# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_hphwlb
_database_code_depnum_ccdc_archive 'CCDC 1858962'
_audit_update_record             
;
2018-07-28 deposited with the CCDC.
2018-10-10 downloaded from the CCDC.
;
_nottingham_internal_coll_name   HPHWLB
_nottingham_internal_coll_number 17703
_nottingham_internal_coll_client HP/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '1.00, 2.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   24/05/2018
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 04/06/2018
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 4/6/2018
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 4/6/2018
_nottingham_internal_refinement_user pczwl
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 4/6/2018
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 4/6/2018
_refine_special_details          ?
_audit_creation_date             2018-06-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 O2'
_chemical_formula_sum            'C18 H16 O2'
_chemical_formula_weight         264.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H16 O2'
_chemical_oxdiff_usercomment     
'HPHWLB #17703 GVA-1446 MOUNTED ON MICROMOUNT IN FOMBLIN FOR HP/HWL'
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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2469(3)
_cell_length_b                   9.0265(3)
_cell_length_c                   9.4627(3)
_cell_angle_alpha                95.548(3)
_cell_angle_beta                 94.576(3)
_cell_angle_gamma                92.972(3)
_cell_volume                     697.62(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8027
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.9000
_cell_measurement_theta_min      4.6880
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.779
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.581
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             280
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0589
0 0 -1 0.0619
-1 0 0 0.1701
5 1 -3 0.2036
0 -1 0 0.0299
0 1 0 0.0299
2 -6 0 0.0689
5 -1 -2 0.2049
1 -4 5 0.0675
0 4 -5 0.0572
3 3 -4 0.1519

_exptl_crystal_size_max          0.411
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.06
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
-0.0000 0.0011 0.9991 0.1547 0.0279 -0.0469
0.0000 -0.0011 -0.9991 -0.1547 -0.0279 0.0469
-0.9997 -0.0009 0.0006 -0.0570 -0.0604 -0.1683
4.9978 1.0000 -3.0014 -0.1190 0.0646 1.0284
0.0008 -0.9991 0.0010 -0.0602 0.1539 -0.0463
-0.0008 0.9991 -0.0010 0.0602 -0.1539 0.0463
2.0039 -5.9931 0.0051 -0.2472 1.0441 0.0588
4.9993 -0.9971 -2.0002 -0.0847 0.4002 0.8890
1.0025 -3.9900 4.9992 0.5898 0.8153 -0.2512
-0.0028 3.9909 -4.9998 -0.5328 -0.7549 0.4195
2.9969 2.9954 -4.0014 -0.2673 -0.3919 0.8313

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11681
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.914
_diffrn_reflns_theta_min         4.712
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 4.2207
_diffrn_detector_type            'Agilent Diffraction Titan S2 detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  16.00   1.00    1.00    --   32.00 102.00 132.07   25
  2  ω    -81.00  18.00   1.00    1.00    --  -42.81 102.00  61.00   99
  3  ω   -112.00 -50.00   1.00    1.00    --  -42.81 -77.00 -30.00   62
  4  ω    -46.00 -12.00   1.00    1.00    --  -42.81 -77.00 -30.00   34
  5  ω    -75.00 -20.00   1.00    1.00    --  -42.81 -38.00  30.00   55
  6  ω     24.00  91.00   1.00    1.00    --   42.81-125.00   0.00   67
  7  ω     64.00  89.00   1.00    1.00    --   42.81  57.00  90.00   25
  8  ω     21.00  46.00   1.00    1.00    --   42.81  57.00  90.00   25
  9  ω     14.00  42.00   1.00    1.00    --   44.00  79.00 169.85   28
 10  ω     18.00  45.00   1.00    1.00    --   48.00  79.00  32.29   27
 11  ω     16.00  41.00   1.00    1.00    --   48.00  81.00 -94.42   25
 12  ω     16.00  41.00   1.00    1.00    --   48.00  81.00-147.04   25
 13  ω     28.00  55.00   1.00    1.00    --   56.00  74.00 -44.31   27
 14  ω     32.00  59.00   1.00    1.00    --   60.00  75.00 122.17   27
 15  ω     96.00 123.00   1.00    1.00    --   60.00  75.00 122.17   27
 16  ω     35.00  67.00   1.00    1.00    --   64.00  77.00-101.41   32
 17  ω    107.00 136.00   1.00    1.00    --   64.00  77.00 -19.10   29
 18  ω     34.00  63.00   1.00    1.00    --   64.00  76.00-156.60   29
 19  ω     35.00  67.00   1.00    1.00    --   64.00  77.00 -19.10   32
 20  ω     34.00  72.00   1.00    1.00    --   64.00  76.00  71.44   38
 21  ω     36.00  85.00   1.00    1.00    --   64.00  77.00 139.64   49
 22  ω     96.00 134.00   1.00    1.00    --   64.00  76.00  71.44   38
 23  ω     38.00  64.00   1.00    1.00    --   68.00  76.00-146.45   26
 24  ω     38.00  70.00   1.00    1.00    --   68.00  75.00  29.06   32
 25  ω     42.00  68.00   1.00    1.00    --   72.00  75.00 -44.36   26
 26  ω     55.00 106.00   1.00    2.00    --   84.00  76.00-174.46   51
 27  ω     59.00 151.00   1.00    2.00    --   88.00  77.00  -9.61   92
 28  ω    116.00 143.00   1.00    2.00    --   96.00  67.00 -51.26   27
 29  ω     70.00 100.00   1.00    2.00    --   96.00  67.00 -51.26   30
 30  ω     26.00 110.00   1.00    2.00    --  103.32-102.00 -41.00   84
 31  ω     52.00  84.00   1.00    2.00    --  103.32 -30.00 120.00   32
 32  ω    140.00 175.00   1.00    2.00    --  103.32  77.00-150.00   35
 33  ω     73.00 100.00   1.00    2.00    --  103.32  77.00-150.00   27
 34  ω     79.00 160.00   1.00    2.00    --  103.32  61.00  90.00   81
 35  ω     74.00 175.00   1.00    2.00    --  103.32  77.00 150.00  101
 36  ω     24.00  70.00   1.00    2.00    --  103.32 -94.00   0.00   46
 37  ω    111.00 138.00   1.00    2.00    --  103.32  77.00  30.00   27
 38  ω     74.00 104.00   1.00    2.00    --  103.32  77.00  30.00   30
 39  ω     74.00 167.00   1.00    2.00    --  103.32  77.00 -90.00   93
 40  ω     33.00 117.00   1.00    2.00    --  103.32-125.00  90.00   84
 41  ω     78.00 105.00   1.00    2.00    --  103.32  77.00  90.00   27
 42  ω     79.00 145.00   1.00    2.00    --  103.32  61.00-150.00   66
 43  ω     95.00 173.00   1.00    2.00    --  103.32 125.00  30.00   78
 44  ω     78.00 143.00   1.00    2.00    --  103.32  61.00 -30.00   65
 45  ω     78.00 105.00   1.00    2.00    --  103.32  77.00   0.00   27
 46  ω    117.00 175.00   1.00    2.00    --  103.32  77.00   0.00   58
 47  ω     25.00 106.00   1.00    2.00    --  103.32 -94.00-180.00   81
 48  ω     74.00 149.00   1.00    2.00    --  103.32  77.00-120.00   75
 49  ω     86.00 113.00   1.00    2.00    --  103.32  61.00  60.00   27
 50  ω     74.00 145.00   1.00    2.00    --  103.32  77.00 120.00   71
 51  ω     34.00  89.00   1.00    2.00    --  103.32 -94.00 120.00   55
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Titan S2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0570468000
_diffrn_orient_matrix_UB_12      0.0604536000
_diffrn_orient_matrix_UB_13      0.1547857000
_diffrn_orient_matrix_UB_21      0.0605795000
_diffrn_orient_matrix_UB_22      -0.1539462000
_diffrn_orient_matrix_UB_23      0.0280734000
_diffrn_orient_matrix_UB_31      0.1682918000
_diffrn_orient_matrix_UB_32      0.0464259000
_diffrn_orient_matrix_UB_33      -0.0469503000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2529
_reflns_number_total             2769
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2769
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.058
_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)+(0.0403P)²+0.1984P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0886
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19)
2.c X=CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
C1 C 0.95424(12) 0.31278(11) 0.68201(11) 0.0214(2) Uani 1 1 d . . . . .
