# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_p212121_a
_database_code_depnum_ccdc_archive 'CCDC 2179467'
loop_
_audit_author_name
_audit_author_address
'Aidan Brock'
;Queensland University of Technology
Australia
;
_audit_update_record             
;
2022-06-16 deposited with the CCDC.	2022-08-16 downloaded from the CCDC.
;
_audit_creation_date             2021-01-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H21 N O3 S'
_chemical_formula_sum            'C14 H21 N O3 S'
_chemical_formula_weight         283.38
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   7.8310(16)
_cell_length_b                   8.2750(17)
_cell_length_c                   22.589(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1463.8(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    27128
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      32.299
_cell_measurement_theta_min      1.803
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.996
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            27128
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.299
_diffrn_reflns_theta_min         1.803
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measurement_device_type  'Eiger 16M'
_diffrn_measurement_method       'Phi scans'
_diffrn_radiation_monochromator  'Silicon double crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'MX2 Beamline Australian Synchrotron'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.875
_reflns_number_gt                4545
_reflns_number_total             4577
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 1929 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(2)
_refine_ls_extinction_coef       0.058(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         4577
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0513P)²+0.2794P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0895
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C1(H1), C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C9(H9A,H9B,
 H9C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.42829(5) 0.76282(4) 0.41771(2) 0.01793(11) Uani 1 1 d . . . . .
O002 O 0.66743(14) 0.55212(12) 0.40534(5) 0.0179(2) Uani 1 1 d . . . . .
O2 O 0.29642(17) 0.80091(16) 0.46029(6) 0.0261(3) Uani 1 1 d . . . . .
O1 O 0.38053(18) 0.74713(18) 0.35653(5) 0.0292(3) Uani 1 1 d . . . . .
N1 N 0.68817(16) 0.38165(15) 0.39491(6) 0.0156(2) Uani 1 1 d . . . . .
C13 C 0.52461(19) 0.57872(19) 0.44189(6) 0.0180(3) Uani 1 1 d . . . . .
H13A H 0.560381 0.587710 0.483793 0.022 Uiso 1 1 calc R U . . .
H13B H 0.442761 0.488073 0.438285 0.022 Uiso 1 1 calc R U . . .
C6 C 1.0011(2) 0.0605(2) 0.37539(7) 0.0208(3) Uani 1 1 d . . . . .
H6 H 1.080818 0.055244 0.407032 0.025 Uiso 1 1 calc R U . . .
C10 C 0.4647(2) 0.3025(2) 0.32409(8) 0.0245(3) Uani 1 1 d . . . . .
H10A H 0.434297 0.214441 0.351138 0.037 Uiso 1 1 calc R U . . .
H10B H 0.441544 0.269143 0.283232 0.037 Uiso 1 1 calc R U . . .
H10C H 0.396558 0.398366 0.333581 0.037 Uiso 1 1 calc R U . . .
C4 C 0.7690(2) 0.19628(19) 0.32508(7) 0.0180(3) Uani 1 1 d . . . . .
C11 C 0.8604(2) 0.2854(2) 0.47804(6) 0.0199(3) Uani 1 1 d . . . . .
H11A H 0.825604 0.379285 0.501563 0.030 Uiso 1 1 calc R U . . .
H11B H 0.974248 0.250011 0.490563 0.030 Uiso 1 1 calc R U . . .
H11C H 0.778541 0.197310 0.483984 0.030 Uiso 1 1 calc R U . . .
C5 C 0.88663(19) 0.18887(18) 0.37130(6) 0.0173(3) Uani 1 1 d . . . . .
C8 C 0.86487(18) 0.33153(17) 0.41250(6) 0.0161(2) Uani 1 1 d . . . . .
C12 C 1.0048(2) 0.4586(2) 0.40225(7) 0.0225(3) Uani 1 1 d . . . . .
H12A H 1.006193 0.489755 0.360394 0.034 Uiso 1 1 calc R U . . .
H12B H 1.115990 0.413241 0.413164 0.034 Uiso 1 1 calc R U . . .
H12C H 0.981392 0.554023 0.426658 0.034 Uiso 1 1 calc R U . . .
C9 C 0.7031(2) 0.4768(2) 0.28727(7) 0.0251(3) Uani 1 1 d . . . . .
H9A H 0.636531 0.574039 0.296243 0.038 Uiso 1 1 calc R U . . .
H9B H 0.678276 0.441355 0.246774 0.038 Uiso 1 1 calc R U . . .
H9C H 0.825104 0.500919 0.290956 0.038 Uiso 1 1 calc R U . . .
C1 C 0.9969(2) -0.0598(2) 0.33241(8) 0.0233(3) Uani 1 1 d . . . . .
H1 H 1.074245 -0.148048 0.334677 0.028 Uiso 1 1 calc R U . . .
C3 C 0.7652(2) 0.0766(2) 0.28173(7) 0.0232(3) Uani 1 1 d . . . . .
H3 H 0.686153 0.082398 0.249894 0.028 Uiso 1 1 calc R U . . .
C7 C 0.6550(2) 0.34221(19) 0.33083(7) 0.0180(3) Uani 1 1 d . . . . .
C2 C 0.8796(2) -0.0517(2) 0.28600(8) 0.0246(3) Uani 1 1 d . . . . .
H2 H 0.877787 -0.134715 0.256956 0.029 Uiso 1 1 calc R U . . .
C14 C 0.5958(2) 0.90309(19) 0.42416(8) 0.0255(3) Uani 1 1 d . . . . .
H14A H 0.552326 1.012067 0.416349 0.038 Uiso 1 1 calc R U . . .
H14B H 0.685413 0.876875 0.395427 0.038 Uiso 1 1 calc R U . . .
H14C H 0.643138 0.898524 0.464285 0.038 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4460(12) . ?
S1 O1 1.4376(12) . ?
S1 C13 1.7855(16) . ?
S1 C14 1.7577(18) . ?
O002 N1 1.4394(16) . ?
O002 C13 1.4074(18) . ?
N1 C8 1.4982(19) . ?
N1 C7 1.5067(19) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C6 H6 0.9500 . ?
C6 C5 1.393(2) . ?
C6 C1 1.391(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 C7 1.534(2) . ?
C4 C5 1.394(2) . ?
C4 C3 1.393(2) . ?
C4 C7 1.508(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 C8 1.529(2) . ?
C5 C8 1.513(2) . ?
C8 C12 1.536(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C9 C7 1.533(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.395(2) . ?
C3 H3 0.9500 . ?
C3 C2 1.393(2) . ?
C2 H2 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
O2 S1 C13 106.52(8) . . ?
O2 S1 C14 109.51(8) . . ?
O1 S1 O2 118.25(8) . . ?
O1 S1 C13 109.08(8) . . ?
O1 S1 C14 109.48(9) . . ?
C14 S1 C13 102.87(8) . . ?
C13 O002 N1 109.81(11) . . ?
O002 N1 C8 109.40(11) . . ?
