# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_rybicaaccl_1wdsf_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2264850'
loop_
_audit_author_name
_audit_author_address
'Subrata Kundu'
;IIT Delhi
India
;
_audit_update_record             
;
2023-05-23 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;
_audit_creation_date             2023-05-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H33 Cl N P'
_chemical_formula_sum            'C22 H33 Cl N P'
_chemical_formula_weight         377.91
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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                   8.8488(4)
_cell_length_b                   16.8077(9)
_cell_length_c                   29.5760(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4398.8(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.191
_cell_measurement_theta_min      2.424
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.951
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1252 before and 0.0576 after correction.
The Ratio of minimum to maximum transmission is 0.9544.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            117468
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.290
_diffrn_reflns_theta_min         2.424
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3958
_reflns_number_total             5461
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         5461
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0625
_refine_ls_restrained_S_all      1.053
_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)+(0.0705P)²+2.3536P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1566
_refine_ls_wR_factor_ref         0.1711
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17), C20(H20), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C13(H13)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C9(H9A,H9B,H9C), C10(H10A,H10B,
 H10C), C8(H8A,H8B,H8C), C18(H18A,H18B,H18C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.86854(7) 0.65906(5) 0.34558(4) 0.0929(3) Uani 1 1 d . . . . .
P1 P 0.67687(7) 0.71527(4) 0.32047(3) 0.0596(2) Uani 1 1 d . . . . .
N1 N 0.49243(18) 0.61215(9) 0.37301(6) 0.0389(4) Uani 1 1 d . . . . .
C17 C 0.6240(4) 0.65717(16) 0.46007(10) 0.0756(9) Uani 1 1 d . . . . .
H17 H 0.541985 0.682483 0.443092 0.091 Uiso 1 1 calc R U . . .
C11 C 0.6106(2) 0.56334(12) 0.39209(8) 0.0447(5) Uani 1 1 d . . . . .
C16 C 0.6706(3) 0.58336(14) 0.43427(9) 0.0574(6) Uani 1 1 d . . . . .
C15 C 0.7813(3) 0.53368(18) 0.45242(11) 0.0786(8) Uani 1 1 d . . . . .
H15 H 0.823884 0.545854 0.480332 0.094 Uiso 1 1 calc R U . . .
C14 C 0.8285(4) 0.46671(19) 0.42945(13) 0.0880(10) Uani 1 1 d . . . . .
H14 H 0.900479 0.433479 0.442406 0.106 Uiso 1 1 calc R U . . .
C13 C 0.7705(3) 0.44863(16) 0.38785(11) 0.0728(8) Uani 1 1 d . . . . .
H13 H 0.805087 0.403723 0.372678 0.087 Uiso 1 1 calc R U . . .
C12 C 0.6604(3) 0.49629(13) 0.36777(9) 0.0540(6) Uani 1 1 d . . . . .
C5 C 0.3283(2) 0.59519(12) 0.38295(8) 0.0451(5) Uani 1 1 d . . . . .
C6 C 0.2520(3) 0.57450(14) 0.33829(8) 0.0549(6) Uani 1 1 d . . . . .
H6A H 0.290907 0.524293 0.327078 0.066 Uiso 1 1 calc R U . . .
H6B H 0.143964 0.568817 0.342895 0.066 Uiso 1 1 calc R U . . .
C7 C 0.2820(3) 0.63972(15) 0.30395(9) 0.0606(6) Uani 1 1 d . . . . .
H7A H 0.186614 0.659799 0.292478 0.073 Uiso 1 1 calc R U . . .
H7B H 0.338447 0.617984 0.278704 0.073 Uiso 1 1 calc R U . . .
C2 C 0.3722(3) 0.70856(12) 0.32547(7) 0.0466(5) Uani 1 1 d . . . . .
C1 C 0.5195(2) 0.67208(11) 0.34316(7) 0.0397(4) Uani 1 1 d . . . . .
C19 C 0.5646(5) 0.6392(2) 0.50714(12) 0.1018(12) Uani 1 1 d . . . . .
H19A H 0.478135 0.604941 0.504948 0.153 Uiso 1 1 calc R U . . .
H19B H 0.536009 0.688012 0.521713 0.153 Uiso 1 1 calc R U . . .
H19C H 0.641982 0.613431 0.524523 0.153 Uiso 1 1 calc R U . . .
C20 C 0.6047(3) 0.47519(14) 0.32085(9) 0.0618(6) Uani 1 1 d . . . . .
H20 H 0.536258 0.517482 0.310799 0.074 Uiso 1 1 calc R U . . .
C21 C 0.5167(4) 0.39684(16) 0.32074(12) 0.0841(9) Uani 1 1 d . . . . .
H21A H 0.583153 0.353990 0.328810 0.126 Uiso 1 1 calc R U . . .
H21B H 0.476067 0.387489 0.291119 0.126 Uiso 1 1 calc R U . . .
H21C H 0.435593 0.399880 0.342240 0.126 Uiso 1 1 calc R U . . .
C9 C 0.3109(3) 0.52861(15) 0.41732(9) 0.0649(7) Uani 1 1 d . . . . .
H9A H 0.361080 0.481724 0.406435 0.097 Uiso 1 1 calc R U . . .
H9B H 0.205558 0.517393 0.421718 0.097 Uiso 1 1 calc R U . . .
H9C H 0.355144 0.544637 0.445526 0.097 Uiso 1 1 calc R U . . .
C4 C 0.2583(3) 0.67270(14) 0.40004(8) 0.0564(6) Uani 1 1 d . . . . .
H4A H 0.303710 0.686880 0.428783 0.068 Uiso 1 1 calc R U . . .
H4B H 0.150899 0.664937 0.404911 0.068 Uiso 1 1 calc R U . . .
C3 C 0.2820(3) 0.74053(13) 0.36632(9) 0.0548(6) Uani 1 1 d . . . . .
H3 H 0.182171 0.756552 0.355236 0.066 Uiso 1 1 calc R U . . .
C10 C 0.3537(4) 0.81300(16) 0.38835(11) 0.0780(9) Uani 1 1 d . . . . .
H10A H 0.454309 0.800073 0.398020 0.117 Uiso 1 1 calc R U . . .
H10B H 0.294492 0.828831 0.414023 0.117 Uiso 1 1 calc R U . . .
H10C H 0.357559 0.855865 0.366933 0.117 Uiso 1 1 calc R U . . .
C8 C 0.3920(4) 0.77403(16) 0.28951(10) 0.0714(8) Uani 1 1 d . . . . .
H8A H 0.440865 0.752080 0.263350 0.107 Uiso 1 1 calc R U . . .
H8B H 0.452858 0.816221 0.301664 0.107 Uiso 1 1 calc R U . . .
H8C H 0.294793 0.794593 0.281122 0.107 Uiso 1 1 calc R U . . .
C18 C 0.7548(6) 0.7172(2) 0.46272(14) 0.1218(15) Uani 1 1 d . . . . .
H18A H 0.836467 0.694567 0.479801 0.183 Uiso 1 1 calc R U . . .
H18B H 0.720517 0.764946 0.477269 0.183 Uiso 1 1 calc R U . . .
H18C H 0.789205 0.729547 0.432744 0.183 Uiso 1 1 calc R U . . .
C22 C 0.7344(4) 0.4694(2) 0.28668(12) 0.0943(10) Uani 1 1 d . . . . .
H22A H 0.793781 0.517096 0.287834 0.141 Uiso 1 1 calc R U . . .
H22B H 0.693675 0.462839 0.256821 0.141 Uiso 1 1 calc R U . . .
H22C H 0.796850 0.424470 0.293986 0.141 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
Cl1 P1 2.0787(10) . ?
P1 C1 1.708(2) . ?
N1 C11 1.444(2) . ?
N1 C5 1.509(2) . ?
N1 C1 1.361(2) . ?
C17 H17 0.9800 . ?
C17 C16 1.514(4) . ?
C17 C19 1.519(5) . ?
C17 C18 1.537(5) . ?
C11 C16 1.397(3) . ?
C11 C12 1.408(3) . ?
C16 C15 1.395(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.379(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.367(4) . ?
C13 H13 0.9300 . ?
C13 C12 1.394(3) . ?
C12 C20 1.515(4) . ?
C5 C6 1.524(3) . ?
C5 C9 1.520(3) . ?
C5 C4 1.528(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.518(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C2 1.543(3) . ?
C2 C1 1.533(3) . ?
C2 C3 1.544(3) . ?
C2 C8 1.540(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20 0.9800 . ?
C20 C21 1.530(4) . ?
C20 C22 1.532(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.529(3) . ?
C3 H3 0.9800 . ?
C3 C10 1.520(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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 Cl1 109.37(8) . . ?
C11 N1 C5 120.91(15) . . ?
C1 N1 C11 123.13(17) . . ?
C1 N1 C5 115.83(16) . . ?
C16 C17 H17 107.4 . . ?
C16 C17 C19 113.2(2) . . ?
C16 C17 C18 111.0(3) . . ?
C19 C17 H17 107.4 . . ?
C19 C17 C18 110.1(3) . . ?
C18 C17 H17 107.4 . . ?
C16 C11 N1 119.17(19) . . ?
C16 C11 C12 122.0(2) . . ?
C12 C11 N1 118.79(19) . . ?
C11 C16 C17 123.0(2) . . ?
C15 C16 C17 119.2(2) . . ?
C15 C16 C11 117.8(2) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 C16 120.7(3) . . ?
C14 C15 H15 119.6 . . ?
C15 C14 H14 119.6 . . ?
C13 C14 C15 120.7(3) . . ?
C13 C14 H14 119.6 . . ?
C14 C13 H13 119.4 . . ?
C14 C13 C12 121.2(3) . . ?
C12 C13 H13 119.4 . . ?
C11 C12 C20 123.6(2) . . ?
C13 C12 C11 117.4(2) . . ?
C13 C12 C20 118.9(2) . . ?
N1 C5 C6 107.51(18) . . ?
N1 C5 C9 111.51(18) . . ?
N1 C5 C4 107.06(17) . . ?
C6 C5 C4 107.55(19) . . ?
C9 C5 C6 111.54(19) . . ?
C9 C5 C4 111.4(2) . . ?
C5 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C7 C6 C5 109.74(18) . . ?
C7 C6 H6A 109.7 . . ?
C7 C6 H6B 109.7 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 C2 110.87(19) . . ?
H7A C7 H7B 108.1 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C7 C2 C3 108.4(2) . . ?
C1 C2 C7 106.31(17) . . ?
C1 C2 C3 108.14(17) . . ?
C1 C2 C8 115.1(2) . . ?
C8 C2 C7 108.07(19) . . ?
C8 C2 C3 110.52(19) . . ?
N1 C1 P1 135.50(16) . . ?
N1 C1 C2 111.58(17) . . ?
C2 C1 P1 112.91(14) . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 C20 H20 108.0 . . ?
C12 C20 C21 111.7(2) . . ?
C12 C20 C22 112.1(3) . . ?
C21 C20 H20 108.0 . . ?
C21 C20 C22 109.0(2) . . ?
C22 C20 H20 108.0 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C5 C4 C3 111.36(19) . . ?
H4A C4 H4B 108.0 . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
C2 C3 H3 107.4 . . ?
C4 C3 C2 108.77(17) . . ?
C4 C3 H3 107.4 . . ?
C10 C3 C2 113.5(2) . . ?
C10 C3 C4 112.0(2) . . ?
C10 C3 H3 107.4 . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 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
Cl1 P1 C1 N1 0.7(2) . . . . ?
Cl1 P1 C1 C2 -178.49(13) . . . . ?
N1 C11 C16 C17 -3.8(4) . . . . ?
N1 C11 C16 C15 178.1(2) . . . . ?
N1 C11 C12 C13 -177.6(2) . . . . ?
N1 C11 C12 C20 4.5(3) . . . . ?
N1 C5 C6 C7 -53.3(2) . . . . ?
N1 C5 C4 C3 55.3(2) . . . . ?
C17 C16 C15 C14 -178.8(3) . . . . ?
C11 N1 C5 C6 -117.3(2) . . . . ?
C11 N1 C5 C9 5.2(3) . . . . ?
C11 N1 C5 C4 127.4(2) . . . . ?
C11 N1 C1 P1 -4.3(3) . . . . ?
C11 N1 C1 C2 174.91(18) . . . . ?
C11 C16 C15 C14 -0.6(4) . . . . ?
C11 C12 C20 C21 -115.0(3) . . . . ?
C11 C12 C20 C22 122.5(3) . . . . ?
C16 C11 C12 C13 1.5(3) . . . . ?
C16 C11 C12 C20 -176.4(2) . . . . ?
C16 C15 C14 C13 1.7(5) . . . . ?
C15 C14 C13 C12 -1.2(5) . . . . ?
C14 C13 C12 C11 -0.4(4) . . . . ?
C14 C13 C12 C20 177.6(3) . . . . ?
C13 C12 C20 C21 67.1(3) . . . . ?
C13 C12 C20 C22 -55.4(3) . . . . ?
C12 C11 C16 C17 177.1(2) . . . . ?
C12 C11 C16 C15 -1.0(4) . . . . ?
C5 N1 C11 C16 -89.0(2) . . . . ?
C5 N1 C11 C12 90.2(2) . . . . ?
C5 N1 C1 P1 179.87(17) . . . . ?
C5 N1 C1 C2 -1.0(2) . . . . ?
C5 C6 C7 C2 -3.2(3) . . . . ?
C5 C4 C3 C2 -0.7(3) . . . . ?
C5 C4 C3 C10 -127.0(2) . . . . ?
C6 C5 C4 C3 -60.0(2) . . . . ?
C6 C7 C2 C1 58.5(3) . . . . ?
C6 C7 C2 C3 -57.6(3) . . . . ?
C6 C7 C2 C8 -177.4(2) . . . . ?
C7 C2 C1 P1 122.05(17) . . . . ?
C7 C2 C1 N1 -57.3(2) . . . . ?
C7 C2 C3 C4 59.0(2) . . . . ?
C7 C2 C3 C10 -175.6(2) . . . . ?
C1 N1 C11 C16 95.3(3) . . . . ?
C1 N1 C11 C12 -85.5(2) . . . . ?
C1 N1 C5 C6 58.7(2) . . . . ?
C1 N1 C5 C9 -178.80(19) . . . . ?
C1 N1 C5 C4 -56.7(2) . . . . ?
C1 C2 C3 C4 -55.9(2) . . . . ?
C1 C2 C3 C10 69.5(2) . . . . ?
