# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_r20210602c
_database_code_depnum_ccdc_archive 'CCDC 2162957'
loop_
_audit_author_name
_audit_author_address
DMCAT-FBrB
;Tianjin University
China
;
_audit_update_record             
;
2022-03-29 deposited with the CCDC.	2022-04-26 downloaded from the CCDC.
;
_audit_creation_date             2021-06-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br2 C6 F4, C16 H22 Cl2 N2 O4'
_chemical_formula_sum            'C22 H22 Br2 Cl2 F4 N2 O4'
_chemical_formula_weight         685.13
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
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'
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      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                   7.4110(3)
_cell_length_b                   9.0343(6)
_cell_length_c                   9.7976(6)
_cell_angle_alpha                76.870(5)
_cell_angle_beta                 88.723(5)
_cell_angle_gamma                84.956(4)
_cell_volume                     636.36(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    6334
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.9410
_cell_measurement_theta_min      2.3090
_shelx_estimated_absorpt_T_max   0.724
_shelx_estimated_absorpt_T_min   0.608
_exptl_absorpt_coefficient_mu    3.457
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.788
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9700
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.756
_diffrn_reflns_theta_min         2.134
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    4.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00    4.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00    4.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0170715000
_diffrn_orient_matrix_UB_12      -0.0522752000
_diffrn_orient_matrix_UB_13      -0.0438718000
_diffrn_orient_matrix_UB_21      -0.0219291000
_diffrn_orient_matrix_UB_22      0.0594623000
_diffrn_orient_matrix_UB_23      -0.0596839000
_diffrn_orient_matrix_UB_31      0.0919753000
_diffrn_orient_matrix_UB_32      0.0166861000
_diffrn_orient_matrix_UB_33      -0.0062723000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3599
_reflns_number_total             4262
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       0.038(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         4262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.046
_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)+(0.0313P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0726
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.62121(2) 0.13312(2) 0.09797(2) 0.02313(8) Uani 1 1 d . . . . .
F1 F 0.66689(16) 0.35449(13) -0.18785(12) 0.0279(3) Uani 1 1 d . . . . .
F2 F 0.43102(16) 0.34903(13) 0.26568(11) 0.0278(3) Uani 1 1 d . . . . .
C9 C 0.5846(2) 0.4240(2) -0.09295(19) 0.0196(4) Uani 1 1 d . . . . .
C10 C 0.5521(2) 0.34287(19) 0.04133(19) 0.0185(3) Uani 1 1 d . . . . .
C11 C 0.4663(2) 0.4214(2) 0.13391(18) 0.0192(3) Uani 1 1 d . . . . .
Cl1 Cl 0.70183(9) 1.11489(9) 0.48847(6) 0.05260(19) Uani 1 1 d . . . . .
O1 O 0.7487(2) 0.78611(15) 1.17109(14) 0.0289(3) Uani 1 1 d . . . . .
O2 O 0.8106(2) 0.56548(16) 1.32568(14) 0.0340(4) Uani 1 1 d . . . . .
N1 N 0.8801(2) 0.80971(18) 0.90816(16) 0.0243(3) Uani 1 1 d . . . . .
H1 H 0.830364 0.859374 0.968937 0.029 Uiso 1 1 calc R . . . .
C1 C 0.8632(3) 1.1545(2) 0.6055(2) 0.0341(5) Uani 1 1 d . . . . .
H1A H 0.987086 1.132997 0.570887 0.041 Uiso 1 1 calc R . . . .
H1B H 0.846911 1.263975 0.607175 0.041 Uiso 1 1 calc R . . . .
C2 C 0.8429(3) 1.0598(2) 0.7521(2) 0.0246(4) Uani 1 1 d . . . . .
H2A H 0.715039 1.072226 0.782019 0.030 Uiso 1 1 calc R . . . .
H2B H 0.918306 1.098111 0.816537 0.030 Uiso 1 1 calc R . . . .
C3 C 0.8977(3) 0.8917(2) 0.76409(19) 0.0213(4) Uani 1 1 d . . . . .
H3A H 0.819302 0.850869 0.703355 0.026 Uiso 1 1 calc R . . . .
H3B H 1.024609 0.877940 0.732529 0.026 Uiso 1 1 calc R . . . .
C4 C 1.0249(2) 0.5762(2) 0.86157(19) 0.0193(3) Uani 1 1 d . . . . .
H4 H 1.041800 0.627146 0.766675 0.023 Uiso 1 1 calc R . . . .
C5 C 0.9372(2) 0.65852(19) 0.95459(18) 0.0180(3) Uani 1 1 d . . . . .
C6 C 0.9123(2) 0.5783(2) 1.09511(18) 0.0181(3) Uani 1 1 d . . . . .
C7 C 0.8169(2) 0.6555(2) 1.19720(19) 0.0208(4) Uani 1 1 d . . . . .