O002 N1 C7 110.49(11) . . ?
C8 N1 C7 110.75(11) . . ?
S1 C13 H13A 110.4 . . ?
S1 C13 H13B 110.4 . . ?
O002 C13 S1 106.84(10) . . ?
O002 C13 H13A 110.4 . . ?
O002 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
C1 C6 C5 118.96(14) . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
C5 C4 C7 111.25(13) . . ?
C3 C4 C5 120.63(14) . . ?
C3 C4 C7 128.11(14) . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
C6 C5 C4 120.57(14) . . ?
C6 C5 C8 128.80(13) . . ?
C4 C5 C8 110.62(12) . . ?
N1 C8 C11 107.74(12) . . ?
N1 C8 C5 99.02(11) . . ?
N1 C8 C12 115.42(12) . . ?
C11 C8 C12 109.46(12) . . ?
C5 C8 C11 113.78(12) . . ?
C5 C8 C12 111.17(13) . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
C6 C1 H1 119.8 . . ?
C6 C1 C2 120.36(15) . . ?
C2 C1 H1 119.8 . . ?
C4 C3 H3 120.7 . . ?
C2 C3 C4 118.65(15) . . ?
C2 C3 H3 120.7 . . ?
N1 C7 C10 108.03(12) . . ?
N1 C7 C4 98.85(11) . . ?
N1 C7 C9 114.64(13) . . ?
C4 C7 C10 113.28(13) . . ?
C4 C7 C9 112.40(13) . . ?
C9 C7 C10 109.32(13) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.82(15) . . ?
C3 C2 H2 119.6 . . ?
S1 C14 H14A 109.5 . . ?
S1 C14 H14B 109.5 . . ?
S1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
O002 N1 C8 C11 88.89(13) . . . . ?
O002 N1 C8 C5 -152.46(11) . . . . ?
O002 N1 C8 C12 -33.75(16) . . . . ?
O002 N1 C7 C10 -90.55(14) . . . . ?
O002 N1 C7 C4 151.33(11) . . . . ?
O002 N1 C7 C9 31.61(17) . . . . ?
O2 S1 C13 O002 -172.33(10) . . . . ?
O1 S1 C13 O002 58.99(12) . . . . ?
N1 O002 C13 S1 -144.78(10) . . . . ?
C13 O002 N1 C8 -125.01(12) . . . . ?
C13 O002 N1 C7 112.81(13) . . . . ?
C6 C5 C8 N1 -160.33(15) . . . . ?
C6 C5 C8 C11 -46.3(2) . . . . ?
C6 C5 C8 C12 77.8(2) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C4 C5 C8 N1 18.52(15) . . . . ?
C4 C5 C8 C11 132.54(14) . . . . ?
C4 C5 C8 C12 -103.32(14) . . . . ?
C4 C3 C2 C1 -0.6(3) . . . . ?
C5 C6 C1 C2 0.0(2) . . . . ?
C5 C4 C3 C2 0.9(3) . . . . ?
C5 C4 C7 N1 -17.11(16) . . . . ?
C5 C4 C7 C10 -131.20(15) . . . . ?
C5 C4 C7 C9 104.26(16) . . . . ?
C8 N1 C7 C10 148.07(12) . . . . ?
C8 N1 C7 C4 29.95(15) . . . . ?
C8 N1 C7 C9 -89.77(15) . . . . ?
C1 C6 C5 C4 0.4(2) . . . . ?
C1 C6 C5 C8 179.10(15) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C3 C4 C5 C8 -179.78(15) . . . . ?
C3 C4 C7 N1 161.71(16) . . . . ?
C3 C4 C7 C10 47.6(2) . . . . ?
C3 C4 C7 C9 -76.9(2) . . . . ?
C7 N1 C8 C11 -149.09(12) . . . . ?
C7 N1 C8 C5 -30.44(14) . . . . ?
C7 N1 C8 C12 88.27(15) . . . . ?
C7 C4 C5 C6 178.10(14) . . . . ?
C7 C4 C5 C8 -0.86(18) . . . . ?
C7 C4 C3 C2 -177.81(16) . . . . ?
C14 S1 C13 O002 -57.17(11) . . . . ?

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

data_p21onc_a
_database_code_depnum_ccdc_archive 'CCDC 2179468'
loop_
_audit_author_name
_audit_author_address
'Aidan Brock'
;Queensland University of Technology
Australia
;
_audit_update_record             
;
2022-06-16 deposited with the CCDC.	2022-08-16 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_p21onc_a            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.958 Why?
RESPONSE: Crystals were small and weakly diffracting, requiring synchrotron radiation. This is reflected in the relatively low resolution of the diffraction data. Nevertheless, the connectivity is unambiguous.
;
# Added during the CSD deposition process: Thursday 16 June 2022 04:52 AM
# end Validation Reply Form

_audit_creation_date             2021-01-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H19 N O3 S'
_chemical_formula_sum            'C13 H19 N O3 S'
_chemical_formula_weight         269.35
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.307(3)
_cell_length_b                   10.929(2)
_cell_length_c                   10.159(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.12(3)
_cell_angle_gamma                90
_cell_volume                     1366.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18820
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.099
_cell_measurement_theta_min      1.655
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0935
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18820
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.099
_diffrn_reflns_theta_min         1.655
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Eiger 16M'
_diffrn_measurement_method       'Phi scans'
_diffrn_radiation_monochromator  'Silicon double crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'MX2 Beamline Australian Synchrotron'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2557
_reflns_number_total             2866
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.129
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2866
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0650
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1192P)²+0.5918P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1960
_refine_ls_wR_factor_ref         0.2008
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{O002, O0}
{O003, O1}
{C00J, C00K}
3. Uiso/Uaniso restraints and constraints
Uanis(O005) = Uanis(O2)
Uanis(O002) = Uanis(O0)
Uanis(O003) = Uanis(O1)
Uanis(C00J) = Uanis(C00K)
4. Others
 Fixed Sof: S2(0.75) O002(0.75) O003(0.75) O005(0.75) C00J(0.75) H00A(0.75)
 H00B(0.75) H00C(0.75) S1(0.25) O2(0.25) O0(0.25) O1(0.25) C00K(0.25)
 H00D(0.25) H00E(0.25) H00F(0.25)
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C1(H1), C2(H2), C3(H3)
5.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,
 H12C), C00J(H00A,H00B,H00C), C00K(H00D,H00E,H00F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.74989(5) 0.32833(5) 0.68001(6) 0.0328(2) Uani 0.75 1 d . . P A 1
O002 O 0.65001(11) 0.30215(14) 0.74769(16) 0.0430(4) Uani 0.75 1 d . . P A 1
O003 O 0.84988(12) 0.30206(14) 0.74815(16) 0.0433(4) Uani 0.75 1 d . . P A 1
N1 N 0.75008(11) 0.54531(15) 0.74885(14) 0.0325(4) Uani 1 1 d . . . . .
