# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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. 
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data_[F-PPA]ZnBr4
_database_code_depnum_ccdc_archive 'CCDC 2302288'
loop_
_audit_author_name
_audit_author_address
'Yuyin Wang'
;Jining University
China
;
_audit_update_record             
;
2024-02-11 deposited with the CCDC.	2024-02-15 downloaded from the CCDC.
;
_audit_creation_date             2023-10-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br4 Zn, C10 H14 F N2'
_chemical_formula_sum            'C10 H14 Br4 F N2 Zn'
_chemical_formula_weight         566.24
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.0955(3)
_cell_length_b                   20.9526(8)
_cell_length_c                   9.8012(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.2500(10)
_cell_angle_gamma                90
_cell_volume                     1624.64(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7455
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.61
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.397
_shelx_estimated_absorpt_T_min   0.397
_exptl_absorpt_coefficient_mu    11.344
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.3925
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1355 before and 0.0651 after correction.
The Ratio of minimum to maximum transmission is 0.5264.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light gray'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    gray
_exptl_crystal_density_diffrn    2.315
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1068
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            25662
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.303
_diffrn_reflns_theta_min         2.338
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2828
_reflns_number_total             4032
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.693
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       0.0013(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   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         4032
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.019
_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)+(0.0425P)²+0.2705P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0890
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C8(H8A,H8B), C10(H10A,H10B), C9(H9A,H9B), C7(H7A,H7B)
1.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C1(H1), C2(H2)
;
_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 0.84851(5) 0.52789(2) 0.13245(4) 0.04032(14) Uani 1 1 d . . . . .
Br2 Br 0.61083(5) 0.61442(3) 0.39511(5) 0.04475(15) Uani 1 1 d . . . . .
Br3 Br 1.10781(5) 0.59462(3) 0.47990(5) 0.04279(15) Uani 1 1 d . . . . .
Br4 Br 0.86303(6) 0.70923(3) 0.16167(5) 0.04891(15) Uani 1 1 d . . . . .
Zn1 Zn 0.86280(6) 0.61594(3) 0.29981(5) 0.03539(15) Uani 1 1 d . . . . .
F006 F 0.4447(3) 0.57087(13) 1.0480(3) 0.0454(6) Uani 1 1 d . . . . .
N2 N 0.6187(4) 0.61313(16) 0.8610(3) 0.0294(8) Uani 1 1 d . . . . .
N1 N 0.8248(4) 0.55477(17) 0.6872(3) 0.0320(8) Uani 1 1 d . . . . .
H1A H 0.780848 0.569229 0.601855 0.038 Uiso 1 1 calc R U . . .
H1B H 0.911220 0.529354 0.681630 0.038 Uiso 1 1 calc R U . . .
C5 C 0.3955(5) 0.6285(2) 0.9918(4) 0.0309(9) Uani 1 1 d . . . . .
C4 C 0.4798(5) 0.6529(2) 0.8947(4) 0.0306(9) Uani 1 1 d . . . . .
C8 C 0.6949(5) 0.5176(2) 0.7394(4) 0.0359(10) Uani 1 1 d . . . . .
H8A H 0.746782 0.497278 0.826874 0.043 Uiso 1 1 calc R U . . .
H8B H 0.651053 0.484356 0.672668 0.043 Uiso 1 1 calc R U . . .
C10 C 0.7429(5) 0.6514(2) 0.7997(4) 0.0338(9) Uani 1 1 d . . . . .
H10A H 0.686676 0.668934 0.710284 0.041 Uiso 1 1 calc R U . . .
H10B H 0.785695 0.686611 0.861360 0.041 Uiso 1 1 calc R U . . .
C9 C 0.8872(5) 0.6096(2) 0.7806(4) 0.0342(10) Uani 1 1 d . . . . .
H9A H 0.966238 0.634501 0.740673 0.041 Uiso 1 1 calc R U . . .
H9B H 0.946504 0.593769 0.870734 0.041 Uiso 1 1 calc R U . . .
C7 C 0.5508(5) 0.5594(2) 0.7616(4) 0.0345(10) Uani 1 1 d . . . . .
H7A H 0.471041 0.534133 0.799870 0.041 Uiso 1 1 calc R U . . .
H7B H 0.491957 0.576902 0.672906 0.041 Uiso 1 1 calc R U . . .
C6 C 0.2683(5) 0.6612(2) 1.0333(5) 0.0429(11) Uani 1 1 d . . . . .
H6 H 0.213262 0.644245 1.099227 0.051 Uiso 1 1 calc R U . . .
C3 C 0.4347(6) 0.7114(2) 0.8362(5) 0.0504(13) Uani 1 1 d . . . . .
H3 H 0.489923 0.728421 0.770357 0.060 Uiso 1 1 calc R U . . .
