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

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

data_416-zg
_database_code_depnum_ccdc_archive 'CCDC 1857187'
_audit_update_record             
;
2018-07-21 deposited with the CCDC.
2018-10-02 downloaded from the CCDC.
;
_audit_creation_date             2018-05-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H17 N O'
_chemical_formula_sum            'C18 H17 N O'
_chemical_formula_weight         263.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   9.6173(10)
_cell_length_b                   12.7178(10)
_cell_length_c                   11.2532(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.476(10)
_cell_angle_gamma                90.00
_cell_volume                     1370.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    920
_cell_measurement_temperature    295.05(10)
_cell_measurement_theta_max      24.4110
_cell_measurement_theta_min      3.6220
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4906
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.34
_diffrn_ambient_temperature      295.05(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -95.00  -58.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  178.0000  120.0000 37

#__ type_ start__ end____ width___ exp.time_
  2 omega  -48.00   89.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000  -30.0000 137

#__ type_ start__ end____ width___ exp.time_
  3 omega   11.00   57.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000  120.0000 46
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0289795000
_diffrn_orient_matrix_UB_12      -0.0418847000
_diffrn_orient_matrix_UB_13      0.0311581000
_diffrn_orient_matrix_UB_21      -0.0594499000
_diffrn_orient_matrix_UB_22      -0.0003079000
_diffrn_orient_matrix_UB_23      -0.0424021000
_diffrn_orient_matrix_UB_31      0.0334316000
_diffrn_orient_matrix_UB_32      -0.0368294000
_diffrn_orient_matrix_UB_33      -0.0351788000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1744
_reflns_number_total             2690
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2690
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0608
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1625
_refine_ls_wR_factor_ref         0.1982
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C2(H2), C3(H3), C17(H17), C4(H4), C18(H18), C14(H14),
 C16(H16), C15(H15)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.06616(19) 0.16596(13) 0.18275(16) 0.0564(5) Uani 1 d . . .
N1 N 0.0855(2) -0.16431(15) 0.20328(18) 0.0484(6) Uani 1 d . . .
H1 H 0.0549 -0.2124 0.2477 0.058 Uiso 1 calc . . R
C1 C 0.1600(2) -0.18240(19) 0.1058(2) 0.0437(6) Uani 1 d . . .
C10 C 0.1285(2) 0.10836(19) 0.1174(2) 0.0411(6) Uani 1 d . . .
C13 C 0.3089(2) 0.33203(18) 0.0996(2) 0.0442(6) Uani 1 d . . .
C5 C 0.2645(3) -0.08528(19) -0.0447(2) 0.0482(7) Uani 1 d . . .
H5 H 0.2852 -0.0224 -0.0814 0.058 Uiso 1 calc . . R
C12 C 0.2066(3) 0.27389(19) 0.0126(2) 0.0505(7) Uani 1 d . . .
H12A H 0.2253 0.2935 -0.0677 0.061 Uiso 1 calc . . R
H12B H 0.1133 0.2983 0.0240 0.061 Uiso 1 calc . . R
C11 C 0.2072(3) 0.15489(18) 0.0204(2) 0.0463(6) Uani 1 d . . .
H11A H 0.1677 0.1270 -0.0557 0.056 Uiso 1 calc . . R
H11B H 0.3034 0.1313 0.0325 0.056 Uiso 1 calc . . R
C6 C 0.1892(2) -0.08488(18) 0.0564(2) 0.0391(6) Uani 1 d . . .
C8 C 0.0681(2) -0.05970(19) 0.2181(2) 0.0454(6) Uani 1 d . . .
C7 C 0.1290(2) -0.00556(18) 0.1292(2) 0.0399(6) Uani 1 d . . .
C2 C 0.2034(3) -0.27773(19) 0.0611(2) 0.0542(7) Uani 1 d . . .
H2 H 0.1825 -0.3412 0.0964 0.065 Uiso 1 calc . . R
C3 C 0.2781(3) -0.2750(2) -0.0367(2) 0.0564(7) Uani 1 d . . .
H3 H 0.3093 -0.3373 -0.0683 0.068 Uiso 1 calc . . R
C17 C 0.4597(3) 0.3459(2) 0.2833(3) 0.0631(8) Uani 1 d . . .
H17 H 0.4989 0.3154 0.3539 0.076 Uiso 1 calc . . R
C4 C 0.3073(3) -0.1794(2) -0.0888(2) 0.0552(7) Uani 1 d . . .
H4 H 0.3573 -0.1792 -0.1556 0.066 Uiso 1 calc . . R
C18 C 0.3682(3) 0.2886(2) 0.2053(2) 0.0532(7) Uani 1 d . . .
H18 H 0.3463 0.2199 0.2244 0.064 Uiso 1 calc . . R
C14 C 0.3447(3) 0.4343(2) 0.0747(3) 0.0584(8) Uani 1 d . . .
H14 H 0.3068 0.4651 0.0039 0.070 Uiso 1 calc . . R
C9 C -0.0084(3) -0.0198(2) 0.3180(2) 0.0663(8) Uani 1 d . . .
H9A H -0.1048 -0.0089 0.2901 0.099 Uiso 1 calc . . GR
H9B H 0.0321 0.0456 0.3466 0.099 Uiso 1 calc . . GR
H9C H -0.0018 -0.0703 0.3817 0.099 Uiso 1 calc . . GR
C16 C 0.4924(3) 0.4477(2) 0.2558(3) 0.0682(9) Uani 1 d . . .
H16 H 0.5534 0.4865 0.3079 0.082 Uiso 1 calc . . R
C15 C 0.4348(3) 0.4921(2) 0.1515(3) 0.0691(9) Uani 1 d . . .
H15 H 0.4566 0.5610 0.1327 0.083 Uiso 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 1.234(3) . ?
N1 H1 0.8600 . ?
N1 C1 1.386(3) . ?
N1 C8 1.353(3) . ?
C1 C6 1.398(3) . ?
C1 C2 1.392(3) . ?
C10 C11 1.507(3) . ?
C10 C7 1.455(3) . ?
C13 C12 1.513(3) . ?
C13 C18 1.384(3) . ?
C13 C14 1.381(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.407(3) . ?
C5 C4 1.374(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.516(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C6 C7 1.454(3) . ?
C8 C7 1.389(3) . ?
C8 C9 1.490(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(4) . ?
C17 C16 1.375(4) . ?
C4 H4 0.9300 . ?
C18 H18 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.377(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C16 H16 0.9300 . ?
C16 C15 1.370(4) . ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1 125.0 . . ?
C8 N1 H1 125.0 . . ?
C8 N1 C1 109.92(19) . . ?
N1 C1 C6 107.8(2) . . ?
N1 C1 C2 128.8(2) . . ?
C2 C1 C6 123.4(2) . . ?
O1 C10 C11 120.3(2) . . ?
O1 C10 C7 122.3(2) . . ?
C7 C10 C11 117.4(2) . . ?
C18 C13 C12 123.4(2) . . ?
C14 C13 C12 119.2(2) . . ?
C14 C13 C18 117.3(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.4(2) . . ?
C13 C12 H12A 108.1 . . ?
C13 C12 H12B 108.1 . . ?
C13 C12 C11 116.9(2) . . ?
H12A C12 H12B 107.3 . . ?
C11 C12 H12A 108.1 . . ?
C11 C12 H12B 108.1 . . ?
C10 C11 C12 115.8(2) . . ?
C10 C11 H11A 108.3 . . ?
C10 C11 H11B 108.3 . . ?
C12 C11 H11A 108.3 . . ?
C12 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C1 C6 C5 117.2(2) . . ?
C1 C6 C7 106.6(2) . . ?
C5 C6 C7 136.2(2) . . ?
N1 C8 C7 109.4(2) . . ?
N1 C8 C9 120.3(2) . . ?
C7 C8 C9 130.3(2) . . ?
C6 C7 C10 129.6(2) . . ?
C8 C7 C10 124.2(2) . . ?
C8 C7 C6 106.2(2) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 C1 117.8(2) . . ?
C3 C2 H2 121.1 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.3(2) . . ?
C4 C3 H3 119.9 . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.7(3) . . ?
C5 C4 C3 122.0(2) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C13 C18 C17 121.3(3) . . ?
C13 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C13 C14 H14 119.0 . . ?
C15 C14 C13 122.0(3) . . ?
C15 C14 H14 119.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C17 C16 H16 120.1 . . ?
C15 C16 C17 119.9(3) . . ?
C15 C16 H16 120.1 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.8(3) . . ?
C16 C15 H15 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C10 C11 C12 1.6(3) . . . . ?
O1 C10 C7 C6 176.0(2) . . . . ?
O1 C10 C7 C8 -4.2(4) . . . . ?
N1 C1 C6 C5 -179.8(2) . . . . ?
N1 C1 C6 C7 0.2(3) . . . . ?
N1 C1 C2 C3 -179.2(2) . . . . ?
N1 C8 C7 C10 179.3(2) . . . . ?
N1 C8 C7 C6 -0.8(3) . . . . ?
C1 N1 C8 C7 1.0(3) . . . . ?
C1 N1 C8 C9 -179.6(2) . . . . ?
C1 C6 C7 C10 -179.8(2) . . . . ?
C1 C6 C7 C8 0.4(3) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C13 C12 C11 C10 80.5(3) . . . . ?
C13 C14 C15 C16 0.4(4) . . . . ?
C5 C6 C7 C10 0.2(5) . . . . ?
C5 C6 C7 C8 -179.6(3) . . . . ?
C12 C13 C18 C17 -178.9(2) . . . . ?
C12 C13 C14 C15 178.6(2) . . . . ?
C11 C10 C7 C6 -3.6(4) . . . . ?
C11 C10 C7 C8 176.3(2) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
C6 C5 C4 C3 0.2(4) . . . . ?
C8 N1 C1 C6 -0.7(3) . . . . ?
C8 N1 C1 C2 178.3(3) . . . . ?
C7 C10 C11 C12 -178.8(2) . . . . ?
C2 C1 C6 C5 1.1(4) . . . . ?
C2 C1 C6 C7 -178.9(2) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C17 C16 C15 C14 -0.1(4) . . . . ?
C4 C5 C6 C1 -1.0(4) . . . . ?
C4 C5 C6 C7 179.0(3) . . . . ?
C18 C13 C12 C11 -21.0(3) . . . . ?
C18 C13 C14 C15 -0.5(4) . . . . ?
C18 C17 C16 C15 -0.2(4) . . . . ?
C14 C13 C12 C11 160.1(2) . . . . ?
C14 C13 C18 C17 0.1(4) . . . . ?
C9 C8 C7 C10 0.0(4) . . . . ?
C9 C8 C7 C6 179.9(3) . . . . ?
C16 C17 C18 C13 0.2(4) . . . . ?