C2 C 0.83276(13) 0.20634(11) 0.74930(11) 0.0240(2) Uani 1 1 d . . . . .
H2 H 0.722612 0.247654 0.750110 0.029 Uiso 1 1 calc R . . . .
C3 C 0.90836(16) 0.19921(12) 0.90129(12) 0.0305(3) Uani 1 1 d . . . . .
C4 C 1.08092(15) 0.24909(11) 0.90302(12) 0.0289(3) Uani 1 1 d . . . . .
C5 C 1.20776(19) 0.24296(14) 1.00837(14) 0.0418(3) Uani 1 1 d . . . . .
H5 H 1.189227 0.199333 1.093524 0.050 Uiso 1 1 calc R . . . .
C6 C 1.36043(18) 0.30124(15) 0.98694(16) 0.0487(4) Uani 1 1 d . . . . .
H6 H 1.447738 0.297732 1.058143 0.058 Uiso 1 1 calc R . . . .
C7 C 1.38864(16) 0.36524(15) 0.86238(16) 0.0447(4) Uani 1 1 d . . . . .
H7 H 1.494569 0.405773 0.849921 0.054 Uiso 1 1 calc R . . . .
C8 C 1.26310(14) 0.37035(12) 0.75606(13) 0.0319(3) Uani 1 1 d . . . . .
H8 H 1.282050 0.413165 0.670576 0.038 Uiso 1 1 calc R . . . .
C9 C 1.10971(13) 0.31143(11) 0.77793(11) 0.0236(2) Uani 1 1 d . . . . .
O10 O 0.97445(9) 0.27312(8) 0.53580(8) 0.02452(18) Uani 1 1 d . . . . .
H10 H 1.0061(17) 0.1839(17) 0.5252(15) 0.037 Uiso 1 1 d R . . . .
C11 C 0.89102(14) 0.46913(11) 0.68964(12) 0.0287(2) Uani 1 1 d . . . . .
H11A H 0.788065 0.467298 0.629954 0.043 Uiso 1 1 calc GR . . . .
H11B H 0.971327 0.537943 0.655350 0.043 Uiso 1 1 calc GR . . . .
H11C H 0.873082 0.502496 0.788530 0.043 Uiso 1 1 calc GR . . . .
C12 C 0.82057(12) 0.04693(11) 0.67887(10) 0.0215(2) Uani 1 1 d . . . . .
O13 O 0.94282(9) -0.00877(8) 0.63805(8) 0.02663(18) Uani 1 1 d . . . . .
C14 C 0.66219(12) -0.04296(11) 0.66784(10) 0.0206(2) Uani 1 1 d . . . . .
C15 C 0.66320(13) -0.19640(12) 0.62858(11) 0.0244(2) Uani 1 1 d . . . . .
H15 H 0.762447 -0.239962 0.608953 0.029 Uiso 1 1 calc R . . . .
C16 C 0.51978(14) -0.28459(12) 0.61836(12) 0.0303(3) Uani 1 1 d . . . . .
H16 H 0.521439 -0.388950 0.593306 0.036 Uiso 1 1 calc R . . . .
C17 C 0.37321(14) -0.22210(13) 0.64435(12) 0.0297(2) Uani 1 1 d . . . . .
H17 H 0.275145 -0.283431 0.636979 0.036 Uiso 1 1 calc R . . . .
C18 C 0.37079(13) -0.07030(13) 0.68099(12) 0.0291(2) Uani 1 1 d . . . . .
H18 H 0.270641 -0.026928 0.697590 0.035 Uiso 1 1 calc R . . . .
C19 C 0.51442(13) 0.01881(12) 0.69355(11) 0.0256(2) Uani 1 1 d . . . . .
H19 H 0.512143 0.122892 0.719908 0.031 Uiso 1 1 calc R . . . .
C20 C 0.8295(2) 0.15570(15) 1.00897(15) 0.0487(4) Uani 1 1 d . . . . .
H20A H 0.885855 0.154673 1.100383 0.058 Uiso 1 1 calc R . . . .
H20B H 0.716754 0.125694 0.994388 0.058 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.5661(14) . ?
C1 C9 1.5119(14) . ?
C1 O10 1.4202(12) . ?
C1 C11 1.5269(13) . ?
C2 C3 1.5298(16) . ?
C2 C12 1.5211(13) . ?
C3 C4 1.4685(17) . ?
C3 C20 1.3314(17) . ?
C4 C5 1.3933(17) . ?
C4 C9 1.3907(16) . ?
C5 C6 1.377(2) . ?
C6 C7 1.392(2) . ?
C7 C8 1.3907(18) . ?
C8 C9 1.3854(16) . ?
C12 O13 1.2230(12) . ?
C12 C14 1.4924(14) . ?
C14 C15 1.3995(14) . ?
C14 C19 1.3952(14) . ?
C15 C16 1.3825(15) . ?
C16 C17 1.3896(16) . ?
C17 C18 1.3821(17) . ?
C18 C19 1.3872(16) . ?

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
C9 C1 C2 103.16(8) . . ?
C9 C1 C11 110.48(8) . . ?
O10 C1 C2 114.99(8) . . ?
O10 C1 C9 113.45(8) . . ?
O10 C1 C11 105.55(8) . . ?
C11 C1 C2 109.24(8) . . ?
C3 C2 C1 104.54(9) . . ?
C12 C2 C1 113.70(8) . . ?
C12 C2 C3 106.01(8) . . ?
C4 C3 C2 106.70(9) . . ?
C20 C3 C2 125.42(13) . . ?
C20 C3 C4 127.88(13) . . ?
C5 C4 C3 129.51(11) . . ?
C9 C4 C3 110.33(10) . . ?
C9 C4 C5 120.15(12) . . ?
C6 C5 C4 118.86(13) . . ?
C5 C6 C7 120.93(12) . . ?
C8 C7 C6 120.57(13) . . ?
C9 C8 C7 118.33(12) . . ?
C4 C9 C1 111.22(10) . . ?
C8 C9 C1 127.52(10) . . ?
C8 C9 C4 121.15(11) . . ?
O13 C12 C2 119.52(9) . . ?
O13 C12 C14 120.54(9) . . ?
