# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2026

####################################################################### 
# 
# 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_dp370_0m
_database_code_depnum_ccdc_archive 'CCDC 2440418'
loop_
_audit_author_name
_audit_author_address
'Daria Gerasimova'
;Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center
Russia
;
_audit_update_record             
;
2025-04-02 deposited with the CCDC.	2026-01-19 downloaded from the CCDC.
;
_audit_creation_date             2025-04-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H18 Br N O2 P, Cl, 0.5(H2 O)'
_chemical_formula_sum            'C17 H19 Br Cl N O2.50 P'
_chemical_formula_weight         423.66
_chemical_melting_point          ?
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      150.00
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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_chemical_absolute_configuration .
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6018(4)
_cell_length_b                   16.2369(9)
_cell_length_c                   16.8101(9)
_cell_angle_alpha                93.138(2)
_cell_angle_beta                 100.567(2)
_cell_angle_gamma                93.351(2)
_cell_volume                     1764.40(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9887
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      29.97
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   0.824
_shelx_estimated_absorpt_T_min   0.366
_exptl_absorpt_coefficient_mu    2.584
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1417 before and 0.0707 after correction.
The Ratio of minimum to maximum transmission is 0.8508.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             860
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 -1.00 1.00 0.1270
0.00 1.00 -1.00 0.0530
0.00 1.00 0.00 0.0370
0.00 -1.00 0.00 0.0390
0.00 1.00 1.00 0.0760
0.00 -1.00 -1.00 0.0780
0.00 0.00 1.00 0.0870
0.00 0.00 -1.00 0.0890
1.00 1.00 0.00 0.1880

_exptl_crystal_size_max          0.487
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.078
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            72687
_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         26.997
_diffrn_reflns_theta_min         2.471
_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-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6497
_reflns_number_total             7719
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     456
_refine_ls_number_reflns         7719
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.050
_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)+(0.0313P)²+1.8211P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0810
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 O2A-H2A = O2B-H2B = O3-H3A = O3-H3B
 0.84 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C5A(H5A), C5B(H5B)
3.b Secondary CH2 refined with riding coordinates:
 C2A(H2AA,H2AB), C3A(H3AA,H3AB), C2B(H2BA,H2BB), C3B(H3BA,H3BB)
3.c Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C8A(H8A), C9A(H9A), C10A(H10A), C11A(H11A), C12A(H12A), C14A(H14A),
 C15A(H15A), C17A(H17A), C18A(H18A), C7B(H7B), C8B(H8B), C9B(H9B), C10B(H10B),
 C11B(H11B), C12B(H12B), C14B(H14B), C15B(H15B), C17B(H17B), C18B(H18B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1A Br 1.41316(4) 0.92697(2) 0.90251(2) 0.03692(9) Uani 1 1 d . . . . .
P1A P 0.14044(10) 0.79938(4) 0.55466(4) 0.02133(14) Uani 1 1 d . . . . .
O1A O 0.2158(3) 0.76469(12) 0.48167(11) 0.0303(4) Uani 1 1 d . . . . .
O2A O -0.0916(3) 0.79921(13) 0.55070(12) 0.0308(4) Uani 1 1 d D . . . .
H2A H -0.149(6) 0.780(2) 0.5043(15) 0.072(14) Uiso 1 1 d D . . . .
N1A N 0.2115(3) 0.64369(13) 0.60427(14) 0.0215(4) Uani 1 1 d . . . . .
H1AA H 0.110(5) 0.6312(19) 0.562(2) 0.037(9) Uiso 1 1 d . . . . .
H1AB H 0.189(6) 0.614(2) 0.645(2) 0.055(11) Uiso 1 1 d . . . . .
C2A C 0.4163(4) 0.62438(16) 0.58435(16) 0.0254(5) Uani 1 1 d . . . . .
H2AA H 0.432808 0.645019 0.531413 0.030 Uiso 1 1 calc R U . . .
H2AB H 0.432646 0.564124 0.582957 0.030 Uiso 1 1 calc R U . . .
C3A C 0.5703(4) 0.66994(16) 0.65353(16) 0.0242(5) Uani 1 1 d . . . . .
H3AA H 0.602581 0.634804 0.699878 0.029 Uiso 1 1 calc R U . . .
H3AB H 0.700075 0.687077 0.635506 0.029 Uiso 1 1 calc R U . . .
C4A C 0.4604(4) 0.74445(15) 0.67634(14) 0.0186(5) Uani 1 1 d . . . . .
C5A C 0.2342(4) 0.73227(15) 0.63703(14) 0.0198(5) Uani 1 1 d . . . . .
H5A H 0.148604 0.738578 0.680018 0.024 Uiso 1 1 calc R U . . .
C6A C 0.2443(4) 0.90231(16) 0.58550(16) 0.0255(6) Uani 1 1 d . . . . .
C7A C 0.4431(5) 0.92876(18) 0.57711(18) 0.0334(6) Uani 1 1 d . . . . .
H7A H 0.525043 0.892248 0.552861 0.040 Uiso 1 1 calc R U . . .
C8A C 0.5212(5) 1.0083(2) 0.6041(2) 0.0444(8) Uani 1 1 d . . . . .
H8A H 0.657369 1.026239 0.598868 0.053 Uiso 1 1 calc R U . . .
C9A C 0.4029(7) 1.0614(2) 0.6385(2) 0.0531(10) Uani 1 1 d . . . . .
