#------------------------------------------------------------------------------
#$Date: 2025-10-06 12:17:36 +0200 (Mon 06 de Oct de 2025) $
#$Revision: 302736 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/39/7063950.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7063950
loop_
_publ_author_name
'Rizbayeva, Tanzilya'
'Smolobochkin, Andrey'
'Gazizov, Almir'
'Babaeva, Olga'
'Lyubina, Anna'
'Sapunova, Anastasiia'
'Voloshina, Alexandra'
'Gerasimova, Daria'
'Burilov, Alexander'
'Pudovik, Michail'
_publ_section_title
;
 Diastereospecific cyclization of 3-arylidene-1-pyrrolinium salts
 containing an alkyltriarylphosphonium fragment: a path to the synthesis
 of new pyrrolizidine derivatives
;
_journal_issue                   34
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14718
_journal_page_last               14727
_journal_paper_doi               10.1039/D5NJ02552D
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C32 H30 Cl N P, Br, C3 H6 O1'
_chemical_formula_sum            'C35 H36 Br Cl N O P'
_chemical_formula_weight         632.98
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-17
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-12-17 deposited with the CCDC.	2025-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                106.349(4)
_cell_angle_beta                 103.089(5)
_cell_angle_gamma                102.213(5)
_cell_formula_units_Z            2
_cell_length_a                   10.4277(18)
_cell_length_b                   12.208(2)
_cell_length_c                   14.862(3)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    120.00
_cell_measurement_theta_max      29.96
_cell_measurement_theta_min      2.18
_cell_volume                     1689.8(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120.00
_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_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            56123
_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         26.999
_diffrn_reflns_theta_min         1.916
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.369
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.4857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1107 before and 0.0648 after correction.
The Ratio of minimum to maximum transmission is 0.6511.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.594
_exptl_crystal_size_mid          0.458
_exptl_crystal_size_min          0.397
_refine_diff_density_max         1.009
_refine_diff_density_min         -0.698
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         7379
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0377
_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)+(0.0502P)²+1.3773P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1030
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6254
_reflns_number_total             7379
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5nj02552d2.cif
_cod_data_source_block           dp273_0m
_cod_depositor_comments
'Adding full bibliography for 7063950--7063958.cif.'
_cod_original_cell_volume        1689.9(5)
_cod_database_code               7063950
_shelx_shelxl_version_number     2019/1
_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.
;
_shelx_estimated_absorpt_t_max   0.613
_shelx_estimated_absorpt_t_min   0.497
_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
 O17-C2 \\sim O17A-C2A
 with sigma of 0.02
 C2-C33 \\sim C2A-C33A
 with sigma of 0.02
 C2-C36 \\sim C2A-C36A
 with sigma of 0.02
 O17-C33 \\sim O17A-C33A
 with sigma of 0.04
 O17-C36 \\sim O17A-C36A
 with sigma of 0.04
 C33-C36 \\sim C33A-C36A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C36A) = Uanis(C33A) = Uanis(C2) = Uanis(C36) = Uanis(C2A) = Uanis(C33)
Uanis(O17A) = Uanis(O17)
4. Others
 Sof(O17A)=Sof(C2A)=Sof(C33A)=Sof(H33D)=Sof(H33E)=Sof(H33F)=Sof(C36A)=
 Sof(H36D)=Sof(H36E)=Sof(H36F)=1-FVAR(1)
 Sof(O17)=Sof(C2)=Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(H33C)=Sof(C36)=Sof(H36A)=
 Sof(H36B)=Sof(H36C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C8(H8), C10(H10)
5.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C19(H19A,H19B), C26(H26A,H26B), C35(H35A,H35B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C12(H12), C13(H13), C15(H15), C16(H16), C18(H18),
 C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29),
  C30(H30), C31(H31), C32(H32), C34(H34)
5.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C36(H36A,H36B,H36C), C33A(H33D,H33E,H33F), C36A(H36D,
 H36E,H36F)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.07553(2) 0.20449(2) 0.35347(2) 0.03356(9) Uani 1 1 d . . . . .
Cl1 Cl -0.15304(7) -0.44341(7) 0.00480(5) 0.05083(19) Uani 1 1 d . . . . .
P1 P 0.36876(5) 0.30122(4) 0.65752(4) 0.01920(12) Uani 1 1 d . . . . .