C14 C12 C2 119.84(9) . . ?
C15 C14 C12 117.87(9) . . ?
C19 C14 C12 123.20(9) . . ?
C19 C14 C15 118.92(10) . . ?
C16 C15 C14 120.00(10) . . ?
C15 C16 C17 120.66(10) . . ?
C18 C17 C16 119.68(10) . . ?
C17 C18 C19 120.09(10) . . ?
C18 C19 C14 120.63(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O10 H10 O13 0.858(16) 2.189(15) 2.8154(10) 129.7(12) . yes
O10 H10 O13 0.858(16) 2.183(15) 2.9077(10) 142.0(13) 2_756 yes

loop_
_audit_author_email
''
william.lewis@nottingham.ac.uk
''
_olex2_date_sample_data_collection 2018-05-24
_olex2_date_sample_submission    2018-05-24
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_original_sample_id HP689
_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 1.192
_oxdiff_exptl_absorpt_empirical_full_min 0.787
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether, n-pentane'
####################################################################### 
# 
# 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_hphwlc
_database_code_depnum_ccdc_archive 'CCDC 1858964'
_audit_update_record             
;
2018-07-28 deposited with the CCDC.
2018-10-10 downloaded from the CCDC.
;
_nottingham_internal_coll_name   HPHWLC
_nottingham_internal_coll_number 17704
_nottingham_internal_coll_client HP/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '70.00, 17.50'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   24/05/2018
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 04/06/2018
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 4/6/2018
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 4/6/2018
_nottingham_internal_refinement_user pczwl
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 5/6/2018
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 5/6/2018
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_vrf_PLAT915_hphwlc              
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         32 %     
RESPONSE: The polarity of the crystal is not of interest in this study.
;
_audit_creation_date             2018-06-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 O3'
_chemical_formula_sum            'C14 H14 O3'
_chemical_formula_weight         230.25
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H14 O3'
_chemical_oxdiff_usercomment     
'HPHWLC #17704 GVB-1517 IN FOMBLIN ON MICROMOUNT FOR HP/HWL'
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'
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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   23.9951(5)
_cell_length_b                   14.2011(3)
_cell_length_c                   6.89980(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2351.15(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3461
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.1790
_cell_measurement_theta_min      6.2290
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.813
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             976
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 1 0 0.0063
2 -1 0 0.0093
0 -1 0 0.0228
0 1 0 0.0288
0 0 1 0.2585
0 0 -1 0.4476
0 -15 0 0.0079

_exptl_crystal_recrystallization_method 
'crystallised from a mixture of diethyl ether and n-pentane'
_exptl_crystal_size_max          0.706
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.016
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
-1.9999 0.9948 -0.0002 0.0018 0.2253 0.0198
1.9999 -0.9948 0.0002 -0.0018 -0.2253 -0.0198
0.0006 -0.9999 0.0000 -0.0595 -0.0162 -0.0179
-0.0006 0.9999 -0.0000 0.0595 0.0162 0.0179
-0.0015 0.0054 1.0000 -0.0592 -0.0183 0.2145
0.0015 -0.0054 -1.0000 0.0592 0.0183 -0.2145
0.0091 -14.9968 0.2004 -0.9037 -0.2466 -0.2263

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8261
_diffrn_reflns_point_group_measured_fraction_full 0.709
_diffrn_reflns_point_group_measured_fraction_max 0.673
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.603
_diffrn_reflns_theta_min         3.617
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.2349
_diffrn_detector_type            'Agilent Diffraction Atlas S2 detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00  30.00   1.00   17.50    --  -43.08  38.00-180.00   80
  2  ω     29.00 103.00   1.00   17.50    --   43.08-134.00-108.00   74
  3  ω      6.00 122.00   1.00   17.50    --   43.08  19.00 -90.00  116
  4  ω     25.00 109.00   1.00   70.00    --  106.43 -94.00-150.00   84
  5  ω     32.00  91.00   1.00   70.00    --  106.43 -30.00-150.00   59
  6  ω     32.00  91.00   1.00   70.00    --  106.43 -30.00-120.00   59
  7  ω     35.00  98.00   1.00   70.00    --  106.43 -45.00-180.00   63
  8  ω     35.00  90.00   1.00   70.00    --  106.43 -45.00 -60.00   55
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas S2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0287012000
_diffrn_orient_matrix_UB_12      0.0594805000
_diffrn_orient_matrix_UB_13      -0.0595272000
_diffrn_orient_matrix_UB_21      -0.1046116000
_diffrn_orient_matrix_UB_22      0.0161338000
_diffrn_orient_matrix_UB_23      -0.0185355000
_diffrn_orient_matrix_UB_31      -0.0009931000
_diffrn_orient_matrix_UB_32      0.0179530000
_diffrn_orient_matrix_UB_33      0.2144389000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_reflns_Friedel_coverage         0.274
_reflns_Friedel_fraction_full    0.362
_reflns_Friedel_fraction_max     0.317
_reflns_number_gt                2917
_reflns_number_total             3250
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3250
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0361
_refine_ls_restrained_S_all      1.039
_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)+(0.0534P)²+0.3148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0957
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.2(3)
 -0.2(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C35(H35A,H35B), C36(H36A,H36B)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C25(H25), C26(H26), C27(H27), C28(H28)
3.c X=CH2 refined with riding coordinates:
 C17(H17A,H17B), C37(H37A,H37B)
3.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C31(H31A,H31B,H31C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
C1 C 0.41146(10) 1.00370(17) 0.6659(4) 0.0228(5) Uani 1 1 d . . . . .
C2 C 0.40698(10) 0.89358(17) 0.6960(4) 0.0231(5) Uani 1 1 d . . . . .
C3 C 0.34759(10) 0.87904(18) 0.7680(4) 0.0258(5) Uani 1 1 d . . . . .
C4 C 0.33083(10) 0.96842(18) 0.8584(4) 0.0234(5) Uani 1 1 d . . . . .
C5 C 0.28659(11) 0.9878(2) 0.9832(4) 0.0314(6) Uani 1 1 d . . . . .
H5 H 0.261607 0.939368 1.021719 0.038 Uiso 1 1 calc R . . . .
C6 C 0.27986(11) 1.0791(2) 1.0498(4) 0.0347(7) Uani 1 1 d . . . . .
H6 H 0.249731 1.093525 1.134034 0.042 Uiso 1 1 calc R . . . .
C7 C 0.31657(11) 1.1501(2) 0.9950(4) 0.0333(6) Uani 1 1 d . . . . .
H7 H 0.311316 1.212251 1.042461 0.040 Uiso 1 1 calc R . . . .
C8 C 0.36089(11) 1.13086(18) 0.8714(4) 0.0286(6) Uani 1 1 d . . . . .
H8 H 0.386111 1.179135 0.834101 0.034 Uiso 1 1 calc R . . . .
C9 C 0.36744(10) 1.03932(18) 0.8038(4) 0.0228(5) Uani 1 1 d . . . . .
O10 O 0.46490(7) 1.03693(13) 0.7261(3) 0.0291(4) Uani 1 1 d . . . . .
H10 H 0.4853(15) 1.061(3) 0.640(5) 0.044 Uiso 1 1 d R . . . .
C11 C 0.39845(12) 1.03421(19) 0.4585(4) 0.0308(6) Uani 1 1 d . . . . .