_olex2_date_sample_data_collection 2018-05-29
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_lilh_0306_4_2
_database_code_depnum_ccdc_archive 'CCDC 1857322'
_audit_update_record             
;
2018-07-25 deposited with the CCDC.
2018-10-02 downloaded from the CCDC.
;
_audit_creation_date             2018-03-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H17 N O'
_chemical_formula_sum            'C18 H17 N O'
_chemical_formula_weight         263.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/c 1'
_space_group_name_Hall           '-I 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z+1/2'
4 '-x+1/2, y+1/2, -z+1'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z+1/2'
8 'x+1/2, -y+1/2, z'

_cell_length_a                   22.0489(5)
_cell_length_b                   15.0516(3)
_cell_length_c                   18.1612(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.711(3)
_cell_angle_gamma                90.00
_cell_volume                     5708.6(2)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    4318
_cell_measurement_temperature    290.04(10)
_cell_measurement_theta_max      69.8630
_cell_measurement_theta_min      10.3330
_exptl_absorpt_coefficient_mu    0.590
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31328
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10519
_diffrn_reflns_theta_full        69.96
_diffrn_reflns_theta_max         69.96
_diffrn_reflns_theta_min         10.28
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.04(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  73.00   1.00    1.00    --   54.00 -57.00 120.00   88
  2  ω     50.00 104.00   1.00    1.00    --   54.00-125.00  90.00   54
  3  ω     64.00  90.00   1.00    1.00    --  108.00-111.00  90.00   26
  4  ω     40.00 125.00   1.00    1.00    --  108.00 -50.00   0.00   85
  5  ω     81.00 108.00   1.00    1.00    --  108.00-111.00 -60.00   27
  6  ω     38.00  97.00   1.00    1.00    --  108.00 -50.00  90.00   59
  7  ω     41.00 116.00   1.00    1.00    --   54.00  57.00  30.00   75
  8  ω    108.00 157.00   1.00    1.00    --  108.00 111.00 120.00   49
  9  ω    105.00 171.00   1.00    1.00    --  108.00 111.00  90.00   66
 10  ω    100.00 177.00   1.00    1.00    --  108.00 111.00 150.00   77
 11  ω     80.00 105.00   1.00    1.00    --  108.00 178.00 -60.00   25
 12  ω     97.00 132.00   1.00    1.00    --  108.00  63.00-180.00   35
 13  ω     86.00 169.00   1.00    1.00    --  108.00  50.00-120.00   83
 14  ω     68.00 122.00   1.00    1.00    --   54.00  57.00 -90.00   54
;
_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      -0.0633538000
_diffrn_orient_matrix_UB_12      0.0362810000
_diffrn_orient_matrix_UB_13      0.0067506000
_diffrn_orient_matrix_UB_21      0.0241495000
_diffrn_orient_matrix_UB_22      -0.0180923000
_diffrn_orient_matrix_UB_23      0.0881368000
_diffrn_orient_matrix_UB_31      0.0291196000
_diffrn_orient_matrix_UB_32      0.0939538000
_diffrn_orient_matrix_UB_33      0.0143786000
_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'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4402
_reflns_number_total             5245
_reflns_odcompleteness_completeness 98.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0585P)²+1.6154P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1155
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C28(H28A,H28B), C29(H29A,H29B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C26(H26), C31(H31),
  C32(H32), C33(H33), C34(H34), C35(H35)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C0AA(H0AA,H0AB,H0AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.45105(5) 0.73036(8) 0.54394(6) 0.0522(3) Uani 1 d . . .
N1 N 0.44181(5) 0.49938(8) 0.37692(6) 0.0342(3) Uani 1 d . . .
C1 C 0.41093(6) 0.47679(9) 0.42976(7) 0.0311(3) Uani 1 d . . .
C2 C 0.38119(6) 0.39712(9) 0.43717(8) 0.0375(3) Uani 1 d . . .
H2 H 0.3796 0.3493 0.4042 0.045 Uiso 1 calc . . R
C3 C 0.35409(6) 0.39273(10) 0.49606(9) 0.0426(3) Uani 1 d . . .
H3 H 0.3337 0.3407 0.5029 0.051 Uiso 1 calc . . R
C4 C 0.35665(7) 0.46467(11) 0.54550(9) 0.0436(4) Uani 1 d . . .
H4 H 0.3380 0.4596 0.5846 0.052 Uiso 1 calc . . R
C5 C 0.38624(6) 0.54318(10) 0.53756(8) 0.0376(3) Uani 1 d . . .
H5 H 0.3875 0.5908 0.5707 0.045 Uiso 1 calc . . R
C6 C 0.41436(6) 0.54992(9) 0.47868(7) 0.0305(3) Uani 1 d . . .
C7 C 0.44931(6) 0.61842(9) 0.45390(7) 0.0308(3) Uani 1 d . . .
C8 C 0.46443(6) 0.58329(9) 0.39211(7) 0.0329(3) Uani 1 d . . .
H8 H 0.4871 0.6131 0.3645 0.040 Uiso 1 calc . . R
C9 C 0.44989(8) 0.44122(11) 0.31736(9) 0.0500(4) Uani 1 d . . .
H9A H 0.4087 0.4261 0.2816 0.075 Uiso 1 calc . . GR
H9B H 0.4716 0.3881 0.3410 0.075 Uiso 1 calc . . GR
H9C H 0.4747 0.4709 0.2900 0.075 Uiso 1 calc . . GR
C10 C 0.46694(6) 0.70552(10) 0.48845(8) 0.0347(3) Uani 1 d . . .
C11 C 0.50773(6) 0.76479(9) 0.45546(8) 0.0331(3) Uani 1 d . . .
H11A H 0.5467 0.7333 0.4577 0.040 Uiso 1 calc . . R
H11B H 0.4846 0.7769 0.4013 0.040 Uiso 1 calc . . R
C12 C 0.52535(8) 0.85229(11) 0.49866(10) 0.0505(4) Uani 1 d . . .
H12A H 0.4876 0.8897 0.4862 0.061 Uiso 1 calc . . R
H12B H 0.5390 0.8407 0.5541 0.061 Uiso 1 calc . . R
C13 C 0.57780(7) 0.90187(9) 0.47932(8) 0.0396(3) Uani 1 d . . .
