# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_p-i_298k
_database_code_depnum_ccdc_archive 'CCDC 2424321'
loop_
_audit_author_name
_audit_author_address
'Ryo Tsunashima'
;yamaguchi
Japan
;
_audit_update_record             
;
2025-02-17 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;
_audit_creation_date             2025-01-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(I), C6 H14 N3 P, H4 N'
_chemical_formula_sum            'C6 H18 I3 N4 P'
_chemical_formula_weight         557.91
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H18N4I3P
_chemical_oxdiff_usercomment     'solid solution 7-3'
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        'C m c e'
_space_group_name_Hall           '-C 2bc 2'
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                   14.1583(4)
_cell_length_b                   14.4657(4)
_cell_length_c                   14.2413(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2916.76(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6138
_cell_measurement_temperature    298
_cell_measurement_theta_max      30.6570
_cell_measurement_theta_min      2.4720
_shelx_estimated_absorpt_T_max   0.404
_shelx_estimated_absorpt_T_min   0.254
_exptl_absorpt_coefficient_mu    6.516
_exptl_absorpt_correction_T_max  0.36921
_exptl_absorpt_correction_T_min  0.35719
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.541
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       sphere
_exptl_crystal_F_000             2048
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
11 -9 15 0.0803
19 3 6 0.0657
12 14 -9 0.0668
-11 9 -15 0.0897
-18 -1 -8 0.1034
-3 -20 5 0.1539
-9 -1 18 0.1388
7 15 -12 0.0711
9 6 -17 0.0619
5 -17 -11 0.1060
-8 15 11 0.1588
15 11 7 0.0418
11 -5 16 0.0619

_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_exptl_crystal_size_rad          0.109
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
10.5537 -8.7042 14.7301 -0.3157 0.7557 0.5738
18.8641 3.3376 5.6948 -0.3693 0.8908 -0.2647
11.8223 13.6361 -9.0377 -0.1123 0.2773 -0.9542
-10.5155 8.7321 -14.7417 0.3152 -0.7544 -0.5758
-18.3646 -1.1964 -7.7858 0.3807 -0.9172 0.1175
-3.0496 -19.5819 4.7200 0.4420 0.1811 0.8786
-9.3011 -0.8815 17.7377 -0.6267 -0.2625 0.7337
6.5979 15.0971 -11.7605 -0.0411 -0.0142 -0.9991
9.0659 5.5742 -17.0215 0.4526 0.1906 -0.8711
5.0217 -16.5755 -10.5452 0.9106 0.3778 0.1677
-7.8488 14.7889 11.3421 -0.8779 -0.4778 -0.0327
15.2077 11.2075 6.8976 -0.6531 0.6169 -0.4392
10.5940 -4.9632 16.2981 -0.4931 0.7182 0.4909

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6393
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.469
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -78.00 -23.00   0.25    0.25    --   -5.68 -62.00 134.00  220
  2  ω    -14.00  21.00   0.25    0.25    --    6.15 -97.00  39.00  140
  3  ω    -17.00  40.00   0.25    0.25    --    6.15 -99.00-120.00  228
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0024914000
_diffrn_orient_matrix_UB_12      -0.0313885000
_diffrn_orient_matrix_UB_13      -0.0381969000
_diffrn_orient_matrix_UB_21      0.0470066000
_diffrn_orient_matrix_UB_22      -0.0143646000
_diffrn_orient_matrix_UB_23      0.0091359000
_diffrn_orient_matrix_UB_31      -0.0171270000
_diffrn_orient_matrix_UB_32      -0.0348105000
_diffrn_orient_matrix_UB_33      0.0306548000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1499
_reflns_number_total             1542
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       0.00064(3)
_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   1.136
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1542
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0177
_refine_ls_R_factor_gt           0.0170
_refine_ls_restrained_S_all      1.142
_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)+(0.0216P)²+5.4840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0436
_refine_ls_wR_factor_ref         0.0439
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H,H,H,H,H,H,H,H,H,H) groups
2. Restrained distances
 C1-H1B = C1-H1A
 1.09 with sigma of 0.02
 N1-H1E = N1-H1C = N1-H1D
 1.06 with sigma of 0.02
 H1A-H1B
 1.78 with sigma of 0.04
 P1-H1A = P1-H1B
 1.7 with sigma of 0.04
 H1E-H1C = H1E-H1D = H1C-H1D
 1.75 with sigma of 0.04
3. Others
 Fixed Sof: P1(0.5) C1(0.5) N2(0.5) H1A(0.5) H1B(0.5)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_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
I001 I 0.500000 0.53844(2) 0.27372(2) 0.02879(9) Uani 1 2 d S T P . .
I002 I 0.500000 0.72886(2) 0.51941(2) 0.03097(9) Uani 1 2 d S T P . .
I003 I 0.250000 0.74494(2) 0.250000 0.03429(10) Uani 1 2 d S T P . .
P1 P 0.84295(19) 0.5688(3) 0.5713(3) 0.0265(6) Uani 0.5 1 d . . P A -1
N1 N 0.500000 0.7918(3) 0.2748(3) 0.0365(8) Uani 1 2 d DS T P . .
N3 N 0.69501(16) 0.55958(16) 0.44023(16) 0.0247(5) Uani 1 1 d . . . . .
C4 C 0.6340(3) 0.500000 0.500000 0.0280(8) Uani 1 2 d S T P . .
C2 C 0.7555(2) 0.6244(2) 0.4991(2) 0.0319(6) Uani 1 1 d . . . . .
C3 C 0.7554(2) 0.5014(2) 0.3740(2) 0.0321(6) Uani 1 1 d . . . . .
C1 C 0.8859(3) 0.4841(5) 0.4842(5) 0.0257(17) Uani 0.5 1 d D . P . .
N2 N 0.8102(5) 0.5660(8) 0.5660(9) 0.026(2) Uani 0.5 1 d . . P A 1
H4 H 0.597(2) 0.540(2) 0.540(2) 0.031 Uiso 1 1 d . U . . .
H2A H 0.712(2) 0.665(2) 0.540(2) 0.031 Uiso 1 1 d . U . . .
H2B H 0.794(2) 0.661(2) 0.451(2) 0.031 Uiso 1 1 d . U . . .
H3A H 0.792(2) 0.550(2) 0.331(2) 0.031 Uiso 1 1 d . U . . .
H3 H 0.656(2) 0.592(2) 0.408(2) 0.031 Uiso 1 1 d . U . . .
H1A H 0.923(5) 0.477(5) 0.554(3) 0.031 Uiso 0.5 1 d D U P B -2
H3B H 0.713(2) 0.467(2) 0.332(2) 0.031 Uiso 1 1 d . U . . .
H1B H 0.912(5) 0.556(2) 0.470(5) 0.031 Uiso 0.5 1 d D U P C -2
H1C H 0.5644(17) 0.764(2) 0.253(2) 0.031 Uiso 1 1 d D U . . .
H1D H 0.500000 0.8625(14) 0.258(3) 0.031 Uiso 1 2 d DS U P . .
H1E H 0.500000 0.781(3) 0.3486(13) 0.031 Uiso 1 2 d DS U P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I001 0.02862(15) 0.02875(16) 0.02900(15) -0.00137(10) 0.000 0.000
I002 0.03142(15) 0.02794(16) 0.03355(16) 0.00296(10) 0.000 0.000
I003 0.03461(16) 0.03276(17) 0.03551(16) 0.000 0.00275(12) 0.000
P1 0.0270(16) 0.0246(9) 0.0280(10) 0.0020(7) -0.0069(13) -0.0051(12)
N1 0.040(2) 0.032(2) 0.037(2) 0.0061(16) 0.000 0.000
N3 0.0253(11) 0.0223(11) 0.0265(11) 0.0051(9) -0.0057(10) 0.0032(9)
C4 0.0201(18) 0.026(2) 0.038(2) 0.0029(17) 0.000 0.000
C2 0.0316(15) 0.0183(13) 0.0458(17) -0.0051(12) -0.0018(14) -0.0015(11)
C3 0.0321(15) 0.0410(17) 0.0234(13) -0.0065(12) -0.0003(12) 0.0015(12)
C1 0.018(2) 0.029(5) 0.030(5) -0.003(3) -0.001(2) 0.000(2)
N2 0.022(5) 0.031(3) 0.027(3) -0.011(2) 0.000(4) 0.004(4)

_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 C2 1.800(4) . ?
P1 C1 1.847(6) . ?
N1 H1C 1.043(17) . ?
N1 H1D 1.051(18) . ?
N1 H1E 1.062(18) . ?
N3 C4 1.488(3) . ?
N3 C2 1.522(3) . ?
N3 C3 1.527(4) . ?
N3 H3 0.85(3) . ?
C4 H4 0.96(3) . ?
C4 H4 0.96(3) 4_566 ?
C2 N2 1.491(11) . ?
C2 H2A 1.03(3) . ?
C2 H2B 1.02(3) . ?
C3 N2 1.509(12) 4_566 ?
C3 H3A 1.06(3) . ?
C3 H3B 0.98(4) . ?
C1 C1 0.645(9) 4_566 ?
C1 N2 1.478(11) 4_566 ?
C1 H1A 1.13(2) . ?
C1 H1B 1.13(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
C2 P1 C1 98.0(3) . . ?
H1C N1 H1D 107.9(18) . . ?
H1C N1 H1E 103.7(18) . . ?
H1D N1 H1E 112(3) . . ?
C4 N3 C2 111.6(2) . . ?
C4 N3 C3 111.1(2) . . ?
C4 N3 H3 104(2) . . ?
C2 N3 C3 111.4(2) . . ?
C2 N3 H3 109(2) . . ?
C3 N3 H3 110(2) . . ?
N3 C4 N3 109.0(3) 4_566 . ?
N3 C4 H4 107.8(19) . . ?
N3 C4 H4 107.8(19) 4_566 4_566 ?
N3 C4 H4 109(2) 4_566 . ?
N3 C4 H4 109(2) . 4_566 ?
H4 C4 H4 114(4) . 4_566 ?
P1 C2 H2A 109.6(18) . . ?
P1 C2 H2B 104.2(18) . . ?
N3 C2 P1 115.2(2) . . ?
N3 C2 H2A 109.3(18) . . ?
N3 C2 H2B 104.7(18) . . ?
N2 C2 P1 12.5(4) . . ?
N2 C2 N3 107.1(5) . . ?
N2 C2 H2A 105.3(19) . . ?
N2 C2 H2B 116.3(19) . . ?
H2A C2 H2B 114(3) . . ?
N3 C3 H3A 105.2(18) . . ?
N3 C3 H3B 108(2) . . ?
N2 C3 N3 107.1(4) 4_566 . ?
N2 C3 H3A 120.0(18) 4_566 . ?
N2 C3 H3B 109(2) 4_566 . ?
H3A C3 H3B 107(3) . . ?
C1 C1 P1 19.24(18) 4_566 . ?
C1 C1 N2 133.5(4) 4_566 4_566 ?
C1 C1 H1A 57(4) 4_566 . ?
C1 C1 H1B 57(4) 4_566 . ?
N2 C1 P1 114.3(5) 4_566 . ?
H1A C1 H1B 95(3) . . ?
C2 N2 C3 117.5(5) . 4_566 ?
C1 N2 C2 110.2(9) 4_566 . ?
C1 N2 C3 109.3(8) 4_566 4_566 ?

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
P1 C2 N2 C3 175(3) . . . 4_566 ?
P1 C2 N2 C1 -59(2) . . . 4_566 ?
N3 C2 N2 C3 -52.9(9) . . . 4_566 ?
N3 C2 N2 C1 73.0(6) . . . 4_566 ?
C4 N3 C2 P1 65.9(3) . . . . ?
C4 N3 C2 N2 55.6(5) . . . . ?
C4 N3 C3 N2 -55.5(5) . . . 4_566 ?
C2 P1 C1 C1 130(4) . . . 4_566 ?
C2 P1 C1 N2 -47.1(8) . . . 4_566 ?
C2 N3 C4 N3 -62.59(17) . . . 4_566 ?
C2 N3 C3 N2 69.6(5) . . . 4_566 ?
C3 N3 C4 N3 62.42(16) . . . 4_566 ?
C3 N3 C2 P1 -58.9(3) . . . . ?
C3 N3 C2 N2 -69.2(5) . . . . ?
C1 P1 C2 N3 43.2(3) . . . . ?
C1 P1 C2 N2 95(3) . . . . ?

_shelx_res_file                  
;
TITL 300_re1_a.res in Cmca
    p-i_298k.res
    created by SHELXL-2018/3 at 12:00:33 on 08-Jan-2025
REM Old TITL 300_re1 in Cmce
REM SHELXT solution in Cmca: R1 0.055, Rweak 0.004, Alpha 0.012
REM <I/s> 1.557 for 121 systematic absences, Orientation as input
REM Formula found by SHELXT: C6 N5 I3
CELL 0.71073 14.1583 14.4657 14.2413 90 90 90
ZERR 8 0.0004 0.0004 0.0003 0 0 0
LATT 7
SYMM -X,0.5-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM +X,-Y,-Z
SFAC C H I N P
UNIT 48 144 24 32 8
DFIX 1.09 C1 H1b C1 H1a
DANG 1.78 H1a H1b
DANG 1.7 P1 H1a P1 H1b
DFIX 1.06 N1 H1e N1 H1c N1 H1d
DANG 1.75 H1e H1c H1e H1d H1c H1d

L.S. 12
PLAN  5
SIZE 0.17 0.25 0.29
TEMP 24.85
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\p-I_298K.hkl">
REM </olex2.extras>

WGHT    0.021600    5.484000
EXTI    0.000640
FVAR       0.11353
I001  3    0.500000    0.538440    0.273718    10.50000    0.02862    0.02875 =
         0.02900   -0.00137    0.00000    0.00000
I002  3    0.500000    0.728860    0.519413    10.50000    0.03142    0.02794 =
         0.03355    0.00296    0.00000    0.00000
I003  3    0.250000    0.744936    0.250000    10.50000    0.03461    0.03276 =
         0.03551    0.00000    0.00275    0.00000
PART -1
P1    5    0.842946    0.568789    0.571299    10.50000    0.02696    0.02462 =
         0.02799    0.00201   -0.00695   -0.00515

PART 0
N1    4    0.500000    0.791781    0.274850    10.50000    0.04046    0.03176 =
         0.03721    0.00610    0.00000    0.00000

N3    4    0.695005    0.559583    0.440234    11.00000    0.02535    0.02230 =
         0.02646    0.00508   -0.00570    0.00325
C4    1    0.633955    0.500000    0.500000    10.50000    0.02010    0.02584 =
         0.03808    0.00285    0.00000    0.00000
C2    1    0.755476    0.624442    0.499085    11.00000    0.03160    0.01831 =
         0.04582   -0.00507   -0.00177   -0.00146
C3    1    0.755437    0.501358    0.374007    11.00000    0.03211    0.04097 =
         0.02335   -0.00652   -0.00029    0.00145
C1    1    0.885879    0.484053    0.484183    10.50000    0.01789    0.02899 =
         0.03014   -0.00259   -0.00088   -0.00010
PART 1
N2    4    0.810157    0.565968    0.566045    10.50000    0.02156    0.03061 =
         0.02654   -0.01127   -0.00011    0.00443
PART 0
H4    2    0.597206    0.539715    0.539914    11.00000   -1.20000
H2A   2    0.712247    0.664807    0.540406    11.00000   -1.20000
H2B   2    0.793992    0.661109    0.451283    11.00000   -1.20000
H3A   2    0.791878    0.549668    0.331372    11.00000   -1.20000
H3    2    0.655729    0.591584    0.408446    11.00000   -1.20000
PART -2
H1A   2    0.923104    0.477222    0.553768    10.50000   -1.20000
PART 0
H3B   2    0.712575    0.466742    0.332459    11.00000   -1.20000
PART -2
H1B   2    0.912241    0.556472    0.470297    10.50000   -1.20000
PART 0
H1C   2    0.564382    0.763941    0.253119    11.00000   -1.20000
H1D   2    0.500000    0.862509    0.257889    10.50000   -1.20000
H1E   2    0.500000    0.780890    0.348575    10.50000   -1.20000
HKLF 4




REM  300_re1_a.res in Cmca
REM wR2 = 0.0439, GooF = S = 1.136, Restrained GooF = 1.142 for all data
REM R1 = 0.0170 for 1499 Fo > 4sig(Fo) and 0.0177 for all 1542 data
REM 115 parameters refined using 9 restraints

END

WGHT      0.0216      5.4841

REM Highest difference peak  0.612,  deepest hole -0.551,  1-sigma level  0.088
Q1    1   0.5000  0.7750  0.5582  10.50000  0.05    0.61
Q2    1   0.5000  0.5814  0.2260  10.50000  0.05    0.49
Q3    1   0.2534  0.7800  0.2041  11.00000  0.05    0.47
Q4    1   0.5000  0.5838  0.3171  10.50000  0.05    0.40
Q5    1   0.5000  0.4955  0.3209  10.50000  0.05    0.39
;
_shelx_res_checksum              89916
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.362
_oxdiff_exptl_absorpt_empirical_full_min 0.506
####################################################################### 
# 
# 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_p-i_410k
_database_code_depnum_ccdc_archive 'CCDC 2424322'
loop_
_audit_author_name
_audit_author_address
'Ryo Tsunashima'
;yamaguchi
Japan
;
_audit_update_record             
;
2025-02-17 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;
_audit_creation_date             2025-01-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(I), C5.708 H13.539 N3 P, 0.5(H6 N2)'
_chemical_formula_sum            'C5.71 H16.54 I3 N4 P'
_chemical_formula_weight         552.93
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6N4H18PI3
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        'C m c e'
_space_group_name_Hall           '-C 2bc 2'
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                   14.2452(5)
_cell_length_b                   14.5204(6)
_cell_length_c                   14.3176(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2961.54(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5991
_cell_measurement_temperature    410
_cell_measurement_theta_max      30.7120
_cell_measurement_theta_min      2.4780
_shelx_estimated_absorpt_T_max   0.446
_shelx_estimated_absorpt_T_min   0.233
_exptl_absorpt_coefficient_mu    6.417
_exptl_absorpt_correction_T_max  0.02993
_exptl_absorpt_correction_T_min  0.01299
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       sphere
_exptl_crystal_F_000             2022
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-8 7 17 0.0490
-9 -15 -10 0.1271
-3 -13 -15 0.1228
11 -5 -16 0.0929
17 4 -10 0.0827
-1 20 2 0.1244
7 14 13 0.1048
12 -1 16 0.0991
9 -16 9 0.1407
-4 -18 -9 0.1178
-10 -7 -16 0.1104
-6 19 -4 0.1287
-17 -4 11 0.0807

_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_exptl_crystal_size_rad          0.115
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-8.0693 7.2670 17.0425 -0.4371 0.6313 0.6407
-9.3550 -14.7335 -10.3825 -0.0926 0.1394 -0.9859
-2.7306 -13.4602 -14.9517 0.1368 -0.1937 -0.9715
10.6886 -4.8845 -16.4036 0.4942 -0.7149 -0.4947
16.8439 4.3808 -10.1305 0.5628 -0.8176 0.1220
-1.3345 20.2719 2.4671 0.5395 0.3692 0.7567
7.3701 13.6282 13.1054 -0.0501 -0.0377 0.9980
11.8581 -0.7354 16.2623 -0.6092 -0.4218 0.6715
9.1305 -15.5837 9.3252 -0.8194 -0.5641 -0.1021
-4.1420 -17.5721 -9.4751 -0.2031 -0.1368 -0.9696
-10.2486 -7.3615 -15.7571 0.3400 0.2371 -0.9100
-5.8447 19.1560 -4.0153 0.7387 0.5074 0.4438
-16.6446 -3.8420 10.6620 -0.5655 0.8205 -0.0837

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6301
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.457
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      410
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  27.00   0.25    0.33    --    6.15  98.00 146.00  216
  2  ω     -9.00  39.00   0.25    0.33    --    6.15 -99.00-120.00  192
  3  ω    -17.00  28.00   0.25    0.33    --    6.15 -98.00  39.00  180
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0024825000
_diffrn_orient_matrix_UB_12      0.0313831000
_diffrn_orient_matrix_UB_13      -0.0378523000
_diffrn_orient_matrix_UB_21      -0.0468596000
_diffrn_orient_matrix_UB_22      0.0140477000
_diffrn_orient_matrix_UB_23      0.0088653000
_diffrn_orient_matrix_UB_31      0.0166817000
_diffrn_orient_matrix_UB_32      0.0346917000
_diffrn_orient_matrix_UB_33      0.0306973000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1456
_reflns_number_total             1564
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.828
_refine_diff_density_min         -0.891
_refine_diff_density_rms         0.159
_refine_ls_extinction_coef       0.00028(6)
_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   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         1564
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0701P)²+0.0137P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0953
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All H(H,H,H) groups, All C(H,H) groups, All N(H) groups, All N(H,H,H,H) groups
2. Restrained distances
 C3-H3B = C3-H3A
 0.97 with sigma of 0.02
 C2-H2A = C2-H2B
 0.97 with sigma of 0.02
 C1-H1A = C1-H1B
 0.97 with sigma of 0.02
 N1-H1C = N1-H1D = N1-H1E
 1.06 with sigma of 0.02
 H3A-H3B
 1.57 with sigma of 0.04
 H2A-H2B
 1.57 with sigma of 0.04
 H1A-H1B
 1.57 with sigma of 0.04
 P1-H1B = P1-H1A
 1.53 with sigma of 0.04
 H1C-H1D = H1C-H1E = H1D-H1E
 1.75 with sigma of 0.04
3. Others
 Fixed Sof: P1(0.5) H4A(0.5) H4B(0.5) C1(0.5) N2(0.5) H1A(0.5) H1B(0.5) H1C(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
I001 I 0.500000 0.53630(3) 0.27345(3) 0.05358(19) Uani 1 2 d S T P . .
I002 I 0.500000 0.72875(3) 0.51781(3) 0.05661(19) Uani 1 2 d S T P . .
I003 I 0.250000 0.74448(3) 0.250000 0.06025(19) Uani 1 2 d S T P . .
P1 P 0.8415(3) 0.4310(4) 0.4285(4) 0.0500(9) Uani 0.5 1 d . . P A -1
N3 N 0.6948(2) 0.5593(3) 0.4403(2) 0.0477(7) Uani 1 1 d . . . . .
H3 H 0.650(4) 0.587(5) 0.403(5) 0.057 Uiso 0.77(10) 1 d . U . B 2
N1 N 0.500000 0.7891(5) 0.2727(4) 0.0642(14) Uani 1 2 d DS T P . .
C4 C 0.6350(4) 0.500000 0.500000 0.0518(14) Uani 1 2 d S T P . .
H4A H 0.595052 0.461864 0.461069 0.062 Uiso 0.5 1 calc R U P . .
H4B H 0.595051 0.538136 0.538930 0.062 Uiso 0.5 1 calc R U P . .
C2 C 0.7547(3) 0.5009(4) 0.3746(4) 0.0476(18) Uani 0.85(2) 1 d D . . . .
C3 C 0.7550(3) 0.6234(3) 0.4985(3) 0.0564(11) Uani 1 1 d D . . . .
C1 C 0.8844(5) 0.4849(9) 0.4845(11) 0.052(3) Uani 0.5 1 d D . P . .
N2 N 0.8091(8) 0.4344(13) 0.4354(13) 0.054(4) Uani 0.5 1 d . . P A 1
H3A H 0.788(3) 0.661(3) 0.452(3) 0.065 Uiso 1 1 d D U . . .
H3B H 0.717(3) 0.661(3) 0.540(3) 0.065 Uiso 1 1 d D U . . .
H2A H 0.716(3) 0.466(3) 0.331(3) 0.065 Uiso 1 1 d D U . . .
H2B H 0.790(3) 0.542(3) 0.334(3) 0.065 Uiso 1 1 d D U . . .
H1A H 0.929(7) 0.522(9) 0.449(13) 0.11(6) Uiso 0.5 1 d D . P C -2
H1B H 0.921(7) 0.432(5) 0.506(7) 0.06(3) Uiso 0.5 1 d D . P D -2
H1C H 0.444(5) 0.743(5) 0.260(4) 0.069 Uiso 0.5 1 d D U P . .
H1D H 0.500000 0.842(3) 0.221(3) 0.069 Uiso 1 2 d DS U P . .
H1E H 0.500000 0.819(4) 0.339(2) 0.069 Uiso 1 2 d DS U P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I001 0.0548(3) 0.0554(3) 0.0505(3) -0.00173(17) 0.000 0.000
I002 0.0586(3) 0.0544(3) 0.0568(3) 0.00403(18) 0.000 0.000
I003 0.0622(3) 0.0600(3) 0.0585(3) 0.000 0.00344(18) 0.000
P1 0.052(3) 0.0508(14) 0.0474(15) 0.0030(11) 0.0093(18) 0.0082(19)
N3 0.0502(16) 0.0464(17) 0.0464(19) 0.0069(15) -0.0066(14) 0.0059(14)
N1 0.073(4) 0.063(4) 0.056(4) 0.004(3) 0.000 0.000
C4 0.038(3) 0.055(4) 0.062(4) 0.004(3) 0.000 0.000
C2 0.052(3) 0.057(3) 0.034(3) -0.0040(19) -0.0005(18) 0.0017(17)
C3 0.055(3) 0.044(2) 0.070(3) -0.0038(19) -0.0026(19) -0.0002(19)
C1 0.039(3) 0.051(10) 0.065(11) -0.003(6) 0.002(4) 0.001(4)
N2 0.046(8) 0.065(6) 0.052(6) -0.010(5) 0.001(6) -0.004(6)

_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 C2 1.776(7) . ?
P1 C1 1.276(11) . ?
N3 H3 0.93(7) . ?
N3 C4 1.483(5) . ?
N3 C2 1.526(6) . ?
N3 C3 1.516(5) . ?
N1 H1C 1.06(2) . ?
N1 H1D 1.069(19) . ?
N1 H1E 1.036(19) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C2 N2 1.514(19) . ?
C2 H2A 0.978(19) . ?
C2 H2B 0.98(2) . ?
C3 N2 1.481(17) 4_566 ?
C3 H3A 0.984(19) . ?
C3 H3B 0.975(19) . ?
C1 C1 0.625(16) 4_566 ?
C1 N2 1.476(19) . ?
C1 N2 1.96(2) 4_566 ?
C1 H1A 0.98(2) . ?
C1 H1B 0.98(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
C1 P1 C2 104.8(7) . . ?
C4 N3 H3 101(4) . . ?
C4 N3 C2 110.7(3) . . ?
C4 N3 C3 111.4(3) . . ?
C2 N3 H3 105(4) . . ?
C3 N3 H3 116(4) . . ?
C3 N3 C2 111.4(3) . . ?
H1C N1 H1D 110(4) . . ?
H1C N1 H1E 114(4) . . ?
H1D N1 H1E 110(4) . . ?
N3 C4 N3 109.8(5) . 4_566 ?
N3 C4 H4A 109.7 4_566 . ?
N3 C4 H4A 109.7 . . ?
N3 C4 H4B 109.7 . . ?
N3 C4 H4B 109.7 4_566 . ?
H4A C4 H4B 108.2 . . ?
P1 C2 H2A 112(3) . . ?
P1 C2 H2B 104(3) . . ?
N3 C2 P1 116.0(4) . . ?
N3 C2 H2A 111(3) . . ?
N3 C2 H2B 108(3) . . ?
N2 C2 P1 13.8(5) . . ?
N2 C2 N3 106.7(7) . . ?
N2 C2 H2A 109(3) . . ?
N2 C2 H2B 118(3) . . ?
H2A C2 H2B 104(3) . . ?
N3 C3 H3A 104(3) . . ?
N3 C3 H3B 111(4) . . ?
N2 C3 N3 107.3(7) 4_566 . ?
N2 C3 H3A 120(3) 4_566 . ?
N2 C3 H3B 103(3) 4_566 . ?
H3A C3 H3B 112(3) . . ?
P1 C1 N2 118.2(6) . 4_566 ?
P1 C1 N2 18.0(6) . . ?
C1 C1 P1 151.4(4) 4_566 . ?
C1 C1 N2 33.2(4) 4_566 4_566 ?
C1 C1 N2 133.4(6) 4_566 . ?
C1 C1 H1A 89(10) 4_566 . ?
C1 C1 H1B 109(8) 4_566 . ?
N2 C1 N2 100.3(9) . 4_566 ?
H1A C1 H1B 105(4) . . ?
C2 N2 C1 103.6(11) . 4_566 ?
C3 N2 C2 117.5(8) 4_566 . ?
C3 N2 C1 104.5(11) 4_566 4_566 ?
C1 N2 C2 109.2(14) . . ?
C1 N2 C3 110.8(14) . 4_566 ?
C1 N2 C1 13.4(4) . 4_566 ?

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
P1 C2 N2 C3 -172(5) . . . 4_566 ?
P1 C2 N2 C1 61(3) . . . . ?
P1 C2 N2 C1 74(4) . . . 4_566 ?
P1 C1 N2 C2 -110(3) . . . . ?
P1 C1 N2 C3 119(4) . . . 4_566 ?
P1 C1 N2 C1 -177(6) . . . 4_566 ?
N3 C2 N2 C3 53.8(14) . . . 4_566 ?
N3 C2 N2 C1 -73.4(9) . . . . ?
N3 C2 N2 C1 -60.7(7) . . . 4_566 ?
C4 N3 C2 P1 -66.4(5) . . . . ?
C4 N3 C2 N2 -55.5(8) . . . . ?
C4 N3 C3 N2 55.3(8) . . . 4_566 ?
C2 P1 C1 C1 47(9) . . . 4_566 ?
C2 P1 C1 N2 52(3) . . . . ?
C2 P1 C1 N2 46.2(15) . . . 4_566 ?
C2 N3 C4 N3 62.4(3) . . . 4_566 ?
C2 N3 C3 N2 -68.8(8) . . . 4_566 ?
C3 N3 C4 N3 -62.1(3) . . . 4_566 ?
C3 N3 C2 P1 58.1(5) . . . . ?
C3 N3 C2 N2 69.0(8) . . . . ?
C1 P1 C2 N3 -48.8(8) . . . . ?
C1 P1 C2 N2 -98(4) . . . . ?
C1 C1 N2 C2 67(6) 4_566 . . . ?
C1 C1 N2 C3 -64(6) 4_566 . . 4_566 ?
N2 C1 N2 C2 65.6(11) 4_566 . . . ?
N2 C1 N2 C3 -65.4(11) 4_566 . . 4_566 ?
N2 C1 N2 C1 -2(5) 4_566 . . 4_566 ?

_shelx_res_file                  
;
TITL 419_re1_a.res in Cmca
    p-i_410k.res
    created by SHELXL-2018/3 at 12:02:04 on 08-Jan-2025
REM Old TITL 419_re1_a.res in Cmca
REM SHELXT solution in Cmca: R1 0.065, Rweak 0.004, Alpha 0.013
REM <I/s> 0.874 for 123 systematic absences, Orientation as input
REM Formula found by SHELXT: C6 I3 N3 P2
CELL 0.71073 14.2452 14.5204 14.3176 90 90 90
ZERR 8 0.0005 0.0006 0.0005 0 0 0
LATT 7
SYMM -X,0.5-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM +X,-Y,-Z
SFAC C H I N P
UNIT 45.66 132.31 24 32 8
DFIX 0.97 C3 H3b C3 H3a
DANG 1.57 H3a H3b
DFIX 0.97 C2 H2a C2 H2b
DANG 1.57 H2a H2b
DFIX 0.97 C1 H1a C1 H1b
DANG 1.57 H1a H1b
DANG 1.53 P1 H1b P1 H1a
DFIX 1.06 N1 H1c N1 H1d N1 H1e
DANG 1.75 H1c H1d H1c H1e H1d H1e

L.S. 15
PLAN  5
SIZE 0.15 0.26 0.32
TEMP 136.85
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
acta
OMIT 4 6 2
REM <olex2.extras>
REM <HklSrc "%.\\p-I_410K.hkl">
REM </olex2.extras>

WGHT    0.070100    0.013700
EXTI    0.000276
FVAR       0.11150
I001  3    0.500000    0.536303    0.273454    10.50000    0.05483    0.05536 =
         0.05054   -0.00173    0.00000    0.00000
I002  3    0.500000    0.728746    0.517812    10.50000    0.05864    0.05437 =
         0.05681    0.00403    0.00000    0.00000
I003  3    0.250000    0.744483    0.250000    10.50000    0.06219    0.06000 =
         0.05854    0.00000    0.00344    0.00000
PART -1
P1    5    0.841474    0.430960    0.428506    10.50000    0.05187    0.05076 =
         0.04741    0.00296    0.00926    0.00820
PART 0
N3    4    0.694840    0.559276    0.440278    11.00000    0.05022    0.04645 =
         0.04638    0.00694   -0.00655    0.00592
PART 2
H3    2    0.650215    0.587242    0.402505     0.76957   -1.20000

PART 0
N1    4    0.500000    0.789078    0.272653    10.50000    0.07280    0.06350 =
         0.05644    0.00440    0.00000    0.00000

C4    1    0.634983    0.500000    0.500000    10.50000    0.03843    0.05457 =
         0.06235    0.00363    0.00000    0.00000
AFIX  23
H4A   2    0.595052    0.461864    0.461069    10.50000   -1.20000
H4B   2    0.595051    0.538136    0.538930    10.50000   -1.20000
AFIX   0
C2    1    0.754650    0.500862    0.374650     0.85378    0.05150    0.05695 =
         0.03427   -0.00397   -0.00046    0.00168
C3    1    0.755020    0.623401    0.498519    11.00000    0.05518    0.04401 =
         0.07009   -0.00376   -0.00256   -0.00018
C1    1    0.884376    0.484889    0.484471    10.50000    0.03857    0.05146 =
         0.06493   -0.00332    0.00211    0.00114
PART 1
N2    4    0.809137    0.434387    0.435403    10.50000    0.04610    0.06514 =
         0.05170   -0.01010    0.00143   -0.00352
PART 0
H3A   2    0.788313    0.661051    0.451970    11.00000   -1.20000
H3B   2    0.716672    0.660891    0.540217    11.00000   -1.20000
H2A   2    0.715595    0.465603    0.331353    11.00000   -1.20000
H2B   2    0.790095    0.542447    0.334379    11.00000   -1.20000
PART -2
H1A   2    0.929044    0.522142    0.448970    10.50000    0.11288
H1B   2    0.920525    0.431799    0.506206    10.50000    0.05745
PART 0
H1C   2    0.443784    0.742985    0.260352    10.50000   -1.20000
H1D   2    0.500000    0.841759    0.220533    10.50000   -1.20000
H1E   2    0.500000    0.818575    0.338552    10.50000   -1.20000
HKLF 4




REM  419_re1_a.res in Cmca
REM wR2 = 0.0953, GooF = S = 1.089, Restrained GooF = 1.085 for all data
REM R1 = 0.0339 for 1456 Fo > 4sig(Fo) and 0.0356 for all 1564 data
REM 116 parameters refined using 15 restraints

END

WGHT      0.0701      0.0137

REM Highest difference peak  0.828,  deepest hole -0.891,  1-sigma level  0.159
Q1    1   0.5000  0.7437  0.5780  10.50000  0.05    0.83
Q2    1   0.2424  0.7557  0.3138  11.00000  0.05    0.78
Q3    1   0.5000  0.7223  0.4553  10.50000  0.05    0.74
Q4    1   0.5460  0.4875  0.2776  11.00000  0.05    0.71
Q5    1   0.5000  0.5229  0.3336  10.50000  0.05    0.71
;
_shelx_res_checksum              3836
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.782
_oxdiff_exptl_absorpt_empirical_full_min 0.653
####################################################################### 
# 
# 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_p-i_253k
_database_code_depnum_ccdc_archive 'CCDC 2424323'
loop_
_audit_author_name
_audit_author_address
'Ryo Tsunashima'
;yamaguchi
Japan
;
_audit_update_record             
;
2025-02-17 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;
_audit_creation_date             2025-01-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(I), C6 H14 N3 P, H4 N'
_chemical_formula_sum            'C6 H18 I3 N4 P'
_chemical_formula_weight         557.91
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H18N3IP
_chemical_oxdiff_usercomment     'solid solution 7-3'
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        'C m c e'
_space_group_name_Hall           '-C 2bc 2'
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                   14.1395(5)
_cell_length_b                   14.4681(5)
_cell_length_c                   14.2255(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2910.13(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6324
_cell_measurement_temperature    253
_cell_measurement_theta_max      30.6960
_cell_measurement_theta_min      2.4790
_shelx_estimated_absorpt_T_max   0.403
_shelx_estimated_absorpt_T_min   0.237
_exptl_absorpt_coefficient_mu    6.531
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.547
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2048
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 20 0 0.1295
8 4 18 0.1492
5 -12 15 0.1474
-8 -9 -16 0.0668
-3 17 -11 0.1195
-6 12 15 0.0835
-19 1 7 0.0658
3 -13 -15 0.0855
19 0 -7 0.1073
-16 -3 11 0.0825

_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.3767 20.2446 -0.4157 0.6580 0.1936 0.7277
8.4878 3.5689 17.7961 -0.5466 -0.1649 0.8210
5.3223 -12.1376 15.1920 -0.9486 -0.2825 0.1430
-8.3252 -9.0398 -15.9013 0.3027 0.0927 -0.9486
-2.9185 16.6854 -11.1442 0.9428 0.2799 0.1810
-6.3315 12.2804 14.6732 -0.1890 0.6280 0.7549
-18.8139 0.5231 6.6562 -0.2825 0.9514 -0.1226
3.4212 -13.3092 -14.7835 0.1539 -0.5091 -0.8468
18.8555 -0.4017 -6.5450 0.2822 -0.9504 0.1309
-16.3768 -3.4134 10.9827 -0.5656 0.8207 -0.0816

