# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_az14466875_100k
_database_code_depnum_ccdc_archive 'CCDC 2382092'
loop_
_audit_author_name
_audit_author_address
'Okky Dwichandra Putra'
;AstraZeneca
Sweden
;
_audit_update_record             
;
2024-09-05 deposited with the CCDC.	2024-11-01 downloaded from the CCDC.
;
_audit_creation_date             2024-05-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
okky.putra@astrazeneca.com
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H15 N O'
_chemical_formula_sum            'C14 H15 N O'
_chemical_formula_weight         213.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     David
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   11.83321(10)
_cell_length_b                   6.75791(5)
_cell_length_c                   14.58577(12)
_cell_angle_alpha                90
_cell_angle_beta                 106.2749(9)
_cell_angle_gamma                90
_cell_volume                     1119.653(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    31963
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.6890
_cell_measurement_theta_min      3.1630
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.908
_exptl_absorpt_coefficient_mu    0.624
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.782
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             456
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 0 1 0.0410
-2 0 -1 0.0279
1 -2 -2 0.0829
0 4 5 0.0476
3 0 -5 0.0258
-3 0 5 0.0217
-1 -2 2 0.0733
4 2 -5 0.0431
0 0 1 0.0261

_exptl_crystal_preparation       
'The material was recrystallised from a mixture of acetonitrile and diethylether  by slow evaporation'
_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of acetonitrile and diethylether  by slow evaporation'
_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.048
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.9980 0.0003 1.0005 -0.2713 0.1602 0.0548
-1.9980 -0.0003 -1.0005 0.2713 -0.1602 -0.0548
1.0031 -1.9985 -1.9982 0.0600 -0.0683 0.4994
-0.0083 3.9974 4.9968 -0.3913 0.2969 -0.9439
3.0034 0.0001 -4.9959 0.2451 0.4442 0.2919
-3.0034 -0.0001 4.9959 -0.2451 -0.4442 -0.2919
-0.9998 -1.9986 1.9988 -0.1702 -0.3854 0.2832
4.0012 1.9988 -4.9957 0.2147 0.7668 -0.0558
-0.0010 0.0001 0.9995 -0.1003 -0.0314 -0.0323

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0073
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            44123
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.687
_diffrn_reflns_theta_min         3.892
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00  65.00   0.50    1.16    --   52.65 -41.00  -0.00  176
  2  ω     41.00 129.00   0.50    1.16    --   52.65  41.00 153.00  176
  3  ω    -90.00  -1.00   0.50    1.16    --  -77.66  41.00 153.00  178
  4  ω    -90.00  -1.00   0.50    1.16    --  -77.66  41.00 153.00  178
  5  ω   -154.00 -65.00   0.50    1.16    --  -77.66 -41.00  -0.00  178
  6  ω     26.00 115.00   0.50    3.08    --  102.45 -41.00  -0.00  178
  7  ω     90.00 178.00   0.50    3.08    --  102.45  41.00 153.00  176
  8  ω     90.00 178.00   0.50    3.08    --  102.45  41.00 153.00  176
  9  ω    -19.00  20.00   0.50    1.16    --   18.00 100.00-157.87   78
 10  ω     -4.00  24.00   0.50    1.16    --   30.00  95.00-104.49   56
 11  ω     14.00  43.00   0.50    1.16    --   38.00  79.00 -83.88   58
 12  ω   -129.00 -41.00   0.50    1.16    --  -53.15 -41.00  -0.00  176
 13  ω    -65.00  23.00   0.50    1.16    --  -53.15  41.00 153.00  176
 14  ω   -129.00 -41.00   0.50    1.16    --  -53.15 -41.00  -0.00  176
 15  ω     38.00 127.00   0.50    1.16    --   58.00  72.00 -78.17  178
 16  ω   -145.00 -56.00   0.50    1.16    --  -74.00 -64.00-144.51  178
 17  ω    -94.00  -5.00   0.50    1.16    --  -77.66  61.00-120.00  178
 18  ω   -150.00 -61.00   0.50    1.16    --  -77.66 -61.00 -90.00  178
 19  ω   -143.00 -86.00   0.50    1.16    --  -77.66 -95.00 120.00  114
 20  ω   -156.00 -68.00   0.50    3.08    --  -86.25 -68.00-167.28  176
 21  ω   -155.00 -67.00   0.50    3.08    --  -86.25 -71.00-114.40  176
 22  ω   -156.00 -68.00   0.50    3.08    --  -86.25 -68.00-167.28  176
 23  ω     30.00 119.00   0.50    3.08    --  102.45 -61.00 150.00  178
