# 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 2021

####################################################################### 
# 
# 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_compound7a_ML092
_database_code_depnum_ccdc_archive 'CCDC 2062043'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson'
;Saint Marys University
Canada
;
_audit_update_record             
;
2021-02-09 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

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

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H45 N4, F6 P, C H2 Cl2'
_chemical_formula_sum            'C28 H47 Cl2 F6 N4 P'
_chemical_formula_weight         655.56

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.1649(14)
_cell_length_b                   11.6494(14)
_cell_length_c                   13.3995(16)
_cell_angle_alpha                95.442(2)
_cell_angle_beta                 100.844(2)
_cell_angle_gamma                111.6480(10)
_cell_volume                     1565.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    6390
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      27.89

_exptl_crystal_description       'rectangualr prism'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             692
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.320
_shelx_estimated_absorpt_T_min   0.896
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6415
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16587
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.912
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6139
_reflns_number_gt                4474
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (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)+(0.0499P)²+0.9122P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'dual space'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6139
_refine_ls_number_parameters     530
_refine_ls_number_restraints     266
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1221
_refine_ls_wR_factor_gt          0.1113
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_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
C28A C 0.517(2) 0.8506(12) 0.3956(11) 0.062(4) Uani 0.462(3) 1 d D U P A 1
H28A H 0.442145 0.878299 0.382804 0.075 Uiso 0.462(3) 1 calc R U P A 1
H28B H 0.549492 0.851836 0.331863 0.075 Uiso 0.462(3) 1 calc R U P A 1
Cl1A Cl 0.6459(3) 0.9634(3) 0.4956(3) 0.0402(7) Uani 0.462(3) 1 d D U P A 1
Cl2A Cl 0.4533(5) 0.6961(5) 0.4139(4) 0.081(2) Uani 0.462(3) 1 d D U P A 1
C28B C 0.5441(16) 0.8547(15) 0.3885(11) 0.046(4) Uani 0.395(3) 1 d D U P B 2
H28C H 0.496715 0.890575 0.338789 0.056 Uiso 0.395(3) 1 calc R U P B 2
H28D H 0.594402 0.817532 0.352374 0.056 Uiso 0.395(3) 1 calc R U P B 2
Cl1B Cl 0.6525(8) 0.9724(8) 0.4945(6) 0.116(3) Uani 0.395(3) 1 d D U P B 2
Cl2B Cl 0.4311(6) 0.7406(5) 0.4389(5) 0.0836(17) Uani 0.395(3) 1 d D U P B 2
C28C C 0.571(5) 0.834(2) 0.390(3) 0.063(6) Uani 0.143(3) 1 d D U P C 3
H28E H 0.542508 0.843176 0.317604 0.076 Uiso 0.143(3) 1 calc R U P C 3
H28F H 0.666156 0.849177 0.403470 0.076 Uiso 0.143(3) 1 calc R U P C 3
Cl1C Cl 0.5527(19) 0.9527(14) 0.4733(11) 0.179(6) Uani 0.143(3) 1 d D U P C 3
Cl2C Cl 0.482(2) 0.6808(19) 0.4030(18) 0.129(6) Uani 0.143(3) 1 d D U P C 3
P1 P 0.67129(6) 0.89493(6) 0.14355(5) 0.02895(16) Uani 1 1 d . . . . .
F1 F 0.80971(14) 0.99666(15) 0.13379(12) 0.0532(4) Uani 1 1 d . . . . .
F2 F 0.53375(13) 0.79367(13) 0.15382(12) 0.0447(4) Uani 1 1 d . . . . .
F3A F 0.7423(16) 0.8470(15) 0.2362(10) 0.039(2) Uani 0.67(5) 1 d D . P D 1
F4A F 0.6040(15) 0.9355(8) 0.0456(10) 0.051(3) Uani 0.67(5) 1 d D . P D 1
F5A F 0.6651(14) 0.9990(12) 0.2188(12) 0.0432(18) Uani 0.67(5) 1 d D . P D 1
F6A F 0.6828(15) 0.7849(13) 0.0629(10) 0.0474(19) Uani 0.67(5) 1 d D . P D 1
F3B F 0.764(3) 0.857(3) 0.224(2) 0.040(4) Uani 0.33(5) 1 d D . P D 2
F4B F 0.5770(13) 0.9473(14) 0.073(2) 0.042(3) Uani 0.33(5) 1 d D . P D 2
F5B F 0.659(3) 0.990(2) 0.244(2) 0.039(3) Uani 0.33(5) 1 d D . P D 2
F6B F 0.675(3) 0.815(3) 0.0525(17) 0.042(3) Uani 0.33(5) 1 d D . P D 2
N1 N 0.49316(17) 0.43847(17) 0.14921(15) 0.0291(4) Uani 1 1 d . . . . .
N2 N 0.52472(18) 0.26679(18) 0.20365(16) 0.0332(5) Uani 1 1 d . . . . .
N3 N 0.12871(18) 0.13684(17) 0.24535(14) 0.0266(4) Uani 1 1 d D . . . .
H3N H 0.066(2) 0.0599(17) 0.2233(18) 0.035(7) Uiso 1 1 d D . . . .
N4 N 0.23895(19) 0.06341(17) 0.14235(16) 0.0297(4) Uani 1 1 d D . . . .
H4N H 0.285(2) 0.082(2) 0.0967(16) 0.036(7) Uiso 1 1 d D . . . .
C1 C 0.4420(2) 0.3271(2) 0.18280(17) 0.0270(5) Uani 1 1 d . . . . .
C2 C 0.3137(2) 0.2856(2) 0.19787(17) 0.0271(5) Uani 1 1 d . . . . .
H2 H 0.280498 0.348438 0.210584 0.033 Uiso 1 1 calc R U . . .
C3 C 0.2272(2) 0.1603(2) 0.19639(17) 0.0244(5) Uani 1 1 d . . . . .
C4 C 0.4060(2) 0.4947(2) 0.1014(2) 0.0343(6) Uani 1 1 d . . . . .
H4A H 0.325656 0.428931 0.056074 0.052 Uiso 1 1 calc R U . . .
H4B H 0.451862 0.554622 0.060687 0.052 Uiso 1 1 calc R U . . .
H4C H 0.381608 0.538597 0.155110 0.052 Uiso 1 1 calc R U . . .
C5 C 0.6298(2) 0.5280(2) 0.1965(2) 0.0398(6) Uani 1 1 d . . . . .
H5A H 0.628442 0.603398 0.234554 0.060 Uiso 1 1 calc R U . . .
H5B H 0.677721 0.550964 0.142401 0.060 Uiso 1 1 calc R U . . .
H5C H 0.674543 0.489280 0.244135 0.060 Uiso 1 1 calc R U . . .
C6 C 0.6205(2) 0.2675(2) 0.1425(2) 0.0414(6) Uani 1 1 d . . . . .
H6A H 0.606295 0.307744 0.082910 0.062 Uiso 1 1 calc R U . . .
H6B H 0.608446 0.180986 0.118325 0.062 Uiso 1 1 calc R U . . .
H6C H 0.710818 0.314225 0.185244 0.062 Uiso 1 1 calc R U . . .
C7 C 0.5191(3) 0.1906(3) 0.2837(2) 0.0461(7) Uani 1 1 d . . . . .
H7A H 0.463286 0.205748 0.327364 0.069 Uiso 1 1 calc R U . . .
H7B H 0.608870 0.212884 0.325998 0.069 Uiso 1 1 calc R U . . .
H7C H 0.481194 0.101624 0.251704 0.069 Uiso 1 1 calc R U . . .
C8 C 0.1115(2) 0.21415(19) 0.33191(16) 0.0245(5) Uani 1 1 d . . . . .
C9 C 0.2427(2) 0.2941(2) 0.40979(18) 0.0364(6) Uani 1 1 d . . . . .
H9A H 0.302425 0.354962 0.375903 0.044 Uiso 1 1 calc R U . . .
H9B H 0.287021 0.239748 0.436378 0.044 Uiso 1 1 calc R U . . .
C10 C 0.2140(3) 0.3647(3) 0.4998(2) 0.0496(7) Uani 1 1 d . . . . .
H10 H 0.299718 0.419078 0.550073 0.060 Uiso 1 1 calc R U . . .
C11 C 0.1259(3) 0.2696(3) 0.5547(2) 0.0498(7) Uani 1 1 d . . . . .
H11A H 0.171241 0.216308 0.581872 0.060 Uiso 1 1 calc R U . . .
H11B H 0.108805 0.314384 0.613389 0.060 Uiso 1 1 calc R U . . .
C12 C -0.0047(3) 0.1883(2) 0.47758(19) 0.0364(6) Uani 1 1 d . . . . .
H12 H -0.062481 0.125443 0.512443 0.044 Uiso 1 1 calc R U . . .
C13 C 0.0231(2) 0.1195(2) 0.38731(18) 0.0303(5) Uani 1 1 d . . . . .
H13A H -0.061742 0.065115 0.337825 0.036 Uiso 1 1 calc R U . . .
H13B H 0.068057 0.065380 0.413385 0.036 Uiso 1 1 calc R U . . .
C14 C 0.1435(3) 0.4463(3) 0.4585(2) 0.0565(8) Uani 1 1 d . . . . .
H14A H 0.126781 0.492721 0.516498 0.068 Uiso 1 1 calc R U . . .
H14B H 0.200459 0.508356 0.423752 0.068 Uiso 1 1 calc R U . . .
C15 C 0.0126(3) 0.3650(2) 0.3824(2) 0.0450(7) Uani 1 1 d . . . . .
H15 H -0.033320 0.419233 0.356013 0.054 Uiso 1 1 calc R U . . .
C16 C -0.0758(3) 0.2693(3) 0.4364(2) 0.0430(6) Uani 1 1 d . . . . .
H16A H -0.095259 0.313651 0.494028 0.052 Uiso 1 1 calc R U . . .
H16B H -0.161046 0.215824 0.386885 0.052 Uiso 1 1 calc R U . . .
C17 C 0.0399(2) 0.2959(2) 0.29209(19) 0.0335(5) Uani 1 1 d . . . . .
H17A H -0.044939 0.242785 0.242007 0.040 Uiso 1 1 calc R U . . .
H17B H 0.095357 0.357561 0.256179 0.040 Uiso 1 1 calc R U . . .
C18 C 0.1720(2) -0.07415(19) 0.13691(17) 0.0256(5) Uani 1 1 d . . . . .
C19 C 0.1773(2) -0.1119(2) 0.24318(18) 0.0313(5) Uani 1 1 d . U . . .
H19A H 0.128779 -0.074731 0.281400 0.038 Uiso 1 1 calc R U . . .
H19B H 0.270774 -0.079902 0.283311 0.038 Uiso 1 1 calc R U . . .
C20 C 0.1143(2) -0.2556(2) 0.2305(2) 0.0337(5) Uani 1 1 d . U . . .
H20 H 0.127608 -0.275124 0.301867 0.040 Uiso 1 1 calc R U . E 1
C21 C 0.1884(2) -0.3149(2) 0.17376(18) 0.0328(5) Uani 1 1 d . . . . .
H21A H 0.155547 -0.406321 0.173608 0.039 Uiso 1 1 calc R U . F 1
H21B H 0.284890 -0.276163 0.205973 0.039 Uiso 1 1 calc R U . F 1
C22A C 0.1584(6) -0.2879(6) 0.0614(6) 0.0259(14) Uani 0.5 1 d D U P G 1
H22A H 0.198023 -0.330120 0.016714 0.031 Uiso 0.5 1 calc R U P G 1
C23A C 0.2253(7) -0.1452(7) 0.0692(6) 0.0296(16) Uani 0.5 1 d D U P G 1
H23A H 0.322043 -0.117403 0.097510 0.036 Uiso 0.5 1 calc R U P G 1
H23B H 0.211537 -0.124564 -0.000924 0.036 Uiso 0.5 1 calc R U P G 1
C24A C -0.0250(7) -0.2961(7) 0.1922(5) 0.0296(14) Uani 0.5 1 d D U P G 1
H24A H -0.060528 -0.251056 0.237248 0.035 Uiso 0.5 1 calc R U P G 1
H24B H -0.069622 -0.387222 0.191198 0.035 Uiso 0.5 1 calc R U P G 1
C25A C -0.0509(5) -0.2680(5) 0.0821(5) 0.0277(12) Uani 0.5 1 d D U P G 1
H25 H -0.148814 -0.299064 0.052518 0.033 Uiso 0.5 1 calc R U P G 1
C26A C 0.0087(6) -0.3334(5) 0.0142(4) 0.0324(11) Uani 0.5 1 d D U P G 1
H26A H -0.006451 -0.313973 -0.056314 0.039 Uiso 0.5 1 calc R U P G 1
H26B H -0.034558 -0.425470 0.009173 0.039 Uiso 0.5 1 calc R U P G 1
C27A C 0.0135(8) -0.1258(7) 0.0850(7) 0.0276(17) Uani 0.5 1 d D U P G 1
H27A H -0.027722 -0.082548 0.125931 0.033 Uiso 0.5 1 calc R U P G 1
H27B H -0.001001 -0.107850 0.014040 0.033 Uiso 0.5 1 calc R U P G 1
C22B C 0.2148(6) -0.2648(7) 0.0765(6) 0.0305(15) Uani 0.5 1 d D U P G 2
H22B H 0.275477 -0.297203 0.048557 0.037 Uiso 0.5 1 calc R U P G 2
C23B C 0.2732(7) -0.1212(7) 0.0952(6) 0.0277(15) Uani 0.5 1 d D U P G 2
H23C H 0.287481 -0.091129 0.030005 0.033 Uiso 0.5 1 calc R U P G 2
H23D H 0.359802 -0.087632 0.146458 0.033 Uiso 0.5 1 calc R U P G 2
C24B C -0.0313(7) -0.3084(7) 0.1470(6) 0.0355(16) Uani 0.5 1 d D U P G 2
H24C H -0.071979 -0.401273 0.136369 0.043 Uiso 0.5 1 calc R U P G 2
H24D H -0.091187 -0.275911 0.174570 0.043 Uiso 0.5 1 calc R U P G 2
C25B C -0.0145(6) -0.2664(6) 0.0441(5) 0.0354(13) Uani 0.5 1 d D U P G 2
H25B H -0.103018 -0.299269 -0.006232 0.039 Uiso 0.5 1 calc R U P G 2
C26B C 0.0793(7) -0.3136(5) -0.0001(5) 0.0358(12) Uani 0.5 1 d D U P G 2
H26C H 0.041134 -0.406513 -0.014064 0.043 Uiso 0.5 1 calc R U P G 2
H26D H 0.089784 -0.284205 -0.066094 0.043 Uiso 0.5 1 calc R U P G 2
C27B C 0.0456(8) -0.1213(7) 0.0625(7) 0.0306(17) Uani 0.5 1 d D U P G 2
H27C H 0.057676 -0.092109 -0.003363 0.037 Uiso 0.5 1 calc R U P G 2
H27D H -0.015456 -0.089073 0.088492 0.037 Uiso 0.5 1 calc R U P G 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C28A Cl2A 1.735(12) . ?
C28A Cl1A 1.774(12) . ?
C28A H28A 0.9900 . ?
C28A H28B 0.9900 . ?
C28B Cl2B 1.752(11) . ?
C28B Cl1B 1.767(12) . ?
C28B H28C 0.9900 . ?
C28B H28D 0.9900 . ?
C28C Cl2C 1.741(17) . ?
C28C Cl1C 1.786(17) . ?
C28C H28E 0.9900 . ?
C28C H28F 0.9900 . ?
P1 F6B 1.48(2) . ?
P1 F5A 1.532(13) . ?
P1 F3B 1.57(2) . ?
P1 F4A 1.588(6) . ?
P1 F2 1.5945(14) . ?
P1 F1 1.6012(15) . ?
P1 F3A 1.603(10) . ?
P1 F4B 1.604(12) . ?
P1 F6A 1.655(12) . ?
P1 F5B 1.71(2) . ?
N1 C1 1.369(3) . ?
N1 C4 1.450(3) . ?
N1 C5 1.468(3) . ?
N2 C1 1.358(3) . ?
N2 C7 1.452(3) . ?
N2 C6 1.463(3) . ?
N3 C3 1.341(3) . ?
N3 C8 1.485(3) . ?
N3 H3N 0.888(16) . ?
N4 C3 1.344(3) . ?
N4 C18 1.485(3) . ?
N4 H4N 0.862(16) . ?
C1 C2 1.393(3) . ?
C2 C3 1.419(3) . ?
C2 H2 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
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 C17 1.526(3) . ?
C8 C9 1.528(3) . ?
C8 C13 1.539(3) . ?
C9 C10 1.544(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C14 1.523(4) . ?
C10 C11 1.536(4) . ?
C10 H10 1.0000 . ?
C11 C12 1.523(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C16 1.521(3) . ?
C12 C13 1.531(3) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.519(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C17 1.530(3) . ?
C15 C16 1.533(4) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C27B 1.444(10) . ?
C18 C23A 1.512(9) . ?
C18 C19 1.527(3) . ?
C18 C23B 1.589(9) . ?
C18 C27A 1.628(9) . ?
C19 C20 1.535(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C24A 1.420(8) . ?
C20 C21 1.517(3) . ?
C20 C24B 1.649(8) . ?
C20 H20 1.0000 . ?
C21 C22B 1.513(8) . ?
C21 C22A 1.567(8) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22A C23A 1.534(8) . ?
C22A C26A 1.536(8) . ?
C22A H22A 1.0000 . ?
C23A H23A 0.9900 . ?
C23A H23B 0.9900 . ?
C24A C25A 1.539(7) . ?
C24A H24A 0.9900 . ?
C24A H24B 0.9900 . ?
C25A C26A 1.524(7) . ?
C25A C27A 1.537(8) . ?
C25A H25 1.0000 . ?
C26A H26A 0.9900 . ?
C26A H26B 0.9900 . ?
C27A H27A 0.9900 . ?
C27A H27B 0.9900 . ?
C22B C26B 1.527(7) . ?
C22B C23B 1.530(8) . ?
C22B H22B 1.0000 . ?
C23B H23C 0.9900 . ?
C23B H23D 0.9900 . ?
C24B C25B 1.528(8) . ?
C24B H24C 0.9900 . ?
C24B H24D 0.9900 . ?
C25B C26B 1.532(8) . ?
C25B C27B 1.546(8) . ?
C25B H25B 1.0000 . ?
C26B H26C 0.9900 . ?
C26B H26D 0.9900 . ?
C27B H27C 0.9900 . ?
C27B H27D 0.9900 . ?

