# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_22gtu364_321_min_01_0ma
_database_code_depnum_ccdc_archive 'CCDC 2246880'
loop_
_audit_author_name
_audit_author_address
'CEYLAN '
;Gebze Technical University
Turkey
;
_audit_update_record             
;
2023-06-06 deposited with the CCDC.	2023-06-21 downloaded from the CCDC.
;
_audit_creation_date             2023-03-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H13 N O'
_chemical_formula_sum            'C11 H13 N O'
_chemical_formula_weight         175.22
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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                   9.291(3)
_cell_length_b                   13.506(5)
_cell_length_c                   15.467(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1940.9(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2512
_cell_measurement_temperature    298.96
_cell_measurement_theta_max      20.73
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4215
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1478 before and 0.0638 after correction.
The Ratio of minimum to maximum transmission is 0.5656.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.286
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12431
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.130
_diffrn_reflns_theta_max         25.130
_diffrn_reflns_theta_min         2.002
_diffrn_ambient_temperature      298.96
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.99
_diffrn_source_power             0.0495
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                2598
_reflns_number_total             3431
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.090
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 991 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.1(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3431
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0507P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1101
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C15(H15), C16(H16), C17(H17),
 C18(H18), C20(H20)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C22(H22A,H22B,H22C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.1609(2) 0.2548(2) 0.46736(17) 0.0799(9) Uani 1 1 d . . . . .
H1 H 0.089054 0.249452 0.497828 0.120 Uiso 1 1 calc R U . . .
N1 N 0.2140(3) 0.1215(2) 0.31111(18) 0.0528(7) Uani 1 1 d . . . . .
C1 C 0.1187(4) 0.2729(3) 0.3807(3) 0.0665(10) Uani 1 1 d . . . . .
H1A H 0.194787 0.308842 0.351383 0.080 Uiso 1 1 calc R U . . .
H1B H 0.033428 0.314420 0.380631 0.080 Uiso 1 1 calc R U . . .
C2 C 0.0873(4) 0.1796(3) 0.3318(3) 0.0612(10) Uani 1 1 d . . . . .
H2A H 0.022215 0.139118 0.365827 0.073 Uiso 1 1 calc R U . . .
H2B H 0.038301 0.196584 0.278433 0.073 Uiso 1 1 calc R U . . .
C3 C 0.2973(4) 0.1371(2) 0.2388(2) 0.0507(8) Uani 1 1 d . . . . .
C4 C 0.2884(4) 0.2102(3) 0.1763(2) 0.0616(10) Uani 1 1 d . . . . .
H4 H 0.219158 0.259854 0.179491 0.074 Uiso 1 1 calc R U . . .
C5 C 0.3863(4) 0.2067(3) 0.1090(2) 0.0696(11) Uani 1 1 d . . . . .
H5 H 0.382315 0.254574 0.065866 0.084 Uiso 1 1 calc R U . . .
C6 C 0.4902(4) 0.1332(3) 0.1047(3) 0.0719(11) Uani 1 1 d . . . . .
H6 H 0.554261 0.132357 0.058562 0.086 Uiso 1 1 calc R U . . .
C7 C 0.5000(4) 0.0620(3) 0.1673(3) 0.0658(10) Uani 1 1 d . . . . .
H7 H 0.570835 0.013523 0.163773 0.079 Uiso 1 1 calc R U . . .
C8 C 0.4038(3) 0.0622(3) 0.2363(2) 0.0542(9) Uani 1 1 d . . . . .
C9 C 0.3788(4) 0.0015(3) 0.3099(3) 0.0614(10) Uani 1 1 d . . . . .
H9 H 0.431881 -0.054073 0.325398 0.074 Uiso 1 1 calc R U . . .
C10 C 0.2639(4) 0.0386(3) 0.3536(2) 0.0571(9) Uani 1 1 d . . . . .
C11 C 0.1948(5) 0.0004(3) 0.4337(3) 0.0809(12) Uani 1 1 d . . . . .
H11A H 0.195519 0.051041 0.477263 0.121 Uiso 1 1 calc R U . . .
H11B H 0.247017 -0.056300 0.454236 0.121 Uiso 1 1 calc R U . . .
H11C H 0.097208 -0.018326 0.421437 0.121 Uiso 1 1 calc R U . . .
O2 O 0.4093(2) 0.2301(2) 0.55305(17) 0.0736(8) Uani 1 1 d . . . . .
H2 H 0.342747 0.251586 0.523719 0.110 Uiso 1 1 calc R U . . .
N2 N 0.4243(3) 0.3737(2) 0.70038(17) 0.0507(7) Uani 1 1 d . . . . .
C12 C 0.3601(4) 0.2109(3) 0.6374(3) 0.0652(10) Uani 1 1 d . . . . .
H12A H 0.437306 0.180748 0.670437 0.078 Uiso 1 1 calc R U . . .
H12B H 0.281354 0.163833 0.634662 0.078 Uiso 1 1 calc R U . . .
C13 C 0.3096(3) 0.3034(3) 0.6835(2) 0.0619(10) Uani 1 1 d . . . . .
H13A H 0.236296 0.335413 0.648692 0.074 Uiso 1 1 calc R U . . .
H13B H 0.265727 0.284586 0.738016 0.074 Uiso 1 1 calc R U . . .
C14 C 0.5188(3) 0.3660(2) 0.7692(2) 0.0455(8) Uani 1 1 d . . . . .
C15 C 0.5249(4) 0.2973(3) 0.8353(2) 0.0579(9) Uani 1 1 d . . . . .
H15 H 0.460054 0.245000 0.838415 0.069 Uiso 1 1 calc R U . . .
C16 C 0.6316(4) 0.3098(3) 0.8965(2) 0.0677(11) Uani 1 1 d . . . . .
H16 H 0.637996 0.264876 0.941985 0.081 Uiso 1 1 calc R U . . .