C19 C17 C16 C11 123.4(3) . . . . ?
C19 C17 C16 C15 -58.4(4) . . . . ?
C9 C5 C6 C7 -175.8(2) . . . . ?
C9 C5 C4 C3 177.5(2) . . . . ?
C4 C5 C6 C7 61.7(2) . . . . ?
C3 C2 C1 P1 -121.68(17) . . . . ?
C3 C2 C1 N1 59.0(2) . . . . ?
C8 C2 C1 P1 2.4(2) . . . . ?
C8 C2 C1 N1 -176.91(19) . . . . ?
C8 C2 C3 C4 177.3(2) . . . . ?
C8 C2 C3 C10 -57.3(3) . . . . ?
C18 C17 C16 C11 -112.1(3) . . . . ?
C18 C17 C16 C15 66.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_bicppritu_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2264853'
loop_
_audit_author_name
_audit_author_address
'Subrata Kundu'
;IIT Delhi
India
;
_audit_update_record             
;
2023-05-23 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;
_audit_creation_date             2023-05-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C22 H33 N P)'
_chemical_formula_sum            'C44 H66 N2 P2'
_chemical_formula_weight         684.92
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   24.690(3)
_cell_length_b                   35.674(4)
_cell_length_c                   18.131(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     15970(3)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    5713
_cell_measurement_temperature    109(2)
_cell_measurement_theta_max      0.989
_cell_measurement_theta_min      0.972
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Multi-scan
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             5984
_exptl_crystal_preparation       'slow evaporation'
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1027
_diffrn_reflns_av_unetI/netI     0.0873
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            39142
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.006
_diffrn_ambient_temperature      109.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-IV CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_full    0.924
_reflns_Friedel_fraction_max     0.914
_reflns_number_gt                5713
_reflns_number_total             7829
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Flack x determined using 1994 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.43(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     498
_refine_ls_number_reflns         7829
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0703
_refine_ls_restrained_S_all      1.031
_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)+(0.0871P)²+46.6752P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1684
_refine_ls_wR_factor_ref         0.1942
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C7-C10_2 \\sim C7A-C10_2
 with sigma of 0.02
 C7-C10_2 \\sim C7-C10A
 with sigma of 0.02
 C7A-C10_2 \\sim C7A-C10A
 with sigma of 0.02
 C4-C10_2 \\sim C4-C10A
 with sigma of 0.02
 C5-C10_2 \\sim C5-C10A
 with sigma of 0.02
 C8-C10_2 \\sim C8-C10A
 with sigma of 0.02
 C6-C10_2 \\sim C6-C10A
 with sigma of 0.02
 C10_2-C11_2 \\sim C10A-C11_2
 with sigma of 0.02
 C2_1-C10_1 \\sim C2_1-C20A
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
Uanis(C10_2) = Uanis(C2_1)
3. Others
 Fixed Sof: H2AA(0.5) H2AB(0.5) H2BC(0.5) H2BD(0.5) H3BC(0.5) H3BD(0.5)
 H3AA(0.5) H3AB(0.5) C7(0.5) H7A(0.5) H7B(0.5) H7C(0.5) C7A(0.5) H7AA(0.5)
 H7AB(0.5) H7AC(0.5) C4(0.5) H4A(0.5) H4B(0.5) C5(0.5) H5A(0.5) H5B(0.5)
 C8(0.5) H8(0.5) C6(0.5) H6(0.5) C9(0.5) H9A(0.5) H9B(0.5) H9C(0.5) C10(0.5)
 H10A(0.5) H10B(0.5) H10C(0.5) C10A(0.5) C20A(0.4) H20A(0.4) H20B(0.4)
 H20C(0.4) C10(0.6) H10A(0.6) H10B(0.6) H10C(0.6) C10(0.5)
4.a Ternary CH refined with riding coordinates:
 C8(H8), C6(H6), C7(H7), C20(H20), C17(H17), C12(H12), C14(H14)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2AA,H2AB), C2(H2BC,H2BD), C3(H3BC,H3BD), C3(H3AA,H3AB), C4(H4A,H4B),
 C5(H5A,H5B), C6(H6A,H6B), C4(H4A,H4B), C3(H3A,H3B)
4.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C3(H3), C4(H4), C5(H5)
4.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C7(H7A,H7B,H7C), C7A(H7AA,H7AB,H7AC), C9(H9A,H9B,H9C),
 C10(H10A,H10B,H10C), C20A(H20A,H20B,H20C), C22(H22A,H22B,H22C), C19(H19A,H19B,
 H19C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C21(H21A,H21B,
 H21C), C18(H18A,H18B,H18C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C20(H20A,
 H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6916(2) 0.42251(16) 0.7517(5) 0.0381(14) Uani 1 1 d . . . . .
H1A H 0.712845 0.399321 0.750480 0.057 Uiso 1 1 calc R U . . .
H1B H 0.700149 0.436505 0.796732 0.057 Uiso 1 1 calc R U . . .
H1C H 0.700473 0.437844 0.708507 0.057 Uiso 1 1 calc R U . . .
C2 C 0.6171(3) 0.3900(2) 0.6831(7) 0.078(3) Uani 1 1 d . . . . .
H2AA H 0.638085 0.400195 0.641035 0.094 Uiso 0.5 1 calc R U P A 1
H2AB H 0.630233 0.364159 0.691628 0.094 Uiso 0.5 1 calc R U P A 1
H2BC H 0.640633 0.367724 0.677413 0.094 Uiso 0.5 1 calc R U P B 2
H2BD H 0.617892 0.405130 0.637275 0.094 Uiso 0.5 1 calc R U P B 2
C3 C 0.6171(3) 0.3903(2) 0.8205(6) 0.075(3) Uani 1 1 d . . . . .
H3BC H 0.631231 0.364610 0.813643 0.090 Uiso 0.5 1 calc R U P C 2
H3BD H 0.637182 0.401472 0.862380 0.090 Uiso 0.5 1 calc R U P C 2
H3AA H 0.617935 0.405849 0.865794 0.090 Uiso 0.5 1 calc R U P D 1
H3AB H 0.640392 0.367994 0.826892 0.090 Uiso 0.5 1 calc R U P D 1
C7 C 0.4676(5) 0.3911(3) 0.7186(9) 0.037(3) Uani 0.5 1 d . . P E 1
H7A H 0.453415 0.401603 0.672544 0.055 Uiso 0.5 1 calc R U P E 1
H7B H 0.447866 0.401753 0.760485 0.055 Uiso 0.5 1 calc R U P E 1
H7C H 0.462985 0.363789 0.718209 0.055 Uiso 0.5 1 calc R U P E 1
C7A C 0.4699(5) 0.3909(4) 0.7838(8) 0.035(3) Uani 0.5 1 d . . P E 2
H7AA H 0.464309 0.363736 0.780161 0.052 Uiso 0.5 1 calc R U P E 2
H7AB H 0.448313 0.403582 0.745963 0.052 Uiso 0.5 1 calc R U P E 2
H7AC H 0.458787 0.399576 0.832711 0.052 Uiso 0.5 1 calc R U P E 2
C4 C 0.5587(5) 0.3870(4) 0.8436(9) 0.033(3) Uani 0.5 1 d . . P E 2
H4A H 0.550190 0.403717 0.885574 0.040 Uiso 0.5 1 calc R U P E 2
H4B H 0.549204 0.360856 0.856767 0.040 Uiso 0.5 1 calc R U P E 2
C5 C 0.5586(6) 0.3874(4) 0.6589(10) 0.033(3) Uani 0.5 1 d . . P E 1
H5A H 0.551408 0.403729 0.615891 0.040 Uiso 0.5 1 calc R U P E 1
H5B H 0.548654 0.361269 0.646280 0.040 Uiso 0.5 1 calc R U P E 1
C8 C 0.5509(5) 0.3785(4) 0.7941(8) 0.027(3) Uani 0.5 1 d . . P E 1
H8 H 0.550426 0.351236 0.781691 0.032 Uiso 0.5 1 calc R U P E 1
C6 C 0.5538(6) 0.3786(4) 0.7083(10) 0.035(3) Uani 0.5 1 d . . P E 2
H6 H 0.552789 0.351189 0.720040 0.042 Uiso 0.5 1 calc R U P E 2
C9 C 0.5204(6) 0.3837(4) 0.8660(8) 0.047(4) Uani 0.5 1 d . . P E 1
H9A H 0.535425 0.366917 0.903512 0.070 Uiso 0.5 1 calc R U P E 1
H9B H 0.482004 0.377826 0.858369 0.070 Uiso 0.5 1 calc R U P E 1
H9C H 0.523935 0.409757 0.882515 0.070 Uiso 0.5 1 calc R U P E 1
C10 C 0.5237(8) 0.3850(6) 0.6359(10) 0.067(5) Uani 0.5 1 d . . P E 2
H10A H 0.521702 0.411961 0.625740 0.101 Uiso 0.5 1 calc R U P E 2
H10B H 0.486923 0.374783 0.639762 0.101 Uiso 0.5 1 calc R U P E 2
H10C H 0.542988 0.372433 0.595713 0.101 Uiso 0.5 1 calc R U P E 2
C10A C 0.5284(5) 0.4006(3) 0.7256(10) 0.034(3) Uani 0.5 1 d D . P E 1
C20A C 0.3575(7) 0.4478(4) 0.2619(16) 0.048(6) Uani 0.4 1 d D . P F 2
H20A H 0.375894 0.446069 0.309688 0.071 Uiso 0.4 1 calc R U P F 2
H20B H 0.378295 0.434047 0.224714 0.071 Uiso 0.4 1 calc R U P F 2
H20C H 0.321141 0.437030 0.265926 0.071 Uiso 0.4 1 calc R U P F 2
P1_1 P 0.46413(5) 0.48189(4) 0.24041(11) 0.0315(4) Uani 1 1 d . . . . .
N1_1 N 0.40001(15) 0.54855(11) 0.2485(3) 0.0212(9) Uani 1 1 d . . . . .
C11_1 C 0.44314(18) 0.57542(13) 0.2508(4) 0.0219(11) Uani 1 1 d . . . . .
C12_1 C 0.4640(2) 0.58665(16) 0.3189(3) 0.0276(13) Uani 1 1 d . . . . .
C13_1 C 0.5013(3) 0.61608(17) 0.3197(4) 0.0353(15) Uani 1 1 d . . . . .
H13_1 H 0.515582 0.624509 0.365444 0.042 Uiso 1 1 calc R U . . .
C14_1 C 0.5177(2) 0.63301(16) 0.2557(4) 0.0397(15) Uani 1 1 d . . . . .
H14_1 H 0.542138 0.653574 0.257427 0.048 Uiso 1 1 calc R U . . .
C15_1 C 0.4987(3) 0.62017(18) 0.1884(4) 0.0351(14) Uani 1 1 d . . . . .
H15_1 H 0.511367 0.631561 0.144259 0.042 Uiso 1 1 calc R U . . .
C16_1 C 0.4619(2) 0.59124(15) 0.1841(3) 0.0230(12) Uani 1 1 d . . . . .
C5_1 C 0.34221(18) 0.56213(15) 0.2515(4) 0.0295(12) Uani 1 1 d . . . . .
C6_1 C 0.3160(2) 0.5430(2) 0.3172(4) 0.0451(18) Uani 1 1 d . . . . .
H6A_1 H 0.277518 0.550703 0.320904 0.054 Uiso 1 1 calc R U . . .
H6B_1 H 0.334582 0.550693 0.363186 0.054 Uiso 1 1 calc R U . . .
C7_1 C 0.3196(3) 0.5003(3) 0.3081(7) 0.086(4) Uani 1 1 d . . . . .
H7_1 H 0.281824 0.492901 0.294391 0.103 Uiso 1 1 calc R U . . .
C2_1 C 0.3530(2) 0.49022(16) 0.2385(5) 0.0501(18) Uani 1 1 d D . . . .
C1_1 C 0.40799(19) 0.51046(14) 0.2434(4) 0.0265(12) Uani 1 1 d . . . . .
C20_1 C 0.4496(2) 0.56781(18) 0.3915(3) 0.0323(14) Uani 1 1 d . . . . .
H20_1 H 0.425552 0.545968 0.380431 0.039 Uiso 1 1 calc R U . . .
C22_1 C 0.4194(3) 0.5940(2) 0.4435(4) 0.053(2) Uani 1 1 d . . . . .
H22A_1 H 0.442406 0.615521 0.455425 0.079 Uiso 1 1 calc R U . . .
H22B_1 H 0.410245 0.580497 0.488948 0.079 Uiso 1 1 calc R U . . .
H22C_1 H 0.386092 0.602729 0.419699 0.079 Uiso 1 1 calc R U . . .
C17_1 C 0.4441(2) 0.57697(18) 0.1092(3) 0.0314(14) Uani 1 1 d . . . . .
H17_1 H 0.418548 0.555572 0.116833 0.038 Uiso 1 1 calc R U . . .
C19_1 C 0.4148(3) 0.6074(2) 0.0645(4) 0.0441(17) Uani 1 1 d . . . . .
H19A_1 H 0.382762 0.615912 0.091707 0.066 Uiso 1 1 calc R U . . .
H19B_1 H 0.403523 0.597057 0.016773 0.066 Uiso 1 1 calc R U . . .
H19C_1 H 0.439257 0.628608 0.056382 0.066 Uiso 1 1 calc R U . . .
C8_1 C 0.3385(2) 0.60422(15) 0.2576(4) 0.0330(14) Uani 1 1 d . . . . .
H8A_1 H 0.358782 0.612671 0.300948 0.050 Uiso 1 1 calc R U . . .
H8B_1 H 0.300460 0.611630 0.262492 0.050 Uiso 1 1 calc R U . . .
H8C_1 H 0.353874 0.615704 0.213139 0.050 Uiso 1 1 calc R U . . .
C4_1 C 0.3146(2) 0.54795(19) 0.1812(4) 0.0373(15) Uani 1 1 d . . . . .
H4A_1 H 0.275440 0.553709 0.183569 0.045 Uiso 1 1 calc R U . . .
H4B_1 H 0.329932 0.561256 0.138050 0.045 Uiso 1 1 calc R U . . .
C3_1 C 0.3222(3) 0.5061(2) 0.1711(7) 0.083(4) Uani 1 1 d . . . . .
H3A_1 H 0.342993 0.501109 0.125451 0.100 Uiso 1 1 calc R U . . .
H3B_1 H 0.286470 0.493657 0.166627 0.100 Uiso 1 1 calc R U . . .