H11A H 0.395640 1.103001 0.452928 0.046 Uiso 1 1 calc GR . . . .
H11B H 0.363041 1.006219 0.417365 0.046 Uiso 1 1 calc GR . . . .
H11C H 0.428327 1.012977 0.372041 0.046 Uiso 1 1 calc GR . . . .
C12 C 0.44846(11) 0.87078(18) 0.8584(4) 0.0245(5) Uani 1 1 d . . . . .
O13 O 0.44377(8) 0.88495(13) 1.0292(3) 0.0308(4) Uani 1 1 d . . . . .
O14 O 0.49440(7) 0.83019(13) 0.7856(3) 0.0306(4) Uani 1 1 d . . . . .
C15 C 0.49058(13) 0.8239(2) 0.5760(4) 0.0341(7) Uani 1 1 d . . . . .
H15A H 0.505975 0.763366 0.529208 0.041 Uiso 1 1 calc R . . . .
H15B H 0.511186 0.876181 0.513741 0.041 Uiso 1 1 calc R . . . .
C16 C 0.42857(12) 0.83067(19) 0.5322(4) 0.0311(6) Uani 1 1 d . . . . .
H16A H 0.410712 0.767851 0.535658 0.037 Uiso 1 1 calc R . . . .
H16B H 0.421914 0.859779 0.403931 0.037 Uiso 1 1 calc R . . . .
C17 C 0.31688(12) 0.8019(2) 0.7501(5) 0.0401(7) Uani 1 1 d . . . . .
H17A H 0.279815 0.800943 0.798447 0.048 Uiso 1 1 calc R . . . .
H17B H 0.331922 0.747702 0.688780 0.048 Uiso 1 1 calc R . . . .
C21 C 0.40461(10) 0.45840(17) 0.1577(4) 0.0227(5) Uani 1 1 d . . . . .
C22 C 0.39859(10) 0.56773(17) 0.1979(4) 0.0220(5) Uani 1 1 d . . . . .
C23 C 0.33927(10) 0.57739(18) 0.2747(4) 0.0250(5) Uani 1 1 d . . . . .
C24 C 0.32522(10) 0.48560(18) 0.3620(4) 0.0229(5) Uani 1 1 d . . . . .
C25 C 0.28292(10) 0.4616(2) 0.4911(4) 0.0295(6) Uani 1 1 d . . . . .
H25 H 0.256935 0.507536 0.534154 0.035 Uiso 1 1 calc R . . . .
C26 C 0.27953(11) 0.3696(2) 0.5553(4) 0.0315(6) Uani 1 1 d . . . . .
H26 H 0.250740 0.352116 0.642685 0.038 Uiso 1 1 calc R . . . .
C27 C 0.31777(11) 0.3023(2) 0.4936(4) 0.0305(6) Uani 1 1 d . . . . .
H27 H 0.314857 0.239485 0.539702 0.037 Uiso 1 1 calc R . . . .
C28 C 0.36011(11) 0.32601(18) 0.3656(4) 0.0264(5) Uani 1 1 d . . . . .
H28 H 0.386344 0.280198 0.323805 0.032 Uiso 1 1 calc R . . . .
C29 C 0.36319(10) 0.41811(17) 0.3002(4) 0.0218(5) Uani 1 1 d . . . . .
O30 O 0.45856(7) 0.42482(13) 0.2089(3) 0.0291(4) Uani 1 1 d . . . . .
H30 H 0.4853(15) 0.427(2) 0.123(5) 0.044 Uiso 1 1 d R . . . .
C31 C 0.38937(12) 0.4323(2) -0.0500(4) 0.0311(6) Uani 1 1 d . . . . .
H31A H 0.417142 0.458527 -0.139038 0.047 Uiso 1 1 calc GR . . . .
H31B H 0.352542 0.457934 -0.081383 0.047 Uiso 1 1 calc GR . . . .
H31C H 0.388621 0.363571 -0.063131 0.047 Uiso 1 1 calc GR . . . .
C32 C 0.43945(11) 0.59002(18) 0.3617(4) 0.0246(5) Uani 1 1 d . . . . .
O33 O 0.43525(8) 0.57253(14) 0.5316(3) 0.0325(4) Uani 1 1 d . . . . .
O34 O 0.48428(7) 0.63485(14) 0.2935(3) 0.0320(4) Uani 1 1 d . . . . .
C35 C 0.48044(13) 0.6456(2) 0.0840(4) 0.0360(7) Uani 1 1 d . . . . .
H35A H 0.502352 0.596295 0.017122 0.043 Uiso 1 1 calc R . . . .
H35B H 0.494338 0.708176 0.043245 0.043 Uiso 1 1 calc R . . . .
C36 C 0.41877(12) 0.63548(19) 0.0389(4) 0.0308(6) Uani 1 1 d . . . . .
H36A H 0.412890 0.608426 -0.091722 0.037 Uiso 1 1 calc R . . . .
H36B H 0.399396 0.696900 0.047261 0.037 Uiso 1 1 calc R . . . .
C37 C 0.30702(12) 0.6529(2) 0.2639(5) 0.0383(7) Uani 1 1 d . . . . .
H37A H 0.270393 0.651354 0.316069 0.046 Uiso 1 1 calc R . . . .
H37B H 0.320523 0.708668 0.203977 0.046 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.581(3) . ?
C1 C9 1.509(3) . ?
C1 O10 1.428(3) . ?
C1 C11 1.527(4) . ?
C2 C3 1.523(3) . ?
C2 C12 1.533(4) . ?
C2 C16 1.531(4) . ?
C3 C4 1.470(4) . ?
C3 C17 1.326(4) . ?
C4 C5 1.394(4) . ?
C4 C9 1.388(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.390(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.390(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.390(4) . ?
O10 H10 0.84(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O13 1.201(3) . ?
C12 O14 1.341(3) . ?
O14 C15 1.452(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.521(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9500 . ?
C17 H17B 0.9500 . ?
C21 C22 1.584(3) . ?
C21 C29 1.510(3) . ?
C21 O30 1.424(3) . ?
C21 C31 1.525(4) . ?
C22 C23 1.525(3) . ?
C22 C32 1.529(4) . ?
C22 C36 1.538(4) . ?
C23 C24 1.475(4) . ?
C23 C37 1.325(4) . ?
C24 C25 1.393(4) . ?
C24 C29 1.389(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.382(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.391(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.388(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.386(4) . ?
O30 H30 0.87(4) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 O33 1.202(3) . ?
C32 O34 1.336(3) . ?
O34 C35 1.456(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C36 1.519(4) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 H37A 0.9500 . ?
C37 H37B 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
C9 C1 C2 101.6(2) . . ?
C9 C1 C11 110.7(2) . . ?
O10 C1 C2 110.5(2) . . ?
O10 C1 C9 109.5(2) . . ?
O10 C1 C11 111.3(2) . . ?
C11 C1 C2 112.9(2) . . ?
C3 C2 C1 103.9(2) . . ?
C3 C2 C12 109.9(2) . . ?
C3 C2 C16 118.6(2) . . ?
C12 C2 C1 105.11(19) . . ?
C16 C2 C1 117.2(2) . . ?
C16 C2 C12 101.3(2) . . ?
C4 C3 C2 106.1(2) . . ?
