# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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. 
# 
#######################################################################

data_m
_database_code_depnum_ccdc_archive 'CCDC 1405631'
loop_
_audit_author_name
_audit_author_address
'Marek Necas'
;Department of Chemistry, Masaryk University
Czech Republic
;
_audit_update_record             
;
2022-09-18 deposited with the CCDC.	2023-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H30 N3 P S'
_chemical_formula_weight         279.42

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   11.1802(6)
_cell_length_b                   9.6493(6)
_cell_length_c                   15.1332(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1632.59(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4057
_cell_measurement_theta_min      2.4720
_cell_measurement_theta_max      29.2470

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.284
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76196
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode MicroMax-007HF DW 1.2 kW'
_diffrn_measurement_device_type  'AFC11 (Right): Eulerian 3 circle CCD'
_diffrn_measurement_method       'Profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6934
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.097
_diffrn_reflns_theta_max         25.345
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             2896
_reflns_number_gt                2696
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_max     0.931
_reflns_Friedel_fraction_full    0.937

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       
;
Rigaku CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)
MSCServDetCCD = {5.7.3.4}
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0530P)²+0.0557P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.41(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2896
_refine_ls_number_parameters     164
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.32660(6) 0.08074(9) 0.71569(6) 0.0210(2) Uani 1 1 d . . . . .
P1 P 0.16169(6) 0.14342(9) 0.73058(5) 0.0150(2) Uani 1 1 d . . . . .
N1 N 0.1229(2) 0.2710(3) 0.66407(18) 0.0183(6) Uani 1 1 d . . . . .
H1A H 0.070378 0.329229 0.686427 0.022 Uiso 1 1 calc R U . . .
N2 N 0.0566(2) 0.0245(3) 0.71437(18) 0.0167(6) Uani 1 1 d . . . . .
H2A H -0.008235 0.053849 0.687287 0.020 Uiso 1 1 calc R U . . .
N3 N 0.1274(2) 0.1945(3) 0.83203(17) 0.0173(6) Uani 1 1 d . . . . .
H3A H 0.070764 0.145610 0.857635 0.021 Uiso 1 1 calc R U . . .
C1 C 0.1620(3) 0.3041(4) 0.5724(2) 0.0197(8) Uani 1 1 d . . . . .
C2 C 0.0711(3) 0.4061(4) 0.5351(2) 0.0279(9) Uani 1 1 d . . . . .
H2B H -0.008179 0.362753 0.534078 0.042 Uiso 1 1 calc R U . . .
H2C H 0.094218 0.432121 0.474885 0.042 Uiso 1 1 calc R U . . .
H2D H 0.068637 0.489157 0.572369 0.042 Uiso 1 1 calc R U . . .
C3 C 0.2853(4) 0.3733(4) 0.5759(2) 0.0277(9) Uani 1 1 d . . . . .
H3B H 0.281144 0.456285 0.613122 0.042 Uiso 1 1 calc R U . . .
H3C H 0.309910 0.399566 0.516048 0.042 Uiso 1 1 calc R U . . .
H3D H 0.343644 0.308343 0.600775 0.042 Uiso 1 1 calc R U . . .
C4 C 0.1653(3) 0.1753(4) 0.5146(2) 0.0282(9) Uani 1 1 d . . . . .
H4A H 0.085092 0.134727 0.511363 0.042 Uiso 1 1 calc R U . . .
H4B H 0.220886 0.107706 0.540026 0.042 Uiso 1 1 calc R U . . .
H4C H 0.192077 0.200589 0.455041 0.042 Uiso 1 1 calc R U . . .
C5 C 0.0567(3) -0.1249(3) 0.7392(2) 0.0198(7) Uani 1 1 d . . . . .
C6 C 0.1258(3) -0.2095(4) 0.6716(3) 0.0280(8) Uani 1 1 d . . . . .
H6A H 0.088490 -0.199004 0.613340 0.042 Uiso 1 1 calc R U . . .
H6B H 0.124720 -0.307459 0.688735 0.042 Uiso 1 1 calc R U . . .
H6C H 0.208669 -0.176739 0.669003 0.042 Uiso 1 1 calc R U . . .
C7 C -0.0743(3) -0.1699(4) 0.7397(3) 0.0281(8) Uani 1 1 d . . . . .
H7A H -0.117846 -0.117522 0.784883 0.042 Uiso 1 1 calc R U . . .
H7B H -0.079266 -0.269126 0.752848 0.042 Uiso 1 1 calc R U . . .
H7C H -0.109759 -0.151789 0.681588 0.042 Uiso 1 1 calc R U . . .
C8 C 0.1095(3) -0.1438(4) 0.8313(2) 0.0262(8) Uani 1 1 d . . . . .
H8A H 0.065538 -0.085952 0.873520 0.039 Uiso 1 1 calc R U . . .
H8B H 0.193868 -0.116275 0.830853 0.039 Uiso 1 1 calc R U . . .
H8C H 0.102995 -0.241272 0.848840 0.039 Uiso 1 1 calc R U . . .
C9 C 0.1761(3) 0.3086(4) 0.8870(2) 0.0179(8) Uani 1 1 d . . . . .
C10 C 0.1283(4) 0.4488(4) 0.8544(3) 0.0276(8) Uani 1 1 d . . . . .
H10A H 0.040737 0.445668 0.851858 0.041 Uiso 1 1 calc R U . . .
H10B H 0.160199 0.467999 0.795370 0.041 Uiso 1 1 calc R U . . .
H10C H 0.153418 0.522061 0.895218 0.041 Uiso 1 1 calc R U . . .
C11 C 0.3123(3) 0.3099(5) 0.8860(3) 0.0301(9) Uani 1 1 d . . . . .
H11A H 0.340585 0.327507 0.825757 0.045 Uiso 1 1 calc R U . . .
H11B H 0.342432 0.219901 0.906215 0.045 Uiso 1 1 calc R U . . .
H11C H 0.341584 0.382992 0.925411 0.045 Uiso 1 1 calc R U . . .
C12 C 0.1321(3) 0.2830(4) 0.9812(2) 0.0279(9) Uani 1 1 d . . . . .
H12A H 0.044484 0.283113 0.982080 0.042 Uiso 1 1 calc R U . . .
H12B H 0.162129 0.356353 1.020133 0.042 Uiso 1 1 calc R U . . .
H12C H 0.161606 0.192984 1.001912 0.042 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
S1 P1 1.9535(10) . ?
P1 N1 1.649(3) . ?
P1 N3 1.657(3) . ?
P1 N2 1.660(3) . ?
N1 C1 1.489(4) . ?
N1 H1A 0.8800 . ?
N2 C5 1.489(4) . ?
N2 H2A 0.8800 . ?
N3 C9 1.483(5) . ?
N3 H3A 0.8800 . ?
C1 C4 1.520(5) . ?
C1 C2 1.524(5) . ?
C1 C3 1.532(5) . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C2 H2D 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C3 H3D 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.521(5) . ?
C5 C8 1.525(5) . ?
C5 C7 1.527(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C11 1.524(5) . ?
C9 C12 1.528(5) . ?
C9 C10 1.535(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 P1 N3 106.41(14) . . ?
N1 P1 N2 103.89(14) . . ?
N3 P1 N2 100.31(14) . . ?
N1 P1 S1 114.16(11) . . ?
N3 P1 S1 114.64(10) . . ?
N2 P1 S1 115.89(10) . . ?
C1 N1 P1 130.7(2) . . ?
C1 N1 H1A 114.7 . . ?
P1 N1 H1A 114.7 . . ?
C5 N2 P1 129.1(2) . . ?
C5 N2 H2A 115.4 . . ?
P1 N2 H2A 115.4 . . ?
C9 N3 P1 131.0(2) . . ?
C9 N3 H3A 114.5 . . ?
P1 N3 H3A 114.5 . . ?
N1 C1 C4 111.6(3) . . ?
N1 C1 C2 106.7(3) . . ?
C4 C1 C2 109.3(3) . . ?
N1 C1 C3 109.0(3) . . ?
C4 C1 C3 110.8(3) . . ?
C2 C1 C3 109.4(3) . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C2 H2D 109.5 . . ?
H2B C2 H2D 109.5 . . ?
H2C C2 H2D 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C3 H3D 109.5 . . ?
H3B C3 H3D 109.5 . . ?
H3C C3 H3D 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 C6 110.5(3) . . ?
N2 C5 C8 110.3(3) . . ?
C6 C5 C8 110.8(3) . . ?
N2 C5 C7 106.0(3) . . ?
C6 C5 C7 109.7(3) . . ?
C8 C5 C7 109.4(3) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 C11 111.5(3) . . ?
N3 C9 C12 106.6(3) . . ?
C11 C9 C12 109.4(3) . . ?
N3 C9 C10 110.2(3) . . ?
C11 C9 C10 109.7(3) . . ?
C12 C9 C10 109.3(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
N3 P1 N1 C1 159.8(3) . . . . ?
N2 P1 N1 C1 -94.8(3) . . . . ?
S1 P1 N1 C1 32.3(3) . . . . ?
N1 P1 N2 C5 164.5(3) . . . . ?
N3 P1 N2 C5 -85.6(3) . . . . ?
S1 P1 N2 C5 38.4(3) . . . . ?
N1 P1 N3 C9 -65.4(3) . . . . ?
N2 P1 N3 C9 -173.4(3) . . . . ?
S1 P1 N3 C9 61.7(3) . . . . ?
P1 N1 C1 C4 44.2(4) . . . . ?
P1 N1 C1 C2 163.6(3) . . . . ?
P1 N1 C1 C3 -78.4(4) . . . . ?
P1 N2 C5 C6 -81.3(4) . . . . ?
P1 N2 C5 C8 41.5(4) . . . . ?
P1 N2 C5 C7 159.9(3) . . . . ?
P1 N3 C9 C11 -47.1(4) . . . . ?
P1 N3 C9 C12 -166.4(3) . . . . ?
P1 N3 C9 C10 75.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A S1 0.88 2.89 3.692(3) 151.5 3_455 yes