C14 C 0.56392(9) 0.97198(10) 0.42705(10) 0.0531(4) Uani 1 d . . .
H14 H 0.5216 0.9891 0.4032 0.064 Uiso 1 calc . . R
C15 C 0.61331(12) 1.01722(11) 0.40996(10) 0.0651(6) Uani 1 d . . .
H15 H 0.6036 1.0639 0.3745 0.078 Uiso 1 calc . . R
C16 C 0.67577(10) 0.99324(12) 0.44503(11) 0.0616(5) Uani 1 d . . .
H16 H 0.7084 1.0237 0.4337 0.074 Uiso 1 calc . . R
C17 C 0.68994(8) 0.92478(12) 0.49644(11) 0.0565(4) Uani 1 d . . .
H17 H 0.7324 0.9084 0.5204 0.068 Uiso 1 calc . . R
C18 C 0.64152(7) 0.87940(11) 0.51332(9) 0.0459(4) Uani 1 d . . .
H18 H 0.6521 0.8325 0.5485 0.055 Uiso 1 calc . . R
O2 O 0.31570(5) 0.54124(7) 0.20536(6) 0.0497(3) Uani 1 d . . .
N2 N 0.30884(5) 0.76152(8) 0.37612(6) 0.0370(3) Uani 1 d . . .
C0AA C 0.29689(8) 0.81388(12) 0.43718(10) 0.0534(4) Uani 1 d . . .
H0AA H 0.2695 0.7813 0.4592 0.080 Uiso 1 calc . . GR
H0AB H 0.2765 0.8687 0.4158 0.080 Uiso 1 calc . . GR
H0AC H 0.3368 0.8263 0.4769 0.080 Uiso 1 calc . . GR
C19 C 0.34362(6) 0.78966(9) 0.32904(8) 0.0359(3) Uani 1 d . . .
C20 C 0.37314(7) 0.87112(10) 0.32781(9) 0.0442(4) Uani 1 d . . .
H20 H 0.3722 0.9164 0.3623 0.053 Uiso 1 calc . . R
C21 C 0.40396(8) 0.88180(11) 0.27298(10) 0.0514(4) Uani 1 d . . .
H21 H 0.4240 0.9355 0.2703 0.062 Uiso 1 calc . . R
C22 C 0.40560(7) 0.81367(11) 0.22168(10) 0.0498(4) Uani 1 d . . .
H22 H 0.4268 0.8229 0.1856 0.060 Uiso 1 calc . . R
C23 C 0.37639(7) 0.73256(10) 0.22307(8) 0.0405(3) Uani 1 d . . .
H23 H 0.3780 0.6875 0.1887 0.049 Uiso 1 calc . . R
C24 C 0.34432(6) 0.72011(9) 0.27755(7) 0.0322(3) Uani 1 d . . .
C25 C 0.30827(6) 0.64815(9) 0.29540(7) 0.0307(3) Uani 1 d . . .
C26 C 0.28806(6) 0.67757(9) 0.35556(7) 0.0340(3) Uani 1 d . . .
H26 H 0.2636 0.6444 0.3788 0.041 Uiso 1 calc . . R
C27 C 0.29509(6) 0.56192(9) 0.25824(7) 0.0327(3) Uani 1 d . . .
C28 C 0.25442(6) 0.49729(9) 0.28602(7) 0.0319(3) Uani 1 d . . .
H28A H 0.2138 0.5252 0.2816 0.038 Uiso 1 calc . . R
H28B H 0.2757 0.4844 0.3406 0.038 Uiso 1 calc . . R
C29 C 0.24183(8) 0.41056(11) 0.24091(9) 0.0466(4) Uani 1 d . . .
H29A H 0.2275 0.4234 0.1857 0.056 Uiso 1 calc . . R
H29B H 0.2814 0.3770 0.2530 0.056 Uiso 1 calc . . R
C30 C 0.19186(7) 0.35498(9) 0.26004(8) 0.0390(3) Uani 1 d . . .
C31 C 0.12783(7) 0.36080(11) 0.21540(9) 0.0451(4) Uani 1 d . . .
H31 H 0.1158 0.3981 0.1723 0.054 Uiso 1 calc . . R
C32 C 0.08143(7) 0.31199(11) 0.23399(9) 0.0488(4) Uani 1 d . . .
H32 H 0.0388 0.3161 0.2029 0.059 Uiso 1 calc . . R
C33 C 0.09813(7) 0.25748(10) 0.29826(9) 0.0449(4) Uani 1 d . . .
H33 H 0.0670 0.2254 0.3113 0.054 Uiso 1 calc . . R
C34 C 0.16135(8) 0.25107(10) 0.34288(9) 0.0493(4) Uani 1 d . . .
H34 H 0.1731 0.2142 0.3863 0.059 Uiso 1 calc . . R
C35 C 0.20787(8) 0.29913(10) 0.32383(9) 0.0468(4) Uani 1 d . . .
H35 H 0.2505 0.2937 0.3545 0.056 Uiso 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 1.2267(17) . ?
N1 C1 1.3852(16) . ?
N1 C8 1.3534(18) . ?
N1 C9 1.4463(18) . ?
C1 C2 1.3939(19) . ?
C1 C6 1.4014(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.396(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.4012(18) . ?
C6 C7 1.4429(18) . ?
C7 C8 1.3748(18) . ?
C7 C10 1.4516(19) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.5196(18) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.518(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.509(2) . ?
C13 C14 1.386(2) . ?
C13 C18 1.383(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.401(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.367(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.358(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(2) . ?
C18 H18 0.9300 . ?
O2 C27 1.2269(16) . ?
N2 C0AA 1.4517(18) . ?
N2 C19 1.3855(18) . ?
N2 C26 1.3550(18) . ?
C0AA H0AA 0.9600 . ?
C0AA H0AB 0.9600 . ?
C0AA H0AC 0.9600 . ?
C19 C20 1.392(2) . ?
C19 C24 1.407(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.383(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.394(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.384(2) . ?
C23 H23 0.9300 . ?
C23 C24 1.4008(19) . ?
C24 C25 1.4407(18) . ?
C25 C26 1.3787(18) . ?
C25 C27 1.4487(19) . ?
C26 H26 0.9300 . ?
C27 C28 1.5150(17) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.5187(19) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.5098(19) . ?
C30 C31 1.387(2) . ?
C30 C35 1.382(2) . ?
C31 H31 0.9300 . ?
C31 C32 1.386(2) . ?
C32 H32 0.9300 . ?
C32 C33 1.377(2) . ?
C33 H33 0.9300 . ?
C33 C34 1.373(2) . ?
C34 H34 0.9300 . ?
C34 C35 1.387(2) . ?
C35 H35 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C9 125.12(12) . . ?
C8 N1 C1 108.59(11) . . ?
C8 N1 C9 126.26(12) . . ?
N1 C1 C2 128.98(13) . . ?
N1 C1 C6 107.93(11) . . ?
C2 C1 C6 123.08(12) . . ?
C1 C2 H2 121.7 . . ?
C3 C2 C1 116.67(14) . . ?
C3 C2 H2 121.7 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.43(14) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.34(13) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.79(14) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C5 118.68(12) . . ?
C1 C6 C7 106.79(11) . . ?
C5 C6 C7 134.52(13) . . ?
C6 C7 C10 127.31(11) . . ?
C8 C7 C6 105.88(11) . . ?
C8 C7 C10 126.78(12) . . ?
N1 C8 C7 110.80(11) . . ?
N1 C8 H8 124.6 . . ?
C7 C8 H8 124.6 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 C7 121.53(13) . . ?
O1 C10 C11 120.41(13) . . ?
C7 C10 C11 118.04(11) . . ?
