# Electronic Supplementary Material (ESI) for RSC Advances.
# 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. 
# 
#######################################################################

data_cycleHgBr4
_database_code_depnum_ccdc_archive 'CCDC 2338144'
loop_
_audit_author_name
_audit_author_address
'souad chkoundali'
;University of Sfax
Tunisia
;
_audit_update_record             
;
2024-03-06 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 13 mars 2023                                             #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C8 H10 N O), Br4 Hg '
_chemical_formula_sum            'C16 H20 Br4 Hg N2 O2'
_chemical_formula_weight         792.57
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'C m c a'
_space_group_name_Hall           '-C 2bc 2'
_space_group_IT_number           64
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'x+1/2, -y, z-1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   20.8238(19)
_cell_length_b                   15.3516(14)
_cell_length_c                   13.7001(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4379.6(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9907
_cell_measurement_theta_min      2.2195
_cell_measurement_theta_max      27.4874
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.0479659
_diffrn_orient_matrix_UB_21      -0.0101950
_diffrn_orient_matrix_UB_31      0.0428782
_diffrn_orient_matrix_UB_12      0.0299726
_diffrn_orient_matrix_UB_22      0.0104912
_diffrn_orient_matrix_UB_32      0.0360234
_diffrn_orient_matrix_UB_13      -0.0190663
_diffrn_orient_matrix_UB_23      0.0703070
_diffrn_orient_matrix_UB_33      -0.0046119


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.404
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             2928
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    14.339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.354
_exptl_absorpt_correction_T_max  0.564

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

# Total exposition time  [*] :      4 h     2 min.                             #
#                                                                              #
#  [*] fast scan not included                                                  #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Fast     5.0  1.00    34.0   180  180.0    0.0    0.0    0.0   54.7 150.0 #
#  2 Fast@    5.0  1.00    34.0   180  180.0    0.0    0.0  180.0   54.7 150.0 #
#  3 Omega   25.0  0.50    34.0   194   97.0    0.1    2.7   72.0  -44.5 150.0 #
#  4 Omega   25.0  0.50    34.0   194   97.0    0.1    2.7  144.0  -44.5 150.0 #
#  5 Omega   25.0  0.50    34.0   194   97.0    0.1    2.7  288.0  -44.5 150.0 #
#                                                                              #
#  @: attenuated beam                                                          #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean 7.39
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_reflns_av_uneti/neti     0.0150
_diffrn_reflns_av_r_equivalents  0.0289
_diffrn_reflns_number            25323
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.654
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             2584
_reflns_number_gt                2403
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019_2 (Sheldrick, 2019)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0151P)²+6.7392P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2584
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0168
_refine_ls_R_factor_gt           0.0150
_refine_ls_wR_factor_ref         0.0352
_refine_ls_wR_factor_gt          0.0345
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.987
_refine_diff_density_rms         0.105

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
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'
Hg Hg -2.3894 9.2266 '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'