N1 N 0.3734(2) 0.02455(16) 0.64672(14) 0.0261(4) Uani 1 1 d . . . . .
C1 C 0.2603(2) 0.39793(19) 0.66440(16) 0.0233(4) Uani 1 1 d . . . . .
C3 C 0.0270(3) -0.3622(2) 0.18794(19) 0.0369(6) Uani 1 1 d . . . . .
H3 H 0.018443 -0.443822 0.179281 0.044 Uiso 1 1 calc R U . . .
C4 C 0.4951(2) 0.35556(17) 0.60377(16) 0.0215(4) Uani 1 1 d . . . . .
C5 C 0.1110(2) -0.2733(2) 0.27571(18) 0.0304(5) Uani 1 1 d . . . . .
H5 H 0.159469 -0.295074 0.326994 0.036 Uiso 1 1 calc R U . . .
C6 C 0.2726(2) -0.05256(18) 0.47017(16) 0.0227(4) Uani 1 1 d . . . . .
C7 C -0.0318(3) -0.2126(2) 0.12479(18) 0.0372(6) Uani 1 1 d . . . . .
H7 H -0.080903 -0.191903 0.073048 0.045 Uiso 1 1 calc R U . . .
C8 C 0.3493(2) 0.06231(18) 0.56023(15) 0.0216(4) Uani 1 1 d . . . . .
H8 H 0.438798 0.103051 0.553693 0.026 Uiso 1 1 calc R U . . .
C9 C 0.2831(3) -0.15633(19) 0.50471(18) 0.0312(5) Uani 1 1 d . . . . .
H9A H 0.318475 -0.212350 0.461649 0.037 Uiso 1 1 calc R U . . .
H9B H 0.192495 -0.200267 0.505923 0.037 Uiso 1 1 calc R U . . .
C10 C 0.2645(2) 0.14998(17) 0.58037(15) 0.0203(4) Uani 1 1 d . . . . .
H10 H 0.206747 0.150156 0.516755 0.024 Uiso 1 1 calc R U . . .
C11 C -0.0437(2) -0.3311(2) 0.11367(18) 0.0348(6) Uani 1 1 d . . . . .
C12 C 0.4604(2) 0.32264(19) 0.50147(16) 0.0244(4) Uani 1 1 d . . . . .
H12 H 0.374174 0.266532 0.460829 0.029 Uiso 1 1 calc R U . . .
C13 C 0.0515(3) 0.4428(2) 0.6023(2) 0.0329(5) Uani 1 1 d . . . . .
H13 H -0.040460 0.417302 0.559870 0.040 Uiso 1 1 calc R U . . .
C14 C 0.4529(2) 0.30784(18) 0.77922(15) 0.0233(4) Uani 1 1 d . . . . .
C15 C 0.4531(3) 0.3338(3) 0.94546(19) 0.0416(6) Uani 1 1 d . . . . .
H15 H 0.413802 0.355801 0.997102 0.050 Uiso 1 1 calc R U . . .
C16 C 0.6208(2) 0.44063(19) 0.66365(17) 0.0259(4) Uani 1 1 d . . . . .
H16 H 0.644190 0.463485 0.733281 0.031 Uiso 1 1 calc R U . . .
C18 C 0.1255(2) 0.3607(2) 0.60361(17) 0.0263(4) Uani 1 1 d . . . . .
H18 H 0.083851 0.279212 0.562963 0.032 Uiso 1 1 calc R U . . .
C19 C 0.3856(3) -0.0964(2) 0.60927(18) 0.0327(5) Uani 1 1 d . . . . .
H19A H 0.362817 -0.141970 0.652001 0.039 Uiso 1 1 calc R U . . .
H19B H 0.480692 -0.092883 0.607530 0.039 Uiso 1 1 calc R U . . .
C20 C 0.2090(2) -0.05190(19) 0.38188(16) 0.0245(4) Uani 1 1 d . . . . .
H20 H 0.218625 0.025213 0.377091 0.029 Uiso 1 1 calc R U . . .
C21 C 0.3946(3) 0.3412(2) 0.85487(17) 0.0320(5) Uani 1 1 d . . . . .
H21 H 0.315575 0.368550 0.844133 0.038 Uiso 1 1 calc R U . . .