C17 C 0.7289(4) 0.3867(3) 0.8923(2) 0.0665(11) Uani 1 1 d . . . . .
H17 H 0.799932 0.392332 0.934429 0.080 Uiso 1 1 calc R U . . .
C18 C 0.7224(4) 0.4546(3) 0.8273(3) 0.0629(10) Uani 1 1 d . . . . .
H18 H 0.788017 0.506577 0.825085 0.075 Uiso 1 1 calc R U . . .
C19 C 0.6162(3) 0.4454(2) 0.7639(2) 0.0502(8) Uani 1 1 d . . . . .
C20 C 0.5761(4) 0.5008(3) 0.6892(2) 0.0582(9) Uani 1 1 d . . . . .
H20 H 0.621500 0.557745 0.669112 0.070 Uiso 1 1 calc R U . . .
C21 C 0.4604(4) 0.4562(3) 0.6523(2) 0.0545(9) Uani 1 1 d . . . . .
C22 C 0.3758(4) 0.4860(3) 0.5750(2) 0.0793(13) Uani 1 1 d . . . . .
H22A H 0.383470 0.435644 0.531454 0.119 Uiso 1 1 calc R U . . .
H22B H 0.412737 0.547332 0.552721 0.119 Uiso 1 1 calc R U . . .
H22C H 0.276664 0.494370 0.590844 0.119 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
O1 H1 0.8200 . ?
O1 C1 1.418(5) . ?
N1 C2 1.450(4) . ?
N1 C3 1.377(4) . ?
N1 C10 1.379(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.499(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.384(5) . ?
C3 C8 1.415(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.368(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.392(5) . ?
C8 C9 1.421(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.359(5) . ?
C10 C11 1.488(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
O2 H2 0.8200 . ?
O2 C12 1.406(5) . ?
N2 C13 1.451(4) . ?
N2 C14 1.384(4) . ?
N2 C21 1.381(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.514(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.381(5) . ?
C14 C19 1.405(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.379(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.363(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.396(5) . ?
C19 C20 1.427(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.358(5) . ?
C21 C22 1.487(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C3 N1 C2 123.6(3) . . ?
C3 N1 C10 108.8(3) . . ?
C10 N1 C2 127.4(3) . . ?
O1 C1 H1A 109.1 . . ?
O1 C1 H1B 109.1 . . ?
O1 C1 C2 112.6(3) . . ?
H1A C1 H1B 107.8 . . ?
C2 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
N1 C2 C1 114.1(3) . . ?
N1 C2 H2A 108.7 . . ?
N1 C2 H2B 108.7 . . ?
C1 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
N1 C3 C4 130.0(3) . . ?
N1 C3 C8 107.8(3) . . ?
C4 C3 C8 122.2(3) . . ?
C3 C4 H4 121.3 . . ?
C5 C4 C3 117.5(3) . . ?
C5 C4 H4 121.3 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(4) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 121.1(4) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.9(3) . . ?
C8 C7 H7 120.1 . . ?
C3 C8 C9 106.0(3) . . ?
C7 C8 C3 118.1(3) . . ?
C7 C8 C9 135.9(3) . . ?
C8 C9 H9 125.8 . . ?
C10 C9 C8 108.3(3) . . ?
C10 C9 H9 125.8 . . ?
N1 C10 C11 122.3(3) . . ?
C9 C10 N1 109.0(3) . . ?
C9 C10 C11 128.7(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 O2 H2 109.5 . . ?
C14 N2 C13 123.7(3) . . ?
C21 N2 C13 127.6(3) . . ?
C21 N2 C14 108.7(3) . . ?
O2 C12 H12A 109.1 . . ?
O2 C12 H12B 109.1 . . ?
O2 C12 C13 112.7(4) . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
N2 C13 C12 113.4(3) . . ?
N2 C13 H13A 108.9 . . ?
N2 C13 H13B 108.9 . . ?
C12 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
N2 C14 C19 107.8(3) . . ?
C15 C14 N2 130.2(3) . . ?
C15 C14 C19 121.9(3) . . ?
C14 C15 H15 121.5 . . ?
C16 C15 C14 117.1(3) . . ?
C16 C15 H15 121.5 . . ?
C15 C16 H16 119.0 . . ?
C17 C16 C15 122.0(3) . . ?
C17 C16 H16 119.0 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.9(4) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.3(4) . . ?
C19 C18 H18 120.3 . . ?
C14 C19 C20 106.3(3) . . ?
C18 C19 C14 118.8(3) . . ?
C18 C19 C20 134.9(4) . . ?
C19 C20 H20 125.9 . . ?
C21 C20 C19 108.3(3) . . ?
C21 C20 H20 125.9 . . ?
N2 C21 C22 121.5(4) . . ?
C20 C21 N2 108.9(3) . . ?
C20 C21 C22 129.5(4) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N1 -71.5(4) . . . . ?
N1 C3 C4 C5 -178.9(3) . . . . ?
N1 C3 C8 C7 178.9(3) . . . . ?
N1 C3 C8 C9 0.4(4) . . . . ?
C2 N1 C3 C4 4.9(5) . . . . ?
C2 N1 C3 C8 -175.4(3) . . . . ?
C2 N1 C10 C9 175.1(3) . . . . ?
C2 N1 C10 C11 -4.2(5) . . . . ?
C3 N1 C2 C1 -85.9(4) . . . . ?
C3 N1 C10 C9 0.5(4) . . . . ?
C3 N1 C10 C11 -178.7(3) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C3 C8 C9 C10 -0.1(4) . . . . ?
C4 C3 C8 C7 -1.3(5) . . . . ?
C4 C3 C8 C9 -179.8(3) . . . . ?
C4 C5 C6 C7 -0.4(6) . . . . ?
C5 C6 C7 C8 0.6(6) . . . . ?
C6 C7 C8 C3 0.3(5) . . . . ?