O005 O 0.74959(16) 0.46771(15) 0.63151(17) 0.0350(4) Uani 0.75 1 d . . P A 1
C6 C 0.69378(15) 0.75203(16) 0.75071(19) 0.0308(4) Uani 1 1 d . . . . .
C5 C 0.80621(15) 0.75196(16) 0.75039(19) 0.0308(4) Uani 1 1 d . . . . .
C8 C 0.64843(14) 0.62368(16) 0.74827(18) 0.0309(4) Uani 1 1 d . . . . .
C7 C 0.85166(14) 0.62360(16) 0.74820(19) 0.0312(4) Uani 1 1 d . . . . .
C4 C 0.86392(15) 0.86148(17) 0.7521(2) 0.0353(4) Uani 1 1 d . . . . .
H4 H 0.941109 0.861333 0.752157 0.042 Uiso 1 1 calc R U . . .
C1 C 0.63617(15) 0.86130(17) 0.7525(2) 0.0354(4) Uani 1 1 d . . . . .
H1 H 0.558978 0.861070 0.752930 0.043 Uiso 1 1 calc R U . . .
C11 C 0.57835(16) 0.60336(18) 0.6265(2) 0.0381(4) Uani 1 1 d . . . . .
H11A H 0.621813 0.618106 0.547374 0.057 Uiso 1 1 calc R U . . .
H11B H 0.516606 0.659960 0.628004 0.057 Uiso 1 1 calc R U . . .
H11C H 0.551538 0.518928 0.625833 0.057 Uiso 1 1 calc R U . . .
C9 C 0.91688(17) 0.59679(18) 0.8729(2) 0.0385(5) Uani 1 1 d . . . . .
H9A H 0.870506 0.608536 0.950131 0.058 Uiso 1 1 calc R U . . .
H9B H 0.979116 0.652546 0.877867 0.058 Uiso 1 1 calc R U . . .
H9C H 0.942903 0.512067 0.870609 0.058 Uiso 1 1 calc R U . . .
C10 C 0.92124(16) 0.60332(19) 0.6260(2) 0.0384(5) Uani 1 1 d . . . . .
H10A H 0.948167 0.518934 0.625291 0.058 Uiso 1 1 calc R U . . .
H10B H 0.982908 0.660030 0.627304 0.058 Uiso 1 1 calc R U . . .
H10C H 0.877326 0.617957 0.546996 0.058 Uiso 1 1 calc R U . . .
C12 C 0.58366(17) 0.59665(18) 0.8731(2) 0.0387(5) Uani 1 1 d . . . . .
H12A H 0.557329 0.512057 0.870515 0.058 Uiso 1 1 calc R U . . .
H12B H 0.521647 0.652666 0.878487 0.058 Uiso 1 1 calc R U . . .
H12C H 0.630458 0.607892 0.950308 0.058 Uiso 1 1 calc R U . . .
C2 C 0.69324(16) 0.97083(17) 0.7538(2) 0.0379(5) Uani 1 1 d . . . . .
H2 H 0.654873 1.046249 0.754679 0.046 Uiso 1 1 calc R U . . .
C3 C 0.80676(16) 0.97085(18) 0.7539(2) 0.0380(5) Uani 1 1 d . . . . .
H3 H 0.845069 1.046306 0.755061 0.046 Uiso 1 1 calc R U . . .
C00J C 0.7497(2) 0.2587(2) 0.5161(3) 0.0645(8) Uani 0.75 1 d . . P A 1
H00A H 0.745750 0.169513 0.524642 0.097 Uiso 0.75 1 calc R U P A 1
H00B H 0.816471 0.281226 0.469754 0.097 Uiso 0.75 1 calc R U P A 1
H00C H 0.686608 0.288170 0.466290 0.097 Uiso 0.75 1 calc R U P A 1
S1 S 0.75008(17) 0.32765(19) 0.8207(3) 0.0469(6) Uani 0.25 1 d . . P A 2
O2 O 0.7504(5) 0.4684(5) 0.8697(5) 0.0350(4) Uani 0.25 1 d . . P A 2
O0 O 0.65001(11) 0.30215(14) 0.74769(16) 0.0430(4) Uani 0.25 1 d . . P A 2
O1 O 0.84988(12) 0.30206(14) 0.74815(16) 0.0433(4) Uani 0.25 1 d . . P A 2
C00K C 0.7497(2) 0.2587(2) 0.5161(3) 0.0645(8) Uani 0.25 1 d . . P B 2
H00D H 0.684386 0.309331 0.525491 0.097 Uiso 0.25 1 calc R U P B 2
H00E H 0.814419 0.310137 0.525823 0.097 Uiso 0.25 1 calc R U P B 2
H00F H 0.749961 0.195208 0.584234 0.097 Uiso 0.25 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
S2 O002 1.4384(16) . ?
S2 O003 1.4396(17) . ?
S2 O005 1.6010(18) . ?
S2 C00J 1.830(3) . ?
N1 O005 1.463(2) . ?
N1 C8 1.516(2) . ?
N1 C7 1.515(2) . ?
N1 O2 1.488(5) . ?
C6 C5 1.384(3) . ?
C6 C8 1.510(2) . ?
C6 C1 1.389(3) . ?
C5 C7 1.511(2) . ?
C5 C4 1.392(3) . ?
C8 C11 1.523(3) . ?
C8 C12 1.528(3) . ?
C7 C9 1.526(3) . ?
C7 C10 1.526(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.387(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.388(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C2 H2 0.9500 . ?
C2 C3 1.397(3) . ?
C3 H3 0.9500 . ?
C00J H00A 0.9800 . ?
C00J H00B 0.9800 . ?
C00J H00C 0.9800 . ?
S1 O2 1.617(5) . ?
S1 O0 1.463(3) . ?
S1 O1 1.461(3) . ?
S1 C00K 2.199(4) 4_566 ?
C00K H00D 0.9800 . ?
C00K H00E 0.9800 . ?
C00K H00F 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
O002 S2 O003 117.45(10) . . ?
O002 S2 O005 109.57(10) . . ?
O002 S2 C00J 110.63(12) . . ?
O003 S2 O005 109.83(10) . . ?
O003 S2 C00J 110.75(12) . . ?
O005 S2 C00J 96.63(11) . . ?
O005 N1 C8 108.80(14) . . ?
O005 N1 C7 109.02(13) . . ?
C7 N1 C8 111.21(15) . . ?
O2 N1 C8 108.8(2) . . ?
O2 N1 C7 108.8(3) . . ?
N1 O005 S2 107.50(13) . . ?
C5 C6 C8 111.66(14) . . ?
C5 C6 C1 120.73(15) . . ?
C1 C6 C8 127.61(18) . . ?
C6 C5 C7 111.77(14) . . ?
C6 C5 C4 120.65(15) . . ?
C4 C5 C7 127.59(18) . . ?
N1 C8 C11 112.75(15) . . ?