C8 C 0.7096(3) 0.6294(3) 1.4301(2) 0.0394(6) Uani 1 1 d . . . . .
H8A H 0.580584 0.643429 1.406237 0.059 Uiso 1 1 calc GR . . . .
H8B H 0.752982 0.728182 1.432505 0.059 Uiso 1 1 calc GR . . . .
H8C H 0.726927 0.559828 1.522329 0.059 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
Br1 C10 1.8776(17) . ?
F1 C9 1.3429(19) . ?
F2 C11 1.340(2) . ?
C9 C10 1.380(3) . ?
C9 C11 1.383(2) 2_665 ?
C10 C11 1.385(2) . ?
Cl1 C1 1.788(3) . ?
O1 C7 1.216(2) . ?
O2 C7 1.337(2) . ?
O2 C8 1.449(2) . ?
N1 H1 0.8800 . ?
N1 C3 1.446(2) . ?
N1 C5 1.370(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.507(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.516(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4 0.9500 . ?
C4 C5 1.415(2) . ?
C4 C6 1.404(2) 2_767 ?
C5 C6 1.419(2) . ?
C6 C7 1.478(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 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
F1 C9 C10 120.68(16) . . ?
F1 C9 C11 118.06(16) . 2_665 ?
C10 C9 C11 121.26(15) . 2_665 ?
C9 C10 Br1 121.56(13) . . ?
C9 C10 C11 117.74(16) . . ?
C11 C10 Br1 120.71(14) . . ?
F2 C11 C9 118.45(15) . 2_665 ?
F2 C11 C10 120.55(16) . . ?
C9 C11 C10 121.01(16) 2_665 . ?
C7 O2 C8 116.32(16) . . ?
C3 N1 H1 118.4 . . ?
C5 N1 H1 118.4 . . ?
C5 N1 C3 123.19(15) . . ?
Cl1 C1 H1A 109.3 . . ?
Cl1 C1 H1B 109.3 . . ?
H1A C1 H1B 107.9 . . ?
C2 C1 Cl1 111.66(16) . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C1 C2 C3 112.94(16) . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
N1 C3 C2 109.57(15) . . ?
N1 C3 H3A 109.8 . . ?
N1 C3 H3B 109.8 . . ?
C2 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 H4 118.9 . . ?
C6 C4 H4 118.9 2_767 . ?
C6 C4 C5 122.17(16) 2_767 . ?
N1 C5 C4 120.18(16) . . ?
N1 C5 C6 122.43(15) . . ?
C4 C5 C6 117.39(15) . . ?
C4 C6 C5 120.43(15) 2_767 . ?
C4 C6 C7 119.09(16) 2_767 . ?
C5 C6 C7 120.47(16) . . ?
O1 C7 O2 121.79(16) . . ?
O1 C7 C6 125.38(17) . . ?
O2 C7 C6 112.83(15) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
Br1 C10 C11 F2 0.0(2) . . . . ?
Br1 C10 C11 C9 179.89(13) . . . 2_665 ?
F1 C9 C10 Br1 0.2(2) . . . . ?
F1 C9 C10 C11 -179.82(17) . . . . ?
C9 C10 C11 F2 180.00(16) . . . . ?
C9 C10 C11 C9 -0.1(3) . . . 2_665 ?
C11 C9 C10 Br1 -179.89(13) 2_665 . . . ?
C11 C9 C10 C11 0.1(3) 2_665 . . . ?
Cl1 C1 C2 C3 69.0(2) . . . . ?
N1 C5 C6 C4 -179.17(16) . . . 2_767 ?
N1 C5 C6 C7 1.9(3) . . . . ?
C1 C2 C3 N1 178.11(17) . . . . ?
C3 N1 C5 C4 2.7(3) . . . . ?
C3 N1 C5 C6 -177.37(17) . . . . ?
C4 C5 C6 C4 0.7(3) . . . 2_767 ?
C4 C5 C6 C7 -178.17(17) . . . . ?
C4 C6 C7 O1 -176.26(18) 2_767 . . . ?
C4 C6 C7 O2 3.3(2) 2_767 . . . ?
C5 N1 C3 C2 -173.11(16) . . . . ?
C5 C6 C7 O1 2.7(3) . . . . ?
C5 C6 C7 O2 -177.81(17) . . . . ?
C6 C4 C5 N1 179.16(16) 2_767 . . . ?
C6 C4 C5 C6 -0.8(3) 2_767 . . . ?
C8 O2 C7 O1 3.3(3) . . . . ?
C8 O2 C7 C6 -176.27(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.374
_oxdiff_exptl_absorpt_empirical_full_min 0.793
####################################################################### 
# 
# 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_r20210629a
_database_code_depnum_ccdc_archive 'CCDC 2162959'
loop_
_audit_author_name
_audit_author_address
DMCAT-FIB
;Tianjin University
China
;
_audit_update_record             
;
2022-03-29 deposited with the CCDC.	2022-04-26 downloaded from the CCDC.