H9A H 0.457145 1.116131 0.656489 0.064 Uiso 1 1 calc R U . . .
C10A C 0.2080(7) 1.0362(2) 0.6469(2) 0.0563(10) Uani 1 1 d . . . . .
H10A H 0.127147 1.073603 0.670706 0.068 Uiso 1 1 calc R U . . .
C11A C 0.1263(5) 0.95651(19) 0.6211(2) 0.0399(7) Uani 1 1 d . . . . .
H11A H -0.009108 0.939095 0.627785 0.048 Uiso 1 1 calc R U . . .
C12A C 0.5376(4) 0.81234(15) 0.72339(14) 0.0203(5) Uani 1 1 d . . . . .
H12A H 0.440069 0.851138 0.731765 0.024 Uiso 1 1 calc R U . . .
C13A C 0.7515(4) 0.83548(15) 0.76393(14) 0.0197(5) Uani 1 1 d . . . . .
C14A C 0.8099(4) 0.91981(16) 0.78131(16) 0.0241(5) Uani 1 1 d . . . . .
H14A H 0.711420 0.959213 0.766158 0.029 Uiso 1 1 calc R U . . .
C15A C 1.0070(4) 0.94689(17) 0.81992(15) 0.0259(6) Uani 1 1 d . . . . .
H15A H 1.045475 1.004340 0.829998 0.031 Uiso 1 1 calc R U . . .
C16A C 1.1470(4) 0.88942(17) 0.84362(14) 0.0243(5) Uani 1 1 d . . . . .
C17A C 1.0954(4) 0.80521(17) 0.82840(15) 0.0250(5) Uani 1 1 d . . . . .
H17A H 1.193919 0.766285 0.845214 0.030 Uiso 1 1 calc R U . . .
C18A C 0.8980(4) 0.77890(16) 0.78831(15) 0.0226(5) Uani 1 1 d . . . . .
H18A H 0.861650 0.721392 0.777231 0.027 Uiso 1 1 calc R U . . .
Br1B Br 0.85770(4) 0.59249(2) -0.08952(2) 0.02766(8) Uani 1 1 d . . . . .
P1B P -0.00067(10) 0.75118(4) 0.27587(4) 0.01989(13) Uani 1 1 d . . . . .
O1B O -0.2049(3) 0.75296(12) 0.30152(11) 0.0289(4) Uani 1 1 d . . . . .
O2B O 0.1917(3) 0.78505(12) 0.33738(11) 0.0291(4) Uani 1 1 d D . . . .
H2B H 0.209(10) 0.777(4) 0.3884(14) 0.15(2) Uiso 1 1 d D . . . .
N1B N 0.0525(3) 0.59024(14) 0.31754(13) 0.0224(4) Uani 1 1 d . . . . .
H1BA H -0.018(5) 0.6074(18) 0.3550(18) 0.028(8) Uiso 1 1 d . . . . .
H1BB H -0.011(6) 0.537(2) 0.299(2) 0.053(11) Uiso 1 1 d . . . . .
C2B C 0.2796(4) 0.58680(17) 0.34782(16) 0.0265(6) Uani 1 1 d . . . . .
H2BA H 0.308805 0.537175 0.378531 0.032 Uiso 1 1 calc R U . . .
H2BB H 0.336594 0.636721 0.383108 0.032 Uiso 1 1 calc R U . . .
C3B C 0.3701(4) 0.58282(17) 0.27021(15) 0.0250(5) Uani 1 1 d . . . . .
H3BA H 0.508780 0.612271 0.279404 0.030 Uiso 1 1 calc R U . . .
H3BB H 0.381185 0.524736 0.251252 0.030 Uiso 1 1 calc R U . . .
C4B C 0.2190(4) 0.62483(15) 0.20907(15) 0.0203(5) Uani 1 1 d . . . . .
C5B C 0.0303(4) 0.64240(15) 0.24562(14) 0.0199(5) Uani 1 1 d . . . . .
H5B H -0.095975 0.620731 0.205916 0.024 Uiso 1 1 calc R U . . .
C6B C 0.0056(4) 0.80473(15) 0.18648(15) 0.0238(5) Uani 1 1 d . . . . .
C7B C -0.1739(5) 0.80421(17) 0.12928(17) 0.0317(6) Uani 1 1 d . . . . .
H7B H -0.299940 0.780018 0.139920 0.038 Uiso 1 1 calc R U . . .
C8B C -0.1688(6) 0.8394(2) 0.05597(19) 0.0454(8) Uani 1 1 d . . . . .
H8B H -0.291790 0.838754 0.016374 0.054 Uiso 1 1 calc R U . . .
C9B C 0.0120(6) 0.87492(19) 0.04035(18) 0.0445(8) Uani 1 1 d . . . . .
H9B H 0.013717 0.899063 -0.009757 0.053 Uiso 1 1 calc R U . . .
C10B C 0.1926(6) 0.87568(18) 0.09770(18) 0.0391(7) Uani 1 1 d . . . . .
H10B H 0.317829 0.900287 0.086684 0.047 Uiso 1 1 calc R U . . .
C11B C 0.1910(5) 0.84079(17) 0.17070(17) 0.0302(6) Uani 1 1 d . . . . .
H11B H 0.314640 0.841233 0.209926 0.036 Uiso 1 1 calc R U . . .
C12B C 0.2277(4) 0.64222(15) 0.13314(15) 0.0212(5) Uani 1 1 d . . . . .