N1 C8 C12 108.63(15) . . ?
C6 C8 N1 102.69(14) . . ?
C6 C8 C11 110.95(16) . . ?
C6 C8 C12 111.07(15) . . ?
C11 C8 C12 110.51(16) . . ?
N1 C7 C9 108.69(15) . . ?
N1 C7 C10 112.71(15) . . ?
C5 C7 N1 102.64(14) . . ?
C5 C7 C9 111.11(16) . . ?
C5 C7 C10 110.82(16) . . ?
C10 C7 C9 110.61(16) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 C5 118.84(18) . . ?
C3 C4 H4 120.6 . . ?
C6 C1 H1 120.5 . . ?
C2 C1 C6 118.90(18) . . ?
C2 C1 H1 120.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.41(16) . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 120.47(16) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
S2 C00J H00A 109.5 . . ?
S2 C00J H00B 109.5 . . ?
S2 C00J H00C 109.5 . . ?
H00A C00J H00B 109.5 . . ?
H00A C00J H00C 109.5 . . ?
H00B C00J H00C 109.5 . . ?
O2 S1 C00K 97.5(2) . 4_566 ?
O0 S1 O2 109.8(3) . . ?
O0 S1 C00K 111.86(16) . 4_566 ?
O1 S1 O2 109.7(2) . . ?
O1 S1 O0 114.57(19) . . ?
O1 S1 C00K 112.14(16) . 4_566 ?
N1 O2 S1 106.5(3) . . ?
S1 C00K H00D 109.5 4_565 . ?
S1 C00K H00E 109.5 4_565 . ?
S1 C00K H00F 109.5 4_565 . ?
H00D C00K H00E 109.5 . . ?
H00D C00K H00F 109.5 . . ?
H00E C00K H00F 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
O002 S2 O005 N1 65.49(15) . . . . ?
O003 S2 O005 N1 -64.92(15) . . . . ?
O005 N1 C8 C6 -121.46(16) . . . . ?
O005 N1 C8 C11 -2.0(2) . . . . ?
O005 N1 C8 C12 120.84(16) . . . . ?
O005 N1 C7 C5 121.23(16) . . . . ?
O005 N1 C7 C9 -121.03(16) . . . . ?
O005 N1 C7 C10 2.0(2) . . . . ?
C6 C5 C7 N1 -0.6(2) . . . . ?
C6 C5 C7 C9 -116.7(2) . . . . ?
C6 C5 C7 C10 119.9(2) . . . . ?
C6 C5 C4 C3 -0.2(3) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
C5 C6 C8 N1 1.0(2) . . . . ?
C5 C6 C8 C11 -119.8(2) . . . . ?
C5 C6 C8 C12 116.9(2) . . . . ?
C5 C6 C1 C2 0.1(3) . . . . ?
C5 C4 C3 C2 0.0(3) . . . . ?
C8 N1 O005 S2 -119.39(14) . . . . ?
C8 N1 C7 C5 1.26(17) . . . . ?
C8 N1 C7 C9 119.00(16) . . . . ?
C8 N1 C7 C10 -118.00(17) . . . . ?
C8 N1 O2 S1 119.2(3) . . . . ?
C8 C6 C5 C7 -0.2(3) . . . . ?
C8 C6 C5 C4 179.86(16) . . . . ?
C8 C6 C1 C2 -179.59(19) . . . . ?
C7 N1 O005 S2 119.16(14) . . . . ?
C7 N1 C8 C6 -1.37(17) . . . . ?
C7 N1 C8 C11 118.10(16) . . . . ?
C7 N1 C8 C12 -119.07(16) . . . . ?
C7 N1 O2 S1 -119.4(3) . . . . ?
C7 C5 C4 C3 179.91(19) . . . . ?
C4 C5 C7 N1 179.28(19) . . . . ?
C4 C5 C7 C9 63.3(3) . . . . ?
C4 C5 C7 C10 -60.1(3) . . . . ?
C1 C6 C5 C7 -179.96(16) . . . . ?
C1 C6 C5 C4 0.1(4) . . . . ?
C1 C6 C8 N1 -179.31(19) . . . . ?
C1 C6 C8 C11 60.0(3) . . . . ?
C1 C6 C8 C12 -63.4(3) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C00J S2 O005 N1 -179.82(14) . . . . ?
O2 N1 C8 C6 118.5(3) . . . . ?
O2 N1 C8 C11 -122.1(3) . . . . ?
O2 N1 C8 C12 0.8(3) . . . . ?
O2 N1 C7 C5 -118.6(3) . . . . ?
O2 N1 C7 C9 -0.9(3) . . . . ?
O2 N1 C7 C10 122.1(3) . . . . ?
O0 S1 O2 N1 -63.2(4) . . . . ?
O1 S1 O2 N1 63.5(4) . . . . ?
C00K S1 O2 N1 -179.7(3) 4_566 . . . ?

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

data_p21onm_a
_database_code_depnum_ccdc_archive 'CCDC 2179470'
loop_
_audit_author_name
_audit_author_address
'Aidan Brock'
;Queensland University of Technology
Australia
;
_audit_update_record             
;
2022-06-16 deposited with the CCDC.	2022-08-16 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_p21onm_a            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.951 Why?
RESPONSE: Crystals were small and weakly diffracting, requiring synchrotron radiation. This is reflected in the relatively low resolution of the diffraction data. Nevertheless, the connectivity is unambiguous.
;
# Added during the CSD deposition process: Thursday 16 June 2022 04:52 AM
# end Validation Reply Form

_audit_creation_date             2020-10-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H13 N O2'
_chemical_formula_sum            'C12 H13 N O2'
_chemical_formula_weight         203.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   7.9850(16)
_cell_length_b                   6.6850(13)
_cell_length_c                   9.4400(19)
_cell_angle_alpha                90
_cell_angle_beta                 100.86(3)
_cell_angle_gamma                90
_cell_volume                     494.88(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6912
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.328
_cell_measurement_theta_min      2.197
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.782
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6912
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.782
_diffrn_reflns_theta_full        25.244
_diffrn_reflns_theta_max         29.328
_diffrn_reflns_theta_min         2.197
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.782
_diffrn_measurement_device_type  'Eiger 2 9M'
_diffrn_measurement_method       'Phi scans'
_diffrn_radiation_monochromator  'Silicon double crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.7108
_diffrn_source                   'MX1 Beamline Australian Synchrotron'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1093
_reflns_number_total             1144
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.017(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1144
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0660P)²+0.0938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1126
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H11A(0.5) H11B(0.5) H11C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C3(H3), C4(H4)
3.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.26101(12) 0.250000 0.56627(11) 0.0246(3) Uani 1 2 d S T P . .
O1 O 0.48415(13) 0.250000 0.38405(10) 0.0256(3) Uani 1 2 d S T P . .
N1 N 0.70595(14) 0.250000 0.57208(11) 0.0168(3) Uani 1 2 d S T P . .