 24  ω     80.00 169.00   0.50    3.08    --  102.45  77.00-120.00  178
 25  ω     54.00 178.00   0.50    3.08    --  102.45  15.00 -90.00  248
 26  ω     80.00 169.00   0.50    3.08    --  102.45  77.00 -60.00  178
 27  ω     86.00 175.00   0.50    3.08    --  102.45  61.00 -90.00  178
 28  ω     37.00 105.00   0.50    3.08    --  102.45 -95.00   0.00  136
 29  ω     95.00 172.00   0.50    3.08    --  102.45 125.00   0.00  154
 30  ω     37.00 105.00   0.50    3.08    --  102.45 -95.00  30.00  136
 31  ω     80.00 169.00   0.50    3.08    --  102.45  77.00 -90.00  178
 32  ω     80.00 169.00   0.50    3.08    --  102.45  77.00-150.00  178
 33  ω     86.00 175.00   0.50    3.08    --  102.45  61.00 -60.00  178
 34  ω     80.00 169.00   0.50    3.08    --  102.45  77.00-180.00  178
 35  ω     95.00 172.00   0.50    3.08    --  102.45 125.00  30.00  154
 36  ω     37.00 105.00   0.50    3.08    --  102.45 -95.00  90.00  136
 37  ω     95.00 172.00   0.50    3.08    --  102.45 125.00 120.00  154
 38  ω     86.00 175.00   0.50    3.08    --  102.45  61.00-120.00  178
 39  ω     34.00 111.00   0.50    3.08    --  102.45-125.00  90.00  154
 40  ω     37.00 105.00   0.50    3.08    --  102.45 -95.00-180.00  136
 41  ω     30.00 119.00   0.50    3.08    --  102.45 -61.00 150.00  178
 42  ω     86.00 175.00   0.50    3.08    --  102.45  61.00-120.00  178
 43  ω     95.00 172.00   0.50    3.08    --  102.45 125.00  60.00  154
 44  ω      5.00  32.00   0.50    1.16    --   34.00  87.00  28.73   54
 45  ω     13.00  41.00   0.50    1.16    --   38.00  80.00 125.42   56
 46  ω     13.00  39.00   0.50    1.16    --   38.00  81.00-153.26   52
 47  ω     15.00  43.00   0.50    1.16    --   38.00  78.00  44.57   56
 48  ω     43.00 131.00   0.50    1.16    --   62.00  71.00  -1.59  176
 49  ω     46.00 135.00   0.50    1.16    --   66.00  72.00  55.30  178
 50  ω   -140.00 -52.00   0.50    1.16    --  -70.00 -67.00 116.59  176
 51  ω   -141.00 -52.00   0.50    1.16    --  -70.00 -65.00 -55.09  178
 52  ω   -145.00 -56.00   0.50    1.16    --  -74.00 -66.00 -11.45  178
 53  ω   -145.00 -56.00   0.50    1.16    --  -74.00 -64.00  64.86  178
 54  ω   -100.00 -11.00   0.50    1.16    --  -77.66  77.00  30.00  178
 55  ω   -147.00 -59.00   0.50    1.16    --  -78.00 -71.00 152.06  176
 56  ω     86.00 175.00   0.50    3.08    --  102.45  61.00   0.00  178
 57  ω     80.00 169.00   0.50    3.08    --  102.45  77.00  30.00  178
 58  ω     80.00 169.00   0.50    3.08    --  102.45  77.00 -30.00  178
 59  ω     34.00 111.00   0.50    3.08    --  102.45-125.00 -30.00  154
 60  ω     80.00 169.00   0.50    3.08    --  102.45  77.00 150.00  178
 61  ω     80.00 169.00   0.50    3.08    --  102.45  77.00  60.00  178
 62  ω     80.00 169.00   0.50    3.08    --  102.45  77.00  90.00  178
 63  ω     41.00 135.00   0.50    3.08    --  107.25 -85.00 121.50  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0854757000
_diffrn_orient_matrix_UB_12      0.0274804000
_diffrn_orient_matrix_UB_13      -0.1004406000
_diffrn_orient_matrix_UB_21      0.0958399000
_diffrn_orient_matrix_UB_22      0.1135783000
_diffrn_orient_matrix_UB_23      -0.0312890000
_diffrn_orient_matrix_UB_31      0.0435955000
_diffrn_orient_matrix_UB_32      -0.1957517000
_diffrn_orient_matrix_UB_33      -0.0322325000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2310
_reflns_number_total             2383
_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 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.104a 64-bit (release 22-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0024(3)
_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   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2383
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.051
_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)+(0.0325P)²+0.4727P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0804
_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 Ternary CH refined with riding coordinates:
 C8(H8), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_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 0.80115(6) 0.52177(10) 0.47361(4) 0.01894(17) Uani 1 1 d . . . . .