H12B H 0.109879 0.666762 0.105605 0.025 Uiso 1 1 calc R U . . .
C13B C 0.3888(4) 0.62978(15) 0.08506(15) 0.0200(5) Uani 1 1 d . . . . .
C14B C 0.5498(4) 0.57780(15) 0.10376(15) 0.0214(5) Uani 1 1 d . . . . .
H14B H 0.563200 0.549305 0.152127 0.026 Uiso 1 1 calc R U . . .
C15B C 0.6897(4) 0.56733(15) 0.05283(15) 0.0211(5) Uani 1 1 d . . . . .
H15B H 0.798169 0.531622 0.066086 0.025 Uiso 1 1 calc R U . . .
C16B C 0.6718(4) 0.60872(16) -0.01722(15) 0.0221(5) Uani 1 1 d . . . . .
C17B C 0.5140(4) 0.66099(17) -0.03809(16) 0.0256(6) Uani 1 1 d . . . . .
H17B H 0.502348 0.689407 -0.086470 0.031 Uiso 1 1 calc R U . . .
C18B C 0.3744(4) 0.67068(16) 0.01327(15) 0.0246(5) Uani 1 1 d . . . . .
H18B H 0.265573 0.706106 -0.000585 0.029 Uiso 1 1 calc R U . . .
Cl1A Cl -0.17965(10) 0.57917(4) 0.46639(4) 0.02966(15) Uani 1 1 d . . . . .
O3 O -0.3392(3) 0.74104(14) 0.43398(13) 0.0343(5) Uani 1 1 d D . . . .
H3A H -0.297(9) 0.6907(19) 0.444(4) 0.14(2) Uiso 1 1 d D . . . .
H3B H -0.287(8) 0.754(3) 0.392(2) 0.12(2) Uiso 1 1 d D . . . .
Cl1B Cl -0.14919(11) 0.42728(4) 0.23731(4) 0.02910(15) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1A C16A 1.900(3) . ?
P1A O1A 1.5005(19) . ?
P1A O2A 1.521(2) . ?
P1A C5A 1.849(2) . ?
P1A C6A 1.781(3) . ?
O2A H2A 0.838(19) . ?
N1A H1AA 0.89(3) . ?
N1A H1AB 0.89(4) . ?
N1A C2A 1.497(3) . ?
N1A C5A 1.501(3) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C2A C3A 1.522(4) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C3A C4A 1.513(3) . ?
C4A C5A 1.515(3) . ?
C4A C12A 1.339(3) . ?
C5A H5A 1.0000 . ?
C6A C7A 1.391(4) . ?
C6A C11A 1.391(4) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.383(4) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.369(5) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.362(6) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.387(5) . ?
C11A H11A 0.9500 . ?
C12A H12A 0.9500 . ?
C12A C13A 1.469(3) . ?
C13A C14A 1.401(3) . ?
C13A C18A 1.395(3) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.378(4) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.375(4) . ?
C16A C17A 1.388(4) . ?
C17A H17A 0.9500 . ?
C17A C18A 1.384(4) . ?
C18A H18A 0.9500 . ?
Br1B C16B 1.898(2) . ?
P1B O1B 1.4902(19) . ?
P1B O2B 1.536(2) . ?
P1B C5B 1.844(2) . ?
P1B C6B 1.782(3) . ?
O2B H2B 0.86(2) . ?
N1B H1BA 0.89(3) . ?
N1B H1BB 0.95(4) . ?
N1B C2B 1.498(3) . ?
N1B C5B 1.504(3) . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
C2B C3B 1.531(3) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C3B C4B 1.516(3) . ?
C4B C5B 1.521(3) . ?
C4B C12B 1.333(3) . ?
C5B H5B 1.0000 . ?
C6B C7B 1.382(4) . ?
C6B C11B 1.402(4) . ?
C7B H7B 0.9500 . ?
C7B C8B 1.391(4) . ?
C8B H8B 0.9500 . ?
C8B C9B 1.370(5) . ?
C9B H9B 0.9500 . ?
C9B C10B 1.388(5) . ?
C10B H10B 0.9500 . ?
C10B C11B 1.381(4) . ?
C11B H11B 0.9500 . ?
C12B H12B 0.9500 . ?
C12B C13B 1.466(3) . ?
C13B C14B 1.397(3) . ?
C13B C18B 1.400(3) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.381(3) . ?
C15B H15B 0.9500 . ?
C15B C16B 1.377(3) . ?
C16B C17B 1.389(4) . ?
C17B H17B 0.9500 . ?
C17B C18B 1.384(4) . ?
C18B H18B 0.9500 . ?
O3 H3A 0.89(2) . ?
O3 H3B 0.864(19) . ?

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
O1A P1A O2A 117.97(12) . . ?
O1A P1A C5A 105.54(11) . . ?
O1A P1A C6A 112.60(12) . . ?
O2A P1A C5A 105.29(11) . . ?
O2A P1A C6A 106.73(12) . . ?
C6A P1A C5A 108.12(12) . . ?
P1A O2A H2A 107(3) . . ?
H1AA N1A H1AB 109(3) . . ?
C2A N1A H1AA 111(2) . . ?
C2A N1A H1AB 108(2) . . ?
C2A N1A C5A 106.43(19) . . ?
C5A N1A H1AA 116(2) . . ?
C5A N1A H1AB 106(2) . . ?
N1A C2A H2AA 111.1 . . ?
N1A C2A H2AB 111.1 . . ?