C8 C 0.53887(16) 0.250000 0.51521(13) 0.0173(3) Uani 1 2 d S T P . .
C1 C 0.48024(16) 0.250000 0.77380(13) 0.0172(3) Uani 1 2 d S T P . .
C9 C 0.41236(16) 0.250000 0.61820(14) 0.0178(3) Uani 1 2 d S T P . .
C7 C 0.78592(15) 0.250000 0.72695(13) 0.0162(3) Uani 1 2 d S T P . .
C6 C 0.65533(16) 0.250000 0.82494(13) 0.0167(3) Uani 1 2 d S T P . .
C5 C 0.71293(18) 0.250000 0.97475(14) 0.0211(3) Uani 1 2 d S T P . .
H5 H 0.831957 0.250000 1.012446 0.025 Uiso 1 2 calc R U P . .
C11 C 0.81994(16) 0.250000 0.46645(14) 0.0207(3) Uani 1 2 d S T P . .
H11A H 0.789387 0.139114 0.398597 0.031 Uiso 0.5 1 calc R U P A -1
H11B H 0.938203 0.233992 0.516877 0.031 Uiso 0.5 1 calc R U P A -1
H11C H 0.808161 0.376894 0.413519 0.031 Uiso 0.5 1 calc R U P A -1
C2 C 0.36488(18) 0.250000 0.86955(16) 0.0216(3) Uani 1 2 d S T P . .
H2 H 0.245630 0.250000 0.832840 0.026 Uiso 1 2 calc R U P . .
C3 C 0.42429(19) 0.250000 1.01644(15) 0.0244(3) Uani 1 2 d S T P . .
H3 H 0.346520 0.250000 1.081202 0.029 Uiso 1 2 calc R U P . .
C10 C 0.89470(11) 0.44142(14) 0.75671(10) 0.0218(3) Uani 1 1 d . . . . .
H10A H 0.984707 0.439254 0.699056 0.033 Uiso 1 1 calc R U . . .
H10B H 0.946411 0.447660 0.859362 0.033 Uiso 1 1 calc R U . . .
H10C H 0.822104 0.558973 0.730638 0.033 Uiso 1 1 calc R U . . .
C4 C 0.5985(2) 0.250000 1.06878(14) 0.0251(3) Uani 1 2 d S T P . .
H4 H 0.640092 0.250000 1.169930 0.030 Uiso 1 2 calc R U P . .


_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
O2 C9 1.2156(17) . ?
O1 C8 1.2328(16) . ?
N1 C8 1.3410(17) . ?
N1 C7 1.4810(16) . ?
N1 C11 1.4713(15) . ?
C8 C9 1.5283(17) . ?
C1 C9 1.4668(19) . ?
C1 C6 1.3904(19) . ?
C1 C2 1.4068(18) . ?
C7 C6 1.5187(16) . ?
C7 C10 1.5424(11) 4_565 ?
C7 C10 1.5424(11) . ?
C6 C5 1.4023(18) . ?
C5 H5 0.9500 . ?
C5 C4 1.3885(19) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C2 H2 0.9500 . ?
C2 C3 1.378(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C4 H4 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
C8 N1 C7 127.34(10) . . ?
C8 N1 C11 115.12(10) . . ?
C11 N1 C7 117.54(10) . . ?
O1 C8 N1 122.66(11) . . ?
O1 C8 C9 119.16(12) . . ?
N1 C8 C9 118.18(11) . . ?
C6 C1 C9 120.35(11) . . ?
C6 C1 C2 120.94(13) . . ?
C2 C1 C9 118.70(13) . . ?
O2 C9 C8 118.01(12) . . ?
O2 C9 C1 123.75(12) . . ?
C1 C9 C8 118.25(12) . . ?
N1 C7 C6 112.55(10) . . ?
N1 C7 C10 107.64(6) . . ?
N1 C7 C10 107.64(6) . 4_565 ?
C6 C7 C10 108.47(6) . 4_565 ?
C6 C7 C10 108.47(6) . . ?
C10 C7 C10 112.12(10) . 4_565 ?
C1 C6 C7 123.33(12) . . ?
C1 C6 C5 117.87(12) . . ?
C5 C6 C7 118.81(12) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 120.96(13) . . ?
C4 C5 H5 119.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.23(14) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.39(12) . . ?
C4 C3 H3 120.3 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.61(13) . . ?
C3 C4 H4 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C8 C9 O2 0.000(0) . . . . ?
O1 C8 C9 C1 180.000(0) . . . . ?
N1 C8 C9 O2 180.000(0) . . . . ?
N1 C8 C9 C1 0.000(0) . . . . ?
N1 C7 C6 C1 0.000(1) . . . . ?
N1 C7 C6 C5 180.000(0) . . . . ?
C8 N1 C7 C6 0.000(0) . . . . ?
C8 N1 C7 C10 -119.47(6) . . . . ?
C8 N1 C7 C10 119.47(6) . . . 4_565 ?
C1 C6 C5 C4 0.000(1) . . . . ?
C1 C2 C3 C4 0.000(1) . . . . ?
C9 C1 C6 C7 0.000(1) . . . . ?
C9 C1 C6 C5 180.000(1) . . . . ?
C9 C1 C2 C3 180.000(1) . . . . ?
C7 N1 C8 O1 180.000(0) . . . . ?
C7 N1 C8 C9 0.000(0) . . . . ?
C7 C6 C5 C4 180.000(1) . . . . ?
C6 C1 C9 O2 180.000(0) . . . . ?
C6 C1 C9 C8 0.000(1) . . . . ?
C6 C1 C2 C3 0.000(1) . . . . ?
C6 C5 C4 C3 0.000(1) . . . . ?
C11 N1 C8 O1 0.000(0) . . . . ?
C11 N1 C8 C9 180.000(0) . . . . ?
C11 N1 C7 C6 180.000(0) . . . . ?
C11 N1 C7 C10 -60.53(6) . . . 4_565 ?
C11 N1 C7 C10 60.53(6) . . . . ?
C2 C1 C9 O2 0.000(1) . . . . ?
C2 C1 C9 C8 180.000(0) . . . . ?
C2 C1 C6 C7 180.000(0) . . . . ?
C2 C1 C6 C5 0.000(1) . . . . ?
C2 C3 C4 C5 0.000(1) . . . . ?
C10 C7 C6 C1 118.99(7) . . . . ?
C10 C7 C6 C1 -118.99(7) 4_565 . . . ?
C10 C7 C6 C5 61.01(7) 4_565 . . . ?
C10 C7 C6 C5 -61.01(7) . . . . ?

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

data_pna21_a
_database_code_depnum_ccdc_archive 'CCDC 2179469'
loop_
_audit_author_name
_audit_author_address
'Aidan Brock'
;Queensland University of Technology
Australia
;
_audit_update_record             
;
2022-06-16 deposited with the CCDC.	2022-08-16 downloaded from the CCDC.