C10 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 C10 113.03(11) . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C11 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 C11 113.38(12) . . ?
C13 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C14 C13 C12 121.22(15) . . ?
C18 C13 C12 121.30(14) . . ?
C18 C13 C14 117.48(15) . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.33(17) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.45(16) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.73(16) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.25(17) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 119.1 . . ?
C17 C18 C13 121.76(16) . . ?
C17 C18 H18 119.1 . . ?
C19 N2 C0AA 125.27(13) . . ?
C26 N2 C0AA 126.06(13) . . ?
C26 N2 C19 108.67(12) . . ?
N2 C0AA H0AA 109.5 . . ?
N2 C0AA H0AB 109.5 . . ?
N2 C0AA H0AC 109.5 . . ?
H0AA C0AA H0AB 109.5 . . ?
H0AA C0AA H0AC 109.5 . . ?
H0AB C0AA H0AC 109.5 . . ?
N2 C19 C20 129.32(14) . . ?
N2 C19 C24 108.00(12) . . ?
C20 C19 C24 122.67(14) . . ?
C19 C20 H20 121.5 . . ?
C21 C20 C19 117.02(15) . . ?
C21 C20 H20 121.5 . . ?
C20 C21 H21 119.3 . . ?
C20 C21 C22 121.32(14) . . ?
C22 C21 H21 119.3 . . ?
C21 C22 H22 119.2 . . ?
C23 C22 C21 121.65(15) . . ?
C23 C22 H22 119.2 . . ?
C22 C23 H23 120.9 . . ?
C22 C23 C24 118.30(15) . . ?
C24 C23 H23 120.9 . . ?
C19 C24 C25 106.57(11) . . ?
C23 C24 C19 119.04(13) . . ?
C23 C24 C25 134.38(13) . . ?
C24 C25 C27 127.69(12) . . ?
C26 C25 C24 106.19(12) . . ?
C26 C25 C27 126.12(12) . . ?
N2 C26 C25 110.57(12) . . ?
N2 C26 H26 124.7 . . ?
C25 C26 H26 124.7 . . ?
O2 C27 C25 121.51(12) . . ?
O2 C27 C28 120.34(12) . . ?
C25 C27 C28 118.15(11) . . ?
C27 C28 H28A 108.9 . . ?
C27 C28 H28B 108.9 . . ?
C27 C28 C29 113.43(11) . . ?
H28A C28 H28B 107.7 . . ?
C29 C28 H28A 108.9 . . ?
C29 C28 H28B 108.9 . . ?
C28 C29 H29A 109.2 . . ?
C28 C29 H29B 109.2 . . ?
H29A C29 H29B 107.9 . . ?
C30 C29 C28 111.89(11) . . ?
C30 C29 H29A 109.2 . . ?
C30 C29 H29B 109.2 . . ?
C31 C30 C29 120.76(14) . . ?
C35 C30 C29 121.38(14) . . ?
C35 C30 C31 117.82(13) . . ?
C30 C31 H31 119.5 . . ?
C32 C31 C30 121.10(14) . . ?
C32 C31 H31 119.5 . . ?
C31 C32 H32 119.8 . . ?
C33 C32 C31 120.31(15) . . ?
C33 C32 H32 119.8 . . ?
C32 C33 H33 120.4 . . ?
C34 C33 C32 119.15(14) . . ?
C34 C33 H33 120.4 . . ?
C33 C34 H34 119.7 . . ?
C33 C34 C35 120.56(15) . . ?
C35 C34 H34 119.7 . . ?
C30 C35 C34 121.05(15) . . ?
C30 C35 H35 119.5 . . ?
C34 C35 H35 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C10 C11 C12 0.68(19) . . . . ?
N1 C1 C2 C3 179.71(12) . . . . ?
N1 C1 C6 C5 -179.99(11) . . . . ?
N1 C1 C6 C7 -0.48(13) . . . . ?
C1 N1 C8 C7 -0.31(15) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C1 C6 C7 C8 0.29(13) . . . . ?
C1 C6 C7 C10 -177.81(12) . . . . ?
C2 C1 C6 C5 -0.47(18) . . . . ?
C2 C1 C6 C7 179.04(11) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C1 0.44(18) . . . . ?
C4 C5 C6 C7 -178.90(13) . . . . ?
C5 C6 C7 C8 179.69(14) . . . . ?
C5 C6 C7 C10 1.6(2) . . . . ?
C6 C1 C2 C3 0.29(19) . . . . ?
C6 C7 C8 N1 0.01(14) . . . . ?
C6 C7 C10 O1 -2.0(2) . . . . ?
C6 C7 C10 C11 176.11(11) . . . . ?
C7 C10 C11 C12 -177.50(12) . . . . ?
C8 N1 C1 C2 -178.99(13) . . . . ?
C8 N1 C1 C6 0.49(14) . . . . ?
C8 C7 C10 O1 -179.77(13) . . . . ?
C8 C7 C10 C11 -1.61(19) . . . . ?
C9 N1 C1 C2 -0.8(2) . . . . ?
C9 N1 C1 C6 178.71(13) . . . . ?
C9 N1 C8 C7 -178.50(13) . . . . ?
C10 C7 C8 N1 178.13(11) . . . . ?
C10 C11 C12 C13 166.46(12) . . . . ?
C11 C12 C13 C14 100.06(17) . . . . ?
C11 C12 C13 C18 -80.27(18) . . . . ?
C12 C13 C14 C15 179.91(14) . . . . ?
C12 C13 C18 C17 -179.53(14) . . . . ?
C13 C14 C15 C16 -0.5(2) . . . . ?
C14 C13 C18 C17 0.2(2) . . . . ?
C14 C15 C16 C17 0.4(3) . . . . ?
C15 C16 C17 C18 0.0(3) . . . . ?
C16 C17 C18 C13 -0.3(2) . . . . ?
C18 C13 C14 C15 0.2(2) . . . . ?
O2 C27 C28 C29 -1.67(18) . . . . ?
N2 C19 C20 C21 -178.74(13) . . . . ?
N2 C19 C24 C23 179.53(11) . . . . ?
N2 C19 C24 C25 0.03(13) . . . . ?
C0AA N2 C19 C20 -1.2(2) . . . . ?
C0AA N2 C19 C24 179.94(12) . . . . ?
C0AA N2 C26 C25 -179.91(12) . . . . ?
C19 N2 C26 C25 0.12(14) . . . . ?
C19 C20 C21 C22 -0.4(2) . . . . ?
C19 C24 C25 C26 0.04(13) . . . . ?
C19 C24 C25 C27 179.82(12) . . . . ?
C20 C19 C24 C23 0.55(19) . . . . ?
C20 C19 C24 C25 -178.95(12) . . . . ?
C20 C21 C22 C23 0.2(2) . . . . ?
C21 C22 C23 C24 0.4(2) . . . . ?
C22 C23 C24 C19 -0.71(19) . . . . ?
C22 C23 C24 C25 178.62(13) . . . . ?
C23 C24 C25 C26 -179.34(14) . . . . ?
C23 C24 C25 C27 0.4(2) . . . . ?
C24 C19 C20 C21 0.0(2) . . . . ?
C24 C25 C26 N2 -0.10(14) . . . . ?
C24 C25 C27 O2 1.0(2) . . . . ?
C24 C25 C27 C28 -178.58(12) . . . . ?
C25 C27 C28 C29 177.89(12) . . . . ?
C26 N2 C19 C20 178.79(13) . . . . ?
C26 N2 C19 C24 -0.09(14) . . . . ?
C26 C25 C27 O2 -179.29(13) . . . . ?
C26 C25 C27 C28 1.15(19) . . . . ?
C27 C25 C26 N2 -179.88(11) . . . . ?
C27 C28 C29 C30 -169.69(12) . . . . ?
C28 C29 C30 C31 93.31(16) . . . . ?
C28 C29 C30 C35 -84.43(18) . . . . ?
C29 C30 C31 C32 -178.03(14) . . . . ?
C29 C30 C35 C34 177.30(14) . . . . ?
C30 C31 C32 C33 1.0(2) . . . . ?
C31 C30 C35 C34 -0.5(2) . . . . ?
C31 C32 C33 C34 -1.0(2) . . . . ?
C32 C33 C34 C35 0.3(2) . . . . ?
C33 C34 C35 C30 0.5(2) . . . . ?
C35 C30 C31 C32 -0.2(2) . . . . ?