N1A C2A C3A 103.2(2) . . ?
H2AA C2A H2AB 109.1 . . ?
C3A C2A H2AA 111.1 . . ?
C3A C2A H2AB 111.1 . . ?
C2A C3A H3AA 111.0 . . ?
C2A C3A H3AB 111.0 . . ?
H3AA C3A H3AB 109.0 . . ?
C4A C3A C2A 103.9(2) . . ?
C4A C3A H3AA 111.0 . . ?
C4A C3A H3AB 111.0 . . ?
C3A C4A C5A 109.2(2) . . ?
C12A C4A C3A 128.9(2) . . ?
C12A C4A C5A 121.9(2) . . ?
P1A C5A H5A 108.8 . . ?
N1A C5A P1A 109.61(16) . . ?
N1A C5A C4A 103.15(19) . . ?
N1A C5A H5A 108.8 . . ?
C4A C5A P1A 117.24(17) . . ?
C4A C5A H5A 108.8 . . ?
C7A C6A P1A 121.5(2) . . ?
C11A C6A P1A 119.2(2) . . ?
C11A C6A C7A 119.4(3) . . ?
C6A C7A H7A 120.1 . . ?
C8A C7A C6A 119.9(3) . . ?
C8A C7A H7A 120.1 . . ?
C7A C8A H8A 119.9 . . ?
C9A C8A C7A 120.3(3) . . ?
C9A C8A H8A 119.9 . . ?
C8A C9A H9A 119.8 . . ?
C10A C9A C8A 120.4(3) . . ?
C10A C9A H9A 119.8 . . ?
C9A C10A H10A 119.7 . . ?
C9A C10A C11A 120.6(3) . . ?
C11A C10A H10A 119.7 . . ?
C6A C11A H11A 120.3 . . ?
C10A C11A C6A 119.5(3) . . ?
C10A C11A H11A 120.3 . . ?
C4A C12A H12A 115.4 . . ?
C4A C12A C13A 129.3(2) . . ?
C13A C12A H12A 115.4 . . ?
C14A C13A C12A 117.7(2) . . ?
C18A C13A C12A 124.2(2) . . ?
C18A C13A C14A 118.1(2) . . ?
C13A C14A H14A 119.3 . . ?
C15A C14A C13A 121.5(2) . . ?
C15A C14A H14A 119.3 . . ?
C14A C15A H15A 120.5 . . ?
C16A C15A C14A 118.9(2) . . ?
C16A C15A H15A 120.5 . . ?
C15A C16A Br1A 118.7(2) . . ?
C15A C16A C17A 121.6(2) . . ?
C17A C16A Br1A 119.7(2) . . ?
C16A C17A H17A 120.6 . . ?
C18A C17A C16A 118.9(2) . . ?
C18A C17A H17A 120.6 . . ?
C13A C18A H18A 119.5 . . ?
C17A C18A C13A 121.1(2) . . ?
C17A C18A H18A 119.5 . . ?
O1B P1B O2B 117.83(11) . . ?
O1B P1B C5B 106.59(11) . . ?
O1B P1B C6B 112.18(12) . . ?
O2B P1B C5B 108.91(11) . . ?
O2B P1B C6B 105.93(12) . . ?
C6B P1B C5B 104.63(11) . . ?
P1B O2B H2B 123(4) . . ?
H1BA N1B H1BB 104(3) . . ?
C2B N1B H1BA 114.5(19) . . ?
C2B N1B H1BB 111(2) . . ?
C2B N1B C5B 106.47(19) . . ?
C5B N1B H1BA 113.2(19) . . ?
C5B N1B H1BB 107(2) . . ?
N1B C2B H2BA 111.0 . . ?
N1B C2B H2BB 111.0 . . ?
N1B C2B C3B 103.7(2) . . ?
H2BA C2B H2BB 109.0 . . ?
C3B C2B H2BA 111.0 . . ?
C3B C2B H2BB 111.0 . . ?
C2B C3B H3BA 110.8 . . ?
C2B C3B H3BB 110.8 . . ?
H3BA C3B H3BB 108.9 . . ?
C4B C3B C2B 104.8(2) . . ?
C4B C3B H3BA 110.8 . . ?
C4B C3B H3BB 110.8 . . ?
C3B C4B C5B 108.8(2) . . ?
C12B C4B C3B 130.1(2) . . ?
C12B C4B C5B 121.0(2) . . ?
P1B C5B H5B 108.4 . . ?
N1B C5B P1B 111.10(16) . . ?
N1B C5B C4B 103.22(19) . . ?
N1B C5B H5B 108.4 . . ?
C4B C5B P1B 117.02(17) . . ?
C4B C5B H5B 108.4 . . ?
C7B C6B P1B 118.5(2) . . ?
C7B C6B C11B 120.1(2) . . ?
C11B C6B P1B 121.2(2) . . ?
C6B C7B H7B 120.2 . . ?
C6B C7B C8B 119.5(3) . . ?
C8B C7B H7B 120.2 . . ?
C7B C8B H8B 119.7 . . ?
C9B C8B C7B 120.6(3) . . ?
C9B C8B H8B 119.7 . . ?
C8B C9B H9B 120.0 . . ?
C8B C9B C10B 120.1(3) . . ?
C10B C9B H9B 120.0 . . ?
C9B C10B H10B 119.9 . . ?
C11B C10B C9B 120.2(3) . . ?
C11B C10B H10B 119.9 . . ?
