C4 C3 119.34(18) . . ?
C10 C4 C3 118.03(16) . . ?
C6 C5 H5 119.8 . . ?
C10 C5 C6 120.37(17) . . ?
C10 C5 H5 119.8 . . ?
C2 C3 C4 122.80(18) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?

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 C12 C13 F1 0.1(2) . . . . ?
Br1 C12 C13 C14 -178.92(14) . . . . ?
Br2 C15 C16 F3 1.5(2) . . . . ?
Br2 C15 C16 C17 -179.18(14) . . . 2_755 ?
Br2 C15 C17 F4 -0.1(2) . . . . ?
Br2 C15 C17 C16 179.18(14) . . . 2_755 ?
F2 C14 C13 F1 0.2(3) . . . . ?
F2 C14 C13 C12 179.21(16) . . . . ?
O2 C4 C3 C2 -179.37(19) . . . . ?
C14 C12 C13 F1 179.25(16) 2_567 . . . ?
C14 C12 C13 C14 0.3(3) 2_567 . . . ?
C9 C8 C7 C6 -1.1(3) . . . . ?
C9 C10 C4 O2 177.72(18) . . . . ?
C9 C10 C4 C3 -1.7(3) . . . . ?
C9 C10 C5 C6 -0.7(3) . . . . ?
C16 C15 C17 F4 -179.80(16) . . . . ?
C16 C15 C17 C16 -0.6(3) . . . 2_755 ?
C12 C14 C13 F1 -179.26(16) 2_567 . . . ?
C12 C14 C13 C12 -0.3(3) 2_567 . . . ?
C17 C15 C16 F3 -178.81(16) . . . . ?
C17 C15 C16 C17 0.5(3) . . . 2_755 ?
C8 C9 C10 C4 -178.33(17) . . . . ?
C8 C9 C10 C5 0.8(3) . . . . ?
C8 C9 C1 O1 -1.4(3) . . . . ?
C8 C9 C1 C2 179.51(17) . . . . ?
C7 C6 C5 C10 -0.2(3) . . . . ?
C10 C9 C8 C7 0.1(3) . . . . ?
C10 C9 C1 O1 178.21(18) . . . . ?
C10 C9 C1 C2 -0.9(3) . . . . ?
C10 C4 C3 C2 0.1(3) . . . . ?
C11 C2 C1 O1 0.3(3) . . . . ?
C11 C2 C1 C9 179.41(17) . . . . ?
C11 C2 C3 C4 -179.05(18) . . . . ?
C1 C9 C8 C7 179.76(17) . . . . ?
C1 C9 C10 C4 2.0(3) . . . . ?
C1 C9 C10 C5 -178.87(17) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C4 C10 C5 C6 178.37(17) . . . . ?
C5 C6 C7 C8 1.1(3) . . . . ?
C5 C10 C4 O2 -1.3(3) . . . . ?
C5 C10 C4 C3 179.26(17) . . . . ?
C3 C2 C1 O1 -179.83(19) . . . . ?
C3 C2 C1 C9 -0.8(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_2015620
_database_code_depnum_ccdc_archive 'CCDC 1471066'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-07-06 downloaded from the CCDC.
;
_audit_creation_date             2016-03-03
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C6 F4 I2, C11 H8 O2'
_chemical_formula_sum            'C17 H8 F4 I2 O2'
_chemical_formula_weight         574.03
_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'
F F 0.0171 0.0103 '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                   17.0631(12)
_cell_length_b                   4.1837(3)
_cell_length_c                   24.5252(19)
_cell_angle_alpha                90
_cell_angle_beta                 100.088(5)
_cell_angle_gamma                90
_cell_volume                     1723.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4888
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.27
_cell_measurement_theta_min      2.61
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.697
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0735 before and 0.0426 after correction.
The Ratio of minimum to maximum transmission is 0.7082.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.212
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            15020
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.578
_diffrn_reflns_theta_min         1.593
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.983
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3001
_reflns_number_total             3937
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         1.704
_refine_diff_density_min         -0.956
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3937
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.020
_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)+(0.0308P)²+3.7047P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0795
_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:
 C6(H6), C5(H5), C3(H3), C7(H7), C8(H8)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_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
I2 I -0.06978(2) 1.15275(8) 0.15194(2) 0.04261(11) Uani 1 1 d . . . . .
I1 I 0.30180(2) 0.61075(8) 0.11132(2) 0.04031(10) Uani 1 1 d . . . . .
F2 F 0.10357(15) 1.2176(8) 0.22293(11) 0.0487(7) Uani 1 1 d . . . . .
F3 F -0.01352(16) 0.7737(9) 0.05132(13) 0.0624(9) Uani 1 1 d . . . . .
F1 F 0.24528(14) 1.0061(8) 0.20794(11) 0.0460(7) Uani 1 1 d . . . . .
F4 F 0.12906(18) 0.5637(9) 0.03629(13) 0.0666(10) Uani 1 1 d . . . . .