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6432
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.471
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      253
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  64.00   0.25    0.17    --   -5.68  71.00  50.00  364
  2  ω    -16.00  39.00   0.25    0.17    --    6.15 -99.00-150.00  220
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0023918000
_diffrn_orient_matrix_UB_12      0.0314373000
_diffrn_orient_matrix_UB_13      -0.0381592000
_diffrn_orient_matrix_UB_21      -0.0466342000
_diffrn_orient_matrix_UB_22      0.0152422000
_diffrn_orient_matrix_UB_23      0.0099217000
_diffrn_orient_matrix_UB_31      0.0182697000
_diffrn_orient_matrix_UB_32      0.0344279000
_diffrn_orient_matrix_UB_33      0.0305166000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1493
_reflns_number_total             1547
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.925
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       0.00102(5)
_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   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1547
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0224
_refine_ls_R_factor_gt           0.0211
_refine_ls_restrained_S_all      1.090
_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)+(0.0312P)²+4.1922P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0522
_refine_ls_wR_factor_ref         0.0527
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All H(H,H,H) groups, All C(H,H) groups, All N(H) groups, All N(H,H,H,H) groups
2. Restrained distances
 C1-H1A = C1-H1B
 1.09 with sigma of 0.02
 N1-H1C = N1-H1D = N1-H1E
 1.06 with sigma of 0.02
 H1A-H1B
 1.78 with sigma of 0.04
 H1C-H1D = H1C-H1E = H1D-H1E
 1.75 with sigma of 0.04
3. Others
 Fixed Sof: P1(0.5) H4A(0.5) H4B(0.5) C1(0.5) N2(0.5) H1A(0.5) H1B(0.5)
4.a Ternary CH refined with riding coordinates:
 N3(H3)
4.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
I001 I 0.500000 0.46065(2) 0.72612(2) 0.02498(11) Uani 1 2 d S T P . .
I002 I 0.500000 0.27105(2) 0.47967(2) 0.02679(11) Uani 1 2 d S T P . .
I003 I 0.750000 0.25494(2) 0.750000 0.03017(11) Uani 1 2 d S T P . .
P1 P 0.1565(2) 0.5684(3) 0.5709(3) 0.0220(6) Uani 0.5 1 d . . P A 1
N1 N 0.500000 0.2071(3) 0.7243(3) 0.0320(9) Uani 1 2 d DS T P . .
N3 N 0.30484(18) 0.44008(17) 0.55984(16) 0.0218(5) Uani 1 1 d . . . . .
H3 H 0.347003 0.401428 0.599099 0.026 Uiso 1 1 calc R U . . .
C3 C 0.2442(2) 0.3753(2) 0.5008(2) 0.0286(7) Uani 1 1 d . . . . .
C4 C 0.3659(3) 0.500000 0.500000 0.0264(9) Uani 1 2 d S T P . .
H4A H 0.406494 0.538459 0.539834 0.032 Uiso 0.5 1 calc R U P . .
H4B H 0.406491 0.461540 0.460164 0.032 Uiso 0.5 1 calc R U P . .
C2 C 0.2446(2) 0.4985(2) 0.6259(2) 0.0287(7) Uani 1 1 d . . . . .
C1 C 0.1129(4) 0.5165(5) 0.5162(5) 0.0234(16) Uani 0.5 1 d D . P . .
N2 N 0.1905(6) 0.5669(10) 0.5675(9) 0.025(2) Uani 0.5 1 d . . P A -1
H3A H 0.205(3) 0.341(3) 0.546(3) 0.029 Uiso 1 1 d . U . . .
H3B H 0.290(3) 0.335(3) 0.460(3) 0.029 Uiso 1 1 d . U . . .
H2A H 0.209(3) 0.454(3) 0.667(3) 0.029 Uiso 1 1 d . U . . .
H2B H 0.291(3) 0.535(3) 0.665(3) 0.029 Uiso 1 1 d . U . . .
H1A H 0.068(4) 0.480(4) 0.566(4) 0.022(16) Uiso 0.5 1 d D . P B -1
H1B H 0.071(5) 0.571(4) 0.482(5) 0.04(2) Uiso 0.5 1 d D . P C -1
H1C H 0.500000 0.1361(16) 0.742(4) 0.048 Uiso 1 2 d DS U P . .
H1D H 0.500000 0.220(4) 0.6509(15) 0.048 Uiso 1 2 d DS U P . .
H1E H 0.565(2) 0.235(3) 0.748(3) 0.048 Uiso 1 1 d D U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I001 0.02903(18) 0.02501(18) 0.02090(16) -0.00109(10) 0.000 0.000
I002 0.03137(19) 0.02403(18) 0.02497(17) 0.00224(10) 0.000 0.000
I003 0.0346(2) 0.02923(19) 0.02674(18) 0.000 0.00284(12) 0.000
P1 0.0264(17) 0.0202(10) 0.0195(9) 0.0021(7) 0.0038(13) 0.0025(15)
N1 0.041(2) 0.027(2) 0.028(2) 0.0057(16) 0.000 0.000
N3 0.0265(13) 0.0190(12) 0.0199(12) 0.0030(9) -0.0035(9) 0.0010(10)
C3 0.0312(19) 0.0158(16) 0.0389(19) -0.0038(12) -0.0045(14) -0.0007(14)
C4 0.022(2) 0.029(2) 0.028(2) 0.0034(16) 0.000 0.000
C2 0.0330(19) 0.0367(19) 0.0165(15) -0.0047(12) -0.0009(12) 0.0032(14)
C1 0.021(3) 0.022(5) 0.027(5) -0.005(3) 0.001(2) 0.001(3)
N2 0.020(5) 0.026(4) 0.027(4) -0.010(3) -0.003(4) -0.006(5)

_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 C3 1.801(5) 4_566 ?
P1 C2 1.785(5) . ?
P1 C1 1.245(7) . ?
P1 C1 1.851(6) 4_566 ?
N1 H1C 1.058(18) . ?
N1 H1D 1.059(18) . ?
N1 H1E 1.066(18) . ?
N3 H3 0.9900 . ?
N3 C3 1.523(4) . ?
N3 C4 1.490(4) . ?
N3 C2 1.525(4) . ?
C3 H3A 0.98(4) . ?
C3 H3B 1.05(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C2 N2 1.501(13) . ?
C2 H2A 1.00(4) . ?
C2 H2B 1.01(4) . ?
C1 C1 0.663(10) 4_566 ?
C1 N2 1.506(12) . ?
C1 H1A 1.09(2) . ?
C1 H1B 1.09(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
C3 P1 C1 98.7(3) 4_566 4_566 ?
C2 P1 C3 91.4(2) . 4_566 ?
C2 P1 C1 98.6(3) . 4_566 ?
C1 P1 C3 105.1(4) . 4_566 ?
C1 P1 C2 106.1(5) . . ?
C1 P1 C1 10.23(19) . 4_566 ?
H1C N1 H1D 114(3) . . ?
H1C N1 H1E 107(2) . . ?
H1D N1 H1E 104(2) . . ?
C3 N3 H3 107.6 . . ?
C3 N3 C2 111.5(2) . . ?
C4 N3 H3 107.6 . . ?
C4 N3 C3 111.7(2) . . ?
C4 N3 C2 110.7(2) . . ?
C2 N3 H3 107.6 . . ?
P1 C3 H3A 102(2) 4_566 . ?
P1 C3 H3B 112(2) 4_566 . ?
N3 C3 P1 114.9(3) . 4_566 ?
N3 C3 H3A 106(2) . . ?
N3 C3 H3B 107(2) . . ?
H3A C3 H3B 115(3) . . ?
N3 C4 N3 109.2(3) 4_566 . ?
N3 C4 H4A 109.8 . . ?
N3 C4 H4A 109.8 4_566 . ?
N3 C4 H4B 109.8 4_566 . ?
N3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
P1 C2 H2A 106(2) . . ?
P1 C2 H2B 114(2) . . ?
N3 C2 P1 115.7(2) . . ?
N3 C2 H2A 106(2) . . ?
N3 C2 H2B 106(2) . . ?
N2 C2 P1 13.7(4) . . ?
N2 C2 N3 108.0(5) . . ?
N2 C2 H2A 119(2) . . ?
N2 C2 H2B 107(2) . . ?
H2A C2 H2B 110(3) . . ?
P1 C1 P1 130.9(5) . 4_566 ?
P1 C1 N2 17.1(5) . . ?
P1 C1 H1A 108(4) 4_566 . ?
P1 C1 H1A 100(4) . . ?
P1 C1 H1B 111(5) 4_566 . ?
P1 C1 H1B 96(4) . . ?
C1 C1 P1 19.5(2) 4_566 4_566 ?
C1 C1 P1 150.3(3) 4_566 . ?
C1 C1 N2 133.2(5) 4_566 . ?
C1 C1 H1A 96(4) 4_566 . ?
C1 C1 H1B 102(5) 4_566 . ?
N2 C1 P1 113.8(5) . 4_566 ?
N2 C1 H1A 111(4) . . ?
N2 C1 H1B 105(4) . . ?
H1A C1 H1B 109(3) . . ?
C2 N2 C1 108.7(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
P1 C2 N2 C1 -53(2) . . . . ?
P1 C1 N2 C2 -65.0(9) 4_566 . . . ?
P1 C1 N2 C2 112(2) . . . . ?
N3 C2 N2 C1 73.2(7) . . . . ?
C3 P1 C2 N3 -56.8(3) 4_566 . . . ?
C3 P1 C2 N2 2(3) 4_566 . . . ?
C3 P1 C1 P1 49.1(9) 4_566 . . 4_566 ?
C3 P1 C1 C1 52(4) 4_566 . . 4_566 ?
C3 P1 C1 N2 46(2) 4_566 . . . ?
C3 N3 C4 N3 62.58(19) . . . 4_566 ?
C3 N3 C2 P1 -57.9(3) . . . . ?
C3 N3 C2 N2 -70.2(5) . . . . ?
C4 N3 C3 P1 -66.0(3) . . . 4_566 ?
C4 N3 C2 P1 67.0(3) . . . . ?
C4 N3 C2 N2 54.8(5) . . . . ?
C2 P1 C1 P1 -46.9(9) . . . 4_566 ?
C2 P1 C1 C1 -44(4) . . . 4_566 ?
C2 P1 C1 N2 -50(2) . . . . ?
C2 N3 C3 P1 58.4(3) . . . 4_566 ?
C2 N3 C4 N3 -62.32(18) . . . 4_566 ?
C1 P1 C2 N3 42.2(4) 4_566 . . . ?
C1 P1 C2 N3 49.3(5) . . . . ?
C1 P1 C2 N2 108(3) . . . . ?
C1 P1 C2 N2 100(3) 4_566 . . . ?
C1 P1 C1 P1 -3(3) 4_566 . . 4_566 ?
C1 P1 C1 N2 -6(5) 4_566 . . . ?
C1 C1 N2 C2 -63(3) 4_566 . . . ?

_shelx_res_file                  
;
TITL 253_re1_a.res in Cmca
    p-i_253k.res
    created by SHELXL-2018/3 at 11:59:21 on 08-Jan-2025
REM Old TITL 253_re1_a.res in Cmca
REM SHELXT solution in Cmca: R1 0.068, Rweak 0.005, Alpha 0.015
REM <I/s> 1.302 for 121 systematic absences, Orientation as input
REM Formula found by SHELXT: C6 I3 N5
CELL 0.71073 14.1395 14.4681 14.2255 90 90 90
ZERR 8 0.0005 0.0005 0.0004 0 0 0
LATT 7
SYMM -X,0.5-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM +X,-Y,-Z
SFAC C H I N P
UNIT 48 144 24 32 8
DFIX 1.09 C1 H1a C1 H1b
DANG 1.78 H1a H1b
DFIX 1.06 N1 H1c N1 H1d N1 H1e
DANG 1.75 H1c H1d H1c H1e H1d H1e

L.S. 8 0 0
PLAN  6
SIZE 0.17 0.24 0.31
TEMP -20.15
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\p-I_253K.hkl">
REM </olex2.extras>

WGHT    0.031200    4.192200
EXTI    0.001018
FVAR       0.13345
I001  3    0.500000    0.460653    0.726120    10.50000    0.02903    0.02501 =
         0.02090   -0.00109    0.00000    0.00000
I002  3    0.500000    0.271046    0.479675    10.50000    0.03137    0.02403 =
         0.02497    0.00224    0.00000    0.00000
I003  3    0.750000    0.254940    0.750000    10.50000    0.03456    0.02923 =
         0.02674    0.00000    0.00284    0.00000
PART 1
P1    5    0.156494    0.568419    0.570919    10.50000    0.02645    0.02017 =
         0.01952    0.00212    0.00377    0.00253

PART 0
N1    4    0.500000    0.207133    0.724275    10.50000    0.04149    0.02697 =
         0.02751    0.00568    0.00000    0.00000

N3    4    0.304842    0.440084    0.559839    11.00000    0.02653    0.01902 =
         0.01993    0.00302   -0.00352    0.00102
AFIX  13
H3    2    0.347003    0.401428    0.599099    11.00000   -1.20000
AFIX   0
C3    1    0.244230    0.375260    0.500790    11.00000    0.03121    0.01583 =
         0.03887   -0.00383   -0.00445   -0.00069
C4    1    0.365885    0.500000    0.500000    10.50000    0.02181    0.02905 =
         0.02834    0.00344    0.00000    0.00000
AFIX  23
H4A   2    0.406494    0.538459    0.539834    10.50000   -1.20000
H4B   2    0.406491    0.461540    0.460164    10.50000   -1.20000
AFIX   0
C2    1    0.244599    0.498542    0.625905    11.00000    0.03296    0.03668 =
         0.01645   -0.00466   -0.00090    0.00317
C1    1    0.112878    0.516476    0.516189    10.50000    0.02091    0.02204 =
         0.02732   -0.00477    0.00100    0.00103
PART -1
N2    4    0.190474    0.566880    0.567543    10.50000    0.02002    0.02603 =
         0.02748   -0.00960   -0.00346   -0.00585
PART 0
H3A   2    0.204783    0.340992    0.545731    11.00000   -1.20000
H3B   2    0.290298    0.334685    0.460294    11.00000   -1.20000
H2A   2    0.209319    0.453772    0.666585    11.00000   -1.20000
H2B   2    0.290735    0.534716    0.665429    11.00000   -1.20000
PART -1
H1A   2    0.067584    0.479943    0.565584    10.50000    0.02196
H1B   2    0.071485    0.570762    0.482097    10.50000    0.04037
PART 0
H1C   2    0.500000    0.136094    0.742028    10.50000   -1.20000
H1D   2    0.500000    0.219572    0.650935    10.50000   -1.20000
H1E   2    0.565270    0.235480    0.748184    11.00000   -1.20000
HKLF 4




REM  253_re1_a.res in Cmca
REM wR2 = 0.0527, GooF = S = 1.092, Restrained GooF = 1.090 for all data
REM R1 = 0.0211 for 1493 Fo > 4sig(Fo) and 0.0224 for all 1547 data
REM 111 parameters refined using 9 restraints

END

WGHT      0.0312      4.1922

REM Highest difference peak  0.925,  deepest hole -0.551,  1-sigma level  0.126
Q1    1   0.5000  0.1995  0.4840  10.50000  0.05    0.92
Q2    1   0.5000  0.3398  0.4783  10.50000  0.05    0.81
Q3    1   0.5000  0.4009  0.7719  10.50000  0.05    0.67
Q4    1   0.5000  0.5246  0.7255  10.50000  0.05    0.62
Q5    1   0.7500  0.3242  0.7500  10.50000  0.05    0.59
Q6    1   0.7500  0.1758  0.7500  10.50000  0.05    0.58
;
_shelx_res_checksum              8368
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.874
_oxdiff_exptl_absorpt_empirical_full_min 0.593
####################################################################### 
# 
# 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_pta-br_425_1
_database_code_depnum_ccdc_archive 'CCDC 2424518'
loop_
_audit_author_name
_audit_author_address
'Ryo Tsunashima'
;yamaguchi
Japan
;
_audit_update_record             
;
2025-02-17 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;
_audit_creation_date             2025-01-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(Br), N, 2(C7)'
_chemical_formula_sum            'C14 Br3 N'
_chemical_formula_weight         421.88
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H18N3Br3P
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'

_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      cubic
_space_group_IT_number           221
_space_group_name_H-M_alt        'P m -3 m'
_space_group_name_Hall           '-P 4 2 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x, y, -z'
'x, -y, -z'
'z, x, y'
'z, -x, -y'
'-z, -x, y'
'-z, x, -y'
'y, z, x'
'-y, z, -x'
'y, -z, -x'
'-y, -z, x'
'y, x, -z'
'-y, -x, -z'
'y, -x, z'
'-y, x, z'
'x, z, -y'
'-x, z, y'
'-x, -z, -y'
'x, -z, y'
'z, y, -x'
'z, -y, x'
'-z, y, x'
'-z, -y, -x'
'-x, -y, -z'
'x, y, -z'
'x, -y, z'
'-x, y, z'
'-z, -x, -y'
'-z, x, y'
'z, x, -y'
'z, -x, y'
'-y, -z, -x'
'y, -z, x'
'-y, z, x'
'y, z, -x'
'-y, -x, z'
'y, x, z'
'-y, x, -z'
'y, -x, -z'
'-x, -z, y'
'x, -z, -y'
'x, z, y'
'-x, z, -y'
'-z, -y, x'
'-z, y, -x'
'z, -y, -x'
'z, y, x'

_cell_length_a                   7.0146(4)
_cell_length_b                   7.0146(4)
_cell_length_c                   7.0146(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     345.15(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    341
_cell_measurement_temperature    415
_cell_measurement_theta_max      18.9030
_cell_measurement_theta_min      2.8900
_shelx_estimated_absorpt_T_max   0.335
_shelx_estimated_absorpt_T_min   0.201
_exptl_absorpt_coefficient_mu    8.744
_exptl_absorpt_correction_T_max  0.538
_exptl_absorpt_correction_T_min  0.323
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.030
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             196
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -9 4 0.0880
9 2 4 0.0635
0 9 -3 0.0824
-8 3 -5 0.0862
-8 -5 -3 0.0857
3 -6 8 0.0940
-7 7 1 0.0893
-1 4 -9 0.0546
7 -6 -5 0.0660
-10 2 1 0.0824

_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.6616 -8.6356 4.0010 -0.0697 -0.2799 0.9575
8.6283 2.4825 4.1483 0.2048 0.8626 0.4626
-0.3246 9.4423 -2.9163 0.1270 0.5213 -0.8438
-7.8797 2.8085 -5.2577 -0.1153 -0.4930 -0.8624
-7.9545 -5.0489 -3.0254 -0.2278 -0.9555 -0.1872
2.8640 -5.7132 7.5275 -0.3568 0.0826 0.9305
-6.7652 7.1222 1.1690 -0.5824 0.1414 -0.8005
-0.9205 4.0377 -8.9649 0.6069 -0.1428 -0.7818
6.5135 -5.5719 -4.9471 0.8482 -0.2041 0.4889
-9.6499 1.6369 1.4339 -0.7404 -0.4047 -0.5366

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       2
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            1544
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.606
_diffrn_reflns_theta_min         2.904
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      415
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  11.00   0.25    2.20    --   -5.68 -59.00  26.00  300
  2  ω    -16.00  39.00   0.25    2.20    --    6.15 -99.00   0.00  220
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0636938000
_diffrn_orient_matrix_UB_12      -0.0084625000
_diffrn_orient_matrix_UB_13      -0.0780531000
_diffrn_orient_matrix_UB_21      0.0599602000
_diffrn_orient_matrix_UB_22      0.0700337000
_diffrn_orient_matrix_UB_23      0.0413157000
_diffrn_orient_matrix_UB_31      0.0506777000
_diffrn_orient_matrix_UB_32      -0.0723661000
_diffrn_orient_matrix_UB_33      0.0494114000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                58
_reflns_number_total             135
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.134
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     10
_refine_ls_number_reflns         135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1203
_refine_ls_R_factor_gt           0.0729
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1586P)²+0.0619P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2556
_refine_ls_wR_factor_ref         0.2999
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   .
_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
Br01 Br 0.500000 0.000000 0.000000 0.177(3) Uani 1 16 d S T P . .
N1 N 0.000000 0.000000 0.000000 0.159(13) Uani 1 48 d S T P . .
C2 C 0.759(2) 0.500000 0.500000 0.151(6) Uani 1 8 d S T P . .
C1 C 0.6473(12) 0.3527(12) 0.3527(12) 0.167(6) Uani 1 6 d S T P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br01 0.169(3) 0.182(3) 0.182(3) 0.000 0.000 0.000
N1 0.159(13) 0.159(13) 0.159(13) 0.000 0.000 0.000
C2 0.108(10) 0.173(9) 0.173(9) 0.000 0.000 0.000
C1 0.167(6) 0.167(6) 0.167(6) -0.005(7) 0.005(7) 0.005(7)

_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
C2 C1 1.656(7) . ?
C2 C1 1.656(7) 27_565 ?
C2 C1 1.656(7) 26_556 ?
C2 C1 1.656(7) 4_566 ?

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
C1 C2 C1 123.8(16) . 4_566 ?
C1 C2 C1 77.2(7) . 26_556 ?
C1 C2 C1 77.2(7) 4_566 26_556 ?
C1 C2 C1 77.2(7) 4_566 27_565 ?
C1 C2 C1 123.8(16) 27_565 26_556 ?
C1 C2 C1 77.2(7) . 27_565 ?
C2 C1 C2 101.5(10) . 33_666 ?
C2 C1 C2 101.5(10) . 29_666 ?
C2 C1 C2 101.5(10) 33_666 29_666 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C1 C2 52.2(8) 4_566 . . 33_666 ?
C1 C2 C1 C2 -52.2(8) 4_566 . . 29_666 ?
C1 C2 C1 C2 12.6(13) 26_556 . . 29_666 ?
C1 C2 C1 C2 116.96(19) 26_556 . . 33_666 ?
C1 C2 C1 C2 -12.6(13) 27_565 . . 33_666 ?
C1 C2 C1 C2 -116.96(19) 27_565 . . 29_666 ?

_shelx_res_file                  
;
TITL pta-br_425_1_a.res in Pm-3m
    pta-br_425_1.res
    created by SHELXL-2018/3 at 14:02:14 on 08-Jan-2025
REM Old TITL pta-Br_425_1 in Pm-3m
REM SHELXT solution in Pm-3m: R1 0.085, Rweak 0.097, Alpha 0.018
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Formula found by SHELXT: C14 N Br3
CELL 0.71073 7.0146 7.0146 7.0146 90 90 90
ZERR 1 0.0004 0.0004 0.0004 0 0 0
LATT 1
SYMM -X,-Y,+Z
SYMM -X,+Y,-Z
SYMM +X,-Y,-Z
SYMM +Z,+X,+Y
SYMM +Z,-X,-Y
SYMM -Z,-X,+Y
SYMM -Z,+X,-Y
SYMM +Y,+Z,+X
SYMM -Y,+Z,-X
SYMM +Y,-Z,-X
SYMM -Y,-Z,+X
SYMM +Y,+X,-Z
SYMM -Y,-X,-Z
SYMM +Y,-X,+Z
SYMM -Y,+X,+Z
SYMM +X,+Z,-Y
SYMM -X,+Z,+Y
SYMM -X,-Z,-Y
SYMM +X,-Z,+Y
SYMM +Z,+Y,-X
SYMM +Z,-Y,+X
SYMM -Z,+Y,+X
SYMM -Z,-Y,-X
SFAC Br C N
UNIT 3 14 1

L.S. 4 0 0
PLAN  1
SIZE 0.16 0.19 0.27
TEMP 141.85
CONF
list 4
MORE -1
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\pta-Br_425_1.hkl">
REM </olex2.extras>

WGHT    0.158600    0.061900
FVAR       1.22185
BR01  1    0.500000    0.000000    0.000000    10.06250    0.16932    0.18151 =
         0.18151    0.00000    0.00000    0.00000
N1    3    0.000000    0.000000    0.000000    10.02083    0.15865    0.15865 =
         0.15865    0.00000    0.00000    0.00000
C2    2    0.758551    0.500000    0.500000    10.12500    0.10811    0.17294 =
         0.17294    0.00000    0.00000    0.00000
C1    2    0.647255    0.352745    0.352745    10.16667    0.16726    0.16726 =
         0.16726   -0.00479    0.00479    0.00479
HKLF 4




REM  pta-br_425_1_a.res in Pm-3m
REM wR2 = 0.2999, GooF = S = 1.101, Restrained GooF = 1.101 for all data
REM R1 = 0.0729 for 58 Fo > 4sig(Fo) and 0.1203 for all 135 data
REM 10 parameters refined using 0 restraints

END

WGHT      0.1586      0.0619

REM Highest difference peak  0.742,  deepest hole -0.433,  1-sigma level  0.134
Q1    1   0.5000  0.5000  0.5000  10.02083  0.05    0.23
;
_shelx_res_checksum              93431
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.630
_oxdiff_exptl_absorpt_empirical_full_min 0.767
####################################################################### 
# 
# 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_391k_cubic_rt1
_database_code_depnum_ccdc_archive 'CCDC 2424528'
loop_
_audit_author_name
_audit_author_address
'Ryo Tsunashima'
;yamaguchi
Japan
;
_audit_update_record             
;
2025-02-17 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;
_audit_creation_date             2024-12-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(Br), N, 2(C6.318)'
_chemical_formula_sum            'C12.60 Br3 N'
_chemical_formula_weight         405.07
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H18NBr3P
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'

_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      cubic
_space_group_IT_number           221
_space_group_name_H-M_alt        'P m -3 m'
_space_group_name_Hall           '-P 4 2 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x, y, -z'
'x, -y, -z'
'z, x, y'
'z, -x, -y'
'-z, -x, y'
'-z, x, -y'
'y, z, x'
'-y, z, -x'
'y, -z, -x'
'-y, -z, x'
'y, x, -z'
'-y, -x, -z'
'y, -x, z'
'-y, x, z'
'x, z, -y'
'-x, z, y'
'-x, -z, -y'
'x, -z, y'
'z, y, -x'
'z, -y, x'
'-z, y, x'
'-z, -y, -x'
'-x, -y, -z'
'x, y, -z'
'x, -y, z'
'-x, y, z'
'-z, -x, -y'
'-z, x, y'
'z, x, -y'
'z, -x, y'
'-y, -z, -x'
'y, -z, x'
'-y, z, x'
'y, z, -x'
'-y, -x, z'
'y, x, z'
'-y, x, -z'
'y, -x, -z'
'-x, -z, y'
'x, -z, -y'
'x, z, y'
'-x, z, -y'
'-z, -y, x'
'-z, y, -x'
'z, -y, -x'
'z, y, x'

_cell_length_a                   6.9497(9)
_cell_length_b                   6.9497(9)
_cell_length_c                   6.9497(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     335.66(13)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    432
_cell_measurement_temperature    391
_cell_measurement_theta_max      20.6550
_cell_measurement_theta_min      2.9140
_shelx_estimated_absorpt_T_max   0.346
_shelx_estimated_absorpt_T_min   0.242
_exptl_absorpt_coefficient_mu    8.987
_exptl_absorpt_correction_T_max  0.507
_exptl_absorpt_correction_T_min  0.233
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.004
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             188
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 -4 -7 0.0841
-1 9 -3 0.0431
4 3 -9 0.0555
0 -3 -9 0.0814
-7 -1 -7 0.1063
6 2 8 0.0905
9 -3 0 0.1016
-8 5 4 0.0552
0 -4 -9 0.0820
0 -10 -2 0.0770
4 8 -4 0.0636
-4 -9 3 0.1066
-2 -9 -4 0.0800
5 -9 0 0.0847
3 -8 -5 0.0769

_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.7368 -4.4785 -7.2935 0.0257 0.0470 -0.9986
-0.9850 9.2856 -2.9636 0.4963 0.8102 0.3119
3.5220 2.8082 -8.7148 0.3876 0.6374 -0.6659
0.1670 -3.0665 -9.3153 -0.2580 0.4693 -0.8445
-7.0631 -0.5247 -6.7733 -0.6415 0.7488 -0.1669
5.7039 1.5096 7.8363 0.6066 -0.7073 0.3630
9.2154 -3.1846 0.4049 0.5212 -0.6114 -0.5954
-7.5089 4.6516 4.1523 -0.2569 0.3039 0.9174
0.0200 -4.0968 -8.9123 -0.3326 0.3851 -0.8609
-0.1125 -9.6344 -1.8251 -0.6428 -0.4449 -0.6236
4.2541 8.0479 -3.7029 0.8217 0.5658 -0.0677
-3.7297 -8.6066 2.9300 -0.8227 -0.5668 -0.0436
-2.4962 -8.7093 -3.7972 -0.7859 -0.1482 -0.6003
4.7454 -8.5293 0.3011 -0.1738 -0.7355 -0.6548
2.5057 -8.1466 -4.8113 -0.3655 -0.2548 -0.8953

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            1499
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.411
_diffrn_reflns_theta_min         2.931
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      391
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  11.00   0.25    2.20    --   -5.68 -59.00  26.00  300
  2  ω    -16.00  39.00   0.25    2.20    --    6.15 -99.00   0.00  220
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0784320000
_diffrn_orient_matrix_UB_12      0.0642989000
_diffrn_orient_matrix_UB_13      0.0079368000
_diffrn_orient_matrix_UB_21      -0.0424548000
_diffrn_orient_matrix_UB_22      0.0601115000
_diffrn_orient_matrix_UB_23      -0.0709327000
_diffrn_orient_matrix_UB_31      -0.0500065000
_diffrn_orient_matrix_UB_32      0.0515192000
_diffrn_orient_matrix_UB_33      0.0727998000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                73
_reflns_number_total             132
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.742
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     12
_refine_ls_number_reflns         132
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0455P)²+0.3511P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1308
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   .
_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 0.500000 0.000000 0.000000 0.1446(14) Uani 1 16 d S T P . .
N1 N 0.000000 0.000000 0.000000 0.171(14) Uani 1 48 d S T P . .
C2 C 0.3612(10) 0.3612(10) 0.3612(10) 0.110(6) Uani 0.84(3) 6 d S T . . .
C1 C 0.500000 0.2432(15) 0.500000 0.112(6) Uani 0.98(4) 8 d S T . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.156(2) 0.1391(16) 0.1391(16) 0.000 0.000 0.000
N1 0.171(14) 0.171(14) 0.171(14) 0.000 0.000 0.000
C2 0.110(6) 0.110(6) 0.110(6) -0.002(4) -0.002(4) -0.002(4)
C1 0.134(8) 0.067(7) 0.134(8) 0.000 0.000 0.000

_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
C2 C2 1.929(14) 28_655 ?
C2 C2 1.929(14) 27_565 ?
C2 C2 1.929(14) 26_556 ?
C2 C1 1.592(8) 5 ?
C2 C1 1.592(8) . ?
C2 C1 1.592(8) 9 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C2 C2 90.001(1) 28_655 26_556 ?
C2 C2 C2 90.001(2) 27_565 28_655 ?
C2 C2 C2 90.001(1) 27_565 26_556 ?
C1 C2 C2 52.7(2) . 26_556 ?
C1 C2 C2 52.7(2) 9 26_556 ?
C1 C2 C2 52.7(2) 9 27_565 ?
C1 C2 C2 121.0(5) . 27_565 ?
C1 C2 C2 121.0(5) 9 28_655 ?
C1 C2 C2 52.7(2) 5 28_655 ?
C1 C2 C2 121.0(5) 5 26_556 ?
C1 C2 C2 52.7(2) 5 27_565 ?
C1 C2 C2 52.7(2) . 28_655 ?
C1 C2 C1 104.9(6) 5 . ?
C1 C2 C1 104.9(6) 9 . ?
C1 C2 C1 104.9(6) 9 5 ?
C2 C1 C2 74.6(5) 3_656 28_655 ?
C2 C1 C2 118.0(10) 26_556 28_655 ?
C2 C1 C2 74.6(5) . 26_556 ?
C2 C1 C2 118.0(10) . 3_656 ?
C2 C1 C2 74.6(5) . 28_655 ?
C2 C1 C2 74.6(5) 3_656 26_556 ?

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
C2 C2 C1 C2 0.000(2) 27_565 . . 3_656 ?
C2 C2 C1 C2 125.5(7) 28_655 . . 26_556 ?
C2 C2 C1 C2 62.7(3) 28_655 . . 3_656 ?
C2 C2 C1 C2 -62.7(3) 27_565 . . 28_655 ?
C2 C2 C1 C2 -62.7(3) 26_556 . . 3_656 ?
C2 C2 C1 C2 -125.5(7) 26_556 . . 28_655 ?
C2 C2 C1 C2 62.7(3) 27_565 . . 26_556 ?
C1 C2 C1 C2 -55.1(5) 9 . . 3_656 ?
C1 C2 C1 C2 -117.9(2) 9 . . 28_655 ?
C1 C2 C1 C2 7.6(9) 9 . . 26_556 ?
C1 C2 C1 C2 55.1(5) 5 . . 3_656 ?
C1 C2 C1 C2 117.9(2) 5 . . 26_556 ?
C1 C2 C1 C2 -7.6(9) 5 . . 28_655 ?

_shelx_res_file                  
;
TITL 391k_cubic_rt1_a.res in Pm-3m
    391k_cubic_rt1.res
    created by SHELXL-2018/3 at 14:16:28 on 25-Dec-2024
REM Old TITL 391k_cubic_rt1_a.res in Pm-3m
REM SHELXT solution in Pm-3m: R1 0.257, Rweak 0.167, Alpha 0.040
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Formula found by SHELXT: P3 Br
CELL 0.71073 6.9497 6.9497 6.9497 90 90 90
ZERR 1 0.0009 0.0009 0.0009 0 0 0
LATT 1
SYMM -X,-Y,+Z
SYMM -X,+Y,-Z
SYMM +X,-Y,-Z
SYMM +Z,+X,+Y
SYMM +Z,-X,-Y
SYMM -Z,-X,+Y
SYMM -Z,+X,-Y
SYMM +Y,+Z,+X
SYMM -Y,+Z,-X
SYMM +Y,-Z,-X
SYMM -Y,-Z,+X
SYMM +Y,+X,-Z
SYMM -Y,-X,-Z
SYMM +Y,-X,+Z
SYMM -Y,+X,+Z
SYMM +X,+Z,-Y
SYMM -X,+Z,+Y
SYMM -X,-Z,-Y
SYMM +X,-Z,+Y
SYMM +Z,+Y,-X
SYMM +Z,-Y,+X
SYMM -Z,+Y,+X
SYMM -Z,-Y,-X
SFAC Br C N
UNIT 3 12.6 1

L.S. 4
PLAN  5
SIZE 0.15 0.21 0.22
TEMP 117.85
CONF
list 4
fmap 2
MORE -1
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\391k_cubic_rt1.hkl">
REM </olex2.extras>

WGHT    0.045500    0.351100
FVAR       1.22432
BR1   1    0.500000    0.000000    0.000000    10.06250    0.15556    0.13910 =
         0.13910    0.00000    0.00000    0.00000
N1    3    0.000000    0.000000    0.000000    10.02083    0.17091    0.17091 =
         0.17091    0.00000    0.00000    0.00000
C2    2    0.361196    0.361196    0.361196     0.14078    0.10976    0.10976 =
         0.10976   -0.00211   -0.00211   -0.00211
C1    2    0.500000    0.243165    0.500000     0.12249    0.13446    0.06666 =
         0.13446    0.00000    0.00000    0.00000
HKLF 4




REM  391k_cubic_rt1_a.res in Pm-3m
REM wR2 = 0.1308, GooF = S = 1.088, Restrained GooF = 1.088 for all data
REM R1 = 0.0492 for 73 Fo > 4sig(Fo) and 0.0766 for all 132 data
REM 12 parameters refined using 0 restraints

END

WGHT      0.0492      0.3289

REM Highest difference peak  0.331,  deepest hole -0.742,  1-sigma level  0.072
Q1    1   0.0000  0.1003  0.0000  10.12500  0.05    0.33
Q2    1   0.4187  0.1048  0.5000  10.50000  0.05    0.18
Q3    1   0.5000  0.1573  0.5000  10.12500  0.05    0.17
Q4    1   0.4221  0.1026  0.4221  10.50000  0.05    0.16
Q5    1   0.2391  0.2391  0.5000  10.25000  0.05    0.11
;
_shelx_res_checksum              39726
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.394
_oxdiff_exptl_absorpt_empirical_full_min 0.769
####################################################################### 
# 
# 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_m_pta-br_420_1
_database_code_depnum_ccdc_archive 'CCDC 2424520'
loop_
_audit_author_name
_audit_author_address
'Ryo Tsunashima'
;yamaguchi
Japan
;
_audit_update_record             
;
2025-02-17 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;
_audit_creation_date             2025-01-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(Br), N, 2(C6.15)'
_chemical_formula_sum            'C12.30 Br3 N'
_chemical_formula_weight         401.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H18N3Br3P
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'

_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      cubic
_space_group_IT_number           221
_space_group_name_H-M_alt        'P m -3 m'
_space_group_name_Hall           '-P 4 2 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x, y, -z'
'x, -y, -z'
'z, x, y'
'z, -x, -y'
'-z, -x, y'
'-z, x, -y'
'y, z, x'
'-y, z, -x'
'y, -z, -x'
'-y, -z, x'
'y, x, -z'
'-y, -x, -z'
'y, -x, z'
'-y, x, z'
'x, z, -y'
'-x, z, y'
'-x, -z, -y'
'x, -z, y'
'z, y, -x'
'z, -y, x'
'-z, y, x'
'-z, -y, -x'
'-x, -y, -z'
'x, y, -z'
'x, -y, z'
'-x, y, z'
'-z, -x, -y'
'-z, x, y'
'z, x, -y'
'z, -x, y'
'-y, -z, -x'
'y, -z, x'
'-y, z, x'
'y, z, -x'
'-y, -x, z'
'y, x, z'
'-y, x, -z'
'y, -x, -z'
'-x, -z, y'
'x, -z, -y'
'x, z, y'
'-x, z, -y'
'-z, -y, x'
'-z, y, -x'
'z, -y, -x'
'z, y, x'

_cell_length_a                   7.0028(4)
_cell_length_b                   7.0028(4)
_cell_length_c                   7.0028(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     343.41(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    364
_cell_measurement_temperature    410
_cell_measurement_theta_max      22.9120
_cell_measurement_theta_min      2.8920
_shelx_estimated_absorpt_T_max   0.334
_shelx_estimated_absorpt_T_min   0.227
_exptl_absorpt_coefficient_mu    8.783
_exptl_absorpt_correction_T_max  0.420
_exptl_absorpt_correction_T_min  0.219
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.941
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             186
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 3 9 0.0821
-4 9 -2 0.0702
3 0 -9 0.0865
5 -6 -6 0.0839
5 -9 1 0.0770
2 -7 7 0.0972
-10 -1 2 0.0960
-7 3 6 0.0733
3 7 6 0.0912
9 4 2 0.0880
10 3 0 0.0916
7 -4 -6 0.0798
1 -6 -7 0.0770

_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.9950 2.6922 8.6130 -0.0694 -0.2785 0.9579
-4.1512 8.6278 -2.4046 0.2037 0.8583 0.4709
2.9364 -0.3930 -9.4188 0.1260 0.5169 -0.8467
5.1518 -6.3334 -5.5339 -0.0459 -0.2042 -0.9779
4.6710 -8.6667 0.6774 -0.1800 -0.7608 -0.6235
1.9068 -6.8952 6.8147 -0.2323 -0.9715 0.0475
-9.5419 -0.6721 2.3892 -0.7701 0.1857 0.6102
-7.2341 3.2013 5.8828 -0.3136 0.0776 0.9464
3.0005 6.8159 6.4951 0.7233 -0.1710 0.6691
8.6786 4.3116 1.8869 0.9700 -0.2320 -0.0726
9.5101 2.6118 -0.2506 0.9090 -0.2182 -0.3550
6.8862 -3.5179 -6.1162 0.2642 -0.0658 -0.9622
1.0905 -6.4311 -7.4134 -0.3860 0.0897 -0.9181

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            1404
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.257
_diffrn_reflns_theta_min         2.909
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      410
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  11.00   0.25    2.20    --   -5.68 -59.00  26.00  300
  2  ω    -16.00  39.00   0.25    2.20    --    6.15 -99.00   0.00  220
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0783297000
_diffrn_orient_matrix_UB_12      0.0636379000
_diffrn_orient_matrix_UB_13      0.0083874000
_diffrn_orient_matrix_UB_21      -0.0412851000
_diffrn_orient_matrix_UB_22      0.0600412000
_diffrn_orient_matrix_UB_23      -0.0702560000
_diffrn_orient_matrix_UB_31      -0.0494233000
_diffrn_orient_matrix_UB_32      0.0509662000
_diffrn_orient_matrix_UB_33      0.0723626000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                86
_reflns_number_total             101
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.437
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     12
_refine_ls_number_reflns         101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0620
_refine_ls_restrained_S_all      1.437
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0364P)²+0.2437P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1313
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   .
_atom_sites_solution_primary     iterative
_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
Br01 Br 0.000000 0.000000 0.500000 0.1691(19) Uani 1 16 d S T P . .
N1 N 0.000000 0.000000 0.000000 0.168(14) Uani 1 48 d S T P . .
C2 C 0.500000 0.500000 0.751(2) 0.134(10) Uani 0.90(5) 8 d S T . . .
C1 C 0.3626(14) 0.3626(14) 0.6374(14) 0.162(11) Uani 0.86(4) 6 d S T . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br01 0.172(2) 0.172(2) 0.163(3) 0.000 0.000 0.000
N1 0.168(14) 0.168(14) 0.168(14) 0.000 0.000 0.000
C2 0.157(14) 0.157(14) 0.087(10) 0.000 0.000 0.000
C1 0.162(11) 0.162(11) 0.162(11) 0.015(7) 0.015(7) -0.015(7)

_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
C2 C1 1.577(10) . ?
C2 C1 1.577(10) 2_665 ?
C2 C1 1.577(10) 28_655 ?
C2 C1 1.577(10) 27_565 ?
C1 C1 1.92(2) 28_655 ?
C1 C1 1.92(2) 26_556 ?
C1 C1 1.92(2) 27_565 ?

