# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2341483'
loop_
_audit_author_name
_audit_author_address
'Andrea Ienco'
;Cnr Iccom
Italy
;
_audit_update_record             
;
2024-03-19 deposited with the CCDC.	2024-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_sum            'C6 H13 Cl4 Ga N3 P'
_chemical_formula_moiety         'C6 H13 N3 P, Cl4 Ga'
_chemical_formula_weight         369.68

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'
Ga Ga -1.2846 0.7763 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   13.3420(9)
_cell_length_b                   8.2734(6)
_cell_length_c                   11.9648(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1320.72(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9830
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      72.46

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.859
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    11.235
_shelx_estimated_absorpt_T_min   0.5588
_shelx_estimated_absorpt_T_max   0.7536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_correction_T_min  0.4643
_exptl_absorpt_correction_T_max  0.7472

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16021
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.965
_diffrn_reflns_theta_max         72.470
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1408
_reflns_number_gt                1373
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0315P)²+1.1295P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1408
_refine_ls_number_parameters     84
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0229
_refine_ls_wR_factor_ref         0.0603
_refine_ls_wR_factor_gt          0.0600
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.001
_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
Ga1 Ga 0.34297(2) 0.250000 0.39707(2) 0.01061(11) Uani 1 2 d S T P . .
Cl1 Cl 0.30946(3) 0.46216(5) 0.49937(3) 0.01740(13) Uani 1 1 d . . . . .
Cl2 Cl 0.26010(4) 0.250000 0.24216(5) 0.01582(15) Uani 1 2 d S T P . .
Cl3 Cl 0.50268(4) 0.250000 0.36120(5) 0.01569(15) Uani 1 2 d S T P . .
P1 P 0.60862(5) 0.250000 0.77397(5) 0.01512(15) Uani 1 2 d S T P . .
N1 N 0.40437(15) 0.250000 0.72207(17) 0.0118(4) Uani 1 2 d S T P . .
H1 H 0.3588(18) 0.25000(2) 0.668(2) 0.014 Uiso 1 2 calc R U P . .
N2 N 0.45193(11) 0.39830(18) 0.89066(12) 0.0145(3) Uani 1 1 d . . . . .
C1 C 0.50687(18) 0.250000 0.6684(2) 0.0144(5) Uani 1 2 d S T P . .
H1A H 0.5135(2) 0.345(2) 0.6212(12) 0.017 Uiso 1 1 d R U . . .
C2 C 0.55824(13) 0.4176(2) 0.86047(15) 0.0156(3) Uani 1 1 d . . . . .
H2A H 0.5978(7) 0.4256(3) 0.9289(11) 0.019 Uiso 1 1 calc R U . . .
H2B H 0.56627(19) 0.5189(17) 0.8196(7) 0.019 Uiso 1 1 calc R U . . .
C3 C 0.38769(13) 0.4003(2) 0.79435(15) 0.0146(4) Uani 1 1 d . . . . .
H3A H 0.4013(2) 0.4974(15) 0.7500(7) 0.017 Uiso 1 1 calc R U . . .
H3B H 0.3176(11) 0.4043(2) 0.8185(4) 0.017 Uiso 1 1 calc R U . . .
C4 C 0.4351(2) 0.250000 0.9551(2) 0.0166(5) Uani 1 2 d S T P . .
H4A H 0.4796(11) 0.25000(2) 1.0196(16) 0.020 Uiso 1 2 calc R U P . .
H4B H 0.3665(17) 0.25000(2) 0.9828(7) 0.020 Uiso 1 2 calc R U P . .


_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
Ga1 Cl2 2.1582(6) . ?
Ga1 Cl3 2.1737(6) . ?
Ga1 Cl1 2.1862(5) . ?
Ga1 Cl1 2.1862(5) 7_565 ?
P1 C1 1.854(3) . ?
P1 C2 1.8566(19) 7_565 ?
P1 C2 1.8566(19) . ?
N1 C1 1.511(3) . ?
N1 C3 1.531(2) 7_565 ?
N1 C3 1.531(2) . ?
N1 H1 0.89(3) . ?
N2 C3 1.436(2) . ?
N2 C4 1.467(2) . ?
N2 C2 1.472(2) . ?
C1 H1A 0.97(2) . ?
C1 H1A 0.972(7) 7_565 ?
C2 H2A 0.976(16) . ?
C2 H2B 0.976(16) . ?
C3 H3A 0.980(15) . ?
C3 H3B 0.980(15) . ?
C4 H4A 0.97(2) . ?
C4 H4B 0.97(2) . ?