C6B C11B H11B 120.2 . . ?
C10B C11B C6B 119.5(3) . . ?
C10B C11B H11B 120.2 . . ?
C4B C12B H12B 114.6 . . ?
C4B C12B C13B 130.7(2) . . ?
C13B C12B H12B 114.6 . . ?
C14B C13B C12B 125.0(2) . . ?
C14B C13B C18B 117.9(2) . . ?
C18B C13B C12B 117.1(2) . . ?
C13B C14B H14B 119.6 . . ?
C15B C14B C13B 120.8(2) . . ?
C15B C14B H14B 119.6 . . ?
C14B C15B H15B 120.0 . . ?
C16B C15B C14B 119.9(2) . . ?
C16B C15B H15B 120.0 . . ?
C15B C16B Br1B 120.45(19) . . ?
C15B C16B C17B 121.1(2) . . ?
C17B C16B Br1B 118.41(19) . . ?
C16B C17B H17B 120.8 . . ?
C18B C17B C16B 118.4(2) . . ?
C18B C17B H17B 120.8 . . ?
C13B C18B H18B 119.1 . . ?
C17B C18B C13B 121.9(2) . . ?
C17B C18B H18B 119.1 . . ?
H3A O3 H3B 104(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
Br1A C16A C17A C18A 177.38(19) . . . . ?
P1A C6A C7A C8A -177.9(2) . . . . ?
P1A C6A C11A C10A 178.6(3) . . . . ?
O1A P1A C5A N1A -40.51(19) . . . . ?
O1A P1A C5A C4A 76.6(2) . . . . ?
O1A P1A C6A C7A -33.8(3) . . . . ?
O1A P1A C6A C11A 148.3(2) . . . . ?
O2A P1A C5A N1A 84.99(18) . . . . ?
O2A P1A C5A C4A -157.94(18) . . . . ?
O2A P1A C6A C7A -164.8(2) . . . . ?
O2A P1A C6A C11A 17.3(3) . . . . ?
N1A C2A C3A C4A -31.2(3) . . . . ?
C2A N1A C5A P1A 95.7(2) . . . . ?
C2A N1A C5A C4A -29.9(2) . . . . ?
C2A C3A C4A C5A 13.3(3) . . . . ?
C2A C3A C4A C12A -167.0(2) . . . . ?
C3A C4A C5A P1A -110.8(2) . . . . ?
C3A C4A C5A N1A 9.8(2) . . . . ?
C3A C4A C12A C13A 2.4(4) . . . . ?
C4A C12A C13A C14A 154.5(3) . . . . ?
C4A C12A C13A C18A -27.5(4) . . . . ?
C5A P1A C6A C7A 82.4(2) . . . . ?
C5A P1A C6A C11A -95.5(2) . . . . ?
C5A N1A C2A C3A 38.7(2) . . . . ?
C5A C4A C12A C13A -177.9(2) . . . . ?
C6A P1A C5A N1A -161.22(17) . . . . ?
C6A P1A C5A C4A -44.1(2) . . . . ?
C6A C7A C8A C9A -0.6(5) . . . . ?
C7A C6A C11A C10A 0.7(5) . . . . ?
C7A C8A C9A C10A 0.5(5) . . . . ?
C8A C9A C10A C11A 0.2(6) . . . . ?
C9A C10A C11A C6A -0.7(6) . . . . ?
C11A C6A C7A C8A 0.0(4) . . . . ?
C12A C4A C5A P1A 69.5(3) . . . . ?
C12A C4A C5A N1A -169.9(2) . . . . ?
C12A C13A C14A C15A 179.4(2) . . . . ?
C12A C13A C18A C17A -178.1(2) . . . . ?
C13A C14A C15A C16A -1.7(4) . . . . ?
C14A C13A C18A C17A -0.1(4) . . . . ?
C14A C15A C16A Br1A -176.29(19) . . . . ?
C14A C15A C16A C17A 1.1(4) . . . . ?
C15A C16A C17A C18A 0.1(4) . . . . ?
C16A C17A C18A C13A -0.5(4) . . . . ?
C18A C13A C14A C15A 1.3(4) . . . . ?
Br1B C16B C17B C18B 177.9(2) . . . . ?
P1B C6B C7B C8B -174.5(2) . . . . ?
P1B C6B C11B C10B 174.6(2) . . . . ?
O1B P1B C5B N1B -67.48(19) . . . . ?
O1B P1B C5B C4B 174.36(17) . . . . ?
O1B P1B C6B C7B -32.5(2) . . . . ?
O1B P1B C6B C11B 152.8(2) . . . . ?
O2B P1B C5B N1B 60.61(19) . . . . ?
O2B P1B C5B C4B -57.6(2) . . . . ?
O2B P1B C6B C7B -162.4(2) . . . . ?
O2B P1B C6B C11B 23.0(2) . . . . ?
N1B C2B C3B C4B 26.8(3) . . . . ?
C2B N1B C5B P1B -94.4(2) . . . . ?
C2B N1B C5B C4B 31.9(2) . . . . ?
C2B C3B C4B C5B -7.6(3) . . . . ?
C2B C3B C4B C12B 176.1(3) . . . . ?
C3B C4B C5B P1B 107.9(2) . . . . ?
C3B C4B C5B N1B -14.5(3) . . . . ?
C3B C4B C12B C13B -2.9(5) . . . . ?
C4B C12B C13B C14B 16.5(4) . . . . ?
