# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_hmt70074
_database_code_depnum_ccdc_archive 'CCDC 1590512'
loop_
_audit_author_name
_audit_author_address
'Zhiyong Jiang' 'Henan University'
_audit_update_record             
;
2017-12-11 deposited with the CCDC.	2019-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 Br F O'
_chemical_formula_weight         243.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.8209(6)
_cell_length_b                   6.9066(8)
_cell_length_c                   8.6288(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.372(7)
_cell_angle_gamma                90
_cell_volume                     458.47(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    5.892
_shelx_estimated_absorpt_T_min   0.344
_shelx_estimated_absorpt_T_max   0.650
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3410
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.211
_diffrn_reflns_theta_max         67.062
_diffrn_reflns_theta_full        67.062
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.930
_reflns_number_total             1530
_reflns_number_gt                1336
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_max     0.846
_reflns_Friedel_fraction_full    0.846

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0505P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 497 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1530
_refine_ls_number_parameters     118
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0855
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.89866(7) 0.49638(2) 0.60061(7) 0.0660(3) Uani 1 1 d . . . . .
C1 C 0.6489(7) 0.491(3) 0.3177(6) 0.0510(16) Uani 1 1 d . . . . .
H1 H 0.7452 0.4868 0.2685 0.061 Uiso 1 1 calc R U . . .
C2 C 0.6706(6) 0.495(3) 0.4785(6) 0.0477(11) Uani 1 1 d . . . . .
C3 C 0.5288(7) 0.498(3) 0.5553(6) 0.0528(13) Uani 1 1 d . . . . .
H3 H 0.5447 0.4983 0.6647 0.063 Uiso 1 1 calc R U . . .
C4 C 0.3654(7) 0.501(3) 0.4661(6) 0.0518(13) Uani 1 1 d . . . . .
H4 H 0.2700 0.5048 0.5166 0.062 Uiso 1 1 calc R U . . .
C5 C 0.3375(6) 0.499(3) 0.3020(6) 0.0477(11) Uani 1 1 d . . . . .
C6 C 0.4830(6) 0.494(3) 0.2284(5) 0.0452(11) Uani 1 1 d . . . . .
C7 C 0.4619(7) 0.495(3) 0.0530(6) 0.0551(15) Uani 1 1 d . . . . .
C8 C 0.2784(9) 0.464(3) -0.0327(7) 0.067(5) Uani 1 1 d . . . . .
H8 H 0.2505 0.3261 -0.0326 0.080 Uiso 1 1 calc R U . . .
C9 C 0.1487(9) 0.5749(13) 0.0420(8) 0.063(2) Uani 1 1 d . . . . .
H9A H 0.0328 0.5594 -0.0194 0.076 Uiso 1 1 calc R U . . .
H9B H 0.1772 0.7117 0.0470 0.076 Uiso 1 1 calc R U . . .
C10 C 0.1564(6) 0.494(3) 0.2080(6) 0.0578(14) Uani 1 1 d . . . . .
H10A H 0.0801 0.5684 0.2620 0.069 Uiso 1 1 calc R U . . .
H10B H 0.1150 0.3609 0.2007 0.069 Uiso 1 1 calc R U . . .
F1 F 0.2697(6) 0.526(3) -0.1862(4) 0.121(4) Uani 1 1 d . . . . .
O1 O 0.5835(5) 0.501(3) -0.0146(4) 0.0689(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
Br1 C2 1.901(5) . ?
C1 C2 1.367(7) . ?
C1 C6 1.385(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.390(7) . ?
C3 C4 1.368(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.400(7) . ?
C5 C10 1.501(7) . ?
C6 C7 1.492(6) . ?
C7 O1 1.203(7) . ?
C7 C8 1.506(11) . ?
C8 F1 1.380(12) . ?
C8 C9 1.504(15) . ?
C8 H8 0.9800 . ?
C9 C10 1.530(12) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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 119.9(4) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C1 C2 C3 121.3(4) . . ?
C1 C2 Br1 119.7(4) . . ?
C3 C2 Br1 119.0(4) . . ?
C4 C3 C2 118.5(4) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 122.1(4) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C4 C5 C6 118.0(5) . . ?
C4 C5 C10 120.6(4) . . ?
C6 C5 C10 121.3(4) . . ?
C1 C6 C5 120.3(4) . . ?
C1 C6 C7 119.1(4) . . ?
C5 C6 C7 120.6(5) . . ?
O1 C7 C6 122.6(5) . . ?
O1 C7 C8 122.3(5) . . ?
C6 C7 C8 114.8(6) . . ?
F1 C8 C9 109.6(14) . . ?
F1 C8 C7 107.9(9) . . ?
C9 C8 C7 112.1(12) . . ?
F1 C8 H8 109.1 . . ?
C9 C8 H8 109.1 . . ?
C7 C8 H8 109.1 . . ?
C8 C9 C10 107.4(9) . . ?
C8 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
C8 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
C5 C10 C9 111.8(7) . . ?
C5 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C5 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?