N1 N 0.53170(8) 0.26862(14) 0.42488(7) 0.0273(2) Uani 1 1 d . . . . .
C1 C 0.90407(8) 0.39681(14) 0.33182(7) 0.0197(2) Uani 1 1 d . . . . .
H1 H 0.952679 0.409144 0.395562 0.024 Uiso 1 1 calc R U . . .
C2 C 0.94512(9) 0.29549(15) 0.26458(7) 0.0229(2) Uani 1 1 d . . . . .
H2 H 1.021624 0.238725 0.282598 0.027 Uiso 1 1 calc R U . . .
C3 C 0.87466(9) 0.27692(15) 0.17111(7) 0.0236(2) Uani 1 1 d . . . . .
H3 H 0.902750 0.207002 0.125391 0.028 Uiso 1 1 calc R U . . .
C4 C 0.76318(9) 0.36084(15) 0.14480(7) 0.0239(2) Uani 1 1 d . . . . .
H4 H 0.715056 0.348696 0.080890 0.029 Uiso 1 1 calc R U . . .
C5 C 0.72166(9) 0.46260(15) 0.21159(7) 0.0215(2) Uani 1 1 d . . . . .
H5 H 0.645402 0.520269 0.193060 0.026 Uiso 1 1 calc R U . . .
C6 C 0.79169(8) 0.48048(14) 0.30601(7) 0.0177(2) Uani 1 1 d . . . . .
C7 C 0.74679(8) 0.58987(14) 0.37727(6) 0.0171(2) Uani 1 1 d . . . . .
C8 C 0.66170(8) 0.76588(14) 0.45003(7) 0.0192(2) Uani 1 1 d . . . . .
H8 H 0.607200 0.866797 0.464333 0.023 Uiso 1 1 calc R U . . .
C9 C 0.74224(9) 0.64424(15) 0.52946(7) 0.0209(2) Uani 1 1 d . . . . .
H9A H 0.798835 0.728650 0.576009 0.025 Uiso 1 1 calc R U . . .
H9B H 0.697102 0.562833 0.563337 0.025 Uiso 1 1 calc R U . . .
C10 C 0.74763(8) 0.82108(14) 0.38888(7) 0.0182(2) Uani 1 1 d . . . . .
C11 C 0.86611(9) 0.91353(15) 0.43874(7) 0.0226(2) Uani 1 1 d . . . . .
H11A H 0.907561 0.829865 0.492542 0.034 Uiso 1 1 calc R U . . .
H11B H 0.853807 1.045285 0.462322 0.034 Uiso 1 1 calc R U . . .
H11C H 0.913300 0.925004 0.393472 0.034 Uiso 1 1 calc R U . . .
C12 C 0.69160(9) 0.93783(15) 0.29784(7) 0.0234(2) Uani 1 1 d . . . . .
H12A H 0.741083 0.927198 0.254269 0.035 Uiso 1 1 calc R U . . .
H12B H 0.684472 1.077176 0.313965 0.035 Uiso 1 1 calc R U . . .
H12C H 0.613293 0.884022 0.266854 0.035 Uiso 1 1 calc R U . . .
C13 C 0.61402(8) 0.59704(14) 0.37510(7) 0.0192(2) Uani 1 1 d . . . . .
H13 H 0.563072 0.649709 0.313211 0.023 Uiso 1 1 calc R U . . .
C14 C 0.56675(8) 0.41516(15) 0.40404(7) 0.0215(2) 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
O1 C7 1.4469(10) . ?
O1 C9 1.4672(11) . ?
N1 C14 1.1471(14) . ?
C1 H1 0.9500 . ?
C1 C2 1.3905(14) . ?
C1 C6 1.3962(13) . ?
C2 H2 0.9500 . ?
C2 C3 1.3902(14) . ?
C3 H3 0.9500 . ?
C3 C4 1.3876(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.3898(14) . ?
C5 H5 0.9500 . ?
C5 C6 1.3994(13) . ?
C6 C7 1.4894(13) . ?
C7 C10 1.5714(13) . ?
C7 C13 1.5632(13) . ?
C8 H8 1.0000 . ?
C8 C9 1.5190(13) . ?
C8 C10 1.5738(13) . ?
C8 C13 1.5713(13) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5209(13) . ?
C10 C12 1.5271(13) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 1.0000 . ?
C13 C14 1.4609(14) . ?

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
C7 O1 C9 102.04(7) . . ?
C2 C1 H1 119.9 . . ?
C2 C1 C6 120.26(9) . . ?
C6 C1 H1 119.9 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.28(9) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.78(9) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.26(9) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.29(9) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 119.14(9) . . ?