C17 C3 C2 127.0(3) . . ?
C17 C3 C4 126.9(3) . . ?
C5 C4 C3 129.8(2) . . ?
C9 C4 C3 109.8(2) . . ?
C9 C4 C5 120.4(2) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 C4 118.5(3) . . ?
C6 C5 H5 120.7 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.0(3) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 120.8 . . ?
C9 C8 C7 118.4(3) . . ?
C9 C8 H8 120.8 . . ?
C4 C9 C1 111.8(2) . . ?
C4 C9 C8 121.1(2) . . ?
C8 C9 C1 127.2(2) . . ?
C1 O10 H10 117(3) . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O13 C12 C2 128.4(2) . . ?
O13 C12 O14 121.1(3) . . ?
O14 C12 C2 110.5(2) . . ?
C12 O14 C15 110.3(2) . . ?
O14 C15 H15A 110.8 . . ?
O14 C15 H15B 110.8 . . ?
O14 C15 C16 104.8(2) . . ?
H15A C15 H15B 108.9 . . ?
C16 C15 H15A 110.8 . . ?
C16 C15 H15B 110.8 . . ?
C2 C16 H16A 111.2 . . ?
C2 C16 H16B 111.2 . . ?
C15 C16 C2 102.8(2) . . ?
C15 C16 H16A 111.2 . . ?
C15 C16 H16B 111.2 . . ?
H16A C16 H16B 109.1 . . ?
C3 C17 H17A 120.0 . . ?
C3 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?
C29 C21 C22 101.4(2) . . ?
C29 C21 C31 111.2(2) . . ?
O30 C21 C22 111.6(2) . . ?
O30 C21 C29 108.1(2) . . ?
O30 C21 C31 111.7(2) . . ?
C31 C21 C22 112.4(2) . . ?
C23 C22 C21 103.55(19) . . ?
C23 C22 C32 108.9(2) . . ?
C23 C22 C36 119.0(2) . . ?
C32 C22 C21 105.9(2) . . ?
C32 C22 C36 101.3(2) . . ?
C36 C22 C21 117.4(2) . . ?
C24 C23 C22 106.0(2) . . ?
C37 C23 C22 126.8(3) . . ?
C37 C23 C24 127.2(3) . . ?
C25 C24 C23 130.1(2) . . ?
C29 C24 C23 109.5(2) . . ?
C29 C24 C25 120.4(2) . . ?
C24 C25 H25 120.7 . . ?
C26 C25 C24 118.6(3) . . ?
C26 C25 H25 120.7 . . ?
C25 C26 H26 119.6 . . ?
C25 C26 C27 120.8(3) . . ?
C27 C26 H26 119.6 . . ?
C26 C27 H27 119.6 . . ?
C28 C27 C26 120.7(3) . . ?
C28 C27 H27 119.6 . . ?
C27 C28 H28 120.8 . . ?
C29 C28 C27 118.4(3) . . ?
C29 C28 H28 120.8 . . ?
C24 C29 C21 111.7(2) . . ?
C28 C29 C21 127.2(2) . . ?
C28 C29 C24 121.1(2) . . ?
C21 O30 H30 119(2) . . ?
C21 C31 H31A 109.5 . . ?
C21 C31 H31B 109.5 . . ?
C21 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O33 C32 C22 128.6(3) . . ?
O33 C32 O34 120.7(3) . . ?
O34 C32 C22 110.8(2) . . ?
C32 O34 C35 110.4(2) . . ?
O34 C35 H35A 110.8 . . ?
O34 C35 H35B 110.8 . . ?
O34 C35 C36 104.8(2) . . ?
H35A C35 H35B 108.9 . . ?
C36 C35 H35A 110.8 . . ?
C36 C35 H35B 110.8 . . ?
C22 C36 H36A 111.2 . . ?
C22 C36 H36B 111.2 . . ?
C35 C36 C22 102.7(2) . . ?
C35 C36 H36A 111.2 . . ?
C35 C36 H36B 111.2 . . ?
H36A C36 H36B 109.1 . . ?
C23 C37 H37A 120.0 . . ?
C23 C37 H37B 120.0 . . ?
H37A C37 H37B 120.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O10 H10 O13 0.84(4) 2.02(4) 2.807(3) 156(4) 2_674 yes
O30 H30 O33 0.87(4) 2.01(4) 2.827(3) 156(3) 2_664 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -24.8(3) . . . . ?
C1 C2 C3 C17 154.1(3) . . . . ?
C1 C2 C12 O13 75.3(3) . . . . ?
C1 C2 C12 O14 -104.6(2) . . . . ?
C1 C2 C16 C15 84.8(3) . . . . ?
C2 C1 C9 C4 -16.9(3) . . . . ?
C2 C1 C9 C8 164.4(3) . . . . ?
C2 C3 C4 C5 -164.0(3) . . . . ?
C2 C3 C4 C9 15.2(3) . . . . ?
C2 C12 O14 C15 1.9(3) . . . . ?
C3 C2 C12 O13 -36.0(4) . . . . ?
C3 C2 C12 O14 144.1(2) . . . . ?
C3 C2 C16 C15 -149.2(2) . . . . ?
C3 C4 C5 C6 179.7(3) . . . . ?
C3 C4 C9 C1 1.7(3) . . . . ?
C3 C4 C9 C8 -179.5(2) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C5 C4 C9 C1 -179.0(2) . . . . ?
C5 C4 C9 C8 -0.2(4) . . . . ?
C5 C6 C7 C8 0.2(4) . . . . ?
C6 C7 C8 C9 0.2(4) . . . . ?
C7 C8 C9 C1 178.4(3) . . . . ?
C7 C8 C9 C4 -0.2(4) . . . . ?
C9 C1 C2 C3 24.7(2) . . . . ?
C9 C1 C2 C12 -90.7(2) . . . . ?
C9 C1 C2 C16 157.7(2) . . . . ?
C9 C4 C5 C6 0.5(4) . . . . ?
O10 C1 C2 C3 140.9(2) . . . . ?
O10 C1 C2 C12 25.4(3) . . . . ?
O10 C1 C2 C16 -86.1(3) . . . . ?
O10 C1 C9 C4 -133.7(2) . . . . ?
O10 C1 C9 C8 47.5(3) . . . . ?
C11 C1 C2 C3 -93.8(2) . . . . ?
C11 C1 C2 C12 150.7(2) . . . . ?
C11 C1 C2 C16 39.2(3) . . . . ?
C11 C1 C9 C4 103.3(3) . . . . ?
C11 C1 C9 C8 -75.5(3) . . . . ?
C12 C2 C3 C4 87.2(2) . . . . ?
C12 C2 C3 C17 -93.8(3) . . . . ?
C12 C2 C16 C15 -28.9(3) . . . . ?
C12 O14 C15 C16 -21.2(3) . . . . ?
O13 C12 O14 C15 -178.1(3) . . . . ?
O14 C15 C16 C2 31.2(3) . . . . ?
C16 C2 C3 C4 -157.0(2) . . . . ?
C16 C2 C3 C17 21.9(4) . . . . ?
C16 C2 C12 O13 -162.2(3) . . . . ?
C16 C2 C12 O14 17.8(3) . . . . ?
C17 C3 C4 C5 17.0(5) . . . . ?
C17 C3 C4 C9 -163.8(3) . . . . ?