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
C6 C1 C2 C3 1(3) . . . . ?
C6 C1 C2 Br1 -178.7(18) . . . . ?
C1 C2 C3 C4 -1(3) . . . . ?
Br1 C2 C3 C4 178.8(15) . . . . ?
C2 C3 C4 C5 1(4) . . . . ?
C3 C4 C5 C6 0(3) . . . . ?
C3 C4 C5 C10 177(2) . . . . ?
C2 C1 C6 C5 -1(3) . . . . ?
C2 C1 C6 C7 179(2) . . . . ?
C4 C5 C6 C1 0(3) . . . . ?
C10 C5 C6 C1 -177(2) . . . . ?
C4 C5 C6 C7 -179(3) . . . . ?
C10 C5 C6 C7 3(3) . . . . ?
C1 C6 C7 O1 -3(4) . . . . ?
C5 C6 C7 O1 176(2) . . . . ?
C1 C6 C7 C8 170(2) . . . . ?
C5 C6 C7 C8 -10(3) . . . . ?
O1 C7 C8 F1 -24(3) . . . . ?
C6 C7 C8 F1 162.1(19) . . . . ?
O1 C7 C8 C9 -144.9(18) . . . . ?
C6 C7 C8 C9 41(3) . . . . ?
F1 C8 C9 C10 176.8(14) . . . . ?
C7 C8 C9 C10 -63.5(17) . . . . ?
C4 C5 C10 C9 156.1(19) . . . . ?
C6 C5 C10 C9 -26(3) . . . . ?
C8 C9 C10 C5 54.8(18) . . . . ?

_refine_diff_density_max         0.430
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_hm23026
_database_code_depnum_ccdc_archive 'CCDC 1840318'
loop_
_audit_author_name
_audit_author_address
'Zhiyong Jiang'
;Henan University
China
;
_audit_update_record             
;
2018-04-29 deposited with the CCDC.	2019-05-30 downloaded from the CCDC.
;
_audit_creation_date             2018-04-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H10 Cl2 O'
_chemical_formula_sum            'C10 H10 Cl2 O'
_chemical_formula_weight         217.08
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H15O3N2Cl2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   5.04728(18)
_cell_length_b                   19.5159(6)
_cell_length_c                   20.2528(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1994.94(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3155
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6540
_cell_measurement_theta_min      4.3940
_shelx_estimated_absorpt_T_max   0.610
_shelx_estimated_absorpt_T_min   0.474
_exptl_absorpt_coefficient_mu    5.490
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8713
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.069
_diffrn_reflns_theta_max         67.069
_diffrn_reflns_theta_min         4.366
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -101.00  -26.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -37.0000  -90.0000 75

#__ type_ start__ end____ width___ exp.time_
  2 omega  -98.00  -42.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000 -180.0000 56

#__ type_ start__ end____ width___ exp.time_
  3 omega   26.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461   57.0000  -90.0000 60

#__ type_ start__ end____ width___ exp.time_
  4 omega   18.00   65.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461  -77.0000  150.0000 47

#__ type_ start__ end____ width___ exp.time_
  5 omega   14.00   68.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461  -19.0000  -60.0000 54

#__ type_ start__ end____ width___ exp.time_
  6 omega  -35.00  -10.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461  -19.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega   58.00  106.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461  178.0000 -180.0000 48