_refine_diff_density_max         0.341
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.047



####################################################################### 
# 
# 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_at-fk-32
_database_code_depnum_ccdc_archive 'CCDC 2207982'
loop_
_audit_author_name
_audit_author_address
'Manpreet Kaur'
;Department of Chemistry, Keene State College
United States of America
;
_audit_update_record             
;
2022-09-18 deposited with the CCDC.	2023-03-16 downloaded from the CCDC.
;
_audit_creation_date             2018-06-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H15 N2 O3 P'
_chemical_formula_sum            'C17 H15 N2 O3 P'
_chemical_formula_weight         326.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H15 N2 O3 P1'
_chemical_oxdiff_usercomment     "Pourayoubi's AT-FK-32"
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0129(7)
_cell_length_b                   10.0163(7)
_cell_length_c                   10.4720(7)
_cell_angle_alpha                64.525(7)
_cell_angle_beta                 76.954(6)
_cell_angle_gamma                66.104(7)
_cell_volume                     778.78(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2984
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.3210
_cell_measurement_theta_min      4.1170
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.927
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8741
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.808
_diffrn_reflns_theta_min         3.386
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0416
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00  39.00   1.00    1.00    --  -23.96  77.00 -90.00   89
  2  ω     58.00  83.00   1.00    1.00    --   26.15  57.00 -90.00   25
  3  ω     -1.00  93.00   1.00    1.00    --   26.15  77.00-180.00   94
  4  ω    -14.00  65.00   1.00    1.00    --   26.15 -99.00   0.00   79
  5  ω    -22.00   3.00   1.00    1.00    --  -23.96 -77.00 150.00   25
  6  ω    -39.00  53.00   1.00    1.00    --   26.15 -77.00  60.00   92
  7  ω    -92.00 -66.00   1.00    1.00    --  -23.96 -77.00 150.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku, Oxford diffraction'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0594742000
_diffrn_orient_matrix_UB_12      -0.0769472000
_diffrn_orient_matrix_UB_13      0.0174312000
_diffrn_orient_matrix_UB_21      -0.0481205000
_diffrn_orient_matrix_UB_22      -0.0225308000
_diffrn_orient_matrix_UB_23      -0.0264479000
_diffrn_orient_matrix_UB_31      0.0398120000
_diffrn_orient_matrix_UB_32      0.0241800000
_diffrn_orient_matrix_UB_33      -0.0681783000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4123
_reflns_number_total             5069
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         5069
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.036
_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)+(0.0516P)²+0.1670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1159
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11),
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
;
_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
P1 P 0.71080(4) 0.67234(4) 0.27654(3) 0.02030(10) Uani 1 1 d . . . . .
O1 O 0.87095(11) 0.68064(12) 0.21503(11) 0.0267(2) Uani 1 1 d . . . . .
O3 O 0.68247(12) 0.51368(11) 0.31306(10) 0.0243(2) Uani 1 1 d . . . . .
O4 O 0.66857(12) 0.66698(13) 0.43357(10) 0.0272(2) Uani 1 1 d . . . . .
N1 N 0.31607(12) 0.97577(13) 0.08761(12) 0.0212(2) Uani 1 1 d . . . . .
N2 N 0.56754(13) 0.81755(14) 0.17603(12) 0.0220(2) Uani 1 1 d . . . . .
H2 H 0.596(2) 0.879(2) 0.097(2) 0.039(5) Uiso 1 1 d . . . . .
C1 C 0.39916(14) 0.84954(15) 0.19260(13) 0.0190(2) Uani 1 1 d . . . . .
C2 C 0.32462(16) 0.75603(16) 0.30861(14) 0.0240(3) Uani 1 1 d . . . . .
H2A H 0.386190 0.668444 0.383473 0.029 Uiso 1 1 calc R . . . .
C3 C 0.15839(17) 0.79562(17) 0.31036(16) 0.0279(3) Uani 1 1 d . . . . .
H3 H 0.104282 0.733805 0.386636 0.033 Uiso 1 1 calc R . . . .
C4 C 0.07086(16) 0.92511(18) 0.20119(16) 0.0288(3) Uani 1 1 d . . . . .
H4 H -0.043112 0.952947 0.200517 0.035 Uiso 1 1 calc R . . . .
C5 C 0.15419(15) 1.01283(17) 0.09306(15) 0.0254(3) Uani 1 1 d . . . . .
H5 H 0.094327 1.103546 0.019123 0.031 Uiso 1 1 calc R . . . .
C6 C 0.68160(15) 0.45635(15) 0.21240(14) 0.0222(2) Uani 1 1 d . . . . .
C7 C 0.57356(17) 0.37873(17) 0.24404(16) 0.0290(3) Uani 1 1 d . . . . .
H7 H 0.500654 0.372895 0.325810 0.035 Uiso 1 1 calc R . . . .
C8 C 0.5733(2) 0.30962(19) 0.15465(19) 0.0369(3) Uani 1 1 d . . . . .
H8 H 0.499302 0.256306 0.174795 0.044 Uiso 1 1 calc R . . . .
C9 C 0.6803(2) 0.31783(19) 0.03613(19) 0.0383(4) Uani 1 1 d . . . . .
H9 H 0.680919 0.268647 -0.024031 0.046 Uiso 1 1 calc R . . . .
C10 C 0.78649(19) 0.3978(2) 0.00513(18) 0.0362(3) Uani 1 1 d . . . . .
H10 H 0.859239 0.403951 -0.076759 0.043 Uiso 1 1 calc R . . . .
C11 C 0.78723(17) 0.46892(18) 0.09283(16) 0.0288(3) Uani 1 1 d . . . . .
H11 H 0.858776 0.525108 0.071295 0.035 Uiso 1 1 calc R . . . .
C12 C 0.73188(15) 0.74086(16) 0.48442(14) 0.0219(2) Uani 1 1 d . . . . .
C13 C 0.83015(18) 0.64512(17) 0.59660(16) 0.0286(3) Uani 1 1 d . . . . .
H13 H 0.858383 0.533747 0.633116 0.034 Uiso 1 1 calc R . . . .
C14 C 0.88708(19) 0.7147(2) 0.65521(17) 0.0346(3) Uani 1 1 d . . . . .
H14 H 0.954855 0.650526 0.732744 0.041 Uiso 1 1 calc R . . . .
C15 C 0.8459(2) 0.8767(2) 0.60162(19) 0.0388(4) Uani 1 1 d . . . . .
H15 H 0.883670 0.923878 0.643203 0.047 Uiso 1 1 calc R . . . .
C16 C 0.7498(2) 0.9697(2) 0.4876(2) 0.0449(4) Uani 1 1 d . . . . .
H16 H 0.724097 1.080840 0.449141 0.054 Uiso 1 1 calc R . . . .
C17 C 0.6905(2) 0.90242(18) 0.42860(18) 0.0367(3) Uani 1 1 d . . . . .
H17 H 0.622509 0.966548 0.351174 0.044 Uiso 1 1 calc R . . . .


_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 1.4618(10) . Yes
P1 O3 1.5808(10) . Yes
P1 O4 1.5843(10) . Yes
P1 N2 1.6327(12) . Yes
O3 C6 1.4031(15) . Yes
O4 C12 1.4054(15) . Yes
N1 C1 1.3331(17) . Yes
N1 C5 1.3459(16) . No
N2 H2 0.84(2) . No
N2 C1 1.4039(15) . Yes
C1 C2 1.4024(17) . No
C2 H2A 0.9500 . No
C2 C3 1.3838(19) . No
C3 H3 0.9500 . No
C3 C4 1.384(2) . No
C4 H4 0.9500 . No
C4 C5 1.383(2) . No
C5 H5 0.9500 . No
C6 C7 1.3815(18) . No
C6 C11 1.3833(19) . No
C7 H7 0.9500 . No
C7 C8 1.384(2) . No
C8 H8 0.9500 . No
C8 C9 1.383(3) . No
C9 H9 0.9500 . No
C9 C10 1.386(2) . No
C10 H10 0.9500 . No
C10 C11 1.386(2) . No
C11 H11 0.9500 . No
C12 C13 1.3772(19) . No
C12 C17 1.377(2) . No
C13 H13 0.9500 . No
C13 C14 1.3879(19) . No
C14 H14 0.9500 . No
C14 C15 1.381(2) . No
C15 H15 0.9500 . No
C15 C16 1.378(3) . No
C16 H16 0.9500 . No
C16 C17 1.387(2) . No
C17 H17 0.9500 . No

