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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jwg1805
_database_code_depnum_ccdc_archive 'CCDC 2128187'
loop_
_audit_author_name
_audit_author_address
'Adrian C. Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2021-12-13 deposited with the CCDC.	2022-02-16 downloaded from the CCDC.
;
_audit_creation_date             2018-10-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 N O'
_chemical_formula_sum            'C20 H21 N O'
_chemical_formula_weight         291.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H21 N1 O1'
_chemical_oxdiff_usercomment     'Richard Mandle RM2102'
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      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                   5.6557(4)
_cell_length_b                   10.2172(9)
_cell_length_c                   14.8788(10)
_cell_angle_alpha                70.217(7)
_cell_angle_beta                 81.954(6)
_cell_angle_gamma                88.731(6)
_cell_volume                     800.78(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1663
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      70.6090
_cell_measurement_theta_min      6.4680
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.572
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.541
_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    1.208
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             312
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0543
2 0 -5 0.0875
0 0 1 0.0695
0 -5 -1 0.0382
0 5 1 0.0227
-4 -1 -1 0.1700
3 1 5 0.1752
1 -4 -5 0.0516
0 -3 5 0.0489
0 -1 -1 0.0306
-3 -1 3 0.1316
-1 1 5 0.0608

_exptl_crystal_size_max          0.357
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.061
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
0.0003 -0.0002 -1.0009 -0.0404 -0.0423 0.0946
2.0023 -0.0012 -5.0043 0.1224 0.0605 0.8250
-0.0003 0.0002 1.0009 0.0404 0.0423 -0.0946
-0.0008 -4.9930 -0.9856 -0.4355 0.6281 -0.0946
0.0008 4.9930 0.9856 0.4355 -0.6281 0.0946
-4.0011 -0.9983 -0.9982 -0.7681 -0.4527 -0.6470
2.9994 0.9992 5.0016 0.7674 0.4859 0.0926
1.0011 -3.9953 -4.9922 -0.3558 0.4608 0.4977
-0.0024 -2.9947 5.0136 -0.0352 0.6140 -0.5866
0.0001 -0.9987 -0.9978 -0.1194 0.0918 0.0568
-3.0021 -0.9976 3.0055 -0.4444 -0.1472 -0.8495
-1.0018 0.9996 5.0013 0.1187 -0.0585 -0.6112

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4627
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         4.601
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  12.00   1.00    2.00    --    0.00  57.00 120.00   31
  2  ω     36.00  63.00   1.00    2.00    --    0.00  37.00-120.00   27
  3  ω     -7.00  20.00   1.00    2.00    --    0.00  37.00-120.00   27
  4  ω     39.00  67.00   1.00    2.00    --    0.00  57.00 120.00   28
  5  ω    -13.00  61.00   1.00    7.00    --   54.00 -57.00-120.00   74
  6  ω     58.00  85.00   1.00    7.00    --   54.00-125.00  60.00   27
  7  ω     39.00 126.00   1.00    7.00    --   54.00  37.00-150.00   87
  8  ω     29.00 126.00   1.00    7.00    --   54.00  37.00 120.00   97
  9  ω    -13.00  65.00   1.00    7.00    --   54.00 -57.00 -30.00   78
 10  ω     20.00  95.00   1.00    7.00    --   54.00 -99.00 150.00   75
 11  ω    109.00 167.00   1.00    7.00    --  108.00 111.00-120.00   58
 12  ω     91.00 129.00   1.00    7.00    --  108.00  37.00  90.00   38
 13  ω    152.00 178.00   1.00    7.00    --  108.00  37.00  90.00   26
 14  ω     64.00 113.00   1.00    7.00    --  108.00-111.00-120.00   49
 15  ω     51.00 102.00   1.00    7.00    --  108.00 -50.00 120.00   51
 16  ω     35.00 137.00   1.00    7.00    --  108.00 -25.00 150.00  102
 17  ω     74.00 134.00   1.00    7.00    --  108.00 -25.00 -90.00   60
 18  ω     38.00 100.00   1.00    7.00    --  108.00-111.00-180.00   62
 19  ω     38.00  66.00   1.00    7.00    --  108.00 -25.00 -90.00   28
 20  ω     74.00 153.00   1.00    7.00    --  108.00  25.00-180.00   79
 21  ω     45.00 122.00   1.00    7.00    --  108.00 -63.00-150.00   77
 22  ω     70.00 101.00   1.00    7.00    --  108.00-111.00 120.00   31
 23  ω     54.00 112.00   1.00    7.00    --  108.00-111.00   0.00   58
 24  ω     41.00 125.00   1.00    7.00    --  108.00 -63.00 -30.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1621248000
_diffrn_orient_matrix_UB_12      0.0792266000
_diffrn_orient_matrix_UB_13      0.0403814000
_diffrn_orient_matrix_UB_21      0.1360559000
_diffrn_orient_matrix_UB_22      -0.1341917000
_diffrn_orient_matrix_UB_23      0.0423722000
_diffrn_orient_matrix_UB_31      0.1758948000
_diffrn_orient_matrix_UB_32      0.0375627000
_diffrn_orient_matrix_UB_33      -0.0944802000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2291
_reflns_number_total             2832
_reflns_odcompleteness_completeness 99.30
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2832
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.032
_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)+(0.0680P)²+0.1347P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1288
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C20(H20A,H20B), C14(H14A,H14B), C16(H16A,H16B), C19(H19A,
 H19B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C5(H5), C1(H1), C2(H2), C8(H8), C4(H4), C11(H11), C9(H9)
;
_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 0.3231(2) 0.82579(11) 0.49711(8) 0.0299(3) Uani 1 1 d . . . . .
N1 N 1.3753(2) 0.27017(15) 1.07672(10) 0.0331(4) Uani 1 1 d . . . . .
C7 C 0.7413(3) 0.60802(16) 0.70701(11) 0.0242(3) Uani 1 1 d . . . . .
C6 C 0.8816(3) 0.53438(17) 0.78524(11) 0.0241(3) Uani 1 1 d . . . . .
C12 C 0.6143(3) 0.53594(16) 0.66402(11) 0.0256(4) Uani 1 1 d . . . . .
H12 H 0.6244 0.4397 0.6828 0.031 Uiso 1 1 calc R . . . .
C5 C 1.0874(3) 0.59568(17) 0.79831(11) 0.0263(4) Uani 1 1 d . . . . .
H5 H 1.1394 0.6833 0.7558 0.032 Uiso 1 1 calc R . . . .
C15 C 0.0439(3) 0.86167(17) 0.38613(11) 0.0272(4) Uani 1 1 d . . . . .
H15A H 0.1604 0.9228 0.3364 0.033 Uiso 1 1 calc R . . . .
H15B H -0.0512 0.9177 0.4180 0.033 Uiso 1 1 calc R . . . .
C1 C 0.8073(3) 0.40244(16) 0.85094(11) 0.0249(3) Uani 1 1 d . . . . .
H1 H 0.6709 0.3599 0.8437 0.030 Uiso 1 1 calc R . . . .
C2 C 0.9321(3) 0.33444(17) 0.92597(11) 0.0253(4) Uani 1 1 d . . . . .
H2 H 0.8797 0.2472 0.9690 0.030 Uiso 1 1 calc R . . . .
C13 C 1.2692(3) 0.32699(17) 1.01489(12) 0.0270(4) Uani 1 1 d . . . . .
C10 C 0.4577(3) 0.74725(17) 0.56464(11) 0.0255(4) Uani 1 1 d . . . . .
C8 C 0.7248(3) 0.75310(17) 0.67573(11) 0.0275(4) Uani 1 1 d . . . . .
H8 H 0.8091 0.8040 0.7028 0.033 Uiso 1 1 calc R . . . .
C4 C 1.2145(3) 0.52871(17) 0.87292(11) 0.0269(4) Uani 1 1 d . . . . .
H4 H 1.3508 0.5711 0.8804 0.032 Uiso 1 1 calc R . . . .
C11 C 0.4729(3) 0.60365(17) 0.59387(11) 0.0272(4) Uani 1 1 d . . . . .
H11 H 0.3889 0.5530 0.5666 0.033 Uiso 1 1 calc R . . . .
C3 C 1.1378(3) 0.39741(17) 0.93700(11) 0.0250(4) Uani 1 1 d . . . . .
C17 C -0.2408(3) 0.89720(17) 0.26250(11) 0.0271(4) Uani 1 1 d . . . . .
H17 H -0.3391 0.9586 0.2897 0.033 Uiso 1 1 calc R . . . .
C20 C -0.3858(3) 0.84004(18) 0.20254(11) 0.0290(4) Uani 1 1 d . . . . .
H20A H -0.3358 0.7496 0.2003 0.035 Uiso 1 1 calc R . . . .
H20B H -0.5574 0.8408 0.2203 0.035 Uiso 1 1 calc R . . . .
C14 C 0.1718(3) 0.75428(17) 0.45848(11) 0.0279(4) Uani 1 1 d . . . . .
H14A H 0.0570 0.6944 0.5098 0.034 Uiso 1 1 calc R . . . .
H14B H 0.2664 0.6970 0.4275 0.034 Uiso 1 1 calc R . . . .
C16 C -0.1183(3) 0.79358(17) 0.33966(11) 0.0269(4) Uani 1 1 d . . . . .
H16A H -0.0238 0.7332 0.3114 0.032 Uiso 1 1 calc R . . . .
H16B H -0.2390 0.7361 0.3894 0.032 Uiso 1 1 calc R . . . .
C9 C 0.5863(3) 0.82224(17) 0.60577(11) 0.0277(4) Uani 1 1 d . . . . .
H9 H 0.5785 0.9187 0.5859 0.033 Uiso 1 1 calc R . . . .
C19 C -0.2870(3) 0.96250(19) 0.11157(12) 0.0351(4) Uani 1 1 d . . . . .
H19A H -0.3941 1.0398 0.0948 0.042 Uiso 1 1 calc R . . . .
H19B H -0.2296 0.9353 0.0561 0.042 Uiso 1 1 calc R . . . .
C18 C -0.0873(3) 0.98371(19) 0.16682(12) 0.0361(4) Uani 1 1 d . . . . .
H18A H -0.0607 1.0799 0.1609 0.043 Uiso 1 1 calc R . . . .
H18B H 0.0617 0.9410 0.1527 0.043 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
O1 C10 1.3691(19) . ?
O1 C14 1.4305(18) . ?
N1 C13 1.149(2) . ?
C7 C6 1.480(2) . ?
C7 C12 1.392(2) . ?
C7 C8 1.401(2) . ?
C6 C5 1.401(2) . ?
C6 C1 1.403(2) . ?
C12 H12 0.9300 . ?
C12 C11 1.388(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.380(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.506(2) . ?
C15 C16 1.528(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.379(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.397(2) . ?
C13 C3 1.437(2) . ?
C10 C11 1.386(2) . ?
C10 C9 1.399(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.393(2) . ?
C11 H11 0.9300 . ?
C17 H17 0.9800 . ?
C17 C20 1.545(2) . ?
C17 C16 1.512(2) . ?
C17 C18 1.548(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C19 1.544(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C9 H9 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C18 1.546(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?