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
C1 C2 C1 119.3(15) . 2_665 ?
C1 C2 C1 119.3(15) 28_655 27_565 ?
C1 C2 C1 75.2(7) 2_665 28_655 ?
C1 C2 C1 75.2(7) . 28_655 ?
C1 C2 C1 75.2(7) 2_665 27_565 ?
C1 C2 C1 75.2(7) . 27_565 ?
C2 C1 C2 104.1(9) . 33_666 ?
C2 C1 C2 104.1(9) . 29_666 ?
C2 C1 C2 104.1(9) 33_666 29_666 ?
C2 C1 C1 52.4(3) . 28_655 ?
C2 C1 C1 120.3(8) 33_666 27_565 ?
C2 C1 C1 52.4(3) 29_666 27_565 ?
C2 C1 C1 52.4(3) . 27_565 ?
C2 C1 C1 52.4(3) 29_666 26_556 ?
C2 C1 C1 52.4(3) 33_666 26_556 ?
C2 C1 C1 120.3(8) . 26_556 ?
C2 C1 C1 52.4(3) 33_666 28_655 ?
C2 C1 C1 120.3(8) 29_666 28_655 ?
C1 C1 C1 90.000(3) 26_556 27_565 ?
C1 C1 C1 90.000(3) 28_655 27_565 ?
C1 C1 C1 90.000(4) 28_655 26_556 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C1 C2 54.4(8) 2_665 . . 33_666 ?
C1 C2 C1 C2 -8.8(13) 28_655 . . 33_666 ?
C1 C2 C1 C2 117.6(3) 27_565 . . 33_666 ?
C1 C2 C1 C2 -54.4(8) 2_665 . . 29_666 ?
C1 C2 C1 C2 -117.6(3) 28_655 . . 29_666 ?
C1 C2 C1 C2 8.8(13) 27_565 . . 29_666 ?
C1 C2 C1 C1 63.2(5) 2_665 . . 28_655 ?
C1 C2 C1 C1 -63.2(5) 28_655 . . 26_556 ?
C1 C2 C1 C1 -63.2(5) 2_665 . . 27_565 ?
C1 C2 C1 C1 0.000(1) 2_665 . . 26_556 ?
C1 C2 C1 C1 126.4(11) 27_565 . . 28_655 ?
C1 C2 C1 C1 63.2(5) 27_565 . . 26_556 ?
C1 C2 C1 C1 -126.4(11) 28_655 . . 27_565 ?

_shelx_res_file                  
;
TITL m_pta-br_420_1_a.res in Pm-3m
    m_pta-br_420_1.res
    created by SHELXL-2018/3 at 13:58:20 on 08-Jan-2025
REM Old TITL M_pta-Br_420_1 in Pm-3m
REM SHELXT solution in Pm-3m: R1 0.124, Rweak 0.301, Alpha 0.033
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Formula found by SHELXT: C8 N7 Br3
CELL 0.71073 7.0028 7.0028 7.0028 90 90 90
ZERR 1 0.0004 0.0004 0.0004 0 0 0
LATT 1
SYMM -X,-Y,+Z
SYMM -X,+Y,-Z
SYMM +X,-Y,-Z
SYMM +Z,+X,+Y
SYMM +Z,-X,-Y
SYMM -Z,-X,+Y
SYMM -Z,+X,-Y
SYMM +Y,+Z,+X
SYMM -Y,+Z,-X
SYMM +Y,-Z,-X
SYMM -Y,-Z,+X
SYMM +Y,+X,-Z
SYMM -Y,-X,-Z
SYMM +Y,-X,+Z
SYMM -Y,+X,+Z
SYMM +X,+Z,-Y
SYMM -X,+Z,+Y
SYMM -X,-Z,-Y
SYMM +X,-Z,+Y
SYMM +Z,+Y,-X
SYMM +Z,-Y,+X
SYMM -Z,+Y,+X
SYMM -Z,-Y,-X
SFAC Br C N
UNIT 3 12.3 1

L.S. 10
PLAN  5
SIZE 0.16 0.2 0.24
TEMP 136.85
CONF
LIST 6
MORE -1
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\M_pta-Br_420_1.hkl">
REM </olex2.extras>

WGHT    0.036400    0.243700
FVAR       1.26053
BR01  1    0.000000    0.000000    0.500000    10.06250    0.17220    0.17220 =
         0.16299    0.00000    0.00000    0.00000
N1    3    0.000000    0.000000    0.000000    10.02083    0.16785    0.16785 =
         0.16785    0.00000    0.00000    0.00000
C2    2    0.500000    0.500000    0.751118     0.11247    0.15726    0.15726 =
         0.08742    0.00000    0.00000    0.00000
C1    2    0.362592    0.362592    0.637408     0.14377    0.16160    0.16160 =
         0.16160    0.01468    0.01468   -0.01468
HKLF 4




REM  m_pta-br_420_1_a.res in Pm-3m
REM wR2 = 0.1313, GooF = S = 1.437, Restrained GooF = 1.437 for all data
REM R1 = 0.0620 for 86 Fo > 4sig(Fo) and 0.0717 for all 101 data
REM 12 parameters refined using 0 restraints

END

WGHT      0.0363      0.2487

REM Highest difference peak  0.295,  deepest hole -0.189,  1-sigma level  0.061
Q1    1   0.0000  0.0450  0.0450  10.25000  0.05    0.30
Q2    1   0.5000  0.5000  0.9158  10.12500  0.05    0.15
Q3    1   0.1011  0.0000  0.4021  10.50000  0.05    0.13
Q4    1   0.5000  0.5000  1.0000  10.06250  0.05    0.12
Q5    1   0.5692  0.5692  0.8899  10.50000  0.05    0.12
;
_shelx_res_checksum              67344
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.367
_oxdiff_exptl_absorpt_empirical_full_min 0.772
####################################################################### 
# 
# 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_p-bf4_391k
_database_code_depnum_ccdc_archive 'CCDC 2424324'
loop_
_audit_author_name
_audit_author_address
'Ryo Tsunashima'
;yamaguchi
Japan
;
_audit_update_record             
;
2025-02-17 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT242_p-bf4_391k          
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         B1 Check
RESPONSE: due to disorder of BF4 anion
;
# Added during the CSD deposition process: Monday 17 February 2025 06:06 AM
# end Validation Reply Form

_audit_creation_date             2025-01-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H12 N2.902 P1.098, 3(B F4), 0.5(H8 N2)'
_chemical_formula_sum            'C6 H16 B3 F12 N3.90 P1.10'
_chemical_formula_weight         437.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H18N4PB4F12
_chemical_oxdiff_usercomment     35
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'
B B 0.0013 0.0007 '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'
P P 0.1023 0.0942 '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      tetragonal
_space_group_IT_number           86
_space_group_name_H-M_alt        'P 42/n'
_space_group_name_Hall           '-P 4bc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x+1/2, z+1/2'
'-x+1/2, -y+1/2, z'
'y+1/2, -x, z+1/2'
'-x, -y, -z'
'y, -x-1/2, -z-1/2'
'x-1/2, y-1/2, -z'
'-y-1/2, x, -z-1/2'

_cell_length_a                   10.4847(3)
_cell_length_b                   10.4847(3)
_cell_length_c                   14.8469(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1632.10(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3636
_cell_measurement_temperature    391
_cell_measurement_theta_max      30.1080
_cell_measurement_theta_min      2.3810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.780
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             875
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0121
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.824
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7333
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.824
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.183
_diffrn_reflns_theta_min         2.378
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      391
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.824
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00  47.00   0.25    3.00    --   13.22 -74.00   1.00  436
  2  ω     48.00  96.00   0.25    3.00    --   13.22 178.00 -90.00  192
  3  ω    -21.00   4.00   0.25    3.00    --   13.22  77.00   0.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0510816000
_diffrn_orient_matrix_UB_12      0.0224767000
_diffrn_orient_matrix_UB_13      -0.0270483000
_diffrn_orient_matrix_UB_21      0.0106133000
_diffrn_orient_matrix_UB_22      0.0504450000
_diffrn_orient_matrix_UB_23      0.0308689000
_diffrn_orient_matrix_UB_31      0.0431089000
_diffrn_orient_matrix_UB_32      -0.0390312000
_diffrn_orient_matrix_UB_33      0.0244480000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1439
_reflns_number_total             2002
_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 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2002
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0638
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1334P)²+0.3795P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1990
_refine_ls_wR_factor_ref         0.2220
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups, All F(H,H,H,H)
  groups
2. Restrained distances
 N1-H1A = N1-H1B = N1-H1C = N1-H1D
 1.06 with sigma of 0.02
 H1A-H1B = H1A-H1C = H1A-H1D = H1B-H1C = H1B-H1D = H1C-H1D
 1.75 with sigma of 0.04
3. Others
 Sof(H1BC)=Sof(H1BD)=Sof(H4A)=Sof(H4B)=Sof(N2)=1-FVAR(1)
 Sof(P1)=Sof(H1AA)=Sof(H1AB)=Sof(H2A)=Sof(H2B)=FVAR(1)
 Sof(F2)=Sof(F3)=Sof(F8)=Sof(F5)=1-FVAR(2)
 Sof(F1)=Sof(F6)=Sof(F4)=Sof(F7)=FVAR(2)
 Sof(F9)=Sof(F11)=1-FVAR(3)
 Sof(F10)=Sof(F12)=FVAR(3)
 Fixed Sof: H3A(0.5) H3B(0.5) H1A(0.5) H1B(0.5) H1C(0.5) H1D(0.5)
4.a Ternary CH refined with riding coordinates:
 N3(H3)
4.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C1(H1AA,H1AB), C1(H1BC,H1BD), C2(H2A,H2B), C4(H4A,H4B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
P1 P 0.75004(18) 0.8946(2) 0.58591(17) 0.0561(6) Uani 0.549(8) 1 d . . P A 1
N3 N 0.63487(14) 0.75038(15) 0.44985(11) 0.0416(5) Uani 1 1 d . . . . .
H3 H 0.560164 0.750187 0.410173 0.050 Uiso 1 1 calc R U . . .
F1 F 0.5379(8) 0.8633(7) 0.2828(9) 0.114(3) Uani 0.486(14) 1 d . . P B 1
N1 N 0.750000 1.250000 0.24178(18) 0.0557(7) Uani 1 2 d DS T P . .
F10 F 0.3483(14) 0.709(2) 0.4561(11) 0.093(3) Uani 0.35(3) 1 d . . P C 1
F12 F 0.208(2) 0.8449(15) 0.5607(8) 0.083(4) Uani 0.35(3) 1 d . . P C -1
F6 F 0.5407(11) 1.0743(12) 0.3108(6) 0.113(3) Uani 0.486(14) 1 d . . P B 1
F4 F 0.3907(6) 0.9904(8) 0.2238(7) 0.089(2) Uani 0.486(14) 1 d . . P B 1
F7 F 0.5918(8) 1.0052(7) 0.1754(4) 0.088(2) Uani 0.486(14) 1 d . . P B 1
C3 C 0.750000 0.750000 0.39185(18) 0.0504(7) Uani 1 2 d S T P . .
H3A H 0.749752 0.675013 0.353588 0.060 Uiso 0.5 1 calc R U P . .
H3B H 0.750250 0.824988 0.353589 0.060 Uiso 0.5 1 calc R U P . .
C1 C 0.6288(2) 0.6311(2) 0.50693(16) 0.0541(6) Uani 1 1 d . . . . .
H1AA H 0.627276 0.558312 0.466581 0.065 Uiso 0.549(8) 1 calc R U P A 1
H1AB H 0.548209 0.631769 0.538981 0.065 Uiso 0.549(8) 1 calc R U P A 1
H1BC H 0.555754 0.632960 0.546979 0.065 Uiso 0.451(8) 1 calc R U P A 2
H1BD H 0.624053 0.555277 0.469606 0.065 Uiso 0.451(8) 1 calc R U P A 2
C2 C 0.6281(2) 0.8694(2) 0.50694(16) 0.0532(6) Uani 1 1 d . . . . .
H2A H 0.547598 0.868213 0.539121 0.064 Uiso 0.549(8) 1 calc R U P A 1
H2B H 0.626236 0.942303 0.466754 0.064 Uiso 0.549(8) 1 calc R U P A 1
C4 C 0.750000 0.750000 0.6318(2) 0.0681(11) Uani 1 2 d S T P . .
H4A H 0.674203 0.749494 0.669295 0.082 Uiso 0.451(8) 1 calc R U P A 2
H4B H 0.825797 0.750505 0.669295 0.082 Uiso 0.451(8) 1 calc R U P A 2
B2 B 0.250000 0.750000 0.5067(2) 0.0518(8) Uani 1 2 d S T P . .
B1 B 0.5162(3) 0.9841(2) 0.24997(15) 0.0500(6) Uani 1 1 d . . . . .
N2 N 0.7492(8) 0.8653(9) 0.5588(6) 0.0581(19) Uani 0.451(8) 1 d . . P A 2
F2 F 0.4952(7) 0.9078(8) 0.3244(4) 0.092(2) Uani 0.514(14) 1 d . . P B 2
F3 F 0.4239(12) 0.9597(10) 0.1892(6) 0.117(3) Uani 0.514(14) 1 d . . P B 2
F8 F 0.6358(7) 0.9624(8) 0.2158(9) 0.118(3) Uani 0.514(14) 1 d . . P B 2
F5 F 0.5098(9) 1.1098(6) 0.2775(7) 0.093(2) Uani 0.514(14) 1 d . . P B 2
F9 F 0.3533(6) 0.7699(19) 0.4510(5) 0.102(3) Uani 0.65(3) 1 d . . P C 2
F11 F 0.272(2) 0.8539(7) 0.5626(5) 0.106(3) Uani 0.65(3) 1 d . . P C 2
H1A H 0.695(5) 1.276(6) 0.299(3) 0.127 Uiso 0.5 1 d D U P D -1
H1B H 0.767(9) 1.150(2) 0.244(3) 0.127 Uiso 0.5 1 d D U P E -1
H1C H 0.840(4) 1.295(8) 0.244(3) 0.127 Uiso 0.5 1 d D U P F -1
H1D H 0.702(5) 1.275(6) 0.183(2) 0.127 Uiso 0.5 1 d D U P G -1

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0504(7) 0.0619(10) 0.0558(12) -0.0199(7) 0.0002(6) -0.0003(5)
N3 0.0340(8) 0.0514(9) 0.0394(8) 0.0005(6) -0.0061(6) -0.0002(6)
F1 0.122(5) 0.088(4) 0.131(7) 0.045(4) -0.027(4) 0.027(3)
N1 0.0612(16) 0.0494(14) 0.0565(15) 0.000 0.000 0.0006(11)
F10 0.055(4) 0.107(8) 0.116(6) 0.010(6) 0.024(4) 0.009(4)
F12 0.098(7) 0.059(5) 0.093(4) -0.020(3) 0.003(5) 0.016(4)
F6 0.130(6) 0.126(7) 0.084(4) -0.053(4) 0.020(4) -0.038(5)
F4 0.056(2) 0.102(4) 0.109(5) 0.011(4) -0.018(3) 0.003(2)
F7 0.090(4) 0.106(4) 0.069(3) -0.003(2) 0.030(2) 0.021(3)
C3 0.0504(15) 0.0703(18) 0.0303(11) 0.000 0.000 -0.0001(12)
C1 0.0540(11) 0.0489(11) 0.0593(12) 0.0049(9) 0.0009(9) -0.0098(8)
C2 0.0529(11) 0.0475(11) 0.0593(12) -0.0048(9) 0.0014(9) 0.0086(8)
C4 0.0529(17) 0.121(3) 0.0306(13) 0.000 0.000 0.0012(17)
B2 0.0466(16) 0.0590(19) 0.0497(17) 0.000 0.000 0.0012(14)
B1 0.0509(13) 0.0495(13) 0.0497(12) -0.0004(9) -0.0006(9) 0.0007(9)
N2 0.073(4) 0.058(4) 0.043(3) -0.012(3) 0.001(3) 0.000(3)
F2 0.108(4) 0.094(4) 0.074(3) 0.033(2) -0.002(2) 0.017(3)
F3 0.142(8) 0.129(6) 0.080(4) 0.020(3) -0.054(4) -0.042(5)
F8 0.085(4) 0.126(5) 0.143(7) -0.031(5) 0.044(4) 0.025(3)
F5 0.102(4) 0.060(2) 0.117(6) -0.015(3) 0.019(4) 0.005(2)
F9 0.0512(17) 0.165(8) 0.089(2) 0.016(4) 0.0113(15) -0.015(3)
F11 0.157(8) 0.070(2) 0.092(2) -0.0113(17) -0.012(4) -0.032(3)

_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 C1 1.749(3) 3_665 ?
P1 C2 1.755(3) . ?
P1 C4 1.663(3) . ?
N3 H3 0.9800 . ?
N3 C3 1.483(2) . ?
N3 C1 1.512(2) . ?
N3 C2 1.510(2) . ?
F1 B1 1.376(5) . ?
N1 H1A 1.063(19) . ?
N1 H1B 1.065(19) . ?
N1 H1C 1.061(19) . ?
N1 H1D 1.044(19) . ?
F10 B2 1.346(13) . ?
F12 B2 1.351(10) . ?
F6 B1 1.333(8) . ?
F4 B1 1.374(7) . ?
F7 B1 1.379(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C1 H1AA 0.9700 . ?
C1 H1AB 0.9700 . ?
C1 H1BC 0.9700 . ?
C1 H1BD 0.9700 . ?
C1 N2 1.493(8) 3_665 ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N2 1.486(9) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N2 1.624(8) 3_665 ?
C4 N2 1.624(8) . ?
B2 F9 1.378(7) 3_565 ?
B2 F9 1.378(7) . ?
B2 F11 1.389(6) . ?
B2 F11 1.389(6) 3_565 ?
B1 F2 1.382(5) . ?
B1 F3 1.347(8) . ?
B1 F8 1.371(5) . ?
B1 F5 1.382(7) . ?

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
C1 P1 C2 93.32(16) 3_665 . ?
C4 P1 C1 97.74(15) . 3_665 ?
C4 P1 C2 97.83(15) . . ?
C3 N3 H3 107.6 . . ?
C3 N3 C1 110.93(13) . . ?
C3 N3 C2 111.49(13) . . ?
C1 N3 H3 107.6 . . ?
C2 N3 H3 107.6 . . ?
C2 N3 C1 111.53(17) . . ?
H1A N1 H1B 109(3) . . ?
H1A N1 H1C 111(3) . . ?
H1A N1 H1D 110(3) . . ?
H1B N1 H1C 107(3) . . ?
H1B N1 H1D 111(3) . . ?
H1C N1 H1D 110(3) . . ?
N3 C3 N3 109.0(2) 3_665 . ?
N3 C3 H3A 109.9 . . ?
N3 C3 H3A 109.9 3_665 . ?
N3 C3 H3B 109.9 . . ?
N3 C3 H3B 109.9 3_665 . ?
H3A C3 H3B 108.3 . . ?
P1 C1 H1AA 107.8 3_665 . ?
P1 C1 H1AB 107.8 3_665 . ?
N3 C1 P1 118.20(16) . 3_665 ?
N3 C1 H1AA 107.8 . . ?
N3 C1 H1AB 107.8 . . ?
N3 C1 H1BC 111.1 . . ?
N3 C1 H1BD 111.1 . . ?
H1AA C1 H1AB 107.1 . . ?
H1BC C1 H1BD 109.0 . . ?
N2 C1 N3 103.4(4) 3_665 . ?
N2 C1 H1BC 111.1 3_665 . ?
N2 C1 H1BD 111.1 3_665 . ?
P1 C2 H2A 107.9 . . ?
P1 C2 H2B 107.9 . . ?
N3 C2 P1 117.74(15) . . ?
N3 C2 H2A 107.9 . . ?
N3 C2 H2B 107.9 . . ?
H2A C2 H2B 107.2 . . ?
N2 C2 N3 103.1(4) . . ?
P1 C4 P1 131.6(3) . 3_665 ?
H4A C4 H4B 110.0 . . ?
N2 C4 H4A 112.5 3_665 . ?
N2 C4 H4A 112.5 . . ?
N2 C4 H4B 112.5 . . ?
N2 C4 H4B 112.5 3_665 . ?
F10 B2 F10 112.2(14) . 3_565 ?
F10 B2 F12 81.4(14) 3_565 . ?
F10 B2 F12 144.4(19) . . ?
F10 B2 F9 102.7(5) . 3_565 ?
F10 B2 F9 27.3(4) 3_565 3_565 ?
F10 B2 F11 117.2(16) 3_565 3_565 ?
F10 B2 F11 102.1(16) . 3_565 ?
F12 B2 F9 102.4(15) . 3_565 ?
F12 B2 F11 99.8(4) . 3_565 ?
F9 B2 F11 127.4(16) 3_565 . ?
F9 B2 F11 96.3(13) 3_565 3_565 ?
F9 B2 F11 96.3(13) . . ?
F9 B2 F11 127.4(16) . 3_565 ?
F11 B2 F11 106.5(6) . 3_565 ?
F1 B1 F7 109.7(5) . . ?
F6 B1 F1 112.5(5) . . ?
F6 B1 F4 110.0(6) . . ?
F6 B1 F7 108.6(5) . . ?
F4 B1 F1 107.6(5) . . ?
F4 B1 F7 108.4(4) . . ?
F3 B1 F2 108.1(5) . . ?
F3 B1 F8 112.2(5) . . ?
F3 B1 F5 110.1(6) . . ?
F8 B1 F2 110.2(5) . . ?
F8 B1 F5 108.2(5) . . ?
F5 B1 F2 107.9(4) . . ?
C1 N2 C4 111.0(5) 3_665 . ?
C2 N2 C1 117.6(6) . 3_665 ?
C2 N2 C4 111.8(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
N3 C2 N2 C1 61.3(7) . . . 3_665 ?
N3 C2 N2 C4 -68.9(6) . . . . ?
C3 N3 C1 P1 63.2(2) . . . 3_665 ?
C3 N3 C1 N2 58.1(4) . . . 3_665 ?
C3 N3 C2 P1 -62.9(2) . . . . ?
C3 N3 C2 N2 -58.1(4) . . . . ?
C1 P1 C2 N3 50.3(2) 3_665 . . . ?
C1 P1 C4 P1 -47.11(11) 3_665 . . 3_665 ?
C1 N3 C3 N3 -62.35(12) . . . 3_665 ?
C1 N3 C2 P1 61.7(2) . . . . ?
C1 N3 C2 N2 66.5(4) . . . . ?
C2 P1 C4 P1 47.34(10) . . . 3_665 ?
C2 N3 C3 N3 62.60(12) . . . 3_665 ?
C2 N3 C1 P1 -61.7(2) . . . 3_665 ?
C2 N3 C1 N2 -66.9(4) . . . 3_665 ?
C4 P1 C2 N3 -48.0(2) . . . . ?
N2 C4 N2 C1 -66.6(5) 3_665 . . 3_665 ?
N2 C4 N2 C2 67.0(6) 3_665 . . . ?

_shelx_res_file                  
;
TITL RT_p42n in P42/n #86
    p-bf4_391k.res
    created by SHELXL-2018/3 at 11:28:26 on 08-Jan-2025
REM reset to P42/n #86
CELL 0.71073 10.484682 10.484682 14.846949 90 90 90
ZERR 4 0.000281 0.000281 0.00065 0 0 0
LATT 1
SYMM -Y,0.5+X,0.5+Z
SYMM 0.5-X,0.5-Y,+Z
SYMM 0.5+Y,-X,0.5+Z
SFAC C H B F N P
UNIT 24 64 12 48 15.61 4.39
DFIX 1.06 N1 H1a N1 H1b N1 H1c N1 H1d
DANG 1.75 H1a H1b H1a H1c H1a H1d H1b H1c H1b H1d H1c H1d

L.S. 8 0 0
PLAN  5
TEMP 117.85
CONF
BOND
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\p-BF4_391K.hkl">
REM </olex2.extras>

WGHT    0.133400    0.379500
FVAR       2.14373   0.54912   0.48623   0.34797
PART 1
P1    6    0.750035    0.894627    0.585906    21.00000    0.05043    0.06191 =
         0.05584   -0.01987    0.00022   -0.00026
PART 0
N3    5    0.634866    0.750382    0.449846    11.00000    0.03397    0.05142 =
         0.03941    0.00049   -0.00607   -0.00022
AFIX  13
H3    2    0.560164    0.750187    0.410173    11.00000   -1.20000
AFIX   0

PART 1
F1    4    0.537911    0.863286    0.282758    31.00000    0.12193    0.08807 =
         0.13137    0.04536   -0.02693    0.02693

PART 0
N1    5    0.750000    1.250000    0.241784    10.50000    0.06124    0.04938 =
         0.05653    0.00000    0.00000    0.00060

PART 1
F10   4    0.348349    0.709100    0.456080    41.00000    0.05488    0.10700 =
         0.11634    0.00973    0.02411    0.00868
PART -1
F12   4    0.208463    0.844936    0.560705    41.00000    0.09753    0.05888 =
         0.09308   -0.01951    0.00289    0.01596

PART 1
F6    4    0.540719    1.074323    0.310752    31.00000    0.12990    0.12626 =
         0.08365   -0.05299    0.01978   -0.03753
F4    4    0.390726    0.990409    0.223784    31.00000    0.05635    0.10159 =
         0.10870    0.01100   -0.01760    0.00276
F7    4    0.591821    1.005227    0.175420    31.00000    0.08963    0.10614 =
         0.06940   -0.00299    0.02989    0.02063

PART 0
C3    1    0.750000    0.750000    0.391853    10.50000    0.05043    0.07032 =
         0.03034    0.00000    0.00000   -0.00006
AFIX  23
H3A   2    0.749752    0.675013    0.353588    10.50000   -1.20000
H3B   2    0.750250    0.824988    0.353589    10.50000   -1.20000
AFIX   0
C1    1    0.628825    0.631059    0.506931    11.00000    0.05403    0.04893 =
         0.05931    0.00494    0.00085   -0.00981
PART 1
AFIX  23
H1AA  2    0.627276    0.558312    0.466581    21.00000   -1.20000
H1AB  2    0.548209    0.631769    0.538981    21.00000   -1.20000
AFIX  23
PART 2
H1BC  2    0.555754    0.632960    0.546979   -21.00000   -1.20000
H1BD  2    0.624053    0.555277    0.469606   -21.00000   -1.20000
AFIX   0
PART 0
C2    1    0.628107    0.869385    0.506943    11.00000    0.05288    0.04747 =
         0.05933   -0.00477    0.00141    0.00863
PART 1
AFIX  23
H2A   2    0.547598    0.868213    0.539121    21.00000   -1.20000
H2B   2    0.626236    0.942303    0.466754    21.00000   -1.20000
AFIX   0
PART 0
C4    1    0.750000    0.750000    0.631836    10.50000    0.05288    0.12077 =
         0.03060    0.00000    0.00000    0.00122
PART 2
AFIX  23
H4A   2    0.674203    0.749494    0.669295   -21.00000   -1.20000
H4B   2    0.825797    0.750505    0.669295   -21.00000   -1.20000
AFIX   0

PART 0
B2    3    0.250000    0.750000    0.506659    10.50000    0.04661    0.05899 =
         0.04973    0.00000    0.00000    0.00117

B1    3    0.516215    0.984062    0.249965    11.00000    0.05087    0.04951 =
         0.04972   -0.00036   -0.00059    0.00071
PART 2
N2    5    0.749231    0.865342    0.558814   -21.00000    0.07275    0.05838 =
         0.04331   -0.01191    0.00077    0.00048

F2    4    0.495245    0.907763    0.324413   -31.00000    0.10834    0.09396 =
         0.07370    0.03272   -0.00239    0.01663
F3    4    0.423867    0.959732    0.189239   -31.00000    0.14230    0.12864 =
         0.07995    0.02044   -0.05351   -0.04165
F8    4    0.635805    0.962357    0.215843   -31.00000    0.08525    0.12637 =
         0.14315   -0.03130    0.04440    0.02475
F5    4    0.509751    1.109801    0.277484   -31.00000    0.10193    0.05955 =
         0.11748   -0.01499    0.01902    0.00472
F9    4    0.353326    0.769930    0.451011   -41.00000    0.05118    0.16550 =
         0.08930    0.01563    0.01126   -0.01521
F11   4    0.271893    0.853865    0.562585   -41.00000    0.15656    0.06976 =
         0.09201   -0.01134   -0.01202   -0.03187
PART -1
H1A   2    0.694879    1.276073    0.298953    10.50000   -1.20000
H1B   2    0.767352    1.149951    0.243860    10.50000   -1.20000
H1C   2    0.840466    1.295323    0.243517    10.50000   -1.20000
H1D   2    0.702289    1.274808    0.182643    10.50000   -1.20000
HKLF 4




REM  RT_p42n in P42/n #86
REM wR2 = 0.2220, GooF = S = 1.093, Restrained GooF = 1.091 for all data
REM R1 = 0.0638 for 1439 Fo > 4sig(Fo) and 0.0796 for all 2002 data
REM 198 parameters refined using 10 restraints

END

WGHT      0.1334      0.3795

REM Highest difference peak  0.336,  deepest hole -0.232,  1-sigma level  0.065
Q1    1   0.5683  0.9547  0.3235  11.00000  0.05    0.34
Q2    1   0.5563  0.9209  0.1853  11.00000  0.05    0.32
Q3    1   0.7500  1.2500  0.2626  10.50000  0.05    0.30
Q4    1   0.5022  0.8697  0.2084  11.00000  0.05    0.29
Q5    1   0.6265  1.0079  0.3047  11.00000  0.05    0.28
;
_shelx_res_checksum              50156
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 4.393
_oxdiff_exptl_absorpt_empirical_full_min 0.503
####################################################################### 
# 
# 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_pta-br_322k
_database_code_depnum_ccdc_archive 'CCDC 2424522'
loop_
_audit_author_name
_audit_author_address
'Ryo Tsunashima'
;yamaguchi
Japan
;
_audit_update_record             
;
2025-02-17 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;
_audit_creation_date             2025-01-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(Br), C6 H14 N3 P, H4 N'
_chemical_formula_sum            'C6 H18 Br3 N4 P'
_chemical_formula_weight         416.94
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H18N3I3P
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'
N N 0.0061 0.0033 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   13.7974(4)
_cell_length_b                   9.9483(3)
_cell_length_c                   9.6610(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1326.08(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3924
_cell_measurement_temperature    322
_cell_measurement_theta_max      30.0710
_cell_measurement_theta_min      2.9210
_shelx_estimated_absorpt_T_max   0.320
_shelx_estimated_absorpt_T_min   0.236
_exptl_absorpt_coefficient_mu    9.221
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.088
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 9 10 0.0606
16 -3 7 0.0834
6 -11 -8 0.1183
-7 -6 -11 0.1062
-16 7 -3 0.0543
-8 11 7 0.0562
8 -4 12 0.0635
15 8 -3 0.0727
-14 0 -10 0.0841
-17 -7 0 0.0823
2 4 -13 0.0923
11 2 -11 0.0811
2 -12 6 0.1190
-9 -11 -5 0.0983

_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.5742 9.1116 10.3437 0.5697 0.5994 0.5623
15.8440 -2.7593 7.4308 -0.1890 -0.2033 0.9607
5.6004 -10.6456 -7.9494 -0.6720 -0.7089 -0.2142
-6.7222 -6.2358 -11.2529 -0.3833 -0.4016 -0.8317
-16.2824 6.9654 -3.1200 0.4527 0.4810 -0.7508
-7.7117 10.8300 6.7588 0.6858 0.7239 0.0756
7.5370 -3.8800 11.9804 -0.3343 0.3198 0.8865
15.3077 8.1505 -2.8273 0.6567 -0.6203 0.4288
-13.7626 -0.1480 -9.6222 0.0078 -0.0110 -0.9999
-16.7856 -7.0846 -0.0387 -0.5658 0.5335 -0.6287
2.1550 4.0488 -12.9578 0.3911 -0.7150 -0.5796
11.4451 2.2387 -10.8002 0.2830 -0.9504 -0.1292
2.3925 -12.4280 6.0950 -0.9150 0.1205 0.3851
-8.9153 -11.1396 -5.4269 -0.7820 -0.0641 -0.6200