C22 C 0.1258(2) -0.15237(19) 0.29013(16) 0.0249(4) Uani 1 1 d . . . . .
C23 C 0.0527(3) -0.1245(2) 0.21258(17) 0.0328(5) Uani 1 1 d . . . . .
H23 H 0.061179 -0.043079 0.220259 0.039 Uiso 1 1 calc R U . . .
C24 C 0.5699(2) 0.26893(19) 0.79582(17) 0.0283(5) Uani 1 1 d . . . . .
H24 H 0.609746 0.246320 0.744541 0.034 Uiso 1 1 calc R U . . .
C25 C 0.1099(3) 0.5604(2) 0.6616(2) 0.0381(6) Uani 1 1 d . . . . .
H25 H 0.058543 0.615887 0.660290 0.046 Uiso 1 1 calc R U . . .
C26 C 0.1714(2) 0.0951(2) 0.63345(17) 0.0281(5) Uani 1 1 d . . . . .
H26A H 0.150017 0.158145 0.681083 0.034 Uiso 1 1 calc R U . . .
H26B H 0.084025 0.038113 0.585587 0.034 Uiso 1 1 calc R U . . .
C27 C 0.6277(3) 0.2635(2) 0.88761(19) 0.0383(6) Uani 1 1 d . . . . .
H27 H 0.708117 0.238233 0.899644 0.046 Uiso 1 1 calc R U . . .
C28 C 0.5529(2) 0.3726(2) 0.45982(17) 0.0277(5) Uani 1 1 d . . . . .
H28 H 0.530852 0.349202 0.390221 0.033 Uiso 1 1 calc R U . . .
C29 C 0.2443(3) 0.5980(2) 0.7236(2) 0.0393(6) Uani 1 1 d . . . . .
H29 H 0.284272 0.679280 0.765210 0.047 Uiso 1 1 calc R U . . .
C30 C 0.7105(2) 0.4910(2) 0.62064(19) 0.0309(5) Uani 1 1 d . . . . .
H30 H 0.795249 0.549528 0.660880 0.037 Uiso 1 1 calc R U . . .
C31 C 0.5685(3) 0.2948(3) 0.9613(2) 0.0453(7) Uani 1 1 d . . . . .
H31 H 0.607323 0.289378 1.023672 0.054 Uiso 1 1 calc R U . . .
C32 C 0.6772(2) 0.4564(2) 0.51903(19) 0.0302(5) Uani 1 1 d . . . . .
H32 H 0.739954 0.490423 0.489882 0.036 Uiso 1 1 calc R U . . .
C34 C 0.3202(3) 0.5181(2) 0.72532(18) 0.0326(5) Uani 1 1 d . . . . .
H34 H 0.412395 0.544402 0.767427 0.039 Uiso 1 1 calc R U . . .
C35 C 0.2566(3) 0.0308(2) 0.68661(18) 0.0328(5) Uani 1 1 d . . . . .
H35A H 0.290819 0.075423 0.758385 0.039 Uiso 1 1 calc R U . . .
H35B H 0.199253 -0.050579 0.675038 0.039 Uiso 1 1 calc R U . . .