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
Cl2 Ga1 Cl3 109.43(3) . . ?
Cl2 Ga1 Cl1 112.093(16) . . ?
Cl3 Ga1 Cl1 108.121(17) . . ?
Cl2 Ga1 Cl1 112.093(16) . 7_565 ?
Cl3 Ga1 Cl1 108.122(16) . 7_565 ?
Cl1 Ga1 Cl1 106.82(3) . 7_565 ?
C1 P1 C2 96.58(8) . 7_565 ?
C1 P1 C2 96.58(8) . . ?
C2 P1 C2 96.68(12) 7_565 . ?
C1 N1 C3 111.81(12) . 7_565 ?
C1 N1 C3 111.81(12) . . ?
C3 N1 C3 108.64(18) 7_565 . ?
C1 N1 H1 108.1 . . ?
C3 N1 H1 108.1 7_565 . ?
C3 N1 H1 108.1 . . ?
C3 N2 C4 109.88(15) . . ?
C3 N2 C2 112.13(14) . . ?
C4 N2 C2 111.57(16) . . ?
N1 C1 P1 111.93(16) . . ?
N1 C1 H1A 109.2 . . ?
P1 C1 H1A 109.2 . . ?
N1 C1 H1A 109.2(7) . 7_565 ?
P1 C1 H1A 109.2(6) . 7_565 ?
H1A C1 H1A 107.9 . 7_565 ?
N2 C2 P1 113.85(12) . . ?
N2 C2 H2A 108.8 . . ?
P1 C2 H2A 108.8 . . ?
N2 C2 H2B 108.8 . . ?
P1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
N2 C3 N1 110.93(14) . . ?
N2 C3 H3A 109.5 . . ?
N1 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 108.0 . . ?
N2 C4 N2 113.56(19) 7_565 . ?
N2 C4 H4A 108.9 7_565 . ?
N2 C4 H4A 108.9 . . ?
N2 C4 H4B 108.9 7_565 . ?
N2 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?

_refine_diff_density_max         0.911
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.085



####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2341485'
loop_
_audit_author_name
_audit_author_address
'Andrea Ienco'
;Cnr Iccom
Italy
;
_audit_update_record             
;
2024-03-19 deposited with the CCDC.	2024-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H13 N3 O P, Cl4 Ga'
_chemical_formula_sum            'C6 H13 Cl4 Ga N3 O P'
_chemical_formula_weight         385.68

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'
Ga Ga -1.2846 0.7763 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   13.7699(10)
_cell_length_b                   8.1328(6)
_cell_length_c                   12.1428(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1359.85(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9833
_cell_measurement_theta_min      4.86
_cell_measurement_theta_max      72.24

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.884
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.055
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.035
_exptl_absorpt_coefficient_mu    11.002

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_exptl_absorpt_correction_T_min  0.2394
_exptl_absorpt_correction_T_max  0.7536