;
_audit_creation_date             2020-10-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H17 N O2'
_chemical_formula_sum            'C13 H17 N O2'
_chemical_formula_weight         219.27
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   11.509(2)
_cell_length_b                   14.815(3)
_cell_length_c                   7.0560(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1203.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15914
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.506
_cell_measurement_theta_min      2.241
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.923
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15914
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        25.244
_diffrn_reflns_theta_max         29.506
_diffrn_reflns_theta_min         2.241
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_device_type  'Eiger 2 9M'
_diffrn_measurement_method       'Phi scans'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.7108
_diffrn_source                   'MX1 Beamline Australian Synchrotron'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.827
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.842
_reflns_number_gt                2863
_reflns_number_total             2881
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 1287 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_extinction_coef       0.021(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2881
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0504P)²+0.1676P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0919
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C4(H4), C1(H1), C3(H3), C2(H2)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.12354(8) 0.35495(7) 0.32792(15) 0.0176(2) Uani 1 1 d . . . . .
O2 O 0.06232(11) 0.32597(9) 0.03734(18) 0.0269(3) Uani 1 1 d . . . . .
N1 N 0.22774(10) 0.38612(8) 0.42230(17) 0.0150(3) Uani 1 1 d . . . . .
C5 C 0.29044(13) 0.45354(10) 0.6951(2) 0.0158(3) Uani 1 1 d . . . . .
C6 C 0.33380(13) 0.36606(10) 0.6939(2) 0.0161(3) Uani 1 1 d . . . . .
C13 C 0.13812(14) 0.35314(10) 0.1374(2) 0.0195(3) Uani 1 1 d . . . . .
H13 H 0.208998 0.373578 0.083405 0.023 Uiso 1 1 calc R U . . .
C7 C 0.27883(13) 0.31087(10) 0.5376(2) 0.0159(3) Uani 1 1 d . . . . .
C4 C 0.32928(14) 0.51583(11) 0.8285(2) 0.0215(3) Uani 1 1 d . . . . .
H4 H 0.299724 0.575699 0.829282 0.026 Uiso 1 1 calc R U . . .
C11 C 0.07685(13) 0.46562(10) 0.6309(2) 0.0188(3) Uani 1 1 d . . . . .
H11A H 0.018754 0.467720 0.529495 0.028 Uiso 1 1 calc R U . . .
H11B H 0.067513 0.518371 0.713357 0.028 Uiso 1 1 calc R U . . .
H11C H 0.066218 0.410420 0.705485 0.028 Uiso 1 1 calc R U . . .
C12 C 0.21630(14) 0.55095(10) 0.4239(2) 0.0212(3) Uani 1 1 d . . . . .
H12A H 0.295263 0.551448 0.371925 0.032 Uiso 1 1 calc R U . . .
H12B H 0.204697 0.604578 0.502977 0.032 Uiso 1 1 calc R U . . .
H12C H 0.159932 0.551197 0.319819 0.032 Uiso 1 1 calc R U . . .
C8 C 0.19919(13) 0.46618(9) 0.5440(2) 0.0150(3) Uani 1 1 d . . . . .
C1 C 0.41514(13) 0.33839(11) 0.8274(2) 0.0202(3) Uani 1 1 d . . . . .
H1 H 0.443418 0.278147 0.827626 0.024 Uiso 1 1 calc R U . . .
C9 C 0.36737(14) 0.26131(11) 0.4142(3) 0.0232(3) Uani 1 1 d . . . . .
H9A H 0.327730 0.234204 0.305233 0.035 Uiso 1 1 calc R U . . .
H9B H 0.405014 0.213822 0.488860 0.035 Uiso 1 1 calc R U . . .
H9C H 0.426151 0.304141 0.369320 0.035 Uiso 1 1 calc R U . . .
C10 C 0.18964(13) 0.24401(10) 0.6185(3) 0.0206(3) Uani 1 1 d . . . . .
H10A H 0.136545 0.275993 0.703843 0.031 Uiso 1 1 calc R U . . .
H10B H 0.230202 0.196469 0.688850 0.031 Uiso 1 1 calc R U . . .
H10C H 0.145290 0.216941 0.514464 0.031 Uiso 1 1 calc R U . . .
C3 C 0.41226(15) 0.48892(12) 0.9609(2) 0.0250(3) Uani 1 1 d . . . . .
H3 H 0.440270 0.530954 1.051718 0.030 Uiso 1 1 calc R U . . .
C2 C 0.45442(14) 0.40059(12) 0.9607(2) 0.0239(3) Uani 1 1 d . . . . .
H2 H 0.510388 0.382753 1.052307 0.029 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 N1 1.4474(15) . ?
O1 C13 1.3548(19) . ?
O2 C13 1.192(2) . ?
N1 C7 1.5000(18) . ?
N1 C8 1.5005(17) . ?
C5 C6 1.389(2) . ?
C5 C4 1.392(2) . ?
C5 C8 1.508(2) . ?
C6 C7 1.512(2) . ?
C6 C1 1.390(2) . ?
C13 H13 0.9500 . ?
C7 C9 1.528(2) . ?
C7 C10 1.536(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.394(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 C8 1.536(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 C8 1.5276(19) . ?
C1 H1 0.9500 . ?
C1 C2 1.392(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C3 H3 0.9500 . ?
C3 C2 1.396(3) . ?
C2 H2 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
C13 O1 N1 111.11(11) . . ?
O1 N1 C7 109.71(10) . . ?
O1 N1 C8 109.50(10) . . ?
C7 N1 C8 111.29(11) . . ?
C6 C5 C4 120.49(14) . . ?
C6 C5 C8 111.20(13) . . ?
C4 C5 C8 128.27(13) . . ?
C5 C6 C7 111.02(13) . . ?
C5 C6 C1 120.88(14) . . ?
C1 C6 C7 128.08(14) . . ?
O1 C13 H13 119.9 . . ?
O2 C13 O1 120.25(15) . . ?
O2 C13 H13 119.9 . . ?
N1 C7 C6 99.08(11) . . ?
N1 C7 C9 108.03(12) . . ?
N1 C7 C10 114.76(12) . . ?
C6 C7 C9 113.36(13) . . ?
C6 C7 C10 110.91(13) . . ?
C9 C7 C10 110.34(12) . . ?
C5 C4 H4 120.5 . . ?
C5 C4 C3 118.92(15) . . ?
C3 C4 H4 120.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
N1 C8 C5 98.86(11) . . ?
N1 C8 C11 115.16(12) . . ?
N1 C8 C12 107.72(12) . . ?
C5 C8 C11 110.79(12) . . ?
C5 C8 C12 113.85(12) . . ?
C12 C8 C11 110.13(12) . . ?
C6 C1 H1 120.6 . . ?
C6 C1 C2 118.78(15) . . ?
C2 C1 H1 120.6 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C3 H3 119.8 . . ?
C4 C3 C2 120.37(15) . . ?
C2 C3 H3 119.8 . . ?