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 O3 117.56(6) . . Yes
O1 P1 O4 115.37(5) . . Yes
O1 P1 N2 110.96(6) . . Yes
O3 P1 O4 94.55(5) . . Yes
O3 P1 N2 107.96(6) . . Yes
O4 P1 N2 109.17(6) . . Yes
C6 O3 P1 124.68(9) . . Yes
C12 O4 P1 121.68(8) . . Yes
C1 N1 C5 118.18(11) . . No
P1 N2 H2 117.9(13) . . Yes
C1 N2 P1 129.39(9) . . Yes
C1 N2 H2 112.3(13) . . Yes
N1 C1 N2 114.18(11) . . Yes
N1 C1 C2 122.77(12) . . No
C2 C1 N2 123.05(12) . . No
C1 C2 H2A 121.1 . . No
C3 C2 C1 117.76(13) . . No
C3 C2 H2A 121.1 . . No
C2 C3 H3 120.0 . . No
C4 C3 C2 120.10(12) . . No
C4 C3 H3 120.0 . . No
C3 C4 H4 121.0 . . No
C5 C4 C3 118.04(12) . . No
C5 C4 H4 121.0 . . No
N1 C5 C4 123.12(14) . . No
N1 C5 H5 118.4 . . No
C4 C5 H5 118.4 . . No
C7 C6 O3 115.53(12) . . No
C7 C6 C11 121.77(13) . . No
C11 C6 O3 122.62(12) . . No
C6 C7 H7 120.5 . . No
C6 C7 C8 118.91(14) . . No
C8 C7 H7 120.5 . . No
C7 C8 H8 119.9 . . No
C9 C8 C7 120.30(15) . . No
C9 C8 H8 119.9 . . No
C8 C9 H9 120.0 . . No
C8 C9 C10 119.99(14) . . No
C10 C9 H9 120.0 . . No
C9 C10 H10 119.8 . . No
C11 C10 C9 120.41(15) . . No
C11 C10 H10 119.8 . . No
C6 C11 C10 118.60(14) . . No
C6 C11 H11 120.7 . . No
C10 C11 H11 120.7 . . No
C13 C12 O4 116.95(12) . . No
C17 C12 O4 121.12(12) . . No
C17 C12 C13 121.86(13) . . No
C12 C13 H13 120.7 . . No
C12 C13 C14 118.62(13) . . No
C14 C13 H13 120.7 . . No
C13 C14 H14 119.8 . . No
C15 C14 C13 120.48(14) . . No
C15 C14 H14 119.8 . . No
C14 C15 H15 120.1 . . No
C16 C15 C14 119.76(14) . . No
C16 C15 H15 120.1 . . No
C15 C16 H16 119.7 . . No
C15 C16 C17 120.57(15) . . No
C17 C16 H16 119.7 . . No
C12 C17 C16 118.69(15) . . No
C12 C17 H17 120.7 . . No
C16 C17 H17 120.7 . . No

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 N1 0.84(2) 2.08(2) 2.9229(16) 174.7(18) 2_675 yes
C5 H5 O1 0.95 2.53 3.3365(19) 142.2 2_675 yes
C10 H10 O1 0.95 2.55 3.4416(18) 155.5 2_765 yes
C11 H11 O1 0.95 2.63 3.2819(18) 125.9 . yes
C13 H13 O1 0.95 2.77 3.3965(18) 124.4 2_766 yes

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 O3 C6 C7 -144.85(11) . . . . ?
P1 O3 C6 C11 38.37(17) . . . . ?
P1 O4 C12 C13 -118.04(12) . . . . ?
P1 O4 C12 C17 65.07(16) . . . . ?
P1 N2 C1 N1 -177.58(9) . . . . ?
P1 N2 C1 C2 1.74(19) . . . . ?
O1 P1 O3 C6 -66.22(11) . . . . ?
O1 P1 O4 C12 30.49(12) . . . . ?
O1 P1 N2 C1 177.02(11) . . . . ?
O3 P1 O4 C12 153.96(10) . . . . ?
O3 P1 N2 C1 46.85(13) . . . . ?
O3 C6 C7 C8 -175.72(13) . . . . ?
O3 C6 C11 C10 174.90(13) . . . . ?
O4 P1 O3 C6 172.01(10) . . . . ?
O4 P1 N2 C1 -54.74(13) . . . . ?
O4 C12 C13 C14 -176.21(13) . . . . ?
O4 C12 C17 C16 176.73(15) . . . . ?
N1 C1 C2 C3 1.87(19) . . . . ?
N2 P1 O3 C6 60.17(11) . . . . ?
N2 P1 O4 C12 -95.24(11) . . . . ?
N2 C1 C2 C3 -177.39(12) . . . . ?
C1 N1 C5 C4 -0.9(2) . . . . ?
C1 C2 C3 C4 -0.97(19) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C3 C4 C5 N1 1.7(2) . . . . ?
C5 N1 C1 N2 178.35(11) . . . . ?
C5 N1 C1 C2 -0.97(18) . . . . ?
C6 C7 C8 C9 0.3(2) . . . . ?
C7 C6 C11 C10 -1.7(2) . . . . ?
C7 C8 C9 C10 -1.1(2) . . . . ?
C8 C9 C10 C11 0.5(2) . . . . ?
C9 C10 C11 C6 0.9(2) . . . . ?
C11 C6 C7 C8 1.1(2) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
C13 C12 C17 C16 0.0(2) . . . . ?
C13 C14 C15 C16 -1.1(3) . . . . ?
C14 C15 C16 C17 1.8(3) . . . . ?
C15 C16 C17 C12 -1.2(3) . . . . ?
C17 C12 C13 C14 0.7(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'POLYMER LOOP'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.288
_oxdiff_exptl_absorpt_empirical_full_min 0.708
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_mpsab
_database_code_depnum_ccdc_archive 'CCDC 2207987'
loop_
_audit_author_name
_audit_author_address
'Marek Necas'
;Department of Chemistry, Masaryk University
Czech Republic
;
_audit_update_record             
;
2022-09-18 deposited with the CCDC.	2023-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 N6 P S'
_chemical_formula_weight         342.36

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   9.4456(2)
_cell_length_b                   12.1063(2)
_cell_length_c                   14.6424(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1674.38(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7478
_cell_measurement_theta_min      3.8900
_cell_measurement_theta_max      29.6500

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.297
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85058
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode MicroMax-007HF DW 1.2 kW'
_diffrn_measurement_device_type  'AFC11 (Right): Eulerian 3 circle CCD'
_diffrn_measurement_method       'Profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9054
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.069
_diffrn_reflns_theta_max         25.344
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             2985
_reflns_number_gt                2917
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_max     0.953
_reflns_Friedel_fraction_full    0.952