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5109
_diffrn_reflns_point_group_measured_fraction_full 0.770
_diffrn_reflns_point_group_measured_fraction_max 0.760
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         2.939
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      322
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  11.00   0.25    2.20    --   -5.68 -59.00  26.00  300
  2  ω    -16.00  39.00   0.25    2.20    --    6.15 -99.00   0.00  220
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0038744000
_diffrn_orient_matrix_UB_12      0.0707208000
_diffrn_orient_matrix_UB_13      -0.0074379000
_diffrn_orient_matrix_UB_21      -0.0356807000
_diffrn_orient_matrix_UB_22      0.0089556000
_diffrn_orient_matrix_UB_23      0.0520420000
_diffrn_orient_matrix_UB_31      0.0368202000
_diffrn_orient_matrix_UB_32      0.0012297000
_diffrn_orient_matrix_UB_33      0.0512338000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.439
_reflns_Friedel_fraction_full    0.516
_reflns_Friedel_fraction_max     0.494
_reflns_number_gt                1973
_reflns_number_total             2060
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.997
_refine_diff_density_rms         0.118
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.007(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2060
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      1.049
_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)+(0.1150P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1310
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H,H,H) groups, All N(H) groups
2. Restrained distances
 N1-H1C = N1-H1D = N1-H1E = N1-H1F
 1.05 with sigma of 0.02
 H1C-H1D = H1C-H1E = H1C-H1F = H1D-H1E = H1D-H1F = H1E-H1F
 1.75 with sigma of 0.04
3.a Ternary CH refined with riding coordinates:
 N3(H3), N4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C5(H5A,H5B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C1(H1A,H1B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
Br01 Br 0.27744(6) 0.46397(9) 0.71132(13) 0.0405(3) Uani 1 1 d . . . . .
Br02 Br -0.01469(7) 0.78153(10) 0.41533(13) 0.0458(3) Uani 1 1 d . . . . .
Br03 Br 0.24620(8) 1.00725(10) 0.6670(2) 0.0470(3) Uani 1 1 d . . . . .
P1 P 0.56880(17) 0.0856(3) 0.4325(4) 0.0477(7) Uani 1 1 d . . . . .
N2 N 0.4281(5) 0.2416(9) 0.2981(9) 0.0359(16) Uani 1 1 d . . . . .
N3 N 0.5643(5) 0.3658(7) 0.4116(9) 0.0360(16) Uani 1 1 d . . . . .
H3 H 0.604509 0.446110 0.399436 0.043 Uiso 1 1 calc R U . . .
N4 N 0.4391(6) 0.2670(8) 0.5545(9) 0.0389(18) Uani 1 1 d . . . . .
H4 H 0.398270 0.283242 0.635746 0.047 Uiso 1 1 calc R U . . .
N1 N 0.2285(6) 0.7137(9) 0.4678(13) 0.052(2) Uani 1 1 d D . . . .
C6 C 0.5083(7) 0.3840(11) 0.5405(12) 0.039(2) Uani 1 1 d . . . . .
H6A H 0.472474 0.467850 0.536962 0.046 Uiso 1 1 calc R U . . .
H6B H 0.551735 0.387025 0.619365 0.046 Uiso 1 1 calc R U . . .
C5 C 0.3733(6) 0.2583(10) 0.4285(14) 0.045(2) Uani 1 1 d . . . . .
H5A H 0.329445 0.182921 0.439744 0.054 Uiso 1 1 calc R U . . .
H5B H 0.334607 0.339500 0.422845 0.054 Uiso 1 1 calc R U . . .
C2 C 0.6309(5) 0.2480(10) 0.4180(13) 0.0393(18) Uani 1 1 d . . . . .
H2A H 0.673694 0.258763 0.496957 0.047 Uiso 1 1 calc R U . . .
H2B H 0.670815 0.247312 0.335348 0.047 Uiso 1 1 calc R U . . .
C3 C 0.4920(7) 0.1360(11) 0.5766(13) 0.046(2) Uani 1 1 d . . . . .
H3A H 0.444668 0.065702 0.593209 0.055 Uiso 1 1 calc R U . . .
H3B H 0.531756 0.143807 0.658977 0.055 Uiso 1 1 calc R U . . .
C4 C 0.4946(7) 0.3580(10) 0.2856(11) 0.038(2) Uani 1 1 d . . . . .
H4A H 0.456984 0.440246 0.279967 0.046 Uiso 1 1 calc R U . . .
H4B H 0.532099 0.349796 0.201088 0.046 Uiso 1 1 calc R U . . .
C1 C 0.4810(8) 0.1155(11) 0.2937(14) 0.050(3) Uani 1 1 d . . . . .
H1A H 0.515108 0.110846 0.206075 0.060 Uiso 1 1 calc R U . . .
H1B H 0.434243 0.042691 0.294904 0.060 Uiso 1 1 calc R U . . .
H1C H 0.283(5) 0.650(8) 0.505(10) 0.060 Uiso 1 1 d D U . . .
H1D H 0.213(7) 0.694(11) 0.362(4) 0.060 Uiso 1 1 d D U . . .
H1E H 0.246(7) 0.817(3) 0.479(12) 0.060 Uiso 1 1 d D U . . .
H1F H 0.163(4) 0.695(9) 0.523(9) 0.060 Uiso 1 1 d D U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br01 0.0338(5) 0.0365(5) 0.0512(6) 0.0009(4) 0.0014(4) 0.0027(3)
Br02 0.0494(5) 0.0415(5) 0.0466(6) -0.0047(5) -0.0045(5) 0.0063(4)
Br03 0.0398(5) 0.0416(5) 0.0596(7) 0.0061(5) 0.0035(5) -0.0015(4)
P1 0.0394(11) 0.0334(12) 0.0704(19) -0.0002(11) -0.0051(13) 0.0065(10)
N2 0.028(3) 0.037(4) 0.043(4) 0.013(4) -0.003(3) 0.008(3)
N3 0.034(3) 0.024(3) 0.049(4) 0.000(3) 0.003(4) -0.008(2)
N4 0.036(4) 0.038(4) 0.042(5) 0.001(3) 0.012(4) 0.010(3)
N1 0.047(5) 0.045(5) 0.063(6) 0.015(4) -0.008(4) 0.001(3)
C6 0.040(4) 0.032(5) 0.045(6) -0.004(4) 0.001(4) 0.000(3)
C5 0.028(3) 0.038(5) 0.068(7) 0.005(5) -0.003(5) 0.005(3)
C2 0.023(3) 0.041(4) 0.054(5) -0.005(5) -0.001(5) 0.001(3)
C3 0.052(5) 0.031(5) 0.054(7) 0.014(5) 0.005(4) 0.004(4)
C4 0.054(5) 0.024(4) 0.036(5) 0.001(4) 0.003(4) 0.004(4)
C1 0.058(6) 0.031(5) 0.062(7) -0.017(5) -0.003(5) -0.008(4)

_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 C2 1.834(10) . ?
P1 C3 1.820(12) . ?
P1 C1 1.831(13) . ?
N2 C5 1.479(15) . ?
N2 C4 1.483(13) . ?
N2 C1 1.452(14) . ?
N3 H3 0.9800 . ?
N3 C6 1.476(14) . ?
N3 C2 1.490(11) . ?
N3 C4 1.554(13) . ?
N4 H4 0.9800 . ?
N4 C6 1.512(13) . ?
N4 C5 1.520(15) . ?
N4 C3 1.509(13) . ?
N1 H1C 1.05(2) . ?
N1 H1D 1.06(2) . ?
N1 H1E 1.06(2) . ?
N1 H1F 1.07(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 P1 C2 95.1(5) . . ?
C3 P1 C1 97.5(5) . . ?
C1 P1 C2 96.4(5) . . ?
C5 N2 C4 107.3(8) . . ?
C1 N2 C5 112.3(8) . . ?
C1 N2 C4 111.2(8) . . ?
C6 N3 H3 107.3 . . ?
C6 N3 C2 112.6(8) . . ?
C6 N3 C4 110.0(6) . . ?
C2 N3 H3 107.3 . . ?
C2 N3 C4 112.1(8) . . ?
C4 N3 H3 107.3 . . ?
C6 N4 H4 107.9 . . ?
C6 N4 C5 110.4(8) . . ?
C5 N4 H4 107.9 . . ?
C3 N4 H4 107.9 . . ?
C3 N4 C6 111.9(8) . . ?
C3 N4 C5 110.7(8) . . ?
H1C N1 H1D 111(4) . . ?
H1C N1 H1E 113(4) . . ?
H1C N1 H1F 109(4) . . ?
H1D N1 H1E 109(4) . . ?
H1D N1 H1F 106(4) . . ?
H1E N1 H1F 108(4) . . ?
N3 C6 N4 108.1(8) . . ?
N3 C6 H6A 110.1 . . ?
N3 C6 H6B 110.1 . . ?
N4 C6 H6A 110.1 . . ?
N4 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
N2 C5 N4 112.5(6) . . ?
N2 C5 H5A 109.1 . . ?
N2 C5 H5B 109.1 . . ?
N4 C5 H5A 109.1 . . ?
N4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
P1 C2 H2A 108.7 . . ?
P1 C2 H2B 108.7 . . ?
N3 C2 P1 114.0(5) . . ?
N3 C2 H2A 108.7 . . ?
N3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
P1 C3 H3A 108.7 . . ?
P1 C3 H3B 108.7 . . ?
N4 C3 P1 114.3(7) . . ?
N4 C3 H3A 108.7 . . ?
N4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
N2 C4 N3 111.0(8) . . ?
N2 C4 H4A 109.4 . . ?
N2 C4 H4B 109.4 . . ?
N3 C4 H4A 109.4 . . ?
N3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
P1 C1 H1A 108.1 . . ?
P1 C1 H1B 108.1 . . ?
N2 C1 P1 116.9(8) . . ?
N2 C1 H1A 108.1 . . ?
N2 C1 H1B 108.1 . . ?
H1A C1 H1B 107.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N3 C2 P1 65.0(10) . . . . ?
C6 N3 C4 N2 -61.5(9) . . . . ?
C6 N4 C5 N2 59.0(10) . . . . ?
C6 N4 C3 P1 -63.5(11) . . . . ?
C5 N2 C4 N3 58.7(9) . . . . ?
C5 N2 C1 P1 -57.9(11) . . . . ?
C5 N4 C6 N3 -57.5(10) . . . . ?
C5 N4 C3 P1 60.1(10) . . . . ?
C2 P1 C3 N4 50.2(8) . . . . ?
C2 P1 C1 N2 -49.7(9) . . . . ?
C2 N3 C6 N4 -67.3(9) . . . . ?
C2 N3 C4 N2 64.7(10) . . . . ?
C3 P1 C2 N3 -50.4(9) . . . . ?
C3 P1 C1 N2 46.3(9) . . . . ?
C3 N4 C6 N3 66.2(11) . . . . ?
C3 N4 C5 N2 -65.4(10) . . . . ?
C4 N2 C5 N4 -58.4(9) . . . . ?
C4 N2 C1 P1 62.3(11) . . . . ?
C4 N3 C6 N4 58.6(9) . . . . ?
C4 N3 C2 P1 -59.8(10) . . . . ?
C1 P1 C2 N3 47.7(9) . . . . ?
C1 P1 C3 N4 -46.9(9) . . . . ?
C1 N2 C5 N4 64.1(10) . . . . ?
C1 N2 C4 N3 -64.4(11) . . . . ?

_shelx_res_file                  
;
TITL 325_re2_a.res in Pna2(1)
    pta-br_322k.res
    created by SHELXL-2018/3 at 13:46:36 on 08-Jan-2025
REM Old TITL 325_re2 in Pna2(1)
REM SHELXT solution in Pna2(1): R1 0.080, Rweak 0.012, Alpha 0.002
REM <I/s> 0.455 for 145 systematic absences, Orientation as input
REM Flack x = -0.073 ( 0.031 ) from 591 Parsons' quotients
REM Formula found by SHELXT: C7 N3 P Br3
CELL 0.71073 13.7974 9.9483 9.661 90 90 90
ZERR 4 0.0004 0.0003 0.0003 0 0 0
LATT -1
SYMM -X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,+Z
SYMM 0.5-X,0.5+Y,0.5+Z
SFAC C H Br N P
UNIT 24 72 12 16 4
DFIX 1.05 N1 H1c N1 H1d N1 H1e N1 H1f
DANG 1.75 H1c H1d H1c H1e H1c H1f H1d H1e H1d H1f H1e H1f

L.S. 8
PLAN  7
SIZE 0.16 0.18 0.22
TEMP 48.85
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\pta-Br_322K.hkl">
REM </olex2.extras>

WGHT    0.115000
FVAR       0.29189
BR01  3    0.277441    0.463972    0.711319    11.00000    0.03385    0.03646 =
         0.05118    0.00093    0.00139    0.00267
BR02  3   -0.014691    0.781534    0.415331    11.00000    0.04936    0.04150 =
         0.04656   -0.00472   -0.00447    0.00632
BR03  3    0.246204    1.007249    0.666959    11.00000    0.03976    0.04158 =
         0.05956    0.00608    0.00346   -0.00154
P1    5    0.568804    0.085648    0.432489    11.00000    0.03937    0.03340 =
         0.07042   -0.00024   -0.00509    0.00649
N2    4    0.428093    0.241557    0.298063    11.00000    0.02760    0.03681 =
         0.04325    0.01332   -0.00330    0.00782
N3    4    0.564307    0.365763    0.411606    11.00000    0.03431    0.02420 =
         0.04942    0.00008    0.00290   -0.00819
AFIX  13
H3    2    0.604509    0.446110    0.399436    11.00000   -1.20000
AFIX   0
N4    4    0.439107    0.266956    0.554462    11.00000    0.03620    0.03829 =
         0.04225    0.00095    0.01226    0.00973
AFIX  13
H4    2    0.398270    0.283242    0.635746    11.00000   -1.20000
AFIX   0

N1    4    0.228480    0.713663    0.467789    11.00000    0.04720    0.04466 =
         0.06282    0.01530   -0.00771    0.00067
C6    1    0.508316    0.384037    0.540457    11.00000    0.03955    0.03178 =
         0.04462   -0.00403    0.00074    0.00008
AFIX  23
H6A   2    0.472474    0.467850    0.536962    11.00000   -1.20000
H6B   2    0.551735    0.387025    0.619365    11.00000   -1.20000
AFIX   0
C5    1    0.373333    0.258309    0.428528    11.00000    0.02822    0.03768 =
         0.06799    0.00517   -0.00284    0.00490
AFIX  23
H5A   2    0.329445    0.182921    0.439744    11.00000   -1.20000
H5B   2    0.334607    0.339500    0.422845    11.00000   -1.20000
AFIX   0
C2    1    0.630934    0.248027    0.418031    11.00000    0.02318    0.04089 =
         0.05394   -0.00473   -0.00071    0.00149
AFIX  23
H2A   2    0.673694    0.258763    0.496957    11.00000   -1.20000
H2B   2    0.670815    0.247312    0.335348    11.00000   -1.20000
AFIX   0
C3    1    0.491989    0.135979    0.576573    11.00000    0.05211    0.03130 =
         0.05382    0.01365    0.00516    0.00364
AFIX  23
H3A   2    0.444668    0.065702    0.593209    11.00000   -1.20000
H3B   2    0.531756    0.143807    0.658977    11.00000   -1.20000
AFIX   0
C4    1    0.494565    0.358021    0.285561    11.00000    0.05421    0.02444 =
         0.03603    0.00079    0.00347    0.00378
AFIX  23
H4A   2    0.456984    0.440246    0.279967    11.00000   -1.20000
H4B   2    0.532099    0.349796    0.201088    11.00000   -1.20000
AFIX   0
C1    1    0.480996    0.115501    0.293736    11.00000    0.05773    0.03099 =
         0.06182   -0.01712   -0.00325   -0.00764
AFIX  23
H1A   2    0.515108    0.110846    0.206075    11.00000   -1.20000
H1B   2    0.434243    0.042691    0.294904    11.00000   -1.20000
AFIX   0
H1C   2    0.282726    0.649826    0.505370    11.00000   -1.20000
H1D   2    0.213432    0.693740    0.361642    11.00000   -1.20000
H1E   2    0.245956    0.816900    0.479295    11.00000   -1.20000
H1F   2    0.162646    0.695023    0.522935    11.00000   -1.20000
HKLF 4




REM  325_re2_a.res in Pna2(1)
REM wR2 = 0.1310, GooF = S = 1.051, Restrained GooF = 1.049 for all data
REM R1 = 0.0491 for 1973 Fo > 4sig(Fo) and 0.0505 for all 2060 data
REM 139 parameters refined using 11 restraints

END

WGHT      0.1150      0.0000

REM Highest difference peak  0.599,  deepest hole -0.997,  1-sigma level  0.118
Q1    1  -0.0164  0.8437  0.5162  11.00000  0.05    0.60
Q2    1   0.2761  0.5263  0.8059  11.00000  0.05    0.57
Q3    1  -0.0176  0.7259  0.3320  11.00000  0.05    0.57
Q4    1   0.2740  0.3987  0.6185  11.00000  0.05    0.56
Q5    1  -0.0101  0.8454  0.3175  11.00000  0.05    0.53
Q6    1   0.2436  1.0798  0.5722  11.00000  0.05    0.52
Q7    1  -0.0187  0.7337  0.4991  11.00000  0.05    0.51
;
_shelx_res_checksum              18057
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.484
_oxdiff_exptl_absorpt_empirical_full_min 0.700
####################################################################### 
# 
# 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_rt1225_inv
_database_code_depnum_ccdc_archive 'CCDC 2424529'
loop_
_audit_author_name
_audit_author_address
'Ryo Tsunashima'
;yamaguchi
Japan
;
_audit_update_record             
;
2025-02-17 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;
_audit_creation_date             2025-01-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(Br), C6 H14 N3 P, H4 N'
_chemical_formula_sum            'C6 H18 Br3 N4 P'
_chemical_formula_weight         416.94
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H18N3Br3P
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'
N N 0.0061 0.0033 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   13.7604(3)
_cell_length_b                   9.9259(3)
_cell_length_c                   9.6119(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1312.84(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4328
_cell_measurement_temperature    253
_cell_measurement_theta_max      30.8200
_cell_measurement_theta_min      2.9330
_shelx_estimated_absorpt_T_max   0.317
_shelx_estimated_absorpt_T_min   0.213
_exptl_absorpt_coefficient_mu    9.314
_exptl_absorpt_correction_T_max  0.520
_exptl_absorpt_correction_T_min  0.259
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.109
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
12 -4 -6 0.0109
-9 4 -14 0.0976
-2 -2 19 0.1197
-11 -4 11 0.1341
0 6 -17 0.0756
-6 -12 -6 0.1560
-6 -10 10 0.1176
-3 0 -19 0.0648
-13 -1 -3 0.1099
-3 14 1 0.0876
1 10 14 0.0710
11 8 4 0.0285

_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
12.3304 -3.6443 -6.2812 -0.3278 0.3865 0.8621
-8.5378 3.7273 -14.1511 0.3824 -0.9199 0.0867
-2.4421 -2.3654 18.7959 -0.2204 0.5249 -0.8221
-10.6668 -4.0758 10.5418 -0.2481 -0.2159 -0.9444
-0.2991 6.1360 -17.4270 0.5032 -0.5854 0.6357
-6.2423 -11.6355 -6.0102 -0.7547 -0.6456 -0.1169
-6.2839 -10.0531 10.0483 -0.7031 -0.0580 -0.7087
-2.7796 -0.4011 -18.9767 0.0645 -0.8289 0.5556
-13.3484 -0.6527 -3.2172 0.0669 -0.8185 -0.5706
-3.3413 13.5529 0.8147 0.9828 -0.0242 -0.1830
1.2437 9.5866 14.0205 0.6169 0.6532 -0.4390
10.6269 8.1123 4.2644 0.4784 0.7806 0.4023

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.803
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5489
_diffrn_reflns_point_group_measured_fraction_full 0.751
_diffrn_reflns_point_group_measured_fraction_max 0.582
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.230
_diffrn_reflns_theta_min         2.950
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      253
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.803
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  11.00   0.25    2.20    --   -5.68 -59.00  26.00  300
  2  ω    -16.00  39.00   0.25    2.20    --    6.15 -99.00   0.00  220
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0075661943
_diffrn_orient_matrix_UB_12      0.0708795817
_diffrn_orient_matrix_UB_13      -0.0037905507
_diffrn_orient_matrix_UB_21      0.0522435019
_diffrn_orient_matrix_UB_22      0.0089408503
_diffrn_orient_matrix_UB_23      0.0358408541
_diffrn_orient_matrix_UB_31      0.0515596105
_diffrn_orient_matrix_UB_32      0.0014257626
_diffrn_orient_matrix_UB_33      -0.0368601025
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.373
_reflns_Friedel_fraction_full    0.475
_reflns_Friedel_fraction_max     0.334
_reflns_number_gt                2181
_reflns_number_total             2279
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.162
_refine_ls_abs_structure_details 
;
 Flack x determined using 574 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.025(8)
_refine_ls_extinction_coef       0.0110(6)
_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   1.117
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2279
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0237
_refine_ls_R_factor_gt           0.0224
_refine_ls_restrained_S_all      1.116
_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)+(0.0317P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0509
_refine_ls_wR_factor_ref         0.0512
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H,H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 N4(H4), N3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C3(H3A,H3B), C4(H4A,H4B), C2(H2A,H2B), C5(H5A,H5B), C1(H1A,H1B)
;
_atom_sites_solution_hydrogens   mixed
_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
Br01 Br 0.27743(3) 0.46336(4) 0.71125(6) 0.02760(12) Uani 1 1 d . . . . .
Br02 Br -0.01624(3) 0.78138(4) 0.41454(6) 0.03209(12) Uani 1 1 d . . . . .
Br03 Br 0.24582(3) 1.00867(4) 0.66608(8) 0.03252(12) Uani 1 1 d . . . . .
P1 P 0.56805(7) 0.08462(11) 0.43128(14) 0.0290(3) Uani 1 1 d . . . . .
N4 N 0.5644(2) 0.3664(3) 0.4108(4) 0.0232(7) Uani 1 1 d . . . . .
H4 H 0.605004 0.447914 0.399183 0.028 Uiso 1 1 calc R U . . .
N2 N 0.4296(2) 0.2459(3) 0.2996(4) 0.0240(7) Uani 1 1 d . . . . .
N1 N 0.2264(3) 0.7152(4) 0.4703(7) 0.0380(10) Uani 1 1 d . . . . .
N3 N 0.4380(3) 0.2677(3) 0.5538(4) 0.0251(8) Uani 1 1 d . . . . .
H3 H 0.396220 0.284804 0.635712 0.030 Uiso 1 1 calc R U . . .
C6 C 0.5086(3) 0.3823(5) 0.5417(5) 0.0275(10) Uani 1 1 d . . . . .
H6A H 0.473482 0.468221 0.540866 0.033 Uiso 1 1 calc R U . . .
H6B H 0.552946 0.382185 0.621479 0.033 Uiso 1 1 calc R U . . .
C3 C 0.6318(2) 0.2469(4) 0.4173(6) 0.0276(8) Uani 1 1 d . . . . .
H3A H 0.674969 0.257306 0.497721 0.033 Uiso 1 1 calc R U . . .
H3B H 0.672353 0.246039 0.333504 0.033 Uiso 1 1 calc R U . . .
C4 C 0.3730(3) 0.2607(4) 0.4260(6) 0.0305(10) Uani 1 1 d . . . . .
H4A H 0.328497 0.184143 0.435028 0.037 Uiso 1 1 calc R U . . .
H4B H 0.333894 0.343049 0.420124 0.037 Uiso 1 1 calc R U . . .
C2 C 0.4894(3) 0.1351(4) 0.5762(5) 0.0288(10) Uani 1 1 d . . . . .
H2A H 0.440510 0.064735 0.591131 0.035 Uiso 1 1 calc R U . . .
H2B H 0.528765 0.141406 0.660865 0.035 Uiso 1 1 calc R U . . .
C5 C 0.4954(3) 0.3593(4) 0.2868(5) 0.0257(9) Uani 1 1 d . . . . .
H5A H 0.457822 0.443003 0.281163 0.031 Uiso 1 1 calc R U . . .
H5B H 0.533190 0.350451 0.200835 0.031 Uiso 1 1 calc R U . . .
C1 C 0.4795(3) 0.1159(5) 0.2908(5) 0.0304(10) Uani 1 1 d . . . . .
H1A H 0.513385 0.110828 0.201323 0.036 Uiso 1 1 calc R U . . .
H1B H 0.430654 0.044075 0.292367 0.036 Uiso 1 1 calc R U . . .
H1C H 0.170(4) 0.729(5) 0.450(6) 0.036 Uiso 1 1 d . U . . .
H1D H 0.263(4) 0.706(6) 0.408(8) 0.036 Uiso 1 1 d . U . . .
H1E H 0.234(4) 0.664(6) 0.530(7) 0.036 Uiso 1 1 d . U . . .
H1F H 0.236(4) 0.796(6) 0.497(7) 0.036 Uiso 1 1 d . U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br01 0.02389(18) 0.02791(19) 0.0310(2) -0.00023(18) 0.00075(17) 0.00236(14)
Br02 0.0356(2) 0.0326(2) 0.0280(2) -0.0035(2) -0.0032(2) 0.00502(15)
Br03 0.02792(19) 0.0325(2) 0.0372(3) 0.0052(2) 0.00184(18) -0.00156(16)
P1 0.0253(4) 0.0226(5) 0.0392(8) -0.0004(5) -0.0030(5) 0.0050(4)
N4 0.0259(14) 0.0177(14) 0.0259(19) -0.0001(15) 0.0030(15) -0.0035(11)
N2 0.0217(15) 0.0241(15) 0.026(2) 0.0044(15) -0.0042(14) 0.0038(13)
N1 0.033(2) 0.036(2) 0.045(3) 0.013(2) -0.0021(19) 0.0025(17)
N3 0.0233(16) 0.0253(17) 0.027(2) 0.0032(15) 0.0078(14) 0.0063(13)
C6 0.034(2) 0.022(2) 0.026(3) -0.0050(19) 0.0000(17) -0.0001(16)
C3 0.0160(13) 0.0292(19) 0.038(2) -0.005(2) 0.002(2) 0.0018(14)
C4 0.0177(14) 0.032(2) 0.042(3) 0.002(2) -0.0020(19) 0.0030(14)
C2 0.032(2) 0.023(2) 0.031(3) 0.0083(19) 0.0021(18) 0.0022(16)
C5 0.034(2) 0.023(2) 0.020(3) 0.0045(18) 0.0009(16) 0.0012(15)
C1 0.034(2) 0.023(2) 0.034(3) -0.008(2) -0.0023(19) 0.0001(16)

_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 C3 1.840(4) . ?
P1 C2 1.834(5) . ?
P1 C1 1.845(5) . ?
N4 H4 0.9900 . ?
N4 C6 1.483(6) . ?
N4 C3 1.506(5) . ?
N4 C5 1.525(6) . ?
N2 C4 1.451(6) . ?
N2 C5 1.450(5) . ?
N2 C1 1.464(5) . ?
N1 H1C 0.81(5) . ?
N1 H1D 0.79(7) . ?
N1 H1E 0.77(7) . ?
N1 H1F 0.86(6) . ?
N3 H3 0.9900 . ?
N3 C6 1.500(5) . ?
N3 C4 1.522(7) . ?
N3 C2 1.509(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 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
C3 P1 C1 96.6(2) . . ?
C2 P1 C3 95.6(2) . . ?
C2 P1 C1 96.9(2) . . ?
C6 N4 H4 107.5 . . ?
C6 N4 C3 111.6(4) . . ?
C6 N4 C5 110.2(3) . . ?
C3 N4 H4 107.5 . . ?
C3 N4 C5 112.3(3) . . ?
C5 N4 H4 107.5 . . ?
C4 N2 C1 112.9(3) . . ?
C5 N2 C4 109.1(3) . . ?
C5 N2 C1 112.8(3) . . ?
H1C N1 H1D 117(6) . . ?
H1C N1 H1E 115(6) . . ?
H1C N1 H1F 94(5) . . ?
H1D N1 H1E 114(6) . . ?
H1D N1 H1F 104(6) . . ?
H1E N1 H1F 112(7) . . ?
C6 N3 H3 107.9 . . ?
C6 N3 C4 110.7(4) . . ?
C6 N3 C2 111.7(3) . . ?
C4 N3 H3 107.9 . . ?
C2 N3 H3 107.9 . . ?
C2 N3 C4 110.5(3) . . ?
N4 C6 N3 108.6(3) . . ?
N4 C6 H6A 110.0 . . ?
N4 C6 H6B 110.0 . . ?
N3 C6 H6A 110.0 . . ?
N3 C6 H6B 110.0 . . ?
H6A C6 H6B 108.3 . . ?
P1 C3 H3A 108.9 . . ?
P1 C3 H3B 108.9 . . ?
N4 C3 P1 113.5(2) . . ?
N4 C3 H3A 108.9 . . ?
N4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
N2 C4 N3 111.4(3) . . ?
N2 C4 H4A 109.4 . . ?
N2 C4 H4B 109.4 . . ?
N3 C4 H4A 109.4 . . ?
N3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
P1 C2 H2A 108.8 . . ?
P1 C2 H2B 108.8 . . ?
N3 C2 P1 114.0(3) . . ?
N3 C2 H2A 108.8 . . ?
N3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
N4 C5 H5A 109.4 . . ?
N4 C5 H5B 109.4 . . ?
N2 C5 N4 111.0(4) . . ?
N2 C5 H5A 109.4 . . ?
N2 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
P1 C1 H1A 108.6 . . ?
P1 C1 H1B 108.6 . . ?
N2 C1 P1 114.6(3) . . ?
N2 C1 H1A 108.6 . . ?
N2 C1 H1B 108.6 . . ?
H1A C1 H1B 107.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N4 C3 P1 64.9(5) . . . . ?
C6 N4 C5 N2 -60.1(4) . . . . ?
C6 N3 C4 N2 57.8(4) . . . . ?
C6 N3 C2 P1 -63.1(5) . . . . ?
C3 P1 C2 N3 49.5(3) . . . . ?
C3 P1 C1 N2 -49.1(4) . . . . ?
C3 N4 C6 N3 -68.8(4) . . . . ?
C3 N4 C5 N2 65.0(4) . . . . ?
C4 N2 C5 N4 59.9(4) . . . . ?
C4 N2 C1 P1 -61.3(4) . . . . ?
C4 N3 C6 N4 -55.8(4) . . . . ?
C4 N3 C2 P1 60.6(4) . . . . ?
C2 P1 C3 N4 -50.1(4) . . . . ?
C2 P1 C1 N2 47.4(4) . . . . ?
C2 N3 C6 N4 67.8(5) . . . . ?
C2 N3 C4 N2 -66.5(4) . . . . ?
C5 N4 C6 N3 56.7(4) . . . . ?
C5 N4 C3 P1 -59.5(5) . . . . ?
C5 N2 C4 N3 -58.9(4) . . . . ?
C5 N2 C1 P1 63.0(5) . . . . ?
C1 P1 C3 N4 47.5(4) . . . . ?
C1 P1 C2 N3 -47.8(3) . . . . ?
C1 N2 C4 N3 67.3(4) . . . . ?
C1 N2 C5 N4 -66.4(5) . . . . ?

_shelx_res_file                  
;
TITL rt1225_inv_a.res in Pna2(1)
    rt1225_inv.res
    created by SHELXL-2018/3 at 13:43:02 on 08-Jan-2025
REM Old TITL RT1225_inv in P2(1)cn
REM SHELXT solution in Pna2(1): R1 0.056, Rweak 0.019, Alpha 0.004
REM <I/s> 0.529 for 141 systematic absences, Orientation a'=c, b'=-b, c'=a
REM Flack x = 0.036 ( 0.008 ) from 552 Parsons' quotients
REM Formula found by SHELXT: C8 N2 P Br3
CELL 0.71073 13.7604 9.9259 9.6119 90 90 90
ZERR 4 0.0003 0.0003 0.0003 0 0 0
LATT -1
SYMM -X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,+Z
SYMM 0.5-X,0.5+Y,0.5+Z
SFAC C H Br N P
UNIT 24 72 12 16 4

L.S. 4 0 0
PLAN  3
SIZE 0.16 0.2 0.24
TEMP -20.15
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\RT1225_inv.hkl">
REM </olex2.extras>

WGHT    0.031700
EXTI    0.010963
FVAR       0.34005
BR01  3    0.277434    0.463358    0.711250    11.00000    0.02389    0.02791 =
         0.03100   -0.00023    0.00075    0.00236
BR02  3   -0.016243    0.781385    0.414539    11.00000    0.03563    0.03260 =
         0.02803   -0.00348   -0.00320    0.00502
BR03  3    0.245819    1.008673    0.666080    11.00000    0.02792    0.03249 =
         0.03715    0.00521    0.00184   -0.00156
P1    5    0.568046    0.084621    0.431284    11.00000    0.02526    0.02265 =
         0.03917   -0.00042   -0.00301    0.00498
N4    4    0.564395    0.366352    0.410790    11.00000    0.02586    0.01768 =
         0.02594   -0.00010    0.00299   -0.00347
AFIX  13
H4    2    0.605004    0.447914    0.399183    11.00000   -1.20000
AFIX   0
N2    4    0.429625    0.245917    0.299611    11.00000    0.02166    0.02408 =
         0.02639    0.00441   -0.00420    0.00379

N1    4    0.226385    0.715185    0.470335    11.00000    0.03338    0.03553 =
         0.04497    0.01275   -0.00207    0.00250
N3    4    0.438049    0.267722    0.553789    11.00000    0.02326    0.02526 =
         0.02676    0.00323    0.00778    0.00630
AFIX  13
H3    2    0.396220    0.284804    0.635712    11.00000   -1.20000
AFIX   0
C6    1    0.508593    0.382326    0.541707    11.00000    0.03443    0.02164 =
         0.02636   -0.00501    0.00000   -0.00013
AFIX  23
H6A   2    0.473482    0.468221    0.540866    11.00000   -1.20000
H6B   2    0.552946    0.382185    0.621479    11.00000   -1.20000
AFIX   0
C3    1    0.631813    0.246943    0.417325    11.00000    0.01602    0.02923 =
         0.03756   -0.00460    0.00184    0.00182
AFIX  23
H3A   2    0.674969    0.257306    0.497721    11.00000   -1.20000
H3B   2    0.672353    0.246039    0.333504    11.00000   -1.20000
AFIX   0
C4    1    0.372998    0.260727    0.425981    11.00000    0.01766    0.03153 =
         0.04224    0.00214   -0.00200    0.00297
AFIX  23
H4A   2    0.328497    0.184143    0.435028    11.00000   -1.20000
H4B   2    0.333894    0.343049    0.420124    11.00000   -1.20000
AFIX   0
C2    1    0.489364    0.135102    0.576183    11.00000    0.03202    0.02293 =
         0.03139    0.00834    0.00208    0.00225
AFIX  23
H2A   2    0.440510    0.064735    0.591131    11.00000   -1.20000
H2B   2    0.528765    0.141406    0.660865    11.00000   -1.20000
AFIX   0
C5    1    0.495425    0.359333    0.286788    11.00000    0.03357    0.02339 =
         0.02025    0.00448    0.00094    0.00118
AFIX  23
H5A   2    0.457822    0.443003    0.281163    11.00000   -1.20000
H5B   2    0.533190    0.350451    0.200835    11.00000   -1.20000
AFIX   0
C1    1    0.479485    0.115930    0.290833    11.00000    0.03437    0.02323 =
         0.03350   -0.00835   -0.00231    0.00014
AFIX  23
H1A   2    0.513385    0.110828    0.201323    11.00000   -1.20000
H1B   2    0.430654    0.044075    0.292367    11.00000   -1.20000
AFIX   0
H1C   2    0.170077    0.728763    0.449967    11.00000   -1.20000
H1D   2    0.263173    0.706097    0.407860    11.00000   -1.20000
H1E   2    0.233992    0.664258    0.529845    11.00000   -1.20000
H1F   2    0.236194    0.796457    0.496997    11.00000   -1.20000
HKLF 4




REM  rt1225_inv_a.res in Pna2(1)
REM wR2 = 0.0512, GooF = S = 1.117, Restrained GooF = 1.116 for all data
REM R1 = 0.0224 for 2181 Fo > 4sig(Fo) and 0.0237 for all 2279 data
REM 140 parameters refined using 1 restraints

END

WGHT      0.0317      0.0000

REM Highest difference peak  0.458,  deepest hole -0.744,  1-sigma level  0.162
Q1    1   0.2485  0.4265  0.6598  11.00000  0.05    0.46
Q2    1   0.4811 -0.0117  0.2069  11.00000  0.05    0.44
Q3    1   0.2924  0.5153  0.6573  11.00000  0.05    0.43
;
_shelx_res_checksum              84132
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.424
_oxdiff_exptl_absorpt_empirical_full_min 0.714
####################################################################### 
# 
# 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_pta-br_298k
_database_code_depnum_ccdc_archive 'CCDC 2424525'
loop_
_audit_author_name
_audit_author_address
'Ryo Tsunashima'
;yamaguchi
Japan
;
_audit_update_record             
;
2025-02-17 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;
_audit_creation_date             2025-01-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(Br), C6 H14 N3 P, H4 N'
_chemical_formula_sum            'C6 H18 Br3 N4 P'
_chemical_formula_weight         416.94
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H18N3Br3P
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'
N N 0.0061 0.0033 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   13.7833(4)
_cell_length_b                   9.9419(3)
_cell_length_c                   9.6453(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1321.72(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4113
_cell_measurement_temperature    298
_cell_measurement_theta_max      30.8060
_cell_measurement_theta_min      2.9250
_shelx_estimated_absorpt_T_max   0.319
_shelx_estimated_absorpt_T_min   0.272
_exptl_absorpt_coefficient_mu    9.251
_exptl_absorpt_correction_T_max  0.30518
_exptl_absorpt_correction_T_min  0.29079
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.095
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       sphere
_exptl_crystal_F_000             808
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 8 11 0.0555
16 -2 8 0.0729
-14 0 -9 0.0953
-8 11 6 0.0505
8 -4 12 0.0543
14 8 -4 0.0798
1 7 -12 0.1006
-11 2 -11 0.0956
-17 -5 -5 0.1003
-15 -8 3 0.1062
0 -10 -9 0.0994
1 -4 -13 0.1033
14 -2 -10 0.0990

_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_size_rad          0.093
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.7870 7.7826 10.9902 0.4831 0.5074 0.7135
15.6351 -2.3344 7.7496 -0.1627 -0.1756 0.9709
-14.3450 0.2569 -9.1678 0.0313 0.0369 -0.9988
-8.1361 10.8371 6.4716 0.6869 0.7252 0.0462
7.9364 -3.6586 11.8964 -0.3172 0.3037 0.8984
14.4678 8.4434 -3.9191 0.6828 -0.6453 0.3427
1.4534 7.4068 -11.5059 0.6159 -0.5851 -0.5276
-11.4579 1.5651 -10.8775 0.1478 -0.1436 -0.9785
-17.1735 -4.6093 -4.5193 -0.3588 0.3365 -0.8706
-14.9915 -8.2685 3.2469 -0.6674 0.6305 -0.3963
0.3883 -10.4863 -9.0132 -0.6731 -0.5778 -0.4617
0.8296 -3.9127 -13.0432 -0.1760 -0.7446 -0.6439
13.5724 -2.1036 -9.5147 -0.0251 -0.9996 0.0091

