# Supplementary Information (SI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_e23ab7a
_database_code_depnum_ccdc_archive 'CCDC 2374662'
loop_
_audit_author_name
_audit_author_address
'Gabriele Kociok-Kohn'
;University of Bath
United Kingdom
;
_audit_update_record             
;
2024-07-30 deposited with the CCDC.	2024-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H26 N2 P, Br '
_chemical_formula_sum            'C22 H26 Br N2 P'
_chemical_formula_weight         429.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.4539(5)
_cell_length_b                   16.8444(9)
_cell_length_c                   13.8253(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.865(7)
_cell_angle_gamma                90
_cell_volume                     2070.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7811
_cell_measurement_theta_min      3.3850
_cell_measurement_theta_max      29.5550

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.641
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.091
_exptl_absorpt_coefficient_mu    2.071
_shelx_estimated_absorpt_T_min   0.350
_shelx_estimated_absorpt_T_max   0.834
_exptl_absorpt_correction_T_min  0.74544
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.866
_oxdiff_exptl_absorpt_empirical_full_max 1.367
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      149.9(5)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0734
_diffrn_reflns_number            17883
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.133
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4729
_reflns_number_gt                3891
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  
;
 SHELXL-2019/2 (Sheldrick, 2019)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0783P)²+5.8002P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4729
_refine_ls_number_parameters     241
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1511
_refine_ls_wR_factor_gt          0.1427
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br 0.08033(5) 0.65129(2) 0.29666(3) 0.02559(15) Uani 1 1 d . . . . .
P P 0.31709(9) 0.43359(5) 0.28521(6) 0.00933(18) Uani 1 1 d . . . . .
N1 N 0.3370(3) 0.52882(17) 0.2886(2) 0.0139(6) Uani 1 1 d D . . . .
H1 H 0.265(4) 0.560(2) 0.282(3) 0.022(12) Uiso 1 1 d D . . . .
N2 N 0.5216(3) 0.56534(19) 0.1501(2) 0.0171(6) Uani 1 1 d . . . . .
C1 C 0.2574(4) 0.3970(2) 0.3870(3) 0.0113(6) Uani 1 1 d . . . . .
C2 C 0.1888(4) 0.4481(2) 0.4378(3) 0.0134(7) Uani 1 1 d . . . . .
H2 H 0.174602 0.502522 0.419152 0.016 Uiso 1 1 calc R U . . .
C3 C 0.1420(4) 0.4187(2) 0.5153(3) 0.0162(7) Uani 1 1 d . . . . .
H3 H 0.095913 0.453309 0.550036 0.019 Uiso 1 1 calc R U . . .
C4 C 0.1614(4) 0.3393(2) 0.5428(3) 0.0176(7) Uani 1 1 d . . . . .
H4 H 0.129385 0.319793 0.596485 0.021 Uiso 1 1 calc R U . . .
C5 C 0.2276(4) 0.2883(2) 0.4921(3) 0.0186(7) Uani 1 1 d . . . . .
H5 H 0.239960 0.233713 0.510291 0.022 Uiso 1 1 calc R U . . .
C6 C 0.2759(4) 0.3173(2) 0.4144(3) 0.0179(7) Uani 1 1 d . . . . .
H6 H 0.321711 0.282429 0.379767 0.021 Uiso 1 1 calc R U . . .
C7 C 0.1776(4) 0.4067(2) 0.1655(2) 0.0107(6) Uani 1 1 d . . . . .
C8 C 0.0619(4) 0.3534(2) 0.1605(3) 0.0153(7) Uani 1 1 d . . . . .
H8 H 0.054841 0.330780 0.221567 0.018 Uiso 1 1 calc R U . . .
C9 C -0.0429(4) 0.3339(2) 0.0652(3) 0.0191(7) Uani 1 1 d . . . . .
H9 H -0.122082 0.297949 0.061208 0.023 Uiso 1 1 calc R U . . .
C10 C -0.0320(4) 0.3669(2) -0.0241(3) 0.0181(7) Uani 1 1 d . . . . .
H10 H -0.103920 0.353500 -0.088969 0.022 Uiso 1 1 calc R U . . .
C11 C 0.0835(4) 0.4192(2) -0.0189(3) 0.0165(7) Uani 1 1 d . . . . .