C9_1 C 0.3314(4) 0.4772(3) 0.3665(6) 0.085(3) Uani 1 1 d . . . . .
H9A_1 H 0.368240 0.482298 0.383873 0.127 Uiso 1 1 calc R U . . .
H9B_1 H 0.328704 0.450976 0.350799 0.127 Uiso 1 1 calc R U . . .
H9C_1 H 0.305617 0.481834 0.406620 0.127 Uiso 1 1 calc R U . . .
C10_1 C 0.3566(5) 0.4478(3) 0.2144(7) 0.031(3) Uani 0.6 1 d D . P F 1
H10A_1 H 0.378912 0.445735 0.169882 0.047 Uiso 0.6 1 calc R U P F 1
H10B_1 H 0.320174 0.438300 0.204213 0.047 Uiso 0.6 1 calc R U P F 1
H10C_1 H 0.373061 0.433136 0.254219 0.047 Uiso 0.6 1 calc R U P F 1
C21_1 C 0.5005(3) 0.5530(2) 0.4308(4) 0.0423(16) Uani 1 1 d . . . . .
H21A_1 H 0.520127 0.536037 0.397760 0.063 Uiso 1 1 calc R U . . .
H21B_1 H 0.489814 0.539458 0.475487 0.063 Uiso 1 1 calc R U . . .
H21C_1 H 0.523924 0.574116 0.444134 0.063 Uiso 1 1 calc R U . . .
C18_1 C 0.4931(3) 0.5627(2) 0.0640(4) 0.0395(16) Uani 1 1 d . . . . .
H18A_1 H 0.519046 0.583144 0.057003 0.059 Uiso 1 1 calc R U . . .
H18B_1 H 0.480598 0.553730 0.015769 0.059 Uiso 1 1 calc R U . . .
H18C_1 H 0.510664 0.542050 0.090510 0.059 Uiso 1 1 calc R U . . .
P1_2 P 0.48557(6) 0.47110(5) 0.74966(17) 0.0570(6) Uani 1 1 d . . . . .
N1_2 N 0.59717(16) 0.44753(12) 0.7515(4) 0.0352(12) Uani 1 1 d . . . . .
C1_2 C 0.62117(19) 0.48436(14) 0.7522(4) 0.0319(13) Uani 1 1 d . . . . .
C2_2 C 0.6353(2) 0.50219(19) 0.6861(4) 0.0368(15) Uani 1 1 d . . . . .
C3_2 C 0.6591(2) 0.5370(2) 0.6895(4) 0.0406(17) Uani 1 1 d . . . . .
H3_2 H 0.668299 0.549492 0.644896 0.049 Uiso 1 1 calc R U . . .
C4_2 C 0.6700(2) 0.55425(17) 0.7560(5) 0.0422(17) Uani 1 1 d . . . . .
H4_2 H 0.686929 0.578163 0.757105 0.051 Uiso 1 1 calc R U . . .
C5_2 C 0.6561(2) 0.53647(18) 0.8208(4) 0.0378(16) Uani 1 1 d . . . . .
H5_2 H 0.663707 0.548473 0.866398 0.045 Uiso 1 1 calc R U . . .
C6_2 C 0.6312(2) 0.50135(17) 0.8213(4) 0.0349(15) Uani 1 1 d . . . . .
C7_2 C 0.6318(2) 0.41304(16) 0.7507(5) 0.0459(17) Uani 1 1 d . . . . .
C10_2 C 0.5296(6) 0.3997(4) 0.7720(14) 0.0501(18) Uani 0.5 1 d D . P E 2
C11_2 C 0.5419(2) 0.44204(17) 0.7503(6) 0.056(2) Uani 1 1 d D . . . .
C12_2 C 0.6231(3) 0.4857(2) 0.6101(4) 0.0505(19) Uani 1 1 d . . . . .
H12_2 H 0.603592 0.461478 0.617635 0.061 Uiso 1 1 calc R U . . .
C13_2 C 0.6758(4) 0.4772(3) 0.5678(5) 0.064(2) Uani 1 1 d . . . . .
H13A_2 H 0.694104 0.500776 0.555625 0.097 Uiso 1 1 calc R U . . .
H13B_2 H 0.667127 0.463669 0.522301 0.097 Uiso 1 1 calc R U . . .
H13C_2 H 0.699569 0.461783 0.598624 0.097 Uiso 1 1 calc R U . . .
C14_2 C 0.6151(3) 0.4852(2) 0.8936(4) 0.0488(19) Uani 1 1 d . . . . .
H14_2 H 0.594224 0.461609 0.884212 0.059 Uiso 1 1 calc R U . . .
C15_2 C 0.6649(4) 0.4752(3) 0.9411(5) 0.066(2) Uani 1 1 d . . . . .
H15A_2 H 0.687853 0.457456 0.914346 0.100 Uiso 1 1 calc R U . . .
H15B_2 H 0.652871 0.463903 0.987561 0.100 Uiso 1 1 calc R U . . .
H15C_2 H 0.685541 0.498081 0.951651 0.100 Uiso 1 1 calc R U . . .
C20_2 C 0.5865(4) 0.5113(3) 0.5651(5) 0.071(3) Uani 1 1 d . . . . .
H20A_2 H 0.553632 0.516894 0.593349 0.107 Uiso 1 1 calc R U . . .
H20B_2 H 0.576577 0.498767 0.518902 0.107 Uiso 1 1 calc R U . . .
H20C_2 H 0.605632 0.534688 0.553974 0.107 Uiso 1 1 calc R U . . .
C21_2 C 0.5790(3) 0.5119(2) 0.9379(5) 0.064(2) Uani 1 1 d . . . . .
H21A_2 H 0.600461 0.533508 0.954238 0.096 Uiso 1 1 calc R U . . .
H21B_2 H 0.564406 0.498803 0.981021 0.096 Uiso 1 1 calc R U . . .
H21C_2 H 0.549084 0.520621 0.906774 0.096 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
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C7_2 1.516(7) . ?
C2 H2AA 0.9900 . ?
C2 H2AB 0.9900 . ?
C2 H2BC 0.9900 . ?
C2 H2BD 0.9900 . ?
C2 C5 1.514(16) . ?
C2 C6 1.680(18) . ?
C2 C7_2 1.520(13) . ?
C3 H3BC 0.9900 . ?
C3 H3BD 0.9900 . ?
C3 H3AA 0.9900 . ?
C3 H3AB 0.9900 . ?
C3 C4 1.506(15) . ?
C3 C8 1.753(15) . ?
C3 C7_2 1.546(12) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 C10A 1.546(16) . ?
C7A H7AA 0.9800 . ?
C7A H7AB 0.9800 . ?
C7A H7AC 0.9800 . ?
C7A C10_2 1.521(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C10_2 1.55(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C10A 1.50(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.517(19) . ?
C8 C10A 1.57(2) . ?
C6 H6 1.0000 . ?
C6 C10 1.53(2) . ?
C6 C10_2 1.50(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10A C11_2 1.579(13) . ?
C20A H20A 0.9800 . ?
C20A H20B 0.9800 . ?
C20A H20C 0.9800 . ?
C20A C2_1 1.574(16) . ?
P1_1 P1_1 2.193(3) 2_665 ?
P1_1 C1_1 1.721(5) . ?
N1_1 C11_1 1.433(6) . ?
N1_1 C5_1 1.508(6) . ?
N1_1 C1_1 1.376(6) . ?
C11_1 C12_1 1.396(9) . ?
C11_1 C16_1 1.414(8) . ?
C12_1 C13_1 1.397(8) . ?
C12_1 C20_1 1.519(9) . ?
C13_1 H13_1 0.9500 . ?
C13_1 C14_1 1.370(10) . ?
C14_1 H14_1 0.9500 . ?
C14_1 C15_1 1.385(10) . ?
C15_1 H15_1 0.9500 . ?
C15_1 C16_1 1.378(8) . ?
C16_1 C17_1 1.515(9) . ?
C5_1 C6_1 1.518(9) . ?
C5_1 C8_1 1.508(7) . ?
C5_1 C4_1 1.532(9) . ?
C6_1 H6A_1 0.9900 . ?
C6_1 H6B_1 0.9900 . ?
C6_1 C7_1 1.537(12) . ?
C7_1 H7_1 1.0000 . ?
C7_1 C2_1 1.551(13) . ?
C7_1 C9_1 1.372(13) . ?
C2_1 C1_1 1.540(7) . ?
C2_1 C3_1 1.546(13) . ?
C2_1 C10_1 1.576(11) . ?
C20_1 H20_1 1.0000 . ?
C20_1 C22_1 1.523(9) . ?
C20_1 C21_1 1.538(9) . ?
C22_1 H22A_1 0.9800 . ?
C22_1 H22B_1 0.9800 . ?
C22_1 H22C_1 0.9800 . ?
C17_1 H17_1 1.0000 . ?
C17_1 C19_1 1.536(9) . ?
C17_1 C18_1 1.548(8) . ?
C19_1 H19A_1 0.9800 . ?
C19_1 H19B_1 0.9800 . ?
C19_1 H19C_1 0.9800 . ?
C8_1 H8A_1 0.9800 . ?
C8_1 H8B_1 0.9800 . ?
C8_1 H8C_1 0.9800 . ?
C4_1 H4A_1 0.9900 . ?
C4_1 H4B_1 0.9900 . ?
C4_1 C3_1 1.517(11) . ?
C3_1 H3A_1 0.9900 . ?
C3_1 H3B_1 0.9900 . ?
C9_1 H9A_1 0.9800 . ?
C9_1 H9B_1 0.9800 . ?
C9_1 H9C_1 0.9800 . ?
C10_1 H10A_1 0.9800 . ?
C10_1 H10B_1 0.9800 . ?
C10_1 H10C_1 0.9800 . ?
C21_1 H21A_1 0.9800 . ?
C21_1 H21B_1 0.9800 . ?
C21_1 H21C_1 0.9800 . ?
C18_1 H18A_1 0.9800 . ?
C18_1 H18B_1 0.9800 . ?
C18_1 H18C_1 0.9800 . ?
P1_2 P1_2 2.182(3) 2_665 ?
P1_2 C11_2 1.735(6) . ?
N1_2 C1_2 1.441(7) . ?
N1_2 C7_2 1.498(7) . ?
N1_2 C11_2 1.378(7) . ?
C1_2 C2_2 1.401(9) . ?
C1_2 C6_2 1.413(10) . ?
C2_2 C3_2 1.376(9) . ?
C2_2 C12_2 1.527(11) . ?
C3_2 H3_2 0.9500 . ?
C3_2 C4_2 1.380(11) . ?
C4_2 H4_2 0.9500 . ?
C4_2 C5_2 1.378(10) . ?
C5_2 H5_2 0.9500 . ?
C5_2 C6_2 1.396(9) . ?
C6_2 C14_2 1.487(10) . ?
C10_2 C11_2 1.590(15) . ?
C12_2 H12_2 1.0000 . ?
C12_2 C13_2 1.539(12) . ?
C12_2 C20_2 1.523(11) . ?
C13_2 H13A_2 0.9800 . ?
C13_2 H13B_2 0.9800 . ?
C13_2 H13C_2 0.9800 . ?
C14_2 H14_2 1.0000 . ?
C14_2 C15_2 1.542(12) . ?
C14_2 C21_2 1.533(10) . ?
C15_2 H15A_2 0.9800 . ?
C15_2 H15B_2 0.9800 . ?
C15_2 H15C_2 0.9800 . ?
C20_2 H20A_2 0.9800 . ?
C20_2 H20B_2 0.9800 . ?
C20_2 H20C_2 0.9800 . ?
C21_2 H21A_2 0.9800 . ?
C21_2 H21B_2 0.9800 . ?
C21_2 H21C_2 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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7_2 C1 H1A 109.5 . . ?
C7_2 C1 H1B 109.5 . . ?
C7_2 C1 H1C 109.5 . . ?
H2AA C2 H2AB 106.9 . . ?
H2BC C2 H2BD 109.8 . . ?
C5 C2 H2AA 107.4 . . ?
C5 C2 H2AB 107.4 . . ?
C5 C2 C7_2 119.6(8) . . ?
C6 C2 H2BC 112.2 . . ?
C6 C2 H2BD 112.2 . . ?
C7_2 C2 H2AA 107.4 . . ?
C7_2 C2 H2AB 107.4 . . ?
C7_2 C2 H2BC 112.2 . . ?
C7_2 C2 H2BD 112.2 . . ?
C7_2 C2 C6 97.6(8) . . ?
H3BC C3 H3BD 107.0 . . ?
H3AA C3 H3AB 109.9 . . ?
C4 C3 H3BC 107.4 . . ?
C4 C3 H3BD 107.4 . . ?
C4 C3 C7_2 119.6(8) . . ?
C8 C3 H3AA 112.4 . . ?
C8 C3 H3AB 112.4 . . ?
C7_2 C3 H3BC 107.4 . . ?
C7_2 C3 H3BD 107.4 . . ?
C7_2 C3 H3AA 112.4 . . ?
C7_2 C3 H3AB 112.4 . . ?
C7_2 C3 C8 96.9(8) . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C10A C7 H7A 109.5 . . ?
C10A C7 H7B 109.5 . . ?
C10A C7 H7C 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
C10_2 C7A H7AA 109.5 . . ?
C10_2 C7A H7AB 109.5 . . ?
C10_2 C7A H7AC 109.5 . . ?
C3 C4 H4A 111.6 . . ?
C3 C4 H4B 111.6 . . ?
C3 C4 C10_2 100.8(12) . . ?
H4A C4 H4B 109.4 . . ?
C10_2 C4 H4A 111.6 . . ?
C10_2 C4 H4B 111.6 . . ?
C2 C5 H5A 111.2 . . ?
C2 C5 H5B 111.2 . . ?
H5A C5 H5B 109.1 . . ?
C10A C5 C2 102.8(12) . . ?
C10A C5 H5A 111.2 . . ?
C10A C5 H5B 111.2 . . ?
C3 C8 H8 107.8 . . ?
C9 C8 C3 101.5(11) . . ?
C9 C8 H8 107.8 . . ?
C9 C8 C10A 116.2(12) . . ?
C10A C8 C3 115.1(9) . . ?
C10A C8 H8 107.8 . . ?
C2 C6 H6 108.5 . . ?
C10 C6 C2 100.5(14) . . ?
C10 C6 H6 108.5 . . ?
C10_2 C6 C2 117.2(10) . . ?
C10_2 C6 H6 108.5 . . ?
C10_2 C6 C10 113.0(15) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C10A C8 107.3(12) . . ?