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 C14 117.81(12) . . ?
C12 C7 C6 121.51(14) . . ?
C12 C7 C8 117.44(14) . . ?
C8 C7 C6 121.01(14) . . ?
C5 C6 C7 121.36(14) . . ?
C5 C6 C1 117.84(14) . . ?
C1 C6 C7 120.76(14) . . ?
C7 C12 H12 119.1 . . ?
C11 C12 C7 121.90(15) . . ?
C11 C12 H12 119.1 . . ?
C6 C5 H5 119.3 . . ?
C4 C5 C6 121.39(15) . . ?
C4 C5 H5 119.3 . . ?
H15A C15 H15B 108.0 . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
C14 C15 C16 111.35(13) . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C6 C1 H1 119.3 . . ?
C2 C1 C6 121.42(14) . . ?
C2 C1 H1 119.3 . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.62(15) . . ?
C3 C2 H2 120.2 . . ?
N1 C13 C3 179.47(17) . . ?
O1 C10 C11 125.23(14) . . ?
O1 C10 C9 115.21(14) . . ?
C11 C10 C9 119.56(15) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.48(15) . . ?
C9 C8 H8 119.3 . . ?
C5 C4 H4 120.1 . . ?
C5 C4 C3 119.72(14) . . ?
C3 C4 H4 120.1 . . ?
C12 C11 H11 120.2 . . ?
C10 C11 C12 119.63(14) . . ?
C10 C11 H11 120.2 . . ?
C2 C3 C13 119.94(14) . . ?
C4 C3 C2 120.01(14) . . ?
C4 C3 C13 120.06(14) . . ?
C20 C17 H17 110.2 . . ?
C20 C17 C18 87.98(12) . . ?
C16 C17 H17 110.2 . . ?
C16 C17 C20 117.79(13) . . ?
C16 C17 C18 118.59(13) . . ?
C18 C17 H17 110.2 . . ?
C17 C20 H20A 113.8 . . ?
C17 C20 H20B 113.8 . . ?
H20A C20 H20B 111.0 . . ?
C19 C20 C17 89.14(12) . . ?
C19 C20 H20A 113.8 . . ?
C19 C20 H20B 113.8 . . ?
O1 C14 C15 108.03(13) . . ?
O1 C14 H14A 110.1 . . ?
O1 C14 H14B 110.1 . . ?
C15 C14 H14A 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
C17 C16 C15 113.44(13) . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 C10 119.98(15) . . ?
C8 C9 H9 120.0 . . ?
C20 C19 H19A 114.0 . . ?
C20 C19 H19B 114.0 . . ?
C20 C19 C18 88.14(12) . . ?
H19A C19 H19B 111.2 . . ?
C18 C19 H19A 114.0 . . ?
C18 C19 H19B 114.0 . . ?
C17 C18 H18A 113.8 . . ?
C17 C18 H18B 113.8 . . ?
C19 C18 C17 88.94(12) . . ?
C19 C18 H18A 113.8 . . ?
C19 C18 H18B 113.8 . . ?
H18A C18 H18B 111.0 . . ?


_olex2_date_sample_data_collection 2018-10-05
_olex2_date_sample_submission    2018-10-05
_olex2_exptl_crystal_mounting_method 'oil on micromount '
_olex2_submission_original_sample_id 'Richard Mandle RM2102'
_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 1.592
_oxdiff_exptl_absorpt_empirical_full_min 0.689
####################################################################### 
# 
# 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_jwg1702
_database_code_depnum_ccdc_archive 'CCDC 2128188'
loop_
_audit_author_name
_audit_author_address
'Adrian C. Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2021-12-13 deposited with the CCDC.	2022-02-16 downloaded from the CCDC.
;
_audit_creation_date             2017-10-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H23 N O'
_chemical_formula_sum            'C21 H23 N O'
_chemical_formula_weight         305.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H23 N1 O1'
_chemical_oxdiff_usercomment     'Richard Mandle RM1281'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.1243(2)
_cell_length_b                   6.58920(10)
_cell_length_c                   21.5514(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.406(2)
_cell_angle_gamma                90
_cell_volume                     1659.86(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6233
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      70.8000
_cell_measurement_theta_min      6.4880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.574
_exptl_absorpt_correction_T_max  0.591
_exptl_absorpt_correction_T_min  0.114
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
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    1.222
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 0 -3 0.0729
1 -1 -1 0.1082
-5 1 4 0.0551
0 2 1 0.1313
-5 0 3 0.0543
0 0 1 0.0346
0 0 -1 0.0346
-5 2 2 0.0623

_exptl_crystal_size_max          0.297
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.069
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
5.0000 0.0000 -3.0000 0.0135 -0.1513 -0.6187
1.0000 -1.0000 -1.0000 0.0539 -0.2540 -0.0701
-5.0000 1.0000 4.0000 -0.0230 0.3906 0.5657
0.0000 2.0000 1.0000 -0.0885 0.4527 -0.1070
-5.0000 -0.0000 3.0000 -0.0135 0.1513 0.6187
0.0000 0.0000 1.0000 0.0694 0.0260 0.0009
-0.0000 -0.0000 -1.0000 -0.0694 -0.0260 -0.0009
-5.0000 2.0000 2.0000 -0.2409 0.5520 0.5098