C6 C 0.7176(3) 0.8318(14) 0.0367(2) 0.0532(14) Uani 1 1 d . . . . .
H6 H 0.7573 0.9188 0.0183 0.064 Uiso 1 1 calc R . . . .
C5 C 0.7403(3) 0.6698(12) 0.0866(2) 0.0443(12) Uani 1 1 d . . . . .
H5 H 0.7950 0.6464 0.1020 0.053 Uiso 1 1 calc R . . . .
C10 C 0.6830(3) 0.5439(12) 0.1134(2) 0.0364(11) Uani 1 1 d . . . . .
C4 C 0.7059(3) 0.3726(12) 0.1664(2) 0.0410(12) Uani 1 1 d . . . . .
C3 C 0.6411(3) 0.2514(13) 0.1944(2) 0.0411(11) Uani 1 1 d . . . . .
H3 H 0.6555 0.1453 0.2289 0.049 Uiso 1 1 calc R . . . .
C2 C 0.5634(3) 0.2844(12) 0.1734(2) 0.0376(11) Uani 1 1 d . . . . .
C11 C 0.4987(3) 0.1611(14) 0.2007(2) 0.0524(14) Uani 1 1 d . . . . .
H11A H 0.5218 0.0473 0.2347 0.079 Uiso 1 1 calc GR . . . .
H11B H 0.4651 0.0144 0.1756 0.079 Uiso 1 1 calc GR . . . .
H11C H 0.4664 0.3401 0.2100 0.079 Uiso 1 1 calc GR . . . .
C7 C 0.6386(3) 0.8680(13) 0.0137(2) 0.0478(13) Uani 1 1 d . . . . .
H7 H 0.6238 0.9783 -0.0204 0.057 Uiso 1 1 calc R . . . .
C8 C 0.5801(3) 0.7408(12) 0.0409(2) 0.0404(11) Uani 1 1 d . . . . .
H8 H 0.5254 0.7638 0.0252 0.048 Uiso 1 1 calc R . . . .
C9 C 0.6013(3) 0.5839(11) 0.09010(19) 0.0331(10) Uani 1 1 d . . . . .
C1 C 0.5397(3) 0.4476(12) 0.11915(19) 0.0349(10) Uani 1 1 d . . . . .
O1 O 0.46942(18) 0.4698(10) 0.09848(14) 0.0508(10) Uani 1 1 d . . . . .
O2 O 0.77521(18) 0.3248(10) 0.18674(15) 0.0544(10) Uani 1 1 d . . . . .
C16 C 0.0500(3) 0.8349(12) 0.0903(2) 0.0402(11) Uani 1 1 d . . . . .
C15 C 0.0410(2) 1.0000(11) 0.13743(19) 0.0316(10) Uani 1 1 d . . . . .
C14 C 0.1081(3) 1.0545(11) 0.17676(19) 0.0338(10) Uani 1 1 d . . . . .
C13 C 0.1817(2) 0.9452(11) 0.16889(19) 0.0329(10) Uani 1 1 d . . . . .
C12 C 0.1907(2) 0.7781(11) 0.12171(19) 0.0319(10) Uani 1 1 d . . . . .
C17 C 0.1237(3) 0.7266(12) 0.0826(2) 0.0399(11) 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
I2 C15 2.085(4) . ?
I1 C12 2.078(4) . ?
F2 C14 1.336(5) . ?
F3 C16 1.339(5) . ?
F1 C13 1.339(5) . ?
F4 C17 1.341(5) . ?
C6 H6 0.9500 . ?
C6 C5 1.392(8) . ?
C6 C7 1.375(7) . ?
C5 H5 0.9500 . ?
C5 C10 1.375(7) . ?
C10 C4 1.475(7) . ?
C10 C9 1.421(6) . ?
C4 C3 1.489(7) . ?
C4 O2 1.217(5) . ?
C3 H3 0.9500 . ?
C3 C2 1.343(6) . ?
C2 C11 1.482(7) . ?
C2 C1 1.486(7) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C7 H7 0.9500 . ?
C7 C8 1.400(7) . ?
C8 H8 0.9500 . ?
C8 C9 1.365(7) . ?
C9 C1 1.483(6) . ?
C1 O1 1.221(5) . ?
C16 C15 1.377(7) . ?
C16 C17 1.381(6) . ?
C15 C14 1.380(6) . ?
C14 C13 1.383(6) . ?
C13 C12 1.383(6) . ?
C12 C17 1.374(6) . ?

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
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C7 C6 C5 121.0(5) . . ?
C6 C5 H5 120.2 . . ?
C10 C5 C6 119.7(5) . . ?
C10 C5 H5 120.2 . . ?
C5 C10 C4 120.4(4) . . ?
C5 C10 C9 119.5(5) . . ?
C9 C10 C4 120.1(4) . . ?
C10 C4 C3 117.9(4) . . ?
