# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_20170446
_database_code_depnum_ccdc_archive 'CCDC 1565428'
_audit_update_record             
;
2017-07-28 deposited with the CCDC.
2017-12-22 downloaded from the CCDC.
;
_audit_creation_date             2017-04-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
N-(8-quinolyl)-N-(2-tetrahydrofuranyl)propionamide
_chemical_formula_moiety         'C16 H18 N2 O2'
_chemical_formula_sum            'C16 H18 N2 O2'
_chemical_formula_weight         270.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         C38H70N2O2
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                   9.5527(3)
_cell_length_b                   12.3620(5)
_cell_length_c                   12.0679(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.577(3)
_cell_angle_gamma                90
_cell_volume                     1423.66(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1685
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.2470
_cell_measurement_theta_min      3.6620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)
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    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0270
_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       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5395
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.968
_diffrn_reflns_theta_max         66.968
_diffrn_reflns_theta_min         5.125
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_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      4.00  36.00   1.00    1.50    --  -33.50  19.00-180.00   32
  2  ω    -67.00 -41.00   1.00    1.50    --  -33.50 178.00-120.00   26
  3  ω    -69.00 -30.00   1.00    1.50    --  -33.50  19.00-180.00   39
  4  ω   -101.00 -75.00   1.00    1.50    --  -33.50 178.00-120.00   26
  5  ω    -35.00   7.00   1.00    1.50    --  -33.50  37.00-120.00   42
  6  ω     69.00  99.00   1.00    1.50    --   36.47  57.00 120.00   30
  7  ω     42.00  68.00   1.00    1.50    --   36.47 -99.00  30.00   26
  8  ω     26.00  59.00   1.00    1.50    --   36.47 -77.00  60.00   33
  9  ω    -33.00  11.00   1.00    1.50    --   36.47 -77.00  60.00   44
 10  ω     -3.00  63.00   1.00    1.50    --   36.47 -99.00 -90.00   66
 11  ω     -2.00  32.00   1.00    1.50    --   36.47 -99.00  30.00   34
 12  ω     61.00  87.00   1.00    7.50    --  108.00 -30.00 -90.00   26
 13  ω     41.00  99.00   1.00    7.50    --  108.00 -45.00 -30.00   58
 14  ω     39.00  81.00   1.00    7.50    --  108.00 -30.00  90.00   42
 15  ω     65.00  91.00   1.00    7.50    --  108.00 -30.00 -30.00   26
 16  ω     67.00 115.00   1.00    7.50    --  108.00-111.00 -90.00   48
 17  ω     40.00 106.00   1.00    7.50    --  108.00 -94.00 150.00   66
 18  ω     68.00 107.00   1.00    7.50    --  108.00 -94.00   0.00   39
 19  ω     39.00  91.00   1.00    7.50    --  108.00 -30.00-120.00   52
 20  ω     54.00  91.00   1.00    7.50    --  108.00 -30.00 120.00   37