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5100
_diffrn_reflns_point_group_measured_fraction_full 0.772
_diffrn_reflns_point_group_measured_fraction_max 0.762
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.365
_diffrn_reflns_theta_min         2.942
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  11.00   0.25    2.20    --   -5.68 -59.00  26.00  300
  2  ω    -16.00  39.00   0.25    2.20    --    6.15 -99.00   0.00  220
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0038681000
_diffrn_orient_matrix_UB_12      0.0707617000
_diffrn_orient_matrix_UB_13      -0.0074848000
_diffrn_orient_matrix_UB_21      -0.0357227000
_diffrn_orient_matrix_UB_22      0.0089785000
_diffrn_orient_matrix_UB_23      0.0521207000
_diffrn_orient_matrix_UB_31      0.0368482000
_diffrn_orient_matrix_UB_32      0.0012718000
_diffrn_orient_matrix_UB_33      0.0513282000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.441
_reflns_Friedel_fraction_full    0.520
_reflns_Friedel_fraction_max     0.498
_reflns_number_gt                1994
_reflns_number_total             2061
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.760
_refine_diff_density_min         -1.108
_refine_diff_density_rms         0.124
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.018(13)
_refine_ls_extinction_coef       0.0027(10)
_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   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2061
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1111P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1268
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H,H,H) groups, All N(H) groups
2. Restrained distances
 N1-H1D = N1-H1E = N1-H1F = N1-H1C
 1.05 with sigma of 0.02
 H1C-H1D = H1C-H1E = H1D-H1E = H1D-H1F = H1E-H1F = H1C-H1F
 1.75 with sigma of 0.04
3.a Ternary CH refined with riding coordinates:
 N4(H4), N3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C3(H3A,H3B), C4(H4A,H4B), C2(H2A,H2B), C5(H5A,H5B), C1(H1A,H1B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
Br01 Br 0.27749(6) 0.46358(9) 0.71097(13) 0.0371(3) Uani 1 1 d . . . . .
Br02 Br -0.01525(6) 0.78156(10) 0.41472(12) 0.0419(3) Uani 1 1 d . . . . .
Br03 Br 0.24615(7) 1.00773(9) 0.66634(19) 0.0429(3) Uani 1 1 d . . . . .
P1 P 0.56851(15) 0.0852(2) 0.4314(3) 0.0417(6) Uani 1 1 d . . . . .
N4 N 0.5645(4) 0.3669(6) 0.4112(9) 0.0324(15) Uani 1 1 d . . . . .
H4 H 0.604666 0.447362 0.399166 0.039 Uiso 1 1 calc R U . . .
N2 N 0.4287(5) 0.2432(8) 0.2982(9) 0.0341(16) Uani 1 1 d . . . . .
N1 N 0.2279(6) 0.7143(9) 0.4666(13) 0.049(2) Uani 1 1 d D . . . .
N3 N 0.4387(5) 0.2671(8) 0.5532(9) 0.0350(17) Uani 1 1 d . . . . .
H3 H 0.397409 0.284003 0.634125 0.042 Uiso 1 1 calc R U . . .
C6 C 0.5089(6) 0.3836(10) 0.5405(11) 0.036(2) Uani 1 1 d . . . . .
H6A H 0.473599 0.467993 0.538666 0.043 Uiso 1 1 calc R U . . .
H6B H 0.552569 0.384765 0.619370 0.043 Uiso 1 1 calc R U . . .
C3 C 0.6314(5) 0.2476(9) 0.4179(12) 0.0358(17) Uani 1 1 d . . . . .
H3A H 0.673890 0.257876 0.497359 0.043 Uiso 1 1 calc R U . . .
H3B H 0.671652 0.246864 0.335431 0.043 Uiso 1 1 calc R U . . .
C4 C 0.3732(6) 0.2596(10) 0.4266(13) 0.041(2) Uani 1 1 d . . . . .
H4A H 0.328927 0.184445 0.436884 0.049 Uiso 1 1 calc R U . . .
H4B H 0.334860 0.341222 0.420784 0.049 Uiso 1 1 calc R U . . .
C2 C 0.4902(7) 0.1341(11) 0.5763(12) 0.041(2) Uani 1 1 d . . . . .
H2A H 0.442035 0.064355 0.590962 0.049 Uiso 1 1 calc R U . . .
H2B H 0.529139 0.140476 0.659822 0.049 Uiso 1 1 calc R U . . .
C5 C 0.4950(6) 0.3586(10) 0.2862(10) 0.0337(19) Uani 1 1 d . . . . .
H5A H 0.457506 0.440969 0.280374 0.040 Uiso 1 1 calc R U . . .
H5B H 0.532607 0.350251 0.201575 0.040 Uiso 1 1 calc R U . . .
C1 C 0.4803(7) 0.1153(11) 0.2923(13) 0.045(3) Uani 1 1 d . . . . .
H1A H 0.514042 0.110244 0.204217 0.054 Uiso 1 1 calc R U . . .
H1B H 0.432842 0.043307 0.293958 0.054 Uiso 1 1 calc R U . . .
H1C H 0.164(4) 0.712(9) 0.405(8) 0.054 Uiso 1 1 d D U . . .
H1D H 0.287(5) 0.722(9) 0.398(8) 0.054 Uiso 1 1 d D U . . .
H1E H 0.235(6) 0.631(6) 0.532(8) 0.054 Uiso 1 1 d D U . . .
H1F H 0.222(6) 0.803(6) 0.528(8) 0.054 Uiso 1 1 d D U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br01 0.0307(4) 0.0335(4) 0.0470(6) 0.0006(4) 0.0014(4) 0.0026(3)
Br02 0.0444(5) 0.0381(5) 0.0432(5) -0.0039(5) -0.0039(5) 0.0061(3)
Br03 0.0360(5) 0.0385(5) 0.0543(7) 0.0055(5) 0.0029(4) -0.0016(4)
P1 0.0339(10) 0.0289(11) 0.0624(17) -0.0003(10) -0.0048(11) 0.0063(9)
N4 0.029(3) 0.023(3) 0.045(4) -0.001(3) 0.003(3) -0.005(2)
N2 0.027(3) 0.030(3) 0.045(4) 0.011(4) -0.005(3) 0.006(3)
N1 0.044(4) 0.043(5) 0.061(6) 0.013(4) -0.006(4) 0.002(3)
N3 0.034(3) 0.031(4) 0.040(4) 0.001(3) 0.011(3) 0.007(3)
C6 0.037(4) 0.028(5) 0.043(5) -0.006(4) -0.001(4) 0.002(3)
C3 0.022(3) 0.035(4) 0.050(5) -0.004(5) 0.000(4) 0.001(3)
C4 0.025(3) 0.031(4) 0.065(6) 0.004(5) -0.003(4) 0.003(3)
C2 0.041(5) 0.032(5) 0.050(6) 0.013(5) 0.003(4) 0.002(4)
C5 0.047(5) 0.025(4) 0.029(5) 0.003(4) 0.002(4) 0.004(3)
C1 0.048(5) 0.029(5) 0.058(7) -0.021(5) -0.006(5) -0.003(4)

_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 C3 1.837(9) . ?
P1 C2 1.832(11) . ?
P1 C1 1.835(11) . ?
N4 H4 0.9800 . ?
N4 C6 1.473(13) . ?
N4 C3 1.504(10) . ?
N4 C5 1.541(12) . ?
N2 C4 1.464(14) . ?
N2 C5 1.472(13) . ?
N2 C1 1.458(13) . ?
N1 H1C 1.07(2) . ?
N1 H1D 1.06(2) . ?
N1 H1E 1.04(2) . ?
N1 H1F 1.07(2) . ?
N3 H3 0.9800 . ?
N3 C6 1.515(12) . ?
N3 C4 1.520(14) . ?
N3 C2 1.517(12) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 P1 C3 95.7(5) . . ?
C2 P1 C1 97.1(5) . . ?
C1 P1 C3 96.7(5) . . ?
C6 N4 H4 107.6 . . ?
C6 N4 C3 111.8(8) . . ?
C6 N4 C5 110.2(6) . . ?
C3 N4 H4 107.6 . . ?
C3 N4 C5 111.9(7) . . ?
C5 N4 H4 107.6 . . ?
C4 N2 C5 107.7(8) . . ?
C1 N2 C4 112.7(8) . . ?
C1 N2 C5 111.9(7) . . ?
H1C N1 H1D 107(4) . . ?
H1C N1 H1E 113(4) . . ?
H1C N1 H1F 106(4) . . ?
H1D N1 H1E 112(4) . . ?
H1D N1 H1F 110(4) . . ?
H1E N1 H1F 109(4) . . ?
C6 N3 H3 107.7 . . ?
C6 N3 C4 110.6(8) . . ?
C6 N3 C2 112.3(7) . . ?
C4 N3 H3 107.7 . . ?
C2 N3 H3 107.7 . . ?
C2 N3 C4 110.7(8) . . ?
N4 C6 N3 108.3(8) . . ?
N4 C6 H6A 110.0 . . ?
N4 C6 H6B 110.0 . . ?
N3 C6 H6A 110.0 . . ?
N3 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
P1 C3 H3A 108.8 . . ?
P1 C3 H3B 108.8 . . ?
N4 C3 P1 114.0(5) . . ?
N4 C3 H3A 108.8 . . ?
N4 C3 H3B 108.8 . . ?
H3A C3 H3B 107.6 . . ?
N2 C4 N3 112.0(6) . . ?
N2 C4 H4A 109.2 . . ?
N2 C4 H4B 109.2 . . ?
N3 C4 H4A 109.2 . . ?
N3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
P1 C2 H2A 108.9 . . ?
P1 C2 H2B 108.9 . . ?
N3 C2 P1 113.3(7) . . ?
N3 C2 H2A 108.9 . . ?
N3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
N4 C5 H5A 109.3 . . ?
N4 C5 H5B 109.3 . . ?
N2 C5 N4 111.4(7) . . ?
N2 C5 H5A 109.3 . . ?
N2 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
P1 C1 H1A 108.3 . . ?
P1 C1 H1B 108.3 . . ?
N2 C1 P1 115.9(7) . . ?
N2 C1 H1A 108.3 . . ?
N2 C1 H1B 108.3 . . ?
H1A C1 H1B 107.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N4 C3 P1 65.1(9) . . . . ?
C6 N4 C5 N2 -60.6(9) . . . . ?
C6 N3 C4 N2 58.9(9) . . . . ?
C6 N3 C2 P1 -63.1(10) . . . . ?
C3 P1 C2 N3 49.4(8) . . . . ?
C3 P1 C1 N2 -49.1(9) . . . . ?
C3 N4 C6 N3 -67.9(9) . . . . ?
C3 N4 C5 N2 64.4(9) . . . . ?
C4 N2 C5 N4 59.2(9) . . . . ?
C4 N2 C1 P1 -59.4(10) . . . . ?
C4 N3 C6 N4 -56.7(9) . . . . ?
C4 N3 C2 P1 61.1(9) . . . . ?
C2 P1 C3 N4 -50.5(9) . . . . ?
C2 P1 C1 N2 47.5(9) . . . . ?
C2 N3 C6 N4 67.5(11) . . . . ?
C2 N3 C4 N2 -66.2(9) . . . . ?
C5 N4 C6 N3 57.2(9) . . . . ?
C5 N4 C3 P1 -59.1(10) . . . . ?
C5 N2 C4 N3 -58.8(9) . . . . ?
C5 N2 C1 P1 62.2(11) . . . . ?
C1 P1 C3 N4 47.4(9) . . . . ?
C1 P1 C2 N3 -48.1(8) . . . . ?
C1 N2 C4 N3 65.1(10) . . . . ?
C1 N2 C5 N4 -65.2(10) . . . . ?

_shelx_res_file                  
;
TITL pta-br_300k_re2_a.res in Pna2(1)
    pta-br_298k.res
    created by SHELXL-2018/3 at 13:44:54 on 08-Jan-2025
REM Old TITL pta-Br_300K_re2 in Pna2(1)
REM SHELXT solution in Pna2(1): R1 0.077, Rweak 0.014, Alpha 0.003
REM <I/s> 0.490 for 144 systematic absences, Orientation as input
REM Flack x = -0.057 ( 0.032 ) from 598 Parsons' quotients
REM Formula found by SHELXT: C7 N3 P Br3
CELL 0.71073 13.7833 9.9419 9.6453 90 90 90
ZERR 4 0.0004 0.0003 0.0003 0 0 0
LATT -1
SYMM -X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,+Z
SYMM 0.5-X,0.5+Y,0.5+Z
SFAC C H Br N P
UNIT 24 72 12 16 4
DFIX 1.05 N1 H1d N1 H1e N1 H1f N1 H1c
DANG 1.75 H1c H1d H1c H1e H1d H1e H1d H1f H1e H1f H1c H1f

L.S. 15
PLAN  6
SIZE 0.16 0.18 0.19
TEMP 24.85
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\pta-Br_298K.hkl">
REM </olex2.extras>

WGHT    0.111100
EXTI    0.002714
FVAR       0.30238
BR01  3    0.277494    0.463582    0.710968    11.00000    0.03070    0.03352 =
         0.04697    0.00060    0.00140    0.00260
BR02  3   -0.015252    0.781562    0.414722    11.00000    0.04441    0.03808 =
         0.04318   -0.00392   -0.00391    0.00605
BR03  3    0.246155    1.007730    0.666340    11.00000    0.03598    0.03850 =
         0.05432    0.00545    0.00290   -0.00158
P1    5    0.568511    0.085191    0.431418    11.00000    0.03393    0.02891 =
         0.06236   -0.00031   -0.00482    0.00629
N4    4    0.564464    0.366899    0.411177    11.00000    0.02931    0.02261 =
         0.04536   -0.00112    0.00288   -0.00536
AFIX  13
H4    2    0.604666    0.447362    0.399166    11.00000   -1.20000
AFIX   0
N2    4    0.428676    0.243171    0.298235    11.00000    0.02679    0.03022 =
         0.04544    0.01123   -0.00531    0.00616

N1    4    0.227889    0.714343    0.466589    11.00000    0.04385    0.04295 =
         0.06094    0.01308   -0.00606    0.00233
N3    4    0.438653    0.267091    0.553219    11.00000    0.03394    0.03069 =
         0.04045    0.00070    0.01107    0.00732
AFIX  13
H3    2    0.397409    0.284003    0.634125    11.00000   -1.20000
AFIX   0
C6    1    0.508889    0.383599    0.540527    11.00000    0.03706    0.02772 =
         0.04264   -0.00557   -0.00135    0.00229
AFIX  23
H6A   2    0.473599    0.467993    0.538666    11.00000   -1.20000
H6B   2    0.552569    0.384765    0.619370    11.00000   -1.20000
AFIX   0
C3    1    0.631387    0.247598    0.417908    11.00000    0.02247    0.03540 =
         0.04966   -0.00434    0.00019    0.00076
AFIX  23
H3A   2    0.673890    0.257876    0.497359    11.00000   -1.20000
H3B   2    0.671652    0.246864    0.335431    11.00000   -1.20000
AFIX   0
C4    1    0.373213    0.259613    0.426603    11.00000    0.02539    0.03118 =
         0.06506    0.00388   -0.00259    0.00345
AFIX  23
H4A   2    0.328927    0.184445    0.436884    11.00000   -1.20000
H4B   2    0.334860    0.341222    0.420784    11.00000   -1.20000
AFIX   0
C2    1    0.490167    0.134106    0.576341    11.00000    0.04074    0.03227 =
         0.05013    0.01322    0.00309    0.00192
AFIX  23
H2A   2    0.442035    0.064355    0.590962    11.00000   -1.20000
H2B   2    0.529139    0.140476    0.659822    11.00000   -1.20000
AFIX   0
C5    1    0.495039    0.358629    0.286174    11.00000    0.04717    0.02523 =
         0.02858    0.00269    0.00237    0.00440
AFIX  23
H5A   2    0.457506    0.440969    0.280374    11.00000   -1.20000
H5B   2    0.532607    0.350251    0.201575    11.00000   -1.20000
AFIX   0
C1    1    0.480289    0.115346    0.292306    11.00000    0.04841    0.02857 =
         0.05757   -0.02098   -0.00592   -0.00347
AFIX  23
H1A   2    0.514042    0.110244    0.204217    11.00000   -1.20000
H1B   2    0.432842    0.043307    0.293958    11.00000   -1.20000
AFIX   0
H1C   2    0.163827    0.712130    0.404738    11.00000   -1.20000
H1D   2    0.287091    0.722276    0.397583    11.00000   -1.20000
H1E   2    0.234809    0.631043    0.531915    11.00000   -1.20000
H1F   2    0.222446    0.803038    0.528298    11.00000   -1.20000
HKLF 4




REM  pta-br_300k_re2_a.res in Pna2(1)
REM wR2 = 0.1268, GooF = S = 1.069, Restrained GooF = 1.067 for all data
REM R1 = 0.0481 for 1994 Fo > 4sig(Fo) and 0.0492 for all 2061 data
REM 140 parameters refined using 11 restraints

END

WGHT      0.1111      0.0000

REM Highest difference peak  0.760,  deepest hole -1.108,  1-sigma level  0.124
Q1    1  -0.0192  0.7262  0.5026  11.00000  0.05    0.76
Q2    1  -0.0164  0.7245  0.3307  11.00000  0.05    0.74
Q3    1  -0.0205  0.8438  0.5130  11.00000  0.05    0.68
Q4    1   0.2779  0.4031  0.6201  11.00000  0.05    0.64
Q5    1   0.2817  0.5200  0.6210  11.00000  0.05    0.61
Q6    1   0.2769  0.5239  0.8024  11.00000  0.05    0.58
;
_shelx_res_checksum              78947
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.555
_oxdiff_exptl_absorpt_empirical_full_min 0.669
####################################################################### 
# 
# 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_401k_cubic_rt
_database_code_depnum_ccdc_archive 'CCDC 2424519'
loop_
_audit_author_name
_audit_author_address
'Ryo Tsunashima'
;yamaguchi
Japan
;
_audit_update_record             
;
2025-02-17 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;
_audit_creation_date             2025-01-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(Br), N, 2(C6.228)'
_chemical_formula_sum            'C12.46 Br3 N'
_chemical_formula_weight         403.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H18N3Br3P
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'

_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      cubic
_space_group_IT_number           221
_space_group_name_H-M_alt        'P m -3 m'
_space_group_name_Hall           '-P 4 2 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x, y, -z'
'x, -y, -z'
'z, x, y'
'z, -x, -y'
'-z, -x, y'
'-z, x, -y'
'y, z, x'
'-y, z, -x'
'y, -z, -x'
'-y, -z, x'
'y, x, -z'
'-y, -x, -z'
'y, -x, z'
'-y, x, z'
'x, z, -y'
'-x, z, y'
'-x, -z, -y'
'x, -z, y'
'z, y, -x'
'z, -y, x'
'-z, y, x'
'-z, -y, -x'
'-x, -y, -z'
'x, y, -z'
'x, -y, z'
'-x, y, z'
'-z, -x, -y'
'-z, x, y'
'z, x, -y'
'z, -x, y'
'-y, -z, -x'
'y, -z, x'
'-y, z, x'
'y, z, -x'
'-y, -x, z'
'y, x, z'
'-y, x, -z'
'y, -x, -z'
'-x, -z, y'
'x, -z, -y'
'x, z, y'
'-x, z, -y'
'-z, -y, x'
'-z, y, -x'
'z, -y, -x'
'z, y, x'

_cell_length_a                   6.9822(4)
_cell_length_b                   6.9822(4)
_cell_length_c                   6.9822(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     340.39(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    432
_cell_measurement_temperature    401
_cell_measurement_theta_max      23.5180
_cell_measurement_theta_min      2.8990
_shelx_estimated_absorpt_T_max   0.331
_shelx_estimated_absorpt_T_min   0.246
_exptl_absorpt_coefficient_mu    8.861
_exptl_absorpt_correction_T_max  0.367
_exptl_absorpt_correction_T_min  0.216
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.968
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             187
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -3 -9 0.0821
-5 -9 1 0.0762
-1 -6 7 0.0867
4 3 8 0.0942
5 9 0 0.0767
3 8 -5 0.0891
-10 1 -2 0.1022
-6 -4 -6 0.0825
2 -7 -7 0.1021
9 -4 -1 0.0986
8 2 5 0.0869
1 7 7 0.0785
-5 6 5 0.0945
-4 8 3 0.0961
4 -6 7 0.0923
0 -10 1 0.0861
7 -2 -7 0.0988

_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.9789 -2.7041 -8.5823 -0.0694 -0.2785 0.9579
-4.5083 -8.6655 1.1953 0.1876 0.7921 0.5808
-1.4383 -6.3573 7.3849 0.2306 0.9632 -0.1383
4.1760 3.1929 8.3156 0.0559 0.2222 -0.9734
4.7996 8.5890 -0.0320 -0.1695 -0.7175 -0.6757
2.8550 7.8074 -5.2791 -0.2290 -0.9604 -0.1589
-9.6040 1.3909 -1.5978 -0.8308 0.2000 0.5195
-6.4727 -3.8518 -6.3191 -0.2112 0.0532 0.9760
1.7578 -6.8163 -6.8901 0.6298 -0.1484 0.7625
9.0594 -3.6892 -1.0949 0.9567 -0.2291 -0.1794
8.1010 2.2485 5.0932 0.4516 -0.1104 -0.8854
0.6563 6.5189 7.3489 -0.4248 0.0990 -0.8999
-4.9672 6.4955 5.4963 -0.8502 0.2018 -0.4862
-4.4376 8.1427 3.3218 -0.8955 -0.0726 -0.4392
3.9495 -6.0250 6.7086 0.6388 0.6731 -0.3728
0.1993 -9.7701 1.2053 0.6282 0.6650 0.4040
6.7876 -1.7410 -6.9274 0.7024 -0.6642 0.2560

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            1523
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.594
_diffrn_reflns_theta_min         2.917
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      401
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  11.00   0.25    2.20    --   -5.68 -59.00  26.00  300
  2  ω    -16.00  39.00   0.25    2.20    --    6.15 -99.00   0.00  220
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0786560000
_diffrn_orient_matrix_UB_12      -0.0637146000
_diffrn_orient_matrix_UB_13      -0.0083091000
_diffrn_orient_matrix_UB_21      -0.0412784000
_diffrn_orient_matrix_UB_22      -0.0602022000
_diffrn_orient_matrix_UB_23      0.0705607000
_diffrn_orient_matrix_UB_31      -0.0494544000
_diffrn_orient_matrix_UB_32      -0.0513020000
_diffrn_orient_matrix_UB_33      -0.0725237000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                70
_reflns_number_total             134
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     12
_refine_ls_number_reflns         134
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0572P)²+0.2006P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1422
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   .
_atom_sites_solution_primary     iterative
_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
Br01 Br 0.500000 0.500000 1.000000 0.1561(14) Uani 1 16 d S T P . .
N1 N 0.500000 0.500000 0.500000 0.166(12) Uani 1 48 d S T P . .
C2 C 0.000000 0.2533(16) 1.000000 0.116(6) Uani 0.92(4) 8 d S T . . .
C1 C 0.1382(11) 0.1382(11) 0.8618(11) 0.134(6) Uani 0.87(3) 6 d S T . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br01 0.1561(16) 0.1561(16) 0.156(2) 0.000 0.000 0.000
N1 0.166(12) 0.166(12) 0.166(12) 0.000 0.000 0.000
C2 0.135(7) 0.078(6) 0.135(7) 0.000 0.000 0.000
C1 0.134(6) 0.134(6) 0.134(6) 0.003(4) 0.003(4) -0.003(4)

_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
C2 C1 1.584(8) 28 ?
C2 C1 1.584(8) 26_557 ?
C2 C1 1.584(8) 3_557 ?
C2 C1 1.584(8) . ?
C1 C1 1.930(16) 28 ?
C1 C1 1.930(16) 26_557 ?
C1 C1 1.930(16) 27 ?

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
C1 C2 C1 119.0(10) 28 26_557 ?
C1 C2 C1 75.1(5) 28 . ?
C1 C2 C1 75.1(5) 26_557 3_557 ?
C1 C2 C1 119.0(10) 3_557 . ?
C1 C2 C1 75.1(5) 26_557 . ?
C1 C2 C1 75.1(5) 28 3_557 ?
C2 C1 C2 104.3(6) . 29_656 ?
C2 C1 C2 104.3(6) . 9_546 ?
C2 C1 C2 104.3(6) 29_656 9_546 ?
C2 C1 C1 52.5(2) . 28 ?
C2 C1 C1 52.5(2) . 26_557 ?
C2 C1 C1 120.5(5) 29_656 26_557 ?
C2 C1 C1 52.5(2) 29_656 27 ?
C2 C1 C1 52.5(2) 9_546 27 ?
C2 C1 C1 120.5(5) 9_546 28 ?
C2 C1 C1 52.5(2) 29_656 28 ?
C2 C1 C1 120.5(5) . 27 ?
C2 C1 C1 52.5(2) 9_546 26_557 ?
C1 C1 C1 89.999(2) 26_557 27 ?
C1 C1 C1 89.999(3) 28 27 ?
C1 C1 C1 89.999(2) 28 26_557 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C1 C2 -8.5(9) 28 . . 29_656 ?
C1 C2 C1 C2 54.6(5) 3_557 . . 29_656 ?
C1 C2 C1 C2 117.67(19) 26_557 . . 29_656 ?
C1 C2 C1 C2 8.5(9) 26_557 . . 9_546 ?
C1 C2 C1 C2 -117.67(19) 28 . . 9_546 ?
C1 C2 C1 C2 -54.6(5) 3_557 . . 9_546 ?
C1 C2 C1 C1 126.2(7) 26_557 . . 28 ?
C1 C2 C1 C1 63.1(4) 26_557 . . 27 ?
C1 C2 C1 C1 63.1(4) 3_557 . . 28 ?
C1 C2 C1 C1 -63.1(4) 28 . . 27 ?
C1 C2 C1 C1 -126.2(7) 28 . . 26_557 ?
C1 C2 C1 C1 -63.1(4) 3_557 . . 26_557 ?
C1 C2 C1 C1 0.000(2) 3_557 . . 27 ?

_shelx_res_file                  
;
TITL 401k_cubic_rt_a.res in Pm-3m
    401k_cubic_rt.res
    created by SHELXL-2018/3 at 11:51:48 on 08-Jan-2025
REM Old TITL 401k_cubic_rt in Pm-3m
REM SHELXT solution in Pm-3m: R1 0.099, Rweak 0.111, Alpha 0.020
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Formula found by SHELXT: C8 N7 Br3
CELL 0.71073 6.9822 6.9822 6.9822 90 90 90
ZERR 1 0.0004 0.0004 0.0004 0 0 0
LATT 1
SYMM -X,-Y,+Z
SYMM -X,+Y,-Z
SYMM +X,-Y,-Z
SYMM +Z,+X,+Y
SYMM +Z,-X,-Y
SYMM -Z,-X,+Y
SYMM -Z,+X,-Y
SYMM +Y,+Z,+X
SYMM -Y,+Z,-X
SYMM +Y,-Z,-X
SYMM -Y,-Z,+X
SYMM +Y,+X,-Z
SYMM -Y,-X,-Z
SYMM +Y,-X,+Z
SYMM -Y,+X,+Z
SYMM +X,+Z,-Y
SYMM -X,+Z,+Y
SYMM -X,-Z,-Y
SYMM +X,-Z,+Y
SYMM +Z,+Y,-X
SYMM +Z,-Y,+X
SYMM -Z,+Y,+X
SYMM -Z,-Y,-X
SFAC Br C N
UNIT 3 12.46 1

L.S. 4
PLAN  5
SIZE 0.16 0.21 0.22
TEMP 127.85
CONF
list 4
MORE -1
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\401k_cubic_rt.hkl">
REM </olex2.extras>

WGHT    0.057200    0.200600
FVAR       1.24898
BR01  1    0.500000    0.500000    1.000000    10.06250    0.15614    0.15614 =
         0.15601    0.00000    0.00000    0.00000
N1    3    0.500000    0.500000    0.500000    10.02083    0.16562    0.16562 =
         0.16562    0.00000    0.00000    0.00000
C2    2    0.000000    0.253304    1.000000     0.11518    0.13485    0.07813 =
         0.13485    0.00000    0.00000    0.00000
C1    2    0.138244    0.138244    0.861756     0.14432    0.13420    0.13420 =
         0.13420    0.00309    0.00309   -0.00309
HKLF 4




REM  401k_cubic_rt_a.res in Pm-3m
REM wR2 = 0.1422, GooF = S = 1.070, Restrained GooF = 1.070 for all data
REM R1 = 0.0404 for 70 Fo > 4sig(Fo) and 0.0657 for all 134 data
REM 12 parameters refined using 0 restraints

END

WGHT      0.0570      0.2007

REM Highest difference peak  0.158,  deepest hole -0.224,  1-sigma level  0.065
Q1    1   0.0946  0.3829  1.0618  11.00000  0.05    0.16
Q2    1   0.1690  0.1690  1.0000  10.25000  0.05    0.09
Q3    1   0.3343  0.3343  1.0000  10.25000  0.05    0.07
Q4    1   0.3882  0.5000  1.1148  10.50000  0.05    0.06
Q5    1   0.5000  0.2394  1.0000  10.25000  0.05    0.06
;
_shelx_res_checksum              87425
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.657
_oxdiff_exptl_absorpt_empirical_full_min 0.723
####################################################################### 
# 
# 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_382k_rt1_inv
_database_code_depnum_ccdc_archive 'CCDC 2424526'
loop_
_audit_author_name
_audit_author_address
'Ryo Tsunashima'
;yamaguchi
Japan
;
_audit_update_record             
;
2025-02-17 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT971_382k_rt1_inv        
;
PROBLEM: Check Calcd Resid. Dens.  0.28Ang From Br2             2.52 eA-3
RESPONSE: due to disorder of the Br ion
;
# Added during the CSD deposition process: Monday 17 February 2025 06:15 AM
# end Validation Reply Form

_audit_creation_date             2025-01-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(Br), C6 H14 N3 P, H4 N'
_chemical_formula_sum            'C6 H18 Br3 N4 P'
_chemical_formula_weight         416.94
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H18N3Br3P
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'
N N 0.0061 0.0033 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   13.8322(8)
_cell_length_b                   9.9354(7)
_cell_length_c                   9.7055(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1333.81(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2159
_cell_measurement_temperature    382
_cell_measurement_theta_max      26.0390
_cell_measurement_theta_min      2.9150
_shelx_estimated_absorpt_T_max   0.305
_shelx_estimated_absorpt_T_min   0.208
_exptl_absorpt_coefficient_mu    9.167
_exptl_absorpt_correction_T_max  0.240
_exptl_absorpt_correction_T_min  0.106
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.076
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
12 -4 -7 0.0510
-5 7 -15 0.0715
-12 2 10 0.0792
-2 -5 18 0.0675
8 -3 -15 0.0847
-10 -10 1 0.0897
-6 5 16 0.0501
8 11 2 0.0420

_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
12.2883 -3.5274 -6.9809 -0.3028 0.3573 0.8835
-4.5357 7.3716 -15.2854 0.6142 -0.7163 0.3312
-11.6974 2.3814 9.5187 0.2074 -0.2461 -0.9468
-1.6195 -5.3061 17.9034 -0.4379 0.5085 -0.7414
7.8850 -2.8201 -15.4260 -0.1893 -0.1654 0.9679
-9.6027 -9.9610 0.8821 -0.6459 -0.5510 -0.5284
-6.0489 5.2076 15.9028 0.3444 0.2979 -0.8903
8.4807 10.9006 2.0325 0.7081 0.6048 0.3645

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.789
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5572
_diffrn_reflns_point_group_measured_fraction_full 0.766
_diffrn_reflns_point_group_measured_fraction_max 0.579
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.584
_diffrn_reflns_theta_min         2.934
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      382
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.789
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  11.00   0.25    2.20    --   -5.68 -59.00  26.00  300
  2  ω    -16.00  39.00   0.25    2.20    --    6.15 -99.00   0.00  220
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0066044498
_diffrn_orient_matrix_UB_12      0.0708513981
_diffrn_orient_matrix_UB_13      -0.0040553171
_diffrn_orient_matrix_UB_21      0.0517739282
_diffrn_orient_matrix_UB_22      0.0085582234
_diffrn_orient_matrix_UB_23      0.0356244016
_diffrn_orient_matrix_UB_31      0.0512061300
_diffrn_orient_matrix_UB_32      0.0004374725
_diffrn_orient_matrix_UB_33      -0.0366492789
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.391
_reflns_Friedel_fraction_full    0.507
_reflns_Friedel_fraction_max     0.344
_reflns_number_gt                1723
_reflns_number_total             2368
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         2.596
_refine_diff_density_min         -1.127
_refine_diff_density_rms         0.377
_refine_ls_abs_structure_details 
;
 Flack x determined using 457 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2368
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.1106
_refine_ls_R_factor_gt           0.0870
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1440P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1889
_refine_ls_wR_factor_ref         0.2076
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All Br(H,H,H,H) groups
2. Restrained distances
 N1-H1E = N1-H1D = N1-H1F = N1-H1C
 1.03 with sigma of 0.02
 H1E-H1D = H1E-H1F = H1E-H1C = H1D-H1F = H1D-H1C = H1F-H1C
 1.75 with sigma of 0.04
3. Others
 Sof(Br2A)=1-FVAR(1)
 Sof(Br2)=FVAR(1)
 Fixed Sof: Br3(0.75) Br4(0.25)
4.a Ternary CH refined with riding coordinates:
 N3(H3), N4(H4)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C3(H3A,H3B), C5(H5A,H5B), C2(H2A,H2B), C4(H4A,H4B), C1(H1A,H1B)
;
_atom_sites_solution_hydrogens   mixed
_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 0.74616(14) 0.49312(18) 0.6826(4) 0.0745(7) Uani 1 1 d . . . . .
Br2 Br 0.501(3) 0.763(5) 0.461(2) 0.089(10) Uani 0.12(3) 1 d . . P A -1
P1 P 0.5686(3) 0.0875(5) 0.4435(8) 0.0912(17) Uani 1 1 d . . . . .
N2 N 0.4271(9) 0.2379(13) 0.3085(14) 0.057(3) Uani 1 1 d . . . . .
N1 N 0.2345(11) 0.7203(17) 0.470(2) 0.087(5) Uani 1 1 d D . . . .
N3 N 0.5641(8) 0.3645(12) 0.4283(15) 0.061(3) Uani 1 1 d . . . . .
H3 H 0.604188 0.445211 0.418250 0.074 Uiso 1 1 calc R U . . .
C6 C 0.5066(11) 0.3819(18) 0.553(2) 0.068(5) Uani 1 1 d . . . . .
H6A H 0.469143 0.464188 0.546684 0.081 Uiso 1 1 calc R U . . .
H6B H 0.549014 0.389009 0.632348 0.081 Uiso 1 1 calc R U . . .
N4 N 0.4397(11) 0.2633(15) 0.5709(14) 0.065(3) Uani 1 1 d . . . . .
H4 H 0.399604 0.278437 0.652698 0.078 Uiso 1 1 calc R U . . .
C3 C 0.4914(12) 0.134(2) 0.5869(19) 0.072(5) Uani 1 1 d . . . . .
H3A H 0.443906 0.062794 0.600152 0.086 Uiso 1 1 calc R U . . .
H3B H 0.530551 0.137885 0.669686 0.086 Uiso 1 1 calc R U . . .
C5 C 0.3720(9) 0.2555(16) 0.441(2) 0.068(4) Uani 1 1 d . . . . .
H5A H 0.327662 0.180571 0.452213 0.081 Uiso 1 1 calc R U . . .
H5B H 0.333858 0.337265 0.435683 0.081 Uiso 1 1 calc R U . . .
C2 C 0.6291(9) 0.2496(16) 0.432(2) 0.067(4) Uani 1 1 d . . . . .
H2A H 0.671651 0.259162 0.511317 0.080 Uiso 1 1 calc R U . . .
H2B H 0.668975 0.250656 0.350292 0.080 Uiso 1 1 calc R U . . .
C4 C 0.4968(10) 0.3598(19) 0.3052(18) 0.062(4) Uani 1 1 d . . . . .
H4A H 0.535119 0.355741 0.221625 0.075 Uiso 1 1 calc R U . . .
H4B H 0.459124 0.442079 0.302464 0.075 Uiso 1 1 calc R U . . .
C1 C 0.4828(15) 0.113(2) 0.315(2) 0.086(6) Uani 1 1 d . . . . .
H1A H 0.515752 0.103288 0.226882 0.103 Uiso 1 1 calc R U . . .
H1B H 0.436695 0.039410 0.320639 0.103 Uiso 1 1 calc R U . . .
Br3 Br 0.2784(3) 0.4664(3) 0.7226(5) 0.0527(6) Uani 0.75 1 d . . P B -1
H1C H 0.303(4) 0.714(10) 0.425(10) 0.063 Uiso 1 1 d D U . . .
H1D H 0.181(5) 0.712(10) 0.394(8) 0.063 Uiso 1 1 d D U . . .
H1E H 0.227(7) 0.816(5) 0.517(10) 0.063 Uiso 1 1 d D U . . .
H1F H 0.227(7) 0.646(8) 0.546(8) 0.063 Uiso 1 1 d D U . . .
Br4 Br 0.2495(10) 0.483(2) 0.706(2) 0.102(7) Uani 0.25 1 d . . P C -2
Br2A Br 0.4869(2) 0.7195(7) 0.4277(5) 0.0656(17) Uani 0.88(3) 1 d . . P A -2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0680(10) 0.0741(10) 0.0813(14) -0.0054(9) 0.0068(9) 0.0006(7)
Br2 0.17(3) 0.055(14) 0.041(13) -0.016(8) -0.032(12) -0.022(11)
P1 0.081(3) 0.083(3) 0.110(4) 0.002(3) -0.017(3) 0.010(2)
N2 0.044(6) 0.068(7) 0.060(8) 0.015(6) -0.001(5) 0.006(5)
N1 0.087(10) 0.084(10) 0.090(13) 0.017(9) -0.008(8) 0.007(7)
N3 0.061(6) 0.057(6) 0.066(8) -0.005(6) -0.007(7) -0.012(5)
C6 0.072(9) 0.050(8) 0.081(13) -0.020(8) 0.001(8) -0.004(6)
N4 0.063(8) 0.089(9) 0.042(7) -0.010(6) 0.008(6) 0.009(6)
C3 0.090(11) 0.075(11) 0.051(10) 0.028(8) 0.001(7) -0.007(8)
C5 0.042(5) 0.073(9) 0.089(11) 0.014(9) -0.013(8) 0.004(6)
C2 0.044(5) 0.086(10) 0.071(9) -0.002(9) 0.002(8) -0.006(6)
C4 0.073(9) 0.070(11) 0.044(9) 0.018(8) -0.004(6) 0.010(6)
C1 0.124(15) 0.065(11) 0.069(13) -0.015(10) -0.005(11) -0.011(10)
Br3 0.0423(15) 0.0595(10) 0.0564(15) 0.0008(11) -0.0037(14) 0.0035(11)
Br4 0.063(8) 0.134(12) 0.108(14) 0.046(8) -0.020(8) -0.013(6)
Br2A 0.0757(17) 0.064(2) 0.057(2) 0.005(2) -0.0070(13) -0.0096(10)

_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 C3 1.81(2) . ?
P1 C2 1.818(16) . ?
P1 C1 1.74(2) . ?
N2 C5 1.51(2) . ?
N2 C4 1.55(2) . ?
N2 C1 1.46(3) . ?
N1 H1C 1.05(2) . ?
N1 H1D 1.05(2) . ?
N1 H1E 1.06(2) . ?
N1 H1F 1.04(2) . ?
N3 H3 0.9800 . ?
N3 C6 1.46(2) . ?
N3 C2 1.455(19) . ?
N3 C4 1.51(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 N4 1.51(2) . ?
N4 H4 0.9800 . ?
N4 C3 1.48(2) . ?
N4 C5 1.57(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 P1 C2 95.4(9) . . ?
C1 P1 C3 96.5(8) . . ?
C1 P1 C2 98.3(10) . . ?
C5 N2 C4 104.0(12) . . ?
C1 N2 C5 109.3(13) . . ?
C1 N2 C4 109.7(13) . . ?
H1C N1 H1D 109(4) . . ?
H1C N1 H1E 109(4) . . ?
H1C N1 H1F 110(4) . . ?
H1D N1 H1E 108(4) . . ?
H1D N1 H1F 112(4) . . ?
H1E N1 H1F 109(4) . . ?
C6 N3 H3 107.1 . . ?
C6 N3 C4 108.9(10) . . ?
C2 N3 H3 107.1 . . ?
C2 N3 C6 114.0(15) . . ?
C2 N3 C4 112.2(14) . . ?
C4 N3 H3 107.1 . . ?
N3 C6 H6A 109.7 . . ?
N3 C6 H6B 109.7 . . ?
N3 C6 N4 109.7(13) . . ?
H6A C6 H6B 108.2 . . ?
N4 C6 H6A 109.7 . . ?
N4 C6 H6B 109.7 . . ?
C6 N4 H4 108.7 . . ?
C6 N4 C5 108.3(14) . . ?
C3 N4 C6 113.3(14) . . ?
C3 N4 H4 108.7 . . ?
C3 N4 C5 109.2(13) . . ?
C5 N4 H4 108.7 . . ?
P1 C3 H3A 108.5 . . ?
P1 C3 H3B 108.5 . . ?
N4 C3 P1 115.0(11) . . ?
N4 C3 H3A 108.5 . . ?
N4 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
N2 C5 N4 112.9(9) . . ?
N2 C5 H5A 109.0 . . ?
N2 C5 H5B 109.0 . . ?
N4 C5 H5A 109.0 . . ?
N4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
P1 C2 H2A 108.7 . . ?
P1 C2 H2B 108.7 . . ?
N3 C2 P1 114.3(9) . . ?
N3 C2 H2A 108.7 . . ?
N3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
N2 C4 H4A 109.0 . . ?
N2 C4 H4B 109.0 . . ?
N3 C4 N2 113.0(12) . . ?
N3 C4 H4A 109.0 . . ?
N3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
P1 C1 H1A 107.2 . . ?
P1 C1 H1B 107.2 . . ?
N2 C1 P1 120.6(14) . . ?
N2 C1 H1A 107.2 . . ?
N2 C1 H1B 107.2 . . ?
H1A C1 H1B 106.8 . . ?