C1 C 0.2248(6) 0.7200(2) 0.9745(5) 0.0499(13) Uani 1 1 d . . . . .
H1 H 0.139260 0.743352 1.001268 0.060 Uiso 1 1 calc R U . . .
C2 C 0.3062(6) 0.7446(3) 0.8765(6) 0.0583(14) Uani 1 1 d . . . . .
H2 H 0.274043 0.784244 0.836929 0.070 Uiso 1 1 calc R U . . .


_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 Zn1 2.4550(7) . ?
Br2 Zn1 2.4172(6) . ?
Br3 Zn1 2.4007(6) . ?
Br4 Zn1 2.3781(7) . ?
F006 C5 1.352(5) . ?
N2 C4 1.492(5) . ?
N2 C10 1.507(5) . ?
N2 C7 1.514(5) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 C8 1.483(5) . ?
N1 C9 1.489(5) . ?
C5 C4 1.382(5) . ?
C5 C6 1.369(6) . ?
C4 C3 1.370(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.511(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C9 1.503(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C1 1.373(7) . ?
C3 H3 0.9300 . ?
C3 C2 1.377(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.376(7) . ?
C2 H2 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
Br2 Zn1 Br1 108.92(3) . . ?
Br3 Zn1 Br1 105.42(2) . . ?
Br3 Zn1 Br2 110.29(2) . . ?
Br4 Zn1 Br1 104.06(2) . . ?
Br4 Zn1 Br2 109.48(3) . . ?
Br4 Zn1 Br3 118.11(3) . . ?
C4 N2 C10 112.9(3) . . ?
C4 N2 C7 111.7(3) . . ?
C10 N2 C7 108.7(3) . . ?
H1A N1 H1B 108.0 . . ?
C8 N1 H1A 109.3 . . ?
C8 N1 H1B 109.3 . . ?
C8 N1 C9 111.5(3) . . ?
C9 N1 H1A 109.3 . . ?
C9 N1 H1B 109.3 . . ?
F006 C5 C4 117.7(4) . . ?
F006 C5 C6 120.1(4) . . ?
C6 C5 C4 122.1(4) . . ?
C5 C4 N2 116.9(4) . . ?
C3 C4 N2 123.6(4) . . ?
C3 C4 C5 119.5(4) . . ?
N1 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
N1 C8 C7 111.8(4) . . ?
H8A C8 H8B 107.9 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
N2 C10 H10A 109.7 . . ?
N2 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C9 C10 N2 110.0(3) . . ?
C9 C10 H10A 109.7 . . ?
C9 C10 H10B 109.7 . . ?
N1 C9 C10 110.8(3) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N2 C7 H7A 109.7 . . ?
N2 C7 H7B 109.7 . . ?
C8 C7 N2 109.7(3) . . ?
C8 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C5 C6 H6 121.1 . . ?
C5 C6 C1 117.8(4) . . ?
C1 C6 H6 121.1 . . ?
C4 C3 H3 120.6 . . ?
C4 C3 C2 118.8(4) . . ?
C2 C3 H3 120.6 . . ?
C6 C1 H1 119.6 . . ?
C6 C1 C2 120.7(4) . . ?
C2 C1 H1 119.6 . . ?
C3 C2 H2 119.5 . . ?
C1 C2 C3 120.9(5) . . ?
C1 C2 H2 119.5 . . ?

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
F006 C5 C4 N2 -0.2(5) . . . . ?
F006 C5 C4 C3 -179.4(4) . . . . ?
F006 C5 C6 C1 179.1(4) . . . . ?
N2 C4 C3 C2 -178.9(4) . . . . ?
N2 C10 C9 N1 58.8(4) . . . . ?
N1 C8 C7 N2 -56.6(4) . . . . ?
C5 C4 C3 C2 0.3(7) . . . . ?
C5 C6 C1 C2 0.4(7) . . . . ?
C4 N2 C10 C9 174.9(3) . . . . ?
C4 N2 C7 C8 -175.7(3) . . . . ?
C4 C5 C6 C1 0.4(7) . . . . ?
C4 C3 C2 C1 0.5(8) . . . . ?
C8 N1 C9 C10 -55.4(4) . . . . ?
C10 N2 C4 C5 -158.5(4) . . . . ?
C10 N2 C4 C3 20.7(6) . . . . ?
C10 N2 C7 C8 59.0(4) . . . . ?
C9 N1 C8 C7 54.7(4) . . . . ?
C7 N2 C4 C5 78.6(4) . . . . ?
C7 N2 C4 C3 -102.2(5) . . . . ?
C7 N2 C10 C9 -60.6(4) . . . . ?
C6 C5 C4 N2 178.6(4) . . . . ?
C6 C5 C4 C3 -0.7(7) . . . . ?
C6 C1 C2 C3 -0.8(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