#__ type_ start__ end____ width___ exp.time_
  8 omega   63.00  105.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461   77.0000  -90.0000 42

#__ type_ start__ end____ width___ exp.time_
  9 omega   16.00   43.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461   77.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega   58.00  108.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461  178.0000   60.0000 50

#__ type_ start__ end____ width___ exp.time_
 11 omega   53.00   80.00   1.0000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -130.0000  -26.0000 27

#__ type_ start__ end____ width___ exp.time_
 12 omega   69.00  107.00   1.0000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 38

#__ type_ start__ end____ width___ exp.time_
 13 omega  123.00  177.00   1.0000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 54

#__ type_ start__ end____ width___ exp.time_
 14 omega   42.00   90.00   1.0000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 48

#__ type_ start__ end____ width___ exp.time_
 15 omega   39.00   91.00   1.0000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 52

#__ type_ start__ end____ width___ exp.time_
 16 omega  128.00  163.00   1.0000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  150.0000 35

#__ type_ start__ end____ width___ exp.time_
 17 omega   83.00  109.00   1.0000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   38.00  152.00   1.0000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  120.0000 114

#__ type_ start__ end____ width___ exp.time_
 19 omega   43.00   77.00   1.0000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
 20 omega   47.00   97.00   1.0000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 50

#__ type_ start__ end____ width___ exp.time_
 21 omega   38.00   99.00   1.0000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 61