C6 C7 C8 C9 178.2(4) . . . . ?
C7 C8 C9 C10 -178.2(4) . . . . ?
C8 C3 C4 C5 1.4(5) . . . . ?
C8 C9 C10 N1 -0.3(4) . . . . ?
C8 C9 C10 C11 178.9(4) . . . . ?
C10 N1 C2 C1 100.3(4) . . . . ?
C10 N1 C3 C4 179.7(3) . . . . ?
C10 N1 C3 C8 -0.6(3) . . . . ?
O2 C12 C13 N2 -65.9(4) . . . . ?
N2 C14 C15 C16 -179.0(3) . . . . ?
N2 C14 C19 C18 179.4(3) . . . . ?
N2 C14 C19 C20 0.0(3) . . . . ?
C13 N2 C14 C15 -2.1(5) . . . . ?
C13 N2 C14 C19 178.9(3) . . . . ?
C13 N2 C21 C20 -178.7(3) . . . . ?
C13 N2 C21 C22 2.7(5) . . . . ?
C14 N2 C13 C12 -81.3(4) . . . . ?
C14 N2 C21 C20 0.2(4) . . . . ?
C14 N2 C21 C22 -178.3(3) . . . . ?
C14 C15 C16 C17 -0.4(5) . . . . ?
C14 C19 C20 C21 0.1(4) . . . . ?
C15 C14 C19 C18 0.2(5) . . . . ?
C15 C14 C19 C20 -179.1(3) . . . . ?
C15 C16 C17 C18 0.6(6) . . . . ?
C16 C17 C18 C19 -0.4(5) . . . . ?
C17 C18 C19 C14 0.0(5) . . . . ?
C17 C18 C19 C20 179.2(4) . . . . ?
C18 C19 C20 C21 -179.1(4) . . . . ?
C19 C14 C15 C16 0.0(5) . . . . ?
C19 C20 C21 N2 -0.2(4) . . . . ?
C19 C20 C21 C22 178.2(3) . . . . ?
C21 N2 C13 C12 97.5(4) . . . . ?
C21 N2 C14 C15 178.9(3) . . . . ?
C21 N2 C14 C19 -0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_23gtu174_321_ekt_1_2_siviazot
_database_code_depnum_ccdc_archive 'CCDC 2246881'
loop_
_audit_author_name
_audit_author_address
'Ceylan MUTLU BALCI'
;Gebze Technical University
Turkey
;
_audit_update_record             
;
2023-06-05 deposited with the CCDC.	2023-06-21 downloaded from the CCDC.
;
_audit_creation_date             2023-06-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H36 Cl3 N6 O3 P3'
_chemical_formula_sum            'C42 H36 Cl3 N6 O3 P3'
_chemical_formula_weight         872.03
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   21.743(4)
_cell_length_b                   11.673(2)
_cell_length_c                   16.814(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.289(4)
_cell_angle_gamma                90
_cell_volume                     4074.6(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1472
_cell_measurement_temperature    172.99
_cell_measurement_theta_max      18.71
_cell_measurement_theta_min      2.43
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.932
_exptl_absorpt_coefficient_mu    0.391
_exptl_absorpt_correction_T_max  0.7336
_exptl_absorpt_correction_T_min  0.6316
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1289 before and 0.0627 after correction.
The Ratio of minimum to maximum transmission is 0.8610.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1800
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 -1.00 2.00 0.0590
3.00 -1.00 1.00 0.0360
-3.00 1.00 -1.00 0.0180
-2.00 3.00 -2.00 0.0400
0.00 1.00 0.00 0.0420
-3.00 0.00 1.00 0.0540
-2.00 3.00 2.00 0.0560
3.00 0.00 -1.00 0.0790
3.00 3.00 1.00 0.0550
-3.00 -1.00 -1.00 0.0180
3.00 -1.00 -1.00 0.0600
3.00 0.00 1.00 0.0400
2.00 1.00 -2.00 0.0820
-3.00 1.00 3.00 0.0670

_exptl_crystal_size_max          0.184
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1617
_diffrn_reflns_av_unetI/netI     0.1687
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            41764
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_min         1.962
_diffrn_ambient_temperature      172.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4103
_reflns_number_total             9342
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.978
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.0017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     515
_refine_ls_number_reflns         9342
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1859
_refine_ls_R_factor_gt           0.0699
_refine_ls_restrained_S_all      0.970
_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)+(0.0812P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1537
_refine_ls_wR_factor_ref         0.1984
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C15(H15A,H15B), C16(H16A,H16B), C29(H29A,H29B),
 C30(H30A,H30B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13),
 C18(H18), C19(H19), C20(H20), C21(H21), C24(H24), C25(H25), C26(H26), C27(H27),
  C32(H32), C33(H33), C34(H34), C35(H35), C38(H38), C39(H39), C40(H40), C41(H41)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.30507(8) -0.06916(13) 0.59056(11) 0.0746(5) Uani 1 1 d . . . . .
Cl2 Cl 0.22217(6) -0.16819(10) 0.77717(8) 0.0433(4) Uani 1 1 d . . . . .
Cl3 Cl 0.10070(7) -0.02762(11) 0.50407(8) 0.0530(4) Uani 1 1 d . . . . .
P1 P 0.27805(7) 0.07024(11) 0.64311(9) 0.0404(4) Uani 1 1 d . . . . .
P2 P 0.21451(6) 0.00164(10) 0.75197(8) 0.0326(3) Uani 1 1 d . . . . .
P3 P 0.14642(6) 0.07829(10) 0.59522(8) 0.0349(3) Uani 1 1 d . . . . .
O1 O 0.33200(15) 0.1593(3) 0.6455(2) 0.0469(9) Uani 1 1 d . . . . .
O2 O 0.20637(15) 0.0553(2) 0.83264(18) 0.0344(8) Uani 1 1 d . . . . .