_olex2_date_sample_data_collection 2018-03-06
_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 3.442
_oxdiff_exptl_absorpt_empirical_full_min 0.696
####################################################################### 
# 
# 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_lilh_423_4
_database_code_depnum_ccdc_archive 'CCDC 1857189'
_audit_update_record             
;
2018-07-21 deposited with the CCDC.
2018-10-02 downloaded from the CCDC.
;
_audit_creation_date             2018-05-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_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          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.2569(18)
_cell_length_b                   15.608(2)
_cell_length_c                   10.8924(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.432(19)
_cell_angle_gamma                90.00
_cell_volume                     1517.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1125
_cell_measurement_temperature    232(6)
_cell_measurement_theta_max      27.2420
_cell_measurement_theta_min      4.0810
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0671
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5621
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.37
_diffrn_ambient_temperature      232(6)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -50.00  -17.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273   77.0000   90.0000 22

#__ type_ start__ end____ width___ exp.time_
  2 omega  -38.00   88.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000  120.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega   20.00   87.50   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  -30.0000 45
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0541763000
_diffrn_orient_matrix_UB_12      -0.0162699000
_diffrn_orient_matrix_UB_13      0.0538405000
_diffrn_orient_matrix_UB_21      -0.0581164000
_diffrn_orient_matrix_UB_22      -0.0144986000
_diffrn_orient_matrix_UB_23      0.0261457000
_diffrn_orient_matrix_UB_31      -0.0011442000
_diffrn_orient_matrix_UB_32      -0.0398759000
_diffrn_orient_matrix_UB_33      -0.0314135000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1790
_reflns_number_total             2987
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2987
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1253
_refine_ls_R_factor_gt           0.0812
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0712P)²+0.6736P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1884
_refine_ls_wR_factor_ref         0.2195
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C0AA(H0AA,H0AB,H0AC), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.7235(3) 0.22886(15) 0.3899(2) 0.0592(7) Uani 1 d . . .
N1 N 0.9545(3) 0.44933(18) 0.6467(3) 0.0542(7) Uani 1 d . . .
C0AA C 1.0565(4) 0.5010(3) 0.7422(4) 0.0737(12) Uani 1 d . . .
H0AA H 1.0478 0.5600 0.7160 0.110 Uiso 1 calc . . GR
H0AB H 1.1574 0.4818 0.7517 0.110 Uiso 1 calc . . GR
H0AC H 1.0319 0.4955 0.8220 0.110 Uiso 1 calc . . GR
C1 C 0.8280(4) 0.4795(2) 0.5564(3) 0.0482(8) Uani 1 d . . .
C2 C 0.7740(4) 0.5626(2) 0.5365(4) 0.0612(10) Uani 1 d . . .
H2 H 0.8220 0.6081 0.5859 0.073 Uiso 1 calc . . R
C3 C 0.6452(5) 0.5737(2) 0.4395(4) 0.0697(11) Uani 1 d . . .
H3 H 0.6054 0.6285 0.4227 0.084 Uiso 1 calc . . R
C4 C 0.5732(5) 0.5060(2) 0.3660(4) 0.0660(10) Uani 1 d . . .
H4 H 0.4866 0.5161 0.3012 0.079 Uiso 1 calc . . R
C5 C 0.6286(4) 0.4234(2) 0.3882(3) 0.0547(9) Uani 1 d . . .
H5 H 0.5788 0.3779 0.3398 0.066 Uiso 1 calc . . R
C6 C 0.7599(4) 0.4095(2) 0.4839(3) 0.0457(8) Uani 1 d . . .
C7 C 0.8493(3) 0.3349(2) 0.5305(3) 0.0445(8) Uani 1 d . . .
C8 C 0.9660(4) 0.3642(2) 0.6302(3) 0.0529(8) Uani 1 d . . .
H8 H 1.0418 0.3298 0.6790 0.064 Uiso 1 calc . . R
C9 C 0.8276(4) 0.2484(2) 0.4825(3) 0.0462(8) Uani 1 d . . .
C10 C 0.9429(4) 0.18101(19) 0.5479(3) 0.0490(8) Uani 1 d . . .
H10 H 0.9744 0.1946 0.6390 0.059 Uiso 1 calc . . R
C11 C 0.8780(4) 0.0905(2) 0.5338(4) 0.0587(9) Uani 1 d . . .
H11A H 0.8432 0.0768 0.4439 0.070 Uiso 1 calc . . R
H11B H 0.9572 0.0504 0.5722 0.070 Uiso 1 calc . . R
C12 C 0.7493(4) 0.0779(3) 0.5942(4) 0.0789(13) Uani 1 d . . .
H12A H 0.6631 0.1089 0.5461 0.118 Uiso 1 calc . . GR
H12B H 0.7779 0.0989 0.6801 0.118 Uiso 1 calc . . GR
H12C H 0.7256 0.0181 0.5944 0.118 Uiso 1 calc . . GR
C13 C 1.0809(4) 0.18648(19) 0.4970(3) 0.0454(8) Uani 1 d . . .