#__ type_ start__ end____ width___ exp.time_
 22 omega   26.00   52.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega  -29.00   -3.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 24 omega  142.00  151.00   1.0000   19.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 9
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0040301000
_diffrn_orient_matrix_UB_12      -0.0133649000
_diffrn_orient_matrix_UB_13      0.0749899000
_diffrn_orient_matrix_UB_21      -0.0899339000
_diffrn_orient_matrix_UB_22      0.0742855000
_diffrn_orient_matrix_UB_23      0.0124077000
_diffrn_orient_matrix_UB_31      -0.2916829000
_diffrn_orient_matrix_UB_32      -0.0231149000
_diffrn_orient_matrix_UB_33      -0.0027569000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3017
_reflns_number_total             3534
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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 (Sheldrick, 2008)'
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 1029 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3534
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.032
_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)+(0.0670P)²+0.1539P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1265
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C1'(H1'), C2'(H2')
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C3'(H3'A,H3'B), C4'(H4'A,H4'B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C7'(H7'), C8'(H8'), C10'(H10')
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.4524(9) 0.6731(2) 0.7674(2) 0.0477(10) Uani 1 1 d . . . . .
H1 H 0.2765 0.6934 0.7737 0.057 Uiso 1 1 calc R . . . .
C2 C 0.4476(10) 0.6342(2) 0.7032(3) 0.0532(11) Uani 1 1 d . . . . .
H2 H 0.2947 0.6033 0.7033 0.064 Uiso 1 1 calc R . . . .
C3 C 0.4213(10) 0.6830(3) 0.6451(3) 0.0559(12) Uani 1 1 d . . . . .
H3A H 0.2586 0.7091 0.6495 0.067 Uiso 1 1 calc R . . . .
H3B H 0.4109 0.6569 0.6045 0.067 Uiso 1 1 calc R . . . .
C4 C 0.6554(11) 0.7322(2) 0.6413(2) 0.0518(12) Uani 1 1 d . . . . .
H4A H 0.8051 0.7086 0.6217 0.062 Uiso 1 1 calc R . . . .
H4B H 0.6091 0.7702 0.6126 0.062 Uiso 1 1 calc R . . . .
C5 C 0.7370(10) 0.76029(19) 0.7081(2) 0.0424(9) Uani 1 1 d . . . . .
C6 C 0.6518(9) 0.7310(2) 0.7673(2) 0.0430(10) Uani 1 1 d . . . . .
C7 C 0.7456(12) 0.7577(2) 0.8270(2) 0.0525(11) Uani 1 1 d . . . . .
H7 H 0.6881 0.7386 0.8665 0.063 Uiso 1 1 calc R . . . .
C8 C 0.9208(12) 0.8115(2) 0.8285(3) 0.0581(13) Uani 1 1 d . . . . .
H8 H 0.9855 0.8281 0.8684 0.070 Uiso 1 1 calc R . . . .
C9 C 0.9983(11) 0.8402(2) 0.7697(3) 0.0540(12) Uani 1 1 d . . . . .
C10 C 0.9145(11) 0.8152(2) 0.7100(2) 0.0507(12) Uani 1 1 d . . . . .
H10 H 0.9755 0.8346 0.6709 0.061 Uiso 1 1 calc R . . . .
Cl1 Cl 0.7467(3) 0.58362(6) 0.69467(7) 0.0651(3) Uani 1 1 d . . . . .
Cl2 Cl 1.2146(4) 0.91036(7) 0.77110(8) 0.0889(6) Uani 1 1 d . . . . .
O1 O 0.5028(8) 0.6297(2) 0.8222(2) 0.0598(10) Uani 1 1 d . . . . .
H1A H 0.387(13) 0.619(3) 0.840(3) 0.060(19) Uiso 1 1 d . . . . .
C1' C 0.5328(10) 0.4323(3) 0.4308(3) 0.0517(11) Uani 1 1 d . . . . .
H1' H 0.7068 0.4546 0.4311 0.062 Uiso 1 1 calc R . . . .
C2' C 0.5348(10) 0.3782(3) 0.4849(3) 0.0570(13) Uani 1 1 d . . . . .
H2' H 0.6875 0.3480 0.4781 0.068 Uiso 1 1 calc R . . . .
C3' C 0.5594(11) 0.4117(3) 0.5515(3) 0.0692(16) Uani 1 1 d . . . . .
H3'A H 0.7292 0.4349 0.5541 0.083 Uiso 1 1 calc R . . . .
H3'B H 0.5570 0.3765 0.5853 0.083 Uiso 1 1 calc R . . . .
C4' C 0.3414(12) 0.4631(3) 0.5660(3) 0.0650(15) Uani 1 1 d . . . . .
H4'A H 0.1921 0.4388 0.5851 0.078 Uiso 1 1 calc R . . . .
H4'B H 0.4053 0.4951 0.5990 0.078 Uiso 1 1 calc R . . . .
C5' C 0.2453(12) 0.5030(2) 0.5072(2) 0.0501(11) Uani 1 1 d . . . . .
C6' C 0.3274(9) 0.4873(2) 0.4428(2) 0.0474(11) Uani 1 1 d . . . . .
C7' C 0.2238(12) 0.5243(2) 0.3900(2) 0.0527(11) Uani 1 1 d . . . . .