O3 O 0.09727(16) 0.1789(3) 0.5741(2) 0.0449(9) Uani 1 1 d . . . . .
N1 N 0.27894(18) 0.0390(3) 0.7357(2) 0.0399(10) Uani 1 1 d . . . . .
N2 N 0.14900(18) 0.0219(3) 0.6812(2) 0.0365(10) Uani 1 1 d . . . . .
N3 N 0.21270(19) 0.1201(3) 0.5830(2) 0.0405(10) Uani 1 1 d . . . . .
N4 N 0.43969(19) 0.3298(3) 0.7128(3) 0.0445(11) Uani 1 1 d . . . . .
N5 N 0.26707(18) 0.2578(3) 0.9288(2) 0.0326(9) Uani 1 1 d . . . . .
N6 N 0.06176(19) 0.4059(3) 0.5105(2) 0.0391(10) Uani 1 1 d . . . . .
C1 C 0.3976(2) 0.1337(5) 0.6976(4) 0.0533(15) Uani 1 1 d . . . . .
H1A H 0.425774 0.120266 0.661941 0.064 Uiso 1 1 calc R U . . .
H1B H 0.397339 0.063258 0.730398 0.064 Uiso 1 1 calc R U . . .
C2 C 0.4228(3) 0.2316(5) 0.7551(3) 0.0544(15) Uani 1 1 d . . . . .
H2A H 0.389820 0.254966 0.781659 0.065 Uiso 1 1 calc R U . . .
H2B H 0.461426 0.206197 0.799619 0.065 Uiso 1 1 calc R U . . .
C3 C 0.4959(2) 0.3372(4) 0.6895(3) 0.0409(12) Uani 1 1 d . . . . .
C4 C 0.5476(2) 0.2639(4) 0.7074(3) 0.0476(14) Uani 1 1 d . . . . .
H4 H 0.548619 0.197660 0.740619 0.057 Uiso 1 1 calc R U . . .
C5 C 0.5978(3) 0.2882(5) 0.6762(4) 0.0563(15) Uani 1 1 d . . . . .
H5 H 0.634076 0.238698 0.688513 0.068 Uiso 1 1 calc R U . . .
C6 C 0.5962(3) 0.3838(6) 0.6273(4) 0.0637(17) Uani 1 1 d . . . . .
H6 H 0.631124 0.397878 0.605569 0.076 Uiso 1 1 calc R U . . .
C7 C 0.5451(3) 0.4594(5) 0.6091(3) 0.0584(17) Uani 1 1 d . . . . .
H7 H 0.544788 0.525376 0.575880 0.070 Uiso 1 1 calc R U . . .
C8 C 0.4930(3) 0.4358(4) 0.6414(3) 0.0443(14) Uani 1 1 d . . . . .
C9 C 0.4322(3) 0.4906(4) 0.6356(3) 0.0488(14) Uani 1 1 d . . . . .
C10 C 0.4021(3) 0.5884(5) 0.5936(4) 0.0676(19) Uani 1 1 d . . . . .
H10 H 0.422234 0.634372 0.561888 0.081 Uiso 1 1 calc R U . . .
C11 C 0.3412(4) 0.6157(5) 0.6001(4) 0.074(2) Uani 1 1 d . . . . .
H11 H 0.319845 0.682379 0.573144 0.088 Uiso 1 1 calc R U . . .
C12 C 0.3111(3) 0.5471(6) 0.6454(4) 0.077(2) Uani 1 1 d . . . . .
H12 H 0.269814 0.568377 0.648718 0.092 Uiso 1 1 calc R U . . .
C13 C 0.3398(3) 0.4493(6) 0.6854(4) 0.0652(18) Uani 1 1 d . . . . .
H13 H 0.318902 0.402378 0.715562 0.078 Uiso 1 1 calc R U . . .
C14 C 0.4007(3) 0.4217(5) 0.6798(3) 0.0479(14) Uani 1 1 d . . . . .
C15 C 0.2547(2) 0.0491(4) 0.9128(3) 0.0384(12) Uani 1 1 d . . . . .
H15A H 0.298113 0.045562 0.905228 0.046 Uiso 1 1 calc R U . . .
H15B H 0.248277 -0.020974 0.942507 0.046 Uiso 1 1 calc R U . . .
C16 C 0.2497(2) 0.1528(4) 0.9631(3) 0.0371(12) Uani 1 1 d . . . . .
H16A H 0.204978 0.159502 0.965731 0.045 Uiso 1 1 calc R U . . .
H16B H 0.278340 0.142786 1.020655 0.045 Uiso 1 1 calc R U . . .
C17 C 0.3308(2) 0.2917(4) 0.9389(3) 0.0353(12) Uani 1 1 d . . . . .
C18 C 0.3880(2) 0.2362(4) 0.9803(3) 0.0392(12) Uani 1 1 d . . . . .
H18 H 0.388020 0.164403 1.006928 0.047 Uiso 1 1 calc R U . . .
C19 C 0.4449(2) 0.2902(4) 0.9811(3) 0.0434(13) Uani 1 1 d . . . . .
H19 H 0.484771 0.254693 1.009335 0.052 Uiso 1 1 calc R U . . .
C20 C 0.4454(3) 0.3942(4) 0.9420(4) 0.0521(15) Uani 1 1 d . . . . .
H20 H 0.485405 0.427527 0.942572 0.063 Uiso 1 1 calc R U . . .
C21 C 0.3887(3) 0.4504(4) 0.9020(3) 0.0457(13) Uani 1 1 d . . . . .
H21 H 0.389466 0.522718 0.876336 0.055 Uiso 1 1 calc R U . . .
C22 C 0.3303(2) 0.3988(4) 0.9001(3) 0.0327(11) Uani 1 1 d . . . . .
C23 C 0.2625(2) 0.4309(4) 0.8654(3) 0.0352(12) Uani 1 1 d . . . . .