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11210
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.067
_diffrn_reflns_theta_max         67.067
_diffrn_reflns_theta_min         3.815
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_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    -21.00  22.00   1.00    4.50    --    0.00  57.00   0.00   43
  2  ω     23.00  69.00   1.00    4.50    --    0.00  57.00   0.00   46
  3  ω     33.00  94.00   1.00   20.00    --   54.00  57.00 -60.00   61
  4  ω     52.00  89.00   1.00   20.00    --   54.00  57.00  30.00   37
  5  ω     55.00 117.00   1.00   20.00    --   54.00  57.00  60.00   62
  6  ω    153.00 178.00   1.00   20.00    --  108.00 111.00   0.00   25
  7  ω    139.00 178.00   1.00   20.00    --  108.00  77.00  60.00   39
  8  ω    108.00 177.00   1.00   20.00    --  108.00  50.00  90.00   69
  9  ω    100.00 172.00   1.00   20.00    --  108.00 111.00  30.00   72
 10  ω    123.00 169.00   1.00   20.00    --  108.00  77.00 -90.00   46
 11  ω    109.00 151.00   1.00   20.00    --  108.00 178.00-120.00   42
 12  ω     87.00 159.00   1.00   20.00    --  108.00  50.00-150.00   72
 13  ω     82.00 115.00   1.00   20.00    --  108.00  77.00  60.00   33
 14  ω     30.00 126.00   1.00   20.00    --   54.00  37.00 150.00   96
 15  ω     46.00 122.00   1.00   20.00    --  108.00 -63.00   0.00   76
 16  ω     58.00 105.00   1.00   20.00    --   54.00-125.00-120.00   47
 17  ω     57.00 101.00   1.00   20.00    --  108.00-111.00 -30.00   44
 18  ω     49.00 116.00   1.00   20.00    --  108.00-111.00  30.00   67
 19  ω     41.00 134.00   1.00   20.00    --  108.00 -37.00 -90.00   93
 20  ω     85.00 143.00   1.00   20.00    --  108.00 -91.00-150.00   58
 21  ω     59.00 114.00   1.00   20.00    --  108.00-111.00-150.00   55
 22  ω     39.00 120.00   1.00   20.00    --  108.00   0.00-120.00   81
 23  ω     34.00  75.00   1.00   20.00    --   54.00-125.00-150.00   41
 24  ω      2.00  96.00   1.00   20.00    --   54.00 -99.00   0.00   94
 25  ω     38.00 129.00   1.00   20.00    --  108.00 -50.00 120.00   91
 26  ω     41.00  76.00   1.00   20.00    --  108.00-111.00 150.00   35
 27  ω     -8.00  72.00   1.00   20.00    --   54.00 -37.00 150.00   80
 28  ω    -52.00 -26.00   1.00    4.50    --    0.00 -57.00 120.00   26
 29  ω    -69.00 -15.00   1.00    4.50    --    0.00 -57.00-150.00   54
 30  ω    -13.00  21.00   1.00    4.50    --    0.00 -57.00-150.00   34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0443704000
_diffrn_orient_matrix_UB_12      -0.0789787000
_diffrn_orient_matrix_UB_13      0.0694501000
_diffrn_orient_matrix_UB_21      -0.0146781000
_diffrn_orient_matrix_UB_22      0.2133623000
_diffrn_orient_matrix_UB_23      0.0259578000
_diffrn_orient_matrix_UB_31      -0.1231800000
_diffrn_orient_matrix_UB_32      -0.0539671000
_diffrn_orient_matrix_UB_33      0.0009331000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2766
_reflns_number_total             2962
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_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         0.204
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2962
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.057
_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)+(0.0632P)²+0.5127P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1093
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C14(H14A,H14B), C16(H16A,H16B), C19(H19A,H19B), C18(H18A,
 H18B), C21(H21A,H21B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C8(H8), C1(H1), C12(H12), C2(H2), C11(H11), C9(H9)
;
_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 0.12164(7) 0.36838(13) 0.46125(4) 0.0254(2) Uani 1 1 d . . . . .
N1 N 0.71517(9) 1.56382(17) 0.70686(5) 0.0321(3) Uani 1 1 d . . . . .
C7 C 0.42243(9) 0.99050(18) 0.58201(5) 0.0206(3) Uani 1 1 d . . . . .
C3 C 0.19679(10) 0.52140(18) 0.48542(5) 0.0214(3) Uani 1 1 d . . . . .
C5 C 0.37581(9) 0.69897(18) 0.50474(6) 0.0219(3) Uani 1 1 d . . . . .
H5 H 0.4476 0.7126 0.4974 0.026 Uiso 1 1 calc R . . . .
C6 C 0.34308(9) 0.83420(17) 0.54630(5) 0.0207(3) Uani 1 1 d . . . . .
C4 C 0.30388(10) 0.54434(18) 0.47406(5) 0.0225(3) Uani 1 1 d . . . . .
H4 H 0.3271 0.4568 0.4461 0.027 Uiso 1 1 calc R . . . .
C10 C 0.57373(10) 1.28156(18) 0.65195(5) 0.0228(3) Uani 1 1 d . . . . .
C8 C 0.53871(10) 0.94554(18) 0.60825(5) 0.0224(3) Uani 1 1 d . . . . .
H8 H 0.5658 0.8172 0.6020 0.027 Uiso 1 1 calc R . . . .
C1 C 0.23282(10) 0.81309(18) 0.55480(6) 0.0232(3) Uani 1 1 d . . . . .
H1 H 0.2078 0.9046 0.5810 0.028 Uiso 1 1 calc R . . . .
C12 C 0.38392(10) 1.18415(18) 0.59275(6) 0.0229(3) Uani 1 1 d . . . . .
H12 H 0.3069 1.2160 0.5766 0.028 Uiso 1 1 calc R . . . .
C2 C 0.16074(10) 0.65908(18) 0.52501(6) 0.0241(3) Uani 1 1 d . . . . .
H2 H 0.0881 0.6473 0.5314 0.029 Uiso 1 1 calc R . . . .
C15 C 0.04654(10) 0.09110(19) 0.39323(6) 0.0243(3) Uani 1 1 d . . . . .
H15A H -0.0202 0.1737 0.3744 0.029 Uiso 1 1 calc R . . . .
H15B H 0.0324 0.0188 0.4296 0.029 Uiso 1 1 calc R . . . .
C11 C 0.45812(10) 1.32909(18) 0.62695(6) 0.0242(3) Uani 1 1 d . . . . .
H11 H 0.4312 1.4575 0.6333 0.029 Uiso 1 1 calc R . . . .
C9 C 0.61361(10) 1.08767(19) 0.64312(6) 0.0241(3) Uani 1 1 d . . . . .
H9 H 0.6901 1.0546 0.6606 0.029 Uiso 1 1 calc R . . . .
C17 C -0.04518(10) -0.17925(19) 0.31113(6) 0.0244(3) Uani 1 1 d . . . . .
H17 H -0.1052 -0.0810 0.2919 0.029 Uiso 1 1 calc R . . . .
C13 C 0.65278(10) 1.43598(19) 0.68410(6) 0.0255(3) Uani 1 1 d . . . . .
C14 C 0.14932(10) 0.22769(19) 0.41672(6) 0.0244(3) Uani 1 1 d . . . . .
H14A H 0.2161 0.1484 0.4379 0.029 Uiso 1 1 calc R . . . .
H14B H 0.1654 0.2998 0.3809 0.029 Uiso 1 1 calc R . . . .
C16 C 0.06318(10) -0.06204(19) 0.34344(6) 0.0258(3) Uani 1 1 d . . . . .
H16A H 0.0896 0.0091 0.3107 0.031 Uiso 1 1 calc R . . . .
H16B H 0.1223 -0.1576 0.3643 0.031 Uiso 1 1 calc R . . . .
C19 C -0.17503(11) -0.45643(19) 0.30859(6) 0.0285(3) Uani 1 1 d . . . . .
H19A H -0.2488 -0.3907 0.2932 0.034 Uiso 1 1 calc R . . . .
H19B H -0.1852 -0.5835 0.3291 0.034 Uiso 1 1 calc R . . . .
C18 C -0.09050(10) -0.31857(19) 0.35533(6) 0.0262(3) Uani 1 1 d . . . . .
H18A H -0.1286 -0.2412 0.3819 0.031 Uiso 1 1 calc R . . . .
H18B H -0.0291 -0.3970 0.3830 0.031 Uiso 1 1 calc R . . . .
C21 C -0.03109(13) -0.3237(2) 0.25803(7) 0.0384(3) Uani 1 1 d . . . . .
H21A H -0.0442 -0.2522 0.2174 0.046 Uiso 1 1 calc R . . . .
H21B H 0.0455 -0.3802 0.2688 0.046 Uiso 1 1 calc R . . . .
C20 C -0.11986(13) -0.4924(2) 0.25326(7) 0.0373(3) Uani 1 1 d . . . . .
H20A H -0.0833 -0.6246 0.2574 0.045 Uiso 1 1 calc R . . . .
H20B H -0.1771 -0.4862 0.2122 0.045 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
O1 C3 1.3660(14) . ?
O1 C14 1.4367(14) . ?
N1 C13 1.1512(17) . ?
C7 C6 1.4782(16) . ?
C7 C8 1.4042(16) . ?
C7 C12 1.3989(17) . ?
C3 C4 1.3920(16) . ?
C3 C2 1.3928(17) . ?
C5 H5 0.9300 . ?
C5 C6 1.3939(17) . ?
C5 C4 1.3891(16) . ?
C6 C1 1.4036(16) . ?
C4 H4 0.9300 . ?
C10 C11 1.3970(17) . ?
C10 C9 1.3968(17) . ?
C10 C13 1.4426(17) . ?
C8 H8 0.9300 . ?
C8 C9 1.3798(16) . ?
C1 H1 0.9300 . ?
C1 C2 1.3812(16) . ?
C12 H12 0.9300 . ?
C12 C11 1.3829(17) . ?
C2 H2 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.5113(16) . ?
C15 C16 1.5250(17) . ?
C11 H11 0.9300 . ?
C9 H9 0.9300 . ?
C17 H17 0.9800 . ?
C17 C16 1.5237(16) . ?
C17 C18 1.5265(17) . ?
C17 C21 1.5325(17) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C18 1.5304(16) . ?
C19 C20 1.5327(19) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C20 1.5316(19) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?

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
C3 O1 C14 118.72(9) . . ?
C8 C7 C6 120.50(10) . . ?
C12 C7 C6 121.47(10) . . ?
C12 C7 C8 117.99(11) . . ?
O1 C3 C4 124.88(11) . . ?
O1 C3 C2 115.36(10) . . ?
C4 C3 C2 119.75(11) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.66(10) . . ?
C5 C6 C7 121.53(10) . . ?
C5 C6 C1 117.66(11) . . ?
C1 C6 C7 120.78(10) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.53(11) . . ?
C5 C4 H4 120.2 . . ?
C11 C10 C13 119.84(11) . . ?
C9 C10 C11 120.04(11) . . ?
C9 C10 C13 120.04(11) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.41(11) . . ?
C9 C8 H8 119.3 . . ?
C6 C1 H1 119.4 . . ?
C2 C1 C6 121.28(11) . . ?
C2 C1 H1 119.4 . . ?
C7 C12 H12 119.3 . . ?
C11 C12 C7 121.31(10) . . ?
C11 C12 H12 119.3 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 C3 120.03(10) . . ?
C1 C2 H2 120.0 . . ?
H15A C15 H15B 107.9 . . ?
C14 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
C14 C15 C16 112.22(10) . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.65(11) . . ?
C12 C11 H11 120.2 . . ?
C10 C9 H9 120.2 . . ?
C8 C9 C10 119.57(10) . . ?
C8 C9 H9 120.2 . . ?
C16 C17 H17 108.2 . . ?
C16 C17 C18 115.42(10) . . ?
C16 C17 C21 113.73(10) . . ?
C18 C17 H17 108.2 . . ?
C18 C17 C21 102.85(10) . . ?
C21 C17 H17 108.2 . . ?
N1 C13 C10 176.61(13) . . ?
O1 C14 C15 106.85(9) . . ?
O1 C14 H14A 110.4 . . ?
O1 C14 H14B 110.4 . . ?
C15 C14 H14A 110.4 . . ?
C15 C14 H14B 110.4 . . ?
H14A C14 H14B 108.6 . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
C17 C16 C15 113.44(10) . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
H19A C19 H19B 108.9 . . ?
C18 C19 H19A 110.9 . . ?
C18 C19 H19B 110.9 . . ?
C18 C19 C20 104.45(10) . . ?
C20 C19 H19A 110.9 . . ?
C20 C19 H19B 110.9 . . ?
C17 C18 C19 103.60(10) . . ?
C17 C18 H18A 111.0 . . ?
C17 C18 H18B 111.0 . . ?
C19 C18 H18A 111.0 . . ?
C19 C18 H18B 111.0 . . ?
H18A C18 H18B 109.0 . . ?
C17 C21 H21A 110.4 . . ?
C17 C21 H21B 110.4 . . ?
H21A C21 H21B 108.6 . . ?
C20 C21 C17 106.57(11) . . ?
C20 C21 H21A 110.4 . . ?
C20 C21 H21B 110.4 . . ?
C19 C20 H20A 110.5 . . ?
C19 C20 H20B 110.5 . . ?
C21 C20 C19 106.23(11) . . ?
C21 C20 H20A 110.5 . . ?
C21 C20 H20B 110.5 . . ?
H20A C20 H20B 108.7 . . ?