C14 C 1.2223(4) 0.1888(2) 0.5806(3) 0.0555(9) Uani 1 d . . .
H14 H 1.2326 0.1885 0.6679 0.067 Uiso 1 calc . . R
C15 C 1.3490(4) 0.1914(2) 0.5356(4) 0.0629(10) Uani 1 d . . .
H15 H 1.4437 0.1927 0.5926 0.075 Uiso 1 calc . . R
C16 C 1.3342(5) 0.1921(2) 0.4069(4) 0.0678(11) Uani 1 d . . .
H16 H 1.4188 0.1944 0.3763 0.081 Uiso 1 calc . . R
C17 C 1.1941(5) 0.1895(3) 0.3233(4) 0.0697(11) Uani 1 d . . .
H17 H 1.1842 0.1893 0.2361 0.084 Uiso 1 calc . . R
C18 C 1.0672(4) 0.1872(2) 0.3679(3) 0.0595(9) Uani 1 d . . .
H18 H 0.9726 0.1861 0.3106 0.071 Uiso 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 C9 1.234(4) . ?
N1 C0AA 1.450(4) . ?
N1 C1 1.395(4) . ?
N1 C8 1.348(4) . ?
C0AA H0AA 0.9600 . ?
C0AA H0AB 0.9600 . ?
C0AA H0AC 0.9600 . ?
C1 C2 1.386(5) . ?
C1 C6 1.396(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(5) . ?
C6 C7 1.440(4) . ?
C7 C8 1.389(4) . ?
C7 C9 1.442(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.533(4) . ?
C10 H10 0.9800 . ?
C10 C11 1.527(5) . ?
C10 C13 1.523(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.518(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.381(5) . ?
C13 C18 1.378(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.372(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.373(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.386(5) . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C0AA 125.6(3) . . ?
C8 N1 C0AA 125.7(3) . . ?
C8 N1 C1 108.6(3) . . ?
N1 C0AA H0AA 109.5 . . ?
N1 C0AA H0AB 109.5 . . ?
N1 C0AA H0AC 109.5 . . ?
H0AA C0AA H0AB 109.5 . . ?
H0AA C0AA H0AC 109.5 . . ?
H0AB C0AA H0AC 109.5 . . ?
N1 C1 C6 107.6(3) . . ?
C2 C1 N1 128.7(3) . . ?
C2 C1 C6 123.7(3) . . ?
C1 C2 H2 121.9 . . ?
C3 C2 C1 116.1(3) . . ?
C3 C2 H2 121.9 . . ?
C2 C3 H3 118.9 . . ?
C2 C3 C4 122.1(4) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.7(4) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.0(3) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C7 107.6(3) . . ?
C5 C6 C1 118.3(3) . . ?
C5 C6 C7 134.1(3) . . ?
C6 C7 C9 128.1(3) . . ?
C8 C7 C6 105.3(3) . . ?
C8 C7 C9 126.6(3) . . ?
N1 C8 C7 110.8(3) . . ?
N1 C8 H8 124.6 . . ?
C7 C8 H8 124.6 . . ?
O1 C9 C7 122.1(3) . . ?
O1 C9 C10 120.4(3) . . ?
C7 C9 C10 117.5(3) . . ?
C9 C10 H10 107.7 . . ?
C11 C10 C9 112.4(3) . . ?
C11 C10 H10 107.7 . . ?
C13 C10 C9 109.9(2) . . ?
C13 C10 H10 107.7 . . ?
C13 C10 C11 111.2(3) . . ?
C10 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 C10 114.2(3) . . ?
C12 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C10 120.1(3) . . ?
C18 C13 C10 120.9(3) . . ?
C18 C13 C14 119.0(3) . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.7(3) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.8(4) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.5(4) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 C17 120.1(4) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C9 C10 C11 -27.9(4) . . . . ?
O1 C9 C10 C13 96.5(3) . . . . ?
N1 C1 C2 C3 -179.9(3) . . . . ?
N1 C1 C6 C5 178.8(3) . . . . ?
N1 C1 C6 C7 -0.9(3) . . . . ?
C0AA N1 C1 C2 1.0(5) . . . . ?
C0AA N1 C1 C6 -179.3(3) . . . . ?
C0AA N1 C8 C7 179.8(3) . . . . ?
C1 N1 C8 C7 -0.3(3) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C1 C6 C7 C8 0.7(3) . . . . ?
C1 C6 C7 C9 -177.2(3) . . . . ?
C2 C1 C6 C5 -1.5(5) . . . . ?
C2 C1 C6 C7 178.8(3) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
C3 C4 C5 C6 -1.3(5) . . . . ?
C4 C5 C6 C1 1.9(5) . . . . ?
C4 C5 C6 C7 -178.5(3) . . . . ?
C5 C6 C7 C8 -178.9(3) . . . . ?
C5 C6 C7 C9 3.1(6) . . . . ?
C6 C1 C2 C3 0.5(5) . . . . ?
C6 C7 C8 N1 -0.3(3) . . . . ?
C6 C7 C9 O1 0.5(5) . . . . ?
C6 C7 C9 C10 178.2(3) . . . . ?
C7 C9 C10 C11 154.4(3) . . . . ?
C7 C9 C10 C13 -81.2(3) . . . . ?
C8 N1 C1 C2 -178.9(3) . . . . ?
C8 N1 C1 C6 0.8(3) . . . . ?
C8 C7 C9 O1 -177.0(3) . . . . ?
C8 C7 C9 C10 0.7(4) . . . . ?
C9 C7 C8 N1 177.7(3) . . . . ?
C9 C10 C11 C12 -62.0(4) . . . . ?
C9 C10 C13 C14 131.4(3) . . . . ?
C9 C10 C13 C18 -50.1(4) . . . . ?
C10 C13 C14 C15 178.3(3) . . . . ?
C10 C13 C18 C17 -178.0(3) . . . . ?
C11 C10 C13 C14 -103.5(4) . . . . ?
C11 C10 C13 C18 75.0(4) . . . . ?
C13 C10 C11 C12 174.3(3) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
C14 C13 C18 C17 0.5(5) . . . . ?
C14 C15 C16 C17 -0.5(6) . . . . ?
C15 C16 C17 C18 0.8(6) . . . . ?
C16 C17 C18 C13 -0.7(6) . . . . ?
C18 C13 C14 C15 -0.2(5) . . . . ?