C24 C 0.2323(3) 0.5278(4) 0.8243(3) 0.0420(13) Uani 1 1 d . . . . .
H24 H 0.256576 0.589427 0.812139 0.050 Uiso 1 1 calc R U . . .
C25 C 0.1656(3) 0.5324(5) 0.8013(3) 0.0482(14) Uani 1 1 d . . . . .
H25 H 0.144002 0.598521 0.773764 0.058 Uiso 1 1 calc R U . . .
C26 C 0.1299(2) 0.4416(4) 0.8180(3) 0.0386(12) Uani 1 1 d . . . . .
H26 H 0.084235 0.446239 0.800203 0.046 Uiso 1 1 calc R U . . .
C27 C 0.1590(2) 0.3457(4) 0.8596(3) 0.0379(12) Uani 1 1 d . . . . .
H27 H 0.134309 0.284508 0.871462 0.046 Uiso 1 1 calc R U . . .
C28 C 0.2257(2) 0.3413(4) 0.8837(3) 0.0337(11) Uani 1 1 d . . . . .
C29 C 0.1075(3) 0.2787(4) 0.6289(3) 0.0435(13) Uani 1 1 d . . . . .
H29A H 0.150402 0.312849 0.635154 0.052 Uiso 1 1 calc R U . . .
H29B H 0.104846 0.256935 0.684640 0.052 Uiso 1 1 calc R U . . .
C30 C 0.0554(3) 0.3613(4) 0.5880(3) 0.0463(14) Uani 1 1 d . . . . .
H30A H 0.013209 0.322598 0.577022 0.056 Uiso 1 1 calc R U . . .
H30B H 0.056306 0.425829 0.626575 0.056 Uiso 1 1 calc R U . . .
C31 C 0.0947(2) 0.5057(4) 0.5038(3) 0.0389(12) Uani 1 1 d . . . . .
C32 C 0.1273(3) 0.5836(4) 0.5646(3) 0.0467(14) Uani 1 1 d . . . . .
H32 H 0.130664 0.571624 0.621624 0.056 Uiso 1 1 calc R U . . .
C33 C 0.1542(3) 0.6776(4) 0.5398(4) 0.0503(15) Uani 1 1 d . . . . .
H33 H 0.177179 0.730894 0.580530 0.060 Uiso 1 1 calc R U . . .
C34 C 0.1490(2) 0.6974(4) 0.4565(3) 0.0468(14) Uani 1 1 d . . . . .
H34 H 0.167686 0.764283 0.441171 0.056 Uiso 1 1 calc R U . . .
C35 C 0.1172(2) 0.6211(4) 0.3964(3) 0.0419(13) Uani 1 1 d . . . . .
H35 H 0.113642 0.635222 0.339597 0.050 Uiso 1 1 calc R U . . .
C36 C 0.0898(2) 0.5219(4) 0.4191(3) 0.0334(11) Uani 1 1 d . . . . .
C37 C 0.0521(2) 0.4287(4) 0.3736(3) 0.0343(11) Uani 1 1 d . . . . .
C38 C 0.0315(2) 0.4001(4) 0.2890(3) 0.0394(12) Uani 1 1 d . . . . .
H38 H 0.042828 0.446001 0.248855 0.047 Uiso 1 1 calc R U . . .
C39 C -0.0059(2) 0.3027(5) 0.2655(3) 0.0488(14) Uani 1 1 d . . . . .
H39 H -0.020728 0.281626 0.208433 0.059 Uiso 1 1 calc R U . . .
C40 C -0.0222(2) 0.2350(4) 0.3249(4) 0.0484(14) Uani 1 1 d . . . . .
H40 H -0.048387 0.169190 0.307062 0.058 Uiso 1 1 calc R U . . .
C41 C -0.0016(2) 0.2606(4) 0.4076(4) 0.0467(14) Uani 1 1 d . . . . .
H41 H -0.012339 0.213317 0.447470 0.056 Uiso 1 1 calc R U . . .
C42 C 0.0357(2) 0.3586(4) 0.4316(3) 0.0374(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 P1 2.021(2) . ?
Cl2 P2 2.0237(17) . ?
Cl3 P3 1.9900(18) . ?
P1 O1 1.559(3) . ?
P1 N1 1.593(4) . ?
P1 N3 1.589(4) . ?
P2 O2 1.551(3) . ?
P2 N1 1.567(4) . ?
P2 N2 1.579(4) . ?
P3 O3 1.557(3) . ?
P3 N2 1.574(4) . ?
P3 N3 1.592(4) . ?
O1 C1 1.465(6) . ?
O2 C15 1.444(5) . ?
O3 C29 1.460(5) . ?
N4 C2 1.452(6) . ?
N4 C3 1.391(6) . ?
N4 C14 1.378(6) . ?
N5 C16 1.451(5) . ?
N5 C17 1.402(6) . ?
N5 C28 1.389(5) . ?
N6 C30 1.448(6) . ?
N6 C31 1.389(6) . ?
N6 C42 1.393(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.492(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.374(7) . ?
C3 C8 1.399(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.374(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(8) . ?
C6 H6 0.9500 . ?
C6 C7 1.380(8) . ?
C7 H7 0.9500 . ?
C7 C8 1.422(7) . ?
C8 C9 1.445(7) . ?
C9 C10 1.399(7) . ?
C9 C14 1.403(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.397(9) . ?
C11 H11 0.9500 . ?
C11 C12 1.394(9) . ?
C12 H12 0.9500 . ?
C12 C13 1.377(9) . ?
C13 H13 0.9500 . ?
C13 C14 1.391(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.498(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.392(6) . ?
C17 C22 1.409(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(7) . ?
C19 H19 0.9500 . ?
C19 C20 1.382(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.382(7) . ?
C21 H21 0.9500 . ?
C21 C22 1.398(6) . ?
C22 C23 1.464(7) . ?