C7 C10A C11_2 115.8(10) . . ?
C5 C10A C7 110.3(12) . . ?
C5 C10A C8 107.7(12) . . ?
C5 C10A C11_2 114.8(11) . . ?
C8 C10A C11_2 99.8(10) . . ?
H20A C20A H20B 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C2_1 C20A H20A 109.5 . . ?
C2_1 C20A H20B 109.5 . . ?
C2_1 C20A H20C 109.5 . . ?
C1_1 P1_1 P1_1 107.55(18) . 2_665 ?
C11_1 N1_1 C5_1 119.1(4) . . ?
C1_1 N1_1 C11_1 123.8(4) . . ?
C1_1 N1_1 C5_1 117.1(4) . . ?
C12_1 C11_1 N1_1 119.5(5) . . ?
C12_1 C11_1 C16_1 121.5(4) . . ?
C16_1 C11_1 N1_1 119.0(5) . . ?
C11_1 C12_1 C13_1 117.9(6) . . ?
C11_1 C12_1 C20_1 123.5(5) . . ?
C13_1 C12_1 C20_1 118.6(5) . . ?
C12_1 C13_1 H13_1 119.4 . . ?
C14_1 C13_1 C12_1 121.2(6) . . ?
C14_1 C13_1 H13_1 119.4 . . ?
C13_1 C14_1 H14_1 120.0 . . ?
C13_1 C14_1 C15_1 120.0(5) . . ?
C15_1 C14_1 H14_1 120.0 . . ?
C14_1 C15_1 H15_1 119.3 . . ?
C16_1 C15_1 C14_1 121.4(6) . . ?
C16_1 C15_1 H15_1 119.3 . . ?
C11_1 C16_1 C17_1 122.6(5) . . ?
C15_1 C16_1 C11_1 117.8(5) . . ?
C15_1 C16_1 C17_1 119.6(5) . . ?
N1_1 C5_1 C6_1 106.8(5) . . ?
N1_1 C5_1 C4_1 106.5(5) . . ?
C6_1 C5_1 C4_1 108.4(5) . . ?
C8_1 C5_1 N1_1 112.3(4) . . ?
C8_1 C5_1 C6_1 111.4(6) . . ?
C8_1 C5_1 C4_1 111.2(5) . . ?
C5_1 C6_1 H6A_1 109.7 . . ?
C5_1 C6_1 H6B_1 109.7 . . ?
C5_1 C6_1 C7_1 109.7(6) . . ?
H6A_1 C6_1 H6B_1 108.2 . . ?
C7_1 C6_1 H6A_1 109.7 . . ?
C7_1 C6_1 H6B_1 109.7 . . ?
C6_1 C7_1 H7_1 103.5 . . ?
C6_1 C7_1 C2_1 110.3(6) . . ?
C2_1 C7_1 H7_1 103.5 . . ?
C9_1 C7_1 C6_1 121.6(11) . . ?
C9_1 C7_1 H7_1 103.5 . . ?
C9_1 C7_1 C2_1 112.2(7) . . ?
C7_1 C2_1 C20A 92.2(12) . . ?
C7_1 C2_1 C10_1 118.5(7) . . ?
C1_1 C2_1 C20A 111.9(8) . . ?
C1_1 C2_1 C7_1 108.3(7) . . ?
C1_1 C2_1 C3_1 108.0(6) . . ?
C1_1 C2_1 C10_1 114.6(6) . . ?
C3_1 C2_1 C20A 126.8(10) . . ?
C3_1 C2_1 C7_1 107.3(6) . . ?
C3_1 C2_1 C10_1 99.2(8) . . ?
N1_1 C1_1 P1_1 134.6(4) . . ?
N1_1 C1_1 C2_1 109.9(4) . . ?
C2_1 C1_1 P1_1 115.5(4) . . ?
C12_1 C20_1 H20_1 108.1 . . ?
C12_1 C20_1 C22_1 112.3(6) . . ?
C12_1 C20_1 C21_1 111.2(5) . . ?
C22_1 C20_1 H20_1 108.1 . . ?
C22_1 C20_1 C21_1 108.9(6) . . ?
C21_1 C20_1 H20_1 108.1 . . ?
C20_1 C22_1 H22A_1 109.5 . . ?
C20_1 C22_1 H22B_1 109.5 . . ?
C20_1 C22_1 H22C_1 109.5 . . ?
H22A_1 C22_1 H22B_1 109.5 . . ?
H22A_1 C22_1 H22C_1 109.5 . . ?
H22B_1 C22_1 H22C_1 109.5 . . ?
C16_1 C17_1 H17_1 108.4 . . ?
C16_1 C17_1 C19_1 111.9(5) . . ?
C16_1 C17_1 C18_1 111.0(5) . . ?
C19_1 C17_1 H17_1 108.4 . . ?
C19_1 C17_1 C18_1 108.8(5) . . ?
C18_1 C17_1 H17_1 108.4 . . ?
C17_1 C19_1 H19A_1 109.5 . . ?
C17_1 C19_1 H19B_1 109.5 . . ?
C17_1 C19_1 H19C_1 109.5 . . ?
H19A_1 C19_1 H19B_1 109.5 . . ?
H19A_1 C19_1 H19C_1 109.5 . . ?
H19B_1 C19_1 H19C_1 109.5 . . ?
C5_1 C8_1 H8A_1 109.5 . . ?
C5_1 C8_1 H8B_1 109.5 . . ?
C5_1 C8_1 H8C_1 109.5 . . ?
H8A_1 C8_1 H8B_1 109.5 . . ?
H8A_1 C8_1 H8C_1 109.5 . . ?
H8B_1 C8_1 H8C_1 109.5 . . ?
C5_1 C4_1 H4A_1 109.3 . . ?
C5_1 C4_1 H4B_1 109.3 . . ?
H4A_1 C4_1 H4B_1 107.9 . . ?
C3_1 C4_1 C5_1 111.8(6) . . ?
C3_1 C4_1 H4A_1 109.3 . . ?
C3_1 C4_1 H4B_1 109.3 . . ?
C2_1 C3_1 H3A_1 109.9 . . ?
C2_1 C3_1 H3B_1 109.9 . . ?
C4_1 C3_1 C2_1 109.0(7) . . ?
C4_1 C3_1 H3A_1 109.9 . . ?
C4_1 C3_1 H3B_1 109.9 . . ?
H3A_1 C3_1 H3B_1 108.3 . . ?
C7_1 C9_1 H9A_1 109.5 . . ?
C7_1 C9_1 H9B_1 109.5 . . ?
C7_1 C9_1 H9C_1 109.5 . . ?
H9A_1 C9_1 H9B_1 109.5 . . ?
H9A_1 C9_1 H9C_1 109.5 . . ?
H9B_1 C9_1 H9C_1 109.5 . . ?
C2_1 C10_1 H10A_1 109.5 . . ?
C2_1 C10_1 H10B_1 109.5 . . ?
C2_1 C10_1 H10C_1 109.5 . . ?
H10A_1 C10_1 H10B_1 109.5 . . ?
H10A_1 C10_1 H10C_1 109.5 . . ?
H10B_1 C10_1 H10C_1 109.5 . . ?
C20_1 C21_1 H21A_1 109.5 . . ?
C20_1 C21_1 H21B_1 109.5 . . ?
C20_1 C21_1 H21C_1 109.5 . . ?
H21A_1 C21_1 H21B_1 109.5 . . ?
H21A_1 C21_1 H21C_1 109.5 . . ?
H21B_1 C21_1 H21C_1 109.5 . . ?
C17_1 C18_1 H18A_1 109.5 . . ?
C17_1 C18_1 H18B_1 109.5 . . ?
C17_1 C18_1 H18C_1 109.5 . . ?
H18A_1 C18_1 H18B_1 109.5 . . ?
H18A_1 C18_1 H18C_1 109.5 . . ?
H18B_1 C18_1 H18C_1 109.5 . . ?
C11_2 P1_2 P1_2 107.6(2) . 2_665 ?
C1_2 N1_2 C7_2 121.0(4) . . ?
C11_2 N1_2 C1_2 122.4(4) . . ?
C11_2 N1_2 C7_2 116.6(5) . . ?
C2_2 C1_2 N1_2 120.6(6) . . ?
C2_2 C1_2 C6_2 121.3(5) . . ?
C6_2 C1_2 N1_2 118.1(6) . . ?
C1_2 C2_2 C12_2 123.3(6) . . ?
C3_2 C2_2 C1_2 118.6(7) . . ?
C3_2 C2_2 C12_2 118.1(6) . . ?
C2_2 C3_2 H3_2 119.2 . . ?
C2_2 C3_2 C4_2 121.6(7) . . ?
C4_2 C3_2 H3_2 119.2 . . ?
C3_2 C4_2 H4_2 120.3 . . ?
C5_2 C4_2 C3_2 119.4(6) . . ?
C5_2 C4_2 H4_2 120.3 . . ?
C4_2 C5_2 H5_2 119.0 . . ?
C4_2 C5_2 C6_2 121.9(7) . . ?
C6_2 C5_2 H5_2 119.0 . . ?
C1_2 C6_2 C14_2 124.6(6) . . ?
C5_2 C6_2 C1_2 117.1(6) . . ?
C5_2 C6_2 C14_2 118.2(7) . . ?
C1 C7_2 C2 111.2(7) . . ?
C1 C7_2 C3 109.6(7) . . ?
C2 C7_2 C3 108.8(6) . . ?
N1_2 C7_2 C1 111.9(5) . . ?
N1_2 C7_2 C2 108.4(6) . . ?
N1_2 C7_2 C3 106.8(6) . . ?
C7A C10_2 C4 105.7(14) . . ?
C7A C10_2 C11_2 114.7(12) . . ?
C4 C10_2 C11_2 113.4(13) . . ?
C6 C10_2 C7A 112.8(14) . . ?
C6 C10_2 C4 108.1(13) . . ?
C6 C10_2 C11_2 102.2(14) . . ?
C10A C11_2 P1_2 112.8(6) . . ?
N1_2 C11_2 C10A 110.3(7) . . ?
N1_2 C11_2 P1_2 135.2(5) . . ?
N1_2 C11_2 C10_2 108.7(7) . . ?
C10_2 C11_2 P1_2 114.5(7) . . ?
C2_2 C12_2 H12_2 107.7 . . ?
C2_2 C12_2 C13_2 111.1(6) . . ?
C13_2 C12_2 H12_2 107.7 . . ?
C20_2 C12_2 C2_2 111.7(7) . . ?
C20_2 C12_2 H12_2 107.7 . . ?
C20_2 C12_2 C13_2 110.7(7) . . ?
C12_2 C13_2 H13A_2 109.5 . . ?
C12_2 C13_2 H13B_2 109.5 . . ?
C12_2 C13_2 H13C_2 109.5 . . ?
H13A_2 C13_2 H13B_2 109.5 . . ?
H13A_2 C13_2 H13C_2 109.5 . . ?
H13B_2 C13_2 H13C_2 109.5 . . ?
C6_2 C14_2 H14_2 108.3 . . ?
C6_2 C14_2 C15_2 111.6(6) . . ?
C6_2 C14_2 C21_2 112.0(6) . . ?
C15_2 C14_2 H14_2 108.3 . . ?
C21_2 C14_2 H14_2 108.3 . . ?
C21_2 C14_2 C15_2 108.3(7) . . ?
C14_2 C15_2 H15A_2 109.5 . . ?
C14_2 C15_2 H15B_2 109.5 . . ?
C14_2 C15_2 H15C_2 109.5 . . ?
H15A_2 C15_2 H15B_2 109.5 . . ?
H15A_2 C15_2 H15C_2 109.5 . . ?
H15B_2 C15_2 H15C_2 109.5 . . ?
C12_2 C20_2 H20A_2 109.5 . . ?
C12_2 C20_2 H20B_2 109.5 . . ?
C12_2 C20_2 H20C_2 109.5 . . ?
H20A_2 C20_2 H20B_2 109.5 . . ?
H20A_2 C20_2 H20C_2 109.5 . . ?
H20B_2 C20_2 H20C_2 109.5 . . ?
C14_2 C21_2 H21A_2 109.5 . . ?
C14_2 C21_2 H21B_2 109.5 . . ?
C14_2 C21_2 H21C_2 109.5 . . ?
H21A_2 C21_2 H21B_2 109.5 . . ?
H21A_2 C21_2 H21C_2 109.5 . . ?
H21B_2 C21_2 H21C_2 109.5 . . ?

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
C2 C5 C10A C7 -166.4(11) . . . . ?
C2 C5 C10A C8 -49.6(12) . . . . ?
C2 C5 C10A C11_2 60.6(14) . . . . ?
C2 C6 C10_2 C7A 172.4(12) . . . . ?
C2 C6 C10_2 C4 -71.1(14) . . . . ?
C2 C6 C10_2 C11_2 48.8(17) . . . . ?
C3 C4 C10_2 C7A 170.1(11) . . . . ?
C3 C4 C10_2 C6 49.0(13) . . . . ?
C3 C4 C10_2 C11_2 -63.5(15) . . . . ?
C3 C8 C10A C7 -171.3(9) . . . . ?
C3 C8 C10A C5 70.0(13) . . . . ?
C3 C8 C10A C11_2 -50.2(13) . . . . ?
C7 C10A C11_2 P1_2 -10.3(17) . . . . ?
C7 C10A C11_2 N1_2 -177.5(12) . . . . ?
C7A C10_2 C11_2 P1_2 4(2) . . . . ?
C7A C10_2 C11_2 N1_2 171.6(14) . . . . ?
C4 C3 C7_2 C1 162.7(10) . . . . ?
C4 C3 C7_2 C2 -75.6(11) . . . . ?
C4 C3 C7_2 N1_2 41.3(12) . . . . ?
C4 C10_2 C11_2 P1_2 -117.6(12) . . . . ?
C4 C10_2 C11_2 N1_2 50.2(16) . . . . ?
C5 C2 C7_2 C1 -161.7(10) . . . . ?
C5 C2 C7_2 C3 77.4(11) . . . . ?
C5 C2 C7_2 N1_2 -38.4(13) . . . . ?
C5 C10A C11_2 P1_2 120.1(11) . . . . ?
C5 C10A C11_2 N1_2 -47.1(15) . . . . ?
C8 C3 C7_2 C1 -171.3(6) . . . . ?
C8 C3 C7_2 C2 -49.5(7) . . . . ?
C8 C3 C7_2 N1_2 67.3(7) . . . . ?