H11 H 0.090889 0.441031 -0.080370 0.020 Uiso 1 1 calc R U . . .
C12 C 0.1880(4) 0.4399(2) 0.0749(3) 0.0131(7) Uani 1 1 d . . . . .
H12 H 0.266194 0.476320 0.078211 0.016 Uiso 1 1 calc R U . . .
C13 C 0.4931(4) 0.3863(2) 0.3002(3) 0.0119(6) Uani 1 1 d . . . . .
C14 C 0.5212(4) 0.3510(2) 0.2168(3) 0.0155(7) Uani 1 1 d . . . . .
H14 H 0.446015 0.351418 0.150474 0.019 Uiso 1 1 calc R U . . .
C15 C 0.6591(4) 0.3156(2) 0.2314(3) 0.0205(8) Uani 1 1 d . . . . .
H15 H 0.677939 0.290936 0.175125 0.025 Uiso 1 1 calc R U . . .
C16 C 0.7701(4) 0.3158(2) 0.3281(3) 0.0201(8) Uani 1 1 d . . . . .
H16 H 0.865091 0.292194 0.337450 0.024 Uiso 1 1 calc R U . . .
C17 C 0.7429(4) 0.3504(2) 0.4106(3) 0.0205(8) Uani 1 1 d . . . . .
H17 H 0.818930 0.350331 0.476584 0.025 Uiso 1 1 calc R U . . .
C18 C 0.6042(4) 0.3852(2) 0.3973(3) 0.0170(7) Uani 1 1 d . . . . .
H18 H 0.584977 0.408238 0.454279 0.020 Uiso 1 1 calc R U . . .
C19 C 0.4739(4) 0.5767(2) 0.3160(3) 0.0154(7) Uani 1 1 d . . . . .
H19A H 0.562367 0.542022 0.346524 0.019 Uiso 1 1 calc R U . . .
H19B H 0.472265 0.616433 0.368425 0.019 Uiso 1 1 calc R U . . .
C20 C 0.4892(4) 0.6194(2) 0.2229(3) 0.0168(7) Uani 1 1 d . . . . .
H20A H 0.394620 0.648246 0.187126 0.020 Uiso 1 1 calc R U . . .
H20B H 0.570999 0.659043 0.246739 0.020 Uiso 1 1 calc R U . . .
C21 C 0.6782(4) 0.5379(3) 0.1889(3) 0.0280(9) Uani 1 1 d . . . . .
H21A H 0.697126 0.503130 0.137798 0.042 Uiso 1 1 calc R U . . .
H21B H 0.696209 0.508569 0.253148 0.042 Uiso 1 1 calc R U . . .
H21C H 0.745824 0.583809 0.201610 0.042 Uiso 1 1 calc R U . . .
C22 C 0.4912(6) 0.6059(3) 0.0513(3) 0.0318(10) Uani 1 1 d . . . . .
H22A H 0.514078 0.570156 0.002655 0.048 Uiso 1 1 calc R U . . .
H22B H 0.554272 0.653485 0.061223 0.048 Uiso 1 1 calc R U . . .
H22C H 0.384977 0.621269 0.023913 0.048 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P N1 1.614(3) . ?
P C7 1.789(3) . ?
P C13 1.792(3) . ?
P C1 1.795(3) . ?
N1 C19 1.462(4) . ?
N1 H1 0.835(19) . ?
N2 C20 1.465(5) . ?
N2 C22 1.466(5) . ?
N2 C21 1.467(5) . ?
C1 C6 1.389(5) . ?
C1 C2 1.401(5) . ?
C2 C3 1.382(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.397(5) . ?
C7 C12 1.405(5) . ?
C8 C9 1.392(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.395(5) . ?
C13 C14 1.401(5) . ?
C14 C15 1.385(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.392(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.523(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
N1 P C7 108.73(16) . . ?
N1 P C13 110.13(15) . . ?
C7 P C13 110.95(15) . . ?
N1 P C1 112.53(16) . . ?
C7 P C1 108.00(15) . . ?
C13 P C1 106.49(15) . . ?
C19 N1 P 129.8(2) . . ?
C19 N1 H1 107(3) . . ?
P N1 H1 122(3) . . ?