 21  ω     45.00  88.00   1.00    7.50    --  108.00 -45.00-180.00   43
 22  ω     55.00 145.00   1.00    7.50    --  108.00   0.00  90.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0375184000
_diffrn_orient_matrix_UB_12      0.1183587000
_diffrn_orient_matrix_UB_13      0.0280388000
_diffrn_orient_matrix_UB_21      0.0368623000
_diffrn_orient_matrix_UB_22      -0.0325846000
_diffrn_orient_matrix_UB_23      0.1209634000
_diffrn_orient_matrix_UB_31      0.1528015000
_diffrn_orient_matrix_UB_32      -0.0212535000
_diffrn_orient_matrix_UB_33      -0.0302050000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1892
_reflns_number_total             2542
_reflns_odcompleteness_completeness 99.96
_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 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7b (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2542
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.043
_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)+(0.0686P)²+0.1687P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1442
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C12-C11 = C12A-C11A = C13-C12 = C10-C11A = C11-C10
 1.55 with sigma of 0.02
 C10-O1 = C10-O1A = O1-C13 = O1A-C13A
 1.43 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C12) = Uanis(C12A)
Uanis(C11) = Uanis(C11A)
Uanis(C13) = Uanis(C13A)
Uanis(O1) = Uanis(O1A)
Uanis(O2) = Uanis(O2A)
4. Others
 Sof(H10A)=Sof(C11A)=Sof(H11C)=Sof(H11D)=Sof(C12A)=Sof(H12C)=Sof(H12D)=
 Sof(C13A)=Sof(H13C)=Sof(H13D)=Sof(O1A)=1-FVAR(1)
 Sof(H10)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C13)=
 Sof(H13A)=Sof(H13B)=Sof(O1)=FVAR(1)
 Sof(O2A)=1-FVAR(2)
 Sof(O2)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C10(H10), C10(H10A)
5.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C11A(H11C,H11D), C12(H12A,H12B), C12A(H12C,H12D), C13(H13A,
 H13B), C13A(H13C,H13D), C15(H15A,H15B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C9(H9)
5.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9006(3) 0.3790(2) 0.34447(19) 0.0848(7) Uani 1 1 d . . . . .
H1 H 0.8558 0.4004 0.2780 0.102 Uiso 1 1 calc R . . . .
C2 C 1.0442(3) 0.4014(2) 0.3593(2) 0.0886(7) Uani 1 1 d . . . . .
H2 H 1.0922 0.4358 0.3039 0.106 Uiso 1 1 calc R . . . .
C3 C 1.1111(2) 0.37227(19) 0.4553(2) 0.0755(6) Uani 1 1 d . . . . .
H3 H 1.2065 0.3856 0.4667 0.091 Uiso 1 1 calc R . . . .
C4 C 1.03570(18) 0.32133(15) 0.53852(17) 0.0583(5) Uani 1 1 d . . . . .
C5 C 0.89202(17) 0.30025(14) 0.51521(14) 0.0523(4) Uani 1 1 d . . . . .
C6 C 0.81483(17) 0.24573(15) 0.59585(15) 0.0530(4) Uani 1 1 d . . . . .
C7 C 0.8783(2) 0.21906(16) 0.69560(16) 0.0637(5) Uani 1 1 d . . . . .
H7 H 0.8266 0.1845 0.7487 0.076 Uiso 1 1 calc R . . . .
C8 C 1.0204(2) 0.24286(18) 0.71963(18) 0.0707(6) Uani 1 1 d . . . . .
H8 H 1.0614 0.2252 0.7886 0.085 Uiso 1 1 calc R . . . .
C9 C 1.0973(2) 0.29136(18) 0.64263(19) 0.0687(5) Uani 1 1 d . . . . .
H9 H 1.1918 0.3052 0.6583 0.082 Uiso 1 1 calc R . . . .
C10 C 0.6425(2) 0.10682(19) 0.5272(2) 0.0766(6) Uani 1 1 d D . . . .