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
N3 C6 N4 C3 62(2) . . . . ?
N3 C6 N4 C5 -59.6(17) . . . . ?
C6 N3 C2 P1 64.2(18) . . . . ?
C6 N3 C4 N2 -63.4(15) . . . . ?
C6 N4 C3 P1 -59.7(19) . . . . ?
C6 N4 C5 N2 59.8(16) . . . . ?
C3 P1 C2 N3 -50.3(16) . . . . ?
C3 P1 C1 N2 49.9(18) . . . . ?
C3 N4 C5 N2 -63.9(16) . . . . ?
C5 N2 C4 N3 58.9(15) . . . . ?
C5 N2 C1 P1 -59(2) . . . . ?
C5 N4 C3 P1 61.0(16) . . . . ?
C2 P1 C3 N4 48.8(14) . . . . ?
C2 P1 C1 N2 -46.6(19) . . . . ?
C2 N3 C6 N4 -64.2(17) . . . . ?
C2 N3 C4 N2 63.8(16) . . . . ?
C4 N2 C5 N4 -56.9(14) . . . . ?
C4 N2 C1 P1 55(2) . . . . ?
C4 N3 C6 N4 61.8(17) . . . . ?
C4 N3 C2 P1 -60.2(18) . . . . ?
C1 P1 C3 N4 -50.1(15) . . . . ?
C1 P1 C2 N3 47.1(18) . . . . ?
C1 N2 C5 N4 60.2(17) . . . . ?
C1 N2 C4 N3 -57.9(18) . . . . ?

_shelx_res_file                  
;
TITL 382k_rt1_inv_a.res in Pna2(1)
    382k_rt1_inv.res
    created by SHELXL-2018/3 at 13:51:59 on 08-Jan-2025
REM Old TITL 382k_RT1_inv in P2(1)cn
REM SHELXT solution in Pna2(1): R1 0.135, Rweak 0.048, Alpha 0.004
REM <I/s> 0.459 for 147 systematic absences, Orientation a'=c, b'=-b, c'=a
REM Flack x = 0.109 ( 0.025 ) from 468 Parsons' quotients
REM Formula found by SHELXT: C8 N3 Br3
CELL 0.71073 13.8322 9.9354 9.7055 90 90 90
ZERR 4 0.0008 0.0007 0.0008 0 0 0
LATT -1
SYMM -X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,+Z
SYMM 0.5-X,0.5+Y,0.5+Z
SFAC C H Br N P
UNIT 24 72 12 16 4
DFIX 1.03 N1 H1e N1 H1d N1 H1f N1 H1c
DANG 1.75 H1e H1d H1e H1f H1e H1c H1d H1f H1d H1c H1f H1c

L.S. 12
PLAN  7
SIZE 0.17 0.22 0.25
TEMP 107
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\382k_RT1_inv.hkl">
REM </olex2.extras>

WGHT    0.144000
FVAR       0.23852   0.11900
BR1   3    0.746158    0.493122    0.682557    11.00000    0.06795    0.07413 =
         0.08130   -0.00544    0.00679    0.00065
PART -1
BR2   3    0.500946    0.763068    0.460616    21.00000    0.16933    0.05504 =
         0.04141   -0.01557   -0.03221   -0.02178

PART 0
P1    5    0.568580    0.087543    0.443502    11.00000    0.08102    0.08264 =
         0.10993    0.00229   -0.01660    0.00968
N2    4    0.427083    0.237901    0.308512    11.00000    0.04449    0.06763 =
         0.06038    0.01548   -0.00065    0.00579

N1    4    0.234480    0.720261    0.470485    11.00000    0.08727    0.08366 =
         0.08986    0.01658   -0.00842    0.00679
N3    4    0.564050    0.364527    0.428324    11.00000    0.06088    0.05698 =
         0.06627   -0.00481   -0.00657   -0.01205
AFIX  13
H3    2    0.604188    0.445211    0.418250    11.00000   -1.20000
AFIX   0
C6    1    0.506605    0.381894    0.553085    11.00000    0.07196    0.04978 =
         0.08138   -0.01958    0.00128   -0.00444
AFIX  23
H6A   2    0.469143    0.464188    0.546684    11.00000   -1.20000
H6B   2    0.549014    0.389009    0.632348    11.00000   -1.20000
AFIX   0
N4    4    0.439655    0.263347    0.570851    11.00000    0.06288    0.08921 =
         0.04213   -0.01019    0.00837    0.00870
AFIX  13
H4    2    0.399604    0.278437    0.652698    11.00000   -1.20000
AFIX   0
C3    1    0.491355    0.133514    0.586933    11.00000    0.08963    0.07495 =
         0.05110    0.02796    0.00123   -0.00682
AFIX  23
H3A   2    0.443906    0.062794    0.600152    11.00000   -1.20000
H3B   2    0.530551    0.137885    0.669686    11.00000   -1.20000
AFIX   0
C5    1    0.371961    0.255475    0.441118    11.00000    0.04212    0.07266 =
         0.08876    0.01394   -0.01285    0.00386
AFIX  23
H5A   2    0.327662    0.180571    0.452213    11.00000   -1.20000
H5B   2    0.333858    0.337265    0.435683    11.00000   -1.20000
AFIX   0
C2    1    0.629093    0.249568    0.432492    11.00000    0.04378    0.08595 =
         0.07110   -0.00217    0.00167   -0.00633
AFIX  23
H2A   2    0.671651    0.259162    0.511317    11.00000   -1.20000
H2B   2    0.668975    0.250656    0.350292    11.00000   -1.20000
AFIX   0
C4    1    0.496794    0.359774    0.305221    11.00000    0.07284    0.06992 =
         0.04386    0.01792   -0.00400    0.00983
AFIX  23
H4A   2    0.535119    0.355741    0.221625    11.00000   -1.20000
H4B   2    0.459124    0.442079    0.302464    11.00000   -1.20000
AFIX   0
C1    1    0.482753    0.112788    0.314532    11.00000    0.12401    0.06485 =
         0.06949   -0.01470   -0.00478   -0.01086
AFIX  23
H1A   2    0.515752    0.103288    0.226882    11.00000   -1.20000
H1B   2    0.436695    0.039410    0.320639    11.00000   -1.20000
AFIX   0

PART -1
BR3   3    0.278375    0.466373    0.722588    10.75000    0.04225    0.05951 =
         0.05639    0.00082   -0.00373    0.00354
PART 0
H1C   2    0.303006    0.713650    0.424984    11.00000   -1.20000
H1D   2    0.181165    0.712132    0.393791    11.00000   -1.20000
H1E   2    0.227034    0.816140    0.516966    11.00000   -1.20000
H1F   2    0.227060    0.646451    0.546290    11.00000   -1.20000

PART -2
BR4   3    0.249523    0.482688    0.705682    10.25000    0.06281    0.13418 =
         0.10792    0.04591   -0.02041   -0.01266

BR2A  3    0.486943    0.719516    0.427663   -21.00000    0.07573    0.06389 =
         0.05703    0.00515   -0.00697   -0.00955
HKLF 4




REM  382k_rt1_inv_a.res in Pna2(1)
REM wR2 = 0.2076, GooF = S = 1.023, Restrained GooF = 1.022 for all data
REM R1 = 0.0870 for 1723 Fo > 4sig(Fo) and 0.1106 for all 2368 data
REM 158 parameters refined using 11 restraints

END

WGHT      0.1275      0.0000

REM Highest difference peak  2.596,  deepest hole -1.127,  1-sigma level  0.377
Q1    1   0.2528  0.7576  0.4395  11.00000  0.05    0.98
Q2    1   0.5684  0.2371  0.6120  11.00000  0.05    0.84
Q3    1   0.5846  0.2470  0.2969  11.00000  0.05    0.72
Q4    1   0.5121  0.2925  0.6327  11.00000  0.05    0.63
Q5    1   0.4918  0.3612  0.5845  11.00000  0.05    0.58
Q6    1   0.4176  0.3685  0.4612  11.00000  0.05    0.58
Q7    1   0.5137  0.1279  0.5639  11.00000  0.05    0.55
;
_shelx_res_checksum              33672
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.871
_oxdiff_exptl_absorpt_empirical_full_min 0.584
####################################################################### 
# 
# 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_p-br_354k
_database_code_depnum_ccdc_archive 'CCDC 2424524'
loop_
_audit_author_name
_audit_author_address
'Ryo Tsunashima'
;yamaguchi
Japan
;
_audit_update_record             
;
2025-02-17 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;
_audit_creation_date             2025-01-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(Br), C6 H14 N3 P, H4 N'
_chemical_formula_sum            'C6 H18 Br3 N4 P'
_chemical_formula_weight         416.94
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H18N3Br3P
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'
N N 0.0061 0.0033 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   13.8180(5)
_cell_length_b                   9.9528(4)
_cell_length_c                   9.6881(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1332.38(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3509
_cell_measurement_temperature    354
_cell_measurement_theta_max      29.3700
_cell_measurement_theta_min      2.9160
_shelx_estimated_absorpt_T_max   0.340
_shelx_estimated_absorpt_T_min   0.261
_exptl_absorpt_coefficient_mu    9.177
_exptl_absorpt_correction_T_max  0.31248
_exptl_absorpt_correction_T_min  0.29786
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.079
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       sphere
_exptl_crystal_F_000             808
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
17 7 -1 0.0908
9 9 -8 0.0917
-12 1 -11 0.0817
-17 -6 -2 0.0819
8 -4 12 0.0485
16 -3 8 0.0793
-3 10 9 0.0736
-14 10 1 0.0869
-16 4 -6 0.0911
-9 -4 -11 0.0846
5 -11 -8 0.0811

_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_crystal_size_rad          0.092
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
16.5830 7.3441 -0.5639 0.5876 -0.5543 0.5895
9.3614 8.8724 -8.3079 0.7242 -0.6860 -0.0701
-11.9142 1.3083 -10.7256 0.1246 -0.1216 -0.9847
-17.2324 -6.3316 -1.6117 -0.5027 0.4734 -0.7234
7.6973 -3.8313 11.9770 -0.3284 0.3143 0.8907
15.6835 -2.5277 7.7114 -0.1742 -0.1800 0.9681
-2.5275 10.0202 9.3954 0.6300 0.6669 0.3979
-14.0053 9.6589 1.3048 0.6190 0.6519 -0.4380
-16.3368 4.4056 -6.0709 0.2924 0.3051 -0.9063
-9.4873 -4.3347 -11.1539 -0.2618 -0.2803 -0.9235
5.1205 -10.5563 -8.2512 -0.6662 -0.7045 -0.2446

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5119
_diffrn_reflns_point_group_measured_fraction_full 0.769
_diffrn_reflns_point_group_measured_fraction_max 0.758
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.934
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      354
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  11.00   0.25    2.20    --   -5.68 -59.00  26.00  300
  2  ω    -16.00  39.00   0.25    2.20    --    6.15 -99.00   0.00  220
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0038780000
_diffrn_orient_matrix_UB_12      0.0706956000
_diffrn_orient_matrix_UB_13      -0.0073005000
_diffrn_orient_matrix_UB_21      -0.0355875000
_diffrn_orient_matrix_UB_22      0.0088713000
_diffrn_orient_matrix_UB_23      0.0519490000
_diffrn_orient_matrix_UB_31      0.0367949000
_diffrn_orient_matrix_UB_32      0.0011024000
_diffrn_orient_matrix_UB_33      0.0510734000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.435
_reflns_Friedel_fraction_full    0.512
_reflns_Friedel_fraction_max     0.491
_reflns_number_gt                1929
_reflns_number_total             2067
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.756
_refine_diff_density_min         -0.799
_refine_diff_density_rms         0.114
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.013(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2067
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1157P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1367
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H,H,H) groups, All N(H) groups
2. Restrained distances
 N1-H1C = N1-H1D = N1-H1E = N1-H1F
 1.05 with sigma of 0.02
 H1C-H1D = H1C-H1E = H1C-H1F = H1D-H1E = H1D-H1F = H1F-H1E
 1.75 with sigma of 0.04
3.a Ternary CH refined with riding coordinates:
 N3(H3), N4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C3(H3A,H3B), C5(H5A,H5B), C2(H2A,H2B), C4(H4A,H4B), C1(H1A,H1B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.27718(7) 0.53495(10) 0.70946(15) 0.0498(3) Uani 1 1 d . . . . .
Br2 Br -0.01373(7) 0.21866(11) 0.41474(14) 0.0556(3) Uani 1 1 d . . . . .
Br3 Br 0.24619(9) -0.00685(11) 0.6665(2) 0.0575(3) Uani 1 1 d . . . . .
P1 P 0.56904(19) 0.9138(3) 0.4317(4) 0.0626(8) Uani 1 1 d . . . . .
N2 N 0.4274(6) 0.7613(9) 0.2947(9) 0.0430(18) Uani 1 1 d . . . . .
N3 N 0.5639(5) 0.6346(7) 0.4117(10) 0.0446(18) Uani 1 1 d . . . . .
H3 H 0.604119 0.554319 0.400109 0.054 Uiso 1 1 calc R U . . .
N1 N 0.2303(7) 0.2860(11) 0.4642(14) 0.062(3) Uani 1 1 d D . . . .
N4 N 0.4388(6) 0.7345(9) 0.5544(10) 0.047(2) Uani 1 1 d . . . . .
H4 H 0.398342 0.718704 0.635862 0.056 Uiso 1 1 calc R U . . .
C6 C 0.5080(7) 0.6167(12) 0.5394(13) 0.048(2) Uani 1 1 d . . . . .
H6A H 0.551329 0.613137 0.618055 0.058 Uiso 1 1 calc R U . . .
H6B H 0.471947 0.533198 0.535591 0.058 Uiso 1 1 calc R U . . .
C3 C 0.4923(8) 0.8652(13) 0.5747(15) 0.059(3) Uani 1 1 d . . . . .
H3A H 0.531820 0.857921 0.657042 0.071 Uiso 1 1 calc R U . . .
H3B H 0.445261 0.935931 0.590454 0.071 Uiso 1 1 calc R U . . .
C5 C 0.3730(6) 0.7430(11) 0.4287(15) 0.054(2) Uani 1 1 d . . . . .
H5A H 0.334783 0.661436 0.423035 0.064 Uiso 1 1 calc R U . . .
H5B H 0.328744 0.817698 0.440606 0.064 Uiso 1 1 calc R U . . .
C2 C 0.6305(6) 0.7522(11) 0.4205(15) 0.049(2) Uani 1 1 d . . . . .
H2A H 0.671964 0.752507 0.339712 0.059 Uiso 1 1 calc R U . . .
H2B H 0.671539 0.741569 0.500944 0.059 Uiso 1 1 calc R U . . .
C4 C 0.4949(7) 0.6415(11) 0.2862(11) 0.046(2) Uani 1 1 d . . . . .
H4A H 0.532778 0.647463 0.202181 0.055 Uiso 1 1 calc R U . . .
H4B H 0.456870 0.559686 0.281980 0.055 Uiso 1 1 calc R U . . .
C1 C 0.4815(9) 0.8852(13) 0.2944(15) 0.063(3) Uani 1 1 d . . . . .
H1A H 0.435347 0.958601 0.296413 0.075 Uiso 1 1 calc R U . . .
H1B H 0.515658 0.890807 0.207143 0.075 Uiso 1 1 calc R U . . .
H1C H 0.217(7) 0.313(12) 0.360(4) 0.075 Uiso 1 1 d D U . . .
H1D H 0.275(6) 0.355(8) 0.514(10) 0.075 Uiso 1 1 d D U . . .
H1E H 0.162(4) 0.282(10) 0.515(10) 0.075 Uiso 1 1 d D U . . .
H1F H 0.258(7) 0.187(4) 0.466(13) 0.075 Uiso 1 1 d D U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0425(5) 0.0463(5) 0.0607(6) -0.0019(5) 0.0020(4) -0.0023(4)
Br2 0.0608(6) 0.0506(6) 0.0553(6) 0.0053(6) -0.0051(6) -0.0077(4)
Br3 0.0500(5) 0.0522(6) 0.0703(8) -0.0076(5) 0.0047(5) 0.0006(4)
P1 0.0528(14) 0.0461(15) 0.089(2) 0.0001(14) -0.0091(16) -0.0078(11)
N2 0.037(4) 0.043(4) 0.049(5) -0.014(4) -0.003(3) -0.007(3)
N3 0.042(4) 0.031(3) 0.061(5) 0.003(4) -0.001(4) 0.010(3)
N1 0.060(5) 0.055(6) 0.073(7) -0.016(5) -0.007(5) -0.002(4)
N4 0.041(4) 0.049(5) 0.050(5) 0.000(4) 0.012(4) -0.010(3)
C6 0.052(5) 0.039(5) 0.054(7) 0.006(5) 0.003(4) -0.003(4)
C3 0.067(7) 0.043(6) 0.067(8) -0.016(6) 0.004(5) 0.000(4)
C5 0.033(4) 0.048(5) 0.080(7) -0.005(6) -0.002(5) -0.005(4)
C2 0.030(3) 0.052(5) 0.065(6) 0.008(6) -0.002(5) 0.000(4)
C4 0.063(6) 0.035(5) 0.040(6) -0.007(4) 0.004(4) -0.005(4)
C1 0.074(7) 0.046(6) 0.068(8) 0.025(6) -0.004(6) 0.009(5)

_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 C3 1.811(14) . ?
P1 C2 1.822(11) . ?
P1 C1 1.821(14) . ?
N2 C5 1.510(16) . ?
N2 C4 1.516(14) . ?
N2 C1 1.441(16) . ?
N3 H3 0.9800 . ?
N3 C6 1.469(15) . ?
N3 C2 1.492(12) . ?
N3 C4 1.546(14) . ?
N1 H1C 1.06(2) . ?
N1 H1D 1.04(2) . ?
N1 H1E 1.07(2) . ?
N1 H1F 1.06(2) . ?
N4 H4 0.9800 . ?
N4 C6 1.519(14) . ?
N4 C3 1.509(15) . ?
N4 C5 1.522(16) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 P1 C2 94.8(6) . . ?
C3 P1 C1 97.3(6) . . ?
C1 P1 C2 97.3(6) . . ?
C5 N2 C4 104.9(8) . . ?
C1 N2 C5 111.3(9) . . ?
C1 N2 C4 110.7(8) . . ?
C6 N3 H3 107.2 . . ?
C6 N3 C2 111.8(9) . . ?
C6 N3 C4 110.1(7) . . ?
C2 N3 H3 107.2 . . ?
C2 N3 C4 113.0(8) . . ?
C4 N3 H3 107.2 . . ?
H1C N1 H1D 112(4) . . ?
H1C N1 H1E 108(4) . . ?
H1C N1 H1F 108(4) . . ?
H1D N1 H1E 110(4) . . ?
H1D N1 H1F 113(4) . . ?
H1E N1 H1F 106(4) . . ?
C6 N4 H4 108.2 . . ?
C6 N4 C5 110.0(9) . . ?
C3 N4 H4 108.2 . . ?
C3 N4 C6 111.7(8) . . ?
C3 N4 C5 110.4(9) . . ?
C5 N4 H4 108.2 . . ?
N3 C6 N4 108.5(9) . . ?
N3 C6 H6A 110.0 . . ?
N3 C6 H6B 110.0 . . ?
N4 C6 H6A 110.0 . . ?
N4 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
P1 C3 H3A 108.6 . . ?
P1 C3 H3B 108.6 . . ?
N4 C3 P1 114.7(9) . . ?
N4 C3 H3A 108.6 . . ?
N4 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
N2 C5 N4 113.4(7) . . ?
N2 C5 H5A 108.9 . . ?
N2 C5 H5B 108.9 . . ?
N4 C5 H5A 108.9 . . ?
N4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
P1 C2 H2A 108.7 . . ?
P1 C2 H2B 108.7 . . ?
N3 C2 P1 114.1(6) . . ?
N3 C2 H2A 108.7 . . ?
N3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
N2 C4 N3 111.8(8) . . ?
N2 C4 H4A 109.3 . . ?
N2 C4 H4B 109.3 . . ?
N3 C4 H4A 109.3 . . ?
N3 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
P1 C1 H1A 107.7 . . ?
P1 C1 H1B 107.7 . . ?
N2 C1 P1 118.5(8) . . ?
N2 C1 H1A 107.7 . . ?
N2 C1 H1B 107.7 . . ?
H1A C1 H1B 107.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N3 C2 P1 -66.3(11) . . . . ?
C6 N3 C4 N2 62.6(10) . . . . ?
C6 N4 C3 P1 62.5(12) . . . . ?
C6 N4 C5 N2 -59.5(11) . . . . ?
C3 P1 C2 N3 51.9(10) . . . . ?
C3 P1 C1 N2 -47.0(11) . . . . ?
C3 N4 C6 N3 -65.2(13) . . . . ?
C3 N4 C5 N2 64.2(11) . . . . ?
C5 N2 C4 N3 -58.4(10) . . . . ?
C5 N2 C1 P1 56.6(12) . . . . ?
C5 N4 C6 N3 57.7(11) . . . . ?
C5 N4 C3 P1 -60.2(11) . . . . ?
C2 P1 C3 N4 -50.5(10) . . . . ?
C2 P1 C1 N2 48.8(11) . . . . ?
C2 N3 C6 N4 67.2(10) . . . . ?
C2 N3 C4 N2 -63.2(11) . . . . ?
C4 N2 C5 N4 58.0(10) . . . . ?
C4 N2 C1 P1 -59.7(13) . . . . ?
C4 N3 C6 N4 -59.2(10) . . . . ?
C4 N3 C2 P1 58.5(11) . . . . ?
C1 P1 C3 N4 47.5(10) . . . . ?
C1 P1 C2 N3 -46.2(11) . . . . ?
C1 N2 C5 N4 -61.8(11) . . . . ?
C1 N2 C4 N3 61.7(12) . . . . ?

_shelx_res_file                  
;
TITL 360_re1_a.res in Pna2(1)
    p-br_354k.res
    created by SHELXL-2018/3 at 11:47:11 on 08-Jan-2025
REM Old TITL 360_re1 in Pna2(1)
REM SHELXT solution in Pna2(1): R1 0.084, Rweak 0.016, Alpha 0.003
REM <I/s> 0.367 for 147 systematic absences, Orientation as input
REM Flack x = -0.060 ( 0.029 ) from 568 Parsons' quotients
REM Formula found by SHELXT: C7 N3 P Br3
CELL 0.71073 13.818 9.9528 9.6881 90 90 90
ZERR 4 0.0005 0.0004 0.0004 0 0 0
LATT -1
SYMM -X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,+Z
SYMM 0.5-X,0.5+Y,0.5+Z
SFAC C H Br N P
UNIT 24 72 12 16 4
DFIX 1.05 N1 H1c N1 H1d N1 H1e N1 H1f
DANG 1.75 H1c H1d H1c H1e H1c H1f H1d H1e H1d H1f H1f H1e

L.S. 8
PLAN  7
SIZE 0.15 0.19 0.2
TEMP 80.85
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\p-Br_354K.hkl">
REM </olex2.extras>

WGHT    0.115700
FVAR       0.28042
BR1   3    0.277181    0.534948    0.709460    11.00000    0.04252    0.04627 =
         0.06068   -0.00186    0.00196   -0.00228
BR2   3   -0.013735    0.218659    0.414739    11.00000    0.06076    0.05058 =
         0.05534    0.00532   -0.00514   -0.00767
BR3   3    0.246195   -0.006853    0.666503    11.00000    0.04995    0.05222 =
         0.07035   -0.00763    0.00467    0.00064
P1    5    0.569044    0.913793    0.431716    11.00000    0.05276    0.04606 =
         0.08884    0.00011   -0.00909   -0.00784
N2    4    0.427404    0.761299    0.294718    11.00000    0.03674    0.04330 =
         0.04911   -0.01443   -0.00335   -0.00651
N3    4    0.563866    0.634598    0.411699    11.00000    0.04219    0.03105 =
         0.06055    0.00258   -0.00081    0.00950
AFIX  13
H3    2    0.604119    0.554319    0.400109    11.00000   -1.20000
AFIX   0

N1    4    0.230265    0.285993    0.464196    11.00000    0.05973    0.05482 =
         0.07271   -0.01581   -0.00745   -0.00201
N4    4    0.438815    0.734483    0.554393    11.00000    0.04123    0.04931 =
         0.04998    0.00003    0.01232   -0.01039
AFIX  13
H4    2    0.398342    0.718704    0.635862    11.00000   -1.20000
AFIX   0
C6    1    0.507993    0.616747    0.539376    11.00000    0.05212    0.03913 =
         0.05378    0.00573    0.00313   -0.00293
AFIX  23
H6A   2    0.551329    0.613137    0.618055    11.00000   -1.20000
H6B   2    0.471947    0.533198    0.535591    11.00000   -1.20000
AFIX   0
C3    1    0.492253    0.865176    0.574675    11.00000    0.06668    0.04312 =
         0.06670   -0.01604    0.00360   -0.00040
AFIX  23
H3A   2    0.531820    0.857921    0.657042    11.00000   -1.20000
H3B   2    0.445261    0.935931    0.590454    11.00000   -1.20000
AFIX   0
C5    1    0.373028    0.742978    0.428656    11.00000    0.03312    0.04792 =
         0.07958   -0.00510   -0.00244   -0.00487
AFIX  23
H5A   2    0.334783    0.661436    0.423035    11.00000   -1.20000
H5B   2    0.328744    0.817698    0.440606    11.00000   -1.20000
AFIX   0
C2    1    0.630477    0.752220    0.420478    11.00000    0.02991    0.05250 =
         0.06547    0.00762   -0.00174    0.00030
AFIX  23
H2A   2    0.671964    0.752507    0.339712    11.00000   -1.20000
H2B   2    0.671539    0.741569    0.500944    11.00000   -1.20000
AFIX   0
C4    1    0.494875    0.641523    0.286233    11.00000    0.06327    0.03532 =
         0.03960   -0.00729    0.00437   -0.00536
AFIX  23
H4A   2    0.532778    0.647463    0.202181    11.00000   -1.20000
H4B   2    0.456870    0.559686    0.281980    11.00000   -1.20000
AFIX   0
C1    1    0.481468    0.885153    0.294394    11.00000    0.07433    0.04584 =
         0.06797    0.02539   -0.00414    0.00900
AFIX  23
H1A   2    0.435347    0.958601    0.296413    11.00000   -1.20000
H1B   2    0.515658    0.890807    0.207143    11.00000   -1.20000
AFIX   0
H1C   2    0.217213    0.313032    0.359745    11.00000   -1.20000
H1D   2    0.275408    0.354675    0.513902    11.00000   -1.20000
H1E   2    0.161780    0.281930    0.515380    11.00000   -1.20000
H1F   2    0.258136    0.186522    0.466079    11.00000   -1.20000
HKLF 4




REM  360_re1_a.res in Pna2(1)
REM wR2 = 0.1367, GooF = S = 1.047, Restrained GooF = 1.045 for all data
REM R1 = 0.0499 for 1929 Fo > 4sig(Fo) and 0.0525 for all 2067 data
REM 139 parameters refined using 11 restraints

END

WGHT      0.1157      0.0000

REM Highest difference peak  0.756,  deepest hole -0.799,  1-sigma level  0.114
Q1    1  -0.0130  0.2666  0.3443  11.00000  0.05    0.76
Q2    1   0.2351  0.5003  0.7386  11.00000  0.05    0.72
Q3    1   0.2422  0.5724  0.6653  11.00000  0.05    0.71
Q4    1  -0.0173  0.2621  0.4896  11.00000  0.05    0.68
Q5    1   0.2644  0.5007  0.6212  11.00000  0.05    0.63
Q6    1   0.2426 -0.0613  0.7429  11.00000  0.05    0.55
Q7    1  -0.0125  0.1459  0.5079  11.00000  0.05    0.48
;
_shelx_res_checksum              16973
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.409
_oxdiff_exptl_absorpt_empirical_full_min 0.745
####################################################################### 
# 
# 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_364k_rt
_database_code_depnum_ccdc_archive 'CCDC 2424527'
loop_
_audit_author_name
_audit_author_address
'Ryo Tsunashima'
;yamaguchi
Japan
;
_audit_update_record             
;
2025-02-17 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;
_audit_creation_date             2025-01-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(Br), C6 H14 N3 P, H4 N'
_chemical_formula_sum            'C6 H18 Br3 N4 P'
_chemical_formula_weight         416.94
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H18N3Br3P
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'
N N 0.0061 0.0033 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   13.8355(5)
_cell_length_b                   9.9594(4)
_cell_length_c                   9.7006(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1336.68(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3280
_cell_measurement_temperature    364
_cell_measurement_theta_max      28.4400
_cell_measurement_theta_min      2.9280
_shelx_estimated_absorpt_T_max   0.322
_shelx_estimated_absorpt_T_min   0.238
_exptl_absorpt_coefficient_mu    9.148
_exptl_absorpt_correction_T_max  0.231
_exptl_absorpt_correction_T_min  0.079
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.072
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
9 -4 12 0.0602
16 8 0 0.1039
-12 2 -11 0.0821
-16 -8 -1 0.0859
16 -2 8 0.0780
-4 9 10 0.0763
-14 9 3 0.0875
-16 3 -7 0.0798
-10 -3 -11 0.0857
9 -10 -7 0.1047
11 10 -6 0.0939

_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
8.5917 -4.0767 11.6166 -0.3373 0.2613 0.9044
15.9192 8.1121 0.2236 0.6336 -0.4831 0.6043
-11.8228 1.7505 -10.7378 0.1541 -0.1213 -0.9806
-16.3071 -7.6072 -1.1843 -0.5926 0.4515 -0.6671
15.5002 -1.6374 8.1385 -0.1133 -0.1433 0.9832
-4.1828 9.2448 9.8635 0.5666 0.7418 0.3588
-14.0961 9.1612 3.1093 0.5702 0.7431 -0.3502
-16.4651 3.2193 -6.6176 0.2104 0.2705 -0.9394
-10.4578 -3.0293 -11.1545 -0.1753 -0.2335 -0.9564
9.4628 -9.8424 -7.1457 -0.6076 -0.7938 -0.0267
10.6322 9.9950 -6.0741 0.7909 -0.6052 0.0906

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.787
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5578
_diffrn_reflns_point_group_measured_fraction_full 0.769
_diffrn_reflns_point_group_measured_fraction_max 0.579
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.576
_diffrn_reflns_theta_min         2.931
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      364
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.787
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  11.00   0.25    2.20    --   -5.68 -59.00  26.00  300
  2  ω    -16.00  39.00   0.25    2.20    --    6.15 -99.00   0.00  220
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0038967000
_diffrn_orient_matrix_UB_12      0.0706546000
_diffrn_orient_matrix_UB_13      -0.0071220000
_diffrn_orient_matrix_UB_21      -0.0355573000
_diffrn_orient_matrix_UB_22      0.0087976000
_diffrn_orient_matrix_UB_23      0.0518775000
_diffrn_orient_matrix_UB_31      0.0367410000
_diffrn_orient_matrix_UB_32      0.0009882000
_diffrn_orient_matrix_UB_33      0.0510287000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.395
_reflns_Friedel_fraction_full    0.515
_reflns_Friedel_fraction_max     0.346
_reflns_number_gt                2108
_reflns_number_total             2370
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.042
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.135
_refine_ls_abs_structure_details 
;
 Flack x determined using 554 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2370
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0743P)²+0.7164P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1137
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H,H,H) groups, All N(H) groups
2. Restrained distances
 N1-H1C = N1-H1D = N1-H1E = N1-H1F
 1.04 with sigma of 0.02
 H1C-H1D = H1C-H1E = H1C-H1F = H1D-H1E = H1D-H1F = H1E-H1F
 1.75 with sigma of 0.04
3.a Ternary CH refined with riding coordinates:
 N4(H4), N3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C4(H4A,H4B), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C1(H1A,H1B)
;
_atom_sites_solution_hydrogens   mixed
_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
Br01 Br 0.27686(6) 0.53447(9) 0.70923(13) 0.0547(2) Uani 1 1 d . . . . .
Br02 Br -0.01345(6) 0.21893(9) 0.41490(12) 0.0608(3) Uani 1 1 d . . . . .
Br03 Br 0.24608(7) -0.00680(9) 0.66677(18) 0.0628(3) Uani 1 1 d . . . . .
P1 P 0.56881(18) 0.9131(3) 0.4319(4) 0.0694(7) Uani 1 1 d . . . . .
N2 N 0.4280(5) 0.7619(7) 0.2942(8) 0.0453(15) Uani 1 1 d . . . . .
N1 N 0.2306(6) 0.2839(9) 0.4624(12) 0.069(2) Uani 1 1 d D . . . .
N4 N 0.5639(4) 0.6345(6) 0.4115(9) 0.0493(15) Uani 1 1 d . . . . .
H4 H 0.604331 0.554537 0.399849 0.059 Uiso 1 1 calc R U . . .
N3 N 0.4386(6) 0.7360(8) 0.5547(8) 0.0525(18) Uani 1 1 d . . . . .
H3 H 0.397907 0.720885 0.635880 0.063 Uiso 1 1 calc R U . . .
C6 C 0.5081(6) 0.6166(10) 0.5397(12) 0.056(2) Uani 1 1 d . . . . .
H6A H 0.551421 0.612743 0.618172 0.067 Uiso 1 1 calc R U . . .
H6B H 0.471825 0.533256 0.535948 0.067 Uiso 1 1 calc R U . . .
C4 C 0.3735(5) 0.7433(9) 0.4277(13) 0.058(2) Uani 1 1 d . . . . .
H4A H 0.335846 0.661347 0.421984 0.069 Uiso 1 1 calc R U . . .
H4B H 0.328655 0.817427 0.438946 0.069 Uiso 1 1 calc R U . . .
C2 C 0.4922(7) 0.8667(11) 0.5738(12) 0.063(3) Uani 1 1 d . . . . .
H2A H 0.531501 0.860093 0.656362 0.075 Uiso 1 1 calc R U . . .
H2B H 0.445373 0.937701 0.588584 0.075 Uiso 1 1 calc R U . . .
C3 C 0.6299(5) 0.7527(9) 0.4201(13) 0.0559(19) Uani 1 1 d . . . . .
H3A H 0.671132 0.753277 0.339227 0.067 Uiso 1 1 calc R U . . .
H3B H 0.671184 0.742090 0.500193 0.067 Uiso 1 1 calc R U . . .
C5 C 0.4966(6) 0.6421(10) 0.2871(10) 0.051(2) Uani 1 1 d . . . . .
H5A H 0.535050 0.648570 0.203742 0.061 Uiso 1 1 calc R U . . .
H5B H 0.458944 0.560091 0.281787 0.061 Uiso 1 1 calc R U . . .
C1 C 0.4826(8) 0.8855(11) 0.2960(13) 0.069(3) Uani 1 1 d . . . . .
H1A H 0.436639 0.959101 0.298407 0.083 Uiso 1 1 calc R U . . .
H1B H 0.516937 0.891908 0.209109 0.083 Uiso 1 1 calc R U . . .
H1C H 0.295(3) 0.237(8) 0.428(9) 0.083 Uiso 1 1 d D U . . .
H1D H 0.173(4) 0.217(6) 0.435(9) 0.083 Uiso 1 1 d D U . . .
H1E H 0.222(6) 0.371(5) 0.403(8) 0.083 Uiso 1 1 d D U . . .
H1F H 0.233(6) 0.299(9) 0.568(3) 0.083 Uiso 1 1 d D U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br01 0.0494(4) 0.0530(4) 0.0618(5) -0.0020(4) 0.0017(4) -0.0016(3)
Br02 0.0685(5) 0.0577(5) 0.0563(5) 0.0061(6) -0.0055(5) -0.0077(4)
Br03 0.0565(4) 0.0589(5) 0.0729(7) -0.0085(5) 0.0051(5) 0.0004(4)
P1 0.0619(13) 0.0547(13) 0.092(2) -0.0005(13) -0.0094(15) -0.0085(11)
N2 0.037(3) 0.050(4) 0.049(4) -0.015(3) -0.001(3) -0.007(3)
N1 0.068(5) 0.060(5) 0.078(6) -0.017(4) -0.009(4) -0.001(4)
N4 0.050(3) 0.038(3) 0.060(4) 0.003(3) 0.002(4) 0.012(2)
N3 0.050(4) 0.058(4) 0.050(4) 0.000(3) 0.015(3) -0.010(3)
C6 0.062(5) 0.039(4) 0.067(7) 0.012(4) -0.001(4) 0.003(3)
C4 0.036(3) 0.056(5) 0.082(7) -0.003(5) -0.004(4) -0.008(3)
C2 0.070(6) 0.051(5) 0.067(7) -0.020(5) -0.001(5) 0.002(4)
C3 0.038(3) 0.061(5) 0.068(6) 0.008(5) -0.001(5) 0.004(3)
C5 0.069(5) 0.042(5) 0.041(5) -0.010(4) 0.005(4) -0.002(3)
C1 0.089(7) 0.048(5) 0.072(7) 0.027(5) 0.003(5) 0.009(5)

_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 C2 1.798(12) . ?
P1 C3 1.812(9) . ?
P1 C1 1.799(13) . ?
N2 C4 1.510(14) . ?
N2 C5 1.526(12) . ?
N2 C1 1.444(13) . ?
N1 H1C 1.06(2) . ?
N1 H1D 1.07(2) . ?
N1 H1E 1.05(2) . ?
N1 H1F 1.03(2) . ?
N4 H4 0.9800 . ?
N4 C6 1.475(13) . ?
N4 C3 1.492(11) . ?
N4 C5 1.526(13) . ?
N3 H3 0.9800 . ?
N3 C6 1.536(12) . ?
N3 C4 1.528(14) . ?
N3 C2 1.509(12) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 P1 C3 95.5(5) . . ?
C2 P1 C1 97.5(5) . . ?
C1 P1 C3 97.4(5) . . ?
C4 N2 C5 104.7(7) . . ?
C1 N2 C4 110.8(7) . . ?
C1 N2 C5 110.0(7) . . ?
H1C N1 H1D 106(4) . . ?
H1C N1 H1E 107(4) . . ?
H1C N1 H1F 111(4) . . ?
H1D N1 H1E 107(4) . . ?
H1D N1 H1F 111(4) . . ?
H1E N1 H1F 116(4) . . ?
C6 N4 H4 107.3 . . ?
C6 N4 C3 111.7(8) . . ?
C6 N4 C5 110.7(6) . . ?
C3 N4 H4 107.3 . . ?
C3 N4 C5 112.3(7) . . ?
C5 N4 H4 107.3 . . ?
C6 N3 H3 108.4 . . ?
C4 N3 H3 108.4 . . ?
C4 N3 C6 109.2(8) . . ?
C2 N3 H3 108.4 . . ?
C2 N3 C6 111.9(7) . . ?
C2 N3 C4 110.4(8) . . ?
N4 C6 N3 108.3(7) . . ?
N4 C6 H6A 110.0 . . ?
N4 C6 H6B 110.0 . . ?
N3 C6 H6A 110.0 . . ?
N3 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
N2 C4 N3 113.7(5) . . ?
N2 C4 H4A 108.8 . . ?
N2 C4 H4B 108.8 . . ?
N3 C4 H4A 108.8 . . ?
N3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
P1 C2 H2A 108.6 . . ?
P1 C2 H2B 108.6 . . ?
N3 C2 P1 114.7(7) . . ?
N3 C2 H2A 108.6 . . ?
N3 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
P1 C3 H3A 108.7 . . ?
P1 C3 H3B 108.7 . . ?
N4 C3 P1 114.4(5) . . ?
N4 C3 H3A 108.7 . . ?
N4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
N2 C5 N4 112.5(7) . . ?
N2 C5 H5A 109.1 . . ?
N2 C5 H5B 109.1 . . ?
N4 C5 H5A 109.1 . . ?
N4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
P1 C1 H1A 107.5 . . ?
P1 C1 H1B 107.5 . . ?
N2 C1 P1 119.1(7) . . ?
N2 C1 H1A 107.5 . . ?
N2 C1 H1B 107.5 . . ?
H1A C1 H1B 107.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N4 C3 P1 -66.1(10) . . . . ?
C6 N4 C5 N2 62.1(9) . . . . ?
C6 N3 C4 N2 -60.1(9) . . . . ?
C6 N3 C2 P1 61.9(11) . . . . ?
C4 N2 C5 N4 -57.8(8) . . . . ?
C4 N2 C1 P1 56.5(11) . . . . ?
C4 N3 C6 N4 57.6(9) . . . . ?
C4 N3 C2 P1 -59.9(9) . . . . ?
C2 P1 C3 N4 51.8(9) . . . . ?
C2 P1 C1 N2 -47.8(9) . . . . ?
C2 N3 C6 N4 -64.8(11) . . . . ?
C2 N3 C4 N2 63.3(9) . . . . ?
C3 P1 C2 N3 -50.2(8) . . . . ?
C3 P1 C1 N2 48.8(10) . . . . ?
C3 N4 C6 N3 66.7(9) . . . . ?
C3 N4 C5 N2 -63.4(9) . . . . ?
C5 N2 C4 N3 58.0(8) . . . . ?
C5 N2 C1 P1 -58.8(11) . . . . ?
C5 N4 C6 N3 -59.1(9) . . . . ?
C5 N4 C3 P1 58.9(10) . . . . ?
C1 P1 C2 N3 48.0(8) . . . . ?
C1 P1 C3 N4 -46.6(9) . . . . ?
C1 N2 C4 N3 -60.5(9) . . . . ?
C1 N2 C5 N4 61.3(10) . . . . ?