_olex2_date_sample_data_collection 2017-10-06
_olex2_date_sample_submission    2017-10-06
_olex2_exptl_crystal_mounting_method 'oil on micromount 200 micrometres'
_olex2_submission_original_sample_id 'Richard Mandle RM1281'
_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 1.417
_oxdiff_exptl_absorpt_empirical_full_min 0.569
####################################################################### 
# 
# 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_jwg1703
_database_code_depnum_ccdc_archive 'CCDC 2128191'
loop_
_audit_author_name
_audit_author_address
'Adrian C. Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2021-12-13 deposited with the CCDC.	2022-02-16 downloaded from the CCDC.
;
_audit_creation_date             2017-11-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H25 N O'
_chemical_formula_sum            'C22 H25 N O'
_chemical_formula_weight         319.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H25 N1 O1'
_chemical_oxdiff_usercomment     'Richard Mandle RM1899'
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      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                   7.0753(4)
_cell_length_b                   9.7137(5)
_cell_length_c                   13.3506(8)
_cell_angle_alpha                78.906(5)
_cell_angle_beta                 83.156(5)
_cell_angle_gamma                82.858(5)
_cell_volume                     889.13(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2092
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      70.6430
_cell_measurement_theta_min      7.5100
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.556
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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    1.193
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0367
0 0 -1 0.0367
-4 -3 -1 0.0797
3 4 -3 0.0516
-3 -4 3 0.0516
0 -5 -3 0.1184
0 5 2 0.1027
1 1 0 0.0456
1 -5 1 0.1335
-2 2 5 0.1159

_exptl_crystal_recrystallization_method 'Evaporation of ethanol solution'
_exptl_crystal_size_max          0.325
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.073
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 -0.0000 1.0000 -0.0737 -0.0915 -0.0131
0.0000 0.0000 -1.0000 0.0737 0.0915 0.0131
-4.0000 -3.0000 -1.0000 -0.1722 -0.0664 0.9299
3.0000 4.0000 -3.0000 0.6510 0.2722 -0.7261
-3.0000 -4.0000 3.0000 -0.6510 -0.2722 0.7261
0.0000 -5.0000 -3.0000 -0.4807 0.6187 0.2609
-0.0000 5.0000 2.0000 0.5544 -0.5273 -0.2479
1.0000 1.0000 -0.0000 0.0966 0.0222 -0.2403
1.0000 -5.0000 1.0000 -0.8192 0.3440 0.0127
-2.0000 2.0000 5.0000 -0.0001 -0.7772 0.2379

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5477
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         3.390
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00  18.00   1.00    1.00    --    0.00 -57.00  90.00   25
  2  ω     49.00 110.00   1.00    1.00    --   54.00-125.00 120.00   61
  3  ω     57.00  98.00   1.00    1.50    --  108.00-111.00 150.00   41
  4  ω     40.00  98.00   1.00    1.50    --  108.00 -50.00  60.00   58
  5  ω     40.00  91.00   1.00    1.00    --   54.00  37.00   0.00   51
  6  ω     87.00 131.00   1.00    1.50    --  108.00  63.00   0.00   44
  7  ω    104.00 168.00   1.00    1.50    --  108.00  63.00 -60.00   64
  8  ω    101.00 151.00   1.00    1.50    --  108.00 111.00-180.00   50
  9  ω     99.00 162.00   1.00    1.50    --  108.00  63.00 -90.00   63
 10  ω    101.00 169.00   1.00    1.50    --  108.00 111.00-150.00   68
 11  ω     44.00 129.00   1.00    1.50    --  108.00 -50.00-150.00   85
 12  ω     77.00 138.00   1.00    1.50    --  108.00 -91.00-120.00   61
 13  ω     46.00 115.00   1.00    1.50    --  108.00-111.00-150.00   69
 14  ω     37.00  71.00   1.00    1.50    --  108.00 -91.00-120.00   34
 15  ω     18.00  80.00   1.00    1.00    --   54.00 -99.00 -60.00   62
 16  ω     39.00 109.00   1.00    1.50    --  108.00-111.00  60.00   70
 17  ω     35.00 132.00   1.00    1.50    --  108.00 -25.00 120.00   97
 18  ω    110.00 149.00   1.00    1.50    --  108.00 111.00 120.00   39
 19  ω     30.00  69.00   1.00    1.00    --    0.00  57.00-120.00   39
 20  ω    -18.00  79.00   1.00    1.00    --   54.00 -37.00  90.00   97
 21  ω     -5.00  80.00   1.00    1.00    --   54.00 -37.00 -30.00   85
 22  ω     30.00 126.00   1.00    1.00    --   54.00  37.00 -90.00   96
 23  ω    -20.00  12.00   1.00    1.00    --    0.00  57.00-120.00   32
 24  ω    -63.00 -21.00   1.00    1.00    --    0.00 -57.00  90.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0437847000
_diffrn_orient_matrix_UB_12      0.1403435000
_diffrn_orient_matrix_UB_13      -0.0736671000
_diffrn_orient_matrix_UB_21      0.0911131000
_diffrn_orient_matrix_UB_22      -0.0688692000
_diffrn_orient_matrix_UB_23      -0.0914537000
_diffrn_orient_matrix_UB_31      -0.1959612000
_diffrn_orient_matrix_UB_32      -0.0443480000
_diffrn_orient_matrix_UB_33      -0.0130571000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2667
_reflns_number_total             3180
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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         0.202
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.027
_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)+(0.0583P)²+0.2169P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1138
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C18(H18A,H18B), C19(H19A,
 H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13)
;
_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 0.37244(13) 0.81331(10) 0.74439(7) 0.0240(2) Uani 1 1 d . . . . .
N1 N 1.66894(17) 0.09328(13) 0.92325(10) 0.0305(3) Uani 1 1 d . . . . .
C1 C 1.53205(19) 0.16486(14) 0.90172(10) 0.0229(3) Uani 1 1 d . . . . .
C2 C 1.36255(19) 0.25779(14) 0.87677(10) 0.0210(3) Uani 1 1 d . . . . .
C3 C 1.37814(19) 0.38191(14) 0.80507(11) 0.0222(3) Uani 1 1 d . . . . .
H3 H 1.4968 0.4031 0.7717 0.027 Uiso 1 1 calc R . . . .
C4 C 1.21577(19) 0.47336(14) 0.78400(11) 0.0219(3) Uani 1 1 d . . . . .
H4 H 1.2260 0.5556 0.7356 0.026 Uiso 1 1 calc R . . . .
C5 C 1.03661(19) 0.44398(13) 0.83435(10) 0.0196(3) Uani 1 1 d . . . . .
C6 C 1.02413(19) 0.31800(14) 0.90518(11) 0.0221(3) Uani 1 1 d . . . . .
H6 H 0.9055 0.2964 0.9384 0.027 Uiso 1 1 calc R . . . .
C7 C 1.18441(19) 0.22541(14) 0.92661(11) 0.0230(3) Uani 1 1 d . . . . .
H7 H 1.1739 0.1421 0.9738 0.028 Uiso 1 1 calc R . . . .
C8 C 0.86345(18) 0.54322(13) 0.81346(10) 0.0197(3) Uani 1 1 d . . . . .
C9 C 0.83259(18) 0.61046(13) 0.71342(10) 0.0200(3) Uani 1 1 d . . . . .
H9 H 0.9238 0.5944 0.6596 0.024 Uiso 1 1 calc R . . . .
C10 C 0.66870(19) 0.70047(13) 0.69315(10) 0.0202(3) Uani 1 1 d . . . . .
H10 H 0.6498 0.7430 0.6260 0.024 Uiso 1 1 calc R . . . .
C11 C 0.53203(19) 0.72764(13) 0.77286(10) 0.0197(3) Uani 1 1 d . . . . .
C12 C 0.5631(2) 0.66577(14) 0.87327(11) 0.0230(3) Uani 1 1 d . . . . .
H12 H 0.4750 0.6860 0.9273 0.028 Uiso 1 1 calc R . . . .
C13 C 0.72673(19) 0.57359(14) 0.89237(11) 0.0225(3) Uani 1 1 d . . . . .
H13 H 0.7454 0.5311 0.9596 0.027 Uiso 1 1 calc R . . . .
C14 C 0.2295(2) 0.84853(16) 0.82364(11) 0.0282(3) Uani 1 1 d . . . . .
H14A H 0.2781 0.9090 0.8625 0.034 Uiso 1 1 calc R . . . .
H14B H 0.1961 0.7635 0.8703 0.034 Uiso 1 1 calc R . . . .
C15 C 0.0551(2) 0.92406(15) 0.77366(11) 0.0276(3) Uani 1 1 d . . . . .
H15A H -0.0412 0.9505 0.8266 0.033 Uiso 1 1 calc R . . . .
H15B H 0.0025 0.8594 0.7401 0.033 Uiso 1 1 calc R . . . .
C16 C 0.09592(19) 1.05586(14) 0.69517(11) 0.0241(3) Uani 1 1 d . . . . .
H16A H 0.1718 1.0274 0.6357 0.029 Uiso 1 1 calc R . . . .
H16B H 0.1719 1.1116 0.7246 0.029 Uiso 1 1 calc R . . . .
C17 C -0.08381(19) 1.14849(14) 0.66003(10) 0.0217(3) Uani 1 1 d . . . . .
H17 H -0.1531 1.1828 0.7200 0.026 Uiso 1 1 calc R . . . .
C18 C -0.0284(2) 1.27677(15) 0.58130(11) 0.0255(3) Uani 1 1 d . . . . .
H18A H 0.0492 1.3300 0.6118 0.031 Uiso 1 1 calc R . . . .
H18B H 0.0484 1.2451 0.5232 0.031 Uiso 1 1 calc R . . . .
C19 C -0.2024(2) 1.37283(14) 0.54360(11) 0.0252(3) Uani 1 1 d . . . . .
H19A H -0.1604 1.4503 0.4917 0.030 Uiso 1 1 calc R . . . .
H19B H -0.2729 1.4121 0.6003 0.030 Uiso 1 1 calc R . . . .
C20 C -0.3336(2) 1.29259(15) 0.49866(12) 0.0298(3) Uani 1 1 d . . . . .
H20A H -0.2676 1.2613 0.4378 0.036 Uiso 1 1 calc R . . . .
H20B H -0.4465 1.3547 0.4788 0.036 Uiso 1 1 calc R . . . .
C21 C -0.3935(2) 1.16510(15) 0.57699(13) 0.0308(3) Uani 1 1 d . . . . .
H21A H -0.4694 1.1117 0.5455 0.037 Uiso 1 1 calc R . . . .
H21B H -0.4725 1.1973 0.6342 0.037 Uiso 1 1 calc R . . . .
C22 C -0.2196(2) 1.06926(14) 0.61662(12) 0.0272(3) Uani 1 1 d . . . . .
H22A H -0.2632 0.9937 0.6697 0.033 Uiso 1 1 calc R . . . .
H22B H -0.1503 1.0270 0.5610 0.033 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
O1 C11 1.3634(15) . ?
O1 C14 1.4343(17) . ?
N1 C1 1.1515(18) . ?
C1 C2 1.4403(18) . ?
C2 C3 1.3949(19) . ?
C2 C7 1.3958(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.3839(18) . ?
C4 H4 0.9300 . ?
C4 C5 1.3975(18) . ?
C5 C6 1.4004(18) . ?
C5 C8 1.4807(17) . ?
C6 H6 0.9300 . ?
C6 C7 1.3790(19) . ?
C7 H7 0.9300 . ?
C8 C9 1.3987(19) . ?
C8 C13 1.3922(19) . ?
C9 H9 0.9300 . ?
C9 C10 1.3834(18) . ?
C10 H10 0.9300 . ?
C10 C11 1.3916(19) . ?
C11 C12 1.3907(19) . ?
C12 H12 0.9300 . ?
C12 C13 1.3897(19) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.5129(19) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.5244(19) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.5304(18) . ?
C17 H17 0.9800 . ?
C17 C18 1.5265(19) . ?
C17 C22 1.5294(19) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.5234(18) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.5237(19) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.527(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.5301(19) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?