H10 H 0.5445 0.1017 0.4999 0.092 Uiso 0.553(4) 1 calc R . P A 1
H10A H 0.5404 0.1012 0.5171 0.092 Uiso 0.447(4) 1 calc R . P A 2
C11 C 0.7405(11) 0.0752(10) 0.4351(10) 0.078(2) Uani 0.553(4) 1 d D . P A 1
H11A H 0.6974 0.0905 0.3625 0.093 Uiso 0.553(4) 1 calc R . P A 1
H11B H 0.8285 0.1142 0.4431 0.093 Uiso 0.553(4) 1 calc R . P A 1
C11A C 0.7011(15) 0.0706(14) 0.4216(12) 0.078(2) Uani 0.447(4) 1 d D . P A 2
H11C H 0.7318 0.1310 0.3776 0.093 Uiso 0.447(4) 1 calc R . P A 2
H11D H 0.6348 0.0270 0.3778 0.093 Uiso 0.447(4) 1 calc R . P A 2
C12 C 0.7635(5) -0.0446(4) 0.4504(4) 0.0829(10) Uani 0.553(4) 1 d D . P A 1
H12A H 0.8530 -0.0685 0.4243 0.100 Uiso 0.553(4) 1 calc R . P A 1
H12B H 0.6882 -0.0875 0.4164 0.100 Uiso 0.553(4) 1 calc R . P A 1
C12A C 0.8230(7) 0.0041(5) 0.4677(5) 0.0829(10) Uani 0.447(4) 1 d D . P A 2
H12C H 0.8984 0.0509 0.4953 0.100 Uiso 0.447(4) 1 calc R . P A 2
H12D H 0.8585 -0.0425 0.4107 0.100 Uiso 0.447(4) 1 calc R . P A 2
C13 C 0.761(3) -0.0427(16) 0.5764(14) 0.093(2) Uani 0.553(4) 1 d D . P A 1
H13A H 0.7341 -0.1139 0.6020 0.111 Uiso 0.553(4) 1 calc R . P A 1
H13B H 0.8544 -0.0278 0.6067 0.111 Uiso 0.553(4) 1 calc R . P A 1
C13A C 0.767(3) -0.062(2) 0.5610(18) 0.093(2) Uani 0.447(4) 1 d D . P A 2
H13C H 0.7114 -0.1236 0.5348 0.111 Uiso 0.447(4) 1 calc R . P A 2
H13D H 0.8401 -0.0860 0.6141 0.111 Uiso 0.447(4) 1 calc R . P A 2
C14 C 0.56541(19) 0.28748(19) 0.5790(2) 0.0730(6) Uani 1 1 d . . . . .
C15 C 0.6003(2) 0.3969(2) 0.6269(2) 0.0812(7) Uani 1 1 d . . . . .
H15A H 0.6721 0.3888 0.6858 0.097 Uiso 1 1 calc R . . . .
H15B H 0.6382 0.4420 0.5697 0.097 Uiso 1 1 calc R . . . .
C16 C 0.4766(3) 0.4520(3) 0.6721(3) 0.1092(11) Uani 1 1 d . . . . .
H16A H 0.4063 0.4624 0.6137 0.164 Uiso 1 1 calc GR . . . .
H16B H 0.5046 0.5209 0.7022 0.164 Uiso 1 1 calc GR . . . .
H16C H 0.4392 0.4082 0.7294 0.164 Uiso 1 1 calc GR . . . .
N1 N 0.82474(17) 0.33020(16) 0.41739(14) 0.0689(5) Uani 1 1 d . . . . .
N2 N 0.67200(15) 0.21603(14) 0.57067(14) 0.0625(4) Uani 1 1 d . . . . .
O1 O 0.668(3) 0.0342(16) 0.6184(12) 0.099(2) Uani 0.553(4) 1 d D . P A 1
O1A O 0.685(4) 0.023(2) 0.6014(16) 0.099(2) Uani 0.447(4) 1 d D . P A 2
O2 O 0.4555(17) 0.2766(16) 0.5252(16) 0.096(2) Uani 0.37(2) 1 d . . P B 1
O2A O 0.4404(10) 0.2581(10) 0.5630(12) 0.096(2) Uani 0.63(2) 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.403(4) . ?
C1 N1 1.312(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.347(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.410(3) . ?
C4 C5 1.413(2) . ?
C4 C9 1.413(3) . ?
C5 C6 1.418(2) . ?
C5 N1 1.369(2) . ?
C6 C7 1.364(3) . ?
C6 N2 1.432(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.406(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.351(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9800 . ?
C10 H10A 0.9800 . ?
C10 C11 1.536(12) . ?
C10 C11A 1.484(14) . ?
C10 N2 1.471(3) . ?
C10 O1 1.432(12) . ?
C10 O1A 1.420(16) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.508(13) . ?
C11A H11C 0.9700 . ?