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12108
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.856
_diffrn_reflns_theta_max         72.232
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1431
_reflns_number_gt                1402
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0671P)²+3.0642P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1431
_refine_ls_number_parameters     90
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
Ga1 Ga 0.65956(4) 0.750000 0.59241(4) 0.0182(2) Uani 1 2 d S T P . .
Cl1 Cl 0.68888(6) 0.53413(11) 0.49130(6) 0.0269(2) Uani 1 1 d . . . . .
Cl2 Cl 0.74357(8) 0.750000 0.74304(9) 0.0236(3) Uani 1 2 d S T P . .
Cl3 Cl 0.50590(7) 0.750000 0.63616(9) 0.0228(3) Uani 1 2 d S T P . .
P1 P 0.40194(7) 0.750000 0.22189(8) 0.0151(3) Uani 1 2 d S T P . .
O1 O 0.3019(2) 0.750000 0.2662(3) 0.0240(7) Uani 1 2 d S T P . .
N1 N 0.5955(3) 0.750000 0.2679(3) 0.0170(8) Uani 1 2 d S T P . .
H1 H 0.639(3) 0.75000(2) 0.316(4) 0.020 Uiso 1 2 calc R U P . .
N2 N 0.54163(18) 0.5992(3) 0.1040(2) 0.0170(5) Uani 1 1 d . . . . .
C1 C 0.4985(3) 0.750000 0.3255(3) 0.0178(9) Uani 1 2 d S T P . .
H1A H 0.4931(4) 0.843(4) 0.370(2) 0.021 Uiso 1 1 d R U . . .
C2 C 0.4392(2) 0.5777(4) 0.1374(2) 0.0167(6) Uani 1 1 d . . . . .
H2A H 0.4321(3) 0.475(3) 0.1789(12) 0.020 Uiso 1 1 calc R U . . .
H2B H 0.3979(12) 0.5710(5) 0.0721(19) 0.020 Uiso 1 1 calc R U . . .
C3 C 0.6081(2) 0.5968(4) 0.1960(3) 0.0185(6) Uani 1 1 d . . . . .
H3A H 0.674(2) 0.5920(4) 0.1689(8) 0.022 Uiso 1 1 calc R U . . .
H3B H 0.5965(4) 0.499(3) 0.2399(13) 0.022 Uiso 1 1 calc R U . . .
C4 C 0.5560(3) 0.750000 0.0398(4) 0.0208(9) Uani 1 2 d S T P . .
H4A H 0.620(3) 0.75000(2) 0.0104(14) 0.025 Uiso 1 2 calc R U P . .
H4B H 0.512(2) 0.75000(2) -0.021(3) 0.025 Uiso 1 2 calc R U P . .


_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
Ga1 Cl2 2.1642(11) . ?
Ga1 Cl1 2.1801(9) . ?
Ga1 Cl1 2.1801(9) 7_575 ?
Ga1 Cl3 2.1816(11) . ?
P1 O1 1.479(3) . ?
P1 C2 1.811(3) . ?
P1 C2 1.811(3) 7_575 ?
P1 C1 1.830(4) . ?
N1 C1 1.507(5) . ?
N1 C3 1.531(4) . ?
N1 C3 1.531(4) 7_575 ?
N1 H1 0.84(6) . ?
N2 C3 1.444(4) . ?
N2 C4 1.466(4) . ?
N2 C2 1.478(4) . ?
C1 H1A 0.93(4) . ?
C1 H1A 0.928(13) 7_575 ?
C2 H2A 0.98(3) . ?
C2 H2B 0.98(3) . ?
C3 H3A 0.97(3) . ?
C3 H3B 0.97(3) . ?
C4 H4A 0.96(4) . ?
C4 H4B 0.96(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
Cl2 Ga1 Cl1 112.15(3) . . ?
Cl2 Ga1 Cl1 112.14(3) . 7_575 ?
Cl1 Ga1 Cl1 107.28(5) . 7_575 ?
Cl2 Ga1 Cl3 108.22(5) . . ?
Cl1 Ga1 Cl3 108.47(3) . . ?
Cl1 Ga1 Cl3 108.47(3) 7_575 . ?
O1 P1 C2 118.02(12) . . ?
O1 P1 C2 118.02(12) . 7_575 ?
C2 P1 C2 101.4(2) . 7_575 ?
O1 P1 C1 115.3(2) . . ?
C2 P1 C1 100.57(13) . . ?
C2 P1 C1 100.57(13) 7_575 . ?
C1 N1 C3 111.4(2) . . ?
C1 N1 C3 111.4(2) . 7_575 ?
C3 N1 C3 108.9(3) . 7_575 ?
C1 N1 H1 108.3 . . ?
C3 N1 H1 108.3 . . ?
C3 N1 H1 108.3 7_575 . ?
C3 N2 C4 109.7(3) . . ?
C3 N2 C2 113.0(2) . . ?
C4 N2 C2 112.0(3) . . ?
N1 C1 P1 109.0(3) . . ?
N1 C1 H1A 109.9 . . ?
P1 C1 H1A 109.9 . . ?
N1 C1 H1A 109.9(13) . 7_575 ?
P1 C1 H1A 109.9(13) . 7_575 ?
H1A C1 H1A 108.3 . 7_575 ?
N2 C2 P1 109.5(2) . . ?
N2 C2 H2A 109.8 . . ?
P1 C2 H2A 109.8 . . ?
N2 C2 H2B 109.8 . . ?
P1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
N2 C3 N1 111.0(3) . . ?
N2 C3 H3A 109.4 . . ?
N1 C3 H3A 109.4 . . ?
N2 C3 H3B 109.4 . . ?
N1 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
N2 C4 N2 113.5(3) 7_575 . ?
N2 C4 H4A 108.9 7_575 . ?
N2 C4 H4A 108.9 . . ?
N2 C4 H4B 108.9 7_575 . ?
N2 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?