_shelx_res_file                  
;
TITL 364k_rt_a.res in Pna2(1)
    364k_rt.res
    created by SHELXL-2018/3 at 13:49:05 on 08-Jan-2025
REM Old TITL 364k_RT in Pna2(1)
REM SHELXT solution in Pna2(1): R1 0.078, Rweak 0.035, Alpha 0.003
REM <I/s> 0.538 for 147 systematic absences, Orientation as input
REM Flack x = -0.069 ( 0.011 ) from 553 Parsons' quotients
REM Formula found by SHELXT: C7 N3 P Br3
CELL 0.71073 13.8355 9.9594 9.7006 90 90 90
ZERR 4 0.0005 0.0004 0.0004 0 0 0
LATT -1
SYMM -X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,+Z
SYMM 0.5-X,0.5+Y,0.5+Z
SFAC C H Br N P
UNIT 24 72 12 16 4
DFIX 1.04 N1 H1c N1 H1d N1 H1e N1 H1f
DANG 1.75 H1c H1d H1c H1e H1c H1f H1d H1e H1d H1f H1e H1f

L.S. 16
PLAN  7
SIZE 0.16 0.19 0.22
TEMP 90.85
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\364k_RT.hkl">
REM </olex2.extras>

WGHT    0.074300    0.716400
FVAR       0.27733
BR01  3    0.276855    0.534474    0.709232    11.00000    0.04936    0.05300 =
         0.06182   -0.00203    0.00167   -0.00164
BR02  3   -0.013450    0.218931    0.414898    11.00000    0.06852    0.05767 =
         0.05628    0.00608   -0.00552   -0.00770
BR03  3    0.246080   -0.006800    0.666771    11.00000    0.05655    0.05889 =
         0.07288   -0.00855    0.00507    0.00039
P1    5    0.568807    0.913127    0.431896    11.00000    0.06189    0.05474 =
         0.09163   -0.00045   -0.00936   -0.00852
N2    4    0.427972    0.761948    0.294191    11.00000    0.03727    0.04975 =
         0.04873   -0.01468   -0.00062   -0.00743
N1    4    0.230554    0.283913    0.462352    11.00000    0.06805    0.06038 =
         0.07783   -0.01720   -0.00913   -0.00126
N4    4    0.563875    0.634508    0.411490    11.00000    0.04962    0.03799 =
         0.06029    0.00341    0.00152    0.01223
AFIX  13
H4    2    0.604331    0.554537    0.399849    11.00000   -1.20000
AFIX   0
N3    4    0.438618    0.736037    0.554686    11.00000    0.04963    0.05835 =
         0.04952    0.00000    0.01477   -0.00961
AFIX  13
H3    2    0.397907    0.720885    0.635880    11.00000   -1.20000
AFIX   0
C6    1    0.508062    0.616554    0.539692    11.00000    0.06151    0.03892 =
         0.06707    0.01196   -0.00066    0.00330
AFIX  23
H6A   2    0.551421    0.612743    0.618172    11.00000   -1.20000
H6B   2    0.471825    0.533256    0.535948    11.00000   -1.20000
AFIX   0
C4    1    0.373474    0.743339    0.427685    11.00000    0.03583    0.05571 =
         0.08212   -0.00334   -0.00376   -0.00773
AFIX  23
H4A   2    0.335846    0.661347    0.421984    11.00000   -1.20000
H4B   2    0.328655    0.817427    0.438946    11.00000   -1.20000
AFIX   0
C2    1    0.492201    0.866655    0.573830    11.00000    0.07038    0.05053 =
         0.06729   -0.01951   -0.00085    0.00234
AFIX  23
H2A   2    0.531501    0.860093    0.656362    11.00000   -1.20000
H2B   2    0.445373    0.937701    0.588584    11.00000   -1.20000
AFIX   0
C3    1    0.629903    0.752654    0.420101    11.00000    0.03826    0.06108 =
         0.06838    0.00784   -0.00076    0.00374
AFIX  23
H3A   2    0.671132    0.753277    0.339227    11.00000   -1.20000
H3B   2    0.671184    0.742090    0.500193    11.00000   -1.20000
AFIX   0
C5    1    0.496564    0.642117    0.287059    11.00000    0.06886    0.04172 =
         0.04104   -0.01043    0.00536   -0.00208
AFIX  23
H5A   2    0.535050    0.648570    0.203742    11.00000   -1.20000
H5B   2    0.458944    0.560091    0.281787    11.00000   -1.20000
AFIX   0
C1    1    0.482558    0.885541    0.296010    11.00000    0.08853    0.04770 =
         0.07185    0.02664    0.00285    0.00915
AFIX  23
H1A   2    0.436639    0.959101    0.298407    11.00000   -1.20000
H1B   2    0.516937    0.891908    0.209109    11.00000   -1.20000
AFIX   0
H1C   2    0.294848    0.236672    0.427662    11.00000   -1.20000
H1D   2    0.172836    0.217417    0.435348    11.00000   -1.20000
H1E   2    0.221958    0.370528    0.402551    11.00000   -1.20000
H1F   2    0.232632    0.298961    0.567854    11.00000   -1.20000
HKLF 4




REM  364k_rt_a.res in Pna2(1)
REM wR2 = 0.1137, GooF = S = 1.069, Restrained GooF = 1.068 for all data
REM R1 = 0.0451 for 2108 Fo > 4sig(Fo) and 0.0513 for all 2370 data
REM 139 parameters refined using 11 restraints

END

WGHT      0.0739      0.7326

REM Highest difference peak  1.042,  deepest hole -0.628,  1-sigma level  0.135
Q1    1   0.2265  0.5016  0.7065  11.00000  0.05    1.04
Q2    1   0.2406  0.5648  0.6649  11.00000  0.05    0.96
Q3    1  -0.0030  0.2745  0.4551  11.00000  0.05    0.95
Q4    1   0.0192  0.2775  0.4010  11.00000  0.05    0.93
Q5    1   0.2571  0.4994  0.6375  11.00000  0.05    0.84
Q6    1   0.0405  0.1864  0.4227  11.00000  0.05    0.78
Q7    1   0.2461 -0.0539  0.7252  11.00000  0.05    0.70
;
_shelx_res_checksum              41954
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.704
_oxdiff_exptl_absorpt_empirical_full_min 0.724
####################################################################### 
# 
# 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_pta-br_345k
_database_code_depnum_ccdc_archive 'CCDC 2424521'
loop_
_audit_author_name
_audit_author_address
'Ryo Tsunashima'
;yamaguchi
Japan
;
_audit_update_record             
;
2025-02-17 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;
_audit_creation_date             2025-01-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(Br), C6 H14 N3 P, H4 N'
_chemical_formula_sum            'C6 H18 Br3 N4 P'
_chemical_formula_weight         416.94
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H18N3Br3P
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'
N N 0.0061 0.0033 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   13.8098(4)
_cell_length_b                   9.9529(3)
_cell_length_c                   9.6797(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1330.45(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3687
_cell_measurement_temperature    345
_cell_measurement_theta_max      30.0720
_cell_measurement_theta_min      2.9160
_shelx_estimated_absorpt_T_max   0.359
_shelx_estimated_absorpt_T_min   0.274
_exptl_absorpt_coefficient_mu    9.190
_exptl_absorpt_correction_T_max  0.32898
_exptl_absorpt_correction_T_min  0.31385
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.082
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       sphere
_exptl_crystal_F_000             808
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
15 -2 8 0.0762
-1 11 9 0.0761
-15 9 -2 0.0814
-10 -4 -11 0.0875
1 -11 -9 0.0710
15 7 -5 0.0703
-7 3 -12 0.0894
-17 -3 -5 0.0954
-15 -7 5 0.1046
7 -3 12 0.0510
-13 10 3 0.0650

_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_crystal_size_rad          0.088
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
15.1032 -1.9984 8.3847 -0.1441 -0.1197 0.9823
-1.2881 10.7706 8.6977 0.6924 0.5942 0.4093
-14.5019 9.2210 -1.5666 0.6069 0.5172 -0.6035
-10.3542 -4.2892 -10.7736 -0.2643 -0.2297 -0.9367
0.7658 -10.6128 -8.9089 -0.6817 -0.5851 -0.4392
14.7080 7.4768 -5.2119 0.6241 -0.7280 0.2836
-6.9752 3.4259 -12.2968 0.3054 -0.3604 -0.8814
-17.2510 -3.3186 -5.4339 -0.2618 0.3022 -0.9166
-15.0149 -7.4131 4.8553 -0.6182 0.7210 -0.3130
7.0508 -3.3940 12.2839 -0.3028 0.3573 0.8835
-12.6574 10.2432 2.8733 0.6537 0.6915 -0.3075

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5122
_diffrn_reflns_point_group_measured_fraction_full 0.770
_diffrn_reflns_point_group_measured_fraction_max 0.760
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         2.935
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      345
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  11.00   0.25    2.20    --   -5.68 -59.00  26.00  300
  2  ω    -16.00  39.00   0.25    2.20    --    6.15 -99.00   0.00  220
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0038946000
_diffrn_orient_matrix_UB_12      0.0706896000
_diffrn_orient_matrix_UB_13      -0.0073518000
_diffrn_orient_matrix_UB_21      -0.0356093000
_diffrn_orient_matrix_UB_22      0.0089196000
_diffrn_orient_matrix_UB_23      0.0519933000
_diffrn_orient_matrix_UB_31      0.0368159000
_diffrn_orient_matrix_UB_32      0.0011342000
_diffrn_orient_matrix_UB_33      0.0511081000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.438
_reflns_Friedel_fraction_full    0.515
_reflns_Friedel_fraction_max     0.494
_reflns_number_gt                1955
_reflns_number_total             2067
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.876
_refine_diff_density_rms         0.111
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.012(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2067
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.051
_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)+(0.1176P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1363
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H,H,H) groups, All N(H) groups
2. Restrained distances
 N1-H1C = N1-H1D = N1-H1E = N1-H1F
 1.05 with sigma of 0.02
 H1C-H1D = H1C-H1E = H1C-H1F = H1D-H1E = H1D-H1F = H1E-H1F
 1.75 with sigma of 0.04
3.a Ternary CH refined with riding coordinates:
 N3(H3), N4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C3(H3A,H3B), C2(H2A,H2B), C5(H5A,H5B), C4(H4A,H4B), C1(H1A,H1B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
Br01 Br 0.72268(7) 0.53542(10) 0.71018(14) 0.0466(3) Uani 1 1 d . . . . .
Br02 Br 1.01405(7) 0.21850(11) 0.41477(14) 0.0522(3) Uani 1 1 d . . . . .
Br03 Br 0.75378(8) -0.00693(11) 0.6668(2) 0.0540(3) Uani 1 1 d . . . . .
P1 P 0.43102(18) 0.9141(3) 0.4316(4) 0.0568(8) Uani 1 1 d . . . . .
N2 N 0.5723(6) 0.7602(9) 0.2959(9) 0.0408(17) Uani 1 1 d . . . . .
N3 N 0.4359(5) 0.6342(7) 0.4116(9) 0.0413(17) Uani 1 1 d . . . . .
H3 H 0.395784 0.553703 0.400045 0.050 Uiso 1 1 calc R U . . .
N1 N 0.7700(7) 0.2861(10) 0.4642(14) 0.060(3) Uani 1 1 d D . . . .
N4 N 0.5611(6) 0.7341(9) 0.5539(10) 0.0450(19) Uani 1 1 d . . . . .
H4 H 0.601803 0.718320 0.635190 0.054 Uiso 1 1 calc R U . . .
C6 C 0.4922(7) 0.6163(12) 0.5398(13) 0.045(2) Uani 1 1 d . . . . .
H6A H 0.528383 0.532847 0.535979 0.055 Uiso 1 1 calc R U . . .
H6B H 0.449016 0.612759 0.618738 0.055 Uiso 1 1 calc R U . . .
C3 C 0.5078(8) 0.8649(12) 0.5752(14) 0.055(3) Uani 1 1 d . . . . .
H3A H 0.554952 0.935500 0.591395 0.065 Uiso 1 1 calc R U . . .
H3B H 0.468186 0.857350 0.657563 0.065 Uiso 1 1 calc R U . . .
C2 C 0.3690(6) 0.7515(10) 0.4187(14) 0.046(2) Uani 1 1 d . . . . .
H2A H 0.326949 0.740898 0.498134 0.055 Uiso 1 1 calc R U . . .
H2B H 0.328574 0.751826 0.336750 0.055 Uiso 1 1 calc R U . . .
C5 C 0.6270(6) 0.7424(11) 0.4279(15) 0.052(2) Uani 1 1 d . . . . .
H5A H 0.671204 0.817280 0.439454 0.062 Uiso 1 1 calc R U . . .
H5B H 0.665254 0.660911 0.422236 0.062 Uiso 1 1 calc R U . . .
C4 C 0.5050(7) 0.6412(11) 0.2860(11) 0.044(2) Uani 1 1 d . . . . .
H4A H 0.542796 0.559225 0.281331 0.053 Uiso 1 1 calc R U . . .
H4B H 0.467142 0.647939 0.201891 0.053 Uiso 1 1 calc R U . . .
C1 C 0.5184(9) 0.8863(13) 0.2944(14) 0.059(3) Uani 1 1 d . . . . .
H1A H 0.484403 0.892166 0.206881 0.071 Uiso 1 1 calc R U . . .
H1B H 0.564833 0.959412 0.296746 0.071 Uiso 1 1 calc R U . . .
H1C H 0.836(5) 0.296(9) 0.522(10) 0.071 Uiso 1 1 d D U . . .
H1D H 0.721(5) 0.360(7) 0.497(11) 0.071 Uiso 1 1 d D U . . .
H1E H 0.787(8) 0.299(11) 0.358(4) 0.071 Uiso 1 1 d D U . . .
H1F H 0.743(7) 0.187(4) 0.479(12) 0.071 Uiso 1 1 d D U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br01 0.0397(5) 0.0430(5) 0.0571(6) -0.0016(4) -0.0018(4) 0.0025(4)
Br02 0.0570(5) 0.0474(6) 0.0520(6) 0.0052(6) 0.0052(6) 0.0070(4)
Br03 0.0465(5) 0.0487(6) 0.0667(8) -0.0072(5) -0.0045(5) -0.0012(4)
P1 0.0481(13) 0.0410(14) 0.081(2) 0.0005(13) 0.0069(15) 0.0066(11)
N2 0.034(3) 0.039(4) 0.049(5) -0.015(4) 0.001(3) 0.009(3)
N3 0.040(3) 0.029(3) 0.055(5) 0.005(4) -0.001(4) -0.008(3)
N1 0.052(5) 0.055(6) 0.073(7) -0.016(5) 0.006(4) 0.002(4)
N4 0.041(4) 0.046(4) 0.048(5) -0.001(4) -0.015(4) 0.010(3)
C6 0.047(5) 0.037(5) 0.053(6) 0.002(5) 0.000(4) 0.002(4)
C3 0.062(6) 0.040(6) 0.061(7) -0.015(5) -0.006(5) 0.002(4)
C2 0.028(3) 0.047(5) 0.063(6) 0.003(6) -0.001(5) 0.001(3)
C5 0.034(4) 0.042(5) 0.080(7) -0.004(6) 0.003(5) 0.003(4)
C4 0.059(6) 0.036(5) 0.038(5) -0.006(4) -0.004(4) 0.005(4)
C1 0.070(7) 0.044(6) 0.064(8) 0.018(6) 0.002(6) -0.011(5)

_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 C3 1.816(13) . ?
P1 C2 1.835(10) . ?
P1 C1 1.816(14) . ?
N2 C5 1.494(16) . ?
N2 C4 1.509(14) . ?
N2 C1 1.460(15) . ?
N3 H3 0.9800 . ?
N3 C6 1.475(15) . ?
N3 C2 1.490(11) . ?
N3 C4 1.547(14) . ?
N1 H1C 1.07(2) . ?
N1 H1D 1.05(2) . ?
N1 H1E 1.07(2) . ?
N1 H1F 1.06(2) . ?
N4 H4 0.9800 . ?
N4 C6 1.516(14) . ?
N4 C3 1.509(14) . ?
N4 C5 1.524(16) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 P1 C2 95.0(6) . . ?
C1 P1 C3 97.5(5) . . ?
C1 P1 C2 97.2(6) . . ?
C5 N2 C4 105.8(8) . . ?
C1 N2 C5 111.6(8) . . ?
C1 N2 C4 111.1(8) . . ?
C6 N3 H3 107.2 . . ?
C6 N3 C2 112.5(9) . . ?
C6 N3 C4 110.0(7) . . ?
C2 N3 H3 107.2 . . ?
C2 N3 C4 112.5(8) . . ?
C4 N3 H3 107.2 . . ?
H1C N1 H1D 109(4) . . ?
H1C N1 H1E 108(4) . . ?
H1C N1 H1F 108(4) . . ?
H1D N1 H1E 111(4) . . ?
H1D N1 H1F 113(4) . . ?
H1E N1 H1F 109(4) . . ?
C6 N4 H4 108.0 . . ?
C6 N4 C5 110.1(9) . . ?
C3 N4 H4 108.0 . . ?
C3 N4 C6 112.0(8) . . ?
C3 N4 C5 110.7(9) . . ?
C5 N4 H4 108.0 . . ?
N3 C6 N4 108.3(9) . . ?
N3 C6 H6A 110.0 . . ?
N3 C6 H6B 110.0 . . ?
N4 C6 H6A 110.0 . . ?
N4 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
P1 C3 H3A 108.7 . . ?
P1 C3 H3B 108.7 . . ?
N4 C3 P1 114.3(8) . . ?
N4 C3 H3A 108.7 . . ?
N4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
P1 C2 H2A 108.8 . . ?
P1 C2 H2B 108.8 . . ?
N3 C2 P1 113.9(5) . . ?
N3 C2 H2A 108.8 . . ?
N3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
N2 C5 N4 112.9(7) . . ?
N2 C5 H5A 109.0 . . ?
N2 C5 H5B 109.0 . . ?
N4 C5 H5A 109.0 . . ?
N4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
N2 C4 N3 111.5(8) . . ?
N2 C4 H4A 109.3 . . ?
N2 C4 H4B 109.3 . . ?
N3 C4 H4A 109.3 . . ?
N3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
P1 C1 H1A 107.9 . . ?
P1 C1 H1B 107.9 . . ?
N2 C1 P1 117.6(8) . . ?
N2 C1 H1A 107.9 . . ?
N2 C1 H1B 107.9 . . ?
H1A C1 H1B 107.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N3 C2 P1 65.4(11) . . . . ?
C6 N3 C4 N2 -62.1(10) . . . . ?
C6 N4 C3 P1 -63.2(12) . . . . ?
C6 N4 C5 N2 59.7(10) . . . . ?
C3 P1 C2 N3 -51.0(10) . . . . ?
C3 P1 C1 N2 47.1(10) . . . . ?
C3 N4 C6 N3 65.7(12) . . . . ?
C3 N4 C5 N2 -64.7(10) . . . . ?
C2 P1 C3 N4 50.4(9) . . . . ?
C2 P1 C1 N2 -48.9(10) . . . . ?
C2 N3 C6 N4 -67.1(10) . . . . ?
C2 N3 C4 N2 64.1(10) . . . . ?
C5 N2 C4 N3 58.6(9) . . . . ?
C5 N2 C1 P1 -57.6(11) . . . . ?
C5 N4 C6 N3 -58.0(10) . . . . ?
C5 N4 C3 P1 60.2(11) . . . . ?
C4 N2 C5 N4 -58.3(10) . . . . ?
C4 N2 C1 P1 60.3(12) . . . . ?
C4 N3 C6 N4 59.1(10) . . . . ?
C4 N3 C2 P1 -59.5(11) . . . . ?
C1 P1 C3 N4 -47.6(10) . . . . ?
C1 P1 C2 N3 47.3(10) . . . . ?
C1 N2 C5 N4 62.7(11) . . . . ?
C1 N2 C4 N3 -62.6(12) . . . . ?

_shelx_res_file                  
;
TITL 350_re1_a.res in Pna2(1)
    pta-br_345k.res
    created by SHELXL-2018/3 at 13:41:08 on 08-Jan-2025
REM Old TITL 350_re1 in Pna2(1)
REM SHELXT solution in Pna2(1): R1 0.081, Rweak 0.014, Alpha 0.004
REM <I/s> 0.444 for 146 systematic absences, Orientation as input
REM Flack x = -0.074 ( 0.030 ) from 584 Parsons' quotients
REM Formula found by SHELXT: C7 N3 P Br3
CELL 0.71073 13.8098 9.9529 9.6797 90 90 90
ZERR 4 0.0004 0.0003 0.0004 0 0 0
LATT -1
SYMM -X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,+Z
SYMM 0.5-X,0.5+Y,0.5+Z
SFAC C H Br N P
UNIT 24 72 12 16 4
DFIX 1.05 N1 H1c N1 H1d N1 H1e N1 H1f
DANG 1.75 H1c H1d H1c H1e H1c H1f H1d H1e H1d H1f H1e H1f

L.S. 8
PLAN  7
SIZE 0.14 0.19 0.19
TEMP 77
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\pta-Br_345K.hkl">
REM </olex2.extras>

WGHT    0.117600
FVAR       0.28574
BR01  3    0.722678    0.535423    0.710177    11.00000    0.03968    0.04301 =
         0.05714   -0.00157   -0.00184    0.00250
BR02  3    1.014046    0.218501    0.414772    11.00000    0.05701    0.04742 =
         0.05202    0.00520    0.00519    0.00701
BR03  3    0.753781   -0.006927    0.666773    11.00000    0.04647    0.04874 =
         0.06668   -0.00720   -0.00450   -0.00117
P1    5    0.431020    0.914102    0.431566    11.00000    0.04808    0.04104 =
         0.08121    0.00046    0.00695    0.00657
N2    4    0.572339    0.760173    0.295903    11.00000    0.03371    0.03925 =
         0.04936   -0.01507    0.00113    0.00916
N3    4    0.435883    0.634156    0.411625    11.00000    0.04015    0.02937 =
         0.05451    0.00455   -0.00090   -0.00763
AFIX  13
H3    2    0.395784    0.553703    0.400045    11.00000   -1.20000
AFIX   0

N1    4    0.770014    0.286059    0.464216    11.00000    0.05244    0.05468 =
         0.07340   -0.01639    0.00589    0.00154
N4    4    0.561058    0.734129    0.553908    11.00000    0.04128    0.04586 =
         0.04771   -0.00111   -0.01454    0.01029
AFIX  13
H4    2    0.601803    0.718320    0.635190    11.00000   -1.20000
AFIX   0
C6    1    0.492204    0.616300    0.539793    11.00000    0.04664    0.03709 =
         0.05260    0.00249    0.00010    0.00187
AFIX  23
H6A   2    0.528383    0.532847    0.535979    11.00000   -1.20000
H6B   2    0.449016    0.612759    0.618738    11.00000   -1.20000
AFIX   0
C3    1    0.507849    0.864934    0.575227    11.00000    0.06230    0.04038 =
         0.06084   -0.01486   -0.00613    0.00200
AFIX  23
H3A   2    0.554952    0.935500    0.591395    11.00000   -1.20000
H3B   2    0.468186    0.857350    0.657563    11.00000   -1.20000
AFIX   0
C2    1    0.369039    0.751535    0.418658    11.00000    0.02770    0.04714 =
         0.06266    0.00343   -0.00139    0.00095
AFIX  23
H2A   2    0.326949    0.740898    0.498134    11.00000   -1.20000
H2B   2    0.328574    0.751826    0.336750    11.00000   -1.20000
AFIX   0
C5    1    0.626959    0.742423    0.427914    11.00000    0.03383    0.04207 =
         0.08014   -0.00429    0.00347    0.00309
AFIX  23
H5A   2    0.671204    0.817280    0.439454    11.00000   -1.20000
H5B   2    0.665254    0.660911    0.422236    11.00000   -1.20000
AFIX   0
C4    1    0.504965    0.641212    0.286048    11.00000    0.05947    0.03591 =
         0.03776   -0.00629   -0.00359    0.00451
AFIX  23
H4A   2    0.542796    0.559225    0.281331    11.00000   -1.20000
H4B   2    0.467142    0.647939    0.201891    11.00000   -1.20000
AFIX   0
C1    1    0.518408    0.886312    0.294358    11.00000    0.06976    0.04362 =
         0.06419    0.01798    0.00246   -0.01105
AFIX  23
H1A   2    0.484403    0.892166    0.206881    11.00000   -1.20000
H1B   2    0.564833    0.959412    0.296746    11.00000   -1.20000
AFIX   0
H1C   2    0.835515    0.295887    0.521749    11.00000   -1.20000
H1D   2    0.721325    0.359918    0.497144    11.00000   -1.20000
H1E   2    0.787318    0.298865    0.357693    11.00000   -1.20000
H1F   2    0.743000    0.187339    0.478844    11.00000   -1.20000
HKLF 4




REM  350_re1_a.res in Pna2(1)
REM wR2 = 0.1363, GooF = S = 1.053, Restrained GooF = 1.051 for all data
REM R1 = 0.0503 for 1955 Fo > 4sig(Fo) and 0.0522 for all 2067 data
REM 139 parameters refined using 11 restraints

END

WGHT      0.1176      0.0000

REM Highest difference peak  0.692,  deepest hole -0.876,  1-sigma level  0.111
Q1    1   1.0166  0.2765  0.3386  11.00000  0.05    0.69
Q2    1   1.0202  0.2647  0.4881  11.00000  0.05    0.62
Q3    1   0.7545 -0.0723  0.7489  11.00000  0.05    0.53
Q4    1   0.7233  0.4835  0.6247  11.00000  0.05    0.53
Q5    1   0.7367  0.5909  0.6326  11.00000  0.05    0.52
Q6    1   1.0158  0.1544  0.5117  11.00000  0.05    0.50
Q7    1   0.7417  0.5000  0.7832  11.00000  0.05    0.50
;
_shelx_res_checksum              44293
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.442
_oxdiff_exptl_absorpt_empirical_full_min 0.709
####################################################################### 
# 
# 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_373k_rt2_inv
_database_code_depnum_ccdc_archive 'CCDC 2424523'
loop_
_audit_author_name
_audit_author_address
'Ryo Tsunashima'
;yamaguchi
Japan
;
_audit_update_record             
;
2025-02-17 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;
_audit_creation_date             2025-01-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(Br), C6 H14 N3 P, H4 N'
_chemical_formula_sum            'C6 H18 Br3 N4 P'
_chemical_formula_weight         416.94
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H18N3Br3P
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'
N N 0.0061 0.0033 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   13.8318(6)
_cell_length_b                   9.9497(4)
_cell_length_c                   9.7003(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1334.98(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2860
_cell_measurement_temperature    373
_cell_measurement_theta_max      26.8090
_cell_measurement_theta_min      2.9180
_shelx_estimated_absorpt_T_max   0.305
_shelx_estimated_absorpt_T_min   0.208
_exptl_absorpt_coefficient_mu    9.159
_exptl_absorpt_correction_T_max  0.119
_exptl_absorpt_correction_T_min  0.057
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.074
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
7 -1 -17 0.0834
13 4 4 0.0746
5 5 17 0.0851
-13 -3 1 0.0806
-8 -5 -14 0.1030
10 -3 -12 0.0793
7 6 -14 0.1028
4 9 -13 0.1030
-5 13 -2 0.0989
-10 3 12 0.0893
-6 -7 14 0.0820
-5 -13 0 0.1065
2 13 5 0.0937
-7 8 -13 0.1004
13 -5 -4 0.0823
6 -8 13 0.1176

_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
6.8520 -1.1849 -16.7847 -0.0631 -0.2523 0.9656
12.7741 4.2195 3.7584 0.1974 0.8324 0.5178
5.3776 4.5629 16.7756 0.2197 0.9152 -0.3379
-13.2285 -3.4868 0.9209 -0.1612 -0.6831 -0.7123
-8.3356 -4.8560 -13.9165 -0.2319 -0.9693 0.0816
10.1415 -3.1610 -12.3037 -0.2430 0.0608 0.9681
6.8789 6.2046 -14.4738 0.4503 -0.1051 0.8867
4.2249 9.4801 -13.0511 0.6943 -0.1640 0.7007
-5.3059 12.8664 -1.7933 0.9533 -0.2283 -0.1976
-10.1535 3.3306 12.1966 0.2555 -0.0637 -0.9647
-6.4710 -6.8105 14.3303 -0.4954 0.1160 -0.8609
-4.9110 -13.0934 -0.1257 -0.8928 -0.3717 -0.2545
1.6992 13.4457 5.0070 0.9199 0.3819 -0.0887
-6.5731 7.6994 -13.3502 0.6424 -0.7498 0.1585
12.5882 -4.7663 -3.7302 -0.4073 0.4790 0.7776
6.4936 -7.6912 13.4381 -0.6416 0.7489 -0.1658

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.789
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5607
_diffrn_reflns_point_group_measured_fraction_full 0.764
_diffrn_reflns_point_group_measured_fraction_max 0.577
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.585
_diffrn_reflns_theta_min         2.933
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      373
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.789
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  11.00   0.25    2.20    --   -5.68 -59.00  26.00  300
  2  ω    -16.00  39.00   0.25    2.20    --    6.15 -99.00   0.00  220
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0067451896
_diffrn_orient_matrix_UB_12      0.0707554558
_diffrn_orient_matrix_UB_13      -0.0039879354
_diffrn_orient_matrix_UB_21      0.0518538775
_diffrn_orient_matrix_UB_22      0.0085970004
_diffrn_orient_matrix_UB_23      0.0355938516
_diffrn_orient_matrix_UB_31      0.0511292138
_diffrn_orient_matrix_UB_32      0.0006090148
_diffrn_orient_matrix_UB_33      -0.0366980801
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.388
_reflns_Friedel_fraction_full    0.503
_reflns_Friedel_fraction_max     0.341
_reflns_number_gt                2008
_reflns_number_total             2361
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.634
_refine_diff_density_min         -0.815
_refine_diff_density_rms         0.229
_refine_ls_abs_structure_details 
;
 Flack x determined using 511 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.071(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2361
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0582
_refine_ls_restrained_S_all      1.154
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0806P)²+0.1269P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1331
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All Br(H,H,H,H) groups
2. Restrained distances
 N1-H1E = N1-H1D = N1-H1F = N1-H1C
 1.03 with sigma of 0.02
 H1E-H1D = H1E-H1F = H1E-H1C = H1D-H1F = H1D-H1C = H1F-H1C
 1.75 with sigma of 0.04
3. Others
 Fixed Sof: Br3(0.75) Br4(0.25)
4.a Ternary CH refined with riding coordinates:
 N3(H3), N4(H4)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C3(H3A,H3B), C5(H5A,H5B), C2(H2A,H2B), C4(H4A,H4B), C1(H1A,H1B)
;
_atom_sites_solution_hydrogens   mixed
_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 0.74601(9) 0.49318(11) 0.6809(3) 0.0664(4) Uani 1 1 d . . . . .
Br2 Br 0.48687(8) 0.71972(12) 0.42906(17) 0.0654(4) Uani 1 1 d . . . A -1
P1 P 0.5685(2) 0.0871(3) 0.4458(5) 0.0766(9) Uani 1 1 d . . . . .
N2 N 0.4279(6) 0.2374(8) 0.3074(9) 0.0471(18) Uani 1 1 d . . . . .
N1 N 0.2307(7) 0.7189(11) 0.4759(15) 0.073(3) Uani 1 1 d D . . . .
N3 N 0.5645(5) 0.3654(7) 0.4270(10) 0.0528(19) Uani 1 1 d . . . . .
H3 H 0.604999 0.445474 0.416131 0.063 Uiso 1 1 calc R U . . .
C6 C 0.5070(7) 0.3834(11) 0.5540(14) 0.058(3) Uani 1 1 d . . . . .
H6A H 0.469914 0.465970 0.548465 0.069 Uiso 1 1 calc R U . . .
H6B H 0.549600 0.389174 0.633223 0.069 Uiso 1 1 calc R U . . .
N4 N 0.4398(7) 0.2646(9) 0.5692(9) 0.056(2) Uani 1 1 d . . . . .
H4 H 0.399160 0.278827 0.650632 0.067 Uiso 1 1 calc R U . . .
C3 C 0.4930(8) 0.1337(14) 0.5859(14) 0.068(3) Uani 1 1 d . . . . .
H3A H 0.445916 0.062834 0.600273 0.082 Uiso 1 1 calc R U . . .
H3B H 0.532464 0.139114 0.668437 0.082 Uiso 1 1 calc R U . . .
C5 C 0.3740(6) 0.2558(11) 0.4411(16) 0.062(3) Uani 1 1 d . . . . .
H5A H 0.329695 0.181051 0.452916 0.074 Uiso 1 1 calc R U . . .
H5B H 0.335713 0.337269 0.435295 0.074 Uiso 1 1 calc R U . . .
C2 C 0.6293(6) 0.2486(11) 0.4328(16) 0.059(2) Uani 1 1 d . . . . .
H2A H 0.671827 0.258712 0.511598 0.071 Uiso 1 1 calc R U . . .
H2B H 0.669242 0.248313 0.350668 0.071 Uiso 1 1 calc R U . . .
C4 C 0.4968(7) 0.3592(12) 0.3026(12) 0.053(3) Uani 1 1 d . . . . .
H4A H 0.535172 0.354577 0.219065 0.064 Uiso 1 1 calc R U . . .
H4B H 0.458800 0.441038 0.299010 0.064 Uiso 1 1 calc R U . . .
C1 C 0.4836(9) 0.1146(14) 0.3110(16) 0.074(3) Uani 1 1 d . . . . .
H1A H 0.518507 0.108453 0.224467 0.089 Uiso 1 1 calc R U . . .
H1B H 0.438128 0.040449 0.312851 0.089 Uiso 1 1 calc R U . . .
Br3 Br 0.2796(4) 0.4663(4) 0.7246(5) 0.0480(6) Uani 0.75 1 d . . P B -1
H1C H 0.296(3) 0.767(7) 0.446(9) 0.058 Uiso 1 1 d D U . . .
H1D H 0.221(5) 0.638(5) 0.410(7) 0.058 Uiso 1 1 d D U . . .
H1E H 0.173(4) 0.788(6) 0.457(8) 0.058 Uiso 1 1 d D U . . .
H1F H 0.234(6) 0.697(8) 0.580(3) 0.058 Uiso 1 1 d D U . . .
Br4 Br 0.2589(12) 0.4652(19) 0.708(3) 0.080(6) Uani 0.25 1 d . . P C -2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0598(6) 0.0621(6) 0.0772(8) -0.0082(6) 0.0047(5) -0.0004(4)
Br2 0.0724(6) 0.0629(6) 0.0608(6) 0.0079(7) -0.0046(7) -0.0078(4)
P1 0.0674(16) 0.0626(17) 0.100(3) 0.0010(17) -0.0089(18) 0.0083(13)
N2 0.041(4) 0.048(4) 0.052(5) 0.011(3) -0.003(3) 0.004(3)
N1 0.076(6) 0.066(6) 0.077(7) 0.015(5) -0.010(5) 0.005(4)
N3 0.057(4) 0.041(4) 0.060(5) -0.004(4) 0.006(4) -0.015(3)
C6 0.063(6) 0.038(5) 0.073(8) -0.012(5) -0.004(5) -0.002(4)
N4 0.061(5) 0.061(5) 0.045(5) -0.001(4) 0.014(4) 0.010(4)
C3 0.075(7) 0.063(8) 0.065(8) 0.028(6) -0.005(5) -0.002(5)
C5 0.038(4) 0.060(6) 0.088(8) 0.008(6) -0.001(5) 0.012(4)
C2 0.041(4) 0.067(6) 0.069(6) -0.005(6) -0.006(6) -0.001(4)
C4 0.069(6) 0.048(6) 0.042(6) 0.006(5) -0.001(4) -0.002(4)
C1 0.094(9) 0.054(7) 0.074(9) -0.024(6) 0.005(7) -0.018(6)
Br3 0.0381(15) 0.0495(9) 0.0564(12) -0.0019(8) -0.0047(14) 0.0010(8)
Br4 0.053(8) 0.098(6) 0.088(11) 0.020(5) -0.002(6) -0.008(4)