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

_computing_data_collection       
;
Rigaku CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)
MSCServDetCCD = {5.7.3.4}
;
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0377P)²+0.3432P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1337 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2985
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0246
_refine_ls_wR_factor_ref         0.0636
_refine_ls_wR_factor_gt          0.0628
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.19802(6) 0.53719(5) -0.02748(5) 0.02186(16) Uani 1 1 d . . . . .
P1 P 0.34535(6) 0.49876(5) 0.05848(5) 0.01612(15) Uani 1 1 d . . . . .
N1 N 0.4637(2) 0.59925(16) 0.06486(16) 0.0193(4) Uani 1 1 d . . . . .
H1A H 0.431594 0.666261 0.054211 0.023 Uiso 1 1 calc R U . . .
N2 N 0.4270(2) 0.38133(17) 0.03542(14) 0.0183(5) Uani 1 1 d . . . . .
H2A H 0.442254 0.336723 0.081850 0.022 Uiso 1 1 calc R U . . .
N3 N 0.3002(2) 0.47901(18) 0.16682(16) 0.0196(5) Uani 1 1 d . . . . .
H3A H 0.346130 0.519064 0.207307 0.023 Uiso 1 1 calc R U . . .
N4 N 0.8407(2) 0.66891(17) 0.06064(18) 0.0222(4) Uani 1 1 d . . . . .
N5 N 0.5727(3) 0.38598(19) -0.19758(16) 0.0271(5) Uani 1 1 d . . . . .
N6 N 0.0321(2) 0.25805(18) 0.18044(15) 0.0217(5) Uani 1 1 d . . . . .
C1 C 0.6093(2) 0.5914(2) 0.08516(17) 0.0180(5) Uani 1 1 d . . . . .
C2 C 0.7006(3) 0.6687(2) 0.04719(18) 0.0191(5) Uani 1 1 d . . . . .
H2B H 0.661337 0.724688 0.009450 0.023 Uiso 1 1 calc R U . . .
C3 C 0.8950(3) 0.5883(2) 0.1129(2) 0.0238(5) Uani 1 1 d . . . . .
H3B H 0.994531 0.585665 0.121730 0.029 Uiso 1 1 calc R U . . .
C4 C 0.8117(3) 0.5090(2) 0.1542(2) 0.0246(6) Uani 1 1 d . . . . .
H4B H 0.853908 0.453618 0.191275 0.029 Uiso 1 1 calc R U . . .
C5 C 0.6664(3) 0.5105(2) 0.14144(19) 0.0218(6) Uani 1 1 d . . . . .
H5B H 0.607330 0.457478 0.170405 0.026 Uiso 1 1 calc R U . . .
C6 C 0.4748(3) 0.34510(19) -0.05030(17) 0.0185(5) Uani 1 1 d . . . . .
C7 C 0.5191(3) 0.4183(2) -0.11736(18) 0.0222(6) Uani 1 1 d . . . . .
H7A H 0.511055 0.495237 -0.105710 0.027 Uiso 1 1 calc R U . . .
C8 C 0.5838(4) 0.2778(3) -0.2136(2) 0.0375(8) Uani 1 1 d . . . . .
H8A H 0.623695 0.254042 -0.269785 0.045 Uiso 1 1 calc R U . . .
C9 C 0.5398(4) 0.1994(2) -0.1518(2) 0.0394(8) Uani 1 1 d . . . . .
H9A H 0.547799 0.123027 -0.165941 0.047 Uiso 1 1 calc R U . . .
C10 C 0.4838(3) 0.2326(2) -0.06904(18) 0.0278(6) Uani 1 1 d . . . . .
H10A H 0.452128 0.179683 -0.025738 0.033 Uiso 1 1 calc R U . . .
C11 C 0.1980(2) 0.4064(2) 0.20185(17) 0.0168(5) Uani 1 1 d . . . . .
C12 C 0.1298(3) 0.3282(2) 0.14803(18) 0.0195(5) Uani 1 1 d . . . . .
H12A H 0.153528 0.324261 0.085069 0.023 Uiso 1 1 calc R U . . .
C13 C 0.0005(3) 0.2622(2) 0.26957(19) 0.0242(6) Uani 1 1 d . . . . .
H13A H -0.068392 0.212676 0.293114 0.029 Uiso 1 1 calc R U . . .
C14 C 0.0648(3) 0.3364(2) 0.32864(19) 0.0244(6) Uani 1 1 d . . . . .
H14A H 0.041370 0.336589 0.391742 0.029 Uiso 1 1 calc R U . . .
C15 C 0.1637(3) 0.4102(2) 0.29433(19) 0.0215(5) Uani 1 1 d . . . . .
H15A H 0.207467 0.462644 0.333427 0.026 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
S1 P1 1.9331(9) . ?
P1 N2 1.652(2) . ?
P1 N1 1.655(2) . ?
P1 N3 1.660(2) . ?
N1 C1 1.410(3) . ?
N1 H1A 0.8800 . ?
N2 C6 1.404(3) . ?
N2 H2A 0.8800 . ?
N3 C11 1.403(3) . ?
N3 H3A 0.8800 . ?
N4 C2 1.338(3) . ?
N4 C3 1.341(4) . ?
N5 C8 1.334(4) . ?
N5 C7 1.338(3) . ?
N6 C13 1.340(3) . ?
N6 C12 1.340(3) . ?
C1 C2 1.389(4) . ?
C1 C5 1.390(4) . ?
C2 H2B 0.9500 . ?
C3 C4 1.381(4) . ?
C3 H3B 0.9500 . ?
C4 C5 1.385(4) . ?
C4 H4B 0.9500 . ?
C5 H5B 0.9500 . ?
C6 C7 1.387(4) . ?
C6 C10 1.392(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.375(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.382(4) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C12 1.391(4) . ?
C11 C15 1.393(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.386(4) . ?
C13 H13A 0.9500 . ?
C14 C15 1.387(4) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 P1 N1 109.18(10) . . ?
N2 P1 N3 101.02(11) . . ?
N1 P1 N3 103.02(11) . . ?
N2 P1 S1 114.22(9) . . ?
N1 P1 S1 110.25(8) . . ?
N3 P1 S1 118.17(8) . . ?
C1 N1 P1 128.41(16) . . ?
C1 N1 H1A 115.8 . . ?
P1 N1 H1A 115.8 . . ?
C6 N2 P1 126.97(17) . . ?
C6 N2 H2A 116.5 . . ?
P1 N2 H2A 116.5 . . ?
C11 N3 P1 128.05(18) . . ?
C11 N3 H3A 116.0 . . ?
P1 N3 H3A 116.0 . . ?
C2 N4 C3 117.4(2) . . ?
C8 N5 C7 118.1(2) . . ?
C13 N6 C12 118.3(2) . . ?
C2 C1 C5 118.1(2) . . ?
C2 C1 N1 118.4(2) . . ?
C5 C1 N1 123.4(2) . . ?
N4 C2 C1 123.8(2) . . ?
N4 C2 H2B 118.1 . . ?
C1 C2 H2B 118.1 . . ?
N4 C3 C4 122.6(2) . . ?
N4 C3 H3B 118.7 . . ?
C4 C3 H3B 118.7 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4B 120.1 . . ?
C5 C4 H4B 120.1 . . ?
C4 C5 C1 118.3(2) . . ?
C4 C5 H5B 120.9 . . ?
C1 C5 H5B 120.9 . . ?
C7 C6 C10 117.8(2) . . ?
C7 C6 N2 122.0(2) . . ?
C10 C6 N2 120.1(2) . . ?
N5 C7 C6 123.3(2) . . ?
N5 C7 H7A 118.4 . . ?
C6 C7 H7A 118.4 . . ?
N5 C8 C9 122.6(3) . . ?
N5 C8 H8A 118.7 . . ?
C9 C8 H8A 118.7 . . ?
C8 C9 C10 119.4(3) . . ?
C8 C9 H9A 120.3 . . ?
C10 C9 H9A 120.3 . . ?
C9 C10 C6 118.8(3) . . ?
C9 C10 H10A 120.6 . . ?
C6 C10 H10A 120.6 . . ?
C12 C11 C15 117.7(2) . . ?
C12 C11 N3 122.6(2) . . ?
C15 C11 N3 119.7(2) . . ?
N6 C12 C11 123.4(2) . . ?
N6 C12 H12A 118.3 . . ?
C11 C12 H12A 118.3 . . ?
N6 C13 C14 122.3(2) . . ?
N6 C13 H13A 118.8 . . ?
C14 C13 H13A 118.8 . . ?
C13 C14 C15 119.1(2) . . ?
C13 C14 H14A 120.5 . . ?
C15 C14 H14A 120.5 . . ?
C14 C15 C11 119.2(3) . . ?
C14 C15 H15A 120.4 . . ?
C11 C15 H15A 120.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A N4 0.88 2.17 3.038(3) 167.0 3_465 yes
N2 H2A N6 0.88 2.03 2.888(3) 164.7 3 yes
N3 H3A N5 0.88 1.96 2.838(3) 173.5 2_665 yes

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.037



####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 2207985'
loop_
_audit_author_name
_audit_author_address
'Michal Dusek'
;Institute of Physics of the Czech Academy of Sciences
Czech Republic
;
_audit_update_record             
;
2022-09-18 deposited with the CCDC.	2023-03-16 downloaded from the CCDC.
;
_publcif_datablock.id            {04d221a3-83ec-4d38-b534-2129a391a38a}

#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H28 Cl1 N2 O2 P1'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C18 H28 Cl1 N2 O2 P1'
_chemical_formula_weight         370.9
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ycb'
_symmetry_Int_Tables_number      14

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2

_cell_length_a                   11.2653(2)
_cell_length_b                   19.0533(4)
_cell_length_c                   8.9226(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.3906(19)
_cell_angle_gamma                90
_cell_volume                     1889.49(7)

loop_
_jana_cell_twin_matrix_id
_jana_cell_twin_volume_fraction
_jana_cell_twin_matrix_1_1
_jana_cell_twin_matrix_1_2
_jana_cell_twin_matrix_1_3
_jana_cell_twin_matrix_2_1
_jana_cell_twin_matrix_2_2
_jana_cell_twin_matrix_2_3
_jana_cell_twin_matrix_3_1
_jana_cell_twin_matrix_3_2
_jana_cell_twin_matrix_3_3
? ? ? ? ? ? ? ? ? ? ?
_cell_formula_units_Z            4

_cell_measurement_reflns_used    17129
_cell_measurement_theta_min      3.97
_cell_measurement_theta_max      67.07
_cell_measurement_temperature    120.00(10)
_cell_special_details            ?

_exptl_crystal_density_diffrn    1.3037
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             792

_exptl_absorpt_coefficient_mu    2.691
_exptl_crystal_description       'polygon shape'
_exptl_crystal_size_max          0.433
_exptl_crystal_size_mid          0.255
_exptl_crystal_size_min          0.111
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            white
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33a (release 28-03-2014 CrysAlis171 .NET)
(compiled Mar 28 2014,12:25:20)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.289
_exptl_absorpt_correction_T_max  1
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      120
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3745
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            29189
_diffrn_reflns_theta_min         3.98
_diffrn_reflns_theta_max         67.23
_diffrn_reflns_theta_full        67.23
_diffrn_measured_fraction_theta_max 1
_diffrn_measured_fraction_theta_full 1
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0111
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_reduction_process 
;
Integration of the CCD images was done by program CrysAlisPro
(Agilent Technologies, 2010). The same program was used for indexing of the
crystal shape and absorption correction.
;

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          x-ray

#=======================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
The refinement was carried out against all reflections.  The conventional
R-factor is always based on F. The goodness of fit as well as the weighted
R-factor are based on F and F² for refinement carried out on F and F²,
respectively. The threshold expression is used only for calculating
R-factors etc. and it is not relevant to the choice of reflections for
refinement.