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
C11 O1 C14 118.05(10) . . ?
N1 C1 C2 178.02(15) . . ?
C3 C2 C1 119.73(12) . . ?
C3 C2 C7 120.34(12) . . ?
C7 C2 C1 119.90(12) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.55(12) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 120.97(12) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 118.46(12) . . ?
C4 C5 C8 121.01(12) . . ?
C6 C5 C8 120.53(12) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.26(12) . . ?
C7 C6 H6 119.4 . . ?
C2 C7 H7 120.3 . . ?
C6 C7 C2 119.40(13) . . ?
C6 C7 H7 120.3 . . ?
C9 C8 C5 120.89(12) . . ?
C13 C8 C5 121.36(12) . . ?
C13 C8 C9 117.75(12) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.14(13) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.27(12) . . ?
C11 C10 H10 119.9 . . ?
O1 C11 C10 115.66(11) . . ?
O1 C11 C12 124.82(12) . . ?
C12 C11 C10 119.50(12) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.61(13) . . ?
C13 C12 H12 120.2 . . ?
C8 C13 H13 119.2 . . ?
C12 C13 C8 121.68(13) . . ?
C12 C13 H13 119.2 . . ?
O1 C14 H14A 110.1 . . ?
O1 C14 H14B 110.1 . . ?
O1 C14 C15 108.21(11) . . ?
H14A C14 H14B 108.4 . . ?
C15 C14 H14A 110.1 . . ?
C15 C14 H14B 110.1 . . ?
C14 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C14 C15 C16 113.82(12) . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C15 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
C15 C16 C17 114.09(11) . . ?
H16A C16 H16B 107.6 . . ?
C17 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C16 C17 H17 107.7 . . ?
C18 C17 C16 110.18(11) . . ?
C18 C17 H17 107.7 . . ?
C18 C17 C22 110.11(11) . . ?
C22 C17 C16 113.30(11) . . ?
C22 C17 H17 107.7 . . ?
C17 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?
C19 C18 C17 112.38(11) . . ?
C19 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
C18 C19 H19A 109.4 . . ?
C18 C19 H19B 109.4 . . ?
C18 C19 C20 111.23(11) . . ?
H19A C19 H19B 108.0 . . ?
C20 C19 H19A 109.4 . . ?
C20 C19 H19B 109.4 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 C21 110.51(12) . . ?
H20A C20 H20B 108.1 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
C20 C21 H21A 109.3 . . ?
C20 C21 H21B 109.3 . . ?
C20 C21 C22 111.54(12) . . ?
H21A C21 H21B 108.0 . . ?
C22 C21 H21A 109.3 . . ?
C22 C21 H21B 109.3 . . ?
C17 C22 C21 112.58(11) . . ?
C17 C22 H22A 109.1 . . ?
C17 C22 H22B 109.1 . . ?
C21 C22 H22A 109.1 . . ?
C21 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?


_olex2_date_sample_data_collection 2017-10-09
_olex2_date_sample_submission    2017-10-06
_olex2_exptl_crystal_mounting_method 'oil on 200 micrometre micromount'
_olex2_submission_original_sample_id RM1899
_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 1.380
_oxdiff_exptl_absorpt_empirical_full_min 0.813
####################################################################### 
# 
# 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_jwg1806
_database_code_depnum_ccdc_archive 'CCDC 2128189'
loop_
_audit_author_name
_audit_author_address
'Adrian C. Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2021-12-13 deposited with the CCDC.	2022-02-16 downloaded from the CCDC.
;
_audit_creation_date             2018-10-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 N O'
_chemical_formula_sum            'C19 H19 N O'
_chemical_formula_weight         277.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H19 N O'
_chemical_oxdiff_usercomment     'Richard Mandle RM2094'
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      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                   5.4374(3)
_cell_length_b                   10.4374(4)
_cell_length_c                   13.6579(6)
_cell_angle_alpha                104.161(4)
_cell_angle_beta                 92.138(4)
_cell_angle_gamma                95.945(4)
_cell_volume                     745.94(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4143
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      70.8980
_cell_measurement_theta_min      4.3760
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             296
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 5 0.0570
0 1 -5 0.0501
-3 1 -5 0.1066
3 -1 5 0.1262
0 1 0 0.0100
0 -1 0 0.0277
0 -5 -4 0.0326
0 -5 4 0.0412
1 -5 1 0.0546
-1 5 -3 0.0629

_exptl_crystal_recrystallization_method 'ethanol/water/DCM diffusion'
_exptl_crystal_size_max          0.361
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.038
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
-0.0005 -1.0020 5.0027 -0.0122 -0.0251 0.5640
0.0005 1.0020 -5.0027 0.0122 0.0251 -0.5640
-2.9987 1.0041 -5.0044 -0.8414 -0.0171 -0.6147
2.9987 -1.0041 5.0044 0.8414 0.0171 0.6147
0.0003 0.9999 -0.0005 0.0101 0.1528 0.0049
-0.0003 -0.9999 0.0005 -0.0101 -0.1528 -0.0049
-0.0013 -4.9978 -3.9992 -0.0487 -0.8664 -0.4794
-0.0016 -5.0012 4.0042 -0.0520 -0.6620 0.4308
0.9982 -5.0006 1.0035 0.2338 -0.7246 0.1064
-0.9981 5.0014 -3.0044 -0.2329 0.6735 -0.3339