C4B C12B C13B C18B -166.2(3) . . . . ?
C5B P1B C6B C7B 82.6(2) . . . . ?
C5B P1B C6B C11B -92.1(2) . . . . ?
C5B N1B C2B C3B -37.0(3) . . . . ?
C5B C4B C12B C13B -178.8(2) . . . . ?
C6B P1B C5B N1B 173.52(17) . . . . ?
C6B P1B C5B C4B 55.4(2) . . . . ?
C6B C7B C8B C9B -0.5(5) . . . . ?
C7B C6B C11B C10B 0.0(4) . . . . ?
C7B C8B C9B C10B 0.4(5) . . . . ?
C8B C9B C10B C11B -0.1(5) . . . . ?
C9B C10B C11B C6B -0.1(4) . . . . ?
C11B C6B C7B C8B 0.3(4) . . . . ?
C12B C4B C5B P1B -75.4(3) . . . . ?
C12B C4B C5B N1B 162.2(2) . . . . ?
C12B C13B C14B C15B 177.2(2) . . . . ?
C12B C13B C18B C17B -177.7(2) . . . . ?
C13B C14B C15B C16B 0.3(4) . . . . ?
C14B C13B C18B C17B -0.3(4) . . . . ?
C14B C15B C16B Br1B -178.10(19) . . . . ?
C14B C15B C16B C17B -0.3(4) . . . . ?
C15B C16B C17B C18B 0.0(4) . . . . ?
C16B C17B C18B C13B 0.3(4) . . . . ?
C18B C13B C14B C15B 0.0(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_dp372_0m
_database_code_depnum_ccdc_archive 'CCDC 2440419'
loop_
_audit_author_name
_audit_author_address
'Daria Gerasimova'
;Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center
Russia
;
_audit_update_record             
;
2025-04-04 deposited with the CCDC.	2026-01-19 downloaded from the CCDC.
;
_audit_creation_date             2025-04-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'Cl, C18 H21 N O3 P, H2 O'
_chemical_formula_sum            'C18 H23 Cl N O4 P'
_chemical_formula_weight         383.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'
_chemical_absolute_configuration .
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
_chemical_melting_point          ?
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      150.00
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;

_cell_length_a                   6.337(4)
_cell_length_b                   16.965(10)
_cell_length_c                   9.393(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.174(12)
_cell_angle_gamma                90
_cell_volume                     979.0(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2518
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      25.29
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.888
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1100 before and 0.0718 after correction.
The Ratio of minimum to maximum transmission is 0.7385.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             404
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 -1.00 1.00 0.1140
-1.00 0.00 -1.00 0.1280
0.00 -1.00 1.00 0.0720
0.00 1.00 -1.00 0.1040
0.00 1.00 0.00 0.0290
0.00 -1.00 0.00 0.0610
0.00 1.00 1.00 0.0490
0.00 -1.00 -1.00 0.1070
1.00 1.00 -1.00 0.1910
1.00 0.00 1.00 0.0990

_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.122
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_unetI/netI     0.0967
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8828
_diffrn_reflns_point_group_measured_fraction_full 0.872
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.989
_diffrn_reflns_theta_min         2.401
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.744
_reflns_Friedel_fraction_max     0.748
_reflns_number_gt                3009
_reflns_number_total             3706
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.994
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.121
_refine_ls_abs_structure_details 
;
 Flack x determined using 855 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.22(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3706
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1137
_refine_ls_R_factor_gt           0.0944
_refine_ls_restrained_S_all      1.132
_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)+(0.0889P)²+2.2789P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2041
_refine_ls_wR_factor_ref         0.2140
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 H2-O4
 1.711 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C5) = Uanis(C2) = Uanis(C3)
4.a Free rotating group:
 O4(H4A,H4B)
4.b Ternary CH refined with riding coordinates:
 C5(H5)
4.c Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B)
4.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15),
 C17(H17), C18(H18)
4.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
4.f Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.0198(4) 0.45679(14) -0.0683(3) 0.0245(6) Uani 1 1 d . . . . .
P1 P 0.7583(3) 0.32114(14) 0.4094(2) 0.0168(5) Uani 1 1 d . . . . .
O1 O 0.5887(11) 0.3669(4) 0.3012(7) 0.0236(16) Uani 1 1 d . . . . .
O2 O 0.9992(11) 0.3340(4) 0.4095(7) 0.0233(16) Uani 1 1 d . . . . .
H2 H 1.006854 0.356230 0.330966 0.035 Uiso 1 1 calc DR U . . .
O3 O -0.0590(14) 0.1101(4) 0.9736(9) 0.042(2) Uani 1 1 d . . . . .
N1 N 0.7720(13) 0.4370(5) 0.6094(9) 0.0217(18) Uani 1 1 d . . . . .
H1A H 0.828559 0.457543 0.537201 0.026 Uiso 1 1 calc R U . . .
H1B H 0.856798 0.452377 0.697816 0.026 Uiso 1 1 calc R U . . .
C2 C 0.5408(16) 0.4651(6) 0.5921(11) 0.0211(12) Uani 1 1 d . . . . .
H2A H 0.460422 0.466893 0.487557 0.025 Uiso 1 1 calc R U . . .
H2B H 0.536537 0.517822 0.636581 0.025 Uiso 1 1 calc R U . . .
C3 C 0.4491(16) 0.4012(6) 0.6767(11) 0.0211(12) Uani 1 1 d . . . . .