C1 C6 C7 120.79(8) . . ?
C5 C6 C7 120.06(9) . . ?
O1 C7 C6 111.80(8) . . ?
O1 C7 C10 102.94(7) . . ?
O1 C7 C13 101.55(7) . . ?
C6 C7 C10 125.17(8) . . ?
C6 C7 C13 123.66(8) . . ?
C13 C7 C10 86.98(7) . . ?
C9 C8 H8 120.9 . . ?
C9 C8 C10 101.16(8) . . ?
C9 C8 C13 99.42(8) . . ?
C10 C8 H8 120.9 . . ?
C13 C8 H8 120.9 . . ?
C13 C8 C10 86.62(7) . . ?
O1 C9 C8 100.14(7) . . ?
O1 C9 H9A 111.7 . . ?
O1 C9 H9B 111.7 . . ?
C8 C9 H9A 111.7 . . ?
C8 C9 H9B 111.7 . . ?
H9A C9 H9B 109.5 . . ?
C7 C10 C8 80.78(7) . . ?
C11 C10 C7 115.92(8) . . ?
C11 C10 C8 118.80(8) . . ?
C11 C10 C12 108.72(8) . . ?
C12 C10 C7 115.59(8) . . ?
C12 C10 C8 115.04(8) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 C8 81.11(7) . . ?
C7 C13 H13 112.2 . . ?
C8 C13 H13 112.2 . . ?
C14 C13 C7 115.60(8) . . ?
C14 C13 C8 120.13(8) . . ?
C14 C13 H13 112.2 . . ?
N1 C14 C13 177.57(11) . . ?

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 C7 C10 C8 -64.91(7) . . . . ?
O1 C7 C10 C11 52.72(10) . . . . ?
O1 C7 C10 C12 -178.35(7) . . . . ?
O1 C7 C13 C8 66.32(7) . . . . ?
O1 C7 C13 C14 -52.92(10) . . . . ?
C1 C2 C3 C4 0.34(15) . . . . ?
C1 C6 C7 O1 -26.88(12) . . . . ?
C1 C6 C7 C10 98.35(11) . . . . ?
C1 C6 C7 C13 -148.58(9) . . . . ?
C2 C1 C6 C5 -0.62(14) . . . . ?
C2 C1 C6 C7 -179.82(9) . . . . ?
C2 C3 C4 C5 -0.24(15) . . . . ?
C3 C4 C5 C6 -0.30(15) . . . . ?
C4 C5 C6 C1 0.72(14) . . . . ?
C4 C5 C6 C7 179.94(9) . . . . ?
C5 C6 C7 O1 153.92(8) . . . . ?
C5 C6 C7 C10 -80.85(12) . . . . ?
C5 C6 C7 C13 32.22(13) . . . . ?
C6 C1 C2 C3 0.09(15) . . . . ?
C6 C7 C10 C8 166.18(9) . . . . ?
C6 C7 C10 C11 -76.18(12) . . . . ?
C6 C7 C10 C12 52.75(13) . . . . ?
C6 C7 C13 C8 -167.42(9) . . . . ?
C6 C7 C13 C14 73.35(12) . . . . ?
C7 O1 C9 C8 -0.28(8) . . . . ?
C9 O1 C7 C6 -178.57(7) . . . . ?
C9 O1 C7 C10 44.68(8) . . . . ?
C9 O1 C7 C13 -44.86(8) . . . . ?
C9 C8 C10 C7 62.90(7) . . . . ?
C9 C8 C10 C11 -51.70(11) . . . . ?
C9 C8 C10 C12 176.92(8) . . . . ?
C9 C8 C13 C7 -64.53(7) . . . . ?
C9 C8 C13 C14 49.98(11) . . . . ?
C10 C7 C13 C8 -36.28(6) . . . . ?
C10 C7 C13 C14 -155.51(8) . . . . ?
C10 C8 C9 O1 -43.72(8) . . . . ?
C10 C8 C13 C7 36.23(6) . . . . ?
C10 C8 C13 C14 150.74(9) . . . . ?
C13 C7 C10 C8 36.25(6) . . . . ?
C13 C7 C10 C11 153.89(8) . . . . ?
C13 C7 C10 C12 -77.18(9) . . . . ?
C13 C8 C9 O1 44.66(8) . . . . ?
C13 C8 C10 C7 -36.05(6) . . . . ?
C13 C8 C10 C11 -150.64(9) . . . . ?