C23 C24 1.385(6) . ?
C23 C28 1.405(6) . ?
C24 H24 0.9500 . ?
C24 C25 1.385(7) . ?
C25 H25 0.9500 . ?
C25 C26 1.390(7) . ?
C26 H26 0.9500 . ?
C26 C27 1.370(6) . ?
C27 H27 0.9500 . ?
C27 C28 1.387(6) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.491(6) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.394(7) . ?
C31 C36 1.410(6) . ?
C32 H32 0.9500 . ?
C32 C33 1.367(7) . ?
C33 H33 0.9500 . ?
C33 C34 1.390(7) . ?
C34 H34 0.9500 . ?
C34 C35 1.370(7) . ?
C35 H35 0.9500 . ?
C35 C36 1.405(6) . ?
C36 C37 1.438(6) . ?
C37 C38 1.399(6) . ?
C37 C42 1.398(6) . ?
C38 H38 0.9500 . ?
C38 C39 1.385(7) . ?
C39 H39 0.9500 . ?
C39 C40 1.399(7) . ?
C40 H40 0.9500 . ?
C40 C41 1.361(7) . ?
C41 H41 0.9500 . ?
C41 C42 1.390(7) . ?

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 Cl1 103.55(15) . . ?
O1 P1 N1 109.7(2) . . ?
O1 P1 N3 107.2(2) . . ?
N1 P1 Cl1 108.79(17) . . ?
N3 P1 Cl1 109.75(17) . . ?
N3 P1 N1 117.0(2) . . ?
O2 P2 Cl2 103.64(12) . . ?
O2 P2 N1 112.4(2) . . ?
O2 P2 N2 106.65(19) . . ?
N1 P2 Cl2 106.68(16) . . ?
N1 P2 N2 118.7(2) . . ?
N2 P2 Cl2 107.71(16) . . ?
O3 P3 Cl3 98.14(14) . . ?
O3 P3 N2 111.1(2) . . ?
O3 P3 N3 109.0(2) . . ?
N2 P3 Cl3 108.72(16) . . ?
N2 P3 N3 117.4(2) . . ?
N3 P3 Cl3 110.80(16) . . ?
C1 O1 P1 118.0(3) . . ?
C15 O2 P2 123.8(3) . . ?
C29 O3 P3 119.5(3) . . ?
P2 N1 P1 118.9(2) . . ?
P3 N2 P2 122.2(2) . . ?
P1 N3 P3 118.6(2) . . ?
C3 N4 C2 123.9(4) . . ?
C14 N4 C2 126.6(4) . . ?
C14 N4 C3 109.0(4) . . ?
C17 N5 C16 123.7(4) . . ?
C28 N5 C16 127.4(4) . . ?
C28 N5 C17 108.9(4) . . ?
C31 N6 C30 124.4(4) . . ?
C31 N6 C42 109.2(4) . . ?
C42 N6 C30 126.4(4) . . ?
O1 C1 H1A 109.7 . . ?
O1 C1 H1B 109.7 . . ?
O1 C1 C2 109.6(4) . . ?
H1A C1 H1B 108.2 . . ?
C2 C1 H1A 109.7 . . ?
C2 C1 H1B 109.7 . . ?
N4 C2 C1 112.7(4) . . ?
N4 C2 H2A 109.0 . . ?
N4 C2 H2B 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
N4 C3 C8 108.8(5) . . ?
C4 C3 N4 129.0(5) . . ?
C4 C3 C8 122.2(5) . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.7(5) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(6) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.7(6) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 120.9 . . ?
C6 C7 C8 118.2(5) . . ?
C8 C7 H7 120.9 . . ?
C3 C8 C7 118.5(5) . . ?
C3 C8 C9 106.6(5) . . ?
C7 C8 C9 134.9(5) . . ?
C10 C9 C8 132.5(6) . . ?
C10 C9 C14 120.5(6) . . ?
C14 C9 C8 106.9(5) . . ?
C9 C10 H10 121.4 . . ?
C11 C10 C9 117.2(6) . . ?
C11 C10 H10 121.4 . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.4(6) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.7(7) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 H13 121.3 . . ?
C12 C13 C14 117.5(7) . . ?
C14 C13 H13 121.3 . . ?
N4 C14 C9 108.7(5) . . ?
N4 C14 C13 129.6(6) . . ?
C13 C14 C9 121.7(6) . . ?
O2 C15 H15A 109.8 . . ?
O2 C15 H15B 109.8 . . ?
O2 C15 C16 109.4(4) . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 H15A 109.8 . . ?
C16 C15 H15B 109.8 . . ?
N5 C16 C15 112.8(4) . . ?
N5 C16 H16A 109.0 . . ?
N5 C16 H16B 109.0 . . ?
C15 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
N5 C17 C22 108.9(4) . . ?
C18 C17 N5 129.3(4) . . ?
C18 C17 C22 121.8(4) . . ?
C17 C18 H18 121.4 . . ?
C19 C18 C17 117.2(5) . . ?
C19 C18 H18 121.4 . . ?
C18 C19 H19 119.1 . . ?
C20 C19 C18 121.9(5) . . ?
C20 C19 H19 119.1 . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.1(5) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 H21 120.7 . . ?
C20 C21 C22 118.6(5) . . ?
C22 C21 H21 120.7 . . ?
C17 C22 C23 106.3(4) . . ?
C21 C22 C17 119.3(4) . . ?
C21 C22 C23 134.4(4) . . ?
C24 C23 C22 132.9(5) . . ?
C24 C23 C28 120.1(5) . . ?
C28 C23 C22 107.0(4) . . ?
C23 C24 H24 120.9 . . ?
C23 C24 C25 118.2(5) . . ?
C25 C24 H24 120.9 . . ?
C24 C25 H25 119.5 . . ?
C24 C25 C26 121.0(5) . . ?
C26 C25 H25 119.5 . . ?