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13771
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.178
_diffrn_reflns_theta_min         4.399
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  69.00   1.00    1.00    --    0.00  57.00 -90.00   90
  2  ω    -21.00  69.00   1.00    1.00    --    0.00  57.00  30.00   90
  3  ω    -15.00  75.00   1.00    3.50    --   54.00 -57.00 -90.00   90
  4  ω    -19.00  98.00   1.00    3.50    --   54.00 -19.00  60.00  117
  5  ω    -15.00  75.00   1.00    3.50    --   54.00 -57.00   0.00   90
  6  ω     23.00 111.00   1.00    3.50    --   54.00-125.00  30.00   88
  7  ω     33.00 123.00   1.00    3.50    --   54.00  57.00-120.00   90
  8  ω     23.00 111.00   1.00    3.50    --   54.00-125.00-150.00   88
  9  ω     23.00 111.00   1.00    3.50    --   54.00-125.00-180.00   88
 10  ω     86.00 176.00   1.00    3.50    --  108.00  63.00  60.00   90
 11  ω    100.00 178.00   1.00    3.50    --  108.00 111.00-180.00   78
 12  ω     36.00 113.00   1.00    3.50    --  108.00-111.00 -90.00   77
 13  ω     36.00 134.00   1.00    3.50    --  108.00 -37.00  90.00   98
 14  ω     38.00 138.00   1.00    3.50    --  108.00 -77.00 150.00  100
 15  ω     38.00 130.00   1.00    3.50    --  108.00 -50.00 -90.00   92
 16  ω     36.00 134.00   1.00    3.50    --  108.00 -37.00 -60.00   98
 17  ω     36.00 113.00   1.00    3.50    --  108.00-111.00 150.00   77
 18  ω     86.00 176.00   1.00    3.50    --  108.00  63.00-120.00   90
 19  ω     40.00 130.00   1.00    3.50    --  108.00 -63.00-150.00   90
 20  ω     36.00 146.00   1.00    3.50    --  108.00 -91.00 -30.00  110
 21  ω     35.00 178.00   1.00    3.50    --  108.00   0.00  30.00  143
 22  ω    -30.00  70.00   1.00    1.00    --    0.00  77.00 -60.00  100
 23  ω    -30.00  70.00   1.00    1.00    --    0.00  77.00-180.00  100
 24  ω     24.00 124.00   1.00    3.50    --   54.00  77.00  90.00  100
 25  ω     24.00 124.00   1.00    3.50    --   54.00  77.00  30.00  100
 26  ω     24.00 124.00   1.00    3.50    --   54.00  77.00-180.00  100
 27  ω     33.00 123.00   1.00    3.50    --   54.00  57.00 150.00   90
 28  ω     24.00 124.00   1.00    3.50    --   54.00  77.00 -60.00  100
 29  ω     24.00 124.00   1.00    3.50    --   54.00  77.00   0.00  100
 30  ω    -15.00  75.00   1.00    3.50    --   54.00 -57.00-180.00   90
 31  ω     24.00 124.00   1.00    3.50    --   54.00  77.00-120.00  100
 32  ω     78.00 178.00   1.00    3.50    --  108.00  77.00 -90.00  100
 33  ω     82.00 178.00   1.00    3.50    --  108.00  37.00  30.00   96
 34  ω     82.00 178.00   1.00    3.50    --  108.00  37.00-150.00   96
 35  ω     86.00 178.00   1.00    3.50    --  108.00  50.00 -30.00   92
 36  ω     74.00 178.00   1.00    3.50    --  108.00  25.00 150.00  104
 37  ω     78.00 178.00   1.00    3.50    --  108.00  77.00 -30.00  100
 38  ω     78.00 178.00   1.00    3.50    --  108.00  77.00 120.00  100
 39  ω     78.00 178.00   1.00    3.50    --  108.00  77.00  30.00  100
 40  ω     86.00 178.00   1.00    3.50    --  108.00  50.00  90.00   92
 41  ω     78.00 178.00   1.00    3.50    --  108.00  77.00-150.00  100
 42  ω     78.00 178.00   1.00    3.50    --  108.00  77.00-120.00  100
 43  ω     78.00 178.00   1.00    3.50    --  108.00  77.00 150.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2846126000
_diffrn_orient_matrix_UB_12      0.0099873000
_diffrn_orient_matrix_UB_13      -0.0004035000
_diffrn_orient_matrix_UB_21      0.0141543000
_diffrn_orient_matrix_UB_22      0.1528612000
_diffrn_orient_matrix_UB_23      0.0255986000
_diffrn_orient_matrix_UB_31      0.0168322000
_diffrn_orient_matrix_UB_32      0.0049101000
_diffrn_orient_matrix_UB_33      0.1137315000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2363
_reflns_number_total             2867
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2867
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.029
_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)+(0.0559P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1119
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C18(H18A,H18B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13)
;
_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
C1 C 1.2376(2) 0.31942(14) -0.00154(11) 0.0273(3) Uani 1 1 d . . . . .
C2 C 1.1024(2) 0.39061(14) 0.07871(10) 0.0260(3) Uani 1 1 d . . . . .
C3 C 0.8837(2) 0.32980(13) 0.10598(11) 0.0274(3) Uani 1 1 d . . . . .
H3 H 0.8261 0.2421 0.0734 0.033 Uiso 1 1 calc R . . . .
C4 C 0.7535(2) 0.40085(13) 0.18168(11) 0.0262(3) Uani 1 1 d . . . . .
H4 H 0.6071 0.3601 0.1991 0.031 Uiso 1 1 calc R . . . .
C5 C 0.8362(2) 0.53275(13) 0.23289(10) 0.0242(3) Uani 1 1 d . . . . .
C6 C 1.0587(2) 0.59090(13) 0.20493(11) 0.0265(3) Uani 1 1 d . . . . .
H6 H 1.1190 0.6779 0.2383 0.032 Uiso 1 1 calc R . . . .
C7 C 1.1893(2) 0.52162(13) 0.12909(11) 0.0276(3) Uani 1 1 d . . . . .
H7 H 1.3356 0.5622 0.1114 0.033 Uiso 1 1 calc R . . . .
C8 C 0.6906(2) 0.60969(13) 0.31122(10) 0.0243(3) Uani 1 1 d . . . . .
C9 C 0.5263(2) 0.54796(13) 0.36587(10) 0.0261(3) Uani 1 1 d . . . . .
H9 H 0.5128 0.4559 0.3547 0.031 Uiso 1 1 calc R . . . .
C10 C 0.3818(2) 0.61918(13) 0.43662(11) 0.0272(3) Uani 1 1 d . . . . .
H10 H 0.2731 0.5752 0.4719 0.033 Uiso 1 1 calc R . . . .
C11 C 0.4013(2) 0.75675(13) 0.45421(10) 0.0255(3) Uani 1 1 d . . . . .
C12 C 0.5671(3) 0.82119(13) 0.40151(11) 0.0275(3) Uani 1 1 d . . . . .
H12 H 0.5834 0.9135 0.4141 0.033 Uiso 1 1 calc R . . . .
C13 C 0.7066(2) 0.74883(13) 0.33096(11) 0.0267(3) Uani 1 1 d . . . . .
H13 H 0.8141 0.7931 0.2955 0.032 Uiso 1 1 calc R . . . .
C14 C 0.0853(2) 0.77893(13) 0.57470(11) 0.0276(3) Uani 1 1 d . . . . .
H14A H 0.1600 0.7274 0.6156 0.033 Uiso 1 1 calc R . . . .
H14B H -0.0392 0.7205 0.5271 0.033 Uiso 1 1 calc R . . . .
C15 C -0.0298(2) 0.89165(13) 0.64088(11) 0.0277(3) Uani 1 1 d . . . . .
H15A H -0.1055 0.9410 0.5985 0.033 Uiso 1 1 calc R . . . .
H15B H 0.0991 0.9517 0.6850 0.033 Uiso 1 1 calc R . . . .
C16 C -0.2254(2) 0.84384(13) 0.70529(11) 0.0277(3) Uani 1 1 d . . . . .
H16A H -0.3543 0.7836 0.6612 0.033 Uiso 1 1 calc R . . . .
H16B H -0.1497 0.7949 0.7480 0.033 Uiso 1 1 calc R . . . .
C17 C -0.3400(2) 0.95708(14) 0.77077(11) 0.0282(3) Uani 1 1 d . . . . .
H17 H -0.4406 1.0048 0.7338 0.034 Uiso 1 1 calc R . . . .
C18 C -0.4246(3) 0.95115(15) 0.87225(12) 0.0348(4) Uani 1 1 d . . . . .
H18A H -0.4011 0.8721 0.8953 0.042 Uiso 1 1 calc R . . . .
H18B H -0.5734 0.9911 0.8935 0.042 Uiso 1 1 calc R . . . .
C19 C -0.1984(3) 1.04213(15) 0.86436(12) 0.0368(4) Uani 1 1 d . . . . .
H19A H -0.0385 1.0179 0.8824 0.044 Uiso 1 1 calc R . . . .
H19B H -0.2108 1.1370 0.8807 0.044 Uiso 1 1 calc R . . . .
N1 N 1.3473(2) 0.26252(12) -0.06534(10) 0.0336(3) Uani 1 1 d . . . . .
O1 O 0.27069(18) 0.83810(9) 0.52175(7) 0.0294(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
C1 C2 1.4383(19) . ?
C1 N1 1.1517(18) . ?
C2 C3 1.3958(18) . ?
C2 C7 1.3957(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.3815(19) . ?
C4 H4 0.9300 . ?
C4 C5 1.4015(18) . ?
C5 C6 1.4047(18) . ?
C5 C8 1.4802(19) . ?
C6 H6 0.9300 . ?
C6 C7 1.3766(19) . ?
C7 H7 0.9300 . ?
C8 C9 1.3914(18) . ?
C8 C13 1.4034(19) . ?
C9 H9 0.9300 . ?
C9 C10 1.3891(19) . ?
C10 H10 0.9300 . ?
C10 C11 1.3887(19) . ?
C11 C12 1.3938(19) . ?
C11 O1 1.3663(16) . ?
C12 H12 0.9300 . ?
C12 C13 1.3754(19) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.5059(19) . ?
C14 O1 1.4367(15) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.5259(18) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.5040(19) . ?
C17 H17 0.9800 . ?
C17 C18 1.490(2) . ?
C17 C19 1.498(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.498(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?