H3A H 0.470679 0.416163 0.781160 0.025 Uiso 1 1 calc R U . . .
H3B H 0.291568 0.393392 0.633480 0.025 Uiso 1 1 calc R U . . .
C4 C 0.5739(15) 0.3274(6) 0.6627(10) 0.021(2) Uani 1 1 d . . . . .
C5 C 0.7644(16) 0.3506(6) 0.5994(10) 0.0211(12) Uani 1 1 d . . . . .
H5 H 0.900743 0.329244 0.665352 0.025 Uiso 1 1 calc R U . . .
C6 C 0.7095(15) 0.2171(6) 0.4001(11) 0.024(2) Uani 1 1 d . . . . .
C7 C 0.5026(18) 0.1882(7) 0.3303(13) 0.034(3) Uani 1 1 d . . . . .
H7 H 0.388532 0.223829 0.288703 0.041 Uiso 1 1 calc R U . . .
C8 C 0.465(3) 0.1090(8) 0.3220(16) 0.053(4) Uani 1 1 d . . . . .
H8 H 0.327503 0.089384 0.269670 0.063 Uiso 1 1 calc R U . . .
C9 C 0.628(2) 0.0569(7) 0.3900(15) 0.041(3) Uani 1 1 d . . . . .
H9 H 0.598256 0.002015 0.390410 0.049 Uiso 1 1 calc R U . . .
C10 C 0.830(2) 0.0850(7) 0.4563(12) 0.034(3) Uani 1 1 d . . . . .
H10 H 0.942696 0.049340 0.499924 0.041 Uiso 1 1 calc R U . . .
C11 C 0.8709(18) 0.1644(6) 0.4601(12) 0.028(2) Uani 1 1 d . . . . .
H11 H 1.012916 0.183207 0.504938 0.034 Uiso 1 1 calc R U . . .
C12 C 0.5441(16) 0.2541(6) 0.6976(10) 0.022(2) Uani 1 1 d . . . . .
H12 H 0.643845 0.217376 0.674625 0.027 Uiso 1 1 calc R U . . .
C13 C 0.3768(16) 0.2191(6) 0.7684(11) 0.021(2) Uani 1 1 d . . . . .
C14 C 0.2608(16) 0.2654(6) 0.8488(11) 0.024(2) Uani 1 1 d . . . . .
H14 H 0.284598 0.320635 0.857878 0.028 Uiso 1 1 calc R U . . .
C15 C 0.1122(16) 0.2295(6) 0.9141(11) 0.025(2) Uani 1 1 d . . . . .
H15 H 0.030810 0.261143 0.964927 0.030 Uiso 1 1 calc R U . . .
C16 C 0.0798(17) 0.1506(6) 0.9075(11) 0.020(2) Uani 1 1 d . . . . .
C17 C 0.1911(19) 0.1046(6) 0.8284(11) 0.027(2) Uani 1 1 d . . . . .
H17 H 0.168456 0.049227 0.822082 0.033 Uiso 1 1 calc R U . . .
C18 C 0.3349(17) 0.1394(6) 0.7589(11) 0.025(2) Uani 1 1 d . . . . .
H18 H 0.407519 0.107467 0.702797 0.031 Uiso 1 1 calc R U . . .
C19 C -0.162(2) 0.1548(7) 1.0673(13) 0.040(3) Uani 1 1 d . . . . .
H19A H -0.267262 0.191401 1.007849 0.059 Uiso 1 1 calc R U . . .
H19B H -0.051415 0.184691 1.138102 0.059 Uiso 1 1 calc R U . . .
H19C H -0.237218 0.118958 1.120148 0.059 Uiso 1 1 calc R U . . .
O4 O 1.1649(11) 0.3540(5) 0.2043(8) 0.0284(17) Uani 1 1 d DG . . . .
H4A H 1.301727 0.343924 0.211311 0.043 Uiso 1 1 d G U . . .
H4B H 1.137817 0.395524 0.148558 0.043 Uiso 1 1 d G U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.502(7) . ?
P1 O2 1.542(7) . ?
P1 C5 1.844(9) . ?
P1 C6 1.790(11) . ?
O2 H2 0.8400 . ?
O3 C16 1.378(11) . ?
O3 C19 1.434(12) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C2 1.511(12) . ?
N1 C5 1.469(13) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.540(12) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.503(14) . ?
C4 C5 1.522(12) . ?
C4 C12 1.311(14) . ?
C5 H5 1.0000 . ?
C6 C7 1.403(14) . ?
C6 C11 1.372(14) . ?
C7 H7 0.9500 . ?
C7 C8 1.364(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(19) . ?
C9 H9 0.9500 . ?
C9 C10 1.367(18) . ?
C10 H10 0.9500 . ?
C10 C11 1.371(15) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.505(12) . ?
C13 C14 1.414(13) . ?
C13 C18 1.376(14) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(13) . ?
C15 H15 0.9500 . ?
C15 C16 1.354(14) . ?
C16 C17 1.384(13) . ?
C17 H17 0.9500 . ?
C17 C18 1.377(13) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O4 H4A 0.8700 . ?
O4 H4B 0.8702 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 O2 118.1(4) . . ?
O1 P1 C5 110.9(4) . . ?
O1 P1 C6 113.0(5) . . ?
O2 P1 C5 100.1(4) . . ?
O2 P1 C6 107.4(4) . . ?
C6 P1 C5 106.1(4) . . ?