C8 C10A C11_2 P1_2 -125.0(9) . . . . ?
C8 C10A C11_2 N1_2 67.8(12) . . . . ?
C6 C2 C7_2 C1 170.2(7) . . . . ?
C6 C2 C7_2 C3 49.3(8) . . . . ?
C6 C2 C7_2 N1_2 -66.5(8) . . . . ?
C6 C10_2 C11_2 P1_2 126.3(10) . . . . ?
C6 C10_2 C11_2 N1_2 -66.0(14) . . . . ?
C9 C8 C10A C7 -52.9(15) . . . . ?
C9 C8 C10A C5 -171.6(12) . . . . ?
C9 C8 C10A C11_2 68.2(13) . . . . ?
C10 C6 C10_2 C7A 56.2(19) . . . . ?
C10 C6 C10_2 C4 172.7(12) . . . . ?
C10 C6 C10_2 C11_2 -67.5(15) . . . . ?
C20A C2_1 C1_1 P1_1 22.0(14) . . . . ?
C20A C2_1 C1_1 N1_1 -158.8(13) . . . . ?
C20A C2_1 C3_1 C4_1 163.8(13) . . . . ?
P1_1 P1_1 C1_1 N1_1 -3.0(7) 2_665 . . . ?
P1_1 P1_1 C1_1 C2_1 176.0(5) 2_665 . . . ?
N1_1 C11_1 C12_1 C13_1 -172.4(5) . . . . ?
N1_1 C11_1 C12_1 C20_1 9.5(8) . . . . ?
N1_1 C11_1 C16_1 C15_1 172.4(5) . . . . ?
N1_1 C11_1 C16_1 C17_1 -9.1(7) . . . . ?
N1_1 C5_1 C6_1 C7_1 -58.2(7) . . . . ?
N1_1 C5_1 C4_1 C3_1 52.4(7) . . . . ?
C11_1 N1_1 C5_1 C6_1 -122.8(6) . . . . ?
C11_1 N1_1 C5_1 C8_1 -0.5(8) . . . . ?
C11_1 N1_1 C5_1 C4_1 121.5(6) . . . . ?
C11_1 N1_1 C1_1 P1_1 1.7(10) . . . . ?
C11_1 N1_1 C1_1 C2_1 -177.3(6) . . . . ?
C11_1 C12_1 C13_1 C14_1 -1.1(9) . . . . ?
C11_1 C12_1 C20_1 C22_1 -115.6(7) . . . . ?
C11_1 C12_1 C20_1 C21_1 122.1(6) . . . . ?
C11_1 C16_1 C17_1 C19_1 119.0(6) . . . . ?
C11_1 C16_1 C17_1 C18_1 -119.3(6) . . . . ?
C12_1 C11_1 C16_1 C15_1 -4.7(7) . . . . ?
C12_1 C11_1 C16_1 C17_1 173.8(5) . . . . ?
C12_1 C13_1 C14_1 C15_1 -2.3(9) . . . . ?
C13_1 C12_1 C20_1 C22_1 66.4(8) . . . . ?
C13_1 C12_1 C20_1 C21_1 -55.9(8) . . . . ?
C13_1 C14_1 C15_1 C16_1 2.2(9) . . . . ?
C14_1 C15_1 C16_1 C11_1 1.2(9) . . . . ?
C14_1 C15_1 C16_1 C17_1 -177.3(6) . . . . ?
C15_1 C16_1 C17_1 C19_1 -62.6(7) . . . . ?
C15_1 C16_1 C17_1 C18_1 59.2(7) . . . . ?
C16_1 C11_1 C12_1 C13_1 4.6(7) . . . . ?
C16_1 C11_1 C12_1 C20_1 -173.4(5) . . . . ?
C5_1 N1_1 C11_1 C12_1 88.8(7) . . . . ?
C5_1 N1_1 C11_1 C16_1 -88.3(6) . . . . ?
C5_1 N1_1 C1_1 P1_1 -178.4(5) . . . . ?
C5_1 N1_1 C1_1 C2_1 2.6(8) . . . . ?
C5_1 C6_1 C7_1 C2_1 4.8(10) . . . . ?
C5_1 C6_1 C7_1 C9_1 139.3(8) . . . . ?
C5_1 C4_1 C3_1 C2_1 3.3(10) . . . . ?
C6_1 C5_1 C4_1 C3_1 -62.1(7) . . . . ?
C6_1 C7_1 C2_1 C20A 167.4(10) . . . . ?
C6_1 C7_1 C2_1 C1_1 53.5(9) . . . . ?
C6_1 C7_1 C2_1 C3_1 -62.8(9) . . . . ?
C6_1 C7_1 C2_1 C10_1 -173.8(8) . . . . ?
C7_1 C2_1 C1_1 P1_1 122.2(5) . . . . ?
C7_1 C2_1 C1_1 N1_1 -58.6(7) . . . . ?
C7_1 C2_1 C3_1 C4_1 57.3(9) . . . . ?
C1_1 N1_1 C11_1 C12_1 -91.2(7) . . . . ?
C1_1 N1_1 C11_1 C16_1 91.6(7) . . . . ?
C1_1 N1_1 C5_1 C6_1 57.2(7) . . . . ?
C1_1 N1_1 C5_1 C8_1 179.6(5) . . . . ?
C1_1 N1_1 C5_1 C4_1 -58.4(7) . . . . ?
C1_1 C2_1 C3_1 C4_1 -59.2(9) . . . . ?
C20_1 C12_1 C13_1 C14_1 177.0(6) . . . . ?
C8_1 C5_1 C6_1 C7_1 178.8(6) . . . . ?
C8_1 C5_1 C4_1 C3_1 175.1(6) . . . . ?
C4_1 C5_1 C6_1 C7_1 56.2(7) . . . . ?
C3_1 C2_1 C1_1 P1_1 -122.0(6) . . . . ?
C3_1 C2_1 C1_1 N1_1 57.3(8) . . . . ?
C9_1 C7_1 C2_1 C20A 28.4(12) . . . . ?
C9_1 C7_1 C2_1 C1_1 -85.5(10) . . . . ?
C9_1 C7_1 C2_1 C3_1 158.2(9) . . . . ?
C9_1 C7_1 C2_1 C10_1 47.1(13) . . . . ?
C10_1 C2_1 C1_1 P1_1 -12.5(10) . . . . ?
C10_1 C2_1 C1_1 N1_1 166.7(8) . . . . ?
C10_1 C2_1 C3_1 C4_1 -178.9(8) . . . . ?
P1_2 P1_2 C11_2 C10A -162.1(9) 2_665 . . . ?
P1_2 P1_2 C11_2 N1_2 0.8(12) 2_665 . . . ?
P1_2 P1_2 C11_2 C10_2 164.3(11) 2_665 . . . ?
N1_2 C1_2 C2_2 C3_2 -178.7(5) . . . . ?
N1_2 C1_2 C2_2 C12_2 4.3(8) . . . . ?
N1_2 C1_2 C6_2 C5_2 177.9(5) . . . . ?
N1_2 C1_2 C6_2 C14_2 -4.7(8) . . . . ?
C1_2 N1_2 C7_2 C1 0.6(11) . . . . ?
C1_2 N1_2 C7_2 C2 -122.3(8) . . . . ?
C1_2 N1_2 C7_2 C3 120.6(8) . . . . ?
C1_2 N1_2 C11_2 C10A 162.8(9) . . . . ?
C1_2 N1_2 C11_2 P1_2 -0.4(16) . . . . ?
C1_2 N1_2 C11_2 C10_2 -164.5(11) . . . . ?
C1_2 C2_2 C3_2 C4_2 1.0(9) . . . . ?
C1_2 C2_2 C12_2 C13_2 -116.6(7) . . . . ?
C1_2 C2_2 C12_2 C20_2 119.3(7) . . . . ?
C1_2 C6_2 C14_2 C15_2 115.3(7) . . . . ?
C1_2 C6_2 C14_2 C21_2 -123.1(7) . . . . ?
C2_2 C1_2 C6_2 C5_2 -0.5(7) . . . . ?
C2_2 C1_2 C6_2 C14_2 176.9(6) . . . . ?
C2_2 C3_2 C4_2 C5_2 -0.8(9) . . . . ?
C3_2 C2_2 C12_2 C13_2 66.4(9) . . . . ?
C3_2 C2_2 C12_2 C20_2 -57.7(9) . . . . ?
C3_2 C4_2 C5_2 C6_2 0.0(8) . . . . ?
C4_2 C5_2 C6_2 C1_2 0.6(9) . . . . ?
C4_2 C5_2 C6_2 C14_2 -176.9(6) . . . . ?
C5_2 C6_2 C14_2 C15_2 -67.4(8) . . . . ?
C5_2 C6_2 C14_2 C21_2 54.3(9) . . . . ?
C6_2 C1_2 C2_2 C3_2 -0.3(8) . . . . ?
C6_2 C1_2 C2_2 C12_2 -177.3(6) . . . . ?
C7_2 C2 C5 C10A -16.1(15) . . . . ?
C7_2 C2 C6 C10 136.3(11) . . . . ?
C7_2 C2 C6 C10_2 13.4(15) . . . . ?
C7_2 C3 C4 C10_2 15.7(15) . . . . ?
C7_2 C3 C8 C9 -138.8(9) . . . . ?
C7_2 C3 C8 C10A -12.4(12) . . . . ?
C7_2 N1_2 C1_2 C2_2 87.0(8) . . . . ?
C7_2 N1_2 C1_2 C6_2 -91.4(8) . . . . ?
C7_2 N1_2 C11_2 C10A -16.2(13) . . . . ?
C7_2 N1_2 C11_2 P1_2 -179.3(9) . . . . ?
C7_2 N1_2 C11_2 C10_2 16.5(14) . . . . ?
C11_2 N1_2 C1_2 C2_2 -91.9(9) . . . . ?
C11_2 N1_2 C1_2 C6_2 89.7(9) . . . . ?
C11_2 N1_2 C7_2 C1 179.6(8) . . . . ?
C11_2 N1_2 C7_2 C2 56.7(10) . . . . ?
C11_2 N1_2 C7_2 C3 -60.4(10) . . . . ?
C12_2 C2_2 C3_2 C4_2 178.2(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_sk_ry_bicaacpiritu_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2264852'
loop_
_audit_author_name
_audit_author_address
'Subrata Kundu'
;IIT Delhi
India
;
_audit_update_record             
;
2023-05-23 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;
_audit_creation_date             2023-05-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H33 I N P'
_chemical_formula_sum            'C22 H33 I N P'
_chemical_formula_weight         469.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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                   15.5985(9)
_cell_length_b                   19.4320(13)
_cell_length_c                   29.7451(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     9016.0(9)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.030
_cell_measurement_theta_min      2.504
_shelx_estimated_absorpt_T_max   0.865
_shelx_estimated_absorpt_T_min   0.725
_exptl_absorpt_coefficient_mu    1.497
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0831 before and 0.0668 after correction.
The Ratio of minimum to maximum transmission is 0.8357.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3840
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            81806
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         1.892
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5602
_reflns_number_total             9211
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.631
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     485
_refine_ls_number_reflns         9211
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.012
_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)+(0.0455P)²+10.4224P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1255
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 I1-P1 \\sim I1A-P1
 with sigma of 0.02
 I2-P2 \\sim I2A-P2
 with sigma of 0.02
3. Others
 Sof(I1A)=1-FVAR(1)
 Sof(I1)=FVAR(1)
 Sof(I2A)=1-FVAR(2)
 Sof(I2)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C40(H40), C43(H43), C20(H20), C17(H17), C7(H7), C25(H25)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C33(H33A,H33B), C28(H28A,H28B), C4(H4A,H4B), C3(H3A,H3B),
 C29(H29A,H29B)
4.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C38(H38), C37(H37), C36(H36)
4.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C41(H41A,H41B,H41C), C8(H8A,H8B,H8C), C42(H42A,H42B,
 H42C), C45(H45A,H45B,H45C), C22(H22A,H22B,H22C), C44(H44A,H44B,H44C), C21(H21A,
 H21B,H21C), C18(H18A,H18B,H18C), C9(H9A,H9B,H9C), C19(H19A,H19B,H19C),
 C32(H32A,H32B,H32C), C10(H10A,H10B,H10C), C31(H31A,H31B,H31C)
;
_atom_sites_solution_hydrogens   geom
_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
I2 I 0.4149(5) 0.4618(4) 0.70495(17) 0.0719(9) Uani 0.60(4) 1 d D . P A 1
I1 I 0.8962(3) 0.6772(8) 0.54677(18) 0.0794(14) Uani 0.43(4) 1 d D . P B 1
P2 P 0.25977(9) 0.49613(9) 0.70694(4) 0.0766(4) Uani 1 1 d D . . . .
P1 P 0.92216(8) 0.72082(9) 0.62121(5) 0.0764(4) Uani 1 1 d D . . . .
N1 N 0.7462(2) 0.71923(18) 0.64924(10) 0.0484(8) Uani 1 1 d . . . . .
N2 N 0.23713(19) 0.48603(18) 0.61160(10) 0.0443(8) Uani 1 1 d . . . . .
C39 C 0.3863(2) 0.5048(2) 0.58851(13) 0.0484(10) Uani 1 1 d . . . . .
C11 C 0.7109(2) 0.6848(2) 0.60993(12) 0.0438(10) Uani 1 1 d . . . . .
C34 C 0.3213(2) 0.4588(2) 0.60057(12) 0.0435(9) Uani 1 1 d . . . . .
C12 C 0.7102(2) 0.6132(2) 0.60826(13) 0.0485(10) Uani 1 1 d . . . . .
C35 C 0.3343(3) 0.3878(2) 0.60158(13) 0.0526(11) Uani 1 1 d . . . . .
C1 C 0.8315(3) 0.7329(2) 0.65287(13) 0.0534(11) Uani 1 1 d . . . . .
C27 C 0.1705(3) 0.4986(3) 0.57575(14) 0.0552(11) Uani 1 1 d . . . . .
C13 C 0.6770(3) 0.5822(3) 0.56947(15) 0.0577(12) Uani 1 1 d . . . . .
H13 H 0.676677 0.534496 0.567174 0.069 Uiso 1 1 calc R U . . .
C40 C 0.3752(3) 0.5820(2) 0.58764(16) 0.0592(12) Uani 1 1 d . . . . .
H40 H 0.315261 0.592406 0.594690 0.071 Uiso 1 1 calc R U . . .
C30 C 0.2049(3) 0.4801(3) 0.52925(14) 0.0682(14) Uani 1 1 d . . . . .