H7' H 0.2788 0.5141 0.3473 0.063 Uiso 1 1 calc R . . . .
C8' C 0.0414(12) 0.5757(2) 0.3999(2) 0.0575(13) Uani 1 1 d . . . . .
H8' H -0.0268 0.5999 0.3642 0.069 Uiso 1 1 calc R . . . .
C9' C -0.0387(11) 0.5906(2) 0.4629(3) 0.0560(12) Uani 1 1 d . . . . .
C10' C 0.0620(11) 0.5550(2) 0.5166(2) 0.0548(13) Uani 1 1 d . . . . .
H10' H 0.0064 0.5660 0.5590 0.066 Uiso 1 1 calc R . . . .
Cl1' Cl 0.2346(3) 0.32718(6) 0.48203(7) 0.0626(3) Uani 1 1 d . . . . .
Cl2' Cl -0.2718(4) 0.65570(7) 0.47567(8) 0.0805(5) Uani 1 1 d . . . . .
O1' O 0.4947(8) 0.4041(2) 0.36661(19) 0.0584(9) Uani 1 1 d . . . . .
H1'A H 0.618(18) 0.388(4) 0.351(4) 0.12(3) Uiso 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 H1 0.9800 . ?
C1 C2 1.506(7) . ?
C1 C6 1.513(6) . ?
C1 O1 1.420(6) . ?
C2 H2 0.9800 . ?
C2 C3 1.519(7) . ?
C2 Cl1 1.812(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.524(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.517(6) . ?
C5 C6 1.395(6) . ?
C5 C10 1.397(7) . ?
C6 C7 1.400(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.373(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.372(7) . ?
C9 C10 1.371(7) . ?
C9 Cl2 1.751(5) . ?
C10 H10 0.9300 . ?
O1 H1A 0.71(7) . ?
C1' H1' 0.9800 . ?
C1' C2' 1.521(7) . ?
C1' C6' 1.512(7) . ?
C1' O1' 1.425(6) . ?
C2' H2' 0.9800 . ?
C2' C3' 1.505(8) . ?
C2' Cl1' 1.814(5) . ?
C3' H3'A 0.9700 . ?
C3' H3'B 0.9700 . ?
C3' C4' 1.517(9) . ?
C4' H4'A 0.9700 . ?
C4' H4'B 0.9700 . ?
C4' C5' 1.505(7) . ?
C5' C6' 1.402(7) . ?
C5' C10' 1.386(8) . ?
C6' C7' 1.392(7) . ?
C7' H7' 0.9300 . ?
C7' C8' 1.375(8) . ?
C8' H8' 0.9300 . ?
C8' C9' 1.371(7) . ?
C9' C10' 1.387(8) . ?
C9' Cl2' 1.750(6) . ?
C10' H10' 0.9300 . ?
O1' H1'A 0.76(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
C2 C1 H1 107.5 . . ?
C2 C1 C6 112.7(4) . . ?
C6 C1 H1 107.5 . . ?
O1 C1 H1 107.5 . . ?
O1 C1 C2 112.2(4) . . ?
O1 C1 C6 109.2(4) . . ?
C1 C2 H2 108.7 . . ?
C1 C2 C3 110.7(4) . . ?
C1 C2 Cl1 110.1(4) . . ?
C3 C2 H2 108.7 . . ?
C3 C2 Cl1 109.9(4) . . ?
Cl1 C2 H2 108.7 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C2 C3 C4 111.5(4) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 C3 113.1(4) . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C6 C5 C4 122.3(4) . . ?
C6 C5 C10 119.2(4) . . ?
C10 C5 C4 118.4(4) . . ?
C5 C6 C1 120.8(4) . . ?
C5 C6 C7 119.1(4) . . ?
C7 C6 C1 120.1(4) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.4(4) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 120.8 . . ?
C9 C8 C7 118.5(5) . . ?
C9 C8 H8 120.8 . . ?
C8 C9 Cl2 118.9(4) . . ?
C10 C9 C8 122.1(5) . . ?
C10 C9 Cl2 119.0(4) . . ?
C5 C10 H10 120.2 . . ?
C9 C10 C5 119.7(4) . . ?
C9 C10 H10 120.2 . . ?
C1 O1 H1A 114(5) . . ?
C2' C1' H1' 107.3 . . ?
C6' C1' H1' 107.3 . . ?
C6' C1' C2' 112.5(4) . . ?
O1' C1' H1' 107.3 . . ?
O1' C1' C2' 112.9(4) . . ?
O1' C1' C6' 109.2(4) . . ?
C1' C2' H2' 108.8 . . ?
C1' C2' Cl1' 110.6(3) . . ?
C3' C2' C1' 110.2(5) . . ?
C3' C2' H2' 108.8 . . ?
C3' C2' Cl1' 109.6(4) . . ?
Cl1' C2' H2' 108.8 . . ?
C2' C3' H3'A 108.8 . . ?
C2' C3' H3'B 108.8 . . ?
C2' C3' C4' 113.6(5) . . ?
H3'A C3' H3'B 107.7 . . ?
C4' C3' H3'A 108.8 . . ?
C4' C3' H3'B 108.8 . . ?
C3' C4' H4'A 108.5 . . ?
C3' C4' H4'B 108.5 . . ?
H4'A C4' H4'B 107.5 . . ?
C5' C4' C3' 115.0(5) . . ?
C5' C4' H4'A 108.5 . . ?
C5' C4' H4'B 108.5 . . ?
C6' C5' C4' 121.9(5) . . ?
C10' C5' C4' 119.0(4) . . ?
C10' C5' C6' 119.0(4) . . ?
C5' C6' C1' 120.5(5) . . ?
C7' C6' C1' 120.2(4) . . ?
C7' C6' C5' 119.3(5) . . ?
C6' C7' H7' 119.4 . . ?
C8' C7' C6' 121.2(4) . . ?
C8' C7' H7' 119.4 . . ?
C7' C8' H8' 120.4 . . ?
C9' C8' C7' 119.2(5) . . ?
C9' C8' H8' 120.4 . . ?
C8' C9' C10' 121.0(5) . . ?
C8' C9' Cl2' 119.4(4) . . ?
C10' C9' Cl2' 119.7(4) . . ?
C5' C10' C9' 120.3(4) . . ?
C5' C10' H10' 119.9 . . ?
C9' C10' H10' 119.9 . . ?
C1' O1' H1'A 116(7) . . ?