P1 O2 H2 109.5 . . ?
C16 O3 C19 116.7(8) . . ?
H1A N1 H1B 108.6 . . ?
C2 N1 H1A 110.3 . . ?
C2 N1 H1B 110.3 . . ?
C5 N1 H1A 110.3 . . ?
C5 N1 H1B 110.3 . . ?
C5 N1 C2 107.0(7) . . ?
N1 C2 H2A 111.5 . . ?
N1 C2 H2B 111.5 . . ?
N1 C2 C3 101.6(7) . . ?
H2A C2 H2B 109.3 . . ?
C3 C2 H2A 111.5 . . ?
C3 C2 H2B 111.5 . . ?
C2 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
H3A C3 H3B 108.8 . . ?
C4 C3 C2 105.5(7) . . ?
C4 C3 H3A 110.6 . . ?
C4 C3 H3B 110.6 . . ?
C3 C4 C5 107.7(8) . . ?
C12 C4 C3 131.0(8) . . ?
C12 C4 C5 121.3(9) . . ?
P1 C5 H5 108.2 . . ?
N1 C5 P1 109.0(6) . . ?
N1 C5 C4 104.5(7) . . ?
N1 C5 H5 108.2 . . ?
C4 C5 P1 118.5(7) . . ?
C4 C5 H5 108.2 . . ?
C7 C6 P1 119.9(9) . . ?
C11 C6 P1 121.3(8) . . ?
C11 C6 C7 118.8(10) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.1(12) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.1(13) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.7(11) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.4(11) . . ?
C11 C10 H10 119.8 . . ?
C6 C11 H11 119.6 . . ?
C10 C11 C6 120.8(11) . . ?
C10 C11 H11 119.6 . . ?
C4 C12 H12 114.9 . . ?
C4 C12 C13 130.2(9) . . ?
C13 C12 H12 114.9 . . ?
C14 C13 C12 122.1(9) . . ?
C18 C13 C12 120.4(8) . . ?
C18 C13 C14 117.6(9) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.4(10) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 119.1 . . ?
C16 C15 C14 121.8(9) . . ?
C16 C15 H15 119.1 . . ?
O3 C16 C17 115.3(9) . . ?
C15 C16 O3 125.3(8) . . ?
C15 C16 C17 119.4(9) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.7(9) . . ?
C18 C17 H17 120.1 . . ?
C13 C18 C17 122.0(9) . . ?
C13 C18 H18 119.0 . . ?
C17 C18 H18 119.0 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H4A O4 H4B 104.5 . . ?

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
P1 C6 C7 C8 179.6(9) . . . . ?
P1 C6 C11 C10 178.0(8) . . . . ?
O1 P1 C5 N1 -48.8(7) . . . . ?
O1 P1 C5 C4 70.3(8) . . . . ?
O1 P1 C6 C7 -17.5(9) . . . . ?
O1 P1 C6 C11 162.6(7) . . . . ?
O2 P1 C5 N1 76.6(7) . . . . ?
O2 P1 C5 C4 -164.2(8) . . . . ?
O2 P1 C6 C7 -149.4(8) . . . . ?
O2 P1 C6 C11 30.6(9) . . . . ?
O3 C16 C17 C18 -179.6(10) . . . . ?
N1 C2 C3 C4 -29.1(10) . . . . ?
C2 N1 C5 P1 96.1(7) . . . . ?
C2 N1 C5 C4 -31.4(9) . . . . ?
C2 C3 C4 C5 11.2(11) . . . . ?
C2 C3 C4 C12 -170.4(10) . . . . ?
C3 C4 C5 P1 -109.4(8) . . . . ?
C3 C4 C5 N1 12.0(10) . . . . ?
C3 C4 C12 C13 -2.0(19) . . . . ?
C4 C12 C13 C14 -19.5(17) . . . . ?
C4 C12 C13 C18 161.9(11) . . . . ?
C5 P1 C6 C7 104.2(9) . . . . ?
C5 P1 C6 C11 -75.7(8) . . . . ?
C5 N1 C2 C3 37.9(9) . . . . ?
C5 C4 C12 C13 176.3(10) . . . . ?
C6 P1 C5 N1 -171.8(6) . . . . ?
C6 P1 C5 C4 -52.7(9) . . . . ?
C6 C7 C8 C9 3.8(19) . . . . ?
C7 C6 C11 C10 -2.0(14) . . . . ?
C7 C8 C9 C10 -5(2) . . . . ?
C8 C9 C10 C11 2.2(19) . . . . ?
C9 C10 C11 C6 1.2(16) . . . . ?
C11 C6 C7 C8 -0.5(16) . . . . ?
C12 C4 C5 P1 71.9(12) . . . . ?
C12 C4 C5 N1 -166.6(9) . . . . ?
C12 C13 C14 C15 -178.6(10) . . . . ?
C12 C13 C18 C17 176.7(10) . . . . ?
C13 C14 C15 C16 2.3(17) . . . . ?
C14 C13 C18 C17 -2.0(17) . . . . ?
C14 C15 C16 O3 177.6(11) . . . . ?
C14 C15 C16 C17 -2.7(17) . . . . ?
C15 C16 C17 C18 0.7(17) . . . . ?
C16 C17 C18 C13 1.7(18) . . . . ?
C18 C13 C14 C15 0.1(16) . . . . ?
C19 O3 C16 C15 -5.9(17) . . . . ?
C19 O3 C16 C17 174.5(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