H30A H 0.253140 0.508827 0.522311 0.102 Uiso 1 1 calc R U . . .
H30B H 0.160745 0.487054 0.507222 0.102 Uiso 1 1 calc R U . . .
H30C H 0.222362 0.432708 0.528972 0.102 Uiso 1 1 calc R U . . .
C14 C 0.6453(3) 0.6208(3) 0.53506(14) 0.0653(14) Uani 1 1 d . . . . .
H14 H 0.623903 0.599146 0.509552 0.078 Uiso 1 1 calc R U . . .
C15 C 0.6447(3) 0.6913(3) 0.53759(14) 0.0643(13) Uani 1 1 d . . . . .
H15 H 0.621276 0.716593 0.514067 0.077 Uiso 1 1 calc R U . . .
C38 C 0.4657(3) 0.4768(3) 0.57730(15) 0.0643(13) Uani 1 1 d . . . . .
H38 H 0.510011 0.506147 0.568927 0.077 Uiso 1 1 calc R U . . .
C5 C 0.6899(3) 0.7400(3) 0.68793(15) 0.0638(13) Uani 1 1 d . . . . .
C43 C 0.2668(4) 0.3366(3) 0.61511(16) 0.0712(14) Uani 1 1 d . . . . .
H43 H 0.214691 0.362409 0.622606 0.085 Uiso 1 1 calc R U . . .
C23 C 0.2131(3) 0.5004(3) 0.65463(14) 0.0569(12) Uani 1 1 d . . . . .
C37 C 0.4805(3) 0.4074(3) 0.57823(15) 0.0689(14) Uani 1 1 d . . . . .
H37 H 0.534198 0.390093 0.570713 0.083 Uiso 1 1 calc R U . . .
C36 C 0.4156(3) 0.3637(3) 0.59031(15) 0.0661(13) Uani 1 1 d . . . . .
H36 H 0.426180 0.316638 0.591006 0.079 Uiso 1 1 calc R U . . .
C20 C 0.7420(3) 0.5669(3) 0.64606(17) 0.0670(13) Uani 1 1 d . . . . .
H20 H 0.765609 0.596887 0.669476 0.080 Uiso 1 1 calc R U . . .
C17 C 0.6793(3) 0.8030(3) 0.57547(16) 0.0680(14) Uani 1 1 d . . . . .
H17 H 0.695317 0.817336 0.605926 0.082 Uiso 1 1 calc R U . . .
C2 C 0.8503(4) 0.7712(3) 0.69741(16) 0.0762(16) Uani 1 1 d . . . . .
C6 C 0.7263(4) 0.7039(3) 0.72932(15) 0.0808(16) Uani 1 1 d . . . . .
H6A H 0.722525 0.654411 0.725547 0.097 Uiso 1 1 calc R U . . .
H6B H 0.693403 0.716597 0.755713 0.097 Uiso 1 1 calc R U . . .
C33 C 0.0923(3) 0.4557(3) 0.58806(18) 0.0838(17) Uani 1 1 d . . . . .
H33A H 0.106859 0.407198 0.587460 0.101 Uiso 1 1 calc R U . . .
H33B H 0.046847 0.463621 0.566384 0.101 Uiso 1 1 calc R U . . .
C28 C 0.1442(3) 0.5739(3) 0.57789(18) 0.0787(16) Uani 1 1 d . . . . .
H28A H 0.094838 0.581437 0.558641 0.094 Uiso 1 1 calc R U . . .
H28B H 0.190730 0.602477 0.566966 0.094 Uiso 1 1 calc R U . . .
C41 C 0.3955(4) 0.6122(3) 0.54131(19) 0.0848(17) Uani 1 1 d . . . . .
H41A H 0.455351 0.606066 0.534862 0.127 Uiso 1 1 calc R U . . .
H41B H 0.381995 0.660371 0.541131 0.127 Uiso 1 1 calc R U . . .
H41C H 0.361963 0.589027 0.518881 0.127 Uiso 1 1 calc R U . . .
C24 C 0.1215(3) 0.5297(4) 0.65583(19) 0.0867(19) Uani 1 1 d . . . . .
C7 C 0.8218(4) 0.7255(3) 0.73565(17) 0.0892(18) Uani 1 1 d . . . . .
H7 H 0.823911 0.753861 0.762880 0.107 Uiso 1 1 calc R U . . .
C4 C 0.7011(5) 0.8171(3) 0.6954(2) 0.095(2) Uani 1 1 d . . . . .
H4A H 0.673020 0.842036 0.671264 0.115 Uiso 1 1 calc R U . . .
H4B H 0.673980 0.830151 0.723455 0.115 Uiso 1 1 calc R U . . .
C16 C 0.6784(3) 0.7257(2) 0.57468(13) 0.0510(11) Uani 1 1 d . . . . .
C8 C 0.5967(3) 0.7215(4) 0.6791(2) 0.107(2) Uani 1 1 d . . . . .
H8A H 0.578419 0.742152 0.651421 0.160 Uiso 1 1 calc R U . . .
H8B H 0.561776 0.738314 0.703337 0.160 Uiso 1 1 calc R U . . .
H8C H 0.591022 0.672417 0.677084 0.160 Uiso 1 1 calc R U . . .
C42 C 0.4318(4) 0.6182(3) 0.6225(2) 0.0931(18) Uani 1 1 d . . . . .
H42A H 0.417039 0.602337 0.652042 0.140 Uiso 1 1 calc R U . . .
H42B H 0.422996 0.667009 0.620691 0.140 Uiso 1 1 calc R U . . .
H42C H 0.490968 0.607927 0.616527 0.140 Uiso 1 1 calc R U . . .
C45 C 0.2443(5) 0.2865(3) 0.57710(18) 0.104(2) Uani 1 1 d . . . . .
H45A H 0.226674 0.311924 0.551038 0.156 Uiso 1 1 calc R U . . .
H45B H 0.198555 0.256851 0.586616 0.156 Uiso 1 1 calc R U . . .
H45C H 0.293785 0.259219 0.569842 0.156 Uiso 1 1 calc R U . . .
C3 C 0.7956(6) 0.8368(3) 0.6968(2) 0.116(3) Uani 1 1 d . . . . .
H3A H 0.807198 0.863964 0.723503 0.139 Uiso 1 1 calc R U . . .
H3B H 0.809997 0.864346 0.670669 0.139 Uiso 1 1 calc R U . . .
C25 C 0.0614(4) 0.4760(4) 0.6354(2) 0.110(2) Uani 1 1 d . . . . .
H25 H 0.005789 0.498644 0.631460 0.132 Uiso 1 1 calc R U . . .
C22 C 0.6682(4) 0.5266(3) 0.6671(2) 0.102(2) Uani 1 1 d . . . . .
H22A H 0.624066 0.558027 0.676431 0.153 Uiso 1 1 calc R U . . .
H22B H 0.688782 0.501600 0.692773 0.153 Uiso 1 1 calc R U . . .
H22C H 0.645248 0.494997 0.645467 0.153 Uiso 1 1 calc R U . . .
C29 C 0.1217(4) 0.5948(4) 0.6266(2) 0.115(3) Uani 1 1 d . . . . .
H29A H 0.163650 0.627317 0.637898 0.138 Uiso 1 1 calc R U . . .
H29B H 0.065703 0.616504 0.627443 0.138 Uiso 1 1 calc R U . . .
C44 C 0.2929(5) 0.2948(3) 0.65710(18) 0.116(3) Uani 1 1 d . . . . .
H44A H 0.342800 0.267739 0.650364 0.174 Uiso 1 1 calc R U . . .
H44B H 0.246661 0.264882 0.665610 0.174 Uiso 1 1 calc R U . . .
H44C H 0.305493 0.325660 0.681399 0.174 Uiso 1 1 calc R U . . .
C21 C 0.8124(4) 0.5189(3) 0.6317(2) 0.109(2) Uani 1 1 d . . . . .
H21A H 0.791024 0.487913 0.609252 0.164 Uiso 1 1 calc R U . . .
H21B H 0.832051 0.493124 0.657244 0.164 Uiso 1 1 calc R U . . .
H21C H 0.859122 0.545121 0.619531 0.164 Uiso 1 1 calc R U . . .
C18 C 0.7458(5) 0.8326(3) 0.5432(2) 0.109(2) Uani 1 1 d . . . . .
H18A H 0.802304 0.821173 0.553686 0.164 Uiso 1 1 calc R U . . .
H18B H 0.739788 0.881689 0.541857 0.164 Uiso 1 1 calc R U . . .
H18C H 0.737339 0.813430 0.513793 0.164 Uiso 1 1 calc R U . . .
C9 C 0.9451(5) 0.7916(4) 0.7039(2) 0.134(3) Uani 1 1 d . . . . .
H9A H 0.979594 0.750816 0.706179 0.201 Uiso 1 1 calc R U . . .
H9B H 0.950875 0.818159 0.730985 0.201 Uiso 1 1 calc R U . . .
H9C H 0.963856 0.818509 0.678723 0.201 Uiso 1 1 calc R U . . .
C19 C 0.5914(4) 0.8341(4) 0.5653(3) 0.129(3) Uani 1 1 d . . . . .
H19A H 0.578126 0.827508 0.534048 0.194 Uiso 1 1 calc R U . . .
H19B H 0.592287 0.882446 0.571922 0.194 Uiso 1 1 calc R U . . .
H19C H 0.548696 0.811911 0.583401 0.194 Uiso 1 1 calc R U . . .
C32 C 0.0898(4) 0.5514(5) 0.7036(2) 0.152(4) Uani 1 1 d . . . . .
H32A H 0.098597 0.514148 0.724280 0.228 Uiso 1 1 calc R U . . .
H32B H 0.029854 0.562511 0.702373 0.228 Uiso 1 1 calc R U . . .
H32C H 0.121438 0.590979 0.713560 0.228 Uiso 1 1 calc R U . . .
C10 C 0.8775(5) 0.6651(4) 0.7442(3) 0.134(3) Uani 1 1 d . . . . .
H10A H 0.878272 0.636101 0.718126 0.202 Uiso 1 1 calc R U . . .
H10B H 0.855582 0.639717 0.769414 0.202 Uiso 1 1 calc R U . . .
H10C H 0.934671 0.680461 0.750731 0.202 Uiso 1 1 calc R U . . .
C31 C 0.0466(6) 0.4168(5) 0.6653(3) 0.169(4) Uani 1 1 d . . . . .
H31A H 0.006606 0.385772 0.651493 0.254 Uiso 1 1 calc R U . . .
H31B H 0.023614 0.432726 0.693411 0.254 Uiso 1 1 calc R U . . .
H31C H 0.099791 0.393355 0.670601 0.254 Uiso 1 1 calc R U . . .
I1A I 0.8972(2) 0.6623(7) 0.54732(14) 0.0762(11) Uani 0.57(4) 1 d D . P B 2
I2A I 0.4032(8) 0.4546(6) 0.7075(3) 0.0808(16) Uani 0.40(4) 1 d D . P A 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
I2 P2 2.510(7) . ?
I1 P1 2.405(7) . ?
P2 C23 1.720(4) . ?
P2 I2A 2.379(10) . ?
P1 C1 1.715(5) . ?
P1 I1A 2.505(6) . ?
N1 C11 1.456(5) . ?
N1 C1 1.362(5) . ?
N1 C5 1.502(5) . ?
N2 C34 1.452(5) . ?
N2 C27 1.509(5) . ?
N2 C23 1.363(5) . ?
C39 C34 1.399(6) . ?
C39 C40 1.510(6) . ?
C39 C38 1.393(6) . ?
C11 C12 1.392(6) . ?
C11 C16 1.410(6) . ?
C34 C35 1.396(6) . ?
C12 C13 1.400(6) . ?
C12 C20 1.523(6) . ?
C35 C43 1.503(6) . ?
C35 C36 1.393(6) . ?
C1 C2 1.547(6) . ?
C27 C30 1.526(6) . ?
C27 C33 1.522(6) . ?
C27 C28 1.522(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.362(7) . ?
C40 H40 0.9800 . ?
C40 C41 1.531(7) . ?
C40 C42 1.532(7) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C14 H14 0.9300 . ?
C14 C15 1.371(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.393(6) . ?
C38 H38 0.9300 . ?
C38 C37 1.368(7) . ?
C5 C6 1.526(7) . ?
C5 C4 1.525(8) . ?
C5 C8 1.520(7) . ?
C43 H43 0.9800 . ?
C43 C45 1.533(7) . ?
C43 C44 1.545(7) . ?
C23 C24 1.539(7) . ?
C37 H37 0.9300 . ?
C37 C36 1.369(7) . ?
C36 H36 0.9300 . ?
C20 H20 0.9800 . ?
C20 C22 1.527(7) . ?
C20 C21 1.502(7) . ?
C17 H17 0.9800 . ?
C17 C16 1.503(7) . ?
C17 C18 1.526(7) . ?
C17 C19 1.528(7) . ?
C2 C7 1.509(7) . ?
C2 C3 1.534(9) . ?
C2 C9 1.543(9) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.559(8) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C25 1.539(8) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.545(8) . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C24 C25 1.529(9) . ?
C24 C29 1.534(9) . ?
C24 C32 1.563(7) . ?
C7 H7 0.9800 . ?
C7 C10 1.482(9) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.524(10) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C25 H25 0.9800 . ?
C25 C31 1.473(10) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?

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
C23 P2 I2 113.52(18) . . ?
C23 P2 I2A 114.9(2) . . ?
C1 P1 I1 114.5(2) . . ?
C1 P1 I1A 114.57(18) . . ?
C11 N1 C5 121.2(3) . . ?
C1 N1 C11 121.5(3) . . ?
C1 N1 C5 117.3(3) . . ?
C34 N2 C27 121.4(3) . . ?
C23 N2 C34 122.4(3) . . ?
C23 N2 C27 116.2(3) . . ?
C34 C39 C40 123.8(4) . . ?
C38 C39 C34 117.2(4) . . ?
C38 C39 C40 119.0(4) . . ?
C12 C11 N1 119.4(4) . . ?
C12 C11 C16 122.3(4) . . ?
C16 C11 N1 118.3(4) . . ?
C39 C34 N2 118.8(4) . . ?
C35 C34 N2 119.1(4) . . ?
C35 C34 C39 122.1(4) . . ?
C11 C12 C13 117.5(4) . . ?
C11 C12 C20 124.1(4) . . ?
C13 C12 C20 118.3(4) . . ?
C34 C35 C43 123.9(4) . . ?