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
Cl2A C28A Cl1A 118.0(10) . . ?
Cl2A C28A H28A 107.8 . . ?
Cl1A C28A H28A 107.8 . . ?
Cl2A C28A H28B 107.8 . . ?
Cl1A C28A H28B 107.8 . . ?
H28A C28A H28B 107.1 . . ?
Cl2B C28B Cl1B 106.6(9) . . ?
Cl2B C28B H28C 110.4 . . ?
Cl1B C28B H28C 110.4 . . ?
Cl2B C28B H28D 110.4 . . ?
Cl1B C28B H28D 110.4 . . ?
H28C C28B H28D 108.6 . . ?
Cl2C C28C Cl1C 115.0(18) . . ?
Cl2C C28C H28E 108.5 . . ?
Cl1C C28C H28E 108.5 . . ?
Cl2C C28C H28F 108.5 . . ?
Cl1C C28C H28F 108.5 . . ?
H28E C28C H28F 107.5 . . ?
F6B P1 F3B 95.5(12) . . ?
F5A P1 F4A 92.8(6) . . ?
F6B P1 F2 92.7(12) . . ?
F5A P1 F2 93.3(6) . . ?
F3B P1 F2 97.0(12) . . ?
F4A P1 F2 93.5(5) . . ?
F6B P1 F1 87.4(12) . . ?
F5A P1 F1 86.6(6) . . ?
F3B P1 F1 82.8(12) . . ?
F4A P1 F1 86.7(5) . . ?
F2 P1 F1 179.73(10) . . ?
F5A P1 F3A 91.7(5) . . ?
F4A P1 F3A 175.4(7) . . ?
F2 P1 F3A 87.2(7) . . ?
F1 P1 F3A 92.6(7) . . ?
F6B P1 F4B 92.0(8) . . ?
F3B P1 F4B 172.4(14) . . ?
F2 P1 F4B 83.3(6) . . ?
F1 P1 F4B 96.9(6) . . ?
F5A P1 F6A 178.3(8) . . ?
F4A P1 F6A 87.7(4) . . ?
F2 P1 F6A 88.3(5) . . ?
F1 P1 F6A 91.8(5) . . ?
F3A P1 F6A 87.8(6) . . ?
F6B P1 F5B 176.2(12) . . ?
F3B P1 F5B 88.2(11) . . ?
F2 P1 F5B 86.2(9) . . ?
F1 P1 F5B 93.6(9) . . ?
F4B P1 F5B 84.2(10) . . ?
C1 N1 C4 120.38(18) . . ?
C1 N1 C5 120.42(19) . . ?
C4 N1 C5 114.38(18) . . ?
C1 N2 C7 122.6(2) . . ?
C1 N2 C6 122.2(2) . . ?
C7 N2 C6 115.0(2) . . ?
C3 N3 C8 131.12(18) . . ?
C3 N3 H3N 112.6(16) . . ?
C8 N3 H3N 116.1(16) . . ?
C3 N4 C18 131.10(18) . . ?
C3 N4 H4N 115.5(17) . . ?
C18 N4 H4N 112.8(17) . . ?
N2 C1 N1 116.16(19) . . ?
N2 C1 C2 124.4(2) . . ?
N1 C1 C2 119.4(2) . . ?
C1 C2 C3 127.4(2) . . ?
C1 C2 H2 116.3 . . ?
C3 C2 H2 116.3 . . ?
N3 C3 N4 118.91(19) . . ?
N3 C3 C2 120.44(19) . . ?
N4 C3 C2 120.59(19) . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C17 111.25(18) . . ?
N3 C8 C9 112.65(17) . . ?
C17 C8 C9 110.69(19) . . ?
N3 C8 C13 105.40(16) . . ?
C17 C8 C13 108.52(18) . . ?
C9 C8 C13 108.07(18) . . ?
C8 C9 C10 108.9(2) . . ?
C8 C9 H9A 109.9 . . ?
C10 C9 H9A 109.9 . . ?
C8 C9 H9B 109.9 . . ?
C10 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C14 C10 C11 109.5(2) . . ?
C14 C10 C9 109.8(2) . . ?
C11 C10 C9 109.6(2) . . ?
C14 C10 H10 109.3 . . ?
C11 C10 H10 109.3 . . ?
C9 C10 H10 109.3 . . ?
C12 C11 C10 108.8(2) . . ?
C12 C11 H11A 109.9 . . ?
C10 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
C10 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
C16 C12 C11 110.3(2) . . ?
C16 C12 C13 109.1(2) . . ?
C11 C12 C13 109.4(2) . . ?
C16 C12 H12 109.4 . . ?
C11 C12 H12 109.4 . . ?
C13 C12 H12 109.4 . . ?
C12 C13 C8 110.48(18) . . ?
C12 C13 H13A 109.6 . . ?
C8 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
C8 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C15 C14 C10 110.0(2) . . ?
C15 C14 H14A 109.7 . . ?
C10 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
C10 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C14 C15 C17 109.2(2) . . ?
C14 C15 C16 109.6(2) . . ?
C17 C15 C16 109.6(2) . . ?
C14 C15 H15 109.5 . . ?
C17 C15 H15 109.5 . . ?
C16 C15 H15 109.5 . . ?
C12 C16 C15 109.2(2) . . ?
C12 C16 H16A 109.8 . . ?
C15 C16 H16A 109.8 . . ?
C12 C16 H16B 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
C8 C17 C15 109.8(2) . . ?
C8 C17 H17A 109.7 . . ?
C15 C17 H17A 109.7 . . ?
C8 C17 H17B 109.7 . . ?
C15 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C27B C18 N4 109.2(4) . . ?
N4 C18 C23A 111.1(3) . . ?
C27B C18 C19 118.7(4) . . ?
N4 C18 C19 112.99(18) . . ?
C23A C18 C19 111.7(4) . . ?
C27B C18 C23B 110.7(4) . . ?
N4 C18 C23B 100.7(3) . . ?
C19 C18 C23B 102.8(3) . . ?
N4 C18 C27A 111.7(3) . . ?
C23A C18 C27A 105.6(4) . . ?
C19 C18 C27A 103.3(3) . . ?
C18 C19 C20 109.58(19) . . ?
C18 C19 H19A 109.8 . . ?
C20 C19 H19A 109.8 . . ?
C18 C19 H19B 109.8 . . ?
C20 C19 H19B 109.8 . . ?
H19A C19 H19B 108.2 . . ?
C24A C20 C21 118.7(3) . . ?
C24A C20 C19 108.2(4) . . ?
C21 C20 C19 110.81(19) . . ?
C21 C20 C24B 100.8(3) . . ?
C19 C20 C24B 108.7(3) . . ?
C24A C20 H20 106.1 . . ?
C21 C20 H20 106.1 . . ?
C19 C20 H20 106.1 . . ?
C22B C21 C20 113.9(3) . . ?
C20 C21 C22A 104.1(3) . . ?
C20 C21 H21A 110.9 . . ?
C22A C21 H21A 110.9 . . ?
C20 C21 H21B 110.9 . . ?
C22A C21 H21B 110.9 . . ?
H21A C21 H21B 108.9 . . ?
C23A C22A C26A 109.8(5) . . ?
C23A C22A C21 106.6(5) . . ?
C26A C22A C21 112.1(5) . . ?
C23A C22A H22A 109.5 . . ?
C26A C22A H22A 109.5 . . ?
C21 C22A H22A 109.5 . . ?
C18 C23A C22A 112.7(5) . . ?
C18 C23A H23A 109.0 . . ?
C22A C23A H23A 109.0 . . ?
C18 C23A H23B 109.0 . . ?
C22A C23A H23B 109.0 . . ?
H23A C23A H23B 107.8 . . ?
C20 C24A C25A 108.2(5) . . ?
C20 C24A H24A 110.1 . . ?
C25A C24A H24A 110.1 . . ?
C20 C24A H24B 110.1 . . ?
C25A C24A H24B 110.1 . . ?
H24A C24A H24B 108.4 . . ?
C26A C25A C27A 108.9(5) . . ?
C26A C25A C24A 109.9(5) . . ?
C27A C25A C24A 109.7(5) . . ?
C26A C25A H25 109.5 . . ?
C27A C25A H25 109.5 . . ?
C24A C25A H25 109.5 . . ?
C25A C26A C22A 109.2(5) . . ?
C25A C26A H26A 109.8 . . ?
C22A C26A H26A 109.8 . . ?
C25A C26A H26B 109.8 . . ?
C22A C26A H26B 109.8 . . ?
H26A C26A H26B 108.3 . . ?
C25A C27A C18 109.6(6) . . ?
C25A C27A H27A 109.8 . . ?
C18 C27A H27A 109.8 . . ?
C25A C27A H27B 109.8 . . ?
C18 C27A H27B 109.8 . . ?
H27A C27A H27B 108.2 . . ?
C21 C22B C26B 105.6(5) . . ?
C21 C22B C23B 111.8(5) . . ?
C26B C22B C23B 108.8(5) . . ?
C21 C22B H22B 110.2 . . ?
C26B C22B H22B 110.2 . . ?
C23B C22B H22B 110.2 . . ?
C22B C23B C18 108.4(5) . . ?
C22B C23B H23C 110.0 . . ?
C18 C23B H23C 110.0 . . ?
C22B C23B H23D 110.0 . . ?
C18 C23B H23D 110.0 . . ?
H23C C23B H23D 108.4 . . ?
C25B C24B C20 110.0(5) . . ?
C25B C24B H24C 109.7 . . ?
C20 C24B H24C 109.7 . . ?
C25B C24B H24D 109.7 . . ?
C20 C24B H24D 109.7 . . ?
H24C C24B H24D 108.2 . . ?
C24B C25B C26B 111.1(5) . . ?
C24B C25B C27B 108.5(6) . . ?
C26B C25B C27B 108.6(5) . . ?
C24B C25B H25B 109.5 . . ?
C26B C25B H25B 109.5 . . ?
C27B C25B H25B 109.5 . . ?
C22B C26B C25B 110.1(5) . . ?
C22B C26B H26C 109.6 . . ?
C25B C26B H26C 109.6 . . ?
C22B C26B H26D 109.6 . . ?
C25B C26B H26D 109.6 . . ?
H26C C26B H26D 108.2 . . ?
C18 C27B C25B 109.4(6) . . ?
C18 C27B H27C 109.8 . . ?
C25B C27B H27C 109.8 . . ?
C18 C27B H27D 109.8 . . ?
C25B C27B H27D 109.8 . . ?
H27C C27B H27D 108.2 . . ?