C1 C2 C3 120.55(15) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C7 C6 -149.59(11) . . . . ?
O1 N1 C7 C9 92.10(14) . . . . ?
O1 N1 C7 C10 -31.44(16) . . . . ?
O1 N1 C8 C5 150.57(11) . . . . ?
O1 N1 C8 C11 32.53(15) . . . . ?
O1 N1 C8 C12 -90.79(13) . . . . ?
N1 O1 C13 O2 177.25(14) . . . . ?
C5 C6 C7 N1 15.62(15) . . . . ?
C5 C6 C7 C9 129.85(14) . . . . ?
C5 C6 C7 C10 -105.38(14) . . . . ?
C5 C6 C1 C2 -1.3(2) . . . . ?
C5 C4 C3 C2 -0.8(2) . . . . ?
C6 C5 C4 C3 -0.1(2) . . . . ?
C6 C5 C8 N1 -18.13(15) . . . . ?
C6 C5 C8 C11 103.16(14) . . . . ?
C6 C5 C8 C12 -132.07(14) . . . . ?
C6 C1 C2 C3 0.4(2) . . . . ?
C13 O1 N1 C7 -113.71(13) . . . . ?
C13 O1 N1 C8 123.87(12) . . . . ?
C7 N1 C8 C5 29.11(14) . . . . ?
C7 N1 C8 C11 -88.93(15) . . . . ?
C7 N1 C8 C12 147.75(12) . . . . ?
C7 C6 C1 C2 -179.76(15) . . . . ?
C4 C5 C6 C7 179.84(14) . . . . ?
C4 C5 C6 C1 1.1(2) . . . . ?
C4 C5 C8 N1 163.88(15) . . . . ?
C4 C5 C8 C11 -74.83(19) . . . . ?
C4 C5 C8 C12 49.9(2) . . . . ?
C4 C3 C2 C1 0.6(3) . . . . ?
C8 N1 C7 C6 -28.24(14) . . . . ?
C8 N1 C7 C9 -146.55(12) . . . . ?
C8 N1 C7 C10 89.90(15) . . . . ?
C8 C5 C6 C7 1.68(17) . . . . ?
C8 C5 C6 C1 -177.06(13) . . . . ?
C8 C5 C4 C3 177.75(15) . . . . ?
C1 C6 C7 N1 -165.76(15) . . . . ?
C1 C6 C7 C9 -51.5(2) . . . . ?
C1 C6 C7 C10 73.24(19) . . . . ?

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

data_jcm20ab01
_database_code_depnum_ccdc_archive 'CCDC 2179471'
loop_
_audit_author_name
_audit_author_address
'Aidan Brock'
;Queensland University of Technology
Australia
;
_audit_update_record             
;
2022-06-16 deposited with the CCDC.	2022-08-16 downloaded from the CCDC.
;
_audit_creation_date             2020-09-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'F6 P, C12 H16 N'
_chemical_formula_sum            'C12 H16 F6 N P'
_chemical_formula_weight         319.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 N P F6 H18'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0096 0.0061 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.0667 0.0580 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   18.8169(6)
_cell_length_b                   6.4663(2)
_cell_length_c                   22.5305(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.669(3)
_cell_angle_gamma                90
_cell_volume                     2722.87(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13283
_cell_measurement_temperature    100.1(2)
_cell_measurement_theta_max      30.2710
_cell_measurement_theta_min      2.5940
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.871
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            19340
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         22.269
_diffrn_reflns_theta_min         2.365
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.1(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     30.00  55.00   0.50    5.00    --   -0.94  41.00  68.00   50
  2  ω    -30.00  16.00   0.50    5.00    --   -0.94 -37.00 120.00   92
  3  ω    -78.00  16.00   0.50    5.00    --   -0.94 -37.00  60.00  188
  4  ω    -77.00  16.00   0.50    5.00    --   -0.94 -41.00 -84.00  186
  5  ω    -76.00 -28.00   0.50    5.00    --   -0.94 -37.00 -30.00   96
  6  ω    -73.00 -47.00   0.50    5.00    --   -0.94 -57.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0250849000
_diffrn_orient_matrix_UB_12      -0.0441533000
_diffrn_orient_matrix_UB_13      0.0022827000
_diffrn_orient_matrix_UB_21      0.0053500000
_diffrn_orient_matrix_UB_22      0.0061888000
_diffrn_orient_matrix_UB_23      0.0248860000
_diffrn_orient_matrix_UB_31      -0.0154229000
_diffrn_orient_matrix_UB_32      0.0741362000
_diffrn_orient_matrix_UB_33      -0.0007171000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ag K\a'
_diffrn_radiation_wavelength     0.56087
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Ag) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3184
_reflns_number_total             3518
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     21.90
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3518
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0557P)²+1.6900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1073
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C2(H2), C3(H3)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.58832(2) 1.13154(5) 0.39551(2) 0.01542(10) Uani 1 1 d . . . . .
F1 F 0.54253(4) 1.06802(14) 0.44828(4) 0.02621(19) Uani 1 1 d . . . . .
F3 F 0.51742(5) 1.12066(14) 0.34831(4) 0.0291(2) Uani 1 1 d . . . . .
F5 F 0.65901(4) 1.14235(14) 0.44257(4) 0.0291(2) Uani 1 1 d . . . . .
F4 F 0.60325(5) 0.89227(13) 0.38365(4) 0.0285(2) Uani 1 1 d . . . . .
F2 F 0.63450(5) 1.19296(16) 0.34243(4) 0.0334(2) Uani 1 1 d . . . . .
F6 F 0.57300(6) 1.37006(13) 0.40720(5) 0.0382(2) Uani 1 1 d . . . . .
N1 N 0.39831(5) 0.54737(16) 0.38939(5) 0.0158(2) Uani 1 1 d . . . . .
C8 C 0.41144(6) 0.50374(18) 0.33530(5) 0.0158(2) Uani 1 1 d . . . . .
C6 C 0.32957(6) 0.26311(17) 0.35915(5) 0.0136(2) Uani 1 1 d . . . . .
C5 C 0.36910(6) 0.32555(18) 0.31369(5) 0.0144(2) Uani 1 1 d . . . . .
C7 C 0.34422(6) 0.40578(18) 0.41190(5) 0.0143(2) Uani 1 1 d . . . . .
C1 C 0.28457(7) 0.0927(2) 0.35169(6) 0.0194(2) Uani 1 1 d . . . . .
H1 H 0.257163 0.049319 0.382291 0.023 Uiso 1 1 calc R U . . .
C9 C 0.27793(7) 0.5310(2) 0.42268(6) 0.0203(2) Uani 1 1 d . . . . .
H9A H 0.290428 0.629182 0.455363 0.030 Uiso 1 1 calc R U . . .
H9B H 0.240527 0.437185 0.433339 0.030 Uiso 1 1 calc R U . . .
H9C H 0.260389 0.606833 0.386244 0.030 Uiso 1 1 calc R U . . .