C36 C35 C34 117.4(4) . . ?
C36 C35 C43 118.8(4) . . ?
N1 C1 P1 137.4(3) . . ?
N1 C1 C2 110.3(4) . . ?
C2 C1 P1 112.3(3) . . ?
N2 C27 C30 111.1(3) . . ?
N2 C27 C33 107.1(4) . . ?
N2 C27 C28 108.2(4) . . ?
C33 C27 C30 111.8(4) . . ?
C33 C27 C28 107.4(4) . . ?
C28 C27 C30 111.0(4) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.1(5) . . ?
C14 C13 H13 119.4 . . ?
C39 C40 H40 108.1 . . ?
C39 C40 C41 111.9(4) . . ?
C39 C40 C42 112.3(4) . . ?
C41 C40 H40 108.1 . . ?
C41 C40 C42 108.3(4) . . ?
C42 C40 H40 108.1 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.8(4) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.3 . . ?
C14 C15 C16 121.3(4) . . ?
C16 C15 H15 119.3 . . ?
C39 C38 H38 119.0 . . ?
C37 C38 C39 122.0(5) . . ?
C37 C38 H38 119.0 . . ?
N1 C5 C6 106.1(4) . . ?
N1 C5 C4 107.9(4) . . ?
N1 C5 C8 111.3(4) . . ?
C4 C5 C6 107.0(4) . . ?
C8 C5 C6 112.7(5) . . ?
C8 C5 C4 111.5(5) . . ?
C35 C43 H43 107.7 . . ?
C35 C43 C45 112.5(4) . . ?
C35 C43 C44 112.3(5) . . ?
C45 C43 H43 107.7 . . ?
C45 C43 C44 108.8(5) . . ?
C44 C43 H43 107.7 . . ?
N2 C23 P2 136.4(3) . . ?
N2 C23 C24 110.7(4) . . ?
C24 C23 P2 112.9(3) . . ?
C38 C37 H37 120.3 . . ?
C38 C37 C36 119.5(4) . . ?
C36 C37 H37 120.3 . . ?
C35 C36 H36 119.1 . . ?
C37 C36 C35 121.9(5) . . ?
C37 C36 H36 119.1 . . ?
C12 C20 H20 107.2 . . ?
C12 C20 C22 111.1(4) . . ?
C22 C20 H20 107.2 . . ?
C21 C20 C12 113.3(5) . . ?
C21 C20 H20 107.2 . . ?
C21 C20 C22 110.5(5) . . ?
C16 C17 H17 107.5 . . ?
C16 C17 C18 111.9(4) . . ?
C16 C17 C19 112.6(5) . . ?
C18 C17 H17 107.5 . . ?
C18 C17 C19 109.7(5) . . ?
C19 C17 H17 107.5 . . ?
C7 C2 C1 107.9(4) . . ?
C7 C2 C3 109.5(5) . . ?
C7 C2 C9 109.8(5) . . ?
C3 C2 C1 106.5(5) . . ?
C3 C2 C9 108.7(6) . . ?
C9 C2 C1 114.4(5) . . ?
C5 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
C5 C6 C7 109.2(4) . . ?
H6A C6 H6B 108.3 . . ?
C7 C6 H6A 109.8 . . ?
C7 C6 H6B 109.8 . . ?
C27 C33 H33A 109.8 . . ?
C27 C33 H33B 109.8 . . ?
C27 C33 C25 109.3(4) . . ?
H33A C33 H33B 108.3 . . ?
C25 C33 H33A 109.8 . . ?
C25 C33 H33B 109.8 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 C29 110.7(5) . . ?
H28A C28 H28B 108.1 . . ?
C29 C28 H28A 109.5 . . ?
C29 C28 H28B 109.5 . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C23 C24 C32 114.5(5) . . ?
C25 C24 C23 107.9(5) . . ?
C25 C24 C29 109.8(6) . . ?
C25 C24 C32 110.6(5) . . ?
C29 C24 C23 106.8(5) . . ?
C29 C24 C32 107.1(6) . . ?
C2 C7 C6 110.4(4) . . ?
C2 C7 H7 106.4 . . ?
C6 C7 H7 106.4 . . ?
C10 C7 C2 115.0(6) . . ?
C10 C7 C6 111.5(6) . . ?
C10 C7 H7 106.4 . . ?
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C3 C4 C5 111.2(5) . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
C11 C16 C17 123.3(4) . . ?
C15 C16 C11 117.0(4) . . ?
C15 C16 C17 119.7(4) . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C40 C42 H42A 109.5 . . ?
C40 C42 H42B 109.5 . . ?
C40 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C43 C45 H45A 109.5 . . ?
C43 C45 H45B 109.5 . . ?
C43 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C2 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
C4 C3 C2 109.2(5) . . ?
C4 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
H3A C3 H3B 108.3 . . ?
C33 C25 H25 106.4 . . ?
C24 C25 C33 110.3(4) . . ?
C24 C25 H25 106.4 . . ?
C31 C25 C33 113.7(7) . . ?
C31 C25 C24 112.9(6) . . ?
C31 C25 H25 106.4 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C28 C29 H29A 110.0 . . ?
C28 C29 H29B 110.0 . . ?
C24 C29 C28 108.4(5) . . ?
C24 C29 H29A 110.0 . . ?
C24 C29 H29B 110.0 . . ?
H29A C29 H29B 108.4 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C24 C32 H32A 109.5 . . ?
C24 C32 H32B 109.5 . . ?
C24 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C25 C31 H31A 109.5 . . ?
C25 C31 H31B 109.5 . . ?
C25 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 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
I2 P2 C23 N2 4.9(6) . . . . ?
I2 P2 C23 C24 -173.2(4) . . . . ?
I1 P1 C1 N1 7.1(7) . . . . ?
I1 P1 C1 C2 -171.3(5) . . . . ?
P2 C23 C24 C25 -122.1(4) . . . . ?
P2 C23 C24 C29 119.9(5) . . . . ?
P2 C23 C24 C32 1.5(8) . . . . ?
P1 C1 C2 C7 -121.4(4) . . . . ?
P1 C1 C2 C3 121.1(5) . . . . ?
P1 C1 C2 C9 1.0(7) . . . . ?
N1 C11 C12 C13 -178.9(3) . . . . ?
N1 C11 C12 C20 1.9(6) . . . . ?
N1 C11 C16 C15 -179.7(4) . . . . ?
N1 C11 C16 C17 0.7(6) . . . . ?
N1 C1 C2 C7 59.7(6) . . . . ?
N1 C1 C2 C3 -57.7(6) . . . . ?
N1 C1 C2 C9 -177.8(5) . . . . ?
N1 C5 C6 C7 57.7(5) . . . . ?
N1 C5 C4 C3 -48.5(6) . . . . ?
N2 C34 C35 C43 -2.2(6) . . . . ?
N2 C34 C35 C36 179.3(3) . . . . ?
N2 C27 C33 C25 57.3(6) . . . . ?
N2 C27 C28 C29 -49.8(5) . . . . ?
N2 C23 C24 C25 59.3(6) . . . . ?
N2 C23 C24 C29 -58.7(6) . . . . ?
N2 C23 C24 C32 -177.0(6) . . . . ?
C39 C34 C35 C43 178.9(4) . . . . ?
C39 C34 C35 C36 0.4(6) . . . . ?
C39 C38 C37 C36 0.3(7) . . . . ?
C11 N1 C1 P1 0.3(7) . . . . ?
C11 N1 C1 C2 178.7(4) . . . . ?
C11 N1 C5 C6 121.9(4) . . . . ?
C11 N1 C5 C4 -123.8(5) . . . . ?
C11 N1 C5 C8 -1.1(6) . . . . ?
C11 C12 C13 C14 -1.1(6) . . . . ?
C11 C12 C20 C22 113.0(5) . . . . ?
C11 C12 C20 C21 -122.0(5) . . . . ?
C34 N2 C27 C30 -0.8(6) . . . . ?
C34 N2 C27 C33 121.5(4) . . . . ?
C34 N2 C27 C28 -122.9(4) . . . . ?
C34 N2 C23 P2 0.9(7) . . . . ?
C34 N2 C23 C24 178.9(4) . . . . ?
C34 C39 C40 C41 -122.9(4) . . . . ?
C34 C39 C40 C42 115.2(5) . . . . ?
C34 C39 C38 C37 -0.5(6) . . . . ?
C34 C35 C43 C45 118.5(5) . . . . ?
C34 C35 C43 C44 -118.4(5) . . . . ?
C34 C35 C36 C37 -0.6(6) . . . . ?
C12 C11 C16 C15 0.2(6) . . . . ?
C12 C11 C16 C17 -179.3(4) . . . . ?
C12 C13 C14 C15 -0.3(7) . . . . ?
C1 N1 C11 C12 86.1(5) . . . . ?
C1 N1 C11 C16 -94.0(5) . . . . ?
C1 N1 C5 C6 -57.0(5) . . . . ?
C1 N1 C5 C4 57.3(6) . . . . ?
C1 N1 C5 C8 180.0(5) . . . . ?
C1 C2 C7 C6 -54.2(6) . . . . ?
C1 C2 C7 C10 73.1(6) . . . . ?
C1 C2 C3 C4 62.2(6) . . . . ?
C27 N2 C34 C39 87.3(5) . . . . ?
C27 N2 C34 C35 -91.6(5) . . . . ?
C27 N2 C23 P2 179.7(4) . . . . ?
C27 N2 C23 C24 -2.2(6) . . . . ?
C27 C33 C25 C24 -2.9(8) . . . . ?
C27 C33 C25 C31 -130.9(6) . . . . ?
C27 C28 C29 C24 -7.7(7) . . . . ?
C13 C12 C20 C22 -66.2(6) . . . . ?
C13 C12 C20 C21 58.8(6) . . . . ?
C13 C14 C15 C16 1.8(7) . . . . ?
C40 C39 C34 N2 2.0(6) . . . . ?
C40 C39 C34 C35 -179.1(4) . . . . ?
C40 C39 C38 C37 178.7(4) . . . . ?
C30 C27 C33 C25 179.3(5) . . . . ?
C30 C27 C28 C29 -172.0(4) . . . . ?
C14 C15 C16 C11 -1.7(6) . . . . ?
C14 C15 C16 C17 177.9(4) . . . . ?
C38 C39 C34 N2 -178.8(3) . . . . ?
C38 C39 C34 C35 0.1(6) . . . . ?
C38 C39 C40 C41 58.0(5) . . . . ?
C38 C39 C40 C42 -64.0(6) . . . . ?
C38 C37 C36 C35 0.3(7) . . . . ?
C5 N1 C11 C12 -92.8(5) . . . . ?
C5 N1 C11 C16 87.2(5) . . . . ?
C5 N1 C1 P1 179.2(4) . . . . ?
C5 N1 C1 C2 -2.4(6) . . . . ?
C5 C6 C7 C2 -3.9(7) . . . . ?
C5 C6 C7 C10 -133.1(5) . . . . ?
C5 C4 C3 C2 -8.5(7) . . . . ?
C43 C35 C36 C37 -179.2(4) . . . . ?
C23 N2 C34 C39 -94.0(5) . . . . ?
C23 N2 C34 C35 87.1(5) . . . . ?
C23 N2 C27 C30 -179.6(4) . . . . ?
C23 N2 C27 C33 -57.3(5) . . . . ?
C23 N2 C27 C28 58.2(5) . . . . ?
C23 C24 C25 C33 -54.9(7) . . . . ?
C23 C24 C25 C31 73.6(7) . . . . ?
C23 C24 C29 C28 62.4(6) . . . . ?
C36 C35 C43 C45 -63.0(6) . . . . ?
C36 C35 C43 C44 60.1(6) . . . . ?
C20 C12 C13 C14 178.1(4) . . . . ?
C6 C5 C4 C3 65.3(6) . . . . ?
C33 C27 C28 C29 65.5(5) . . . . ?
C28 C27 C33 C25 -58.7(6) . . . . ?
C7 C2 C3 C4 -54.2(6) . . . . ?
C4 C5 C6 C7 -57.3(6) . . . . ?
C16 C11 C12 C13 1.1(6) . . . . ?
C16 C11 C12 C20 -178.0(4) . . . . ?
C8 C5 C6 C7 179.8(5) . . . . ?
C8 C5 C4 C3 -171.1(5) . . . . ?
C3 C2 C7 C6 61.3(6) . . . . ?
C3 C2 C7 C10 -171.4(5) . . . . ?
C25 C24 C29 C28 -54.4(6) . . . . ?
C29 C24 C25 C33 61.2(7) . . . . ?
C29 C24 C25 C31 -170.3(6) . . . . ?
C18 C17 C16 C11 107.3(5) . . . . ?
C18 C17 C16 C15 -72.3(6) . . . . ?
C9 C2 C7 C6 -179.5(5) . . . . ?
C9 C2 C7 C10 -52.2(7) . . . . ?
C9 C2 C3 C4 -174.1(5) . . . . ?
C19 C17 C16 C11 -128.7(5) . . . . ?
C19 C17 C16 C15 51.8(6) . . . . ?
C32 C24 C25 C33 179.1(6) . . . . ?
C32 C24 C25 C31 -52.4(9) . . . . ?
C32 C24 C29 C28 -174.5(5) . . . . ?
I1A P1 C1 N1 0.1(7) . . . . ?
I1A P1 C1 C2 -178.3(4) . . . . ?
I2A P2 C23 N2 -0.1(7) . . . . ?
I2A P2 C23 C24 -178.2(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_sk_ry_bicaacpbr_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2264851'
loop_
_audit_author_name
_audit_author_address
'Subrata Kundu'
;IIT Delhi
India
;
_audit_update_record             
;
2023-05-23 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;
_audit_creation_date             2023-05-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H33 Br N P'
_chemical_formula_sum            'C22 H33 Br N P'
_chemical_formula_weight         422.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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                   9.2049(8)
_cell_length_b                   16.6408(13)
_cell_length_c                   29.176(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4469.1(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3511
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      26.438
_cell_measurement_theta_min      2.448
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.916
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            120954
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.438
_diffrn_reflns_theta_min         2.448
_diffrn_ambient_temperature      302.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'BRUKER APEX IV'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3383
_reflns_number_total             4589
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4589
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.068
_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)+(0.0383P)²+2.4723P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1067
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Br2-P1 \\sim Br1-P1
 with sigma of 0.02
3. Others
 Sof(Br1)=1-FVAR(1)
 Sof(Br2)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C3(H3), C17(H17), C20(H20)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C4(H4A,H4B)
4.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15)
4.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C18(H18A,H18B,H18C), C21(H21A,H21B,H21C), C8(H8A,H8B,
 H8C), C9(H9A,H9B,H9C), C19(H19A,H19B,H19C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br 0.1236(3) 0.33751(12) 0.65677(14) 0.0696(8) Uani 0.52(2) 1 d D . P A 1
P1 P 0.32452(8) 0.27809(4) 0.67910(3) 0.0607(2) Uani 1 1 d D . . . .