C21 C22 C23 C24 26.2(3) . . . . ?
C21 C22 C23 C37 -153.5(3) . . . . ?
C21 C22 C32 O33 -75.0(3) . . . . ?
C21 C22 C32 O34 105.1(2) . . . . ?
C21 C22 C36 C35 -85.9(3) . . . . ?
C22 C21 C29 C24 18.7(3) . . . . ?
C22 C21 C29 C28 -162.4(2) . . . . ?
C22 C23 C24 C25 162.9(3) . . . . ?
C22 C23 C24 C29 -15.5(3) . . . . ?
C22 C32 O34 C35 -1.6(3) . . . . ?
C23 C22 C32 O33 35.8(4) . . . . ?
C23 C22 C32 O34 -144.1(2) . . . . ?
C23 C22 C36 C35 148.0(2) . . . . ?
C23 C24 C25 C26 -178.5(3) . . . . ?
C23 C24 C29 C21 -2.7(3) . . . . ?
C23 C24 C29 C28 178.3(2) . . . . ?
C24 C25 C26 C27 0.5(4) . . . . ?
C25 C24 C29 C21 178.7(2) . . . . ?
C25 C24 C29 C28 -0.3(4) . . . . ?
C25 C26 C27 C28 -0.2(4) . . . . ?
C26 C27 C28 C29 -0.3(4) . . . . ?
C27 C28 C29 C21 -178.3(2) . . . . ?
C27 C28 C29 C24 0.5(4) . . . . ?
C29 C21 C22 C23 -26.6(2) . . . . ?
C29 C21 C22 C32 87.9(2) . . . . ?
C29 C21 C22 C36 -160.0(2) . . . . ?
C29 C24 C25 C26 -0.2(4) . . . . ?
O30 C21 C22 C23 -141.4(2) . . . . ?
O30 C21 C22 C32 -26.9(3) . . . . ?
O30 C21 C22 C36 85.2(3) . . . . ?
O30 C21 C29 C24 136.1(2) . . . . ?
O30 C21 C29 C28 -44.9(3) . . . . ?
C31 C21 C22 C23 92.2(2) . . . . ?
C31 C21 C22 C32 -153.3(2) . . . . ?
C31 C21 C22 C36 -41.2(3) . . . . ?
C31 C21 C29 C24 -101.0(3) . . . . ?
C31 C21 C29 C28 78.0(3) . . . . ?
C32 C22 C23 C24 -86.1(2) . . . . ?
C32 C22 C23 C37 94.2(3) . . . . ?
C32 C22 C36 C35 28.8(3) . . . . ?
C32 O34 C35 C36 20.9(3) . . . . ?
O33 C32 O34 C35 178.5(3) . . . . ?
O34 C35 C36 C22 -30.8(3) . . . . ?
C36 C22 C23 C24 158.6(2) . . . . ?
C36 C22 C23 C37 -21.1(4) . . . . ?
C36 C22 C32 O33 162.0(3) . . . . ?
C36 C22 C32 O34 -17.8(3) . . . . ?
C37 C23 C24 C25 -17.4(5) . . . . ?
C37 C23 C24 C29 164.2(3) . . . . ?

_olex2_date_sample_data_collection 2018-05-24
_olex2_date_sample_submission    2018-05-24
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_original_sample_id HP738
_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 1.803
_oxdiff_exptl_absorpt_empirical_full_min 0.734
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.2(3)
2 -0.2(3)

####################################################################### 
# 
# 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_snkhld
_database_code_depnum_ccdc_archive 'CCDC 1858963'
_audit_update_record             
;
2018-07-28 deposited with the CCDC.
2018-10-10 downloaded from the CCDC.
;
_nottingham_internal_coll_name   SNKHLD
_nottingham_internal_coll_number 17705
_nottingham_internal_coll_client SNK/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time 1.00
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   24/05/2018
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'SN, XDA 017-09'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 04/06/2018
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 04/06/2018
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 04/06/2018
_nottingham_internal_refinement_user pczwl
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 05/06/2018
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 05/06/2018
_refine_special_details          
;
Atom C15 is disordered over two positions. The occupancies of the two components 
were refined competitively, converging to a ratio of 0.91:0.09. Similarity 
restraints were applied to the thermal parameters of C14, C15 and C15A.
;
_audit_creation_date             2018-06-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 N O3'
_chemical_formula_sum            'C16 H17 N O3'
_chemical_formula_weight         271.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H17 N O3'
_chemical_oxdiff_usercomment     
'SNKHLD #17705 SN-1333 IN FOMBLIN FILM ON A MICROMOUNT FOR SNK/HWL'
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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.5434(6)
_cell_length_b                   8.2224(3)
_cell_length_c                   18.7134(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2853.25(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3755
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.3160
_cell_measurement_theta_min      4.7700
_shelx_estimated_absorpt_T_max   0.886
_shelx_estimated_absorpt_T_min   0.790
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.491
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 0 -5 0.1196
4 0 5 0.1196
0 2 5 0.1254
5 -1 5 0.1314
0 0 -1 0.0874
0 0 1 0.0874
5 -2 5 0.1489
5 -2 -5 0.1553
-1 0 -5 0.0990
-5 2 5 0.1518
-5 2 -1 0.1853
-2 1 -5 0.1233
5 -2 -1 0.1689
-5 -5 -4 0.1161
-5 0 -2 0.1236
-5 -2 -3 0.1230
5 -4 0 0.1612
5 0 2 0.1628
5 1 2 0.1680
3 5 3 0.1567
-2 -3 5 0.1129
-5 0 2 0.1141
-5 -2 4 0.1033
4 3 -5 0.1356
5 2 -4 0.1480
5 0 -1 0.1624

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether'
_exptl_crystal_size_max          0.348
_exptl_crystal_size_mid          0.293
_exptl_crystal_size_min          0.175
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
-3.9944 0.0024 -4.9995 -0.4095 -0.1310 -0.3076
3.9944 -0.0024 4.9995 0.4095 0.1310 0.3076
-0.0042 1.9963 4.9959 0.5006 0.1561 -0.1837
4.9948 -1.0019 4.9999 0.3280 0.1624 0.4928
0.0003 0.0006 -0.9988 -0.0531 -0.0614 -0.0132
-0.0003 -0.0006 0.9988 0.0531 0.0614 0.0132
4.9963 -2.0015 4.9990 0.2104 0.2379 0.6176
4.9989 -1.9957 -4.9893 -0.3206 -0.3761 0.4859
-0.9976 0.0028 -4.9955 -0.3015 -0.2630 -0.1263
-4.9989 1.9957 4.9893 0.3206 0.3761 -0.4859
-4.9973 1.9992 -1.0037 0.0020 0.0077 -0.5649
-1.9980 1.0023 -4.9959 -0.2200 -0.2944 -0.3115
4.9979 -1.9980 -0.9940 -0.1082 -0.1305 0.5386