C25 C26 H26 119.2 . . ?
C27 C26 C25 121.6(5) . . ?
C27 C26 H26 119.2 . . ?
C26 C27 H27 121.2 . . ?
C26 C27 C28 117.6(5) . . ?
C28 C27 H27 121.2 . . ?
N5 C28 C23 108.9(4) . . ?
C27 C28 N5 129.5(4) . . ?
C27 C28 C23 121.5(4) . . ?
O3 C29 H29A 110.6 . . ?
O3 C29 H29B 110.6 . . ?
O3 C29 C30 105.8(4) . . ?
H29A C29 H29B 108.7 . . ?
C30 C29 H29A 110.6 . . ?
C30 C29 H29B 110.6 . . ?
N6 C30 C29 112.6(4) . . ?
N6 C30 H30A 109.1 . . ?
N6 C30 H30B 109.1 . . ?
C29 C30 H30A 109.1 . . ?
C29 C30 H30B 109.1 . . ?
H30A C30 H30B 107.8 . . ?
N6 C31 C32 130.5(5) . . ?
N6 C31 C36 108.0(4) . . ?
C32 C31 C36 121.5(5) . . ?
C31 C32 H32 121.0 . . ?
C33 C32 C31 118.1(5) . . ?
C33 C32 H32 121.0 . . ?
C32 C33 H33 119.1 . . ?
C32 C33 C34 121.8(5) . . ?
C34 C33 H33 119.1 . . ?
C33 C34 H34 119.8 . . ?
C35 C34 C33 120.4(5) . . ?
C35 C34 H34 119.8 . . ?
C34 C35 H35 120.1 . . ?
C34 C35 C36 119.9(5) . . ?
C36 C35 H35 120.1 . . ?
C31 C36 C37 107.1(4) . . ?
C35 C36 C31 118.3(5) . . ?
C35 C36 C37 134.4(4) . . ?
C38 C37 C36 132.9(5) . . ?
C42 C37 C36 107.2(4) . . ?
C42 C37 C38 119.9(5) . . ?
C37 C38 H38 121.0 . . ?
C39 C38 C37 118.0(5) . . ?
C39 C38 H38 121.0 . . ?
C38 C39 H39 119.6 . . ?
C38 C39 C40 120.8(5) . . ?
C40 C39 H39 119.6 . . ?
C39 C40 H40 119.1 . . ?
C41 C40 C39 121.9(5) . . ?
C41 C40 H40 119.1 . . ?
C40 C41 H41 121.2 . . ?
C40 C41 C42 117.7(5) . . ?
C42 C41 H41 121.2 . . ?
N6 C42 C37 108.4(4) . . ?
C41 C42 N6 129.8(5) . . ?
C41 C42 C37 121.8(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 P1 O1 C1 -64.4(4) . . . . ?
Cl1 P1 N1 P2 -96.1(3) . . . . ?
Cl1 P1 N3 P3 92.8(3) . . . . ?
Cl2 P2 O2 C15 63.0(3) . . . . ?
Cl2 P2 N1 P1 108.5(2) . . . . ?
Cl2 P2 N2 P3 -121.2(2) . . . . ?
Cl3 P3 O3 C29 175.9(3) . . . . ?
Cl3 P3 N2 P2 124.0(2) . . . . ?
Cl3 P3 N3 P1 -107.0(2) . . . . ?
P1 O1 C1 C2 -126.9(4) . . . . ?
P2 O2 C15 C16 150.3(3) . . . . ?
P3 O3 C29 C30 175.9(3) . . . . ?
O1 P1 N1 P2 151.3(2) . . . . ?
O1 P1 N3 P3 -155.4(3) . . . . ?
O1 C1 C2 N4 -73.9(5) . . . . ?
O2 P2 N1 P1 -138.5(2) . . . . ?
O2 P2 N2 P3 128.0(3) . . . . ?
O2 C15 C16 N5 -67.1(5) . . . . ?
O3 P3 N2 P2 -129.1(3) . . . . ?
O3 P3 N3 P1 146.1(2) . . . . ?
O3 C29 C30 N6 -67.0(5) . . . . ?
N1 P1 O1 C1 51.6(4) . . . . ?
N1 P1 N3 P3 -31.8(4) . . . . ?
N1 P2 O2 C15 -51.8(4) . . . . ?
N1 P2 N2 P3 0.0(4) . . . . ?
N2 P2 O2 C15 176.5(3) . . . . ?
N2 P2 N1 P1 -13.2(4) . . . . ?
N2 P3 O3 C29 62.1(4) . . . . ?
N2 P3 N3 P1 18.7(4) . . . . ?
N3 P1 O1 C1 179.6(4) . . . . ?
N3 P1 N1 P2 28.9(4) . . . . ?
N3 P3 O3 C29 -68.7(4) . . . . ?
N3 P3 N2 P2 -2.7(4) . . . . ?
N4 C3 C4 C5 179.0(5) . . . . ?
N4 C3 C8 C7 -178.7(4) . . . . ?
N4 C3 C8 C9 0.2(5) . . . . ?
N5 C17 C18 C19 -179.6(5) . . . . ?
N5 C17 C22 C21 -180.0(4) . . . . ?
N5 C17 C22 C23 0.4(5) . . . . ?
N6 C31 C32 C33 -178.1(5) . . . . ?
N6 C31 C36 C35 177.1(4) . . . . ?
N6 C31 C36 C37 0.4(5) . . . . ?
C2 N4 C3 C4 -6.9(8) . . . . ?
C2 N4 C3 C8 172.6(4) . . . . ?
C2 N4 C14 C9 -172.8(5) . . . . ?
C2 N4 C14 C13 6.9(9) . . . . ?
C3 N4 C2 C1 -77.6(6) . . . . ?
C3 N4 C14 C9 -0.8(5) . . . . ?
C3 N4 C14 C13 178.9(5) . . . . ?