The program used for refinement, Jana2006, uses the weighting scheme
based on the experimental expectations, see _refine_ls_weighting_details,
that does not force S to be one. Therefore the values of S are usually larger
than the ones from the SHELX program.
;

_reflns_number_total             3385
_reflns_number_gt                3225
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef F
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_gt          0.0530
_refine_ls_R_factor_all          0.0326
_refine_ls_wR_factor_ref         0.0537
_refine_ls_goodness_of_fit_ref   2.12
_refine_ls_goodness_of_fit_gt    2.14
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         3385
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_number_constraints    106
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(F)+0.0004F²)
_refine_ls_hydrogen_treatment    mixed
_refine_ls_shift/su_max          0.0185
_refine_ls_shift/su_mean         0.0020
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0181 0.0091 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
Cl 0.3639 0.7018 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
N 0.0311 0.0180 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.0492 0.0322 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
P 0.2955 0.4335 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33a (release 28-03-2014 CrysAlis171 .NET)
(compiled Mar 28 2014,12:25:20)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33a (release 28-03-2014 CrysAlis171 .NET)
(compiled Mar 28 2014,12:25:20)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33a (release 28-03-2014 CrysAlis171 .NET)
(compiled Mar 28 2014,12:25:20)
;
_computing_structure_solution    ?
_computing_structure_refinement  ?
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_restr_distance_atom_site_label_1
_restr_distance_site_symmetry_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
? ? ? ? ? ?

loop_
_restr_angle_atom_site_label_1
_restr_angle_site_symmetry_1
_restr_angle_atom_site_label_2
_restr_angle_site_symmetry_2
_restr_angle_atom_site_label_3
_restr_angle_site_symmetry_3
_restr_angle_target
_restr_angle_target_weight_param
? ? ? ? ? ? ? ?

loop_
_restr_torsion_atom_site_label_1
_restr_torsion_site_symmetry_1
_restr_torsion_atom_site_label_2
_restr_torsion_site_symmetry_2
_restr_torsion_atom_site_label_3
_restr_torsion_site_symmetry_3
_restr_torsion_atom_site_label_4
_restr_torsion_site_symmetry_4
_restr_torsion_angle_target
_restr_torsion_weight_param
? ? ? ? ? ? ? ? ? ?

loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_site_symmetry_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
? ? ? ? ? ?

loop_
_restr_equal_angle_atom_site_label_1
_restr_equal_angle_site_symmetry_1
_restr_equal_angle_atom_site_label_2
_restr_equal_angle_site_symmetry_2
_restr_equal_angle_atom_site_label_3
_restr_equal_angle_site_symmetry_3
_restr_equal_angle_class_class_id
_restr_equal_angle_class_target_weight_param
? ? ? ? ? ? ? ?

loop_
_restr_equal_torsion_atom_site_label_1
_restr_equal_torsion_site_symmetry_1
_restr_equal_torsion_atom_site_label_2
_restr_equal_torsion_site_symmetry_2
_restr_equal_torsion_atom_site_label_3
_restr_equal_torsion_site_symmetry_3
_restr_equal_torsion_atom_site_label_4
_restr_equal_torsion_site_symmetry_4
_restr_equal_torsion_class_class_id
_restr_equal_torsion_class_target_weight_param
? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.80897(4) 0.91632(2) 0.03941(5) Uani 0.03624(15) 4 1 d . . .
P1 P 0.49311(3) 1.196108(17) 0.27095(4) Uani 0.01627(13) 4 1 d . . .
O1 O 0.52029(8) 1.11601(5) 0.32873(12) Uani 0.0203(3) 4 1 d . . .
O2 O 0.48581(9) 1.19679(5) 0.10400(12) Uani 0.0201(3) 4 1 d . . .
N1 N 0.37419(10) 1.21364(6) 0.34495(15) Uani 0.0205(4) 4 1 d . . .
N2 N 0.59626(10) 1.24797(6) 0.35860(15) Uani 0.0196(4) 4 1 d . . .
C1 C 0.80384(12) 1.29086(7) 0.39479(18) Uani 0.0216(4) 4 1 d . . .
C2 C 0.27152(12) 1.16568(7) 0.34111(17) Uani 0.0195(4) 4 1 d . . .
C3 C 0.72319(13) 0.97632(8) 0.12283(17) Uani 0.0237(4) 4 1 d . . .
C4 C 0.03920(13) 1.12803(9) 0.43358(19) Uani 0.0294(5) 4 1 d . . .
C5 C 0.68480(11) 1.28599(7) 0.28612(16) Uani 0.0175(4) 4 1 d . . .
C6 C 0.89822(13) 1.33110(8) 0.32378(19) Uani 0.0288(5) 4 1 d . . .
C7 C 0.04553(12) 1.15522(8) 0.27536(18) Uani 0.0265(5) 4 1 d . . .
C8 C 0.85407(14) 1.40384(8) 0.27017(19) Uani 0.0288(5) 4 1 d . . .
C9 C 0.58969(12) 1.07097(7) 0.25737(16) Uani 0.0190(4) 4 1 d . . .
C10 C 0.77270(13) 1.04088(8) 0.16841(18) Uani 0.0246(4) 4 1 d . . .
C11 C 0.64097(13) 1.35907(8) 0.23421(18) Uani 0.0245(4) 4 1 d . . .
C12 C 0.73481(14) 1.39865(8) 0.1611(2) Uani 0.0292(5) 4 1 d . . .
C13 C 0.26589(13) 1.13570(8) 0.49776(19) Uani 0.0273(5) 4 1 d . . .
C14 C 0.15504(15) 1.08914(9) 0.4972(2) Uani 0.0349(5) 4 1 d . . .
C15 C 0.60886(14) 0.95808(8) 0.1447(2) Uani 0.0293(5) 4 1 d . . .
C16 C 0.54197(14) 1.00608(8) 0.21279(19) Uani 0.0273(5) 4 1 d . . .
C17 C 0.70521(13) 1.08870(7) 0.23644(18) Uani 0.0232(4) 4 1 d . . .
C18 C 0.15508(13) 1.20302(8) 0.27528(19) Uani 0.0255(5) 4 1 d . . .
H1c1 H 0.832993 1.244468 0.421845 Uiso 0.0259 4 1 d . . .
H2c1 H 0.791248 1.313922 0.486558 Uiso 0.0259 4 1 d . . .
H1c2 H 0.282215 1.126785 0.276235 Uiso 0.0234 4 1 d . . .
H1c4 H -0.028009 1.096715 0.429468 Uiso 0.0353 4 1 d . . .
H2c4 H 0.028271 1.166711 0.498918 Uiso 0.0353 4 1 d . . .
H1c5 H 0.69615 1.260134 0.197207 Uiso 0.021 4 1 d . . .
H1c6 H 0.918357 1.304932 0.239474 Uiso 0.0345 4 1 d . . .
H2c6 H 0.970631 1.335377 0.396639 Uiso 0.0345 4 1 d . . .
H1c7 H -0.026597 1.180808 0.237742 Uiso 0.0317 4 1 d . . .
H2c7 H 0.050062 1.11632 0.208139 Uiso 0.0317 4 1 d . . .
H1c8 H 0.843349 1.431934 0.356271 Uiso 0.0346 4 1 d . . .
H2c8 H 0.913035 1.426062 0.219634 Uiso 0.0346 4 1 d . . .
H1c10 H 0.852808 1.052454 0.153163 Uiso 0.0295 4 1 d . . .
H1c11 H 0.622915 1.385239 0.319641 Uiso 0.0294 4 1 d . . .
H2c11 H 0.567712 1.355239 0.162704 Uiso 0.0294 4 1 d . . .
H1c12 H 0.747333 1.374753 0.070275 Uiso 0.0351 4 1 d . . .
H2c12 H 0.705701 1.444965 0.133222 Uiso 0.0351 4 1 d . . .
H1c13 H 0.264354 1.173413 0.568764 Uiso 0.0328 4 1 d . . .
H2c13 H 0.337316 1.108868 0.531909 Uiso 0.0328 4 1 d . . .
H1c14 H 0.162136 1.047962 0.437266 Uiso 0.0419 4 1 d . . .
H2c14 H 0.151427 1.073811 0.59884 Uiso 0.0419 4 1 d . . .
H1c15 H 0.5761 0.912911 0.113317 Uiso 0.0352 4 1 d . . .
H1c16 H 0.462236 0.994153 0.22899 Uiso 0.0328 4 1 d . . .
H1c17 H 0.73828 1.13369 0.268727 Uiso 0.0279 4 1 d . . .
H1c18 H 0.158831 1.217699 0.173231 Uiso 0.0306 4 1 d . . .
H2c18 H 0.146265 1.244442 0.33374 Uiso 0.0306 4 1 d . . .
H1n2 H 0.5842(16) 1.2660(10) 0.443(2) Uiso 0.0236 4 1 d . . .
H1n1 H 0.3831(16) 1.2436(10) 0.418(2) Uiso 0.0246 4 1 d . . .


loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O2 . . 1.4785(11) yes
P1 N1 . . 1.6219(13) yes
P1 N2 . . 1.6254(12) yes
O1 C9 . . 1.3839(18) yes
N1 C2 . . 1.4700(18) yes
N1 H1n1 . . 0.86(2) no
N2 C5 . . 1.4658(19) yes
N2 H1n2 . . 0.86(2) no
C1 C5 . . 1.5241(18) no
C1 C6 . . 1.530(2) ?no
C1 H1c1 . . 0.96 no
C1 H2c1 . . 0.96 no
C2 C13 . . 1.521(2) no
C2 C18 . . 1.5233(19) no
C2 H1c2 . . 0.96 no
C3 C10 . . 1.384(2) no
C3 C15 . . 1.378(2) no
C4 C7 . . 1.516(2) no
C4 C14 . . 1.527(2) no
C4 H1c4 . . 0.96 no
C4 H2c4 . . 0.96 no
C5 C11 . . 1.5239(19) no
C5 H1c5 . . 0.96 no
C6 C8 . . 1.523(2) no
C6 H1c6 . . 0.96 no
C6 H2c6 . . 0.96 no
C7 C18 . . 1.534(2) no
C7 H1c7 . . 0.96 no
C7 H2c7 . . 0.96 no
C8 C12 . . 1.528(2) no
C8 H1c8 . . 0.96 no
C8 H2c8 . . 0.96 no
C9 C16 . . 1.381(2) no
C9 C17 . . 1.386(2) no
C10 C17 . . 1.388(2) no
C10 H1c10 . . 0.96 no
C11 C12 . . 1.529(2) no
C11 H1c11 . . 0.96 no
C11 H2c11 . . 0.96 no
C12 H1c12 . . 0.96 no
C12 H2c12 . . 0.96 no
C13 C14 . . 1.531(2) no
C13 H1c13 . . 0.96 no
C13 H2c13 . . 0.96 no
C14 H1c14 . . 0.96 no
C14 H2c14 . . 0.96 no
C15 C16 . . 1.387(2) no
C15 H1c15 . . 0.96 no
C16 H1c16 . . 0.96 no
C17 H1c17 . . 0.96 no
C18 H1c18 . . 0.96 no
C18 H2c18 . . 0.96 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 P1 N1 . . . 119.63(6) yes
O2 P1 N2 . . . 113.41(6) yes
N1 P1 N2 . . . 104.60(6) yes
P1 N1 C2 . . . 124.16(10) yes
P1 N1 H1n1 . . . 116.3(12) nO
C2 N1 H1n1 . . . 115.1(13) nO
P1 N2 C5 . . . 124.94(10) yes
P1 N2 H1n2 . . . 117.6(12) no
C5 N2 H1n2 . . . 113.9(12) no
C5 C1 C6 . . . 111.47(12) no
C5 C1 H1c1 . . . 109.47 no
C5 C1 H2c1 . . . 109.47 no
C6 C1 H1c1 . . . 109.47 no
C6 C1 H2c1 . . . 109.47 no
H1c1 C1 H2c1 . . . 107.4 ?
N1 C2 C13 . . . 111.26(11) ?
N1 C2 C18 . . . 110.09(11) ?
N1 C2 H1c2 . . . 108.56 ?
C13 C2 C18 . . . 111.56(12) ?
C13 C2 H1c2 . . . 107 ?
C18 C2 H1c2 . . . 108.24 ?
C10 C3 C15 . . . 121.58(15) ?
C7 C4 C14 . . . 110.16(14) ?
C7 C4 H1c4 . . . 109.47 ?
C7 C4 H2c4 . . . 109.47 ?
C14 C4 H1c4 . . . 109.47 ?
C14 C4 H2c4 . . . 109.47 ?
H1c4 C4 H2c4 . . . 108.77 ?
N2 C5 C1 . . . 109.93(11) ?
N2 C5 C11 . . . 112.06(11) ?
N2 C5 H1c5 . . . 107.64 ?
C1 C5 C11 . . . 110.22(11) ?
C1 C5 H1c5 . . . 109.57 ?
C11 C5 H1c5 . . . 107.33 ?
C1 C6 C8 . . . 111.89(13) ?
C1 C6 H1c6 . . . 109.47 ?
C1 C6 H2c6 . . . 109.47 ?
C8 C6 H1c6 . . . 109.47 ?
C8 C6 H2c6 . . . 109.47 ?
H1c6 C6 H2c6 . . . 106.94 ?
C4 C7 C18 . . . 111.30(12) ?
C4 C7 H1c7 . . . 109.47 ?
C4 C7 H2c7 . . . 109.47 ?
C18 C7 H1c7 . . . 109.47 ?
C18 C7 H2c7 . . . 109.47 ?
H1c7 C7 H2c7 . . . 107.57 ?
C6 C8 C12 . . . 110.44(12) ?
C6 C8 H1c8 . . . 109.47 ?
C6 C8 H2c8 . . . 109.47 ?
C12 C8 H1c8 . . . 109.47 ?
C12 C8 H2c8 . . . 109.47 ?
H1c8 C8 H2c8 . . . 108.48 ?
O1 C9 C16 . . . 117.72(13) ?
O1 C9 C17 . . . 121.61(12) ?
C16 C9 C17 . . . 120.62(14) ?
C3 C10 C17 . . . 119.25(14) ?
C3 C10 H1c10 . . . 120.38 ?
C17 C10 H1c10 . . . 120.38 ?
C5 C11 C12 . . . 111.60(12) ?
C5 C11 H1c11 . . . 109.47 ?
C5 C11 H2c11 . . . 109.47 ?
C12 C11 H1c11 . . . 109.47 ?
C12 C11 H2c11 . . . 109.47 ?
H1c11 C11 H2c11 . . . 107.26 ?
C8 C12 C11 . . . 110.96(13) ?
C8 C12 H1c12 . . . 109.47 ?
C8 C12 H2c12 . . . 109.47 ?
C11 C12 H1c12 . . . 109.47 ?
C11 C12 H2c12 . . . 109.47 ?
H1c12 C12 H2c12 . . . 107.94 ?
C2 C13 C14 . . . 111.77(12) ?
C2 C13 H1c13 . . . 109.47 ?
C2 C13 H2c13 . . . 109.47 ?
C14 C13 H1c13 . . . 109.47 ?
C14 C13 H2c13 . . . 109.47 ?
H1c13 C13 H2c13 . . . 107.07 ?
C4 C14 C13 . . . 111.53(14) ?
C4 C14 H1c14 . . . 109.47 ?
C4 C14 H2c14 . . . 109.47 ?
C13 C14 H1c14 . . . 109.47 ?
C13 C14 H2c14 . . . 109.47 ?
H1c14 C14 H2c14 . . . 107.33 ?
C3 C15 C16 . . . 118.87(14) ?
C3 C15 H1c15 . . . 120.56 ?
C16 C15 H1c15 . . . 120.56 ?
C9 C16 C15 . . . 120.19(15) ?
C9 C16 H1c16 . . . 119.9 ?
C15 C16 H1c16 . . . 119.9 ?
C9 C17 C10 . . . 119.48(13) ?
C9 C17 H1c17 . . . 120.26 ?
C10 C17 H1c17 . . . 120.26 ?
C2 C18 C7 . . . 111.39(12) ?
C2 C18 H1c18 . . . 109.47 ?
C2 C18 H2c18 . . . 109.47 ?
C7 C18 H1c18 . . . 109.47 ?
C7 C18 H2c18 . . . 109.47 ?
H1c18 C18 H2c18 . . . 107.48 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H1n2 O2 . . 4_575 0.86(2) 2.08(2) 2.8878(17) 157.1(16) yes
N1 H1n1 O2 . . 4_575 0.86(2) 2.180(18) 2.9812(15) 154.7(17) yes


#=======================================================================

# 11. STRUCTURE-FACTOR LIST


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2207986'
loop_
_audit_author_name
_audit_author_address
'Michal Dusek'
;Institute of Physics of the Czech Academy of Sciences
Czech Republic
;
_audit_update_record             
;
2022-09-18 deposited with the CCDC.	2023-03-16 downloaded from the CCDC.
;
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H32 Cl1 N2 O2 P1'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C20 H32 Cl1 N2 O2 P1'
_chemical_formula_weight         398.9
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ycb'
_symmetry_Int_Tables_number      14

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2

_cell_length_a                   6.0515(2)
_cell_length_b                   17.9235(8)
_cell_length_c                   19.3040(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.157(3)
_cell_angle_gamma                90
_cell_volume                     2090.61(14)

loop_
_jana_cell_twin_matrix_id
_jana_cell_twin_volume_fraction
_jana_cell_twin_matrix_1_1
_jana_cell_twin_matrix_1_2
_jana_cell_twin_matrix_1_3
_jana_cell_twin_matrix_2_1
_jana_cell_twin_matrix_2_2
_jana_cell_twin_matrix_2_3
_jana_cell_twin_matrix_3_1
_jana_cell_twin_matrix_3_2
_jana_cell_twin_matrix_3_3
? ? ? ? ? ? ? ? ? ? ?
_cell_formula_units_Z            4

_cell_measurement_reflns_used    5240
_cell_measurement_theta_min      3.35
_cell_measurement_theta_max      66.83
_cell_measurement_temperature    293
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             856

_exptl_absorpt_coefficient_mu    2.467
_exptl_crystal_description       'polygon shape'
_exptl_crystal_size_max          0.497
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.149
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            white
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.626
_exptl_absorpt_correction_T_max  1
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      293
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3784
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            10734
_diffrn_reflns_theta_min         3.37
_diffrn_reflns_theta_max         67.15
_diffrn_reflns_theta_full        66.8
_diffrn_measured_fraction_theta_max 0.97
_diffrn_measured_fraction_theta_full 0.98
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_reduction_process 
;
Integration of the CCD images was done by program CrysAlisPro
(Agilent Technologies, 2010). The same program was used for indexing of the
crystal shape and absorption correction.
;

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          X-ray

#=======================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
The refinement was carried out against all reflections.  The conventional
R-factor is always based on F. The goodness of fit as well as the weighted
R-factor are based on F and F² for refinement carried out on F and F²,
respectively. The threshold expression is used only for calculating
R-factors etc. and it is not relevant to the choice of reflections for
refinement.