_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 C3 1.776(14) . ?
P1 C2 1.817(11) . ?
P1 C1 1.779(16) . ?
N2 C5 1.508(17) . ?
N2 C4 1.542(13) . ?
N2 C1 1.445(17) . ?
N1 H1C 1.05(2) . ?
N1 H1D 1.04(2) . ?
N1 H1E 1.06(2) . ?
N1 H1F 1.03(2) . ?
N3 H3 0.9800 . ?
N3 C6 1.476(15) . ?
N3 C2 1.469(12) . ?
N3 C4 1.528(14) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 N4 1.512(14) . ?
N4 H4 0.9800 . ?
N4 C3 1.505(15) . ?
N4 C5 1.543(17) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 P1 C2 95.4(6) . . ?
C3 P1 C1 97.7(5) . . ?
C1 P1 C2 96.8(6) . . ?
C5 N2 C4 103.7(8) . . ?
C1 N2 C5 110.2(9) . . ?
C1 N2 C4 109.6(8) . . ?
H1C N1 H1D 107(4) . . ?
H1C N1 H1E 107(4) . . ?
H1C N1 H1F 109(4) . . ?
H1D N1 H1E 108(4) . . ?
H1D N1 H1F 117(4) . . ?
H1E N1 H1F 109(4) . . ?
C6 N3 H3 107.4 . . ?
C6 N3 C4 109.5(7) . . ?
C2 N3 H3 107.4 . . ?
C2 N3 C6 113.1(10) . . ?
C2 N3 C4 111.8(8) . . ?
C4 N3 H3 107.4 . . ?
N3 C6 H6A 110.0 . . ?
N3 C6 H6B 110.0 . . ?
N3 C6 N4 108.5(8) . . ?
H6A C6 H6B 108.4 . . ?
N4 C6 H6A 110.0 . . ?
N4 C6 H6B 110.0 . . ?
C6 N4 H4 108.6 . . ?
C6 N4 C5 109.2(9) . . ?
C3 N4 C6 112.7(9) . . ?
C3 N4 H4 108.6 . . ?
C3 N4 C5 109.0(9) . . ?
C5 N4 H4 108.6 . . ?
P1 C3 H3A 108.4 . . ?
P1 C3 H3B 108.4 . . ?
N4 C3 P1 115.5(8) . . ?
N4 C3 H3A 108.4 . . ?
N4 C3 H3B 108.4 . . ?
H3A C3 H3B 107.5 . . ?
N2 C5 N4 114.1(6) . . ?
N2 C5 H5A 108.7 . . ?
N2 C5 H5B 108.7 . . ?
N4 C5 H5A 108.7 . . ?
N4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
P1 C2 H2A 108.6 . . ?
P1 C2 H2B 108.6 . . ?
N3 C2 P1 114.9(6) . . ?
N3 C2 H2A 108.6 . . ?
N3 C2 H2B 108.6 . . ?
H2A C2 H2B 107.5 . . ?
N2 C4 H4A 109.0 . . ?
N2 C4 H4B 109.0 . . ?
N3 C4 N2 112.8(8) . . ?
N3 C4 H4A 109.0 . . ?
N3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
P1 C1 H1A 107.3 . . ?
P1 C1 H1B 107.3 . . ?
N2 C1 P1 120.0(9) . . ?
N2 C1 H1A 107.3 . . ?
N2 C1 H1B 107.3 . . ?
H1A C1 H1B 106.9 . . ?

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
N3 C6 N4 C3 62.7(13) . . . . ?
N3 C6 N4 C5 -58.7(11) . . . . ?
C6 N3 C2 P1 64.2(12) . . . . ?
C6 N3 C4 N2 -63.3(10) . . . . ?
C6 N4 C3 P1 -61.3(13) . . . . ?
C6 N4 C5 N2 60.2(10) . . . . ?
C3 P1 C2 N3 -50.4(11) . . . . ?
C3 P1 C1 N2 47.2(11) . . . . ?
C3 N4 C5 N2 -63.4(11) . . . . ?
C5 N2 C4 N3 58.2(10) . . . . ?
C5 N2 C1 P1 -55.5(12) . . . . ?
C5 N4 C3 P1 60.1(11) . . . . ?
C2 P1 C3 N4 49.2(10) . . . . ?
C2 P1 C1 N2 -49.2(11) . . . . ?
C2 N3 C6 N4 -64.8(11) . . . . ?
C2 N3 C4 N2 62.9(11) . . . . ?
C4 N2 C5 N4 -57.1(9) . . . . ?
C4 N2 C1 P1 57.9(13) . . . . ?
C4 N3 C6 N4 60.7(10) . . . . ?
C4 N3 C2 P1 -60.0(12) . . . . ?
C1 P1 C3 N4 -48.5(10) . . . . ?
C1 P1 C2 N3 48.0(11) . . . . ?
C1 N2 C5 N4 60.1(11) . . . . ?
C1 N2 C4 N3 -59.5(12) . . . . ?

_shelx_res_file                  
;
TITL 373k_rt2_inv_a.res in Pna2(1)
    373k_rt2_inv.res
    created by SHELXL-2018/3 at 13:50:29 on 08-Jan-2025
REM Old TITL 373k_RT2_inv in P2(1)cn
REM SHELXT solution in Pna2(1): R1 0.091, Rweak 0.049, Alpha 0.002
REM <I/s> 0.603 for 147 systematic absences, Orientation a'=c, b'=-b, c'=a
REM Flack x = 0.068 ( 0.015 ) from 508 Parsons' quotients
REM Formula found by SHELXT: C8 N2 P Br3
CELL 0.71073 13.8318 9.9497 9.7003 90 90 90
ZERR 4 0.0006 0.0004 0.0006 0 0 0
LATT -1
SYMM -X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,+Z
SYMM 0.5-X,0.5+Y,0.5+Z
SFAC C H Br N P
UNIT 24 72 12 16 4
DFIX 1.03 N1 H1e N1 H1d N1 H1f N1 H1c
DANG 1.75 H1e H1d H1e H1f H1e H1c H1d H1f H1d H1c H1f H1c

L.S. 12
PLAN  7
SIZE 0.17 0.22 0.25
TEMP 99.85
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\373k_RT2_inv.hkl">
REM </olex2.extras>

WGHT    0.080600    0.126900
FVAR       0.25381
BR1   3    0.746012    0.493178    0.680911    11.00000    0.05983    0.06213 =
         0.07725   -0.00821    0.00471   -0.00043
PART -1
BR2   3    0.486868    0.719724    0.429062    11.00000    0.07241    0.06290 =
         0.06080    0.00790   -0.00457   -0.00783

PART 0
P1    5    0.568547    0.087143    0.445773    11.00000    0.06742    0.06264 =
         0.09976    0.00104   -0.00889    0.00828
N2    4    0.427909    0.237413    0.307368    11.00000    0.04119    0.04828 =
         0.05196    0.01062   -0.00257    0.00389

N1    4    0.230694    0.718908    0.475850    11.00000    0.07638    0.06614 =
         0.07714    0.01477   -0.00963    0.00490
N3    4    0.564464    0.365388    0.426991    11.00000    0.05704    0.04107 =
         0.06039   -0.00391    0.00576   -0.01508
AFIX  13
H3    2    0.604999    0.445474    0.416131    11.00000   -1.20000
AFIX   0
C6    1    0.507042    0.383438    0.553962    11.00000    0.06253    0.03776 =
         0.07318   -0.01245   -0.00361   -0.00220
AFIX  23
H6A   2    0.469914    0.465970    0.548465    11.00000   -1.20000
H6B   2    0.549600    0.389174    0.633223    11.00000   -1.20000
AFIX   0
N4    4    0.439813    0.264596    0.569187    11.00000    0.06073    0.06092 =
         0.04519   -0.00146    0.01388    0.00973
AFIX  13
H4    2    0.399160    0.278827    0.650632    11.00000   -1.20000
AFIX   0
C3    1    0.493040    0.133667    0.585928    11.00000    0.07523    0.06333 =
         0.06539    0.02790   -0.00489   -0.00171
AFIX  23
H3A   2    0.445916    0.062834    0.600273    11.00000   -1.20000
H3B   2    0.532464    0.139114    0.668437    11.00000   -1.20000
AFIX   0
C5    1    0.373977    0.255766    0.441107    11.00000    0.03754    0.05986 =
         0.08790    0.00844   -0.00062    0.01188
AFIX  23
H5A   2    0.329695    0.181051    0.452916    11.00000   -1.20000
H5B   2    0.335713    0.337269    0.435295    11.00000   -1.20000
AFIX   0
C2    1    0.629257    0.248554    0.432818    11.00000    0.04109    0.06710 =
         0.06915   -0.00480   -0.00585   -0.00090
AFIX  23
H2A   2    0.671827    0.258712    0.511598    11.00000   -1.20000
H2B   2    0.669242    0.248313    0.350668    11.00000   -1.20000
AFIX   0
C4    1    0.496786    0.359163    0.302619    11.00000    0.06907    0.04779 =
         0.04211    0.00639   -0.00076   -0.00223
AFIX  23
H4A   2    0.535172    0.354577    0.219065    11.00000   -1.20000
H4B   2    0.458800    0.441038    0.299010    11.00000   -1.20000
AFIX   0
C1    1    0.483623    0.114618    0.310984    11.00000    0.09437    0.05426 =
         0.07412   -0.02435    0.00525   -0.01755
AFIX  23
H1A   2    0.518507    0.108453    0.224467    11.00000   -1.20000
H1B   2    0.438128    0.040449    0.312851    11.00000   -1.20000
AFIX   0

PART -1
BR3   3    0.279622    0.466250    0.724576    10.75000    0.03811    0.04950 =
         0.05638   -0.00190   -0.00469    0.00103
PART 0
H1C   2    0.295531    0.766507    0.446458    11.00000   -1.20000
H1D   2    0.221230    0.638085    0.409534    11.00000   -1.20000
H1E   2    0.173499    0.788118    0.457458    11.00000   -1.20000
H1F   2    0.234125    0.697159    0.580075    11.00000   -1.20000

PART -2
BR4   3    0.258910    0.465203    0.708078    10.25000    0.05342    0.09779 =
         0.08792    0.01970   -0.00183   -0.00773
HKLF 4




REM  373k_rt2_inv_a.res in Pna2(1)
REM wR2 = 0.1331, GooF = S = 1.153, Restrained GooF = 1.154 for all data
REM R1 = 0.0582 for 2008 Fo > 4sig(Fo) and 0.0681 for all 2361 data
REM 148 parameters refined using 11 restraints

END

WGHT      0.0806      0.1269

REM Highest difference peak  1.634,  deepest hole -0.815,  1-sigma level  0.229
Q1    1   0.2456  0.5050  0.6730  11.00000  0.05    1.63
Q2    1   0.5097  0.7641  0.4733  11.00000  0.05    1.42
Q3    1   0.5185  0.7674  0.4046  11.00000  0.05    1.34
Q4    1   0.2619  0.7431  0.4966  11.00000  0.05    0.68
Q5    1   0.2493  0.6887  0.4972  11.00000  0.05    0.62
Q6    1   0.2454  0.7753  0.4478  11.00000  0.05    0.61
Q7    1   0.2555  0.7537  0.3891  11.00000  0.05    0.61
;
_shelx_res_checksum              29118
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.310
_oxdiff_exptl_absorpt_empirical_full_min 0.611
####################################################################### 
# 
# 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_p-bf4_233k
_database_code_depnum_ccdc_archive 'CCDC 2424326'
loop_
_audit_author_name
_audit_author_address
'Ryo Tsunashima'
;yamaguchi
Japan
;
_audit_update_record             
;
2025-02-17 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;
_audit_creation_date             2025-01-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'1.333(C6 H14.017 N3.008 P0.992), 4(B F4), 0.667(H8 N2)'
_chemical_formula_sum            'C8 H24.02 B4 F16 N5.34 P1.32'
_chemical_formula_weight         583.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H18N4PB4F12
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'
B B 0.0013 0.0007 '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'
P P 0.1023 0.0942 '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      tetragonal
_space_group_IT_number           86
_space_group_name_H-M_alt        'P 42/n'
_space_group_name_Hall           '-P 4bc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y, x+1/2, z+1/2'
'y+1/2, -x, z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y, -x-1/2, -z-1/2'
'-y-1/2, x, -z-1/2'

_cell_length_a                   10.35730(10)
_cell_length_b                   10.35730(10)
_cell_length_c                   14.6992(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1576.84(4)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    19984
_cell_measurement_temperature    233
_cell_measurement_theta_max      30.3990
_cell_measurement_theta_min      2.3950
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             880
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -1 0 0.0461
1 1 0 0.0638
-2 1 20 0.0927
2 -2 -20 0.1244
8 9 -11 0.1145
-13 7 1 0.0952
-8 12 -5 0.1083
6 -13 6 0.1006
13 -6 -2 0.1020
-10 7 11 0.0969
-2 14 1 0.0944
6 -13 -6 0.1291
10 -8 11 0.1001
-7 9 -13 0.1155

_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0003 -1.0001 0.0002 -0.0283 0.0410 -0.0831
1.0003 1.0001 -0.0002 0.0283 -0.0410 0.0831
-2.4925 1.4235 20.3148 0.3986 -0.7290 -0.5564
2.2238 -1.7283 -20.3302 -0.4058 0.7424 0.5331
8.2676 9.3650 -10.7253 -0.0866 -0.0629 0.9943
-12.5197 7.4911 0.8953 -0.7902 -0.5434 -0.2835
-7.5904 12.0213 -4.7534 -0.7970 -0.5498 0.2499
6.1518 -12.5865 5.8661 0.7668 0.5294 -0.3629
13.2351 -5.9437 -2.3451 0.7513 0.5162 0.4111
-9.9995 7.4807 10.7388 -0.3896 -0.8218 -0.4157
-1.5970 14.4936 1.2216 -0.3819 -0.7998 0.4631
6.0626 -12.5458 -6.2137 0.4288 0.9009 -0.0669
9.7340 -7.9397 10.5730 0.9733 0.1818 -0.1402
-6.7563 9.4881 -12.5039 -0.9093 -0.1706 0.3796

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28348
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.243
_diffrn_reflns_theta_min         1.966
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      233
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -35.00  22.00   0.25    1.00    --  -12.59 -80.00-110.00  228
  2  ω    -17.00  22.00   0.25    1.00    --  -12.59 -99.00 -60.00  156
  3  ω    -88.00  22.00   0.25    1.00    --  -12.59 -77.00  90.00  440
  4  ω    -17.00  32.00   0.25    1.00    --  -12.59 -99.00 150.00  196
  5  ω     45.00  96.00   0.25    1.00    --   13.22-178.00  30.00  204
  6  ω    -36.00  49.00   0.25    1.00    --   13.22 -80.00-110.00  340
  7  ω    -44.00  68.00   0.25    1.00    --  -12.59  38.00-150.00  448
  8  ω    -48.00  43.00   0.25    1.00    --  -12.59  80.00  13.00  364
  9  ω    -47.00  63.00   0.25    1.00    --  -12.59  77.00  60.00  440
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0513103000
_diffrn_orient_matrix_UB_12      -0.0230164000
_diffrn_orient_matrix_UB_13      0.0275314000
_diffrn_orient_matrix_UB_21      0.0104172000
_diffrn_orient_matrix_UB_22      -0.0514215000
_diffrn_orient_matrix_UB_23      -0.0310060000
_diffrn_orient_matrix_UB_31      0.0441562000
_diffrn_orient_matrix_UB_32      0.0389008000
_diffrn_orient_matrix_UB_33      -0.0246969000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1965
_reflns_number_total             2130
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.882
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2130
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0588
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1179P)²+0.3870P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1593
_refine_ls_wR_factor_ref         0.1635
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.543(3)
 0.457(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups, All N(H,H,H,H)
  groups
3. Restrained distances
 N1-H1A = N1-H1B = N1-H1C = N1-H1D
 1.08 with sigma of 0.02
 H1A-H1B = H1A-H1C = H1B-H1C = H1A-H1D = H1B-H1D = H1C-H1D
 1.75 with sigma of 0.04
4. Others
 Sof(H3BC)=Sof(H3BD)=Sof(H1BC)=Sof(H1BD)=Sof(H2A)=Sof(H2B)=Sof(N2)=1-FVAR(1)
 Sof(P001)=Sof(H3AA)=Sof(H3AB)=Sof(H1AA)=Sof(H1AB)=FVAR(1)
 Fixed Sof: H4A(0.5) H4B(0.5) H1A(0.5) H1B(0.5) H1C(0.5) H1D(0.5)
5.a Ternary CH refined with riding coordinates:
 N3(H3)
5.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C3(H3AA,H3AB), C3(H3BC,H3BD), C1(H1AA,H1AB), C1(H1BC,H1BD),
 C2(H2A,H2B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
P001 P 0.7437(2) 0.8980(2) 0.58624(15) 0.0249(5) Uani 0.496(8) 1 d . . P A 1
N3 N 0.63273(13) 0.74509(17) 0.44794(9) 0.0201(3) Uani 1 1 d . . . . .
H3 H 0.556304 0.741855 0.407556 0.024 Uiso 1 1 calc R U . . .
F4 F 0.4891(2) 0.90787(18) 0.32559(11) 0.0507(5) Uani 1 1 d . . . . .
N1 N 0.750000 1.250000 0.24261(16) 0.0287(5) Uani 1 2 d DS T P . .
F5 F 0.35233(14) 0.71168(19) 0.45129(11) 0.0478(5) Uani 1 1 d . . . . .
F6 F 0.28866(19) 0.85148(15) 0.56156(11) 0.0478(5) Uani 1 1 d . . . . .
F3 F 0.50586(18) 1.11280(17) 0.27557(15) 0.0531(5) Uani 1 1 d . . . . .
F1 F 0.4288(3) 0.9553(3) 0.18320(12) 0.0678(7) Uani 1 1 d . . . . .
F2 F 0.64196(19) 0.9611(2) 0.22253(16) 0.0593(6) Uani 1 1 d . . . . .
C4 C 0.750000 0.750000 0.38897(17) 0.0264(5) Uani 1 2 d S T P . .
H4A H 0.753211 0.673374 0.349918 0.032 Uiso 0.5 1 calc R U P . .
H4B H 0.746787 0.826623 0.349916 0.032 Uiso 0.5 1 calc R U P . .
C3 C 0.6320(2) 0.6239(2) 0.50562(15) 0.0283(4) Uani 1 1 d . . . . .
H3AA H 0.633494 0.549650 0.464308 0.034 Uiso 0.496(8) 1 calc R U P A 1
H3AB H 0.549508 0.621052 0.538243 0.034 Uiso 0.496(8) 1 calc R U P A 1
H3BC H 0.632179 0.546555 0.467216 0.034 Uiso 0.504(8) 1 calc R U P A 2
H3BD H 0.555731 0.621666 0.545067 0.034 Uiso 0.504(8) 1 calc R U P A 2
C1 C 0.6212(2) 0.8659(2) 0.50640(15) 0.0285(4) Uani 1 1 d . . . . .
H1AA H 0.539191 0.860962 0.539451 0.034 Uiso 0.496(8) 1 calc R U P A 1
H1AB H 0.615546 0.940363 0.465428 0.034 Uiso 0.496(8) 1 calc R U P A 1
H1BC H 0.614401 0.943331 0.468349 0.034 Uiso 0.504(8) 1 calc R U P A 2
H1BD H 0.545292 0.861048 0.546039 0.034 Uiso 0.504(8) 1 calc R U P A 2
C2 C 0.750000 0.750000 0.63301(19) 0.0400(8) Uani 1 2 d S T P . .
H2A H 0.672754 0.746420 0.671431 0.048 Uiso 0.504(8) 1 calc R U P A 2
H2B H 0.827247 0.753581 0.671430 0.048 Uiso 0.504(8) 1 calc R U P A 2
B2 B 0.250000 0.750000 0.50648(19) 0.0255(6) Uani 1 2 d S T P . .
B1 B 0.5148(3) 0.9849(3) 0.25115(14) 0.0267(4) Uani 1 1 d . . . . .
N2 N 0.7445(7) 0.8682(7) 0.5620(5) 0.0257(11) Uani 0.504(8) 1 d . . P A 2
H1A H 0.662(3) 1.308(5) 0.252(3) 0.031 Uiso 0.5 1 d D U P B -1
H1B H 0.715(5) 1.155(2) 0.243(3) 0.031 Uiso 0.5 1 d D U P C -1
H1C H 0.780(4) 1.274(4) 0.1733(15) 0.031 Uiso 0.5 1 d D U P D -1
H1D H 0.824(3) 1.282(4) 0.285(3) 0.031 Uiso 0.5 1 d D U P E -1

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P001 0.0231(5) 0.0266(9) 0.0249(9) -0.0108(5) 0.0014(6) -0.0014(6)
N3 0.0165(6) 0.0248(7) 0.0191(6) -0.0002(6) -0.0028(5) 0.0002(6)
F4 0.0596(10) 0.0522(10) 0.0403(8) 0.0194(7) -0.0057(7) -0.0027(8)
N1 0.0325(12) 0.0255(11) 0.0280(10) 0.000 0.000 -0.0001(11)
F5 0.0271(7) 0.0700(12) 0.0461(8) -0.0026(7) 0.0079(6) 0.0049(7)
F6 0.0643(12) 0.0348(8) 0.0444(8) -0.0073(6) -0.0069(7) -0.0123(7)
F3 0.0476(10) 0.0308(8) 0.0808(12) -0.0121(8) 0.0150(9) -0.0009(7)
F1 0.0800(15) 0.0777(14) 0.0456(9) 0.0159(9) -0.0329(10) -0.0333(11)
F2 0.0449(10) 0.0592(12) 0.0738(12) -0.0155(10) 0.0243(9) 0.0061(8)
C4 0.0239(11) 0.0398(14) 0.0154(10) 0.000 0.000 -0.0010(12)
C3 0.0292(10) 0.0237(9) 0.0320(9) 0.0039(7) 0.0036(8) -0.0028(7)
C1 0.0320(11) 0.0241(10) 0.0295(9) -0.0030(8) 0.0004(8) 0.0021(7)
C2 0.0260(12) 0.078(3) 0.0157(11) 0.000 0.000 0.0064(16)
B2 0.0226(12) 0.0276(13) 0.0262(12) 0.000 0.000 -0.0009(12)
B1 0.0287(12) 0.0257(12) 0.0257(9) -0.0007(8) -0.0004(8) 0.0014(8)
N2 0.026(2) 0.024(2) 0.027(3) -0.0075(18) -0.004(2) 0.003(2)

_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
P001 C3 1.764(3) 2_665 ?
P001 C1 1.760(3) . ?
P001 C2 1.682(2) . ?
N3 H3 0.9900 . ?
N3 C4 1.493(2) . ?
N3 C3 1.515(2) . ?
N3 C1 1.523(2) . ?
F4 B1 1.380(3) . ?
N1 H1A 1.099(18) . ?
N1 H1B 1.050(18) . ?
N1 H1C 1.094(17) . ?
N1 H1D 1.045(17) . ?
F5 B2 1.393(2) . ?
F6 B2 1.386(2) . ?
F3 B1 1.376(3) . ?
F1 B1 1.373(3) . ?
F2 B1 1.404(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C3 H3AA 0.9800 . ?
C3 H3AB 0.9800 . ?
C3 H3BC 0.9800 . ?
C3 H3BD 0.9800 . ?
C3 N2 1.527(8) 2_665 ?
C1 H1AA 0.9800 . ?
C1 H1AB 0.9800 . ?
C1 H1BC 0.9800 . ?
C1 H1BD 0.9800 . ?
C1 N2 1.517(7) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 N2 1.609(6) . ?
C2 N2 1.609(6) 2_665 ?

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
C1 P001 C3 93.09(14) . 2_665 ?
C2 P001 C3 97.41(15) . 2_665 ?
C2 P001 C1 97.36(15) . . ?
C4 N3 H3 107.7 . . ?
C4 N3 C3 110.94(13) . . ?
C4 N3 C1 111.30(13) . . ?
C3 N3 H3 107.7 . . ?
C3 N3 C1 111.40(14) . . ?
C1 N3 H3 107.7 . . ?
H1A N1 H1B 103(3) . . ?
H1A N1 H1C 103(3) . . ?
H1A N1 H1D 111(3) . . ?
H1B N1 H1C 109(3) . . ?
H1B N1 H1D 123(3) . . ?
H1C N1 H1D 106(3) . . ?
N3 C4 N3 109.02(18) 2_665 . ?
N3 C4 H4A 109.9 2_665 . ?
N3 C4 H4A 109.9 . . ?
N3 C4 H4B 109.9 2_665 . ?
N3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
P001 C3 H3AA 107.7 2_665 . ?
P001 C3 H3AB 107.7 2_665 . ?
N3 C3 P001 118.61(16) . 2_665 ?
N3 C3 H3AA 107.7 . . ?
N3 C3 H3AB 107.7 . . ?
N3 C3 H3BC 110.8 . . ?
N3 C3 H3BD 110.8 . . ?
N3 C3 N2 104.8(3) . 2_665 ?
H3AA C3 H3AB 107.1 . . ?
H3BC C3 H3BD 108.9 . . ?
N2 C3 H3BC 110.8 2_665 . ?
N2 C3 H3BD 110.8 2_665 . ?
P001 C1 H1AA 107.7 . . ?
P001 C1 H1AB 107.7 . . ?
N3 C1 P001 118.36(16) . . ?
N3 C1 H1AA 107.7 . . ?
N3 C1 H1AB 107.7 . . ?
N3 C1 H1BC 110.8 . . ?
N3 C1 H1BD 110.8 . . ?
H1AA C1 H1AB 107.1 . . ?
H1BC C1 H1BD 108.9 . . ?
N2 C1 N3 104.5(4) . . ?
N2 C1 H1BC 110.8 . . ?
N2 C1 H1BD 110.8 . . ?
P001 C2 P001 131.7(2) 2_665 . ?
H2A C2 H2B 109.6 . . ?
N2 C2 H2A 111.9 . . ?
N2 C2 H2A 111.9 2_665 . ?
N2 C2 H2B 111.9 . . ?
N2 C2 H2B 111.9 2_665 . ?
N2 C2 N2 99.2(7) . 2_665 ?
F5 B2 F5 108.7(2) 2_565 . ?
F6 B2 F5 109.67(9) . . ?
F6 B2 F5 109.67(9) 2_565 2_565 ?
F6 B2 F5 110.12(10) . 2_565 ?
F6 B2 F5 110.13(10) 2_565 . ?
F6 B2 F6 108.5(2) 2_565 . ?
F4 B1 F2 108.5(2) . . ?
F3 B1 F4 109.67(19) . . ?
F3 B1 F2 108.1(2) . . ?
F1 B1 F4 108.8(2) . . ?
F1 B1 F3 111.2(2) . . ?
F1 B1 F2 110.6(2) . . ?
C3 N2 C2 111.3(4) 2_665 . ?
C1 N2 C3 114.4(5) . 2_665 ?
C1 N2 C2 111.6(4) . . ?

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
N3 C1 N2 C3 60.7(5) . . . 2_665 ?
N3 C1 N2 C2 -66.8(5) . . . . ?
C4 N3 C3 P001 63.1(2) . . . 2_665 ?
C4 N3 C3 N2 59.4(3) . . . 2_665 ?
C4 N3 C1 P001 -62.5(2) . . . . ?
C4 N3 C1 N2 -59.1(3) . . . . ?
C3 P001 C1 N3 49.76(18) 2_665 . . . ?
C3 P001 C2 P001 -46.85(10) 2_665 . . 2_665 ?
C3 N3 C4 N3 -62.41(11) . . . 2_665 ?
C3 N3 C1 P001 61.9(2) . . . . ?
C3 N3 C1 N2 65.3(3) . . . . ?
C1 P001 C2 P001 47.25(10) . . . 2_665 ?
C1 N3 C4 N3 62.24(11) . . . 2_665 ?
C1 N3 C3 P001 -61.4(2) . . . 2_665 ?
C1 N3 C3 N2 -65.2(3) . . . 2_665 ?
C2 P001 C1 N3 -48.1(2) . . . . ?
N2 C2 N2 C3 -64.3(4) 2_665 . . 2_665 ?
N2 C2 N2 C1 64.8(5) 2_665 . . . ?

_shelx_res_file                  
;
TITL rt1_a.res in P4(2)/n
    p-bf4_233k.res
    created by SHELXL-2018/3 at 11:26:11 on 08-Jan-2025
REM Old TITL RT1 in P4(2)/n
REM SHELXT solution in P4(2)/n: R1 0.294, Rweak 0.087, Alpha 0.145
REM <I/s> 0.455 for 72 systematic absences, Orientation as input
REM Formula found by SHELXT: C5 B4 N5 F12
CELL 0.71073 10.3573 10.3573 14.6992 90 90 90
ZERR 3 0.0001 0.0001 0.0003 0 0 0
LATT 1
SYMM 0.5-X,0.5-Y,+Z
SYMM -Y,0.5+X,0.5+Z
SYMM 0.5+Y,-X,0.5+Z
SFAC C H B F N P
UNIT 24 72.07 12 48 16.03 3.97
DFIX 1.08 N1 H1a N1 H1b N1 H1c N1 H1d
DANG 1.75 H1a H1b H1a H1c H1b H1c H1a H1d H1b H1d H1c H1d

L.S. 8
PLAN  8
SIZE 0.11 0.22 0.23
TEMP -40.15
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
acta
TWIN 0 1 0 1 0 0 0 0 -1 2
REM <olex2.extras>
REM <HklSrc "%.\\p-BF4_233K.hkl">
REM </olex2.extras>

WGHT    0.117900    0.387000
BASF   0.45737
FVAR       0.46776   0.49575
PART 1
P001  6    0.743723    0.898046    0.586240    21.00000    0.02305    0.02660 =
         0.02490   -0.01083    0.00137   -0.00137
PART 0
N3    5    0.632733    0.745086    0.447939    11.00000    0.01650    0.02485 =
         0.01909   -0.00018   -0.00281    0.00018
AFIX  13
H3    2    0.556304    0.741855    0.407556    11.00000   -1.20000
AFIX   0

F4    4    0.489076    0.907871    0.325590    11.00000    0.05965    0.05222 =
         0.04035    0.01936   -0.00567   -0.00274
N1    5    0.750000    1.250000    0.242611    10.50000    0.03253    0.02552 =
         0.02800    0.00000    0.00000   -0.00005
F5    4    0.352333    0.711677    0.451287    11.00000    0.02710    0.07004 =
         0.04614   -0.00259    0.00785    0.00487
F6    4    0.288664    0.851481    0.561555    11.00000    0.06433    0.03476 =
         0.04441   -0.00731   -0.00690   -0.01230
F3    4    0.505861    1.112803    0.275575    11.00000    0.04755    0.03080 =
         0.08082   -0.01209    0.01496   -0.00087
F1    4    0.428805    0.955310    0.183198    11.00000    0.07997    0.07775 =
         0.04559    0.01592   -0.03295   -0.03331
F2    4    0.641957    0.961100    0.222531    11.00000    0.04493    0.05925 =
         0.07377   -0.01554    0.02434    0.00609
C4    1    0.750000    0.750000    0.388965    10.50000    0.02392    0.03980 =
         0.01539    0.00000    0.00000   -0.00104
AFIX  23
H4A   2    0.753211    0.673374    0.349918    10.50000   -1.20000
H4B   2    0.746787    0.826623    0.349916    10.50000   -1.20000
AFIX   0
C3    1    0.631976    0.623901    0.505618    11.00000    0.02923    0.02375 =
         0.03198    0.00389    0.00357   -0.00279
PART 1
AFIX  23
H3AA  2    0.633494    0.549650    0.464308    21.00000   -1.20000
H3AB  2    0.549508    0.621052    0.538243    21.00000   -1.20000
AFIX  23
PART 2
H3BC  2    0.632179    0.546555    0.467216   -21.00000   -1.20000
H3BD  2    0.555731    0.621666    0.545067   -21.00000   -1.20000
AFIX   0
PART 0
C1    1    0.621216    0.865938    0.506402    11.00000    0.03197    0.02409 =
         0.02950   -0.00298    0.00036    0.00215
PART 1
AFIX  23
H1AA  2    0.539191    0.860962    0.539451    21.00000   -1.20000
H1AB  2    0.615546    0.940363    0.465428    21.00000   -1.20000
AFIX  23
PART 2
H1BC  2    0.614401    0.943331    0.468349   -21.00000   -1.20000
H1BD  2    0.545292    0.861048    0.546039   -21.00000   -1.20000
AFIX   0
PART 0
C2    1    0.750000    0.750000    0.633011    10.50000    0.02598    0.07830 =
         0.01574    0.00000    0.00000    0.00641
PART 2
AFIX  23
H2A   2    0.672754    0.746420    0.671431   -21.00000   -1.20000
H2B   2    0.827247    0.753581    0.671430   -21.00000   -1.20000
AFIX   0

PART 0
B2    3    0.250000    0.750000    0.506480    10.50000    0.02264    0.02763 =
         0.02621    0.00000    0.00000   -0.00091

B1    3    0.514812    0.984872    0.251148    11.00000    0.02874    0.02575 =
         0.02566   -0.00067   -0.00040    0.00141
PART 2
N2    5    0.744520    0.868196    0.562046   -21.00000    0.02589    0.02375 =
         0.02745   -0.00748   -0.00353    0.00331
PART -1
H1A   2    0.661871    1.307565    0.252220    10.50000   -1.20000
H1B   2    0.715418    1.154724    0.243355    10.50000   -1.20000
H1C   2    0.779845    1.274258    0.173266    10.50000   -1.20000
H1D   2    0.824258    1.282219    0.285012    10.50000   -1.20000
HKLF 4




REM  rt1_a.res in P4(2)/n
REM wR2 = 0.1635, GooF = S = 1.070, Restrained GooF = 1.071 for all data
REM R1 = 0.0588 for 1965 Fo > 4sig(Fo) and 0.0622 for all 2130 data
REM 143 parameters refined using 10 restraints

END

WGHT      0.1179      0.3870

REM Highest difference peak  0.882,  deepest hole -0.324,  1-sigma level  0.091
Q1    1   0.5926  1.0067  0.1737  11.00000  0.05    0.88
Q2    1   0.5450  1.0637  0.3169  11.00000  0.05    0.69
Q3    1   0.3802  0.9986  0.2218  11.00000  0.05    0.67
Q4    1   0.5262  0.8564  0.2794  11.00000  0.05    0.61
Q5    1   0.3511  0.7855  0.4547  11.00000  0.05    0.44
Q6    1   0.2141  0.8463  0.5589  11.00000  0.05    0.43
Q7    1   0.6241  0.7680  0.4504  11.00000  0.05    0.39
Q8    1   0.6732  0.6221  0.5353  11.00000  0.05    0.33
;
_shelx_res_checksum              41976
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.871
_oxdiff_exptl_absorpt_empirical_full_min 0.459
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.543(3)
2 0.457(3)