C20 N2 C22 109.3(3) . . ?
C20 N2 C21 111.4(3) . . ?
C22 N2 C21 110.0(3) . . ?
C6 C1 C2 119.6(3) . . ?
C6 C1 P 120.1(3) . . ?
C2 C1 P 120.3(3) . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.7(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 120.4(3) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C12 120.1(3) . . ?
C8 C7 P 121.8(3) . . ?
C12 C7 P 118.1(2) . . ?
C9 C8 C7 119.5(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C8 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 119.5(3) . . ?
C11 C12 H12 120.3 . . ?
C7 C12 H12 120.3 . . ?
C18 C13 C14 119.7(3) . . ?
C18 C13 P 118.9(3) . . ?
C14 C13 P 121.5(3) . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.2(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.0(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C13 120.1(3) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
N1 C19 C20 111.8(3) . . ?
N1 C19 H19A 109.3 . . ?
C20 C19 H19A 109.3 . . ?
N1 C19 H19B 109.3 . . ?
C20 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
N2 C20 C19 113.0(3) . . ?
N2 C20 H20A 109.0 . . ?
C19 C20 H20A 109.0 . . ?
N2 C20 H20B 109.0 . . ?
C19 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 P N1 C19 -131.6(3) . . . . ?
C13 P N1 C19 -9.9(4) . . . . ?
C1 P N1 C19 108.8(3) . . . . ?
N1 P C1 C6 -161.4(3) . . . . ?
C7 P C1 C6 78.6(3) . . . . ?
C13 P C1 C6 -40.7(3) . . . . ?
N1 P C1 C2 20.0(3) . . . . ?
C7 P C1 C2 -100.0(3) . . . . ?
C13 P C1 C2 140.8(3) . . . . ?
C6 C1 C2 C3 0.7(5) . . . . ?
P C1 C2 C3 179.3(3) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C2 C1 C6 C5 -0.4(5) . . . . ?
P C1 C6 C5 -179.0(3) . . . . ?
C4 C5 C6 C1 -0.3(5) . . . . ?
N1 P C7 C8 -133.2(3) . . . . ?
C13 P C7 C8 105.5(3) . . . . ?
C1 P C7 C8 -10.8(3) . . . . ?
N1 P C7 C12 47.6(3) . . . . ?
C13 P C7 C12 -73.7(3) . . . . ?
C1 P C7 C12 170.0(3) . . . . ?
C12 C7 C8 C9 -0.2(5) . . . . ?
P C7 C8 C9 -179.4(3) . . . . ?
C7 C8 C9 C10 0.3(5) . . . . ?
C8 C9 C10 C11 0.2(6) . . . . ?
C9 C10 C11 C12 -0.7(5) . . . . ?
C10 C11 C12 C7 0.8(5) . . . . ?
C8 C7 C12 C11 -0.4(5) . . . . ?
P C7 C12 C11 178.9(3) . . . . ?
N1 P C13 C18 74.3(3) . . . . ?
C7 P C13 C18 -165.3(3) . . . . ?
C1 P C13 C18 -48.0(3) . . . . ?
N1 P C13 C14 -105.5(3) . . . . ?
C7 P C13 C14 15.0(3) . . . . ?
C1 P C13 C14 132.3(3) . . . . ?
C18 C13 C14 C15 -0.2(5) . . . . ?
P C13 C14 C15 179.6(3) . . . . ?
C13 C14 C15 C16 -0.9(6) . . . . ?
C14 C15 C16 C17 1.0(6) . . . . ?
C15 C16 C17 C18 -0.1(6) . . . . ?
C16 C17 C18 C13 -0.9(6) . . . . ?
C14 C13 C18 C17 1.1(5) . . . . ?
P C13 C18 C17 -178.7(3) . . . . ?
P N1 C19 C20 110.5(3) . . . . ?
C22 N2 C20 C19 163.6(3) . . . . ?
C21 N2 C20 C19 -74.7(4) . . . . ?