O17 O 0.5163(4) 0.7896(4) 0.8588(3) 0.0914(13) Uani 0.770(3) 1 d D . P A 1
C2 C 0.6181(6) 0.8382(5) 0.8454(4) 0.0780(9) Uani 0.770(3) 1 d D . P A 1
C33 C 0.7233(6) 0.7674(5) 0.8450(5) 0.0780(9) Uani 0.770(3) 1 d D . P A 1
H33A H 0.686437 0.692917 0.855697 0.117 Uiso 0.770(3) 1 calc R U P A 1
H33B H 0.809282 0.815104 0.897640 0.117 Uiso 0.770(3) 1 calc R U P A 1
H33C H 0.741375 0.748757 0.781310 0.117 Uiso 0.770(3) 1 calc R U P A 1
C36 C 0.6430(6) 0.9501(5) 0.8285(4) 0.0780(9) Uani 0.770(3) 1 d D . P A 1
H36A H 0.627452 0.935055 0.757975 0.117 Uiso 0.770(3) 1 calc R U P A 1
H36B H 0.738443 0.998659 0.864937 0.117 Uiso 0.770(3) 1 calc R U P A 1
H36C H 0.580114 0.992833 0.851026 0.117 Uiso 0.770(3) 1 calc R U P A 1
O17A O 0.6974(14) 0.8605(13) 0.8015(10) 0.0914(13) Uani 0.230(3) 1 d D . P A 2
C2A C 0.7513(17) 0.8051(18) 0.8440(17) 0.0780(9) Uani 0.230(3) 1 d D . P A 2
C33A C 0.6360(17) 0.7107(16) 0.8612(14) 0.0780(9) Uani 0.230(3) 1 d D . P A 2
H33D H 0.627791 0.744352 0.927058 0.117 Uiso 0.230(3) 1 calc R U P A 2
H33E H 0.662254 0.637113 0.855564 0.117 Uiso 0.230(3) 1 calc R U P A 2
H33F H 0.547462 0.692747 0.811577 0.117 Uiso 0.230(3) 1 calc R U P A 2
C36A C 0.8719(15) 0.7644(16) 0.8620(13) 0.0780(9) Uani 0.230(3) 1 d D . P A 2
H36D H 0.915513 0.767031 0.810399 0.117 Uiso 0.230(3) 1 calc R U P A 2
H36E H 0.844827 0.682181 0.861348 0.117 Uiso 0.230(3) 1 calc R U P A 2
H36F H 0.937222 0.816256 0.926267 0.117 Uiso 0.230(3) 1 calc R U P A 2
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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3.00 0.00 2.00 0.3310
-2.00 -1.00 -3.00 0.3180
-2.00 3.00 0.00 0.2380
-2.00 1.00 1.00 0.2340
-1.00 3.00 -2.00 0.2920
-1.00 0.00 1.00 0.2980
-1.00 -1.00 2.00 0.3310
1.00 0.00 0.00 0.3120
1.00 -3.00 2.00 0.3950
1.00 1.00 -2.00 0.2970
1.00 -2.00 -3.00 0.3020
1.00 1.00 3.00 0.3430
2.00 1.00 3.00 0.3470
2.00 -3.00 0.00 0.3780
2.00 -1.00 -1.00 0.3280
3.00 0.00 -2.00 0.3430
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 C10 109.15(10) . . ?
C4 P1 C1 107.07(10) . . ?
C4 P1 C10 110.29(10) . . ?
C14 P1 C1 109.42(10) . . ?
C14 P1 C4 109.64(10) . . ?
C14 P1 C10 111.17(10) . . ?
C8 N1 C35 107.89(17) . . ?
C19 N1 C8 104.62(17) . . ?
C19 N1 C35 114.30(18) . . ?
C18 C1 P1 121.88(17) . . ?
C18 C1 C34 119.6(2) . . ?
C34 C1 P1 118.07(17) . . ?
C5 C3 H3 120.2 . . ?
C11 C3 H3 120.2 . . ?
C11 C3 C5 119.5(2) . . ?
C12 C4 P1 119.03(16) . . ?
C12 C4 C16 120.2(2) . . ?
C16 C4 P1 120.34(17) . . ?
C3 C5 H5 119.3 . . ?
C3 C5 C22 121.3(2) . . ?
C22 C5 H5 119.3 . . ?
C9 C6 C8 106.74(18) . . ?
C20 C6 C8 123.22(19) . . ?
C20 C6 C9 130.0(2) . . ?
C11 C7 H7 120.5 . . ?
C11 C7 C23 119.0(2) . . ?
C23 C7 H7 120.5 . . ?
N1 C8 C6 106.26(16) . . ?
N1 C8 H8 110.4 . . ?
N1 C8 C10 104.94(17) . . ?
C6 C8 H8 110.4 . . ?
C10 C8 C6 114.10(17) . . ?
C10 C8 H8 110.4 . . ?
C6 C9 H9A 111.1 . . ?
C6 C9 H9B 111.1 . . ?
C6 C9 C19 103.53(18) . . ?
H9A C9 H9B 109.0 . . ?
C19 C9 H9A 111.1 . . ?
C19 C9 H9B 111.1 . . ?
P1 C10 H10 110.0 . . ?
C8 C10 P1 113.48(14) . . ?
C8 C10 H10 110.0 . . ?
C8 C10 C26 102.55(17) . . ?