;
_audit_creation_date             2021-06-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 F4 I2, C16 H22 Cl2 N2 O4'
_chemical_formula_sum            'C22 H22 Cl2 F4 I2 N2 O4'
_chemical_formula_weight         779.11
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
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      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                   7.4734(2)
_cell_length_b                   9.3123(5)
_cell_length_c                   9.9081(4)
_cell_angle_alpha                73.840(4)
_cell_angle_beta                 86.669(3)
_cell_angle_gamma                82.978(3)
_cell_volume                     657.13(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    12008
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      37.8320
_cell_measurement_theta_min      2.6520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.657
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.969
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13748
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.602
_diffrn_reflns_theta_min         2.291
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -123.00  57.00   1.00    1.00    --  -33.00  45.00   0.00  180
  2  ω   -123.00  57.00   1.00    1.00    --  -33.00  45.00  90.00  180
  3  ω   -123.00  57.00   1.00    1.00    --  -33.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0338435000
_diffrn_orient_matrix_UB_12      -0.0521426000
_diffrn_orient_matrix_UB_13      0.0597805000
_diffrn_orient_matrix_UB_21      -0.0150790000
_diffrn_orient_matrix_UB_22      0.0570483000
_diffrn_orient_matrix_UB_23      0.0354687000
_diffrn_orient_matrix_UB_31      -0.0881911000
_diffrn_orient_matrix_UB_32      0.0198303000
_diffrn_orient_matrix_UB_33      -0.0269624000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6067
_reflns_number_total             6458
_reflns_odcompleteness_completeness 99.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.385
_refine_diff_density_min         -1.279
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       0.052(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         6458
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0288
_refine_ls_restrained_S_all      1.060
_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)+(0.0367P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0729
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.62301(2) 0.11265(2) 0.11710(2) 0.02027(4) Uani 1 1 d . . . . .
F1 F 0.41438(16) 0.35009(12) 0.26791(11) 0.0266(2) Uani 1 1 d . . . . .
F2 F 0.32174(16) 0.64427(12) 0.17954(11) 0.0263(2) Uani 1 1 d . . . . .
C9 C 0.5506(2) 0.34316(16) 0.04773(16) 0.0173(2) Uani 1 1 d . . . . .
C10 C 0.4589(2) 0.42218(17) 0.13495(16) 0.0185(2) Uani 1 1 d . . . . .
C11 C 0.4099(2) 0.57541(17) 0.08876(16) 0.0189(2) Uani 1 1 d . . . . .
Cl1 Cl 0.70874(8) 1.14582(8) 0.49387(5) 0.04696(15) Uani 1 1 d . . . . .
O1 O 0.8166(2) 0.55285(16) 1.32939(14) 0.0354(3) Uani 1 1 d . . . . .
O2 O 0.7476(2) 0.77369(14) 1.17357(14) 0.0298(3) Uani 1 1 d . . . . .
N1 N 0.8823(2) 0.80883(14) 0.90784(14) 0.0221(2) Uani 1 1 d . . . . .
H1 H 0.836154 0.855443 0.970013 0.026 Uiso 1 1 calc R . . . .
C1 C 0.7166(4) 0.6126(2) 1.4345(2) 0.0411(5) Uani 1 1 d . . . . .
H1A H 0.588031 0.629485 1.413332 0.062 Uiso 1 1 calc GR . . . .
H1B H 0.759299 0.708007 1.434366 0.062 Uiso 1 1 calc GR . . . .
H1C H 0.734623 0.540698 1.527277 0.062 Uiso 1 1 calc GR . . . .
C2 C 0.8192(2) 0.64519(16) 1.19912(16) 0.0185(2) Uani 1 1 d . . . . .
C3 C 0.9130(2) 0.57320(16) 1.09561(15) 0.0164(2) Uani 1 1 d . . . . .
C4 C 0.93725(19) 0.65734(15) 0.95350(15) 0.0161(2) Uani 1 1 d . . . . .
C5 C 1.0247(2) 0.57979(15) 0.86185(15) 0.0172(2) Uani 1 1 d . . . . .
H5 H 1.042654 0.633588 0.766326 0.021 Uiso 1 1 calc R . . . .
C6 C 0.8967(2) 0.89519(16) 0.76278(16) 0.0188(2) Uani 1 1 d . . . . .
H6A H 0.808793 0.866952 0.706367 0.023 Uiso 1 1 calc R . . . .
H6B H 1.019312 0.873520 0.724604 0.023 Uiso 1 1 calc R . . . .
C7 C 0.8594(2) 1.06147(17) 0.75345(18) 0.0229(3) Uani 1 1 d . . . . .