N1 C19 C20 N2 -70.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 Br 0.835(19) 2.39(2) 3.215(3) 169(4) . yes

_refine_diff_density_max         0.768
_refine_diff_density_min         -0.990
_refine_diff_density_rms         0.117



####################################################################### 
# 
# 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_e23ab4
_database_code_depnum_ccdc_archive 'CCDC 2374926'
loop_
_audit_author_name
_audit_author_address
'Gabriele Kociok-Kohn'
;University of Bath
United Kingdom
;
_audit_update_record             
;
2024-07-31 deposited with the CCDC.	2024-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H23 N P, Br'
_chemical_formula_sum            'C25 H23 Br N P'
_chemical_formula_weight         448.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.1188(4)
_cell_length_b                   18.1495(6)
_cell_length_c                   21.2078(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4279.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7411
_cell_measurement_theta_min      3.5590
_cell_measurement_theta_max      29.1730

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_F_000             1840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    2.006
_shelx_estimated_absorpt_T_min   0.422
_shelx_estimated_absorpt_T_max   0.678
_exptl_absorpt_correction_T_min  0.79427
_exptl_absorpt_correction_T_max  1.00000
_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.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.824
_oxdiff_exptl_absorpt_empirical_full_max 1.299
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      149.9(7)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0734
_diffrn_reflns_number            38624
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.954
_diffrn_reflns_theta_max         30.402
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5981
_reflns_number_gt                4300
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  
;
 SHELXL-2019/2 (Sheldrick, 2019)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0263P)²+3.5162P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5981
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.0810
_refine_ls_wR_factor_gt          0.0710
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P 0.63823(4) 0.36811(3) 0.66510(2) 0.01522(11) Uani 1 1 d . . . . .
C1 C 0.76256(17) 0.38069(10) 0.61212(9) 0.0167(4) Uani 1 1 d . . . . .
C2 C 0.85449(18) 0.32824(12) 0.61050(11) 0.0219(4) Uani 1 1 d . . . . .
H2 H 0.853314 0.287843 0.638981 0.026 Uiso 1 1 calc R U . . .
C3 C 0.94742(19) 0.33515(12) 0.56733(11) 0.0265(5) Uani 1 1 d . . . . .
H3 H 1.010694 0.299981 0.566802 0.032 Uiso 1 1 calc R U . . .
C4 C 0.94824(19) 0.39305(12) 0.52508(11) 0.0252(5) Uani 1 1 d . . . . .
H4 H 1.011157 0.397110 0.494971 0.030 Uiso 1 1 calc R U . . .
C5 C 0.85754(19) 0.44509(12) 0.52658(10) 0.0242(5) Uani 1 1 d . . . . .
H5 H 0.858995 0.485044 0.497653 0.029 Uiso 1 1 calc R U . . .
C6 C 0.76446(19) 0.43966(11) 0.56984(10) 0.0211(4) Uani 1 1 d . . . . .
H6 H 0.702549 0.475714 0.570701 0.025 Uiso 1 1 calc R U . . .
C7 C 0.50466(17) 0.37387(11) 0.61805(9) 0.0170(4) Uani 1 1 d . . . . .
C8 C 0.48959(19) 0.32501(12) 0.56791(10) 0.0222(5) Uani 1 1 d . . . . .
H8 H 0.548345 0.288200 0.559828 0.027 Uiso 1 1 calc R U . . .
C9 C 0.3889(2) 0.33038(12) 0.53004(11) 0.0248(5) Uani 1 1 d . . . . .
H9 H 0.377941 0.296820 0.496146 0.030 Uiso 1 1 calc R U . . .
C10 C 0.3040(2) 0.38438(14) 0.54132(11) 0.0312(5) Uani 1 1 d . . . . .
H10 H 0.235252 0.388180 0.514917 0.037 Uiso 1 1 calc R U . . .
C11 C 0.3188(2) 0.43251(16) 0.59056(13) 0.0434(7) Uani 1 1 d . . . . .
H11 H 0.259803 0.469292 0.598209 0.052 Uiso 1 1 calc R U . . .
C12 C 0.4192(2) 0.42804(14) 0.62937(11) 0.0323(6) Uani 1 1 d . . . . .
H12 H 0.429307 0.461682 0.663280 0.039 Uiso 1 1 calc R U . . .
C13 C 0.63552(17) 0.43755(11) 0.72449(9) 0.0168(4) Uani 1 1 d . . . . .
C14 C 0.70867(18) 0.49966(11) 0.72126(10) 0.0210(4) Uani 1 1 d . . . . .