C11A H11D 0.9700 . ?
C11A C12A 1.511(15) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.523(16) . ?
C12A H12C 0.9700 . ?
C12A H12D 0.9700 . ?
C12A C13A 1.51(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 O1 1.409(12) . ?
C13A H13C 0.9700 . ?
C13A H13D 0.9700 . ?
C13A O1A 1.411(15) . ?
C14 C15 1.503(3) . ?
C14 N2 1.355(3) . ?
C14 O2 1.217(19) . ?
C14 O2A 1.255(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.488(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C2 C1 H1 117.6 . . ?
N1 C1 H1 117.6 . . ?
N1 C1 C2 124.9(2) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 117.62(19) . . ?
C3 C4 C9 123.01(18) . . ?
C9 C4 C5 119.38(17) . . ?
C4 C5 C6 118.80(17) . . ?
N1 C5 C4 122.39(17) . . ?
N1 C5 C6 118.81(16) . . ?
C5 C6 N2 119.75(16) . . ?
C7 C6 C5 119.78(16) . . ?
C7 C6 N2 120.44(17) . . ?
C6 C7 H7 119.4 . . ?
C6 C7 C8 121.20(18) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.06(19) . . ?
C9 C8 H8 120.0 . . ?
C4 C9 H9 119.6 . . ?
C8 C9 C4 120.71(18) . . ?
C8 C9 H9 119.6 . . ?
C11 C10 H10 110.1 . . ?
C11A C10 H10A 106.5 . . ?
N2 C10 H10 110.1 . . ?
N2 C10 H10A 106.5 . . ?
N2 C10 C11 112.2(5) . . ?
N2 C10 C11A 120.6(7) . . ?
O1 C10 H10 110.1 . . ?
O1 C10 C11 108.0(8) . . ?
O1 C10 N2 106.1(11) . . ?
O1A C10 H10A 106.5 . . ?
O1A C10 C11A 102.2(10) . . ?
O1A C10 N2 113.7(14) . . ?
C10 C11 H11A 110.8 . . ?
C10 C11 H11B 110.8 . . ?
H11A C11 H11B 108.9 . . ?
C12 C11 C10 104.6(8) . . ?
C12 C11 H11A 110.8 . . ?
C12 C11 H11B 110.8 . . ?
C10 C11A H11C 111.9 . . ?
C10 C11A H11D 111.9 . . ?
C10 C11A C12A 99.4(9) . . ?
H11C C11A H11D 109.6 . . ?
C12A C11A H11C 111.9 . . ?
C12A C11A H11D 111.9 . . ?
C11 C12 H12A 112.6 . . ?
C11 C12 H12B 112.6 . . ?
C11 C12 C13 95.6(9) . . ?
H12A C12 H12B 110.1 . . ?
C13 C12 H12A 112.6 . . ?
C13 C12 H12B 112.6 . . ?
C11A C12A H12C 110.5 . . ?
C11A C12A H12D 110.5 . . ?
C11A C12A C13A 106.1(13) . . ?
H12C C12A H12D 108.7 . . ?
C13A C12A H12C 110.5 . . ?
C13A C12A H12D 110.5 . . ?
C12 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
O1 C13 C12 114.2(14) . . ?
O1 C13 H13A 108.7 . . ?
O1 C13 H13B 108.7 . . ?
C12A C13A H13C 112.9 . . ?
C12A C13A H13D 112.9 . . ?
H13C C13A H13D 110.3 . . ?
O1A C13A C12A 94.1(19) . . ?
O1A C13A H13C 112.9 . . ?
O1A C13A H13D 112.9 . . ?
N2 C14 C15 117.46(17) . . ?
O2 C14 C15 118.4(10) . . ?
O2 C14 N2 121.4(9) . . ?
O2A C14 C15 120.9(5) . . ?
O2A C14 N2 120.8(5) . . ?
C14 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 C14 112.8(2) . . ?