_olex2_date_sample_data_collection 2018-05-16
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_lilh_0426
_database_code_depnum_ccdc_archive 'CCDC 1857188'
_audit_update_record             
;
2018-07-21 deposited with the CCDC.
2018-10-02 downloaded from the CCDC.
;
_audit_creation_date             2018-04-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H16 Br N O'
_chemical_formula_sum            'C18 H16 Br N O'
_chemical_formula_weight         342.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Br Br -0.6763 1.2805 '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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.4795(3)
_cell_length_b                   11.3762(4)
_cell_length_c                   16.2210(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.399(3)
_cell_angle_gamma                90.00
_cell_volume                     1563.38(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1936
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.8960
_cell_measurement_theta_min      6.5000
_exptl_absorpt_coefficient_mu    3.558
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5163
_diffrn_reflns_theta_full        66.59
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_min         4.75
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -4.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega   28.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -30.0000 34

#__ type_ start__ end____ width___ exp.time_
  3 omega  -47.00   14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -63.0000 -180.0000 61

#__ type_ start__ end____ width___ exp.time_
  4 omega   22.00   48.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000   51.0646 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   -1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -90.0000 76

#__ type_ start__ end____ width___ exp.time_
  6 omega   33.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 90

#__ type_ start__ end____ width___ exp.time_
  7 omega   35.00   81.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   60.0000 46

#__ type_ start__ end____ width___ exp.time_
  8 omega   50.00   76.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   35.00   99.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 64

#__ type_ start__ end____ width___ exp.time_
 10 omega   68.00  131.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000 -150.0000 63

#__ type_ start__ end____ width___ exp.time_
 11 omega   57.00  151.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -30.0000 94

#__ type_ start__ end____ width___ exp.time_
 12 omega   51.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  120.0000 37

#__ type_ start__ end____ width___ exp.time_
 13 omega   81.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -117.0000    3.0000 32

#__ type_ start__ end____ width___ exp.time_
 14 omega   97.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000 -180.0000 81

#__ type_ start__ end____ width___ exp.time_
 15 omega   52.00   79.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 16 omega   62.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 17 omega   38.00   63.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  120.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0204288000
_diffrn_orient_matrix_UB_12      -0.0986321000
_diffrn_orient_matrix_UB_13      -0.0637916000
_diffrn_orient_matrix_UB_21      0.0065541000
_diffrn_orient_matrix_UB_22      0.0925257000
_diffrn_orient_matrix_UB_23      -0.0691138000
_diffrn_orient_matrix_UB_31      0.1805285000
_diffrn_orient_matrix_UB_32      0.0077189000
_diffrn_orient_matrix_UB_33      0.0137373000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2226
_reflns_number_total             2685
_reflns_odcompleteness_completeness 97.12
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2685
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0529P)²+0.6831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1183
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C13(H13), C2(H2), C17(H17), C3(H3), C14(H14), C15(H15),
 C16(H16)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br 0.02587(6) 0.84378(4) 0.45982(3) 0.0884(2) Uani 1 d . . .
O1 O 0.1392(3) 0.63319(18) 0.76104(13) 0.0571(5) Uani 1 d . . .
C5 C 0.1286(3) 0.6651(2) 0.57081(18) 0.0482(6) Uani 1 d . . .
H5 H 0.0916 0.7146 0.6113 0.058 Uiso 1 calc . . R
C7 C 0.2316(3) 0.4963(2) 0.66755(16) 0.0433(6) Uani 1 d . . .
C9 C 0.1995(3) 0.5369(2) 0.74951(17) 0.0439(6) Uani 1 d . . .
C8 C 0.3021(4) 0.3913(2) 0.64595(19) 0.0525(7) Uani 1 d . . .
H8 H 0.3351 0.3331 0.6830 0.063 Uiso 1 calc . . R
C1 C 0.2529(4) 0.4863(3) 0.52738(18) 0.0542(7) Uani 1 d . . .
N1 N 0.3160(3) 0.3857(2) 0.56346(16) 0.0601(7) Uani 1 d . . .
C12 C -0.0281(3) 0.3762(3) 0.84278(17) 0.0490(6) Uani 1 d . . .
C11 C 0.1087(4) 0.4431(3) 0.88083(17) 0.0584(7) Uani 1 d . . .
H11A H 0.1476 0.4019 0.9299 0.070 Uiso 1 calc . . R
H11B H 0.0721 0.5198 0.8979 0.070 Uiso 1 calc . . R
C10 C 0.2453(3) 0.4598(3) 0.82296(17) 0.0516(7) Uani 1 d . . .
H10A H 0.3340 0.4951 0.8535 0.062 Uiso 1 calc . . R
H10B H 0.2786 0.3835 0.8034 0.062 Uiso 1 calc . . R
C6 C 0.1984(3) 0.5581(2) 0.59108(16) 0.0440(6) Uani 1 d . . .
C4 C 0.1160(4) 0.6957(3) 0.4885(2) 0.0576(7) Uani 1 d . . .
C13 C -0.0066(4) 0.2661(3) 0.80994(18) 0.0561(7) Uani 1 d . . .
H13 H 0.0946 0.2347 0.8098 0.067 Uiso 1 calc . . R
C18 C 0.3893(6) 0.2887(3) 0.5195(3) 0.0856(12) Uani 1 d . . .
H18A H 0.4771 0.3180 0.4901 0.128 Uiso 1 calc . . GR
H18B H 0.3132 0.2544 0.4812 0.128 Uiso 1 calc . . GR
H18C H 0.4257 0.2301 0.5584 0.128 Uiso 1 calc . . GR
C2 C 0.2378(5) 0.5176(3) 0.4450(2) 0.0701(9) Uani 1 d . . .
H2 H 0.2740 0.4684 0.4040 0.084 Uiso 1 calc . . R
C17 C -0.1787(4) 0.4214(4) 0.8402(3) 0.0794(11) Uani 1 d . . .
H17 H -0.1967 0.4964 0.8606 0.095 Uiso 1 calc . . R
C3 C 0.1680(5) 0.6234(3) 0.4255(2) 0.0703(9) Uani 1 d . . .
H3 H 0.1553 0.6469 0.3707 0.084 Uiso 1 calc . . R
C14 C -0.1314(5) 0.2013(4) 0.7774(2) 0.0762(10) Uani 1 d . . .
H14 H -0.1137 0.1269 0.7559 0.091 Uiso 1 calc . . R
C15 C -0.2809(5) 0.2457(5) 0.7764(3) 0.0980(17) Uani 1 d . . .
H15 H -0.3657 0.2018 0.7551 0.118 Uiso 1 calc . . R
C16 C -0.3039(5) 0.3557(5) 0.8073(4) 0.108(2) Uani 1 d . . .
H16 H -0.4053 0.3871 0.8062 0.130 Uiso 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
Br1 C4 1.899(3) . ?
O1 C9 1.227(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(4) . ?
C5 C4 1.380(4) . ?
C7 C9 1.444(4) . ?
C7 C8 1.386(4) . ?
C7 C6 1.443(4) . ?
C9 C10 1.517(4) . ?
C8 H8 0.9300 . ?
C8 N1 1.350(4) . ?
C1 N1 1.383(4) . ?
C1 C6 1.410(4) . ?
C1 C2 1.384(4) . ?
N1 C18 1.466(4) . ?
C12 C11 1.498(4) . ?
C12 C13 1.377(4) . ?
C12 C17 1.375(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C10 1.533(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C4 C3 1.397(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C2 H2 0.9300 . ?
C2 C3 1.373(5) . ?
C17 H17 0.9300 . ?
C17 C16 1.387(7) . ?
C3 H3 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.364(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.365(7) . ?
C16 H16 0.9300 . ?