H14 H 0.766012 0.504637 0.688327 0.025 Uiso 1 1 calc R U . . .
C15 C 0.6969(2) 0.55431(12) 0.76672(11) 0.0272(5) Uani 1 1 d . . . . .
H15 H 0.747845 0.596303 0.765242 0.033 Uiso 1 1 calc R U . . .
C16 C 0.6123(2) 0.54837(12) 0.81394(11) 0.0257(5) Uani 1 1 d . . . . .
H16 H 0.603251 0.586839 0.843933 0.031 Uiso 1 1 calc R U . . .
C17 C 0.54041(19) 0.48599(13) 0.81753(10) 0.0252(5) Uani 1 1 d . . . . .
H17 H 0.482880 0.481517 0.850426 0.030 Uiso 1 1 calc R U . . .
C18 C 0.55212(18) 0.43050(12) 0.77354(10) 0.0229(5) Uani 1 1 d . . . . .
H18 H 0.503652 0.387537 0.776539 0.028 Uiso 1 1 calc R U . . .
N1 N 0.63800(16) 0.28880(10) 0.70090(9) 0.0192(4) Uani 1 1 d . . . . .
H1 H 0.629(2) 0.2543(14) 0.6767(11) 0.027(7) Uiso 1 1 d . . . . .
C19 C 0.72183(19) 0.27234(12) 0.75267(10) 0.0227(5) Uani 1 1 d . . . . .
H19A H 0.752324 0.319272 0.770296 0.027 Uiso 1 1 calc R U . . .
H19B H 0.791440 0.244831 0.735555 0.027 Uiso 1 1 calc R U . . .
C20 C 0.66569(18) 0.22793(11) 0.80500(10) 0.0187(4) Uani 1 1 d . . . . .
C21 C 0.7312(2) 0.21859(13) 0.86027(11) 0.0279(5) Uani 1 1 d . . . . .
H21 H 0.806250 0.242929 0.865064 0.033 Uiso 1 1 calc R U . . .
C22 C 0.6884(3) 0.17442(14) 0.90826(12) 0.0370(6) Uani 1 1 d . . . . .
H22 H 0.734362 0.168239 0.945658 0.044 Uiso 1 1 calc R U . . .
C23 C 0.5786(3) 0.13904(14) 0.90196(12) 0.0373(6) Uani 1 1 d . . . . .
H23 H 0.549243 0.108338 0.934822 0.045 Uiso 1 1 calc R U . . .
C24 C 0.5121(2) 0.14872(13) 0.84766(12) 0.0323(5) Uani 1 1 d . . . . .
H24 H 0.436242 0.125151 0.843350 0.039 Uiso 1 1 calc R U . . .
C25 C 0.55569(19) 0.19276(12) 0.79932(11) 0.0243(5) Uani 1 1 d . . . . .
H25 H 0.509626 0.198850 0.761950 0.029 Uiso 1 1 calc R U . . .
Br Br 0.65636(2) 0.14270(2) 0.61388(2) 0.02362(7) Uani 1 1 d . . . . .


_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
P N1 1.6275(17) . ?
P C13 1.782(2) . ?
P C7 1.792(2) . ?
P C1 1.796(2) . ?
C1 C6 1.396(3) . ?
C1 C2 1.397(3) . ?
C2 C3 1.386(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.388(3) . ?
C7 C8 1.395(3) . ?
C8 C9 1.382(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.371(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.392(3) . ?
C13 C18 1.400(3) . ?
C14 C15 1.389(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
N1 C19 1.471(3) . ?
N1 H1 0.82(2) . ?
C19 C20 1.507(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C25 1.385(3) . ?
C20 C21 1.390(3) . ?
C21 C22 1.380(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.380(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.387(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

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
N1 P C13 107.21(10) . . ?
N1 P C7 108.06(9) . . ?
C13 P C7 109.77(9) . . ?
N1 P C1 113.92(9) . . ?
C13 P C1 111.42(9) . . ?
C7 P C1 106.38(9) . . ?
C6 C1 C2 119.69(19) . . ?
C6 C1 P 120.72(15) . . ?
C2 C1 P 119.46(16) . . ?