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
C7 N2 C1 N1 147.9(2) . . . . ?
C6 N2 C1 N1 -36.2(3) . . . . ?
C7 N2 C1 C2 -29.1(4) . . . . ?
C6 N2 C1 C2 146.8(2) . . . . ?
C4 N1 C1 N2 165.0(2) . . . . ?
C5 N1 C1 N2 -41.0(3) . . . . ?
C4 N1 C1 C2 -17.9(3) . . . . ?
C5 N1 C1 C2 136.1(2) . . . . ?
N2 C1 C2 C3 -27.1(4) . . . . ?
N1 C1 C2 C3 156.0(2) . . . . ?
C8 N3 C3 N4 160.3(2) . . . . ?
C8 N3 C3 C2 -22.5(3) . . . . ?
C18 N4 C3 N3 -10.1(4) . . . . ?
C18 N4 C3 C2 172.7(2) . . . . ?
C1 C2 C3 N3 156.9(2) . . . . ?
C1 C2 C3 N4 -25.9(4) . . . . ?
C3 N3 C8 C17 90.1(3) . . . . ?
C3 N3 C8 C9 -34.9(3) . . . . ?
C3 N3 C8 C13 -152.5(2) . . . . ?
N3 C8 C9 C10 -176.7(2) . . . . ?
C17 C8 C9 C10 58.1(3) . . . . ?
C13 C8 C9 C10 -60.6(3) . . . . ?
C8 C9 C10 C14 -58.5(3) . . . . ?
C8 C9 C10 C11 61.8(3) . . . . ?
C14 C10 C11 C12 59.7(3) . . . . ?
C9 C10 C11 C12 -60.8(3) . . . . ?
C10 C11 C12 C16 -60.3(3) . . . . ?
C10 C11 C12 C13 59.7(3) . . . . ?
C16 C12 C13 C8 60.2(3) . . . . ?
C11 C12 C13 C8 -60.5(3) . . . . ?
N3 C8 C13 C12 -178.72(18) . . . . ?
C17 C8 C13 C12 -59.5(2) . . . . ?
C9 C8 C13 C12 60.6(2) . . . . ?
C11 C10 C14 C15 -59.9(3) . . . . ?
C9 C10 C14 C15 60.4(3) . . . . ?
C10 C14 C15 C17 -60.5(3) . . . . ?
C10 C14 C15 C16 59.5(3) . . . . ?
C11 C12 C16 C15 60.0(3) . . . . ?
C13 C12 C16 C15 -60.1(3) . . . . ?
C14 C15 C16 C12 -59.1(3) . . . . ?
C17 C15 C16 C12 60.6(3) . . . . ?
N3 C8 C17 C15 174.84(19) . . . . ?
C9 C8 C17 C15 -59.1(2) . . . . ?
C13 C8 C17 C15 59.3(2) . . . . ?
C14 C15 C17 C8 59.5(3) . . . . ?
C16 C15 C17 C8 -60.6(3) . . . . ?
C3 N4 C18 C27B 84.3(4) . . . . ?
C3 N4 C18 C23A -176.6(4) . . . . ?
C3 N4 C18 C19 -50.1(3) . . . . ?
C3 N4 C18 C23B -159.2(4) . . . . ?
C3 N4 C18 C27A 65.8(4) . . . . ?
C27B C18 C19 C20 53.9(4) . . . . ?
N4 C18 C19 C20 -176.33(18) . . . . ?
C23A C18 C19 C20 -50.2(3) . . . . ?
C23B C18 C19 C20 -68.6(3) . . . . ?
C27A C18 C19 C20 62.8(4) . . . . ?
C18 C19 C20 C24A -71.3(3) . . . . ?
C18 C19 C20 C21 60.4(3) . . . . ?
C18 C19 C20 C24B -49.6(4) . . . . ?
C19 C20 C21 C22B -48.1(4) . . . . ?
C24B C20 C21 C22B 66.9(4) . . . . ?
C24A C20 C21 C22A 58.0(5) . . . . ?
C19 C20 C21 C22A -68.1(3) . . . . ?
C20 C21 C22A C23A 66.2(5) . . . . ?
C20 C21 C22A C26A -53.9(5) . . . . ?
N4 C18 C23A C22A -179.9(4) . . . . ?
C19 C18 C23A C22A 52.9(6) . . . . ?
C27A C18 C23A C22A -58.6(6) . . . . ?
C26A C22A C23A C18 60.6(7) . . . . ?
C21 C22A C23A C18 -60.9(6) . . . . ?
C21 C20 C24A C25A -60.8(6) . . . . ?
C19 C20 C24A C25A 66.5(5) . . . . ?
C20 C24A C25A C26A 57.5(6) . . . . ?
C20 C24A C25A C27A -62.2(6) . . . . ?
C27A C25A C26A C22A 61.8(6) . . . . ?
C24A C25A C26A C22A -58.4(6) . . . . ?
C23A C22A C26A C25A -59.4(7) . . . . ?
C21 C22A C26A C25A 58.8(6) . . . . ?
C26A C25A C27A C18 -62.4(6) . . . . ?
C24A C25A C27A C18 57.9(7) . . . . ?
N4 C18 C27A C25A -179.6(4) . . . . ?
C23A C18 C27A C25A 59.5(6) . . . . ?
C19 C18 C27A C25A -57.9(5) . . . . ?
C20 C21 C22B C26B -69.7(5) . . . . ?
C20 C21 C22B C23B 48.4(6) . . . . ?
C21 C22B C23B C18 -58.4(6) . . . . ?
C26B C22B C23B C18 57.8(7) . . . . ?
C27B C18 C23B C22B -60.3(6) . . . . ?
N4 C18 C23B C22B -175.7(4) . . . . ?
C19 C18 C23B C22B 67.5(5) . . . . ?
C21 C20 C24B C25B -59.0(5) . . . . ?
C19 C20 C24B C25B 57.5(6) . . . . ?
C20 C24B C25B C26B 58.5(7) . . . . ?
C20 C24B C25B C27B -60.8(7) . . . . ?
C21 C22B C26B C25B 59.6(6) . . . . ?
C23B C22B C26B C25B -60.5(7) . . . . ?
C24B C25B C26B C22B -58.5(6) . . . . ?
C27B C25B C26B C22B 60.8(7) . . . . ?
N4 C18 C27B C25B 171.3(4) . . . . ?
C19 C18 C27B C25B -57.2(6) . . . . ?
C23B C18 C27B C25B 61.3(7) . . . . ?
C24B C25B C27B C18 59.2(7) . . . . ?
C26B C25B C27B C18 -61.7(7) . . . . ?

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
N3 H3N F1 0.888(16) 2.68(2) 3.291(2) 127.3(19) 1_445 yes
N3 H3N H27A^a 0.888(16) 1.83(2) 2.650(9) 153(2) . yes
N3 H3N H27D^b 0.888(16) 2.17(2) 2.913(9) 140(2) . yes
N4 H4N F4A^a 0.862(16) 2.50(3) 3.33(2) 162(2) 2_665 yes
N4 H4N F6A^a 0.862(16) 2.76(3) 3.484(15) 143(2) 2_665 yes
N4 H4N F6B^b 0.862(16) 2.46(3) 3.23(3) 149(2) 2_665 yes

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_compound8b_ML108
_database_code_depnum_ccdc_archive 'CCDC 2062046'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson'
;Saint Marys University
Canada
;
_audit_update_record             
;
2021-02-09 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

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

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H22 N3, F6 P'
_chemical_formula_sum            'C12 H22 F6 N3 P'
_chemical_formula_weight         353.29

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.0339(11)
_cell_length_b                   13.7156(19)
_cell_length_c                   15.213(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.7100(10)
_cell_angle_gamma                90
_cell_volume                     1635.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    9152
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      28.87

_exptl_crystal_description       'thick rod'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.227
_shelx_estimated_absorpt_T_min   0.895
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7024
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19599
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.022
_diffrn_reflns_theta_max         28.955
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4095
_reflns_number_gt                3268
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (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)+(0.0613P)²+0.5658P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'dual space'
_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_number_reflns         4095
_refine_ls_number_parameters     415
_refine_ls_number_restraints     857
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.1102
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.082
_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
P1 P 0.19263(6) 0.14600(3) 0.32225(3) 0.03479(14) Uani 1 1 d . . . . .
F1A F 0.0980(12) 0.1428(8) 0.2172(4) 0.0500(17) Uani 0.422(9) 1 d D U P A 1
F2A F 0.2831(12) 0.1443(7) 0.4249(4) 0.084(2) Uani 0.422(9) 1 d D U P A 1
F3A F 0.2761(13) 0.2428(6) 0.3051(8) 0.077(2) Uani 0.422(9) 1 d D U P A 1
F4A F 0.0924(12) 0.0462(6) 0.3393(7) 0.064(2) Uani 0.422(9) 1 d D U P A 1
F5A F 0.0358(10) 0.2048(4) 0.3451(5) 0.0642(16) Uani 0.422(9) 1 d D U P A 1
F6A F 0.3420(8) 0.0854(6) 0.2990(5) 0.0755(18) Uani 0.422(9) 1 d D U P A 1
F1B F 0.1638(17) 0.1276(9) 0.2215(7) 0.070(2) Uani 0.239(6) 1 d D U P A 2
F2B F 0.1873(14) 0.1663(7) 0.4285(4) 0.070(2) Uani 0.239(6) 1 d D U P A 2
F3B F 0.223(2) 0.2575(9) 0.3183(11) 0.064(3) Uani 0.239(6) 1 d D U P A 2
F4B F 0.132(3) 0.0417(10) 0.3454(13) 0.064(3) Uani 0.239(6) 1 d D U P A 2
F5B F -0.0168(9) 0.1771(8) 0.3047(7) 0.068(2) Uani 0.239(6) 1 d D U P A 2
F6B F 0.3740(10) 0.1206(8) 0.3462(8) 0.086(2) Uani 0.239(6) 1 d D U P A 2
F1C F 0.075(2) 0.1369(14) 0.2251(9) 0.073(4) Uani 0.249(8) 1 d D U P A 3
F2C F 0.3364(17) 0.1582(12) 0.4106(8) 0.091(3) Uani 0.249(8) 1 d D U P A 3
F3C F 0.2352(16) 0.2579(9) 0.2933(9) 0.041(2) Uani 0.249(8) 1 d D U P A 3
F4C F 0.1951(16) 0.0332(6) 0.3231(8) 0.076(3) Uani 0.249(8) 1 d D U P A 3
F5C F 0.0534(14) 0.1683(11) 0.3588(8) 0.086(2) Uani 0.249(8) 1 d D U P A 3
F6C F 0.3737(10) 0.1269(7) 0.2749(7) 0.072(2) Uani 0.249(8) 1 d D U P A 3
F1D F 0.201(2) 0.1824(13) 0.2312(9) 0.068(3) Uani 0.092(2) 1 d D U P A 4
F2D F 0.182(3) 0.1062(14) 0.4226(10) 0.077(3) Uani 0.092(2) 1 d D U P A 4
F3D F 0.0074(18) 0.1040(13) 0.2881(12) 0.074(3) Uani 0.092(2) 1 d D U P A 4
F4D F 0.3740(19) 0.1918(15) 0.3693(14) 0.079(3) Uani 0.092(2) 1 d D U P A 4
F5D F 0.108(3) 0.2436(12) 0.3457(12) 0.072(3) Uani 0.092(2) 1 d D U P A 4
F6D F 0.267(3) 0.0414(13) 0.3033(12) 0.063(4) Uani 0.092(2) 1 d D U P A 4
N1 N 0.75600(15) 0.51981(9) 0.49815(8) 0.0274(3) Uani 1 1 d . . . . .
N2 N 0.73403(16) 0.17043(9) 0.50702(8) 0.0279(3) Uani 1 1 d . . . . .
N3 N 0.85422(15) 0.42954(9) 0.39191(8) 0.0265(3) Uani 1 1 d . . . . .
C1 C 0.78121(16) 0.43183(10) 0.46688(9) 0.0240(3) Uani 1 1 d . . . . .
C2 C 0.74823(17) 0.34578(10) 0.51093(9) 0.0249(3) Uani 1 1 d . . . . .
H2 H 0.704777 0.350330 0.564037 0.030 Uiso 1 1 calc R U . . .
C3 C 0.77799(17) 0.25520(10) 0.47821(9) 0.0248(3) Uani 1 1 d . . . . .
H3 H 0.835944 0.253748 0.430108 0.030 Uiso 1 1 calc R U . . .
C4 C 0.7060(2) 0.53217(12) 0.58431(11) 0.0346(3) Uani 1 1 d . . . . .
H4A H 0.591551 0.505081 0.579908 0.052 Uiso 1 1 calc R U . . .
H4B H 0.705428 0.601713 0.599022 0.052 Uiso 1 1 calc R U . . .
H4C H 0.787420 0.497987 0.631713 0.052 Uiso 1 1 calc R U . . .
C5 C 0.7777(2) 0.60863(11) 0.44837(11) 0.0351(3) Uani 1 1 d . . . . .
H5A H 0.862829 0.597119 0.412212 0.053 Uiso 1 1 calc R U . . .
H5B H 0.816309 0.661824 0.491000 0.053 Uiso 1 1 calc R U . . .
H5C H 0.668608 0.626374 0.408609 0.053 Uiso 1 1 calc R U . . .
C6 C 0.6358(2) 0.16315(12) 0.57693(11) 0.0364(4) Uani 1 1 d . . . . .
H6A H 0.689266 0.203606 0.628550 0.055 Uiso 1 1 calc R U . . .
H6B H 0.633349 0.095100 0.596238 0.055 Uiso 1 1 calc R U . . .
H6C H 0.519020 0.185860 0.552929 0.055 Uiso 1 1 calc R U . . .
C7 C 0.7633(2) 0.07953(11) 0.46271(11) 0.0378(4) Uani 1 1 d . . . . .
H7A H 0.653434 0.050941 0.433137 0.057 Uiso 1 1 calc R U . . .
H7B H 0.825431 0.033794 0.507675 0.057 Uiso 1 1 calc R U . . .
H7C H 0.830624 0.092878 0.417608 0.057 Uiso 1 1 calc R U . . .
C8A C 0.7808(10) 0.3998(9) 0.3135(5) 0.0250(14) Uani 0.732(6) 1 d D . P B 1
C9A C 0.8594(10) 0.3944(7) 0.2324(5) 0.0317(12) Uani 0.732(6) 1 d D . P B 1
H9A H 0.957828 0.349161 0.243419 0.038 Uiso 0.732(6) 1 calc R U P B 1
H9B H 0.898420 0.459550 0.217420 0.038 Uiso 0.732(6) 1 calc R U P B 1
C10A C 0.7165(6) 0.3566(3) 0.1562(3) 0.0364(9) Uani 0.732(6) 1 d D . P B 1
H10A H 0.763336 0.315417 0.114012 0.044 Uiso 0.732(6) 1 calc R U P B 1
H10B H 0.652337 0.411418 0.122311 0.044 Uiso 0.732(6) 1 calc R U P B 1
C11A C 0.6015(3) 0.2966(2) 0.20402(16) 0.0368(7) Uani 0.732(6) 1 d D . P B 1
H11A H 0.652965 0.232743 0.224775 0.044 Uiso 0.732(6) 1 calc R U P B 1
H11B H 0.486581 0.286425 0.165202 0.044 Uiso 0.732(6) 1 calc R U P B 1
C12A C 0.5964(10) 0.3670(7) 0.2853(4) 0.0367(17) Uani 0.732(6) 1 d D . P B 1
H12A H 0.519153 0.422936 0.265957 0.044 Uiso 0.732(6) 1 calc R U P B 1
H12B H 0.559797 0.332118 0.334823 0.044 Uiso 0.732(6) 1 calc R U P B 1
C8B C 0.758(3) 0.402(2) 0.3159(11) 0.022(3) Uani 0.268(6) 1 d D . P B 2
C9B C 0.863(2) 0.402(2) 0.2445(13) 0.029(3) Uani 0.268(6) 1 d D . P B 2
H9C H 0.978927 0.376794 0.268525 0.035 Uiso 0.268(6) 1 calc R U P B 2
H9D H 0.871474 0.469297 0.221306 0.035 Uiso 0.268(6) 1 calc R U P B 2
C10B C 0.7622(13) 0.3355(9) 0.1703(8) 0.032(2) Uani 0.268(6) 1 d D . P B 2
H10C H 0.781104 0.352778 0.110031 0.039 Uiso 0.268(6) 1 calc R U P B 2
H10D H 0.790075 0.265876 0.182890 0.039 Uiso 0.268(6) 1 calc R U P B 2
C11B C 0.5815(8) 0.3601(7) 0.1794(4) 0.038(2) Uani 0.268(6) 1 d D . P B 2
H11C H 0.498653 0.311941 0.146796 0.046 Uiso 0.268(6) 1 calc R U P B 2
H11D H 0.547806 0.425905 0.155185 0.046 Uiso 0.268(6) 1 calc R U P B 2
C12B C 0.589(2) 0.3561(16) 0.2823(10) 0.027(3) Uani 0.268(6) 1 d D . P B 2
H12C H 0.496225 0.394609 0.298918 0.032 Uiso 0.268(6) 1 calc R U P B 2
H12D H 0.585153 0.288292 0.304132 0.032 Uiso 0.268(6) 1 calc R U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 F5C 1.389(10) . ?
P1 F6B 1.464(7) . ?
P1 F1D 1.488(12) . ?
P1 F1B 1.520(10) . ?
P1 F3A 1.536(8) . ?
P1 F4C 1.547(9) . ?
P1 F3B 1.552(11) . ?
P1 F6A 1.563(4) . ?
P1 F2A 1.572(6) . ?
P1 F3D 1.574(13) . ?
P1 F1C 1.574(13) . ?
P1 F5D 1.577(14) . ?
N1 C1 1.3288(18) . ?
N1 C4 1.4630(19) . ?
N1 C5 1.4650(19) . ?
N2 C3 1.3178(18) . ?
N2 C6 1.4604(18) . ?
N2 C7 1.4607(19) . ?
N3 C8A 1.276(6) . ?
N3 C8B 1.297(16) . ?
N3 C1 1.3930(17) . ?
C1 C2 1.4108(19) . ?
C2 C3 1.3788(19) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8A C9A 1.507(6) . ?
C8A C12A 1.516(6) . ?
C9A C10A 1.530(6) . ?
C9A H9A 0.9900 . ?
C9A H9B 0.9900 . ?
C10A C11A 1.535(5) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A C12A 1.577(6) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C8B C12B 1.483(14) . ?
C8B C9B 1.511(14) . ?
C9B C10B 1.539(14) . ?
C9B H9C 0.9900 . ?
C9B H9D 0.9900 . ?
C10B C11B 1.527(10) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C11B C12B 1.554(13) . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?