O2 C4 C10 122.0(5) . . ?
O2 C4 C3 120.1(5) . . ?
C4 C3 H3 118.3 . . ?
C2 C3 C4 123.4(5) . . ?
C2 C3 H3 118.3 . . ?
C3 C2 C11 123.7(5) . . ?
C3 C2 C1 119.1(4) . . ?
C11 C2 C1 117.2(4) . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C7 H7 120.3 . . ?
C6 C7 C8 119.5(5) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.3(4) . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C1 119.3(4) . . ?
C8 C9 C10 120.1(4) . . ?
C8 C9 C1 120.6(4) . . ?
C9 C1 C2 120.1(4) . . ?
O1 C1 C2 120.0(4) . . ?
O1 C1 C9 119.9(4) . . ?
F3 C16 C15 120.0(4) . . ?
F3 C16 C17 118.8(4) . . ?
C15 C16 C17 121.2(4) . . ?
C16 C15 I2 122.3(3) . . ?
C16 C15 C14 118.0(4) . . ?
C14 C15 I2 119.7(3) . . ?
F2 C14 C15 120.9(4) . . ?
F2 C14 C13 118.4(4) . . ?
C15 C14 C13 120.7(4) . . ?
F1 C13 C14 118.6(4) . . ?
F1 C13 C12 120.0(4) . . ?
C14 C13 C12 121.3(4) . . ?
C13 C12 I1 120.6(3) . . ?
C17 C12 I1 121.8(3) . . ?
C17 C12 C13 117.6(4) . . ?
F4 C17 C16 118.8(4) . . ?
F4 C17 C12 120.0(4) . . ?
C12 C17 C16 121.3(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
I2 C15 C14 F2 -3.3(6) . . . . ?
I2 C15 C14 C13 177.7(3) . . . . ?
I1 C12 C17 F4 0.2(7) . . . . ?
I1 C12 C17 C16 179.0(4) . . . . ?
F2 C14 C13 F1 0.3(7) . . . . ?
F2 C14 C13 C12 -179.2(4) . . . . ?
F3 C16 C15 I2 1.5(7) . . . . ?
F3 C16 C15 C14 179.3(4) . . . . ?
F3 C16 C17 F4 -0.1(7) . . . . ?
F3 C16 C17 C12 -178.9(5) . . . . ?
F1 C13 C12 I1 1.3(6) . . . . ?
F1 C13 C12 C17 -179.0(4) . . . . ?
C6 C5 C10 C4 -179.8(5) . . . . ?
C6 C5 C10 C9 -0.7(7) . . . . ?
C6 C7 C8 C9 0.4(8) . . . . ?
C5 C6 C7 C8 0.2(8) . . . . ?
C5 C10 C4 C3 177.9(5) . . . . ?
C5 C10 C4 O2 -3.2(7) . . . . ?
C5 C10 C9 C8 1.3(7) . . . . ?
C5 C10 C9 C1 180.0(4) . . . . ?
C10 C4 C3 C2 1.4(7) . . . . ?
C10 C9 C1 C2 2.9(7) . . . . ?
C10 C9 C1 O1 -177.2(4) . . . . ?
C4 C10 C9 C8 -179.6(4) . . . . ?
C4 C10 C9 C1 -0.9(7) . . . . ?
C4 C3 C2 C11 179.3(5) . . . . ?
C4 C3 C2 C1 0.5(8) . . . . ?
C3 C2 C1 C9 -2.6(7) . . . . ?
C3 C2 C1 O1 177.4(5) . . . . ?
C11 C2 C1 C9 178.5(4) . . . . ?
C11 C2 C1 O1 -1.4(7) . . . . ?
C7 C6 C5 C10 -0.1(8) . . . . ?
C7 C8 C9 C10 -1.1(7) . . . . ?
C7 C8 C9 C1 -179.8(4) . . . . ?
C8 C9 C1 C2 -178.5(4) . . . . ?
C8 C9 C1 O1 1.5(7) . . . . ?
C9 C10 C4 C3 -1.2(7) . . . . ?
C9 C10 C4 O2 177.7(5) . . . . ?
O2 C4 C3 C2 -177.4(5) . . . . ?
C16 C15 C14 F2 178.9(4) . . . . ?
C16 C15 C14 C13 -0.2(7) . . . . ?
C15 C16 C17 F4 179.2(5) . . . . ?
C15 C16 C17 C12 0.4(8) . . . . ?
C15 C14 C13 F1 179.4(4) . . . . ?
C15 C14 C13 C12 -0.1(7) . . . . ?
C14 C13 C12 I1 -179.1(3) . . . . ?
C14 C13 C12 C17 0.5(7) . . . . ?
C13 C12 C17 F4 -179.5(5) . . . . ?
C13 C12 C17 C16 -0.6(7) . . . . ?
C17 C16 C15 I2 -177.7(4) . . . . ?
C17 C16 C15 C14 0.1(7) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