The program used for refinement, Jana2006, uses the weighting scheme
based on the experimental expectations, see _refine_ls_weighting_details,
that does not force S to be one. Therefore the values of S are usually larger
than the ones from the SHELX program.
;

_reflns_number_total             3644
_reflns_number_gt                2913
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef F
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_gt          0.0607
_refine_ls_R_factor_all          0.0620
_refine_ls_wR_factor_ref         0.0632
_refine_ls_goodness_of_fit_ref   1.62
_refine_ls_goodness_of_fit_gt    1.75
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         3644
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_number_constraints    128
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(F)+0.0004F²)
_refine_ls_hydrogen_treatment    constr
_refine_ls_shift/su_max          0.0131
_refine_ls_shift/su_mean         0.0005
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.37
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0181 0.0091 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
Cl 0.3639 0.7018 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
N 0.0311 0.0180 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.0492 0.0322 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
P 0.2955 0.4335 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis 2007)'
_computing_structure_refinement  
"Jana2006 (Petříček, Dušek & Palatinus, 2006)"
_computing_molecular_graphics    'Diamond (Brandenburg & Putz, 2005)'
_computing_publication_material  
"Jana2006 (Petříček, Dušek & Palatinus, 2006)"

loop_
_restr_distance_atom_site_label_1
_restr_distance_site_symmetry_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
? ? ? ? ? ?

loop_
_restr_angle_atom_site_label_1
_restr_angle_site_symmetry_1
_restr_angle_atom_site_label_2
_restr_angle_site_symmetry_2
_restr_angle_atom_site_label_3
_restr_angle_site_symmetry_3
_restr_angle_target
_restr_angle_target_weight_param
? ? ? ? ? ? ? ?

loop_
_restr_torsion_atom_site_label_1
_restr_torsion_site_symmetry_1
_restr_torsion_atom_site_label_2
_restr_torsion_site_symmetry_2
_restr_torsion_atom_site_label_3
_restr_torsion_site_symmetry_3
_restr_torsion_atom_site_label_4
_restr_torsion_site_symmetry_4
_restr_torsion_angle_target
_restr_torsion_weight_param
? ? ? ? ? ? ? ? ? ?

loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_site_symmetry_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
? ? ? ? ? ?

loop_
_restr_equal_angle_atom_site_label_1
_restr_equal_angle_site_symmetry_1
_restr_equal_angle_atom_site_label_2
_restr_equal_angle_site_symmetry_2
_restr_equal_angle_atom_site_label_3
_restr_equal_angle_site_symmetry_3
_restr_equal_angle_class_class_id
_restr_equal_angle_class_target_weight_param
? ? ? ? ? ? ? ?

loop_
_restr_equal_torsion_atom_site_label_1
_restr_equal_torsion_site_symmetry_1
_restr_equal_torsion_atom_site_label_2
_restr_equal_torsion_site_symmetry_2
_restr_equal_torsion_atom_site_label_3
_restr_equal_torsion_site_symmetry_3
_restr_equal_torsion_atom_site_label_4
_restr_equal_torsion_site_symmetry_4
_restr_equal_torsion_class_class_id
_restr_equal_torsion_class_target_weight_param
? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.90593(12) 0.43084(4) 0.04668(3) Uani 0.0382(2) 4 1 d . . .
P1 P 1.28582(9) 0.18595(3) 0.30042(3) Uani 0.02056(18) 4 1 d . . .
O1 O 1.1406(3) 0.26146(9) 0.30020(8) Uani 0.0257(5) 4 1 d . . .
O2 O 1.4658(3) 0.19048(9) 0.25245(9) Uani 0.0256(5) 4 1 d . . .
N2 N 1.1209(3) 0.11637(12) 0.28084(10) Uani 0.0241(6) 4 1 d . . .
N1 N 1.3435(3) 0.18077(11) 0.38428(11) Uani 0.0264(6) 4 1 d . . .
C1 C 0.8802(4) 0.29047(13) 0.20688(12) Uani 0.0221(7) 4 1 d . . .
C2 C 0.8244(4) 0.33150(13) 0.14702(13) Uani 0.0246(7) 4 1 d . . .
C3 C 1.0901(4) 0.29852(13) 0.23796(12) Uani 0.0203(7) 4 1 d . . .
C4 C 1.1407(4) 0.07162(13) 0.21725(12) Uani 0.0243(7) 4 1 d . . .
C5 C 1.2458(4) 0.34505(13) 0.21078(13) Uani 0.0233(7) 4 1 d . . .
C6 C 1.1890(4) 0.38546(13) 0.15089(13) Uani 0.0255(7) 4 1 d . . .
C7 C 1.4276(4) 0.10976(14) 0.41174(13) Uani 0.0289(8) 4 1 d . . .
C8 C 0.9447(5) 0.02044(16) 0.10867(15) Uani 0.0397(9) 4 1 d . . .
C9 C 1.5970(5) 0.2691(2) 0.45004(18) Uani 0.0545(12) 4 1 d . . .
C10 C 0.9777(4) 0.37835(13) 0.12040(12) Uani 0.0250(7) 4 1 d . . .
C11 C 1.0315(5) -0.05735(15) 0.12639(15) Uani 0.0368(9) 4 1 d . . .
C12 C 1.3619(4) 0.24577(14) 0.43105(13) Uani 0.0271(7) 4 1 d . . .
C13 C 1.2433(6) 0.30364(20) 0.54157(18) Uani 0.0508(12) 4 1 d . . .
C14 C 0.9334(4) 0.10124(14) 0.32368(14) Uani 0.0283(8) 4 1 d . . .
C15 C 1.2515(5) -0.05249(17) 0.16782(16) Uani 0.0394(9) 4 1 d . . .
C16 C 0.9216(5) 0.06701(15) 0.17380(15) Uani 0.0354(9) 4 1 d . . .
C17 C 1.4747(5) 0.32995(17) 0.55911(15) Uani 0.0381(9) 4 1 d . . .
C18 C 1.2320(4) -0.00588(15) 0.23350(14) Uani 0.0315(8) 4 1 d . . .
C19 C 1.2419(5) 0.23309(19) 0.49693(17) Uani 0.0477(11) 4 1 d . . .
C20 C 1.6002(6) 0.3401(2) 0.4946(2) Uani 0.0609(13) 4 1 d . . .
H1c1 H 0.774957 0.25734 0.226083 Uiso 0.0265 4 1 d . . .
H1c2 H 0.679474 0.32697 0.124575 Uiso 0.0296 4 1 d . . .
H1c4 H 1.244846 0.097133 0.189887 Uiso 0.0292 4 1 d . . .
H1c5 H 1.391191 0.34941 0.232953 Uiso 0.028 4 1 d . . .
H1c6 H 1.294934 0.41781 0.130999 Uiso 0.0306 4 1 d . . .
H1c7 H 1.40605 0.071771 0.376961 Uiso 0.0347 4 1 d . . .
H2c7 H 1.582543 0.114402 0.424464 Uiso 0.0347 4 1 d . . .
H3c7 H 1.349355 0.096381 0.451863 Uiso 0.0347 4 1 d . . .
H1c8 H 1.043966 0.044893 0.078876 Uiso 0.0476 4 1 d . . .
H2c8 H 0.803429 0.016572 0.083775 Uiso 0.0476 4 1 d . . .
H1c9 H 1.673008 0.278293 0.40852 Uiso 0.0654 4 1 d . . .
H2c9 H 1.67208 0.229661 0.47544 Uiso 0.0654 4 1 d . . .
H1c11 H 0.926425 -0.083286 0.153048 Uiso 0.0442 4 1 d . . .
H2c11 H 1.050351 -0.084703 0.084371 Uiso 0.0442 4 1 d . . .
H1c12 H 1.292682 0.285706 0.404796 Uiso 0.0325 4 1 d . . .
H1c13 H 1.161574 0.342312 0.517131 Uiso 0.0609 4 1 d . . .
H2c13 H 1.170619 0.293677 0.583562 Uiso 0.0609 4 1 d . . .
H1c14 H 0.957934 0.125123 0.367945 Uiso 0.034 4 1 d . . .
H2c14 H 0.800081 0.120291 0.300927 Uiso 0.034 4 1 d . . .
H3c14 H 0.919469 0.048387 0.330218 Uiso 0.034 4 1 d . . .
H1c15 H 1.360175 -0.03061 0.13964 Uiso 0.0473 4 1 d . . .
H2c15 H 1.301318 -0.101799 0.180254 Uiso 0.0473 4 1 d . . .
H1c16 H 0.810241 0.045491 0.201169 Uiso 0.0424 4 1 d . . .
H2c16 H 0.873365 0.116387 0.160998 Uiso 0.0424 4 1 d . . .
H1c17 H 1.470255 0.376446 0.583675 Uiso 0.0458 4 1 d . . .
H2c17 H 1.550102 0.294247 0.589006 Uiso 0.0458 4 1 d . . .
H1c18 H 1.137283 -0.030981 0.264282 Uiso 0.0378 4 1 d . . .
H2c18 H 1.374819 -0.001613 0.257383 Uiso 0.0378 4 1 d . . .
H1c19 H 1.311772 0.193117 0.52297 Uiso 0.0573 4 1 d . . .
H2c19 H 1.091784 0.218547 0.485175 Uiso 0.0573 4 1 d . . .
H1c20 H 1.750577 0.353521 0.507251 Uiso 0.0731 4 1 d . . .
H2c20 H 1.53689 0.380637 0.467735 Uiso 0.0731 4 1 d . . .


loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O2 . . 1.4701(18) ?
P1 N2 . . 1.629(2) ?
P1 N1 . . 1.640(2) ?
O1 C3 . . 1.392(3) ?
N2 C4 . . 1.477(3) ?
N2 C14 . . 1.465(3) ?
N1 C7 . . 1.459(3) ?
N1 C12 . . 1.474(3) ?
C1 C2 . . 1.395(3) ?
C1 C3 . . 1.382(3) ?
C1 H1c1 . . 0.96 ?
C2 C10 . . 1.372(4) ?
C2 H1c2 . . 0.96 ?
C3 C5 . . 1.383(3) ?
C4 C16 . . 1.532(4) ?
C4 C18 . . 1.521(4) ?
C4 H1c4 . . 0.96 ?
C5 C6 . . 1.391(3) ?
C5 H1c5 . . 0.96 ?
C6 C10 . . 1.384(3) ?
C6 H1c6 . . 0.96 ?
C7 H1c7 . . 0.96 ?
C7 H2c7 . . 0.96 ?
C7 H3c7 . . 0.96 ?
C8 C11 . . 1.522(4) ?
C8 C16 . . 1.522(4) ?
C8 H1c8 . . 0.96 ?
C8 H2c8 . . 0.96 ?
C9 C12 . . 1.509(4) ?
C9 C20 . . 1.535(6) ?
C9 H1c9 . . 0.96 ?
C9 H2c9 . . 0.96 ?
C11 C15 . . 1.517(4) ?
C11 H1c11 . . 0.96 ?
C11 H2c11 . . 0.96 ?
C12 C19 . . 1.516(4) ?
C12 H1c12 . . 0.96 ?
C13 C17 . . 1.499(4) ?
C13 C19 . . 1.530(5) ?
C13 H1c13 . . 0.96 ?
C13 H2c13 . . 0.96 ?
C14 H1c14 . . 0.96 ?
C14 H2c14 . . 0.96 ?
C14 H3c14 . . 0.96 ?
C15 C18 . . 1.528(4) ?
C15 H1c15 . . 0.96 ?
C15 H2c15 . . 0.96 ?
C16 H1c16 . . 0.96 ?
C16 H2c16 . . 0.96 ?
C17 C20 . . 1.505(5) ?
C17 H1c17 . . 0.96 ?
C17 H2c17 . . 0.96 ?
C18 H1c18 . . 0.96 ?
C18 H2c18 . . 0.96 ?
C19 H1c19 . . 0.96 ?
C19 H2c19 . . 0.96 ?
C20 H1c20 . . 0.96 ?
C20 H2c20 . . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 P1 N2 . . . 111.22(10) ?
O2 P1 N1 . . . 120.01(10) ?
N2 P1 N1 . . . 106.27(11) ?
P1 N2 C4 . . . 122.13(16) ?
P1 N2 C14 . . . 119.62(17) ?
C4 N2 C14 . . . 118.00(19) ?
P1 N1 C7 . . . 117.32(17) ?
P1 N1 C12 . . . 124.38(16) ?
C7 N1 C12 . . . 116.97(19) ?
C2 C1 C3 . . . 118.6(2) ?
C2 C1 H1c1 . . . 120.69 ?
C3 C1 H1c1 . . . 120.69 ?
C1 C2 C10 . . . 119.7(2) ?
C1 C2 H1c2 . . . 120.17 ?
C10 C2 H1c2 . . . 120.17 ?
O1 C3 C1 . . . 118.5(2) ?
O1 C3 C5 . . . 119.5(2) ?
C1 C3 C5 . . . 121.8(2) ?
N2 C4 C16 . . . 112.1(2) ?
N2 C4 C18 . . . 111.7(2) ?
N2 C4 H1c4 . . . 106.53 ?
C16 C4 C18 . . . 110.9(2) ?
C16 C4 H1c4 . . . 107.39 ?
C18 C4 H1c4 . . . 107.86 ?
C3 C5 C6 . . . 119.1(2) ?
C3 C5 H1c5 . . . 120.44 ?
C6 C5 H1c5 . . . 120.44 ?
C5 C6 C10 . . . 119.1(2) ?
C5 C6 H1c6 . . . 120.47 ?
C10 C6 H1c6 . . . 120.47 ?
N1 C7 H1c7 . . . 109.47 ?
N1 C7 H2c7 . . . 109.47 ?
N1 C7 H3c7 . . . 109.47 ?
H1c7 C7 H2c7 . . . 109.47 ?
H1c7 C7 H3c7 . . . 109.47 ?
H2c7 C7 H3c7 . . . 109.47 ?
C11 C8 C16 . . . 111.3(2) ?
C11 C8 H1c8 . . . 109.47 ?
C11 C8 H2c8 . . . 109.47 ?
C16 C8 H1c8 . . . 109.47 ?
C16 C8 H2c8 . . . 109.47 ?
H1c8 C8 H2c8 . . . 107.6 ?
C12 C9 C20 . . . 110.4(3) ?
C12 C9 H1c9 . . . 109.47 ?
C12 C9 H2c9 . . . 109.47 ?
C20 C9 H1c9 . . . 109.47 ?
C20 C9 H2c9 . . . 109.47 ?
H1c9 C9 H2c9 . . . 108.54 ?
C2 C10 C6 . . . 121.7(2) ?
C8 C11 C15 . . . 110.4(2) ?
C8 C11 H1c11 . . . 109.47 ?
C8 C11 H2c11 . . . 109.47 ?
C15 C11 H1c11 . . . 109.47 ?
C15 C11 H2c11 . . . 109.47 ?
H1c11 C11 H2c11 . . . 108.57 ?
N1 C12 C9 . . . 114.0(2) ?
N1 C12 C19 . . . 111.8(2) ?
N1 C12 H1c12 . . . 104.46 ?
C9 C12 C19 . . . 109.1(2) ?
C9 C12 H1c12 . . . 107.46 ?
C19 C12 H1c12 . . . 109.83 ?
C17 C13 C19 . . . 111.3(3) ?
C17 C13 H1c13 . . . 109.47 ?
C17 C13 H2c13 . . . 109.47 ?
C19 C13 H1c13 . . . 109.47 ?
C19 C13 H2c13 . . . 109.47 ?
H1c13 C13 H2c13 . . . 107.57 ?
N2 C14 H1c14 . . . 109.47 ?
N2 C14 H2c14 . . . 109.47 ?
N2 C14 H3c14 . . . 109.47 ?
H1c14 C14 H2c14 . . . 109.47 ?
H1c14 C14 H3c14 . . . 109.47 ?
H2c14 C14 H3c14 . . . 109.47 ?
C11 C15 C18 . . . 111.3(2) ?
C11 C15 H1c15 . . . 109.47 ?
C11 C15 H2c15 . . . 109.47 ?
C18 C15 H1c15 . . . 109.47 ?
C18 C15 H2c15 . . . 109.47 ?
H1c15 C15 H2c15 . . . 107.59 ?
C4 C16 C8 . . . 111.5(2) ?
C4 C16 H1c16 . . . 109.47 ?
C4 C16 H2c16 . . . 109.47 ?
C8 C16 H1c16 . . . 109.47 ?
C8 C16 H2c16 . . . 109.47 ?
H1c16 C16 H2c16 . . . 107.41 ?
C13 C17 C20 . . . 111.0(3) ?
C13 C17 H1c17 . . . 109.47 ?
C13 C17 H2c17 . . . 109.47 ?
C20 C17 H1c17 . . . 109.47 ?
C20 C17 H2c17 . . . 109.47 ?
H1c17 C17 H2c17 . . . 107.88 ?
C4 C18 C15 . . . 111.8(2) ?
C4 C18 H1c18 . . . 109.47 ?
C4 C18 H2c18 . . . 109.47 ?
C15 C18 H1c18 . . . 109.47 ?
C15 C18 H2c18 . . . 109.47 ?
H1c18 C18 H2c18 . . . 107 ?
C12 C19 C13 . . . 111.1(3) ?
C12 C19 H1c19 . . . 109.47 ?
C12 C19 H2c19 . . . 109.47 ?
C13 C19 H1c19 . . . 109.47 ?
C13 C19 H2c19 . . . 109.47 ?
H1c19 C19 H2c19 . . . 107.76 ?
C9 C20 C17 . . . 111.8(3) ?
C9 C20 H1c20 . . . 109.47 ?
C9 C20 H2c20 . . . 109.47 ?
C17 C20 H1c20 . . . 109.47 ?
C17 C20 H2c20 . . . 109.47 ?
H1c20 C20 H2c20 . . . 106.98 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C1 H1c1 O2 . . 1_455 0.96 2.30 3.243(3) 166.36 ?
C4 H1c4 O2 . . . 0.96 2.42 2.953(3) 114.55 ?
C12 H1c12 O1 . . . 0.96 2.22 2.807(3) 118.83 ?


#=======================================================================

# 11. STRUCTURE-FACTOR LIST