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
F6B P1 F1B 97.7(5) . . ?
F5C P1 F4C 103.1(6) . . ?
F6B P1 F3B 95.1(7) . . ?
F1B P1 F3B 96.6(7) . . ?
F3A P1 F6A 92.0(4) . . ?
F3A P1 F2A 93.3(5) . . ?
F6A P1 F2A 90.4(4) . . ?
F1D P1 F3D 92.9(9) . . ?
F5C P1 F1C 91.4(8) . . ?
F4C P1 F1C 86.1(8) . . ?
F1D P1 F5D 92.1(9) . . ?
F3D P1 F5D 87.8(9) . . ?
C1 N1 C4 121.30(12) . . ?
C1 N1 C5 121.69(12) . . ?
C4 N1 C5 117.02(12) . . ?
C3 N2 C6 121.99(12) . . ?
C3 N2 C7 121.16(12) . . ?
C6 N2 C7 116.44(12) . . ?
C8A N3 C1 125.5(4) . . ?
C8B N3 C1 117.5(9) . . ?
N1 C1 N3 116.00(12) . . ?
N1 C1 C2 122.02(12) . . ?
N3 C1 C2 121.81(12) . . ?
C3 C2 C1 121.11(12) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
N2 C3 C2 126.47(13) . . ?
N2 C3 H3 116.8 . . ?
C2 C3 H3 116.8 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8A C9A 126.2(5) . . ?
N3 C8A C12A 125.5(6) . . ?
C9A C8A C12A 108.3(5) . . ?
C8A C9A C10A 104.9(4) . . ?
C8A C9A H9A 110.8 . . ?
C10A C9A H9A 110.8 . . ?
C8A C9A H9B 110.8 . . ?
C10A C9A H9B 110.8 . . ?
H9A C9A H9B 108.9 . . ?
C9A C10A C11A 104.7(4) . . ?
C9A C10A H10A 110.8 . . ?
C11A C10A H10A 110.8 . . ?
C9A C10A H10B 110.8 . . ?
C11A C10A H10B 110.8 . . ?
H10A C10A H10B 108.9 . . ?
C10A C11A C12A 99.5(4) . . ?
C10A C11A H11A 111.9 . . ?
C12A C11A H11A 111.9 . . ?
C10A C11A H11B 111.9 . . ?
C12A C11A H11B 111.9 . . ?
H11A C11A H11B 109.6 . . ?
C8A C12A C11A 102.2(5) . . ?
C8A C12A H12A 111.3 . . ?
C11A C12A H12A 111.3 . . ?
C8A C12A H12B 111.3 . . ?
C11A C12A H12B 111.3 . . ?
H12A C12A H12B 109.2 . . ?
N3 C8B C12B 138.7(15) . . ?
N3 C8B C9B 109.0(14) . . ?
C12B C8B C9B 111.6(12) . . ?
C8B C9B C10B 103.8(12) . . ?
C8B C9B H9C 111.0 . . ?
C10B C9B H9C 111.0 . . ?
C8B C9B H9D 111.0 . . ?
C10B C9B H9D 111.0 . . ?
H9C C9B H9D 109.0 . . ?
C11B C10B C9B 99.0(10) . . ?
C11B C10B H10C 112.0 . . ?
C9B C10B H10C 112.0 . . ?
C11B C10B H10D 112.0 . . ?
C9B C10B H10D 112.0 . . ?
H10C C10B H10D 109.6 . . ?
C10B C11B C12B 104.9(9) . . ?
C10B C11B H11C 110.8 . . ?
C12B C11B H11C 110.8 . . ?
C10B C11B H11D 110.8 . . ?
C12B C11B H11D 110.8 . . ?
H11C C11B H11D 108.8 . . ?
C8B C12B C11B 99.3(10) . . ?
C8B C12B H12C 111.9 . . ?
C11B C12B H12C 111.9 . . ?
C8B C12B H12D 111.9 . . ?
C11B C12B H12D 111.9 . . ?
H12C C12B H12D 109.6 . . ?

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
C4 N1 C1 N3 -170.17(12) . . . . ?
C5 N1 C1 N3 9.52(19) . . . . ?
C4 N1 C1 C2 5.2(2) . . . . ?
C5 N1 C1 C2 -175.14(13) . . . . ?
C8A N3 C1 N1 -113.8(8) . . . . ?
C8B N3 C1 N1 -110.4(17) . . . . ?
C8A N3 C1 C2 70.9(8) . . . . ?
C8B N3 C1 C2 74.3(18) . . . . ?
N1 C1 C2 C3 -178.89(13) . . . . ?
N3 C1 C2 C3 -3.8(2) . . . . ?
C6 N2 C3 C2 3.6(2) . . . . ?
C7 N2 C3 C2 176.00(14) . . . . ?
C1 C2 C3 N2 -171.53(13) . . . . ?
C1 N3 C8A C9A -178.3(8) . . . . ?
C1 N3 C8A C12A 4.0(16) . . . . ?
N3 C8A C9A C10A -178.6(11) . . . . ?
C12A C8A C9A C10A -0.5(11) . . . . ?
C8A C9A C10A C11A -27.3(9) . . . . ?
C9A C10A C11A C12A 43.0(6) . . . . ?
N3 C8A C12A C11A -154.9(10) . . . . ?
C9A C8A C12A C11A 27.1(10) . . . . ?
C10A C11A C12A C8A -42.3(7) . . . . ?
C1 N3 C8B C12B -11(5) . . . . ?
C1 N3 C8B C9B -178.9(17) . . . . ?
N3 C8B C9B C10B 160(2) . . . . ?
C12B C8B C9B C10B -11(3) . . . . ?
C8B C9B C10B C11B 35(2) . . . . ?
C9B C10B C11B C12B -46.6(16) . . . . ?
N3 C8B C12B C11B 175(4) . . . . ?
C9B C8B C12B C11B -17(3) . . . . ?
C10B C11B C12B C8B 39(2) . . . . ?

_refine_diff_density_max         0.371
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_compound11_ML115
_database_code_depnum_ccdc_archive 'CCDC 2062049'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson'
;Saint Marys University
Canada
;
_audit_update_record             
;
2021-02-09 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

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

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H18 N3, F6 P'
_chemical_formula_sum            'C13 H18 F6 N3 P'
_chemical_formula_weight         361.27

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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'
'-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                   19.8863(12)
_cell_length_b                   10.6006(6)
_cell_length_c                   14.2336(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.0370(10)
_cell_angle_gamma                90
_cell_volume                     2998.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    9411
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      28.67

_exptl_crystal_description       'thick plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.325
_exptl_crystal_size_min          0.225
_exptl_absorpt_coefficient_mu    0.250
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6915
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17775
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.049
_diffrn_reflns_theta_max         28.868
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3748
_reflns_number_gt                3128
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (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)+(0.0490P)²+2.7104P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'dual space'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3748
_refine_ls_number_parameters     279
_refine_ls_number_restraints     99
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.1008
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.075
_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
P1A P 0.33145(7) 0.94357(10) 0.12462(8) 0.0177(3) Uani 0.766(9) 1 d D U P A 1
F1A F 0.30340(17) 0.8566(3) 0.2058(2) 0.0391(7) Uani 0.766(9) 1 d D U P A 1
F2A F 0.36150(19) 1.0329(4) 0.0466(2) 0.0434(7) Uani 0.766(9) 1 d D U P A 1
F3A F 0.36792(17) 0.8245(3) 0.0794(2) 0.0360(6) Uani 0.766(9) 1 d D U P A 1
F4A F 0.29724(16) 1.0626(2) 0.17248(16) 0.0412(6) Uani 0.766(9) 1 d D U P A 1
F5A F 0.26594(10) 0.9165(3) 0.06334(17) 0.0483(7) Uani 0.766(9) 1 d D U P A 1
F6A F 0.39847(10) 0.9694(3) 0.18989(17) 0.0492(7) Uani 0.766(9) 1 d D U P A 1
P1B P 0.3290(4) 0.9438(7) 0.1225(5) 0.060(2) Uani 0.234(9) 1 d D U P A 2
F1B F 0.3114(8) 0.8616(13) 0.2111(8) 0.074(4) Uani 0.234(9) 1 d D U P A 2
F2B F 0.3439(7) 1.0152(13) 0.0253(8) 0.057(3) Uani 0.234(9) 1 d D U P A 2
F3B F 0.3823(7) 0.8364(13) 0.1012(11) 0.065(4) Uani 0.234(9) 1 d D U P A 2
F4B F 0.2746(5) 1.0479(9) 0.1402(12) 0.069(3) Uani 0.234(9) 1 d D U P A 2
F5B F 0.2755(7) 0.8665(11) 0.0601(9) 0.087(3) Uani 0.234(9) 1 d D U P A 2
F6B F 0.3819(6) 1.0196(12) 0.1761(7) 0.094(3) Uani 0.234(9) 1 d D U P A 2
N1 N 0.33438(6) 0.45524(11) 0.12708(8) 0.0235(3) Uani 1 1 d . . . . .
N2 N 0.55230(6) 0.26078(12) 0.11398(9) 0.0256(3) Uani 1 1 d . . . . .
N3 N 0.43055(6) 0.57676(11) 0.13322(8) 0.0216(2) Uani 1 1 d . . . . .
H3N H 0.4072(9) 0.6409(18) 0.1346(13) 0.032 Uiso 1 1 d . U . . .
C1 C 0.40164(7) 0.46131(13) 0.12545(9) 0.0203(3) Uani 1 1 d . . . . .
C2 C 0.44378(7) 0.35523(13) 0.11961(9) 0.0220(3) Uani 1 1 d . . . . .
H2 H 0.423968 0.273737 0.116090 0.026 Uiso 1 1 calc R U . . .
C3 C 0.51361(7) 0.36569(13) 0.11882(9) 0.0214(3) Uani 1 1 d . . . . .
C4 C 0.29386(7) 0.56760(14) 0.14467(11) 0.0280(3) Uani 1 1 d . . . . .
H4A H 0.312808 0.612514 0.199663 0.042 Uiso 1 1 calc R U . . .
H4B H 0.247515 0.542316 0.156460 0.042 Uiso 1 1 calc R U . . .
H4C H 0.294141 0.623161 0.089653 0.042 Uiso 1 1 calc R U . . .
C5 C 0.29699(7) 0.33881(14) 0.10869(11) 0.0280(3) Uani 1 1 d . . . . .
H5A H 0.325583 0.278733 0.076278 0.042 Uiso 1 1 calc R U . . .
H5B H 0.256866 0.357274 0.069102 0.042 Uiso 1 1 calc R U . . .
H5C H 0.283403 0.302248 0.168344 0.042 Uiso 1 1 calc R U . . .
C6 C 0.52078(8) 0.13875(14) 0.09374(12) 0.0320(3) Uani 1 1 d . . . . .
H6A H 0.501337 0.105523 0.151004 0.048 Uiso 1 1 calc R U . . .
H6B H 0.554698 0.079699 0.071677 0.048 Uiso 1 1 calc R U . . .
H6C H 0.485187 0.149218 0.044970 0.048 Uiso 1 1 calc R U . . .
C7 C 0.62018(7) 0.24845(16) 0.15793(11) 0.0326(3) Uani 1 1 d . . . . .
H7A H 0.653387 0.242790 0.108860 0.049 Uiso 1 1 calc R U . . .
H7B H 0.622329 0.172031 0.196669 0.049 Uiso 1 1 calc R U . . .
H7C H 0.629961 0.322317 0.197493 0.049 Uiso 1 1 calc R U . . .
C8 C 0.49946(7) 0.59550(13) 0.13080(9) 0.0218(3) Uani 1 1 d . . . . .
C9 C 0.52335(7) 0.72007(14) 0.13681(10) 0.0270(3) Uani 1 1 d . . . . .
H9 H 0.492988 0.787873 0.145658 0.032 Uiso 1 1 calc R U . . .
C10 C 0.59100(8) 0.74306(15) 0.12980(11) 0.0317(3) Uani 1 1 d . . . . .
H10 H 0.607847 0.826631 0.135862 0.038 Uiso 1 1 calc R U . . .
C11 C 0.63481(8) 0.64333(16) 0.11376(11) 0.0315(3) Uani 1 1 d . . . . .
H11 H 0.681297 0.659964 0.106631 0.038 Uiso 1 1 calc R U . . .
C12 C 0.61170(7) 0.52113(15) 0.10809(10) 0.0274(3) Uani 1 1 d . . . . .
H12 H 0.642247 0.454855 0.095523 0.033 Uiso 1 1 calc R U . . .
C13 C 0.54299(7) 0.49271(13) 0.12073(9) 0.0219(3) 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
P1A F5A 1.568(2) . ?
P1A F2A 1.592(3) . ?
P1A F1A 1.595(2) . ?
P1A F4A 1.597(2) . ?
P1A F3A 1.603(3) . ?
P1A F6A 1.621(2) . ?
P1B F6B 1.510(9) . ?
P1B F4B 1.571(9) . ?
P1B F1B 1.583(11) . ?
P1B F5B 1.589(10) . ?
P1B F3B 1.592(11) . ?
P1B F2B 1.613(11) . ?
N1 C1 1.3401(17) . ?
N1 C5 1.4599(17) . ?
N1 C4 1.4647(17) . ?
N2 C3 1.3554(17) . ?
N2 C6 1.4616(19) . ?
N2 C7 1.4732(18) . ?
N3 C1 1.3549(17) . ?
N3 C8 1.3863(18) . ?
N3 H3N 0.824(19) . ?
C1 C2 1.4066(19) . ?
C2 C3 1.3937(19) . ?
C2 H2 0.9500 . ?
C3 C13 1.4676(19) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
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 C13 1.402(2) . ?
C8 C9 1.4050(19) . ?
C9 C10 1.374(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.394(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.4168(19) . ?
C12 H12 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
F5A P1A F2A 92.64(15) . . ?
F5A P1A F1A 89.55(17) . . ?
F2A P1A F1A 177.7(2) . . ?
F5A P1A F4A 91.35(12) . . ?
F2A P1A F4A 90.21(18) . . ?
F1A P1A F4A 89.00(14) . . ?
F5A P1A F3A 90.64(15) . . ?
F2A P1A F3A 90.12(19) . . ?
F1A P1A F3A 90.59(17) . . ?
F4A P1A F3A 177.96(16) . . ?
F5A P1A F6A 178.63(14) . . ?
F2A P1A F6A 88.73(15) . . ?
F1A P1A F6A 89.09(17) . . ?
F4A P1A F6A 88.65(11) . . ?
F3A P1A F6A 89.35(14) . . ?
F6B P1B F4B 90.9(6) . . ?
F6B P1B F1B 93.4(8) . . ?
F4B P1B F1B 94.9(8) . . ?
F6B P1B F5B 176.4(8) . . ?
F4B P1B F5B 90.1(6) . . ?
F1B P1B F5B 89.9(8) . . ?
F6B P1B F3B 91.1(7) . . ?
F4B P1B F3B 177.9(8) . . ?
F1B P1B F3B 85.7(8) . . ?
F5B P1B F3B 87.9(6) . . ?
F6B P1B F2B 92.2(7) . . ?
F4B P1B F2B 87.6(8) . . ?
F1B P1B F2B 173.9(9) . . ?
F5B P1B F2B 84.4(7) . . ?
F3B P1B F2B 91.6(8) . . ?
C1 N1 C5 122.68(12) . . ?
C1 N1 C4 121.29(12) . . ?
C5 N1 C4 116.00(11) . . ?
C3 N2 C6 119.73(12) . . ?
C3 N2 C7 124.36(12) . . ?
C6 N2 C7 112.65(12) . . ?
C1 N3 C8 122.97(12) . . ?
C1 N3 H3N 120.7(13) . . ?
C8 N3 H3N 116.1(13) . . ?
N1 C1 N3 117.57(12) . . ?
N1 C1 C2 124.03(12) . . ?
N3 C1 C2 118.37(12) . . ?
C3 C2 C1 122.19(13) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
N2 C3 C2 120.18(13) . . ?
N2 C3 C13 121.83(12) . . ?
C2 C3 C13 117.97(12) . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C13 120.37(12) . . ?
N3 C8 C9 117.75(13) . . ?
C13 C8 C9 121.86(13) . . ?
C10 C9 C8 119.48(14) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 119.77(14) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 120.94(14) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 120.96(14) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C8 C13 C12 116.71(13) . . ?
C8 C13 C3 117.91(12) . . ?
C12 C13 C3 125.29(13) . . ?