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
N1 N 0.63189(9) 0.26327(11) 0.90983(14) 0.0205(4) Uani 1 1 d . . . . .
H1A H 0.6460(12) 0.2047(17) 0.8939(17) 0.025 Uiso 1 1 d . U . . .
H1B H 0.6209(12) 0.2636(15) 0.970(2) 0.025 Uiso 1 1 d . U . . .
H1C H 0.5968(14) 0.2752(17) 0.8762(19) 0.025 Uiso 1 1 d . U . . .
C2 C 0.68157(10) 0.32937(12) 0.89396(13) 0.0167(4) Uani 1 1 d . . . . .
C3 C 0.74428(10) 0.30375(12) 0.87978(15) 0.0192(4) Uani 1 1 d . . . . .
H3 H 0.755114 0.243680 0.877394 0.023 Uiso 1 1 calc R U . . .
C4 C 0.79150(10) 0.36711(13) 0.86900(14) 0.0183(4) Uani 1 1 d . . . . .
H4 H 0.834947 0.350440 0.859049 0.022 Uiso 1 1 calc R U . . .
C5 C 0.77506(10) 0.45514(12) 0.87280(13) 0.0160(4) Uani 1 1 d . . . . .
C6 C 0.71147(10) 0.47875(13) 0.88542(14) 0.0183(4) Uani 1 1 d . . . . .
H6 H 0.700239 0.538720 0.886583 0.022 Uiso 1 1 calc R U . . .
C7 C 0.66392(10) 0.41645(13) 0.89640(14) 0.0191(4) Uani 1 1 d . . . . .
H7 H 0.620344 0.432936 0.905376 0.023 Uiso 1 1 calc R U . . .
C8 C 0.82519(10) 0.52506(13) 0.86662(13) 0.0177(4) Uani 1 1 d . . . . .
O9 O 0.80890(8) 0.60105(9) 0.88007(12) 0.0259(3) Uani 1 1 d . . . . .
C10 C 0.89316(10) 0.50129(14) 0.84616(16) 0.0233(4) Uani 1 1 d . . . . .
H10A H 0.918418 0.554384 0.835949 0.035 Uiso 1 1 calc R U . . .
H10B H 0.895106 0.465006 0.787381 0.035 Uiso 1 1 calc R U . . .
H10C H 0.910728 0.468839 0.901673 0.035 Uiso 1 1 calc R U . . .
Hg1 Hg 0.500000 0.25764(2) 0.64600(2) 0.02288(4) Uani 1 2 d S T P . .
Br1 Br 0.39316(2) 0.17174(2) 0.64602(2) 0.02655(6) Uani 1 1 d . . . . .
Br2 Br 0.500000 0.35170(2) 0.48913(2) 0.02194(7) Uani 1 2 d S T P . .
Br02 Br 0.500000 0.35245(2) 0.80651(2) 0.02165(7) Uani 1 2 d S T P . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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
N1 C2 1.465(3) . ?
N1 H1A 0.97(3) . ?
N1 H1B 0.86(3) . ?
N1 H1C 0.88(3) . ?
C2 C3 1.378(3) . ?
C2 C7 1.387(3) . ?
C3 C4 1.391(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(3) . ?
C5 C8 1.500(3) . ?
C6 C7 1.385(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 O9 1.229(2) . ?
C8 C10 1.488(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
Hg1 Br1 2.5862(3) . ?
Hg1 Br1 2.5862(3) 12_655 ?
Hg1 Br2 2.5891(4) . ?
Hg1 Br02 2.6371(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H1A 113.2(15) . . ?
C2 N1 H1B 109.1(17) . . ?
H1A N1 H1B 108(2) . . ?
C2 N1 H1C 111.3(18) . . ?
H1A N1 H1C 109(2) . . ?
H1B N1 H1C 106(2) . . ?
C3 C2 C7 121.99(18) . . ?
C3 C2 N1 119.50(17) . . ?
C7 C2 N1 118.48(18) . . ?
C2 C3 C4 119.05(18) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 119.99(19) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.56(18) . . ?
C6 C5 C8 119.06(17) . . ?
C4 C5 C8 121.36(18) . . ?
C5 C6 C7 121.12(18) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C2 118.27(19) . . ?
C6 C7 H7 120.9 . . ?
C2 C7 H7 120.9 . . ?
O9 C8 C10 121.57(19) . . ?
O9 C8 C5 118.61(19) . . ?
C10 C8 C5 119.81(17) . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Br1 Hg1 Br1 118.688(13) . 12_655 ?
Br1 Hg1 Br2 106.527(7) . . ?
Br1 Hg1 Br2 106.526(7) 12_655 . ?
Br1 Hg1 Br02 106.339(7) . . ?
Br1 Hg1 Br02 106.338(7) 12_655 . ?
Br2 Hg1 Br02 112.605(12) . . ?

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
C7 C2 C3 C4 1.0(3) . . . . ?
N1 C2 C3 C4 -177.24(18) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C3 C4 C5 C8 176.80(17) . . . . ?
C4 C5 C6 C7 1.4(3) . . . . ?
C8 C5 C6 C7 -176.74(17) . . . . ?
C5 C6 C7 C2 -0.3(3) . . . . ?
C3 C2 C7 C6 -0.9(3) . . . . ?
N1 C2 C7 C6 177.35(18) . . . . ?
C6 C5 C8 O9 5.2(3) . . . . ?
C4 C5 C8 O9 -172.84(18) . . . . ?
C6 C5 C8 C10 -175.76(18) . . . . ?
C4 C5 C8 C10 6.2(3) . . . . ?

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
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# -----------------------
#
# D       H       A       D-H         H...A       D...A      D-H...A   symm publ
# ------------------------------------------------------------------------------
N1 H1A O9 0.97(3) 1.86(3) 2.809(2) 166(2) 16_645 yes
N1 H1B Br1 0.86(3) 2.62(3) 3.426(2) 157(2) 2_655 yes
N1 H1C Br02 0.88(3) 2.53(3) 3.3795(19) 163(2) . yes
C3 H3 O9 0.95 2.56 3.303(2) 134.8 16_645 yes

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