N1 N 0.50714(18) 0.38020(9) 0.62590(6) 0.0397(4) Uani 1 1 d . . . . .
C10 C 0.6861(3) 0.46225(16) 0.58157(10) 0.0681(7) Uani 1 1 d . . . . .
H10A H 0.788008 0.471085 0.576664 0.102 Uiso 1 1 calc R U . . .
H10B H 0.642173 0.510774 0.592716 0.102 Uiso 1 1 calc R U . . .
H10C H 0.641149 0.446962 0.553190 0.102 Uiso 1 1 calc R U . . .
C11 C 0.3951(2) 0.43053(12) 0.60628(8) 0.0471(5) Uani 1 1 d . . . . .
C12 C 0.3469(3) 0.49797(14) 0.63106(10) 0.0582(6) Uani 1 1 d . . . . .
C13 C 0.2430(3) 0.54626(18) 0.61025(12) 0.0801(9) Uani 1 1 d . . . . .
H13 H 0.210930 0.592194 0.625325 0.096 Uiso 1 1 calc R U . . .
C14 C 0.1869(4) 0.5280(2) 0.56833(14) 0.0948(11) Uani 1 1 d . . . . .
H14 H 0.116321 0.561075 0.555489 0.114 Uiso 1 1 calc R U . . .
C15 C 0.2334(4) 0.46134(19) 0.54483(12) 0.0829(9) Uani 1 1 d . . . . .
H15 H 0.193495 0.449542 0.516323 0.099 Uiso 1 1 calc R U . . .
C16 C 0.3397(3) 0.41111(14) 0.56320(9) 0.0599(7) Uani 1 1 d . . . . .
C5 C 0.6657(2) 0.39582(13) 0.61651(8) 0.0471(5) Uani 1 1 d . . . . .
C6 C 0.7379(3) 0.41708(15) 0.66191(9) 0.0581(6) Uani 1 1 d . . . . .
H6A H 0.842010 0.421955 0.657615 0.070 Uiso 1 1 calc R U . . .
H6B H 0.701222 0.468246 0.672852 0.070 Uiso 1 1 calc R U . . .
C7 C 0.7060(3) 0.35218(16) 0.69675(9) 0.0658(7) Uani 1 1 d . . . . .
H7A H 0.651701 0.375009 0.722084 0.079 Uiso 1 1 calc R U . . .
H7B H 0.796705 0.331211 0.708741 0.079 Uiso 1 1 calc R U . . .
C2 C 0.6183(3) 0.28349(14) 0.67520(8) 0.0507(6) Uani 1 1 d . . . . .
C3 C 0.7051(3) 0.24958(14) 0.63428(10) 0.0609(7) Uani 1 1 d . . . . .
H3 H 0.800191 0.232782 0.645986 0.073 Uiso 1 1 calc R U . . .
C4 C 0.7315(3) 0.31701(15) 0.59977(9) 0.0587(6) Uani 1 1 d . . . . .
H4A H 0.835192 0.323893 0.595245 0.070 Uiso 1 1 calc R U . . .
H4B H 0.688678 0.302566 0.570533 0.070 Uiso 1 1 calc R U . . .
C17 C 0.4022(3) 0.51949(15) 0.67841(10) 0.0661(7) Uani 1 1 d . . . . .
H17 H 0.467057 0.476289 0.688531 0.079 Uiso 1 1 calc R U . . .
C18 C 0.4894(4) 0.59744(17) 0.67796(12) 0.0880(10) Uani 1 1 d . . . . .
H18A H 0.525235 0.608329 0.708224 0.132 Uiso 1 1 calc R U . . .
H18B H 0.428080 0.640857 0.668183 0.132 Uiso 1 1 calc R U . . .
H18C H 0.569684 0.592204 0.657178 0.132 Uiso 1 1 calc R U . . .
C20 C 0.3865(4) 0.33760(16) 0.53641(10) 0.0780(9) Uani 1 1 d . . . . .
H20 H 0.466910 0.312556 0.553163 0.094 Uiso 1 1 calc R U . . .
C21 C 0.4410(5) 0.3572(2) 0.48855(12) 0.1006(11) Uani 1 1 d . . . . .
H21A H 0.470724 0.308627 0.473504 0.151 Uiso 1 1 calc R U . . .
H21B H 0.522103 0.393285 0.490615 0.151 Uiso 1 1 calc R U . . .
H21C H 0.364484 0.382153 0.471279 0.151 Uiso 1 1 calc R U . . .
C1 C 0.4773(2) 0.32068(11) 0.65626(7) 0.0414(5) Uani 1 1 d . . . . .
C8 C 0.5955(4) 0.21851(17) 0.71210(10) 0.0780(9) Uani 1 1 d . . . . .
H8A H 0.536726 0.175999 0.699826 0.117 Uiso 1 1 calc R U . . .
H8B H 0.547637 0.241747 0.738153 0.117 Uiso 1 1 calc R U . . .
H8C H 0.687994 0.197297 0.721317 0.117 Uiso 1 1 calc R U . . .
C9 C 0.6353(4) 0.17661(16) 0.61237(12) 0.0861(10) Uani 1 1 d . . . . .
H9A H 0.694514 0.158355 0.587366 0.129 Uiso 1 1 calc R U . . .
H9B H 0.540631 0.190688 0.601149 0.129 Uiso 1 1 calc R U . . .
H9C H 0.626535 0.134548 0.634723 0.129 Uiso 1 1 calc R U . . .
C19 C 0.2782(4) 0.5261(2) 0.71333(12) 0.0983(11) Uani 1 1 d . . . . .
H19A H 0.317863 0.528986 0.743710 0.147 Uiso 1 1 calc R U . . .
H19B H 0.216518 0.479751 0.710906 0.147 Uiso 1 1 calc R U . . .
H19C H 0.222455 0.573679 0.707225 0.147 Uiso 1 1 calc R U . . .
C22 C 0.2633(6) 0.2758(2) 0.53356(13) 0.1236(16) Uani 1 1 d . . . . .
H22A H 0.297395 0.228530 0.518116 0.185 Uiso 1 1 calc R U . . .
H22B H 0.183240 0.298406 0.516852 0.185 Uiso 1 1 calc R U . . .
H22C H 0.232066 0.261927 0.563935 0.185 Uiso 1 1 calc R U . . .
Br1 Br 0.1222(4) 0.3351(2) 0.6444(5) 0.1100(13) Uani 0.48(2) 1 d D . P A 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
Br2 P1 2.196(3) . ?
P1 C1 1.710(2) . ?
P1 Br1 2.322(6) . ?
N1 C11 1.446(3) . ?
N1 C5 1.507(3) . ?
N1 C1 1.357(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10 C5 1.515(3) . ?
C11 C12 1.407(3) . ?
C11 C16 1.395(3) . ?
C12 C13 1.389(4) . ?
C12 C17 1.515(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.362(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.373(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.394(4) . ?
C16 C20 1.514(4) . ?
C5 C6 1.524(3) . ?
C5 C4 1.525(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.512(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C2 1.534(4) . ?
C2 C3 1.543(4) . ?
C2 C1 1.540(3) . ?
C2 C8 1.540(3) . ?
C3 H3 0.9800 . ?
C3 C4 1.527(4) . ?
C3 C9 1.515(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C17 H17 0.9800 . ?
C17 C18 1.525(4) . ?
C17 C19 1.534(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20 0.9800 . ?
C20 C21 1.519(5) . ?
C20 C22 1.533(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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 Br2 112.97(11) . . ?
C1 P1 Br1 108.69(18) . . ?
C11 N1 C5 121.21(16) . . ?
C1 N1 C11 122.46(18) . . ?
C1 N1 C5 116.14(17) . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
C12 C11 N1 118.9(2) . . ?
C16 C11 N1 118.9(2) . . ?
C16 C11 C12 122.2(2) . . ?
C11 C12 C17 123.4(2) . . ?
C13 C12 C11 117.0(3) . . ?
C13 C12 C17 119.5(2) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 C12 121.7(3) . . ?
C14 C13 H13 119.2 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.7(3) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.8(3) . . ?
C16 C15 H15 119.6 . . ?
C11 C16 C20 123.3(2) . . ?
C15 C16 C11 117.7(3) . . ?
C15 C16 C20 119.1(3) . . ?
N1 C5 C10 111.61(19) . . ?
N1 C5 C6 107.71(18) . . ?
N1 C5 C4 107.14(18) . . ?
C10 C5 C6 111.2(2) . . ?
C10 C5 C4 111.3(2) . . ?
C6 C5 C4 107.7(2) . . ?
C5 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
C7 C6 C5 109.5(2) . . ?
C7 C6 H6A 109.8 . . ?
C7 C6 H6B 109.8 . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C6 C7 C2 111.0(2) . . ?
H7A C7 H7B 108.0 . . ?
C2 C7 H7A 109.4 . . ?
C2 C7 H7B 109.4 . . ?
C7 C2 C3 108.5(2) . . ?
C7 C2 C1 106.92(19) . . ?
C7 C2 C8 108.0(2) . . ?
C1 C2 C3 107.81(19) . . ?
C8 C2 C3 110.8(2) . . ?
C8 C2 C1 114.7(2) . . ?
C2 C3 H3 107.3 . . ?
C4 C3 C2 108.89(19) . . ?
C4 C3 H3 107.3 . . ?
C9 C3 C2 113.6(2) . . ?
C9 C3 H3 107.3 . . ?
C9 C3 C4 112.2(2) . . ?
C5 C4 C3 110.9(2) . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.0 . . ?
C12 C17 H17 107.8 . . ?
C12 C17 C18 111.7(2) . . ?
C12 C17 C19 111.9(3) . . ?
C18 C17 H17 107.8 . . ?
C18 C17 C19 109.7(2) . . ?
C19 C17 H17 107.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C20 H20 107.5 . . ?
C16 C20 C21 113.2(2) . . ?
C16 C20 C22 111.0(3) . . ?
C21 C20 H20 107.5 . . ?
C21 C20 C22 109.8(3) . . ?
C22 C20 H20 107.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N1 C1 P1 136.34(17) . . ?
N1 C1 C2 110.91(18) . . ?
C2 C1 P1 112.74(15) . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 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
Br2 P1 C1 N1 -3.7(3) . . . . ?
Br2 P1 C1 C2 175.11(16) . . . . ?
N1 C11 C12 C13 177.8(2) . . . . ?
N1 C11 C12 C17 -2.4(3) . . . . ?
N1 C11 C16 C15 -179.1(2) . . . . ?
N1 C11 C16 C20 2.6(4) . . . . ?
N1 C5 C6 C7 53.4(3) . . . . ?
N1 C5 C4 C3 -55.5(3) . . . . ?
C10 C5 C6 C7 176.0(2) . . . . ?
C10 C5 C4 C3 -177.7(2) . . . . ?
C11 N1 C5 C10 -5.9(3) . . . . ?
C11 N1 C5 C6 116.5(2) . . . . ?
C11 N1 C5 C4 -127.9(2) . . . . ?
C11 N1 C1 P1 5.0(3) . . . . ?
C11 N1 C1 C2 -173.84(19) . . . . ?
C11 C12 C13 C14 1.9(5) . . . . ?
C11 C12 C17 C18 113.1(3) . . . . ?
C11 C12 C17 C19 -123.5(3) . . . . ?
C11 C16 C20 C21 -125.1(3) . . . . ?
C11 C16 C20 C22 110.9(3) . . . . ?
C12 C11 C16 C15 0.2(4) . . . . ?
C12 C11 C16 C20 -178.2(3) . . . . ?
C12 C13 C14 C15 -1.0(6) . . . . ?
C13 C12 C17 C18 -67.0(3) . . . . ?
C13 C12 C17 C19 56.3(3) . . . . ?
C13 C14 C15 C16 -0.4(6) . . . . ?
C14 C15 C16 C11 0.8(5) . . . . ?
C14 C15 C16 C20 179.2(3) . . . . ?
C15 C16 C20 C21 56.6(4) . . . . ?
C15 C16 C20 C22 -67.5(4) . . . . ?
C16 C11 C12 C13 -1.5(4) . . . . ?
C16 C11 C12 C17 178.4(2) . . . . ?
C5 N1 C11 C12 -90.8(3) . . . . ?
C5 N1 C11 C16 88.4(3) . . . . ?
C5 N1 C1 P1 -179.87(18) . . . . ?
C5 N1 C1 C2 1.3(3) . . . . ?
C5 C6 C7 C2 2.9(3) . . . . ?
C6 C5 C4 C3 60.2(3) . . . . ?
C6 C7 C2 C3 57.7(3) . . . . ?
C6 C7 C2 C1 -58.3(3) . . . . ?
C6 C7 C2 C8 177.8(2) . . . . ?
C7 C2 C3 C4 -58.9(3) . . . . ?
C7 C2 C3 C9 175.3(2) . . . . ?
C7 C2 C1 P1 -122.14(18) . . . . ?
C7 C2 C1 N1 57.0(2) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C2 C1 P1 121.41(18) . . . . ?
C3 C2 C1 N1 -59.5(2) . . . . ?
C4 C5 C6 C7 -61.8(3) . . . . ?
C17 C12 C13 C14 -178.0(3) . . . . ?
C1 N1 C11 C12 84.1(3) . . . . ?
C1 N1 C11 C16 -96.7(3) . . . . ?
C1 N1 C5 C10 178.9(2) . . . . ?
C1 N1 C5 C6 -58.7(2) . . . . ?
C1 N1 C5 C4 56.9(2) . . . . ?
C1 C2 C3 C4 56.5(3) . . . . ?
C1 C2 C3 C9 -69.3(3) . . . . ?
C8 C2 C3 C4 -177.2(2) . . . . ?
C8 C2 C3 C9 57.0(3) . . . . ?
C8 C2 C1 P1 -2.5(3) . . . . ?
C8 C2 C1 N1 176.6(2) . . . . ?
C9 C3 C4 C5 127.0(2) . . . . ?
Br1 P1 C1 N1 4.3(4) . . . . ?
Br1 P1 C1 C2 -176.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