C10 C 0.37731(7) 0.2946(2) 0.46832(6) 0.0213(3) Uani 1 1 d . . . . .
H10A H 0.422230 0.228744 0.460610 0.032 Uiso 1 1 calc R U . . .
H10B H 0.344041 0.189018 0.479643 0.032 Uiso 1 1 calc R U . . .
H10C H 0.386863 0.394890 0.500892 0.032 Uiso 1 1 calc R U . . .
C4 C 0.36535(7) 0.2226(2) 0.25903(5) 0.0187(2) Uani 1 1 d . . . . .
H4 H 0.391929 0.268089 0.228118 0.022 Uiso 1 1 calc R U . . .
C12 C 0.46285(7) 0.6175(2) 0.30236(6) 0.0229(3) Uani 1 1 d . . . . .
H12A H 0.460334 0.765507 0.311200 0.034 Uiso 1 1 calc R U . . .
H12B H 0.450806 0.595233 0.259339 0.034 Uiso 1 1 calc R U . . .
H12C H 0.511408 0.566926 0.314735 0.034 Uiso 1 1 calc R U . . .
C2 C 0.28132(7) -0.0120(2) 0.29732(7) 0.0242(3) Uani 1 1 d . . . . .
H2 H 0.251151 -0.129707 0.291056 0.029 Uiso 1 1 calc R U . . .
C11 C 0.43213(8) 0.7144(2) 0.42628(6) 0.0253(3) Uani 1 1 d . . . . .
H11A H 0.483334 0.685583 0.435616 0.038 Uiso 1 1 calc R U . . .
H11B H 0.410011 0.724140 0.463479 0.038 Uiso 1 1 calc R U . . .
H11C H 0.425691 0.845480 0.404475 0.038 Uiso 1 1 calc R U . . .
C3 C 0.32095(7) 0.0505(2) 0.25184(6) 0.0234(3) Uani 1 1 d . . . . .
H3 H 0.317555 -0.025555 0.215535 0.028 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 F1 1.6008(8) . ?
P1 F3 1.6082(8) . ?
P1 F5 1.6033(8) . ?
P1 F4 1.6005(9) . ?
P1 F2 1.6077(9) . ?
P1 F6 1.5965(9) . ?
N1 C8 1.3021(15) . ?
N1 C7 1.5004(15) . ?
N1 C11 1.4629(16) . ?
C8 C5 1.4524(16) . ?
C8 C12 1.4813(16) . ?
C6 C5 1.3938(16) . ?
C6 C7 1.5043(15) . ?
C6 C1 1.3879(16) . ?
C5 C4 1.3944(16) . ?
C7 C9 1.5299(16) . ?
C7 C10 1.5286(16) . ?
C1 H1 0.9500 . ?
C1 C2 1.3950(18) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C4 H4 0.9500 . ?
C4 C3 1.3901(19) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C2 H2 0.9500 . ?
C2 C3 1.395(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C3 H3 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
F1 P1 F3 90.18(5) . . ?
F1 P1 F5 89.81(5) . . ?
F1 P1 F2 179.44(5) . . ?
F5 P1 F3 179.99(7) . . ?
F5 P1 F2 90.15(5) . . ?
F4 P1 F1 89.78(5) . . ?
F4 P1 F3 89.74(5) . . ?
F4 P1 F5 90.25(5) . . ?
F4 P1 F2 89.66(5) . . ?
F2 P1 F3 89.85(5) . . ?
F6 P1 F1 90.13(6) . . ?
F6 P1 F3 89.97(5) . . ?
F6 P1 F5 90.03(5) . . ?
F6 P1 F4 179.70(6) . . ?
F6 P1 F2 90.43(6) . . ?
C8 N1 C7 113.20(10) . . ?
C8 N1 C11 125.06(11) . . ?
C11 N1 C7 121.73(10) . . ?
N1 C8 C5 109.23(10) . . ?
N1 C8 C12 124.57(11) . . ?
C5 C8 C12 126.19(11) . . ?
C5 C6 C7 109.78(10) . . ?
C1 C6 C5 120.74(11) . . ?
C1 C6 C7 129.47(11) . . ?
C6 C5 C8 107.59(10) . . ?
C6 C5 C4 122.29(11) . . ?
C4 C5 C8 130.12(11) . . ?
N1 C7 C6 100.17(9) . . ?
N1 C7 C9 109.16(10) . . ?
N1 C7 C10 109.95(10) . . ?
C6 C7 C9 111.84(10) . . ?
C6 C7 C10 112.84(10) . . ?
C10 C7 C9 112.18(10) . . ?
C6 C1 H1 121.4 . . ?
C6 C1 C2 117.11(12) . . ?
C2 C1 H1 121.4 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C4 H4 121.5 . . ?
C3 C4 C5 116.96(12) . . ?
C3 C4 H4 121.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 C2 H2 118.9 . . ?
C1 C2 C3 122.12(12) . . ?
C3 C2 H2 118.9 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 C3 C2 120.77(12) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?

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
N1 C8 C5 C6 -0.49(13) . . . . ?
N1 C8 C5 C4 -179.72(12) . . . . ?
C8 N1 C7 C6 1.53(13) . . . . ?
C8 N1 C7 C9 -116.02(11) . . . . ?
C8 N1 C7 C10 120.52(11) . . . . ?
C8 C5 C4 C3 178.03(12) . . . . ?
C6 C5 C4 C3 -1.11(18) . . . . ?
C6 C1 C2 C3 -0.3(2) . . . . ?
C5 C6 C7 N1 -1.77(12) . . . . ?
C5 C6 C7 C9 113.77(11) . . . . ?
C5 C6 C7 C10 -118.63(11) . . . . ?
C5 C6 C1 C2 0.39(18) . . . . ?
C5 C4 C3 C2 1.15(19) . . . . ?
C7 N1 C8 C5 -0.73(14) . . . . ?
C7 N1 C8 C12 -179.57(11) . . . . ?
C7 C6 C5 C8 1.49(13) . . . . ?
C7 C6 C5 C4 -179.21(11) . . . . ?
C7 C6 C1 C2 179.85(12) . . . . ?
C1 C6 C5 C8 -178.96(11) . . . . ?
C1 C6 C5 C4 0.35(18) . . . . ?
C1 C6 C7 N1 178.72(12) . . . . ?
C1 C6 C7 C9 -65.74(16) . . . . ?
C1 C6 C7 C10 61.87(16) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C12 C8 C5 C6 178.33(11) . . . . ?
C12 C8 C5 C4 -0.9(2) . . . . ?
C11 N1 C8 C5 178.65(11) . . . . ?
C11 N1 C8 C12 -0.2(2) . . . . ?
C11 N1 C7 C6 -177.87(11) . . . . ?
C11 N1 C7 C9 64.58(14) . . . . ?
C11 N1 C7 C10 -58.88(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.639
_oxdiff_exptl_absorpt_empirical_full_min 0.252