-4.9863 -4.9962 -4.0063 -0.9802 0.3516 0.2691
-4.9942 0.0006 -2.0043 -0.2862 0.0972 -0.3285
-4.9910 -1.9980 -3.0049 -0.5744 0.1867 -0.0921
5.0005 -3.9977 0.0031 -0.2902 0.0818 0.8013
4.9942 -0.0006 2.0043 0.2862 -0.0972 0.3285
4.9927 0.9990 2.0052 0.4038 -0.1726 0.2037
2.9887 4.9965 3.0049 0.8551 -0.3250 -0.4031
-1.9948 -3.0019 4.9889 -0.1592 0.6213 0.3194
-4.9952 -0.0018 1.9911 -0.0738 0.3428 -0.2758
-4.9928 -2.0021 3.9870 -0.2027 0.6165 0.0001
3.9927 3.0021 -4.9862 0.2312 -0.7093 -0.1985
4.9928 2.0021 -3.9870 0.2027 -0.6165 -0.0001
4.9949 0.0012 -0.9922 0.1269 -0.2814 0.2890

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6948
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.493
_diffrn_reflns_theta_min         4.770
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3613
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  28.00   1.00    1.00    --  -38.50  77.00  90.00   93
  2  ω    -31.00   7.00   1.00    1.00    --  -38.50  77.00 -30.00   38
  3  ω     90.00 158.00   1.00    1.00    --  106.13  77.00-180.00   68
  4  ω    153.00 178.00   1.00    1.00    --  106.13  77.00  90.00   25
  5  ω    145.00 177.00   1.00    1.00    --  106.13  77.00  60.00   32
  6  ω     80.00 174.00   1.00    1.00    --  106.13  77.00 -60.00   94
  7  ω    115.00 173.00   1.00    1.00    --  106.13  77.00 150.00   58
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0359593000
_diffrn_orient_matrix_UB_12      0.1176085000
_diffrn_orient_matrix_UB_13      0.0532396000
_diffrn_orient_matrix_UB_21      -0.0441166000
_diffrn_orient_matrix_UB_22      -0.0755975000
_diffrn_orient_matrix_UB_23      0.0614135000
_diffrn_orient_matrix_UB_31      0.0604968000
_diffrn_orient_matrix_UB_32      -0.1247635000
_diffrn_orient_matrix_UB_33      0.0131340000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2541
_reflns_number_total             2841
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2841
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.049
_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)+(0.0459P)²+0.8197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0922
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C14 \\sim C15 \\sim C15A: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
3. Others
 Sof(H14C)=Sof(H14D)=Sof(C15A)=Sof(H15D)=Sof(H15E)=Sof(H15F)=1-FVAR(1)
 Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C14(H14C,H14D), C16(H16A,H16B)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8)
4.c X=CH2 refined with riding coordinates:
 C19(H19A,H19B)
4.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C15(H15A,H15B,H15C), C15A(H15D,H15E,H15F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
C1 C 0.42464(6) 0.71343(13) 0.54055(6) 0.0173(2) Uani 1 1 d . . . . .
C2 C 0.39055(6) 0.86958(13) 0.57763(6) 0.0178(2) Uani 1 1 d . . . . .
C3 C 0.35816(6) 0.96722(14) 0.51589(6) 0.0194(2) Uani 1 1 d . . . . .
C4 C 0.34897(6) 0.85271(14) 0.45628(6) 0.0193(2) Uani 1 1 d . . . . .
C5 C 0.31172(6) 0.87394(15) 0.39211(6) 0.0245(3) Uani 1 1 d . . . . .
H5 H 0.286655 0.972351 0.382586 0.029 Uiso 1 1 calc R . . . .
C6 C 0.31202(6) 0.74869(17) 0.34263(6) 0.0270(3) Uani 1 1 d . . . . .
H6 H 0.287006 0.761572 0.298694 0.032 Uiso 1 1 calc R . . . .
C7 C 0.34854(6) 0.60409(16) 0.35650(6) 0.0261(3) Uani 1 1 d . . . . .
H7 H 0.348445 0.519819 0.321767 0.031 Uiso 1 1 calc R . . . .
C8 C 0.38513(6) 0.58169(15) 0.42058(6) 0.0219(2) Uani 1 1 d . . . . .
H8 H 0.409737 0.482811 0.430319 0.026 Uiso 1 1 calc R . . . .
C9 C 0.38475(6) 0.70768(13) 0.46996(6) 0.0180(2) Uani 1 1 d . . . . .
O9 O 0.50008(4) 0.74099(11) 0.52933(4) 0.02086(19) Uani 1 1 d . . . . .
H9 H 0.5062(8) 0.8073(19) 0.4912(9) 0.031 Uiso 1 1 d R . . . .
C10 C 0.41995(7) 0.55724(14) 0.58345(6) 0.0231(3) Uani 1 1 d . . . . .
H10A H 0.442773 0.468710 0.556656 0.035 Uiso 1 1 calc GR . . . .
H10B H 0.369205 0.530489 0.592182 0.035 Uiso 1 1 calc GR . . . .
H10C H 0.444828 0.571618 0.629215 0.035 Uiso 1 1 calc GR . . . .
C11 C 0.45012(6) 0.95667(14) 0.61841(6) 0.0208(2) Uani 1 1 d . . . . .
O12 O 0.48231(5) 1.07534(11) 0.59844(5) 0.0293(2) Uani 1 1 d . . . . .
O13 O 0.46297(5) 0.88076(11) 0.68030(4) 0.0274(2) Uani 1 1 d . . . . .
C14 C 0.52416(8) 0.93519(19) 0.72252(8) 0.0391(3) Uani 1 1 d . U . . .
H14A H 0.511698 0.931719 0.773941 0.047 Uiso 0.908(5) 1 calc R . P A 1
H14B H 0.536214 1.048905 0.709880 0.047 Uiso 0.908(5) 1 calc R . P A 1
H14C H 0.555645 1.000523 0.690876 0.047 Uiso 0.092(5) 1 calc R . P A 2
H14D H 0.505594 1.009433 0.759888 0.047 Uiso 0.092(5) 1 calc R . P A 2
C15 C 0.58701(8) 0.8291(2) 0.70869(11) 0.0414(5) Uani 0.908(5) 1 d . U P A 1
H15A H 0.627754 0.864691 0.738156 0.062 Uiso 0.908(5) 1 calc GR . P A 1
H15B H 0.600266 0.835949 0.658081 0.062 Uiso 0.908(5) 1 calc GR . P A 1
H15C H 0.574666 0.716501 0.720653 0.062 Uiso 0.908(5) 1 calc GR . P A 1
C15A C 0.5682(9) 0.817(2) 0.7568(10) 0.037(4) Uiso 0.092(5) 1 d . U P A 2
H15D H 0.544856 0.781147 0.801104 0.056 Uiso 0.092(5) 1 calc GR . P A 2
H15E H 0.615270 0.864729 0.767995 0.056 Uiso 0.092(5) 1 calc GR . P A 2
H15F H 0.574766 0.723444 0.724998 0.056 Uiso 0.092(5) 1 calc GR . P A 2
C16 C 0.32882(6) 0.81839(14) 0.62845(6) 0.0220(2) Uani 1 1 d . . . . .
H16A H 0.290773 0.763015 0.600429 0.026 Uiso 1 1 calc R . . . .
H16B H 0.347740 0.739699 0.663834 0.026 Uiso 1 1 calc R . . . .
C17 C 0.29711(6) 0.95656(16) 0.66624(6) 0.0255(3) Uani 1 1 d . . . . .
N18 N 0.27410(7) 1.06460(16) 0.69711(6) 0.0376(3) Uani 1 1 d . . . . .