C26 C10 P1 110.69(14) . . ?
C26 C10 H10 110.0 . . ?
C3 C11 Cl1 119.3(2) . . ?
C3 C11 C7 121.0(2) . . ?
C7 C11 Cl1 119.6(2) . . ?
C4 C12 H12 120.3 . . ?
C28 C12 C4 119.3(2) . . ?
C28 C12 H12 120.3 . . ?
C18 C13 H13 119.7 . . ?
C25 C13 H13 119.7 . . ?
C25 C13 C18 120.6(2) . . ?
C21 C14 P1 120.16(18) . . ?
C24 C14 P1 119.49(17) . . ?
C24 C14 C21 120.1(2) . . ?
C21 C15 H15 119.8 . . ?
C31 C15 H15 119.8 . . ?
C31 C15 C21 120.4(3) . . ?
C4 C16 H16 120.3 . . ?
C30 C16 C4 119.5(2) . . ?
C30 C16 H16 120.3 . . ?
C1 C18 C13 119.8(2) . . ?
C1 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?
N1 C19 C9 106.57(18) . . ?
N1 C19 H19A 110.4 . . ?
N1 C19 H19B 110.4 . . ?
C9 C19 H19A 110.4 . . ?
C9 C19 H19B 110.4 . . ?
H19A C19 H19B 108.6 . . ?
C6 C20 H20 114.9 . . ?
C6 C20 C22 130.2(2) . . ?
C22 C20 H20 114.9 . . ?
C14 C21 H21 120.4 . . ?
C15 C21 C14 119.3(2) . . ?
C15 C21 H21 120.4 . . ?
C5 C22 C20 125.2(2) . . ?
C23 C22 C5 117.4(2) . . ?
C23 C22 C20 117.3(2) . . ?
C7 C23 C22 121.7(2) . . ?
C7 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C14 C24 H24 120.2 . . ?
C27 C24 C14 119.6(2) . . ?
C27 C24 H24 120.2 . . ?
C13 C25 H25 120.1 . . ?
C13 C25 C29 119.8(2) . . ?
C29 C25 H25 120.1 . . ?
C10 C26 H26A 110.9 . . ?
C10 C26 H26B 110.9 . . ?
H26A C26 H26B 108.9 . . ?
C35 C26 C10 104.43(18) . . ?
C35 C26 H26A 110.9 . . ?
C35 C26 H26B 110.9 . . ?
C24 C27 H27 120.0 . . ?
C31 C27 C24 120.0(3) . . ?
C31 C27 H27 120.0 . . ?
C12 C28 H28 119.8 . . ?
C32 C28 C12 120.4(2) . . ?
C32 C28 H28 119.8 . . ?
C25 C29 H29 119.8 . . ?
C34 C29 C25 120.5(2) . . ?
C34 C29 H29 119.8 . . ?
C16 C30 H30 119.9 . . ?
C16 C30 C32 120.3(2) . . ?
C32 C30 H30 119.9 . . ?
C15 C31 H31 119.7 . . ?
C27 C31 C15 120.6(2) . . ?
C27 C31 H31 119.7 . . ?
C28 C32 C30 120.3(2) . . ?
C28 C32 H32 119.9 . . ?
C30 C32 H32 119.9 . . ?
C1 C34 H34 120.2 . . ?
C29 C34 C1 119.6(2) . . ?
C29 C34 H34 120.2 . . ?
N1 C35 C26 107.38(18) . . ?
N1 C35 H35A 110.2 . . ?
N1 C35 H35B 110.2 . . ?
C26 C35 H35A 110.2 . . ?
C26 C35 H35B 110.2 . . ?
H35A C35 H35B 108.5 . . ?
O17 C2 C33 113.0(5) . . ?
O17 C2 C36 125.2(6) . . ?
C36 C2 C33 121.7(5) . . ?
C2 C33 H33A 109.5 . . ?
C2 C33 H33B 109.5 . . ?
C2 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C2 C36 H36A 109.5 . . ?
C2 C36 H36B 109.5 . . ?
C2 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O17A C2A C33A 109.2(14) . . ?
O17A C2A C36A 143.2(18) . . ?
C36A C2A C33A 104.2(14) . . ?
C2A C33A H33D 109.5 . . ?
C2A C33A H33E 109.5 . . ?