C13 C8 C10 C12 77.97(9) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id PSX_2118
_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 1.335
_oxdiff_exptl_absorpt_empirical_full_min 0.868
####################################################################### 
# 
# 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_az14472834_100k_cu
_database_code_depnum_ccdc_archive 'CCDC 2382093'
loop_
_audit_author_name
_audit_author_address
'Okky Dwichandra Putra'
;AstraZeneca
Sweden
;
_audit_update_record             
;
2024-09-05 deposited with the CCDC.	2024-11-01 downloaded from the CCDC.
;
_audit_creation_date             2024-06-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
okky.putra@astrazeneca.com
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 N O2'
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   5.72327(3)
_cell_length_b                   7.75796(5)
_cell_length_c                   24.60196(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1092.349(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    36233
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.2960
_cell_measurement_theta_min      3.5730
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.889
_exptl_absorpt_coefficient_mu    0.750
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             480
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0487
0 -1 0 0.0402
-2 0 -1 0.0616
2 0 1 0.0954
0 0 -1 0.0073
0 0 1 0.0147

_exptl_crystal_preparation       
'The material was recrystallized from chloroform by slow evaporation'
_exptl_crystal_recrystallization_method 
'The material was recrystallised from chloroform by slow evaporation'
_exptl_crystal_size_max          0.161
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.022
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0001 0.9991 -0.0015 -0.0610 0.1308 -0.1361
0.0001 -0.9991 0.0015 0.0610 -0.1308 0.1361
-1.9990 0.0007 -0.9959 -0.1643 0.3336 0.3938
1.9990 -0.0007 0.9959 0.1643 -0.3336 -0.3938
-0.0002 -0.0003 -0.9997 -0.0583 -0.0224 0.0046
0.0002 0.0003 0.9997 0.0583 0.0224 -0.0046

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0075
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            46038
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.502
_diffrn_reflns_theta_min         3.593
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     46.00 118.00   0.50    2.16    --   52.65-146.00 175.00  144
  2  ω   -150.00 -61.00   0.50    2.16    --  -77.66 -62.00  46.00  178
  3  ω   -150.00 -61.00   0.50    2.16    --  -77.66 -62.00  46.00  178
  4  ω     46.00 127.00   0.50    6.29    --  102.45-146.00 175.00  162
  5  ω     86.00 176.00   0.50    6.29    --  102.45  58.00  -3.00  180
  6  ω     95.00 172.00   0.50    6.29    --  102.45 125.00  59.00  154
  7  ω   -119.00 -80.00   0.50    2.16    --  -53.15 -77.00 -90.00   78
  8  ω   -122.00 -76.00   0.50    2.16    --  -53.15-125.00 -30.00   92
  9  ω   -119.00 -80.00   0.50    2.16    --  -53.15 -77.00  90.00   78
 10  ω   -119.00 -80.00   0.50    2.16    --  -53.15 -77.00 -30.00   78
 11  ω    -94.00  -4.00   0.50    2.16    --  -77.66  58.00  -3.00  180
 12  ω     89.00 178.00   0.50    6.29    --  102.45  45.00 -30.00  178
 13  ω     37.00 105.00   0.50    6.29    --  102.45 -95.00 -30.00  136
 14  ω     37.00 105.00   0.50    6.29    --  102.45 -95.00  30.00  136
 15  ω     95.00 172.00   0.50    6.29    --  102.45 125.00-150.00  154
 16  ω     30.00 119.00   0.50    6.29    --  102.45 -61.00-180.00  178
 17  ω     95.00 172.00   0.50    6.29    --  102.45 125.00-150.00  154
 18  ω     34.00 111.00   0.50    6.29    --  102.45-125.00 120.00  154
 19  ω     34.00 111.00   0.50    6.29    --  102.45-125.00 120.00  154
 20  ω     37.00 105.00   0.50    6.29    --  102.45 -95.00-180.00  136
 21  ω   -126.00 -37.00   0.50    2.16    --  -53.15 -58.00-144.00  178
 22  ω   -119.00 -80.00   0.50    2.16    --  -53.15 -77.00-150.00   78
 23  ω   -126.00 -37.00   0.50    2.16    --  -53.15 -57.00 120.00  178
 24  ω   -150.00 -61.00   0.50    2.16    --  -77.66 -61.00 -60.00  178
 25  ω   -150.00 -61.00   0.50    2.16    --  -77.66 -61.00  90.00  178
 26  ω   -150.00 -61.00   0.50    2.16    --  -77.66 -61.00 -30.00  178