C19 C 0.33989(7) 1.12352(15) 0.51704(7) 0.0263(3) Uani 1 1 d . . . . .
H19A H 0.318389 1.172039 0.476183 0.032 Uiso 1 1 calc R . . . .
H19B H 0.348325 1.186705 0.558706 0.032 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.5905(15) . ?
C1 C9 1.5147(14) . ?
C1 O9 1.4327(12) . ?
C1 C10 1.5170(15) . ?
C2 C3 1.5297(15) . ?
C2 C11 1.5217(15) . ?
C2 C16 1.5465(15) . ?
C3 C4 1.4697(16) . ?
C3 C19 1.3293(17) . ?
C4 C5 1.3962(16) . ?
C4 C9 1.3885(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3849(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.3927(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.3901(16) . ?
C8 H8 0.9500 . ?
C8 C9 1.3881(16) . ?
O9 H9 0.906(17) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O12 1.2033(14) . ?
C11 O13 1.3370(14) . ?
O13 C14 1.4533(15) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 H14C 0.9900 . ?
C14 H14D 0.9900 . ?
C14 C15 1.478(2) . ?
C14 C15A 1.423(16) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15A H15D 0.9800 . ?
C15A H15E 0.9800 . ?
C15A H15F 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.4617(17) . ?
C17 N18 1.1424(17) . ?
C19 H19A 0.9500 . ?
C19 H19B 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
C9 C1 C2 102.22(8) . . ?
C9 C1 C10 114.02(9) . . ?
O9 C1 C2 108.93(8) . . ?
O9 C1 C9 110.73(8) . . ?
O9 C1 C10 105.51(9) . . ?
C10 C1 C2 115.45(9) . . ?
C3 C2 C1 104.49(8) . . ?
C3 C2 C16 108.46(9) . . ?
C11 C2 C1 108.07(8) . . ?
C11 C2 C3 114.64(9) . . ?
C11 C2 C16 110.91(9) . . ?
C16 C2 C1 110.04(9) . . ?
C4 C3 C2 106.42(9) . . ?
C19 C3 C2 126.53(11) . . ?
C19 C3 C4 127.02(11) . . ?
C5 C4 C3 129.05(11) . . ?
C9 C4 C3 110.79(9) . . ?
C9 C4 C5 120.16(11) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 C4 118.68(11) . . ?
C6 C5 H5 120.7 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.82(11) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.74(11) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 120.9 . . ?
C9 C8 C7 118.22(11) . . ?
C9 C8 H8 120.9 . . ?
C4 C9 C1 111.55(9) . . ?
C8 C9 C1 126.97(10) . . ?
C8 C9 C4 121.37(10) . . ?
C1 O9 H9 109.5(10) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O12 C11 C2 125.86(10) . . ?
O12 C11 O13 124.00(11) . . ?
O13 C11 C2 110.13(9) . . ?
C11 O13 C14 117.79(10) . . ?
O13 C14 H14A 109.7 . . ?
O13 C14 H14B 109.7 . . ?
O13 C14 H14C 107.6 . . ?
O13 C14 H14D 107.6 . . ?
O13 C14 C15 109.79(12) . . ?
H14A C14 H14B 108.2 . . ?
H14C C14 H14D 107.0 . . ?
C15 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
C15A C14 O13 118.9(7) . . ?
C15A C14 H14C 107.6 . . ?
C15A C14 H14D 107.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C15A H15D 109.5 . . ?
C14 C15A H15E 109.5 . . ?
C14 C15A H15F 109.5 . . ?
H15D C15A H15E 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
C2 C16 H16A 109.1 . . ?
C2 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 C2 112.56(10) . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
N18 C17 C16 177.93(13) . . ?
C3 C19 H19A 120.0 . . ?
C3 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O9 H9 O12 0.906(17) 1.946(17) 2.8469(12) 172.5(14) 5_676 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 19.96(11) . . . . ?
C1 C2 C3 C19 -162.01(11) . . . . ?
C1 C2 C11 O12 100.48(13) . . . . ?
C1 C2 C11 O13 -78.59(11) . . . . ?
C1 C2 C16 C17 177.83(9) . . . . ?
C2 C1 C9 C4 14.38(11) . . . . ?
C2 C1 C9 C8 -169.41(10) . . . . ?
C2 C3 C4 C5 169.04(11) . . . . ?
C2 C3 C4 C9 -11.79(12) . . . . ?
C2 C11 O13 C14 172.73(10) . . . . ?
C3 C2 C11 O12 -15.56(16) . . . . ?
C3 C2 C11 O13 165.36(9) . . . . ?
C3 C2 C16 C17 -68.43(12) . . . . ?
C3 C4 C5 C6 178.40(11) . . . . ?
C3 C4 C9 C1 -2.17(12) . . . . ?
C3 C4 C9 C8 -178.62(10) . . . . ?
C4 C5 C6 C7 0.17(18) . . . . ?
C5 C4 C9 C1 177.09(10) . . . . ?
C5 C4 C9 C8 0.63(16) . . . . ?
C5 C6 C7 C8 0.46(18) . . . . ?
C6 C7 C8 C9 -0.54(17) . . . . ?
C7 C8 C9 C1 -175.88(10) . . . . ?
C7 C8 C9 C4 -0.01(16) . . . . ?
C9 C1 C2 C3 -20.39(10) . . . . ?
C9 C1 C2 C11 -142.89(9) . . . . ?
C9 C1 C2 C16 95.87(10) . . . . ?
C9 C4 C5 C6 -0.71(17) . . . . ?
O9 C1 C2 C3 96.81(9) . . . . ?
O9 C1 C2 C11 -25.68(11) . . . . ?
O9 C1 C2 C16 -146.93(9) . . . . ?
O9 C1 C9 C4 -101.52(10) . . . . ?
O9 C1 C9 C8 74.69(14) . . . . ?
C10 C1 C2 C3 -144.75(9) . . . . ?
C10 C1 C2 C11 92.76(11) . . . . ?
C10 C1 C2 C16 -28.49(13) . . . . ?
C10 C1 C9 C4 139.68(10) . . . . ?
C10 C1 C9 C8 -44.11(15) . . . . ?
C11 C2 C3 C4 138.05(9) . . . . ?
C11 C2 C3 C19 -43.91(16) . . . . ?
C11 C2 C16 C17 58.30(12) . . . . ?
C11 O13 C14 C15 -97.34(15) . . . . ?
C11 O13 C14 C15A -139.3(9) . . . . ?
O12 C11 O13 C14 -6.37(17) . . . . ?
C16 C2 C3 C4 -97.39(10) . . . . ?
C16 C2 C3 C19 80.64(14) . . . . ?
C16 C2 C11 O12 -138.81(12) . . . . ?
C16 C2 C11 O13 42.11(12) . . . . ?
C19 C3 C4 C5 -8.98(19) . . . . ?
C19 C3 C4 C9 170.19(11) . . . . ?

loop_
_audit_author_email
somnath.karad@nottingham.ac.uk
william.lewis@nottingham.ac.uk
''
_olex2_date_sample_data_collection 2018-05-24
_olex2_date_sample_submission    2018-05-24
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_original_sample_id SNK-6-46
_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 1.167
_oxdiff_exptl_absorpt_empirical_full_min 0.883