H7A H 0.734840 1.082383 0.788366 0.027 Uiso 1 1 calc R . . . .
H7B H 0.942874 1.086841 0.815209 0.027 Uiso 1 1 calc R . . . .
C8 C 0.8812(3) 1.1608(2) 0.6054(2) 0.0320(4) Uani 1 1 d . . . . .
H8A H 1.000603 1.131805 0.566021 0.038 Uiso 1 1 calc R . . . .
H8B H 0.877108 1.266689 0.607883 0.038 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 C9 2.0764(15) . ?
F1 C10 1.3447(18) . ?
F2 C11 1.3428(17) . ?
C9 C10 1.385(2) . ?
C9 C11 1.389(2) 2_665 ?
C10 C11 1.381(2) . ?
Cl1 C8 1.788(2) . ?
O1 C1 1.443(2) . ?
O1 C2 1.338(2) . ?
O2 C2 1.2136(19) . ?
N1 H1 0.8800 . ?
N1 C4 1.3740(19) . ?
N1 C6 1.444(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.476(2) . ?
C3 C4 1.421(2) . ?
C3 C5 1.396(2) 2_767 ?
C4 C5 1.398(2) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.517(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.513(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?

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
C10 C9 I1 121.52(11) . . ?
C10 C9 C11 117.09(13) . 2_665 ?
C11 C9 I1 121.39(11) 2_665 . ?
F1 C10 C9 120.23(13) . . ?
F1 C10 C11 118.19(13) . . ?
C11 C10 C9 121.58(14) . . ?
F2 C11 C9 120.53(13) . 2_665 ?
F2 C11 C10 118.15(14) . . ?
C10 C11 C9 121.33(13) . 2_665 ?
C2 O1 C1 116.17(15) . . ?
C4 N1 H1 118.4 . . ?
C4 N1 C6 123.15(13) . . ?
C6 N1 H1 118.4 . . ?
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 113.11(13) . . ?
O2 C2 O1 121.22(14) . . ?
O2 C2 C3 125.67(14) . . ?
C4 C3 C2 120.64(13) . . ?
C5 C3 C2 119.23(13) 2_767 . ?
C5 C3 C4 120.12(13) 2_767 . ?
N1 C4 C3 122.08(13) . . ?
N1 C4 C5 120.97(13) . . ?
C5 C4 C3 116.92(12) . . ?
C3 C5 C4 122.96(13) 2_767 . ?
C3 C5 H5 118.5 2_767 . ?
C4 C5 H5 118.5 . . ?
N1 C6 H6A 109.8 . . ?
N1 C6 H6B 109.8 . . ?
N1 C6 C7 109.29(13) . . ?
H6A C6 H6B 108.3 . . ?
C7 C6 H6A 109.8 . . ?
C7 C6 H6B 109.8 . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C6 112.78(14) . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
Cl1 C8 H8A 109.3 . . ?
Cl1 C8 H8B 109.3 . . ?
C7 C8 Cl1 111.82(14) . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 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
I1 C9 C10 F1 -0.1(2) . . . . ?
I1 C9 C10 C11 -179.70(11) . . . . ?
F1 C10 C11 F2 0.5(2) . . . . ?
F1 C10 C11 C9 -179.21(14) . . . 2_665 ?
C9 C10 C11 F2 -179.80(14) . . . . ?
C9 C10 C11 C9 0.4(3) . . . 2_665 ?
C11 C9 C10 F1 179.23(14) 2_665 . . . ?
C11 C9 C10 C11 -0.4(2) 2_665 . . . ?
O1 C2 C3 C4 -176.48(15) . . . . ?
O1 C2 C3 C5 4.7(2) . . . 2_767 ?
O2 C2 C3 C4 4.4(2) . . . . ?
O2 C2 C3 C5 -174.39(16) . . . 2_767 ?
N1 C4 C5 C3 178.32(14) . . . 2_767 ?
N1 C6 C7 C8 177.02(15) . . . . ?
C1 O1 C2 O2 3.1(3) . . . . ?
C1 O1 C2 C3 -176.02(18) . . . . ?
C2 C3 C4 N1 2.9(2) . . . . ?
C2 C3 C4 C5 -178.88(14) . . . . ?
C3 C4 C5 C3 0.1(2) . . . 2_767 ?
C4 N1 C6 C7 -168.90(14) . . . . ?
C5 C3 C4 N1 -178.30(14) 2_767 . . . ?
C5 C3 C4 C5 -0.1(2) 2_767 . . . ?
C6 N1 C4 C3 -176.64(15) . . . . ?
C6 N1 C4 C5 5.2(2) . . . . ?
C6 C7 C8 Cl1 69.01(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.609
_oxdiff_exptl_absorpt_empirical_full_min 0.597