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
C5 N1 C1 N3 172.85(12) . . . . ?
C4 N1 C1 N3 -5.1(2) . . . . ?
C5 N1 C1 C2 -9.5(2) . . . . ?
C4 N1 C1 C2 172.50(13) . . . . ?
C8 N3 C1 N1 -178.83(12) . . . . ?
C8 N3 C1 C2 3.4(2) . . . . ?
N1 C1 C2 C3 -179.50(12) . . . . ?
N3 C1 C2 C3 -1.9(2) . . . . ?
C6 N2 C3 C2 10.3(2) . . . . ?
C7 N2 C3 C2 -147.83(14) . . . . ?
C6 N2 C3 C13 -168.01(13) . . . . ?
C7 N2 C3 C13 33.9(2) . . . . ?
C1 C2 C3 N2 179.39(13) . . . . ?
C1 C2 C3 C13 -2.3(2) . . . . ?
C1 N3 C8 C13 -0.5(2) . . . . ?
C1 N3 C8 C9 178.19(13) . . . . ?
N3 C8 C9 C10 -176.67(13) . . . . ?
C13 C8 C9 C10 2.0(2) . . . . ?
C8 C9 C10 C11 2.1(2) . . . . ?
C9 C10 C11 C12 -2.3(2) . . . . ?
C10 C11 C12 C13 -1.6(2) . . . . ?
N3 C8 C13 C12 172.98(12) . . . . ?
C9 C8 C13 C12 -5.7(2) . . . . ?
N3 C8 C13 C3 -3.71(19) . . . . ?
C9 C8 C13 C3 177.62(13) . . . . ?
C11 C12 C13 C8 5.4(2) . . . . ?
C11 C12 C13 C3 -178.14(13) . . . . ?
N2 C3 C13 C8 -176.69(12) . . . . ?
C2 C3 C13 C8 4.99(18) . . . . ?
N2 C3 C13 C12 6.9(2) . . . . ?
C2 C3 C13 C12 -171.38(13) . . . . ?

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
N3 H3N F3A^a 0.824(19) 2.230(19) 2.994(4) 154.5(17) . yes
N3 H3N F3B^b 0.824(19) 2.18(2) 2.945(12) 154.6(17) . yes

_refine_diff_density_max         0.445
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_compound7b_ML085
_database_code_depnum_ccdc_archive 'CCDC 2062050'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson'
;Saint Marys University
Canada
;
_audit_update_record             
;
2021-02-09 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

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

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H33 N4, Cl, C H2 Cl2'
_chemical_formula_sum            'C16 H35 Cl3 N4'
_chemical_formula_weight         389.83

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.5341(8)
_cell_length_b                   20.2391(17)
_cell_length_c                   11.4827(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.2170(10)
_cell_angle_gamma                90
_cell_volume                     2180.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    9954
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      28.84

_exptl_crystal_description       'Ã?rregular block'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    0.425
_shelx_estimated_absorpt_T_min   0.816
_shelx_estimated_absorpt_T_max   0.865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7059
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26196
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.012
_diffrn_reflns_theta_max         28.842
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5434
_reflns_number_gt                4769
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (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)+(0.0401P)²+0.5458P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'dual space'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5434
_refine_ls_number_parameters     309
_refine_ls_number_restraints     116
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0789
_refine_ls_wR_factor_gt          0.0749
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.002
_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
Cl1 Cl 0.35390(3) 0.63503(2) 0.38419(2) 0.02471(7) Uani 1 1 d . . . . .
C16A C 0.0244(14) 0.7024(5) 0.3573(11) 0.050(2) Uani 0.469(15) 1 d D U P A 1
H16A H 0.127806 0.696140 0.385585 0.060 Uiso 0.469(15) 1 calc R U P A 1
H16B H -0.028026 0.681498 0.414667 0.060 Uiso 0.469(15) 1 calc R U P A 1
Cl2A Cl -0.0166(5) 0.7876(3) 0.3438(7) 0.0590(11) Uani 0.469(15) 1 d D U P A 1
Cl3A Cl -0.0268(5) 0.6667(2) 0.2161(9) 0.074(2) Uani 0.469(15) 1 d D U P A 1
C16B C 0.0034(17) 0.6923(5) 0.3307(11) 0.045(2) Uani 0.407(15) 1 d D U P B 2
H16C H -0.058853 0.667643 0.375985 0.054 Uiso 0.407(15) 1 calc R U P B 2
H16D H 0.103324 0.682813 0.367457 0.054 Uiso 0.407(15) 1 calc R U P B 2
Cl2B Cl -0.0278(7) 0.7769(4) 0.3452(6) 0.0674(14) Uani 0.407(15) 1 d D U P B 2
Cl3B Cl -0.0257(4) 0.66211(17) 0.1854(5) 0.0446(7) Uani 0.407(15) 1 d D U P B 2
C16C C 0.037(4) 0.7122(10) 0.396(3) 0.050(4) Uani 0.082(5) 1 d D U P C 3
H16E H 0.017181 0.696872 0.472786 0.060 Uiso 0.082(5) 1 calc R U P C 3
H16F H 0.138385 0.702186 0.393598 0.060 Uiso 0.082(5) 1 calc R U P C 3
Cl2C Cl 0.015(2) 0.7968(7) 0.3881(16) 0.068(3) Uani 0.082(5) 1 d D U P C 3
Cl3C Cl -0.0677(18) 0.6671(6) 0.285(2) 0.097(4) Uani 0.082(5) 1 d D U P C 3
C16D C 0.030(4) 0.7155(12) 0.301(4) 0.050(4) Uani 0.0400(19) 1 d D U P D 4
H16G H 0.132723 0.705260 0.327228 0.059 Uiso 0.0400(19) 1 calc R U P D 4
H16H H 0.004266 0.702230 0.217023 0.059 Uiso 0.0400(19) 1 calc R U P D 4
Cl2D Cl 0.006(3) 0.8004(10) 0.312(3) 0.065(5) Uani 0.0400(19) 1 d D U P D 4
Cl3D Cl -0.0691(11) 0.6686(5) 0.3848(15) 0.067(4) Uani 0.0400(19) 1 d D U P D 4
N1 N 0.40928(9) 0.70582(4) 0.71058(7) 0.02112(17) Uani 1 1 d . . . . .
N2 N 0.58558(9) 0.74173(4) 0.61226(7) 0.02167(17) Uani 1 1 d . . . . .
N3 N 0.40482(8) 0.56264(4) 0.63646(7) 0.01827(16) Uani 1 1 d D . . . .
H3N H 0.3838(13) 0.5891(6) 0.5768(10) 0.027 Uiso 1 1 d D U . . .
N4 N 0.60686(8) 0.51668(4) 0.75130(7) 0.01834(16) Uani 1 1 d D . . . .
H4N H 0.5826(13) 0.4781(6) 0.7193(11) 0.028 Uiso 1 1 d D U . . .
C1 C 0.53187(10) 0.69208(4) 0.67053(8) 0.01892(18) Uani 1 1 d . . . . .
C2 C 0.60545(10) 0.63211(4) 0.69200(8) 0.01892(18) Uani 1 1 d . . . . .
H2 H 0.706629 0.633398 0.704955 0.023 Uiso 1 1 calc R U . . .
C3 C 0.53905(10) 0.56972(4) 0.69568(7) 0.01709(17) Uani 1 1 d . . . . .
C4 C 0.37573(12) 0.67682(5) 0.81792(9) 0.0259(2) Uani 1 1 d . . . . .
H4A H 0.297488 0.645149 0.797400 0.039 Uiso 1 1 calc R U . . .
H4B H 0.347109 0.711725 0.868034 0.039 Uiso 1 1 calc R U . . .
H4C H 0.459937 0.653988 0.860828 0.039 Uiso 1 1 calc R U . . .
C5 C 0.29429(11) 0.74411(5) 0.64135(9) 0.0250(2) Uani 1 1 d . . . . .
H5A H 0.317294 0.753446 0.563135 0.037 Uiso 1 1 calc R U . . .
H5B H 0.282929 0.785789 0.682111 0.037 Uiso 1 1 calc R U . . .
H5C H 0.205348 0.718827 0.632281 0.037 Uiso 1 1 calc R U . . .
C6 C 0.57221(12) 0.81091(5) 0.64453(10) 0.0263(2) Uani 1 1 d . . . . .
H6A H 0.530200 0.813560 0.716345 0.039 Uiso 1 1 calc R U . . .
H6B H 0.510768 0.834049 0.579815 0.039 Uiso 1 1 calc R U . . .
H6C H 0.666680 0.831552 0.659110 0.039 Uiso 1 1 calc R U . . .
C7 C 0.68078(12) 0.72772(5) 0.52926(9) 0.0267(2) Uani 1 1 d . . . . .
H7A H 0.779611 0.727682 0.571410 0.040 Uiso 1 1 calc R U . . .
H7B H 0.669153 0.761718 0.467517 0.040 Uiso 1 1 calc R U . . .
H7C H 0.657646 0.684345 0.492977 0.040 Uiso 1 1 calc R U . . .
C8 C 0.29331(10) 0.51257(4) 0.64349(8) 0.01910(18) Uani 1 1 d . . . . .
C9 C 0.15165(10) 0.54870(5) 0.60383(10) 0.0265(2) Uani 1 1 d . . . . .
H9A H 0.142636 0.584479 0.659544 0.040 Uiso 1 1 calc R U . . .
H9B H 0.072591 0.517551 0.601981 0.040 Uiso 1 1 calc R U . . .
H9C H 0.149122 0.567189 0.524605 0.040 Uiso 1 1 calc R U . . .
C10 C 0.29881(12) 0.48676(5) 0.76951(9) 0.0283(2) Uani 1 1 d . . . . .
H10A H 0.384461 0.459692 0.792566 0.042 Uiso 1 1 calc R U . . .
H10B H 0.214020 0.459905 0.772599 0.042 Uiso 1 1 calc R U . . .
H10C H 0.301472 0.524166 0.824057 0.042 Uiso 1 1 calc R U . . .
C11 C 0.30410(11) 0.45592(5) 0.55757(10) 0.0285(2) Uani 1 1 d . . . . .
H11A H 0.298148 0.473608 0.477390 0.043 Uiso 1 1 calc R U . . .
H11B H 0.225753 0.424760 0.558986 0.043 Uiso 1 1 calc R U . . .
H11C H 0.395333 0.433071 0.581215 0.043 Uiso 1 1 calc R U . . .
C12 C 0.73705(10) 0.51474(5) 0.84361(8) 0.02035(18) Uani 1 1 d . . . . .
C13 C 0.73148(12) 0.44798(5) 0.90589(9) 0.0270(2) Uani 1 1 d . . . . .
H13A H 0.646967 0.446404 0.943520 0.041 Uiso 1 1 calc R U . . .
H13B H 0.817306 0.442627 0.966244 0.041 Uiso 1 1 calc R U . . .
H13C H 0.726598 0.412251 0.847702 0.041 Uiso 1 1 calc R U . . .
C14 C 0.87144(11) 0.51726(6) 0.78778(10) 0.0290(2) Uani 1 1 d . . . . .
H14A H 0.869077 0.481110 0.730686 0.043 Uiso 1 1 calc R U . . .
H14B H 0.955899 0.512654 0.849772 0.043 Uiso 1 1 calc R U . . .
H14C H 0.875333 0.559634 0.747169 0.043 Uiso 1 1 calc R U . . .
C15 C 0.73701(12) 0.56981(5) 0.93499(9) 0.0265(2) Uani 1 1 d . . . . .
H15A H 0.745142 0.612747 0.897303 0.040 Uiso 1 1 calc R U . . .
H15B H 0.817918 0.563732 0.999802 0.040 Uiso 1 1 calc R U . . .
H15C H 0.647943 0.568198 0.966354 0.040 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
C16A Cl3A 1.763(9) . ?
C16A Cl2A 1.768(9) . ?
C16A H16A 0.9900 . ?
C16A H16B 0.9900 . ?
C16B Cl2B 1.751(10) . ?
C16B Cl3B 1.753(10) . ?
C16B H16C 0.9900 . ?
C16B H16D 0.9900 . ?
C16C Cl2C 1.725(16) . ?
C16C Cl3C 1.731(16) . ?
C16C H16E 0.9900 . ?
C16C H16F 0.9900 . ?
C16D Cl2D 1.743(17) . ?
C16D Cl3D 1.746(16) . ?
C16D H16G 0.9900 . ?
C16D H16H 0.9900 . ?
N1 C1 1.3584(12) . ?
N1 C4 1.4513(12) . ?
N1 C5 1.4578(13) . ?
N2 C1 1.3569(12) . ?
N2 C7 1.4558(13) . ?
N2 C6 1.4597(12) . ?
N3 C3 1.3461(12) . ?
N3 C8 1.4813(11) . ?
N3 H3N 0.865(11) . ?
N4 C3 1.3534(12) . ?
N4 C12 1.4829(12) . ?
N4 H4N 0.877(11) . ?
C1 C2 1.4017(13) . ?
C2 C3 1.4165(12) . ?
C2 H2 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
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 C11 1.5278(13) . ?
C8 C10 1.5305(13) . ?
C8 C9 1.5324(13) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
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 C15 1.5308(13) . ?
C12 C14 1.5319(14) . ?
C12 C13 1.5342(13) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
Cl3A C16A Cl2A 107.4(6) . . ?
Cl3A C16A H16A 110.2 . . ?
Cl2A C16A H16A 110.2 . . ?
Cl3A C16A H16B 110.2 . . ?
Cl2A C16A H16B 110.2 . . ?
H16A C16A H16B 108.5 . . ?
Cl2B C16B Cl3B 115.5(7) . . ?
Cl2B C16B H16C 108.4 . . ?
Cl3B C16B H16C 108.4 . . ?
Cl2B C16B H16D 108.4 . . ?
Cl3B C16B H16D 108.4 . . ?
H16C C16B H16D 107.5 . . ?
Cl2C C16C Cl3C 115.9(14) . . ?
Cl2C C16C H16E 108.3 . . ?
Cl3C C16C H16E 108.3 . . ?
Cl2C C16C H16F 108.3 . . ?
Cl3C C16C H16F 108.3 . . ?
H16E C16C H16F 107.4 . . ?
Cl2D C16D Cl3D 113.8(15) . . ?
Cl2D C16D H16G 108.8 . . ?
Cl3D C16D H16G 108.8 . . ?
Cl2D C16D H16H 108.8 . . ?
Cl3D C16D H16H 108.8 . . ?
H16G C16D H16H 107.7 . . ?
C1 N1 C4 122.49(8) . . ?
C1 N1 C5 122.22(8) . . ?
C4 N1 C5 114.86(8) . . ?
C1 N2 C7 120.82(8) . . ?
C1 N2 C6 121.84(8) . . ?
C7 N2 C6 116.46(8) . . ?
C3 N3 C8 132.26(8) . . ?
C3 N3 H3N 113.6(8) . . ?
C8 N3 H3N 113.5(8) . . ?
C3 N4 C12 128.87(8) . . ?
C3 N4 H4N 116.1(8) . . ?
C12 N4 H4N 113.6(8) . . ?
N2 C1 N1 115.98(8) . . ?
N2 C1 C2 120.47(9) . . ?
N1 C1 C2 123.47(8) . . ?
C1 C2 C3 124.39(9) . . ?
C1 C2 H2 117.8 . . ?
C3 C2 H2 117.8 . . ?
N3 C3 N4 119.06(8) . . ?
N3 C3 C2 118.02(8) . . ?
N4 C3 C2 122.86(8) . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C11 110.30(8) . . ?
N3 C8 C10 112.36(8) . . ?
C11 C8 C10 111.07(8) . . ?
N3 C8 C9 105.10(7) . . ?
C11 C8 C9 108.84(8) . . ?
C10 C8 C9 108.93(8) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N4 C12 C15 111.63(8) . . ?
N4 C12 C14 110.87(8) . . ?
C15 C12 C14 111.38(8) . . ?
N4 C12 C13 105.23(8) . . ?
C15 C12 C13 108.51(8) . . ?
C14 C12 C13 108.98(8) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C7 N2 C1 N1 -157.02(9) . . . . ?
C6 N2 C1 N1 34.10(13) . . . . ?
C7 N2 C1 C2 26.24(14) . . . . ?
C6 N2 C1 C2 -142.64(10) . . . . ?
C4 N1 C1 N2 -147.91(9) . . . . ?
C5 N1 C1 N2 39.96(13) . . . . ?
C4 N1 C1 C2 28.71(14) . . . . ?
C5 N1 C1 C2 -143.41(9) . . . . ?
N2 C1 C2 C3 -147.25(9) . . . . ?
N1 C1 C2 C3 36.27(14) . . . . ?
C8 N3 C3 N4 20.07(14) . . . . ?
C8 N3 C3 C2 -162.90(9) . . . . ?
C12 N4 C3 N3 -163.85(8) . . . . ?
C12 N4 C3 C2 19.27(14) . . . . ?
C1 C2 C3 N3 24.44(13) . . . . ?
C1 C2 C3 N4 -158.65(9) . . . . ?
C3 N3 C8 C11 -90.48(12) . . . . ?
C3 N3 C8 C10 34.04(13) . . . . ?
C3 N3 C8 C9 152.36(9) . . . . ?
C3 N4 C12 C15 41.32(13) . . . . ?
C3 N4 C12 C14 -83.49(11) . . . . ?
C3 N4 C12 C13 158.84(9) . . . . ?