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
N1 C1 C2 179.54(15) . . ?
C3 C2 C1 120.38(12) . . ?
C3 C2 C7 119.79(12) . . ?
C7 C2 C1 119.82(12) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.52(12) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.72(12) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C6 117.58(12) . . ?
C4 C5 C8 121.31(11) . . ?
C6 C5 C8 121.08(12) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.31(12) . . ?
C7 C6 H6 119.3 . . ?
C2 C7 H7 120.0 . . ?
C6 C7 C2 120.07(12) . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C5 121.94(12) . . ?
C9 C8 C13 117.06(12) . . ?
C13 C8 C5 120.97(12) . . ?
C8 C9 H9 118.9 . . ?
C10 C9 C8 122.24(12) . . ?
C10 C9 H9 118.9 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.34(12) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 119.56(13) . . ?
O1 C11 C10 125.09(12) . . ?
O1 C11 C12 115.34(12) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.24(12) . . ?
C13 C12 H12 119.9 . . ?
C8 C13 H13 119.2 . . ?
C12 C13 C8 121.56(13) . . ?
C12 C13 H13 119.2 . . ?
H14A C14 H14B 108.6 . . ?
C15 C14 H14A 110.4 . . ?
C15 C14 H14B 110.4 . . ?
O1 C14 H14A 110.4 . . ?
O1 C14 H14B 110.4 . . ?
O1 C14 C15 106.66(10) . . ?
C14 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
C14 C15 C16 112.65(11) . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C15 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 C15 112.24(11) . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C16 C17 H17 114.9 . . ?
C18 C17 C16 121.34(12) . . ?
C18 C17 H17 114.9 . . ?
C18 C17 C19 60.16(10) . . ?
C19 C17 C16 119.69(12) . . ?
C19 C17 H17 114.9 . . ?
C17 C18 H18A 117.8 . . ?
C17 C18 H18B 117.8 . . ?
C17 C18 C19 60.19(10) . . ?
H18A C18 H18B 114.9 . . ?
C19 C18 H18A 117.8 . . ?
C19 C18 H18B 117.8 . . ?
C17 C19 H19A 117.8 . . ?
C17 C19 H19B 117.8 . . ?
C18 C19 C17 59.65(10) . . ?
C18 C19 H19A 117.8 . . ?
C18 C19 H19B 117.8 . . ?
H19A C19 H19B 114.9 . . ?
C11 O1 C14 118.76(10) . . ?

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 -178.52(12) . . . . ?
C1 C2 C7 C6 179.04(13) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C3 C2 C7 C6 -0.5(2) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C3 C4 C5 C8 177.67(12) . . . . ?
C4 C5 C6 C7 0.8(2) . . . . ?
C4 C5 C8 C9 25.5(2) . . . . ?
C4 C5 C8 C13 -152.22(13) . . . . ?
C5 C6 C7 C2 -0.5(2) . . . . ?
C5 C8 C9 C10 -177.39(12) . . . . ?
C5 C8 C13 C12 178.14(12) . . . . ?
C6 C5 C8 C9 -156.57(13) . . . . ?
C6 C5 C8 C13 25.69(19) . . . . ?
C7 C2 C3 C4 1.0(2) . . . . ?
C8 C5 C6 C7 -177.15(12) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C9 C8 C13 C12 0.3(2) . . . . ?
C9 C10 C11 C12 -0.7(2) . . . . ?
C9 C10 C11 O1 -179.77(12) . . . . ?
C10 C11 C12 C13 1.4(2) . . . . ?
C10 C11 O1 C14 -4.6(2) . . . . ?
C11 C12 C13 C8 -1.2(2) . . . . ?
C12 C11 O1 C14 176.32(12) . . . . ?
C13 C8 C9 C10 0.4(2) . . . . ?
C14 C15 C16 C17 -179.76(12) . . . . ?
C15 C14 O1 C11 -178.65(11) . . . . ?
C15 C16 C17 C18 -147.37(13) . . . . ?
C15 C16 C17 C19 -76.23(16) . . . . ?
C16 C17 C18 C19 108.62(15) . . . . ?
C16 C17 C19 C18 -111.30(14) . . . . ?
O1 C11 C12 C13 -179.43(12) . . . . ?
O1 C14 C15 C16 -177.85(11) . . . . ?


_olex2_date_sample_data_collection 2018-10-09
_olex2_date_sample_submission    2018-10-05
_olex2_exptl_crystal_mounting_method 'oil on micromount'
_olex2_submission_original_sample_id RM2094
_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 1.304
_oxdiff_exptl_absorpt_empirical_full_min 0.687
####################################################################### 
# 
# 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_jwg1701
_database_code_depnum_ccdc_archive 'CCDC 2128190'
loop_
_audit_author_name
_audit_author_address
'Adrian C. Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2021-12-13 deposited with the CCDC.	2022-02-16 downloaded from the CCDC.
;
_audit_creation_date             2017-10-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H27 N O'
_chemical_formula_sum            'C23 H27 N O'
_chemical_formula_weight         333.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H27 N1 O1'
_chemical_oxdiff_usercomment     'Richard Mandle RM2176'
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      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                   7.4340(6)
_cell_length_b                   9.3359(6)
_cell_length_c                   13.7657(9)
_cell_angle_alpha                80.118(6)
_cell_angle_beta                 82.186(6)
_cell_angle_gamma                81.713(6)
_cell_volume                     925.30(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1481
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      69.9340
_cell_measurement_theta_min      7.3580
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.554
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.564
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
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    1.197
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             360
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 1 2 0.0501
1 -1 -2 0.0540
0 -1 -2 0.0681
0 0 -1 0.0227
0 0 1 0.0288
-1 2 -5 0.0352
-2 -4 -5 0.1035
3 4 4 0.1232
2 -4 3 0.0241
1 5 -4 0.0916

_exptl_crystal_size_max          0.291
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.051
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
-0.9996 0.9991 2.0019 0.0524 -0.0099 -0.3609
0.9996 -0.9991 -2.0019 -0.0524 0.0099 0.3609
0.0000 -0.9984 -2.0020 0.1139 -0.0216 0.2354
0.0003 0.0007 -1.0008 0.0544 0.0637 0.0781
-0.0003 -0.0007 1.0008 -0.0544 -0.0637 -0.0781
-0.9968 2.0037 -5.0031 0.4279 0.5845 0.1063
-1.9999 -3.9942 -5.0057 0.6251 -0.3403 0.4564
2.9998 3.9941 4.0050 -0.7370 0.4354 -0.2528
1.9958 -4.0026 3.0009 -0.4751 -0.7234 0.3338
1.0038 5.0008 -4.0009 0.0254 1.0305 0.0414