C16 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 N1 C5 116.80(18) . . ?
C6 N2 C10 118.46(16) . . ?
C14 N2 C6 121.94(16) . . ?
C14 N2 C10 119.47(17) . . ?
C13 O1 C10 103.6(12) . . ?
C13A O1A C10 118.4(17) . . ?

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 -0.7(4) . . . . ?
C2 C1 N1 C5 0.6(4) . . . . ?
C2 C3 C4 C5 1.8(3) . . . . ?
C2 C3 C4 C9 -178.0(2) . . . . ?
C3 C4 C5 C6 177.82(18) . . . . ?
C3 C4 C5 N1 -1.9(3) . . . . ?
C3 C4 C9 C8 179.9(2) . . . . ?
C4 C5 C6 C7 2.9(3) . . . . ?
C4 C5 C6 N2 -175.15(16) . . . . ?
C4 C5 N1 C1 0.7(3) . . . . ?
C5 C4 C9 C8 0.1(3) . . . . ?
C5 C6 C7 C8 -1.2(3) . . . . ?
C5 C6 N2 C10 93.9(2) . . . . ?
C5 C6 N2 C14 -81.8(2) . . . . ?
C6 C5 N1 C1 -179.0(2) . . . . ?
C6 C7 C8 C9 -1.1(3) . . . . ?
C7 C6 N2 C10 -84.1(2) . . . . ?
C7 C6 N2 C14 100.2(3) . . . . ?
C7 C8 C9 C4 1.7(3) . . . . ?
C9 C4 C5 C6 -2.3(3) . . . . ?
C9 C4 C5 N1 177.92(19) . . . . ?
C10 C11 C12 C13 -34.8(11) . . . . ?
C10 C11A C12A C13A 44.1(14) . . . . ?
C11 C10 N2 C6 -45.8(5) . . . . ?
C11 C10 N2 C14 130.0(5) . . . . ?
C11 C10 O1 C13 -7(2) . . . . ?
C11 C12 C13 O1 34(2) . . . . ?
C11A C10 N2 C6 -60.2(7) . . . . ?
C11A C10 N2 C14 115.6(7) . . . . ?
C11A C10 O1A C13A 2(4) . . . . ?
C11A C12A C13A O1A -41(2) . . . . ?
C12 C13 O1 C10 -18(3) . . . . ?
C12A C13A O1A C10 24(4) . . . . ?
C15 C14 N2 C6 -6.1(3) . . . . ?
C15 C14 N2 C10 178.3(2) . . . . ?
N1 C1 C2 C3 -0.7(4) . . . . ?
N1 C5 C6 C7 -177.36(18) . . . . ?
N1 C5 C6 N2 4.6(3) . . . . ?
N2 C6 C7 C8 176.84(18) . . . . ?
N2 C10 C11 C12 145.5(5) . . . . ?
N2 C10 C11A C12A 100.3(9) . . . . ?
N2 C10 O1 C13 -127.6(18) . . . . ?
N2 C10 O1A C13A -130(3) . . . . ?
N2 C14 C15 C16 -158.0(3) . . . . ?
O1 C10 C11 C12 28.9(16) . . . . ?
O1 C10 N2 C6 71.9(11) . . . . ?
O1 C10 N2 C14 -112.3(11) . . . . ?
O1A C10 C11A C12A -27(2) . . . . ?
O1A C10 N2 C6 61.7(15) . . . . ?
O1A C10 N2 C14 -122.5(15) . . . . ?
O2 C14 C15 C16 40.3(10) . . . . ?
O2 C14 N2 C6 155.1(10) . . . . ?
O2 C14 N2 C10 -20.6(11) . . . . ?
O2A C14 C15 C16 11.6(10) . . . . ?
O2A C14 N2 C6 -175.7(9) . . . . ?
O2A C14 N2 C10 8.7(9) . . . . ?


_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 1.261
_oxdiff_exptl_absorpt_empirical_full_min 0.852
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