C2A C33A H33F 109.5 . . ?
H33D C33A H33E 109.5 . . ?
H33D C33A H33F 109.5 . . ?
H33E C33A H33F 109.5 . . ?
C2A C36A H36D 109.5 . . ?
C2A C36A H36E 109.5 . . ?
C2A C36A H36F 109.5 . . ?
H36D C36A H36E 109.5 . . ?
H36D C36A H36F 109.5 . . ?
H36E C36A H36F 109.5 . . ?
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 C11 1.747(2) . ?
P1 C1 1.798(2) . ?
P1 C4 1.794(2) . ?
P1 C10 1.817(2) . ?
P1 C14 1.794(2) . ?
N1 C8 1.471(3) . ?
N1 C19 1.468(3) . ?
N1 C35 1.477(3) . ?
C1 C18 1.386(3) . ?
C1 C34 1.404(3) . ?
C3 H3 0.9500 . ?
C3 C5 1.389(3) . ?
C3 C11 1.375(4) . ?
C4 C12 1.396(3) . ?
C4 C16 1.402(3) . ?
C5 H5 0.9500 . ?
C5 C22 1.401(3) . ?
C6 C8 1.543(3) . ?
C6 C9 1.510(3) . ?
C6 C20 1.332(3) . ?
C7 H7 0.9500 . ?
C7 C11 1.385(4) . ?
C7 C23 1.387(3) . ?
C8 H8 1.0000 . ?
C8 C10 1.535(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C19 1.539(3) . ?
C10 H10 1.0000 . ?
C10 C26 1.543(3) . ?
C12 H12 0.9500 . ?
C12 C28 1.386(3) . ?
C13 H13 0.9500 . ?
C13 C18 1.391(3) . ?
C13 C25 1.372(4) . ?
C14 C21 1.399(3) . ?
C14 C24 1.397(3) . ?
C15 H15 0.9500 . ?
C15 C21 1.383(3) . ?
C15 C31 1.381(4) . ?
C16 H16 0.9500 . ?
C16 C30 1.382(3) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20 0.9500 . ?
C20 C22 1.480(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.399(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C24 C27 1.387(3) . ?
C25 H25 0.9500 . ?
C25 C29 1.388(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C35 1.535(3) . ?
C27 H27 0.9500 . ?
C27 C31 1.378(4) . ?
C28 H28 0.9500 . ?
C28 C32 1.385(3) . ?
C29 H29 0.9500 . ?
C29 C34 1.383(3) . ?
C30 H30 0.9500 . ?
C30 C32 1.386(4) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C34 H34 0.9500 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
O17 C2 1.190(6) . ?
C2 C33 1.534(8) . ?
C2 C36 1.439(8) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
O17A C2A 1.189(16) . ?
C2A C33A 1.599(16) . ?
C2A C36A 1.445(17) . ?
C33A H33D 0.9800 . ?
C33A H33E 0.9800 . ?
C33A H33F 0.9800 . ?
C36A H36D 0.9800 . ?
C36A H36E 0.9800 . ?
C36A H36F 0.9800 . ?
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 C1 C18 C13 -171.47(17) . . . . ?
P1 C1 C34 C29 172.5(2) . . . . ?
P1 C4 C12 C28 174.30(16) . . . . ?
P1 C4 C16 C30 -173.02(17) . . . . ?
P1 C10 C26 C35 -91.84(18) . . . . ?
P1 C14 C21 C15 173.33(19) . . . . ?
P1 C14 C24 C27 -174.04(18) . . . . ?
N1 C8 C10 P1 83.27(17) . . . . ?
N1 C8 C10 C26 -36.15(19) . . . . ?
C1 P1 C4 C12 -82.69(18) . . . . ?
C1 P1 C4 C16 89.96(19) . . . . ?
C1 P1 C10 C8 173.72(14) . . . . ?
C1 P1 C10 C26 -71.63(17) . . . . ?
C1 P1 C14 C21 24.3(2) . . . . ?
C1 P1 C14 C24 -161.64(17) . . . . ?
C3 C5 C22 C20 177.9(2) . . . . ?
C3 C5 C22 C23 -0.1(3) . . . . ?
C4 P1 C1 C18 108.48(19) . . . . ?