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
N3 H3N Cl1 0.865(11) 2.369(11) 3.2054(8) 162.8(11) . yes
N4 H4N Cl1 0.877(11) 2.697(12) 3.4922(8) 151.4(11) 3_666 yes

_refine_diff_density_max         0.328
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_compound9_ML134
_database_code_depnum_ccdc_archive 'CCDC 2062044'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson'
;Saint Marys University
Canada
;
_audit_update_record             
;
2021-02-09 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

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

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H18 N2 O'
_chemical_formula_sum            'C9 H18 N2 O'
_chemical_formula_weight         170.25

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.014(3)
_cell_length_b                   10.060(2)
_cell_length_c                   10.165(2)
_cell_angle_alpha                90
_cell_angle_beta                 117.450(3)
_cell_angle_gamma                90
_cell_volume                     999.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    2704
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      25.44

_exptl_crystal_description       'thin plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.132
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6248
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11666
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.024
_diffrn_reflns_theta_max         27.643
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2318
_reflns_number_gt                1566
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component 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)+(0.0727P)²+0.0649P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'dual space'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2318
_refine_ls_number_parameters     115
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0946
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1436
_refine_ls_wR_factor_gt          0.1249
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
O1 O 0.02824(18) 0.25396(18) 0.21496(19) 0.0290(4) Uani 1 1 d . . . . .
N1 N 0.0557(2) 0.2833(2) 0.0103(2) 0.0234(5) Uani 1 1 d . . . . .
H1 H 0.032(3) 0.261(3) -0.083(3) 0.035 Uiso 1 1 d . U . . .
N2 N -0.1105(2) 0.13864(19) 0.0067(2) 0.0267(5) Uani 1 1 d . . . . .
C1 C -0.0074(3) 0.2263(2) 0.0831(3) 0.0226(5) Uani 1 1 d . . . . .
C2 C 0.1749(2) 0.3684(2) 0.0909(3) 0.0227(5) Uani 1 1 d . . . . .
H2 H 0.158161 0.422644 0.163429 0.027 Uiso 1 1 calc R U . . .
C3 C 0.3035(3) 0.2874(2) 0.1769(3) 0.0338(7) Uani 1 1 d . . . . .
H3A H 0.319848 0.230106 0.107416 0.041 Uiso 1 1 calc R U . . .
H3B H 0.290836 0.229041 0.247995 0.041 Uiso 1 1 calc R U . . .
C4 C 0.4279(3) 0.3767(3) 0.2611(3) 0.0422(7) Uani 1 1 d . . . . .
H4A H 0.416214 0.426757 0.338338 0.051 Uiso 1 1 calc R U . . .
H4B H 0.510989 0.321028 0.310873 0.051 Uiso 1 1 calc R U . . .
C5 C 0.4457(3) 0.4736(3) 0.1568(3) 0.0409(7) Uani 1 1 d . . . . .
H5A H 0.522461 0.534624 0.214842 0.049 Uiso 1 1 calc R U . . .
H5B H 0.468958 0.423747 0.087399 0.049 Uiso 1 1 calc R U . . .
C6 C 0.3170(3) 0.5536(2) 0.0694(3) 0.0336(6) Uani 1 1 d . . . . .
H6A H 0.329914 0.611647 -0.001746 0.040 Uiso 1 1 calc R U . . .
H6B H 0.299622 0.611146 0.137969 0.040 Uiso 1 1 calc R U . . .
C7 C 0.1930(3) 0.4632(2) -0.0152(3) 0.0277(6) Uani 1 1 d . . . . .
H7A H 0.109588 0.518123 -0.067032 0.033 Uiso 1 1 calc R U . . .
H7B H 0.206062 0.411638 -0.090691 0.033 Uiso 1 1 calc R U . . .
C8 C -0.1584(3) 0.1056(2) -0.1467(3) 0.0317(6) Uani 1 1 d . . . . .
H8A H -0.229192 0.169072 -0.208739 0.048 Uiso 1 1 calc R U . . .
H8B H -0.196795 0.015594 -0.165253 0.048 Uiso 1 1 calc R U . . .
H8C H -0.081904 0.109527 -0.170652 0.048 Uiso 1 1 calc R U . . .
C9 C -0.1802(3) 0.0773(3) 0.0820(3) 0.0322(7) Uani 1 1 d . . . . .
H9A H -0.132386 0.099779 0.187668 0.048 Uiso 1 1 calc R U . . .
H9B H -0.180692 -0.019440 0.070222 0.048 Uiso 1 1 calc R U . . .
H9C H -0.274506 0.109965 0.039150 0.048 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 C1 1.242(3) . ?
N1 C1 1.354(3) . ?
N1 C2 1.462(3) . ?
N1 H1 0.89(3) . ?
N2 C1 1.363(3) . ?
N2 C8 1.436(3) . ?
N2 C9 1.448(3) . ?
C2 C3 1.514(3) . ?
C2 C7 1.520(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.528(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.518(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.512(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.533(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
C1 N1 C2 119.7(2) . . ?
C1 N1 H1 120.6(18) . . ?
C2 N1 H1 119.3(18) . . ?
C1 N2 C8 124.1(2) . . ?
C1 N2 C9 118.7(2) . . ?
C8 N2 C9 117.2(2) . . ?
O1 C1 N1 120.6(2) . . ?
O1 C1 N2 121.7(2) . . ?
N1 C1 N2 117.7(2) . . ?
N1 C2 C3 111.56(19) . . ?
N1 C2 C7 110.3(2) . . ?
C3 C2 C7 110.7(2) . . ?
N1 C2 H2 108.1 . . ?
C3 C2 H2 108.1 . . ?
C7 C2 H2 108.1 . . ?
C2 C3 C4 111.4(2) . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C3 110.9(2) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.0 . . ?
C6 C5 C4 111.3(2) . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 C7 111.4(2) . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C2 C7 C6 110.3(2) . . ?
C2 C7 H7A 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C2 C7 H7B 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 O1 5.7(3) . . . . ?
C2 N1 C1 N2 -174.4(2) . . . . ?
C8 N2 C1 O1 178.3(2) . . . . ?
C9 N2 C1 O1 0.3(3) . . . . ?
C8 N2 C1 N1 -1.6(3) . . . . ?
C9 N2 C1 N1 -179.6(2) . . . . ?
C1 N1 C2 C3 79.6(3) . . . . ?
C1 N1 C2 C7 -156.9(2) . . . . ?
N1 C2 C3 C4 -180.0(2) . . . . ?
C7 C2 C3 C4 56.8(3) . . . . ?
C2 C3 C4 C5 -55.6(3) . . . . ?
C3 C4 C5 C6 54.8(3) . . . . ?
C4 C5 C6 C7 -55.6(3) . . . . ?
N1 C2 C7 C6 179.4(2) . . . . ?
C3 C2 C7 C6 -56.7(3) . . . . ?
C5 C6 C7 C2 56.3(3) . . . . ?

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 H1 O1 0.89(3) 2.04(3) 2.899(3) 163(3) 4_565 yes

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_compound8a_ML081
_database_code_depnum_ccdc_archive 'CCDC 2062048'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson'
;Saint Marys University
Canada
;
_audit_update_record             
;
2021-02-09 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

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

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H24 N3, F6 P'
_chemical_formula_sum            'C13 H24 F6 N3 P'
_chemical_formula_weight         367.32

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.4385(9)
_cell_length_b                   11.3473(9)
_cell_length_c                   14.6522(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1735.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    9894
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      28.78

_exptl_crystal_description       'thick plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.217
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7033
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21271
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.270
_diffrn_reflns_theta_max         29.014
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4325
_reflns_number_gt                3978
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_max     0.907
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (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)+(0.0370P)²+0.1764P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'dual space'
_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 1587 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4325
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0688
_refine_ls_wR_factor_gt          0.0665
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
P1 P 0.21841(4) 0.28359(4) 0.34937(3) 0.02444(11) Uani 1 1 d . . . . .
F1 F 0.06948(10) 0.28664(11) 0.32310(8) 0.0362(3) Uani 1 1 d . . . . .
F2 F 0.36746(10) 0.28041(12) 0.37499(8) 0.0394(3) Uani 1 1 d . . . . .
F3 F 0.18190(11) 0.26436(11) 0.45447(7) 0.0366(3) Uani 1 1 d . . . . .
F4 F 0.25467(12) 0.30238(12) 0.24375(7) 0.0409(3) Uani 1 1 d . . . . .
F5 F 0.21700(13) 0.42277(10) 0.36453(9) 0.0437(3) Uani 1 1 d . . . . .
F6 F 0.22007(13) 0.14407(9) 0.33395(9) 0.0418(3) Uani 1 1 d . . . . .
N1 N 0.42433(15) 0.54602(13) 0.51829(10) 0.0267(3) Uani 1 1 d . . . . .
N2 N 0.86223(14) 0.54282(13) 0.41990(10) 0.0263(3) Uani 1 1 d . . . . .
N3 N 0.50679(14) 0.70613(13) 0.43841(10) 0.0255(3) Uani 1 1 d . . . . .
C1 C 0.52357(16) 0.59337(16) 0.47495(11) 0.0236(3) Uani 1 1 d . . . . .
C2 C 0.64470(17) 0.53830(16) 0.47358(12) 0.0246(3) Uani 1 1 d . . . . .
H2 H 0.658106 0.468480 0.508062 0.030 Uiso 1 1 calc R U . . .
C3 C 0.74408(17) 0.58467(16) 0.42268(11) 0.0249(4) Uani 1 1 d . . . . .
H3 H 0.726009 0.652281 0.386674 0.030 Uiso 1 1 calc R U . . .
C4 C 0.30007(18) 0.60523(18) 0.52732(13) 0.0327(4) Uani 1 1 d . . . . .
H4A H 0.306129 0.685180 0.502401 0.049 Uiso 1 1 calc R U . . .
H4B H 0.276197 0.609241 0.591933 0.049 Uiso 1 1 calc R U . . .
H4C H 0.234858 0.560824 0.493668 0.049 Uiso 1 1 calc R U . . .
C5 C 0.4335(2) 0.43102(17) 0.56310(14) 0.0349(4) Uani 1 1 d . . . . .
H5A H 0.484838 0.377653 0.525353 0.052 Uiso 1 1 calc R U . . .
H5B H 0.347374 0.398110 0.571043 0.052 Uiso 1 1 calc R U . . .
H5C H 0.474254 0.440327 0.622906 0.052 Uiso 1 1 calc R U . . .
C6 C 0.90037(18) 0.44094(16) 0.47419(13) 0.0296(4) Uani 1 1 d . . . . .
H6A H 0.870565 0.451080 0.537121 0.044 Uiso 1 1 calc R U . . .
H6B H 0.993932 0.433806 0.473672 0.044 Uiso 1 1 calc R U . . .
H6C H 0.862249 0.369485 0.448233 0.044 Uiso 1 1 calc R U . . .
C7 C 0.96068(19) 0.5978(2) 0.36354(14) 0.0368(5) Uani 1 1 d . . . . .
H7A H 0.922111 0.660477 0.326637 0.055 Uiso 1 1 calc R U . . .
H7B H 0.998823 0.538447 0.323265 0.055 Uiso 1 1 calc R U . . .
H7C H 1.027265 0.631407 0.402863 0.055 Uiso 1 1 calc R U . . .
C8 C 0.47367(15) 0.72215(15) 0.35562(11) 0.0224(3) Uani 1 1 d . . . . .
C9 C 0.45294(19) 0.84581(15) 0.32204(13) 0.0292(4) Uani 1 1 d . . . . .
H9A H 0.516797 0.864635 0.274254 0.035 Uiso 1 1 calc R U . . .
H9B H 0.464724 0.901978 0.373059 0.035 Uiso 1 1 calc R U . . .
C10 C 0.3173(2) 0.85864(18) 0.28286(15) 0.0363(5) Uani 1 1 d . . . . .
H10A H 0.253743 0.848688 0.332394 0.044 Uiso 1 1 calc R U . . .
H10B H 0.306707 0.938654 0.257013 0.044 Uiso 1 1 calc R U . . .
C11 C 0.2932(2) 0.76775(18) 0.20919(15) 0.0423(5) Uani 1 1 d . . . . .
H11A H 0.352059 0.781950 0.157377 0.051 Uiso 1 1 calc R U . . .
H11B H 0.204272 0.775833 0.186496 0.051 Uiso 1 1 calc R U . . .
C12 C 0.3134(2) 0.64272(18) 0.24561(16) 0.0408(5) Uani 1 1 d . . . . .
H12A H 0.301816 0.585630 0.195189 0.049 Uiso 1 1 calc R U . . .
H12B H 0.248042 0.625627 0.292725 0.049 Uiso 1 1 calc R U . . .
C13 C 0.44764(18) 0.62683(15) 0.28707(12) 0.0255(4) Uani 1 1 d . . . . .
H13A H 0.453411 0.548849 0.317086 0.031 Uiso 1 1 calc R U . . .
H13B H 0.512848 0.629862 0.238065 0.031 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
P1 F5 1.5949(12) . ?
P1 F6 1.5993(12) . ?
P1 F2 1.6009(12) . ?
P1 F3 1.6014(11) . ?
P1 F1 1.6019(12) . ?
P1 F4 1.6073(12) . ?
N1 C1 1.329(2) . ?
N1 C5 1.464(2) . ?
N1 C4 1.467(2) . ?
N2 C3 1.322(2) . ?
N2 C7 1.459(2) . ?
N2 C6 1.459(2) . ?
N3 C8 1.275(2) . ?
N3 C1 1.398(2) . ?
C1 C2 1.411(2) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
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 C13 1.501(2) . ?
C8 C9 1.503(2) . ?
C9 C10 1.535(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.514(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.530(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.538(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