 27  ω   -150.00 -61.00   0.50    2.16    --  -77.66 -61.00   0.00  178
 28  ω   -150.00 -61.00   0.50    2.16    --  -77.66 -61.00 -90.00  178
 29  ω   -150.00 -61.00   0.50    2.16    --  -77.66 -61.00-180.00  178
 30  ω     80.00 169.00   0.50    6.29    --  102.45  77.00-150.00  178
 31  ω     86.00 175.00   0.50    6.29    --  102.45  61.00 120.00  178
 32  ω     80.00 169.00   0.50    6.29    --  102.45  77.00 -90.00  178
 33  ω     80.00 169.00   0.50    6.29    --  102.45  77.00-180.00  178
 34  ω     89.00 178.00   0.50    6.29    --  102.45  45.00  60.00  178
 35  ω     87.00 178.00   0.50    6.29    --  102.45  30.00-180.00  182
 36  ω   -126.00 -37.00   0.50    2.16    --  -53.15 -57.00 -60.00  178
 37  ω   -126.00 -37.00   0.50    2.16    --  -53.15 -57.00  30.00  178
 38  ω   -126.00 -37.00   0.50    2.16    --  -53.15 -57.00-180.00  178
 39  ω   -150.00 -61.00   0.50    2.16    --  -77.66 -61.00 150.00  178
 40  ω   -150.00 -61.00   0.50    2.16    --  -77.66 -61.00  30.00  178
 41  ω   -150.00 -61.00   0.50    2.16    --  -77.66 -61.00-120.00  178
 42  ω   -100.00 -11.00   0.50    2.16    --  -77.66  77.00-150.00  178
 43  ω   -150.00 -61.00   0.50    2.16    --  -77.66 -61.00 120.00  178
 44  ω     80.00 169.00   0.50    6.29    --  102.45  77.00-120.00  178
 45  ω     27.00 116.00   0.50    6.29    --  102.45 -45.00 -60.00  178
 46  ω     80.00 169.00   0.50    6.29    --  102.45  77.00   0.00  178
 47  ω     34.00 111.00   0.50    6.29    --  102.45-125.00 -60.00  154
 48  ω     80.00 169.00   0.50    6.29    --  102.45  77.00 -60.00  178
 49  ω     80.00 169.00   0.50    6.29    --  102.45  77.00 150.00  178
 50  ω     80.00 169.00   0.50    6.29    --  102.45  77.00  60.00  178
 51  ω   -126.00 -37.00   0.50    2.16    --  -53.15 -57.00 -90.00  178
 52  ω   -126.00 -37.00   0.50    2.16    --  -53.15 -57.00   0.00  178
 53  ω   -126.00 -37.00   0.50    2.16    --  -53.15 -57.00  90.00  178
 54  ω   -151.00 -61.00   0.50    2.16    --  -77.66 -58.00-144.00  180
 55  ω   -150.00 -85.00   0.50    2.16    --  -77.66 -61.00  60.00  130
 56  ω    -85.00 -13.00   0.50    2.16    --  -77.66 125.00   0.00  144
 57  ω     80.00 169.00   0.50    6.29    --  102.45  77.00 -30.00  178
 58  ω     80.00 169.00   0.50    6.29    --  102.45  77.00  90.00  178
 59  ω     80.00 169.00   0.50    6.29    --  102.45  77.00  30.00  178
 60  ω     34.00 111.00   0.50    6.29    --  102.45-125.00 -90.00  154
 61  ω     37.00 105.00   0.50    6.29    --  102.45 -95.00 120.00  136
 62  ω     80.00 169.00   0.50    6.29    --  102.45  77.00 120.00  178
 63  ω    -73.00 -48.00   0.50    2.16    --  -77.66  58.00  -3.00   50
 64  ω     55.00  80.00   0.50    2.16    --   50.32  58.00  -3.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0531136000
_diffrn_orient_matrix_UB_12      -0.0609992000
_diffrn_orient_matrix_UB_13      0.0582964000
_diffrn_orient_matrix_UB_21      -0.1779838000
_diffrn_orient_matrix_UB_22      0.1309677000
_diffrn_orient_matrix_UB_23      0.0224130000
_diffrn_orient_matrix_UB_31      -0.1947748000
_diffrn_orient_matrix_UB_32      -0.1362564000
_diffrn_orient_matrix_UB_33      -0.0045619000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2300
_reflns_number_total             2327
_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 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.104a 64-bit (release 22-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 926 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_coef       0.0033(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   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0245
_refine_ls_restrained_S_all      1.061
_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)+(0.0317P)²+0.2487P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0626
_refine_special_details          
;
The absolute structure can be determined reliably from anomalous dispersion Flack parameter: -0.02(3) 
Hooft parameter: -0.03(2)
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5)
;
_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 0.72915(16) 0.57541(12) 0.62935(4) 0.0165(2) Uani 1 1 d . . . . .
O2 O 0.90577(18) 0.65798(13) 0.75023(4) 0.0224(2) Uani 1 1 d . . . . .
N1 N 0.5716(2) 0.14418(17) 0.66496(5) 0.0257(3) Uani 1 1 d . . . . .