C4 P1 C1 C34 -64.1(2) . . . . ?
C4 P1 C10 C8 56.35(17) . . . . ?
C4 P1 C10 C26 171.00(14) . . . . ?
C4 P1 C14 C21 141.42(18) . . . . ?
C4 P1 C14 C24 -44.5(2) . . . . ?
C4 C12 C28 C32 -1.5(3) . . . . ?
C4 C16 C30 C32 -0.9(3) . . . . ?
C5 C3 C11 Cl1 -178.16(19) . . . . ?
C5 C3 C11 C7 0.3(4) . . . . ?
C5 C22 C23 C7 0.3(4) . . . . ?
C6 C8 C10 P1 -160.83(14) . . . . ?
C6 C8 C10 C26 79.8(2) . . . . ?
C6 C9 C19 N1 27.7(3) . . . . ?
C6 C20 C22 C5 -8.2(4) . . . . ?
C6 C20 C22 C23 169.8(2) . . . . ?
C8 N1 C19 C9 -36.2(2) . . . . ?
C8 N1 C35 C26 -10.0(2) . . . . ?
C8 C6 C9 C19 -8.8(2) . . . . ?
C8 C6 C20 C22 -176.6(2) . . . . ?
C8 C10 C26 C35 29.5(2) . . . . ?
C9 C6 C8 N1 -12.7(2) . . . . ?
C9 C6 C8 C10 -127.8(2) . . . . ?
C9 C6 C20 C22 1.6(4) . . . . ?
C10 P1 C1 C18 -10.9(2) . . . . ?
C10 P1 C1 C34 176.53(18) . . . . ?
C10 P1 C4 C12 35.96(19) . . . . ?
C10 P1 C4 C16 -151.39(17) . . . . ?
C10 P1 C14 C21 -96.36(19) . . . . ?
C10 P1 C14 C24 77.72(19) . . . . ?
C10 C26 C35 N1 -12.9(2) . . . . ?
C11 C3 C5 C22 -0.2(4) . . . . ?
C11 C7 C23 C22 -0.2(4) . . . . ?
C12 C4 C16 C30 -0.5(3) . . . . ?
C12 C28 C32 C30 0.2(3) . . . . ?
C13 C25 C29 C34 0.7(4) . . . . ?
C14 P1 C1 C18 -132.76(18) . . . . ?
C14 P1 C1 C34 54.7(2) . . . . ?
C14 P1 C4 C12 158.70(16) . . . . ?
C14 P1 C4 C16 -28.6(2) . . . . ?
C14 P1 C10 C8 -65.49(17) . . . . ?
C14 P1 C10 C26 49.16(18) . . . . ?
C14 C24 C27 C31 0.9(4) . . . . ?
C16 C4 C12 C28 1.6(3) . . . . ?
C16 C30 C32 C28 1.0(3) . . . . ?
C18 C1 C34 C29 -0.3(4) . . . . ?
C18 C13 C25 C29 0.1(4) . . . . ?
C19 N1 C8 C6 29.9(2) . . . . ?
C19 N1 C8 C10 151.15(17) . . . . ?
C19 N1 C35 C26 -125.9(2) . . . . ?
C20 C6 C8 N1 165.9(2) . . . . ?
C20 C6 C8 C10 50.8(3) . . . . ?
C20 C6 C9 C19 172.8(2) . . . . ?
C20 C22 C23 C7 -177.8(2) . . . . ?
C21 C14 C24 C27 0.0(3) . . . . ?
C21 C15 C31 C27 0.6(4) . . . . ?
C23 C7 C11 Cl1 178.4(2) . . . . ?
C23 C7 C11 C3 -0.1(4) . . . . ?
C24 C14 C21 C15 -0.7(3) . . . . ?
C24 C27 C31 C15 -1.2(4) . . . . ?
C25 C13 C18 C1 -0.9(4) . . . . ?
C25 C29 C34 C1 -0.6(4) . . . . ?
C31 C15 C21 C14 0.4(4) . . . . ?
C34 C1 C18 C13 1.0(3) . . . . ?
C35 N1 C8 C6 -92.1(2) . . . . ?
C35 N1 C8 C10 29.1(2) . . . . ?
C35 N1 C19 C9 81.6(2) . . . . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.434 0.000 0.000 248.1 56.1 ?