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
F5 P1 F6 179.86(9) . . ?
F5 P1 F2 89.92(7) . . ?
F6 P1 F2 90.02(7) . . ?
F5 P1 F3 89.93(7) . . ?
F6 P1 F3 90.20(7) . . ?
F2 P1 F3 90.15(6) . . ?
F5 P1 F1 90.18(7) . . ?
F6 P1 F1 89.88(7) . . ?
F2 P1 F1 179.66(7) . . ?
F3 P1 F1 90.17(6) . . ?
F5 P1 F4 90.28(7) . . ?
F6 P1 F4 89.59(7) . . ?
F2 P1 F4 89.99(7) . . ?
F3 P1 F4 179.74(8) . . ?
F1 P1 F4 89.68(6) . . ?
C1 N1 C5 121.61(15) . . ?
C1 N1 C4 123.19(15) . . ?
C5 N1 C4 115.17(15) . . ?
C3 N2 C7 121.40(16) . . ?
C3 N2 C6 121.50(15) . . ?
C7 N2 C6 117.09(15) . . ?
C8 N3 C1 121.94(15) . . ?
N1 C1 N3 117.10(15) . . ?
N1 C1 C2 121.77(16) . . ?
N3 C1 C2 120.82(16) . . ?
C3 C2 C1 120.79(16) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
N2 C3 C2 125.46(16) . . ?
N2 C3 H3 117.3 . . ?
C2 C3 H3 117.3 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C13 125.69(16) . . ?
N3 C8 C9 118.94(16) . . ?
C13 C8 C9 115.33(14) . . ?
C8 C9 C10 110.11(15) . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.2 . . ?
C11 C10 C9 110.84(16) . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 C12 111.09(16) . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C13 111.86(17) . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C8 C13 C12 110.17(15) . . ?
C8 C13 H13A 109.6 . . ?
C12 C13 H13A 109.6 . . ?
C8 C13 H13B 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?

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
C5 N1 C1 N3 -176.85(16) . . . . ?
C4 N1 C1 N3 1.3(2) . . . . ?
C5 N1 C1 C2 -3.2(3) . . . . ?
C4 N1 C1 C2 174.94(16) . . . . ?
C8 N3 C1 N1 -94.6(2) . . . . ?
C8 N3 C1 C2 91.7(2) . . . . ?
N1 C1 C2 C3 175.30(16) . . . . ?
N3 C1 C2 C3 -11.3(3) . . . . ?
C7 N2 C3 C2 179.71(18) . . . . ?
C6 N2 C3 C2 -1.3(3) . . . . ?
C1 C2 C3 N2 176.93(17) . . . . ?
C1 N3 C8 C13 0.4(3) . . . . ?
C1 N3 C8 C9 177.86(15) . . . . ?
N3 C8 C9 C10 -123.50(18) . . . . ?
C13 C8 C9 C10 54.2(2) . . . . ?
C8 C9 C10 C11 -55.2(2) . . . . ?
C9 C10 C11 C12 57.1(2) . . . . ?
C10 C11 C12 C13 -55.7(3) . . . . ?
N3 C8 C13 C12 125.14(19) . . . . ?
C9 C8 C13 C12 -52.4(2) . . . . ?
C11 C12 C13 C8 51.8(2) . . . . ?

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_compound8c_ML150
_database_code_depnum_ccdc_archive 'CCDC 2062047'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson'
;Saint Marys University
Canada
;
_audit_update_record             
;
2021-02-09 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

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

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H22 N3, F6 P'
_chemical_formula_sum            'C11 H22 F6 N3 P'
_chemical_formula_weight         341.28

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.7611(9)
_cell_length_b                   10.3655(8)
_cell_length_c                   14.2459(11)
_cell_angle_alpha                90
_cell_angle_beta                 113.5370(10)
_cell_angle_gamma                90
_cell_volume                     1592.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    9930
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      28.70

_exptl_crystal_description       'thick rod'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.275
_exptl_absorpt_coefficient_mu    0.231
_shelx_estimated_absorpt_T_min   0.884
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6966
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18685
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.910
_diffrn_reflns_theta_max         28.891
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3940
_reflns_number_gt                3336
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (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)+(0.0595P)²+0.5325P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'dual space'
_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_number_reflns         3940
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.1069
_refine_ls_wR_factor_gt          0.1009
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
P1 P 0.02091(3) 0.31185(3) 0.29476(3) 0.02225(11) Uani 1 1 d . . . . .
F1 F 0.00432(9) 0.16896(8) 0.32954(7) 0.0345(2) Uani 1 1 d . . . . .
F2 F 0.03734(8) 0.45555(9) 0.25982(8) 0.0398(2) Uani 1 1 d . . . . .
F3 F -0.12223(8) 0.31536(10) 0.21814(8) 0.0430(3) Uani 1 1 d . . . . .
F4 F 0.16362(9) 0.31021(9) 0.37038(9) 0.0452(3) Uani 1 1 d . . . . .
F5 F -0.01478(11) 0.37000(10) 0.38300(8) 0.0449(3) Uani 1 1 d . . . . .
F6 F 0.05594(11) 0.25428(10) 0.20568(8) 0.0478(3) Uani 1 1 d . . . . .
N1 N 0.63998(11) 0.40693(11) 0.44109(9) 0.0262(2) Uani 1 1 d . . . . .
N2 N 0.33070(10) 0.08170(11) 0.39227(8) 0.0219(2) Uani 1 1 d . . . . .
N3 N 0.53358(10) 0.31436(10) 0.28154(8) 0.0218(2) Uani 1 1 d . . . . .
C1 C 0.55680(12) 0.32068(12) 0.38533(10) 0.0213(3) Uani 1 1 d . . . . .
C2 C 0.48703(12) 0.24565(12) 0.42575(10) 0.0216(3) Uani 1 1 d . . . . .
H2 H 0.499190 0.255375 0.495422 0.026 Uiso 1 1 calc R U . . .
C3 C 0.40080(12) 0.15781(12) 0.36410(10) 0.0201(2) Uani 1 1 d . . . . .
H3 H 0.391418 0.152002 0.294839 0.024 Uiso 1 1 calc R U . . .
C4 C 0.70835(15) 0.48926(15) 0.39736(12) 0.0339(3) Uani 1 1 d . . . . .
H4A H 0.781352 0.442778 0.398285 0.051 Uiso 1 1 calc R U . . .
H4B H 0.734840 0.568333 0.438035 0.051 Uiso 1 1 calc R U . . .
H4C H 0.654430 0.511525 0.326631 0.051 Uiso 1 1 calc R U . . .
C5 C 0.67002(15) 0.42306(15) 0.55075(11) 0.0326(3) Uani 1 1 d . . . . .
H5A H 0.599002 0.461363 0.559984 0.049 Uiso 1 1 calc R U . . .
H5B H 0.742198 0.479860 0.580899 0.049 Uiso 1 1 calc R U . . .
H5C H 0.688945 0.338746 0.584614 0.049 Uiso 1 1 calc R U . . .
C6 C 0.33387(14) 0.08583(15) 0.49571(10) 0.0293(3) Uani 1 1 d . . . . .
H6A H 0.410148 0.044727 0.543329 0.044 Uiso 1 1 calc R U . . .
H6B H 0.261852 0.039725 0.497180 0.044 Uiso 1 1 calc R U . . .
H6C H 0.331747 0.175804 0.516074 0.044 Uiso 1 1 calc R U . . .
C7 C 0.24388(13) -0.00916(14) 0.32106(11) 0.0267(3) Uani 1 1 d . . . . .
H7A H 0.250839 -0.004540 0.254845 0.040 Uiso 1 1 calc R U . . .
H7B H 0.159105 0.012925 0.311992 0.040 Uiso 1 1 calc R U . . .
H7C H 0.263431 -0.096849 0.348537 0.040 Uiso 1 1 calc R U . . .
C8 C 0.59554(12) 0.23871(12) 0.24860(10) 0.0211(3) Uani 1 1 d . . . . .
C9 C 0.69787(13) 0.15141(14) 0.31441(11) 0.0264(3) Uani 1 1 d . . . . .
H9A H 0.707809 0.159130 0.385834 0.040 Uiso 1 1 calc R U . . .
H9B H 0.775411 0.176005 0.308871 0.040 Uiso 1 1 calc R U . . .
H9C H 0.677311 0.062006 0.291562 0.040 Uiso 1 1 calc R U . . .
C10 C 0.56723(13) 0.23662(14) 0.13601(10) 0.0262(3) Uani 1 1 d . . . . .
H10A H 0.540173 0.148483 0.109850 0.031 Uiso 1 1 calc R U . . .
H10B H 0.644757 0.254798 0.126766 0.031 Uiso 1 1 calc R U . . .
C11 C 0.46909(16) 0.33107(17) 0.07154(11) 0.0388(4) Uani 1 1 d . . . . .
H11A H 0.389050 0.307581 0.072905 0.058 Uiso 1 1 calc R U . . .
H11B H 0.462678 0.328494 0.000835 0.058 Uiso 1 1 calc R U . . .
H11C H 0.491953 0.418332 0.099118 0.058 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
P1 F4 1.5918(9) . ?
P1 F5 1.5940(10) . ?
P1 F6 1.5980(10) . ?
P1 F1 1.5983(9) . ?
P1 F3 1.5998(10) . ?
P1 F2 1.6063(9) . ?
N1 C1 1.3291(17) . ?
N1 C5 1.4671(17) . ?
N1 C4 1.4707(18) . ?
N2 C3 1.3144(16) . ?
N2 C6 1.4597(16) . ?
N2 C7 1.4599(17) . ?
N3 C8 1.2803(17) . ?
N3 C1 1.3938(16) . ?
C1 C2 1.4096(18) . ?
C2 C3 1.3847(18) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
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 C9 1.4983(19) . ?
C8 C10 1.5025(17) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.512(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
F4 P1 F5 90.51(6) . . ?
F4 P1 F6 89.82(6) . . ?
F5 P1 F6 179.56(6) . . ?
F4 P1 F1 90.38(5) . . ?
F5 P1 F1 90.16(5) . . ?
F6 P1 F1 90.13(5) . . ?
F4 P1 F3 179.21(6) . . ?
F5 P1 F3 89.58(6) . . ?
F6 P1 F3 90.08(6) . . ?
F1 P1 F3 90.40(5) . . ?
F4 P1 F2 89.70(5) . . ?
F5 P1 F2 89.76(6) . . ?
F6 P1 F2 89.95(6) . . ?
F1 P1 F2 179.89(6) . . ?
F3 P1 F2 89.52(5) . . ?
C1 N1 C5 121.32(12) . . ?
C1 N1 C4 122.25(12) . . ?
C5 N1 C4 116.42(12) . . ?
C3 N2 C6 121.62(11) . . ?
C3 N2 C7 121.67(11) . . ?
C6 N2 C7 116.70(11) . . ?
C8 N3 C1 121.23(11) . . ?
N1 C1 N3 116.83(11) . . ?
N1 C1 C2 122.45(12) . . ?
N3 C1 C2 120.53(12) . . ?
C3 C2 C1 120.14(11) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
N2 C3 C2 126.22(12) . . ?
N2 C3 H3 116.9 . . ?
C2 C3 H3 116.9 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C9 124.97(12) . . ?
N3 C8 C10 118.96(12) . . ?
C9 C8 C10 116.07(11) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 C11 115.40(11) . . ?
C8 C10 H10A 108.4 . . ?
C11 C10 H10A 108.4 . . ?
C8 C10 H10B 108.4 . . ?
C11 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
C5 N1 C1 N3 179.03(12) . . . . ?
C4 N1 C1 N3 -2.16(19) . . . . ?
C5 N1 C1 C2 4.1(2) . . . . ?
C4 N1 C1 C2 -177.08(13) . . . . ?
C8 N3 C1 N1 90.47(15) . . . . ?
C8 N3 C1 C2 -94.50(16) . . . . ?
N1 C1 C2 C3 179.49(12) . . . . ?
N3 C1 C2 C3 4.75(19) . . . . ?
C6 N2 C3 C2 2.4(2) . . . . ?
C7 N2 C3 C2 -179.00(12) . . . . ?
C1 C2 C3 N2 179.49(12) . . . . ?
C1 N3 C8 C9 -0.6(2) . . . . ?
C1 N3 C8 C10 -179.52(11) . . . . ?
N3 C8 C10 C11 2.55(19) . . . . ?
C9 C8 C10 C11 -176.46(13) . . . . ?