C1 C 0.7160(3) 0.43954(18) 0.52332(6) 0.0200(3) Uani 1 1 d . . . . .
H1 H 0.837648 0.403995 0.547073 0.024 Uiso 1 1 calc R U . . .
C2 C 0.7297(3) 0.40195(19) 0.46800(6) 0.0227(3) Uani 1 1 d . . . . .
H2 H 0.861146 0.341562 0.454086 0.027 Uiso 1 1 calc R U . . .
C3 C 0.5514(3) 0.45272(19) 0.43319(6) 0.0225(3) Uani 1 1 d . . . . .
H3 H 0.559658 0.425755 0.395573 0.027 Uiso 1 1 calc R U . . .
C4 C 0.3612(3) 0.5429(2) 0.45352(6) 0.0237(3) Uani 1 1 d . . . . .
H4 H 0.239722 0.578261 0.429678 0.028 Uiso 1 1 calc R U . . .
C5 C 0.3473(3) 0.5819(2) 0.50867(6) 0.0211(3) Uani 1 1 d . . . . .
H5 H 0.217251 0.644568 0.522306 0.025 Uiso 1 1 calc R U . . .
C6 C 0.5242(2) 0.52915(16) 0.54389(5) 0.0166(3) Uani 1 1 d . . . . .
C7 C 0.5024(2) 0.56225(17) 0.60336(5) 0.0163(3) Uani 1 1 d . . . . .
C8 C 0.3599(2) 0.70831(18) 0.63017(5) 0.0187(3) Uani 1 1 d . . . . .
H8A H 0.195046 0.716127 0.618232 0.022 Uiso 1 1 calc R U . . .
H8B H 0.437491 0.822362 0.630423 0.022 Uiso 1 1 calc R U . . .
C9 C 0.4013(2) 0.59716(17) 0.68193(5) 0.0170(3) Uani 1 1 d . . . . .
H9 H 0.301670 0.612004 0.714993 0.020 Uiso 1 1 calc R U . . .
C10 C 0.6665(2) 0.60684(17) 0.68556(5) 0.0162(3) Uani 1 1 d . . . . .
C11 C 0.7840(3) 0.76496(18) 0.71083(6) 0.0190(3) Uani 1 1 d . . . . .
H11A H 0.890267 0.825876 0.685544 0.023 Uiso 1 1 calc R U . . .
H11B H 0.672189 0.846524 0.727588 0.023 Uiso 1 1 calc R U . . .
C12 C 0.8034(2) 0.50193(18) 0.72764(5) 0.0181(3) Uani 1 1 d . . . . .
H12A H 0.702101 0.439315 0.753610 0.022 Uiso 1 1 calc R U . . .
H12B H 0.919868 0.423169 0.711274 0.022 Uiso 1 1 calc R U . . .
C13 C 0.3696(2) 0.43748(18) 0.64350(5) 0.0171(3) Uani 1 1 d . . . . .
H13 H 0.202536 0.421898 0.632622 0.020 Uiso 1 1 calc R U . . .
C14 C 0.4804(3) 0.27305(18) 0.65622(6) 0.0190(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
O1 C7 1.4503(16) . ?
O1 C10 1.4493(16) . ?
O2 C11 1.4539(17) . ?
O2 C12 1.4554(17) . ?
N1 C14 1.148(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.394(2) . ?
C1 C6 1.3944(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3939(19) . ?
C6 C7 1.4907(18) . ?
C7 C8 1.5440(18) . ?
C7 C13 1.5779(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5561(19) . ?
C9 H9 1.0000 . ?
C9 C10 1.5223(18) . ?
C9 C13 1.5690(18) . ?
C10 C11 1.5309(19) . ?
C10 C12 1.5322(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13 1.0000 . ?
C13 C14 1.4586(19) . ?

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
C10 O1 C7 102.18(9) . . ?
C11 O2 C12 91.56(10) . . ?
C2 C1 H1 119.9 . . ?
C2 C1 C6 120.20(13) . . ?
C6 C1 H1 119.9 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.07(14) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.82(13) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.38(14) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.02(14) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C7 120.53(12) . . ?
C5 C6 C1 119.51(12) . . ?
C5 C6 C7 119.91(12) . . ?
O1 C7 C6 111.72(11) . . ?
O1 C7 C8 103.46(10) . . ?
O1 C7 C13 101.45(9) . . ?
C6 C7 C8 126.14(11) . . ?
C6 C7 C13 123.28(11) . . ?
C8 C7 C13 85.90(10) . . ?
C7 C8 H8A 114.9 . . ?
C7 C8 H8B 114.9 . . ?
C7 C8 C9 82.09(10) . . ?