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
O1 H1A O1' 0.71(7) 2.05(7) 2.747(6) 165(7) 2_565
O1' H1'A O1 0.76(9) 2.03(9) 2.771(6) 163(9) 2_664

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 61.4(6) . . . . ?
C1 C6 C7 C8 -178.1(4) . . . . ?
C2 C1 C6 C5 23.3(6) . . . . ?
C2 C1 C6 C7 -159.2(4) . . . . ?
C2 C3 C4 C5 -42.4(6) . . . . ?
C3 C4 C5 C6 15.2(7) . . . . ?
C3 C4 C5 C10 -168.2(4) . . . . ?
C4 C5 C6 C1 -5.5(7) . . . . ?
C4 C5 C6 C7 176.9(4) . . . . ?
C4 C5 C10 C9 -178.0(5) . . . . ?
C5 C6 C7 C8 -0.6(7) . . . . ?
C6 C1 C2 C3 -50.6(5) . . . . ?
C6 C1 C2 Cl1 71.2(4) . . . . ?
C6 C5 C10 C9 -1.2(7) . . . . ?
C6 C7 C8 C9 1.6(8) . . . . ?
C7 C8 C9 C10 -2.6(8) . . . . ?
C7 C8 C9 Cl2 178.3(4) . . . . ?
C8 C9 C10 C5 2.4(8) . . . . ?
C10 C5 C6 C1 177.9(4) . . . . ?
C10 C5 C6 C7 0.3(7) . . . . ?
Cl1 C2 C3 C4 -60.4(5) . . . . ?
Cl2 C9 C10 C5 -178.5(4) . . . . ?
O1 C1 C2 C3 -174.2(4) . . . . ?
O1 C1 C2 Cl1 -52.5(5) . . . . ?
O1 C1 C6 C5 148.6(4) . . . . ?
O1 C1 C6 C7 -33.8(6) . . . . ?
C1' C2' C3' C4' 57.5(6) . . . . ?
C1' C6' C7' C8' -178.5(4) . . . . ?
C2' C1' C6' C5' 27.0(6) . . . . ?
C2' C1' C6' C7' -154.9(4) . . . . ?
C2' C3' C4' C5' -34.8(7) . . . . ?
C3' C4' C5' C6' 7.9(7) . . . . ?
C3' C4' C5' C10' -174.7(5) . . . . ?
C4' C5' C6' C1' -4.4(7) . . . . ?
C4' C5' C6' C7' 177.5(5) . . . . ?
C4' C5' C10' C9' -177.2(5) . . . . ?
C5' C6' C7' C8' -0.3(8) . . . . ?
C6' C1' C2' C3' -52.6(6) . . . . ?
C6' C1' C2' Cl1' 68.8(5) . . . . ?
C6' C5' C10' C9' 0.2(8) . . . . ?
C6' C7' C8' C9' 0.2(8) . . . . ?
C7' C8' C9' C10' 0.2(8) . . . . ?
C7' C8' C9' Cl2' -179.7(4) . . . . ?
C8' C9' C10' C5' -0.4(8) . . . . ?
C10' C5' C6' C1' 178.2(4) . . . . ?
C10' C5' C6' C7' 0.1(7) . . . . ?
Cl1' C2' C3' C4' -64.5(6) . . . . ?
Cl2' C9' C10' C5' 179.5(4) . . . . ?
O1' C1' C2' C3' -176.6(4) . . . . ?
O1' C1' C2' Cl1' -55.2(5) . . . . ?
O1' C1' C6' C5' 153.2(4) . . . . ?
O1' C1' C6' C7' -28.7(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