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
C6 C5 H5 121.1 . . ?
C4 C5 H5 121.1 . . ?
C4 C5 C6 117.8(3) . . ?
C8 C7 C9 127.4(3) . . ?
C8 C7 C6 105.8(2) . . ?
C6 C7 C9 126.7(2) . . ?
O1 C9 C7 121.5(3) . . ?
O1 C9 C10 119.4(3) . . ?
C7 C9 C10 119.1(2) . . ?
C7 C8 H8 124.8 . . ?
N1 C8 C7 110.4(3) . . ?
N1 C8 H8 124.8 . . ?
N1 C1 C6 107.6(3) . . ?
N1 C1 C2 129.8(3) . . ?
C2 C1 C6 122.6(3) . . ?
C8 N1 C1 109.4(3) . . ?
C8 N1 C18 125.1(3) . . ?
C1 N1 C18 125.5(3) . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 C17 117.7(3) . . ?
C17 C12 C11 121.7(3) . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C12 C11 C10 113.7(2) . . ?
H11A C11 H11B 107.7 . . ?
C10 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
C9 C10 C11 112.2(2) . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C5 C6 C7 134.2(3) . . ?
C5 C6 C1 119.0(3) . . ?
C1 C6 C7 106.8(2) . . ?
C5 C4 Br1 118.3(2) . . ?
C5 C4 C3 123.1(3) . . ?
C3 C4 Br1 118.6(2) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 C12 121.6(3) . . ?
C14 C13 H13 119.2 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 C2 H2 121.0 . . ?
C3 C2 C1 118.0(3) . . ?
C3 C2 H2 121.0 . . ?
C12 C17 H17 119.8 . . ?
C12 C17 C16 120.4(4) . . ?
C16 C17 H17 119.8 . . ?
C4 C3 H3 120.2 . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 H3 120.2 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.6 . . ?
C14 C15 C16 118.8(4) . . ?
C16 C15 H15 120.6 . . ?
C17 C16 H16 119.5 . . ?
C15 C16 C17 121.1(4) . . ?
C15 C16 H16 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C4 C3 C2 178.0(3) . . . . ?
O1 C9 C10 C11 51.8(4) . . . . ?
C5 C4 C3 C2 -1.2(6) . . . . ?
C7 C9 C10 C11 -129.7(3) . . . . ?
C7 C8 N1 C1 -0.9(4) . . . . ?
C7 C8 N1 C18 178.1(3) . . . . ?
C9 C7 C8 N1 -178.3(3) . . . . ?
C9 C7 C6 C5 -1.6(5) . . . . ?
C9 C7 C6 C1 178.6(3) . . . . ?
C8 C7 C9 O1 178.4(3) . . . . ?
C8 C7 C9 C10 -0.1(4) . . . . ?
C8 C7 C6 C5 179.2(3) . . . . ?
C8 C7 C6 C1 -0.6(3) . . . . ?
C1 C2 C3 C4 0.4(6) . . . . ?
N1 C1 C6 C5 -179.8(3) . . . . ?
N1 C1 C6 C7 0.1(3) . . . . ?
N1 C1 C2 C3 179.2(3) . . . . ?
C12 C11 C10 C9 65.6(3) . . . . ?
C12 C13 C14 C15 0.4(5) . . . . ?
C12 C17 C16 C15 -0.4(7) . . . . ?
C11 C12 C13 C14 177.6(3) . . . . ?
C11 C12 C17 C16 -177.6(3) . . . . ?
C6 C5 C4 Br1 -178.4(2) . . . . ?
C6 C5 C4 C3 0.9(5) . . . . ?
C6 C7 C9 O1 -0.6(4) . . . . ?
C6 C7 C9 C10 -179.1(2) . . . . ?
C6 C7 C8 N1 0.9(3) . . . . ?
C6 C1 N1 C8 0.5(4) . . . . ?
C6 C1 N1 C18 -178.5(3) . . . . ?
C6 C1 C2 C3 0.6(5) . . . . ?
C4 C5 C6 C7 -179.6(3) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C13 C12 C11 C10 55.6(4) . . . . ?
C13 C12 C17 C16 1.6(5) . . . . ?
C13 C14 C15 C16 0.8(6) . . . . ?
C2 C1 N1 C8 -178.3(4) . . . . ?
C2 C1 N1 C18 2.7(6) . . . . ?
C2 C1 C6 C5 -0.9(5) . . . . ?
C2 C1 C6 C7 178.9(3) . . . . ?
C17 C12 C11 C10 -125.1(3) . . . . ?
C17 C12 C13 C14 -1.6(5) . . . . ?
C14 C15 C16 C17 -0.8(7) . . . . ?

_olex2_date_sample_data_collection 2018-04-28
_olex2_submission_special_instructions 'No special instructions were received'