_refine_diff_density_max         0.391
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_compound12_ML083
_database_code_depnum_ccdc_archive 'CCDC 2062045'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson'
;Saint Marys University
Canada
;
_audit_update_record             
;
2021-02-09 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

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

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H30 N4, C H2 Cl2, 2(Cl), 2(H2 O)'
_chemical_formula_sum            'C22 H36 Cl4 N4 O2'
_chemical_formula_weight         530.35

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.6928(14)
_cell_length_b                   17.170(3)
_cell_length_c                   20.590(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2719.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    9058
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      26.57

_exptl_crystal_description       'thin rod'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.460
_shelx_estimated_absorpt_T_min   0.837
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6522
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32866
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.544
_diffrn_reflns_theta_max         28.858
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6791
_reflns_number_gt                5151
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_max     0.933
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (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)+(0.0363P)²+0.4634P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'dual space'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1803 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         6791
_refine_ls_number_parameters     312
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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
Cl1 Cl 0.82423(11) 0.49209(5) 0.26586(4) 0.02602(18) Uani 1 1 d . . . . .
Cl2 Cl 0.60337(12) 0.34319(5) 0.54941(4) 0.0327(2) Uani 1 1 d . . . . .
Cl3 Cl 0.49165(13) 0.49369(6) 0.13481(5) 0.0430(3) Uani 1 1 d . . . . .
Cl4 Cl 0.70752(19) 0.38936(7) 0.05851(6) 0.0716(4) Uani 1 1 d . . . . .
O1 O 0.1143(4) 0.57083(18) 0.17053(16) 0.0480(8) Uani 1 1 d D . . . .
H1O H 0.039(5) 0.550(3) 0.195(2) 0.072 Uiso 1 1 d D U . . .
H2O H 0.056(6) 0.587(3) 0.1376(17) 0.072 Uiso 1 1 d D U . . .
O2 O 0.7831(4) 0.27613(17) 0.41969(14) 0.0442(7) Uani 1 1 d D . . . .
H3O H 0.754(6) 0.290(3) 0.4587(14) 0.066 Uiso 1 1 d D U . . .
H4O H 0.863(5) 0.241(2) 0.427(2) 0.066 Uiso 1 1 d D U . . .
N1 N 0.5261(4) 0.27808(16) 0.30690(13) 0.0262(7) Uani 1 1 d . . . . .
N2 N 0.0870(4) 0.40299(16) 0.43440(13) 0.0257(6) Uani 1 1 d . . . . .
N3 N 0.5032(4) 0.40837(16) 0.32842(13) 0.0227(6) Uani 1 1 d D . . . .
H3N H 0.585(4) 0.418(2) 0.3000(15) 0.034 Uiso 1 1 d D U . . .
N4 N 0.0913(4) 0.37796(15) 0.32490(12) 0.0195(6) Uani 1 1 d D . . . .
H4N H 0.015(4) 0.4148(17) 0.3191(16) 0.029 Uiso 1 1 d D U . . .
C1 C 0.4557(4) 0.33550(19) 0.33967(15) 0.0210(7) Uani 1 1 d . . . . .
C2 C 0.3208(4) 0.32009(18) 0.39166(15) 0.0227(7) Uani 1 1 d . . . . .
H2A H 0.372495 0.330971 0.434747 0.027 Uiso 1 1 calc R U . . .
H2B H 0.288298 0.264325 0.390509 0.027 Uiso 1 1 calc R U . . .
C3 C 0.1582(4) 0.36909(18) 0.38354(15) 0.0205(7) Uani 1 1 d . . . . .
C4 C 0.6518(5) 0.2950(2) 0.25548(19) 0.0392(10) Uani 1 1 d . . . . .
H4A H 0.603772 0.334515 0.226215 0.059 Uiso 1 1 calc R U . . .
H4B H 0.676048 0.247300 0.230940 0.059 Uiso 1 1 calc R U . . .
H4C H 0.759757 0.314448 0.274841 0.059 Uiso 1 1 calc R U . . .
C5 C 0.5081(5) 0.19418(19) 0.32215(18) 0.0319(8) Uani 1 1 d . . . . .
H5A H 0.621630 0.172994 0.334605 0.048 Uiso 1 1 calc R U . . .
H5B H 0.464826 0.166469 0.283820 0.048 Uiso 1 1 calc R U . . .
H5C H 0.426039 0.187563 0.358126 0.048 Uiso 1 1 calc R U . . .
C6 C -0.0687(5) 0.4519(2) 0.42612(18) 0.0339(9) Uani 1 1 d . . . . .
H6A H -0.039798 0.497168 0.399271 0.051 Uiso 1 1 calc R U . . .
H6B H -0.109612 0.469447 0.468740 0.051 Uiso 1 1 calc R U . . .
H6C H -0.160272 0.421478 0.404846 0.051 Uiso 1 1 calc R U . . .
C7 C 0.1419(5) 0.3914(2) 0.50174(15) 0.0384(10) Uani 1 1 d . . . . .
H7A H 0.044100 0.369796 0.526997 0.058 Uiso 1 1 d R U . . .
H7B H 0.173800 0.442291 0.520824 0.058 Uiso 1 1 d R U . . .
H7C1 H 0.212940 0.341790 0.509508 0.058 Uiso 0.5 1 d R U P . .
H7C2 H 0.265440 0.377290 0.508908 0.058 Uiso 0.5 1 d R U P . .
C8 C 0.4356(4) 0.47671(18) 0.36026(16) 0.0214(7) Uani 1 1 d . . . . .
C9 C 0.3441(5) 0.53057(18) 0.32414(17) 0.0254(8) Uani 1 1 d . . . . .
H9 H 0.327139 0.523086 0.278863 0.031 Uiso 1 1 calc R U . . .
C10 C 0.2771(5) 0.5960(2) 0.35512(18) 0.0315(8) Uani 1 1 d . . . . .
H10 H 0.212731 0.632906 0.330570 0.038 Uiso 1 1 calc R U . . .
C11 C 0.3020(5) 0.6086(2) 0.42072(18) 0.0319(8) Uani 1 1 d . . . . .
C12 C 0.3977(5) 0.5548(2) 0.45526(18) 0.0313(8) Uani 1 1 d . . . . .
H12 H 0.417464 0.563084 0.500273 0.038 Uiso 1 1 calc R U . . .
C13 C 0.4656(4) 0.4890(2) 0.42603(16) 0.0267(8) Uani 1 1 d . . . . .
H13 H 0.531909 0.452722 0.450537 0.032 Uiso 1 1 calc R U . . .
C14 C 0.2291(6) 0.6802(2) 0.4542(2) 0.0533(12) Uani 1 1 d . . . . .
H14A H 0.179414 0.715421 0.421601 0.080 Uiso 1 1 calc R U . . .
H14B H 0.322393 0.707034 0.477621 0.080 Uiso 1 1 calc R U . . .
H14C H 0.138273 0.664531 0.484875 0.080 Uiso 1 1 calc R U . . .
C15 C 0.1290(4) 0.32904(17) 0.27026(15) 0.0194(7) Uani 1 1 d . . . . .
C16 C 0.1836(4) 0.36225(18) 0.21253(15) 0.0236(7) Uani 1 1 d . . . . .
H16 H 0.195596 0.417156 0.208967 0.028 Uiso 1 1 calc R U . . .
C17 C 0.2207(5) 0.3147(2) 0.16001(17) 0.0288(8) Uani 1 1 d . . . . .
H17 H 0.258130 0.337651 0.120428 0.035 Uiso 1 1 calc R U . . .
C18 C 0.2043(5) 0.2341(2) 0.16384(16) 0.0279(8) Uani 1 1 d . . . . .
C19 C 0.1432(4) 0.20256(19) 0.22176(17) 0.0274(8) Uani 1 1 d . . . . .
H19 H 0.127941 0.147803 0.225152 0.033 Uiso 1 1 calc R U . . .
C20 C 0.1043(4) 0.24922(18) 0.27439(16) 0.0244(7) Uani 1 1 d . . . . .
H20 H 0.060864 0.226717 0.313287 0.029 Uiso 1 1 calc R U . . .
C21 C 0.2497(5) 0.1815(2) 0.10809(19) 0.0412(10) Uani 1 1 d . . . . .
H21A H 0.281887 0.130040 0.124750 0.062 Uiso 1 1 calc R U . . .
H21B H 0.347801 0.203683 0.083969 0.062 Uiso 1 1 calc R U . . .
H21C H 0.149199 0.176549 0.079154 0.062 Uiso 1 1 calc R U . . .
C22 C 0.7056(5) 0.4715(2) 0.10906(18) 0.0359(9) Uani 1 1 d . . . . .
H22A H 0.754464 0.516570 0.085317 0.043 Uiso 1 1 calc R U . . .
H22B H 0.779670 0.461637 0.147506 0.043 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
Cl3 C22 1.770(4) . ?
Cl4 C22 1.753(4) . ?
O1 H1O 0.84(2) . ?
O1 H2O 0.86(2) . ?
O2 H3O 0.87(2) . ?
O2 H4O 0.88(2) . ?
N1 C1 1.312(4) . ?
N1 C4 1.463(4) . ?
N1 C5 1.481(4) . ?
N2 C3 1.317(4) . ?
N2 C7 1.463(4) . ?
N2 C6 1.472(4) . ?
N3 C1 1.324(4) . ?
N3 C8 1.441(4) . ?
N3 H3N 0.87(2) . ?
N4 C3 1.321(4) . ?
N4 C15 1.434(4) . ?
N4 H4N 0.87(2) . ?
C1 C2 1.514(4) . ?
C2 C3 1.517(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9866 . ?
C7 H7B 0.9894 . ?
C7 H7C1 1.0244 . ?
C7 H7C2 0.9920 . ?
C8 C9 1.380(5) . ?
C8 C13 1.390(4) . ?
C9 C10 1.391(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(5) . ?
C11 C14 1.517(5) . ?
C12 C13 1.382(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.384(4) . ?
C15 C20 1.386(4) . ?
C16 C17 1.385(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.392(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.392(5) . ?
C18 C21 1.502(5) . ?
C19 C20 1.381(5) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?

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
H1O O1 H2O 104(5) . . ?
H3O O2 H4O 102(4) . . ?
C1 N1 C4 119.7(3) . . ?
C1 N1 C5 125.7(3) . . ?
C4 N1 C5 114.1(3) . . ?
C3 N2 C7 125.0(3) . . ?
C3 N2 C6 119.9(3) . . ?
C7 N2 C6 115.0(3) . . ?
C1 N3 C8 126.2(3) . . ?
C1 N3 H3N 120(2) . . ?
C8 N3 H3N 114(2) . . ?
C3 N4 C15 124.8(3) . . ?
C3 N4 H4N 118(2) . . ?
C15 N4 H4N 117(2) . . ?
N1 C1 N3 120.4(3) . . ?
N1 C1 C2 121.0(3) . . ?
N3 C1 C2 118.6(3) . . ?
C1 C2 C3 113.0(2) . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
N2 C3 N4 120.9(3) . . ?
N2 C3 C2 120.0(3) . . ?
N4 C3 C2 119.1(3) . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.3 . . ?
N2 C7 H7B 109.1 . . ?
H7A C7 H7B 108.2 . . ?
N2 C7 H7C1 114.5 . . ?
H7A C7 H7C1 90.7 . . ?
H7B C7 H7C1 122.7 . . ?
N2 C7 H7C2 116.8 . . ?
H7A C7 H7C2 124.1 . . ?
H7B C7 H7C2 85.3 . . ?
H7C1 C7 H7C2 42.5 . . ?
C9 C8 C13 120.6(3) . . ?
C9 C8 N3 119.0(3) . . ?
C13 C8 N3 120.4(3) . . ?
C8 C9 C10 118.9(3) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C11 C10 C9 121.6(3) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C12 C11 C10 118.2(3) . . ?
C12 C11 C14 120.5(3) . . ?
C10 C11 C14 121.3(4) . . ?
C11 C12 C13 121.7(3) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C12 C13 C8 119.0(3) . . ?
C12 C13 H13 120.5 . . ?
C8 C13 H13 120.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 120.1(3) . . ?
C16 C15 N4 119.6(3) . . ?
C20 C15 N4 120.2(3) . . ?
C15 C16 C17 119.4(3) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C18 121.6(3) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C19 C18 C17 117.8(3) . . ?
C19 C18 C21 120.0(3) . . ?
C17 C18 C21 122.2(3) . . ?
C20 C19 C18 121.3(3) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C15 119.7(3) . . ?
C19 C20 H20 120.1 . . ?
C15 C20 H20 120.1 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Cl4 C22 Cl3 111.0(2) . . ?
Cl4 C22 H22A 109.4 . . ?
Cl3 C22 H22A 109.4 . . ?
Cl4 C22 H22B 109.4 . . ?
Cl3 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?

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
C4 N1 C1 N3 -2.9(5) . . . . ?
C5 N1 C1 N3 168.7(3) . . . . ?
C4 N1 C1 C2 178.0(3) . . . . ?
C5 N1 C1 C2 -10.4(5) . . . . ?
C8 N3 C1 N1 179.3(3) . . . . ?
C8 N3 C1 C2 -1.5(5) . . . . ?
N1 C1 C2 C3 -129.3(3) . . . . ?
N3 C1 C2 C3 51.6(4) . . . . ?
C7 N2 C3 N4 174.4(3) . . . . ?
C6 N2 C3 N4 -0.3(5) . . . . ?
C7 N2 C3 C2 -6.6(5) . . . . ?
C6 N2 C3 C2 178.7(3) . . . . ?
C15 N4 C3 N2 -163.0(3) . . . . ?
C15 N4 C3 C2 18.0(4) . . . . ?
C1 C2 C3 N2 -136.1(3) . . . . ?
C1 C2 C3 N4 43.0(4) . . . . ?
C1 N3 C8 C9 -115.2(4) . . . . ?
C1 N3 C8 C13 66.3(4) . . . . ?
C13 C8 C9 C10 -2.3(5) . . . . ?
N3 C8 C9 C10 179.2(3) . . . . ?
C8 C9 C10 C11 0.8(5) . . . . ?
C9 C10 C11 C12 0.8(6) . . . . ?
C9 C10 C11 C14 179.8(3) . . . . ?
C10 C11 C12 C13 -1.0(6) . . . . ?
C14 C11 C12 C13 180.0(4) . . . . ?
C11 C12 C13 C8 -0.4(5) . . . . ?
C9 C8 C13 C12 2.1(5) . . . . ?
N3 C8 C13 C12 -179.4(3) . . . . ?
C3 N4 C15 C16 -127.3(3) . . . . ?
C3 N4 C15 C20 55.3(4) . . . . ?
C20 C15 C16 C17 -2.9(5) . . . . ?
N4 C15 C16 C17 179.7(3) . . . . ?
C15 C16 C17 C18 0.0(5) . . . . ?
C16 C17 C18 C19 2.2(5) . . . . ?
C16 C17 C18 C21 -177.9(3) . . . . ?
C17 C18 C19 C20 -1.7(5) . . . . ?
C21 C18 C19 C20 178.4(3) . . . . ?
C18 C19 C20 C15 -1.1(5) . . . . ?
C16 C15 C20 C19 3.4(5) . . . . ?
N4 C15 C20 C19 -179.2(3) . . . . ?

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
O1 H1O Cl1 0.84(2) 2.42(2) 3.265(3) 179(5) 1_455 yes
O1 H2O Cl2 0.86(2) 2.50(3) 3.347(3) 170(4) 2_564 yes
O2 H3O Cl2 0.87(2) 2.38(3) 3.220(3) 164(4) . yes
O2 H4O Cl2 0.88(2) 2.40(3) 3.267(3) 174(4) 4_556 yes
N3 H3N Cl1 0.87(2) 2.34(3) 3.134(3) 150(3) . yes
N4 H4N Cl1 0.87(2) 2.26(2) 3.088(3) 158(3) 1_455 yes

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.055