_refine_diff_density_max         0.753
_refine_diff_density_min         -0.812
_refine_diff_density_rms         0.138



####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2341486'
loop_
_audit_author_name
_audit_author_address
'Andrea Ienco'
;Cnr Iccom
Italy
;
_audit_update_record             
;
2024-03-19 deposited with the CCDC.	2024-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H13 N3 O P, I'
_chemical_formula_sum            'C6 H13 I N3 O P'
_chemical_formula_weight         301.06

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'
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.8486(3)
_cell_length_b                   9.6385(3)
_cell_length_c                   12.7790(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.6520(10)
_cell_angle_gamma                90
_cell_volume                     966.31(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9899
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      33.17

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.069
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    3.439
_shelx_estimated_absorpt_T_min   0.820
_shelx_estimated_absorpt_T_max   0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_exptl_absorpt_correction_T_min  0.6978
_exptl_absorpt_correction_T_max  0.7465

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            53622
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.596
_diffrn_reflns_theta_max         33.216
_diffrn_reflns_theta_full        25.242
_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 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3699
_reflns_number_gt                3341
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0096P)²+0.8259P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3699
_refine_ls_number_parameters     116
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0159
_refine_ls_wR_factor_ref         0.0334
_refine_ls_wR_factor_gt          0.0319
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_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
P1 P 0.23468(4) 0.22533(4) 0.74681(3) 0.00951(6) Uani 1 1 d . . . . .
O1 O 0.18370(12) 0.09944(11) 0.68543(8) 0.01345(18) Uani 1 1 d . . . . .
I1 I 0.19829(2) 0.67476(2) 0.49004(2) 0.01144(2) Uani 1 1 d . . . . .
N1 N 0.11389(14) 0.46172(12) 0.83445(8) 0.00999(19) Uani 1 1 d . . . . .
H1 H 0.0237(18) 0.5159(11) 0.8467(3) 0.012 Uiso 1 1 d R U . . .
N2 N 0.39853(14) 0.46954(12) 0.75952(9) 0.0113(2) Uani 1 1 d . . . . .
N3 N 0.35398(14) 0.34479(12) 0.92395(9) 0.0105(2) Uani 1 1 d . . . . .
C1 C 0.05422(16) 0.33648(14) 0.77403(10) 0.0115(2) Uani 1 1 d . . . . .
H1A H -0.0014(7) 0.3654(4) 0.7086(8) 0.014 Uiso 1 1 calc R U . . .
H1B H -0.0283(11) 0.2854(7) 0.8144(5) 0.014 Uiso 1 1 calc R U . . .
C2 C 0.37731(17) 0.34949(14) 0.68760(10) 0.0124(2) Uani 1 1 d . . . . .
H2A H 0.4864(14) 0.3068(6) 0.67611(19) 0.015 Uiso 1 1 calc R U . . .
H2B H 0.3301(6) 0.3800(4) 0.6210(9) 0.015 Uiso 1 1 calc R U . . .
C3 C 0.32790(17) 0.20468(14) 0.87759(10) 0.0114(2) Uani 1 1 d . . . . .
H3A H 0.2525(10) 0.1506(7) 0.9205(6) 0.014 Uiso 1 1 calc R U . . .
H3B H 0.4360(14) 0.1564(6) 0.87430(11) 0.014 Uiso 1 1 calc R U . . .
C4 C 0.24214(17) 0.54469(14) 0.77274(10) 0.0124(2) Uani 1 1 d . . . . .
H4A H 0.1936(7) 0.5667(3) 0.7060(9) 0.015 Uiso 1 1 calc R U . . .
H4B H 0.2663(4) 0.6291(12) 0.8082(5) 0.015 Uiso 1 1 calc R U . . .
C5 C 0.47107(17) 0.42927(15) 0.86259(10) 0.0124(2) Uani 1 1 d . . . . .
H5A H 0.5002(4) 0.5116(11) 0.9014(5) 0.015 Uiso 1 1 calc R U . . .
H5B H 0.5741(14) 0.3778(7) 0.85280(16) 0.015 Uiso 1 1 calc R U . . .
C6 C 0.19760(17) 0.41912(14) 0.93907(10) 0.0111(2) Uani 1 1 d . . . . .
H6A H 0.2208(3) 0.5006(11) 0.9805(6) 0.013 Uiso 1 1 calc R U . . .
H6B H 0.1204(10) 0.3615(8) 0.9767(5) 0.013 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
P1 O1 1.4931(10) . ?
P1 C1 1.8175(13) . ?
P1 C3 1.8160(14) . ?
P1 C2 1.8184(14) . ?
N1 C1 1.5005(17) . ?
N1 C4 1.5233(17) . ?
N1 C6 1.5288(17) . ?
N1 H1 0.897(18) . ?
N2 C4 1.4393(17) . ?
N2 C5 1.4719(17) . ?
N2 C2 1.4841(18) . ?
N3 C6 1.4390(17) . ?
N3 C5 1.4710(17) . ?
N3 C3 1.4864(17) . ?
C1 H1A 0.973(12) . ?
C1 H1B 0.973(12) . ?
C2 H2A 0.965(13) . ?
C2 H2B 0.965(13) . ?
C3 H3A 0.970(13) . ?
C3 H3B 0.970(13) . ?
C4 H4A 0.948(13) . ?
C4 H4B 0.948(13) . ?
C5 H5A 0.960(13) . ?
C5 H5B 0.960(13) . ?
C6 H6A 0.962(13) . ?
C6 H6B 0.962(13) . ?