H8A C8 H8B 112.0 . . ?
C9 C8 H8A 114.9 . . ?
C9 C8 H8B 114.9 . . ?
C8 C9 H9 121.0 . . ?
C8 C9 C13 85.80(10) . . ?
C10 C9 C8 99.93(11) . . ?
C10 C9 H9 121.0 . . ?
C10 C9 C13 100.94(11) . . ?
C13 C9 H9 121.0 . . ?
O1 C10 C9 100.51(10) . . ?
O1 C10 C11 114.43(11) . . ?
O1 C10 C12 115.39(11) . . ?
C9 C10 C11 120.10(12) . . ?
C9 C10 C12 121.54(12) . . ?
C11 C10 C12 85.79(10) . . ?
O2 C11 C10 91.37(10) . . ?
O2 C11 H11A 113.4 . . ?
O2 C11 H11B 113.4 . . ?
C10 C11 H11A 113.4 . . ?
C10 C11 H11B 113.4 . . ?
H11A C11 H11B 110.7 . . ?
O2 C12 C10 91.27(10) . . ?
O2 C12 H12A 113.4 . . ?
O2 C12 H12B 113.4 . . ?
C10 C12 H12A 113.4 . . ?
C10 C12 H12B 113.4 . . ?
H12A C12 H12B 110.7 . . ?
C7 C13 H13 111.6 . . ?
C9 C13 C7 80.62(10) . . ?
C9 C13 H13 111.6 . . ?
C14 C13 C7 117.47(12) . . ?
C14 C13 C9 120.72(11) . . ?
C14 C13 H13 111.6 . . ?
N1 C14 C13 178.06(16) . . ?

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 C7 C8 C9 -63.75(10) . . . . ?
O1 C7 C13 C9 66.05(10) . . . . ?
O1 C7 C13 C14 -53.79(14) . . . . ?
O1 C10 C11 O2 -116.88(11) . . . . ?
O1 C10 C12 O2 115.95(11) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
C1 C6 C7 O1 29.39(17) . . . . ?
C1 C6 C7 C8 156.34(13) . . . . ?
C1 C6 C7 C13 -91.74(16) . . . . ?
C2 C1 C6 C5 -0.5(2) . . . . ?
C2 C1 C6 C7 176.96(13) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C4 C5 C6 C1 1.0(2) . . . . ?
C4 C5 C6 C7 -176.51(13) . . . . ?
C5 C6 C7 O1 -153.18(12) . . . . ?
C5 C6 C7 C8 -26.2(2) . . . . ?
C5 C6 C7 C13 85.69(16) . . . . ?
C6 C1 C2 C3 -0.4(2) . . . . ?
C6 C7 C8 C9 166.02(13) . . . . ?
C6 C7 C13 C9 -168.18(13) . . . . ?
C6 C7 C13 C14 71.98(17) . . . . ?
C7 O1 C10 C9 2.66(12) . . . . ?
C7 O1 C10 C11 -127.47(11) . . . . ?
C7 O1 C10 C12 135.28(12) . . . . ?
C7 C8 C9 C10 63.08(11) . . . . ?
C7 C8 C9 C13 -37.30(9) . . . . ?
C8 C7 C13 C9 -36.86(9) . . . . ?
C8 C7 C13 C14 -156.71(12) . . . . ?
C8 C9 C10 O1 -45.28(12) . . . . ?
C8 C9 C10 C11 81.15(14) . . . . ?
C8 C9 C10 C12 -174.01(12) . . . . ?
C8 C9 C13 C7 36.53(9) . . . . ?
C8 C9 C13 C14 153.00(13) . . . . ?
C9 C10 C11 O2 123.45(13) . . . . ?
C9 C10 C12 O2 -122.15(13) . . . . ?
C10 O1 C7 C6 -179.97(11) . . . . ?
C10 O1 C7 C8 41.61(12) . . . . ?
C10 O1 C7 C13 -46.87(11) . . . . ?
C10 C9 C13 C7 -62.78(11) . . . . ?
C10 C9 C13 C14 53.68(15) . . . . ?
C11 O2 C12 C10 -0.90(10) . . . . ?
C11 C10 C12 O2 0.86(10) . . . . ?
C12 O2 C11 C10 0.90(10) . . . . ?
C12 C10 C11 O2 -0.86(10) . . . . ?
C13 C7 C8 C9 37.05(9) . . . . ?
C13 C9 C10 O1 42.31(12) . . . . ?
C13 C9 C10 C11 168.74(11) . . . . ?
C13 C9 C10 C12 -86.42(14) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id PSX_2283
_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 1.562
_oxdiff_exptl_absorpt_empirical_full_min 0.847