C3 C2 C1 120.0(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.8(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 119.39(19) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C12 C7 C8 120.00(19) . . ?
C12 C7 P 120.80(16) . . ?
C8 C7 P 119.14(15) . . ?
C9 C8 C7 119.7(2) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.7(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C7 C12 C11 119.3(2) . . ?
C7 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C18 119.86(19) . . ?
C14 C13 P 121.89(16) . . ?
C18 C13 P 118.16(15) . . ?
C15 C14 C13 119.3(2) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C16 C15 C14 120.8(2) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 119.8(2) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 120.3(2) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C13 119.9(2) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
C19 N1 P 121.80(14) . . ?
C19 N1 H1 113.0(17) . . ?
P N1 H1 112.7(17) . . ?
N1 C19 C20 113.31(17) . . ?
N1 C19 H19A 108.9 . . ?
C20 C19 H19A 108.9 . . ?
N1 C19 H19B 108.9 . . ?
C20 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C25 C20 C21 118.7(2) . . ?
C25 C20 C19 123.25(19) . . ?
C21 C20 C19 117.98(19) . . ?
C22 C21 C20 120.8(2) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 C23 120.1(2) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C24 C23 C22 119.6(2) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C23 C24 C25 120.2(2) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C20 C25 C24 120.7(2) . . ?
C20 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?

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
N1 P C1 C6 168.62(16) . . . . ?
C13 P C1 C6 -69.94(18) . . . . ?
C7 P C1 C6 49.67(18) . . . . ?
N1 P C1 C2 -7.3(2) . . . . ?
C13 P C1 C2 114.18(17) . . . . ?
C7 P C1 C2 -126.21(17) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
P C1 C2 C3 176.35(17) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
P C1 C6 C5 -175.59(16) . . . . ?
N1 P C7 C12 118.21(19) . . . . ?
C13 P C7 C12 1.6(2) . . . . ?
C1 P C7 C12 -119.08(19) . . . . ?
N1 P C7 C8 -64.47(19) . . . . ?
C13 P C7 C8 178.92(16) . . . . ?
C1 P C7 C8 58.24(18) . . . . ?
C12 C7 C8 C9 -0.6(3) . . . . ?
P C7 C8 C9 -177.95(17) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
C8 C7 C12 C11 0.4(4) . . . . ?
P C7 C12 C11 177.7(2) . . . . ?
C10 C11 C12 C7 -0.3(4) . . . . ?
N1 P C13 C14 136.05(17) . . . . ?
C7 P C13 C14 -106.80(18) . . . . ?
C1 P C13 C14 10.8(2) . . . . ?
N1 P C13 C18 -47.56(18) . . . . ?
C7 P C13 C18 69.59(18) . . . . ?
C1 P C13 C18 -172.83(16) . . . . ?
C18 C13 C14 C15 -0.6(3) . . . . ?
P C13 C14 C15 175.74(16) . . . . ?
C13 C14 C15 C16 -1.4(3) . . . . ?
C14 C15 C16 C17 2.1(3) . . . . ?
C15 C16 C17 C18 -0.9(3) . . . . ?
C16 C17 C18 C13 -1.0(3) . . . . ?
C14 C13 C18 C17 1.8(3) . . . . ?
P C13 C18 C17 -174.70(17) . . . . ?
C13 P N1 C19 -49.33(18) . . . . ?
C7 P N1 C19 -167.59(16) . . . . ?
C1 P N1 C19 74.42(19) . . . . ?
P N1 C19 C20 141.26(15) . . . . ?
N1 C19 C20 C25 13.1(3) . . . . ?
N1 C19 C20 C21 -170.68(18) . . . . ?
C25 C20 C21 C22 0.9(3) . . . . ?
C19 C20 C21 C22 -175.6(2) . . . . ?
C20 C21 C22 C23 -0.4(4) . . . . ?
C21 C22 C23 C24 -0.4(4) . . . . ?
C22 C23 C24 C25 0.9(4) . . . . ?
C21 C20 C25 C24 -0.4(3) . . . . ?
C19 C20 C25 C24 175.8(2) . . . . ?
C23 C24 C25 C20 -0.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 Br 0.82(2) 2.44(3) 3.2371(19) 165(2) . yes

_refine_diff_density_max         0.432
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.078