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5581
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         4.845
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     17.00  42.00   1.00    1.50    --    0.00  57.00  30.00   25
  2  ω     18.00 123.00   1.00    4.50    --   54.00  19.00  60.00  105
  3  ω     82.00 177.00   1.00    4.50    --  108.00  37.00 -30.00   95
  4  ω    132.00 175.00   1.00    4.50    --  108.00  25.00 -90.00   43
  5  ω    101.00 160.00   1.00    4.50    --  108.00 111.00-150.00   59
  6  ω     85.00 170.00   1.00    4.50    --  108.00  37.00  30.00   85
  7  ω     87.00 125.00   1.00    4.50    --  108.00 -63.00-150.00   38
  8  ω     60.00 109.00   1.00    4.50    --  108.00-111.00   0.00   49
  9  ω     62.00 142.00   1.00    4.50    --  108.00 -91.00  30.00   80
 10  ω     88.00 116.00   1.00    4.50    --  108.00-111.00 150.00   28
 11  ω     63.00 125.00   1.00    4.50    --  108.00 -37.00  30.00   62
 12  ω     54.00 107.00   1.00    4.50    --   54.00  37.00 150.00   53
 13  ω     39.00 130.00   1.00    4.50    --  108.00 -37.00 150.00   91
 14  ω     49.00  78.00   1.00    4.50    --   54.00 -77.00  90.00   29
 15  ω     36.00 111.00   1.00    4.50    --   54.00-125.00  60.00   75
 16  ω     39.00 128.00   1.00    4.50    --  108.00 -50.00 -60.00   89
 17  ω     48.00  75.00   1.00    4.50    --  108.00 -63.00-150.00   27
 18  ω     36.00 134.00   1.00    4.50    --  108.00 -91.00-180.00   98
 19  ω     27.00  65.00   1.00    1.50    --    0.00  57.00 -90.00   38
 20  ω     25.00  76.00   1.00    4.50    --   54.00  77.00-150.00   51
 21  ω    -19.00  15.00   1.00    1.50    --    0.00  57.00 -90.00   34
 22  ω    -14.00  70.00   1.00    4.50    --   54.00 -57.00-120.00   84
 23  ω    -16.00  34.00   1.00    4.50    --   54.00 -77.00  90.00   50
 24  ω    -56.00  10.00   1.00    1.50    --    0.00 -57.00 120.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1663935000
_diffrn_orient_matrix_UB_12      -0.0050319000
_diffrn_orient_matrix_UB_13      -0.0543823000
_diffrn_orient_matrix_UB_21      0.0316470000
_diffrn_orient_matrix_UB_22      0.1489124000
_diffrn_orient_matrix_UB_23      -0.0634920000
_diffrn_orient_matrix_UB_31      0.1254836000
_diffrn_orient_matrix_UB_32      -0.0793241000
_diffrn_orient_matrix_UB_33      -0.0780129000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2568
_reflns_number_total             3303
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_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         0.299
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3303
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.027
_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)+(0.0643P)²+0.3230P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1367
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C16(H16A,H16B), C15(H15A,H15B), C18(H18A,H18B), C19(H19A,
 H19B), C22(H22A,H22B), C23(H23A,H23B), C20(H20A,H20B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C4(H4), C9(H9), C1(H1), C5(H5), C11(H11), C2(H2), C12(H12)
;
_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 0.61999(16) 0.20367(13) 0.24797(9) 0.0237(3) Uani 1 1 d . . . . .
N1 N -0.6644(2) 0.89931(18) 0.07738(12) 0.0309(4) Uani 1 1 d . . . . .
C6 C -0.0339(2) 0.56540(19) 0.16036(13) 0.0202(4) Uani 1 1 d . . . . .
C7 C 0.1375(2) 0.46972(19) 0.18093(13) 0.0207(4) Uani 1 1 d . . . . .
C10 C 0.4635(2) 0.28771(18) 0.22026(13) 0.0206(4) Uani 1 1 d . . . . .
C8 C 0.1703(2) 0.40949(19) 0.27799(13) 0.0219(4) Uani 1 1 d . . . . .
H8 H 0.0820 0.4290 0.3303 0.026 Uiso 1 1 calc R . . . .
C4 C -0.3640(2) 0.6188(2) 0.19076(13) 0.0232(4) Uani 1 1 d . . . . .
H4 H -0.4750 0.5945 0.2249 0.028 Uiso 1 1 calc R . . . .
C3 C -0.3592(2) 0.7439(2) 0.11920(13) 0.0216(4) Uani 1 1 d . . . . .
C9 C 0.3313(2) 0.32150(19) 0.29793(13) 0.0222(4) Uani 1 1 d . . . . .
H9 H 0.3516 0.2847 0.3632 0.027 Uiso 1 1 calc R . . . .
C1 C -0.0320(2) 0.6927(2) 0.08963(13) 0.0226(4) Uani 1 1 d . . . . .
H1 H 0.0791 0.7183 0.0564 0.027 Uiso 1 1 calc R . . . .
C5 C -0.2023(2) 0.5306(2) 0.21087(14) 0.0239(4) Uani 1 1 d . . . . .
H5 H -0.2059 0.4472 0.2586 0.029 Uiso 1 1 calc R . . . .
C11 C 0.4315(2) 0.3433(2) 0.12304(14) 0.0243(4) Uani 1 1 d . . . . .
H11 H 0.5173 0.3195 0.0707 0.029 Uiso 1 1 calc R . . . .
C2 C -0.1923(2) 0.7809(2) 0.06841(13) 0.0229(4) Uani 1 1 d . . . . .
H2 H -0.1890 0.8644 0.0207 0.028 Uiso 1 1 calc R . . . .
C12 C 0.2710(2) 0.4344(2) 0.10421(13) 0.0236(4) Uani 1 1 d . . . . .
H12 H 0.2521 0.4729 0.0389 0.028 Uiso 1 1 calc R . . . .
C13 C -0.5283(2) 0.8320(2) 0.09640(13) 0.0236(4) Uani 1 1 d . . . . .
C17 C 1.0712(2) -0.1359(2) 0.33465(14) 0.0241(4) Uani 1 1 d . . . . .
H17 H 1.1379 -0.1756 0.2767 0.029 Uiso 1 1 calc R . . . .
C14 C 0.7492(3) 0.1490(2) 0.17144(14) 0.0299(5) Uani 1 1 d . . . . .
H14A H 0.7783 0.2288 0.1191 0.036 Uiso 1 1 calc R . . . .
H14B H 0.6975 0.0782 0.1429 0.036 Uiso 1 1 calc R . . . .
C16 C 0.8925(2) -0.0488(2) 0.30192(14) 0.0254(4) Uani 1 1 d . . . . .
H16A H 0.8208 -0.1151 0.2817 0.031 Uiso 1 1 calc R . . . .
H16B H 0.8227 -0.0095 0.3584 0.031 Uiso 1 1 calc R . . . .
C15 C 0.9201(3) 0.0773(2) 0.21679(15) 0.0307(5) Uani 1 1 d . . . . .
H15A H 0.9734 0.1515 0.2409 0.037 Uiso 1 1 calc R . . . .
H15B H 1.0077 0.0408 0.1650 0.037 Uiso 1 1 calc R . . . .
C18 C 1.0288(3) -0.2663(2) 0.41384(15) 0.0275(4) Uani 1 1 d . . . . .
H18A H 0.9585 -0.3262 0.3863 0.033 Uiso 1 1 calc R . . . .
H18B H 0.9516 -0.2293 0.4691 0.033 Uiso 1 1 calc R . . . .
C19 C 1.1941(3) -0.3652(2) 0.45455(15) 0.0311(5) Uani 1 1 d . . . . .
H19A H 1.1533 -0.4557 0.4906 0.037 Uiso 1 1 calc R . . . .
H19B H 1.2816 -0.3898 0.3991 0.037 Uiso 1 1 calc R . . . .
C22 C 1.3927(3) -0.1068(2) 0.37211(15) 0.0313(5) Uani 1 1 d . . . . .
H22A H 1.4260 -0.1676 0.3204 0.038 Uiso 1 1 calc R . . . .
H22B H 1.4702 -0.0289 0.3576 0.038 Uiso 1 1 calc R . . . .
C23 C 1.1945(3) -0.0378(2) 0.36652(16) 0.0298(5) Uani 1 1 d . . . . .
H23A H 1.1932 0.0528 0.3199 0.036 Uiso 1 1 calc R . . . .
H23B H 1.1435 -0.0134 0.4312 0.036 Uiso 1 1 calc R . . . .
C20 C 1.2910(3) -0.2972(2) 0.52321(16) 0.0357(5) Uani 1 1 d . . . . .
H20A H 1.3495 -0.3756 0.5686 0.043 Uiso 1 1 calc R . . . .
H20B H 1.1996 -0.2393 0.5625 0.043 Uiso 1 1 calc R . . . .
C21 C 1.4354(3) -0.1997(2) 0.47050(16) 0.0353(5) Uani 1 1 d . . . . .
H21A H 1.4540 -0.1346 0.5151 0.042 Uiso 1 1 calc R . . . .
H21B H 1.5500 -0.2619 0.4588 0.042 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
O1 C10 1.367(2) . ?
O1 C14 1.435(2) . ?
N1 C13 1.149(2) . ?
C6 C7 1.478(2) . ?
C6 C1 1.402(2) . ?
C6 C5 1.400(2) . ?
C7 C8 1.397(2) . ?
C7 C12 1.396(2) . ?
C10 C9 1.396(2) . ?
C10 C11 1.389(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.382(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.394(3) . ?
C4 C5 1.388(2) . ?
C3 C2 1.398(3) . ?
C3 C13 1.441(2) . ?
C9 H9 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.383(2) . ?
C5 H5 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.390(2) . ?
C2 H2 0.9300 . ?
C12 H12 0.9300 . ?
C17 H17 0.9800 . ?
C17 C16 1.534(2) . ?
C17 C18 1.527(3) . ?
C17 C23 1.536(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.510(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C15 1.527(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.536(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.529(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.527(3) . ?
C22 C21 1.523(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.533(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?

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 C14 117.73(14) . . ?
C1 C6 C7 120.89(16) . . ?
C5 C6 C7 120.72(16) . . ?
C5 C6 C1 118.39(16) . . ?
C8 C7 C6 121.07(16) . . ?
C12 C7 C6 121.32(16) . . ?
C12 C7 C8 117.60(16) . . ?
O1 C10 C9 115.57(15) . . ?
O1 C10 C11 125.02(16) . . ?
C11 C10 C9 119.38(16) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.42(16) . . ?
C9 C8 H8 119.3 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C5 C4 C3 119.69(17) . . ?
C4 C3 C2 120.17(16) . . ?
C4 C3 C13 119.30(16) . . ?
C2 C3 C13 120.51(16) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 C10 120.15(16) . . ?
C8 C9 H9 119.9 . . ?
C6 C1 H1 119.4 . . ?
C2 C1 C6 121.17(17) . . ?
C2 C1 H1 119.4 . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 120.99(17) . . ?
C4 C5 H5 119.5 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.84(16) . . ?
C12 C11 H11 120.1 . . ?
C3 C2 H2 120.2 . . ?
C1 C2 C3 119.57(17) . . ?
C1 C2 H2 120.2 . . ?
C7 C12 H12 119.2 . . ?
C11 C12 C7 121.58(17) . . ?
C11 C12 H12 119.2 . . ?
N1 C13 C3 178.3(2) . . ?
C16 C17 H17 107.1 . . ?
C16 C17 C23 112.01(15) . . ?
C18 C17 H17 107.1 . . ?
C18 C17 C16 109.92(15) . . ?
C18 C17 C23 113.37(16) . . ?
C23 C17 H17 107.1 . . ?
O1 C14 H14A 110.0 . . ?
O1 C14 H14B 110.0 . . ?
O1 C14 C15 108.40(15) . . ?
H14A C14 H14B 108.4 . . ?
C15 C14 H14A 110.0 . . ?
C15 C14 H14B 110.0 . . ?
C17 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C15 C16 C17 114.07(15) . . ?
C15 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
C14 C15 C16 115.34(16) . . ?
C14 C15 H15A 108.4 . . ?
C14 C15 H15B 108.4 . . ?
C16 C15 H15A 108.4 . . ?
C16 C15 H15B 108.4 . . ?
H15A C15 H15B 107.5 . . ?
C17 C18 H18A 108.2 . . ?
C17 C18 H18B 108.2 . . ?
C17 C18 C19 116.41(16) . . ?
H18A C18 H18B 107.3 . . ?
C19 C18 H18A 108.2 . . ?
C19 C18 H18B 108.2 . . ?
C18 C19 H19A 108.7 . . ?
C18 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C20 C19 C18 114.38(17) . . ?
C20 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
H22A C22 H22B 107.4 . . ?
C23 C22 H22A 108.2 . . ?
C23 C22 H22B 108.2 . . ?
C21 C22 H22A 108.2 . . ?
C21 C22 H22B 108.2 . . ?
C21 C22 C23 116.27(17) . . ?
C17 C23 H23A 108.7 . . ?
C17 C23 H23B 108.7 . . ?
C22 C23 C17 114.30(16) . . ?
C22 C23 H23A 108.7 . . ?
C22 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
C19 C20 H20A 108.5 . . ?
C19 C20 H20B 108.5 . . ?
C19 C20 C21 115.08(18) . . ?
H20A C20 H20B 107.5 . . ?
C21 C20 H20A 108.5 . . ?
C21 C20 H20B 108.5 . . ?
C22 C21 C20 116.39(17) . . ?
C22 C21 H21A 108.2 . . ?
C22 C21 H21B 108.2 . . ?
C20 C21 H21A 108.2 . . ?
C20 C21 H21B 108.2 . . ?
H21A C21 H21B 107.3 . . ?


_olex2_date_sample_data_collection 2017-09-29
_olex2_date_sample_submission    2017-09-29
_olex2_exptl_crystal_mounting_method 'oil on a micromount 200 micrometres'
_olex2_submission_original_sample_id RM2176
_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 1.242
_oxdiff_exptl_absorpt_empirical_full_min 0.814