C3 C4 C5 C6 -0.6(8) . . . . ?
C3 C8 C9 C10 -177.3(5) . . . . ?
C3 C8 C9 C14 -0.7(5) . . . . ?
C4 C3 C8 C7 0.9(7) . . . . ?
C4 C3 C8 C9 179.8(5) . . . . ?
C4 C5 C6 C7 1.3(9) . . . . ?
C5 C6 C7 C8 -0.8(8) . . . . ?
C6 C7 C8 C3 -0.3(7) . . . . ?
C6 C7 C8 C9 -178.7(5) . . . . ?
C7 C8 C9 C10 1.3(10) . . . . ?
C7 C8 C9 C14 177.9(5) . . . . ?
C8 C3 C4 C5 -0.5(8) . . . . ?
C8 C9 C10 C11 178.4(5) . . . . ?
C8 C9 C14 N4 0.9(5) . . . . ?
C8 C9 C14 C13 -178.8(5) . . . . ?
C9 C10 C11 C12 -1.2(8) . . . . ?
C10 C9 C14 N4 178.1(4) . . . . ?
C10 C9 C14 C13 -1.7(8) . . . . ?
C10 C11 C12 C13 -0.3(9) . . . . ?
C11 C12 C13 C14 0.7(9) . . . . ?
C12 C13 C14 N4 -179.5(5) . . . . ?
C12 C13 C14 C9 0.2(8) . . . . ?
C14 N4 C2 C1 93.2(6) . . . . ?
C14 N4 C3 C4 -179.2(5) . . . . ?
C14 N4 C3 C8 0.4(5) . . . . ?
C14 C9 C10 C11 2.1(8) . . . . ?
C16 N5 C17 C18 0.7(7) . . . . ?
C16 N5 C17 C22 -178.2(4) . . . . ?
C16 N5 C28 C23 177.5(4) . . . . ?
C16 N5 C28 C27 -0.7(7) . . . . ?
C17 N5 C16 C15 -78.5(5) . . . . ?
C17 N5 C28 C23 -0.9(5) . . . . ?
C17 N5 C28 C27 -179.1(5) . . . . ?
C17 C18 C19 C20 -0.6(7) . . . . ?
C17 C22 C23 C24 176.5(5) . . . . ?
C17 C22 C23 C28 -0.9(5) . . . . ?
C18 C17 C22 C21 1.0(7) . . . . ?
C18 C17 C22 C23 -178.6(4) . . . . ?
C18 C19 C20 C21 1.7(8) . . . . ?
C19 C20 C21 C22 -1.4(8) . . . . ?
C20 C21 C22 C17 0.1(7) . . . . ?
C20 C21 C22 C23 179.6(5) . . . . ?
C21 C22 C23 C24 -3.1(9) . . . . ?
C21 C22 C23 C28 179.5(5) . . . . ?
C22 C17 C18 C19 -0.8(7) . . . . ?
C22 C23 C24 C25 -178.0(5) . . . . ?
C22 C23 C28 N5 1.1(5) . . . . ?
C22 C23 C28 C27 179.5(4) . . . . ?
C23 C24 C25 C26 -0.9(7) . . . . ?
C24 C23 C28 N5 -176.7(4) . . . . ?
C24 C23 C28 C27 1.7(7) . . . . ?
C24 C25 C26 C27 1.7(8) . . . . ?
C25 C26 C27 C28 -0.9(7) . . . . ?
C26 C27 C28 N5 177.2(4) . . . . ?
C26 C27 C28 C23 -0.8(7) . . . . ?
C28 N5 C16 C15 103.3(5) . . . . ?
C28 N5 C17 C18 179.2(5) . . . . ?
C28 N5 C17 C22 0.3(5) . . . . ?
C28 C23 C24 C25 -0.8(7) . . . . ?
C30 N6 C31 C32 -0.6(8) . . . . ?
C30 N6 C31 C36 -179.4(4) . . . . ?
C30 N6 C42 C37 179.1(4) . . . . ?
C30 N6 C42 C41 0.2(8) . . . . ?
C31 N6 C30 C29 -91.7(5) . . . . ?
C31 N6 C42 C37 0.0(5) . . . . ?
C31 N6 C42 C41 -178.9(5) . . . . ?
C31 C32 C33 C34 0.9(7) . . . . ?
C31 C36 C37 C38 179.7(5) . . . . ?
C31 C36 C37 C42 -0.4(5) . . . . ?
C32 C31 C36 C35 -1.8(7) . . . . ?
C32 C31 C36 C37 -178.5(4) . . . . ?
C32 C33 C34 C35 -1.1(8) . . . . ?
C33 C34 C35 C36 -0.2(7) . . . . ?
C34 C35 C36 C31 1.6(7) . . . . ?
C34 C35 C36 C37 177.2(5) . . . . ?
C35 C36 C37 C38 3.8(9) . . . . ?
C35 C36 C37 C42 -176.4(5) . . . . ?
C36 C31 C32 C33 0.5(7) . . . . ?
C36 C37 C38 C39 -179.1(5) . . . . ?
C36 C37 C42 N6 0.3(5) . . . . ?
C36 C37 C42 C41 179.3(4) . . . . ?
C37 C38 C39 C40 -0.3(7) . . . . ?
C38 C37 C42 N6 -179.8(4) . . . . ?
C38 C37 C42 C41 -0.8(7) . . . . ?
C38 C39 C40 C41 -0.8(8) . . . . ?
C39 C40 C41 C42 1.1(7) . . . . ?
C40 C41 C42 N6 178.5(4) . . . . ?
C40 C41 C42 C37 -0.3(7) . . . . ?
C42 N6 C30 C29 89.3(6) . . . . ?
C42 N6 C31 C32 178.5(5) . . . . ?
C42 N6 C31 C36 -0.3(5) . . . . ?
C42 C37 C38 C39 1.1(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