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
O1 P1 C1 112.40(6) . . ?
O1 P1 C3 119.29(6) . . ?
C1 P1 C3 100.60(6) . . ?
O1 P1 C2 118.37(6) . . ?
C1 P1 C2 100.61(6) . . ?
C3 P1 C2 102.62(6) . . ?
C1 N1 C4 110.92(10) . . ?
C1 N1 C6 110.72(10) . . ?
C4 N1 C6 108.66(10) . . ?
C1 N1 H1 108.8 . . ?
C4 N1 H1 108.7 . . ?
C6 N1 H1 109.0 . . ?
C4 N2 C5 109.69(10) . . ?
C4 N2 C2 112.59(11) . . ?
C5 N2 C2 112.47(11) . . ?
C6 N3 C5 110.14(11) . . ?
C6 N3 C3 113.43(10) . . ?
C5 N3 C3 111.81(10) . . ?
N1 C1 P1 109.83(8) . . ?
N1 C1 H1A 109.7 . . ?
P1 C1 H1A 109.7 . . ?
N1 C1 H1B 109.7 . . ?
P1 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
N2 C2 P1 108.35(9) . . ?
N2 C2 H2A 110.0 . . ?
P1 C2 H2A 110.0 . . ?
N2 C2 H2B 110.0 . . ?
P1 C2 H2B 110.0 . . ?
H2A C2 H2B 108.4 . . ?
N3 C3 P1 108.33(9) . . ?
N3 C3 H3A 110.0 . . ?
P1 C3 H3A 110.0 . . ?
N3 C3 H3B 110.0 . . ?
P1 C3 H3B 110.0 . . ?
H3A C3 H3B 108.4 . . ?
N2 C4 N1 112.03(11) . . ?
N2 C4 H4A 109.2 . . ?
N1 C4 H4A 109.2 . . ?
N2 C4 H4B 109.2 . . ?
N1 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
N2 C5 N3 113.04(10) . . ?
N2 C5 H5A 109.0 . . ?
N3 C5 H5A 109.0 . . ?
N2 C5 H5B 109.0 . . ?
N3 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
N3 C6 N1 111.28(10) . . ?
N3 C6 H6A 109.4 . . ?
N1 C6 H6A 109.4 . . ?
N3 C6 H6B 109.4 . . ?
N1 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?

_refine_diff_density_max         0.677
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.091



